Literature DB >> 26396854

Crystal structure of (μ-N-allyl-thio-urea-κ(2) S:S)bis-[μ-bis-(di-phenyl-phosphanyl)methane-κ(2) P:P']bis-[bromido-copper(I)] aceto-nitrile disolvate.

Mareeya Hemman1, Chaveng Pakawatchai2, Jaursup Boonmak3, Sujittra Youngme3, Saowanit Saithong2.   

Abstract

The reaction of cuprous bromide with a mixture of 1,1-bis-(di-phenyl-phosphan-yl)methane (dppm: C25H22P2) and N-allyl-thio-urea (ATU: C4H8N2S) in aceto-nitrile yielded the title solvated dinuclear complex, [Cu2Br2(C4H8N2S)(C25H22P2)2]·2C2H3N or [Cu2Br2(ATU)(dppm)2]·2CH3CN. Both Cu(+) ions adopt distorted tetra-hedral geometries, being coordinated by one terminal Br atom, one μ(2)-S atom of the bridging ATU ligand and two P atoms of the bridging dppm ligands. Within the complex, intra-molecular C-H⋯S, C-H⋯π, N-H⋯Br and π-π stacking inter-actions are observed. In the crystal, the components are linked by N-H⋯Br and C-H⋯N hydrogen bonds and weak π-π stacking inter-actions, generating chains propagating in the [100] direction.

Entities:  

Keywords:  C—H⋯π inter­actions; N′-allyl­thio­urea; copper(I) complex; crystal structure; di­phenyl­phosphino­methane; hydrogen bonding; π–π stacking inter­actions

Year:  2015        PMID： 26396854      PMCID： PMC4555395          DOI： 10.1107/S2056989015015637

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Chemical context

Copper(I) complexes with mixed ligands containing diphosphine are of inter­est because of their attractive coordination chemistry and several potential applications resulting from their photophysical properties (Yam et al., 1999 ▸; Jin et al., 2009 ▸; Zhang et al., 2011 ▸, 2014 ▸; Tsiaggali et al., 2013 ▸), anti­bacterial activity and their inter­action ability with native calf thymus DNA (CT–DNA) (Tsiaggali et al., 2013 ▸). One of the diphosphine ligands, 1,1-bis­(diphenylphosphino)methane (dppm: C25H22P2) is a bridging bidentate ligand which is effective in forming various structures with many types of additional ligands, leading to copper(I) complexes as mononuclear, dinuclear, trinuclear and tetra­nuclear models, depending on the nature of the mixed-ligand partners and the stoichiometric ratio between the reactants and experimental conditions (Ruina et al., 1997 ▸; Pérez-Lourido et al.,1998 ▸; Dennehy et al., 2009 ▸; Zhang et al., 2011 ▸). N-allyl­thio­urea (ATU: C4H8N2S) is a substituted thio­urea ligand, which contains sulfur donor atoms that can bind to a copper(I) ion via a variety of bonding modes (Filinchuk et al., 1996 ▸, 2001 ▸; Olijnyk et al., 2003 ▸). A family of allyl­thiuorea–metal complexes has been studied for their potential photonic applications and non-linear optical (NLO) efficiencies (Perumal & Babu, 2008 ▸, 2012 ▸). In this paper, we report the synthesis and structure of a mixed-ligand copper(I) complex with dppm and ATU ligands.

Structural commentary

The title complex [Cu2Br2(ATU)(dppm)2]·2CH3CN, (I), is shown in Fig. 1 ▸. The discrete neutral dinuclear complex contains an asymmetric triply bridged dicopper(I) core forming two six-membered rings in a chair conformation, Cu1—S1—Cu2—P1—C13—P2 and Cu1—S1—Cu2—P3—C38—P4, sharing the Cu1—S1—Cu2 part. Each CuI atom is coordinated by P atoms from the different dppm ligands, one μ 2-S bridging atom of ATU and the bromide ion as a terminal ligand, forming a distorted tetra­hedral environment, as illus­trated by the range of angles around the Cu atoms [100.87 (2)– 116.49 (3)° for Cu1 and 97.45 (3)–119.31 (3)° for Cu2]. Both CuI atoms share a tetra­hedral corner via an S-atom bridge.
Figure 1

The mol­ecular structure of (I) showing 50% probability displacement ellipsoids.

The Cu⋯Cu distance in (I) is 3.3780 (7) Å, which is similar to the Cu⋯Cu distance of 3.375 (2) Å in a copper(I) complex containing an S–bridging ligand and bidentate bridging dppm, [Cu2I2(C3H8N2S)(C25H22P2)2]·1.5CH3CN (Nimthong et al., 2013 ▸) and much longer than 2.8 Å which is the sum of the van der Waals radii of the copper atoms (Yam et al., 2001 ▸). The Cu—P bond lengths in (I) (Table 1 ▸) range from 2.2604 (8) to 2.2803 (8) Å and the Cu—S bond lengths of the bridges, 2.3543 (8) and 2.3520 (8) Å, are likewise similar to the those in the above mentioned complex [Cu—P = 2.2563 (10)–2.2786 (11) Å; Cu—S = 2.3450 (11) and 2.3493 (11) Å]. The Cu1—Br1 and Cu2—Br2 bond lengths of 2.5126 (4) and 2.5238 (4) Å, respectively, are slightly longer than the Cu—Br(terminal) [2.4826 (5) Å] for [CuBr(PPh3)3]·CH3CN (Altaf & Stoeckli-Evans, 2010 ▸)
Table 1

Selected bond lengths ()

Cu1P12.2795(8)Cu2P22.2604(8)
Cu1P42.2803(8)Cu2P32.2730(8)
Cu1S12.3543(8)Cu2S12.3520(8)
Cu1Br12.5126(4)Cu2Br22.5238(4)
The intra­molecular inter­action C44—H44⋯S1 (Table 2 ▸) has an effect on the Cu1–S1–Cu2 plane, bending it from the Cu2P2 plane of the Cu1–S1–Cu2–P3–C38–P4 chair conformation by an angle [72.59 (3)°] that is significantly larger than that for the Cu1–S1–Cu2–P1–C13–P2 plane [45.68 (2)°]. Thus, the C—H⋯S effect might be the influence that leads to the longer distance between the centroids (Cg8: C39–C44, Cg9: C45–C50; Cg4: C7–C12 and Cg5: C13–C18) of the phenyl rings, Cg8⋯Cg9 [4.0356 (17) Å] compared with the Cg4⋯Cg5 distance [3.6097 (19) Å]. The intra­molecular C—H⋯π inter­action (C31—H31⋯Cg6) also imposes a contact, of 3.476 (3) Å, between the Csp 2 atom of the phenyl ring and another phenyl ring centroid (C20–C25) of the other dppm ligand. An inter­action (C12—H12⋯N2) between Cg5 and the NH2 group is also observed. In addition, two intra­molecular N—H⋯Br inter­actions are found between the NH2 group of ATU and Br atoms. A perspective view of all the intra­molecular inter­actions in (I) is depicted in Fig. 2 ▸.
Table 2

Hydrogen-bond geometry (, )

Cg6 is the centroid of the C20C25 ring.

DHA DHHA D A DHA
C12H12N20.952.563.438(4)154
C44H44S10.952.873.751(3)154
C50H50N3i 0.952.573.462(5)156
C55H55CN4ii 0.982.573.338(5)136
N1H1ABr20.84(2)2.74(2)3.580(3)172(4)
N1H1BBr2iii 0.85(2)2.61(2)3.415(3)158(3)
N2H2ABr10.85(2)2.63(2)3.468(3)166(3)
C31H31Cg60.952.973.476(3)115

Symmetry codes: (i) ; (ii) ; (iii) .

Figure 2

Intra­molecular inter­actions in (I)

Supra­molecular features

In the crystal, neighbouring dinuclear mol­ecules form a hydrogen-bonded dimer held together by two N—H⋯Br bonds as a cyclic pattern with its symmetry–equivalent partner, generated by a crystallographic inversion center (symmetry code: −x, 2 − y, −z), which generates (8) loops. Moreover, the dimers are linked together by very weak π–π stacking of the Cg8⋯Cg8iii rings [3.9338 (16) Å, symmetry code: (iii) 1 − x, 2 − y, −z] generating a chain of alternating N—H⋯Br links and π–π stacking running along [100], as shown in Fig. 3 ▸. The N atoms of the aceto­nitrile solvent mol­ecules both accept C—H⋯N inter­actions (C55—H55⋯N4ii and C50—H50⋯N3i; symmetry codes: (i) −x + 1, y + , −z + ; (ii) = −x, y − , −z + ) from the dppm phenyl rings. Numerical details of the hydrogen–bond geometry are given in Table 2 ▸.
Figure 3

A chain in the structure of (I) mediated by N—H⋯Br hydrogen bonds and aromatic π–π stacking.

Database survey

A search of the Cambridge Structural Database (Version 5.36, update November 2014; Groom & Allen, 2014 ▸) found 309 complexes of copper(I) with mixed dppm and other ligands. There are six copper(I) complexes with an ATU ligand, three complexes containing only an ATU ligand and three complexes containing a mixed ATU and other ligands. However, there is only one structure that has a similar core structure and coordination mode to the title compound, [Cu2I2(C3H8N2S)(dppm)2]·1.5CH3CN, studied by Nimthong et al. (2013 ▸).

Synthesis and crystallization

Copper(I) bromide (0.07 g, 0.49 mmol) was added to a solution of 1,1-bis­(di­phenyl­phosphino)methane (0.19 g, 0.50 mmol) in 30 ml aceto­nitrile at 338 K. The mixture was refluxed for two h and a white precipitate was formed. After that, N-allyl­thio­urea (0.06 g, 0.52 mmol) was added and further refluxed for four h and the precipitate slowly disappeared. Colorless crystals were obtained after the clear solution was left to evaporate at room temperature for a few days. The yield was 33% based on CuBr. Calculated for C58H58Br2Cu2N4P4S: C 55.55, H 4.66, N 4.47 and S 2.56%. Found: C 55.28, H 4.28, N 3.68 and S 2.54%. The main IR bands (KBr disc, cm−1): 3282 [ν(NH2)], 3168 [ν(NH2)], 3058 [ν(=C—H)ph], 1580 [ν(C=S)] and 1110 [ν(P—Cph)].

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3 ▸. Hydrogen atoms bonded to carbon were included at geometrically idealized positions and refined as riding with U iso(H) = 1.2U eq(C) or 1.5U eq(Cmethyl). The N—H atoms were located in a difference map and the coordinates were refined with an N—H distance restraint of 0.86 Å and with U iso(H) = 1.2U(N).
Table 3

Experimental details

Crystal data
Chemical formula[Cu2Br2(C4H8N2S)(C25H22P2)2]2C2H3N
M r 1253.92
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c ()13.7569(7), 24.2730(11), 17.8527(8)
()111.317(2)
V (3)5553.5(5)
Z 4
Radiation typeMo K
(mm1)2.40
Crystal size (mm)0.47 0.30 0.13
 
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan (SADABS; Bruker, 2013 ▸)
T min, T max 0.489, 0.745
No. of measured, independent and observed [I > 2(I)] reflections70511, 10194, 8464
R int 0.064
(sin /)max (1)0.603
 
Refinement
R[F 2 > 2(F 2)], wR(F 2), S 0.032, 0.067, 1.04
No. of reflections10194
No. of parameters651
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
max, min (e 3)0.68, 0.39

Computer programs: APEX2 and SAINT (Bruker, 2013 ▸), SHELXS97 (Sheldrick, 2008 ▸), SHELXL2014/7 (Sheldrick, 2015 ▸), Mercury (Macrae et al., 2008 ▸) and WinGX publication routines (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015015637/hb7479sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015015637/hb7479Isup2.hkl CCDC reference: 1419827 Additional supporting information: crystallographic information; 3D view; checkCIF report
[Cu2Br2(C4H8N2S)(C25H22P2)2]·2C2H3NF(000) = 2552
Mr = 1253.92Dx = 1.500 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.7569 (7) ÅCell parameters from 9875 reflections
b = 24.2730 (11) Åθ = 2.9–25.3°
c = 17.8527 (8) ŵ = 2.40 mm−1
β = 111.317 (2)°T = 100 K
V = 5553.5 (5) Å3Block, colourless
Z = 40.47 × 0.30 × 0.13 mm
Bruker APEXII CCD diffractometer8464 reflections with I > 2σ(I)
φ and ω scansRint = 0.064
Absorption correction: multi-scan (SADABS; Bruker, 2013)θmax = 25.4°, θmin = 2.9°
Tmin = 0.489, Tmax = 0.745h = −16→16
70511 measured reflectionsk = −29→29
10194 independent reflectionsl = −21→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.067H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0189P)2 + 10.1133P] where P = (Fo2 + 2Fc2)/3
10194 reflections(Δ/σ)max = 0.003
651 parametersΔρmax = 0.68 e Å−3
3 restraintsΔρmin = −0.39 e Å−3
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
xyzUiso*/Ueq
Cu10.19238 (3)0.77461 (2)0.04894 (2)0.01110 (8)
Cu20.24847 (3)0.90361 (2)0.12313 (2)0.01111 (8)
Br10.09590 (2)0.71918 (2)−0.07468 (2)0.01574 (7)
Br20.22027 (2)1.00599 (2)0.10111 (2)0.01554 (7)
S10.17431 (5)0.86405 (3)−0.00549 (4)0.01173 (15)
P10.11946 (6)0.76195 (3)0.14370 (4)0.01021 (15)
P20.18113 (6)0.87778 (3)0.21589 (4)0.01031 (15)
P30.41788 (6)0.88387 (3)0.14411 (4)0.00975 (15)
P40.36776 (6)0.76019 (3)0.08920 (4)0.01024 (15)
N10.0202 (2)0.93599 (11)−0.05759 (16)0.0189 (6)
N2−0.01468 (19)0.84941 (10)−0.11461 (15)0.0163 (5)
C10.1247 (2)0.69122 (11)0.18132 (17)0.0116 (6)
C20.1656 (2)0.67627 (12)0.26213 (17)0.0165 (6)
H20.19300.70370.30220.020*
C30.1666 (3)0.62129 (12)0.28439 (18)0.0199 (7)
H30.19600.61130.33960.024*
C40.1255 (3)0.58136 (12)0.22736 (19)0.0214 (7)
H40.12620.54390.24300.026*
C50.0828 (3)0.59573 (12)0.14673 (19)0.0218 (7)
H50.05320.56810.10720.026*
C60.0831 (2)0.65008 (12)0.12364 (18)0.0171 (6)
H60.05500.65950.06820.021*
C7−0.0200 (2)0.77548 (11)0.11547 (17)0.0128 (6)
C8−0.0716 (3)0.76700 (16)0.1687 (2)0.0321 (9)
H8−0.03350.75510.22200.039*
C9−0.1775 (3)0.77573 (16)0.1446 (2)0.0328 (9)
H9−0.21180.76990.18150.039*
C10−0.2336 (2)0.79270 (13)0.0679 (2)0.0247 (8)
H10−0.30670.79840.05160.030*
C11−0.1844 (3)0.80142 (15)0.0147 (2)0.0319 (8)
H11−0.22330.8132−0.03860.038*
C12−0.0770 (3)0.79299 (14)0.03881 (19)0.0241 (7)
H12−0.04290.79940.00190.029*
C130.1803 (2)0.80300 (11)0.23586 (16)0.0119 (6)
H13A0.25310.79030.26350.014*
H13B0.14210.79650.27250.014*
C140.0483 (2)0.89986 (11)0.20261 (17)0.0123 (6)
C15−0.0113 (2)0.92542 (13)0.13206 (18)0.0209 (7)
H150.01740.93200.09190.025*
C16−0.1132 (3)0.94168 (14)0.1190 (2)0.0269 (8)
H16−0.15360.95930.07000.032*
C17−0.1553 (2)0.93239 (12)0.17676 (18)0.0176 (7)
H17−0.22460.94390.16820.021*
C18−0.0967 (3)0.90642 (14)0.2469 (2)0.0263 (8)
H18−0.12620.89940.28650.032*
C190.0052 (3)0.89033 (14)0.26059 (19)0.0245 (8)
H190.04530.87280.30970.029*
C200.2572 (2)0.90622 (11)0.31536 (17)0.0122 (6)
C210.2730 (2)0.96361 (12)0.31837 (18)0.0177 (7)
H210.24230.98510.27120.021*
C220.3328 (3)0.98882 (13)0.38964 (19)0.0215 (7)
H220.34311.02760.39120.026*
C230.3778 (2)0.95781 (13)0.45895 (18)0.0192 (7)
H230.41860.97520.50800.023*
C240.3628 (2)0.90128 (12)0.45614 (17)0.0159 (6)
H240.39400.88000.50350.019*
C250.3028 (2)0.87543 (12)0.38493 (17)0.0148 (6)
H250.29290.83670.38380.018*
C260.5171 (2)0.91157 (11)0.23539 (17)0.0118 (6)
C270.6010 (2)0.94399 (11)0.23557 (18)0.0143 (6)
H270.60700.95390.18600.017*
C280.6755 (2)0.96181 (12)0.30703 (18)0.0180 (7)
H280.73340.98280.30630.022*
C290.6658 (2)0.94917 (12)0.37982 (19)0.0186 (7)
H290.71660.96170.42890.022*
C300.5817 (2)0.91827 (12)0.38042 (18)0.0186 (7)
H300.57430.91000.43010.022*
C310.5079 (2)0.89923 (12)0.30910 (17)0.0145 (6)
H310.45080.87770.31030.017*
C320.4624 (2)0.90346 (11)0.06293 (17)0.0124 (6)
C330.5599 (2)0.88860 (12)0.06151 (17)0.0150 (6)
H330.60630.86720.10420.018*
C340.5894 (2)0.90472 (12)−0.00143 (18)0.0189 (7)
H340.65660.8953−0.00110.023*
C350.5212 (2)0.93456 (12)−0.06500 (18)0.0196 (7)
H350.54110.9451−0.10860.024*
C360.4244 (2)0.94896 (12)−0.06488 (18)0.0186 (7)
H360.37740.9691−0.10880.022*
C370.3950 (2)0.93417 (11)−0.00067 (17)0.0138 (6)
H370.32890.9451−0.00030.017*
C380.4531 (2)0.81004 (11)0.16173 (16)0.0111 (6)
H38A0.52480.80540.16230.013*
H38B0.45460.80020.21600.013*
C390.4238 (2)0.75692 (11)0.01009 (17)0.0116 (6)
C400.5075 (2)0.72272 (12)0.01472 (18)0.0161 (6)
H400.53740.69960.06020.019*
C410.5475 (2)0.72216 (12)−0.04627 (18)0.0184 (7)
H410.60400.6984−0.04270.022*
C420.5049 (2)0.75631 (13)−0.11252 (18)0.0191 (7)
H420.53260.7563−0.15410.023*
C430.4223 (2)0.79031 (13)−0.11797 (18)0.0194 (7)
H430.39360.8139−0.16320.023*
C440.3809 (2)0.79025 (12)−0.05756 (17)0.0157 (6)
H440.32290.8131−0.06240.019*
C450.4101 (2)0.69546 (11)0.14349 (16)0.0124 (6)
C460.3359 (2)0.65358 (12)0.12815 (18)0.0157 (6)
H460.26610.66040.09340.019*
C470.3633 (3)0.60202 (12)0.16316 (19)0.0214 (7)
H470.31220.57380.15210.026*
C480.4646 (3)0.59159 (13)0.21408 (19)0.0241 (7)
H480.48340.55610.23710.029*
C490.5384 (3)0.63302 (13)0.23138 (19)0.0245 (7)
H490.60770.62610.26710.029*
C500.5114 (2)0.68490 (12)0.19664 (18)0.0185 (7)
H500.56240.71330.20920.022*
C510.0488 (2)0.88435 (12)−0.06356 (16)0.0137 (6)
C52−0.1207 (2)0.86166 (14)−0.16977 (19)0.0248 (7)
H52A−0.15570.8852−0.14190.030*
H52B−0.16060.8268−0.18480.030*
C53−0.1221 (3)0.89034 (17)−0.2447 (2)0.0373 (9)
H53−0.07870.9217−0.23840.045*
C54−0.1778 (4)0.8755 (2)−0.3166 (3)0.0612 (14)
H54A−0.22220.8443−0.32530.073*
H54B−0.17450.8958−0.36120.073*
C550.1704 (3)0.32731 (15)0.0731 (2)0.0354 (9)
H55A0.09700.32030.06450.053*
H55B0.18460.31550.02560.053*
H55C0.18490.36680.08190.053*
C560.2369 (3)0.29660 (16)0.1434 (2)0.0316 (8)
N30.2868 (3)0.27258 (16)0.1977 (2)0.0492 (9)
N4−0.0747 (3)0.95436 (13)0.43359 (19)0.0373 (8)
C580.0114 (3)0.94818 (14)0.4440 (2)0.0263 (8)
C570.1216 (3)0.94051 (16)0.4589 (2)0.0344 (9)
H57A0.16330.95830.50980.052*
H57B0.13830.95700.41490.052*
H57C0.13760.90100.46210.052*
H1A0.064 (2)0.9555 (14)−0.0224 (18)0.041*
H1B−0.0412 (18)0.9480 (15)−0.082 (2)0.041*
H2A0.012 (3)0.8176 (10)−0.114 (2)0.041*
U11U22U33U12U13U23
Cu10.01203 (18)0.01158 (17)0.01131 (17)0.00084 (13)0.00618 (14)0.00045 (14)
Cu20.01152 (18)0.01144 (17)0.01248 (17)0.00183 (13)0.00689 (14)0.00178 (14)
Br10.01909 (16)0.01499 (15)0.01340 (14)−0.00064 (12)0.00622 (12)−0.00410 (12)
Br20.01744 (16)0.01076 (14)0.02000 (15)0.00327 (11)0.00868 (13)0.00302 (12)
S10.0122 (4)0.0117 (3)0.0114 (3)0.0017 (3)0.0045 (3)0.0010 (3)
P10.0117 (4)0.0099 (3)0.0103 (3)0.0002 (3)0.0055 (3)−0.0005 (3)
P20.0132 (4)0.0090 (3)0.0111 (3)0.0006 (3)0.0072 (3)−0.0001 (3)
P30.0110 (4)0.0089 (3)0.0111 (3)0.0010 (3)0.0061 (3)0.0015 (3)
P40.0123 (4)0.0088 (3)0.0109 (3)0.0010 (3)0.0058 (3)0.0005 (3)
N10.0171 (15)0.0149 (13)0.0213 (15)0.0037 (11)0.0031 (12)−0.0013 (11)
N20.0146 (14)0.0158 (13)0.0160 (13)0.0008 (11)0.0027 (11)0.0011 (11)
C10.0111 (15)0.0117 (14)0.0150 (14)−0.0024 (11)0.0082 (12)0.0001 (12)
C20.0210 (17)0.0159 (15)0.0152 (15)−0.0011 (13)0.0097 (13)−0.0024 (13)
C30.0303 (19)0.0173 (16)0.0159 (15)0.0050 (13)0.0130 (14)0.0052 (13)
C40.033 (2)0.0113 (15)0.0261 (17)0.0003 (13)0.0186 (16)0.0030 (13)
C50.0316 (19)0.0121 (15)0.0242 (17)−0.0049 (13)0.0130 (15)−0.0064 (14)
C60.0220 (17)0.0159 (15)0.0137 (15)0.0000 (13)0.0068 (13)0.0010 (13)
C70.0127 (15)0.0090 (14)0.0176 (15)−0.0008 (11)0.0068 (12)−0.0034 (12)
C80.0231 (19)0.050 (2)0.0283 (19)0.0040 (17)0.0152 (16)0.0097 (17)
C90.0194 (19)0.047 (2)0.041 (2)0.0028 (16)0.0217 (17)0.0022 (19)
C100.0119 (16)0.0184 (16)0.042 (2)−0.0023 (13)0.0079 (15)−0.0130 (15)
C110.0218 (19)0.039 (2)0.031 (2)0.0106 (16)0.0054 (16)0.0025 (17)
C120.0218 (18)0.0294 (18)0.0235 (17)0.0045 (14)0.0109 (15)0.0035 (15)
C130.0144 (15)0.0110 (14)0.0122 (14)−0.0005 (11)0.0068 (12)−0.0014 (12)
C140.0146 (15)0.0078 (13)0.0157 (14)−0.0026 (11)0.0070 (12)−0.0034 (12)
C150.0176 (17)0.0299 (18)0.0190 (16)0.0009 (14)0.0111 (14)0.0073 (14)
C160.0223 (19)0.034 (2)0.0244 (18)0.0060 (15)0.0082 (15)0.0127 (16)
C170.0130 (16)0.0161 (15)0.0253 (17)0.0020 (12)0.0086 (14)−0.0008 (13)
C180.0249 (19)0.037 (2)0.0252 (18)0.0073 (15)0.0190 (15)0.0055 (16)
C190.0241 (18)0.035 (2)0.0179 (16)0.0112 (15)0.0121 (14)0.0116 (15)
C200.0119 (15)0.0138 (14)0.0131 (14)−0.0004 (12)0.0072 (12)−0.0040 (12)
C210.0230 (18)0.0137 (15)0.0168 (15)−0.0006 (12)0.0077 (14)−0.0005 (13)
C220.0281 (19)0.0122 (15)0.0256 (17)−0.0041 (13)0.0114 (15)−0.0033 (14)
C230.0193 (17)0.0229 (17)0.0181 (16)−0.0061 (13)0.0099 (14)−0.0087 (14)
C240.0146 (16)0.0220 (16)0.0136 (14)0.0021 (13)0.0083 (13)0.0009 (13)
C250.0175 (16)0.0149 (15)0.0155 (15)−0.0001 (12)0.0102 (13)−0.0020 (13)
C260.0121 (15)0.0085 (14)0.0150 (14)0.0028 (11)0.0052 (12)0.0000 (12)
C270.0164 (16)0.0111 (14)0.0186 (15)0.0015 (12)0.0100 (13)0.0008 (12)
C280.0135 (16)0.0147 (15)0.0266 (17)0.0000 (12)0.0083 (14)−0.0027 (13)
C290.0153 (16)0.0193 (16)0.0200 (16)0.0029 (13)0.0049 (13)−0.0065 (13)
C300.0191 (17)0.0223 (16)0.0171 (16)0.0037 (13)0.0097 (14)0.0002 (13)
C310.0140 (15)0.0159 (15)0.0153 (15)−0.0019 (12)0.0073 (13)−0.0025 (13)
C320.0172 (16)0.0091 (13)0.0137 (14)−0.0026 (12)0.0088 (12)−0.0020 (12)
C330.0162 (16)0.0143 (15)0.0160 (15)−0.0010 (12)0.0077 (13)−0.0003 (12)
C340.0201 (17)0.0170 (15)0.0265 (17)−0.0015 (13)0.0167 (14)−0.0033 (14)
C350.0289 (19)0.0179 (16)0.0176 (16)−0.0057 (13)0.0151 (14)−0.0010 (13)
C360.0241 (18)0.0151 (15)0.0154 (15)−0.0026 (13)0.0057 (14)0.0030 (13)
C370.0125 (15)0.0116 (14)0.0180 (15)−0.0036 (11)0.0066 (13)0.0009 (12)
C380.0126 (15)0.0111 (14)0.0110 (14)0.0003 (11)0.0060 (12)0.0006 (12)
C390.0112 (15)0.0113 (14)0.0134 (14)−0.0046 (11)0.0059 (12)−0.0044 (12)
C400.0137 (15)0.0167 (15)0.0199 (16)−0.0006 (12)0.0085 (13)−0.0010 (13)
C410.0142 (16)0.0196 (16)0.0256 (17)−0.0005 (13)0.0123 (14)−0.0055 (14)
C420.0207 (17)0.0247 (17)0.0171 (15)−0.0051 (13)0.0131 (14)−0.0069 (14)
C430.0208 (17)0.0234 (17)0.0152 (15)−0.0012 (13)0.0081 (13)0.0007 (13)
C440.0184 (17)0.0132 (15)0.0168 (15)0.0019 (12)0.0081 (13)−0.0011 (12)
C450.0183 (16)0.0109 (14)0.0108 (14)0.0034 (12)0.0088 (13)−0.0015 (12)
C460.0199 (17)0.0126 (14)0.0167 (15)−0.0004 (12)0.0091 (13)−0.0004 (12)
C470.0308 (19)0.0133 (15)0.0237 (17)−0.0030 (13)0.0143 (15)0.0013 (14)
C480.040 (2)0.0106 (15)0.0235 (17)0.0026 (14)0.0132 (16)0.0049 (13)
C490.0267 (19)0.0216 (17)0.0223 (17)0.0063 (14)0.0053 (15)0.0052 (14)
C500.0236 (18)0.0127 (15)0.0199 (16)0.0010 (13)0.0087 (14)0.0008 (13)
C510.0176 (16)0.0156 (15)0.0100 (14)0.0015 (12)0.0076 (12)0.0042 (12)
C520.0163 (17)0.0271 (18)0.0244 (17)0.0004 (14)−0.0004 (14)−0.0026 (15)
C530.029 (2)0.048 (2)0.026 (2)0.0088 (17)−0.0013 (17)0.0047 (18)
C540.063 (3)0.077 (3)0.033 (2)0.026 (3)0.004 (2)0.010 (2)
C550.026 (2)0.033 (2)0.047 (2)−0.0025 (16)0.0120 (18)0.0049 (18)
C560.0210 (19)0.038 (2)0.039 (2)−0.0014 (16)0.0146 (18)−0.0081 (18)
N30.032 (2)0.073 (3)0.042 (2)0.0195 (19)0.0129 (17)0.009 (2)
N40.030 (2)0.0415 (19)0.0396 (19)0.0002 (15)0.0113 (15)−0.0120 (15)
C580.028 (2)0.0248 (18)0.0266 (18)0.0004 (15)0.0112 (16)−0.0045 (15)
C570.031 (2)0.035 (2)0.042 (2)−0.0028 (16)0.0187 (18)−0.0069 (18)
Cu1—P12.2795 (8)C23—C241.386 (4)
Cu1—P42.2803 (8)C23—H230.9500
Cu1—S12.3543 (8)C24—C251.389 (4)
Cu1—Br12.5126 (4)C24—H240.9500
Cu2—P22.2604 (8)C25—H250.9500
Cu2—P32.2730 (8)C26—C271.396 (4)
Cu2—S12.3520 (8)C26—C311.399 (4)
Cu2—Br22.5238 (4)C27—C281.383 (4)
S1—C511.731 (3)C27—H270.9500
P1—C71.828 (3)C28—C291.388 (4)
P1—C11.836 (3)C28—H280.9500
P1—C131.844 (3)C29—C301.382 (4)
P2—C141.835 (3)C29—H290.9500
P2—C201.837 (3)C30—C311.388 (4)
P2—C131.850 (3)C30—H300.9500
P3—C321.830 (3)C31—H310.9500
P3—C261.831 (3)C32—C371.393 (4)
P3—C381.853 (3)C32—C331.398 (4)
P4—C451.827 (3)C33—C341.383 (4)
P4—C391.841 (3)C33—H330.9500
P4—C381.848 (3)C34—C351.386 (4)
N1—C511.329 (4)C34—H340.9500
N1—H1A0.842 (18)C35—C361.378 (4)
N1—H1B0.849 (18)C35—H350.9500
N2—C511.317 (4)C36—C371.394 (4)
N2—C521.464 (4)C36—H360.9500
N2—H2A0.853 (18)C37—H370.9500
C1—C21.393 (4)C38—H38A0.9900
C1—C61.399 (4)C38—H38B0.9900
C2—C31.391 (4)C39—C441.394 (4)
C2—H20.9500C39—C401.397 (4)
C3—C41.370 (4)C40—C411.387 (4)
C3—H30.9500C40—H400.9500
C4—C51.387 (4)C41—C421.388 (4)
C4—H40.9500C41—H410.9500
C5—C61.383 (4)C42—C431.379 (4)
C5—H50.9500C42—H420.9500
C6—H60.9500C43—C441.391 (4)
C7—C121.374 (4)C43—H430.9500
C7—C81.393 (4)C44—H440.9500
C8—C91.377 (5)C45—C501.395 (4)
C8—H80.9500C45—C461.395 (4)
C9—C101.368 (5)C46—C471.388 (4)
C9—H90.9500C46—H460.9500
C10—C111.369 (5)C47—C481.383 (5)
C10—H100.9500C47—H470.9500
C11—C121.396 (5)C48—C491.381 (5)
C11—H110.9500C48—H480.9500
C12—H120.9500C49—C501.393 (4)
C13—H13A0.9900C49—H490.9500
C13—H13B0.9900C50—H500.9500
C14—C151.376 (4)C52—C531.502 (5)
C14—C191.387 (4)C52—H52A0.9900
C15—C161.391 (4)C52—H52B0.9900
C15—H150.9500C53—C541.284 (5)
C16—C171.373 (4)C53—H530.9500
C16—H160.9500C54—H54A0.9500
C17—C181.371 (4)C54—H54B0.9500
C17—H170.9500C55—C561.460 (5)
C18—C191.388 (4)C55—H55A0.9800
C18—H180.9500C55—H55B0.9800
C19—H190.9500C55—H55C0.9800
C20—C251.389 (4)C56—N31.127 (5)
C20—C211.408 (4)N4—C581.140 (4)
C21—C221.382 (4)C58—C571.453 (5)
C21—H210.9500C57—H57A0.9800
C22—C231.387 (4)C57—H57B0.9800
C22—H220.9500C57—H57C0.9800
P1—Cu1—P4116.49 (3)C24—C23—H23120.2
P1—Cu1—S1114.94 (3)C22—C23—H23120.2
P4—Cu1—S1102.27 (3)C23—C24—C25120.8 (3)
P1—Cu1—Br1110.20 (2)C23—C24—H24119.6
P4—Cu1—Br1110.80 (2)C25—C24—H24119.6
S1—Cu1—Br1100.87 (2)C20—C25—C24120.0 (3)
P2—Cu2—P3119.31 (3)C20—C25—H25120.0
P2—Cu2—S1117.01 (3)C24—C25—H25120.0
P3—Cu2—S197.45 (3)C27—C26—C31118.4 (3)
P2—Cu2—Br2107.86 (2)C27—C26—P3123.8 (2)
P3—Cu2—Br2108.88 (2)C31—C26—P3117.7 (2)
S1—Cu2—Br2105.21 (2)C28—C27—C26120.8 (3)
C51—S1—Cu2116.91 (10)C28—C27—H27119.6
C51—S1—Cu1116.25 (10)C26—C27—H27119.6
Cu2—S1—Cu191.74 (3)C27—C28—C29120.2 (3)
C7—P1—C199.56 (13)C27—C28—H28119.9
C7—P1—C13103.87 (13)C29—C28—H28119.9
C1—P1—C13103.55 (13)C30—C29—C28119.5 (3)
C7—P1—Cu1118.18 (10)C30—C29—H29120.2
C1—P1—Cu1115.38 (9)C28—C29—H29120.2
C13—P1—Cu1114.19 (9)C29—C30—C31120.6 (3)
C14—P2—C20101.87 (12)C29—C30—H30119.7
C14—P2—C13103.65 (13)C31—C30—H30119.7
C20—P2—C13102.91 (13)C30—C31—C26120.4 (3)
C14—P2—Cu2118.58 (9)C30—C31—H31119.8
C20—P2—Cu2111.27 (9)C26—C31—H31119.8
C13—P2—Cu2116.49 (9)C37—C32—C33118.8 (3)
C32—P3—C26104.69 (13)C37—C32—P3118.0 (2)
C32—P3—C38104.10 (13)C33—C32—P3123.2 (2)
C26—P3—C3898.03 (12)C34—C33—C32120.6 (3)
C32—P3—Cu2115.68 (10)C34—C33—H33119.7
C26—P3—Cu2117.19 (9)C32—C33—H33119.7
C38—P3—Cu2114.89 (9)C33—C34—C35120.1 (3)
C45—P4—C39103.19 (13)C33—C34—H34119.9
C45—P4—C38101.10 (13)C35—C34—H34119.9
C39—P4—C38103.25 (12)C36—C35—C34119.9 (3)
C45—P4—Cu1113.34 (10)C36—C35—H35120.0
C39—P4—Cu1117.09 (9)C34—C35—H35120.0
C38—P4—Cu1116.76 (9)C35—C36—C37120.4 (3)
C51—N1—H1A116 (3)C35—C36—H36119.8
C51—N1—H1B123 (3)C37—C36—H36119.8
H1A—N1—H1B120 (4)C32—C37—C36120.1 (3)
C51—N2—C52125.7 (3)C32—C37—H37119.9
C51—N2—H2A114 (3)C36—C37—H37119.9
C52—N2—H2A121 (3)P4—C38—P3117.00 (15)
C2—C1—C6118.7 (3)P4—C38—H38A108.0
C2—C1—P1124.8 (2)P3—C38—H38A108.0
C6—C1—P1116.6 (2)P4—C38—H38B108.0
C3—C2—C1120.3 (3)P3—C38—H38B108.0
C3—C2—H2119.9H38A—C38—H38B107.3
C1—C2—H2119.9C44—C39—C40118.5 (3)
C4—C3—C2120.5 (3)C44—C39—P4118.4 (2)
C4—C3—H3119.7C40—C39—P4123.1 (2)
C2—C3—H3119.7C41—C40—C39120.9 (3)
C3—C4—C5119.9 (3)C41—C40—H40119.6
C3—C4—H4120.1C39—C40—H40119.6
C5—C4—H4120.1C40—C41—C42119.9 (3)
C6—C5—C4120.2 (3)C40—C41—H41120.1
C6—C5—H5119.9C42—C41—H41120.1
C4—C5—H5119.9C43—C42—C41120.0 (3)
C5—C6—C1120.4 (3)C43—C42—H42120.0
C5—C6—H6119.8C41—C42—H42120.0
C1—C6—H6119.8C42—C43—C44120.3 (3)
C12—C7—C8118.5 (3)C42—C43—H43119.9
C12—C7—P1119.4 (2)C44—C43—H43119.9
C8—C7—P1122.0 (2)C43—C44—C39120.6 (3)
C9—C8—C7120.5 (3)C43—C44—H44119.7
C9—C8—H8119.7C39—C44—H44119.7
C7—C8—H8119.7C50—C45—C46118.6 (3)
C10—C9—C8120.4 (3)C50—C45—P4124.5 (2)
C10—C9—H9119.8C46—C45—P4116.9 (2)
C8—C9—H9119.8C47—C46—C45120.6 (3)
C9—C10—C11120.0 (3)C47—C46—H46119.7
C9—C10—H10120.0C45—C46—H46119.7
C11—C10—H10120.0C48—C47—C46120.3 (3)
C10—C11—C12119.8 (3)C48—C47—H47119.8
C10—C11—H11120.1C46—C47—H47119.8
C12—C11—H11120.1C49—C48—C47119.8 (3)
C7—C12—C11120.6 (3)C49—C48—H48120.1
C7—C12—H12119.7C47—C48—H48120.1
C11—C12—H12119.7C48—C49—C50120.2 (3)
P1—C13—P2112.99 (15)C48—C49—H49119.9
P1—C13—H13A109.0C50—C49—H49119.9
P2—C13—H13A109.0C49—C50—C45120.5 (3)
P1—C13—H13B109.0C49—C50—H50119.8
P2—C13—H13B109.0C45—C50—H50119.8
H13A—C13—H13B107.8N2—C51—N1121.4 (3)
C15—C14—C19119.0 (3)N2—C51—S1119.8 (2)
C15—C14—P2118.9 (2)N1—C51—S1118.7 (2)
C19—C14—P2122.1 (2)N2—C52—C53112.4 (3)
C14—C15—C16120.7 (3)N2—C52—H52A109.1
C14—C15—H15119.7C53—C52—H52A109.1
C16—C15—H15119.7N2—C52—H52B109.1
C17—C16—C15120.2 (3)C53—C52—H52B109.1
C17—C16—H16119.9H52A—C52—H52B107.9
C15—C16—H16119.9C54—C53—C52124.8 (4)
C18—C17—C16119.5 (3)C54—C53—H53117.6
C18—C17—H17120.3C52—C53—H53117.6
C16—C17—H17120.3C53—C54—H54A120.0
C17—C18—C19120.8 (3)C53—C54—H54B120.0
C17—C18—H18119.6H54A—C54—H54B120.0
C19—C18—H18119.6C56—C55—H55A109.5
C14—C19—C18120.0 (3)C56—C55—H55B109.5
C14—C19—H19120.0H55A—C55—H55B109.5
C18—C19—H19120.0C56—C55—H55C109.5
C25—C20—C21119.0 (3)H55A—C55—H55C109.5
C25—C20—P2125.2 (2)H55B—C55—H55C109.5
C21—C20—P2115.8 (2)N3—C56—C55178.8 (4)
C22—C21—C20120.4 (3)N4—C58—C57178.9 (4)
C22—C21—H21119.8C58—C57—H57A109.5
C20—C21—H21119.8C58—C57—H57B109.5
C21—C22—C23120.3 (3)H57A—C57—H57B109.5
C21—C22—H22119.9C58—C57—H57C109.5
C23—C22—H22119.9H57A—C57—H57C109.5
C24—C23—C22119.5 (3)H57B—C57—H57C109.5
C7—P1—C1—C2−106.2 (3)C38—P3—C26—C31−68.3 (2)
C13—P1—C1—C20.7 (3)Cu2—P3—C26—C3155.1 (2)
Cu1—P1—C1—C2126.2 (2)C31—C26—C27—C282.4 (4)
C7—P1—C1—C673.1 (2)P3—C26—C27—C28−177.5 (2)
C13—P1—C1—C6−180.0 (2)C26—C27—C28—C29−2.2 (4)
Cu1—P1—C1—C6−54.5 (2)C27—C28—C29—C300.5 (4)
C6—C1—C2—C31.1 (4)C28—C29—C30—C310.9 (4)
P1—C1—C2—C3−179.5 (2)C29—C30—C31—C26−0.7 (4)
C1—C2—C3—C4−1.3 (5)C27—C26—C31—C30−0.9 (4)
C2—C3—C4—C50.2 (5)P3—C26—C31—C30178.9 (2)
C3—C4—C5—C61.1 (5)C26—P3—C32—C37−123.4 (2)
C4—C5—C6—C1−1.2 (5)C38—P3—C32—C37134.2 (2)
C2—C1—C6—C50.1 (4)Cu2—P3—C32—C377.2 (3)
P1—C1—C6—C5−179.3 (2)C26—P3—C32—C3357.3 (3)
C1—P1—C7—C12−126.0 (3)C38—P3—C32—C33−45.1 (3)
C13—P1—C7—C12127.4 (2)Cu2—P3—C32—C33−172.1 (2)
Cu1—P1—C7—C12−0.3 (3)C37—C32—C33—C340.8 (4)
C1—P1—C7—C852.1 (3)P3—C32—C33—C34−179.9 (2)
C13—P1—C7—C8−54.6 (3)C32—C33—C34—C35−1.8 (4)
Cu1—P1—C7—C8177.7 (2)C33—C34—C35—C361.0 (4)
C12—C7—C8—C90.4 (5)C34—C35—C36—C370.7 (4)
P1—C7—C8—C9−177.7 (3)C33—C32—C37—C360.9 (4)
C7—C8—C9—C100.2 (6)P3—C32—C37—C36−178.5 (2)
C8—C9—C10—C11−0.4 (5)C35—C36—C37—C32−1.7 (4)
C9—C10—C11—C120.0 (5)C45—P4—C38—P3−165.82 (15)
C8—C7—C12—C11−0.8 (5)C39—P4—C38—P387.62 (17)
P1—C7—C12—C11177.3 (3)Cu1—P4—C38—P3−42.37 (18)
C10—C11—C12—C70.6 (5)C32—P3—C38—P4−77.63 (18)
C7—P1—C13—P2−74.17 (17)C26—P3—C38—P4174.93 (16)
C1—P1—C13—P2−177.80 (15)Cu2—P3—C38—P449.89 (17)
Cu1—P1—C13—P255.94 (17)C45—P4—C39—C44159.7 (2)
C14—P2—C13—P179.86 (17)C38—P4—C39—C44−95.3 (2)
C20—P2—C13—P1−174.31 (14)Cu1—P4—C39—C4434.5 (2)
Cu2—P2—C13—P1−52.29 (17)C45—P4—C39—C40−20.4 (3)
C20—P2—C14—C15130.5 (2)C38—P4—C39—C4084.5 (3)
C13—P2—C14—C15−122.8 (2)Cu1—P4—C39—C40−145.7 (2)
Cu2—P2—C14—C158.1 (3)C44—C39—C40—C410.4 (4)
C20—P2—C14—C19−51.2 (3)P4—C39—C40—C41−179.4 (2)
C13—P2—C14—C1955.5 (3)C39—C40—C41—C420.7 (4)
Cu2—P2—C14—C19−173.6 (2)C40—C41—C42—C43−0.6 (4)
C19—C14—C15—C160.2 (5)C41—C42—C43—C44−0.5 (5)
P2—C14—C15—C16178.6 (3)C42—C43—C44—C391.6 (4)
C14—C15—C16—C170.1 (5)C40—C39—C44—C43−1.5 (4)
C15—C16—C17—C18−0.7 (5)P4—C39—C44—C43178.3 (2)
C16—C17—C18—C191.1 (5)C39—P4—C45—C5074.9 (3)
C15—C14—C19—C180.1 (5)C38—P4—C45—C50−31.7 (3)
P2—C14—C19—C18−178.2 (3)Cu1—P4—C45—C50−157.4 (2)
C17—C18—C19—C14−0.8 (5)C39—P4—C45—C46−103.0 (2)
C14—P2—C20—C25108.9 (3)C38—P4—C45—C46150.4 (2)
C13—P2—C20—C251.7 (3)Cu1—P4—C45—C4624.6 (2)
Cu2—P2—C20—C25−123.8 (2)C50—C45—C46—C47−2.0 (4)
C14—P2—C20—C21−74.1 (2)P4—C45—C46—C47176.1 (2)
C13—P2—C20—C21178.7 (2)C45—C46—C47—C480.3 (4)
Cu2—P2—C20—C2153.2 (2)C46—C47—C48—C491.3 (5)
C25—C20—C21—C22−0.2 (4)C47—C48—C49—C50−1.1 (5)
P2—C20—C21—C22−177.3 (2)C48—C49—C50—C45−0.6 (5)
C20—C21—C22—C230.0 (5)C46—C45—C50—C492.1 (4)
C21—C22—C23—C240.3 (5)P4—C45—C50—C49−175.8 (2)
C22—C23—C24—C25−0.4 (4)C52—N2—C51—N10.2 (5)
C21—C20—C25—C240.1 (4)C52—N2—C51—S1−177.1 (2)
P2—C20—C25—C24177.0 (2)Cu2—S1—C51—N2−148.1 (2)
C23—C24—C25—C200.2 (4)Cu1—S1—C51—N2−41.3 (3)
C32—P3—C26—C274.6 (3)Cu2—S1—C51—N134.5 (3)
C38—P3—C26—C27111.5 (2)Cu1—S1—C51—N1141.3 (2)
Cu2—P3—C26—C27−125.1 (2)C51—N2—C52—C5381.3 (4)
C32—P3—C26—C31−175.2 (2)N2—C52—C53—C54129.7 (4)
D—H···AD—HH···AD···AD—H···A
C12—H12···N20.952.563.438 (4)154
C44—H44···S10.952.873.751 (3)154
C50—H50···N3i0.952.573.462 (5)156
C55—H55C···N4ii0.982.573.338 (5)136
N1—H1A···Br20.84 (2)2.74 (2)3.580 (3)172 (4)
N1—H1B···Br2iii0.85 (2)2.61 (2)3.415 (3)158 (3)
N2—H2A···Br10.85 (2)2.63 (2)3.468 (3)166 (3)
C31—H31···Cg60.952.973.476 (3)115
  6 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  The Cambridge Structural Database in retrospect and prospect.

Authors:  Colin R Groom; Frank H Allen
Journal:  Angew Chem Int Ed Engl       Date:  2014-01-02       Impact factor: 15.336

3.  Syntheses, photophysics, and photochemistry of trinuclear copper(I) thiolate and hexanuclear copper(I) selenolate complexes: X-ray crystal structures of [Cu(6)(mu-dppm)4(mu(3)-SePh)4](BF(4))2 and [Cu(6)(mu-(Ph(2)P)(2)NH(4))(mu(3)-SePh)4](BF(4)2.

Authors:  V W Yam; C H Lam; W K Fung; K K Cheung
Journal:  Inorg Chem       Date:  2001-07-02       Impact factor: 5.165

4.  Copper(I) halide complexes of N-methylbenzothiazole-2-thione: synthesis, structure, luminescence, antibacterial activity and interaction with DNA.

Authors:  M A Tsiaggali; E G Andreadou; A G Hatzidimitriou; A A Pantazaki; P Aslanidis
Journal:  J Inorg Biochem       Date:  2013-01-09       Impact factor: 4.155

5.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

6.  Bis[μ-bis-(diphenyl-phosphan-yl)methane-κ(2) P:P'](μ-1-ethyl-thio-urea-κ(2) S:S)bis-[iodidocopper(I)] acetonitrile sesquisolvate.

Authors:  Ruthairat Nimthong; Yupa Wattanakanjana; Chaveng Pakawatchai
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-12-22
  6 in total

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