Crystal structure of bis-[μ-1,2-bis-(di-phenyl-phosphan-yl)ethane-κ(2) P:P']bis[(N,N'-di-ethyl-thio-urea-κS)iodidocopper(I)].

The binuclear title complex, [Cu2I2(C26H24P2)2(C5H12N2S)2], lies about an inversion centre. The Cu(I) atom displays a distorted tetra-hedral coordination geometry defined by one S atom of an N,N'-di-ethyl-thio-urea ligand, two P atoms derived from two bridging 1,2-bis-(di-phenyl-phosphan-yl)ethane (dppe) ligands and one iodide ion. The dppe ligand bridges two symmetry-related Cu(I) ions, forming a 10-membered Cu2P4C4 ring. An intra-molecular N-H⋯I hydrogen bond is noted. In the crystal, N-H⋯I hydrogen bonds link complex mol-ecules into layers parallel to (-101).

Related literature

For background to the coordination chemistry of copper(I) halides and pseudohalides, see: Dennehy et al. (2011 ▸); Oshio et al. (1996 ▸); Seward et al. (2003 ▸). For their potential applications, see: Corey et al. (1987 ▸); Dias et al. (2006 ▸). For relevant examples of discrete complexes, see: Dennehy et al. (2009 ▸).

Experimental

Crystal data

[Cu2I2(C26H24P2)2(C5H12N2S)2]

M = 1442.11

Monoclinic,

a = 12.2150 (8) Å

b = 15.1836 (9) Å

c = 17.1801 (10) Å

β = 96.414 (2)°

V = 3166.4 (3) Å3

Z = 2

Cu Kα radiation

μ = 10.37 mm−1

T = 100 K

0.16 × 0.15 × 0.08 mm

Data collection

Bruker Prospector CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.433, T max = 0.753

23236 measured reflections

5564 independent reflections

5556 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.063

S = 1.13

5564 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.92 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015 ▸) and SHELXLE (Hübschle et al., 2011 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015014176/tk5371sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015014176/tk5371Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015014176/tk5371fig1.tif

The structure of title complex with displacement ellipsoids drawn at the 50% propbability level. All H atoms are omitted for clarity.

Click here for additional data file.

. DOI: 10.1107/S2056989015014176/tk5371fig2.tif

Part of the crystal structure showing intra/inter-mol­ecular N—H⋯I hydrogen bonds forming a layers as dashed lines.

CCDC reference: 1415379

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Cu2I2(C26H24P2)2(C5H12N2S)2]	F(000) = 1456
Mr = 1442.11	Dx = 1.513 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 12.2150 (8) Å	Cell parameters from 9846 reflections
b = 15.1836 (9) Å	θ = 3.9–66.7°
c = 17.1801 (10) Å	µ = 10.37 mm−1
β = 96.414 (2)°	T = 100 K
V = 3166.4 (3) Å3	Block, colourless
Z = 2	0.16 × 0.15 × 0.08 mm

Bruker Prospector CCD diffractometer	5564 independent reflections
Radiation source: I-mu-S microsource X-ray tube	5556 reflections with I > 2σ(I)
Laterally graded multilayer (Goebel) mirror monochromator	Rint = 0.028
ω and phi scans	θmax = 67.0°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −14→12
Tmin = 0.433, Tmax = 0.753	k = −18→17
23236 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0315P)2 + 3.4263P] where P = (Fo2 + 2Fc2)/3
5564 reflections	(Δ/σ)max = 0.003
345 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.92 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.

	x	y	z	Uiso*/Ueq
I1	0.71658 (2)	0.56133 (2)	0.16309 (2)	0.01039 (6)
Cu1	0.51704 (2)	0.64264 (2)	0.12681 (2)	0.00798 (8)
S1	0.48147 (4)	0.74104 (3)	0.22620 (3)	0.01238 (12)
P1	0.39142 (4)	0.53264 (3)	0.12684 (3)	0.00711 (11)
P2	0.52134 (4)	0.70642 (3)	0.00696 (3)	0.00768 (11)
N1	0.58767 (16)	0.88958 (13)	0.27366 (12)	0.0163 (4)
H1	0.6493	0.9171	0.2902	0.020*
N2	0.69626 (15)	0.77334 (13)	0.24764 (11)	0.0122 (4)
H2	0.7019	0.7167	0.2380	0.015*
C1	0.59546 (18)	0.80593 (15)	0.25058 (12)	0.0109 (4)
C2	0.4851 (2)	0.93892 (15)	0.27369 (17)	0.0198 (5)
H2A	0.4929	0.9817	0.3174	0.024*
H2B	0.4250	0.8977	0.2827	0.024*
C3	0.4547 (3)	0.9875 (2)	0.19789 (19)	0.0348 (7)
H3A	0.5135	1.0289	0.1891	0.052*
H3B	0.3859	1.0199	0.2007	0.052*
H3C	0.4448	0.9452	0.1546	0.052*
C4	0.79787 (18)	0.82441 (16)	0.25912 (14)	0.0149 (5)
H4A	0.8076	0.8487	0.3129	0.018*
H4B	0.7936	0.8743	0.2218	0.018*
C5	0.89514 (18)	0.76646 (16)	0.24646 (14)	0.0162 (5)
H5A	0.8813	0.7370	0.1956	0.024*
H5B	0.9055	0.7222	0.2881	0.024*
H5C	0.9617	0.8027	0.2475	0.024*
C11	0.38548 (18)	0.47611 (14)	0.22045 (13)	0.0103 (4)
C12	0.45710 (18)	0.50116 (14)	0.28549 (13)	0.0124 (4)
H12	0.5106	0.5456	0.2807	0.015*
C13	0.4500 (2)	0.46061 (16)	0.35789 (13)	0.0161 (5)
H13	0.4989	0.4777	0.4022	0.019*
C14	0.3723 (2)	0.39590 (16)	0.36541 (14)	0.0196 (5)
H14	0.3673	0.3692	0.4149	0.024*
C15	0.3015 (2)	0.36998 (17)	0.30053 (15)	0.0201 (5)
H15	0.2486	0.3250	0.3055	0.024*
C16	0.30793 (19)	0.40978 (16)	0.22830 (14)	0.0149 (5)
H16	0.2594	0.3918	0.1840	0.018*
C21	0.24971 (18)	0.57205 (14)	0.10553 (14)	0.0109 (4)
C22	0.1845 (2)	0.55542 (16)	0.03495 (15)	0.0188 (5)
H22	0.2117	0.5190	−0.0035	0.023*
C23	0.0792 (2)	0.59235 (18)	0.02086 (16)	0.0240 (5)
H23	0.0359	0.5819	−0.0277	0.029*
C24	0.0375 (2)	0.64380 (17)	0.07685 (17)	0.0246 (6)
H24	−0.0346	0.6678	0.0674	0.029*
C25	0.1021 (2)	0.66008 (18)	0.14715 (17)	0.0245 (6)
H25	0.0739	0.6953	0.1860	0.029*
C26	0.2072 (2)	0.62539 (17)	0.16094 (14)	0.0177 (5)
H26	0.2510	0.6381	0.2088	0.021*
C27	0.39162 (19)	0.44094 (13)	0.05650 (13)	0.0098 (4)
H27A	0.3228	0.4068	0.0578	0.012*
H27B	0.3910	0.4658	0.0032	0.012*
C28	0.51050 (17)	0.62207 (14)	−0.07137 (12)	0.0090 (4)
H28A	0.4406	0.5891	−0.0713	0.011*
H28B	0.5110	0.6507	−0.1231	0.011*
C31	0.40910 (19)	0.78228 (15)	−0.02656 (12)	0.0126 (4)
C32	0.4258 (2)	0.87216 (18)	−0.03567 (19)	0.0302 (6)
H32	0.4977	0.8963	−0.0252	0.036*
C33	0.3369 (3)	0.9266 (2)	−0.0601 (2)	0.0432 (8)
H33	0.3488	0.9880	−0.0658	0.052*
C34	0.2325 (3)	0.8932 (2)	−0.07599 (18)	0.0343 (7)
H34	0.1728	0.9310	−0.0933	0.041*
C35	0.2148 (2)	0.8042 (2)	−0.06672 (16)	0.0279 (6)
H35	0.1427	0.7805	−0.0779	0.033*
C36	0.3023 (2)	0.74917 (18)	−0.04106 (15)	0.0205 (5)
H36	0.2893	0.6883	−0.0333	0.025*
C41	0.64463 (18)	0.76671 (14)	−0.01297 (13)	0.0114 (4)
C42	0.7191 (2)	0.79247 (18)	0.04993 (15)	0.0239 (6)
H42	0.7029	0.7809	0.1018	0.029*
C43	0.8164 (3)	0.8347 (2)	0.03845 (17)	0.0333 (7)
H43	0.8658	0.8524	0.0823	0.040*
C44	0.8419 (2)	0.8513 (2)	−0.03605 (18)	0.0315 (7)
H44	0.9092	0.8794	−0.0440	0.038*
C45	0.7686 (3)	0.8267 (3)	−0.09912 (18)	0.0423 (9)
H45	0.7856	0.8383	−0.1508	0.051*
C46	0.6708 (3)	0.7853 (2)	−0.08813 (15)	0.0316 (7)
H46	0.6209	0.7694	−0.1323	0.038*

	U11	U22	U33	U12	U13	U23
I1	0.01029 (9)	0.00674 (9)	0.01363 (9)	0.00312 (4)	−0.00089 (6)	−0.00191 (4)
Cu1	0.00902 (16)	0.00693 (16)	0.00820 (15)	−0.00076 (11)	0.00197 (12)	−0.00022 (11)
S1	0.0096 (2)	0.0109 (3)	0.0175 (3)	−0.00149 (19)	0.0049 (2)	−0.0069 (2)
P1	0.0074 (2)	0.0068 (3)	0.0076 (2)	−0.00001 (19)	0.00262 (19)	−0.00070 (19)
P2	0.0097 (3)	0.0057 (2)	0.0078 (2)	0.00084 (19)	0.00168 (19)	0.00046 (19)
N1	0.0105 (9)	0.0122 (10)	0.0262 (11)	−0.0006 (8)	0.0025 (8)	−0.0094 (8)
N2	0.0100 (9)	0.0092 (9)	0.0174 (9)	0.0010 (7)	0.0012 (7)	−0.0073 (7)
C1	0.0121 (10)	0.0117 (11)	0.0096 (10)	0.0003 (8)	0.0036 (8)	−0.0022 (8)
C2	0.0172 (12)	0.0122 (12)	0.0315 (14)	0.0030 (9)	0.0091 (11)	−0.0075 (9)
C3	0.0314 (15)	0.0299 (16)	0.0441 (17)	0.0096 (13)	0.0083 (13)	0.0068 (13)
C4	0.0112 (11)	0.0149 (11)	0.0185 (11)	−0.0007 (9)	0.0012 (9)	−0.0063 (9)
C5	0.0105 (10)	0.0172 (12)	0.0208 (12)	−0.0002 (9)	0.0011 (9)	−0.0089 (9)
C11	0.0117 (10)	0.0088 (10)	0.0112 (10)	0.0041 (8)	0.0052 (8)	0.0014 (8)
C12	0.0144 (10)	0.0090 (10)	0.0146 (11)	0.0020 (8)	0.0051 (9)	−0.0004 (8)
C13	0.0214 (12)	0.0149 (11)	0.0124 (11)	0.0049 (10)	0.0030 (9)	−0.0003 (9)
C14	0.0248 (12)	0.0197 (13)	0.0164 (11)	0.0054 (10)	0.0115 (10)	0.0085 (9)
C15	0.0170 (11)	0.0186 (12)	0.0260 (13)	−0.0024 (10)	0.0088 (10)	0.0076 (10)
C16	0.0106 (10)	0.0166 (12)	0.0181 (11)	−0.0015 (9)	0.0036 (9)	0.0029 (9)
C21	0.0088 (10)	0.0093 (10)	0.0151 (11)	−0.0017 (8)	0.0033 (9)	0.0016 (8)
C22	0.0156 (12)	0.0219 (13)	0.0185 (12)	0.0035 (9)	0.0002 (10)	−0.0044 (9)
C23	0.0166 (12)	0.0239 (14)	0.0297 (14)	0.0046 (11)	−0.0059 (10)	0.0002 (11)
C24	0.0120 (11)	0.0191 (13)	0.0425 (16)	0.0048 (10)	0.0023 (11)	0.0007 (11)
C25	0.0191 (12)	0.0202 (13)	0.0358 (15)	0.0057 (10)	0.0105 (11)	−0.0064 (11)
C26	0.0175 (12)	0.0161 (12)	0.0200 (12)	0.0017 (9)	0.0042 (10)	−0.0048 (9)
C27	0.0112 (11)	0.0082 (11)	0.0101 (10)	0.0002 (8)	0.0017 (8)	−0.0020 (7)
C28	0.0111 (10)	0.0075 (10)	0.0085 (10)	0.0002 (8)	0.0016 (8)	−0.0017 (8)
C31	0.0175 (11)	0.0123 (11)	0.0088 (10)	0.0062 (9)	0.0039 (8)	0.0011 (8)
C32	0.0274 (14)	0.0171 (13)	0.0456 (17)	0.0059 (11)	0.0025 (12)	0.0054 (12)
C33	0.045 (2)	0.0210 (15)	0.064 (2)	0.0149 (14)	0.0092 (17)	0.0142 (15)
C34	0.0319 (15)	0.0399 (18)	0.0315 (15)	0.0273 (14)	0.0049 (12)	0.0107 (13)
C35	0.0188 (13)	0.0409 (17)	0.0238 (13)	0.0122 (12)	0.0018 (10)	−0.0045 (12)
C36	0.0179 (12)	0.0221 (13)	0.0218 (12)	0.0057 (10)	0.0042 (10)	−0.0024 (10)
C41	0.0149 (11)	0.0054 (10)	0.0140 (11)	−0.0001 (8)	0.0027 (9)	0.0020 (8)
C42	0.0278 (14)	0.0278 (14)	0.0154 (12)	−0.0125 (11)	0.0003 (10)	0.0057 (10)
C43	0.0305 (15)	0.0388 (17)	0.0285 (15)	−0.0211 (13)	−0.0067 (12)	0.0108 (13)
C44	0.0245 (14)	0.0330 (16)	0.0371 (16)	−0.0154 (12)	0.0042 (12)	0.0131 (13)
C45	0.0434 (18)	0.063 (2)	0.0220 (14)	−0.0303 (17)	0.0116 (13)	0.0075 (14)
C46	0.0358 (16)	0.0455 (18)	0.0128 (12)	−0.0229 (14)	0.0002 (11)	0.0039 (12)

I1—Cu1	2.7412 (4)	C21—C26	1.394 (3)
Cu1—P1	2.2681 (6)	C21—C22	1.398 (4)
Cu1—P2	2.2813 (6)	C22—C23	1.399 (4)
Cu1—S1	2.3457 (6)	C22—H22	0.9500
S1—C1	1.719 (2)	C23—C24	1.380 (4)
P1—C21	1.829 (2)	C23—H23	0.9500
P1—C11	1.832 (2)	C24—C25	1.389 (4)
P1—C27	1.844 (2)	C24—H24	0.9500
P2—C41	1.827 (2)	C25—C26	1.384 (4)
P2—C31	1.834 (2)	C25—H25	0.9500
P2—C28	1.852 (2)	C26—H26	0.9500
N1—C1	1.337 (3)	C27—C28i	1.530 (3)
N1—C2	1.459 (3)	C27—H27A	0.9900
N1—H1	0.8800	C27—H27B	0.9900
N2—C1	1.333 (3)	C28—C27i	1.530 (3)
N2—C4	1.458 (3)	C28—H28A	0.9900
N2—H2	0.8800	C28—H28B	0.9900
C2—C3	1.507 (4)	C31—C32	1.391 (4)
C2—H2A	0.9900	C31—C36	1.394 (4)
C2—H2B	0.9900	C32—C33	1.391 (4)
C3—H3A	0.9800	C32—H32	0.9500
C3—H3B	0.9800	C33—C34	1.371 (5)
C3—H3C	0.9800	C33—H33	0.9500
C4—C5	1.514 (3)	C34—C35	1.381 (5)
C4—H4A	0.9900	C34—H34	0.9500
C4—H4B	0.9900	C35—C36	1.389 (4)
C5—H5A	0.9800	C35—H35	0.9500
C5—H5B	0.9800	C36—H36	0.9500
C5—H5C	0.9800	C41—C42	1.389 (3)
C11—C12	1.393 (3)	C41—C46	1.393 (3)
C11—C16	1.399 (3)	C42—C43	1.384 (4)
C12—C13	1.399 (3)	C42—H42	0.9500
C12—H12	0.9500	C43—C44	1.374 (4)
C13—C14	1.382 (4)	C43—H43	0.9500
C13—H13	0.9500	C44—C45	1.378 (5)
C14—C15	1.389 (4)	C44—H44	0.9500
C14—H14	0.9500	C45—C46	1.381 (4)
C15—C16	1.390 (3)	C45—H45	0.9500
C15—H15	0.9500	C46—H46	0.9500
C16—H16	0.9500
P1—Cu1—P2	113.37 (2)	C15—C16—H16	119.8
P1—Cu1—S1	106.77 (2)	C11—C16—H16	119.8
P2—Cu1—S1	114.30 (2)	C26—C21—C22	118.6 (2)
P1—Cu1—I1	104.637 (18)	C26—C21—P1	118.01 (18)
P2—Cu1—I1	106.669 (17)	C22—C21—P1	123.33 (18)
S1—Cu1—I1	110.709 (17)	C21—C22—C23	120.1 (2)
C1—S1—Cu1	109.37 (7)	C21—C22—H22	119.9
C21—P1—C11	101.52 (10)	C23—C22—H22	119.9
C21—P1—C27	100.74 (10)	C24—C23—C22	120.6 (2)
C11—P1—C27	102.98 (10)	C24—C23—H23	119.7
C21—P1—Cu1	112.59 (7)	C22—C23—H23	119.7
C11—P1—Cu1	116.01 (8)	C23—C24—C25	119.3 (2)
C27—P1—Cu1	120.36 (7)	C23—C24—H24	120.4
C41—P2—C31	103.26 (10)	C25—C24—H24	120.4
C41—P2—C28	101.76 (10)	C26—C25—C24	120.5 (2)
C31—P2—C28	102.47 (10)	C26—C25—H25	119.8
C41—P2—Cu1	118.97 (7)	C24—C25—H25	119.8
C31—P2—Cu1	117.28 (7)	C25—C26—C21	120.9 (2)
C28—P2—Cu1	110.82 (7)	C25—C26—H26	119.5
C1—N1—C2	125.3 (2)	C21—C26—H26	119.5
C1—N1—H1	117.4	C28i—C27—P1	114.89 (15)
C2—N1—H1	117.4	C28i—C27—H27A	108.5
C1—N2—C4	124.98 (19)	P1—C27—H27A	108.5
C1—N2—H2	117.5	C28i—C27—H27B	108.5
C4—N2—H2	117.5	P1—C27—H27B	108.5
N2—C1—N1	117.4 (2)	H27A—C27—H27B	107.5
N2—C1—S1	120.29 (17)	C27i—C28—P2	108.66 (14)
N1—C1—S1	122.29 (17)	C27i—C28—H28A	110.0
N1—C2—C3	112.4 (2)	P2—C28—H28A	110.0
N1—C2—H2A	109.1	C27i—C28—H28B	110.0
C3—C2—H2A	109.1	P2—C28—H28B	110.0
N1—C2—H2B	109.1	H28A—C28—H28B	108.3
C3—C2—H2B	109.1	C32—C31—C36	118.7 (2)
H2A—C2—H2B	107.9	C32—C31—P2	122.5 (2)
C2—C3—H3A	109.5	C36—C31—P2	118.77 (18)
C2—C3—H3B	109.5	C33—C32—C31	119.8 (3)
H3A—C3—H3B	109.5	C33—C32—H32	120.1
C2—C3—H3C	109.5	C31—C32—H32	120.1
H3A—C3—H3C	109.5	C34—C33—C32	121.2 (3)
H3B—C3—H3C	109.5	C34—C33—H33	119.4
N2—C4—C5	109.97 (19)	C32—C33—H33	119.4
N2—C4—H4A	109.7	C33—C34—C35	119.6 (3)
C5—C4—H4A	109.7	C33—C34—H34	120.2
N2—C4—H4B	109.7	C35—C34—H34	120.2
C5—C4—H4B	109.7	C34—C35—C36	120.0 (3)
H4A—C4—H4B	108.2	C34—C35—H35	120.0
C4—C5—H5A	109.5	C36—C35—H35	120.0
C4—C5—H5B	109.5	C35—C36—C31	120.8 (3)
H5A—C5—H5B	109.5	C35—C36—H36	119.6
C4—C5—H5C	109.5	C31—C36—H36	119.6
H5A—C5—H5C	109.5	C42—C41—C46	117.8 (2)
H5B—C5—H5C	109.5	C42—C41—P2	118.50 (18)
C12—C11—C16	119.4 (2)	C46—C41—P2	123.68 (18)
C12—C11—P1	119.57 (17)	C43—C42—C41	121.2 (2)
C16—C11—P1	121.03 (17)	C43—C42—H42	119.4
C11—C12—C13	119.8 (2)	C41—C42—H42	119.4
C11—C12—H12	120.1	C44—C43—C42	120.3 (3)
C13—C12—H12	120.1	C44—C43—H43	119.8
C14—C13—C12	120.5 (2)	C42—C43—H43	119.8
C14—C13—H13	119.7	C43—C44—C45	119.2 (3)
C12—C13—H13	119.7	C43—C44—H44	120.4
C13—C14—C15	119.9 (2)	C45—C44—H44	120.4
C13—C14—H14	120.0	C44—C45—C46	120.8 (3)
C15—C14—H14	120.0	C44—C45—H45	119.6
C14—C15—C16	120.0 (2)	C46—C45—H45	119.6
C14—C15—H15	120.0	C45—C46—C41	120.7 (3)
C16—C15—H15	120.0	C45—C46—H46	119.6
C15—C16—C11	120.3 (2)	C41—C46—H46	119.6
C4—N2—C1—N1	−7.2 (3)	P1—C21—C26—C25	177.6 (2)
C4—N2—C1—S1	173.37 (18)	C21—P1—C27—C28i	−165.70 (16)
C2—N1—C1—N2	174.1 (2)	C11—P1—C27—C28i	−61.09 (18)
C2—N1—C1—S1	−6.5 (3)	Cu1—P1—C27—C28i	69.95 (17)
Cu1—S1—C1—N2	−33.6 (2)	C41—P2—C28—C27i	66.78 (16)
Cu1—S1—C1—N1	146.99 (17)	C31—P2—C28—C27i	173.40 (15)
C1—N1—C2—C3	−90.6 (3)	Cu1—P2—C28—C27i	−60.70 (15)
C1—N2—C4—C5	−176.4 (2)	C41—P2—C31—C32	−20.2 (2)
C21—P1—C11—C12	−123.32 (18)	C28—P2—C31—C32	−125.7 (2)
C27—P1—C11—C12	132.67 (18)	Cu1—P2—C31—C32	112.8 (2)
Cu1—P1—C11—C12	−0.9 (2)	C41—P2—C31—C36	161.93 (18)
C21—P1—C11—C16	54.8 (2)	C28—P2—C31—C36	56.5 (2)
C27—P1—C11—C16	−49.2 (2)	Cu1—P2—C31—C36	−65.11 (19)
Cu1—P1—C11—C16	177.20 (16)	C36—C31—C32—C33	−1.1 (4)
C16—C11—C12—C13	−0.7 (3)	P2—C31—C32—C33	−178.9 (3)
P1—C11—C12—C13	177.45 (17)	C31—C32—C33—C34	−0.4 (5)
C11—C12—C13—C14	−0.1 (3)	C32—C33—C34—C35	0.8 (5)
C12—C13—C14—C15	0.8 (4)	C33—C34—C35—C36	0.3 (4)
C13—C14—C15—C16	−0.7 (4)	C34—C35—C36—C31	−1.9 (4)
C14—C15—C16—C11	−0.1 (4)	C32—C31—C36—C35	2.2 (4)
C12—C11—C16—C15	0.8 (3)	P2—C31—C36—C35	−179.84 (19)
P1—C11—C16—C15	−177.35 (18)	C31—P2—C41—C42	114.9 (2)
C11—P1—C21—C26	56.7 (2)	C28—P2—C41—C42	−139.1 (2)
C27—P1—C21—C26	162.44 (19)	Cu1—P2—C41—C42	−17.1 (2)
Cu1—P1—C21—C26	−68.06 (19)	C31—P2—C41—C46	−67.9 (2)
C11—P1—C21—C22	−127.0 (2)	C28—P2—C41—C46	38.1 (3)
C27—P1—C21—C22	−21.2 (2)	Cu1—P2—C41—C46	160.1 (2)
Cu1—P1—C21—C22	108.27 (19)	C46—C41—C42—C43	−0.4 (4)
C26—C21—C22—C23	0.3 (4)	P2—C41—C42—C43	177.0 (2)
P1—C21—C22—C23	−176.0 (2)	C41—C42—C43—C44	−0.7 (5)
C21—C22—C23—C24	−1.5 (4)	C42—C43—C44—C45	1.1 (5)
C22—C23—C24—C25	1.2 (4)	C43—C44—C45—C46	−0.4 (6)
C23—C24—C25—C26	0.2 (4)	C44—C45—C46—C41	−0.7 (6)
C24—C25—C26—C21	−1.3 (4)	C42—C41—C46—C45	1.1 (5)
C22—C21—C26—C25	1.1 (4)	P2—C41—C46—C45	−176.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···I1ii	0.88	2.80	3.622 (2)	156
N2—H2···I1	0.88	2.70	3.5517 (19)	162

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1I1i	0.88	2.80	3.622(2)	156
N2H2I1	0.88	2.70	3.5517(19)	162

Symmetry code: (i) .