Literature DB >> 21588134

Diaqua-(1,4,8,11-tetra-aza-cyclo-tetra-decane-κN,N,N,N)copper(II) bis-(2,3,4,5,6-penta-fluoro-benzoate) dihydrate.

Nur Syamimi Ahmad Tajidi1, Norbani Abdullah, Zainudin Arifin, Kong Wai Tan, Seik Weng Ng.   

Abstract

The Cu(II) atom in the title salt, [Cu(C(10)H(24)N(4))(H(2)O)(2)](C(6)F(5)CO(2))(2)·2H(2)O, is chelated by the four N atoms of the 1,4,8,11-tetra-aza-cyclo-tetra-decane (cyclam) ligand and is coordinated by two water mol-ecules in a Jahn-Teller-type tetra-gonally distorted octa-hedral geometry. The Cu(II) atom lies on a center of inversion. The cations, anions and uncoordinated water mol-ecules are linked by N-H⋯O and O-H⋯O hydrogen bonds, forming a layer structure parallel to (001).

Entities:  

Year:  2010        PMID： 21588134      PMCID： PMC3007516          DOI： 10.1107/S1600536810025705

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related (1,4,8,11-tetra­aza­cyclo­tetra­deca­ne)copper carb­oxyl­ates, see: Lindoy et al. (2003 ▶); Hunter et al. (2005 ▶).

Experimental

Crystal data

[Cu(C10H24N4)(H2O)2](C7F5O2)2·2H2O M = 758.08 Triclinic, a = 7.1976 (6) Å b = 8.7632 (7) Å c = 12.1574 (10) Å α = 79.378 (1)° β = 75.408 (1)° γ = 80.606 (1)° V = 723.85 (10) Å3 Z = 1 Mo Kα radiation μ = 0.87 mm−1 T = 100 K 0.35 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.750, T max = 0.958 6996 measured reflections 3306 independent reflections 3028 reflections with I > 2σ(I) R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.111 S = 1.06 3306 reflections 238 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.49 e Å−3 Δρmin = −0.75 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810025705/bt5287sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025705/bt5287Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C10H24N4)(H2O)2](C7F5O2)2·2H2OZ = 1
Mr = 758.08F(000) = 387
Triclinic, P1Dx = 1.739 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1976 (6) ÅCell parameters from 3327 reflections
b = 8.7632 (7) Åθ = 2.4–28.3°
c = 12.1574 (10) ŵ = 0.87 mm−1
α = 79.378 (1)°T = 100 K
β = 75.408 (1)°Plate, purple
γ = 80.606 (1)°0.35 × 0.15 × 0.05 mm
V = 723.85 (10) Å3
Bruker SMART APEX diffractometer3306 independent reflections
Radiation source: fine-focus sealed tube3028 reflections with I > 2σ(I)
graphiteRint = 0.026
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.750, Tmax = 0.958k = −11→11
6996 measured reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0585P)2 + 0.8764P] where P = (Fo2 + 2Fc2)/3
3306 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.49 e Å−3
6 restraintsΔρmin = −0.75 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
Cu10.50000.50000.50000.01239 (13)
F10.30292 (19)1.10724 (17)0.18468 (12)0.0207 (3)
F20.2995 (2)1.34413 (17)0.01066 (13)0.0238 (3)
F3−0.0014 (2)1.41338 (16)−0.09309 (12)0.0232 (3)
F4−0.3014 (2)1.23540 (18)−0.02310 (13)0.0257 (3)
F5−0.29974 (19)0.99746 (17)0.14925 (13)0.0201 (3)
O10.0371 (2)0.94440 (19)0.36194 (14)0.0171 (3)
O2−0.0383 (3)0.78296 (19)0.26114 (14)0.0185 (4)
O1W0.1535 (2)0.4892 (2)0.59710 (15)0.0184 (4)
H110.095 (4)0.418 (3)0.641 (2)0.027 (8)*
H120.059 (3)0.558 (3)0.598 (3)0.030 (9)*
O2W−0.1025 (2)0.77849 (19)0.57103 (14)0.0149 (3)
H21−0.057 (4)0.818 (4)0.5037 (13)0.025 (8)*
H22−0.101 (5)0.843 (3)0.613 (3)0.038 (10)*
N10.4818 (3)0.3368 (2)0.40734 (15)0.0101 (3)
H10.3625 (19)0.321 (3)0.428 (2)0.018 (7)*
N20.4084 (3)0.6798 (2)0.38696 (16)0.0112 (4)
H20.2840 (15)0.687 (3)0.404 (2)0.015 (7)*
C10.4771 (3)0.6699 (3)0.26255 (19)0.0136 (4)
H1A0.61920.67020.23990.016*
H1B0.41760.76270.21790.016*
C20.4258 (3)0.5219 (3)0.23401 (19)0.0142 (4)
H2A0.28610.51550.26600.017*
H2B0.44990.52950.14940.017*
C30.5400 (3)0.3721 (3)0.28057 (18)0.0133 (4)
H3A0.51880.28370.24670.016*
H3B0.67980.38320.25720.016*
C40.5931 (3)0.1921 (2)0.45282 (19)0.0129 (4)
H4A0.73350.19720.42250.016*
H4B0.55910.10020.42890.016*
C50.5434 (3)0.1775 (3)0.58302 (19)0.0139 (4)
H5A0.40410.16790.61370.017*
H5B0.61900.08350.61630.017*
C60.0001 (3)0.9099 (3)0.27439 (18)0.0120 (4)
C70.0021 (3)1.0433 (2)0.17373 (18)0.0109 (4)
C80.1511 (3)1.1355 (3)0.13503 (19)0.0134 (4)
C90.1521 (3)1.2583 (3)0.04536 (19)0.0155 (4)
C10−0.0004 (4)1.2919 (3)−0.00841 (19)0.0160 (5)
C11−0.1512 (3)1.2027 (3)0.0274 (2)0.0160 (4)
C12−0.1483 (3)1.0797 (3)0.11656 (19)0.0133 (4)
U11U22U33U12U13U23
Cu10.0154 (2)0.0093 (2)0.0126 (2)−0.00158 (14)−0.00413 (14)−0.00071 (14)
F10.0142 (6)0.0252 (8)0.0237 (7)−0.0079 (6)−0.0080 (6)0.0036 (6)
F20.0242 (7)0.0200 (7)0.0245 (8)−0.0133 (6)0.0020 (6)0.0023 (6)
F30.0431 (9)0.0114 (7)0.0126 (7)−0.0011 (6)−0.0065 (6)0.0031 (5)
F40.0268 (8)0.0269 (8)0.0255 (8)0.0027 (6)−0.0174 (6)0.0015 (6)
F50.0137 (6)0.0226 (7)0.0254 (7)−0.0070 (5)−0.0070 (5)0.0008 (6)
O10.0234 (8)0.0172 (8)0.0119 (7)−0.0064 (7)−0.0057 (6)0.0003 (6)
O20.0269 (9)0.0103 (8)0.0185 (8)−0.0056 (6)−0.0049 (7)−0.0001 (6)
O1W0.0117 (8)0.0138 (8)0.0253 (9)−0.0024 (6)−0.0008 (7)0.0039 (7)
O2W0.0165 (8)0.0135 (8)0.0143 (8)−0.0046 (6)−0.0025 (6)−0.0002 (6)
N10.0088 (8)0.0090 (8)0.0124 (9)−0.0023 (7)−0.0021 (7)−0.0011 (7)
N20.0096 (8)0.0100 (8)0.0136 (9)−0.0022 (7)−0.0027 (7)−0.0001 (7)
C10.0153 (10)0.0117 (10)0.0132 (10)−0.0033 (8)−0.0043 (8)0.0024 (8)
C20.0164 (10)0.0154 (11)0.0112 (10)−0.0042 (8)−0.0042 (8)0.0000 (8)
C30.0134 (10)0.0147 (10)0.0113 (10)−0.0029 (8)−0.0005 (8)−0.0032 (8)
C40.0139 (10)0.0074 (9)0.0172 (11)0.0000 (8)−0.0041 (8)−0.0014 (8)
C50.0161 (10)0.0089 (10)0.0174 (11)−0.0024 (8)−0.0068 (8)0.0009 (8)
C60.0097 (9)0.0120 (10)0.0121 (10)0.0006 (8)−0.0009 (8)−0.0002 (8)
C70.0121 (10)0.0094 (9)0.0103 (9)−0.0005 (8)−0.0013 (8)−0.0017 (8)
C80.0129 (10)0.0135 (10)0.0140 (10)−0.0016 (8)−0.0031 (8)−0.0024 (8)
C90.0181 (11)0.0118 (10)0.0142 (10)−0.0054 (8)0.0027 (8)−0.0013 (8)
C100.0266 (12)0.0089 (10)0.0093 (10)0.0007 (9)−0.0017 (9)0.0005 (8)
C110.0172 (11)0.0164 (11)0.0145 (10)0.0041 (9)−0.0074 (8)−0.0031 (8)
C120.0133 (10)0.0129 (10)0.0143 (10)−0.0015 (8)−0.0030 (8)−0.0037 (8)
Cu1—N12.0149 (18)C1—C21.525 (3)
Cu1—N1i2.0149 (18)C1—H1A0.9900
Cu1—N22.0313 (18)C1—H1B0.9900
Cu1—N2i2.0313 (18)C2—C31.526 (3)
Cu1—O1W2.4849 (17)C2—H2A0.9900
F1—C81.345 (3)C2—H2B0.9900
F2—C91.337 (3)C3—H3A0.9900
F3—C101.338 (3)C3—H3B0.9900
F4—C111.340 (3)C4—C51.518 (3)
F5—C121.341 (3)C4—H4A0.9900
O1—C61.258 (3)C4—H4B0.9900
O2—C61.236 (3)C5—N2i1.479 (3)
O1W—H110.834 (10)C5—H5A0.9900
O1W—H120.832 (10)C5—H5B0.9900
O2W—H210.833 (10)C6—C71.528 (3)
O2W—H220.830 (10)C7—C81.383 (3)
N1—C31.479 (3)C7—C121.393 (3)
N1—C41.480 (3)C8—C91.383 (3)
N1—H10.859 (10)C9—C101.380 (3)
N2—C5i1.479 (3)C10—C111.376 (3)
N2—C11.482 (3)C11—C121.382 (3)
N2—H20.861 (10)
N1—Cu1—N1i180.00 (9)N1—C3—H3A109.3
N1—Cu1—N293.24 (7)C2—C3—H3A109.3
N1i—Cu1—N286.76 (7)N1—C3—H3B109.3
N1—Cu1—N2i86.76 (7)C2—C3—H3B109.3
N1i—Cu1—N2i93.24 (7)H3A—C3—H3B107.9
N2—Cu1—N2i180.0N1—C4—C5108.02 (17)
N1—Cu1—O1W88.91 (7)N1—C4—H4A110.1
N1i—Cu1—O1W91.09 (7)C5—C4—H4A110.1
N2—Cu1—O1W86.87 (6)N1—C4—H4B110.1
N2i—Cu1—O1W93.13 (6)C5—C4—H4B110.1
Cu1—O1W—H11132 (2)H4A—C4—H4B108.4
Cu1—O1W—H12131 (2)N2i—C5—C4107.48 (17)
H11—O1W—H1297 (3)N2i—C5—H5A110.2
H21—O2W—H22107 (3)C4—C5—H5A110.2
C3—N1—C4111.85 (17)N2i—C5—H5B110.2
C3—N1—Cu1118.22 (13)C4—C5—H5B110.2
C4—N1—Cu1105.50 (13)H5A—C5—H5B108.5
C3—N1—H1110 (2)O2—C6—O1127.9 (2)
C4—N1—H1106 (2)O2—C6—C7117.14 (19)
Cu1—N1—H1104 (2)O1—C6—C7114.94 (19)
C5i—N2—C1112.36 (17)C8—C7—C12116.3 (2)
C5i—N2—Cu1105.50 (13)C8—C7—C6122.22 (19)
C1—N2—Cu1118.01 (14)C12—C7—C6121.49 (19)
C5i—N2—H2106 (2)F1—C8—C9117.3 (2)
C1—N2—H2108.4 (19)F1—C8—C7120.12 (19)
Cu1—N2—H2105.8 (19)C9—C8—C7122.6 (2)
N2—C1—C2111.28 (17)F2—C9—C10120.0 (2)
N2—C1—H1A109.4F2—C9—C8120.5 (2)
C2—C1—H1A109.4C10—C9—C8119.5 (2)
N2—C1—H1B109.4F3—C10—C9119.3 (2)
C2—C1—H1B109.4F3—C10—C11120.9 (2)
H1A—C1—H1B108.0C9—C10—C11119.7 (2)
C3—C2—C1113.62 (18)F4—C11—C10120.3 (2)
C3—C2—H2A108.8F4—C11—C12120.0 (2)
C1—C2—H2A108.8C10—C11—C12119.7 (2)
C3—C2—H2B108.8F5—C12—C11117.48 (19)
C1—C2—H2B108.8F5—C12—C7120.30 (19)
H2A—C2—H2B107.7C11—C12—C7122.2 (2)
N1—C3—C2111.72 (18)
N2—Cu1—N1—C338.53 (15)C12—C7—C8—F1−179.30 (19)
N2i—Cu1—N1—C3−141.47 (15)C6—C7—C8—F11.4 (3)
O1W—Cu1—N1—C3125.34 (15)C12—C7—C8—C90.5 (3)
N2—Cu1—N1—C4164.50 (13)C6—C7—C8—C9−178.8 (2)
N2i—Cu1—N1—C4−15.50 (13)F1—C8—C9—F20.0 (3)
O1W—Cu1—N1—C4−108.70 (13)C7—C8—C9—F2−179.9 (2)
N1—Cu1—N2—C5i−165.17 (14)F1—C8—C9—C10180.0 (2)
N1i—Cu1—N2—C5i14.83 (14)C7—C8—C9—C100.1 (4)
O1W—Cu1—N2—C5i106.10 (14)F2—C9—C10—F3−1.8 (3)
N1—Cu1—N2—C1−38.68 (15)C8—C9—C10—F3178.2 (2)
N1i—Cu1—N2—C1141.32 (15)F2—C9—C10—C11179.7 (2)
O1W—Cu1—N2—C1−127.41 (15)C8—C9—C10—C11−0.3 (3)
C5i—N2—C1—C2179.95 (17)F3—C10—C11—F40.7 (3)
Cu1—N2—C1—C256.8 (2)C9—C10—C11—F4179.1 (2)
N2—C1—C2—C3−69.8 (2)F3—C10—C11—C12−178.7 (2)
C4—N1—C3—C2−179.63 (17)C9—C10—C11—C12−0.3 (3)
Cu1—N1—C3—C2−56.8 (2)F4—C11—C12—F5−0.2 (3)
C1—C2—C3—N169.8 (2)C10—C11—C12—F5179.2 (2)
C3—N1—C4—C5172.46 (17)F4—C11—C12—C7−178.4 (2)
Cu1—N1—C4—C542.67 (18)C10—C11—C12—C71.0 (4)
N1—C4—C5—N2i−58.0 (2)C8—C7—C12—F5−179.24 (19)
O2—C6—C7—C8−132.7 (2)C6—C7—C12—F50.1 (3)
O1—C6—C7—C847.8 (3)C8—C7—C12—C11−1.1 (3)
O2—C6—C7—C1248.0 (3)C6—C7—C12—C11178.2 (2)
O1—C6—C7—C12−131.5 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O2wii0.86 (1)2.17 (2)2.997 (2)157 (3)
N2—H2···O1w0.86 (1)2.70 (3)3.123 (2)112 (2)
O1w—H11···O2ii0.83 (1)1.98 (1)2.785 (2)162 (3)
O1w—H12···O2w0.83 (1)2.10 (2)2.898 (2)160 (3)
O2w—H21···O10.83 (1)1.90 (1)2.723 (2)169 (3)
O2w—H22···O1iii0.83 (1)2.08 (2)2.842 (2)152 (4)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O2wi0.86 (1)2.17 (2)2.997 (2)157 (3)
N2—H2⋯O1w0.86 (1)2.70 (3)3.123 (2)112 (2)
O1w—H11⋯O2i0.83 (1)1.98 (1)2.785 (2)162 (3)
O1w—H12⋯O2w0.83 (1)2.10 (2)2.898 (2)160 (3)
O2w—H21⋯O10.83 (1)1.90 (1)2.723 (2)169 (3)
O2w—H22⋯O1ii0.83 (1)2.08 (2)2.842 (2)152 (4)

Symmetry codes: (i) ; (ii) .

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