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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m423.
Published online 2008 January 25. doi:  10.1107/S1600536808002237
PMCID: PMC2960305

Aqua­chloridobis(1,10-phenanthroline-κ2 N,N′)zinc(II) chloride N,N-dimethyl­formamide solvate

Abstract

The Zn atom in the title salt, [ZnCl(C12H8N2)2(H2O)]Cl·C3H7NO, is chelated by two phenanthroline mol­ecules and is bonded to one chloride ion and one water mol­ecule, resulting in a ZnN4ClO octa­hedral coordination environment with the Cl and O atoms in a cis conformation. The cations and anions are linked by O—H(...)Cl hydrogen bonds across a center of inversion, forming a hydrogen-bonded dimeric association. The dimethyl­formamide solvent mol­ecule is disordered over two orientations in a 0.56 (1):0.44 (1) ratio.

Related literature

The title compound is isostructural with the cobalt and nickel analogs: see Liu, Gao, Huo & Ng (2004 [triangle]); Liu, Liu & Zhong (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m423-scheme1.jpg

Experimental

Crystal data

  • [ZnCl(C12H8N2)2(H2O)]Cl·C3H7NO
  • M r = 587.79
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m423-efi1.jpg
  • a = 9.6743 (3) Å
  • b = 11.6096 (5) Å
  • c = 12.7486 (5) Å
  • α = 67.004 (1)°
  • β = 85.995 (1)°
  • γ = 80.025 (1)°
  • V = 1298.14 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.19 mm−1
  • T = 295 (2) K
  • 0.30 × 0.24 × 0.18 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.660, T max = 0.815
  • 12819 measured reflections
  • 5884 independent reflections
  • 4602 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.103
  • S = 1.11
  • 5884 reflections
  • 383 parameters
  • 61 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.43 e Å−3
  • Δρmin = −0.36 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); method used to solve structure: atomic coordinates taken from the iostructural Co compound (Liu et al., 2004 [triangle] [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002237/hb2689sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002237/hb2689Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

The title compound, (I), is isostructural with its cobalt (Liu, Gao, Huo & Ng, 2004) and nickel analogs (Liu, Liu & Zhong, 2004).

The Zn atom in (I) is chelated by two phenanthroline molecules and bonded to one chloride ion and one water molecule, resulting in a ZnN4ClO octahedral coordination environment with the Cl and O atoms in a cis conformation (Table 1, Fig. 1). The cations and anions are linked by O–H···Cl hydrogen bonds across a center of inversion forming a hydrogen-bonded dimeric association. Details of the hydrogen bonds are given in Table 2.

Experimental

Zinc diacetate dihydrate (1 mmol) and 1,10-phenanthroline (2 mmol) were dissolved in a DMF-water mixture. Several drops of hydrochloric acid were added, and the mixture set aside for the growth of crystals.. The mixture was filtered and colorless blocks of (I) were isolated after several days.

Refinement

The carbon-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) 1.2–1.5Ueq(C).

The water H-atoms were located in a difference map, and were refined with a distance restraint of O–H = 0.85±0.01 Å; their Uiso values were refined.

The DMF solvate molecule is disordered but the disorder components share a nitrogen atom. The C–O distance was restrained to 1.25±0.01 Å, the N–Ccarbonyl distance to 1.35±0.01 Å and the N–Cmethyl distance to 1.45±0.01 Å. The molecule was restrained to be nearly flat. The occupations of the disorder components refined to 0.56 (1):0.44 (1).

Figures

Fig. 1.
View of the molecular structure of (I); displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. Only one disorder component of the DMF molecule is shown.

Crystal data

[ZnCl(C12H8N2)2(H2O)]Cl·C3H7NOZ = 2
Mr = 587.79F(000) = 604
Triclinic, P1Dx = 1.504 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6743 (3) ÅCell parameters from 10359 reflections
b = 11.6096 (5) Åθ = 3.1–27.5°
c = 12.7486 (5) ŵ = 1.19 mm1
α = 67.004 (1)°T = 295 K
β = 85.995 (1)°Block, colorless
γ = 80.025 (1)°0.30 × 0.24 × 0.18 mm
V = 1298.14 (9) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer5884 independent reflections
Radiation source: fine-focus sealed tube4602 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 10.000 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)k = −15→15
Tmin = 0.660, Tmax = 0.815l = −15→16
12819 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0615P)2] where P = (Fo2 + 2Fc2)/3
5884 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.43 e Å3
61 restraintsΔρmin = −0.36 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Zn10.69100 (2)0.67147 (2)0.71925 (2)0.02999 (10)
Cl10.57695 (6)0.68729 (6)0.88327 (5)0.04014 (15)
Cl20.39933 (7)1.05103 (6)0.64297 (5)0.04871 (17)
O1W0.53618 (17)0.80418 (17)0.61027 (14)0.0387 (4)
H1W10.498 (3)0.861 (2)0.634 (2)0.059 (9)*
H1W20.553 (3)0.837 (3)0.5398 (10)0.055 (8)*
N10.88448 (17)0.55649 (18)0.80695 (15)0.0324 (4)
N20.83314 (19)0.80984 (18)0.68954 (16)0.0352 (4)
N30.61286 (18)0.50502 (17)0.72752 (15)0.0316 (4)
N40.78178 (18)0.63714 (18)0.56257 (15)0.0317 (4)
N50.7617 (3)0.0237 (3)0.9642 (3)0.0874 (10)
C10.9880 (2)0.6243 (2)0.80178 (18)0.0324 (5)
C20.9080 (2)0.4331 (2)0.8658 (2)0.0402 (5)
H20.83810.38610.86860.048*
C31.0332 (3)0.3698 (3)0.9242 (2)0.0464 (6)
H31.04540.28260.96510.056*
C41.1368 (3)0.4364 (3)0.9207 (2)0.0481 (6)
H41.22010.39530.96010.058*
C51.1177 (2)0.5674 (3)0.8576 (2)0.0400 (6)
C61.2211 (2)0.6458 (3)0.8478 (2)0.0509 (7)
H61.30630.60920.88550.061*
C71.1979 (3)0.7700 (3)0.7860 (3)0.0532 (7)
H71.26870.81750.77860.064*
C81.0664 (2)0.8316 (3)0.7308 (2)0.0439 (6)
C91.0341 (3)0.9631 (3)0.6682 (2)0.0530 (7)
H91.10071.01500.65960.064*
C100.9053 (3)1.0136 (3)0.6203 (3)0.0553 (7)
H100.88251.10050.57990.066*
C110.8071 (3)0.9338 (2)0.6322 (2)0.0456 (6)
H110.71960.96960.59840.055*
C120.9604 (2)0.7587 (2)0.73849 (18)0.0339 (5)
C130.6459 (2)0.4679 (2)0.63922 (19)0.0324 (5)
C140.5353 (2)0.4368 (2)0.8115 (2)0.0421 (6)
H140.51500.45990.87370.050*
C150.4828 (3)0.3327 (3)0.8111 (3)0.0546 (7)
H150.42870.28780.87160.065*
C160.5120 (3)0.2975 (3)0.7202 (3)0.0527 (7)
H160.47580.22950.71750.063*
C170.5967 (2)0.3644 (2)0.6314 (2)0.0415 (6)
C180.6358 (3)0.3313 (3)0.5352 (2)0.0525 (7)
H180.60260.26360.52910.063*
C190.7204 (3)0.3973 (3)0.4532 (2)0.0541 (7)
H190.74470.37400.39160.065*
C200.7732 (2)0.5017 (3)0.4589 (2)0.0417 (5)
C210.8641 (3)0.5729 (3)0.3765 (2)0.0530 (7)
H210.89310.55190.31420.064*
C220.9091 (3)0.6714 (3)0.3882 (2)0.0501 (7)
H220.96830.71880.33410.060*
C230.8649 (2)0.7005 (2)0.4829 (2)0.0412 (5)
H230.89600.76860.48990.049*
C240.7357 (2)0.5379 (2)0.55131 (18)0.0322 (5)
O10.8615 (13)0.1721 (13)0.8303 (11)0.145 (5)0.560 (9)
C250.8320 (9)0.1203 (9)0.9327 (10)0.153 (5)0.560 (9)
H250.85870.14860.98600.184*0.560 (9)
C260.7138 (10)−0.0335 (9)0.8953 (7)0.105 (3)0.560 (9)
H26A0.73840.01050.81710.157*0.560 (9)
H26B0.6137−0.02870.90200.157*0.560 (9)
H26C0.7571−0.12070.92040.157*0.560 (9)
C270.7266 (10)−0.0410 (11)1.0865 (6)0.137 (4)0.560 (9)
H27A0.8004−0.04061.13290.206*0.560 (9)
H27B0.7166−0.12691.10170.206*0.560 (9)
H27C0.64010.00271.10390.206*0.560 (9)
O1'0.9009 (13)0.1667 (11)0.8546 (11)0.115 (4)0.440 (9)
C25'0.8264 (10)0.0799 (9)0.8675 (9)0.100 (4)0.440 (9)
H25'0.81800.05630.80670.120*0.440 (9)
C26'0.7784 (13)0.0665 (13)1.0524 (9)0.135 (5)0.440 (9)
H26D0.87360.07971.05280.202*0.440 (9)
H26E0.75690.00401.12460.202*0.440 (9)
H26F0.71610.14471.03930.202*0.440 (9)
C27'0.6808 (12)−0.0719 (10)0.9728 (17)0.168 (7)0.440 (9)
H27D0.7428−0.14780.97720.253*0.440 (9)
H27E0.6220−0.04250.90690.253*0.440 (9)
H27F0.6234−0.08951.04010.253*0.440 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.02905 (14)0.03305 (16)0.03096 (15)−0.00828 (10)0.00059 (10)−0.01436 (11)
Cl10.0364 (3)0.0549 (4)0.0340 (3)−0.0079 (3)0.0019 (2)−0.0225 (3)
Cl20.0604 (4)0.0398 (3)0.0463 (4)−0.0088 (3)0.0078 (3)−0.0180 (3)
O1W0.0421 (9)0.0380 (10)0.0353 (9)−0.0009 (7)−0.0029 (7)−0.0151 (8)
N10.0296 (8)0.0378 (10)0.0310 (9)−0.0059 (8)0.0007 (7)−0.0146 (8)
N20.0348 (9)0.0380 (11)0.0381 (10)−0.0104 (8)0.0016 (8)−0.0187 (9)
N30.0311 (9)0.0338 (10)0.0328 (10)−0.0085 (8)0.0026 (7)−0.0149 (8)
N40.0330 (9)0.0334 (10)0.0288 (9)−0.0045 (8)0.0006 (7)−0.0126 (8)
N50.106 (2)0.069 (2)0.099 (2)−0.0437 (19)0.034 (2)−0.0382 (18)
C10.0259 (9)0.0473 (13)0.0299 (11)−0.0061 (9)0.0024 (8)−0.0216 (10)
C20.0375 (11)0.0439 (14)0.0372 (13)−0.0055 (10)0.0016 (10)−0.0140 (11)
C30.0460 (13)0.0473 (15)0.0370 (13)0.0054 (11)−0.0050 (10)−0.0111 (11)
C40.0369 (12)0.0707 (19)0.0369 (13)0.0060 (12)−0.0041 (10)−0.0263 (13)
C50.0291 (10)0.0619 (17)0.0347 (12)−0.0006 (11)−0.0019 (9)−0.0272 (12)
C60.0282 (11)0.081 (2)0.0568 (17)−0.0059 (12)−0.0015 (11)−0.0421 (16)
C70.0324 (12)0.080 (2)0.0638 (18)−0.0224 (13)0.0055 (12)−0.0414 (17)
C80.0368 (12)0.0597 (17)0.0487 (14)−0.0210 (12)0.0099 (11)−0.0315 (13)
C90.0509 (15)0.0574 (18)0.0607 (17)−0.0311 (14)0.0095 (13)−0.0259 (14)
C100.0678 (18)0.0410 (15)0.0591 (17)−0.0207 (14)0.0046 (14)−0.0170 (13)
C110.0455 (13)0.0433 (14)0.0507 (15)−0.0128 (11)0.0008 (11)−0.0186 (12)
C120.0300 (10)0.0463 (14)0.0334 (11)−0.0120 (10)0.0046 (9)−0.0221 (10)
C130.0298 (10)0.0337 (12)0.0373 (12)−0.0033 (9)−0.0034 (9)−0.0178 (10)
C140.0396 (12)0.0439 (14)0.0473 (14)−0.0132 (11)0.0116 (11)−0.0217 (12)
C150.0525 (15)0.0464 (16)0.0701 (19)−0.0239 (13)0.0183 (14)−0.0245 (14)
C160.0493 (14)0.0397 (14)0.078 (2)−0.0167 (12)0.0029 (14)−0.0287 (14)
C170.0383 (12)0.0397 (13)0.0556 (15)−0.0055 (10)−0.0061 (11)−0.0272 (12)
C180.0564 (15)0.0518 (17)0.0673 (19)−0.0064 (13)−0.0096 (14)−0.0413 (15)
C190.0628 (16)0.0637 (19)0.0514 (16)0.0021 (14)−0.0078 (13)−0.0426 (15)
C200.0448 (12)0.0485 (15)0.0347 (12)0.0034 (11)−0.0042 (10)−0.0229 (11)
C210.0577 (15)0.0673 (19)0.0321 (13)0.0035 (14)0.0048 (11)−0.0235 (13)
C220.0520 (15)0.0549 (17)0.0351 (13)−0.0078 (13)0.0126 (11)−0.0108 (12)
C230.0424 (12)0.0421 (14)0.0358 (13)−0.0077 (11)0.0062 (10)−0.0119 (11)
C240.0324 (10)0.0346 (12)0.0303 (11)0.0019 (9)−0.0046 (9)−0.0156 (9)
O10.171 (8)0.152 (8)0.109 (6)−0.028 (6)0.017 (5)−0.050 (5)
C250.202 (9)0.147 (8)0.135 (8)−0.061 (7)0.015 (7)−0.069 (7)
C260.142 (7)0.100 (6)0.083 (5)−0.003 (5)−0.017 (5)−0.049 (5)
C270.172 (8)0.157 (8)0.094 (6)−0.049 (6)0.027 (6)−0.054 (6)
O1'0.147 (7)0.097 (6)0.107 (7)−0.089 (5)0.063 (6)−0.030 (4)
C25'0.139 (8)0.088 (6)0.095 (7)−0.033 (6)0.029 (6)−0.058 (5)
C26'0.144 (8)0.169 (10)0.094 (7)−0.052 (7)0.020 (6)−0.046 (7)
C27'0.149 (9)0.152 (10)0.203 (12)−0.045 (8)0.008 (8)−0.059 (8)

Geometric parameters (Å, °)

Zn1—N12.190 (2)C10—C111.399 (3)
Zn1—N22.198 (2)C10—H100.9300
Zn1—N32.157 (2)C11—H110.9300
Zn1—N42.275 (2)C13—C171.407 (3)
Zn1—O1w2.090 (2)C13—C241.438 (3)
Zn1—Cl12.3520 (6)C14—C151.391 (4)
O1W—H1W10.85 (3)C14—H140.9300
O1W—H1W20.84 (3)C15—C161.369 (4)
N1—C21.319 (3)C15—H150.9300
N1—C11.360 (3)C16—C171.400 (4)
N2—C111.322 (3)C16—H160.9300
N2—C121.350 (3)C17—C181.431 (4)
N3—C141.329 (3)C18—C191.349 (4)
N3—C131.355 (3)C18—H180.9300
N4—C231.314 (3)C19—C201.423 (4)
N4—C241.365 (3)C19—H190.9300
N5—C25'1.320 (10)C20—C241.404 (3)
N5—C251.325 (11)C20—C211.416 (4)
N5—C26'1.424 (8)C21—C221.354 (4)
N5—C261.431 (7)C21—H210.9300
N5—C27'1.432 (9)C22—C231.397 (4)
N5—C271.487 (7)C22—H220.9300
C1—C51.410 (3)C23—H230.9300
C1—C121.435 (3)O1—C251.242 (9)
C2—C31.397 (3)C25—H250.9300
C2—H20.9300C26—H26A0.9600
C3—C41.357 (4)C26—H26B0.9600
C3—H30.9300C26—H26C0.9600
C4—C51.401 (4)C27—H27A0.9600
C4—H40.9300C27—H27B0.9600
C5—C61.433 (4)C27—H27C0.9600
C6—C71.332 (4)O1'—C25'1.291 (19)
C6—H60.9300C25'—H25'0.9300
C7—C81.428 (4)C26'—H26D0.9600
C7—H70.9300C26'—H26E0.9600
C8—C91.408 (4)C26'—H26F0.9600
C8—C121.414 (3)C27'—H27D0.9600
C9—C101.357 (4)C27'—H27E0.9600
C9—H90.9300C27'—H27F0.9600
O1W—Zn1—N396.59 (7)N2—C11—C10122.9 (2)
O1W—Zn1—N1167.57 (6)N2—C11—H11118.5
N3—Zn1—N191.38 (7)C10—C11—H11118.5
O1W—Zn1—N293.77 (7)N2—C12—C8123.0 (2)
N3—Zn1—N2160.59 (7)N2—C12—C1118.07 (19)
N1—Zn1—N275.98 (7)C8—C12—C1118.9 (2)
O1W—Zn1—N486.13 (7)N3—C13—C17122.6 (2)
N3—Zn1—N475.15 (6)N3—C13—C24117.74 (19)
N1—Zn1—N486.72 (6)C17—C13—C24119.6 (2)
N2—Zn1—N489.27 (7)N3—C14—C15123.4 (2)
O1W—Zn1—Cl193.08 (5)N3—C14—H14118.3
N3—Zn1—Cl197.30 (5)C15—C14—H14118.3
N1—Zn1—Cl195.36 (5)C16—C15—C14119.0 (2)
N2—Zn1—Cl198.48 (5)C16—C15—H15120.5
N4—Zn1—Cl1172.25 (5)C14—C15—H15120.5
Zn1—O1W—H1W1114 (2)C15—C16—C17119.6 (2)
Zn1—O1W—H1W2120 (2)C15—C16—H16120.2
H1W1—O1W—H1W2110 (3)C17—C16—H16120.2
C2—N1—C1118.2 (2)C16—C17—C13117.6 (2)
C2—N1—Zn1127.51 (15)C16—C17—C18123.1 (2)
C1—N1—Zn1114.19 (15)C13—C17—C18119.3 (2)
C11—N2—C12118.1 (2)C19—C18—C17120.6 (2)
C11—N2—Zn1127.78 (16)C19—C18—H18119.7
C12—N2—Zn1114.09 (15)C17—C18—H18119.7
C14—N3—C13117.80 (19)C18—C19—C20121.6 (2)
C14—N3—Zn1125.44 (16)C18—C19—H19119.2
C13—N3—Zn1116.76 (14)C20—C19—H19119.2
C23—N4—C24117.9 (2)C24—C20—C21116.6 (2)
C23—N4—Zn1129.65 (17)C24—C20—C19119.4 (2)
C24—N4—Zn1112.42 (13)C21—C20—C19124.0 (2)
C25'—N5—C26'115.4 (8)C22—C21—C20120.2 (2)
C25—N5—C26128.7 (7)C22—C21—H21119.9
C25'—N5—C27'119.3 (10)C20—C21—H21119.9
C26'—N5—C27'125.4 (9)C21—C22—C23118.9 (2)
C25—N5—C27119.5 (8)C21—C22—H22120.6
C26—N5—C27111.8 (6)C23—C22—H22120.6
N1—C1—C5122.3 (2)N4—C23—C22123.6 (2)
N1—C1—C12117.64 (19)N4—C23—H23118.2
C5—C1—C12120.0 (2)C22—C23—H23118.2
N1—C2—C3122.9 (2)N4—C24—C20122.8 (2)
N1—C2—H2118.6N4—C24—C13117.76 (19)
C3—C2—H2118.6C20—C24—C13119.4 (2)
C4—C3—C2119.5 (3)O1—C25—N5118.4 (13)
C4—C3—H3120.2O1—C25—H25120.8
C2—C3—H3120.2N5—C25—H25120.8
C3—C4—C5119.6 (2)N5—C26—H26A109.5
C3—C4—H4120.2N5—C26—H26B109.5
C5—C4—H4120.2N5—C26—H26C109.5
C4—C5—C1117.3 (2)N5—C27—H27A109.5
C4—C5—C6123.9 (2)N5—C27—H27B109.5
C1—C5—C6118.8 (2)N5—C27—H27C109.5
C7—C6—C5121.4 (2)O1'—C25'—N5122.1 (11)
C7—C6—H6119.3O1'—C25'—H25'118.9
C5—C6—H6119.3N5—C25'—H25'118.9
C6—C7—C8121.4 (2)N5—C26'—H26D109.5
C6—C7—H7119.3N5—C26'—H26E109.5
C8—C7—H7119.3H26D—C26'—H26E109.5
C9—C8—C12116.8 (2)N5—C26'—H26F109.5
C9—C8—C7123.9 (2)H26D—C26'—H26F109.5
C12—C8—C7119.4 (3)H26E—C26'—H26F109.5
C10—C9—C8119.7 (2)N5—C27'—H27D109.5
C10—C9—H9120.1N5—C27'—H27E109.5
C8—C9—H9120.1H27D—C27'—H27E109.5
C9—C10—C11119.4 (3)N5—C27'—H27F109.5
C9—C10—H10120.3H27D—C27'—H27F109.5
C11—C10—H10120.3H27E—C27'—H27F109.5
O1W—Zn1—N1—C2−146.2 (3)C7—C8—C9—C10−178.8 (3)
N3—Zn1—N1—C2−16.20 (19)C8—C9—C10—C11−1.1 (4)
N2—Zn1—N1—C2178.7 (2)C12—N2—C11—C100.0 (4)
N4—Zn1—N1—C2−91.24 (19)Zn1—N2—C11—C10178.9 (2)
Cl1—Zn1—N1—C281.27 (19)C9—C10—C11—N20.6 (4)
O1W—Zn1—N1—C136.5 (4)C11—N2—C12—C8−0.2 (3)
N3—Zn1—N1—C1166.52 (14)Zn1—N2—C12—C8−179.21 (17)
N2—Zn1—N1—C11.41 (14)C11—N2—C12—C1179.3 (2)
N4—Zn1—N1—C191.48 (14)Zn1—N2—C12—C10.3 (2)
Cl1—Zn1—N1—C1−96.01 (14)C9—C8—C12—N2−0.2 (3)
O1W—Zn1—N2—C117.4 (2)C7—C8—C12—N2179.5 (2)
N3—Zn1—N2—C11129.6 (2)C9—C8—C12—C1−179.8 (2)
N1—Zn1—N2—C11−179.8 (2)C7—C8—C12—C10.0 (3)
N4—Zn1—N2—C1193.4 (2)N1—C1—C12—N21.0 (3)
Cl1—Zn1—N2—C11−86.3 (2)C5—C1—C12—N2−177.85 (19)
O1W—Zn1—N2—C12−173.77 (15)N1—C1—C12—C8−179.48 (19)
N3—Zn1—N2—C12−51.5 (3)C5—C1—C12—C81.7 (3)
N1—Zn1—N2—C12−0.90 (15)C14—N3—C13—C172.6 (3)
N4—Zn1—N2—C12−87.70 (15)Zn1—N3—C13—C17−177.17 (17)
Cl1—Zn1—N2—C1292.54 (15)C14—N3—C13—C24−176.9 (2)
O1W—Zn1—N3—C14−99.15 (19)Zn1—N3—C13—C243.3 (3)
N1—Zn1—N3—C1490.41 (19)C13—N3—C14—C15−2.3 (4)
N2—Zn1—N3—C14139.0 (2)Zn1—N3—C14—C15177.5 (2)
N4—Zn1—N3—C14176.6 (2)N3—C14—C15—C160.2 (4)
Cl1—Zn1—N3—C14−5.17 (19)C14—C15—C16—C171.7 (4)
O1W—Zn1—N3—C1380.64 (16)C15—C16—C17—C13−1.3 (4)
N1—Zn1—N3—C13−89.80 (16)C15—C16—C17—C18178.0 (3)
N2—Zn1—N3—C13−41.2 (3)N3—C13—C17—C16−0.9 (4)
N4—Zn1—N3—C13−3.56 (15)C24—C13—C17—C16178.7 (2)
Cl1—Zn1—N3—C13174.62 (15)N3—C13—C17—C18179.8 (2)
O1W—Zn1—N4—C2382.8 (2)C24—C13—C17—C18−0.6 (3)
N3—Zn1—N4—C23−179.3 (2)C16—C17—C18—C19−178.5 (3)
N1—Zn1—N4—C23−87.0 (2)C13—C17—C18—C190.8 (4)
N2—Zn1—N4—C23−11.0 (2)C17—C18—C19—C20−0.2 (4)
O1W—Zn1—N4—C24−94.44 (15)C18—C19—C20—C24−0.6 (4)
N3—Zn1—N4—C243.43 (14)C18—C19—C20—C21178.9 (3)
N1—Zn1—N4—C2495.73 (15)C24—C20—C21—C22−0.8 (4)
N2—Zn1—N4—C24171.73 (15)C19—C20—C21—C22179.7 (3)
C2—N1—C1—C5−0.5 (3)C20—C21—C22—C230.4 (4)
Zn1—N1—C1—C5177.05 (16)C24—N4—C23—C22−0.4 (4)
C2—N1—C1—C12−179.31 (19)Zn1—N4—C23—C22−177.58 (18)
Zn1—N1—C1—C12−1.8 (2)C21—C22—C23—N40.3 (4)
C1—N1—C2—C31.0 (3)C23—N4—C24—C200.0 (3)
Zn1—N1—C2—C3−176.18 (17)Zn1—N4—C24—C20177.58 (17)
N1—C2—C3—C4−0.4 (4)C23—N4—C24—C13179.4 (2)
C2—C3—C4—C5−0.8 (4)Zn1—N4—C24—C13−3.0 (2)
C3—C4—C5—C11.2 (3)C21—C20—C24—N40.7 (3)
C3—C4—C5—C6−179.4 (2)C19—C20—C24—N4−179.8 (2)
N1—C1—C5—C4−0.6 (3)C21—C20—C24—C13−178.7 (2)
C12—C1—C5—C4178.2 (2)C19—C20—C24—C130.8 (3)
N1—C1—C5—C6−180.0 (2)N3—C13—C24—N40.0 (3)
C12—C1—C5—C6−1.2 (3)C17—C13—C24—N4−179.6 (2)
C4—C5—C6—C7179.6 (2)N3—C13—C24—C20179.4 (2)
C1—C5—C6—C7−1.1 (4)C17—C13—C24—C20−0.1 (3)
C5—C6—C7—C82.9 (4)C26—N5—C25—O10.8 (4)
C6—C7—C8—C9177.4 (3)C27—N5—C25—O1179.3 (3)
C6—C7—C8—C12−2.3 (4)C26'—N5—C25'—O1'0.8 (3)
C12—C8—C9—C100.9 (4)C27'—N5—C25'—O1'−179.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H1w1···Cl20.85 (3)2.29 (3)3.112 (2)163 (3)
O1w—H1w2···Cl2i0.84 (3)2.24 (3)3.079 (2)172 (3)

Symmetry codes: (i) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2689).

References

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  • Westrip, S. P. (2008). publCIF In preparation.

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