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Acta Cryst. (2008). E64, m423    [ doi:10.1107/S1600536808002237 ]

Aquachloridobis(1,10-phenanthroline-[kappa]2N,N')zinc(II) chloride N,N-dimethylformamide solvate

L.-L. Kong, S. Gao, L.-H. Huo and S. W. Ng

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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.
Aquachloridobis(1,10-phenanthroline-κ2N,N')zinc(II) chloride N,N-dimethylformamide solvate top
Crystal data top
[ZnCl(C12H8N2)2(H2O)]Cl·C3H7NOZ = 2
Mr = 587.79F(000) = 604
Triclinic, P1Dx = 1.504 Mg m−3
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 mm−1
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 top
Rigaku R-AXIS RAPID
diffractometer		5884 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 top
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 = 1.11 w = 1/[σ2(Fo2) + (0.0615P)2]
where P = (Fo2 + 2Fc2)/3
5884 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.43 e Å−3
61 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[ZnCl(C12H8N2)2(H2O)]Cl·C3H7NOγ = 80.025 (1)°
Mr = 587.79V = 1298.14 (9) Å3
Triclinic, P1Z = 2
a = 9.6743 (3) ÅMo Kα radiation
b = 11.6096 (5) ŵ = 1.19 mm−1
c = 12.7486 (5) ÅT = 295 K
α = 67.004 (1)°0.30 × 0.24 × 0.18 mm
β = 85.995 (1)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		5884 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		4602 reflections with I > 2σ(I)
Tmin = 0.660, Tmax = 0.815Rint = 0.022
12819 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.103Δρmax = 0.43 e Å−3
S = 1.11Δρmin = −0.36 e Å−3
5884 reflectionsAbsolute structure: ?
383 parametersFlack parameter: ?
61 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Zn1—N12.190 (2)Zn1—N42.275 (2)
Zn1—N22.198 (2)Zn1—O1w2.090 (2)
Zn1—N32.157 (2)Zn1—Cl12.3520 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

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.

references
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