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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m40.
Published online 2008 December 10. doi:  10.1107/S1600536808041433
PMCID: PMC2967886

μ-Nitrilo­triacetato-tris(1,10-phenanthroline)dizinc(II) nitrate hexa­hydrate

Abstract

The nitrilo­triacetate trianion in the title compound, [Zn2(C6H6NO6)(C12H8N2)3]NO3·6H2O, is engaged in N,O,O′,O"-chelation to the phenanthroline-chelated ZnII unit, giving a distorted octa­hedral geometry for the metal atom. One of the three O atoms of the trianion that is engaged in chelation also binds to the bis­(phenanthroline)-chelated ZnII unit, whose five-coordinate geometry is distorted owing to a long Zn(...)O inter­action [2.401 (2) Å]. The dinuclear cations, nitrate anions and uncoordinated water mol­ecules are linked into a three-dimensional network via O—H(...)O hydrogen bonds between water molecules and carboxylate O atoms.

Related literature

There are no structural examples of N-donor ligands of zinc nitrilo­triacetate. For the isostructural copper analog, see: Tang et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-00m40-scheme1.jpg

Experimental

Crystal data

  • [Zn2(C6H6NO6)(C12H8N2)3]NO3·6H2O
  • M r = 1029.58
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m40-efi1.jpg
  • a = 12.4729 (2) Å
  • b = 15.2672 (2) Å
  • c = 22.5295 (3) Å
  • β = 98.678 (1)°
  • V = 4241.1 (1) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.21 mm−1
  • T = 100 (2) K
  • 0.30 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.712, T max = 0.888
  • 40047 measured reflections
  • 9739 independent reflections
  • 8382 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.100
  • S = 1.03
  • 9739 reflections
  • 562 parameters
  • H-atom parameters constrained
  • Δρmax = 0.96 e Å−3
  • Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041433/ci2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041433/ci2741Isup2.hkl

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

Acknowledgments

The authors thank Universiti Tunku Abdul Rahman and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

An methanol solution of zinc(II) nitrate hexahydrate (0.30 g, 1 mmol) and 1,10-phenanthroline (0.20 g, 1 mmol) was mixed with an aqueous solution of nitrilotriacetic acid (0.19 g, 1 mmol) and sodium hydroxide 0.12 g, 3 mmol). The mixture was briefly heated. The cool solution yielded a white solid. This was recrystallized from a water-methanol mixture to give colourless crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2 times Ueq(C). The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonding, but were not refined; their U(H) values were set to 1.5Ueq(O). For the three phenanthroline groups, the central six-membered ring was refined as a rigid hexagon of 1.39 Å sides.

Figures

Fig. 1.
70% Probability displacement ellipsoid plot (Barbour, 2001) of [Zn2(C12H8N2)3(C6H6NO6)](NO3).6H2O. Hydrogen atoms are drawn as spheres of arbitrary radii. The Zn···O interaction of 2.401 (2) Å is shown as a dashed ...

Crystal data

[Zn2(C6H6NO6)(C12H8N2)3]NO3·6H2OF(000) = 2120
Mr = 1029.58Dx = 1.612 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9988 reflections
a = 12.4729 (2) Åθ = 2.4–28.3°
b = 15.2672 (2) ŵ = 1.21 mm1
c = 22.5295 (3) ÅT = 100 K
β = 98.678 (1)°Block, colourless
V = 4241.1 (1) Å30.30 × 0.20 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer9739 independent reflections
Radiation source: fine-focus sealed tube8382 reflections with I > 2σ(I)
graphiteRint = 0.024
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.712, Tmax = 0.888k = −19→19
40047 measured reflectionsl = −29→29

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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0488P)2 + 6.5337P] where P = (Fo2 + 2Fc2)/3
9739 reflections(Δ/σ)max = 0.001
562 parametersΔρmax = 0.96 e Å3
0 restraintsΔρmin = −0.77 e Å3

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

xyzUiso*/Ueq
Zn10.750335 (19)0.816173 (16)0.426850 (11)0.01349 (7)
Zn20.673278 (19)0.610471 (16)0.308663 (11)0.01354 (7)
O10.72485 (12)0.68771 (10)0.38783 (7)0.0159 (3)
O20.81274 (13)0.68509 (10)0.48001 (7)0.0183 (3)
O30.66383 (13)0.49744 (11)0.25608 (7)0.0183 (3)
O40.74100 (15)0.36654 (12)0.25078 (8)0.0260 (4)
O50.52655 (12)0.60029 (10)0.33869 (7)0.0168 (3)
O60.44311 (13)0.53088 (12)0.40537 (7)0.0219 (4)
O70.8216 (3)0.07755 (19)0.36580 (13)0.0761 (10)
O80.8582 (2)0.10886 (16)0.46045 (10)0.0474 (6)
O90.7954 (2)0.20621 (17)0.39637 (11)0.0552 (7)
O1W0.96509 (15)0.59181 (13)0.56473 (9)0.0317 (4)
H110.91650.61620.54060.048*
H120.94560.54070.57180.048*
O2W0.90578 (15)0.42596 (12)0.58705 (8)0.0296 (4)
H210.88730.40100.55380.044*
H220.85840.41600.60910.044*
O3W0.85426 (17)0.34521 (14)0.47592 (8)0.0345 (4)
H310.83420.29710.45970.052*
H320.90720.36420.46050.052*
O4W0.74367 (14)0.18551 (12)0.25717 (8)0.0261 (4)
H410.75020.24000.26140.039*
H420.76040.16120.29070.039*
O5W0.73622 (14)0.13299 (12)0.13985 (8)0.0267 (4)
H510.67960.10590.12560.040*
H520.73440.14560.17580.040*
O6W0.4344 (2)0.39461 (15)0.48746 (10)0.0490 (6)
H610.43330.43390.46090.073*
H620.47600.41140.51850.073*
N10.72137 (14)0.50942 (12)0.37614 (8)0.0133 (3)
N20.60894 (15)0.69114 (12)0.23799 (8)0.0150 (4)
N30.81863 (15)0.64807 (12)0.27339 (8)0.0154 (4)
N40.90460 (15)0.82165 (12)0.39941 (8)0.0140 (3)
N50.71238 (15)0.88131 (12)0.34426 (8)0.0155 (4)
N60.77717 (15)0.89515 (12)0.50346 (8)0.0153 (4)
N70.59262 (15)0.81921 (12)0.45128 (8)0.0156 (4)
N80.82499 (19)0.12888 (16)0.40803 (10)0.0295 (5)
C10.77454 (17)0.64633 (14)0.43311 (10)0.0145 (4)
C20.79166 (18)0.54821 (14)0.42784 (10)0.0163 (4)
H2A0.86840.53700.42380.020*
H2B0.77690.51930.46510.020*
C30.72086 (18)0.43336 (15)0.27824 (10)0.0170 (4)
C40.77312 (18)0.44007 (14)0.34455 (10)0.0157 (4)
H4A0.76590.38320.36470.019*
H4B0.85140.45300.34680.019*
C50.52224 (17)0.54273 (15)0.37824 (10)0.0159 (4)
C60.61716 (18)0.47836 (15)0.39219 (10)0.0168 (4)
H6A0.62770.46510.43570.020*
H6B0.59720.42300.37050.020*
C70.50481 (18)0.71028 (15)0.22108 (10)0.0181 (4)
H70.45410.69470.24680.022*
C80.46713 (18)0.75248 (15)0.16680 (10)0.0191 (4)
H80.39220.76520.15610.023*
C90.53936 (19)0.77523 (15)0.12924 (10)0.0182 (4)
H90.51490.80400.09230.022*
C110.68324 (9)0.71289 (9)0.20064 (6)0.0151 (4)
C100.65230 (8)0.75528 (10)0.14615 (6)0.0169 (4)
C120.72919 (11)0.77442 (10)0.10935 (5)0.0198 (5)
H12A0.70800.80340.07210.024*
C130.83702 (10)0.75116 (10)0.12705 (6)0.0208 (5)
H130.88960.76420.10190.025*
C140.86796 (8)0.70877 (10)0.18155 (6)0.0174 (4)
C150.79107 (10)0.68964 (9)0.21834 (5)0.0148 (4)
C160.97822 (19)0.68396 (15)0.20203 (11)0.0209 (5)
H161.03290.69520.17790.025*
C171.00403 (18)0.64399 (15)0.25654 (11)0.0204 (5)
H171.07690.62780.27090.024*
C180.92185 (18)0.62707 (15)0.29118 (11)0.0187 (4)
H180.94090.59940.32910.022*
C190.99819 (18)0.78963 (15)0.42686 (10)0.0171 (4)
H191.00140.76680.46630.020*
C201.09217 (18)0.78818 (15)0.39994 (11)0.0196 (5)
H201.15760.76440.42090.023*
C211.08920 (18)0.82129 (15)0.34310 (11)0.0190 (4)
H21A1.15210.81960.32400.023*
C230.89980 (10)0.85564 (9)0.34208 (5)0.0147 (4)
C220.99012 (8)0.85846 (9)0.31275 (6)0.0176 (4)
C240.98156 (9)0.89386 (10)0.25539 (6)0.0219 (5)
H241.04330.89580.23530.026*
C250.88269 (10)0.92642 (9)0.22735 (5)0.0225 (5)
H250.87680.95060.18810.027*
C260.79237 (8)0.92359 (7)0.25667 (5)0.0189 (4)
C270.80092 (8)0.88820 (8)0.31404 (5)0.0153 (4)
C280.68803 (10)0.95545 (11)0.22961 (7)0.0233 (5)
H280.67880.98060.19060.028*
C290.6018 (2)0.94917 (16)0.26064 (12)0.0247 (5)
H290.53230.97030.24350.030*
C300.61725 (19)0.91133 (15)0.31788 (11)0.0194 (4)
H300.55680.90700.33880.023*
C310.87041 (19)0.92828 (15)0.53061 (11)0.0195 (5)
H31A0.93370.92030.51240.023*
C320.8793 (2)0.97433 (16)0.58478 (11)0.0231 (5)
H32A0.94760.99600.60330.028*
C330.7882 (2)0.98778 (15)0.61090 (11)0.0213 (5)
H330.79311.01870.64780.026*
C350.68454 (8)0.90717 (9)0.52979 (6)0.0158 (4)
C340.68572 (9)0.95506 (9)0.58236 (6)0.0182 (4)
C360.59038 (11)0.96703 (9)0.60630 (5)0.0207 (5)
H360.59120.99980.64220.025*
C370.49385 (9)0.93110 (9)0.57767 (5)0.0209 (5)
H370.42870.93930.59400.025*
C380.49266 (8)0.88321 (7)0.52510 (5)0.0181 (4)
C390.58800 (9)0.87124 (8)0.50116 (5)0.0157 (4)
C400.39636 (9)0.84143 (11)0.49471 (7)0.0220 (5)
H400.32900.84890.50890.026*
C410.40267 (19)0.79078 (17)0.44505 (12)0.0236 (5)
H41A0.33970.76290.42460.028*
C420.50283 (18)0.78049 (15)0.42477 (11)0.0195 (5)
H42A0.50650.74440.39080.023*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.01251 (12)0.01347 (13)0.01506 (13)0.00027 (9)0.00391 (9)−0.00111 (9)
Zn20.01236 (12)0.01544 (13)0.01283 (12)0.00060 (9)0.00198 (9)0.00228 (9)
O10.0156 (7)0.0135 (7)0.0187 (8)0.0013 (6)0.0032 (6)0.0011 (6)
O20.0191 (8)0.0181 (8)0.0181 (8)−0.0024 (6)0.0041 (6)−0.0054 (6)
O30.0201 (8)0.0205 (8)0.0138 (7)−0.0001 (6)0.0011 (6)−0.0012 (6)
O40.0311 (10)0.0252 (9)0.0221 (9)0.0042 (7)0.0054 (7)−0.0083 (7)
O50.0132 (7)0.0205 (8)0.0169 (8)0.0015 (6)0.0025 (6)0.0030 (6)
O60.0154 (8)0.0326 (9)0.0185 (8)0.0005 (7)0.0053 (6)0.0046 (7)
O70.124 (3)0.0513 (17)0.0581 (17)−0.0281 (17)0.0291 (18)−0.0287 (14)
O80.0474 (14)0.0583 (15)0.0353 (12)0.0080 (11)0.0028 (10)0.0141 (11)
O90.0716 (18)0.0452 (14)0.0434 (14)0.0175 (13)−0.0092 (12)0.0040 (11)
O1W0.0277 (10)0.0265 (10)0.0376 (11)0.0031 (8)−0.0054 (8)−0.0026 (8)
O2W0.0313 (10)0.0310 (10)0.0262 (9)−0.0033 (8)0.0036 (8)0.0029 (8)
O3W0.0446 (12)0.0342 (11)0.0252 (10)0.0038 (9)0.0067 (8)0.0046 (8)
O4W0.0225 (9)0.0295 (10)0.0264 (9)0.0010 (7)0.0042 (7)−0.0018 (7)
O5W0.0221 (9)0.0335 (10)0.0243 (9)−0.0070 (7)0.0032 (7)0.0007 (7)
O6W0.0672 (16)0.0452 (13)0.0335 (12)−0.0131 (12)0.0046 (11)−0.0019 (10)
N10.0130 (8)0.0140 (8)0.0126 (8)0.0009 (7)0.0013 (7)−0.0027 (7)
N20.0127 (8)0.0169 (9)0.0155 (9)0.0007 (7)0.0027 (7)0.0021 (7)
N30.0136 (9)0.0165 (9)0.0160 (9)0.0005 (7)0.0016 (7)0.0015 (7)
N40.0136 (8)0.0136 (8)0.0147 (9)−0.0003 (7)0.0021 (7)−0.0003 (7)
N50.0149 (9)0.0132 (8)0.0183 (9)0.0005 (7)0.0016 (7)−0.0004 (7)
N60.0165 (9)0.0135 (9)0.0162 (9)−0.0007 (7)0.0034 (7)0.0004 (7)
N70.0150 (9)0.0147 (9)0.0176 (9)−0.0003 (7)0.0039 (7)−0.0025 (7)
N80.0272 (11)0.0340 (12)0.0286 (12)−0.0088 (9)0.0081 (9)−0.0050 (10)
C10.0111 (9)0.0150 (10)0.0187 (10)−0.0017 (8)0.0061 (8)−0.0008 (8)
C20.0187 (10)0.0148 (10)0.0140 (10)0.0013 (8)−0.0018 (8)−0.0016 (8)
C30.0150 (10)0.0212 (11)0.0157 (10)−0.0034 (8)0.0060 (8)−0.0028 (8)
C40.0168 (10)0.0142 (10)0.0161 (10)0.0022 (8)0.0020 (8)−0.0022 (8)
C50.0143 (10)0.0197 (11)0.0133 (10)−0.0027 (8)0.0008 (8)−0.0028 (8)
C60.0179 (10)0.0165 (10)0.0168 (10)0.0001 (8)0.0053 (8)0.0032 (8)
C70.0157 (10)0.0194 (11)0.0198 (11)0.0016 (8)0.0047 (8)0.0022 (9)
C80.0147 (10)0.0205 (11)0.0211 (11)0.0029 (8)−0.0002 (8)0.0014 (9)
C90.0209 (11)0.0167 (10)0.0160 (10)0.0032 (8)−0.0002 (8)0.0011 (8)
C110.0173 (10)0.0120 (9)0.0166 (10)−0.0018 (8)0.0043 (8)−0.0009 (8)
C100.0188 (11)0.0150 (10)0.0169 (10)0.0005 (8)0.0025 (8)−0.0007 (8)
C120.0252 (12)0.0190 (11)0.0154 (10)0.0003 (9)0.0041 (9)0.0023 (8)
C130.0225 (11)0.0206 (11)0.0214 (11)−0.0024 (9)0.0102 (9)0.0013 (9)
C140.0167 (10)0.0154 (10)0.0209 (11)−0.0020 (8)0.0049 (8)−0.0017 (8)
C150.0165 (10)0.0121 (10)0.0163 (10)−0.0008 (8)0.0038 (8)−0.0008 (8)
C160.0160 (11)0.0199 (11)0.0281 (12)−0.0020 (9)0.0076 (9)−0.0020 (9)
C170.0130 (10)0.0208 (11)0.0271 (12)0.0003 (9)0.0022 (9)0.0002 (9)
C180.0147 (10)0.0175 (11)0.0232 (11)−0.0008 (8)0.0003 (8)0.0024 (9)
C190.0159 (10)0.0163 (10)0.0186 (11)−0.0004 (8)0.0011 (8)0.0011 (8)
C200.0117 (10)0.0179 (11)0.0288 (12)0.0008 (8)0.0021 (9)−0.0005 (9)
C210.0154 (10)0.0168 (10)0.0265 (12)−0.0022 (8)0.0082 (9)−0.0018 (9)
C230.0175 (10)0.0122 (9)0.0149 (10)−0.0030 (8)0.0040 (8)−0.0025 (8)
C220.0176 (11)0.0149 (10)0.0209 (11)−0.0038 (8)0.0046 (8)−0.0028 (8)
C240.0241 (12)0.0209 (12)0.0230 (12)−0.0047 (9)0.0104 (9)−0.0005 (9)
C250.0312 (13)0.0198 (11)0.0165 (11)−0.0048 (10)0.0041 (9)0.0022 (9)
C260.0240 (12)0.0135 (10)0.0184 (11)−0.0014 (9)0.0005 (9)0.0006 (8)
C270.0182 (10)0.0112 (9)0.0164 (10)−0.0014 (8)0.0023 (8)−0.0023 (8)
C280.0293 (13)0.0195 (11)0.0188 (11)−0.0002 (10)−0.0041 (9)0.0048 (9)
C290.0205 (11)0.0223 (12)0.0285 (13)0.0045 (9)−0.0056 (9)0.0026 (10)
C300.0173 (11)0.0178 (11)0.0227 (11)0.0026 (9)0.0019 (9)0.0000 (9)
C310.0184 (11)0.0181 (11)0.0221 (11)−0.0022 (9)0.0030 (9)0.0007 (9)
C320.0222 (12)0.0205 (11)0.0249 (12)−0.0061 (9)−0.0020 (9)−0.0019 (9)
C330.0292 (12)0.0174 (11)0.0168 (11)−0.0030 (9)0.0016 (9)−0.0032 (9)
C350.0185 (11)0.0131 (10)0.0161 (10)0.0033 (8)0.0035 (8)0.0023 (8)
C340.0248 (12)0.0123 (10)0.0174 (11)0.0009 (8)0.0028 (9)0.0010 (8)
C360.0292 (12)0.0170 (11)0.0166 (11)0.0035 (9)0.0055 (9)−0.0021 (9)
C370.0230 (12)0.0216 (11)0.0205 (11)0.0049 (9)0.0105 (9)0.0008 (9)
C380.0189 (11)0.0157 (10)0.0205 (11)0.0027 (8)0.0056 (9)0.0019 (8)
C390.0193 (11)0.0140 (10)0.0145 (10)0.0015 (8)0.0046 (8)0.0019 (8)
C400.0155 (11)0.0259 (12)0.0258 (12)0.0014 (9)0.0073 (9)−0.0018 (10)
C410.0141 (11)0.0268 (12)0.0301 (13)−0.0036 (9)0.0036 (9)−0.0046 (10)
C420.0179 (11)0.0206 (11)0.0204 (11)−0.0004 (9)0.0037 (9)−0.0049 (9)

Geometric parameters (Å, °)

Zn1—N62.0907 (19)C8—C91.370 (3)
Zn1—N52.0999 (19)C8—H80.95
Zn1—N42.1096 (18)C9—C101.435 (2)
Zn1—N72.1217 (19)C9—H90.95
Zn1—O12.1532 (15)C11—C101.39
Zn1—O22.4008 (16)C11—C151.39
Zn2—O52.0506 (15)C10—C121.39
Zn2—N22.0761 (18)C12—C131.39
Zn2—O32.0864 (16)C12—H12A0.95
Zn2—O12.1539 (16)C13—C141.39
Zn2—N32.1639 (18)C13—H130.95
Zn2—N12.1853 (18)C14—C151.39
O1—C11.278 (3)C14—C161.434 (3)
O2—C11.242 (3)C16—C171.366 (3)
O3—C31.267 (3)C16—H160.95
O4—C31.238 (3)C17—C181.403 (3)
O5—C51.258 (3)C17—H170.95
O6—C51.250 (3)C18—H180.95
O7—N81.228 (3)C19—C201.399 (3)
O8—N81.230 (3)C19—H190.95
O9—N81.253 (3)C20—C211.372 (3)
O1W—H110.84C20—H200.95
O1W—H120.84C21—C221.436 (3)
O2W—H210.84C21—H21A0.95
O2W—H220.84C23—C221.39
O3W—H310.84C23—C271.39
O3W—H320.84C22—C241.39
O4W—H410.84C24—C251.39
O4W—H420.84C24—H240.95
O5W—H510.84C25—C261.39
O5W—H520.84C25—H250.95
O6W—H610.85C26—C271.39
O6W—H620.85C26—C281.436
N1—C21.472 (3)C28—C291.372 (3)
N1—C41.477 (3)C28—H280.95
N1—C61.479 (3)C29—C301.400 (3)
N2—C71.330 (3)C29—H290.95
N2—C111.383 (2)C30—H300.95
N3—C181.329 (3)C31—C321.398 (3)
N3—C151.389 (2)C31—H31A0.95
N4—C191.329 (3)C32—C331.371 (3)
N4—C231.385 (2)C32—H32A0.95
N5—C301.326 (3)C33—C341.432 (3)
N5—C271.386 (2)C33—H330.95
N6—C311.330 (3)C35—C341.39
N6—C351.388 (2)C35—C391.39
N7—C421.326 (3)C34—C361.39
N7—C391.385 (2)C36—C371.39
C1—C21.520 (3)C36—H360.95
C2—H2A0.99C37—C381.39
C2—H2B0.99C37—H370.95
C3—C41.541 (3)C38—C391.39
C4—H4A0.99C38—C401.4389
C4—H4B0.99C40—C411.372 (3)
C5—C61.534 (3)C40—H400.95
C6—H6A0.99C41—C421.402 (3)
C6—H6B0.99C41—H41A0.95
C7—C81.399 (3)C42—H42A0.95
C7—H70.95
N6—Zn1—N5116.43 (7)C8—C9—C10119.52 (19)
N6—Zn1—N4100.35 (7)C8—C9—H9120.2
N5—Zn1—N479.35 (7)C10—C9—H9120.2
N6—Zn1—N779.19 (7)N2—C11—C10121.81 (11)
N5—Zn1—N797.22 (7)N2—C11—C15118.18 (11)
N4—Zn1—N7175.95 (7)C10—C11—C15120.0
N6—Zn1—O1149.07 (7)C11—C10—C12120.0
N5—Zn1—O194.01 (6)C11—C10—C9117.62 (13)
N4—Zn1—O190.08 (6)C12—C10—C9122.35 (13)
N7—Zn1—O192.31 (6)C13—C12—C10120.0
N6—Zn1—O293.98 (6)C13—C12—H12A120.0
N5—Zn1—O2148.16 (6)C10—C12—H12A120.0
N4—Zn1—O286.43 (6)C12—C13—C14120.0
N7—Zn1—O297.61 (6)C12—C13—H13120.0
O1—Zn1—O257.39 (6)C14—C13—H13120.0
O5—Zn2—N292.12 (7)C15—C14—C13120.0
O5—Zn2—O398.50 (6)C15—C14—C16117.84 (13)
N2—Zn2—O394.19 (7)C13—C14—C16122.16 (13)
O5—Zn2—O186.45 (6)N3—C15—C14121.89 (11)
N2—Zn2—O1110.05 (7)N3—C15—C11118.11 (11)
O3—Zn2—O1155.12 (6)C14—C15—C11120.0
O5—Zn2—N3168.57 (7)C17—C16—C14119.5 (2)
N2—Zn2—N379.01 (7)C17—C16—H16120.3
O3—Zn2—N389.40 (7)C14—C16—H16120.3
O1—Zn2—N389.82 (6)C16—C17—C18119.3 (2)
O5—Zn2—N183.22 (6)C16—C17—H17120.3
N2—Zn2—N1170.41 (7)C18—C17—H17120.3
O3—Zn2—N178.30 (6)N3—C18—C17122.9 (2)
O1—Zn2—N178.12 (6)N3—C18—H18118.5
N3—Zn2—N1106.59 (7)C17—C18—H18118.5
C1—O1—Zn195.76 (13)N4—C19—C20122.6 (2)
C1—O1—Zn2116.02 (13)N4—C19—H19118.7
Zn1—O1—Zn2147.57 (8)C20—C19—H19118.7
C1—O2—Zn185.35 (13)C21—C20—C19119.5 (2)
C3—O3—Zn2115.77 (14)C21—C20—H20120.3
C5—O5—Zn2114.97 (14)C19—C20—H20120.3
H11—O1W—H12109.6C20—C21—C22119.35 (19)
H21—O2W—H22108.8C20—C21—H21A120.3
H31—O3W—H32108.8C22—C21—H21A120.3
H41—O4W—H42109.2N4—C23—C22122.07 (11)
H51—O5W—H52109.8N4—C23—C27117.93 (11)
H61—O6W—H62108.2C22—C23—C27120.0
C2—N1—C4114.71 (17)C23—C22—C24120.0
C2—N1—C6112.08 (17)C23—C22—C21117.54 (12)
C4—N1—C6110.61 (17)C24—C22—C21122.43 (12)
C2—N1—Zn2109.55 (13)C22—C24—C25120.0
C4—N1—Zn2105.36 (13)C22—C24—H24120.0
C6—N1—Zn2103.73 (13)C25—C24—H24120.0
C7—N2—C11119.21 (17)C26—C25—C24120.0
C7—N2—Zn2126.73 (15)C26—C25—H25120.0
C11—N2—Zn2113.09 (12)C24—C25—H25120.0
C18—N3—C15118.52 (18)C25—C26—C27120.0
C18—N3—Zn2130.74 (16)C25—C26—C28122.4
C15—N3—Zn2109.93 (12)C27—C26—C28117.6
C19—N4—C23118.90 (17)N5—C27—C26122.08 (10)
C19—N4—Zn1128.68 (15)N5—C27—C23117.88 (10)
C23—N4—Zn1112.04 (12)C26—C27—C23120.0
C30—N5—C27118.63 (18)C29—C28—C26119.35 (12)
C30—N5—Zn1128.87 (16)C29—C28—H28120.3
C27—N5—Zn1112.42 (12)C26—C28—H28120.3
C31—N6—C35118.67 (18)C28—C29—C30119.2 (2)
C31—N6—Zn1128.25 (16)C28—C29—H29120.4
C35—N6—Zn1112.90 (12)C30—C29—H29120.4
C42—N7—C39119.06 (17)N5—C30—C29123.0 (2)
C42—N7—Zn1128.79 (15)N5—C30—H30118.5
C39—N7—Zn1112.14 (12)C29—C30—H30118.5
O7—N8—O8123.5 (3)N6—C31—C32122.8 (2)
O7—N8—O9117.7 (3)N6—C31—H31A118.6
O8—N8—O9118.8 (2)C32—C31—H31A118.6
O2—C1—O1121.4 (2)C33—C32—C31119.2 (2)
O2—C1—C2119.7 (2)C33—C32—H32A120.4
O1—C1—C2118.79 (19)C31—C32—H32A120.4
N1—C2—C1112.60 (18)C32—C33—C34119.8 (2)
N1—C2—H2A109.1C32—C33—H33120.1
C1—C2—H2A109.1C34—C33—H33120.1
N1—C2—H2B109.1N6—C35—C34122.07 (11)
C1—C2—H2B109.1N6—C35—C39117.91 (11)
H2A—C2—H2B107.8C34—C35—C39120.0
O4—C3—O3125.7 (2)C36—C34—C35120.0
O4—C3—C4116.8 (2)C36—C34—C33122.55 (12)
O3—C3—C4117.45 (19)C35—C34—C33117.41 (12)
N1—C4—C3111.29 (17)C37—C36—C34120.0
N1—C4—H4A109.4C37—C36—H36120.0
C3—C4—H4A109.4C34—C36—H36120.0
N1—C4—H4B109.4C36—C37—C38120.0
C3—C4—H4B109.4C36—C37—H37120.0
H4A—C4—H4B108.0C38—C37—H37120.0
O6—C5—O5124.7 (2)C39—C38—C37120.0
O6—C5—C6116.67 (19)C39—C38—C40117.3
O5—C5—C6118.58 (19)C37—C38—C40122.7
N1—C6—C5115.09 (18)N7—C39—C38122.22 (10)
N1—C6—H6A108.5N7—C39—C35117.63 (10)
C5—C6—H6A108.5C38—C39—C35120.0
N1—C6—H6B108.5C41—C40—C38119.44 (12)
C5—C6—H6B108.5C41—C40—H40120.3
H6A—C6—H6B107.5C38—C40—H40120.3
N2—C7—C8122.4 (2)C40—C41—C42119.5 (2)
N2—C7—H7118.8C40—C41—H41A120.2
C8—C7—H7118.8C42—C41—H41A120.2
C9—C8—C7119.4 (2)N7—C42—C41122.5 (2)
C9—C8—H8120.3N7—C42—H42A118.8
C7—C8—H8120.3C41—C42—H42A118.8
N6—Zn1—O1—C1−26.4 (2)Zn2—O5—C5—O6174.35 (17)
N5—Zn1—O1—C1163.52 (13)Zn2—O5—C5—C6−9.5 (2)
N4—Zn1—O1—C184.20 (13)C2—N1—C6—C596.4 (2)
N7—Zn1—O1—C1−99.07 (13)C4—N1—C6—C5−134.18 (19)
O2—Zn1—O1—C1−1.52 (11)Zn2—N1—C6—C5−21.6 (2)
N6—Zn1—O1—Zn2164.81 (12)O6—C5—C6—N1−160.66 (19)
N5—Zn1—O1—Zn2−5.26 (15)O5—C5—C6—N122.8 (3)
N4—Zn1—O1—Zn2−84.59 (15)C11—N2—C7—C8−0.5 (3)
N7—Zn1—O1—Zn292.14 (15)Zn2—N2—C7—C8−168.38 (17)
O2—Zn1—O1—Zn2−170.30 (17)N2—C7—C8—C90.0 (4)
O5—Zn2—O1—C194.85 (15)C7—C8—C9—C100.1 (3)
N2—Zn2—O1—C1−174.18 (14)C7—N2—C11—C100.8 (2)
O3—Zn2—O1—C1−7.8 (2)Zn2—N2—C11—C10170.29 (8)
N3—Zn2—O1—C1−95.96 (15)C7—N2—C11—C15−177.90 (16)
N1—Zn2—O1—C111.04 (14)Zn2—N2—C11—C15−8.44 (16)
O5—Zn2—O1—Zn1−97.59 (15)N2—C11—C10—C12−178.71 (16)
N2—Zn2—O1—Zn1−6.62 (16)C15—C11—C10—C120.0
O3—Zn2—O1—Zn1159.79 (12)N2—C11—C10—C9−0.67 (18)
N3—Zn2—O1—Zn171.60 (15)C15—C11—C10—C9178.04 (16)
N1—Zn2—O1—Zn1178.60 (16)C8—C9—C10—C110.2 (3)
N6—Zn1—O2—C1169.03 (13)C8—C9—C10—C12178.18 (17)
N5—Zn1—O2—C1−27.66 (19)C11—C10—C12—C130.0
N4—Zn1—O2—C1−90.83 (13)C9—C10—C12—C13−177.94 (17)
N7—Zn1—O2—C189.42 (13)C10—C12—C13—C140.0
O1—Zn1—O2—C11.56 (12)C12—C13—C14—C150.0
O5—Zn2—O3—C3−104.52 (15)C12—C13—C14—C16−179.56 (17)
N2—Zn2—O3—C3162.70 (15)C18—N3—C15—C140.7 (2)
O1—Zn2—O3—C3−4.5 (2)Zn2—N3—C15—C14−170.11 (8)
N3—Zn2—O3—C383.77 (15)C18—N3—C15—C11−178.76 (16)
N1—Zn2—O3—C3−23.31 (15)Zn2—N3—C15—C1110.47 (16)
N2—Zn2—O5—C5168.84 (16)C13—C14—C15—N3−179.41 (16)
O3—Zn2—O5—C574.29 (16)C16—C14—C15—N30.16 (18)
O1—Zn2—O5—C5−81.19 (15)C13—C14—C15—C110.0
N3—Zn2—O5—C5−152.4 (3)C16—C14—C15—C11179.57 (16)
N1—Zn2—O5—C5−2.75 (15)N2—C11—C15—N3−1.81 (17)
O5—Zn2—N1—C2−106.36 (14)C10—C11—C15—N3179.44 (15)
O3—Zn2—N1—C2153.47 (14)N2—C11—C15—C14178.75 (15)
O1—Zn2—N1—C2−18.57 (13)C10—C11—C15—C140.0
N3—Zn2—N1—C267.64 (14)C15—C14—C16—C17−0.8 (3)
O5—Zn2—N1—C4129.76 (13)C13—C14—C16—C17178.72 (17)
O3—Zn2—N1—C429.58 (13)C14—C16—C17—C180.7 (3)
O1—Zn2—N1—C4−142.46 (13)C15—N3—C18—C17−0.8 (3)
N3—Zn2—N1—C4−56.25 (14)Zn2—N3—C18—C17167.69 (17)
O5—Zn2—N1—C613.47 (13)C16—C17—C18—N30.2 (4)
O3—Zn2—N1—C6−86.71 (13)C23—N4—C19—C20−0.5 (3)
O1—Zn2—N1—C6101.26 (13)Zn1—N4—C19—C20171.66 (16)
N3—Zn2—N1—C6−172.53 (13)N4—C19—C20—C210.4 (3)
O5—Zn2—N2—C7−8.24 (19)C19—C20—C21—C221.2 (3)
O3—Zn2—N2—C790.45 (19)C19—N4—C23—C22−1.0 (2)
O1—Zn2—N2—C7−95.24 (19)Zn1—N4—C23—C22−174.41 (8)
N3—Zn2—N2—C7179.0 (2)C19—N4—C23—C27179.55 (15)
O5—Zn2—N2—C11−176.74 (13)Zn1—N4—C23—C276.10 (15)
O3—Zn2—N2—C11−78.06 (13)N4—C23—C22—C24−179.48 (15)
O1—Zn2—N2—C1196.26 (13)C27—C23—C22—C240.0
N3—Zn2—N2—C1110.52 (13)N4—C23—C22—C212.51 (18)
O5—Zn2—N3—C18140.0 (3)C27—C23—C22—C21−178.01 (14)
N2—Zn2—N3—C18179.6 (2)C20—C21—C22—C23−2.6 (3)
O3—Zn2—N3—C18−86.0 (2)C20—C21—C22—C24179.42 (16)
O1—Zn2—N3—C1869.1 (2)C23—C22—C24—C250.0
N1—Zn2—N3—C18−8.4 (2)C21—C22—C24—C25177.91 (15)
O5—Zn2—N3—C15−50.8 (4)C22—C24—C25—C260.0
N2—Zn2—N3—C15−11.14 (12)C24—C25—C26—C270.0
O3—Zn2—N3—C1583.24 (13)C24—C25—C26—C28−179.3
O1—Zn2—N3—C15−121.62 (13)C30—N5—C27—C26−1.5 (2)
N1—Zn2—N3—C15160.84 (12)Zn1—N5—C27—C26175.52 (8)
N6—Zn1—N4—C1966.7 (2)C30—N5—C27—C23−179.38 (15)
N5—Zn1—N4—C19−178.1 (2)Zn1—N5—C27—C23−2.34 (14)
O1—Zn1—N4—C19−84.07 (19)C25—C26—C27—N5−177.82 (15)
O2—Zn1—N4—C19−26.75 (19)C28—C26—C27—N51.56 (15)
N6—Zn1—N4—C23−120.70 (13)C25—C26—C27—C230.0
N5—Zn1—N4—C23−5.48 (12)C28—C26—C27—C23179.4
O1—Zn1—N4—C2388.58 (13)N4—C23—C27—N5−2.60 (14)
O2—Zn1—N4—C23145.90 (13)C22—C23—C27—N5177.91 (14)
N6—Zn1—N5—C30−82.8 (2)N4—C23—C27—C26179.50 (15)
N4—Zn1—N5—C30−179.1 (2)C22—C23—C27—C260.0
N7—Zn1—N5—C30−1.3 (2)C25—C26—C28—C29178.78 (17)
O1—Zn1—N5—C3091.5 (2)C27—C26—C28—C29−0.58 (17)
O2—Zn1—N5—C30115.9 (2)C26—C28—C29—C30−0.4 (3)
N6—Zn1—N5—C27100.57 (13)C27—N5—C30—C290.5 (3)
N4—Zn1—N5—C274.21 (12)Zn1—N5—C30—C29−176.00 (18)
N7—Zn1—N5—C27−177.95 (12)C28—C29—C30—N50.5 (4)
O1—Zn1—N5—C27−85.12 (12)C35—N6—C31—C320.4 (3)
O2—Zn1—N5—C27−60.77 (19)Zn1—N6—C31—C32−174.42 (17)
N5—Zn1—N6—C31−91.3 (2)N6—C31—C32—C33−1.3 (4)
N4—Zn1—N6—C31−8.2 (2)C31—C32—C33—C34−0.3 (3)
N7—Zn1—N6—C31175.9 (2)C31—N6—C35—C342.2 (2)
O1—Zn1—N6—C3199.7 (2)Zn1—N6—C35—C34177.75 (8)
O2—Zn1—N6—C3178.92 (19)C31—N6—C35—C39−179.28 (15)
N5—Zn1—N6—C3593.61 (14)Zn1—N6—C35—C39−3.71 (15)
N4—Zn1—N6—C35176.77 (12)N6—C35—C34—C36178.51 (15)
N7—Zn1—N6—C350.87 (13)C39—C35—C34—C360.0
O1—Zn1—N6—C35−75.31 (19)N6—C35—C34—C33−3.65 (18)
O2—Zn1—N6—C35−96.13 (13)C39—C35—C34—C33177.84 (15)
N6—Zn1—N7—C42−179.5 (2)C32—C33—C34—C36−179.55 (17)
N5—Zn1—N7—C4264.8 (2)C32—C33—C34—C352.7 (3)
O1—Zn1—N7—C42−29.5 (2)C35—C34—C36—C370.0
O2—Zn1—N7—C42−86.9 (2)C33—C34—C36—C37−177.73 (15)
N6—Zn1—N7—C391.96 (12)C34—C36—C37—C380.0
N5—Zn1—N7—C39−113.67 (13)C36—C37—C38—C390.0
O1—Zn1—N7—C39152.00 (13)C36—C37—C38—C40177.4
O2—Zn1—N7—C3994.59 (13)C42—N7—C39—C381.1 (2)
Zn1—O2—C1—O1−2.59 (19)Zn1—N7—C39—C38179.74 (8)
Zn1—O2—C1—C2174.31 (18)C42—N7—C39—C35176.69 (16)
Zn1—O1—C1—O22.9 (2)Zn1—N7—C39—C35−4.64 (15)
Zn2—O1—C1—O2176.23 (15)C37—C38—C39—N7175.52 (15)
Zn1—O1—C1—C2−174.03 (16)C40—C38—C39—N7−2.04 (15)
Zn2—O1—C1—C2−0.7 (2)C37—C38—C39—C350.0
C4—N1—C2—C1141.89 (18)C40—C38—C39—C35−177.6
C6—N1—C2—C1−90.9 (2)N6—C35—C39—N75.71 (15)
Zn2—N1—C2—C123.7 (2)C34—C35—C39—N7−175.72 (14)
O2—C1—C2—N1166.81 (19)N6—C35—C39—C38−178.57 (15)
O1—C1—C2—N1−16.2 (3)C34—C35—C39—C380.0
Zn2—O3—C3—O4−167.15 (19)C39—C38—C40—C411.44 (17)
Zn2—O3—C3—C410.7 (2)C37—C38—C40—C41−176.05 (17)
C2—N1—C4—C3−153.33 (18)C38—C40—C41—C420.1 (3)
C6—N1—C4—C378.7 (2)C39—N7—C42—C410.6 (3)
Zn2—N1—C4—C3−32.78 (19)Zn1—N7—C42—C41−177.86 (18)
O4—C3—C4—N1−165.09 (19)C40—C41—C42—N7−1.1 (4)
O3—C3—C4—N116.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1w—H11···O20.842.032.862 (3)173
O1w—H12···O2w0.841.872.706 (3)179
O2w—H21···O3w0.841.942.778 (3)176
O2w—H22···O5wi0.841.922.731 (3)162
O3w—H31···O90.842.002.803 (3)160
O3w—H32···O1wii0.841.892.732 (3)173
O4w—H41···O40.841.952.768 (3)165
O4w—H42···O70.842.162.989 (4)167
O5w—H51···O6iii0.841.952.790 (2)174
O5w—H52···O4w0.841.922.750 (3)173
O6w—H61···O60.851.952.797 (3)174
O6w—H62···O6iv0.852.052.889 (3)170

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2741).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tang, X., Liang, F., Chen, J., Li, Y., Xu, Y. & Shen, W. (2007). Mater. Chem. Phys.106, 159–163.
  • Westrip, S. P. (2009). publCIF In preparation.

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