supporting information


Acta Cryst. (2009). E65, m40    [ doi:10.1107/S1600536808041433 ]

[mu]-Nitrilo­triacetato-tris(1,10-phenanthroline)dizinc(II) nitrate hexa­hydrate

L. F. Chin, C. H. Ng and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top
[Figure 1] 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 line.
µ-Nitrilotriacetato-tris(1,10-phenanthroline)dizinc(II) nitrate hexahydrate top
Crystal data top
[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 top
Bruker SMART APEX
diffractometer
9739 independent reflections
Radiation source: fine-focus sealed tube8382 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.712, Tmax = 0.888k = 1919
40047 measured reflectionsl = 2929
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.03 w = 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
Crystal data top
[Zn2(C6H6NO6)(C12H8N2)3]NO3·6H2OV = 4241.1 (1) Å3
Mr = 1029.58Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.4729 (2) ŵ = 1.21 mm1
b = 15.2672 (2) ÅT = 100 K
c = 22.5295 (3) Å0.30 × 0.20 × 0.10 mm
β = 98.678 (1)°
Data collection top
Bruker SMART APEX
diffractometer
9739 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
8382 reflections with I > 2σ(I)
Tmin = 0.712, Tmax = 0.888Rint = 0.024
40047 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.100H-atom parameters constrained
S = 1.03Δρmax = 0.96 e Å3
9739 reflectionsΔρmin = 0.77 e Å3
562 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C126.4 (2)Zn2—O5—C5—O6174.35 (17)
N5—Zn1—O1—C1163.52 (13)Zn2—O5—C5—C69.5 (2)
N4—Zn1—O1—C184.20 (13)C2—N1—C6—C596.4 (2)
N7—Zn1—O1—C199.07 (13)C4—N1—C6—C5134.18 (19)
O2—Zn1—O1—C11.52 (11)Zn2—N1—C6—C521.6 (2)
N6—Zn1—O1—Zn2164.81 (12)O6—C5—C6—N1160.66 (19)
N5—Zn1—O1—Zn25.26 (15)O5—C5—C6—N122.8 (3)
N4—Zn1—O1—Zn284.59 (15)C11—N2—C7—C80.5 (3)
N7—Zn1—O1—Zn292.14 (15)Zn2—N2—C7—C8168.38 (17)
O2—Zn1—O1—Zn2170.30 (17)N2—C7—C8—C90.0 (4)
O5—Zn2—O1—C194.85 (15)C7—C8—C9—C100.1 (3)
N2—Zn2—O1—C1174.18 (14)C7—N2—C11—C100.8 (2)
O3—Zn2—O1—C17.8 (2)Zn2—N2—C11—C10170.29 (8)
N3—Zn2—O1—C195.96 (15)C7—N2—C11—C15177.90 (16)
N1—Zn2—O1—C111.04 (14)Zn2—N2—C11—C158.44 (16)
O5—Zn2—O1—Zn197.59 (15)N2—C11—C10—C12178.71 (16)
N2—Zn2—O1—Zn16.62 (16)C15—C11—C10—C120.0
O3—Zn2—O1—Zn1159.79 (12)N2—C11—C10—C90.67 (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—C127.66 (19)C11—C10—C12—C130.0
N4—Zn1—O2—C190.83 (13)C9—C10—C12—C13177.94 (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—C3104.52 (15)C12—C13—C14—C16179.56 (17)
N2—Zn2—O3—C3162.70 (15)C18—N3—C15—C140.7 (2)
O1—Zn2—O3—C34.5 (2)Zn2—N3—C15—C14170.11 (8)
N3—Zn2—O3—C383.77 (15)C18—N3—C15—C11178.76 (16)
N1—Zn2—O3—C323.31 (15)Zn2—N3—C15—C1110.47 (16)
N2—Zn2—O5—C5168.84 (16)C13—C14—C15—N3179.41 (16)
O3—Zn2—O5—C574.29 (16)C16—C14—C15—N30.16 (18)
O1—Zn2—O5—C581.19 (15)C13—C14—C15—C110.0
N3—Zn2—O5—C5152.4 (3)C16—C14—C15—C11179.57 (16)
N1—Zn2—O5—C52.75 (15)N2—C11—C15—N31.81 (17)
O5—Zn2—N1—C2106.36 (14)C10—C11—C15—N3179.44 (15)
O3—Zn2—N1—C2153.47 (14)N2—C11—C15—C14178.75 (15)
O1—Zn2—N1—C218.57 (13)C10—C11—C15—C140.0
N3—Zn2—N1—C267.64 (14)C15—C14—C16—C170.8 (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—C4142.46 (13)C15—N3—C18—C170.8 (3)
N3—Zn2—N1—C456.25 (14)Zn2—N3—C18—C17167.69 (17)
O5—Zn2—N1—C613.47 (13)C16—C17—C18—N30.2 (4)
O3—Zn2—N1—C686.71 (13)C23—N4—C19—C200.5 (3)
O1—Zn2—N1—C6101.26 (13)Zn1—N4—C19—C20171.66 (16)
N3—Zn2—N1—C6172.53 (13)N4—C19—C20—C210.4 (3)
O5—Zn2—N2—C78.24 (19)C19—C20—C21—C221.2 (3)
O3—Zn2—N2—C790.45 (19)C19—N4—C23—C221.0 (2)
O1—Zn2—N2—C795.24 (19)Zn1—N4—C23—C22174.41 (8)
N3—Zn2—N2—C7179.0 (2)C19—N4—C23—C27179.55 (15)
O5—Zn2—N2—C11176.74 (13)Zn1—N4—C23—C276.10 (15)
O3—Zn2—N2—C1178.06 (13)N4—C23—C22—C24179.48 (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—C21178.01 (14)
N2—Zn2—N3—C18179.6 (2)C20—C21—C22—C232.6 (3)
O3—Zn2—N3—C1886.0 (2)C20—C21—C22—C24179.42 (16)
O1—Zn2—N3—C1869.1 (2)C23—C22—C24—C250.0
N1—Zn2—N3—C188.4 (2)C21—C22—C24—C25177.91 (15)
O5—Zn2—N3—C1550.8 (4)C22—C24—C25—C260.0
N2—Zn2—N3—C1511.14 (12)C24—C25—C26—C270.0
O3—Zn2—N3—C1583.24 (13)C24—C25—C26—C28179.3
O1—Zn2—N3—C15121.62 (13)C30—N5—C27—C261.5 (2)
N1—Zn2—N3—C15160.84 (12)Zn1—N5—C27—C26175.52 (8)
N6—Zn1—N4—C1966.7 (2)C30—N5—C27—C23179.38 (15)
N5—Zn1—N4—C19178.1 (2)Zn1—N5—C27—C232.34 (14)
O1—Zn1—N4—C1984.07 (19)C25—C26—C27—N5177.82 (15)
O2—Zn1—N4—C1926.75 (19)C28—C26—C27—N51.56 (15)
N6—Zn1—N4—C23120.70 (13)C25—C26—C27—C230.0
N5—Zn1—N4—C235.48 (12)C28—C26—C27—C23179.4
O1—Zn1—N4—C2388.58 (13)N4—C23—C27—N52.60 (14)
O2—Zn1—N4—C23145.90 (13)C22—C23—C27—N5177.91 (14)
N6—Zn1—N5—C3082.8 (2)N4—C23—C27—C26179.50 (15)
N4—Zn1—N5—C30179.1 (2)C22—C23—C27—C260.0
N7—Zn1—N5—C301.3 (2)C25—C26—C28—C29178.78 (17)
O1—Zn1—N5—C3091.5 (2)C27—C26—C28—C290.58 (17)
O2—Zn1—N5—C30115.9 (2)C26—C28—C29—C300.4 (3)
N6—Zn1—N5—C27100.57 (13)C27—N5—C30—C290.5 (3)
N4—Zn1—N5—C274.21 (12)Zn1—N5—C30—C29176.00 (18)
N7—Zn1—N5—C27177.95 (12)C28—C29—C30—N50.5 (4)
O1—Zn1—N5—C2785.12 (12)C35—N6—C31—C320.4 (3)
O2—Zn1—N5—C2760.77 (19)Zn1—N6—C31—C32174.42 (17)
N5—Zn1—N6—C3191.3 (2)N6—C31—C32—C331.3 (4)
N4—Zn1—N6—C318.2 (2)C31—C32—C33—C340.3 (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—C39179.28 (15)
N5—Zn1—N6—C3593.61 (14)Zn1—N6—C35—C393.71 (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—C3575.31 (19)N6—C35—C34—C333.65 (18)
O2—Zn1—N6—C3596.13 (13)C39—C35—C34—C33177.84 (15)
N6—Zn1—N7—C42179.5 (2)C32—C33—C34—C36179.55 (17)
N5—Zn1—N7—C4264.8 (2)C32—C33—C34—C352.7 (3)
O1—Zn1—N7—C4229.5 (2)C35—C34—C36—C370.0
O2—Zn1—N7—C4286.9 (2)C33—C34—C36—C37177.73 (15)
N6—Zn1—N7—C391.96 (12)C34—C36—C37—C380.0
N5—Zn1—N7—C39113.67 (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—O12.59 (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—C354.64 (15)
Zn2—O1—C1—O2176.23 (15)C37—C38—C39—N7175.52 (15)
Zn1—O1—C1—C2174.03 (16)C40—C38—C39—N72.04 (15)
Zn2—O1—C1—C20.7 (2)C37—C38—C39—C350.0
C4—N1—C2—C1141.89 (18)C40—C38—C39—C35177.6
C6—N1—C2—C190.9 (2)N6—C35—C39—N75.71 (15)
Zn2—N1—C2—C123.7 (2)C34—C35—C39—N7175.72 (14)
O2—C1—C2—N1166.81 (19)N6—C35—C39—C38178.57 (15)
O1—C1—C2—N116.2 (3)C34—C35—C39—C380.0
Zn2—O3—C3—O4167.15 (19)C39—C38—C40—C411.44 (17)
Zn2—O3—C3—C410.7 (2)C37—C38—C40—C41176.05 (17)
C2—N1—C4—C3153.33 (18)C38—C40—C41—C420.1 (3)
C6—N1—C4—C378.7 (2)C39—N7—C42—C410.6 (3)
Zn2—N1—C4—C332.78 (19)Zn1—N7—C42—C41177.86 (18)
O4—C3—C4—N1165.09 (19)C40—C41—C42—N71.1 (4)
O3—C3—C4—N116.9 (3)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+1/2; (iv) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formula[Zn2(C6H6NO6)(C12H8N2)3]NO3·6H2O
Mr1029.58
Crystal system, space groupMonoclinic, P21/c
Temperature (K)100
a, b, c (Å)12.4729 (2), 15.2672 (2), 22.5295 (3)
β (°) 98.678 (1)
V3)4241.1 (1)
Z4
Radiation typeMo Kα
µ (mm1)1.21
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.712, 0.888
No. of measured, independent and
observed [I > 2σ(I)] reflections
40047, 9739, 8382
Rint0.024
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.100, 1.03
No. of reflections9739
No. of parameters562
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.96, 0.77

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
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, y1/2, z+1/2; (iv) x+1, y+1, z+1.
 
Acknowledgements top

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