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

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

doi:10.1107/S1600536808041433

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page m40

doi:10.1107/S1600536808041433

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

Lee Fang Chin,^a Chew Hee Ng ^a and Seik Weng Ng ^b ^*

^aFaculty of Engineering & Science, Universiti Tunku Abdul Rahman, Jalan Genting Kelang, 53100 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 4 December 2008; accepted 7 December 2008; online 10 December 2008)

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 Zn^II 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 Zn^II 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 ).

Experimental

Crystal data

[Zn₂(C₆H₆NO₆)(C₁₂H₈N₂)₃]NO₃·6H₂O
M_r = 1029.58
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.100
S = 1.03
9739 reflections
562 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H11⋯O2	0.84	2.03	2.862 (3)	173
O1w—H12⋯O2w	0.84	1.87	2.706 (3)	179
O2w—H21⋯O3w	0.84	1.94	2.778 (3)	176
O2w—H22⋯O5wⁱ	0.84	1.92	2.731 (3)	162
O3w—H31⋯O9	0.84	2.00	2.803 (3)	160
O3w—H32⋯O1wⁱⁱ	0.84	1.89	2.732 (3)	173
O4w—H41⋯O4	0.84	1.95	2.768 (3)	165
O4w—H42⋯O7	0.84	2.16	2.989 (4)	167
O5w—H51⋯O6ⁱⁱⁱ	0.84	1.95	2.790 (2)	174
O5w—H52⋯O4w	0.84	1.92	2.750 (3)	173
O6w—H61⋯O6	0.85	1.95	2.797 (3)	174
O6w—H62⋯O6^iv	0.85	2.05	2.889 (3)	170
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

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

Supporting information

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

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

checkCIF report

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.

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

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]NO₃·6H₂O	F(000) = 2120
M_r = 1029.58	D_x = 1.612 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9988 reflections
a = 12.4729 (2) Å	θ = 2.4–28.3°
b = 15.2672 (2) Å	µ = 1.21 mm⁻¹
c = 22.5295 (3) Å	T = 100 K
β = 98.678 (1)°	Block, colourless
V = 4241.1 (1) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	9739 independent reflections
Radiation source: fine-focus sealed tube	8382 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.712, T_max = 0.888	k = −19→19
40047 measured reflections	l = −29→29

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0488P)² + 6.5337P] where P = (F_o² + 2F_c²)/3
9739 reflections	(Δ/σ)_max = 0.001
562 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[Zn₂(C₆H₆NO₆)(C₁₂H₈N₂)₃]NO₃·6H₂O	V = 4241.1 (1) Å³
M_r = 1029.58	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.4729 (2) Å	µ = 1.21 mm⁻¹
b = 15.2672 (2) Å	T = 100 K
c = 22.5295 (3) Å	0.30 × 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)
T_min = 0.712, T_max = 0.888	R_int = 0.024
40047 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 1.03	Δρ_max = 0.96 e Å⁻³
9739 reflections	Δρ_min = −0.77 e Å⁻³
562 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.750335 (19)	0.816173 (16)	0.426850 (11)	0.01349 (7)
Zn2	0.673278 (19)	0.610471 (16)	0.308663 (11)	0.01354 (7)
O1	0.72485 (12)	0.68771 (10)	0.38783 (7)	0.0159 (3)
O2	0.81274 (13)	0.68509 (10)	0.48001 (7)	0.0183 (3)
O3	0.66383 (13)	0.49744 (11)	0.25608 (7)	0.0183 (3)
O4	0.74100 (15)	0.36654 (12)	0.25078 (8)	0.0260 (4)
O5	0.52655 (12)	0.60029 (10)	0.33869 (7)	0.0168 (3)
O6	0.44311 (13)	0.53088 (12)	0.40537 (7)	0.0219 (4)
O7	0.8216 (3)	0.07755 (19)	0.36580 (13)	0.0761 (10)
O8	0.8582 (2)	0.10886 (16)	0.46045 (10)	0.0474 (6)
O9	0.7954 (2)	0.20621 (17)	0.39637 (11)	0.0552 (7)
O1W	0.96509 (15)	0.59181 (13)	0.56473 (9)	0.0317 (4)
H11	0.9165	0.6162	0.5406	0.048*
H12	0.9456	0.5407	0.5718	0.048*
O2W	0.90578 (15)	0.42596 (12)	0.58705 (8)	0.0296 (4)
H21	0.8873	0.4010	0.5538	0.044*
H22	0.8584	0.4160	0.6091	0.044*
O3W	0.85426 (17)	0.34521 (14)	0.47592 (8)	0.0345 (4)
H31	0.8342	0.2971	0.4597	0.052*
H32	0.9072	0.3642	0.4605	0.052*
O4W	0.74367 (14)	0.18551 (12)	0.25717 (8)	0.0261 (4)
H41	0.7502	0.2400	0.2614	0.039*
H42	0.7604	0.1612	0.2907	0.039*
O5W	0.73622 (14)	0.13299 (12)	0.13985 (8)	0.0267 (4)
H51	0.6796	0.1059	0.1256	0.040*
H52	0.7344	0.1456	0.1758	0.040*
O6W	0.4344 (2)	0.39461 (15)	0.48746 (10)	0.0490 (6)
H61	0.4333	0.4339	0.4609	0.073*
H62	0.4760	0.4114	0.5185	0.073*
N1	0.72137 (14)	0.50942 (12)	0.37614 (8)	0.0133 (3)
N2	0.60894 (15)	0.69114 (12)	0.23799 (8)	0.0150 (4)
N3	0.81863 (15)	0.64807 (12)	0.27339 (8)	0.0154 (4)
N4	0.90460 (15)	0.82165 (12)	0.39941 (8)	0.0140 (3)
N5	0.71238 (15)	0.88131 (12)	0.34426 (8)	0.0155 (4)
N6	0.77717 (15)	0.89515 (12)	0.50346 (8)	0.0153 (4)
N7	0.59262 (15)	0.81921 (12)	0.45128 (8)	0.0156 (4)
N8	0.82499 (19)	0.12888 (16)	0.40803 (10)	0.0295 (5)
C1	0.77454 (17)	0.64633 (14)	0.43311 (10)	0.0145 (4)
C2	0.79166 (18)	0.54821 (14)	0.42784 (10)	0.0163 (4)
H2A	0.8684	0.5370	0.4238	0.020*
H2B	0.7769	0.5193	0.4651	0.020*
C3	0.72086 (18)	0.43336 (15)	0.27824 (10)	0.0170 (4)
C4	0.77312 (18)	0.44007 (14)	0.34455 (10)	0.0157 (4)
H4A	0.7659	0.3832	0.3647	0.019*
H4B	0.8514	0.4530	0.3468	0.019*
C5	0.52224 (17)	0.54273 (15)	0.37824 (10)	0.0159 (4)
C6	0.61716 (18)	0.47836 (15)	0.39219 (10)	0.0168 (4)
H6A	0.6277	0.4651	0.4357	0.020*
H6B	0.5972	0.4230	0.3705	0.020*
C7	0.50481 (18)	0.71028 (15)	0.22108 (10)	0.0181 (4)
H7	0.4541	0.6947	0.2468	0.022*
C8	0.46713 (18)	0.75248 (15)	0.16680 (10)	0.0191 (4)
H8	0.3922	0.7652	0.1561	0.023*
C9	0.53936 (19)	0.77523 (15)	0.12924 (10)	0.0182 (4)
H9	0.5149	0.8040	0.0923	0.022*
C11	0.68324 (9)	0.71289 (9)	0.20064 (6)	0.0151 (4)
C10	0.65230 (8)	0.75528 (10)	0.14615 (6)	0.0169 (4)
C12	0.72919 (11)	0.77442 (10)	0.10935 (5)	0.0198 (5)
H12A	0.7080	0.8034	0.0721	0.024*
C13	0.83702 (10)	0.75116 (10)	0.12705 (6)	0.0208 (5)
H13	0.8896	0.7642	0.1019	0.025*
C14	0.86796 (8)	0.70877 (10)	0.18155 (6)	0.0174 (4)
C15	0.79107 (10)	0.68964 (9)	0.21834 (5)	0.0148 (4)
C16	0.97822 (19)	0.68396 (15)	0.20203 (11)	0.0209 (5)
H16	1.0329	0.6952	0.1779	0.025*
C17	1.00403 (18)	0.64399 (15)	0.25654 (11)	0.0204 (5)
H17	1.0769	0.6278	0.2709	0.024*
C18	0.92185 (18)	0.62707 (15)	0.29118 (11)	0.0187 (4)
H18	0.9409	0.5994	0.3291	0.022*
C19	0.99819 (18)	0.78963 (15)	0.42686 (10)	0.0171 (4)
H19	1.0014	0.7668	0.4663	0.020*
C20	1.09217 (18)	0.78818 (15)	0.39994 (11)	0.0196 (5)
H20	1.1576	0.7644	0.4209	0.023*
C21	1.08920 (18)	0.82129 (15)	0.34310 (11)	0.0190 (4)
H21A	1.1521	0.8196	0.3240	0.023*
C23	0.89980 (10)	0.85564 (9)	0.34208 (5)	0.0147 (4)
C22	0.99012 (8)	0.85846 (9)	0.31275 (6)	0.0176 (4)
C24	0.98156 (9)	0.89386 (10)	0.25539 (6)	0.0219 (5)
H24	1.0433	0.8958	0.2353	0.026*
C25	0.88269 (10)	0.92642 (9)	0.22735 (5)	0.0225 (5)
H25	0.8768	0.9506	0.1881	0.027*
C26	0.79237 (8)	0.92359 (7)	0.25667 (5)	0.0189 (4)
C27	0.80092 (8)	0.88820 (8)	0.31404 (5)	0.0153 (4)
C28	0.68803 (10)	0.95545 (11)	0.22961 (7)	0.0233 (5)
H28	0.6788	0.9806	0.1906	0.028*
C29	0.6018 (2)	0.94917 (16)	0.26064 (12)	0.0247 (5)
H29	0.5323	0.9703	0.2435	0.030*
C30	0.61725 (19)	0.91133 (15)	0.31788 (11)	0.0194 (4)
H30	0.5568	0.9070	0.3388	0.023*
C31	0.87041 (19)	0.92828 (15)	0.53061 (11)	0.0195 (5)
H31A	0.9337	0.9203	0.5124	0.023*
C32	0.8793 (2)	0.97433 (16)	0.58478 (11)	0.0231 (5)
H32A	0.9476	0.9960	0.6033	0.028*
C33	0.7882 (2)	0.98778 (15)	0.61090 (11)	0.0213 (5)
H33	0.7931	1.0187	0.6478	0.026*
C35	0.68454 (8)	0.90717 (9)	0.52979 (6)	0.0158 (4)
C34	0.68572 (9)	0.95506 (9)	0.58236 (6)	0.0182 (4)
C36	0.59038 (11)	0.96703 (9)	0.60630 (5)	0.0207 (5)
H36	0.5912	0.9998	0.6422	0.025*
C37	0.49385 (9)	0.93110 (9)	0.57767 (5)	0.0209 (5)
H37	0.4287	0.9393	0.5940	0.025*
C38	0.49266 (8)	0.88321 (7)	0.52510 (5)	0.0181 (4)
C39	0.58800 (9)	0.87124 (8)	0.50116 (5)	0.0157 (4)
C40	0.39636 (9)	0.84143 (11)	0.49471 (7)	0.0220 (5)
H40	0.3290	0.8489	0.5089	0.026*
C41	0.40267 (19)	0.79078 (17)	0.44505 (12)	0.0236 (5)
H41A	0.3397	0.7629	0.4246	0.028*
C42	0.50283 (18)	0.78049 (15)	0.42477 (11)	0.0195 (5)
H42A	0.5065	0.7444	0.3908	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01251 (12)	0.01347 (13)	0.01506 (13)	0.00027 (9)	0.00391 (9)	−0.00111 (9)
Zn2	0.01236 (12)	0.01544 (13)	0.01283 (12)	0.00060 (9)	0.00198 (9)	0.00228 (9)
O1	0.0156 (7)	0.0135 (7)	0.0187 (8)	0.0013 (6)	0.0032 (6)	0.0011 (6)
O2	0.0191 (8)	0.0181 (8)	0.0181 (8)	−0.0024 (6)	0.0041 (6)	−0.0054 (6)
O3	0.0201 (8)	0.0205 (8)	0.0138 (7)	−0.0001 (6)	0.0011 (6)	−0.0012 (6)
O4	0.0311 (10)	0.0252 (9)	0.0221 (9)	0.0042 (7)	0.0054 (7)	−0.0083 (7)
O5	0.0132 (7)	0.0205 (8)	0.0169 (8)	0.0015 (6)	0.0025 (6)	0.0030 (6)
O6	0.0154 (8)	0.0326 (9)	0.0185 (8)	0.0005 (7)	0.0053 (6)	0.0046 (7)
O7	0.124 (3)	0.0513 (17)	0.0581 (17)	−0.0281 (17)	0.0291 (18)	−0.0287 (14)
O8	0.0474 (14)	0.0583 (15)	0.0353 (12)	0.0080 (11)	0.0028 (10)	0.0141 (11)
O9	0.0716 (18)	0.0452 (14)	0.0434 (14)	0.0175 (13)	−0.0092 (12)	0.0040 (11)
O1W	0.0277 (10)	0.0265 (10)	0.0376 (11)	0.0031 (8)	−0.0054 (8)	−0.0026 (8)
O2W	0.0313 (10)	0.0310 (10)	0.0262 (9)	−0.0033 (8)	0.0036 (8)	0.0029 (8)
O3W	0.0446 (12)	0.0342 (11)	0.0252 (10)	0.0038 (9)	0.0067 (8)	0.0046 (8)
O4W	0.0225 (9)	0.0295 (10)	0.0264 (9)	0.0010 (7)	0.0042 (7)	−0.0018 (7)
O5W	0.0221 (9)	0.0335 (10)	0.0243 (9)	−0.0070 (7)	0.0032 (7)	0.0007 (7)
O6W	0.0672 (16)	0.0452 (13)	0.0335 (12)	−0.0131 (12)	0.0046 (11)	−0.0019 (10)
N1	0.0130 (8)	0.0140 (8)	0.0126 (8)	0.0009 (7)	0.0013 (7)	−0.0027 (7)
N2	0.0127 (8)	0.0169 (9)	0.0155 (9)	0.0007 (7)	0.0027 (7)	0.0021 (7)
N3	0.0136 (9)	0.0165 (9)	0.0160 (9)	0.0005 (7)	0.0016 (7)	0.0015 (7)
N4	0.0136 (8)	0.0136 (8)	0.0147 (9)	−0.0003 (7)	0.0021 (7)	−0.0003 (7)
N5	0.0149 (9)	0.0132 (8)	0.0183 (9)	0.0005 (7)	0.0016 (7)	−0.0004 (7)
N6	0.0165 (9)	0.0135 (9)	0.0162 (9)	−0.0007 (7)	0.0034 (7)	0.0004 (7)
N7	0.0150 (9)	0.0147 (9)	0.0176 (9)	−0.0003 (7)	0.0039 (7)	−0.0025 (7)
N8	0.0272 (11)	0.0340 (12)	0.0286 (12)	−0.0088 (9)	0.0081 (9)	−0.0050 (10)
C1	0.0111 (9)	0.0150 (10)	0.0187 (10)	−0.0017 (8)	0.0061 (8)	−0.0008 (8)
C2	0.0187 (10)	0.0148 (10)	0.0140 (10)	0.0013 (8)	−0.0018 (8)	−0.0016 (8)
C3	0.0150 (10)	0.0212 (11)	0.0157 (10)	−0.0034 (8)	0.0060 (8)	−0.0028 (8)
C4	0.0168 (10)	0.0142 (10)	0.0161 (10)	0.0022 (8)	0.0020 (8)	−0.0022 (8)
C5	0.0143 (10)	0.0197 (11)	0.0133 (10)	−0.0027 (8)	0.0008 (8)	−0.0028 (8)
C6	0.0179 (10)	0.0165 (10)	0.0168 (10)	0.0001 (8)	0.0053 (8)	0.0032 (8)
C7	0.0157 (10)	0.0194 (11)	0.0198 (11)	0.0016 (8)	0.0047 (8)	0.0022 (9)
C8	0.0147 (10)	0.0205 (11)	0.0211 (11)	0.0029 (8)	−0.0002 (8)	0.0014 (9)
C9	0.0209 (11)	0.0167 (10)	0.0160 (10)	0.0032 (8)	−0.0002 (8)	0.0011 (8)
C11	0.0173 (10)	0.0120 (9)	0.0166 (10)	−0.0018 (8)	0.0043 (8)	−0.0009 (8)
C10	0.0188 (11)	0.0150 (10)	0.0169 (10)	0.0005 (8)	0.0025 (8)	−0.0007 (8)
C12	0.0252 (12)	0.0190 (11)	0.0154 (10)	0.0003 (9)	0.0041 (9)	0.0023 (8)
C13	0.0225 (11)	0.0206 (11)	0.0214 (11)	−0.0024 (9)	0.0102 (9)	0.0013 (9)
C14	0.0167 (10)	0.0154 (10)	0.0209 (11)	−0.0020 (8)	0.0049 (8)	−0.0017 (8)
C15	0.0165 (10)	0.0121 (10)	0.0163 (10)	−0.0008 (8)	0.0038 (8)	−0.0008 (8)
C16	0.0160 (11)	0.0199 (11)	0.0281 (12)	−0.0020 (9)	0.0076 (9)	−0.0020 (9)
C17	0.0130 (10)	0.0208 (11)	0.0271 (12)	0.0003 (9)	0.0022 (9)	0.0002 (9)
C18	0.0147 (10)	0.0175 (11)	0.0232 (11)	−0.0008 (8)	0.0003 (8)	0.0024 (9)
C19	0.0159 (10)	0.0163 (10)	0.0186 (11)	−0.0004 (8)	0.0011 (8)	0.0011 (8)
C20	0.0117 (10)	0.0179 (11)	0.0288 (12)	0.0008 (8)	0.0021 (9)	−0.0005 (9)
C21	0.0154 (10)	0.0168 (10)	0.0265 (12)	−0.0022 (8)	0.0082 (9)	−0.0018 (9)
C23	0.0175 (10)	0.0122 (9)	0.0149 (10)	−0.0030 (8)	0.0040 (8)	−0.0025 (8)
C22	0.0176 (11)	0.0149 (10)	0.0209 (11)	−0.0038 (8)	0.0046 (8)	−0.0028 (8)
C24	0.0241 (12)	0.0209 (12)	0.0230 (12)	−0.0047 (9)	0.0104 (9)	−0.0005 (9)
C25	0.0312 (13)	0.0198 (11)	0.0165 (11)	−0.0048 (10)	0.0041 (9)	0.0022 (9)
C26	0.0240 (12)	0.0135 (10)	0.0184 (11)	−0.0014 (9)	0.0005 (9)	0.0006 (8)
C27	0.0182 (10)	0.0112 (9)	0.0164 (10)	−0.0014 (8)	0.0023 (8)	−0.0023 (8)
C28	0.0293 (13)	0.0195 (11)	0.0188 (11)	−0.0002 (10)	−0.0041 (9)	0.0048 (9)
C29	0.0205 (11)	0.0223 (12)	0.0285 (13)	0.0045 (9)	−0.0056 (9)	0.0026 (10)
C30	0.0173 (11)	0.0178 (11)	0.0227 (11)	0.0026 (9)	0.0019 (9)	0.0000 (9)
C31	0.0184 (11)	0.0181 (11)	0.0221 (11)	−0.0022 (9)	0.0030 (9)	0.0007 (9)
C32	0.0222 (12)	0.0205 (11)	0.0249 (12)	−0.0061 (9)	−0.0020 (9)	−0.0019 (9)
C33	0.0292 (12)	0.0174 (11)	0.0168 (11)	−0.0030 (9)	0.0016 (9)	−0.0032 (9)
C35	0.0185 (11)	0.0131 (10)	0.0161 (10)	0.0033 (8)	0.0035 (8)	0.0023 (8)
C34	0.0248 (12)	0.0123 (10)	0.0174 (11)	0.0009 (8)	0.0028 (9)	0.0010 (8)
C36	0.0292 (12)	0.0170 (11)	0.0166 (11)	0.0035 (9)	0.0055 (9)	−0.0021 (9)
C37	0.0230 (12)	0.0216 (11)	0.0205 (11)	0.0049 (9)	0.0105 (9)	0.0008 (9)
C38	0.0189 (11)	0.0157 (10)	0.0205 (11)	0.0027 (8)	0.0056 (9)	0.0019 (8)
C39	0.0193 (11)	0.0140 (10)	0.0145 (10)	0.0015 (8)	0.0046 (8)	0.0019 (8)
C40	0.0155 (11)	0.0259 (12)	0.0258 (12)	0.0014 (9)	0.0073 (9)	−0.0018 (10)
C41	0.0141 (11)	0.0268 (12)	0.0301 (13)	−0.0036 (9)	0.0036 (9)	−0.0046 (10)
C42	0.0179 (11)	0.0206 (11)	0.0204 (11)	−0.0004 (9)	0.0037 (9)	−0.0049 (9)

Geometric parameters (Å, º) top

Zn1—N6	2.0907 (19)	C8—C9	1.370 (3)
Zn1—N5	2.0999 (19)	C8—H8	0.95
Zn1—N4	2.1096 (18)	C9—C10	1.435 (2)
Zn1—N7	2.1217 (19)	C9—H9	0.95
Zn1—O1	2.1532 (15)	C11—C10	1.39
Zn1—O2	2.4008 (16)	C11—C15	1.39
Zn2—O5	2.0506 (15)	C10—C12	1.39
Zn2—N2	2.0761 (18)	C12—C13	1.39
Zn2—O3	2.0864 (16)	C12—H12A	0.95
Zn2—O1	2.1539 (16)	C13—C14	1.39
Zn2—N3	2.1639 (18)	C13—H13	0.95
Zn2—N1	2.1853 (18)	C14—C15	1.39
O1—C1	1.278 (3)	C14—C16	1.434 (3)
O2—C1	1.242 (3)	C16—C17	1.366 (3)
O3—C3	1.267 (3)	C16—H16	0.95
O4—C3	1.238 (3)	C17—C18	1.403 (3)
O5—C5	1.258 (3)	C17—H17	0.95
O6—C5	1.250 (3)	C18—H18	0.95
O7—N8	1.228 (3)	C19—C20	1.399 (3)
O8—N8	1.230 (3)	C19—H19	0.95
O9—N8	1.253 (3)	C20—C21	1.372 (3)
O1W—H11	0.84	C20—H20	0.95
O1W—H12	0.84	C21—C22	1.436 (3)
O2W—H21	0.84	C21—H21A	0.95
O2W—H22	0.84	C23—C22	1.39
O3W—H31	0.84	C23—C27	1.39
O3W—H32	0.84	C22—C24	1.39
O4W—H41	0.84	C24—C25	1.39
O4W—H42	0.84	C24—H24	0.95
O5W—H51	0.84	C25—C26	1.39
O5W—H52	0.84	C25—H25	0.95
O6W—H61	0.85	C26—C27	1.39
O6W—H62	0.85	C26—C28	1.436
N1—C2	1.472 (3)	C28—C29	1.372 (3)
N1—C4	1.477 (3)	C28—H28	0.95
N1—C6	1.479 (3)	C29—C30	1.400 (3)
N2—C7	1.330 (3)	C29—H29	0.95
N2—C11	1.383 (2)	C30—H30	0.95
N3—C18	1.329 (3)	C31—C32	1.398 (3)
N3—C15	1.389 (2)	C31—H31A	0.95
N4—C19	1.329 (3)	C32—C33	1.371 (3)
N4—C23	1.385 (2)	C32—H32A	0.95
N5—C30	1.326 (3)	C33—C34	1.432 (3)
N5—C27	1.386 (2)	C33—H33	0.95
N6—C31	1.330 (3)	C35—C34	1.39
N6—C35	1.388 (2)	C35—C39	1.39
N7—C42	1.326 (3)	C34—C36	1.39
N7—C39	1.385 (2)	C36—C37	1.39
C1—C2	1.520 (3)	C36—H36	0.95
C2—H2A	0.99	C37—C38	1.39
C2—H2B	0.99	C37—H37	0.95
C3—C4	1.541 (3)	C38—C39	1.39
C4—H4A	0.99	C38—C40	1.4389
C4—H4B	0.99	C40—C41	1.372 (3)
C5—C6	1.534 (3)	C40—H40	0.95
C6—H6A	0.99	C41—C42	1.402 (3)
C6—H6B	0.99	C41—H41A	0.95
C7—C8	1.399 (3)	C42—H42A	0.95
C7—H7	0.95

N6—Zn1—N5	116.43 (7)	C8—C9—C10	119.52 (19)
N6—Zn1—N4	100.35 (7)	C8—C9—H9	120.2
N5—Zn1—N4	79.35 (7)	C10—C9—H9	120.2
N6—Zn1—N7	79.19 (7)	N2—C11—C10	121.81 (11)
N5—Zn1—N7	97.22 (7)	N2—C11—C15	118.18 (11)
N4—Zn1—N7	175.95 (7)	C10—C11—C15	120.0
N6—Zn1—O1	149.07 (7)	C11—C10—C12	120.0
N5—Zn1—O1	94.01 (6)	C11—C10—C9	117.62 (13)
N4—Zn1—O1	90.08 (6)	C12—C10—C9	122.35 (13)
N7—Zn1—O1	92.31 (6)	C13—C12—C10	120.0
N6—Zn1—O2	93.98 (6)	C13—C12—H12A	120.0
N5—Zn1—O2	148.16 (6)	C10—C12—H12A	120.0
N4—Zn1—O2	86.43 (6)	C12—C13—C14	120.0
N7—Zn1—O2	97.61 (6)	C12—C13—H13	120.0
O1—Zn1—O2	57.39 (6)	C14—C13—H13	120.0
O5—Zn2—N2	92.12 (7)	C15—C14—C13	120.0
O5—Zn2—O3	98.50 (6)	C15—C14—C16	117.84 (13)
N2—Zn2—O3	94.19 (7)	C13—C14—C16	122.16 (13)
O5—Zn2—O1	86.45 (6)	N3—C15—C14	121.89 (11)
N2—Zn2—O1	110.05 (7)	N3—C15—C11	118.11 (11)
O3—Zn2—O1	155.12 (6)	C14—C15—C11	120.0
O5—Zn2—N3	168.57 (7)	C17—C16—C14	119.5 (2)
N2—Zn2—N3	79.01 (7)	C17—C16—H16	120.3
O3—Zn2—N3	89.40 (7)	C14—C16—H16	120.3
O1—Zn2—N3	89.82 (6)	C16—C17—C18	119.3 (2)
O5—Zn2—N1	83.22 (6)	C16—C17—H17	120.3
N2—Zn2—N1	170.41 (7)	C18—C17—H17	120.3
O3—Zn2—N1	78.30 (6)	N3—C18—C17	122.9 (2)
O1—Zn2—N1	78.12 (6)	N3—C18—H18	118.5
N3—Zn2—N1	106.59 (7)	C17—C18—H18	118.5
C1—O1—Zn1	95.76 (13)	N4—C19—C20	122.6 (2)
C1—O1—Zn2	116.02 (13)	N4—C19—H19	118.7
Zn1—O1—Zn2	147.57 (8)	C20—C19—H19	118.7
C1—O2—Zn1	85.35 (13)	C21—C20—C19	119.5 (2)
C3—O3—Zn2	115.77 (14)	C21—C20—H20	120.3
C5—O5—Zn2	114.97 (14)	C19—C20—H20	120.3
H11—O1W—H12	109.6	C20—C21—C22	119.35 (19)
H21—O2W—H22	108.8	C20—C21—H21A	120.3
H31—O3W—H32	108.8	C22—C21—H21A	120.3
H41—O4W—H42	109.2	N4—C23—C22	122.07 (11)
H51—O5W—H52	109.8	N4—C23—C27	117.93 (11)
H61—O6W—H62	108.2	C22—C23—C27	120.0
C2—N1—C4	114.71 (17)	C23—C22—C24	120.0
C2—N1—C6	112.08 (17)	C23—C22—C21	117.54 (12)
C4—N1—C6	110.61 (17)	C24—C22—C21	122.43 (12)
C2—N1—Zn2	109.55 (13)	C22—C24—C25	120.0
C4—N1—Zn2	105.36 (13)	C22—C24—H24	120.0
C6—N1—Zn2	103.73 (13)	C25—C24—H24	120.0
C7—N2—C11	119.21 (17)	C26—C25—C24	120.0
C7—N2—Zn2	126.73 (15)	C26—C25—H25	120.0
C11—N2—Zn2	113.09 (12)	C24—C25—H25	120.0
C18—N3—C15	118.52 (18)	C25—C26—C27	120.0
C18—N3—Zn2	130.74 (16)	C25—C26—C28	122.4
C15—N3—Zn2	109.93 (12)	C27—C26—C28	117.6
C19—N4—C23	118.90 (17)	N5—C27—C26	122.08 (10)
C19—N4—Zn1	128.68 (15)	N5—C27—C23	117.88 (10)
C23—N4—Zn1	112.04 (12)	C26—C27—C23	120.0
C30—N5—C27	118.63 (18)	C29—C28—C26	119.35 (12)
C30—N5—Zn1	128.87 (16)	C29—C28—H28	120.3
C27—N5—Zn1	112.42 (12)	C26—C28—H28	120.3
C31—N6—C35	118.67 (18)	C28—C29—C30	119.2 (2)
C31—N6—Zn1	128.25 (16)	C28—C29—H29	120.4
C35—N6—Zn1	112.90 (12)	C30—C29—H29	120.4
C42—N7—C39	119.06 (17)	N5—C30—C29	123.0 (2)
C42—N7—Zn1	128.79 (15)	N5—C30—H30	118.5
C39—N7—Zn1	112.14 (12)	C29—C30—H30	118.5
O7—N8—O8	123.5 (3)	N6—C31—C32	122.8 (2)
O7—N8—O9	117.7 (3)	N6—C31—H31A	118.6
O8—N8—O9	118.8 (2)	C32—C31—H31A	118.6
O2—C1—O1	121.4 (2)	C33—C32—C31	119.2 (2)
O2—C1—C2	119.7 (2)	C33—C32—H32A	120.4
O1—C1—C2	118.79 (19)	C31—C32—H32A	120.4
N1—C2—C1	112.60 (18)	C32—C33—C34	119.8 (2)
N1—C2—H2A	109.1	C32—C33—H33	120.1
C1—C2—H2A	109.1	C34—C33—H33	120.1
N1—C2—H2B	109.1	N6—C35—C34	122.07 (11)
C1—C2—H2B	109.1	N6—C35—C39	117.91 (11)
H2A—C2—H2B	107.8	C34—C35—C39	120.0
O4—C3—O3	125.7 (2)	C36—C34—C35	120.0
O4—C3—C4	116.8 (2)	C36—C34—C33	122.55 (12)
O3—C3—C4	117.45 (19)	C35—C34—C33	117.41 (12)
N1—C4—C3	111.29 (17)	C37—C36—C34	120.0
N1—C4—H4A	109.4	C37—C36—H36	120.0
C3—C4—H4A	109.4	C34—C36—H36	120.0
N1—C4—H4B	109.4	C36—C37—C38	120.0
C3—C4—H4B	109.4	C36—C37—H37	120.0
H4A—C4—H4B	108.0	C38—C37—H37	120.0
O6—C5—O5	124.7 (2)	C39—C38—C37	120.0
O6—C5—C6	116.67 (19)	C39—C38—C40	117.3
O5—C5—C6	118.58 (19)	C37—C38—C40	122.7
N1—C6—C5	115.09 (18)	N7—C39—C38	122.22 (10)
N1—C6—H6A	108.5	N7—C39—C35	117.63 (10)
C5—C6—H6A	108.5	C38—C39—C35	120.0
N1—C6—H6B	108.5	C41—C40—C38	119.44 (12)
C5—C6—H6B	108.5	C41—C40—H40	120.3
H6A—C6—H6B	107.5	C38—C40—H40	120.3
N2—C7—C8	122.4 (2)	C40—C41—C42	119.5 (2)
N2—C7—H7	118.8	C40—C41—H41A	120.2
C8—C7—H7	118.8	C42—C41—H41A	120.2
C9—C8—C7	119.4 (2)	N7—C42—C41	122.5 (2)
C9—C8—H8	120.3	N7—C42—H42A	118.8
C7—C8—H8	120.3	C41—C42—H42A	118.8

N6—Zn1—O1—C1	−26.4 (2)	Zn2—O5—C5—O6	174.35 (17)
N5—Zn1—O1—C1	163.52 (13)	Zn2—O5—C5—C6	−9.5 (2)
N4—Zn1—O1—C1	84.20 (13)	C2—N1—C6—C5	96.4 (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—Zn2	164.81 (12)	O6—C5—C6—N1	−160.66 (19)
N5—Zn1—O1—Zn2	−5.26 (15)	O5—C5—C6—N1	22.8 (3)
N4—Zn1—O1—Zn2	−84.59 (15)	C11—N2—C7—C8	−0.5 (3)
N7—Zn1—O1—Zn2	92.14 (15)	Zn2—N2—C7—C8	−168.38 (17)
O2—Zn1—O1—Zn2	−170.30 (17)	N2—C7—C8—C9	0.0 (4)
O5—Zn2—O1—C1	94.85 (15)	C7—C8—C9—C10	0.1 (3)
N2—Zn2—O1—C1	−174.18 (14)	C7—N2—C11—C10	0.8 (2)
O3—Zn2—O1—C1	−7.8 (2)	Zn2—N2—C11—C10	170.29 (8)
N3—Zn2—O1—C1	−95.96 (15)	C7—N2—C11—C15	−177.90 (16)
N1—Zn2—O1—C1	11.04 (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—C12	0.0
O3—Zn2—O1—Zn1	159.79 (12)	N2—C11—C10—C9	−0.67 (18)
N3—Zn2—O1—Zn1	71.60 (15)	C15—C11—C10—C9	178.04 (16)
N1—Zn2—O1—Zn1	178.60 (16)	C8—C9—C10—C11	0.2 (3)
N6—Zn1—O2—C1	169.03 (13)	C8—C9—C10—C12	178.18 (17)
N5—Zn1—O2—C1	−27.66 (19)	C11—C10—C12—C13	0.0
N4—Zn1—O2—C1	−90.83 (13)	C9—C10—C12—C13	−177.94 (17)
N7—Zn1—O2—C1	89.42 (13)	C10—C12—C13—C14	0.0
O1—Zn1—O2—C1	1.56 (12)	C12—C13—C14—C15	0.0
O5—Zn2—O3—C3	−104.52 (15)	C12—C13—C14—C16	−179.56 (17)
N2—Zn2—O3—C3	162.70 (15)	C18—N3—C15—C14	0.7 (2)
O1—Zn2—O3—C3	−4.5 (2)	Zn2—N3—C15—C14	−170.11 (8)
N3—Zn2—O3—C3	83.77 (15)	C18—N3—C15—C11	−178.76 (16)
N1—Zn2—O3—C3	−23.31 (15)	Zn2—N3—C15—C11	10.47 (16)
N2—Zn2—O5—C5	168.84 (16)	C13—C14—C15—N3	−179.41 (16)
O3—Zn2—O5—C5	74.29 (16)	C16—C14—C15—N3	0.16 (18)
O1—Zn2—O5—C5	−81.19 (15)	C13—C14—C15—C11	0.0
N3—Zn2—O5—C5	−152.4 (3)	C16—C14—C15—C11	179.57 (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—N3	179.44 (15)
O3—Zn2—N1—C2	153.47 (14)	N2—C11—C15—C14	178.75 (15)
O1—Zn2—N1—C2	−18.57 (13)	C10—C11—C15—C14	0.0
N3—Zn2—N1—C2	67.64 (14)	C15—C14—C16—C17	−0.8 (3)
O5—Zn2—N1—C4	129.76 (13)	C13—C14—C16—C17	178.72 (17)
O3—Zn2—N1—C4	29.58 (13)	C14—C16—C17—C18	0.7 (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—C17	167.69 (17)
O5—Zn2—N1—C6	13.47 (13)	C16—C17—C18—N3	0.2 (4)
O3—Zn2—N1—C6	−86.71 (13)	C23—N4—C19—C20	−0.5 (3)
O1—Zn2—N1—C6	101.26 (13)	Zn1—N4—C19—C20	171.66 (16)
N3—Zn2—N1—C6	−172.53 (13)	N4—C19—C20—C21	0.4 (3)
O5—Zn2—N2—C7	−8.24 (19)	C19—C20—C21—C22	1.2 (3)
O3—Zn2—N2—C7	90.45 (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—C7	179.0 (2)	C19—N4—C23—C27	179.55 (15)
O5—Zn2—N2—C11	−176.74 (13)	Zn1—N4—C23—C27	6.10 (15)
O3—Zn2—N2—C11	−78.06 (13)	N4—C23—C22—C24	−179.48 (15)
O1—Zn2—N2—C11	96.26 (13)	C27—C23—C22—C24	0.0
N3—Zn2—N2—C11	10.52 (13)	N4—C23—C22—C21	2.51 (18)
O5—Zn2—N3—C18	140.0 (3)	C27—C23—C22—C21	−178.01 (14)
N2—Zn2—N3—C18	179.6 (2)	C20—C21—C22—C23	−2.6 (3)
O3—Zn2—N3—C18	−86.0 (2)	C20—C21—C22—C24	179.42 (16)
O1—Zn2—N3—C18	69.1 (2)	C23—C22—C24—C25	0.0
N1—Zn2—N3—C18	−8.4 (2)	C21—C22—C24—C25	177.91 (15)
O5—Zn2—N3—C15	−50.8 (4)	C22—C24—C25—C26	0.0
N2—Zn2—N3—C15	−11.14 (12)	C24—C25—C26—C27	0.0
O3—Zn2—N3—C15	83.24 (13)	C24—C25—C26—C28	−179.3
O1—Zn2—N3—C15	−121.62 (13)	C30—N5—C27—C26	−1.5 (2)
N1—Zn2—N3—C15	160.84 (12)	Zn1—N5—C27—C26	175.52 (8)
N6—Zn1—N4—C19	66.7 (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—N5	1.56 (15)
N6—Zn1—N4—C23	−120.70 (13)	C25—C26—C27—C23	0.0
N5—Zn1—N4—C23	−5.48 (12)	C28—C26—C27—C23	179.4
O1—Zn1—N4—C23	88.58 (13)	N4—C23—C27—N5	−2.60 (14)
O2—Zn1—N4—C23	145.90 (13)	C22—C23—C27—N5	177.91 (14)
N6—Zn1—N5—C30	−82.8 (2)	N4—C23—C27—C26	179.50 (15)
N4—Zn1—N5—C30	−179.1 (2)	C22—C23—C27—C26	0.0
N7—Zn1—N5—C30	−1.3 (2)	C25—C26—C28—C29	178.78 (17)
O1—Zn1—N5—C30	91.5 (2)	C27—C26—C28—C29	−0.58 (17)
O2—Zn1—N5—C30	115.9 (2)	C26—C28—C29—C30	−0.4 (3)
N6—Zn1—N5—C27	100.57 (13)	C27—N5—C30—C29	0.5 (3)
N4—Zn1—N5—C27	4.21 (12)	Zn1—N5—C30—C29	−176.00 (18)
N7—Zn1—N5—C27	−177.95 (12)	C28—C29—C30—N5	0.5 (4)
O1—Zn1—N5—C27	−85.12 (12)	C35—N6—C31—C32	0.4 (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—C31	175.9 (2)	C31—N6—C35—C34	2.2 (2)
O1—Zn1—N6—C31	99.7 (2)	Zn1—N6—C35—C34	177.75 (8)
O2—Zn1—N6—C31	78.92 (19)	C31—N6—C35—C39	−179.28 (15)
N5—Zn1—N6—C35	93.61 (14)	Zn1—N6—C35—C39	−3.71 (15)
N4—Zn1—N6—C35	176.77 (12)	N6—C35—C34—C36	178.51 (15)
N7—Zn1—N6—C35	0.87 (13)	C39—C35—C34—C36	0.0
O1—Zn1—N6—C35	−75.31 (19)	N6—C35—C34—C33	−3.65 (18)
O2—Zn1—N6—C35	−96.13 (13)	C39—C35—C34—C33	177.84 (15)
N6—Zn1—N7—C42	−179.5 (2)	C32—C33—C34—C36	−179.55 (17)
N5—Zn1—N7—C42	64.8 (2)	C32—C33—C34—C35	2.7 (3)
O1—Zn1—N7—C42	−29.5 (2)	C35—C34—C36—C37	0.0
O2—Zn1—N7—C42	−86.9 (2)	C33—C34—C36—C37	−177.73 (15)
N6—Zn1—N7—C39	1.96 (12)	C34—C36—C37—C38	0.0
N5—Zn1—N7—C39	−113.67 (13)	C36—C37—C38—C39	0.0
O1—Zn1—N7—C39	152.00 (13)	C36—C37—C38—C40	177.4
O2—Zn1—N7—C39	94.59 (13)	C42—N7—C39—C38	1.1 (2)
Zn1—O2—C1—O1	−2.59 (19)	Zn1—N7—C39—C38	179.74 (8)
Zn1—O2—C1—C2	174.31 (18)	C42—N7—C39—C35	176.69 (16)
Zn1—O1—C1—O2	2.9 (2)	Zn1—N7—C39—C35	−4.64 (15)
Zn2—O1—C1—O2	176.23 (15)	C37—C38—C39—N7	175.52 (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—C35	0.0
C4—N1—C2—C1	141.89 (18)	C40—C38—C39—C35	−177.6
C6—N1—C2—C1	−90.9 (2)	N6—C35—C39—N7	5.71 (15)
Zn2—N1—C2—C1	23.7 (2)	C34—C35—C39—N7	−175.72 (14)
O2—C1—C2—N1	166.81 (19)	N6—C35—C39—C38	−178.57 (15)
O1—C1—C2—N1	−16.2 (3)	C34—C35—C39—C38	0.0
Zn2—O3—C3—O4	−167.15 (19)	C39—C38—C40—C41	1.44 (17)
Zn2—O3—C3—C4	10.7 (2)	C37—C38—C40—C41	−176.05 (17)
C2—N1—C4—C3	−153.33 (18)	C38—C40—C41—C42	0.1 (3)
C6—N1—C4—C3	78.7 (2)	C39—N7—C42—C41	0.6 (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—N1	16.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84	2.03	2.862 (3)	173
O1w—H12···O2w	0.84	1.87	2.706 (3)	179
O2w—H21···O3w	0.84	1.94	2.778 (3)	176
O2w—H22···O5wⁱ	0.84	1.92	2.731 (3)	162
O3w—H31···O9	0.84	2.00	2.803 (3)	160
O3w—H32···O1wⁱⁱ	0.84	1.89	2.732 (3)	173
O4w—H41···O4	0.84	1.95	2.768 (3)	165
O4w—H42···O7	0.84	2.16	2.989 (4)	167
O5w—H51···O6ⁱⁱⁱ	0.84	1.95	2.790 (2)	174
O5w—H52···O4w	0.84	1.92	2.750 (3)	173
O6w—H61···O6	0.85	1.95	2.797 (3)	174
O6w—H62···O6^iv	0.85	2.05	2.889 (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.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₆H₆NO₆)(C₁₂H₈N₂)₃]NO₃·6H₂O
M_r	1029.58
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	12.4729 (2), 15.2672 (2), 22.5295 (3)
β (°)	98.678 (1)
V (Å³)	4241.1 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.21
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.712, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	40047, 9739, 8382
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.100, 1.03
No. of reflections	9739
No. of parameters	562
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O1w—H11···O2	0.84	2.03	2.862 (3)	173
O1w—H12···O2w	0.84	1.87	2.706 (3)	179
O2w—H21···O3w	0.84	1.94	2.778 (3)	176
O2w—H22···O5wⁱ	0.84	1.92	2.731 (3)	162
O3w—H31···O9	0.84	2.00	2.803 (3)	160
O3w—H32···O1wⁱⁱ	0.84	1.89	2.732 (3)	173
O4w—H41···O4	0.84	1.95	2.768 (3)	165
O4w—H42···O7	0.84	2.16	2.989 (4)	167
O5w—H51···O6ⁱⁱⁱ	0.84	1.95	2.790 (2)	174
O5w—H52···O4w	0.84	1.92	2.750 (3)	173
O6w—H61···O6	0.85	1.95	2.797 (3)	174
O6w—H62···O6^iv	0.85	2.05	2.889 (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.

Acknowledgements

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

References

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Tang, X., Liang, F., Chen, J., Li, Y., Xu, Y. & Shen, W. (2007). Mater. Chem. Phys. 106, 159–163. Web of Science CSD CrossRef CAS Google Scholar
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