catena-Poly[[μ-5,5′-imino­ditetra­zolato-κ3N,N′:N′′-bis­[triaqua­zinc(II)]] bis­[[triaqua­zinc(II)]-μ-5,5′-imino­ditetra­zolato-κ3N,N′:N′′] dihydrate]

Liu, Z.-Q.; Dong, W.; Ng, S.W.

doi:10.1107/S160053680705578X

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catena-Poly[[μ-5,5′-iminoditetrazolato-κ³N,N′:N′′-bis[triaquazinc(II)]] bis[[triaquazinc(II)]-μ-5,5′-iminoditetrazolato-κ³N,N′:N′′] dihydrate]

Z.-Q. Liu, W. Dong and S. W. Ng

The title compound, {[Zn₂(C₂HN₉)₂(H₂O)₆][Zn₂(C₂HN₉)₂(H₂O)₆]·2H₂O}_n, consists of one dinuclear [Zn(C₂HN₉)(H₂O)₃]₂ molecule, in which the two C₂HN₉⁻ monoanions each N,N′-chelate a [Zn(H₂O)₃] unit while using a third N atom to bind to the other triaquazinc unit. In the second [Zn(C₂HN₉)(H₂O)₃] unit, the monoanion similarly N,N′-chelates a triaquazinc unit, but the bridging interaction furnishes a zigzag chain structure. For both Zn centres, a mer-ZnN₃O₃ octahedral coordination arises. A network of N—H

N, O—H

N and O—H

O hydrogen bonds helps to establish the structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705578X/hb2619sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680705578X/hb2619Isup2.hkl Contains datablock I

CCDC reference: 672614

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (N-N) = 0.003 Å
R factor = 0.020
wR factor = 0.054
Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.50 Ratio

Author Response: The diffraction measurements were sufficiently good for all H atoms to be refined; their temperature factors were also refined.


Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.38
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1   -H12     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O3   -H31     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.87(3), Rep   0.860(10) ......       3.00 su-Ra
              O4   -H41     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Ra
              O4   -H42     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.840(10) ......       3.00 su-Ra
              O8   -H8      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O1   -H12     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Ra
              O3   -H31     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(3), Rep   0.860(10) ......       3.00 su-Ra
              O4   -H41     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(3), Rep   0.860(10) ......       3.00 su-Ra
              O4   -H42     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.840(10) ......       3.00 su-Ra
              O8   -H8      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     1.99(3), Rep   2.000(10) ......       3.00 su-Ra
              H41  -N3      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.21(3), Rep   2.200(10) ......       3.00 su-Ra
              H61  -N6      1.555   3.565
PLAT736_ALERT_1_C H...A   Calc     2.14(3), Rep   2.150(10) ......       3.00 su-Ra
              H8   -N12     1.555   2.775

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               4048
           Count of symmetry unique reflns         2339
           Completeness (_total/calc)            173.07%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1709
           Fraction of Friedel pairs measured     0.731
           Are heavy atom types Z>Si present        yes
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1         (2)       1.93
PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn2         (2)       1.95
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         22

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  19 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

  16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Bis(5-tetrazolyl)amine is a high-nitrogen fuel; see Jones et al. (2006). Its synthesis in four steps, starting from cyanic chloride, is reported by Nedel'ko et al. (2005). The synthesis from sodium azide and sodium dicyanamide in water is reported by Marecek et al. (2004). For the crystal structures of the copper complexes, see Klapötke et al. (2006); Manfred et al. (2005). The structures of several metal derivatives have been deposited with the Cambridge Structural Database (Version 5.28, November 2006; Allen, 2002) as private communications. The title zinc derivative, (I), (Fig. 1) is readily synthesized from sodium azide, sodium dicyanamide and zinc chloride in a hydothermal reaction.

The complex structure of (I) consists of one dinuclear [Zn(C₂HN₉)₂(H₂O)₃]₂ moiety in which the two C₂HN₉^- monoanions each N,N'-chelate to a Zn(H₂O)₃ triaquazinc unit while using its third nitrogen atom to bind to the other triaquazinc unit. In the second Zn(C₂HN₉)₂(H₂O)₃ unit, the monoanion similarly N,N'-chelates to a triaquazinc unit, but the bridging interaction furnishes a zigzag chain structure (Fig. 1) For both zinc centres, a mer-ZnN₃O₃ octahedral coordination arises (Table 1). Two uncoordinated water molecules complete the structure. A complex network of N—H···N, O—H···N and O—H···O hydrogen bonds helps to establish the structure (Table 2).

Related literature top

For background literature on the ligand, see: Jones et al. (2006); Nedel'ko et al. (2005); Marecek et al. (2004). For related structures, see Klapötke et al. (2006); Manfred et al. (2005). For related literature, see: Allen (2002).

Experimental top

Zinc chloride (40.9 mg, 0.3 mmol), sodium azide (39.0 mg, 0.6 mmol), sodium dicyanamide (26.7 mg, 0.3 mmol) and water (10 ml) were heated in a 25-ml Teflon-lined, stainless-steel Parr bom at 433 K for 72 h. The bomb was then was cooled to room temperature at 10 K h^-1; the colourless blocks of (I) that formed were separated manually.

Computing details top

Data collection: SMART (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. View of a fragment of (I) depicting the coordination geometries of the two zinc atoms; displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. Symmetry codes as in Table 1.

catena-poly[µ-5,5'-iminoditetrazolato-κ³N,N':N''-bis[triaquazinc(II)] bis[[triaquazinc(II)]-µ-5,5'-iminoditetrazolato-κ³N,N':N''] dihydrate] top

Crystal data top

[Zn₂(C₂HN₉)₂(H₂O)₆][Zn₂(C₂HN₉)₂(H₂O)₆]·2H₂O	F(000) = 1128
M_r = 1118.18	D_x = 2.107 Mg m⁻³
Orthorhombic, P2₁2₁2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2ab	Cell parameters from 9121 reflections
a = 10.1201 (1) Å	θ = 1.7–27.5°
b = 23.7418 (3) Å	µ = 2.81 mm⁻¹
c = 7.3346 (1) Å	T = 295 K
V = 1762.28 (4) Å³	Block, colourless
Z = 2	0.32 × 0.17 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	4048 independent reflections
Radiation source: fine-focus sealed tube	3844 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.581, T_max = 0.850	k = −30→30
25915 measured reflections	l = −9→8

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.020	All H-atom parameters refined
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.0363P)²P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4048 reflections	Δρ_max = 0.29 e Å⁻³
345 parameters	Δρ_min = −0.43 e Å⁻³
22 restraints	Absolute structure: Flack (1983), with 1710 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.026 (8)

Crystal data top

[Zn₂(C₂HN₉)₂(H₂O)₆][Zn₂(C₂HN₉)₂(H₂O)₆]·2H₂O	V = 1762.28 (4) Å³
M_r = 1118.18	Z = 2
Orthorhombic, P2₁2₁2	Mo Kα radiation
a = 10.1201 (1) Å	µ = 2.81 mm⁻¹
b = 23.7418 (3) Å	T = 295 K
c = 7.3346 (1) Å	0.32 × 0.17 × 0.06 mm

Data collection top

Bruker APEXII CCD diffractometer	4048 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3844 reflections with I > 2σ(I)
T_min = 0.581, T_max = 0.850	R_int = 0.034
25915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	All H-atom parameters refined
wR(F²) = 0.054	Δρ_max = 0.29 e Å⁻³
S = 1.01	Δρ_min = −0.43 e Å⁻³
4048 reflections	Absolute structure: Flack (1983), with 1710 Friedel pairs
345 parameters	Absolute structure parameter: 0.026 (8)
22 restraints

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

	x	y	z	U_iso*/U_eq
Zn1	0.49499 (2)	0.66550 (1)	0.47415 (3)	0.01664 (6)
Zn2	0.36506 (2)	0.93580 (1)	0.01708 (3)	0.01744 (7)
O1	0.4922 (2)	0.6553 (1)	0.7651 (2)	0.0220 (3)
O2	0.6009 (2)	0.5884 (1)	0.4700 (3)	0.0289 (4)
O3	0.5257 (2)	0.6696 (1)	0.1956 (2)	0.0274 (4)
O4	0.3686 (2)	0.9250 (1)	0.3053 (2)	0.0290 (4)
O5	0.1591 (1)	0.9271 (1)	0.0271 (3)	0.0296 (4)
O6	0.3553 (2)	0.9439 (1)	−0.2721 (2)	0.0250 (3)
O7	1.0000	1.0000	−0.1726 (3)	0.0292 (5)
O8	1.0000	1.0000	0.3201 (3)	0.0287 (5)
N1	0.3582 (1)	0.7342 (1)	0.4689 (3)	0.0199 (4)
N2	0.3877 (2)	0.7884 (1)	0.4371 (3)	0.0286 (5)
N3	0.2826 (2)	0.8193 (1)	0.4451 (3)	0.0285 (5)
N4	0.1772 (2)	0.7861 (1)	0.4804 (3)	0.0194 (4)
N5	0.1544 (2)	0.6870 (1)	0.5283 (3)	0.0263 (4)
N6	0.1094 (2)	0.5914 (1)	0.4621 (3)	0.0265 (4)
N7	0.1864 (2)	0.5479 (1)	0.4106 (3)	0.0272 (4)
N8	0.3081 (2)	0.5631 (1)	0.3983 (3)	0.0240 (4)
N9	0.3177 (2)	0.6185 (1)	0.4429 (3)	0.0192 (4)
N10	0.5769 (2)	0.9319 (1)	0.0183 (3)	0.0175 (3)
N11	0.6602 (2)	0.9751 (1)	0.0585 (2)	0.0186 (4)
N12	0.7751 (2)	0.9552 (1)	0.1032 (3)	0.0225 (4)
N13	0.7735 (2)	0.8986 (1)	0.0949 (3)	0.0223 (4)
N14	0.6126 (2)	0.8310 (1)	0.0127 (3)	0.0262 (4)
N15	0.4512 (2)	0.7600 (1)	−0.0351 (3)	0.0270 (4)
N16	0.3182 (2)	0.7617 (1)	−0.0593 (3)	0.0277 (5)
N17	0.2775 (2)	0.8133 (1)	−0.0559 (3)	0.0269 (4)
N18	0.3817 (2)	0.8482 (1)	−0.0277 (3)	0.0215 (4)
C1	0.22764 (2)	0.7341 (1)	0.4936 (3)	0.0168 (4)
C2	0.19376 (2)	0.6338 (1)	0.4795 (3)	0.0191 (4)
C3	0.65014 (2)	0.8860 (1)	0.0409 (3)	0.0178 (4)
C4	0.48487 (2)	0.8141 (1)	−0.0158 (3)	0.0188 (4)
H5	0.073 (1)	0.691 (1)	0.543 (4)	0.03 (1)*
H14	0.671 (2)	0.807 (1)	0.025 (3)	0.02 (1)*
H11	0.423 (2)	0.641 (1)	0.810 (4)	0.04 (1)*
H12	0.505 (3)	0.688 (1)	0.807 (4)	0.05 (1)*
H21	0.667 (2)	0.580 (1)	0.406 (4)	0.08 (1)*
H22	0.571 (2)	0.560 (1)	0.526 (3)	0.04 (1)*
H31	0.496 (3)	0.702 (1)	0.167 (5)	0.08 (1)*
H32	0.608 (1)	0.669 (1)	0.173 (4)	0.05 (1)*
H41	0.333 (3)	0.894 (1)	0.343 (5)	0.09 (2)*
H42	0.448 (2)	0.927 (2)	0.345 (6)	0.11 (2)*
H51	0.119 (2)	0.905 (1)	0.095 (3)	0.04 (1)*
H52	0.112 (2)	0.946 (1)	−0.043 (3)	0.03 (1)*
H61	0.429 (2)	0.931 (1)	−0.310 (5)	0.10 (2)*
H62	0.345 (3)	0.977 (1)	−0.320 (4)	0.04 (1)*
H7	1.055 (2)	1.018 (1)	−0.236 (4)	0.05 (1)*
H8	1.066 (2)	1.007 (2)	0.253 (4)	0.06 (1)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0119 (1)	0.0156 (1)	0.0225 (1)	0.0007 (1)	0.0007 (1)	0.0002 (1)
Zn2	0.0152 (1)	0.0136 (1)	0.0236 (1)	0.0002 (1)	−0.0010 (1)	0.0002 (1)
O1	0.021 (1)	0.021 (1)	0.025 (1)	−0.005 (1)	0.004 (1)	−0.001 (1)
O2	0.022 (1)	0.019 (1)	0.046 (1)	0.004 (1)	0.006 (1)	0.002 (1)
O3	0.023 (1)	0.033 (1)	0.026 (1)	0.005 (1)	0.005 (1)	0.003 (1)
O4	0.034 (1)	0.029 (1)	0.024 (1)	−0.005 (1)	0.000 (1)	0.005 (1)
O5	0.016 (1)	0.024 (1)	0.049 (1)	−0.002 (1)	0.001 (1)	0.007 (1)
O6	0.029 (1)	0.022 (1)	0.023 (1)	0.005 (7)	−0.001 (1)	0.003 (1)
O7	0.024 (1)	0.032 (1)	0.031 (1)	−0.004 (1)	0.000	0.000
O8	0.025 (1)	0.031 (1)	0.030 (1)	−0.003 (1)	0.000	0.000
N1	0.011 (1)	0.015 (1)	0.033 (1)	0.000 (1)	0.001 (1)	0.000 (1)
N2	0.014 (1)	0.016 (1)	0.056 (1)	0.001 (1)	0.003 (1)	0.004 (1)
N3	0.014 (1)	0.018 (1)	0.053 (1)	0.000 (1)	0.004 (1)	0.006 (1)
N4	0.013 (1)	0.015 (1)	0.031 (1)	−0.001 (1)	0.000 (1)	0.001 (1)
N5	0.011 (1)	0.015 (1)	0.053 (1)	0.002 (1)	0.008 (1)	−0.001 (1)
N6	0.016 (1)	0.019 (1)	0.045 (1)	−0.002 (1)	−0.001 (1)	−0.002 (1)
N7	0.019 (1)	0.019 (1)	0.044 (1)	−0.002 (1)	−0.001 (1)	−0.009 (1)
N8	0.020 (1)	0.019 (1)	0.033 (1)	0.000 (1)	0.001 (1)	−0.006 (1)
N9	0.014 (1)	0.015 (1)	0.029 (1)	0.001 (1)	0.000 (1)	−0.004 (1)
N10	0.015 (1)	0.012 (1)	0.026 (1)	−0.001 (1)	−0.002 (1)	0.000 (1)
N11	0.015 (1)	0.015 (1)	0.025 (1)	0.000 (1)	−0.002 (1)	0.001 (1)
N12	0.018 (1)	0.016 (1)	0.034 (1)	0.001 (1)	−0.006 (1)	0.002 (1)
N13	0.016 (1)	0.016 (1)	0.035 (1)	−0.001 (1)	−0.005 (1)	0.001 (1)
N14	0.015 (1)	0.012 (1)	0.052 (1)	0.002 (1)	−0.008 (1)	−0.002 (1)
N15	0.021 (1)	0.014 (1)	0.046 (1)	0.000 (1)	−0.006 (1)	−0.001 (1)
N16	0.019 (1)	0.014 (1)	0.050 (1)	−0.002 (1)	−0.007 (1)	−0.002 (1)
N17	0.019 (1)	0.018 (1)	0.044 (1)	−0.003 (1)	−0.007 (1)	−0.002 (1)
N18	0.018 (1)	0.017 (1)	0.030 (1)	−0.001 (1)	−0.004 (1)	−0.002 (1)
C1	0.011 (1)	0.017 (1)	0.022 (1)	0.002 (1)	0.000 (1)	0.000 (1)
C2	0.014 (1)	0.017 (1)	0.026 (1)	0.001 (1)	0.001 (1)	0.000 (1)
C3	0.016 (1)	0.016 (1)	0.022 (1)	0.000 (1)	−0.002 (1)	0.000 (1)
C4	0.018 (1)	0.014 (1)	0.024 (1)	−0.001 (1)	−0.003 (1)	−0.001 (1)

Geometric parameters (Å, º) top

Zn1—O2	2.122 (2)	N10—N11	1.360 (2)
Zn1—O1	2.148 (2)	N11—N12	1.297 (2)
Zn1—O3	2.069 (2)	N12—N13	1.345 (2)
Zn1—N1	2.140 (2)	N13—C3	1.343 (3)
Zn1—N4ⁱ	2.199 (2)	N14—C4	1.369 (2)
Zn1—N9	2.125 (2)	N14—C3	1.375 (3)
Zn2—O4	2.130 (2)	N15—C4	1.336 (2)
Zn2—O5	2.096 (1)	N15—N16	1.359 (2)
Zn2—O6	2.132 (2)	N16—N17	1.291 (2)
Zn2—N10	2.146 (2)	N17—N18	1.357 (2)
Zn2—N11ⁱⁱ	2.152 (2)	N18—C4	1.324 (2)
Zn2—N18	2.113 (2)	O1—H11	0.85 (1)
N1—C1	1.334 (2)	O1—H12	0.85 (1)
N1—N2	1.341 (2)	O2—H21	0.84 (1)
N2—N3	1.293 (2)	O2—H22	0.84 (1)
N3—N4	1.351 (2)	O3—H31	0.85 (1)
N4—C1	1.338 (2)	O3—H32	0.85 (1)
N5—C1	1.366 (2)	O4—H41	0.86 (1)
N5—C2	1.371 (2)	O4—H42	0.86 (1)
N6—C2	1.326 (3)	O5—H51	0.82 (1)
N6—N7	1.350 (2)	O5—H52	0.83 (1)
N7—N8	1.287 (3)	O6—H61	0.86 (1)
N8—N9	1.360 (2)	O6—H62	0.86 (1)
N9—C2	1.333 (2)	O7—H7	0.84 (1)
N10—C3	1.329 (2)	O8—H8	0.84 (1)

O3—Zn1—O2	87.17 (7)	N11—N10—Zn2	126.0 (2)
O3—Zn1—N9	92.61 (7)	N12—N11—N10	109.6 (2)
O2—Zn1—N9	88.41 (6)	N12—N11—Zn2ⁱⁱ	120.1 (1)
O3—Zn1—N1	92.48 (7)	N10—N11—Zn2ⁱⁱ	129.6 (1)
O2—Zn1—N1	169.88 (6)	N11—N12—N13	110.0 (2)
N9—Zn1—N1	81.50 (6)	C3—N13—N12	104.3 (2)
O3—Zn1—O1	171.28 (6)	C4—N14—C3	124.2 (2)
O2—Zn1—O1	85.62 (7)	C4—N15—N16	103.7 (2)
N9—Zn1—O1	92.09 (6)	N17—N16—N15	110.1 (2)
N1—Zn1—O1	95.47 (7)	N16—N17—N18	109.5 (2)
O3—Zn1—N4ⁱ	89.94 (7)	C4—N18—N17	104.5 (2)
O2—Zn1—N4ⁱ	91.70 (6)	C4—N18—Zn2	130.8 (1)
N9—Zn1—N4ⁱ	177.45 (7)	N17—N18—Zn2	124.3 (1)
N1—Zn1—N4ⁱ	98.42 (6)	N1—C1—N4	111.5 (2)
O1—Zn1—N4ⁱ	85.38 (7)	N1—C1—N5	124.3 (2)
O5—Zn2—N18	89.26 (6)	N4—C1—N5	124.2 (2)
O5—Zn2—O4	88.29 (7)	N6—C2—N9	112.3 (2)
N18—Zn2—O4	91.94 (7)	N6—C2—N5	122.5 (2)
O5—Zn2—O6	89.87 (7)	N9—C2—N5	125.2 (2)
N18—Zn2—O6	86.46 (7)	N10—C3—N13	111.9 (2)
O4—Zn2—O6	177.58 (6)	N10—C3—N14	127.3 (2)
O5—Zn2—N10	171.56 (6)	N13—C3—N14	120.8 (2)
N18—Zn2—N10	83.05 (6)	N18—C4—N15	112.3 (2)
O4—Zn2—N10	88.49 (7)	N18—C4—N14	125.1 (2)
O6—Zn2—N10	93.12 (7)	N15—C4—N14	122.6 (2)
O5—Zn2—N11ⁱⁱ	88.51 (6)	Zn1—O1—H11	116 (2)
N18—Zn2—N11ⁱⁱ	177.60 (6)	Zn1—O1—H12	105 (2)
O4—Zn2—N11ⁱⁱ	88.90 (7)	H11—O1—H12	112 (2)
O6—Zn2—N11ⁱⁱ	92.63 (6)	Zn1—O2—H21	128 (2)
N10—Zn2—N11ⁱⁱ	99.22 (6)	Zn1—O2—H22	120 (2)
C1—N1—N2	104.2 (2)	H21—O2—H22	111 (2)
C1—N1—Zn1	129.6 (1)	Zn1—O3—H31	103 (3)
N2—N1—Zn1	126.2 (1)	Zn1—O3—H32	110 (2)
N3—N2—N1	110.6 (2)	H31—O3—H32	108 (2)
N2—N3—N4	109.2 (2)	Zn2—O4—H41	114 (3)
C1—N4—N3	104.5 (2)	Zn2—O4—H42	111 (3)
C1—N4—Zn1ⁱⁱⁱ	142.3 (1)	H41—O4—H42	109 (2)
N3—N4—Zn1ⁱⁱⁱ	112.7 (1)	Zn2—O5—H51	125 (2)
C1—N5—C2	123.2 (2)	Zn2—O5—H52	120 (2)
C2—N6—N7	103.7 (2)	H51—O5—H52	116 (2)
N8—N7—N6	110.9 (2)	Zn2—O6—H61	104 (3)
N7—N8—N9	108.9 (2)	Zn2—O6—H62	120 (2)
C2—N9—N8	104.2 (2)	H61—O6—H62	108 (2)
C2—N9—Zn1	129.0 (1)	C1—N5—H5	118 (2)
N8—N9—Zn1	126.4 (1)	C2—N5—H5	115 (2)
C3—N10—N11	104.3 (2)	C4—N14—H14	119 (2)
C3—N10—Zn2	126.4 (1)	C3—N14—H14	116 (2)

O3—Zn1—N1—C1	109.4 (2)	N16—N17—N18—C4	0.3 (3)
O2—Zn1—N1—C1	21.6 (6)	N16—N17—N18—Zn2	−173.2 (2)
N9—Zn1—N1—C1	17.11 (19)	O5—Zn2—N18—C4	−164.9 (2)
O1—Zn1—N1—C1	−74.2 (2)	O4—Zn2—N18—C4	−76.6 (2)
N4ⁱ—Zn1—N1—C1	−160.3 (2)	O6—Zn2—N18—C4	105.2 (2)
O3—Zn1—N1—N2	−69.9 (2)	N10—Zn2—N18—C4	11.6 (2)
O2—Zn1—N1—N2	−157.8 (4)	O5—Zn2—N18—N17	6.7 (2)
N9—Zn1—N1—N2	−162.2 (2)	O4—Zn2—N18—N17	95.0 (2)
O1—Zn1—N1—N2	106.5 (2)	O6—Zn2—N18—N17	−83.2 (2)
N4ⁱ—Zn1—N1—N2	20.4 (2)	N10—Zn2—N18—N17	−176.8 (2)
C1—N1—N2—N3	1.1 (3)	N2—N1—C1—N4	−0.8 (3)
Zn1—N1—N2—N3	−179.5 (2)	Zn1—N1—C1—N4	179.8 (2)
N1—N2—N3—N4	−1.0 (3)	N2—N1—C1—N5	179.3 (2)
N2—N3—N4—C1	0.4 (3)	Zn1—N1—C1—N5	−0.2 (3)
N2—N3—N4—Zn1ⁱⁱⁱ	174.0 (2)	N3—N4—C1—N1	0.3 (3)
C2—N6—N7—N8	0.1 (3)	Zn1ⁱⁱⁱ—N4—C1—N1	−170.0 (2)
N6—N7—N8—N9	0.3 (3)	N3—N4—C1—N5	−179.8 (2)
N7—N8—N9—C2	−0.6 (2)	Zn1ⁱⁱⁱ—N4—C1—N5	9.9 (4)
N7—N8—N9—Zn1	173.3 (2)	C2—N5—C1—N1	−24.1 (4)
O3—Zn1—N9—C2	−112.6 (2)	C2—N5—C1—N4	156.0 (2)
O2—Zn1—N9—C2	160.3 (2)	N7—N6—C2—N9	−0.5 (3)
N1—Zn1—N9—C2	−20.5 (2)	N7—N6—C2—N5	179.0 (2)
O1—Zn1—N9—C2	74.7 (2)	N8—N9—C2—N6	0.7 (3)
O3—Zn1—N9—N8	75.0 (2)	Zn1—N9—C2—N6	−173.0 (2)
O2—Zn1—N9—N8	−12.1 (2)	N8—N9—C2—N5	−178.8 (2)
N1—Zn1—N9—N8	167.1 (2)	Zn1—N9—C2—N5	7.5 (3)
O1—Zn1—N9—N8	−97.7 (2)	C1—N5—C2—N6	−159.0 (2)
N18—Zn2—N10—C3	−17.7 (2)	C1—N5—C2—N9	20.4 (4)
O4—Zn2—N10—C3	74.4 (2)	N11—N10—C3—N13	0.8 (2)
O6—Zn2—N10—C3	−103.8 (2)	Zn2—N10—C3—N13	−159.4 (2)
N11ⁱⁱ—Zn2—N10—C3	163.0 (2)	N11—N10—C3—N14	−178.3 (2)
N18—Zn2—N10—N11	−173.7 (2)	Zn2—N10—C3—N14	21.6 (3)
O4—Zn2—N10—N11	−81.6 (2)	N12—N13—C3—N10	−0.7 (3)
O6—Zn2—N10—N11	100.3 (2)	N12—N13—C3—N14	178.4 (2)
N11ⁱⁱ—Zn2—N10—N11	7.1 (2)	C4—N14—C3—N10	−11.1 (4)
C3—N10—N11—N12	−0.5 (2)	C4—N14—C3—N13	169.9 (2)
Zn2—N10—N11—N12	159.7 (2)	N17—N18—C4—N15	0.1 (3)
C3—N10—N11—Zn2ⁱⁱ	169.1 (2)	Zn2—N18—C4—N15	172.9 (2)
Zn2—N10—N11—Zn2ⁱⁱ	−30.7 (2)	N17—N18—C4—N14	180.0 (2)
N10—N11—N12—N13	0.1 (2)	Zn2—N18—C4—N14	−7.1 (4)
Zn2ⁱⁱ—N11—N12—N13	−170.7 (1)	N16—N15—C4—N18	−0.4 (3)
N11—N12—N13—C3	0.4 (2)	N16—N15—C4—N14	179.7 (2)
C4—N15—N16—N17	0.6 (3)	C3—N14—C4—N18	3.0 (4)
N15—N16—N17—N18	−0.5 (3)	C3—N14—C4—N15	−177.1 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, −y+2, z; (iii) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N2ⁱⁱⁱ	0.84 (1)	1.94 (1)	2.773 (2)	171 (3)
N14—H14···N16^iv	0.82 (1)	2.23 (1)	3.049 (2)	176 (2)
O1—H11···N13ⁱⁱⁱ	0.85 (1)	1.91 (1)	2.754 (2)	175 (2)
O1—H12···N15^v	0.85 (1)	2.14 (2)	2.915 (2)	153 (2)
O2—H21···O6^iv	0.84 (1)	2.22 (1)	3.053 (2)	172 (4)
O2—H22···O8ⁱⁱⁱ	0.84 (1)	1.96 (1)	2.796 (2)	173 (3)
O3—H31···N15	0.85 (1)	2.07 (2)	2.835 (3)	148 (3)
O3—H32···N17^iv	0.85 (1)	1.96 (1)	2.776 (2)	160 (3)
O4—H41···N3	0.86 (1)	2.00 (1)	2.847 (2)	169 (3)
O4—H42···N6ⁱ	0.86 (1)	2.20 (2)	3.000 (3)	155 (3)
O5—H51···O1ⁱⁱⁱ	0.82 (1)	2.19 (1)	3.000 (2)	170 (2)
O5—H52···O7^vi	0.83 (1)	1.96 (1)	2.781 (2)	169 (3)
O6—H61···N6^iv	0.86 (1)	2.20 (1)	3.042 (3)	167 (3)
O6—H62···N7^vii	0.86 (1)	1.84 (1)	2.701 (2)	176 (3)
O7—H7···N8^viii	0.84 (1)	2.12 (1)	2.959 (2)	179 (3)
O8—H8···N12^ix	0.84 (1)	2.15 (1)	2.974 (2)	166 (4)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (iii) x−1/2, −y+3/2, −z+1; (iv) x+1/2, −y+3/2, −z; (v) x, y, z+1; (vi) x−1, y, z; (vii) −x+1/2, y+1/2, −z; (viii) −x+3/2, y+1/2, −z; (ix) −x+2, −y+2, z.

Experimental details

Crystal data
Chemical formula	[Zn₂(C₂HN₉)₂(H₂O)₆][Zn₂(C₂HN₉)₂(H₂O)₆]·2H₂O
M_r	1118.18
Crystal system, space group	Orthorhombic, P2₁2₁2
Temperature (K)	295
a, b, c (Å)	10.1201 (1), 23.7418 (3), 7.3346 (1)
V (Å³)	1762.28 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.81
Crystal size (mm)	0.32 × 0.17 × 0.06

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.581, 0.850
No. of measured, independent and observed [I > 2σ(I)] reflections	25915, 4048, 3844
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.054, 1.01
No. of reflections	4048
No. of parameters	345
No. of restraints	22
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.43
Absolute structure	Flack (1983), with 1710 Friedel pairs
Absolute structure parameter	0.026 (8)

Computer programs: SMART (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Selected bond lengths (Å) top

Zn1—O2	2.122 (2)	Zn2—O4	2.130 (2)
Zn1—O1	2.148 (2)	Zn2—O5	2.096 (1)
Zn1—O3	2.069 (2)	Zn2—O6	2.132 (2)
Zn1—N1	2.140 (2)	Zn2—N10	2.146 (2)
Zn1—N4ⁱ	2.199 (2)	Zn2—N11ⁱⁱ	2.152 (2)
Zn1—N9	2.125 (2)	Zn2—N18	2.113 (2)

Symmetry codes: (i) x+1/2, −y+3/2, −z+1; (ii) −x+1, −y+2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N2ⁱⁱⁱ	0.84 (1)	1.94 (1)	2.773 (2)	171 (3)
N14—H14···N16^iv	0.82 (1)	2.23 (1)	3.049 (2)	176 (2)
O1—H11···N13ⁱⁱⁱ	0.85 (1)	1.91 (1)	2.754 (2)	175 (2)
O1—H12···N15^v	0.85 (1)	2.14 (2)	2.915 (2)	153 (2)
O2—H21···O6^iv	0.84 (1)	2.22 (1)	3.053 (2)	172 (4)
O2—H22···O8ⁱⁱⁱ	0.84 (1)	1.96 (1)	2.796 (2)	173 (3)
O3—H31···N15	0.85 (1)	2.07 (2)	2.835 (3)	148 (3)
O3—H32···N17^iv	0.85 (1)	1.96 (1)	2.776 (2)	160 (3)
O4—H41···N3	0.86 (1)	2.00 (1)	2.847 (2)	169 (3)
O4—H42···N6ⁱ	0.86 (1)	2.20 (2)	3.000 (3)	155 (3)
O5—H51···O1ⁱⁱⁱ	0.82 (1)	2.19 (1)	3.000 (2)	170 (2)
O5—H52···O7^vi	0.83 (1)	1.96 (1)	2.781 (2)	169 (3)
O6—H61···N6^iv	0.86 (1)	2.20 (1)	3.042 (3)	167 (3)
O6—H62···N7^vii	0.86 (1)	1.84 (1)	2.701 (2)	176 (3)
O7—H7···N8^viii	0.84 (1)	2.12 (1)	2.959 (2)	179 (3)
O8—H8···N12^ix	0.84 (1)	2.15 (1)	2.974 (2)	166 (4)

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