[4-Carboxy­imidazole-5-carboxyl­ato(2–)-κ2N1,O5](5,5,7,12,12,14-hexa­methyl-1,4,8,11-tetra­azacyclo­tetra­decane-κ4N,N′,N′′,N′′′)nickel(II) monohydrate

Ou, G.-C.; Zhou, Q.; Ng, S.W.

doi:10.1107/S1600536809046145

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1556

doi:10.1107/S1600536809046145

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[4-Carboxyimidazole-5-carboxylato(2–)-κ²N¹,O⁵](5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ⁴N,N′,N′′,N′′′)nickel(II) monohydrate

Guang-Chuan Ou,^a Qiang Zhou ^a and Seik Weng Ng ^b ^*

^aDepartment of Biology and Chemistry, Hunan University of Science and Engineering, Yongzhou, Hunan 425100, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 2 November 2009; accepted 2 November 2009; online 11 November 2009)

The 4-carboxyimidazole-5-carboxylate(2−) dianion in the title compound, [Ni(C₅H₂N₂O₄)(C₁₆H₃₆N₄)]·H₂O, N,O′-chelates to the Ni^II atom, which shows an octahedral coordination. The macrocycle folds itself around the metal atom and binds to it through four secondary nitrogen atoms; adjacent molecules are linked by N—H⋯O hydrogen bonds into a linear chain. The water molecule is disordered over two positions.

Related literature

For the crystal structures of other nickel salts of the macrocycle, see: Ou et al. (2009a ,b ).

Experimental

Crystal data

[Ni(C₅H₂N₂O₄)(C₁₆H₃₆N₄)]·H₂O
M_r = 515.30
Monoclinic, P 2₁ /c
a = 10.4070 (8) Å
b = 12.7806 (10) Å
c = 19.0947 (14) Å
β = 103.675 (1)°
V = 2467.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 295 K
0.42 × 0.36 × 0.12 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.767, T_max = 0.905
10408 measured reflections
4308 independent reflections
2809 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.163
S = 1.04
4308 reflections
309 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; 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 I, global. DOI: 10.1107/S1600536809046145/xu2666sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046145/xu2666Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of other nickel salts of the macrocycle, see: Ou et al. (2009a,b).

Experimental top

Imidazole-4,5-dicarboxylic acid (0.156 g, 1 mmol) and sodium hydroxide (0.080 g, 2 mmol) were dissolved in water (5 ml). To this solution was added (5,5,7,12,12,14 -hexamethyl-1,4,8,11-tetraazacyclotetradecane)nickel perchlorate (0.54 g, 1 mmol) dissolved in acetonitrile (10 ml). The solution was left to stand at room temperature; blue crystals formed after several weeks.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); 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. Thermal ellipsoid plot (Barbour, 2001) of Ni(C₁₆H₃₆N₄)(C₅H₂N₂O₄).H₂O showing displacement ellipsoids of the 50% probability level. H-atoms are drawn as spheres of arbitrary radii.

[4-Carboxyimidazole-5-carboxylato(2-)- κ²N¹,O⁵](5,5,7,12,12,14-hexamethyl-1,4,8,11- tetraazacyclotetradecane- κ⁴N,N',N'',N''')nickel(II) monohydrate top

Crystal data top

[Ni(C₅H₂N₂O₄)(C₁₆H₃₆N₄)]·H₂O	F(000) = 1104
M_r = 515.30	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2768 reflections
a = 10.4070 (8) Å	θ = 2.6–24.5°
b = 12.7806 (10) Å	µ = 0.83 mm⁻¹
c = 19.0947 (14) Å	T = 295 K
β = 103.675 (1)°	Block, blue
V = 2467.7 (3) Å³	0.42 × 0.36 × 0.12 mm
Z = 4

Data collection top

Bruker SMART area-detector diffractometer	4308 independent reflections
Radiation source: fine-focus sealed tube	2809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.767, T_max = 0.905	k = −15→6
10408 measured reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0959P)² + 0.1761P] where P = (F_o² + 2F_c²)/3
4308 reflections	(Δ/σ)_max = 0.001
309 parameters	Δρ_max = 0.70 e Å⁻³
12 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[Ni(C₅H₂N₂O₄)(C₁₆H₃₆N₄)]·H₂O	V = 2467.7 (3) Å³
M_r = 515.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.4070 (8) Å	µ = 0.83 mm⁻¹
b = 12.7806 (10) Å	T = 295 K
c = 19.0947 (14) Å	0.42 × 0.36 × 0.12 mm
β = 103.675 (1)°

Data collection top

Bruker SMART area-detector diffractometer	4308 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2809 reflections with I > 2σ(I)
T_min = 0.767, T_max = 0.905	R_int = 0.046
10408 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	12 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	Δρ_max = 0.70 e Å⁻³
4308 reflections	Δρ_min = −0.36 e Å⁻³
309 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ni1	0.30812 (5)	0.45585 (4)	0.28750 (3)	0.0245 (2)
O1	0.4614 (3)	0.5510 (3)	0.34989 (16)	0.0336 (8)
O2	0.6725 (3)	0.5949 (3)	0.36493 (17)	0.0376 (8)
O3	0.8653 (3)	0.5250 (3)	0.3258 (2)	0.0538 (11)
H3O	0.7997	0.5424	0.3417	0.081*
O4	0.9127 (4)	0.4070 (3)	0.2526 (3)	0.0829 (16)
O1W	0.7320 (8)	0.3543 (8)	0.0802 (4)	0.073 (3)	0.601 (16)
H1W1	0.7148	0.4042	0.1052	0.110*	0.601 (16)
H1W2	0.6820	0.3546	0.0387	0.110*	0.601 (16)
O1W'	0.7294 (15)	0.4398 (15)	0.0802 (7)	0.091 (6)	0.399 (16)
H1W3	0.7297	0.4873	0.1107	0.136*	0.399 (16)
H1W4	0.6785	0.4513	0.0397	0.136*	0.399 (16)
N1	0.4737 (3)	0.3997 (3)	0.2535 (2)	0.0305 (9)
N2	0.6458 (4)	0.3371 (3)	0.2133 (2)	0.0426 (11)
N3	0.1845 (3)	0.5172 (3)	0.35147 (19)	0.0278 (9)
H3N	0.1082	0.4879	0.3381	0.033*
N4	0.2535 (4)	0.5960 (3)	0.22445 (19)	0.0298 (9)
H4N	0.3176	0.6389	0.2400	0.036*
N5	0.1663 (3)	0.3764 (3)	0.20915 (18)	0.0267 (9)
H5N	0.0897	0.3956	0.2140	0.032*
N6	0.3160 (3)	0.3119 (3)	0.34868 (19)	0.0303 (9)
H6N	0.3832	0.2783	0.3413	0.036*
C1	0.5726 (4)	0.5398 (4)	0.3369 (2)	0.0304 (11)
C2	0.5852 (4)	0.4563 (3)	0.2869 (2)	0.0261 (10)
C3	0.6903 (5)	0.4169 (4)	0.2603 (3)	0.0380 (12)
C4	0.8316 (5)	0.4491 (4)	0.2793 (3)	0.0464 (14)
C5	0.5175 (4)	0.3311 (4)	0.2119 (3)	0.0360 (12)
H5	0.4620	0.2821	0.1839	0.043*
C6	0.1697 (4)	0.6284 (4)	0.3314 (3)	0.0337 (11)
H6A	0.2505	0.6657	0.3531	0.040*
H6B	0.0982	0.6587	0.3492	0.040*
C7	0.1404 (4)	0.6395 (4)	0.2504 (2)	0.0332 (11)
H7A	0.0600	0.6019	0.2284	0.040*
H7B	0.1279	0.7127	0.2371	0.040*
C8	0.2339 (4)	0.5968 (4)	0.1448 (2)	0.0346 (12)
C9	0.3679 (5)	0.5815 (4)	0.1280 (3)	0.0444 (13)
H9A	0.4262	0.6369	0.1497	0.067*
H9B	0.3582	0.5825	0.0767	0.067*
H9C	0.4043	0.5155	0.1469	0.067*
C10	0.1777 (5)	0.7000 (4)	0.1105 (3)	0.0493 (14)
H10A	0.2363	0.7561	0.1303	0.074*
H10B	0.0925	0.7121	0.1202	0.074*
H10C	0.1688	0.6966	0.0593	0.074*
C11	0.1364 (5)	0.5088 (4)	0.1118 (2)	0.0375 (12)
H11A	0.0524	0.5245	0.1232	0.045*
H11B	0.1224	0.5134	0.0598	0.045*
C12	0.1699 (4)	0.3955 (4)	0.1330 (2)	0.0331 (11)
H12	0.2603	0.3823	0.1284	0.040*
C13	0.0766 (5)	0.3224 (4)	0.0799 (3)	0.0425 (13)
H13A	0.0981	0.2510	0.0931	0.064*
H13B	0.0870	0.3346	0.0320	0.064*
H13C	−0.0132	0.3362	0.0817	0.064*
C14	0.1822 (4)	0.2652 (4)	0.2291 (2)	0.0319 (11)
H14A	0.2589	0.2371	0.2150	0.038*
H14B	0.1050	0.2264	0.2038	0.038*
C15	0.1992 (4)	0.2524 (4)	0.3093 (2)	0.0353 (11)
H15A	0.1207	0.2775	0.3230	0.042*
H15B	0.2102	0.1789	0.3219	0.042*
C16	0.3346 (5)	0.3134 (4)	0.4296 (3)	0.0367 (12)
C17	0.4744 (5)	0.3503 (4)	0.4619 (3)	0.0428 (13)
H17A	0.4866	0.4188	0.4439	0.064*
H17B	0.5361	0.3026	0.4488	0.064*
H17C	0.4892	0.3527	0.5134	0.064*
C18	0.3178 (5)	0.2034 (4)	0.4592 (3)	0.0491 (14)
H18A	0.3817	0.1568	0.4471	0.074*
H18B	0.2303	0.1780	0.4382	0.074*
H18C	0.3309	0.2067	0.5106	0.074*
C19	0.2315 (5)	0.3859 (4)	0.4496 (2)	0.0375 (12)
H19A	0.1447	0.3588	0.4267	0.045*
H19B	0.2410	0.3808	0.5012	0.045*
C20	0.2335 (4)	0.5008 (4)	0.4307 (2)	0.0318 (11)
H20	0.3255	0.5248	0.4445	0.038*
C21	0.1539 (5)	0.5646 (4)	0.4740 (3)	0.0475 (14)
H21A	0.1891	0.5531	0.5245	0.071*
H21B	0.0630	0.5431	0.4610	0.071*
H21C	0.1598	0.6377	0.4634	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0140 (3)	0.0301 (3)	0.0302 (3)	−0.0013 (2)	0.0066 (2)	−0.0022 (3)
O1	0.0243 (17)	0.048 (2)	0.0290 (17)	−0.0063 (15)	0.0068 (13)	−0.0025 (15)
O2	0.0233 (18)	0.045 (2)	0.0416 (19)	−0.0127 (15)	0.0028 (14)	0.0012 (16)
O3	0.0214 (18)	0.044 (2)	0.097 (3)	−0.0017 (17)	0.015 (2)	0.006 (2)
O4	0.031 (2)	0.055 (3)	0.174 (5)	−0.006 (2)	0.047 (3)	−0.025 (3)
O1W	0.091 (5)	0.066 (7)	0.076 (5)	0.014 (4)	0.047 (4)	−0.015 (4)
O1W'	0.117 (9)	0.092 (11)	0.081 (7)	−0.016 (7)	0.058 (6)	0.004 (6)
N1	0.020 (2)	0.036 (2)	0.037 (2)	0.0031 (17)	0.0096 (17)	0.0019 (19)
N2	0.026 (2)	0.035 (2)	0.073 (3)	0.0018 (18)	0.025 (2)	−0.005 (2)
N3	0.0220 (19)	0.033 (2)	0.031 (2)	−0.0021 (16)	0.0121 (16)	−0.0006 (17)
N4	0.022 (2)	0.033 (2)	0.032 (2)	−0.0036 (17)	0.0039 (16)	−0.0001 (18)
N5	0.0155 (18)	0.033 (2)	0.032 (2)	0.0015 (15)	0.0064 (15)	−0.0024 (17)
N6	0.022 (2)	0.034 (2)	0.036 (2)	0.0042 (17)	0.0088 (16)	0.0037 (18)
C1	0.020 (2)	0.037 (3)	0.032 (3)	−0.001 (2)	0.0020 (19)	0.010 (2)
C2	0.016 (2)	0.029 (2)	0.034 (2)	−0.0014 (19)	0.0083 (18)	0.008 (2)
C3	0.025 (3)	0.034 (3)	0.058 (3)	0.004 (2)	0.015 (2)	0.009 (3)
C4	0.026 (3)	0.029 (3)	0.090 (4)	0.000 (2)	0.025 (3)	0.007 (3)
C5	0.029 (3)	0.038 (3)	0.044 (3)	0.000 (2)	0.015 (2)	0.001 (2)
C6	0.025 (2)	0.032 (3)	0.046 (3)	0.003 (2)	0.013 (2)	−0.005 (2)
C7	0.020 (2)	0.030 (3)	0.048 (3)	0.002 (2)	0.005 (2)	0.002 (2)
C8	0.026 (3)	0.044 (3)	0.033 (3)	−0.002 (2)	0.004 (2)	0.008 (2)
C9	0.043 (3)	0.053 (3)	0.040 (3)	−0.006 (3)	0.014 (2)	0.006 (3)
C10	0.052 (3)	0.048 (3)	0.044 (3)	−0.005 (3)	0.004 (3)	0.009 (3)
C11	0.028 (3)	0.053 (3)	0.029 (3)	0.005 (2)	0.003 (2)	0.002 (2)
C12	0.022 (2)	0.047 (3)	0.031 (3)	−0.002 (2)	0.0092 (19)	−0.004 (2)
C13	0.036 (3)	0.053 (3)	0.038 (3)	−0.004 (2)	0.007 (2)	−0.011 (2)
C14	0.026 (2)	0.033 (3)	0.037 (3)	−0.006 (2)	0.009 (2)	−0.006 (2)
C15	0.035 (3)	0.028 (3)	0.047 (3)	−0.007 (2)	0.018 (2)	0.001 (2)
C16	0.034 (3)	0.039 (3)	0.039 (3)	0.003 (2)	0.013 (2)	0.007 (2)
C17	0.031 (3)	0.051 (3)	0.044 (3)	0.002 (2)	0.004 (2)	0.004 (3)
C18	0.054 (3)	0.048 (3)	0.050 (3)	0.004 (3)	0.021 (3)	0.012 (3)
C19	0.037 (3)	0.051 (3)	0.027 (3)	−0.003 (2)	0.012 (2)	0.001 (2)
C20	0.024 (2)	0.048 (3)	0.025 (2)	−0.007 (2)	0.0079 (19)	−0.007 (2)
C21	0.052 (3)	0.058 (4)	0.035 (3)	0.010 (3)	0.014 (2)	−0.005 (3)

Geometric parameters (Å, º) top

Ni1—N5	2.098 (3)	C8—C9	1.516 (7)
Ni1—N1	2.106 (4)	C8—C10	1.527 (7)
Ni1—N3	2.123 (3)	C8—C11	1.545 (7)
Ni1—O1	2.132 (3)	C9—H9A	0.9600
Ni1—N4	2.158 (4)	C9—H9B	0.9600
Ni1—N6	2.171 (4)	C9—H9C	0.9600
O1—C1	1.247 (5)	C10—H10A	0.9600
O2—C1	1.265 (5)	C10—H10B	0.9600
O3—C4	1.305 (6)	C10—H10C	0.9600
O3—H3O	0.8400	C11—C12	1.522 (7)
O4—C4	1.210 (6)	C11—H11A	0.9700
O1W—H1W1	0.8400	C11—H11B	0.9700
O1W—H1W2	0.8400	C12—C13	1.541 (6)
O1W'—H1W3	0.8400	C12—H12	0.9800
O1W'—H1W4	0.8400	C13—H13A	0.9600
N1—C5	1.333 (6)	C13—H13B	0.9600
N1—C2	1.388 (5)	C13—H13C	0.9600
N2—C5	1.331 (6)	C14—C15	1.508 (6)
N2—C3	1.366 (6)	C14—H14A	0.9700
N3—C6	1.470 (6)	C14—H14B	0.9700
N3—C20	1.493 (5)	C15—H15A	0.9700
N3—H3N	0.8600	C15—H15B	0.9700
N4—C8	1.485 (6)	C16—C17	1.515 (6)
N4—C7	1.489 (5)	C16—C19	1.533 (7)
N4—H4N	0.8600	C16—C18	1.541 (7)
N5—C14	1.471 (6)	C17—H17A	0.9600
N5—C12	1.484 (5)	C17—H17B	0.9600
N5—H5N	0.8600	C17—H17C	0.9600
N6—C15	1.480 (6)	C18—H18A	0.9600
N6—C16	1.511 (6)	C18—H18B	0.9600
N6—H6N	0.8600	C18—H18C	0.9600
C1—C2	1.458 (7)	C19—C20	1.513 (7)
C2—C3	1.404 (6)	C19—H19A	0.9700
C3—C4	1.487 (7)	C19—H19B	0.9700
C5—H5	0.9300	C20—C21	1.535 (6)
C6—C7	1.511 (6)	C20—H20	0.9800
C6—H6A	0.9700	C21—H21A	0.9600
C6—H6B	0.9700	C21—H21B	0.9600
C7—H7A	0.9700	C21—H21C	0.9600
C7—H7B	0.9700

N5—Ni1—N1	95.99 (14)	C10—C8—C11	107.7 (4)
N5—Ni1—N3	99.73 (13)	C8—C9—H9A	109.5
N1—Ni1—N3	162.72 (14)	C8—C9—H9B	109.5
N5—Ni1—O1	169.03 (13)	H9A—C9—H9B	109.5
N1—Ni1—O1	78.92 (13)	C8—C9—H9C	109.5
N3—Ni1—O1	86.74 (13)	H9A—C9—H9C	109.5
N5—Ni1—N4	87.46 (14)	H9B—C9—H9C	109.5
N1—Ni1—N4	103.71 (14)	C8—C10—H10A	109.5
N3—Ni1—N4	84.20 (14)	C8—C10—H10B	109.5
O1—Ni1—N4	84.36 (13)	H10A—C10—H10B	109.5
N5—Ni1—N6	84.52 (14)	C8—C10—H10C	109.5
N1—Ni1—N6	87.00 (14)	H10A—C10—H10C	109.5
N3—Ni1—N6	87.40 (14)	H10B—C10—H10C	109.5
O1—Ni1—N6	104.75 (13)	C12—C11—C8	119.7 (4)
N4—Ni1—N6	167.25 (14)	C12—C11—H11A	107.4
C1—O1—Ni1	115.5 (3)	C8—C11—H11A	107.4
C4—O3—H3O	109.5	C12—C11—H11B	107.4
H1W1—O1W—H1W2	111.3	C8—C11—H11B	107.4
H1W3—O1W'—H1W4	114.2	H11A—C11—H11B	106.9
C5—N1—C2	104.5 (4)	N5—C12—C11	111.1 (4)
C5—N1—Ni1	145.8 (3)	N5—C12—C13	112.7 (4)
C2—N1—Ni1	109.7 (3)	C11—C12—C13	109.4 (4)
C5—N2—C3	103.8 (4)	N5—C12—H12	107.8
C6—N3—C20	112.9 (4)	C11—C12—H12	107.8
C6—N3—Ni1	104.3 (2)	C13—C12—H12	107.8
C20—N3—Ni1	115.0 (3)	C12—C13—H13A	109.5
C6—N3—H3N	108.1	C12—C13—H13B	109.5
C20—N3—H3N	108.1	H13A—C13—H13B	109.5
Ni1—N3—H3N	108.1	C12—C13—H13C	109.5
C8—N4—C7	114.2 (3)	H13A—C13—H13C	109.5
C8—N4—Ni1	122.1 (3)	H13B—C13—H13C	109.5
C7—N4—Ni1	104.4 (3)	N5—C14—C15	110.3 (4)
C8—N4—H4N	104.9	N5—C14—H14A	109.6
C7—N4—H4N	104.9	C15—C14—H14A	109.6
Ni1—N4—H4N	104.9	N5—C14—H14B	109.6
C14—N5—C12	112.7 (3)	C15—C14—H14B	109.6
C14—N5—Ni1	105.4 (2)	H14A—C14—H14B	108.1
C12—N5—Ni1	116.3 (3)	N6—C15—C14	110.2 (4)
C14—N5—H5N	107.4	N6—C15—H15A	109.6
C12—N5—H5N	107.4	C14—C15—H15A	109.6
Ni1—N5—H5N	107.4	N6—C15—H15B	109.6
C15—N6—C16	114.7 (3)	C14—C15—H15B	109.6
C15—N6—Ni1	103.8 (3)	H15A—C15—H15B	108.1
C16—N6—Ni1	121.2 (3)	N6—C16—C17	107.4 (4)
C15—N6—H6N	105.2	N6—C16—C19	109.6 (4)
C16—N6—H6N	105.2	C17—C16—C19	111.8 (4)
Ni1—N6—H6N	105.2	N6—C16—C18	111.4 (4)
O1—C1—O2	124.0 (5)	C17—C16—C18	108.4 (4)
O1—C1—C2	116.5 (4)	C19—C16—C18	108.3 (4)
O2—C1—C2	119.5 (4)	C16—C17—H17A	109.5
N1—C2—C3	106.5 (4)	C16—C17—H17B	109.5
N1—C2—C1	119.2 (4)	H17A—C17—H17B	109.5
C3—C2—C1	134.3 (4)	C16—C17—H17C	109.5
N2—C3—C2	109.5 (4)	H17A—C17—H17C	109.5
N2—C3—C4	122.0 (4)	H17B—C17—H17C	109.5
C2—C3—C4	128.5 (5)	C16—C18—H18A	109.5
O4—C4—O3	121.0 (5)	C16—C18—H18B	109.5
O4—C4—C3	121.4 (5)	H18A—C18—H18B	109.5
O3—C4—C3	117.6 (5)	C16—C18—H18C	109.5
N2—C5—N1	115.6 (4)	H18A—C18—H18C	109.5
N2—C5—H5	122.2	H18B—C18—H18C	109.5
N1—C5—H5	122.2	C20—C19—C16	118.5 (4)
N3—C6—C7	110.0 (4)	C20—C19—H19A	107.7
N3—C6—H6A	109.7	C16—C19—H19A	107.7
C7—C6—H6A	109.7	C20—C19—H19B	107.7
N3—C6—H6B	109.7	C16—C19—H19B	107.7
C7—C6—H6B	109.7	H19A—C19—H19B	107.1
H6A—C6—H6B	108.2	N3—C20—C19	110.9 (4)
N4—C7—C6	108.7 (3)	N3—C20—C21	111.9 (4)
N4—C7—H7A	109.9	C19—C20—C21	110.4 (4)
C6—C7—H7A	109.9	N3—C20—H20	107.9
N4—C7—H7B	109.9	C19—C20—H20	107.9
C6—C7—H7B	109.9	C21—C20—H20	107.9
H7A—C7—H7B	108.3	C20—C21—H21A	109.5
N4—C8—C9	107.8 (4)	C20—C21—H21B	109.5
N4—C8—C10	113.0 (4)	H21A—C21—H21B	109.5
C9—C8—C10	107.4 (4)	C20—C21—H21C	109.5
N4—C8—C11	109.3 (4)	H21A—C21—H21C	109.5
C9—C8—C11	111.6 (4)	H21B—C21—H21C	109.5

N5—Ni1—O1—C1	−58.3 (8)	C5—N1—C2—C1	179.8 (4)
N1—Ni1—O1—C1	4.9 (3)	Ni1—N1—C2—C1	0.1 (5)
N3—Ni1—O1—C1	175.2 (3)	O1—C1—C2—N1	4.2 (6)
N4—Ni1—O1—C1	−100.3 (3)	O2—C1—C2—N1	−176.7 (4)
N6—Ni1—O1—C1	88.8 (3)	O1—C1—C2—C3	−177.8 (5)
N5—Ni1—N1—C5	−11.8 (6)	O2—C1—C2—C3	1.2 (8)
N3—Ni1—N1—C5	143.7 (6)	C5—N2—C3—C2	0.7 (5)
O1—Ni1—N1—C5	178.1 (6)	C5—N2—C3—C4	178.6 (5)
N4—Ni1—N1—C5	−100.6 (6)	N1—C2—C3—N2	−1.3 (5)
N6—Ni1—N1—C5	72.4 (6)	C1—C2—C3—N2	−179.4 (5)
N5—Ni1—N1—C2	167.8 (3)	N1—C2—C3—C4	−179.1 (5)
N3—Ni1—N1—C2	−36.7 (6)	C1—C2—C3—C4	2.8 (9)
O1—Ni1—N1—C2	−2.3 (3)	N2—C3—C4—O4	1.5 (8)
N4—Ni1—N1—C2	79.0 (3)	C2—C3—C4—O4	179.0 (5)
N6—Ni1—N1—C2	−108.0 (3)	N2—C3—C4—O3	−178.7 (5)
N5—Ni1—N3—C6	−103.8 (3)	C2—C3—C4—O3	−1.2 (8)
N1—Ni1—N3—C6	101.1 (5)	C3—N2—C5—N1	0.3 (6)
O1—Ni1—N3—C6	67.3 (3)	C2—N1—C5—N2	−1.1 (5)
N4—Ni1—N3—C6	−17.3 (3)	Ni1—N1—C5—N2	178.5 (4)
N6—Ni1—N3—C6	172.3 (3)	C20—N3—C6—C7	171.3 (3)
N5—Ni1—N3—C20	132.0 (3)	Ni1—N3—C6—C7	45.7 (4)
N1—Ni1—N3—C20	−23.2 (6)	C8—N4—C7—C6	176.8 (4)
O1—Ni1—N3—C20	−56.9 (3)	Ni1—N4—C7—C6	41.0 (4)
N4—Ni1—N3—C20	−141.6 (3)	N3—C6—C7—N4	−61.4 (5)
N6—Ni1—N3—C20	48.0 (3)	C7—N4—C8—C9	163.5 (4)
N5—Ni1—N4—C8	−44.3 (3)	Ni1—N4—C8—C9	−69.3 (4)
N1—Ni1—N4—C8	51.3 (3)	C7—N4—C8—C10	45.0 (5)
N3—Ni1—N4—C8	−144.3 (3)	Ni1—N4—C8—C10	172.2 (3)
O1—Ni1—N4—C8	128.4 (3)	C7—N4—C8—C11	−75.0 (5)
N6—Ni1—N4—C8	−95.3 (7)	Ni1—N4—C8—C11	52.2 (4)
N5—Ni1—N4—C7	87.1 (3)	N4—C8—C11—C12	−60.0 (5)
N1—Ni1—N4—C7	−177.4 (2)	C9—C8—C11—C12	59.2 (6)
N3—Ni1—N4—C7	−13.0 (3)	C10—C8—C11—C12	176.8 (4)
O1—Ni1—N4—C7	−100.3 (3)	C14—N5—C12—C11	173.0 (3)
N6—Ni1—N4—C7	36.1 (7)	Ni1—N5—C12—C11	−65.2 (4)
N1—Ni1—N5—C14	70.1 (3)	C14—N5—C12—C13	49.8 (5)
N3—Ni1—N5—C14	−102.7 (3)	Ni1—N5—C12—C13	171.6 (3)
O1—Ni1—N5—C14	131.8 (6)	C8—C11—C12—N5	68.9 (5)
N4—Ni1—N5—C14	173.6 (3)	C8—C11—C12—C13	−166.0 (4)
N6—Ni1—N5—C14	−16.3 (3)	C12—N5—C14—C15	171.1 (3)
N1—Ni1—N5—C12	−55.5 (3)	Ni1—N5—C14—C15	43.4 (4)
N3—Ni1—N5—C12	131.7 (3)	C16—N6—C15—C14	174.2 (4)
O1—Ni1—N5—C12	6.2 (9)	Ni1—N6—C15—C14	39.7 (4)
N4—Ni1—N5—C12	48.0 (3)	N5—C14—C15—N6	−58.8 (5)
N6—Ni1—N5—C12	−141.9 (3)	C15—N6—C16—C17	164.8 (4)
N5—Ni1—N6—C15	−12.6 (3)	Ni1—N6—C16—C17	−69.3 (4)
N1—Ni1—N6—C15	−109.0 (3)	C15—N6—C16—C19	−73.6 (5)
N3—Ni1—N6—C15	87.4 (3)	Ni1—N6—C16—C19	52.4 (5)
O1—Ni1—N6—C15	173.3 (3)	C15—N6—C16—C18	46.2 (5)
N4—Ni1—N6—C15	38.6 (7)	Ni1—N6—C16—C18	172.2 (3)
N5—Ni1—N6—C16	−143.4 (3)	N6—C16—C19—C20	−62.3 (5)
N1—Ni1—N6—C16	120.3 (3)	C17—C16—C19—C20	56.6 (5)
N3—Ni1—N6—C16	−43.3 (3)	C18—C16—C19—C20	176.0 (4)
O1—Ni1—N6—C16	42.6 (3)	C6—N3—C20—C19	173.2 (4)
N4—Ni1—N6—C16	−92.1 (7)	Ni1—N3—C20—C19	−67.2 (4)
Ni1—O1—C1—O2	174.8 (3)	C6—N3—C20—C21	49.6 (5)
Ni1—O1—C1—C2	−6.2 (5)	Ni1—N3—C20—C21	169.1 (3)
C5—N1—C2—C3	1.4 (5)	C16—C19—C20—N3	72.5 (5)
Ni1—N1—C2—C3	−178.4 (3)	C16—C19—C20—C21	−163.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···O2	0.84	1.64	2.468 (5)	170
N5—H5n···O4ⁱ	0.86	2.14	2.973 (5)	162

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Ni(C₅H₂N₂O₄)(C₁₆H₃₆N₄)]·H₂O
M_r	515.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.4070 (8), 12.7806 (10), 19.0947 (14)
β (°)	103.675 (1)
V (Å³)	2467.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.42 × 0.36 × 0.12

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.767, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	10408, 4308, 2809
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.163, 1.04
No. of reflections	4308
No. of parameters	309
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.36

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

This work was supported by the Foundation for University Key Teachers of the Education Department of Hunan Province and the Key Subject Construction Project of Hunan Province, China (No. 2006–180).

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–211. CrossRef CAS Google Scholar
Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ou, G.-C., Zhang, M. & Yuan, X.-Y. (2009a). Acta Cryst. E65, m726. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ou, G.-C., Zhou, Q. & Ng, S. W. (2009b). Acta Cryst. E65, m728. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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