Aqua­bis(2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato)nickel(II)

Zhang, H.; Sun, Y.; Chen, X.; Yu, F.; Zou, Z.

doi:10.1107/S1600536809051563

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m5

doi:10.1107/S1600536809051563

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Aquabis(2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9-olato)nickel(II)

Huaihong Zhang,^a,^b Yu Sun,^a Xiaodan Chen,^a Fei Yu ^a and Zhihong Zou ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China, and ^bSchool of Chemistry and Biology, Yancheng Institute of Technology, Yancheng 224003, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 19 November 2009; accepted 30 November 2009; online 4 December 2009)

In the crystal structure of the mononuclear title complex, [Ni(C₁₀H₉N₂O₂)₂(H₂O)], the Ni^II ion is five-coordinated in a distorted square-pyramidal geometry by two N atoms and two O atoms from 2,3-dimethyl-4-oxopyrido[1,2-a]pyrimidin-9-olate ligands and one O atom from a water molecule. O—H⋯O hydrogen bonds between the coordinated water molecule and the ligand connect adjacent molecules, forming a ribbon parallel to the b axis.

Related literature

For the design and synthesis of self-assembling systems with organic ligands containing N and O donors, see: Wei et al. (2009 ); Sun et al. (2008 ); Bayot et al. (2006 ); Chen et al. (2007 ). For structures of quinolin-8-ol complexes, see: Wu et al. (2006 ).

Experimental

Crystal data

[Ni(C₁₀H₉N₂O₂)₂(H₂O)]
M_r = 455.11
Monoclinic, P 2₁ /c
a = 13.4032 (14) Å
b = 12.1313 (12) Å
c = 12.4631 (11) Å
β = 99.386 (1)°
V = 1999.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.01 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.12 mm

Data collection

Rigaku SCXmini CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.751, T_max = 0.888
10283 measured reflections
3520 independent reflections
2242 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.132
S = 1.03
3520 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.85	1.83	2.672 (5)	173
O5—H5B⋯O4ⁱⁱ	0.85	1.85	2.669 (5)	162
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809051563/zq2018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051563/zq2018Isup2.hkl

checkCIF report

Comment top

Considerable attention has been paid to the design and synthesis of complexes with organic ligands containing N and O donors (Wei et al., 2009; Sun et al., 2008; Bayot et al., 2006; Chen, et al., 2007). Quinolin-8-ol is one such ligand and several crystal structures of complexes containing it have been reported (Wu et al., 2006). We report here the synthesis and crystal structure of the title complex (I) (Fig. 1). In (I), the Ni atom is five-coordinated by two pyridine nitrogen atoms and two oxygen atoms from the hydroxy groups and one oxygen atom from a water molecule (Fig. 1). Intermolecular O—H···O hydrogen bonds (Fig.2 and Table 1) connecting the molecules of (I) define the crystal packing.

Related literature top

For the design and synthesis of self-assembling systems with organic ligands containing N and O donors, see: Wei et al. (2009); Sun et al. (2008); Bayot et al. (2006); Chen et al. (2007). For structures of quinolin-8-ol complexes, see: Wu et al. (2006).

Experimental top

All chemicals used (reagent grade) were commercially available. An aqueous solution (5 ml) of Ni(Ac)₂.4H₂O (24.9 mg, 0.1 mmol) was added to an ethanol solution (10 ml) containing 2,3-dimethyl-9-hydroxylpyrido[1,2-a]pyrimidin-4-one (38.0 mg, 0.2 mmol) then filtered off. The resulting solution was continuously stirred for about 30 min and then filtered. The filtrate was slowly evaporated at room temperature over several days and colorless prism crystals suitable for X-ray analysis were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule and the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of compound (I). Hydrogen bonds are shown as dashed lines.

Aquabis(2,3-dimethyl-4-oxo-4H-pyrido[1,2-a]pyrimidin-9- olato)nickel(II) top

Crystal data top

[Ni(C₁₀H₉N₂O₂)₂(H₂O)]	F(000) = 944
M_r = 455.11	D_x = 1.512 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2294 reflections
a = 13.4032 (14) Å	θ = 2.3–23.7°
b = 12.1313 (12) Å	µ = 1.01 mm⁻¹
c = 12.4631 (11) Å	T = 298 K
β = 99.386 (1)°	Prism, colorless
V = 1999.3 (3) Å³	0.30 × 0.20 × 0.12 mm
Z = 4

Data collection top

Rigaku SCXmini CCD area-detector diffractometer	3520 independent reflections
Radiation source: fine-focus sealed tube	2242 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
phi and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 200)	h = −15→15
T_min = 0.751, T_max = 0.888	k = −13→14
10283 measured reflections	l = −8→14

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) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0496P)² + 2.7285P] where P = (F_o² + 2F_c²)/3
3520 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

[Ni(C₁₀H₉N₂O₂)₂(H₂O)]	V = 1999.3 (3) Å³
M_r = 455.11	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.4032 (14) Å	µ = 1.01 mm⁻¹
b = 12.1313 (12) Å	T = 298 K
c = 12.4631 (11) Å	0.30 × 0.20 × 0.12 mm
β = 99.386 (1)°

Data collection top

Rigaku SCXmini CCD area-detector diffractometer	3520 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 200)	2242 reflections with I > 2σ(I)
T_min = 0.751, T_max = 0.888	R_int = 0.045
10283 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
3520 reflections	Δρ_min = −0.41 e Å⁻³
271 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Ni1	0.79535 (4)	0.41721 (5)	0.19800 (5)	0.0428 (2)
N1	0.6831 (2)	0.4337 (3)	0.0534 (3)	0.0351 (9)
N2	0.5489 (3)	0.3281 (3)	−0.0425 (3)	0.0413 (10)
N3	0.9220 (2)	0.3915 (3)	0.3261 (3)	0.0334 (8)
N4	1.0960 (3)	0.4366 (3)	0.3602 (3)	0.0348 (9)
O1	0.7277 (2)	0.2737 (3)	0.1993 (2)	0.0460 (8)
O2	0.4536 (3)	0.3929 (3)	−0.1970 (3)	0.0690 (12)
O3	0.9049 (2)	0.4701 (3)	0.1247 (2)	0.0460 (8)
O4	1.1941 (2)	0.3960 (3)	0.5228 (3)	0.0536 (9)
O5	0.7303 (2)	0.5312 (3)	0.2785 (3)	0.0679 (11)
H5A	0.6697	0.5514	0.2562	0.082*
H5B	0.7550	0.5674	0.3350	0.082*
C1	0.6639 (3)	0.5152 (4)	−0.0221 (4)	0.0404 (11)
C2	0.5870 (4)	0.5058 (4)	−0.1098 (4)	0.0475 (13)
C3	0.5254 (3)	0.4119 (5)	−0.1233 (4)	0.0479 (13)
C4	0.6274 (3)	0.3425 (4)	0.0416 (3)	0.0337 (10)
C5	0.6514 (3)	0.2575 (4)	0.1225 (4)	0.0373 (11)
C6	0.5915 (4)	0.1653 (4)	0.1126 (4)	0.0504 (13)
H6	0.6050	0.1089	0.1634	0.061*
C7	0.5104 (4)	0.1549 (5)	0.0275 (5)	0.0621 (15)
H7	0.4700	0.0922	0.0231	0.075*
C8	0.4899 (4)	0.2337 (5)	−0.0480 (5)	0.0586 (15)
H8	0.4358	0.2252	−0.1045	0.070*
C9	0.7298 (4)	0.6146 (4)	−0.0027 (4)	0.0582 (14)
H9A	0.7661	0.6130	0.0703	0.087*
H9B	0.6887	0.6798	−0.0130	0.087*
H9C	0.7769	0.6149	−0.0530	0.087*
C10	0.5654 (4)	0.5939 (5)	−0.1961 (4)	0.0653 (16)
H10A	0.5696	0.6652	−0.1622	0.098*
H10B	0.4987	0.5834	−0.2365	0.098*
H10C	0.6142	0.5891	−0.2445	0.098*
C11	0.9307 (3)	0.3468 (4)	0.4274 (3)	0.0352 (10)
C12	1.0208 (3)	0.3451 (4)	0.4981 (3)	0.0362 (10)
C13	1.1084 (3)	0.3907 (4)	0.4675 (4)	0.0378 (11)
C14	1.0038 (3)	0.4335 (3)	0.2942 (3)	0.0311 (10)
C15	0.9932 (3)	0.4783 (4)	0.1855 (3)	0.0360 (10)
C16	1.0767 (4)	0.5258 (4)	0.1534 (4)	0.0466 (12)
H16	1.0721	0.5558	0.0841	0.056*
C17	1.1679 (4)	0.5290 (4)	0.2247 (4)	0.0527 (13)
H17	1.2234	0.5623	0.2021	0.063*
C18	1.1788 (3)	0.4855 (4)	0.3254 (4)	0.0480 (13)
H18	1.2410	0.4883	0.3711	0.058*
C19	0.8349 (3)	0.3004 (4)	0.4571 (4)	0.0484 (13)
H19A	0.8131	0.3456	0.5121	0.073*
H19B	0.8470	0.2268	0.4842	0.073*
H19C	0.7833	0.2993	0.3938	0.073*
C20	1.0318 (4)	0.2944 (4)	0.6096 (4)	0.0551 (14)
H20A	0.9703	0.3043	0.6384	0.083*
H20B	1.0866	0.3293	0.6566	0.083*
H20C	1.0457	0.2170	0.6048	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0354 (3)	0.0546 (4)	0.0368 (4)	−0.0007 (3)	0.0008 (3)	0.0014 (3)
N1	0.0296 (19)	0.045 (2)	0.029 (2)	0.0054 (17)	0.0013 (15)	−0.0004 (17)
N2	0.034 (2)	0.052 (3)	0.035 (2)	0.0108 (19)	−0.0008 (17)	−0.0133 (18)
N3	0.0277 (19)	0.043 (2)	0.029 (2)	−0.0016 (16)	0.0040 (15)	0.0005 (16)
N4	0.0308 (19)	0.042 (2)	0.030 (2)	−0.0009 (16)	0.0009 (16)	−0.0070 (16)
O1	0.0438 (19)	0.053 (2)	0.0376 (19)	0.0011 (15)	−0.0052 (15)	0.0100 (15)
O2	0.051 (2)	0.105 (3)	0.044 (2)	0.028 (2)	−0.0141 (18)	−0.015 (2)
O3	0.0358 (18)	0.067 (2)	0.0329 (18)	−0.0040 (16)	−0.0014 (14)	0.0100 (16)
O4	0.042 (2)	0.075 (3)	0.038 (2)	0.0039 (17)	−0.0102 (16)	−0.0068 (16)
O5	0.048 (2)	0.098 (3)	0.048 (2)	0.028 (2)	−0.0204 (16)	−0.032 (2)
C1	0.042 (3)	0.046 (3)	0.035 (3)	0.012 (2)	0.011 (2)	0.007 (2)
C2	0.052 (3)	0.057 (3)	0.034 (3)	0.024 (3)	0.009 (2)	0.005 (2)
C3	0.037 (3)	0.072 (4)	0.032 (3)	0.025 (3)	−0.004 (2)	−0.010 (3)
C4	0.028 (2)	0.043 (3)	0.029 (2)	0.004 (2)	0.0021 (19)	−0.006 (2)
C5	0.034 (3)	0.039 (3)	0.040 (3)	0.003 (2)	0.008 (2)	−0.002 (2)
C6	0.049 (3)	0.042 (3)	0.062 (4)	0.002 (2)	0.014 (3)	0.003 (2)
C7	0.049 (3)	0.043 (3)	0.092 (5)	−0.005 (3)	0.005 (3)	−0.017 (3)
C8	0.037 (3)	0.066 (4)	0.068 (4)	−0.004 (3)	−0.006 (3)	−0.031 (3)
C9	0.062 (3)	0.052 (3)	0.062 (4)	0.005 (3)	0.013 (3)	0.017 (3)
C10	0.071 (4)	0.078 (4)	0.046 (3)	0.034 (3)	0.006 (3)	0.018 (3)
C11	0.040 (3)	0.038 (3)	0.028 (3)	0.003 (2)	0.008 (2)	0.002 (2)
C12	0.047 (3)	0.035 (3)	0.026 (2)	0.004 (2)	0.002 (2)	−0.0003 (19)
C13	0.041 (3)	0.038 (3)	0.030 (3)	0.006 (2)	−0.004 (2)	−0.008 (2)
C14	0.029 (2)	0.037 (2)	0.027 (2)	0.0029 (19)	0.0013 (18)	−0.0050 (18)
C15	0.037 (3)	0.042 (3)	0.028 (3)	−0.001 (2)	0.004 (2)	−0.004 (2)
C16	0.050 (3)	0.060 (3)	0.031 (3)	−0.011 (2)	0.010 (2)	0.000 (2)
C17	0.047 (3)	0.067 (4)	0.046 (3)	−0.014 (3)	0.015 (3)	−0.007 (3)
C18	0.029 (3)	0.067 (3)	0.047 (3)	−0.010 (2)	0.005 (2)	−0.008 (3)
C19	0.046 (3)	0.061 (3)	0.040 (3)	−0.004 (2)	0.012 (2)	0.004 (2)
C20	0.064 (3)	0.060 (3)	0.037 (3)	0.002 (3)	−0.004 (3)	0.007 (2)

Geometric parameters (Å, º) top

Ni1—O3	1.959 (3)	C6—H6	0.9300
Ni1—O1	1.964 (3)	C7—C8	1.338 (8)
Ni1—O5	1.991 (3)	C7—H7	0.9300
Ni1—N3	2.155 (3)	C8—H8	0.9300
Ni1—N1	2.160 (3)	C9—H9A	0.9600
N1—C4	1.329 (5)	C9—H9B	0.9600
N1—C1	1.360 (5)	C9—H9C	0.9600
N2—C4	1.370 (5)	C10—H10A	0.9600
N2—C8	1.387 (6)	C10—H10B	0.9600
N2—C3	1.429 (6)	C10—H10C	0.9600
N3—C14	1.327 (5)	C11—C12	1.374 (6)
N3—C11	1.361 (5)	C11—C19	1.503 (6)
N4—C14	1.368 (5)	C12—C13	1.406 (6)
N4—C18	1.389 (5)	C12—C20	1.505 (6)
N4—C13	1.433 (6)	C14—C15	1.445 (6)
O1—C5	1.297 (5)	C15—C16	1.374 (6)
O2—C3	1.239 (5)	C16—C17	1.390 (7)
O3—C15	1.301 (5)	C16—H16	0.9300
O4—C13	1.241 (5)	C17—C18	1.347 (7)
O5—H5A	0.8499	C17—H17	0.9300
O5—H5B	0.8499	C18—H18	0.9300
C1—C2	1.379 (6)	C19—H19A	0.9600
C1—C9	1.491 (7)	C19—H19B	0.9600
C2—C3	1.401 (7)	C19—H19C	0.9600
C2—C10	1.511 (7)	C20—H20A	0.9600
C4—C5	1.442 (6)	C20—H20B	0.9600
C5—C6	1.370 (6)	C20—H20C	0.9600
C6—C7	1.395 (7)

O3—Ni1—O1	132.53 (14)	N2—C8—H8	119.8
O3—Ni1—O5	115.52 (16)	C1—C9—H9A	109.5
O1—Ni1—O5	111.75 (15)	C1—C9—H9B	109.5
O3—Ni1—N3	80.38 (12)	H9A—C9—H9B	109.5
O1—Ni1—N3	100.05 (13)	C1—C9—H9C	109.5
O5—Ni1—N3	94.82 (13)	H9A—C9—H9C	109.5
O3—Ni1—N1	93.07 (13)	H9B—C9—H9C	109.5
O1—Ni1—N1	80.18 (13)	C2—C10—H10A	109.5
O5—Ni1—N1	93.07 (13)	C2—C10—H10B	109.5
N3—Ni1—N1	171.37 (13)	H10A—C10—H10B	109.5
C4—N1—C1	119.3 (4)	C2—C10—H10C	109.5
C4—N1—Ni1	108.5 (3)	H10A—C10—H10C	109.5
C1—N1—Ni1	132.2 (3)	H10B—C10—H10C	109.5
C4—N2—C8	120.3 (4)	N3—C11—C12	122.3 (4)
C4—N2—C3	120.1 (4)	N3—C11—C19	115.5 (4)
C8—N2—C3	119.6 (4)	C12—C11—C19	122.2 (4)
C14—N3—C11	118.7 (3)	C11—C12—C13	120.4 (4)
C14—N3—Ni1	108.2 (3)	C11—C12—C20	122.8 (4)
C11—N3—Ni1	133.0 (3)	C13—C12—C20	116.8 (4)
C14—N4—C18	120.9 (4)	O4—C13—C12	127.5 (4)
C14—N4—C13	120.4 (4)	O4—C13—N4	117.0 (4)
C18—N4—C13	118.7 (4)	C12—C13—N4	115.5 (4)
C5—O1—Ni1	116.0 (3)	N3—C14—N4	122.7 (4)
C15—O3—Ni1	115.7 (3)	N3—C14—C15	117.7 (4)
Ni1—O5—H5A	120.6	N4—C14—C15	119.6 (4)
Ni1—O5—H5B	129.2	O3—C15—C16	124.7 (4)
H5A—O5—H5B	110.1	O3—C15—C14	117.3 (4)
N1—C1—C2	121.4 (4)	C16—C15—C14	118.0 (4)
N1—C1—C9	115.8 (4)	C15—C16—C17	119.9 (4)
C2—C1—C9	122.8 (4)	C15—C16—H16	120.0
C1—C2—C3	120.8 (4)	C17—C16—H16	120.0
C1—C2—C10	122.5 (5)	C18—C17—C16	122.4 (5)
C3—C2—C10	116.7 (5)	C18—C17—H17	118.8
O2—C3—C2	127.7 (5)	C16—C17—H17	118.8
O2—C3—N2	116.4 (5)	C17—C18—N4	119.1 (4)
C2—C3—N2	115.9 (4)	C17—C18—H18	120.4
N1—C4—N2	122.6 (4)	N4—C18—H18	120.4
N1—C4—C5	117.4 (4)	C11—C19—H19A	109.5
N2—C4—C5	120.0 (4)	C11—C19—H19B	109.5
O1—C5—C6	124.8 (4)	H19A—C19—H19B	109.5
O1—C5—C4	117.8 (4)	C11—C19—H19C	109.5
C6—C5—C4	117.4 (4)	H19A—C19—H19C	109.5
C5—C6—C7	121.0 (5)	H19B—C19—H19C	109.5
C5—C6—H6	119.5	C12—C20—H20A	109.5
C7—C6—H6	119.5	C12—C20—H20B	109.5
C8—C7—C6	121.0 (5)	H20A—C20—H20B	109.5
C8—C7—H7	119.5	C12—C20—H20C	109.5
C6—C7—H7	119.5	H20A—C20—H20C	109.5
C7—C8—N2	120.3 (5)	H20B—C20—H20C	109.5
C7—C8—H8	119.8

O3—Ni1—N1—C4	133.7 (3)	N1—C4—C5—O1	−2.3 (6)
O1—Ni1—N1—C4	1.0 (3)	N2—C4—C5—O1	178.5 (4)
O5—Ni1—N1—C4	−110.5 (3)	N1—C4—C5—C6	177.6 (4)
O3—Ni1—N1—C1	−44.8 (4)	N2—C4—C5—C6	−1.6 (6)
O1—Ni1—N1—C1	−177.5 (4)	O1—C5—C6—C7	179.7 (4)
O5—Ni1—N1—C1	71.0 (4)	C4—C5—C6—C7	−0.1 (7)
O3—Ni1—N3—C14	6.0 (3)	C5—C6—C7—C8	1.1 (8)
O1—Ni1—N3—C14	137.8 (3)	C6—C7—C8—N2	−0.4 (8)
O5—Ni1—N3—C14	−109.1 (3)	C4—N2—C8—C7	−1.4 (7)
O3—Ni1—N3—C11	−176.6 (4)	C3—N2—C8—C7	−179.5 (5)
O1—Ni1—N3—C11	−44.9 (4)	C14—N3—C11—C12	1.0 (6)
O5—Ni1—N3—C11	68.3 (4)	Ni1—N3—C11—C12	−176.2 (3)
O3—Ni1—O1—C5	−87.5 (3)	C14—N3—C11—C19	−179.6 (4)
O5—Ni1—O1—C5	87.0 (3)	Ni1—N3—C11—C19	3.3 (6)
N3—Ni1—O1—C5	−173.6 (3)	N3—C11—C12—C13	0.2 (7)
N1—Ni1—O1—C5	−2.4 (3)	C19—C11—C12—C13	−179.2 (4)
O1—Ni1—O3—C15	−102.8 (3)	N3—C11—C12—C20	−179.0 (4)
O5—Ni1—O3—C15	82.8 (3)	C19—C11—C12—C20	1.7 (7)
N3—Ni1—O3—C15	−8.0 (3)	C11—C12—C13—O4	179.3 (4)
N1—Ni1—O3—C15	177.7 (3)	C20—C12—C13—O4	−1.6 (7)
C4—N1—C1—C2	0.9 (6)	C11—C12—C13—N4	−0.3 (6)
Ni1—N1—C1—C2	179.3 (3)	C20—C12—C13—N4	178.9 (4)
C4—N1—C1—C9	179.9 (4)	C14—N4—C13—O4	179.8 (4)
Ni1—N1—C1—C9	−1.7 (6)	C18—N4—C13—O4	−1.2 (6)
N1—C1—C2—C3	0.5 (7)	C14—N4—C13—C12	−0.6 (6)
C9—C1—C2—C3	−178.4 (4)	C18—N4—C13—C12	178.4 (4)
N1—C1—C2—C10	−178.7 (4)	C11—N3—C14—N4	−2.0 (6)
C9—C1—C2—C10	2.4 (7)	Ni1—N3—C14—N4	175.8 (3)
C1—C2—C3—O2	179.4 (4)	C11—N3—C14—C15	178.7 (4)
C10—C2—C3—O2	−1.4 (7)	Ni1—N3—C14—C15	−3.5 (4)
C1—C2—C3—N2	−0.9 (6)	C18—N4—C14—N3	−177.2 (4)
C10—C2—C3—N2	178.3 (4)	C13—N4—C14—N3	1.8 (6)
C4—N2—C3—O2	179.7 (4)	C18—N4—C14—C15	2.2 (6)
C8—N2—C3—O2	−2.1 (6)	C13—N4—C14—C15	−178.8 (4)
C4—N2—C3—C2	0.0 (6)	Ni1—O3—C15—C16	−171.8 (4)
C8—N2—C3—C2	178.2 (4)	Ni1—O3—C15—C14	8.5 (5)
C1—N1—C4—N2	−1.9 (6)	N3—C14—C15—O3	−2.9 (6)
Ni1—N1—C4—N2	179.4 (3)	N4—C14—C15—O3	177.8 (4)
C1—N1—C4—C5	179.0 (4)	N3—C14—C15—C16	177.5 (4)
Ni1—N1—C4—C5	0.3 (4)	N4—C14—C15—C16	−1.9 (6)
C8—N2—C4—N1	−176.8 (4)	O3—C15—C16—C17	−179.2 (4)
C3—N2—C4—N1	1.4 (6)	C14—C15—C16—C17	0.4 (7)
C8—N2—C4—C5	2.3 (6)	C15—C16—C17—C18	0.8 (8)
C3—N2—C4—C5	−179.5 (4)	C16—C17—C18—N4	−0.6 (8)
Ni1—O1—C5—C6	−176.6 (3)	C14—N4—C18—C17	−0.9 (7)
Ni1—O1—C5—C4	3.3 (5)	C13—N4—C18—C17	−179.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	1.83	2.672 (5)	173
O5—H5B···O4ⁱⁱ	0.85	1.85	2.669 (5)	162

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

Experimental details

Crystal data
Chemical formula	[Ni(C₁₀H₉N₂O₂)₂(H₂O)]
M_r	455.11
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.4032 (14), 12.1313 (12), 12.4631 (11)
β (°)	99.386 (1)
V (Å³)	1999.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.01
Crystal size (mm)	0.30 × 0.20 × 0.12

Data collection
Diffractometer	Rigaku SCXmini CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 200)
T_min, T_max	0.751, 0.888
No. of measured, independent and observed [I > 2σ(I)] reflections	10283, 3520, 2242
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.132, 1.03
No. of reflections	3520
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.41

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.85	1.83	2.672 (5)	173
O5—H5B···O4ⁱⁱ	0.85	1.85	2.669 (5)	162

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

References

Bayot, D., Degand, M., Tinant, B. & Devillers, M. (2006). Inorg. Chem. Commun. 359, 1390–1394. CAS Google Scholar
Chen, K., Zhang, Y.-L., Feng, M.-Q. & Liu, C.-H. (2007). Acta Cryst. E63, m2033. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, Y., Jiang, X.-D. & Li, X.-B. (2008). Acta Cryst. E64, m801. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wei, Y.-F., Li, Z.-S., Zhang, H.-H. & Wang, Y.-H. (2009). Acta Cryst. E65, m91. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, H., Dong, X.-W., Liu, H.-Y. & Ma, J.-F. (2006). Acta Cryst. E62, m281–m282. Web of Science CSD CrossRef IUCr Journals Google Scholar

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m5

doi:10.1107/S1600536809051563

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