Bis[4-(4-chloro­benzo­yl)-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ2O,O′]bis­(methanol-κO)nickel(II)

Zhang, X.; Huang, M.; Du, C.; Han, J.

doi:10.1107/S1600536810038973

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1361

https://doi.org/10.1107/S1600536810038973

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Bis[4-(4-chlorobenzoyl)-3-methyl-1-phenyl-1H-pyrazol-5-olato-κ²O,O′]bis(methanol-κO)nickel(II)

Xin Zhang,^a ^* Meng Huang,^a Cong Du ^a and Junjing Han ^a

^aCollege of Chemistry, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: zxin_tj@126.com

(Received 7 September 2010; accepted 29 September 2010; online 9 October 2010)

The molecular structure of the neutral mononuclear title complex, [Ni(C₁₇H₁₂ClN₂O₂)₂(CH₃OH)₂], is centrosymmetric. The Ni^II atom, which is located on an inversion center, is in a distorted octahedral coordination, defined by four O atoms from two ligands as well as two O atoms from two methanol molecules. Intermolecular O—H⋯N hydrogen bonds between the hydroxy group of methanol and a pyrazole N atom link the molecules, forming a two-dimensional network parallel to (100).

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Harrop et al. (2003 ); Yu et al. (1993 ); Wu et al. (1993 ). For the antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997 , 2004 ).

Experimental

Crystal data

[Ni(C₁₇H₁₂ClN₂O₂)₂(CH₄O)₂]
M_r = 746.27
Monoclinic, P 2₁ /c
a = 11.8398 (7) Å
b = 12.3162 (7) Å
c = 13.2104 (8) Å
β = 114.706 (1)°
V = 1750.03 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.834, T_max = 0.872
8808 measured reflections
3089 independent reflections
2534 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.03
3089 reflections
225 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2ⁱ	0.85	2.00	2.795 (2)	156
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; 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, global. DOI: https://doi.org/10.1107/S1600536810038973/bh2312sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810038973/bh2312Isup2.hkl

checkCIF report

Comment top

In recent years, Schiff base complexes with metals have generated a wide interest because they possess a large spectrum of biological, pharmaceutical and catalytic properties, such as antitumor and antioxidative activities, as well as the inhibition of lipid peroxidation, among others (Harrop et al., 2003; Yu et al., 1993; Wu et al., 1993). The Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes have also been widely studied for their high antibacterial activity (Li et al., 1997, 2004). In this paper, we report the synthesis and crystal structure of the title compound, (I), containing a β-ketoamine ligand with organic chlorine, based on a pyrazolone derivative.

The molecular structure of (I) reveals a neutral centrosymmetric mononuclear complex, with the asymmetric unit comprising a half molecule (Fig. 1). The distorted octahedral Ni^II center, which locates on a crystallographic inversion center, is coordinated to four O donors from a couple of ligands, and two O atoms from two methanol molecules. The equatorial Ni—O bond lengths are comparable with an average value of 2.0345 (6) Å, which are significantly shorter than that of the axial Ni—O distance of 2.0651 (16) Å. The cis bond angles around the Ni^II center range from 88.47 (7) to 91.53 (7)°. Intermolecular hydrogen bonds (Table 1) link the molecules together, forming a two-dimensional network (Fig. 2).

Related literature top

For general background to Schiff base compounds in coordination chemistry, see: Harrop et al. (2003); Yu et al. (1993); Wu et al. (1993). For the antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997, 2004).

Experimental top

A mixture of Ni(OAc)₂.4H₂O (24.8 mg, 0.10 mmol), 4(Z)-4-((4-chlorophenyl)(hydroxy)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (62.6 mg, 0.20 mmol) and methanol (12 ml) was heated at 433 K for 2 days in a sealed Teflon-lined stainless steel vessel (20 mL) under autogenous pressure. After the reaction system was slowly cooled down to the room temperature, it was placed to stand at room temperature for a period of four weeks, affording green block crystals in 60% yield.

Structure description top

For general background to Schiff base compounds in coordination chemistry, see: Harrop et al. (2003); Yu et al. (1993); Wu et al. (1993). For the antibacterial properties of Schiff bases derived from 4-acyl-5-pyrazolones and their metal complexes, see: Li et al. (1997, 2004).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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 (I), with anisotropic displacement ellipsoids drawn at the 30° probability level. [Symmetry code:(i)1-x,-y,-z.]
	Fig. 2. The two-dimensional supra-molecular network of (I) produced by the inter-molecular O-H···N weak hydrogen-bonding interactions.

Bis[4-(4-chlorobenzoyl)-3-methyl-1-phenyl-1H-pyrazol-5-olato- κ²O,O']bis(methanol-κO)nickel(II) top

Crystal data top

[Ni(C₁₇H₁₂ClN₂O₂)₂(CH₄O)₂]	F(000) = 772
M_r = 746.27	D_x = 1.416 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3041 reflections
a = 11.8398 (7) Å	θ = 2.4–25.4°
b = 12.3162 (7) Å	µ = 0.76 mm⁻¹
c = 13.2104 (8) Å	T = 296 K
β = 114.706 (1)°	Block, green
V = 1750.03 (18) Å³	0.24 × 0.22 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2534 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −14→8
T_min = 0.834, T_max = 0.872	k = −14→14
8808 measured reflections	l = −15→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0466P)² + 0.7427P] where P = (F_o² + 2F_c²)/3
3089 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³
0 constraints

Crystal data top

[Ni(C₁₇H₁₂ClN₂O₂)₂(CH₄O)₂]	V = 1750.03 (18) Å³
M_r = 746.27	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8398 (7) Å	µ = 0.76 mm⁻¹
b = 12.3162 (7) Å	T = 296 K
c = 13.2104 (8) Å	0.24 × 0.22 × 0.18 mm
β = 114.706 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3089 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2534 reflections with I > 2σ(I)
T_min = 0.834, T_max = 0.872	R_int = 0.021
8808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
3089 reflections	Δρ_min = −0.34 e Å⁻³
225 parameters

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

	x	y	z	U_iso*/U_eq
Ni1	0.5000	0.0000	0.0000	0.03539 (14)
Cl1	0.04928 (8)	0.55881 (7)	−0.33203 (7)	0.0790 (3)
O1	0.39759 (15)	0.13217 (12)	−0.07861 (12)	0.0421 (4)
O2	0.61693 (14)	0.09579 (12)	0.12531 (12)	0.0423 (4)
O3	0.39208 (16)	−0.01739 (13)	0.08784 (14)	0.0476 (4)
H3A	0.3970	−0.0784	0.1196	0.071*
C1	0.1856 (2)	0.2801 (2)	−0.1767 (2)	0.0613 (7)
H1	0.1567	0.2100	−0.1765	0.074*
C2	0.1060 (3)	0.3578 (2)	−0.2451 (3)	0.0667 (8)
H2	0.0234	0.3406	−0.2893	0.080*
C3	0.1491 (3)	0.4595 (2)	−0.2474 (2)	0.0529 (6)
C4	0.2709 (3)	0.4855 (2)	−0.1845 (2)	0.0609 (8)
H4	0.3006	0.5545	−0.1887	0.073*
C5	0.3491 (2)	0.4082 (2)	−0.1151 (2)	0.0553 (7)
H5	0.4317	0.4258	−0.0716	0.066*
C6	0.3072 (2)	0.30524 (18)	−0.10879 (18)	0.0407 (5)
C7	0.3925 (2)	0.22122 (17)	−0.03395 (18)	0.0379 (5)
C8	0.4653 (2)	0.24382 (18)	0.08010 (18)	0.0403 (5)
C9	0.4556 (2)	0.32600 (19)	0.1533 (2)	0.0457 (6)
N2	0.54567 (19)	0.31717 (16)	0.25322 (17)	0.0483 (5)
N1	0.61951 (18)	0.22984 (15)	0.24962 (15)	0.0427 (5)
C11	0.5709 (2)	0.17991 (17)	0.14723 (18)	0.0376 (5)
C10	0.3568 (3)	0.4093 (2)	0.1350 (2)	0.0698 (9)
H10A	0.3632	0.4354	0.2056	0.105*
H10B	0.2764	0.3771	0.0947	0.105*
H10C	0.3674	0.4687	0.0928	0.105*
C12	0.7225 (2)	0.19863 (18)	0.34771 (19)	0.0429 (6)
C13	0.7201 (3)	0.2167 (2)	0.4506 (2)	0.0538 (7)
H13	0.6501	0.2468	0.4548	0.065*
C14	0.8222 (3)	0.1898 (2)	0.5459 (2)	0.0695 (9)
H14	0.8211	0.2023	0.6149	0.083*
C15	0.9255 (3)	0.1449 (3)	0.5412 (2)	0.0766 (10)
H15	0.9942	0.1273	0.6063	0.092*
C16	0.9266 (3)	0.1260 (3)	0.4383 (3)	0.0714 (9)
H16	0.9963	0.0949	0.4345	0.086*
C17	0.8256 (2)	0.1529 (2)	0.3416 (2)	0.0543 (7)
H17	0.8270	0.1402	0.2727	0.065*
C20	0.2607 (3)	−0.0031 (2)	0.0339 (3)	0.0652 (8)
H20A	0.2394	0.0676	0.0512	0.098*
H20B	0.2207	−0.0576	0.0595	0.098*
H20C	0.2335	−0.0097	−0.0452	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0489 (3)	0.0260 (2)	0.0311 (2)	0.00240 (17)	0.01650 (18)	−0.00093 (16)
Cl1	0.0751 (5)	0.0799 (6)	0.0691 (5)	0.0358 (4)	0.0176 (4)	0.0205 (4)
O1	0.0575 (10)	0.0310 (8)	0.0355 (8)	0.0043 (7)	0.0170 (7)	−0.0009 (7)
O2	0.0486 (9)	0.0340 (8)	0.0383 (9)	0.0065 (7)	0.0124 (7)	−0.0067 (7)
O3	0.0580 (11)	0.0439 (10)	0.0459 (10)	0.0027 (8)	0.0266 (8)	0.0103 (7)
C1	0.0505 (16)	0.0468 (16)	0.0721 (19)	−0.0082 (12)	0.0114 (14)	0.0034 (13)
C2	0.0428 (15)	0.067 (2)	0.0699 (19)	−0.0032 (13)	0.0034 (14)	0.0038 (15)
C3	0.0528 (16)	0.0539 (16)	0.0483 (15)	0.0150 (13)	0.0173 (13)	0.0065 (12)
C4	0.0630 (18)	0.0404 (15)	0.0701 (19)	0.0015 (12)	0.0187 (15)	0.0158 (13)
C5	0.0474 (15)	0.0422 (14)	0.0627 (17)	−0.0024 (12)	0.0096 (13)	0.0075 (12)
C6	0.0470 (14)	0.0345 (12)	0.0400 (13)	0.0002 (10)	0.0175 (11)	−0.0025 (10)
C7	0.0440 (13)	0.0309 (12)	0.0397 (12)	−0.0017 (9)	0.0186 (10)	0.0005 (9)
C8	0.0500 (14)	0.0307 (12)	0.0375 (12)	0.0033 (10)	0.0155 (11)	−0.0027 (10)
C9	0.0525 (15)	0.0374 (13)	0.0437 (13)	0.0047 (11)	0.0165 (12)	−0.0054 (11)
N2	0.0574 (13)	0.0392 (11)	0.0458 (12)	0.0072 (9)	0.0191 (10)	−0.0108 (9)
N1	0.0508 (12)	0.0353 (10)	0.0380 (10)	0.0050 (9)	0.0147 (9)	−0.0063 (8)
C11	0.0464 (13)	0.0319 (11)	0.0348 (12)	−0.0017 (10)	0.0174 (10)	−0.0035 (9)
C10	0.080 (2)	0.0624 (18)	0.0577 (18)	0.0262 (16)	0.0197 (16)	−0.0109 (14)
C12	0.0522 (14)	0.0317 (12)	0.0372 (12)	−0.0025 (10)	0.0112 (11)	−0.0012 (10)
C13	0.0681 (18)	0.0466 (15)	0.0426 (14)	0.0009 (13)	0.0192 (13)	−0.0045 (11)
C14	0.099 (2)	0.0566 (18)	0.0400 (15)	0.0049 (17)	0.0166 (16)	−0.0028 (13)
C15	0.084 (2)	0.065 (2)	0.0479 (17)	0.0118 (17)	−0.0044 (16)	−0.0003 (14)
C16	0.0635 (19)	0.072 (2)	0.0637 (19)	0.0156 (16)	0.0115 (15)	0.0039 (16)
C17	0.0572 (16)	0.0520 (16)	0.0481 (15)	0.0063 (13)	0.0166 (13)	0.0006 (12)
C20	0.0612 (19)	0.0661 (19)	0.079 (2)	0.0106 (14)	0.0405 (16)	0.0183 (15)

Geometric parameters (Å, º) top

Ni1—O2	2.0330 (15)	C8—C9	1.438 (3)
Ni1—O2ⁱ	2.0330 (15)	C9—N2	1.309 (3)
Ni1—O1	2.0361 (15)	C9—C10	1.497 (3)
Ni1—O1ⁱ	2.0361 (15)	N2—N1	1.399 (3)
Ni1—O3ⁱ	2.0651 (16)	N1—C11	1.374 (3)
Ni1—O3	2.0651 (16)	N1—C12	1.411 (3)
Cl1—C3	1.744 (3)	C10—H10A	0.9600
O1—C7	1.259 (3)	C10—H10B	0.9600
O2—C11	1.259 (3)	C10—H10C	0.9600
O3—C20	1.425 (3)	C12—C17	1.378 (3)
O3—H3A	0.8505	C12—C13	1.389 (3)
C1—C6	1.376 (3)	C13—C14	1.373 (4)
C1—C2	1.382 (4)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.367 (4)
C2—C3	1.357 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—C16	1.385 (4)
C3—C4	1.368 (4)	C15—H15	0.9300
C4—C5	1.377 (4)	C16—C17	1.376 (4)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.376 (3)	C17—H17	0.9300
C5—H5	0.9300	C20—H20A	0.9600
C6—C7	1.494 (3)	C20—H20B	0.9600
C7—C8	1.416 (3)	C20—H20C	0.9600
C8—C11	1.429 (3)

O2—Ni1—O2ⁱ	180.00 (10)	C7—C8—C9	132.1 (2)
O2—Ni1—O1	90.52 (6)	C11—C8—C9	105.41 (19)
O2ⁱ—Ni1—O1	89.48 (6)	N2—C9—C8	111.0 (2)
O2—Ni1—O1ⁱ	89.48 (6)	N2—C9—C10	118.2 (2)
O2ⁱ—Ni1—O1ⁱ	90.52 (6)	C8—C9—C10	130.6 (2)
O1—Ni1—O1ⁱ	180.00 (5)	C9—N2—N1	106.68 (18)
O2—Ni1—O3ⁱ	91.53 (7)	C11—N1—N2	111.53 (18)
O2ⁱ—Ni1—O3ⁱ	88.47 (7)	C11—N1—C12	128.86 (19)
O1—Ni1—O3ⁱ	90.39 (6)	N2—N1—C12	119.36 (18)
O1ⁱ—Ni1—O3ⁱ	89.61 (6)	O2—C11—N1	123.5 (2)
O2—Ni1—O3	88.47 (7)	O2—C11—C8	131.4 (2)
O2ⁱ—Ni1—O3	91.53 (7)	N1—C11—C8	105.20 (18)
O1—Ni1—O3	89.61 (6)	C9—C10—H10A	109.5
O1ⁱ—Ni1—O3	90.39 (6)	C9—C10—H10B	109.5
O3ⁱ—Ni1—O3	180.00 (6)	H10A—C10—H10B	109.5
C7—O1—Ni1	126.33 (14)	C9—C10—H10C	109.5
C11—O2—Ni1	116.87 (14)	H10A—C10—H10C	109.5
C20—O3—Ni1	120.58 (16)	H10B—C10—H10C	109.5
C20—O3—H3A	101.0	C17—C12—C13	120.3 (2)
Ni1—O3—H3A	116.0	C17—C12—N1	120.3 (2)
C6—C1—C2	120.9 (3)	C13—C12—N1	119.4 (2)
C6—C1—H1	119.6	C14—C13—C12	119.2 (3)
C2—C1—H1	119.6	C14—C13—H13	120.4
C3—C2—C1	119.5 (3)	C12—C13—H13	120.4
C3—C2—H2	120.2	C15—C14—C13	121.1 (3)
C1—C2—H2	120.2	C15—C14—H14	119.4
C2—C3—C4	120.9 (2)	C13—C14—H14	119.4
C2—C3—Cl1	120.0 (2)	C14—C15—C16	119.3 (3)
C4—C3—Cl1	119.0 (2)	C14—C15—H15	120.4
C3—C4—C5	119.1 (2)	C16—C15—H15	120.4
C3—C4—H4	120.4	C17—C16—C15	120.6 (3)
C5—C4—H4	120.4	C17—C16—H16	119.7
C6—C5—C4	121.3 (2)	C15—C16—H16	119.7
C6—C5—H5	119.4	C16—C17—C12	119.4 (3)
C4—C5—H5	119.4	C16—C17—H17	120.3
C5—C6—C1	118.2 (2)	C12—C17—H17	120.3
C5—C6—C7	121.1 (2)	O3—C20—H20A	109.5
C1—C6—C7	120.6 (2)	O3—C20—H20B	109.5
O1—C7—C8	122.9 (2)	H20A—C20—H20B	109.5
O1—C7—C6	116.40 (19)	O3—C20—H20C	109.5
C8—C7—C6	120.69 (19)	H20A—C20—H20C	109.5
C7—C8—C11	122.5 (2)	H20B—C20—H20C	109.5

O2—Ni1—O1—C7	−22.71 (18)	C6—C7—C8—C9	18.3 (4)
O2ⁱ—Ni1—O1—C7	157.29 (18)	C7—C8—C9—N2	−179.0 (2)
O3ⁱ—Ni1—O1—C7	−114.24 (18)	C11—C8—C9—N2	1.7 (3)
O3—Ni1—O1—C7	65.76 (18)	C7—C8—C9—C10	6.5 (5)
O1—Ni1—O2—C11	30.69 (16)	C11—C8—C9—C10	−172.8 (3)
O1ⁱ—Ni1—O2—C11	−149.31 (16)	C8—C9—N2—N1	0.8 (3)
O3ⁱ—Ni1—O2—C11	121.10 (16)	C10—C9—N2—N1	176.1 (2)
O3—Ni1—O2—C11	−58.90 (16)	C9—N2—N1—C11	−3.2 (3)
O2—Ni1—O3—C20	132.23 (18)	C9—N2—N1—C12	−177.8 (2)
O2ⁱ—Ni1—O3—C20	−47.77 (18)	Ni1—O2—C11—N1	155.00 (18)
O1—Ni1—O3—C20	41.70 (18)	Ni1—O2—C11—C8	−25.3 (3)
O1ⁱ—Ni1—O3—C20	−138.30 (18)	N2—N1—C11—O2	−176.1 (2)
C6—C1—C2—C3	1.6 (5)	C12—N1—C11—O2	−2.0 (4)
C1—C2—C3—C4	1.3 (5)	N2—N1—C11—C8	4.1 (3)
C1—C2—C3—Cl1	−179.2 (2)	C12—N1—C11—C8	178.1 (2)
C2—C3—C4—C5	−2.5 (5)	C7—C8—C11—O2	−2.6 (4)
Cl1—C3—C4—C5	178.1 (2)	C9—C8—C11—O2	176.8 (2)
C3—C4—C5—C6	0.7 (5)	C7—C8—C11—N1	177.1 (2)
C4—C5—C6—C1	2.1 (4)	C9—C8—C11—N1	−3.4 (3)
C4—C5—C6—C7	179.5 (3)	C11—N1—C12—C17	36.5 (4)
C2—C1—C6—C5	−3.3 (4)	N2—N1—C12—C17	−149.9 (2)
C2—C1—C6—C7	179.3 (3)	C11—N1—C12—C13	−145.0 (2)
Ni1—O1—C7—C8	3.6 (3)	N2—N1—C12—C13	28.7 (3)
Ni1—O1—C7—C6	−178.18 (14)	C17—C12—C13—C14	0.8 (4)
C5—C6—C7—O1	−126.5 (2)	N1—C12—C13—C14	−177.7 (2)
C1—C6—C7—O1	50.9 (3)	C12—C13—C14—C15	−0.4 (4)
C5—C6—C7—C8	51.8 (3)	C13—C14—C15—C16	−0.3 (5)
C1—C6—C7—C8	−130.8 (3)	C14—C15—C16—C17	0.6 (5)
O1—C7—C8—C11	15.7 (4)	C15—C16—C17—C12	−0.2 (5)
C6—C7—C8—C11	−162.5 (2)	C13—C12—C17—C16	−0.5 (4)
O1—C7—C8—C9	−163.6 (2)	N1—C12—C17—C16	178.0 (3)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2ⁱⁱ	0.85	2.00	2.795 (2)	156

Symmetry code: (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ni(C₁₇H₁₂ClN₂O₂)₂(CH₄O)₂]
M_r	746.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.8398 (7), 12.3162 (7), 13.2104 (8)
β (°)	114.706 (1)
V (Å³)	1750.03 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.834, 0.872
No. of measured, independent and observed [I > 2σ(I)] reflections	8808, 3089, 2534
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.03
No. of reflections	3089
No. of parameters	225
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.34

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), 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
O3—H3A···N2ⁱ	0.85	2.00	2.795 (2)	156.0

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 20771083).

References

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