Bis(4-acetyl-3-methyl-1-phenyl-1H-pyrazol-5-olato-κO,O')bis-(N,N-dimethyl-formamide-κO)nickel(II).

The title complex, [Ni(C(12)H(11)N(2)O(2))(2)(C(3)H(7)NO)(2)], lies on on an inversion center. The Ni(II) ion is coordinated in a slightly distorted octa-hedral coordination enviroment by four O atoms from two bis-chelating 4-acety-3-methyl-1-phenyl-1H-pyrazol-5-olate ligands in the equatorial plane and two O atoms from two N,N-dimethyl-formamide ligands in the axial sites. In the crystal structure, weak inter-molecular π-π stacking inter-actions with centroid-centroid distances of 3.7467 (13) Å link mol-ecules into chains extending alongthe b axis.

Related literature

For related structures: Shi et al. (2005 ▶); Zhu et al. (2010a ▶,b ▶, 2005 ▶).

Experimental

Crystal data

[Ni(C12H11N2O2)2(C3H7NO)2]

M = 635.36

Monoclinic,

a = 8.7201 (17) Å

b = 17.119 (3) Å

c = 9.852 (2) Å

β = 101.56 (3)°

V = 1440.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.73 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.868, T max = 0.931

10320 measured reflections

2529 independent reflections

2279 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.078

S = 1.09

2529 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810026231/lh5075sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810026231/lh5075Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C12H11N2O2)2(C3H7NO)2]	F(000) = 668
Mr = 635.36	Dx = 1.464 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4482 reflections
a = 8.7201 (17) Å	θ = 2.4–27.9°
b = 17.119 (3) Å	µ = 0.73 mm−1
c = 9.852 (2) Å	T = 113 K
β = 101.56 (3)°	Block, green
V = 1440.9 (5) Å3	0.20 × 0.18 × 0.10 mm
Z = 2

Rigaku Saturn CCD diffractometer	2529 independent reflections
Radiation source: rotating anode	2279 reflections with I > 2σ(I)
confocal	Rint = 0.031
Detector resolution: 7.31 pixels mm-1	θmax = 25.0°, θmin = 2.4°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −19→20
Tmin = 0.868, Tmax = 0.931	l = −11→11
10320 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.048P)2 + 0.3836P] where P = (Fo2 + 2Fc2)/3
2529 reflections	(Δ/σ)max = 0.001
200 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ni1	0.5000	1.0000	0.5000	0.01056 (12)
O1	0.58951 (13)	1.05337 (7)	0.68398 (11)	0.0138 (3)
O2	0.41750 (13)	0.91066 (7)	0.60044 (12)	0.0145 (3)
O3	0.71254 (13)	0.94193 (7)	0.51507 (12)	0.0147 (3)
N1	0.71370 (16)	1.03649 (8)	0.91454 (14)	0.0136 (3)
N2	0.73040 (17)	0.97910 (9)	1.01841 (15)	0.0167 (3)
N3	0.92677 (16)	0.91367 (8)	0.42588 (15)	0.0141 (3)
C1	0.62073 (19)	1.01164 (9)	0.79249 (18)	0.0121 (4)
C2	0.57338 (19)	0.93439 (10)	0.82039 (18)	0.0134 (4)
C3	0.64609 (19)	0.91963 (10)	0.96176 (18)	0.0153 (4)
C4	0.6431 (2)	0.84786 (11)	1.04694 (19)	0.0208 (4)
H4A	0.7047	0.8567	1.1404	0.031*
H4B	0.6880	0.8041	1.0040	0.031*
H4C	0.5348	0.8356	1.0525	0.031*
C5	0.46612 (18)	0.88950 (10)	0.72430 (17)	0.0124 (4)
C6	0.4005 (2)	0.81431 (10)	0.76739 (18)	0.0185 (4)
H6A	0.3372	0.7888	0.6860	0.028*
H6B	0.3348	0.8254	0.8350	0.028*
H6C	0.4865	0.7797	0.8092	0.028*
C7	0.79488 (19)	1.10812 (10)	0.94735 (17)	0.0134 (4)
C8	0.74278 (19)	1.17723 (10)	0.87719 (17)	0.0145 (4)
H8	0.6550	1.1766	0.8025	0.017*
C9	0.8205 (2)	1.24649 (10)	0.91776 (18)	0.0177 (4)
H9	0.7846	1.2936	0.8709	0.021*
C10	0.9504 (2)	1.24833 (11)	1.02602 (19)	0.0206 (4)
H10	1.0017	1.2963	1.0544	0.025*
C11	1.0036 (2)	1.17911 (11)	1.09167 (18)	0.0212 (4)
H11	1.0938	1.1795	1.1640	0.025*
C12	0.9269 (2)	1.10923 (10)	1.05317 (18)	0.0174 (4)
H12	0.9646	1.0621	1.0990	0.021*
C13	0.78377 (19)	0.94216 (10)	0.41739 (18)	0.0138 (4)
H13	0.7326	0.9641	0.3316	0.017*
C14	1.0109 (2)	0.87896 (11)	0.5542 (2)	0.0208 (4)
H14A	0.9697	0.8998	0.6323	0.031*
H14B	1.1225	0.8916	0.5665	0.031*
H14C	0.9973	0.8221	0.5500	0.031*
C15	1.0048 (2)	0.91441 (11)	0.30838 (19)	0.0210 (4)
H15A	0.9379	0.9406	0.2298	0.031*
H15B	1.0247	0.8606	0.2826	0.031*
H15C	1.1044	0.9425	0.3337	0.031*

	U11	U22	U33	U12	U13	U23
Ni1	0.01054 (17)	0.01073 (18)	0.00993 (18)	0.00035 (11)	0.00088 (12)	−0.00072 (11)
O1	0.0168 (6)	0.0137 (6)	0.0102 (6)	−0.0004 (5)	0.0011 (5)	0.0003 (5)
O2	0.0146 (6)	0.0137 (6)	0.0149 (7)	−0.0005 (4)	0.0023 (5)	−0.0013 (5)
O3	0.0136 (6)	0.0163 (6)	0.0145 (6)	0.0012 (5)	0.0035 (5)	−0.0007 (5)
N1	0.0177 (7)	0.0117 (8)	0.0104 (7)	−0.0010 (6)	0.0008 (6)	0.0010 (6)
N2	0.0196 (8)	0.0168 (8)	0.0123 (8)	−0.0003 (6)	−0.0004 (6)	0.0034 (6)
N3	0.0129 (7)	0.0145 (8)	0.0150 (7)	0.0012 (5)	0.0031 (6)	0.0008 (6)
C1	0.0097 (8)	0.0145 (9)	0.0122 (9)	0.0020 (6)	0.0022 (6)	−0.0020 (7)
C2	0.0131 (8)	0.0122 (9)	0.0149 (9)	0.0014 (6)	0.0028 (7)	0.0009 (7)
C3	0.0145 (8)	0.0154 (9)	0.0158 (9)	0.0002 (7)	0.0028 (7)	0.0003 (7)
C4	0.0226 (9)	0.0202 (10)	0.0177 (9)	−0.0033 (7)	−0.0006 (7)	0.0049 (8)
C5	0.0113 (8)	0.0128 (8)	0.0134 (9)	0.0039 (6)	0.0032 (7)	−0.0016 (7)
C6	0.0221 (9)	0.0156 (9)	0.0173 (9)	−0.0041 (7)	0.0030 (7)	−0.0005 (7)
C7	0.0147 (8)	0.0157 (9)	0.0106 (8)	−0.0015 (7)	0.0048 (7)	−0.0027 (7)
C8	0.0133 (8)	0.0163 (9)	0.0137 (9)	0.0001 (6)	0.0019 (7)	−0.0011 (7)
C9	0.0207 (9)	0.0152 (9)	0.0180 (9)	−0.0005 (7)	0.0060 (7)	0.0020 (7)
C10	0.0246 (9)	0.0190 (10)	0.0182 (10)	−0.0090 (8)	0.0039 (8)	−0.0015 (8)
C11	0.0196 (9)	0.0264 (11)	0.0151 (9)	−0.0068 (7)	−0.0024 (7)	0.0000 (8)
C12	0.0190 (9)	0.0170 (9)	0.0155 (9)	−0.0010 (7)	0.0018 (7)	0.0022 (7)
C13	0.0141 (8)	0.0104 (8)	0.0153 (9)	0.0000 (6)	−0.0010 (7)	−0.0010 (7)
C14	0.0160 (9)	0.0217 (10)	0.0234 (10)	0.0037 (7)	0.0007 (7)	0.0068 (8)
C15	0.0191 (9)	0.0236 (10)	0.0219 (10)	−0.0001 (7)	0.0083 (8)	−0.0008 (8)

Ni1—O2i	2.0301 (12)	C5—C6	1.504 (2)
Ni1—O2	2.0301 (12)	C6—H6A	0.9800
Ni1—O1i	2.0402 (12)	C6—H6B	0.9800
Ni1—O1	2.0402 (12)	C6—H6C	0.9800
Ni1—O3i	2.0820 (12)	C7—C12	1.390 (3)
Ni1—O3	2.0820 (12)	C7—C8	1.399 (2)
O1—C1	1.269 (2)	C8—C9	1.384 (2)
O2—C5	1.262 (2)	C8—H8	0.9500
O3—C13	1.246 (2)	C9—C10	1.392 (3)
N1—C1	1.376 (2)	C9—H9	0.9500
N1—N2	1.405 (2)	C10—C11	1.385 (3)
N1—C7	1.420 (2)	C10—H10	0.9500
N2—C3	1.313 (2)	C11—C12	1.386 (3)
N3—C13	1.326 (2)	C11—H11	0.9500
N3—C14	1.455 (2)	C12—H12	0.9500
N3—C15	1.456 (2)	C13—H13	0.9500
C1—C2	1.428 (2)	C14—H14A	0.9800
C2—C5	1.417 (2)	C14—H14B	0.9800
C2—C3	1.432 (2)	C14—H14C	0.9800
C3—C4	1.491 (2)	C15—H15A	0.9800
C4—H4A	0.9800	C15—H15B	0.9800
C4—H4B	0.9800	C15—H15C	0.9800
C4—H4C	0.9800
O2i—Ni1—O2	180.0	O2—C5—C6	116.45 (15)
O2i—Ni1—O1i	90.81 (5)	C2—C5—C6	120.89 (15)
O2—Ni1—O1i	89.19 (5)	C5—C6—H6A	109.5
O2i—Ni1—O1	89.19 (5)	C5—C6—H6B	109.5
O2—Ni1—O1	90.81 (5)	H6A—C6—H6B	109.5
O1i—Ni1—O1	180.0	C5—C6—H6C	109.5
O2i—Ni1—O3i	90.17 (5)	H6A—C6—H6C	109.5
O2—Ni1—O3i	89.84 (5)	H6B—C6—H6C	109.5
O1i—Ni1—O3i	88.50 (5)	C12—C7—C8	119.80 (16)
O1—Ni1—O3i	91.50 (5)	C12—C7—N1	118.86 (15)
O2i—Ni1—O3	89.83 (5)	C8—C7—N1	121.32 (15)
O2—Ni1—O3	90.16 (5)	C9—C8—C7	119.33 (16)
O1i—Ni1—O3	91.50 (5)	C9—C8—H8	120.3
O1—Ni1—O3	88.50 (5)	C7—C8—H8	120.3
O3i—Ni1—O3	179.999 (1)	C8—C9—C10	121.12 (17)
C1—O1—Ni1	118.40 (11)	C8—C9—H9	119.4
C5—O2—Ni1	127.18 (11)	C10—C9—H9	119.4
C13—O3—Ni1	121.20 (11)	C11—C10—C9	118.91 (17)
C1—N1—N2	112.16 (14)	C11—C10—H10	120.5
C1—N1—C7	130.19 (14)	C9—C10—H10	120.5
N2—N1—C7	117.63 (14)	C10—C11—C12	120.87 (17)
C3—N2—N1	105.38 (14)	C10—C11—H11	119.6
C13—N3—C14	120.62 (15)	C12—C11—H11	119.6
C13—N3—C15	122.03 (15)	C11—C12—C7	119.92 (17)
C14—N3—C15	117.34 (14)	C11—C12—H12	120.0
O1—C1—N1	123.46 (15)	C7—C12—H12	120.0
O1—C1—C2	131.43 (16)	O3—C13—N3	123.95 (16)
N1—C1—C2	105.10 (14)	O3—C13—H13	118.0
C5—C2—C1	123.45 (16)	N3—C13—H13	118.0
C5—C2—C3	131.18 (16)	N3—C14—H14A	109.5
C1—C2—C3	105.17 (14)	N3—C14—H14B	109.5
N2—C3—C2	112.18 (15)	H14A—C14—H14B	109.5
N2—C3—C4	118.10 (16)	N3—C14—H14C	109.5
C2—C3—C4	129.68 (16)	H14A—C14—H14C	109.5
C3—C4—H4A	109.5	H14B—C14—H14C	109.5
C3—C4—H4B	109.5	N3—C15—H15A	109.5
H4A—C4—H4B	109.5	N3—C15—H15B	109.5
C3—C4—H4C	109.5	H15A—C15—H15B	109.5
H4A—C4—H4C	109.5	N3—C15—H15C	109.5
H4B—C4—H4C	109.5	H15A—C15—H15C	109.5
O2—C5—C2	122.64 (15)	H15B—C15—H15C	109.5
O2i—Ni1—O1—C1	−156.12 (12)	N1—N2—C3—C2	0.82 (19)
O2—Ni1—O1—C1	23.88 (12)	N1—N2—C3—C4	178.73 (15)
O1i—Ni1—O1—C1	20 (22)	C5—C2—C3—N2	−175.27 (17)
O3i—Ni1—O1—C1	113.74 (12)	C1—C2—C3—N2	−0.32 (19)
O3—Ni1—O1—C1	−66.26 (12)	C5—C2—C3—C4	7.1 (3)
O2i—Ni1—O2—C5	97 (5)	C1—C2—C3—C4	−177.93 (17)
O1i—Ni1—O2—C5	157.07 (13)	Ni1—O2—C5—C2	10.4 (2)
O1—Ni1—O2—C5	−22.93 (13)	Ni1—O2—C5—C6	−171.37 (10)
O3i—Ni1—O2—C5	−114.44 (13)	C1—C2—C5—O2	8.4 (3)
O3—Ni1—O2—C5	65.57 (13)	C3—C2—C5—O2	−177.46 (16)
O2i—Ni1—O3—C13	−39.74 (12)	C1—C2—C5—C6	−169.79 (15)
O2—Ni1—O3—C13	140.26 (12)	C3—C2—C5—C6	4.4 (3)
O1i—Ni1—O3—C13	51.07 (13)	C1—N1—C7—C12	−154.26 (17)
O1—Ni1—O3—C13	−128.93 (13)	N2—N1—C7—C12	23.8 (2)
O3i—Ni1—O3—C13	82 (18)	C1—N1—C7—C8	26.9 (3)
C1—N1—N2—C3	−1.06 (18)	N2—N1—C7—C8	−155.00 (15)
C7—N1—N2—C3	−179.46 (14)	C12—C7—C8—C9	−2.4 (2)
Ni1—O1—C1—N1	164.19 (12)	N1—C7—C8—C9	176.44 (15)
Ni1—O1—C1—C2	−16.5 (2)	C7—C8—C9—C10	0.7 (2)
N2—N1—C1—O1	−179.70 (14)	C8—C9—C10—C11	1.3 (3)
C7—N1—C1—O1	−1.6 (3)	C9—C10—C11—C12	−1.6 (3)
N2—N1—C1—C2	0.86 (18)	C10—C11—C12—C7	0.0 (3)
C7—N1—C1—C2	179.00 (16)	C8—C7—C12—C11	2.0 (2)
O1—C1—C2—C5	−4.3 (3)	N1—C7—C12—C11	−176.81 (15)
N1—C1—C2—C5	175.11 (15)	Ni1—O3—C13—N3	172.39 (12)
O1—C1—C2—C3	−179.71 (17)	C14—N3—C13—O3	0.4 (3)
N1—C1—C2—C3	−0.33 (17)	C15—N3—C13—O3	179.29 (16)