[N,N'-Ethyl­enebis(salicylideneiminato)]nickel(II) chloro­form solvate

In the crystal structure of the title compound, [Cu(C₈H₇NO)₂]·CHCl₃, the nickel complex and the solvent mol­ecule both have crystallographic mirror symmetry. The Ni atom exists in square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.046
• wR factor = 0.147
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.507     0.764
            Tmin' and Tmax expected:      0.582     0.761
            RR' =      0.869
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.85
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         C9
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C8     -   C8_b   ...       1.41 Ang.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

[N,N'-Ethylenebis(salicylideneiminato)]nickel(II) chloroform solvate

Crystal data

[Cu(C8H7NO)2]·CHCl3	F(000) = 904
Mr = 444.37	Dx = 1.616 Mg m^−3
Orthorhombic, Pnnm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2 2n	Cell parameters from 14841 reflections
a = 6.997 (1) Å	θ = 3.1–27.5°
b = 14.221 (3) Å	µ = 1.51 mm^−1
c = 18.355 (4) Å	T = 295 K
V = 1826.4 (6) Å^3	Prism, red
Z = 4	0.35 × 0.26 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2150 independent reflections
Radiation source: fine-focus sealed tube	1766 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→8
Tmin = 0.507, Tmax = 0.764	k = −18→18
16264 measured reflections	l = −22→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0952P)^2 + 0.4858P] where P = (Fo^2 + 2Fc^2)/3
2150 reflections	(Δ/σ)max = 0.001
118 parameters	Δρmax = 0.73 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.28236 (7)	0.53352 (3)	0.5000	0.0510 (2)
Cl1	0.5341 (3)	0.8731 (1)	0.5000	0.1346 (8)
Cl2	0.1787 (3)	0.8807 (1)	0.42380 (7)	0.1529 (8)
O1	0.3366 (3)	0.6257 (1)	0.4324 (1)	0.0613 (5)
N1	0.2246 (4)	0.4430 (2)	0.4316 (2)	0.0644 (6)
C1	0.3311 (4)	0.6187 (2)	0.3608 (2)	0.062 (1)
C2	0.3954 (6)	0.6952 (3)	0.3185 (2)	0.080 (1)
C3	0.3875 (7)	0.6910 (4)	0.2437 (2)	0.101 (1)
C4	0.3129 (7)	0.6139 (4)	0.2078 (2)	0.106 (2)
C5	0.2545 (6)	0.5382 (4)	0.2472 (2)	0.089 (1)
C6	0.2649 (5)	0.5373 (3)	0.3243 (2)	0.069 (1)
C7	0.2185 (4)	0.4541 (3)	0.3618 (2)	0.072 (1)
C8	0.1844 (8)	0.3501 (3)	0.4617 (2)	0.110 (2)
C9	0.2939 (8)	0.8391 (4)	0.5000	0.081 (1)
H2	0.4433	0.7487	0.3412	0.096*
H3	0.4335	0.7414	0.2166	0.121*
H4	0.3029	0.6138	0.1573	0.128*
H5	0.2065	0.4858	0.2230	0.107*
H7	0.1804	0.4028	0.3339	0.086*
H8a	0.0607	0.3290	0.4443	0.132*
H8b	0.2799	0.3061	0.4443	0.132*
H9	0.2873	0.7702	0.5000	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0453 (3)	0.0457 (3)	0.0621 (3)	0.0057 (2)	0.000	0.000
Cl1	0.119 (1)	0.0677 (9)	0.217 (2)	−0.0041 (9)	0.000	0.000
Cl2	0.211 (2)	0.153 (1)	0.0949 (8)	0.076 (1)	−0.0315 (9)	0.0025 (8)
O1	0.074 (1)	0.055 (1)	0.055 (1)	0.004 (1)	0.002 (1)	0.001 (1)
N1	0.051 (1)	0.056 (1)	0.086 (2)	0.003 (1)	0.003 (1)	−0.012 (1)
C1	0.059 (2)	0.068 (2)	0.059 (2)	0.017 (1)	0.003 (1)	0.000 (1)
C2	0.091 (2)	0.082 (2)	0.068 (2)	0.020 (2)	0.006 (2)	0.012 (1)
C3	0.112 (3)	0.120 (4)	0.071 (2)	0.037 (3)	0.010 (2)	0.028 (2)
C4	0.108 (3)	0.153 (5)	0.058 (2)	0.038 (3)	−0.004 (2)	−0.004 (2)
C5	0.072 (2)	0.129 (4)	0.066 (2)	0.018 (2)	−0.005 (2)	−0.022 (2)
C6	0.051 (2)	0.092 (2)	0.065 (2)	0.015 (1)	−0.004 (1)	−0.015 (1)
C7	0.052 (2)	0.078 (2)	0.085 (2)	0.004 (1)	−0.001 (1)	−0.028 (2)
C8	0.144 (4)	0.058 (2)	0.127 (3)	−0.022 (2)	0.033 (3)	−0.014 (2)
C9	0.111 (4)	0.056 (3)	0.077 (3)	0.013 (2)	0.000	0.000

Geometric parameters (Å, º)

Ni1—O1	1.844 (2)	C4—C5	1.360 (7)
Ni1—O1^i	1.844 (2)	C5—C6	1.418 (5)
Ni1—N1	1.843 (3)	C6—C7	1.407 (5)
Ni1—N1^i	1.843 (3)	C8—C8^i	1.406 (9)
Cl1—C9	1.749 (6)	C9—Cl2^i	1.719 (3)
Cl2—C9	1.719 (3)	C2—H2	0.93
O1—C1	1.318 (3)	C3—H3	0.93
N1—C7	1.292 (5)	C4—H4	0.93
N1—C8	1.459 (5)	C5—H5	0.93
C1—C2	1.411 (5)	C7—H7	0.93
C1—C6	1.415 (5)	C8—H8a	0.97
C2—C3	1.375 (5)	C8—H8b	0.97
C3—C4	1.382 (8)	C9—H9	0.98
O1—Ni1—O1^i	84.6 (1)	Cl2^i—C9—Cl2	108.9 (3)
O1—Ni1—N1	94.8 (1)	Cl2^i—C9—Cl1	110.8 (2)
O1—Ni1—N1^i	178.9 (1)	Cl2—C9—Cl1	110.8 (2)
O1^i—Ni1—N1	178.9 (1)	C3—C2—H2	119.9
O1^i—Ni1—N1^i	94.8 (1)	C1—C2—H2	119.9
N1—Ni1—N1^i	85.9 (2)	C2—C3—H3	119.1
C1—O1—Ni1	127.7 (2)	C4—C3—H3	119.1
C7—N1—C8	118.6 (3)	C5—C4—H4	120.4
C7—N1—Ni1	126.7 (2)	C3—C4—H4	120.4
C8—N1—Ni1	114.6 (3)	C4—C5—H5	119.2
O1—C1—C2	118.8 (3)	C6—C5—H5	119.2
O1—C1—C6	122.9 (3)	N1—C7—H7	117.3
C2—C1—C6	118.3 (3)	C6—C7—H7	117.3
C3—C2—C1	120.2 (4)	C8^i—C8—H8a	109.2
C2—C3—C4	121.7 (5)	N1—C8—H8a	109.2
C5—C4—C3	119.2 (4)	C8^i—C8—H8b	109.2
C4—C5—C6	121.5 (4)	N1—C8—H8b	109.2
C7—C6—C1	122.2 (3)	H8a—C8—H8b	107.9
C7—C6—C5	118.9 (4)	Cl2^i—C9—H9	108.8
C1—C6—C5	118.8 (4)	Cl2—C9—H9	108.8
N1—C7—C6	125.4 (3)	Cl1—C9—H9	108.8
C8^i—C8—N1	112.2 (2)
N1—Ni1—O1—C1	−0.4 (2)	O1—C1—C6—C7	−6.7 (5)
O1^i—Ni1—O1—C1	−179.5 (2)	C2—C1—C6—C7	172.7 (3)
N1^i—Ni1—N1—C7	175.1 (2)	O1—C1—C6—C5	176.6 (3)
O1—Ni1—N1—C7	−3.9 (3)	C2—C1—C6—C5	−4.0 (5)
N1^i—Ni1—N1—C8	−5.5 (3)	C4—C5—C6—C7	−174.3 (4)
O1—Ni1—N1—C8	175.4 (3)	C4—C5—C6—C1	2.4 (6)
Ni1—O1—C1—C2	−174.1 (2)	C8—N1—C7—C6	−175.9 (4)
Ni1—O1—C1—C6	5.3 (4)	Ni1—N1—C7—C6	3.4 (5)
O1—C1—C2—C3	−178.5 (3)	C1—C6—C7—N1	2.3 (5)
C6—C1—C2—C3	2.0 (5)	C5—C6—C7—N1	178.9 (3)
C1—C2—C3—C4	1.6 (6)	C7—N1—C8—C8^i	−176.2 (2)
C2—C3—C4—C5	−3.3 (7)	Ni1—N1—C8—C8^i	4.4 (3)
C3—C4—C5—C6	1.2 (7)

Symmetry code: (i) x, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.98	2.43	3.292 (5)	147
C9—H9···O1^i	0.98	2.43	3.292 (5)	147

Symmetry code: (i) x, y, −z+1.