{6,6'-Dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethylidyne)]diphenolato}nickel(II) chloro­form solvate

The title compound, [Ni(C₁₈H₁₈N₂O₄)]·CHCl₃, has been synthesized by the solid-state reaction of Ni(OAc)₂·4H₂O and the Schiff base ligand N,N'-ethyl­ene-bis­(3-methoxy­salicylaldehyde) [abbreviated as H₂(3-MeO-salen)]. The Ni atom adopts a slightly deformed square-planar coordination geometry in which the 3-MeO-salen ligand acts as a cis-N₂O₂ donor.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.041
• wR factor = 0.116
• Data-to-parameter ratio = 18.0

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:      0.509     0.775
            Tmin(prime) and Tmax expected:      0.654     0.775
            RR(prime) =      0.778
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.76
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C19

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   0 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: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

[N,N'-Bis(3-methoxysalicylidene)-1,2-ethanediyldiamino]nickel(II) chloroform solvate

Crystal data

[Ni(C18H18N2O4)]·CHCl3	F(000) = 1032
Mr = 504.42	Dx = 1.603 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16249 reflections
a = 11.381 (2) Å	θ = 3.1–27.5°
b = 13.842 (3) Å	µ = 1.34 mm^−1
c = 13.268 (3) Å	T = 296 K
β = 91.43 (3)°	Prism, brown
V = 2089.5 (8) Å^3	0.31 × 0.21 × 0.19 mm
Z = 4

Data collection

Rigaku RAXIS-RAPID diffractometer	4767 independent reflections
Radiation source: fine-focus sealed tube	3682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −14→14
Tmin = 0.509, Tmax = 0.775	k = −17→17
19480 measured reflections	l = −17→17

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0642P)^2 + 0.4559P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
4767 reflections	Δρmax = 0.93 e Å^−3
265 parameters	Δρmin = −0.71 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0030 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.04386 (2)	0.52021 (2)	0.37836 (2)	0.03693 (12)
Cl1	0.36147 (11)	0.46165 (8)	0.17518 (11)	0.1037 (4)
Cl2	0.28247 (11)	0.65875 (9)	0.16338 (9)	0.1054 (4)
Cl3	0.48918 (9)	0.61001 (9)	0.27803 (10)	0.1005 (4)
N1	−0.04144 (17)	0.40681 (15)	0.37763 (16)	0.0410 (5)
N2	−0.09779 (17)	0.58275 (16)	0.35819 (16)	0.0428 (5)
O1	0.18695 (14)	0.46057 (11)	0.39843 (14)	0.0439 (4)
O2	0.40558 (16)	0.41030 (13)	0.42879 (18)	0.0585 (5)
O3	0.13161 (15)	0.63236 (12)	0.38046 (14)	0.0459 (4)
O4	0.28959 (18)	0.76867 (15)	0.40517 (18)	0.0639 (6)
C1	0.2079 (2)	0.36731 (17)	0.39990 (18)	0.0393 (5)
C2	0.3269 (2)	0.33675 (18)	0.4152 (2)	0.0445 (6)
C3	0.3557 (3)	0.2400 (2)	0.4158 (2)	0.0545 (7)
H3A	0.4337	0.2212	0.4249	0.065*
C4	0.2682 (3)	0.1701 (2)	0.4027 (2)	0.0601 (8)
H4A	0.2884	0.1050	0.4029	0.072*
C5	0.1548 (3)	0.1961 (2)	0.3897 (2)	0.0522 (7)
H5A	0.0973	0.1488	0.3818	0.063*
C6	0.1220 (2)	0.29591 (17)	0.38812 (18)	0.0413 (5)
C7	0.5272 (2)	0.3866 (2)	0.4334 (3)	0.0679 (9)
H7A	0.5727	0.4446	0.4423	0.102*
H7B	0.5486	0.3555	0.3718	0.102*
H7C	0.5426	0.3438	0.4891	0.102*
C8	0.0000 (2)	0.32016 (19)	0.37902 (19)	0.0442 (6)
H8A	−0.0535	0.2695	0.3737	0.053*
C9	−0.1706 (2)	0.4205 (2)	0.3787 (2)	0.0514 (7)
H9A	−0.1981	0.4162	0.4472	0.062*
H9B	−0.2096	0.3708	0.3386	0.062*
C10	−0.1976 (2)	0.5187 (2)	0.3355 (3)	0.0570 (7)
H10A	−0.2106	0.5140	0.2631	0.068*
H10B	−0.2683	0.5444	0.3648	0.068*
C11	−0.1155 (2)	0.6745 (2)	0.3580 (2)	0.0474 (6)
H11A	−0.1925	0.6956	0.3478	0.057*
C12	−0.0267 (2)	0.74670 (18)	0.37211 (19)	0.0450 (6)
C13	−0.0614 (3)	0.8447 (2)	0.3751 (2)	0.0581 (7)
H13A	−0.1404	0.8605	0.3665	0.070*
C14	0.0179 (3)	0.9152 (2)	0.3903 (3)	0.0675 (9)
H14A	−0.0064	0.9793	0.3930	0.081*
C15	0.1372 (3)	0.8923 (2)	0.4022 (2)	0.0615 (8)
H15A	0.1918	0.9412	0.4142	0.074*
C16	0.1745 (3)	0.7974 (2)	0.3963 (2)	0.0501 (6)
C17	0.0925 (2)	0.72121 (17)	0.38227 (18)	0.0416 (5)
C18	0.3770 (3)	0.8404 (2)	0.3949 (3)	0.0756 (10)
H18A	0.4527	0.8102	0.3913	0.113*
H18B	0.3762	0.8829	0.4521	0.113*
H18C	0.3615	0.8768	0.3345	0.113*
C19	0.3486 (2)	0.5712 (2)	0.2404 (2)	0.0596 (7)
H19A	0.3010	0.5613	0.3000	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.02973 (17)	0.03757 (19)	0.04363 (19)	−0.00574 (12)	0.00346 (11)	−0.00145 (12)
Cl1	0.1021 (8)	0.0845 (7)	0.1251 (10)	0.0027 (6)	0.0147 (7)	−0.0191 (6)
Cl2	0.1134 (8)	0.1183 (9)	0.0844 (7)	0.0526 (7)	0.0020 (6)	0.0266 (6)
Cl3	0.0598 (5)	0.1206 (9)	0.1211 (9)	−0.0260 (5)	0.0001 (5)	0.0227 (7)
N1	0.0351 (10)	0.0460 (12)	0.0419 (11)	−0.0108 (9)	0.0024 (8)	−0.0035 (9)
N2	0.0347 (10)	0.0500 (13)	0.0438 (12)	−0.0005 (9)	0.0021 (8)	−0.0028 (9)
O1	0.0328 (8)	0.0308 (8)	0.0684 (12)	−0.0050 (7)	0.0043 (7)	−0.0011 (7)
O2	0.0359 (9)	0.0439 (10)	0.0955 (16)	−0.0015 (8)	0.0004 (9)	−0.0026 (10)
O3	0.0379 (9)	0.0373 (9)	0.0625 (11)	−0.0044 (7)	0.0028 (8)	0.0032 (8)
O4	0.0556 (12)	0.0473 (11)	0.0880 (15)	−0.0165 (10)	−0.0112 (11)	0.0107 (10)
C1	0.0416 (12)	0.0361 (12)	0.0405 (13)	−0.0020 (10)	0.0078 (10)	−0.0011 (9)
C2	0.0433 (13)	0.0409 (13)	0.0494 (14)	−0.0011 (11)	0.0041 (11)	−0.0014 (10)
C3	0.0555 (16)	0.0426 (14)	0.0655 (18)	0.0089 (13)	0.0025 (13)	−0.0029 (12)
C4	0.077 (2)	0.0341 (14)	0.0692 (19)	0.0055 (14)	−0.0003 (15)	−0.0038 (12)
C5	0.0641 (18)	0.0370 (13)	0.0556 (16)	−0.0114 (13)	0.0047 (13)	−0.0050 (11)
C6	0.0494 (13)	0.0361 (12)	0.0386 (12)	−0.0076 (11)	0.0080 (10)	−0.0029 (9)
C7	0.0407 (15)	0.0638 (19)	0.099 (3)	0.0053 (14)	−0.0012 (15)	−0.0018 (17)
C8	0.0458 (13)	0.0452 (14)	0.0419 (13)	−0.0195 (12)	0.0048 (10)	−0.0026 (10)
C9	0.0332 (12)	0.0644 (18)	0.0566 (16)	−0.0157 (12)	0.0011 (11)	−0.0029 (13)
C10	0.0352 (13)	0.0662 (18)	0.0694 (19)	−0.0069 (13)	−0.0053 (12)	−0.0058 (14)
C11	0.0390 (13)	0.0578 (16)	0.0457 (14)	0.0070 (12)	0.0055 (10)	0.0000 (11)
C12	0.0514 (15)	0.0446 (14)	0.0391 (13)	0.0056 (12)	0.0063 (11)	0.0012 (10)
C13	0.0688 (19)	0.0520 (17)	0.0541 (17)	0.0146 (15)	0.0116 (14)	0.0010 (13)
C14	0.097 (3)	0.0395 (15)	0.066 (2)	0.0099 (17)	0.0136 (18)	0.0035 (13)
C15	0.089 (2)	0.0377 (14)	0.0578 (18)	−0.0079 (15)	0.0017 (16)	0.0013 (12)
C16	0.0618 (16)	0.0432 (14)	0.0451 (15)	−0.0086 (13)	−0.0032 (12)	0.0060 (11)
C17	0.0511 (14)	0.0381 (13)	0.0355 (12)	−0.0032 (11)	0.0029 (10)	0.0027 (9)
C18	0.072 (2)	0.062 (2)	0.092 (3)	−0.0322 (18)	−0.0071 (18)	0.0162 (17)
C19	0.0430 (14)	0.0694 (19)	0.0669 (19)	0.0043 (14)	0.0095 (13)	0.0115 (15)

Geometric parameters (Å, º)

Ni1—O1	1.8392 (17)	C6—C8	1.430 (4)
Ni1—N2	1.843 (2)	C7—H7A	0.9600
Ni1—N1	1.846 (2)	C7—H7B	0.9600
Ni1—O3	1.8458 (17)	C7—H7C	0.9600
Cl1—C19	1.754 (4)	C8—H8A	0.9300
Cl2—C19	1.744 (3)	C9—C10	1.505 (4)
Cl3—C19	1.749 (3)	C9—H9A	0.9700
N1—C8	1.289 (3)	C9—H9B	0.9700
N1—C9	1.482 (3)	C10—H10A	0.9700
N2—C11	1.286 (3)	C10—H10B	0.9700
N2—C10	1.466 (3)	C11—C12	1.430 (4)
O1—C1	1.313 (3)	C11—H11A	0.9300
O2—C2	1.365 (3)	C12—C17	1.406 (4)
O2—C7	1.423 (3)	C12—C13	1.413 (4)
O3—C17	1.308 (3)	C13—C14	1.341 (5)
O4—C16	1.371 (4)	C13—H13A	0.9300
O4—C18	1.415 (3)	C14—C15	1.400 (5)
C1—C6	1.396 (3)	C14—H14A	0.9300
C1—C2	1.429 (3)	C15—C16	1.383 (4)
C2—C3	1.379 (4)	C15—H15A	0.9300
C3—C4	1.396 (4)	C16—C17	1.417 (4)
C3—H3A	0.9300	C18—H18A	0.9600
C4—C5	1.347 (4)	C18—H18B	0.9600
C4—H4A	0.9300	C18—H18C	0.9600
C5—C6	1.431 (4)	C19—H19A	0.9800
C5—H5A	0.9300
O1—Ni1—N2	178.65 (8)	N1—C9—H9A	110.2
O1—Ni1—N1	94.75 (8)	C10—C9—H9A	110.2
N2—Ni1—N1	86.60 (9)	N1—C9—H9B	110.2
O1—Ni1—O3	84.18 (7)	C10—C9—H9B	110.2
N2—Ni1—O3	94.48 (9)	H9A—C9—H9B	108.5
N1—Ni1—O3	178.85 (9)	N2—C10—C9	108.6 (2)
C8—N1—C9	118.8 (2)	N2—C10—H10A	110.0
C8—N1—Ni1	126.80 (18)	C9—C10—H10A	110.0
C9—N1—Ni1	114.40 (17)	N2—C10—H10B	110.0
C11—N2—C10	118.4 (2)	C9—C10—H10B	110.0
C11—N2—Ni1	126.92 (18)	H10A—C10—H10B	108.4
C10—N2—Ni1	114.58 (17)	N2—C11—C12	125.4 (2)
C1—O1—Ni1	127.09 (15)	N2—C11—H11A	117.3
C2—O2—C7	117.9 (2)	C12—C11—H11A	117.3
C17—O3—Ni1	127.37 (17)	C17—C12—C13	120.5 (3)
C16—O4—C18	117.4 (2)	C17—C12—C11	121.0 (2)
O1—C1—C6	124.6 (2)	C13—C12—C11	118.6 (3)
O1—C1—C2	117.7 (2)	C14—C13—C12	121.1 (3)
C6—C1—C2	117.7 (2)	C14—C13—H13A	119.5
O2—C2—C3	124.7 (2)	C12—C13—H13A	119.5
O2—C2—C1	114.5 (2)	C13—C14—C15	119.9 (3)
C3—C2—C1	120.8 (2)	C13—C14—H14A	120.0
C2—C3—C4	120.2 (3)	C15—C14—H14A	120.0
C2—C3—H3A	119.9	C16—C15—C14	120.5 (3)
C4—C3—H3A	119.9	C16—C15—H15A	119.8
C5—C4—C3	120.6 (3)	C14—C15—H15A	119.8
C5—C4—H4A	119.7	O4—C16—C15	124.4 (3)
C3—C4—H4A	119.7	O4—C16—C17	114.8 (2)
C4—C5—C6	120.5 (3)	C15—C16—C17	120.8 (3)
C4—C5—H5A	119.7	O3—C17—C12	124.2 (2)
C6—C5—H5A	119.7	O3—C17—C16	118.6 (2)
C1—C6—C8	121.2 (2)	C12—C17—C16	117.2 (2)
C1—C6—C5	120.0 (2)	O4—C18—H18A	109.5
C8—C6—C5	118.7 (2)	O4—C18—H18B	109.5
O2—C7—H7A	109.5	H18A—C18—H18B	109.5
O2—C7—H7B	109.5	O4—C18—H18C	109.5
H7A—C7—H7B	109.5	H18A—C18—H18C	109.5
O2—C7—H7C	109.5	H18B—C18—H18C	109.5
H7A—C7—H7C	109.5	Cl2—C19—Cl3	109.41 (18)
H7B—C7—H7C	109.5	Cl2—C19—Cl1	110.63 (19)
N1—C8—C6	125.0 (2)	Cl3—C19—Cl1	108.63 (16)
N1—C8—H8A	117.5	Cl2—C19—H19A	109.4
C6—C8—H8A	117.5	Cl3—C19—H19A	109.4
N1—C9—C10	107.7 (2)	Cl1—C19—H19A	109.4
O1—Ni1—N1—C8	−7.1 (2)	Ni1—N1—C8—C6	4.4 (4)
N2—Ni1—N1—C8	172.9 (2)	C1—C6—C8—N1	2.2 (4)
O1—Ni1—N1—C9	170.93 (18)	C5—C6—C8—N1	179.3 (2)
N2—Ni1—N1—C9	−9.09 (18)	C8—N1—C9—C10	−157.5 (2)
N1—Ni1—N2—C11	173.6 (2)	Ni1—N1—C9—C10	24.4 (3)
O3—Ni1—N2—C11	−5.9 (2)	C11—N2—C10—C9	−157.9 (2)
N1—Ni1—N2—C10	−9.48 (19)	Ni1—N2—C10—C9	24.9 (3)
O3—Ni1—N2—C10	170.94 (19)	N1—C9—C10—N2	−30.1 (3)
N1—Ni1—O1—C1	5.7 (2)	C10—N2—C11—C12	−175.8 (2)
O3—Ni1—O1—C1	−174.8 (2)	Ni1—N2—C11—C12	1.0 (4)
O1—Ni1—O3—C17	−171.1 (2)	N2—C11—C12—C17	3.6 (4)
Ni1—O1—C1—C6	−1.4 (3)	N2—C11—C12—C13	−176.7 (3)
Ni1—O1—C1—C2	178.97 (17)	C17—C12—C13—C14	−1.7 (4)
C7—O2—C2—C3	6.9 (4)	C11—C12—C13—C14	178.6 (3)
C7—O2—C2—C1	−173.2 (3)	C12—C13—C14—C15	0.8 (5)
O1—C1—C2—O2	1.3 (3)	C13—C14—C15—C16	1.4 (5)
C6—C1—C2—O2	−178.3 (2)	C18—O4—C16—C15	−16.2 (4)
O1—C1—C2—C3	−178.8 (2)	C18—O4—C16—C17	165.1 (3)
C6—C1—C2—C3	1.5 (4)	C14—C15—C16—O4	178.8 (3)
O2—C2—C3—C4	179.0 (3)	C14—C15—C16—C17	−2.6 (4)
C1—C2—C3—C4	−0.9 (4)	Ni1—O3—C17—C12	−7.1 (4)
C2—C3—C4—C5	−0.3 (5)	Ni1—O3—C17—C16	172.28 (17)
C3—C4—C5—C6	0.7 (5)	C13—C12—C17—O3	179.9 (2)
O1—C1—C6—C8	−3.7 (4)	C11—C12—C17—O3	−0.5 (4)
C2—C1—C6—C8	175.9 (2)	C13—C12—C17—C16	0.5 (4)
O1—C1—C6—C5	179.2 (2)	C11—C12—C17—C16	−179.8 (2)
C2—C1—C6—C5	−1.1 (3)	O4—C16—C17—O3	0.9 (3)
C4—C5—C6—C1	0.0 (4)	C15—C16—C17—O3	−177.8 (2)
C4—C5—C6—C8	−177.1 (3)	O4—C16—C17—C12	−179.6 (2)
C9—N1—C8—C6	−173.6 (2)	C15—C16—C17—C12	1.7 (4)