Di-μ-chloro-bis­({2-[(2-hydroxy­ethyl)imino­methyl]phenolato-κ³N,O,O′}nickel(II)) methanol solvate

The title compound, [Ni₂Cl₂(C₉H₁₀NO₂)₂]·CH₃OH, is a dinuclear unit built up by two nickel(II) complexes, bridged by two Cl atoms. The coordination geometry around each Ni^II atom can be considered as distorted square-pyramidal, with the tridendate chelate Schiff base ligands coordinating in a trans conformation through their imine N atom and phen­oxy and alk­oxy O atoms.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.041
• wR factor = 0.104
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni1    -   Cl1     ..      13.40 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni1    -   Cl2     ..      14.20 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni2    -   Cl1     ..      13.46 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni2    -   Cl2     ..      12.81 su
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Ni2    -   O3      ..      10.08 su

Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.490
           From the CIF: _refine_ls_abs_structure_Flack_su    0.040
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.49
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.19
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O1      ..       6.38 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   O2      ..       7.92 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1      ..       5.89 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni2    -   O4      ..       8.77 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni2    -   N2      ..       7.50 su
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           71.28
           From the CIF: _reflns_number_total               2421
           Count of symmetry unique reflns         2456
           Completeness (_total/calc)             98.57%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Di-µ-chloro-bis({2-[(2-hydroxyethyl)iminomethyl]phenolato- κ³N,O,O'}nickel(II)) methanol solvate

Crystal data

[Ni2Cl2(C9H10NO2)2]·CH4O	F(000) = 1128
Mr = 548.68	Dx = 1.647 Mg m^−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4020 reflections
a = 9.6183 (4) Å	θ = 0.2–41.1°
b = 11.7082 (5) Å	µ = 4.63 mm^−1
c = 19.6458 (8) Å	T = 100 K
V = 2212.37 (16) Å^3	Plate, green
Z = 4	0.3 × 0.3 × 0.15 mm

Data collection

Bruker SMART 6000 diffractometer	2421 independent reflections
Radiation source: fine-focus sealed tube	2119 reflections with I > 2σ(I)
Crossed Goebel mirrors monochromator	Rint = 0.076
ω and φ scans	θmax = 71.3°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = 0→11
Tmin = 0.332, Tmax = 0.498	k = 0→14
17341 measured reflections	l = 0→23

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 atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.0664P)^2 + 0.2378P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max = 0.001
2421 reflections	Δρmax = 0.83 e Å^−3
280 parameters	Δρmin = −0.38 e Å^−3
0 restraints	Absolute structure: (Flack, 1983), with how many Friedel pairs?
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.49 (4)

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
C1	0.9858 (6)	0.1551 (6)	0.5909 (3)	0.0239 (12)
C2	1.0576 (7)	0.2455 (6)	0.5598 (3)	0.0289 (14)
H2	1.0294	0.3203	0.5681	0.035*
C3	1.1676 (7)	0.2261 (6)	0.5176 (3)	0.0291 (14)
H3	1.2124	0.2877	0.4973	0.035*
C4	1.2144 (6)	0.1154 (6)	0.5043 (3)	0.0273 (14)
H4	1.2887	0.1026	0.4750	0.033*
C5	1.1478 (7)	0.0259 (6)	0.5356 (3)	0.0278 (14)
H5	1.1789	−0.0481	0.5276	0.033*
C6	1.0329 (6)	0.0430 (5)	0.5797 (3)	0.0221 (12)
C7	0.9694 (6)	−0.0576 (6)	0.6084 (3)	0.0238 (13)
H7	1.0084	−0.1279	0.5974	0.029*
C8	0.8041 (7)	−0.1675 (5)	0.6719 (3)	0.0268 (13)
H8A	0.8773	−0.2238	0.6773	0.032*
H8B	0.7366	−0.1963	0.6394	0.032*
C9	0.7346 (7)	−0.1423 (5)	0.7403 (3)	0.0248 (12)
H9A	0.6769	−0.2060	0.7544	0.030*
H9B	0.8040	−0.1284	0.7752	0.030*
C10	0.5685 (6)	0.3076 (5)	0.9087 (3)	0.0218 (12)
C11	0.4883 (7)	0.2561 (6)	0.9607 (3)	0.0258 (13)
H11	0.4945	0.1776	0.9672	0.031*
C12	0.4011 (7)	0.3189 (6)	1.0021 (3)	0.0301 (14)
H12	0.3495	0.2827	1.0359	0.036*
C13	0.3905 (7)	0.4375 (6)	0.9932 (3)	0.0309 (14)
H13	0.3341	0.4806	1.0218	0.037*
C14	0.4643 (7)	0.4897 (5)	0.9416 (3)	0.0241 (13)
H14	0.4542	0.5678	0.9348	0.029*
C15	0.5541 (6)	0.4280 (5)	0.8993 (3)	0.0211 (12)
C16	0.6269 (6)	0.4890 (5)	0.8461 (3)	0.0221 (12)
H16	0.6109	0.5672	0.8432	0.027*
C17	0.7755 (7)	0.5214 (5)	0.7519 (3)	0.0254 (13)
H17A	0.8586	0.5565	0.7705	0.030*
H17B	0.7116	0.5814	0.7385	0.030*
C18	0.8124 (6)	0.4480 (5)	0.6909 (3)	0.0238 (13)
H18A	0.7292	0.4256	0.6664	0.029*
H18B	0.8733	0.4891	0.6601	0.029*
C19	0.5969 (8)	−0.0528 (6)	0.8940 (3)	0.0327 (15)
H19A	0.6948	−0.0650	0.8882	0.049*
H19B	0.5485	−0.1239	0.8883	0.049*
H19C	0.5795	−0.0234	0.9388	0.049*
Cl1	0.59492 (13)	0.21032 (11)	0.69991 (7)	0.0223 (3)
Cl2	0.89045 (14)	0.12436 (12)	0.80086 (7)	0.0229 (3)
N1	0.8623 (5)	−0.0576 (5)	0.6484 (3)	0.0245 (11)
N2	0.7103 (5)	0.4467 (4)	0.8030 (3)	0.0222 (10)
Ni1	0.76067 (9)	0.07531 (7)	0.67939 (4)	0.0117 (2)
Ni2	0.76472 (8)	0.28812 (7)	0.79694 (4)	0.0104 (2)
O1	0.8742 (5)	0.1795 (4)	0.6300 (2)	0.0255 (9)
O2	0.6505 (4)	−0.0411 (4)	0.7293 (2)	0.0221 (9)
H22	0.627 (8)	−0.016 (6)	0.773 (4)	0.026*
O3	0.6531 (5)	0.2418 (4)	0.8723 (2)	0.0243 (9)
O4	0.8826 (4)	0.3483 (4)	0.7188 (2)	0.0257 (9)
H42	0.868 (8)	0.292 (7)	0.688 (4)	0.031*
O5	0.5489 (5)	0.0273 (4)	0.8445 (2)	0.0277 (9)
H5A	0.5618	0.0924	0.8584	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.019 (3)	0.032 (3)	0.020 (3)	0.005 (3)	0.000 (2)	0.001 (2)
C2	0.030 (3)	0.027 (3)	0.029 (3)	0.002 (3)	0.002 (3)	0.006 (3)
C3	0.023 (3)	0.040 (4)	0.024 (3)	0.002 (3)	−0.003 (2)	0.009 (3)
C4	0.016 (3)	0.039 (4)	0.027 (3)	0.005 (2)	0.004 (2)	−0.003 (3)
C5	0.022 (3)	0.037 (4)	0.024 (3)	0.003 (3)	0.000 (2)	−0.004 (3)
C6	0.022 (3)	0.029 (3)	0.015 (3)	0.002 (2)	−0.001 (2)	0.000 (2)
C7	0.018 (3)	0.031 (3)	0.023 (3)	0.002 (3)	0.002 (2)	−0.008 (3)
C8	0.028 (3)	0.019 (3)	0.034 (3)	0.002 (2)	−0.001 (3)	−0.004 (3)
C9	0.026 (3)	0.018 (3)	0.030 (3)	0.002 (3)	0.000 (3)	0.003 (2)
C10	0.018 (3)	0.027 (3)	0.021 (3)	0.001 (2)	−0.002 (2)	0.002 (2)
C11	0.027 (3)	0.026 (3)	0.024 (3)	0.006 (3)	0.005 (3)	0.002 (3)
C12	0.032 (3)	0.035 (4)	0.023 (3)	0.004 (3)	0.006 (3)	0.000 (3)
C13	0.025 (3)	0.038 (4)	0.030 (3)	0.008 (3)	0.007 (3)	0.000 (3)
C14	0.028 (3)	0.023 (3)	0.021 (3)	0.003 (3)	0.002 (2)	−0.006 (2)
C15	0.020 (3)	0.021 (3)	0.022 (3)	0.000 (2)	0.000 (2)	−0.001 (2)
C16	0.015 (3)	0.028 (3)	0.023 (3)	0.001 (2)	0.000 (2)	−0.001 (2)
C17	0.026 (3)	0.025 (3)	0.025 (3)	−0.001 (3)	0.005 (2)	−0.003 (2)
C18	0.025 (3)	0.025 (3)	0.022 (3)	−0.001 (2)	0.000 (2)	0.004 (2)
C19	0.034 (4)	0.031 (4)	0.032 (4)	−0.003 (3)	0.000 (3)	−0.003 (3)
Cl1	0.0181 (6)	0.0200 (6)	0.0287 (6)	0.0026 (5)	−0.0014 (5)	−0.0017 (6)
Cl2	0.0200 (6)	0.0211 (6)	0.0276 (7)	0.0039 (5)	−0.0005 (5)	−0.0004 (5)
N1	0.021 (2)	0.027 (3)	0.025 (3)	0.000 (2)	0.002 (2)	−0.002 (2)
N2	0.020 (2)	0.023 (2)	0.023 (2)	−0.0008 (19)	−0.0003 (19)	0.002 (2)
Ni1	0.0097 (4)	0.0099 (4)	0.0156 (4)	0.0019 (3)	0.0023 (3)	−0.0008 (3)
Ni2	0.0091 (4)	0.0089 (4)	0.0132 (4)	0.0008 (3)	0.0021 (3)	0.0000 (3)
O1	0.026 (2)	0.025 (2)	0.025 (2)	0.0060 (18)	0.0076 (18)	0.0010 (17)
O2	0.022 (2)	0.022 (2)	0.023 (2)	0.0039 (17)	−0.0001 (16)	−0.0039 (17)
O3	0.026 (2)	0.018 (2)	0.028 (2)	0.0050 (17)	−0.0018 (17)	−0.0009 (17)
O4	0.021 (2)	0.024 (2)	0.032 (2)	0.0002 (18)	0.0021 (18)	−0.0030 (18)
O5	0.029 (2)	0.025 (2)	0.029 (2)	−0.0008 (19)	0.0030 (18)	0.0047 (19)

Geometric parameters (Å, º)

C1—O1	1.351 (7)	C13—H13	0.9300
C1—C2	1.404 (9)	C14—C15	1.400 (8)
C1—C6	1.406 (9)	C14—H14	0.9300
C2—C3	1.363 (9)	C15—C16	1.447 (8)
C2—H2	0.9300	C16—N2	1.267 (8)
C3—C4	1.397 (10)	C16—H16	0.9300
C3—H3	0.9300	C17—N2	1.473 (8)
C4—C5	1.373 (10)	C17—C18	1.516 (8)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.419 (9)	C17—H17B	0.9700
C5—H5	0.9300	C18—O4	1.455 (7)
C6—C7	1.442 (9)	C18—H18A	0.9700
C7—N1	1.295 (8)	C18—H18B	0.9700
C7—H7	0.9300	C19—O5	1.428 (8)
C8—N1	1.477 (8)	C19—H19A	0.9600
C8—C9	1.531 (8)	C19—H19B	0.9600
C8—H8A	0.9700	C19—H19C	0.9600
C8—H8B	0.9700	Cl1—Ni1	2.2809 (15)
C9—O2	1.450 (7)	Cl1—Ni2	2.6704 (16)
C9—H9A	0.9700	Cl2—Ni2	2.2681 (15)
C9—H9B	0.9700	N1—Ni1	1.937 (5)
C10—O3	1.329 (8)	N2—Ni2	1.932 (5)
C10—C11	1.416 (9)	Ni1—O1	1.903 (4)
C10—C15	1.428 (9)	Ni1—O2	1.986 (4)
C11—C12	1.380 (9)	Ni2—O3	1.907 (4)
C11—H11	0.9300	Ni2—O4	2.034 (5)
C12—C13	1.404 (10)	O2—H22	0.93 (8)
C12—H12	0.9300	O4—H42	0.90 (8)
C13—C14	1.380 (9)	O5—H5A	0.8200
O1—C1—C2	118.6 (6)	N2—C16—H16	116.7
O1—C1—C6	122.9 (6)	C15—C16—H16	116.7
C2—C1—C6	118.5 (6)	N2—C17—C18	107.5 (5)
C3—C2—C1	121.4 (6)	N2—C17—H17A	110.2
C3—C2—H2	119.3	C18—C17—H17A	110.2
C1—C2—H2	119.3	N2—C17—H17B	110.2
C2—C3—C4	121.2 (7)	C18—C17—H17B	110.2
C2—C3—H3	119.4	H17A—C17—H17B	108.5
C4—C3—H3	119.4	O4—C18—C17	105.4 (5)
C5—C4—C3	118.3 (6)	O4—C18—H18A	110.7
C5—C4—H4	120.8	C17—C18—H18A	110.7
C3—C4—H4	120.8	O4—C18—H18B	110.7
C4—C5—C6	121.9 (6)	C17—C18—H18B	110.7
C4—C5—H5	119.0	H18A—C18—H18B	108.8
C6—C5—H5	119.0	O5—C19—H19A	109.5
C1—C6—C5	118.6 (6)	O5—C19—H19B	109.5
C1—C6—C7	124.4 (5)	H19A—C19—H19B	109.5
C5—C6—C7	117.0 (6)	O5—C19—H19C	109.5
N1—C7—C6	125.1 (6)	H19A—C19—H19C	109.5
N1—C7—H7	117.4	H19B—C19—H19C	109.5
C6—C7—H7	117.4	Ni1—Cl1—Ni2	86.28 (5)
N1—C8—C9	105.8 (5)	C7—N1—C8	119.4 (5)
N1—C8—H8A	110.6	C7—N1—Ni1	126.3 (5)
C9—C8—H8A	110.6	C8—N1—Ni1	114.2 (4)
N1—C8—H8B	110.6	C16—N2—C17	119.5 (5)
C9—C8—H8B	110.6	C16—N2—Ni2	126.1 (4)
H8A—C8—H8B	108.7	C17—N2—Ni2	114.4 (4)
O2—C9—C8	105.7 (4)	O1—Ni1—N1	93.7 (2)
O2—C9—H9A	110.6	O1—Ni1—O2	176.42 (18)
C8—C9—H9A	110.6	N1—Ni1—O2	82.7 (2)
O2—C9—H9B	110.6	O1—Ni1—Cl1	92.68 (14)
C8—C9—H9B	110.6	N1—Ni1—Cl1	164.91 (16)
H9A—C9—H9B	108.7	O2—Ni1—Cl1	90.88 (13)
O3—C10—C11	118.4 (6)	O3—Ni2—N2	94.18 (19)
O3—C10—C15	124.2 (5)	O3—Ni2—O4	176.22 (19)
C11—C10—C15	117.4 (6)	N2—Ni2—O4	82.2 (2)
C12—C11—C10	122.0 (6)	O3—Ni2—Cl2	91.91 (13)
C12—C11—H11	119.0	N2—Ni2—Cl2	162.62 (15)
C10—C11—H11	119.0	O4—Ni2—Cl2	91.22 (13)
C11—C12—C13	119.8 (6)	O3—Ni2—Cl1	96.47 (14)
C11—C12—H12	120.1	N2—Ni2—Cl1	101.90 (15)
C13—C12—H12	120.1	O4—Ni2—Cl1	85.44 (13)
C14—C13—C12	119.5 (6)	Cl2—Ni2—Cl1	93.55 (5)
C14—C13—H13	120.2	C1—O1—Ni1	127.6 (4)
C12—C13—H13	120.2	C9—O2—Ni1	109.7 (4)
C13—C14—C15	121.7 (6)	C9—O2—H22	105 (5)
C13—C14—H14	119.2	Ni1—O2—H22	111 (5)
C15—C14—H14	119.2	C10—O3—Ni2	126.7 (4)
C14—C15—C10	119.5 (6)	C18—O4—Ni2	107.7 (3)
C14—C15—C16	118.2 (6)	C18—O4—H42	105 (5)
C10—C15—C16	122.2 (6)	Ni2—O4—H42	99 (5)
N2—C16—C15	126.6 (6)	C19—O5—H5A	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H22···O5	0.93 (8)	1.68 (8)	2.591 (6)	167 (7)
O4—H42···O1	0.90 (8)	1.75 (8)	2.637 (6)	169 (7)
O5—H5A···O3	0.82	1.98	2.758 (6)	160