{6,6'-Dimethyl-2,2'-[propane-1,3-diylbis(nitrilo­methyl­idyne)]diphenolato}cobalt(II)

In the title mononuclear cobalt(II) compound, [Co(C₁₉H₂₀N₂O₂)], the Co atom is coordinated by two N and two O atoms, giving a square-planar geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.083
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group Cmc21   ....    A21am
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O1      ..       7.20 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   N1      ..       5.10 su
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.02

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.31
           From the CIF: _reflns_number_total               2014
           Count of symmetry unique reflns         1155
           Completeness (_total/calc)            174.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       859
           Fraction of Friedel pairs measured     0.744
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Cobalt compounds have been of great interest in coordination chemistry (Billson et al., 2000; Kotera et al., 2003; Fritsky et al., 2003). A new cobalt(II) compound, (I), derived from the tetradentate chelating Schiff base ligand, is described here.

The crystal structure of (I), possesses mirror plane symmetry, is shown in Fig. 1. The coordination sites are occupied by the four donor atoms of the Schiff base ligand, giving a slightly distorted square-planar geometry. All the bond lengths (Table 1) around the metal center are comparable to those in similar compounds (Cador et al., 2003; Kennedy et al., 1984). The crystal packing of (I) is shown in Fig. 2.

S2. Experimental

All the chemicals were of AR grade. 3-Methyl-2-hydroxybenzaldehyde (135.1 mg, 1.0 mmol), propane-1,3-diamine (36.9 mg, 0.5 mmol) and Co(CH₃COO)₂·4H₂O (125.1 mg, 0.5 mmol) were refluxed in methanol (50 ml) for 30 min. The mixture was cooled to room temperature and filtered. After keeping the filtrate in air for 5 d, brown block-shaped crystals suitable for X-ray analysis were obtained.

S3. Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H distances of 0.93–0.97 Å and U_iso(H) = 1.2 or 1.5U_eq(C).

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), with anisotropic displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The molecular packing of (I).

{6,6'-Dimethyl-2,2'-[propane-1,3- diylbis(nitrilomethylidyne)]diphenolato}cobalt(II)

Crystal data

[Co(C19H20N2O2)]	Dx = 1.446 Mg m^−3
Mr = 367.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, A21am	Cell parameters from 3132 reflections
a = 7.529 (1) Å	θ = 2.7–24.5°
b = 10.398 (2) Å	µ = 1.03 mm^−1
c = 21.553 (3) Å	T = 298 K
V = 1687.3 (4) Å^3	Flake, red
Z = 4	0.37 × 0.31 × 0.18 mm
F(000) = 764

Data collection

Bruker SMART APEX CCD area-detector diffractometer	2014 independent reflections
Radiation source: fine-focus sealed tube	1858 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ϕ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→9
Tmin = 0.702, Tmax = 0.836	k = −13→13
9543 measured reflections	l = −27→27

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)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0344P)^2 + 0.5503P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
2014 reflections	Δρmax = 0.27 e Å^−3
113 parameters	Δρmin = −0.28 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (2)

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
Co1	0.47925 (5)	0.95280 (3)	1.0000	0.04172 (13)
O1	0.5165 (2)	0.82171 (16)	0.94371 (9)	0.0546 (5)
N1	0.4326 (3)	1.0706 (2)	0.93542 (13)	0.0560 (7)
C1	0.4312 (3)	0.8056 (3)	0.89170 (13)	0.0497 (6)
C2	0.4226 (4)	0.6808 (3)	0.86533 (14)	0.0607 (7)
C3	0.3269 (5)	0.6628 (4)	0.81191 (15)	0.0760 (10)
H3	0.3213	0.5807	0.7949	0.091*
C4	0.2376 (6)	0.7626 (4)	0.78207 (16)	0.0839 (11)
H4	0.1696	0.7468	0.7469	0.101*
C5	0.2519 (5)	0.8838 (4)	0.80549 (15)	0.0743 (10)
H5	0.1985	0.9517	0.7846	0.089*
C6	0.3454 (4)	0.9084 (3)	0.86036 (14)	0.0550 (7)
C7	0.5126 (6)	0.5720 (3)	0.89908 (19)	0.0821 (13)
H7A	0.4781	0.4916	0.8808	0.123*
H7B	0.4779	0.5732	0.9419	0.123*
H7C	0.6391	0.5819	0.8961	0.123*
C8	0.3666 (4)	1.0356 (3)	0.88272 (16)	0.0591 (8)
H8	0.3289	1.1013	0.8565	0.071*
C9	0.4602 (6)	1.2108 (3)	0.94263 (17)	0.0774 (10)
H9A	0.3453	1.2531	0.9426	0.093*
H9B	0.5261	1.2423	0.9071	0.093*
C10	0.5569 (6)	1.2475 (4)	1.0000	0.0773 (15)
H10A	0.6724	1.2061	1.0000	0.093*
H10B	0.5759	1.3397	1.0000	0.093*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.0329 (2)	0.02682 (18)	0.0654 (3)	0.0022 (2)	0.000	0.000
O1	0.0471 (14)	0.0432 (9)	0.0735 (12)	0.0077 (8)	−0.0060 (9)	−0.0042 (8)
N1	0.0501 (18)	0.0327 (10)	0.0850 (16)	0.0028 (8)	0.0094 (11)	0.0089 (10)
C1	0.0415 (15)	0.0502 (14)	0.0573 (15)	−0.0021 (10)	0.0093 (10)	0.0041 (12)
C2	0.0596 (17)	0.0563 (16)	0.0662 (17)	−0.0037 (12)	0.0107 (13)	−0.0069 (13)
C3	0.085 (3)	0.082 (2)	0.0614 (18)	−0.0108 (18)	0.0044 (17)	−0.0163 (16)
C4	0.091 (3)	0.106 (3)	0.0544 (18)	−0.006 (2)	−0.0026 (17)	−0.009 (2)
C5	0.073 (2)	0.096 (3)	0.0540 (18)	0.009 (2)	0.0057 (15)	0.0174 (18)
C6	0.0515 (15)	0.0566 (16)	0.0570 (15)	−0.0006 (13)	0.0120 (12)	0.0111 (13)
C7	0.088 (4)	0.0446 (15)	0.114 (3)	0.0051 (17)	−0.015 (2)	−0.0191 (15)
C8	0.0543 (18)	0.0496 (16)	0.0732 (19)	0.0054 (12)	0.0103 (15)	0.0199 (14)
C9	0.073 (2)	0.0362 (13)	0.123 (3)	0.0027 (18)	0.001 (2)	0.0109 (14)
C10	0.046 (2)	0.046 (2)	0.139 (5)	0.0014 (18)	0.000	0.000

Geometric parameters (Å, º)

Co1—O1^i	1.846 (2)	C4—H4	0.9300
Co1—O1	1.846 (2)	C5—C6	1.399 (5)
Co1—N1^i	1.887 (2)	C5—H5	0.9300
Co1—N1	1.887 (2)	C6—C8	1.417 (4)
O1—C1	1.303 (3)	C7—H7A	0.9600
N1—C8	1.292 (4)	C7—H7B	0.9600
N1—C9	1.481 (3)	C7—H7C	0.9600
C1—C2	1.419 (4)	C8—H8	0.9300
C1—C6	1.420 (4)	C9—C10	1.485 (5)
C2—C3	1.371 (5)	C9—H9A	0.9700
C2—C7	1.506 (5)	C9—H9B	0.9700
C3—C4	1.394 (6)	C10—C9^i	1.485 (5)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.362 (5)	C10—H10B	0.9700
O1^i—Co1—O1	82.16 (12)	C5—C6—C8	121.0 (3)
O1^i—Co1—N1^i	91.31 (9)	C5—C6—C1	119.6 (3)
O1—Co1—N1^i	172.84 (10)	C8—C6—C1	119.3 (3)
O1^i—Co1—N1	172.84 (10)	C2—C7—H7A	109.5
O1—Co1—N1	91.31 (9)	C2—C7—H7B	109.5
N1^i—Co1—N1	95.05 (15)	H7A—C7—H7B	109.5
C1—O1—Co1	125.83 (17)	C2—C7—H7C	109.5
C8—N1—C9	115.0 (3)	H7A—C7—H7C	109.5
C8—N1—Co1	122.50 (19)	H7B—C7—H7C	109.5
C9—N1—Co1	122.4 (2)	N1—C8—C6	127.3 (3)
O1—C1—C2	119.0 (2)	N1—C8—H8	116.4
O1—C1—C6	122.5 (3)	C6—C8—H8	116.4
C2—C1—C6	118.5 (3)	N1—C9—C10	114.1 (3)
C3—C2—C1	119.0 (3)	N1—C9—H9A	108.7
C3—C2—C7	122.7 (3)	C10—C9—H9A	108.7
C1—C2—C7	118.2 (3)	N1—C9—H9B	108.7
C2—C3—C4	122.6 (3)	C10—C9—H9B	108.7
C2—C3—H3	118.7	H9A—C9—H9B	107.6
C4—C3—H3	118.7	C9^i—C10—C9	112.8 (4)
C5—C4—C3	118.7 (4)	C9^i—C10—H10A	109.0
C5—C4—H4	120.7	C9—C10—H10A	109.0
C3—C4—H4	120.7	C9^i—C10—H10B	109.0
C4—C5—C6	121.5 (3)	C9—C10—H10B	109.0
C4—C5—H5	119.3	H10A—C10—H10B	107.8
C6—C5—H5	119.3

Symmetry code: (i) x, y, −z+2.