Bis[2-(cyclo­hexyl­imino­meth­yl)-4-nitro­phenolato]cobalt(II)

The title compound, [Co(C₁₃H₁₅N₂O₃)₂], is isostructural with the zinc(II) compound reported previously. The Co atom is coordinated by four donor atoms from two Schiff base ligands, forming a tetra­hedral geometry.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 17.5

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S1. Comment

Cobalt compounds are of great interest in coordination chemistry (Billson et al., 2000; Kotera et al., 2003; Fritsky et al., 2003). As part of our investigations on non-covalent interactions in metal complexes (Chen, 2005), the new title Co^II complex, (I), has been prepared and its crystal structure is presented here.

Complex (I) is a mononuclear cobalt(II) compound (Fig. 1), which is isostructural with the zinc compound bis[2-(cyclohexyliminomethyl)-4-nitrophenolato]zinc(II) (You, 2005), and structurally similar with the cobalt compound bis[4-chloro-2-(cyclohexyliminomethyl)phenolato]cobalt(II) (Li & Zhang, 2005). In (I), the Co atom is coordinated by four donor atoms from two Schiff base ligands, forming a tetrahedral geometry. The Schiff base acts as a bidentate ligand and ligates to the metal via the phenolate O and imine N atoms. All the bond lengths (Table 1) around the metal center are comparable to those in similar complexes (Fun et al., 1999; Iyere et al., 2004; Elerman et al., 1996).

S2. Experimental

All the chemicals were of AR grade. 5-Nitro-2-hydroxybenzaldehyde (16.7 mg, 0.1 mmol), cyclohexylamine (9.9 mg, 0.1 mmol) and CoCl₂·4H₂O (20.2 mg, 0.1 mmol) were refluxed in 30 ml MeOH for 30 min. The mixture was cooled to room temperature and filtered. After keeping the filtrate in air for 11 d, red block crystals suitable for X-ray analysis were obtained.

S3. Refinement

All the H atoms were positioned geometrically and refined as riding atoms, with C—H distances of 0.93–0.98 Å and U_iso(H) = 1.2U_eq(parent C-atom).

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 compound (I), showing the labelling scheme and displacement ellipsoids drawn at the 30% probability level.

(I)

Crystal data

[Co(C13H15N2O3)2]	Z = 2
Mr = 553.47	F(000) = 578
Triclinic, P1	Dx = 1.423 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.765 (1) Å	Cell parameters from 5677 reflections
b = 11.135 (1) Å	θ = 2.3–27.4°
c = 12.410 (1) Å	µ = 0.71 mm^−1
α = 113.698 (1)°	T = 298 K
β = 104.064 (1)°	Block, red
γ = 95.105 (1)°	0.20 × 0.16 × 0.10 mm
V = 1291.84 (19) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5834 independent reflections
Radiation source: fine-focus sealed tube	4950 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ϕ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
Tmin = 0.871, Tmax = 0.932	k = −14→14
15016 measured reflections	l = −15→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0538P)^2 + 0.2812P] where P = (Fo^2 + 2Fc^2)/3
5834 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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

	x	y	z	Uiso*/Ueq
Co1	0.96670 (2)	0.79077 (2)	0.59431 (2)	0.04198 (10)
O1	0.85602 (13)	0.66690 (13)	0.43260 (12)	0.0486 (3)
O2	0.32733 (16)	0.61265 (19)	0.05856 (16)	0.0782 (5)
O3	0.35281 (15)	0.81668 (19)	0.19317 (17)	0.0745 (5)
O4	1.14781 (13)	0.85335 (15)	0.62309 (13)	0.0518 (3)
O5	1.56691 (16)	0.7751 (2)	1.02264 (17)	0.0750 (5)
O6	1.68770 (14)	0.89811 (18)	0.97386 (17)	0.0733 (5)
N1	0.86357 (15)	0.93420 (15)	0.61478 (13)	0.0407 (3)
N2	0.38829 (16)	0.7098 (2)	0.15649 (17)	0.0549 (4)
N3	0.99439 (14)	0.70069 (15)	0.70580 (13)	0.0388 (3)
N4	1.58130 (16)	0.83807 (18)	0.96389 (17)	0.0540 (4)
C1	0.74658 (18)	0.68143 (18)	0.37277 (16)	0.0405 (4)
C2	0.69371 (17)	0.79898 (18)	0.41709 (16)	0.0392 (4)
C3	0.57429 (18)	0.80323 (19)	0.34325 (17)	0.0433 (4)
H3	0.5387	0.8789	0.3713	0.052*
C4	0.50920 (18)	0.6983 (2)	0.23083 (17)	0.0440 (4)
C5	0.5580 (2)	0.5827 (2)	0.18681 (18)	0.0501 (5)
H5	0.5127	0.5115	0.1106	0.060*
C6	0.6731 (2)	0.5754 (2)	0.25696 (18)	0.0512 (5)
H6	0.7048	0.4973	0.2275	0.061*
C7	0.75592 (18)	0.91578 (18)	0.53224 (17)	0.0426 (4)
H7	0.7128	0.9868	0.5490	0.051*
C8	0.90651 (19)	1.06745 (18)	0.72353 (16)	0.0440 (4)
H8	0.8282	1.1034	0.7342	0.053*
C9	0.9936 (3)	1.1635 (2)	0.7021 (2)	0.0605 (6)
H9A	0.9474	1.1718	0.6287	0.073*
H9B	1.0711	1.1293	0.6888	0.073*
C10	1.0340 (3)	1.3015 (2)	0.8141 (2)	0.0670 (6)
H10A	1.0944	1.3610	0.8015	0.080*
H10B	0.9572	1.3396	0.8215	0.080*
C11	1.0984 (2)	1.2923 (2)	0.9321 (2)	0.0668 (6)
H11A	1.1814	1.2657	0.9293	0.080*
H11B	1.1160	1.3797	1.0016	0.080*
C12	1.0129 (3)	1.1926 (2)	0.9504 (2)	0.0703 (7)
H12A	0.9351	1.2255	0.9645	0.084*
H12B	1.0599	1.1837	1.0232	0.084*
C13	0.9724 (3)	1.0554 (2)	0.83917 (19)	0.0634 (6)
H13A	1.0491	1.0176	0.8303	0.076*
H13B	0.9129	0.9955	0.8520	0.076*
C14	1.23186 (17)	0.78238 (17)	0.78096 (16)	0.0386 (4)
C15	1.24520 (18)	0.84666 (18)	0.70432 (17)	0.0434 (4)
C16	1.3732 (2)	0.9053 (2)	0.7178 (2)	0.0579 (5)
H16	1.3841	0.9464	0.6677	0.069*
C17	1.4815 (2)	0.9039 (2)	0.8013 (2)	0.0562 (5)
H17	1.5645	0.9441	0.8085	0.067*
C18	1.46565 (18)	0.84157 (18)	0.87529 (18)	0.0446 (4)
C19	1.34494 (17)	0.78290 (18)	0.86681 (17)	0.0417 (4)
H19	1.3371	0.7427	0.9183	0.050*
C20	1.10951 (17)	0.71205 (18)	0.77479 (16)	0.0394 (4)
H20	1.1143	0.6700	0.8266	0.047*
C21	0.88472 (17)	0.61355 (18)	0.70900 (16)	0.0398 (4)
H21	0.9095	0.6091	0.7885	0.048*
C22	0.76253 (18)	0.6725 (2)	0.69888 (19)	0.0478 (4)
H22A	0.7798	0.7597	0.7686	0.057*
H22B	0.7409	0.6849	0.6239	0.057*
C23	0.64722 (19)	0.5813 (2)	0.6966 (2)	0.0540 (5)
H23A	0.6653	0.5760	0.7749	0.065*
H23B	0.5696	0.6187	0.6857	0.065*
C24	0.62213 (19)	0.4422 (2)	0.5927 (2)	0.0543 (5)
H24A	0.5979	0.4466	0.5140	0.065*
H24B	0.5499	0.3849	0.5942	0.065*
C25	0.7435 (2)	0.3829 (2)	0.6057 (2)	0.0558 (5)
H25A	0.7264	0.2945	0.5377	0.067*
H25B	0.7645	0.3734	0.6821	0.067*
C26	0.85958 (19)	0.47217 (19)	0.60622 (19)	0.0486 (4)
H26A	0.8418	0.4754	0.5271	0.058*
H26B	0.9370	0.4348	0.6183	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.03937 (15)	0.04773 (16)	0.03899 (15)	0.01415 (11)	0.00682 (10)	0.02107 (12)
O1	0.0484 (7)	0.0497 (7)	0.0413 (7)	0.0202 (6)	0.0059 (6)	0.0161 (6)
O2	0.0563 (10)	0.0854 (12)	0.0633 (11)	−0.0018 (9)	−0.0140 (8)	0.0255 (9)
O3	0.0473 (9)	0.0888 (13)	0.0807 (12)	0.0265 (9)	0.0061 (8)	0.0361 (10)
O4	0.0425 (7)	0.0650 (9)	0.0548 (8)	0.0105 (6)	0.0079 (6)	0.0371 (7)
O5	0.0510 (9)	0.1031 (14)	0.0776 (12)	0.0198 (9)	0.0035 (8)	0.0545 (11)
O6	0.0358 (8)	0.0792 (11)	0.0885 (12)	0.0064 (7)	0.0020 (8)	0.0319 (10)
N1	0.0422 (8)	0.0425 (8)	0.0341 (7)	0.0113 (6)	0.0085 (6)	0.0150 (6)
N2	0.0382 (9)	0.0702 (12)	0.0546 (10)	0.0053 (8)	0.0056 (8)	0.0318 (9)
N3	0.0353 (7)	0.0427 (8)	0.0373 (7)	0.0098 (6)	0.0093 (6)	0.0173 (6)
N4	0.0370 (9)	0.0545 (10)	0.0544 (10)	0.0121 (7)	0.0031 (7)	0.0140 (8)
C1	0.0426 (9)	0.0424 (9)	0.0365 (9)	0.0110 (7)	0.0099 (7)	0.0180 (8)
C2	0.0392 (9)	0.0399 (9)	0.0364 (9)	0.0083 (7)	0.0077 (7)	0.0170 (7)
C3	0.0401 (9)	0.0449 (10)	0.0461 (10)	0.0120 (8)	0.0105 (8)	0.0221 (8)
C4	0.0375 (9)	0.0518 (11)	0.0421 (10)	0.0035 (8)	0.0057 (8)	0.0247 (9)
C5	0.0506 (11)	0.0491 (11)	0.0375 (10)	0.0036 (9)	0.0049 (8)	0.0125 (8)
C6	0.0546 (12)	0.0448 (10)	0.0449 (11)	0.0146 (9)	0.0101 (9)	0.0126 (9)
C7	0.0445 (10)	0.0407 (9)	0.0405 (9)	0.0136 (8)	0.0106 (8)	0.0163 (8)
C8	0.0437 (10)	0.0432 (10)	0.0361 (9)	0.0120 (8)	0.0085 (8)	0.0100 (8)
C9	0.0772 (15)	0.0509 (12)	0.0472 (11)	0.0055 (11)	0.0163 (11)	0.0189 (10)
C10	0.0839 (17)	0.0461 (12)	0.0584 (14)	0.0015 (11)	0.0138 (12)	0.0177 (10)
C11	0.0566 (13)	0.0552 (13)	0.0581 (13)	0.0060 (10)	−0.0035 (10)	0.0085 (11)
C12	0.0975 (19)	0.0607 (14)	0.0335 (10)	0.0089 (13)	0.0041 (11)	0.0126 (10)
C13	0.0905 (17)	0.0506 (12)	0.0386 (11)	0.0042 (11)	0.0075 (11)	0.0183 (9)
C14	0.0362 (9)	0.0374 (9)	0.0378 (9)	0.0092 (7)	0.0079 (7)	0.0137 (7)
C15	0.0407 (9)	0.0428 (10)	0.0435 (10)	0.0090 (8)	0.0081 (8)	0.0184 (8)
C16	0.0490 (11)	0.0638 (13)	0.0660 (14)	0.0014 (10)	0.0112 (10)	0.0393 (12)
C17	0.0389 (10)	0.0554 (12)	0.0679 (14)	0.0005 (9)	0.0101 (9)	0.0263 (11)
C18	0.0362 (9)	0.0404 (9)	0.0444 (10)	0.0090 (7)	0.0030 (8)	0.0113 (8)
C19	0.0399 (9)	0.0401 (9)	0.0394 (9)	0.0103 (7)	0.0061 (7)	0.0150 (8)
C20	0.0402 (9)	0.0421 (9)	0.0365 (9)	0.0115 (7)	0.0102 (7)	0.0182 (8)
C21	0.0363 (9)	0.0459 (10)	0.0360 (9)	0.0077 (7)	0.0082 (7)	0.0187 (8)
C22	0.0410 (10)	0.0507 (11)	0.0502 (11)	0.0131 (8)	0.0155 (8)	0.0193 (9)
C23	0.0381 (10)	0.0680 (13)	0.0566 (12)	0.0117 (9)	0.0166 (9)	0.0266 (11)
C24	0.0391 (10)	0.0646 (13)	0.0526 (12)	−0.0010 (9)	0.0070 (9)	0.0258 (10)
C25	0.0533 (12)	0.0482 (11)	0.0607 (13)	0.0053 (9)	0.0145 (10)	0.0214 (10)
C26	0.0451 (10)	0.0482 (11)	0.0525 (11)	0.0133 (8)	0.0164 (9)	0.0204 (9)

Geometric parameters (Å, º)

Co1—O4	1.906 (2)	C11—C12	1.501 (4)
Co1—O1	1.916 (2)	C11—H11A	0.9700
Co1—N1	1.994 (2)	C11—H11B	0.9700
Co1—N3	1.994 (2)	C12—C13	1.524 (3)
O1—C1	1.293 (2)	C12—H12A	0.9700
O2—N2	1.228 (2)	C12—H12B	0.9700
O3—N2	1.224 (2)	C13—H13A	0.9700
O4—C15	1.297 (2)	C13—H13B	0.9700
O5—N4	1.222 (2)	C14—C19	1.407 (2)
O6—N4	1.226 (2)	C14—C15	1.426 (3)
N1—C7	1.283 (2)	C14—C20	1.440 (2)
N1—C8	1.484 (2)	C15—C16	1.412 (3)
N2—C4	1.450 (2)	C16—C17	1.365 (3)
N3—C20	1.286 (2)	C16—H16	0.9300
N3—C21	1.479 (2)	C17—C18	1.386 (3)
N4—C18	1.462 (2)	C17—H17	0.9300
C1—C6	1.415 (3)	C18—C19	1.362 (3)
C1—C2	1.430 (2)	C19—H19	0.9300
C2—C3	1.403 (2)	C20—H20	0.9300
C2—C7	1.438 (2)	C21—C22	1.522 (3)
C3—C4	1.368 (3)	C21—C26	1.523 (3)
C3—H3	0.9300	C21—H21	0.9800
C4—C5	1.387 (3)	C22—C23	1.520 (3)
C5—C6	1.361 (3)	C22—H22A	0.9700
C5—H5	0.9300	C22—H22B	0.9700
C6—H6	0.9300	C23—C24	1.512 (3)
C7—H7	0.9300	C23—H23A	0.9700
C8—C13	1.502 (3)	C23—H23B	0.9700
C8—C9	1.506 (3)	C24—C25	1.519 (3)
C8—H8	0.9800	C24—H24A	0.9700
C9—C10	1.534 (3)	C24—H24B	0.9700
C9—H9A	0.9700	C25—C26	1.523 (3)
C9—H9B	0.9700	C25—H25A	0.9700
C10—C11	1.508 (3)	C25—H25B	0.9700
C10—H10A	0.9700	C26—H26A	0.9700
C10—H10B	0.9700	C26—H26B	0.9700
O4—Co1—O1	120.86 (6)	C13—C12—H12A	109.2
O4—Co1—N1	113.14 (6)	C11—C12—H12B	109.2
O1—Co1—N1	95.95 (6)	C13—C12—H12B	109.2
O4—Co1—N3	95.93 (6)	H12A—C12—H12B	107.9
O1—Co1—N3	110.11 (6)	C8—C13—C12	110.42 (19)
N1—Co1—N3	122.81 (6)	C8—C13—H13A	109.6
C1—O1—Co1	126.49 (12)	C12—C13—H13A	109.6
C15—O4—Co1	126.20 (12)	C8—C13—H13B	109.6
C7—N1—C8	116.31 (15)	C12—C13—H13B	109.6
C7—N1—Co1	120.99 (12)	H13A—C13—H13B	108.1
C8—N1—Co1	122.70 (11)	C19—C14—C15	118.97 (17)
O3—N2—O2	122.99 (19)	C19—C14—C20	116.53 (16)
O3—N2—C4	118.53 (18)	C15—C14—C20	124.47 (16)
O2—N2—C4	118.47 (19)	O4—C15—C16	118.48 (18)
C20—N3—C21	117.09 (15)	O4—C15—C14	124.18 (17)
C20—N3—Co1	121.24 (13)	C16—C15—C14	117.33 (17)
C21—N3—Co1	121.62 (11)	C17—C16—C15	122.6 (2)
O5—N4—O6	123.86 (18)	C17—C16—H16	118.7
O5—N4—C18	118.59 (17)	C15—C16—H16	118.7
O6—N4—C18	117.55 (19)	C16—C17—C18	118.85 (18)
O1—C1—C6	118.85 (17)	C16—C17—H17	120.6
O1—C1—C2	123.81 (16)	C18—C17—H17	120.6
C6—C1—C2	117.33 (16)	C19—C18—C17	121.48 (18)
C3—C2—C1	118.53 (16)	C19—C18—N4	119.30 (18)
C3—C2—C7	116.99 (16)	C17—C18—N4	119.22 (18)
C1—C2—C7	124.47 (16)	C18—C19—C14	120.73 (18)
C4—C3—C2	121.32 (17)	C18—C19—H19	119.6
C4—C3—H3	119.3	C14—C19—H19	119.6
C2—C3—H3	119.3	N3—C20—C14	127.42 (17)
C3—C4—C5	121.05 (17)	N3—C20—H20	116.3
C3—C4—N2	119.02 (18)	C14—C20—H20	116.3
C5—C4—N2	119.92 (18)	N3—C21—C22	110.36 (15)
C6—C5—C4	118.89 (18)	N3—C21—C26	110.04 (14)
C6—C5—H5	120.6	C22—C21—C26	111.37 (15)
C4—C5—H5	120.6	N3—C21—H21	108.3
C5—C6—C1	122.85 (18)	C22—C21—H21	108.3
C5—C6—H6	118.6	C26—C21—H21	108.3
C1—C6—H6	118.6	C23—C22—C21	111.09 (17)
N1—C7—C2	128.08 (17)	C23—C22—H22A	109.4
N1—C7—H7	116.0	C21—C22—H22A	109.4
C2—C7—H7	116.0	C23—C22—H22B	109.4
N1—C8—C13	111.06 (16)	C21—C22—H22B	109.4
N1—C8—C9	110.83 (15)	H22A—C22—H22B	108.0
C13—C8—C9	111.50 (18)	C24—C23—C22	110.79 (17)
N1—C8—H8	107.8	C24—C23—H23A	109.5
C13—C8—H8	107.8	C22—C23—H23A	109.5
C9—C8—H8	107.8	C24—C23—H23B	109.5
C8—C9—C10	110.01 (18)	C22—C23—H23B	109.5
C8—C9—H9A	109.7	H23A—C23—H23B	108.1
C10—C9—H9A	109.7	C23—C24—C25	110.51 (17)
C8—C9—H9B	109.7	C23—C24—H24A	109.5
C10—C9—H9B	109.7	C25—C24—H24A	109.5
H9A—C9—H9B	108.2	C23—C24—H24B	109.5
C11—C10—C9	111.6 (2)	C25—C24—H24B	109.5
C11—C10—H10A	109.3	H24A—C24—H24B	108.1
C9—C10—H10A	109.3	C24—C25—C26	110.81 (17)
C11—C10—H10B	109.3	C24—C25—H25A	109.5
C9—C10—H10B	109.3	C26—C25—H25A	109.5
H10A—C10—H10B	108.0	C24—C25—H25B	109.5
C12—C11—C10	111.30 (19)	C26—C25—H25B	109.5
C12—C11—H11A	109.4	H25A—C25—H25B	108.1
C10—C11—H11A	109.4	C25—C26—C21	110.45 (16)
C12—C11—H11B	109.4	C25—C26—H26A	109.6
C10—C11—H11B	109.4	C21—C26—H26A	109.6
H11A—C11—H11B	108.0	C25—C26—H26B	109.6
C11—C12—C13	111.9 (2)	C21—C26—H26B	109.6
C11—C12—H12A	109.2	H26A—C26—H26B	108.1