Aqua­chlorido{6,6′-dimeth­oxy-2,2′-[ethane-1,2-diylbis(nitrilo­methanylyl­idene)]diphenolato-κ2O1,N,N′,O1′}cobalt(III) dimethyl­formamide monosolvate

Wei, Y.; Pang, T.; Liu, J.; Li, M.; Liang, L.

doi:10.1107/S1600536812011324

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m455-m456

doi:10.1107/S1600536812011324

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Aquachlorido{6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolato-κ²O¹,N,N′,O^1′}cobalt(III) dimethylformamide monosolvate

Yun Wei,^a Ting Pang,^a Jiacheng Liu,^a ^* Meng Li ^a and Lili Liang ^a

^aCollege of Chemistry and Chemical Engineering, Key Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Key Laboratory of Polymer Materials of Gansu Province, Key Laboratory of Bioelectrochemistry and Environmental Analysis of Gansu, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: jcliu8@nwnu.edu.cn

(Received 2 March 2012; accepted 15 March 2012; online 21 March 2012)

In the title compound, [Co(C₁₈H₁₈N₂O₄)Cl(H₂O)]·C₃H₇NO, the Co^III ion is six-coordinated by a tetradentate 6,6′-dimethoxy-2,2′-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolate ligand, with a chloride ion and an aqua ligand in the apical positions. The compound crystallized as a dimethylformamide (DMF) monosolvate. In the crystal, complex molecules are linked via O—H_water⋯O hydrogen bonds to form a dimer-like arrangement. These dimers are linked via a C—H⋯Cl interaction, and the DMF molecule is linked to the complex molecule by C—H⋯O interactions.

Related literature

For related literature on metal complexes of Schiff bases, see: Aurangzeb et al. (1994 ); Hulme et al. (1997 ); Li et al. (2008 ); Wang et al. (1979 ); Xing (2009 ). For transition metal complexes of Schiff bases derived from o-vanillin, with antibacterial activity, see: Liu et al. (1990 ); Viswanathamurthi et al. (2000 ); Yeap et al. (2003 ). For the crystal structure of the ligand, see: Xia et al. (2006 ). For the crystal structure of the monohydrate form of the title complex, see: Xing (2009).

Experimental

Crystal data

[Co(C₁₈H₁₈N₂O₄)Cl(H₂O)]·C₃H₇NO
M_r = 511.84
Monoclinic, P 2₁ /c
a = 13.1384 (13) Å
b = 13.3144 (19) Å
c = 14.0120 (9) Å
β = 110.198 (6)°
V = 2300.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.812, T_max = 0.840
12275 measured reflections
4034 independent reflections
2827 reflections with I > 2σ(I)
R_int = 0.087

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.140
S = 1.01
4034 reflections
293 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O2ⁱ	0.96	1.98	2.830 (3)	146
O5—H5A⋯O4ⁱ	0.96	2.22	2.964 (4)	134
O5—H5B⋯O1ⁱ	0.96	2.11	2.840 (3)	131
O5—H5B⋯O3ⁱ	0.96	1.97	2.854 (3)	151
C9—H9B⋯O6ⁱⁱ	0.97	2.47	3.355 (7)	152
C10—H10⋯O6ⁱⁱ	0.93	2.56	3.287 (7)	135
C17—H17A⋯Cl5ⁱⁱⁱ	0.96	2.79	3.744 (4)	175
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812011324/su2386sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011324/su2386Isup2.hkl

checkCIF report

Comment top

Polydentate Schiff base ligands and their metal complexes have been studied for decades (Aurangzeb et al., 1994, Hulme et al., 1997; Li et al., 2008; Wang et al., 1979; Xing, 2009). Transition metal complexes of Schiff bases derived from o-vanillin have attracted more attention during past years due to their antibacterial activity (Liu et al., 1990; Viswanathamurthi et al., 2000; Yeap et al., 2003). Herein, we report on the synthesis and crystal structure of the title cobalt(III) complex.

The molecular structure of the title compound is illustrated in Fig. 1. The Co^III ion is coordinated to two N and two O atoms of the tetradentate 6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenolate ligand, a Cl^- ion and one water molecule. The compound crystallized with a molecule of dimethylformamide, used as solvent. The crystal structure of the ligand has been reported previously (Xia et al., 2006), as has the monohydrate form of the title complex (Xing, 2009). The Cl5—Co1—O5 bond angle is 178.77 (7)° suggesting that the Co^III ion has a slightly distorted octahedral environment, with atoms N1, N2, O1 and O2 occupying the equatorial positions, while atoms Cl5 and O5_water occupy the axial positions.

In the crystal, complex molecules are linked via O-H_water···O hydrogen bonds to form a dimer-like arrangement. These dimers are linked via a C-H···Cl interaction, and the DMF molecule is linked to the complex molecule by C-H···O interactions (Table 1).

Related literature top

For related literature on metal complexes of Schiff bases, see: Aurangzeb et al. (1994); Hulme et al. (1997); Li et al. (2008); Wang et al. (1979); Xing (2009). For transition metal complexes of Schiff bases derived from o-vanillin, with antibacterial activity, see: Liu et al. (1990); Viswanathamurthi et al. (2000); Yeap et al. (2003). For the crystal structure of the ligand, see: Xia et al. (2006). For the crystal structure of the monohydrate form of the title complex, see: Xing (2009).

Experimental top

A colourless solution of 6,6'-dimethoxy-2,2'-[ethane-1,2-diylbis(nitrilomethanylylidene)]diphenol (54.5 mg,0.2 mmol) in DMF (3 ml) was slowly added to a solution of CoCl₂ (64 mg, 0.2 mmol) in CH₃CN(15 ml), forming a dark red solution that was stirred for 30 min at room temperature. Slow evaporation of the solvent at room temperature gave red block-like crystals of the title compound, suitable for X-ray analysis. The crystals were collected by filtration, washed with cold acetonitrile, and dried under vacuum (yield 77%).

Structure description top

For related literature on metal complexes of Schiff bases, see: Aurangzeb et al. (1994); Hulme et al. (1997); Li et al. (2008); Wang et al. (1979); Xing (2009). For transition metal complexes of Schiff bases derived from o-vanillin, with antibacterial activity, see: Liu et al. (1990); Viswanathamurthi et al. (2000); Yeap et al. (2003). For the crystal structure of the ligand, see: Xia et al. (2006). For the crystal structure of the monohydrate form of the title complex, see: Xing (2009).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. A view of the molecular structure of the title complex, with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Aquachlorido{6,6'-dimethoxy-2,2'-[ethane-1,2- diylbis(nitrilomethanylylidene)]diphenolato- κ²O¹,N,N',O^1'}cobalt(III) dimethylformamide monosolvate top

Crystal data top

[Co(C₁₈H₁₈N₂O₄)Cl(H₂O)]·C₃H₇NO	F(000) = 1064
M_r = 511.84	D_x = 1.478 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2594 reflections
a = 13.1384 (13) Å	θ = 2.3–22.5°
b = 13.3144 (19) Å	µ = 0.90 mm⁻¹
c = 14.0120 (9) Å	T = 293 K
β = 110.198 (6)°	Block, red
V = 2300.4 (4) Å³	0.24 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4034 independent reflections
Radiation source: fine-focus sealed tube	2827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
φ and ω scans	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −15→15
T_min = 0.812, T_max = 0.840	k = −15→14
12275 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0689P)²] where P = (F_o² + 2F_c²)/3
4034 reflections	(Δ/σ)_max = 0.001
293 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Co(C₁₈H₁₈N₂O₄)Cl(H₂O)]·C₃H₇NO	V = 2300.4 (4) Å³
M_r = 511.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.1384 (13) Å	µ = 0.90 mm⁻¹
b = 13.3144 (19) Å	T = 293 K
c = 14.0120 (9) Å	0.24 × 0.22 × 0.20 mm
β = 110.198 (6)°

Data collection top

Bruker APEXII CCD diffractometer	4034 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2827 reflections with I > 2σ(I)
T_min = 0.812, T_max = 0.840	R_int = 0.087
12275 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.01	Δρ_max = 0.70 e Å⁻³
4034 reflections	Δρ_min = −0.39 e Å⁻³
293 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.90848 (4)	0.14998 (3)	0.92275 (3)	0.0496 (2)
Cl5	0.92093 (9)	0.30523 (7)	0.98338 (7)	0.0715 (4)
O1	0.90866 (18)	0.09840 (17)	1.04805 (16)	0.0522 (8)
O2	1.06060 (18)	0.13508 (17)	0.97448 (17)	0.0539 (8)
O3	0.94754 (18)	0.02362 (19)	1.22469 (16)	0.0611 (9)
O4	1.26159 (19)	0.1281 (2)	1.08943 (19)	0.0673 (10)
O5	0.89466 (17)	0.01086 (16)	0.86955 (15)	0.0533 (8)
N1	0.9079 (2)	0.1957 (2)	0.7953 (2)	0.0535 (10)
N2	0.7567 (2)	0.1638 (2)	0.8674 (2)	0.0569 (10)
C1	1.1284 (3)	0.1773 (2)	0.9372 (3)	0.0515 (11)
C2	1.2396 (3)	0.1745 (3)	0.9968 (3)	0.0606 (14)
C3	1.3174 (3)	0.2134 (3)	0.9619 (3)	0.0751 (17)
C4	1.2861 (4)	0.2591 (4)	0.8665 (4)	0.0822 (17)
C5	1.1799 (4)	0.2652 (3)	0.8074 (3)	0.0737 (17)
C6	1.0988 (3)	0.2252 (3)	0.8418 (3)	0.0578 (12)
C7	0.9889 (3)	0.2273 (3)	0.7741 (3)	0.0594 (14)
C8	0.7993 (3)	0.1895 (3)	0.7181 (3)	0.0698 (16)
C9	0.7199 (3)	0.2143 (3)	0.7682 (3)	0.0743 (16)
C10	0.6880 (3)	0.1424 (3)	0.9111 (3)	0.0586 (12)
C11	0.7150 (3)	0.1020 (3)	1.0106 (3)	0.0541 (12)
C12	0.6303 (3)	0.0808 (3)	1.0478 (3)	0.0663 (14)
C13	0.6511 (3)	0.0418 (3)	1.1417 (3)	0.0727 (17)
C14	0.7565 (3)	0.0214 (3)	1.2036 (3)	0.0665 (16)
C15	0.8411 (3)	0.0409 (3)	1.1708 (2)	0.0543 (11)
C16	0.8231 (3)	0.0820 (2)	1.0729 (2)	0.0499 (11)
C17	0.9757 (3)	−0.0122 (3)	1.3268 (2)	0.0700 (16)
C18	1.3706 (3)	0.1101 (4)	1.1502 (3)	0.0778 (17)
O6	0.5199 (4)	0.9040 (5)	0.2962 (4)	0.192 (3)
N3	0.6662 (5)	0.9626 (6)	0.4178 (4)	0.134 (3)
C19	0.7766 (5)	0.9485 (6)	0.4778 (4)	0.168 (4)
C20	0.6114 (8)	1.0463 (11)	0.4401 (8)	0.236 (8)
C21	0.6116 (6)	0.9002 (6)	0.3479 (5)	0.141 (3)
H3	1.39040	0.20920	1.00180	0.0900*
H4	1.33860	0.28570	0.84310	0.0980*
H5	1.16020	0.29590	0.74400	0.0890*
H5A	0.87980	−0.03370	0.91700	0.0800*
H5B	0.96130	−0.00860	0.86080	0.0800*
H7	0.97560	0.25380	0.70950	0.0710*
H8A	0.78620	0.12230	0.68970	0.0840*
H8B	0.79280	0.23660	0.66340	0.0840*
H9A	0.71680	0.28640	0.77700	0.0890*
H9B	0.64820	0.19090	0.72730	0.0890*
H10	0.61510	0.15420	0.87490	0.0700*
H12	0.55890	0.09390	1.00710	0.0790*
H13	0.59420	0.02860	1.16480	0.0870*
H14	0.76990	−0.00570	1.26800	0.0800*
H17A	0.95880	0.03830	1.36800	0.0840*
H17B	1.05190	−0.02680	1.35360	0.0840*
H17C	0.93540	−0.07210	1.32750	0.0840*
H18A	1.40490	0.07070	1.11250	0.0940*
H18B	1.37300	0.07430	1.21040	0.0940*
H18C	1.40800	0.17290	1.16890	0.0940*
H19A	0.80250	0.88730	0.45800	0.2020*
H19B	0.78360	0.94460	0.54820	0.2020*
H19C	0.81850	1.00400	0.46800	0.2020*
H20A	0.53720	1.04620	0.39530	0.3540*
H20B	0.64610	1.10710	0.43080	0.3540*
H20C	0.61390	1.04200	0.50920	0.3540*
H21	0.65020	0.84530	0.33730	0.1690*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0578 (3)	0.0354 (3)	0.0523 (3)	0.0018 (2)	0.0148 (2)	0.0031 (2)
Cl5	0.0952 (8)	0.0478 (5)	0.0697 (6)	0.0027 (5)	0.0262 (5)	−0.0019 (4)
O1	0.0540 (13)	0.0457 (14)	0.0556 (13)	0.0024 (11)	0.0173 (11)	0.0083 (10)
O2	0.0593 (14)	0.0420 (13)	0.0586 (14)	−0.0011 (11)	0.0179 (11)	0.0085 (10)
O3	0.0649 (16)	0.0616 (16)	0.0533 (14)	0.0079 (13)	0.0158 (12)	0.0069 (11)
O4	0.0587 (16)	0.0688 (18)	0.0702 (16)	0.0024 (13)	0.0171 (13)	0.0054 (13)
O5	0.0599 (14)	0.0371 (12)	0.0615 (13)	−0.0006 (11)	0.0192 (11)	0.0021 (10)
N1	0.0674 (19)	0.0372 (16)	0.0520 (16)	−0.0020 (14)	0.0157 (15)	0.0019 (12)
N2	0.0667 (19)	0.0432 (17)	0.0551 (17)	0.0056 (14)	0.0136 (16)	0.0072 (13)
C1	0.064 (2)	0.0339 (18)	0.060 (2)	−0.0031 (16)	0.0259 (19)	−0.0050 (15)
C2	0.069 (3)	0.050 (2)	0.067 (2)	−0.0035 (19)	0.029 (2)	−0.0060 (17)
C3	0.072 (3)	0.070 (3)	0.087 (3)	−0.008 (2)	0.032 (2)	−0.006 (2)
C4	0.083 (3)	0.082 (3)	0.095 (3)	−0.016 (3)	0.048 (3)	−0.003 (3)
C5	0.097 (3)	0.059 (3)	0.074 (3)	−0.012 (2)	0.041 (3)	0.0032 (19)
C6	0.070 (2)	0.044 (2)	0.062 (2)	−0.0035 (18)	0.026 (2)	−0.0028 (16)
C7	0.086 (3)	0.041 (2)	0.052 (2)	0.0026 (19)	0.025 (2)	0.0048 (15)
C8	0.082 (3)	0.066 (3)	0.052 (2)	−0.002 (2)	0.011 (2)	0.0086 (17)
C9	0.069 (3)	0.074 (3)	0.067 (2)	0.006 (2)	0.007 (2)	0.017 (2)
C10	0.055 (2)	0.046 (2)	0.066 (2)	0.0043 (17)	0.0098 (19)	0.0027 (16)
C11	0.056 (2)	0.044 (2)	0.059 (2)	0.0013 (17)	0.0158 (17)	−0.0028 (15)
C12	0.056 (2)	0.069 (3)	0.072 (2)	0.0048 (19)	0.0197 (19)	−0.002 (2)
C13	0.070 (3)	0.080 (3)	0.075 (3)	0.001 (2)	0.034 (2)	−0.001 (2)
C14	0.077 (3)	0.066 (3)	0.060 (2)	0.002 (2)	0.028 (2)	0.0043 (18)
C15	0.064 (2)	0.0418 (19)	0.056 (2)	0.0031 (17)	0.0192 (18)	−0.0021 (15)
C16	0.060 (2)	0.0353 (18)	0.056 (2)	0.0043 (16)	0.0222 (17)	−0.0025 (14)
C17	0.083 (3)	0.067 (3)	0.054 (2)	0.010 (2)	0.016 (2)	0.0007 (18)
C18	0.061 (3)	0.076 (3)	0.086 (3)	0.004 (2)	0.012 (2)	−0.002 (2)
O6	0.128 (4)	0.242 (7)	0.143 (4)	−0.093 (4)	−0.033 (3)	0.061 (4)
N3	0.121 (4)	0.159 (6)	0.096 (3)	−0.056 (4)	0.005 (3)	0.032 (3)
C19	0.148 (6)	0.189 (8)	0.115 (4)	−0.095 (6)	−0.021 (4)	0.057 (5)
C20	0.215 (11)	0.292 (18)	0.224 (11)	−0.008 (10)	0.105 (8)	−0.032 (11)
C21	0.138 (6)	0.134 (6)	0.103 (4)	−0.075 (5)	−0.019 (4)	0.041 (4)

Geometric parameters (Å, º) top

Co1—Cl5	2.2193 (11)	C11—C12	1.411 (6)
Co1—O1	1.885 (2)	C11—C16	1.412 (5)
Co1—O2	1.887 (3)	C12—C13	1.352 (6)
Co1—O5	1.982 (2)	C13—C14	1.384 (6)
Co1—N1	1.884 (3)	C14—C15	1.366 (6)
Co1—N2	1.883 (3)	C15—C16	1.419 (4)
O1—C16	1.305 (5)	C3—H3	0.9300
O2—C1	1.305 (5)	C4—H4	0.9300
O3—C15	1.360 (4)	C5—H5	0.9300
O3—C17	1.430 (4)	C7—H7	0.9300
O4—C2	1.375 (5)	C8—H8B	0.9700
O4—C18	1.411 (5)	C8—H8A	0.9700
O5—H5A	0.9600	C9—H9B	0.9700
O5—H5B	0.9600	C9—H9A	0.9700
O6—C21	1.173 (9)	C10—H10	0.9300
N1—C7	1.271 (5)	C12—H12	0.9300
N1—C8	1.465 (5)	C13—H13	0.9300
N2—C10	1.286 (5)	C14—H14	0.9300
N2—C9	1.468 (5)	C17—H17A	0.9600
N3—C19	1.416 (9)	C17—H17B	0.9600
N3—C20	1.419 (15)	C17—H17C	0.9600
N3—C21	1.296 (10)	C18—H18B	0.9600
C1—C6	1.409 (5)	C18—H18C	0.9600
C1—C2	1.411 (6)	C18—H18A	0.9600
C2—C3	1.378 (6)	C19—H19A	0.9600
C3—C4	1.395 (7)	C19—H19B	0.9600
C4—C5	1.357 (7)	C19—H19C	0.9600
C5—C6	1.416 (7)	C20—H20A	0.9600
C6—C7	1.428 (6)	C20—H20B	0.9600
C8—C9	1.482 (6)	C20—H20C	0.9600
C10—C11	1.420 (6)	C21—H21	0.9300

Cl5—Co1—O1	90.38 (7)	C11—C16—C15	117.8 (4)
Cl5—Co1—O2	91.29 (8)	O1—C16—C15	116.8 (3)
Cl5—Co1—O5	178.77 (8)	O1—C16—C11	125.4 (3)
Cl5—Co1—N1	92.15 (9)	C2—C3—H3	120.00
Cl5—Co1—N2	89.67 (9)	C4—C3—H3	120.00
O1—Co1—O2	86.75 (10)	C5—C4—H4	120.00
O1—Co1—O5	88.87 (9)	C3—C4—H4	120.00
O1—Co1—N1	177.47 (11)	C4—C5—H5	120.00
O1—Co1—N2	94.58 (11)	C6—C5—H5	120.00
O2—Co1—O5	89.63 (10)	N1—C7—H7	118.00
O2—Co1—N1	93.16 (11)	C6—C7—H7	117.00
O2—Co1—N2	178.35 (11)	C9—C8—H8B	110.00
O5—Co1—N1	88.60 (10)	H8A—C8—H8B	108.00
O5—Co1—N2	89.42 (11)	C9—C8—H8A	110.00
N1—Co1—N2	85.46 (12)	N1—C8—H8A	110.00
Co1—O1—C16	125.8 (2)	N1—C8—H8B	110.00
Co1—O2—C1	125.4 (2)	N2—C9—H9A	110.00
C15—O3—C17	118.2 (3)	N2—C9—H9B	110.00
C2—O4—C18	119.0 (3)	C8—C9—H9A	110.00
Co1—O5—H5A	109.00	C8—C9—H9B	110.00
Co1—O5—H5B	109.00	H9A—C9—H9B	109.00
H5A—O5—H5B	110.00	C11—C10—H10	117.00
Co1—N1—C7	126.8 (3)	N2—C10—H10	118.00
Co1—N1—C8	111.5 (2)	C11—C12—H12	120.00
C7—N1—C8	121.8 (3)	C13—C12—H12	119.00
C9—N2—C10	119.8 (3)	C12—C13—H13	120.00
Co1—N2—C10	126.9 (3)	C14—C13—H13	120.00
Co1—N2—C9	113.0 (2)	C15—C14—H14	120.00
C19—N3—C21	123.4 (7)	C13—C14—H14	120.00
C20—N3—C21	118.7 (8)	O3—C17—H17B	109.00
C19—N3—C20	117.9 (7)	H17A—C17—H17C	109.00
C2—C1—C6	117.6 (4)	O3—C17—H17C	110.00
O2—C1—C2	117.5 (3)	H17A—C17—H17B	109.00
O2—C1—C6	124.9 (4)	O3—C17—H17A	110.00
O4—C2—C1	114.1 (3)	H17B—C17—H17C	109.00
O4—C2—C3	124.4 (4)	O4—C18—H18C	110.00
C1—C2—C3	121.6 (4)	H18A—C18—H18C	109.00
C2—C3—C4	119.7 (4)	H18B—C18—H18C	110.00
C3—C4—C5	120.8 (5)	H18A—C18—H18B	109.00
C4—C5—C6	120.4 (4)	O4—C18—H18A	109.00
C5—C6—C7	118.3 (4)	O4—C18—H18B	109.00
C1—C6—C5	120.0 (4)	O6—C21—N3	128.4 (8)
C1—C6—C7	121.6 (4)	N3—C19—H19A	109.00
N1—C7—C6	125.1 (4)	N3—C19—H19B	109.00
N1—C8—C9	107.6 (3)	N3—C19—H19C	110.00
N2—C9—C8	106.9 (3)	H19A—C19—H19B	109.00
N2—C10—C11	125.0 (4)	H19A—C19—H19C	110.00
C12—C11—C16	119.2 (3)	H19B—C19—H19C	109.00
C10—C11—C16	122.4 (4)	N3—C20—H20A	109.00
C10—C11—C12	118.5 (4)	N3—C20—H20B	109.00
C11—C12—C13	121.1 (4)	N3—C20—H20C	109.00
C12—C13—C14	120.5 (4)	H20A—C20—H20B	110.00
C13—C14—C15	120.4 (4)	H20A—C20—H20C	109.00
O3—C15—C14	125.5 (3)	H20B—C20—H20C	110.00
C14—C15—C16	121.0 (3)	O6—C21—H21	116.00
O3—C15—C16	113.5 (3)	N3—C21—H21	116.00

Cl5—Co1—O1—C16	90.4 (2)	Co1—N2—C10—C11	−1.2 (6)
O2—Co1—O1—C16	−178.3 (2)	C10—N2—C9—C8	−155.7 (3)
O5—Co1—O1—C16	−88.6 (2)	C19—N3—C21—O6	178.1 (8)
N2—Co1—O1—C16	0.7 (2)	C20—N3—C21—O6	2.1 (13)
Cl5—Co1—O2—C1	−73.5 (2)	O2—C1—C6—C5	−177.6 (3)
O1—Co1—O2—C1	−163.8 (3)	C2—C1—C6—C7	176.8 (4)
O5—Co1—O2—C1	107.3 (3)	O2—C1—C2—O4	−1.3 (5)
N1—Co1—O2—C1	18.7 (3)	O2—C1—C6—C7	−3.0 (6)
Cl5—Co1—N1—C7	75.7 (3)	O2—C1—C2—C3	177.3 (3)
Cl5—Co1—N1—C8	−105.3 (2)	C2—C1—C6—C5	2.2 (5)
O2—Co1—N1—C7	−15.8 (3)	C6—C1—C2—C3	−2.6 (5)
O2—Co1—N1—C8	163.3 (2)	C6—C1—C2—O4	178.9 (3)
O5—Co1—N1—C7	−105.3 (3)	C1—C2—C3—C4	1.7 (6)
O5—Co1—N1—C8	73.7 (2)	O4—C2—C3—C4	−180.0 (4)
N2—Co1—N1—C7	165.2 (3)	C2—C3—C4—C5	−0.4 (7)
N2—Co1—N1—C8	−15.8 (2)	C3—C4—C5—C6	0.1 (7)
Cl5—Co1—N2—C9	83.4 (2)	C4—C5—C6—C7	−175.8 (4)
Cl5—Co1—N2—C10	−89.9 (3)	C4—C5—C6—C1	−1.0 (6)
O1—Co1—N2—C9	173.8 (2)	C5—C6—C7—N1	−178.8 (4)
O1—Co1—N2—C10	0.5 (3)	C1—C6—C7—N1	6.6 (6)
O5—Co1—N2—C9	−97.4 (2)	N1—C8—C9—N2	−41.8 (4)
O5—Co1—N2—C10	89.3 (3)	N2—C10—C11—C16	0.7 (6)
N1—Co1—N2—C9	−8.8 (2)	N2—C10—C11—C12	−179.0 (4)
N1—Co1—N2—C10	177.9 (3)	C10—C11—C12—C13	179.7 (4)
Co1—O1—C16—C11	−1.3 (4)	C16—C11—C12—C13	0.0 (6)
Co1—O1—C16—C15	178.8 (2)	C12—C11—C16—C15	0.1 (5)
Co1—O2—C1—C2	167.5 (2)	C12—C11—C16—O1	−179.7 (3)
Co1—O2—C1—C6	−12.7 (5)	C10—C11—C16—O1	0.6 (5)
C17—O3—C15—C16	176.4 (3)	C10—C11—C16—C15	−179.5 (3)
C17—O3—C15—C14	−4.1 (5)	C11—C12—C13—C14	−0.2 (6)
C18—O4—C2—C3	−6.1 (6)	C12—C13—C14—C15	0.3 (6)
C18—O4—C2—C1	172.4 (3)	C13—C14—C15—C16	−0.2 (6)
Co1—N1—C8—C9	36.3 (3)	C13—C14—C15—O3	−179.7 (4)
C7—N1—C8—C9	−144.6 (4)	O3—C15—C16—C11	179.6 (3)
Co1—N1—C7—C6	6.2 (6)	C14—C15—C16—O1	179.8 (3)
C8—N1—C7—C6	−172.7 (4)	C14—C15—C16—C11	0.0 (5)
Co1—N2—C9—C8	30.5 (4)	O3—C15—C16—O1	−0.6 (4)
C9—N2—C10—C11	−174.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.96	1.98	2.830 (3)	146
O5—H5A···O4ⁱ	0.96	2.22	2.964 (4)	134
O5—H5B···O1ⁱ	0.96	2.11	2.840 (3)	131
O5—H5B···O3ⁱ	0.96	1.97	2.854 (3)	151
C9—H9B···O6ⁱⁱ	0.97	2.47	3.355 (7)	152
C10—H10···O6ⁱⁱ	0.93	2.56	3.287 (7)	135
C17—H17A···Cl5ⁱⁱⁱ	0.96	2.79	3.744 (4)	175

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₁₈H₁₈N₂O₄)Cl(H₂O)]·C₃H₇NO
M_r	511.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.1384 (13), 13.3144 (19), 14.0120 (9)
β (°)	110.198 (6)
V (Å³)	2300.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.812, 0.840
No. of measured, independent and observed [I > 2σ(I)] reflections	12275, 4034, 2827
R_int	0.087
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.140, 1.01
No. of reflections	4034
No. of parameters	293
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.39

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O2ⁱ	0.96	1.98	2.830 (3)	146
O5—H5A···O4ⁱ	0.96	2.22	2.964 (4)	134
O5—H5B···O1ⁱ	0.96	2.11	2.840 (3)	131
O5—H5B···O3ⁱ	0.96	1.97	2.854 (3)	151
C9—H9B···O6ⁱⁱ	0.97	2.47	3.355 (7)	152
C10—H10···O6ⁱⁱ	0.93	2.56	3.287 (7)	135
C17—H17A···Cl5ⁱⁱⁱ	0.96	2.79	3.744 (4)	175

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1/2, z+1/2.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20871099) and the Natural Science Foundation of Gansu Province (grant No. 0710RJZA113) for financial support. The authors also thank the Key Laboratory of Eco-Environment-Related Polymer Materials (Northwest Normal University), Ministry of Education, for financial support.

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