Dichlorido(dimethyl­formamide-κO)[1,4,7-tris­(2-cyano­ethyl)-1,4,7-triaza­cyclo­nonane-κ3N1,N4,N7]cobalt(II)

Zhang, Z.; Geng, Z.-R.; Zhao, Q.; Wang, Z.-L.

doi:10.1107/S160053680802179X

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1041-m1042

doi:10.1107/S160053680802179X

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Dichlorido(dimethylformamide-κO)[1,4,7-tris(2-cyanoethyl)-1,4,7-triazacyclononane-κ³N¹,N⁴,N⁷]cobalt(II)

Zhong Zhang,^a Zhi-Rong Geng,^a Qun Zhao ^a and Zhi-Lin Wang ^a ^*

^aCoordination Chemistry Institute, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: zzkltl@yahoo.com.cn

(Received 8 June 2008; accepted 13 July 2008; online 19 July 2008)

The title compound, [CoCl₂(C₁₅H₂₄N₆)(C₃H₇NO)], crystallizes as a monomeric complex. The coordination environment around the Co^II center could be described as a distorted octahedron consisting of three N donors from the facially coordinating triaza macrocyclic ligand, one O donor from dimethylformamide and two Cl⁻ ions. Neutral complex molecules are associated via intermolecular C—H⋯Cl hydrogen bonds to form two-dimensional layers. C—H⋯O hydrogen bonds are also present.

Related literature

For related literature, see: Scarpellini et al. (2005 ); Tei et al. (1998 , 2003 ).

Experimental

Crystal data

[CoCl₂(C₁₅H₂₄N₆)(C₃H₇NO)]
M_r = 491.33
Monoclinic, P 2₁ /n
a = 9.787 (2) Å
b = 19.710 (5) Å
c = 12.370 (3) Å
β = 97.936 (4)°
V = 2363.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.97 mm⁻¹
T = 298 (2) K
0.32 × 0.26 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.746, T_max = 0.800
12542 measured reflections
4630 independent reflections
3320 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.154
S = 1.07
4630 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.90 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cl1—Co1	2.4382 (14)
Cl2—Co1	2.4096 (13)
Co1—O1	2.114 (3)
Co1—N2	2.194 (4)
Co1—N3	2.200 (4)
Co1—N1	2.232 (4)

O1—Co1—N2	87.78 (12)
O1—Co1—N3	168.01 (13)
N2—Co1—N3	80.93 (13)
O1—Co1—N1	93.00 (13)
N2—Co1—N1	81.07 (14)
N3—Co1—N1	81.30 (13)
O1—Co1—Cl2	90.45 (9)
N2—Co1—Cl2	173.80 (10)
N3—Co1—Cl2	100.34 (10)
N1—Co1—Cl2	93.09 (10)
O1—Co1—Cl1	91.12 (9)
N2—Co1—Cl1	93.38 (10)
N3—Co1—Cl1	93.58 (10)
N1—Co1—Cl1	172.94 (10)
Cl2—Co1—Cl1	92.60 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cl2ⁱ	0.97	2.75	3.658 (4)	157
C2—H2A⋯O1	0.97	2.58	3.120 (5)	116
C3—H3A⋯Cl2ⁱ	0.97	2.81	3.774 (4)	170
C7—H7A⋯Cl2	0.97	2.65	3.419 (4)	136
C10—H10A⋯O1	0.97	2.47	3.149 (6)	127
C10—H10B⋯Cl1	0.97	2.73	3.218 (4)	111
C11—H11A⋯Cl1ⁱ	0.97	2.62	3.525 (5)	156
C11—H11B⋯Cl2ⁱⁱ	0.97	2.65	3.502 (5)	147
C13—H13A⋯Cl1	0.97	2.72	3.460 (5)	133
C16—H16⋯Cl2	0.93	2.80	3.325 (5)	117
C17—H17A⋯O1	0.96	2.34	2.741 (7)	105
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802179X/ww2123sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802179X/ww2123Isup2.hkl

checkCIF report

Comment top

Structural investigations on metal complexes with nitrile pendant arm derivatives of 1,4,7-triazacyclononane ([9]aneN₃) reveal that these triazamacrocyclic ligands can either be used as building-blocks to assemble multi-dimensional polymeric networks (Tei et al., 1998) or only act as tridentate ligands in the formation of mononuclear complexes with the pendant nitrile groups not involved in metal coordination (Tei et al., 2003). In this paper, we report the crystal structure of the title compound, (I), which is a monomeric Co^II complex of a [9]aneN₃ derivative containing three pendant 2-cyanoethyl arms.

The molecular structure of (I) (Fig. 1) shows the Co^II ion is six-coordinated with three tertiary N donors from the nitrile-functionalized [9]aneN₃, one O donor from dimethylformamide ligand and two Cl^- ions completing an octahedral geometry. All bond distances and angles around the octahedral Co^II ion (Table 1) are generally within the normal ranges (Scarpellini et al., 2005). Three pendant 2-cyanoethyl arms attached to the triazamacrocycle adopt different conformations relative to the macrocycle framework and none of them participates in the coordination to the Co^II ion.

The crystal packing of (I) is dominated by intermolecular C—H···Cl hydrogen bonds (Table 2), which link the complex molecules to form two-dimensional hydrogen-bonded layers parallel to (010) plane (Fig. 2).

Related literature top

For related literature, see: Scarpellini et al. (2005); Tei et al. (1998, 2003).

Experimental top

The triazamacrocyclic ligand 1,4,7-tris(2-cyanoethyl)-1,4,7-triazacyclononane was prepared following a literature procedure (Tei et al., 1998). A mixture of the triazamacrocyclic ligand (29 mg, 0.1 mmol) and CoCl₂.6H₂O (24 mg, 0.1 mmol) in MeOH (10 ml) was stirred under reflux for 2 h. The precipitated pink solid was filtered off and subsequently redissolved in dimethylformamide. Purple single crystals of (I) suitable for X-ray diffraction analysis were obtained by slow diffusion of diethyl ether into the dimethylformamide solution. (yield 23 mg, 46.8%) Elemental analysis found: C 44.13; H 6.41; N 19.81%; calculated for C₁₈H₃₁Cl₂CoN₇O: C 44.00; H 6.36; N 19.96%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level (arbitrary sphere for H atoms).
	Fig. 2. Partial packing diagram of the title compound, showing the two-dimensional network formed through intermolecular C—H···Cl hydrogen bonds (dashed lines). For clarity, H atoms not involved in hydrogen bonding have been omitted.

Dichlorido(dimethylformamide-κO)[1,4,7-tris(2-cyanoethyl)-1,4,7- triazacyclononane-κ³N¹,N⁴,N⁷]cobalt(II) top

Crystal data top

[CoCl₂(C₁₅H₂₄N₆)(C₃H₇NO)]	F(000) = 1028
M_r = 491.33	D_x = 1.381 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 915 reflections
a = 9.787 (2) Å	θ = 3.2–26.3°
b = 19.710 (5) Å	µ = 0.98 mm⁻¹
c = 12.370 (3) Å	T = 298 K
β = 97.936 (4)°	Block, purple
V = 2363.5 (10) Å³	0.32 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4630 independent reflections
Radiation source: sealed tube	3320 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
ω and ϕ scans	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→12
T_min = 0.746, T_max = 0.800	k = −22→24
12542 measured reflections	l = −14→15

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0683P)² + 1.5989P] where P = (F_o² + 2F_c²)/3
4630 reflections	(Δ/σ)_max < 0.001
264 parameters	Δρ_max = 0.90 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

[CoCl₂(C₁₅H₂₄N₆)(C₃H₇NO)]	V = 2363.5 (10) Å³
M_r = 491.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.787 (2) Å	µ = 0.98 mm⁻¹
b = 19.710 (5) Å	T = 298 K
c = 12.370 (3) Å	0.32 × 0.26 × 0.24 mm
β = 97.936 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	4630 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3320 reflections with I > 2σ(I)
T_min = 0.746, T_max = 0.800	R_int = 0.052
12542 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.07	Δρ_max = 0.90 e Å⁻³
4630 reflections	Δρ_min = −0.78 e Å⁻³
264 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2270 (4)	0.8211 (2)	0.3872 (3)	0.0324 (9)
H1A	0.2422	0.7803	0.4311	0.039*
H1B	0.2274	0.8595	0.4364	0.039*
C2	0.3432 (4)	0.8292 (2)	0.3190 (4)	0.0361 (10)
H2A	0.3394	0.8744	0.2878	0.043*
H2B	0.4308	0.8245	0.3658	0.043*
C3	0.3572 (5)	0.7079 (2)	0.2715 (3)	0.0379 (10)
H3A	0.3539	0.7075	0.3495	0.046*
H3B	0.4479	0.6923	0.2594	0.046*
C4	0.2498 (5)	0.6602 (2)	0.2164 (4)	0.0389 (10)
H4A	0.2658	0.6531	0.1415	0.047*
H4B	0.2586	0.6167	0.2533	0.047*
C5	0.0698 (5)	0.6922 (2)	0.3276 (4)	0.0373 (10)
H5A	0.1510	0.6860	0.3812	0.045*
H5B	0.0049	0.6564	0.3381	0.045*
C6	0.0060 (4)	0.7591 (2)	0.3466 (3)	0.0303 (9)
H6A	−0.0840	0.7617	0.3028	0.036*
H6B	−0.0072	0.7624	0.4227	0.036*
C7	0.0145 (4)	0.8814 (2)	0.3205 (3)	0.0304 (9)
H7A	−0.0535	0.8830	0.2556	0.037*
H7B	0.0790	0.9182	0.3148	0.037*
C8	−0.0598 (5)	0.8954 (3)	0.4193 (3)	0.0381 (10)
H8A	−0.1046	0.9393	0.4088	0.046*
H8B	−0.1318	0.8617	0.4201	0.046*
C9	0.0240 (6)	0.8954 (3)	0.5263 (4)	0.0466 (12)
C10	0.4320 (4)	0.7942 (3)	0.1517 (3)	0.0385 (10)
H10A	0.3992	0.8346	0.1115	0.046*
H10B	0.4295	0.7572	0.0997	0.046*
C11	0.5839 (5)	0.8060 (3)	0.2025 (4)	0.0446 (12)
H11A	0.6046	0.7777	0.2669	0.054*
H11B	0.6442	0.7920	0.1505	0.054*
C12	0.6122 (6)	0.8753 (3)	0.2321 (5)	0.0509 (13)
C13	0.0065 (5)	0.6472 (2)	0.1419 (4)	0.0413 (11)
H13A	0.0278	0.6533	0.0683	0.050*
H13B	−0.0832	0.6675	0.1447	0.050*
C14	−0.0065 (6)	0.5711 (2)	0.1614 (5)	0.0510 (13)
H14A	−0.0061	0.5636	0.2390	0.061*
H14B	−0.0950	0.5559	0.1244	0.061*
C15	0.0989 (6)	0.5305 (3)	0.1257 (5)	0.0522 (13)
C16	0.1312 (5)	0.9111 (2)	0.0171 (4)	0.0413 (11)
H16	0.0671	0.8850	−0.0274	0.050*
C17	0.2703 (6)	1.0089 (3)	0.0374 (5)	0.0666 (17)
H17A	0.2868	0.9934	0.1116	0.100*
H17B	0.2374	1.0548	0.0355	0.100*
H17C	0.3546	1.0068	0.0060	0.100*
C18	0.1187 (6)	0.9877 (3)	−0.1311 (5)	0.0618 (16)
H18A	0.0484	0.9566	−0.1617	0.093*
H18B	0.1924	0.9880	−0.1749	0.093*
H18C	0.0802	1.0325	−0.1296	0.093*
Cl1	0.17722 (12)	0.74778 (6)	−0.02560 (9)	0.0444 (3)
Cl2	−0.11597 (11)	0.80786 (5)	0.07777 (8)	0.0339 (2)
Co1	0.12259 (6)	0.78880 (3)	0.14939 (5)	0.03397 (19)
N1	0.0910 (4)	0.81680 (18)	0.3190 (3)	0.0329 (8)
N2	0.3359 (4)	0.77830 (18)	0.2297 (3)	0.0371 (9)
N3	0.1097 (4)	0.68609 (18)	0.2168 (3)	0.0319 (8)
N4	0.0843 (4)	0.8938 (2)	0.6097 (3)	0.0441 (10)
N5	0.6313 (5)	0.9298 (2)	0.2543 (4)	0.0551 (12)
N6	0.1858 (5)	0.4987 (2)	0.0935 (4)	0.0492 (10)
N7	0.1708 (4)	0.9672 (2)	−0.0227 (3)	0.0470 (10)
O1	0.1717 (3)	0.88941 (16)	0.1096 (2)	0.0372 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.030 (2)	0.039 (2)	0.025 (2)	0.0038 (18)	−0.0088 (16)	−0.0029 (17)
C2	0.029 (2)	0.042 (2)	0.036 (2)	−0.0020 (18)	−0.0027 (17)	0.0042 (19)
C3	0.039 (2)	0.049 (3)	0.024 (2)	0.014 (2)	−0.0005 (18)	−0.0011 (19)
C4	0.046 (3)	0.035 (2)	0.036 (2)	0.013 (2)	0.006 (2)	0.0042 (19)
C5	0.046 (3)	0.035 (2)	0.032 (2)	0.001 (2)	0.0073 (19)	0.0015 (19)
C6	0.025 (2)	0.041 (2)	0.0255 (19)	0.0005 (18)	0.0034 (15)	0.0055 (17)
C7	0.025 (2)	0.041 (2)	0.024 (2)	0.0045 (17)	−0.0016 (16)	−0.0021 (17)
C8	0.033 (2)	0.050 (3)	0.034 (2)	0.004 (2)	0.0127 (19)	0.001 (2)
C9	0.056 (3)	0.055 (3)	0.033 (3)	0.004 (2)	0.018 (2)	−0.008 (2)
C10	0.032 (2)	0.056 (3)	0.026 (2)	0.001 (2)	−0.0023 (17)	−0.005 (2)
C11	0.023 (2)	0.065 (3)	0.045 (3)	0.000 (2)	0.0059 (19)	0.004 (2)
C12	0.042 (3)	0.044 (3)	0.069 (4)	−0.005 (2)	0.016 (3)	0.001 (3)
C13	0.040 (3)	0.041 (3)	0.042 (3)	−0.002 (2)	0.003 (2)	0.001 (2)
C14	0.055 (3)	0.042 (3)	0.056 (3)	−0.003 (2)	0.007 (2)	−0.001 (2)
C15	0.045 (3)	0.048 (3)	0.061 (3)	0.006 (2)	−0.002 (2)	−0.010 (3)
C16	0.047 (3)	0.037 (2)	0.039 (3)	−0.002 (2)	0.003 (2)	0.012 (2)
C17	0.061 (4)	0.070 (4)	0.060 (4)	−0.030 (3)	−0.023 (3)	0.017 (3)
C18	0.061 (4)	0.063 (3)	0.062 (4)	−0.003 (3)	0.009 (3)	0.038 (3)
Cl1	0.0365 (6)	0.0568 (7)	0.0392 (6)	0.0011 (5)	0.0027 (4)	−0.0050 (5)
Cl2	0.0330 (6)	0.0353 (5)	0.0324 (5)	−0.0002 (4)	0.0005 (4)	0.0006 (4)
Co1	0.0342 (3)	0.0336 (3)	0.0330 (3)	−0.0002 (2)	0.0007 (2)	0.0012 (2)
N1	0.0301 (19)	0.0342 (18)	0.0343 (19)	0.0050 (15)	0.0037 (15)	0.0049 (15)
N2	0.035 (2)	0.0317 (19)	0.046 (2)	0.0012 (15)	0.0081 (17)	0.0029 (16)
N3	0.034 (2)	0.0365 (18)	0.0241 (17)	−0.0024 (16)	0.0012 (14)	0.0022 (15)
N4	0.042 (2)	0.052 (2)	0.038 (2)	−0.0023 (19)	0.0052 (18)	−0.0134 (19)
N5	0.050 (3)	0.060 (3)	0.060 (3)	−0.011 (2)	0.024 (2)	−0.011 (2)
N6	0.047 (3)	0.045 (2)	0.052 (2)	0.006 (2)	−0.002 (2)	−0.014 (2)
N7	0.042 (2)	0.055 (2)	0.042 (2)	−0.012 (2)	−0.0004 (17)	0.0153 (19)
O1	0.0345 (17)	0.0401 (17)	0.0354 (17)	−0.0036 (14)	−0.0015 (13)	0.0082 (14)

Geometric parameters (Å, º) top

C1—N1	1.477 (5)	C10—H10A	0.9700
C1—C2	1.515 (6)	C10—H10B	0.9700
C1—H1A	0.9700	C11—C12	1.432 (8)
C1—H1B	0.9700	C11—H11A	0.9700
C2—N2	1.487 (6)	C11—H11B	0.9700
C2—H2A	0.9700	C12—N5	1.119 (6)
C2—H2B	0.9700	C13—N3	1.486 (6)
C3—N2	1.486 (6)	C13—C14	1.526 (7)
C3—C4	1.501 (7)	C13—H13A	0.9700
C3—H3A	0.9700	C13—H13B	0.9700
C3—H3B	0.9700	C14—C15	1.423 (7)
C4—N3	1.464 (6)	C14—H14A	0.9700
C4—H4A	0.9700	C14—H14B	0.9700
C4—H4B	0.9700	C15—N6	1.170 (6)
C5—N3	1.481 (5)	C16—O1	1.235 (5)
C5—C6	1.491 (6)	C16—N7	1.291 (6)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—N7	1.405 (6)
C6—N1	1.477 (5)	C17—H17A	0.9600
C6—H6A	0.9700	C17—H17B	0.9600
C6—H6B	0.9700	C17—H17C	0.9600
C7—N1	1.478 (5)	C18—N7	1.426 (6)
C7—C8	1.531 (6)	C18—H18A	0.9600
C7—H7A	0.9700	C18—H18B	0.9600
C7—H7B	0.9700	C18—H18C	0.9600
C8—C9	1.458 (7)	Cl1—Co1	2.4382 (14)
C8—H8A	0.9700	Cl2—Co1	2.4096 (13)
C8—H8B	0.9700	Co1—O1	2.114 (3)
C9—N4	1.116 (6)	Co1—N2	2.194 (4)
C10—N2	1.470 (6)	Co1—N3	2.200 (4)
C10—C11	1.550 (6)	Co1—N1	2.232 (4)

N1—C1—C2	112.0 (3)	C14—C13—H13A	107.8
N1—C1—H1A	109.2	N3—C13—H13B	107.8
C2—C1—H1A	109.2	C14—C13—H13B	107.8
N1—C1—H1B	109.2	H13A—C13—H13B	107.1
C2—C1—H1B	109.2	C15—C14—C13	115.1 (5)
H1A—C1—H1B	107.9	C15—C14—H14A	108.5
N2—C2—C1	112.4 (4)	C13—C14—H14A	108.5
N2—C2—H2A	109.1	C15—C14—H14B	108.5
C1—C2—H2A	109.1	C13—C14—H14B	108.5
N2—C2—H2B	109.1	H14A—C14—H14B	107.5
C1—C2—H2B	109.1	N6—C15—C14	177.6 (6)
H2A—C2—H2B	107.9	O1—C16—N7	125.1 (5)
N2—C3—C4	111.7 (3)	O1—C16—H16	117.5
N2—C3—H3A	109.3	N7—C16—H16	117.5
C4—C3—H3A	109.3	N7—C17—H17A	109.5
N2—C3—H3B	109.3	N7—C17—H17B	109.5
C4—C3—H3B	109.3	H17A—C17—H17B	109.5
H3A—C3—H3B	107.9	N7—C17—H17C	109.5
N3—C4—C3	112.2 (4)	H17A—C17—H17C	109.5
N3—C4—H4A	109.2	H17B—C17—H17C	109.5
C3—C4—H4A	109.2	N7—C18—H18A	109.5
N3—C4—H4B	109.2	N7—C18—H18B	109.5
C3—C4—H4B	109.2	H18A—C18—H18B	109.5
H4A—C4—H4B	107.9	N7—C18—H18C	109.5
N3—C5—C6	112.8 (3)	H18A—C18—H18C	109.5
N3—C5—H5A	109.0	H18B—C18—H18C	109.5
C6—C5—H5A	109.0	O1—Co1—N2	87.78 (12)
N3—C5—H5B	109.0	O1—Co1—N3	168.01 (13)
C6—C5—H5B	109.0	N2—Co1—N3	80.93 (13)
H5A—C5—H5B	107.8	O1—Co1—N1	93.00 (13)
N1—C6—C5	112.5 (3)	N2—Co1—N1	81.07 (14)
N1—C6—H6A	109.1	N3—Co1—N1	81.30 (13)
C5—C6—H6A	109.1	O1—Co1—Cl2	90.45 (9)
N1—C6—H6B	109.1	N2—Co1—Cl2	173.80 (10)
C5—C6—H6B	109.1	N3—Co1—Cl2	100.34 (10)
H6A—C6—H6B	107.8	N1—Co1—Cl2	93.09 (10)
N1—C7—C8	117.6 (4)	O1—Co1—Cl1	91.12 (9)
N1—C7—H7A	107.9	N2—Co1—Cl1	93.38 (10)
C8—C7—H7A	107.9	N3—Co1—Cl1	93.58 (10)
N1—C7—H7B	107.9	N1—Co1—Cl1	172.94 (10)
C8—C7—H7B	107.9	Cl2—Co1—Cl1	92.60 (4)
H7A—C7—H7B	107.2	C6—N1—C1	113.8 (3)
C9—C8—C7	117.1 (4)	C6—N1—C7	111.0 (3)
C9—C8—H8A	108.0	C1—N1—C7	111.2 (3)
C7—C8—H8A	108.0	C6—N1—Co1	100.5 (2)
C9—C8—H8B	108.0	C1—N1—Co1	108.7 (3)
C7—C8—H8B	108.0	C7—N1—Co1	111.2 (2)
H8A—C8—H8B	107.3	C10—N2—C3	110.8 (3)
N4—C9—C8	177.2 (6)	C10—N2—C2	112.0 (3)
N2—C10—C11	115.5 (4)	C3—N2—C2	112.4 (3)
N2—C10—H10A	108.4	C10—N2—Co1	109.8 (3)
C11—C10—H10A	108.4	C3—N2—Co1	109.0 (3)
N2—C10—H10B	108.4	C2—N2—Co1	102.6 (3)
C11—C10—H10B	108.4	C4—N3—C5	113.5 (3)
H10A—C10—H10B	107.5	C4—N3—C13	112.0 (3)
C12—C11—C10	112.8 (4)	C5—N3—C13	112.0 (4)
C12—C11—H11A	109.0	C4—N3—Co1	102.5 (3)
C10—C11—H11A	109.0	C5—N3—Co1	108.2 (3)
C12—C11—H11B	109.0	C13—N3—Co1	108.0 (3)
C10—C11—H11B	109.0	C16—N7—C17	121.4 (4)
H11A—C11—H11B	107.8	C16—N7—C18	120.9 (5)
N5—C12—C11	178.4 (7)	C17—N7—C18	117.6 (4)
N3—C13—C14	118.2 (4)	C16—O1—Co1	119.1 (3)
N3—C13—H13A	107.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl2ⁱ	0.97	2.75	3.658 (4)	157
C2—H2A···O1	0.97	2.58	3.120 (5)	116
C3—H3A···Cl2ⁱ	0.97	2.81	3.774 (4)	170
C7—H7A···Cl2	0.97	2.65	3.419 (4)	136
C10—H10A···O1	0.97	2.47	3.149 (6)	127
C10—H10B···Cl1	0.97	2.73	3.218 (4)	111
C11—H11A···Cl1ⁱ	0.97	2.62	3.525 (5)	156
C11—H11B···Cl2ⁱⁱ	0.97	2.65	3.502 (5)	147
C13—H13A···Cl1	0.97	2.72	3.460 (5)	133
C16—H16···Cl2	0.93	2.80	3.325 (5)	117
C17—H17A···O1	0.96	2.34	2.741 (7)	105

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[CoCl₂(C₁₅H₂₄N₆)(C₃H₇NO)]
M_r	491.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	9.787 (2), 19.710 (5), 12.370 (3)
β (°)	97.936 (4)
V (Å³)	2363.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.98
Crystal size (mm)	0.32 × 0.26 × 0.24

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.746, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	12542, 4630, 3320
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.154, 1.07
No. of reflections	4630
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.90, −0.78

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top

Cl1—Co1	2.4382 (14)	Co1—N2	2.194 (4)
Cl2—Co1	2.4096 (13)	Co1—N3	2.200 (4)
Co1—O1	2.114 (3)	Co1—N1	2.232 (4)

O1—Co1—N2	87.78 (12)	N3—Co1—Cl2	100.34 (10)
O1—Co1—N3	168.01 (13)	N1—Co1—Cl2	93.09 (10)
N2—Co1—N3	80.93 (13)	O1—Co1—Cl1	91.12 (9)
O1—Co1—N1	93.00 (13)	N2—Co1—Cl1	93.38 (10)
N2—Co1—N1	81.07 (14)	N3—Co1—Cl1	93.58 (10)
N3—Co1—N1	81.30 (13)	N1—Co1—Cl1	172.94 (10)
O1—Co1—Cl2	90.45 (9)	Cl2—Co1—Cl1	92.60 (4)
N2—Co1—Cl2	173.80 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cl2ⁱ	0.97	2.75	3.658 (4)	157
C2—H2A···O1	0.97	2.58	3.120 (5)	116
C3—H3A···Cl2ⁱ	0.97	2.81	3.774 (4)	170
C7—H7A···Cl2	0.97	2.65	3.419 (4)	136
C10—H10A···O1	0.97	2.47	3.149 (6)	127
C10—H10B···Cl1	0.97	2.73	3.218 (4)	111
C11—H11A···Cl1ⁱ	0.97	2.62	3.525 (5)	156
C11—H11B···Cl2ⁱⁱ	0.97	2.65	3.502 (5)	147
C13—H13A···Cl1	0.97	2.72	3.460 (5)	133
C16—H16···Cl2	0.93	2.80	3.325 (5)	117
C17—H17A···O1	0.96	2.34	2.741 (7)	105

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x+1, y, z.

Acknowledgements

This project was supported by the Natural Science Foundation of China (grant No. 20475026).

References

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