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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1396.
Published online 2008 October 15. doi:  10.1107/S1600536808032595
PMCID: PMC2959638

Acrylato[tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine]cobalt(II) perchlorate–dimethyl­formamide–methanol (2/2/3)

Abstract

In the title complex, [Co(C3H3O2)(C27H27N7)]ClO4·C3H7NO·1.5CH4O, the CoII ion is five-coordinated by four N atoms from a tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine (mentb) ligand and one O atom from an acrylate ligand in a distorted trigonal–bipyramidal geometry with approximate mol­ecular C 3 symmetry. The atoms of the acrylate ligand are disordered over two sites, with approximate occupancies of 0.90 and 0.10. In addition, the solvent hemimethanol mol­ecule is disordered over two positions with equal occupancies. The crystal structure is stabilized by weak intermolecular O—H(...)O hydrogen bonds.

Related literature

For background information, see: Youngme et al. (2007 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1396-scheme1.jpg

Experimental

Crystal data

  • [Co(C3H3O2)(C27H27N7)]ClO4·C3H7NO·1.5CH4O
  • M r = 800.15
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1396-efi1.jpg
  • a = 11.3398 (3) Å
  • b = 13.9507 (4) Å
  • c = 14.4270 (5) Å
  • α = 108.443 (1)°
  • β = 110.738 (1)°
  • γ = 100.278 (1)°
  • V = 1913.24 (10) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 153 (2) K
  • 0.35 × 0.32 × 0.26 mm

Data collection

  • Rigaku R-AXIS Spider diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.823, T max = 0.864
  • 15711 measured reflections
  • 7032 independent reflections
  • 6085 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.147
  • S = 1.07
  • 7032 reflections
  • 519 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 1.26 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808032595/lh2706sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032595/lh2706Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors acknowledge financial support and grants from Qing Lan Talent Engineering Funds (grant No. QL-05-03A) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation of Gansu Province (grant No. 3YS061-A25-023,24) is also acknowledged.

supplementary crystallographic information

Comment

The asymmetric unit of the title compound (I), (Fig. 1), consists of a discrete [Co(mentb)(acrylate)] cation, a perchlorate anion, a DMF molecule and 1.5 molecules of methanol. The cobalt ion is five-coordinate with a N4O ligand set. The mentb ligand acts as a tetradentate N-donor, and an O atom of the carboxylate group of the acrylate ligand completes the coordination. The coordination geometry of the CoII ion may be best described as distorted trigonal bipyramidal (τ = 0.87), with approximate site symmetry C3. The parameter τ is defined as (β - α)/60 [where β = O1—Co—N7, α = N3—Co—N5] and its value varies from 0 (in regular square-based pyramidal) to 1 (in regular trigonal bipyramidal) [Youngme et al., 2007]. This geometry is assumed by the CoII ion presumably to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the CoII ion protrudes towards atom O1 and is 0.528 (2) Å from the plane of atoms N1/N3/N5. The axial positions are occupied by atoms N7 and O1. The three benzimidazole ring arms of the mentb ligand form a cone-shaped cavity. The distance between CoII and O2 is 3.076 (2) A, so atom O2 is not considered to be coordinated. The angles and distances in the mentb and salicylate are normally equal [for standard bond lengths, see: Allen et al., 1987]. The crystal structure is stabilized by weak intermolecular O-H···O hydrogen bonds and weak π···π stacking interactions (Fig. 2). The significant stacking interactions have ring centroid···ring centroid distances in the range 3.456 (2)-3.646 (2)Å.

Experimental

To a stirred solution of tris(1-methyl-1H-benzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Co(ClO4)2 (H2O)6 (0.0732 g, 0.2 mmol), followed by a solution of Na(acrylate) (0.0188 g, 0.2 mmol) in MeOH (5 ml). A red crystalline product formed rapidly. The precipitate was filtered off, washed with MeOH and absolute Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to a red solution that was allowed to evaporate at room temperature. The red crystals suitable for X-ray diffraction studies were obtained after four weeks. Yield, 0.106 g (66%). (found: C, 51.67; H, 5.38; N,14.21. Calcd. for C34.50H43ClN8O8.50Co: C, 51.79; H, 5.42; N, 14.00)

Refinement

All H atoms were found in difference electron maps and were subsequently refined in a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and O—H distance 0.84 Å and Uiso(H) = 1.2 Ueq of the carrier atom,

Figures

Fig. 1.
Molecular structure and atom numbering for the components of (I). Hydrogen atoms have been omitted for clarity and the displacement ellipsoids are shown at the 30% probability level.
Fig. 2.
The packing of the cations. Neither the disorder or H atoms are shown.

Crystal data

[Co(C3H3O2)(C27H27N7)]ClO4·C3H7NO·1.5CH4OZ = 2
Mr = 800.15F(000) = 836
Triclinic, P1Dx = 1.389 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.3398 (3) ÅCell parameters from 7032 reflections
b = 13.9507 (4) Åθ = 3.0–25.5°
c = 14.4270 (5) ŵ = 0.58 mm1
α = 108.443 (1)°T = 153 K
β = 110.738 (1)°Block, red
γ = 100.278 (1)°0.35 × 0.32 × 0.26 mm
V = 1913.24 (10) Å3

Data collection

Rigaku R-AXIS Spider diffractometer7032 independent reflections
Radiation source: Rotating Anode6085 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 25.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −13→13
Tmin = 0.823, Tmax = 0.864k = −15→16
15711 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0954P)2 + 1.1776P] where P = (Fo2 + 2Fc2)/3
7032 reflections(Δ/σ)max = 0.001
519 parametersΔρmax = 1.26 e Å3
6 restraintsΔρmin = −0.44 e Å3

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 (Å2)

xyzUiso*/UeqOcc. (<1)
Co0.85373 (3)0.66082 (3)0.32233 (3)0.02259 (13)
Cl0.39694 (7)0.32230 (6)0.32447 (6)0.03835 (19)
O10.9876 (2)0.71250 (18)0.27486 (15)0.0330 (7)0.901 (5)
O20.9039 (2)0.56682 (14)0.12161 (16)0.0361 (7)0.901 (5)
O1'0.932 (2)0.6236 (16)0.2363 (16)0.044 (7)0.099 (5)
O2'0.986 (3)0.7549 (7)0.218 (3)0.13 (2)0.099 (5)
O30.3275 (3)0.3884 (3)0.2891 (3)0.0793 (10)
O40.3064 (3)0.2197 (2)0.2890 (2)0.0725 (8)
O50.4629 (2)0.3703 (2)0.4417 (2)0.0591 (7)
O60.4972 (2)0.3160 (2)0.28583 (19)0.0499 (6)
O71.6359 (3)1.0565 (2)0.7244 (3)0.0626 (7)
O80.4466 (2)0.78673 (17)0.33218 (19)0.0411 (5)
H8O0.42660.83300.30980.049*
N10.9381 (2)0.79702 (17)0.46404 (16)0.0234 (4)
N20.9256 (2)0.91605 (17)0.60230 (17)0.0261 (5)
N30.6689 (2)0.64681 (16)0.21381 (16)0.0240 (4)
N40.4473 (2)0.58321 (17)0.14350 (17)0.0259 (5)
N50.8638 (2)0.52411 (17)0.34938 (17)0.0263 (5)
N60.8178 (2)0.41123 (19)0.42099 (18)0.0301 (5)
N70.7151 (2)0.64080 (17)0.40828 (17)0.0238 (4)
N101.5434 (3)1.0109 (2)0.8268 (3)0.0549 (8)
C10.7256 (2)0.7501 (2)0.4742 (2)0.0272 (5)
H1A0.70610.75090.53600.033*
H1B0.66070.77500.42930.033*
C20.8638 (2)0.8210 (2)0.5149 (2)0.0241 (5)
C30.8707 (3)0.9685 (2)0.6741 (2)0.0366 (7)
H3A0.77310.93780.63750.044*
H3B0.89701.04530.69170.044*
H3C0.90510.95770.74130.044*
C41.0501 (3)0.9576 (2)0.6089 (2)0.0269 (5)
C51.1554 (3)1.0522 (2)0.6819 (2)0.0345 (6)
H51.15001.10300.74090.041*
C61.2672 (3)1.0684 (2)0.6645 (2)0.0373 (7)
H61.34111.13180.71310.045*
C71.2759 (3)0.9943 (2)0.5770 (3)0.0360 (6)
H71.35481.00880.56740.043*
C81.1712 (3)0.9002 (2)0.5046 (2)0.0283 (6)
H81.17700.84960.44560.034*
C91.0573 (2)0.8826 (2)0.5214 (2)0.0238 (5)
C100.5791 (2)0.5790 (2)0.3218 (2)0.0260 (5)
H10A0.51290.59830.34750.031*
H10B0.56370.50150.30130.031*
C110.5648 (2)0.60425 (19)0.2267 (2)0.0240 (5)
C120.3149 (3)0.5384 (2)0.1345 (2)0.0318 (6)
H12A0.31720.48670.16730.038*
H12B0.25030.50250.05760.038*
H12C0.28850.59600.17260.038*
C130.4752 (3)0.61622 (19)0.0702 (2)0.0256 (5)
C140.3922 (3)0.6132 (2)−0.0293 (2)0.0308 (6)
H140.29780.5849−0.05920.037*
C150.4537 (3)0.6533 (2)−0.0823 (2)0.0334 (6)
H150.40050.6532−0.15010.040*
C160.5937 (3)0.6943 (2)−0.0384 (2)0.0332 (6)
H160.63260.7216−0.07720.040*
C170.6760 (3)0.6959 (2)0.0598 (2)0.0296 (6)
H170.77040.72310.08870.036*
C180.6152 (2)0.65610 (19)0.11455 (19)0.0233 (5)
C190.7642 (3)0.5831 (2)0.4753 (2)0.0283 (6)
H19A0.69110.54490.48590.034*
H19B0.83660.63380.54750.034*
C200.8152 (2)0.5053 (2)0.4155 (2)0.0263 (5)
C210.7751 (3)0.3659 (3)0.4873 (3)0.0378 (7)
H21A0.73470.41190.52370.045*
H21B0.85260.36130.54200.045*
H21C0.70960.29420.44040.045*
C220.8701 (3)0.3637 (2)0.3524 (2)0.0312 (6)
C230.8903 (3)0.2653 (2)0.3241 (2)0.0393 (7)
H230.86610.21580.35210.047*
C240.9470 (3)0.2433 (3)0.2537 (3)0.0450 (8)
H240.96260.17680.23240.054*
C250.9826 (3)0.3152 (3)0.2123 (2)0.0429 (8)
H251.02390.29750.16520.051*
C260.9593 (3)0.4119 (2)0.2381 (2)0.0342 (6)
H260.98230.46040.20870.041*
C270.9011 (3)0.4354 (2)0.3086 (2)0.0283 (6)
C280.9799 (2)0.65979 (16)0.18204 (15)0.0300 (6)
C291.0710 (3)0.7152 (3)0.1482 (3)0.0325 (8)0.901 (5)
H291.13270.78430.19840.039*0.901 (5)
C29'1.036 (4)0.643 (5)0.120 (4)0.055 (11)0.099 (5)
H29'1.06520.58330.12120.066*0.099 (5)
C301.0707 (4)0.6743 (3)0.0539 (3)0.0543 (9)
H30A1.01000.60530.00210.065*
H30B1.13110.71330.03660.065*
C311.4675 (7)0.9251 (4)0.8413 (5)0.102 (2)
H31A1.44600.85640.78200.122*
H31B1.38470.93730.84040.122*
H31C1.52080.92420.91100.122*
C321.5733 (5)1.1192 (3)0.9011 (4)0.0640 (11)
H32A1.61631.16920.87880.077*
H32B1.63341.13070.97480.077*
H32C1.49041.13120.90020.077*
C331.5787 (4)0.9898 (3)0.7467 (3)0.0533 (9)
H331.55830.91670.70230.064*
C340.3940 (4)0.7816 (4)0.4049 (4)0.0641 (11)
H34A0.42980.73690.44030.077*
H34B0.29660.75050.36540.077*
H34C0.41860.85380.46000.077*
C350.103 (2)0.0960 (19)0.008 (2)0.097 (5)*0.25
H35A0.15370.15820.07830.116*0.25
H35B0.03710.04500.01430.116*0.25
H35C0.05620.1191−0.04770.116*0.25
O90.192 (2)0.0453 (16)−0.0210 (17)0.119 (6)*0.25
H9O0.1654−0.0198−0.03420.143*0.25
O9'0.0197 (16)−0.0281 (13)−0.0351 (13)0.103 (5)*0.25
H9O'−0.0390−0.0076−0.07060.123*0.25
C35'0.1498 (19)0.0451 (19)0.001 (2)0.097 (5)*0.25
H35D0.19910.0079−0.03300.116*0.25
H35E0.19860.07230.08040.116*0.25
H35F0.14030.1049−0.01920.116*0.25

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co0.0241 (2)0.0256 (2)0.01876 (19)0.00885 (15)0.01064 (14)0.00814 (15)
Cl0.0424 (4)0.0413 (4)0.0393 (4)0.0115 (3)0.0212 (3)0.0237 (3)
O10.0313 (11)0.0420 (16)0.0238 (12)0.0071 (10)0.0163 (9)0.0093 (10)
O20.0368 (12)0.0301 (12)0.0278 (12)0.0009 (10)0.0079 (9)0.0081 (10)
O1'0.047 (13)0.025 (13)0.070 (17)0.016 (10)0.028 (12)0.028 (12)
O2'0.041 (16)0.22 (5)0.034 (18)−0.03 (2)0.002 (13)0.00 (3)
O30.0489 (15)0.098 (2)0.131 (3)0.0352 (16)0.0395 (17)0.089 (2)
O40.093 (2)0.0444 (15)0.0691 (19)−0.0045 (14)0.0426 (17)0.0164 (13)
O50.0536 (14)0.0789 (18)0.0389 (13)0.0181 (13)0.0253 (11)0.0135 (13)
O60.0583 (14)0.0663 (16)0.0415 (13)0.0240 (12)0.0330 (11)0.0274 (12)
O70.0648 (16)0.0669 (17)0.093 (2)0.0363 (14)0.0515 (16)0.0508 (16)
O80.0404 (11)0.0401 (12)0.0503 (13)0.0156 (10)0.0258 (10)0.0196 (10)
N10.0243 (10)0.0256 (11)0.0207 (10)0.0088 (9)0.0105 (8)0.0091 (9)
N20.0313 (11)0.0252 (11)0.0237 (11)0.0114 (9)0.0145 (9)0.0085 (9)
N30.0266 (10)0.0237 (11)0.0188 (10)0.0068 (9)0.0090 (8)0.0072 (8)
N40.0244 (10)0.0252 (11)0.0228 (11)0.0064 (9)0.0084 (9)0.0066 (9)
N50.0277 (11)0.0273 (11)0.0240 (11)0.0110 (9)0.0108 (9)0.0102 (9)
N60.0313 (11)0.0347 (12)0.0279 (12)0.0128 (10)0.0110 (9)0.0184 (10)
N70.0230 (10)0.0272 (11)0.0215 (10)0.0085 (9)0.0101 (8)0.0096 (9)
N100.069 (2)0.0374 (15)0.062 (2)0.0160 (14)0.0381 (17)0.0153 (14)
C10.0267 (12)0.0308 (14)0.0262 (13)0.0126 (11)0.0151 (11)0.0089 (11)
C20.0267 (12)0.0269 (13)0.0214 (12)0.0109 (10)0.0113 (10)0.0112 (10)
C30.0473 (17)0.0342 (15)0.0338 (15)0.0167 (13)0.0264 (13)0.0090 (12)
C40.0316 (13)0.0245 (13)0.0268 (13)0.0109 (11)0.0117 (11)0.0134 (11)
C50.0442 (16)0.0217 (13)0.0295 (14)0.0074 (12)0.0126 (12)0.0064 (11)
C60.0383 (15)0.0247 (14)0.0377 (16)0.0017 (12)0.0117 (13)0.0099 (12)
C70.0310 (14)0.0309 (15)0.0452 (17)0.0062 (12)0.0160 (13)0.0175 (13)
C80.0297 (13)0.0266 (13)0.0314 (14)0.0098 (11)0.0145 (11)0.0140 (11)
C90.0257 (12)0.0235 (12)0.0233 (12)0.0085 (10)0.0089 (10)0.0129 (10)
C100.0241 (12)0.0290 (13)0.0254 (13)0.0075 (10)0.0115 (10)0.0120 (11)
C110.0250 (12)0.0209 (12)0.0223 (12)0.0075 (10)0.0092 (10)0.0058 (10)
C120.0261 (13)0.0324 (14)0.0308 (14)0.0065 (11)0.0097 (11)0.0104 (12)
C130.0309 (13)0.0190 (12)0.0222 (12)0.0080 (10)0.0101 (10)0.0047 (10)
C140.0316 (13)0.0274 (14)0.0229 (13)0.0095 (11)0.0054 (11)0.0050 (11)
C150.0416 (15)0.0335 (15)0.0196 (13)0.0139 (12)0.0080 (11)0.0096 (11)
C160.0428 (15)0.0335 (15)0.0253 (14)0.0126 (12)0.0167 (12)0.0127 (12)
C170.0328 (13)0.0280 (13)0.0231 (13)0.0090 (11)0.0113 (11)0.0061 (11)
C180.0272 (12)0.0201 (12)0.0183 (12)0.0073 (10)0.0084 (10)0.0047 (10)
C190.0304 (13)0.0337 (14)0.0246 (13)0.0112 (11)0.0137 (11)0.0143 (11)
C200.0232 (12)0.0333 (14)0.0235 (12)0.0100 (11)0.0085 (10)0.0145 (11)
C210.0373 (15)0.0484 (18)0.0414 (17)0.0171 (13)0.0180 (13)0.0324 (15)
C220.0299 (13)0.0350 (15)0.0248 (13)0.0121 (12)0.0058 (11)0.0141 (12)
C230.0465 (17)0.0358 (16)0.0332 (15)0.0196 (14)0.0088 (13)0.0179 (13)
C240.060 (2)0.0393 (17)0.0343 (16)0.0317 (16)0.0127 (15)0.0139 (14)
C250.0554 (19)0.0497 (18)0.0280 (15)0.0328 (16)0.0175 (14)0.0138 (14)
C260.0420 (15)0.0389 (16)0.0276 (14)0.0224 (13)0.0157 (12)0.0153 (12)
C270.0288 (13)0.0289 (13)0.0233 (13)0.0131 (11)0.0065 (10)0.0095 (11)
C280.0235 (13)0.0390 (16)0.0241 (14)0.0085 (12)0.0083 (11)0.0120 (13)
C290.0312 (17)0.037 (2)0.0329 (17)0.0101 (15)0.0172 (14)0.0168 (16)
C29'0.039 (19)0.08 (3)0.09 (3)0.04 (2)0.04 (2)0.06 (3)
C300.058 (2)0.076 (3)0.0445 (19)0.0227 (19)0.0338 (17)0.0312 (19)
C310.159 (6)0.052 (3)0.113 (4)0.012 (3)0.100 (4)0.023 (3)
C320.079 (3)0.045 (2)0.063 (2)0.0224 (19)0.033 (2)0.0117 (18)
C330.061 (2)0.047 (2)0.064 (2)0.0267 (18)0.0360 (19)0.0236 (18)
C340.065 (2)0.094 (3)0.070 (3)0.049 (2)0.049 (2)0.045 (2)

Geometric parameters (Å, °)

Co—O1'1.772 (13)C12—H12A0.9800
Co—O11.988 (2)C12—H12B0.9800
Co—N12.053 (2)C12—H12C0.9800
Co—N32.054 (2)C13—C141.393 (4)
Co—N52.078 (2)C13—C181.407 (4)
Co—N72.351 (2)C14—C151.375 (4)
Cl—O31.415 (3)C14—H140.9500
Cl—O41.416 (3)C15—C161.408 (4)
Cl—O61.436 (2)C15—H150.9500
Cl—O51.442 (3)C16—C171.385 (4)
O1—C281.2697 (10)C16—H160.9500
O2—C281.2403 (10)C17—C181.390 (4)
O1'—C281.2697 (10)C17—H170.9500
O2'—C281.2401 (10)C19—C201.497 (4)
O7—C331.229 (5)C19—H19A0.9900
O8—C341.391 (4)C19—H19B0.9900
O8—H8O0.8400C21—H21A0.9800
N1—C21.321 (3)C21—H21B0.9800
N1—C91.395 (3)C21—H21C0.9800
N2—C21.350 (3)C22—C231.389 (4)
N2—C41.384 (3)C22—C271.398 (4)
N2—C31.462 (3)C23—C241.370 (5)
N3—C111.325 (3)C23—H230.9500
N3—C181.402 (3)C24—C251.390 (5)
N4—C111.344 (3)C24—H240.9500
N4—C131.387 (4)C25—C261.381 (4)
N4—C121.462 (3)C25—H250.9500
N5—C201.327 (3)C26—C271.385 (4)
N5—C271.400 (3)C26—H260.9500
N6—C201.345 (3)C28—C29'1.27 (4)
N6—C221.382 (4)C28—C291.488 (4)
N6—C211.466 (4)C29—C301.297 (5)
N7—C101.470 (3)C29—H290.9500
N7—C191.470 (3)C29'—C301.31 (4)
N7—C11.476 (3)C29'—H29'0.9500
N10—C331.318 (5)C30—H30A0.9500
N10—C321.443 (5)C30—H30B0.9500
N10—C311.461 (6)C31—H31A0.9800
C1—C21.486 (3)C31—H31B0.9800
C1—H1A0.9900C31—H31C0.9800
C1—H1B0.9900C32—H32A0.9800
C3—H3A0.9800C32—H32B0.9800
C3—H3B0.9800C32—H32C0.9800
C3—H3C0.9800C33—H330.9500
C4—C51.395 (4)C34—H34A0.9800
C4—C91.401 (4)C34—H34B0.9800
C5—C61.372 (4)C34—H34C0.9800
C5—H50.9500C35—O91.441 (3)
C6—C71.403 (4)C35—H35A0.9800
C6—H60.9500C35—H35B0.9800
C7—C81.387 (4)C35—H35C0.9800
C7—H70.9500O9—H9O0.8400
C8—C91.391 (4)O9'—C35'1.439 (3)
C8—H80.9500O9'—H9O'0.8400
C10—C111.484 (4)C35'—H35D0.9800
C10—H10A0.9900C35'—H35E0.9800
C10—H10B0.9900C35'—H35F0.9800
O1'—Co—O134.4 (6)C14—C15—H15119.2
O1'—Co—N1123.9 (7)C16—C15—H15119.2
O1—Co—N191.92 (8)C17—C16—C15121.6 (3)
O1'—Co—N3101.8 (7)C17—C16—H16119.2
O1—Co—N3108.26 (9)C15—C16—H16119.2
N1—Co—N3114.07 (8)C16—C17—C18117.4 (3)
O1'—Co—N587.5 (5)C16—C17—H17121.3
O1—Co—N5113.55 (9)C18—C17—H17121.3
N1—Co—N5112.69 (8)C17—C18—N3131.4 (2)
N3—Co—N5114.27 (8)C17—C18—C13120.3 (2)
O1'—Co—N7158.7 (6)N3—C18—C13108.3 (2)
O1—Co—N7166.76 (8)N7—C19—C20106.8 (2)
N1—Co—N775.20 (8)N7—C19—H19A110.4
N3—Co—N775.19 (8)C20—C19—H19A110.4
N5—Co—N775.09 (8)N7—C19—H19B110.4
O3—Cl—O4110.2 (2)C20—C19—H19B110.4
O3—Cl—O6109.93 (17)H19A—C19—H19B108.6
O4—Cl—O6111.49 (18)N5—C20—N6112.5 (2)
O3—Cl—O5108.3 (2)N5—C20—C19121.7 (2)
O4—Cl—O5108.69 (18)N6—C20—C19125.7 (2)
O6—Cl—O5108.10 (14)N6—C21—H21A109.5
C28—O1—Co121.23 (17)N6—C21—H21B109.5
C28—O1'—Co139.7 (14)H21A—C21—H21B109.5
C34—O8—H8O109.5N6—C21—H21C109.5
C2—N1—C9105.8 (2)H21A—C21—H21C109.5
C2—N1—Co117.75 (17)H21B—C21—H21C109.5
C9—N1—Co136.15 (17)N6—C22—C23131.5 (3)
C2—N2—C4107.0 (2)N6—C22—C27106.3 (2)
C2—N2—C3127.1 (2)C23—C22—C27122.1 (3)
C4—N2—C3125.9 (2)C24—C23—C22116.4 (3)
C11—N3—C18105.5 (2)C24—C23—H23121.8
C11—N3—Co117.02 (16)C22—C23—H23121.8
C18—N3—Co136.71 (17)C23—C24—C25122.1 (3)
C11—N4—C13107.2 (2)C23—C24—H24118.9
C11—N4—C12126.3 (2)C25—C24—H24118.9
C13—N4—C12126.5 (2)C26—C25—C24121.5 (3)
C20—N5—C27105.8 (2)C26—C25—H25119.3
C20—N5—Co117.45 (17)C24—C25—H25119.3
C27—N5—Co136.56 (18)C25—C26—C27117.3 (3)
C20—N6—C22107.2 (2)C25—C26—H26121.3
C20—N6—C21127.4 (2)C27—C26—H26121.3
C22—N6—C21125.3 (2)C26—C27—C22120.4 (3)
C10—N7—C19111.3 (2)C26—C27—N5131.4 (3)
C10—N7—C1112.0 (2)C22—C27—N5108.1 (2)
C19—N7—C1112.4 (2)O2'—C28—O2144.7 (14)
C10—N7—Co107.01 (15)O2'—C28—C29'111 (3)
C19—N7—Co107.62 (15)O2—C28—C29'85 (3)
C1—N7—Co106.10 (15)O2'—C28—O1'103 (2)
C33—N10—C32121.7 (3)O2—C28—O1'71.9 (11)
C33—N10—C31121.1 (3)C29'—C28—O1'146 (3)
C32—N10—C31117.2 (4)O2'—C28—O154.9 (17)
N7—C1—C2107.9 (2)O2—C28—O1123.8 (2)
N7—C1—H1A110.1C29'—C28—O1148 (2)
C2—C1—H1A110.1O1'—C28—O152.9 (10)
N7—C1—H1B110.1O2'—C28—C2974.2 (17)
C2—C1—H1B110.1O2—C28—C29120.1 (2)
H1A—C1—H1B108.4C29'—C28—C2937 (3)
N1—C2—N2112.7 (2)O1'—C28—C29163.6 (11)
N1—C2—C1121.5 (2)O1—C28—C29116.1 (2)
N2—C2—C1125.7 (2)C30—C29—C28123.5 (4)
N2—C3—H3A109.5C30—C29—H29118.2
N2—C3—H3B109.5C28—C29—H29118.2
H3A—C3—H3B109.5C28—C29'—C30145 (4)
N2—C3—H3C109.5C28—C29'—H29'107.4
H3A—C3—H3C109.5C30—C29'—H29'107.4
H3B—C3—H3C109.5C29—C30—C29'41 (3)
N2—C4—C5132.2 (3)C29—C30—H30A120.0
N2—C4—C9106.0 (2)C29'—C30—H30A81.9
C5—C4—C9121.8 (3)C29—C30—H30B120.0
C6—C5—C4116.9 (3)C29'—C30—H30B153.8
C6—C5—H5121.6H30A—C30—H30B120.0
C4—C5—H5121.6N10—C31—H31A109.5
C5—C6—C7122.0 (3)N10—C31—H31B109.5
C5—C6—H6119.0H31A—C31—H31B109.5
C7—C6—H6119.0N10—C31—H31C109.5
C8—C7—C6121.1 (3)H31A—C31—H31C109.5
C8—C7—H7119.5H31B—C31—H31C109.5
C6—C7—H7119.5N10—C32—H32A109.5
C7—C8—C9117.5 (3)N10—C32—H32B109.5
C7—C8—H8121.3H32A—C32—H32B109.5
C9—C8—H8121.3N10—C32—H32C109.5
C8—C9—N1130.8 (2)H32A—C32—H32C109.5
C8—C9—C4120.8 (2)H32B—C32—H32C109.5
N1—C9—C4108.4 (2)O7—C33—N10125.8 (4)
N7—C10—C11108.0 (2)O7—C33—H33117.1
N7—C10—H10A110.1N10—C33—H33117.1
C11—C10—H10A110.1O8—C34—H34A109.5
N7—C10—H10B110.1O8—C34—H34B109.5
C11—C10—H10B110.1H34A—C34—H34B109.5
H10A—C10—H10B108.4O8—C34—H34C109.5
N3—C11—N4113.1 (2)H34A—C34—H34C109.5
N3—C11—C10122.5 (2)H34B—C34—H34C109.5
N4—C11—C10124.3 (2)O9—C35—H35A109.5
N4—C12—H12A109.5O9—C35—H35B109.5
N4—C12—H12B109.5H35A—C35—H35B109.5
H12A—C12—H12B109.5O9—C35—H35C109.5
N4—C12—H12C109.5H35A—C35—H35C109.5
H12A—C12—H12C109.5H35B—C35—H35C109.5
H12B—C12—H12C109.5C35—O9—H9O109.5
N4—C13—C14131.7 (2)C35'—O9'—H9O'109.5
N4—C13—C18105.9 (2)O9'—C35'—H35D109.5
C14—C13—C18122.4 (3)O9'—C35'—H35E109.5
C15—C14—C13116.7 (3)H35D—C35'—H35E109.5
C15—C14—H14121.7O9'—C35'—H35F109.5
C13—C14—H14121.7H35D—C35'—H35F109.5
C14—C15—C16121.6 (2)H35E—C35'—H35F109.5
O1'—Co—O1—C2824.9 (11)C1—N7—C10—C1184.9 (2)
N1—Co—O1—C28−175.5 (2)Co—N7—C10—C11−31.0 (2)
N3—Co—O1—C28−59.3 (2)C18—N3—C11—N41.0 (3)
N5—Co—O1—C2868.7 (2)Co—N3—C11—N4−170.57 (16)
N7—Co—O1—C28−162.4 (3)C18—N3—C11—C10178.6 (2)
O1—Co—O1'—C28−33.8 (17)Co—N3—C11—C107.1 (3)
N1—Co—O1'—C28−59 (3)C13—N4—C11—N3−1.2 (3)
N3—Co—O1'—C2871 (3)C12—N4—C11—N3−178.7 (2)
N5—Co—O1'—C28−174 (2)C13—N4—C11—C10−178.8 (2)
N7—Co—O1'—C28150.8 (11)C12—N4—C11—C103.7 (4)
O1'—Co—N1—C2173.3 (7)N7—C10—C11—N319.1 (3)
O1—Co—N1—C2159.57 (19)N7—C10—C11—N4−163.5 (2)
N3—Co—N1—C248.6 (2)C11—N4—C13—C14179.7 (3)
N5—Co—N1—C2−83.86 (19)C12—N4—C13—C14−2.8 (4)
N7—Co—N1—C2−17.37 (17)C11—N4—C13—C180.8 (3)
O1'—Co—N1—C90.4 (7)C12—N4—C13—C18178.3 (2)
O1—Co—N1—C9−13.3 (2)N4—C13—C14—C15−179.9 (3)
N3—Co—N1—C9−124.3 (2)C18—C13—C14—C15−1.2 (4)
N5—Co—N1—C9103.3 (2)C13—C14—C15—C160.6 (4)
N7—Co—N1—C9169.8 (2)C14—C15—C16—C170.3 (4)
O1'—Co—N3—C11139.2 (6)C15—C16—C17—C18−0.6 (4)
O1—Co—N3—C11174.25 (17)C16—C17—C18—N3−179.8 (3)
N1—Co—N3—C11−85.03 (19)C16—C17—C18—C130.0 (4)
N5—Co—N3—C1146.6 (2)C11—N3—C18—C17179.4 (3)
N7—Co—N3—C11−19.08 (17)Co—N3—C18—C17−11.6 (4)
O1'—Co—N3—C18−28.9 (6)C11—N3—C18—C13−0.4 (3)
O1—Co—N3—C186.1 (3)Co—N3—C18—C13168.59 (18)
N1—Co—N3—C18106.8 (2)N4—C13—C18—C17179.9 (2)
N5—Co—N3—C18−121.5 (2)C14—C13—C18—C170.9 (4)
N7—Co—N3—C18172.8 (2)N4—C13—C18—N3−0.2 (3)
O1'—Co—N5—C20179.8 (8)C14—C13—C18—N3−179.3 (2)
O1—Co—N5—C20156.76 (18)C10—N7—C19—C2082.3 (2)
N1—Co—N5—C2053.9 (2)C1—N7—C19—C20−151.1 (2)
N3—Co—N5—C20−78.4 (2)Co—N7—C19—C20−34.6 (2)
N7—Co—N5—C20−12.61 (18)C27—N5—C20—N60.0 (3)
O1'—Co—N5—C27−6.6 (8)Co—N5—C20—N6175.43 (16)
O1—Co—N5—C27−29.6 (3)C27—N5—C20—C19−179.9 (2)
N1—Co—N5—C27−132.4 (2)Co—N5—C20—C19−4.5 (3)
N3—Co—N5—C2795.2 (2)C22—N6—C20—N5−0.9 (3)
N7—Co—N5—C27161.0 (3)C21—N6—C20—N5178.5 (2)
O1'—Co—N7—C10−56.6 (18)C22—N6—C20—C19179.0 (2)
O1—Co—N7—C10134.8 (3)C21—N6—C20—C19−1.5 (4)
N1—Co—N7—C10148.29 (17)N7—C19—C20—N528.7 (3)
N3—Co—N7—C1027.88 (15)N7—C19—C20—N6−151.2 (2)
N5—Co—N7—C10−92.81 (16)C20—N6—C22—C23−177.3 (3)
O1'—Co—N7—C1963.2 (18)C21—N6—C22—C233.3 (5)
O1—Co—N7—C19−105.4 (4)C20—N6—C22—C271.4 (3)
N1—Co—N7—C19−91.96 (16)C21—N6—C22—C27−178.0 (2)
N3—Co—N7—C19147.62 (17)N6—C22—C23—C24−179.1 (3)
N5—Co—N7—C1926.94 (16)C27—C22—C23—C242.3 (4)
O1'—Co—N7—C1−176.3 (18)C22—C23—C24—C25−0.1 (5)
O1—Co—N7—C115.1 (4)C23—C24—C25—C26−1.7 (5)
N1—Co—N7—C128.55 (15)C24—C25—C26—C271.1 (4)
N3—Co—N7—C1−91.87 (16)C25—C26—C27—C221.1 (4)
N5—Co—N7—C1147.44 (16)C25—C26—C27—N5−179.3 (3)
C10—N7—C1—C2−150.4 (2)N6—C22—C27—C26178.2 (2)
C19—N7—C1—C283.4 (3)C23—C22—C27—C26−2.9 (4)
Co—N7—C1—C2−34.0 (2)N6—C22—C27—N5−1.5 (3)
C9—N1—C2—N2−0.4 (3)C23—C22—C27—N5177.4 (2)
Co—N1—C2—N2−175.23 (16)C20—N5—C27—C26−178.7 (3)
C9—N1—C2—C1177.3 (2)Co—N5—C27—C267.2 (5)
Co—N1—C2—C12.5 (3)C20—N5—C27—C220.9 (3)
C4—N2—C2—N10.2 (3)Co—N5—C27—C22−173.20 (19)
C3—N2—C2—N1177.5 (2)Co—O1'—C28—O2'13 (3)
C4—N2—C2—C1−177.4 (2)Co—O1'—C28—O2−131 (3)
C3—N2—C2—C1−0.1 (4)Co—O1'—C28—C29'−180 (4)
N7—C1—C2—N124.3 (3)Co—O1'—C28—O138.1 (18)
N7—C1—C2—N2−158.3 (2)Co—O1'—C28—C2990 (4)
C2—N2—C4—C5−179.8 (3)Co—O1—C28—O2'125.3 (17)
C3—N2—C4—C52.7 (4)Co—O1—C28—O2−11.5 (4)
C2—N2—C4—C90.2 (3)Co—O1—C28—C29'−163 (4)
C3—N2—C4—C9−177.3 (2)Co—O1—C28—O1'−24.6 (12)
N2—C4—C5—C6179.7 (3)Co—O1—C28—C29169.7 (2)
C9—C4—C5—C6−0.3 (4)O2'—C28—C29—C30−140.1 (15)
C4—C5—C6—C70.5 (4)O2—C28—C29—C304.6 (5)
C5—C6—C7—C8−0.6 (5)C29'—C28—C29—C3026 (3)
C6—C7—C8—C90.4 (4)O1'—C28—C29—C30139 (3)
C7—C8—C9—N1−179.5 (3)O1—C28—C29—C30−176.6 (3)
C7—C8—C9—C4−0.2 (4)O2'—C28—C29'—C30−26 (8)
C2—N1—C9—C8179.8 (3)O2—C28—C29'—C30121 (7)
Co—N1—C9—C8−6.8 (4)O1'—C28—C29'—C30168 (5)
C2—N1—C9—C40.5 (3)O1—C28—C29'—C30−82 (7)
Co—N1—C9—C4173.88 (18)C29—C28—C29'—C30−40 (6)
N2—C4—C9—C8−179.8 (2)C28—C29—C30—C29'−24 (2)
C5—C4—C9—C80.2 (4)C28—C29'—C30—C2943 (6)
N2—C4—C9—N1−0.4 (3)C32—N10—C33—O7−2.0 (6)
C5—C4—C9—N1179.6 (2)C31—N10—C33—O7175.7 (5)
C19—N7—C10—C11−148.3 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H8O···O7i0.841.942.765 (4)169

Symmetry codes: (i) −x+2, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2706).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2004). RAPID-AUTO Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Youngme, S., Phatchimkun, J., Sukangpanya, U., Pakawatchai, C., Chaichit, N., Kongsaeree, P., Krzystek, J. & Murphy, B. (2007). Polyhedron, 26, 871–882.

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