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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): m1455.
Published online 2008 October 25. doi:  10.1107/S1600536808033758
PMCID: PMC2959500

(2-Hydroxy­benzoato-κO 1)[tris­(1-methyl­benzimidazol-2-ylmethyl-κN 3)amine-κN]cobalt(II) perchlorate dimethyl­formamide sesquisolvate

Abstract

In the title complex, [Co(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NO, the CoII ion is five-coordinated by four N atoms from a tris­(N-methyl­benzimidazol-2-ylmeth­yl)amine (Mentb) ligand and one O atom from a salicylate ligand in a distorted trigonal–bipyramidal geometry with approximate mol­ecular C 3 symmetry. The perchlorate ion is disordered over two sites with equal occupancy. One dimethyl­formamide solvent mol­ecule lies on a general position and is disordered over two coplanar orientations with equal occupancy. A second dimethyl­formamide mol­ecule is disordered about a twofold rotation axis. There is an intra­molecular O—H(...)O hydrogen bond in the cation.

Related literature

For related literature, see: Allen et al. (1987 [triangle]); Youngme et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1455-scheme1.jpg

Experimental

Crystal data

  • [Co(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NO
  • M r = 854.69
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1455-efi1.jpg
  • a = 27.7516 (5) Å
  • b = 11.4051 (2) Å
  • c = 25.0827 (5) Å
  • β = 102.9130 (10)°
  • V = 7738.1 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.58 mm−1
  • T = 153 (2) K
  • 0.35 × 0.25 × 0.21 mm

Data collection

  • Rigaku R-Axis Spider diffractometer
  • Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995 [triangle]) T min = 0.823, T max = 0.888
  • 36824 measured reflections
  • 8867 independent reflections
  • 6936 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.121
  • S = 1.00
  • 8867 reflections
  • 600 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.55 e Å−3
  • Δρmin = −0.69 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]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808033758/lh2710sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033758/lh2710Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The asymmetric unit of the title compound consists of a discrete [Co(Mentb)(salicylate)] cation (Fig. 1), a perchlorate anion and 1.5 molecules of DMF. The CoII ion is five-coordinate with a N4O ligand set. The Mentb ligand acts as a tetradentate N-donor, and an O atom of carboxylate groups of the salicylate completes the coordination. The coordination geometry of the CoII may be best described as distorted trigonal bipyramid (τ = 0.84), with approximat site symmetry C3. The parameter τ is defined as (β - α)/60 [where β = O1—Co—N7, α = N1—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 to relieve the steric crowding. The equatorial plane is occupied by three N atoms of three benzimidazolyl groups, while the CoII ion protrudes towards O1 and is 0.528 (2) Å from the plane of atoms N1/N3/N5. The axial positions are occupyied by N7 and O1. The three benzimidazole ring arms of the Mentb ligand form a cone-shaped cavity. The distance between CoII and O2 is 3.167 (2) A, therefore O2 is not considered to be coordinated. The distances in the Mentb and salicylate are normally equal [Allen et al., 1987]. There is a weak intramolecular O-H···O hydrogen bond and the crystal structure is stabilized by weak π···π stacking interactions with ring centroid···ring centroid distances of 3.623Å(1).

Experimental

To a stirred solution of tris(N-methylbenzimidazol-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(salicylate) (0.0320 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 three weeks. Yield, 0.091 g (53%). (found: C, 54.23; H, 4.98; N,14.01. Calcd. for C38.50H42.50ClN8.50O8.50Co: C, 54.10; H, 5.01; N, 13.93)

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 with Uiso(H) = 1.2 or 1.1 Ueq(C) of the carrier atom. The H atom bonded to O3 was refined isotropically.

Figures

Fig. 1.
The cation of of the title compound with displacement ellipsoids shown at the 30% probability level. Hydrogen atoms bonded to C atoms are not shown and the dashed line indicates a hydrogen bond.

Crystal data

[Co(C7H5O3)(C27H27N7)]ClO4·1.5C3H7NOF(000) = 3560
Mr = 854.69Dx = 1.467 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 8867 reflections
a = 27.7516 (5) Åθ = 3.0–27.5°
b = 11.4051 (2) ŵ = 0.58 mm1
c = 25.0827 (5) ÅT = 153 K
β = 102.913 (1)°Block, red
V = 7738.1 (2) Å30.35 × 0.25 × 0.21 mm
Z = 8

Data collection

Rigaku R-Axis Spider diffractometer8867 independent reflections
Radiation source: rotating anode6936 reflections with I > 2σ(I)
graphiteRint = 0.029
ω scansθmax = 27.5°, θmin = 3.0°
Absorption correction: empirical (using intensity measurements) (ABSCOR; Higashi, 1995)h = −36→36
Tmin = 0.823, Tmax = 0.888k = −13→14
36824 measured reflectionsl = −32→32

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121w = 1/[σ2(Fo2) + (0.068P)2 + 9.5996P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.003
8867 reflectionsΔρmax = 0.55 e Å3
600 parametersΔρmin = −0.69 e Å3
8 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00040 (8)

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)
Co0.643165 (9)0.84449 (2)0.588680 (11)0.02494 (9)
Cl0.55437 (2)0.47251 (5)0.39942 (3)0.04547 (16)
O10.68856 (6)0.98332 (13)0.60019 (7)0.0343 (3)
O20.63229 (6)1.11734 (14)0.60628 (7)0.0363 (4)
O30.65477 (7)1.33445 (15)0.61296 (9)0.0483 (4)
O40.5566 (2)0.5994 (6)0.4022 (3)0.0536 (14)0.50
O50.5532 (3)0.4355 (6)0.4534 (2)0.0541 (15)0.50
O4'0.5477 (4)0.5840 (9)0.3758 (6)0.170 (6)0.50
O5'0.5428 (4)0.4645 (10)0.4537 (2)0.149 (6)0.50
O60.51748 (9)0.4069 (3)0.36336 (10)0.0897 (9)
O70.60101 (8)0.4325 (2)0.39541 (13)0.0805 (8)
O80.69071 (10)1.5259 (2)0.73387 (11)0.0745 (7)
N10.69868 (6)0.73142 (15)0.57844 (7)0.0268 (3)
N20.72198 (7)0.58434 (16)0.53149 (7)0.0308 (4)
N30.61529 (6)0.80894 (16)0.65624 (7)0.0298 (4)
N40.58874 (7)0.68285 (18)0.71079 (8)0.0354 (4)
N50.58656 (6)0.87214 (15)0.52153 (7)0.0270 (4)
N60.51379 (6)0.82005 (16)0.46910 (8)0.0310 (4)
N70.60565 (6)0.66102 (15)0.57089 (7)0.0282 (4)
N80.71852 (8)1.34132 (19)0.75418 (9)0.0435 (5)
C10.63219 (8)0.59755 (19)0.53486 (9)0.0309 (4)
H1A0.61690.61440.49610.037*
H1B0.63050.51200.54080.037*
C20.68453 (8)0.63739 (18)0.54816 (9)0.0280 (4)
C30.71908 (9)0.4812 (2)0.49655 (10)0.0392 (5)
H3A0.72800.41120.51930.047*
H3B0.74200.49010.47230.047*
H3C0.68530.47290.47460.047*
C40.76444 (8)0.64746 (18)0.55368 (9)0.0300 (4)
C50.81369 (9)0.6297 (2)0.55124 (10)0.0376 (5)
H50.82340.56700.53100.045*
C60.84761 (8)0.7087 (2)0.57998 (10)0.0398 (5)
H60.88160.69990.57950.048*
C70.83338 (8)0.8009 (2)0.60954 (10)0.0369 (5)
H70.85780.85340.62860.044*
C80.78428 (8)0.81783 (19)0.61179 (9)0.0307 (4)
H80.77480.88060.63210.037*
C90.74962 (7)0.73929 (18)0.58308 (8)0.0275 (4)
C100.61014 (8)0.6048 (2)0.62462 (9)0.0346 (5)
H10A0.64290.56680.63630.042*
H10B0.58420.54430.62270.042*
C110.60428 (7)0.69829 (19)0.66407 (9)0.0309 (4)
C120.57561 (10)0.5741 (2)0.73431 (11)0.0467 (6)
H12A0.57160.51170.70680.056*
H12B0.54450.58480.74610.056*
H12C0.60190.55250.76590.056*
C130.59032 (8)0.7915 (2)0.73578 (10)0.0368 (5)
C140.57893 (10)0.8257 (3)0.78514 (11)0.0483 (6)
H140.56720.77130.80800.058*
C150.58553 (12)0.9414 (3)0.79863 (12)0.0591 (8)
H150.57840.96830.83190.071*
C160.60248 (12)1.0213 (3)0.76483 (12)0.0583 (8)
H160.60701.10090.77600.070*
C170.61291 (10)0.9877 (2)0.71532 (11)0.0444 (6)
H170.62371.04290.69210.053*
C180.60693 (8)0.8704 (2)0.70135 (9)0.0344 (5)
C190.55367 (7)0.68142 (18)0.54340 (9)0.0311 (4)
H19A0.53320.68970.57080.037*
H19B0.54090.61450.51920.037*
C200.55149 (7)0.79069 (18)0.51077 (8)0.0281 (4)
C210.47023 (8)0.7489 (2)0.44631 (10)0.0385 (5)
H21A0.47670.70090.41630.046*
H21B0.44190.80040.43250.046*
H21C0.46290.69770.47490.046*
C220.52446 (8)0.92923 (19)0.45085 (9)0.0311 (4)
C230.49798 (9)1.0012 (2)0.40966 (9)0.0376 (5)
H230.46660.97900.38820.045*
C240.51983 (9)1.1062 (2)0.40184 (10)0.0415 (6)
H240.50301.15780.37410.050*
C250.56612 (9)1.1395 (2)0.43353 (10)0.0388 (5)
H250.58001.21250.42650.047*
C260.59188 (8)1.06819 (19)0.47479 (9)0.0330 (5)
H260.62321.09100.49630.040*
C270.57031 (8)0.96123 (18)0.48382 (8)0.0288 (4)
C280.67583 (8)1.08797 (19)0.60662 (8)0.0297 (4)
C290.71489 (8)1.18065 (18)0.61520 (8)0.0298 (4)
C300.76472 (8)1.1523 (2)0.62112 (10)0.0359 (5)
H300.77391.07240.61950.043*
C310.80089 (9)1.2374 (2)0.62929 (11)0.0446 (6)
H310.83451.21660.63230.053*
C320.78756 (10)1.3542 (2)0.63310 (11)0.0445 (6)
H320.81231.41320.63920.053*
C330.73888 (10)1.3848 (2)0.62805 (10)0.0407 (5)
H330.73021.46470.63110.049*
C340.70224 (9)1.29931 (19)0.61845 (9)0.0346 (5)
C350.6705 (3)1.2899 (6)0.7445 (3)0.0629 (17)0.50
H35A0.64551.35080.73290.075*0.50
H35B0.66561.25300.77810.075*0.50
H35C0.66751.23050.71570.075*0.50
C360.7614 (3)1.2675 (7)0.7674 (3)0.0648 (18)0.50
H36A0.76111.21260.73730.078*0.50
H36B0.76111.22360.80090.078*0.50
H36C0.79131.31600.77310.078*0.50
C370.7221 (2)1.4602 (5)0.7472 (2)0.0475 (12)0.50
H370.75461.49150.75440.057*0.50
C35'0.7025 (3)1.2156 (6)0.7539 (3)0.0683 (18)0.50
H35D0.66631.21140.74360.082*0.50
H35E0.71431.18190.79040.082*0.50
H35F0.71641.17140.72740.082*0.50
C36'0.7701 (2)1.3623 (10)0.7691 (3)0.080 (3)0.50
H36D0.77661.44600.76510.097*0.50
H36E0.78671.31680.74540.097*0.50
H36F0.78281.33880.80730.097*0.50
C37'0.6846 (2)1.4203 (5)0.7383 (2)0.0480 (12)0.50
H37'0.65141.39320.72920.058*0.50
O90.5719 (3)1.3091 (6)0.7098 (5)0.179 (5)0.50
N90.5049 (3)1.2538 (6)0.7471 (4)0.123 (4)0.50
C380.5482 (3)1.3038 (6)0.7456 (5)0.190 (10)0.50
H380.56351.34270.77860.209*0.50
C390.4840 (6)1.1958 (13)0.6957 (4)0.160 (6)0.50
H39A0.49041.11140.69960.176*0.50
H39B0.49931.22720.66710.176*0.50
H39C0.44831.20980.68580.176*0.50
C400.4795 (5)1.2510 (9)0.7916 (5)0.178 (9)0.50
H40A0.44681.21540.77880.196*0.50
H40B0.47571.33110.80420.196*0.50
H40C0.49871.20460.82190.196*0.50
H3O0.6388 (14)1.273 (2)0.6093 (19)0.105 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Co0.01968 (14)0.02878 (15)0.02593 (15)0.00379 (10)0.00417 (10)−0.00125 (10)
Cl0.0303 (3)0.0401 (3)0.0677 (4)−0.0048 (2)0.0147 (3)−0.0054 (3)
O10.0290 (8)0.0313 (8)0.0419 (9)0.0008 (6)0.0066 (7)−0.0045 (7)
O20.0282 (8)0.0369 (8)0.0412 (9)0.0054 (6)0.0021 (7)−0.0030 (7)
O30.0406 (10)0.0359 (9)0.0617 (12)0.0087 (8)−0.0028 (9)−0.0007 (8)
O40.039 (3)0.039 (3)0.088 (4)0.009 (2)0.026 (3)−0.005 (2)
O50.073 (4)0.059 (3)0.034 (2)−0.026 (3)0.018 (2)−0.005 (2)
O4'0.071 (5)0.055 (5)0.360 (19)−0.005 (3)−0.008 (8)0.070 (8)
O5'0.096 (6)0.219 (12)0.165 (8)−0.092 (7)0.097 (6)−0.155 (8)
O60.0636 (15)0.137 (2)0.0601 (15)−0.0444 (16)−0.0049 (12)0.0005 (15)
O70.0498 (13)0.0572 (13)0.145 (3)0.0048 (10)0.0438 (15)−0.0073 (14)
O80.0856 (18)0.0598 (14)0.0745 (16)0.0111 (13)0.0105 (14)−0.0031 (12)
N10.0214 (8)0.0309 (8)0.0279 (9)0.0041 (6)0.0048 (7)0.0005 (7)
N20.0303 (9)0.0347 (9)0.0282 (9)0.0084 (7)0.0081 (7)−0.0008 (7)
N30.0260 (8)0.0377 (9)0.0261 (9)0.0038 (7)0.0067 (7)0.0004 (7)
N40.0282 (9)0.0460 (11)0.0327 (10)0.0032 (8)0.0082 (8)0.0073 (8)
N50.0216 (8)0.0318 (9)0.0277 (9)0.0050 (6)0.0056 (7)−0.0001 (7)
N60.0215 (8)0.0392 (10)0.0309 (9)0.0067 (7)0.0027 (7)−0.0035 (8)
N70.0219 (8)0.0307 (9)0.0312 (9)0.0043 (6)0.0043 (7)−0.0005 (7)
N80.0383 (11)0.0563 (13)0.0327 (11)0.0034 (9)0.0014 (9)−0.0020 (9)
C10.0275 (10)0.0319 (10)0.0326 (11)0.0043 (8)0.0048 (9)−0.0049 (9)
C20.0261 (10)0.0302 (10)0.0270 (10)0.0071 (8)0.0043 (8)0.0016 (8)
C30.0453 (13)0.0380 (12)0.0345 (12)0.0099 (10)0.0095 (10)−0.0068 (10)
C40.0290 (10)0.0343 (11)0.0276 (10)0.0059 (8)0.0084 (8)0.0039 (8)
C50.0335 (12)0.0435 (12)0.0401 (13)0.0112 (9)0.0175 (10)0.0042 (10)
C60.0253 (10)0.0526 (14)0.0453 (14)0.0070 (10)0.0160 (10)0.0086 (11)
C70.0266 (10)0.0455 (12)0.0389 (12)−0.0012 (9)0.0082 (9)0.0080 (10)
C80.0276 (10)0.0364 (11)0.0288 (11)0.0035 (8)0.0081 (8)0.0038 (9)
C90.0233 (9)0.0329 (10)0.0267 (10)0.0066 (8)0.0066 (8)0.0065 (8)
C100.0329 (11)0.0349 (11)0.0359 (12)0.0049 (9)0.0076 (9)0.0061 (9)
C110.0222 (9)0.0385 (11)0.0309 (11)0.0040 (8)0.0036 (8)0.0046 (9)
C120.0444 (14)0.0499 (14)0.0482 (15)0.0031 (11)0.0155 (12)0.0151 (12)
C130.0278 (11)0.0500 (13)0.0329 (12)0.0034 (9)0.0077 (9)0.0017 (10)
C140.0449 (14)0.0683 (17)0.0354 (13)0.0009 (12)0.0168 (11)0.0040 (12)
C150.074 (2)0.0709 (19)0.0400 (15)−0.0026 (16)0.0300 (15)−0.0112 (14)
C160.076 (2)0.0564 (17)0.0509 (17)−0.0079 (14)0.0318 (16)−0.0155 (13)
C170.0511 (15)0.0488 (14)0.0379 (13)−0.0048 (11)0.0197 (12)−0.0071 (11)
C180.0273 (10)0.0470 (13)0.0298 (11)0.0035 (9)0.0079 (9)−0.0007 (9)
C190.0216 (9)0.0326 (10)0.0374 (12)0.0009 (8)0.0029 (8)−0.0009 (9)
C200.0203 (9)0.0343 (10)0.0293 (10)0.0060 (8)0.0049 (8)−0.0036 (8)
C210.0221 (10)0.0480 (13)0.0413 (13)0.0037 (9)−0.0018 (9)−0.0089 (10)
C220.0271 (10)0.0389 (11)0.0277 (10)0.0117 (8)0.0070 (8)−0.0015 (9)
C230.0321 (11)0.0519 (14)0.0281 (11)0.0171 (10)0.0049 (9)0.0002 (10)
C240.0459 (14)0.0485 (13)0.0315 (12)0.0238 (11)0.0116 (10)0.0068 (10)
C250.0492 (14)0.0357 (12)0.0357 (12)0.0135 (10)0.0185 (11)0.0035 (9)
C260.0332 (11)0.0352 (11)0.0328 (11)0.0063 (9)0.0120 (9)−0.0020 (9)
C270.0270 (10)0.0348 (10)0.0254 (10)0.0105 (8)0.0079 (8)−0.0012 (8)
C280.0276 (10)0.0351 (11)0.0250 (10)0.0029 (8)0.0030 (8)−0.0014 (8)
C290.0327 (11)0.0336 (10)0.0223 (10)0.0017 (8)0.0042 (8)−0.0011 (8)
C300.0337 (11)0.0384 (12)0.0370 (12)−0.0007 (9)0.0108 (10)−0.0087 (9)
C310.0360 (12)0.0503 (14)0.0491 (15)−0.0065 (10)0.0131 (11)−0.0109 (12)
C320.0498 (15)0.0435 (13)0.0403 (14)−0.0128 (11)0.0103 (11)−0.0028 (11)
C330.0522 (15)0.0318 (11)0.0356 (12)−0.0020 (10)0.0042 (11)0.0027 (10)
C340.0415 (12)0.0332 (11)0.0258 (11)0.0040 (9)0.0008 (9)0.0012 (9)
C350.073 (4)0.062 (4)0.052 (4)−0.028 (3)0.011 (3)−0.011 (3)
C360.074 (5)0.072 (4)0.048 (4)0.027 (4)0.013 (3)0.007 (3)
C370.047 (3)0.044 (3)0.047 (3)−0.005 (2)0.000 (2)−0.001 (2)
C35'0.106 (6)0.055 (4)0.044 (3)0.011 (4)0.019 (4)−0.004 (3)
C36'0.027 (3)0.170 (9)0.040 (3)0.015 (4)−0.001 (2)−0.005 (5)
C37'0.035 (3)0.059 (3)0.046 (3)0.002 (2)0.002 (2)−0.006 (3)
O90.075 (5)0.085 (4)0.389 (16)−0.020 (4)0.079 (7)0.035 (7)
N90.161 (9)0.078 (4)0.111 (7)0.050 (8)−0.012 (7)0.027 (8)
C380.045 (5)0.052 (5)0.47 (3)−0.007 (4)0.040 (10)0.051 (9)
C390.187 (14)0.228 (15)0.076 (7)−0.104 (12)0.051 (8)−0.026 (8)
C400.129 (13)0.099 (9)0.24 (2)0.009 (8)−0.107 (14)−0.014 (10)

Geometric parameters (Å, °)

Co—O12.0038 (15)C13—C181.395 (3)
Co—N32.0543 (17)C13—C141.400 (3)
Co—N52.0546 (17)C14—C151.364 (4)
Co—N12.0687 (16)C14—H140.9500
Co—N72.3353 (17)C15—C161.396 (4)
Cl—O71.397 (2)C15—H150.9500
Cl—O4'1.398 (10)C16—C171.390 (3)
Cl—O61.419 (2)C16—H160.9500
Cl—O51.424 (4)C17—C181.384 (3)
Cl—O41.450 (7)C17—H170.9500
Cl—O5'1.470 (3)C19—C201.485 (3)
O1—C281.265 (3)C19—H19A0.9900
O2—C281.252 (3)C19—H19B0.9900
O3—C341.354 (3)C21—H21A0.9800
O3—H3O0.82 (3)C21—H21B0.9800
O8—C371.142 (6)C21—H21C0.9800
O8—C37'1.225 (6)C22—C231.394 (3)
N1—C21.322 (3)C22—C271.402 (3)
N1—C91.395 (2)C23—C241.376 (4)
N2—C21.347 (3)C23—H230.9500
N2—C41.387 (3)C24—C251.404 (4)
N2—C31.458 (3)C24—H240.9500
N3—C111.323 (3)C25—C261.383 (3)
N3—C181.394 (3)C25—H250.9500
N4—C111.348 (3)C26—C271.399 (3)
N4—C131.385 (3)C26—H260.9500
N4—C121.454 (3)C28—C291.495 (3)
N5—C201.329 (3)C29—C301.396 (3)
N5—C271.393 (3)C29—C341.405 (3)
N6—C201.346 (3)C30—C311.378 (3)
N6—C221.381 (3)C30—H300.9500
N6—C211.462 (3)C31—C321.391 (4)
N7—C191.472 (3)C31—H310.9500
N7—C101.472 (3)C32—C331.373 (4)
N7—C11.477 (3)C32—H320.9500
N8—C37'1.300 (6)C33—C341.390 (3)
N8—C371.373 (6)C33—H330.9500
N8—C36'1.418 (7)C35—H35A0.9800
N8—C351.426 (6)C35—H35B0.9800
N8—C361.435 (7)C35—H35C0.9800
N8—C35'1.501 (7)C36—H36A0.9800
C1—C21.487 (3)C36—H36B0.9800
C1—H1A0.9900C36—H36C0.9800
C1—H1B0.9900C37—H370.9500
C3—H3A0.9800C35'—H35D0.9800
C3—H3B0.9800C35'—H35E0.9800
C3—H3C0.9800C35'—H35F0.9800
C4—C91.395 (3)C36'—H36D0.9800
C4—C51.397 (3)C36'—H36E0.9800
C5—C61.383 (4)C36'—H36F0.9800
C5—H50.9500C37'—H37'0.9500
C6—C71.393 (3)O9—C381.229 (3)
C6—H60.9500N9—C381.338 (3)
C7—C81.390 (3)N9—C401.448 (3)
C7—H70.9500N9—C391.450 (3)
C8—C91.392 (3)C38—H380.9500
C8—H80.9500C39—H39A0.9800
C10—C111.488 (3)C39—H39B0.9800
C10—H10A0.9900C39—H39C0.9800
C10—H10B0.9900C40—H40A0.9800
C12—H12A0.9800C40—H40B0.9800
C12—H12B0.9800C40—H40C0.9800
C12—H12C0.9800
O1—Co—N3112.19 (7)N4—C13—C14131.2 (2)
O1—Co—N5109.74 (7)C18—C13—C14122.6 (2)
N3—Co—N5110.28 (7)C15—C14—C13116.4 (2)
O1—Co—N192.79 (6)C15—C14—H14121.8
N3—Co—N1114.05 (7)C13—C14—H14121.8
N5—Co—N1116.62 (7)C14—C15—C16121.7 (2)
O1—Co—N7167.07 (6)C14—C15—H15119.1
N3—Co—N775.33 (7)C16—C15—H15119.1
N5—Co—N775.78 (7)C17—C16—C15121.9 (3)
N1—Co—N774.35 (6)C17—C16—H16119.1
O7—Cl—O4'107.6 (5)C15—C16—H16119.1
O7—Cl—O6109.26 (18)C18—C17—C16117.1 (2)
O4'—Cl—O6101.7 (5)C18—C17—H17121.5
O7—Cl—O5100.9 (4)C16—C17—H17121.5
O4'—Cl—O5130.0 (7)C17—C18—N3131.3 (2)
O6—Cl—O5106.4 (3)C17—C18—C13120.3 (2)
O7—Cl—O4107.4 (2)N3—C18—C13108.4 (2)
O6—Cl—O4125.1 (3)N7—C19—C20107.80 (16)
O5—Cl—O4105.1 (4)N7—C19—H19A110.1
O7—Cl—O5'116.4 (5)C20—C19—H19A110.1
O4'—Cl—O5'114.4 (8)N7—C19—H19B110.1
O6—Cl—O5'106.4 (4)C20—C19—H19B110.1
O4—Cl—O5'91.9 (5)H19A—C19—H19B108.5
C28—O1—Co125.40 (14)N5—C20—N6113.01 (19)
C34—O3—H3O104 (3)N5—C20—C19122.49 (19)
C37—O8—C37'55.9 (4)N6—C20—C19124.46 (19)
C2—N1—C9105.39 (16)N6—C21—H21A109.5
C2—N1—Co116.30 (13)N6—C21—H21B109.5
C9—N1—Co135.93 (14)H21A—C21—H21B109.5
C2—N2—C4106.70 (17)N6—C21—H21C109.5
C2—N2—C3127.30 (19)H21A—C21—H21C109.5
C4—N2—C3126.00 (18)H21B—C21—H21C109.5
C11—N3—C18105.86 (18)N6—C22—C23131.3 (2)
C11—N3—Co116.92 (14)N6—C22—C27105.83 (18)
C18—N3—Co137.05 (15)C23—C22—C27122.9 (2)
C11—N4—C13107.02 (19)C24—C23—C22116.2 (2)
C11—N4—C12128.5 (2)C24—C23—H23121.9
C13—N4—C12124.4 (2)C22—C23—H23121.9
C20—N5—C27105.11 (17)C23—C24—C25122.1 (2)
C20—N5—Co116.76 (14)C23—C24—H24118.9
C27—N5—Co137.81 (15)C25—C24—H24118.9
C20—N6—C22107.13 (18)C26—C25—C24121.3 (2)
C20—N6—C21126.7 (2)C26—C25—H25119.4
C22—N6—C21126.20 (19)C24—C25—H25119.4
C19—N7—C10111.79 (17)C25—C26—C27117.7 (2)
C19—N7—C1111.19 (17)C25—C26—H26121.1
C10—N7—C1113.26 (16)C27—C26—H26121.1
C19—N7—Co107.24 (12)N5—C27—C26131.3 (2)
C10—N7—Co105.81 (13)N5—C27—C22108.91 (19)
C1—N7—Co107.11 (12)C26—C27—C22119.7 (2)
C37'—N8—C3749.1 (4)O2—C28—O1123.2 (2)
C37'—N8—C36'125.7 (5)O2—C28—C29118.65 (19)
C37—N8—C36'76.7 (5)O1—C28—C29118.11 (18)
C37'—N8—C3569.4 (4)C30—C29—C34118.1 (2)
C37—N8—C35118.4 (4)C30—C29—C28121.39 (19)
C36'—N8—C35164.8 (6)C34—C29—C28120.5 (2)
C37'—N8—C36169.8 (5)C31—C30—C29121.6 (2)
C37—N8—C36121.9 (5)C31—C30—H30119.2
C36'—N8—C3645.7 (4)C29—C30—H30119.2
C35—N8—C36119.6 (5)C30—C31—C32119.2 (2)
C37'—N8—C35'117.8 (4)C30—C31—H31120.4
C37—N8—C35'166.5 (4)C32—C31—H31120.4
C36'—N8—C35'116.3 (6)C33—C32—C31120.5 (2)
C35—N8—C35'48.8 (4)C33—C32—H32119.7
C36—N8—C35'70.8 (5)C31—C32—H32119.7
N7—C1—C2107.99 (17)C32—C33—C34120.3 (2)
N7—C1—H1A110.1C32—C33—H33119.9
C2—C1—H1A110.1C34—C33—H33119.9
N7—C1—H1B110.1O3—C34—C33117.9 (2)
C2—C1—H1B110.1O3—C34—C29121.9 (2)
H1A—C1—H1B108.4C33—C34—C29120.2 (2)
N1—C2—N2113.07 (18)N8—C35—H35A109.5
N1—C2—C1121.77 (17)N8—C35—H35B109.5
N2—C2—C1125.16 (19)N8—C35—H35C109.5
N2—C3—H3A109.5N8—C36—H36A109.5
N2—C3—H3B109.5N8—C36—H36B109.5
H3A—C3—H3B109.5N8—C36—H36C109.5
N2—C3—H3C109.5O8—C37—N8127.9 (5)
H3A—C3—H3C109.5O8—C37—H37116.1
H3B—C3—H3C109.5N8—C37—H37116.1
N2—C4—C9106.12 (17)N8—C35'—H35D109.5
N2—C4—C5131.3 (2)N8—C35'—H35E109.5
C9—C4—C5122.6 (2)H35D—C35'—H35E109.5
C6—C5—C4116.2 (2)N8—C35'—H35F109.5
C6—C5—H5121.9H35D—C35'—H35F109.5
C4—C5—H5121.9H35E—C35'—H35F109.5
C5—C6—C7121.9 (2)N8—C36'—H36D109.5
C5—C6—H6119.1N8—C36'—H36E109.5
C7—C6—H6119.1H36D—C36'—H36E109.5
C8—C7—C6121.6 (2)N8—C36'—H36F109.5
C8—C7—H7119.2H36D—C36'—H36F109.5
C6—C7—H7119.2H36E—C36'—H36F109.5
C7—C8—C9117.4 (2)O8—C37'—N8127.1 (5)
C7—C8—H8121.3O8—C37'—H37'116.4
C9—C8—H8121.3N8—C37'—H37'116.4
C8—C9—C4120.37 (18)C38—N9—C40128.8 (11)
C8—C9—N1130.91 (19)C38—N9—C39110.7 (11)
C4—C9—N1108.70 (18)C40—N9—C39120.5 (9)
N7—C10—C11107.28 (17)O9—C38—N9132.3 (10)
N7—C10—H10A110.3O9—C38—H38113.9
C11—C10—H10A110.3N9—C38—H38113.9
N7—C10—H10B110.3N9—C39—H39A109.5
C11—C10—H10B110.3N9—C39—H39B109.5
H10A—C10—H10B108.5H39A—C39—H39B109.5
N3—C11—N4112.5 (2)N9—C39—H39C109.5
N3—C11—C10121.43 (19)H39A—C39—H39C109.5
N4—C11—C10126.0 (2)H39B—C39—H39C109.5
N4—C12—H12A109.5N9—C40—H40A109.5
N4—C12—H12B109.5N9—C40—H40B109.5
H12A—C12—H12B109.5H40A—C40—H40B109.5
N4—C12—H12C109.5N9—C40—H40C109.5
H12A—C12—H12C109.5H40A—C40—H40C109.5
H12B—C12—H12C109.5H40B—C40—H40C109.5
N4—C13—C18106.18 (19)
N3—Co—O1—C28−66.15 (18)N7—C10—C11—N4155.0 (2)
N5—Co—O1—C2856.81 (18)C11—N4—C13—C180.6 (2)
N1—Co—O1—C28176.42 (17)C12—N4—C13—C18176.9 (2)
N7—Co—O1—C28170.2 (3)C11—N4—C13—C14−179.0 (3)
O1—Co—N1—C2−153.11 (15)C12—N4—C13—C14−2.7 (4)
N3—Co—N1—C291.05 (16)N4—C13—C14—C15178.7 (3)
N5—Co—N1—C2−39.37 (17)C18—C13—C14—C15−0.9 (4)
N7—Co—N1—C225.44 (15)C13—C14—C15—C160.3 (5)
O1—Co—N1—C96.3 (2)C14—C15—C16—C170.9 (5)
N3—Co—N1—C9−109.53 (19)C15—C16—C17—C18−1.5 (5)
N5—Co—N1—C9120.05 (19)C16—C17—C18—N3−178.1 (3)
N7—Co—N1—C9−175.1 (2)C16—C17—C18—C131.0 (4)
O1—Co—N3—C11−150.67 (15)C11—N3—C18—C17178.9 (3)
N5—Co—N3—C1186.68 (16)Co—N3—C18—C174.1 (4)
N1—Co—N3—C11−46.80 (17)C11—N3—C18—C13−0.3 (2)
N7—Co—N3—C1118.23 (15)Co—N3—C18—C13−175.14 (16)
O1—Co—N3—C1823.7 (2)N4—C13—C18—C17−179.5 (2)
N5—Co—N3—C18−98.9 (2)C14—C13—C18—C170.2 (4)
N1—Co—N3—C18127.6 (2)N4—C13—C18—N3−0.1 (2)
N7—Co—N3—C18−167.4 (2)C14—C13—C18—N3179.5 (2)
O1—Co—N5—C20−175.68 (13)C10—N7—C19—C20146.98 (18)
N3—Co—N5—C20−51.60 (16)C1—N7—C19—C20−85.3 (2)
N1—Co—N5—C2080.57 (15)Co—N7—C19—C2031.44 (19)
N7—Co—N5—C2016.56 (14)C27—N5—C20—N6−0.1 (2)
O1—Co—N5—C27−3.2 (2)Co—N5—C20—N6174.69 (13)
N3—Co—N5—C27120.84 (19)C27—N5—C20—C19−177.83 (18)
N1—Co—N5—C27−107.00 (19)Co—N5—C20—C19−3.1 (2)
N7—Co—N5—C27−171.0 (2)C22—N6—C20—N5−0.2 (2)
O1—Co—N7—C19−143.9 (3)C21—N6—C20—N5178.40 (19)
N3—Co—N7—C1988.90 (14)C22—N6—C20—C19177.54 (19)
N5—Co—N7—C19−26.95 (13)C21—N6—C20—C19−3.9 (3)
N1—Co—N7—C19−150.39 (14)N7—C19—C20—N5−21.8 (3)
O1—Co—N7—C1096.7 (3)N7—C19—C20—N6160.68 (18)
N3—Co—N7—C10−30.56 (12)C20—N6—C22—C23−178.7 (2)
N5—Co—N7—C10−146.40 (13)C21—N6—C22—C232.7 (4)
N1—Co—N7—C1090.16 (13)C20—N6—C22—C270.3 (2)
O1—Co—N7—C1−24.4 (4)C21—N6—C22—C27−178.25 (19)
N3—Co—N7—C1−151.66 (14)N6—C22—C23—C24−179.7 (2)
N5—Co—N7—C192.50 (14)C27—C22—C23—C241.4 (3)
N1—Co—N7—C1−30.94 (13)C22—C23—C24—C25−0.1 (3)
C19—N7—C1—C2147.90 (17)C23—C24—C25—C26−0.7 (3)
C10—N7—C1—C2−85.2 (2)C24—C25—C26—C270.2 (3)
Co—N7—C1—C231.04 (19)C20—N5—C27—C26−179.0 (2)
C9—N1—C2—N2−1.4 (2)Co—N5—C27—C268.0 (3)
Co—N1—C2—N2163.89 (13)C20—N5—C27—C220.3 (2)
C9—N1—C2—C1178.62 (19)Co—N5—C27—C22−172.74 (15)
Co—N1—C2—C1−16.1 (3)C25—C26—C27—N5−179.8 (2)
C4—N2—C2—N11.4 (2)C25—C26—C27—C221.0 (3)
C3—N2—C2—N1−178.2 (2)N6—C22—C27—N5−0.4 (2)
C4—N2—C2—C1−178.7 (2)C23—C22—C27—N5178.79 (18)
C3—N2—C2—C11.8 (3)N6—C22—C27—C26178.98 (17)
N7—C1—C2—N1−13.2 (3)C23—C22—C27—C26−1.9 (3)
N7—C1—C2—N2166.79 (19)Co—O1—C28—O2−0.3 (3)
C2—N2—C4—C9−0.7 (2)Co—O1—C28—C29179.49 (14)
C3—N2—C4—C9178.8 (2)O2—C28—C29—C30173.9 (2)
C2—N2—C4—C5177.7 (2)O1—C28—C29—C30−5.9 (3)
C3—N2—C4—C5−2.8 (4)O2—C28—C29—C34−5.0 (3)
N2—C4—C5—C6−178.0 (2)O1—C28—C29—C34175.2 (2)
C9—C4—C5—C60.2 (3)C34—C29—C30—C31−0.8 (3)
C4—C5—C6—C7−0.2 (4)C28—C29—C30—C31−179.7 (2)
C5—C6—C7—C80.2 (4)C29—C30—C31—C321.6 (4)
C6—C7—C8—C9−0.3 (3)C30—C31—C32—C33−0.9 (4)
C7—C8—C9—C40.3 (3)C31—C32—C33—C34−0.7 (4)
C7—C8—C9—N1178.3 (2)C32—C33—C34—O3−179.0 (2)
N2—C4—C9—C8178.29 (19)C32—C33—C34—C291.6 (4)
C5—C4—C9—C8−0.3 (3)C30—C29—C34—O3179.8 (2)
N2—C4—C9—N1−0.1 (2)C28—C29—C34—O3−1.3 (3)
C5—C4—C9—N1−178.68 (19)C30—C29—C34—C33−0.9 (3)
C2—N1—C9—C8−177.3 (2)C28—C29—C34—C33178.1 (2)
Co—N1—C9—C821.8 (3)C37'—O8—C37—N8−1.2 (5)
C2—N1—C9—C40.9 (2)C37'—N8—C37—O81.3 (5)
Co—N1—C9—C4−160.00 (16)C36'—N8—C37—O8−178.3 (7)
C19—N7—C10—C11−80.0 (2)C35—N8—C37—O8−0.6 (8)
C1—N7—C10—C11153.41 (17)C36—N8—C37—O8175.4 (6)
Co—N7—C10—C1136.38 (18)C35'—N8—C37—O817 (2)
C18—N3—C11—N40.7 (2)C37—O8—C37'—N81.3 (5)
Co—N3—C11—N4176.74 (14)C37—N8—C37'—O8−1.2 (5)
C18—N3—C11—C10−178.19 (19)C36'—N8—C37'—O8−0.7 (8)
Co—N3—C11—C10−2.1 (3)C35—N8—C37'—O8177.1 (7)
C13—N4—C11—N3−0.8 (2)C36—N8—C37'—O8−31 (3)
C12—N4—C11—N3−177.0 (2)C35'—N8—C37'—O8−177.0 (5)
C13—N4—C11—C10178.0 (2)C40—N9—C38—O9179.5 (4)
C12—N4—C11—C101.9 (4)C39—N9—C38—O90.4 (4)
N7—C10—C11—N3−26.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3O···O20.82 (3)1.78 (2)2.550 (4)154 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2710).

References

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