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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m19.
Published online 2007 December 6. doi:  10.1107/S1600536807061661
PMCID: PMC2914911

(Salicylato)[tris­(1-methyl-1H-benz­imidazol-2-ylmeth­yl)amine]copper(II) perchlorate dimethyl­formamide disolvate

Abstract

In the title complex, [Cu(C7H5O3)(C27H27N7)]ClO4·2C3H7NO, the CuII ion is five-coordinated by four N atoms from the tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine ligand and an O atom of the monodentate salicylate ligand. The N4O donor set defines a coordination geometry inter­mediate between square-pyramidal and trigonal–bipyramidal. The crystal structure is stabilized by O—H(...)O inter­actions. The atoms of the aromatic ring of the salicylate ligand are disordered over two sites of equal occupancy. In addition, one of the dimethyl­formamide solvent mol­ecules is partially disordered over two positions, of approximately equal occupancy.

Related literature

For related literature, see: Addison et al. (1984 [triangle]); Allen et al. (1987 [triangle]); Spek (2003 [triangle]); Youngme et al. (2007 [triangle]).

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Object name is e-64-00m19-scheme1.jpg

Experimental

Crystal data

  • [Cu(C7H5O3)(C27H27N7)]ClO4·2C3H7NO
  • M r = 895.85
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-00m19-efi1.jpg
  • a = 12.3507 (4) Å
  • b = 12.6632 (5) Å
  • c = 14.4152 (4) Å
  • α = 85.721 (1)°
  • β = 70.886 (1)°
  • γ = 76.503 (1)°
  • V = 2071.40 (12) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.66 mm−1
  • T = 153 (2) K
  • 0.54 × 0.52 × 0.39 mm

Data collection

  • Rigaku R-AXIS SPIDER diffractometer
  • Absorption correction: multi-scan (Higashi, 1995 [triangle]) T min = 0.718, T max = 0.783
  • 17142 measured reflections
  • 7660 independent reflections
  • 7110 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.134
  • S = 1.05
  • 7660 reflections
  • 603 parameters
  • 24 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.88 e Å−3
  • Δρmin = −0.86 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, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2000 [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/S1600536807061661/tk2203sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061661/tk2203Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

The asymmetric unit of the title complex, (Fig. 1), comprises a [Cu(Mentb)(salicylate)] cation, a perchlorate anion, and two dimethylformamide (DMF) molecules of crystallization, where Mentb = tris(N-methylbenzimidazol-2-ylmethyl)amine. The Cu atom is five-coordinate within a N4O ligand set. The Mentb ligand functions as a tetradentate N-donor, and an O atom of a monodentate salicylate anion completes the coordination environment. The coordination environment of the CuII centre has an intermediate coordination geometry as seen in the value of τ = 0.45, cf.τ = 0 for an ideal square pyramid and τ = 1 for an ideal trigonal bipyramid (Addison et al., 1984). The Cu···O2 distance of 2.960 (2) Å indicates that the O2 atom is non-coordinating. The distances and angles in Mentb and salicylate are as expected (Allen et al., 1987). O—H···O Hydrogen-bonding interactions play an important role in the crystal packing (Table 1). The atoms of the aromatic ring of the salicylate ligand are disordered over two sites with equal occupancy and one of the lattice DMF molecules is partially disordered over two positions, of approximately equal occupancy.

Experimental

To a stired solution of tris(N-methylbenzimidazol-2-ylmethyl)amine (0.0899 g, 0.2 mmol) in hot MeOH (10 ml) was added Cu(ClO4)2(H2O)6 (0.0741 g, 0.2 mmol), followed by a solution of Na(salicylate) (0.0320 g, 0.2 mmol) in MeOH (5 ml). A blue-green 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 yield a blue-green solution that was allowed to evaporate at room temperature. Blue-green crystals suitable for X-ray diffraction studies were obtained after two weeks. Yield, 0.12 g (67%). Analysis found: C 53.63, H 5.18, N 14.07, Cu 7.09%. C40H46ClCuN9O9 requires: C 53.45, H 5.15, N 13.95, Cu 7.41%.

Refinement

The aromatic ring of the salicylate ligand was disordered over two sites and from refinement, these were determined to be of equal occupancy. One of the lattice dimethylformamide molecules is partially disordered over two positions and from refinement, the major component was found to have an occupancy factor = 0.552 (15). All H atoms were geometrically positioned and refined using a riding-model approximation with C—H distances ranging from 0.95 to 0.99 Å and O—H = 0.83 (1) Å, and with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 0.52Ueq(O).

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. The salicylate anion is disordered over two positions of equal occupancy ...

Crystal data

[Cu(C7H5O3)(C27H27N7)]ClO4·2C3H7NOZ = 2
Mr = 895.85F000 = 934
Triclinic, P1Dx = 1.436 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 12.3507 (4) ÅCell parameters from 18119 reflections
b = 12.6632 (5) Åθ = 3.2–27.5º
c = 14.4152 (4) ŵ = 0.66 mm1
α = 85.721 (1)ºT = 153 (2) K
β = 70.886 (1)ºBlock, blue
γ = 76.503 (1)º0.54 × 0.52 × 0.39 mm
V = 2071.40 (12) Å3

Data collection

Rigaku R-axis Spider diffractometer7660 independent reflections
Radiation source: Rotating Anode7110 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 153(2) Kθmax = 25.5º
ω scansθmin = 3.2º
Absorption correction: multi-scan(Higashi, 1995)h = −14→14
Tmin = 0.718, Tmax = 0.783k = −15→15
17142 measured reflectionsl = −16→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.134  w = 1/[σ2(Fo2) + (0.0705P)2 + 2.6589P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.006
7660 reflectionsΔρmax = 0.88 e Å3
603 parametersΔρmin = −0.86 e Å3
24 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0075 (10)

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)
Cu0.23086 (3)0.18111 (2)0.28279 (2)0.02632 (13)
Cl0.46206 (8)0.24356 (7)0.61206 (7)0.0542 (2)
O10.12367 (17)0.19029 (15)0.20785 (14)0.0333 (4)
O20.21747 (19)0.30068 (18)0.10096 (16)0.0440 (5)
O40.5081 (4)0.2148 (5)0.6893 (3)0.136 (2)
O50.5122 (4)0.1574 (3)0.5410 (5)0.155 (3)
O60.3371 (3)0.2617 (3)0.6404 (2)0.0865 (11)
O70.4971 (3)0.3351 (3)0.5646 (3)0.0789 (9)
O80.7130 (4)0.1796 (3)0.2226 (4)0.1226 (17)
O90.4655 (2)0.3831 (2)0.1943 (2)0.0642 (7)
N10.1330 (2)0.12553 (17)0.42437 (16)0.0303 (5)
N20.1388 (2)0.08381 (18)0.57588 (17)0.0347 (5)
N30.35227 (19)0.05833 (17)0.20799 (15)0.0272 (5)
N40.54005 (19)−0.03060 (18)0.16286 (16)0.0309 (5)
N50.1866 (2)0.33208 (17)0.33286 (16)0.0305 (5)
N60.2204 (2)0.45780 (17)0.41241 (16)0.0299 (5)
N70.3577 (2)0.16453 (18)0.35884 (17)0.0317 (5)
N80.7165 (3)0.3526 (3)0.2367 (3)0.0630 (9)
N90.3491 (3)0.5382 (2)0.1623 (2)0.0463 (6)
C10.3300 (3)0.0824 (2)0.4377 (2)0.0339 (6)
H1A0.36510.00830.41000.041*
H1B0.36360.09130.48950.041*
C20.2003 (3)0.0973 (2)0.48048 (19)0.0310 (6)
C30.1859 (4)0.0485 (3)0.6570 (2)0.0516 (9)
H3A0.2275−0.02800.64770.062*
H3B0.12120.05680.71930.062*
H3C0.24060.09290.65830.062*
C40.0213 (3)0.1061 (2)0.5821 (2)0.0356 (6)
C5−0.0806 (3)0.1079 (2)0.6602 (2)0.0441 (7)
H5−0.07860.08910.72480.053*
C6−0.1852 (3)0.1383 (3)0.6399 (2)0.0487 (8)
H6−0.25690.14100.69190.058*
C7−0.1888 (3)0.1654 (2)0.5443 (2)0.0433 (7)
H7−0.26260.18600.53320.052*
C8−0.0868 (3)0.1625 (2)0.4663 (2)0.0363 (6)
H8−0.08890.18010.40160.044*
C90.0192 (3)0.1327 (2)0.48621 (19)0.0307 (6)
C100.4740 (2)0.1227 (2)0.2862 (2)0.0360 (6)
H10A0.52980.08320.31960.043*
H10B0.50580.18340.24840.043*
C110.4568 (2)0.0481 (2)0.21948 (19)0.0294 (5)
C120.6630 (2)−0.0650 (3)0.1588 (2)0.0382 (7)
H12A0.6853−0.00720.18520.046*
H12B0.7128−0.07990.09050.046*
H12C0.6731−0.13100.19800.046*
C130.4861 (2)−0.0758 (2)0.11005 (18)0.0292 (5)
C140.5307 (3)−0.1582 (2)0.0407 (2)0.0364 (6)
H140.6105−0.19660.02250.044*
C150.4529 (3)−0.1815 (2)−0.0005 (2)0.0390 (7)
H150.4801−0.2368−0.04910.047*
C160.3349 (3)−0.1261 (2)0.0271 (2)0.0358 (6)
H160.2841−0.1450−0.00300.043*
C170.2903 (2)−0.0445 (2)0.09713 (19)0.0305 (6)
H170.2100−0.00750.11610.037*
C180.3680 (2)−0.0191 (2)0.13840 (18)0.0265 (5)
C190.3507 (3)0.2711 (2)0.4003 (2)0.0400 (7)
H19A0.42590.29400.36990.048*
H19B0.33650.26430.47190.048*
C200.2527 (3)0.3542 (2)0.38059 (19)0.0301 (6)
C210.2778 (3)0.5092 (2)0.4650 (2)0.0394 (7)
H21A0.31250.45480.50530.047*
H21B0.21960.56710.50730.047*
H21C0.33960.54000.41760.047*
C220.1228 (2)0.5066 (2)0.38473 (19)0.0292 (5)
C230.0509 (3)0.6106 (2)0.4013 (2)0.0361 (6)
H230.06620.66450.43480.043*
C24−0.0432 (3)0.6311 (2)0.3666 (2)0.0388 (7)
H24−0.09440.70100.37670.047*
C25−0.0660 (3)0.5522 (2)0.3167 (2)0.0362 (6)
H25−0.13240.56960.29440.043*
C260.0066 (2)0.4492 (2)0.2993 (2)0.0318 (6)
H26−0.00800.39600.26470.038*
C270.1017 (2)0.4270 (2)0.33478 (18)0.0273 (5)
C280.1456 (2)0.2419 (2)0.12643 (18)0.0308 (6)
O30.1645 (6)0.3536 (6)−0.0564 (5)0.0758 (18)0.50
C290.0846 (10)0.2304 (10)0.0545 (6)0.037 (4)*0.50
C300.0955 (13)0.2819 (11)−0.0356 (8)0.040 (4)*0.50
C310.0378 (17)0.2540 (18)−0.0951 (13)0.039 (3)0.50
H310.04650.2886−0.15710.047*0.50
C32−0.032 (2)0.1780 (18)−0.0685 (13)0.043 (4)0.50
H32−0.06200.1558−0.11490.051*0.50
C33−0.0584 (13)0.1344 (16)0.0255 (10)0.034 (3)0.50
H33−0.11850.09530.05270.041*0.50
C340.0142 (17)0.1550 (15)0.0749 (12)0.058 (5)0.50
H340.01580.11110.13100.069*0.50
O3'−0.0091 (4)0.0935 (4)0.1671 (3)0.0461 (10)0.50
C29'0.0772 (7)0.2233 (7)0.0627 (5)0.019 (3)*0.50
C34'0.0954 (15)0.2843 (13)−0.0231 (8)0.049 (4)0.50
H34'0.14670.3325−0.03360.058*0.50
C33'0.044 (2)0.280 (2)−0.0947 (15)0.063 (5)0.50
H33'0.05430.3244−0.15130.076*0.50
C32'−0.025 (2)0.2027 (19)−0.0751 (14)0.057 (5)0.50
H32'−0.06740.1970−0.11810.069*0.50
C31'−0.0328 (15)0.1338 (18)0.0054 (8)0.045 (4)0.50
H31'−0.06510.07230.00720.054*0.50
C30'0.0039 (13)0.1504 (10)0.0836 (7)0.022 (2)*0.50
C350.6697 (8)0.3959 (11)0.3338 (4)0.246 (8)
H35A0.62660.47120.33250.296*
H35B0.73400.39370.36010.296*
H35C0.61620.35250.37570.296*
C360.7496 (7)0.4342 (8)0.1654 (6)0.204 (6)
H36A0.82810.44250.16080.245*
H36B0.69290.50340.18530.245*
H36C0.75040.41240.10130.245*
C370.7209 (7)0.2688 (3)0.1846 (4)0.044 (3)0.448 (15)
H370.73040.27790.11660.053*0.448 (15)
C37'0.7054 (10)0.2553 (4)0.2738 (6)0.181 (12)0.552 (15)
H37'0.69120.24400.34230.217*0.552 (15)
C380.3954 (5)0.6093 (3)0.2048 (4)0.0790 (14)
H38A0.46370.56740.22180.095*
H38B0.33490.64300.26420.095*
H38C0.41910.66590.15740.095*
C390.2527 (4)0.5877 (4)0.1252 (4)0.0725 (12)
H39A0.22450.53070.10360.087*
H39B0.28010.63500.06960.087*
H39C0.18850.63070.17740.087*
C400.3882 (3)0.4317 (3)0.1615 (3)0.0477 (8)
H400.35310.38930.13310.057*
H3O'0.026 (5)0.117 (4)0.199 (4)0.024 (15)*0.50
H3O0.191 (6)0.365 (6)−0.013 (4)0.040 (19)*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cu0.0330 (2)0.02317 (18)0.02454 (19)0.00196 (13)−0.01623 (14)−0.00412 (12)
Cl0.0642 (5)0.0541 (5)0.0705 (6)−0.0295 (4)−0.0514 (5)0.0309 (4)
O10.0366 (10)0.0345 (10)0.0295 (10)0.0003 (8)−0.0167 (8)−0.0024 (8)
O20.0433 (12)0.0474 (12)0.0464 (12)−0.0162 (10)−0.0163 (10)−0.0021 (10)
O40.130 (3)0.239 (5)0.110 (3)−0.122 (4)−0.101 (3)0.117 (3)
O50.133 (4)0.066 (2)0.317 (7)0.039 (2)−0.164 (5)−0.075 (3)
O60.0596 (18)0.153 (3)0.0614 (18)−0.045 (2)−0.0287 (15)0.025 (2)
O70.087 (2)0.0645 (18)0.088 (2)−0.0302 (16)−0.0294 (18)0.0329 (16)
O80.084 (3)0.074 (2)0.182 (5)−0.035 (2)0.006 (3)0.003 (3)
O90.0589 (16)0.0487 (14)0.093 (2)−0.0068 (12)−0.0405 (15)0.0104 (14)
N10.0414 (13)0.0237 (10)0.0252 (11)0.0002 (9)−0.0141 (10)−0.0045 (8)
N20.0560 (15)0.0253 (11)0.0275 (11)−0.0089 (10)−0.0197 (11)0.0012 (9)
N30.0307 (11)0.0278 (11)0.0233 (10)−0.0001 (9)−0.0127 (9)−0.0019 (8)
N40.0282 (11)0.0333 (12)0.0268 (11)−0.0002 (9)−0.0085 (9)0.0032 (9)
N50.0416 (13)0.0233 (11)0.0301 (11)−0.0006 (9)−0.0201 (10)−0.0021 (9)
N60.0423 (13)0.0244 (11)0.0268 (11)−0.0076 (9)−0.0156 (10)−0.0012 (9)
N70.0403 (13)0.0263 (11)0.0323 (12)0.0006 (9)−0.0217 (10)−0.0025 (9)
N80.062 (2)0.0539 (19)0.089 (3)−0.0119 (15)−0.0444 (19)−0.0043 (17)
N90.0543 (16)0.0393 (14)0.0481 (16)−0.0129 (12)−0.0197 (13)0.0074 (12)
C10.0459 (16)0.0279 (13)0.0297 (13)0.0034 (11)−0.0222 (12)−0.0013 (11)
C20.0483 (16)0.0199 (12)0.0267 (13)−0.0009 (11)−0.0184 (12)−0.0034 (10)
C30.078 (2)0.055 (2)0.0323 (16)−0.0202 (18)−0.0302 (17)0.0130 (14)
C40.0589 (19)0.0199 (12)0.0307 (14)−0.0118 (12)−0.0154 (13)−0.0022 (10)
C50.066 (2)0.0352 (16)0.0333 (15)−0.0229 (15)−0.0110 (15)0.0009 (12)
C60.060 (2)0.0383 (16)0.0436 (18)−0.0239 (15)−0.0012 (16)−0.0061 (13)
C70.0446 (17)0.0330 (15)0.0524 (19)−0.0146 (13)−0.0105 (15)−0.0052 (13)
C80.0454 (16)0.0245 (13)0.0395 (15)−0.0073 (12)−0.0136 (13)−0.0042 (11)
C90.0437 (15)0.0186 (12)0.0287 (13)−0.0048 (10)−0.0105 (12)−0.0052 (10)
C100.0338 (14)0.0403 (15)0.0376 (15)−0.0028 (12)−0.0199 (12)−0.0016 (12)
C110.0300 (13)0.0311 (13)0.0258 (12)−0.0012 (10)−0.0115 (11)0.0016 (10)
C120.0273 (14)0.0456 (17)0.0350 (15)0.0017 (12)−0.0094 (12)0.0066 (12)
C130.0331 (14)0.0271 (13)0.0220 (12)−0.0020 (10)−0.0059 (11)0.0047 (10)
C140.0411 (16)0.0294 (14)0.0270 (13)0.0014 (12)−0.0021 (12)0.0011 (11)
C150.0551 (18)0.0273 (14)0.0266 (13)−0.0040 (13)−0.0055 (13)−0.0030 (11)
C160.0506 (17)0.0307 (14)0.0277 (13)−0.0109 (12)−0.0132 (12)−0.0009 (11)
C170.0366 (14)0.0294 (13)0.0234 (12)−0.0051 (11)−0.0085 (11)0.0008 (10)
C180.0325 (13)0.0240 (12)0.0193 (11)−0.0012 (10)−0.0070 (10)0.0007 (9)
C190.0570 (19)0.0273 (14)0.0467 (17)−0.0006 (13)−0.0364 (15)−0.0046 (12)
C200.0429 (15)0.0247 (12)0.0260 (13)−0.0050 (11)−0.0172 (12)−0.0005 (10)
C210.0560 (19)0.0321 (14)0.0387 (16)−0.0144 (13)−0.0228 (14)−0.0031 (12)
C220.0377 (14)0.0236 (12)0.0242 (12)−0.0060 (10)−0.0077 (11)0.0005 (10)
C230.0467 (17)0.0231 (13)0.0360 (15)−0.0058 (12)−0.0102 (13)−0.0041 (11)
C240.0409 (16)0.0229 (13)0.0460 (17)0.0005 (11)−0.0095 (13)−0.0033 (12)
C250.0340 (14)0.0298 (14)0.0409 (16)−0.0017 (11)−0.0110 (12)0.0018 (12)
C260.0358 (14)0.0266 (13)0.0326 (14)−0.0028 (11)−0.0128 (12)−0.0019 (11)
C270.0343 (14)0.0211 (12)0.0241 (12)−0.0026 (10)−0.0085 (11)0.0000 (9)
C280.0296 (13)0.0290 (13)0.0315 (14)0.0018 (11)−0.0109 (11)−0.0070 (11)
O30.085 (4)0.093 (5)0.060 (4)−0.039 (4)−0.033 (3)0.040 (3)
C310.050 (6)0.042 (9)0.033 (5)−0.017 (5)−0.021 (4)0.010 (4)
C320.043 (6)0.045 (9)0.047 (6)−0.011 (6)−0.020 (4)−0.008 (5)
C330.022 (6)0.043 (5)0.034 (5)−0.003 (4)−0.007 (5)−0.004 (4)
C340.049 (8)0.060 (7)0.066 (7)0.005 (4)−0.034 (6)0.000 (4)
O3'0.046 (3)0.053 (3)0.048 (3)−0.020 (2)−0.022 (2)0.012 (2)
C34'0.059 (6)0.065 (7)0.022 (4)−0.009 (3)−0.020 (4)0.016 (4)
C33'0.091 (11)0.062 (13)0.044 (6)−0.008 (7)−0.041 (7)0.012 (6)
C32'0.085 (12)0.051 (11)0.051 (7)0.011 (7)−0.055 (8)−0.015 (5)
C31'0.029 (7)0.058 (7)0.045 (8)−0.003 (5)−0.009 (6)−0.020 (6)
C350.223 (10)0.52 (2)0.068 (4)−0.264 (14)−0.006 (5)−0.058 (8)
C360.091 (5)0.354 (16)0.136 (7)−0.021 (7)−0.039 (5)0.118 (9)
C370.041 (4)0.050 (5)0.044 (4)−0.016 (3)−0.009 (3)−0.009 (3)
C37'0.084 (9)0.099 (10)0.39 (4)0.017 (7)−0.125 (16)−0.079 (15)
C380.132 (4)0.047 (2)0.078 (3)−0.034 (2)−0.051 (3)0.009 (2)
C390.071 (3)0.070 (3)0.076 (3)−0.006 (2)−0.034 (2)0.025 (2)
C400.0492 (19)0.0411 (17)0.057 (2)−0.0154 (15)−0.0198 (16)0.0012 (15)

Geometric parameters (Å, °)

Cu—O11.9441 (19)C14—H140.9500
Cu—N31.983 (2)C15—C161.400 (4)
Cu—N51.983 (2)C15—H150.9500
Cu—N72.153 (2)C16—C171.384 (4)
Cu—N12.165 (2)C16—H160.9500
Cl—O71.386 (3)C17—C181.387 (4)
Cl—O41.397 (3)C17—H170.9500
Cl—O61.427 (3)C19—C201.496 (4)
Cl—O51.435 (5)C19—H19A0.9900
O1—C281.280 (3)C19—H19B0.9900
O2—C281.237 (3)C21—H21A0.9800
O8—C37'1.220 (3)C21—H21B0.9800
O8—C371.229 (3)C21—H21C0.9800
O9—C401.221 (4)C22—C231.394 (4)
N1—C21.316 (4)C22—C271.398 (4)
N1—C91.382 (4)C23—C241.375 (4)
N2—C21.356 (4)C23—H230.9500
N2—C41.386 (4)C24—C251.402 (4)
N2—C31.467 (4)C24—H240.9500
N3—C111.331 (3)C25—C261.387 (4)
N3—C181.391 (3)C25—H250.9500
N4—C111.345 (3)C26—C271.392 (4)
N4—C131.387 (4)C26—H260.9500
N4—C121.461 (3)C28—C291.4997 (10)
N5—C201.313 (3)C28—C29'1.5001 (10)
N5—C271.393 (3)O3—C301.3399 (10)
N6—C201.347 (3)O3—H3O0.828 (10)
N6—C221.388 (4)C29—C301.3899 (10)
N6—C211.462 (3)C29—C341.3899 (10)
N7—C101.477 (4)C30—C311.3898 (10)
N7—C191.489 (3)C31—C321.3899 (10)
N7—C11.492 (4)C31—H310.9500
N8—C37'1.325 (3)C32—C331.3897 (10)
N8—C371.326 (3)C32—H320.9500
N8—C351.425 (3)C33—C341.3903 (10)
N8—C361.434 (3)C33—H330.9500
N9—C401.321 (4)C34—H340.9500
N9—C381.437 (5)O3'—C30'1.3398 (10)
N9—C391.455 (5)O3'—H3O'0.830 (10)
C1—C21.487 (4)C29'—C30'1.3896 (10)
C1—H1A0.9900C29'—C34'1.3901 (10)
C1—H1B0.9900C34'—C33'1.3899 (10)
C3—H3A0.9800C34'—H34'0.9500
C3—H3B0.9800C33'—C32'1.3899 (10)
C3—H3C0.9800C33'—H33'0.9500
C4—C51.383 (4)C32'—C31'1.3898 (10)
C4—C91.406 (4)C32'—H32'0.9500
C5—C61.379 (5)C31'—C30'1.3903 (10)
C5—H50.9500C31'—H31'0.9500
C6—C71.408 (5)C35—H35A0.9800
C6—H60.9500C35—H35B0.9800
C7—C81.382 (4)C35—H35C0.9800
C7—H70.9500C36—H36A0.9800
C8—C91.392 (4)C36—H36B0.9800
C8—H80.9500C36—H36C0.9800
C10—C111.491 (4)C37—H370.9500
C10—H10A0.9900C37'—H37'0.9500
C10—H10B0.9900C38—H38A0.9800
C12—H12A0.9800C38—H38B0.9800
C12—H12B0.9800C38—H38C0.9800
C12—H12C0.9800C39—H39A0.9800
C13—C141.386 (4)C39—H39B0.9800
C13—C181.406 (4)C39—H39C0.9800
C14—C151.376 (5)C40—H400.9500
O1—Cu—N396.36 (8)C17—C18—N3131.4 (2)
O1—Cu—N5100.54 (8)C17—C18—C13120.5 (2)
N3—Cu—N5149.64 (10)N3—C18—C13108.1 (2)
O1—Cu—N7176.47 (8)N7—C19—C20109.5 (2)
N3—Cu—N780.21 (9)N7—C19—H19A109.8
N5—Cu—N782.24 (9)C20—C19—H19A109.8
O1—Cu—N1102.12 (9)N7—C19—H19B109.8
N3—Cu—N1110.14 (8)C20—C19—H19B109.8
N5—Cu—N190.79 (9)H19A—C19—H19B108.2
N7—Cu—N179.92 (9)N5—C20—N6113.0 (2)
O7—Cl—O4110.4 (2)N5—C20—C19122.9 (2)
O7—Cl—O6109.2 (2)N6—C20—C19124.0 (2)
O4—Cl—O6114.4 (2)N6—C21—H21A109.5
O7—Cl—O5106.2 (3)N6—C21—H21B109.5
O4—Cl—O5107.9 (3)H21A—C21—H21B109.5
O6—Cl—O5108.5 (2)N6—C21—H21C109.5
C28—O1—Cu117.26 (16)H21A—C21—H21C109.5
C37'—O8—C3760.9 (5)H21B—C21—H21C109.5
C2—N1—C9105.7 (2)N6—C22—C23131.5 (3)
C2—N1—Cu110.55 (19)N6—C22—C27106.2 (2)
C9—N1—Cu141.28 (18)C23—C22—C27122.3 (3)
C2—N2—C4106.6 (2)C24—C23—C22116.4 (3)
C2—N2—C3127.4 (3)C24—C23—H23121.8
C4—N2—C3125.9 (3)C22—C23—H23121.8
C11—N3—C18105.9 (2)C23—C24—C25122.2 (3)
C11—N3—Cu113.72 (17)C23—C24—H24118.9
C18—N3—Cu140.14 (18)C25—C24—H24118.9
C11—N4—C13106.8 (2)C26—C25—C24121.2 (3)
C11—N4—C12127.3 (2)C26—C25—H25119.4
C13—N4—C12126.0 (2)C24—C25—H25119.4
C20—N5—C27106.0 (2)C25—C26—C27117.3 (3)
C20—N5—Cu114.92 (18)C25—C26—H26121.4
C27—N5—Cu139.03 (18)C27—C26—H26121.4
C20—N6—C22106.6 (2)C26—C27—N5131.1 (2)
C20—N6—C21126.7 (2)C26—C27—C22120.7 (2)
C22—N6—C21126.7 (2)N5—C27—C22108.2 (2)
C10—N7—C19111.9 (2)O2—C28—O1124.0 (2)
C10—N7—C1109.9 (2)O2—C28—C29116.3 (4)
C19—N7—C1111.5 (2)O1—C28—C29119.7 (4)
C10—N7—Cu106.43 (16)O2—C28—C29'122.4 (4)
C19—N7—Cu110.25 (16)O1—C28—C29'113.6 (3)
C1—N7—Cu106.65 (17)C29—C28—C29'6.1 (6)
C37'—N8—C3755.8 (5)C30—O3—H3O117 (5)
C37'—N8—C3589.1 (7)C30—C29—C34114.2 (6)
C37—N8—C35142.0 (6)C30—C29—C28127.5 (8)
C37'—N8—C36159.2 (7)C34—C29—C28118.1 (8)
C37—N8—C36104.8 (6)O3—C30—C31126.7 (10)
C35—N8—C36111.5 (7)O3—C30—C29114.6 (9)
C40—N9—C38121.4 (3)C31—C30—C29118.7 (10)
C40—N9—C39121.2 (3)C30—C31—C32123.3 (19)
C38—N9—C39117.3 (3)C30—C31—H31118.3
C2—C1—N7109.2 (2)C32—C31—H31118.3
C2—C1—H1A109.8C33—C32—C31120 (2)
N7—C1—H1A109.8C33—C32—H32119.8
C2—C1—H1B109.8C31—C32—H32119.8
N7—C1—H1B109.8C32—C33—C34111.6 (17)
H1A—C1—H1B108.3C32—C33—H33124.2
N1—C2—N2113.1 (3)C34—C33—H33124.2
N1—C2—C1120.4 (2)C29—C34—C33129.7 (12)
N2—C2—C1126.5 (2)C29—C34—H34115.1
N2—C3—H3A109.5C33—C34—H34115.1
N2—C3—H3B109.5C30'—O3'—H3O'108 (4)
H3A—C3—H3B109.5C30'—C29'—C34'121.5 (5)
N2—C3—H3C109.5C30'—C29'—C28124.7 (6)
H3A—C3—H3C109.5C34'—C29'—C28113.8 (7)
H3B—C3—H3C109.5C33'—C34'—C29'124.5 (13)
C5—C4—N2132.5 (3)C33'—C34'—H34'117.7
C5—C4—C9121.9 (3)C29'—C34'—H34'117.7
N2—C4—C9105.5 (3)C34'—C33'—C32'113.3 (19)
C6—C5—C4116.9 (3)C34'—C33'—H33'123.3
C6—C5—H5121.6C32'—C33'—H33'123.3
C4—C5—H5121.6C31'—C32'—C33'121.9 (19)
C5—C6—C7121.9 (3)C31'—C32'—H32'119.0
C5—C6—H6119.1C33'—C32'—H32'119.1
C7—C6—H6119.1C32'—C31'—C30'123.4 (15)
C8—C7—C6121.1 (3)C32'—C31'—H31'118.3
C8—C7—H7119.4C30'—C31'—H31'118.3
C6—C7—H7119.4O3'—C30'—C29'118.5 (7)
C7—C8—C9117.4 (3)O3'—C30'—C31'127.2 (9)
C7—C8—H8121.3C29'—C30'—C31'113.5 (8)
C9—C8—H8121.3N8—C35—H35A109.5
N1—C9—C8130.1 (3)N8—C35—H35B109.5
N1—C9—C4109.1 (3)H35A—C35—H35B109.5
C8—C9—C4120.8 (3)N8—C35—H35C109.5
N7—C10—C11107.0 (2)H35A—C35—H35C109.5
N7—C10—H10A110.3H35B—C35—H35C109.5
C11—C10—H10A110.3N8—C36—H36A109.5
N7—C10—H10B110.3N8—C36—H36B109.5
C11—C10—H10B110.3H36A—C36—H36B109.5
H10A—C10—H10B108.6N8—C36—H36C109.5
N3—C11—N4112.9 (2)H36A—C36—H36C109.5
N3—C11—C10120.6 (2)H36B—C36—H36C109.5
N4—C11—C10126.5 (2)O8—C37—N8121.2 (5)
N4—C12—H12A109.5O8—C37—H37119.4
N4—C12—H12B109.5N8—C37—H37119.4
H12A—C12—H12B109.5O8—C37'—N8122.0 (6)
N4—C12—H12C109.5O8—C37'—H37'119.0
H12A—C12—H12C109.5N8—C37'—H37'119.0
H12B—C12—H12C109.5N9—C38—H38A109.5
C14—C13—N4131.1 (3)N9—C38—H38B109.5
C14—C13—C18122.5 (3)H38A—C38—H38B109.5
N4—C13—C18106.4 (2)N9—C38—H38C109.5
C15—C14—C13116.3 (3)H38A—C38—H38C109.5
C15—C14—H14121.8H38B—C38—H38C109.5
C13—C14—H14121.8N9—C39—H39A109.5
C14—C15—C16121.8 (3)N9—C39—H39B109.5
C14—C15—H15119.1H39A—C39—H39B109.5
C16—C15—H15119.1N9—C39—H39C109.5
C17—C16—C15121.8 (3)H39A—C39—H39C109.5
C17—C16—H16119.1H39B—C39—H39C109.5
C15—C16—H16119.1O9—C40—N9125.6 (3)
C16—C17—C18117.0 (3)O9—C40—H40117.2
C16—C17—H17121.5N9—C40—H40117.2
C18—C17—H17121.5
N3—Cu—O1—C28−81.64 (19)C16—C17—C18—N3178.8 (3)
N5—Cu—O1—C2873.03 (19)C16—C17—C18—C13−0.7 (4)
N1—Cu—O1—C28166.14 (18)C11—N3—C18—C17−179.1 (3)
O1—Cu—N1—C2169.54 (17)Cu—N3—C18—C17−5.8 (5)
N3—Cu—N1—C268.04 (18)C11—N3—C18—C130.4 (3)
N5—Cu—N1—C2−89.50 (18)Cu—N3—C18—C13173.7 (2)
N7—Cu—N1—C2−7.53 (17)C14—C13—C18—C170.1 (4)
O1—Cu—N1—C9−32.1 (3)N4—C13—C18—C17179.1 (2)
N3—Cu—N1—C9−133.6 (3)C14—C13—C18—N3−179.5 (2)
N5—Cu—N1—C968.9 (3)N4—C13—C18—N3−0.5 (3)
N7—Cu—N1—C9150.8 (3)C10—N7—C19—C20121.5 (3)
O1—Cu—N3—C11161.35 (18)C1—N7—C19—C20−115.0 (3)
N5—Cu—N3—C1137.7 (3)Cu—N7—C19—C203.2 (3)
N7—Cu—N3—C11−17.86 (18)C27—N5—C20—N6−1.5 (3)
N1—Cu—N3—C11−93.24 (19)Cu—N5—C20—N6179.33 (18)
O1—Cu—N3—C18−11.6 (3)C27—N5—C20—C19176.3 (3)
N5—Cu—N3—C18−135.3 (3)Cu—N5—C20—C19−2.8 (4)
N7—Cu—N3—C18169.2 (3)C22—N6—C20—N51.5 (3)
N1—Cu—N3—C1893.8 (3)C21—N6—C20—N5−178.0 (3)
O1—Cu—N5—C20−174.3 (2)C22—N6—C20—C19−176.4 (3)
N3—Cu—N5—C20−51.5 (3)C21—N6—C20—C194.2 (4)
N7—Cu—N5—C203.5 (2)N7—C19—C20—N5−0.5 (4)
N1—Cu—N5—C2083.3 (2)N7—C19—C20—N6177.1 (3)
O1—Cu—N5—C277.0 (3)C20—N6—C22—C23177.3 (3)
N3—Cu—N5—C27129.7 (3)C21—N6—C22—C23−3.3 (5)
N7—Cu—N5—C27−175.2 (3)C20—N6—C22—C27−0.8 (3)
N1—Cu—N5—C27−95.5 (3)C21—N6—C22—C27178.7 (2)
N3—Cu—N7—C1029.85 (17)N6—C22—C23—C24−177.2 (3)
N5—Cu—N7—C10−125.28 (19)C27—C22—C23—C240.5 (4)
N1—Cu—N7—C10142.53 (18)C22—C23—C24—C25−0.3 (4)
N3—Cu—N7—C19151.4 (2)C23—C24—C25—C26−0.5 (5)
N5—Cu—N7—C19−3.7 (2)C24—C25—C26—C271.0 (4)
N1—Cu—N7—C19−95.9 (2)C25—C26—C27—N5177.2 (3)
N3—Cu—N7—C1−87.44 (17)C25—C26—C27—C22−0.7 (4)
N5—Cu—N7—C1117.43 (17)C20—N5—C27—C26−177.1 (3)
N1—Cu—N7—C125.23 (16)Cu—N5—C27—C261.7 (5)
C10—N7—C1—C2−153.0 (2)C20—N5—C27—C221.0 (3)
C19—N7—C1—C282.3 (3)Cu—N5—C27—C22179.8 (2)
Cu—N7—C1—C2−38.1 (2)N6—C22—C27—C26178.2 (2)
C9—N1—C2—N20.7 (3)C23—C22—C27—C26−0.1 (4)
Cu—N1—C2—N2166.89 (17)N6—C22—C27—N5−0.1 (3)
C9—N1—C2—C1−179.7 (2)C23—C22—C27—N5−178.4 (2)
Cu—N1—C2—C1−13.6 (3)Cu—O1—C28—O2−12.6 (3)
C4—N2—C2—N1−0.5 (3)Cu—O1—C28—C29165.8 (6)
C3—N2—C2—N1177.3 (3)Cu—O1—C28—C29'166.4 (4)
C4—N2—C2—C1−180.0 (2)O2—C28—C29—C30−3.1 (17)
C3—N2—C2—C1−2.2 (4)O1—C28—C29—C30178.4 (13)
N7—C1—C2—N136.4 (3)C29'—C28—C29—C30173 (9)
N7—C1—C2—N2−144.1 (2)O2—C28—C29—C34172.3 (14)
C2—N2—C4—C5−178.4 (3)O1—C28—C29—C34−6.2 (17)
C3—N2—C4—C53.8 (5)C29'—C28—C29—C34−11 (8)
C2—N2—C4—C90.0 (3)C34—C29—C30—O3−179.2 (16)
C3—N2—C4—C9−177.9 (3)C28—C29—C30—O3−4(2)
N2—C4—C5—C6177.5 (3)C34—C29—C30—C310(3)
C9—C4—C5—C6−0.7 (4)C28—C29—C30—C31175.2 (15)
C4—C5—C6—C70.5 (4)O3—C30—C31—C32180 (2)
C5—C6—C7—C80.1 (5)C29—C30—C31—C321(3)
C6—C7—C8—C9−0.6 (4)C30—C31—C32—C337(4)
C2—N1—C9—C8178.0 (3)C31—C32—C33—C34−15 (3)
Cu—N1—C9—C819.0 (5)C30—C29—C34—C33−10 (3)
C2—N1—C9—C4−0.7 (3)C28—C29—C34—C33174.4 (19)
Cu—N1—C9—C4−159.7 (2)C32—C33—C34—C2917 (3)
C7—C8—C9—N1−178.2 (3)O2—C28—C29'—C30'173.7 (10)
C7—C8—C9—C40.5 (4)O1—C28—C29'—C30'−5.3 (13)
C5—C4—C9—N1179.1 (2)C29—C28—C29'—C30'170 (9)
N2—C4—C9—N10.5 (3)O2—C28—C29'—C34'−4.7 (13)
C5—C4—C9—C80.2 (4)O1—C28—C29'—C34'176.3 (10)
N2—C4—C9—C8−178.4 (2)C29—C28—C29'—C34'−9(8)
C19—N7—C10—C11−155.3 (2)C30'—C29'—C34'—C33'0(3)
C1—N7—C10—C1180.4 (3)C28—C29'—C34'—C33'178.7 (19)
Cu—N7—C10—C11−34.8 (2)C29'—C34'—C33'—C32'−3(4)
C18—N3—C11—N4−0.2 (3)C34'—C33'—C32'—C31'−4(4)
Cu—N3—C11—N4−175.55 (17)C33'—C32'—C31'—C30'15 (4)
C18—N3—C11—C10177.2 (2)C34'—C29'—C30'—O3'179.5 (14)
Cu—N3—C11—C101.9 (3)C28—C29'—C30'—O3'1(2)
C13—N4—C11—N30.0 (3)C34'—C29'—C30'—C31'9(2)
C12—N4—C11—N3−178.5 (2)C28—C29'—C30'—C31'−169.1 (13)
C13—N4—C11—C10−177.3 (3)C32'—C31'—C30'—O3'174 (2)
C12—N4—C11—C104.3 (4)C32'—C31'—C30'—C29'−16 (3)
N7—C10—C11—N324.1 (3)C37'—O8—C37—N81.9 (7)
N7—C10—C11—N4−158.9 (2)C37'—N8—C37—O8−1.8 (7)
C11—N4—C13—C14179.2 (3)C35—N8—C37—O8−27.8 (14)
C12—N4—C13—C14−2.3 (4)C36—N8—C37—O8169.9 (7)
C11—N4—C13—C180.3 (3)C37—O8—C37'—N8−1.9 (7)
C12—N4—C13—C18178.8 (2)C37—N8—C37'—O81.9 (7)
N4—C13—C14—C15−178.1 (3)C35—N8—C37'—O8166.2 (10)
C18—C13—C14—C150.7 (4)C36—N8—C37'—O8−21 (2)
C13—C14—C15—C16−0.9 (4)C38—N9—C40—O9−0.9 (6)
C14—C15—C16—C170.3 (4)C39—N9—C40—O9−177.2 (4)
C15—C16—C17—C180.5 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3'—H3O'···O10.84 (6)1.72 (6)2.493 (6)152 (5)
O3—H3O···O20.83 (7)1.87 (6)2.562 (7)140 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2203).

References

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