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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1252.
Published online 2010 September 11. doi:  10.1107/S160053681003610X
PMCID: PMC2983134

(Dimethyl­formamide-κO)(2-hy­droxy­benzoato-κ2 O 1,O 1′)[tris­(1-methyl-1H-benzimidazol-2-ylmethyl-κN 3)amine-κN]manganese(II) perchlorate dimethyl­formamide monosolvate

Abstract

In the title complex, [Mn(C7H5O3)(C27H27N7)(C3H7NO)]ClO4·C3H7NO, the MnII ion is coordinated in a slightly distorted monocapped trigonal-prismatic geometry. The tris­(1-methyl-1H-benzimidazol-2-ylmeth­yl)amine (Mentb) ligand coordinates in a tetra­dentate mode and the coordination is completed by a bis-chelating salicylate ligand and a dimethyl­formamide ligand. The hy­droxy group and the ortho H atoms of the salicylate ligand were refined as disordered over two sites with occupancies of 0.581 (8) and 0.419 (8). Both disorder components of the hy­droxy group form intra­molecular O—H(...)O hydrogen bonds.

Related literature

For the biological activity of benzimidazole compounds, see: Horton et al. (2003 [triangle]). For related structures, see: Wu et al. (2005 [triangle], 2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1252-scheme1.jpg

Experimental

Crystal data

  • [Mn(C7H5O3)(C27H27N7)(C3H7NO)]ClO4·C3H7NO
  • M r = 887.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1252-efi1.jpg
  • a = 12.3689 (13) Å
  • b = 12.4809 (13) Å
  • c = 15.3759 (16) Å
  • α = 69.925 (1)°
  • β = 87.926 (1)°
  • γ = 74.704 (1)°
  • V = 2146.6 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.43 mm−1
  • T = 296 K
  • 0.38 × 0.36 × 0.32 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.853, T max = 0.874
  • 15941 measured reflections
  • 7890 independent reflections
  • 6197 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.163
  • S = 1.10
  • 7890 reflections
  • 560 parameters
  • 16 restraints
  • H-atom parameters constrained
  • Δρmax = 0.54 e Å−3
  • Δρmin = −0.57 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681003610X/lh5127sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681003610X/lh5127Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support and a grant from the ‘Qing Lan’ Talent Engineering Funds and Students’ Science and Technology Innovation Funds (grant No. DXS2010–040) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and Long Yuan ‘Qing Nian’ of Gansu Province is also acknowledged.

supplementary crystallographic information

Comment

We are interested in tris(2-benzimidazolylmethyl)amine and its derivatives and we have previously reported the crystal structure of some related complexes (Wu et al., 2009; Wu et al., 2005). The benzimidazole core is of a wide interest because of its diverse biological activities, and it is well known in medicinal chemistry (Horton et al. 2003). The asymmetric unit of the title compound consists of a [Mn(Mentb)(salicylato)(DMF)] cation, a perchlorate anion, and one solvent molecule of DMF. The cation is shown in Fig. 1. The MnII ion is coordinated in a slightly distorted monocapped trigonal-prismatic geometry. The tris(1-methyl-1H-benzimidazol-2-ylmethyl)amine (Mentb) ligand coordinates in a tetradentate mode and the coordination is completed by a bis-chelating salicylato ligand and dimethylformamide ligand. The hydroxy group of the salicylato ligand is disordered over two sites with occupancies 0.581 (8) and 0.419 (8). Both disorder components form intramolecular O-H···O hydrogen bonds.

Experimental

To a stirred solution of Mentb (0.5 mmol) in hot methanol (20 ml), Mn(ClO4)2.6 H2O (0.5 mmol) and a solution of Na(salicylato) (0.5 mmol) in methanol (5 ml) was added. A colorless microcrystalline precipitate was produced and collected by filtration. After drying in air the colorless product was redissolved in DMF/methanol (1:1) and filtered. Light-yellow block-shaped crystals suitable for X-ray diffraction studies were obtained by vapor diffusion of diethyl ether into the filtrate for 4 weeks at room temperature. (Yield 0.12 g, 67%). Elemental analysis found: C, 54.09%; H, 5.59%; N, 14.13%; calcd. for C40 H46 O9 N9 Mn Cl: C, 54.15%; H, 5.23%; N, 14.21%.

Refinement

All H atoms were geometrically positioned and refined using a riding-model approximation with C—H distances from 0.93 to 0.97 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl,O). The hydroxy group and the ortho-H atom of the salicylato ligand were refined as disordered over two sites with occupancies 0.581 (8) and 0.419 (8). In the final refinement cycles restraints were applied to some anisotropic displacement parameters (EADP, SIMU and DELU instructions in SHELXL97, Sheldrick, 2008) to obtain more sensible values i.e. EADP C30 C30' C34 C34', SIMU N8 C36 C37, DELU MN1 O1 O2 C36 C37.

Figures

Fig. 1.
The cation of the title compound with displacement ellipsoides drawn at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

[Mn(C7H5O3)(C27H27N7)(C3H7NO)]ClO4·C3H7NOZ = 2
Mr = 887.25F(000) = 926
Triclinic, P1Dx = 1.373 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3689 (13) ÅCell parameters from 9784 reflections
b = 12.4809 (13) Åθ = 1.7–27.7°
c = 15.3759 (16) ŵ = 0.43 mm1
α = 69.925 (1)°T = 296 K
β = 87.926 (1)°Block, light-yellow
γ = 74.704 (1)°0.38 × 0.36 × 0.32 mm
V = 2146.6 (4) Å3

Data collection

Bruker SMART APEX diffractometer7890 independent reflections
Radiation source: fine-focus sealed tube6197 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 25.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→14
Tmin = 0.853, Tmax = 0.874k = −15→15
15941 measured reflectionsl = −18→18

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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.10w = 1/[σ2(Fo2) + (0.1005P)2 + 0.2919P] where P = (Fo2 + 2Fc2)/3
7890 reflections(Δ/σ)max = 0.001
560 parametersΔρmax = 0.54 e Å3
16 restraintsΔρmin = −0.57 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)
C10.7376 (2)0.8865 (3)0.89825 (18)0.0441 (6)
H1A0.75820.82300.95770.053*
H1B0.72410.96140.90830.053*
C20.8306 (2)0.8753 (2)0.83346 (18)0.0411 (6)
C30.9618 (3)0.9470 (4)0.9088 (2)0.0655 (9)
H3A0.89630.98300.93460.098*
H3B1.00201.00470.87910.098*
H3C1.00940.88260.95750.098*
C40.9896 (2)0.8843 (3)0.7675 (2)0.0495 (7)
C51.0948 (3)0.8994 (4)0.7409 (2)0.0690 (10)
H51.13830.92380.77460.083*
C61.1304 (3)0.8764 (4)0.6627 (3)0.0844 (12)
H61.20010.88600.64230.101*
C71.0658 (3)0.8387 (4)0.6119 (3)0.0794 (11)
H71.09380.82360.55900.095*
C80.9612 (3)0.8234 (3)0.6387 (2)0.0621 (9)
H80.91780.79930.60480.075*
C90.9239 (2)0.8458 (3)0.71914 (19)0.0472 (7)
C100.5833 (2)0.9924 (2)0.78241 (19)0.0441 (6)
H10A0.64001.03160.75320.053*
H10B0.53081.04430.80860.053*
C110.5227 (2)0.9678 (2)0.71201 (17)0.0397 (6)
C120.4095 (3)1.1790 (3)0.6354 (2)0.0643 (9)
H12A0.32891.20330.63370.096*
H12B0.43491.22450.57840.096*
H12C0.43991.19180.68640.096*
C130.4097 (2)0.9988 (2)0.59389 (17)0.0423 (6)
C140.3347 (2)1.0450 (3)0.51700 (19)0.0522 (7)
H140.29861.12540.49230.063*
C150.3163 (3)0.9653 (3)0.47902 (19)0.0561 (8)
H150.26650.99230.42740.067*
C160.3711 (3)0.8456 (3)0.5166 (2)0.0556 (8)
H160.35700.79430.48940.067*
C170.4458 (2)0.8004 (3)0.59322 (19)0.0488 (7)
H170.48100.71980.61830.059*
C180.4666 (2)0.8785 (2)0.63128 (16)0.0399 (6)
C190.5560 (2)0.8445 (3)0.92604 (18)0.0446 (6)
H19A0.48080.87210.89690.053*
H19B0.55670.87980.97320.053*
C200.5877 (2)0.7134 (2)0.96938 (17)0.0411 (6)
C210.4895 (3)0.7020 (4)1.1177 (2)0.0723 (10)
H21A0.53820.70671.16270.108*
H21B0.44250.65201.14880.108*
H21C0.44340.77981.08380.108*
C220.5982 (3)0.5329 (3)1.06591 (19)0.0520 (7)
C230.5914 (3)0.4311 (4)1.1384 (2)0.0670 (10)
H230.55350.43501.19100.080*
C240.6433 (3)0.3254 (4)1.1283 (3)0.0754 (11)
H240.64100.25561.17550.091*
C250.6995 (3)0.3191 (3)1.0496 (3)0.0720 (10)
H250.73370.24541.04520.086*
C260.7057 (3)0.4213 (3)0.9769 (2)0.0602 (8)
H260.74300.41710.92410.072*
C270.6544 (2)0.5283 (3)0.98641 (19)0.0466 (7)
C280.7141 (3)0.6110 (3)0.66229 (19)0.0504 (7)
C290.7189 (3)0.5550 (3)0.5908 (2)0.0539 (8)
C300.6454 (4)0.4871 (3)0.5915 (3)0.0749 (11)0.581 (8)
C30'0.6454 (4)0.4871 (3)0.5915 (3)0.0749 (11)0.419 (8)
H30'0.59620.47280.63870.090*0.419 (8)
C310.6466 (5)0.4406 (4)0.5206 (4)0.1059 (17)
H310.59590.39790.51890.127*
C320.7223 (6)0.4582 (5)0.4537 (4)0.117 (2)
H320.72250.42700.40680.141*
C330.7980 (5)0.5207 (5)0.4542 (3)0.1068 (17)
H330.85070.52950.40930.128*
C340.7953 (4)0.5708 (4)0.5220 (2)0.0740 (11)0.581 (8)
H340.84500.61540.52170.089*0.581 (8)
C34'0.7953 (4)0.5708 (4)0.5220 (2)0.0740 (11)0.419 (8)
C350.9528 (3)0.5539 (3)0.8186 (2)0.0605 (8)
H350.95880.60370.75880.073*
C361.0375 (4)0.3827 (4)0.9514 (3)0.0990 (11)
H36A0.96340.40170.97270.148*
H36B1.09110.38390.99450.148*
H36C1.05440.30530.94680.148*
C371.1502 (4)0.4571 (5)0.8161 (4)0.1028 (11)
H37A1.16900.38420.80380.154*
H37B1.20750.45590.85710.154*
H37C1.14470.52220.75890.154*
C380.8240 (8)0.1803 (7)0.6898 (7)0.186 (5)
H380.84280.15150.64130.223*
C390.8823 (10)0.2884 (7)0.7733 (7)0.221 (6)
H39A0.80690.30220.79310.332*
H39B0.90140.36240.74800.332*
H39C0.93320.23680.82540.332*
C400.9828 (8)0.2465 (10)0.6515 (7)0.248 (7)
H40A0.98650.20170.61120.373*
H40B1.05050.21630.69080.373*
H40C0.97460.32810.61500.373*
Cl0.25816 (7)0.06650 (8)0.87509 (6)0.0620 (2)
Mn10.69993 (3)0.72415 (3)0.78373 (2)0.03771 (15)
N10.82321 (19)0.8399 (2)0.76340 (15)0.0446 (5)
N20.9278 (2)0.9023 (2)0.84077 (16)0.0463 (6)
N30.53926 (18)0.86162 (19)0.70643 (14)0.0387 (5)
N40.44709 (19)1.05312 (19)0.64708 (15)0.0430 (5)
N50.64677 (19)0.6439 (2)0.92610 (14)0.0423 (5)
N60.5571 (2)0.6524 (2)1.05338 (15)0.0497 (6)
N70.63642 (18)0.88007 (19)0.85613 (14)0.0383 (5)
N81.0432 (3)0.4710 (3)0.8591 (3)0.0839 (8)
N90.8900 (4)0.2366 (4)0.7067 (4)0.1084 (15)
O10.6542 (2)0.58442 (19)0.73067 (14)0.0578 (5)
O20.76700 (19)0.6868 (2)0.65364 (14)0.0567 (5)
O30.86189 (19)0.5726 (2)0.85104 (15)0.0619 (6)
O40.5786 (5)0.4636 (5)0.6574 (4)0.089 (2)0.581 (8)
H40.58270.50000.69210.134*0.581 (8)
O4'0.8645 (8)0.6282 (9)0.5211 (7)0.113 (4)0.419 (8)
H4'0.84510.66700.55530.170*0.419 (8)
O50.3371 (3)0.1263 (3)0.8814 (2)0.1019 (10)
O60.2796 (3)0.0238 (4)0.8013 (2)0.1131 (12)
O70.2718 (4)−0.0358 (3)0.9587 (2)0.1162 (12)
O80.1490 (3)0.1332 (4)0.8762 (3)0.1210 (13)
O90.7465 (5)0.1614 (5)0.7262 (6)0.231 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0370 (15)0.0586 (17)0.0417 (13)−0.0167 (13)0.0033 (11)−0.0207 (12)
C20.0369 (15)0.0447 (15)0.0409 (13)−0.0135 (11)0.0001 (10)−0.0116 (11)
C30.061 (2)0.091 (3)0.0614 (19)−0.0396 (19)−0.0005 (15)−0.0326 (18)
C40.0390 (16)0.0599 (18)0.0479 (15)−0.0193 (13)0.0044 (12)−0.0123 (13)
C50.0460 (19)0.098 (3)0.067 (2)−0.0360 (19)0.0088 (15)−0.0218 (19)
C60.053 (2)0.129 (4)0.080 (2)−0.046 (2)0.0261 (19)−0.034 (2)
C70.065 (2)0.116 (3)0.064 (2)−0.032 (2)0.0289 (18)−0.035 (2)
C80.053 (2)0.084 (2)0.0551 (17)−0.0226 (17)0.0146 (14)−0.0290 (16)
C90.0381 (16)0.0556 (17)0.0465 (14)−0.0159 (13)0.0072 (11)−0.0137 (12)
C100.0420 (16)0.0414 (15)0.0489 (14)−0.0115 (12)0.0029 (11)−0.0156 (12)
C110.0359 (14)0.0409 (14)0.0375 (12)−0.0076 (11)0.0063 (10)−0.0099 (10)
C120.076 (2)0.0404 (16)0.0592 (18)−0.0012 (15)0.0006 (16)−0.0070 (14)
C130.0368 (15)0.0477 (15)0.0332 (12)−0.0090 (12)0.0065 (10)−0.0047 (11)
C140.0395 (16)0.0588 (18)0.0404 (14)−0.0049 (13)0.0003 (11)−0.0011 (13)
C150.0432 (17)0.080 (2)0.0360 (13)−0.0149 (15)−0.0015 (12)−0.0094 (14)
C160.0479 (18)0.075 (2)0.0497 (16)−0.0200 (16)0.0023 (13)−0.0267 (15)
C170.0408 (16)0.0550 (17)0.0489 (15)−0.0116 (13)0.0001 (12)−0.0168 (13)
C180.0321 (14)0.0483 (15)0.0339 (12)−0.0108 (11)0.0030 (10)−0.0076 (11)
C190.0353 (15)0.0556 (17)0.0442 (14)−0.0126 (12)0.0076 (11)−0.0192 (12)
C200.0321 (14)0.0537 (16)0.0380 (13)−0.0149 (12)0.0031 (10)−0.0141 (11)
C210.075 (3)0.097 (3)0.0548 (18)−0.036 (2)0.0285 (17)−0.0307 (18)
C220.0440 (17)0.064 (2)0.0435 (14)−0.0255 (14)−0.0028 (12)−0.0049 (13)
C230.060 (2)0.078 (3)0.0538 (18)−0.0344 (19)0.0000 (15)0.0004 (16)
C240.071 (3)0.063 (2)0.073 (2)−0.035 (2)−0.0107 (19)0.0135 (18)
C250.064 (2)0.051 (2)0.092 (3)−0.0200 (17)−0.010 (2)−0.0078 (18)
C260.055 (2)0.0536 (19)0.069 (2)−0.0184 (15)0.0030 (15)−0.0143 (15)
C270.0378 (16)0.0525 (17)0.0474 (14)−0.0189 (13)−0.0010 (11)−0.0094 (12)
C280.0545 (18)0.0442 (16)0.0440 (15)0.0014 (14)−0.0091 (13)−0.0143 (12)
C290.062 (2)0.0465 (16)0.0483 (15)−0.0029 (14)−0.0081 (14)−0.0182 (13)
C300.093 (3)0.060 (2)0.077 (2)−0.018 (2)−0.007 (2)−0.0309 (19)
C30'0.093 (3)0.060 (2)0.077 (2)−0.018 (2)−0.007 (2)−0.0309 (19)
C310.127 (4)0.090 (3)0.126 (4)−0.025 (3)−0.017 (4)−0.068 (3)
C320.166 (6)0.113 (4)0.090 (3)−0.016 (4)−0.006 (4)−0.071 (3)
C330.141 (5)0.113 (4)0.071 (3)−0.017 (4)0.020 (3)−0.052 (3)
C340.088 (3)0.072 (2)0.060 (2)−0.009 (2)0.0062 (19)−0.0311 (18)
C34'0.088 (3)0.072 (2)0.060 (2)−0.009 (2)0.0062 (19)−0.0311 (18)
C350.051 (2)0.061 (2)0.0617 (18)−0.0101 (15)−0.0041 (15)−0.0144 (15)
C360.076 (2)0.102 (2)0.098 (2)0.0174 (18)−0.0213 (17)−0.0365 (17)
C370.0629 (17)0.112 (2)0.118 (2)0.0057 (18)−0.0074 (16)−0.041 (2)
C380.170 (8)0.118 (5)0.215 (9)−0.071 (6)−0.107 (7)0.045 (5)
C390.272 (12)0.129 (6)0.229 (10)0.046 (7)−0.139 (9)−0.079 (7)
C400.149 (8)0.282 (13)0.184 (9)−0.041 (8)−0.018 (7)0.071 (9)
Cl0.0475 (5)0.0849 (6)0.0735 (5)−0.0237 (4)0.0139 (4)−0.0485 (5)
Mn10.0338 (2)0.0419 (2)0.0362 (2)−0.00857 (17)0.00105 (15)−0.01302 (17)
N10.0364 (13)0.0580 (14)0.0446 (12)−0.0174 (11)0.0058 (9)−0.0212 (10)
N20.0381 (13)0.0575 (14)0.0465 (12)−0.0189 (11)0.0002 (10)−0.0169 (11)
N30.0331 (12)0.0415 (12)0.0391 (11)−0.0095 (9)−0.0003 (8)−0.0110 (9)
N40.0419 (13)0.0385 (12)0.0405 (11)−0.0057 (10)0.0037 (9)−0.0073 (9)
N50.0388 (13)0.0437 (12)0.0411 (11)−0.0125 (10)0.0021 (9)−0.0096 (10)
N60.0447 (14)0.0639 (16)0.0401 (12)−0.0200 (12)0.0080 (10)−0.0140 (11)
N70.0312 (12)0.0452 (12)0.0390 (10)−0.0110 (9)0.0032 (8)−0.0146 (9)
N80.0567 (15)0.0949 (19)0.0960 (17)0.0071 (14)−0.0185 (13)−0.0462 (14)
N90.098 (3)0.084 (3)0.122 (3)−0.033 (2)−0.036 (3)0.000 (2)
O10.0665 (15)0.0555 (12)0.0525 (11)−0.0134 (10)−0.0004 (10)−0.0221 (9)
O20.0659 (15)0.0589 (13)0.0497 (10)−0.0154 (11)0.0010 (9)−0.0249 (10)
O30.0425 (13)0.0660 (14)0.0571 (12)0.0012 (10)−0.0013 (10)−0.0078 (10)
O40.100 (4)0.090 (4)0.100 (4)−0.054 (3)0.022 (3)−0.040 (3)
O4'0.132 (8)0.133 (8)0.121 (7)−0.073 (6)0.068 (6)−0.080 (6)
O50.096 (2)0.145 (3)0.114 (2)−0.074 (2)0.0280 (18)−0.077 (2)
O60.124 (3)0.180 (4)0.100 (2)−0.085 (3)0.046 (2)−0.098 (2)
O70.172 (4)0.075 (2)0.094 (2)−0.025 (2)0.024 (2)−0.0268 (17)
O80.062 (2)0.141 (3)0.145 (3)0.0034 (19)0.0054 (19)−0.054 (3)
O90.145 (5)0.131 (4)0.347 (9)−0.087 (4)−0.056 (5)0.048 (5)

Geometric parameters (Å, °)

C1—N71.463 (3)C23—H230.9300
C1—C21.504 (4)C24—C251.389 (6)
C1—H1A0.9700C24—H240.9300
C1—H1B0.9700C25—C261.395 (5)
C2—N11.312 (3)C25—H250.9300
C2—N21.349 (4)C26—C271.374 (5)
C3—N21.462 (4)C26—H260.9300
C3—H3A0.9600C27—N51.402 (4)
C3—H3B0.9600C28—O21.254 (4)
C3—H3C0.9600C28—O11.264 (4)
C4—N21.387 (4)C28—C291.483 (4)
C4—C51.391 (4)C29—C341.390 (5)
C4—C91.392 (4)C29—C301.395 (5)
C5—C61.362 (6)C30—O41.288 (6)
C5—H50.9300C30—C311.398 (6)
C6—C71.402 (6)C31—C321.366 (8)
C6—H60.9300C31—H310.9300
C7—C81.386 (5)C32—C331.370 (8)
C7—H70.9300C32—H320.9300
C8—C91.396 (4)C33—C341.384 (6)
C8—H80.9300C33—H330.9300
C9—N11.405 (4)C34—H340.9300
C10—N71.470 (3)C35—O31.211 (4)
C10—C111.495 (4)C35—N81.306 (4)
C10—H10A0.9700C35—H350.9300
C10—H10B0.9700C36—N81.481 (6)
C11—N31.319 (3)C36—H36A0.9600
C11—N41.348 (3)C36—H36B0.9600
C12—N41.464 (4)C36—H36C0.9600
C12—H12A0.9600C37—N81.454 (6)
C12—H12B0.9600C37—H37A0.9600
C12—H12C0.9600C37—H37B0.9600
C13—N41.385 (4)C37—H37C0.9600
C13—C141.386 (4)C38—O91.131 (11)
C13—C181.400 (4)C38—N91.293 (8)
C14—C151.382 (5)C38—H380.9300
C14—H140.9300C39—N91.376 (9)
C15—C161.387 (5)C39—H39A0.9600
C15—H150.9300C39—H39B0.9600
C16—C171.381 (4)C39—H39C0.9600
C16—H160.9300C40—N91.409 (10)
C17—C181.376 (4)C40—H40A0.9600
C17—H170.9300C40—H40B0.9600
C18—N31.412 (3)C40—H40C0.9600
C19—N71.473 (3)Cl—O81.390 (3)
C19—C201.485 (4)Cl—O61.400 (3)
C19—H19A0.9700Cl—O51.400 (3)
C19—H19B0.9700Cl—O71.444 (3)
C20—N51.326 (4)Mn1—N52.228 (2)
C20—N61.354 (3)Mn1—O22.286 (2)
C21—N61.466 (4)Mn1—N32.297 (2)
C21—H21A0.9600Mn1—N12.308 (2)
C21—H21B0.9600Mn1—O32.338 (2)
C21—H21C0.9600Mn1—O12.358 (2)
C22—N61.390 (4)Mn1—N72.502 (2)
C22—C231.393 (4)O4—H40.8200
C22—C271.395 (4)O4'—H4'0.8200
C23—C241.365 (6)
N7—C1—C2108.1 (2)O4—C30—C29121.4 (4)
N7—C1—H1A110.1O4—C30—C31119.3 (5)
C2—C1—H1A110.1C29—C30—C31119.2 (5)
N7—C1—H1B110.1C32—C31—C30119.8 (5)
C2—C1—H1B110.1C32—C31—H31120.1
H1A—C1—H1B108.4C30—C31—H31120.1
N1—C2—N2113.9 (2)C31—C32—C33121.5 (4)
N1—C2—C1122.5 (2)C31—C32—H32119.2
N2—C2—C1123.6 (2)C33—C32—H32119.2
N2—C3—H3A109.5C32—C33—C34119.3 (5)
N2—C3—H3B109.5C32—C33—H33120.3
H3A—C3—H3B109.5C34—C33—H33120.3
N2—C3—H3C109.5C33—C34—C29120.5 (5)
H3A—C3—H3C109.5C33—C34—H34119.8
H3B—C3—H3C109.5C29—C34—H34119.8
N2—C4—C5131.1 (3)O3—C35—N8126.7 (3)
N2—C4—C9106.0 (2)O3—C35—H35116.7
C5—C4—C9122.9 (3)N8—C35—H35116.7
C6—C5—C4116.1 (3)N8—C36—H36A109.5
C6—C5—H5122.0N8—C36—H36B109.5
C4—C5—H5122.0H36A—C36—H36B109.5
C5—C6—C7122.4 (3)N8—C36—H36C109.5
C5—C6—H6118.8H36A—C36—H36C109.5
C7—C6—H6118.8H36B—C36—H36C109.5
C8—C7—C6121.3 (3)N8—C37—H37A109.5
C8—C7—H7119.3N8—C37—H37B109.5
C6—C7—H7119.3H37A—C37—H37B109.5
C7—C8—C9116.9 (3)N8—C37—H37C109.5
C7—C8—H8121.5H37A—C37—H37C109.5
C9—C8—H8121.5H37B—C37—H37C109.5
C4—C9—C8120.3 (3)O9—C38—N9128.5 (12)
C4—C9—N1108.9 (2)O9—C38—H38115.7
C8—C9—N1130.7 (3)N9—C38—H38115.8
N7—C10—C11109.1 (2)N9—C39—H39A109.5
N7—C10—H10A109.9N9—C39—H39B109.5
C11—C10—H10A109.9H39A—C39—H39B109.5
N7—C10—H10B109.9N9—C39—H39C109.5
C11—C10—H10B109.9H39A—C39—H39C109.5
H10A—C10—H10B108.3H39B—C39—H39C109.5
N3—C11—N4113.7 (2)N9—C40—H40A109.5
N3—C11—C10123.5 (2)N9—C40—H40B109.5
N4—C11—C10122.8 (2)H40A—C40—H40B109.5
N4—C12—H12A109.5N9—C40—H40C109.5
N4—C12—H12B109.5H40A—C40—H40C109.5
H12A—C12—H12B109.5H40B—C40—H40C109.5
N4—C12—H12C109.5O8—Cl—O6115.7 (2)
H12A—C12—H12C109.5O8—Cl—O5111.7 (2)
H12B—C12—H12C109.5O6—Cl—O5110.3 (2)
N4—C13—C14131.1 (3)O8—Cl—O7103.8 (2)
N4—C13—C18106.1 (2)O6—Cl—O7106.7 (2)
C14—C13—C18122.8 (3)O5—Cl—O7108.0 (2)
C15—C14—C13116.5 (3)N5—Mn1—O2144.47 (8)
C15—C14—H14121.8N5—Mn1—N3103.75 (8)
C13—C14—H14121.8O2—Mn1—N393.62 (8)
C14—C15—C16121.0 (3)N5—Mn1—N1118.65 (8)
C14—C15—H15119.5O2—Mn1—N186.93 (8)
C16—C15—H15119.5N3—Mn1—N1101.58 (8)
C17—C16—C15122.1 (3)N5—Mn1—O378.95 (8)
C17—C16—H16119.0O2—Mn1—O381.04 (8)
C15—C16—H16119.0N3—Mn1—O3173.46 (8)
C18—C17—C16117.8 (3)N1—Mn1—O381.99 (9)
C18—C17—H17121.1N5—Mn1—O192.95 (8)
C16—C17—H17121.1O2—Mn1—O156.05 (8)
C17—C18—C13119.7 (2)N3—Mn1—O189.21 (8)
C17—C18—N3131.7 (3)N1—Mn1—O1142.21 (8)
C13—C18—N3108.6 (2)O3—Mn1—O184.68 (8)
N7—C19—C20109.3 (2)N5—Mn1—N770.46 (8)
N7—C19—H19A109.8O2—Mn1—N7145.07 (8)
C20—C19—H19A109.8N3—Mn1—N769.47 (7)
N7—C19—H19B109.8N1—Mn1—N768.01 (8)
C20—C19—H19B109.8O3—Mn1—N7117.06 (8)
H19A—C19—H19B108.3O1—Mn1—N7147.91 (8)
N5—C20—N6113.1 (2)C2—N1—C9104.7 (2)
N5—C20—C19121.9 (2)C2—N1—Mn1113.35 (18)
N6—C20—C19125.0 (2)C9—N1—Mn1135.86 (19)
N6—C21—H21A109.5C2—N2—C4106.4 (2)
N6—C21—H21B109.5C2—N2—C3128.0 (3)
H21A—C21—H21B109.5C4—N2—C3125.5 (3)
N6—C21—H21C109.5C11—N3—C18104.8 (2)
H21A—C21—H21C109.5C11—N3—Mn1115.48 (17)
H21B—C21—H21C109.5C18—N3—Mn1136.64 (18)
N6—C22—C23132.0 (3)C11—N4—C13106.9 (2)
N6—C22—C27105.8 (2)C11—N4—C12127.0 (3)
C23—C22—C27122.3 (3)C13—N4—C12126.1 (2)
C24—C23—C22116.6 (4)C20—N5—C27105.0 (2)
C24—C23—H23121.7C20—N5—Mn1119.63 (17)
C22—C23—H23121.7C27—N5—Mn1135.29 (19)
C23—C24—C25121.9 (3)C20—N6—C22107.0 (2)
C23—C24—H24119.0C20—N6—C21126.9 (3)
C25—C24—H24119.0C22—N6—C21126.1 (3)
C24—C25—C26121.3 (4)C1—N7—C10111.3 (2)
C24—C25—H25119.4C1—N7—C19111.7 (2)
C26—C25—H25119.4C10—N7—C19110.9 (2)
C27—C26—C25117.4 (3)C1—N7—Mn1106.10 (16)
C27—C26—H26121.3C10—N7—Mn1108.06 (15)
C25—C26—H26121.3C19—N7—Mn1108.56 (16)
C26—C27—C22120.5 (3)C35—N8—C37123.1 (4)
C26—C27—N5130.3 (3)C35—N8—C36119.6 (4)
C22—C27—N5109.3 (3)C37—N8—C36117.3 (3)
O2—C28—O1120.1 (3)C38—N9—C39128.2 (10)
O2—C28—C29120.1 (3)C38—N9—C40117.3 (9)
O1—C28—C29119.8 (3)C39—N9—C40114.6 (8)
C34—C29—C30119.5 (3)C28—O1—Mn190.11 (18)
C34—C29—C28120.6 (3)C28—O2—Mn193.71 (18)
C30—C29—C28119.9 (3)C35—O3—Mn1127.9 (2)
N7—C1—C2—N1−13.4 (4)N5—Mn1—N3—C18−115.2 (2)
N7—C1—C2—N2165.4 (2)O2—Mn1—N3—C1833.6 (2)
N2—C4—C5—C6−178.3 (4)N1—Mn1—N3—C18121.2 (2)
C9—C4—C5—C61.2 (5)O3—Mn1—N3—C18−1.4 (8)
C4—C5—C6—C7−0.5 (7)O1—Mn1—N3—C18−22.3 (2)
C5—C6—C7—C80.3 (7)N7—Mn1—N3—C18−177.8 (3)
C6—C7—C8—C9−0.8 (6)N3—C11—N4—C130.3 (3)
N2—C4—C9—C8177.9 (3)C10—C11—N4—C13179.2 (2)
C5—C4—C9—C8−1.7 (5)N3—C11—N4—C12179.3 (3)
N2—C4—C9—N1−0.4 (3)C10—C11—N4—C12−1.8 (4)
C5—C4—C9—N1−180.0 (3)C14—C13—N4—C11−178.0 (3)
C7—C8—C9—C41.4 (5)C18—C13—N4—C110.3 (3)
C7—C8—C9—N1179.2 (3)C14—C13—N4—C123.0 (5)
N7—C10—C11—N3−15.4 (4)C18—C13—N4—C12−178.7 (3)
N7—C10—C11—N4165.7 (2)N6—C20—N5—C270.6 (3)
N4—C13—C14—C15179.3 (3)C19—C20—N5—C27−177.1 (2)
C18—C13—C14—C151.3 (4)N6—C20—N5—Mn1177.20 (17)
C13—C14—C15—C16−0.2 (4)C19—C20—N5—Mn1−0.4 (3)
C14—C15—C16—C170.1 (5)C26—C27—N5—C20179.7 (3)
C15—C16—C17—C18−1.0 (5)C22—C27—N5—C20−0.1 (3)
C16—C17—C18—C132.1 (4)C26—C27—N5—Mn13.8 (5)
C16—C17—C18—N3−178.0 (3)C22—C27—N5—Mn1−175.91 (19)
N4—C13—C18—C17179.3 (2)O2—Mn1—N5—C20−164.32 (18)
C14—C13—C18—C17−2.3 (4)N3—Mn1—N5—C20−47.3 (2)
N4—C13—C18—N3−0.7 (3)N1—Mn1—N5—C2064.4 (2)
C14—C13—C18—N3177.8 (3)O3—Mn1—N5—C20138.8 (2)
N7—C19—C20—N5−24.6 (3)O1—Mn1—N5—C20−137.2 (2)
N7—C19—C20—N6158.0 (2)N7—Mn1—N5—C2014.67 (19)
N6—C22—C23—C24−179.4 (3)O2—Mn1—N5—C2711.1 (3)
C27—C22—C23—C240.3 (5)N3—Mn1—N5—C27128.1 (2)
C22—C23—C24—C25−0.4 (5)N1—Mn1—N5—C27−120.2 (2)
C23—C24—C25—C260.2 (6)O3—Mn1—N5—C27−45.8 (2)
C24—C25—C26—C270.2 (5)O1—Mn1—N5—C2738.2 (3)
C25—C26—C27—C22−0.4 (5)N7—Mn1—N5—C27−170.0 (3)
C25—C26—C27—N5179.9 (3)N5—C20—N6—C22−0.8 (3)
N6—C22—C27—C26179.8 (3)C19—C20—N6—C22176.7 (3)
C23—C22—C27—C260.1 (5)N5—C20—N6—C21−178.4 (3)
N6—C22—C27—N5−0.4 (3)C19—C20—N6—C21−0.9 (5)
C23—C22—C27—N5179.9 (3)C23—C22—N6—C20−179.6 (3)
O2—C28—C29—C3410.5 (5)C27—C22—N6—C200.7 (3)
O1—C28—C29—C34−171.4 (3)C23—C22—N6—C21−1.9 (5)
O2—C28—C29—C30−168.7 (3)C27—C22—N6—C21178.4 (3)
O1—C28—C29—C309.4 (5)C2—C1—N7—C10−77.4 (3)
C34—C29—C30—O4175.3 (5)C2—C1—N7—C19158.1 (2)
C28—C29—C30—O4−5.5 (6)C2—C1—N7—Mn140.0 (2)
C34—C29—C30—C31−2.9 (6)C11—C10—N7—C1151.1 (2)
C28—C29—C30—C31176.3 (4)C11—C10—N7—C19−83.9 (3)
O4—C30—C31—C32−175.6 (6)C11—C10—N7—Mn134.9 (2)
C29—C30—C31—C322.6 (7)C20—C19—N7—C1−83.4 (3)
C30—C31—C32—C330.0 (9)C20—C19—N7—C10151.8 (2)
C31—C32—C33—C34−2.3 (9)C20—C19—N7—Mn133.2 (2)
C32—C33—C34—C291.9 (7)N5—Mn1—N7—C194.11 (16)
C30—C29—C34—C330.7 (6)O2—Mn1—N7—C1−86.9 (2)
C28—C29—C34—C33−178.6 (4)N3—Mn1—N7—C1−152.17 (17)
N2—C2—N1—C9−1.1 (3)N1—Mn1—N7—C1−39.69 (16)
C1—C2—N1—C9177.9 (3)O3—Mn1—N7—C128.29 (18)
N2—C2—N1—Mn1156.12 (19)O1—Mn1—N7—C1156.51 (16)
C1—C2—N1—Mn1−24.9 (3)N5—Mn1—N7—C10−146.41 (18)
C4—C9—N1—C20.9 (3)O2—Mn1—N7—C1032.6 (2)
C8—C9—N1—C2−177.2 (3)N3—Mn1—N7—C10−32.69 (16)
C4—C9—N1—Mn1−148.4 (2)N1—Mn1—N7—C1079.79 (17)
C8—C9—N1—Mn133.6 (5)O3—Mn1—N7—C10147.77 (16)
N5—Mn1—N1—C2−16.9 (2)O1—Mn1—N7—C10−84.0 (2)
O2—Mn1—N1—C2−171.0 (2)N5—Mn1—N7—C19−26.04 (16)
N3—Mn1—N1—C296.0 (2)O2—Mn1—N7—C19152.94 (16)
O3—Mn1—N1—C2−89.6 (2)N3—Mn1—N7—C1987.69 (17)
O1—Mn1—N1—C2−160.06 (17)N1—Mn1—N7—C19−159.83 (18)
N7—Mn1—N1—C233.94 (19)O3—Mn1—N7—C19−91.85 (17)
N5—Mn1—N1—C9130.5 (2)O1—Mn1—N7—C1936.4 (2)
O2—Mn1—N1—C9−23.5 (3)O3—C35—N8—C37−178.0 (4)
N3—Mn1—N1—C9−116.6 (3)O3—C35—N8—C364.8 (6)
O3—Mn1—N1—C957.8 (3)O9—C38—N9—C39−0.2 (12)
O1—Mn1—N1—C9−12.6 (3)O9—C38—N9—C40179.0 (8)
N7—Mn1—N1—C9−178.6 (3)O2—C28—O1—Mn11.5 (3)
N1—C2—N2—C40.9 (3)C29—C28—O1—Mn1−176.6 (2)
C1—C2—N2—C4−178.1 (3)N5—Mn1—O1—C28−162.24 (17)
N1—C2—N2—C3178.3 (3)O2—Mn1—O1—C28−0.87 (16)
C1—C2—N2—C3−0.6 (5)N3—Mn1—O1—C2894.03 (17)
C5—C4—N2—C2179.3 (3)N1—Mn1—O1—C28−14.0 (2)
C9—C4—N2—C2−0.2 (3)O3—Mn1—O1—C28−83.63 (17)
C5—C4—N2—C31.7 (6)N7—Mn1—O1—C28141.01 (17)
C9—C4—N2—C3−177.8 (3)O1—C28—O2—Mn1−1.6 (3)
N4—C11—N3—C18−0.7 (3)C29—C28—O2—Mn1176.5 (2)
C10—C11—N3—C18−179.7 (2)N5—Mn1—O2—C2834.2 (2)
N4—C11—N3—Mn1162.72 (17)N3—Mn1—O2—C28−85.73 (18)
C10—C11—N3—Mn1−16.2 (3)N1—Mn1—O2—C28172.85 (18)
C17—C18—N3—C11−179.1 (3)O3—Mn1—O2—C2890.48 (18)
C13—C18—N3—C110.9 (3)O1—Mn1—O2—C280.88 (16)
C17—C18—N3—Mn122.9 (4)N7—Mn1—O2—C28−144.18 (17)
C13—C18—N3—Mn1−157.14 (19)N8—C35—O3—Mn1177.4 (3)
N5—Mn1—N3—C1188.48 (18)N5—Mn1—O3—C35−172.7 (3)
O2—Mn1—N3—C11−122.76 (18)O2—Mn1—O3—C3536.8 (3)
N1—Mn1—N3—C11−35.17 (19)N3—Mn1—O3—C3572.2 (8)
O3—Mn1—N3—C11−157.7 (6)N1—Mn1—O3—C35−51.3 (3)
O1—Mn1—N3—C11−178.67 (18)O1—Mn1—O3—C3593.3 (3)
N7—Mn1—N3—C1125.83 (17)N7—Mn1—O3—C35−111.5 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4'—H4'···O20.821.822.554 (8)149
O4—H4···O10.821.792.530 (5)149

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5127).

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