Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021034/lh2366sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021034/lh2366Isup2.hkl |
CCDC reference: 650527
The ligand N,N,N',N'-tetrakis(benzimidazol-2-ylmethyl)ethane-1,2-diamine (edtb) was synthesized as reported by Hendriks, et al. (1982).
The edtb (0.58 g, 1.0 mmol) in 20 ml hot absolute methanol was added slowly to MnCl2 ˙4H2O (0.20 g, 1.0 mmol) solution of 10 ml me thanol. The mixture was stirred for 1 h. After filtration, the brownish solution was allowed to stand at room temperature. Yellow block-shaped crystals suitable for X-ray analysis were obtained in several days in 55% yield.
All H atoms bonded to C atoms were placed in calclulated positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, with Uiso(H) = 1.2Ueq(C). H atoms bonded to N atoms were located in a difference map and were refined with distance restraints of N—H =0.86 (1) Å and Uiso(H) =1.2Ueq(N). Similarly located water H atoms were refined with distance restraints of O–H = 0.82 (1) Å, H–H=1.39 (1) Å and Uiso(H)=1.5Ueq(O). During the refinement of the structure, electron density peaks were located that were believed to be highly disordered solvent molecule molecules (possibly methanol and water solvent). Attempts made to model the solvent molecules were not successful. The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 276.0 Å3 containing approximately 26 electrons. In the final cycles of refinement, this contribution to the electron density was removed from the observed data. The density, the F(000) value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003). Similar treatment of disordered solvent molecules were carried out by Suresh et al. (2006) and references cited therein.
Recently, studies of ligands containing polybenzimidazole groups and their metal coordination compounds have been widely carried out (Chen et al., 2004; Liao et al.,2001). In a continuation of our work, we report herein the crystal structure of the title compound (I).
In the molecular structure of (I) (Fig. 1) the MnII is coordinated by three benzimidazole N atoms, two amino N atoms of an edtb ligand and one chloride anion, forming a distorted octahedron coordination geometry. Unlike the related structure (Chen et al., 2004), in (I) there is an uncoordinated benzimidazole group extending away from the central Mn atom.
There are a number of N(or C)–H···Cl, N–H···O and O–H···N hydrogen bonds which stabilize the crystal structure (Table 2 & Fig. 2).
Some work related to this study has been published (Chen et al., 2004; Liao et al., 2001) and the disordered solvent molecule was treated using the SQUEEZE routine in PLATON (Spek, 2003).
For related literature, see: Hendriks et al. (1982); Suresh et al. (2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and H atoms as small spheres. | |
Fig. 2. Part of the crystal structure of (I), showing hydrogen bonds as dashed lines. |
[MnCl(C34H32N10)]Cl·H2O | Z = 2 |
Mr = 724.55 | F(000) = 750 |
Triclinic, P1 | Dx = 1.276 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.790 (2) Å | Cell parameters from 8006 reflections |
b = 12.657 (3) Å | θ = 2.4–27.2° |
c = 16.039 (4) Å | µ = 0.53 mm−1 |
α = 76.380 (4)° | T = 299 K |
β = 84.743 (4)° | Block, yellow |
γ = 77.753 (4)° | 0.20 × 0.10 × 0.10 mm |
V = 1885.8 (8) Å3 |
Bruker SMART APEX CCD area-detector diffractometer | 8156 independent reflections |
Radiation source: fine focus sealed Siemens Mo tube | 6487 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
0.3° wide ω exposures scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −12→12 |
Tmin = 0.901, Tmax = 0.949 | k = −16→16 |
20876 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0763P)2 + 0.1012P] where P = (Fo2 + 2Fc2)/3 |
8156 reflections | (Δ/σ)max = 0.003 |
453 parameters | Δρmax = 0.41 e Å−3 |
7 restraints | Δρmin = −0.18 e Å−3 |
[MnCl(C34H32N10)]Cl·H2O | γ = 77.753 (4)° |
Mr = 724.55 | V = 1885.8 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.790 (2) Å | Mo Kα radiation |
b = 12.657 (3) Å | µ = 0.53 mm−1 |
c = 16.039 (4) Å | T = 299 K |
α = 76.380 (4)° | 0.20 × 0.10 × 0.10 mm |
β = 84.743 (4)° |
Bruker SMART APEX CCD area-detector diffractometer | 8156 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | 6487 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.949 | Rint = 0.025 |
20876 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 7 restraints |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.41 e Å−3 |
8156 reflections | Δρmin = −0.18 e Å−3 |
453 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.87099 (3) | 0.97239 (2) | 0.217963 (17) | 0.03531 (10) | |
Cl1 | 1.11136 (6) | 0.95010 (5) | 0.16532 (4) | 0.06023 (17) | |
Cl2 | 0.55649 (7) | 0.70808 (6) | 0.54994 (4) | 0.06850 (19) | |
C1 | 0.6092 (2) | 1.08254 (18) | 0.31676 (14) | 0.0442 (5) | |
H1A | 0.5343 | 1.0785 | 0.3607 | 0.053* | |
H1B | 0.5801 | 1.1472 | 0.2713 | 0.053* | |
C2 | 0.7393 (2) | 1.09219 (16) | 0.35430 (12) | 0.0399 (4) | |
C3 | 0.9568 (2) | 1.07967 (16) | 0.37531 (12) | 0.0402 (4) | |
C4 | 1.1023 (2) | 1.0563 (2) | 0.37460 (14) | 0.0512 (5) | |
H4 | 1.1551 | 1.0073 | 0.3434 | 0.061* | |
C5 | 1.1646 (3) | 1.1088 (2) | 0.42214 (16) | 0.0602 (6) | |
H5 | 1.2617 | 1.0954 | 0.4224 | 0.072* | |
C6 | 1.0875 (3) | 1.1808 (2) | 0.46945 (16) | 0.0636 (7) | |
H6 | 1.1344 | 1.2147 | 0.5003 | 0.076* | |
C7 | 0.9446 (3) | 1.2040 (2) | 0.47242 (15) | 0.0577 (6) | |
H7 | 0.8932 | 1.2519 | 0.5050 | 0.069* | |
C8 | 0.8793 (2) | 1.15160 (17) | 0.42380 (13) | 0.0444 (5) | |
C9 | 0.6374 (2) | 0.88249 (17) | 0.35197 (13) | 0.0433 (5) | |
H9A | 0.5498 | 0.8579 | 0.3533 | 0.052* | |
H9B | 0.6440 | 0.9012 | 0.4065 | 0.052* | |
C10 | 0.7564 (2) | 0.79014 (16) | 0.34047 (12) | 0.0371 (4) | |
C11 | 0.8914 (2) | 0.62402 (17) | 0.36215 (14) | 0.0454 (5) | |
C12 | 0.9565 (3) | 0.5139 (2) | 0.38902 (18) | 0.0659 (7) | |
H12 | 0.9187 | 0.4656 | 0.4337 | 0.079* | |
C13 | 1.0806 (3) | 0.4800 (2) | 0.3457 (2) | 0.0751 (8) | |
H13 | 1.1271 | 0.4066 | 0.3614 | 0.090* | |
C14 | 1.1386 (3) | 0.5522 (2) | 0.2794 (2) | 0.0683 (7) | |
H14 | 1.2226 | 0.5259 | 0.2521 | 0.082* | |
C15 | 1.0743 (2) | 0.66171 (18) | 0.25345 (16) | 0.0537 (5) | |
H15 | 1.1128 | 0.7098 | 0.2089 | 0.064* | |
C16 | 0.9500 (2) | 0.69731 (16) | 0.29630 (13) | 0.0398 (4) | |
C17 | 0.5418 (2) | 0.98934 (19) | 0.21419 (14) | 0.0471 (5) | |
H17A | 0.5241 | 1.0645 | 0.1796 | 0.056* | |
H17B | 0.4533 | 0.9729 | 0.2405 | 0.056* | |
C18 | 0.6014 (2) | 0.90988 (18) | 0.15694 (13) | 0.0443 (5) | |
H18A | 0.6230 | 0.8350 | 0.1917 | 0.053* | |
H18B | 0.5321 | 0.9120 | 0.1168 | 0.053* | |
C19 | 0.6979 (3) | 1.03940 (18) | 0.03887 (14) | 0.0526 (5) | |
H19A | 0.5974 | 1.0612 | 0.0336 | 0.063* | |
H19B | 0.7389 | 1.0229 | −0.0151 | 0.063* | |
C20 | 0.7528 (2) | 1.13286 (16) | 0.05581 (12) | 0.0415 (4) | |
C21 | 0.8023 (2) | 1.29872 (18) | 0.03526 (14) | 0.0465 (5) | |
C22 | 0.8184 (3) | 1.4076 (2) | 0.00745 (17) | 0.0625 (6) | |
H22 | 0.7959 | 1.4478 | −0.0477 | 0.075* | |
C23 | 0.8689 (3) | 1.4538 (2) | 0.0644 (2) | 0.0710 (8) | |
H23 | 0.8777 | 1.5277 | 0.0482 | 0.085* | |
C24 | 0.9071 (3) | 1.3929 (2) | 0.14568 (19) | 0.0633 (6) | |
H24 | 0.9438 | 1.4264 | 0.1819 | 0.076* | |
C25 | 0.8922 (2) | 1.28452 (18) | 0.17394 (16) | 0.0527 (5) | |
H25 | 0.9180 | 1.2443 | 0.2285 | 0.063* | |
C26 | 0.8371 (2) | 1.23728 (16) | 0.11812 (13) | 0.0425 (4) | |
C27 | 0.8169 (2) | 0.84426 (19) | 0.07694 (14) | 0.0471 (5) | |
H27A | 0.8430 | 0.7839 | 0.1261 | 0.057* | |
H27B | 0.9024 | 0.8666 | 0.0503 | 0.057* | |
C28 | 0.7526 (2) | 0.80061 (16) | 0.01401 (13) | 0.0410 (4) | |
C29 | 0.7187 (2) | 0.76308 (17) | −0.10898 (13) | 0.0431 (4) | |
C30 | 0.7182 (3) | 0.7509 (2) | −0.19289 (14) | 0.0555 (6) | |
H30 | 0.7730 | 0.7857 | −0.2369 | 0.067* | |
C31 | 0.6319 (3) | 0.6843 (2) | −0.20722 (17) | 0.0619 (7) | |
H31 | 0.6282 | 0.6742 | −0.2625 | 0.074* | |
C32 | 0.5511 (3) | 0.6322 (2) | −0.14177 (19) | 0.0658 (7) | |
H32 | 0.4940 | 0.5884 | −0.1543 | 0.079* | |
C33 | 0.5523 (3) | 0.64310 (19) | −0.05903 (17) | 0.0554 (6) | |
H33 | 0.4982 | 0.6070 | −0.0152 | 0.067* | |
C34 | 0.6384 (2) | 0.71082 (16) | −0.04299 (13) | 0.0417 (4) | |
N1 | 0.63796 (16) | 0.98180 (13) | 0.28227 (10) | 0.0377 (3) | |
N2 | 0.72994 (18) | 0.93848 (13) | 0.10858 (10) | 0.0412 (4) | |
N3 | 0.86515 (17) | 1.04362 (13) | 0.33155 (10) | 0.0395 (4) | |
N4 | 0.7413 (2) | 1.15652 (15) | 0.40989 (12) | 0.0468 (4) | |
H4A | 0.6662 (16) | 1.1952 (18) | 0.4266 (15) | 0.056* | |
N5 | 0.86186 (16) | 0.80181 (13) | 0.28470 (10) | 0.0373 (3) | |
N6 | 0.76745 (19) | 0.68611 (14) | 0.38818 (11) | 0.0446 (4) | |
H6A | 0.709 (2) | 0.6652 (19) | 0.4270 (12) | 0.053* | |
N7 | 0.80471 (18) | 1.13265 (13) | 0.12867 (10) | 0.0427 (4) | |
N8 | 0.7508 (2) | 1.22867 (15) | −0.00237 (11) | 0.0490 (4) | |
H8 | 0.712 (2) | 1.245 (2) | −0.0505 (10) | 0.059* | |
N9 | 0.7908 (2) | 0.82004 (15) | −0.07105 (11) | 0.0469 (4) | |
H9 | 0.845 (2) | 0.8612 (17) | −0.0990 (14) | 0.056* | |
N10 | 0.66146 (19) | 0.73513 (14) | 0.03392 (11) | 0.0456 (4) | |
O3 | 0.5832 (2) | 0.3045 (2) | 0.85843 (11) | 0.0745 (5) | |
H3A | 0.586 (3) | 0.312 (3) | 0.8063 (7) | 0.112* | |
H3B | 0.5049 (19) | 0.299 (3) | 0.8824 (18) | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.04063 (18) | 0.03138 (16) | 0.03312 (16) | −0.00702 (12) | −0.00128 (11) | −0.00574 (11) |
Cl1 | 0.0523 (3) | 0.0513 (3) | 0.0703 (4) | −0.0121 (3) | 0.0189 (3) | −0.0064 (3) |
Cl2 | 0.0570 (4) | 0.0882 (5) | 0.0553 (3) | −0.0074 (3) | 0.0099 (3) | −0.0170 (3) |
C1 | 0.0394 (11) | 0.0460 (11) | 0.0481 (11) | −0.0003 (9) | −0.0046 (9) | −0.0185 (9) |
C2 | 0.0452 (11) | 0.0369 (10) | 0.0366 (10) | −0.0053 (8) | −0.0031 (8) | −0.0084 (8) |
C3 | 0.0464 (11) | 0.0397 (10) | 0.0345 (9) | −0.0139 (8) | −0.0067 (8) | −0.0017 (8) |
C4 | 0.0468 (12) | 0.0569 (13) | 0.0478 (12) | −0.0118 (10) | −0.0042 (9) | −0.0051 (10) |
C5 | 0.0531 (14) | 0.0727 (17) | 0.0561 (14) | −0.0267 (12) | −0.0152 (11) | 0.0009 (12) |
C6 | 0.0824 (19) | 0.0700 (16) | 0.0481 (13) | −0.0398 (14) | −0.0201 (12) | −0.0034 (12) |
C7 | 0.0789 (18) | 0.0573 (14) | 0.0452 (12) | −0.0247 (12) | −0.0061 (11) | −0.0163 (10) |
C8 | 0.0563 (13) | 0.0393 (11) | 0.0389 (10) | −0.0149 (9) | −0.0054 (9) | −0.0048 (8) |
C9 | 0.0391 (10) | 0.0445 (11) | 0.0432 (11) | −0.0063 (8) | 0.0037 (8) | −0.0075 (9) |
C10 | 0.0390 (10) | 0.0377 (10) | 0.0356 (9) | −0.0104 (8) | −0.0039 (8) | −0.0068 (8) |
C11 | 0.0505 (12) | 0.0365 (10) | 0.0476 (11) | −0.0100 (9) | −0.0074 (9) | −0.0028 (9) |
C12 | 0.0762 (18) | 0.0393 (12) | 0.0729 (17) | −0.0086 (12) | −0.0054 (14) | 0.0040 (11) |
C13 | 0.0788 (19) | 0.0382 (13) | 0.096 (2) | 0.0074 (12) | −0.0110 (16) | −0.0050 (13) |
C14 | 0.0573 (15) | 0.0476 (14) | 0.093 (2) | 0.0070 (11) | −0.0019 (14) | −0.0183 (13) |
C15 | 0.0504 (13) | 0.0423 (12) | 0.0657 (14) | −0.0062 (10) | 0.0041 (11) | −0.0116 (10) |
C16 | 0.0417 (11) | 0.0338 (10) | 0.0437 (10) | −0.0061 (8) | −0.0065 (8) | −0.0077 (8) |
C17 | 0.0404 (11) | 0.0544 (13) | 0.0483 (12) | −0.0034 (9) | −0.0109 (9) | −0.0173 (10) |
C18 | 0.0443 (11) | 0.0480 (12) | 0.0447 (11) | −0.0096 (9) | −0.0098 (9) | −0.0147 (9) |
C19 | 0.0736 (15) | 0.0485 (12) | 0.0380 (11) | −0.0147 (11) | −0.0132 (10) | −0.0077 (9) |
C20 | 0.0458 (11) | 0.0396 (10) | 0.0364 (10) | −0.0058 (8) | −0.0017 (8) | −0.0055 (8) |
C21 | 0.0452 (11) | 0.0431 (11) | 0.0471 (11) | −0.0076 (9) | −0.0034 (9) | −0.0021 (9) |
C22 | 0.0679 (16) | 0.0460 (13) | 0.0659 (15) | −0.0157 (12) | −0.0068 (12) | 0.0078 (11) |
C23 | 0.0720 (17) | 0.0419 (13) | 0.097 (2) | −0.0219 (12) | −0.0014 (15) | −0.0019 (13) |
C24 | 0.0687 (16) | 0.0483 (13) | 0.0801 (18) | −0.0223 (12) | −0.0067 (13) | −0.0173 (12) |
C25 | 0.0590 (14) | 0.0447 (12) | 0.0568 (13) | −0.0165 (10) | −0.0105 (11) | −0.0072 (10) |
C26 | 0.0424 (11) | 0.0338 (10) | 0.0484 (11) | −0.0069 (8) | −0.0023 (9) | −0.0039 (8) |
C27 | 0.0489 (12) | 0.0522 (12) | 0.0458 (11) | −0.0121 (10) | −0.0053 (9) | −0.0187 (9) |
C28 | 0.0456 (11) | 0.0391 (10) | 0.0404 (10) | −0.0081 (9) | −0.0016 (8) | −0.0132 (8) |
C29 | 0.0447 (11) | 0.0412 (11) | 0.0437 (11) | −0.0019 (9) | −0.0034 (9) | −0.0155 (9) |
C30 | 0.0649 (15) | 0.0576 (14) | 0.0414 (11) | 0.0023 (11) | −0.0043 (10) | −0.0176 (10) |
C31 | 0.0724 (16) | 0.0589 (15) | 0.0555 (14) | 0.0136 (12) | −0.0259 (13) | −0.0302 (12) |
C32 | 0.0642 (16) | 0.0579 (15) | 0.0855 (19) | −0.0012 (12) | −0.0214 (14) | −0.0383 (14) |
C33 | 0.0572 (14) | 0.0483 (13) | 0.0681 (15) | −0.0134 (10) | −0.0035 (11) | −0.0245 (11) |
C34 | 0.0443 (11) | 0.0369 (10) | 0.0460 (11) | −0.0045 (8) | −0.0033 (8) | −0.0158 (8) |
N1 | 0.0355 (8) | 0.0378 (8) | 0.0400 (8) | −0.0033 (6) | −0.0066 (6) | −0.0105 (7) |
N2 | 0.0529 (10) | 0.0391 (9) | 0.0338 (8) | −0.0118 (7) | −0.0049 (7) | −0.0090 (7) |
N3 | 0.0397 (9) | 0.0416 (9) | 0.0375 (8) | −0.0056 (7) | −0.0044 (7) | −0.0102 (7) |
N4 | 0.0511 (11) | 0.0439 (10) | 0.0479 (10) | −0.0054 (8) | −0.0010 (8) | −0.0188 (8) |
N5 | 0.0372 (8) | 0.0330 (8) | 0.0390 (8) | −0.0044 (6) | −0.0004 (7) | −0.0056 (6) |
N6 | 0.0498 (10) | 0.0395 (9) | 0.0425 (9) | −0.0140 (8) | 0.0025 (8) | −0.0022 (7) |
N7 | 0.0531 (10) | 0.0352 (9) | 0.0397 (9) | −0.0092 (7) | −0.0082 (7) | −0.0052 (7) |
N8 | 0.0589 (11) | 0.0450 (10) | 0.0383 (9) | −0.0088 (8) | −0.0103 (8) | 0.0022 (8) |
N9 | 0.0548 (11) | 0.0498 (10) | 0.0406 (9) | −0.0203 (8) | 0.0070 (8) | −0.0133 (8) |
N10 | 0.0553 (10) | 0.0448 (10) | 0.0411 (9) | −0.0174 (8) | 0.0031 (8) | −0.0134 (7) |
O3 | 0.0684 (12) | 0.1107 (16) | 0.0462 (9) | −0.0287 (11) | −0.0056 (8) | −0.0102 (10) |
Mn1—N5 | 2.1889 (16) | C18—N2 | 1.482 (3) |
Mn1—N7 | 2.1978 (17) | C18—H18A | 0.9700 |
Mn1—N3 | 2.2063 (17) | C18—H18B | 0.9700 |
Mn1—N1 | 2.4071 (17) | C19—N2 | 1.484 (3) |
Mn1—Cl1 | 2.4078 (8) | C19—C20 | 1.487 (3) |
Mn1—N2 | 2.4938 (17) | C19—H19A | 0.9700 |
C1—N1 | 1.470 (3) | C19—H19B | 0.9700 |
C1—C2 | 1.497 (3) | C20—N7 | 1.315 (3) |
C1—H1A | 0.9700 | C20—N8 | 1.342 (3) |
C1—H1B | 0.9700 | C21—N8 | 1.379 (3) |
C2—N3 | 1.316 (3) | C21—C22 | 1.383 (3) |
C2—N4 | 1.345 (3) | C21—C26 | 1.404 (3) |
C3—C4 | 1.392 (3) | C22—C23 | 1.370 (4) |
C3—C8 | 1.393 (3) | C22—H22 | 0.9300 |
C3—N3 | 1.395 (2) | C23—C24 | 1.388 (4) |
C4—C5 | 1.375 (3) | C23—H23 | 0.9300 |
C4—H4 | 0.9300 | C24—C25 | 1.375 (3) |
C5—C6 | 1.380 (4) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.388 (3) |
C6—C7 | 1.366 (4) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—N7 | 1.395 (3) |
C7—C8 | 1.404 (3) | C27—N2 | 1.476 (3) |
C7—H7 | 0.9300 | C27—C28 | 1.499 (3) |
C8—N4 | 1.376 (3) | C27—H27A | 0.9700 |
C9—N1 | 1.473 (3) | C27—H27B | 0.9700 |
C9—C10 | 1.497 (3) | C28—N10 | 1.312 (3) |
C9—H9A | 0.9700 | C28—N9 | 1.360 (3) |
C9—H9B | 0.9700 | C29—N9 | 1.374 (3) |
C10—N5 | 1.312 (2) | C29—C34 | 1.384 (3) |
C10—N6 | 1.346 (2) | C29—C30 | 1.391 (3) |
C11—N6 | 1.386 (3) | C30—C31 | 1.380 (4) |
C11—C12 | 1.388 (3) | C30—H30 | 0.9300 |
C11—C16 | 1.399 (3) | C31—C32 | 1.381 (4) |
C12—C13 | 1.381 (4) | C31—H31 | 0.9300 |
C12—H12 | 0.9300 | C32—C33 | 1.367 (4) |
C13—C14 | 1.393 (4) | C32—H32 | 0.9300 |
C13—H13 | 0.9300 | C33—C34 | 1.401 (3) |
C14—C15 | 1.377 (3) | C33—H33 | 0.9300 |
C14—H14 | 0.9300 | C34—N10 | 1.388 (3) |
C15—C16 | 1.384 (3) | N4—H4A | 0.851 (10) |
C15—H15 | 0.9300 | N6—H6A | 0.843 (10) |
C16—N5 | 1.399 (2) | N8—H8 | 0.855 (10) |
C17—N1 | 1.479 (3) | N9—H9 | 0.847 (10) |
C17—C18 | 1.511 (3) | O3—H3A | 0.819 (10) |
C17—H17A | 0.9700 | O3—H3B | 0.835 (10) |
C17—H17B | 0.9700 | ||
N5—Mn1—N7 | 156.40 (6) | C20—C19—H19B | 109.3 |
N5—Mn1—N3 | 98.35 (6) | H19A—C19—H19B | 108.0 |
N7—Mn1—N3 | 95.05 (6) | N7—C20—N8 | 112.80 (18) |
N5—Mn1—N1 | 74.97 (6) | N7—C20—C19 | 124.59 (18) |
N7—Mn1—N1 | 90.68 (6) | N8—C20—C19 | 122.59 (18) |
N3—Mn1—N1 | 72.89 (6) | N8—C21—C22 | 133.0 (2) |
N5—Mn1—Cl1 | 100.73 (4) | N8—C21—C26 | 105.36 (18) |
N7—Mn1—Cl1 | 94.39 (5) | C22—C21—C26 | 121.6 (2) |
N3—Mn1—Cl1 | 105.02 (5) | C23—C22—C21 | 117.3 (2) |
N1—Mn1—Cl1 | 174.68 (4) | C23—C22—H22 | 121.4 |
N5—Mn1—N2 | 85.00 (6) | C21—C22—H22 | 121.4 |
N7—Mn1—N2 | 73.08 (6) | C22—C23—C24 | 121.6 (2) |
N3—Mn1—N2 | 145.62 (6) | C22—C23—H23 | 119.2 |
N1—Mn1—N2 | 75.08 (6) | C24—C23—H23 | 119.2 |
Cl1—Mn1—N2 | 107.93 (5) | C25—C24—C23 | 121.7 (2) |
N1—C1—C2 | 108.90 (16) | C25—C24—H24 | 119.2 |
N1—C1—H1A | 109.9 | C23—C24—H24 | 119.2 |
C2—C1—H1A | 109.9 | C24—C25—C26 | 117.6 (2) |
N1—C1—H1B | 109.9 | C24—C25—H25 | 121.2 |
C2—C1—H1B | 109.9 | C26—C25—H25 | 121.2 |
H1A—C1—H1B | 108.3 | C25—C26—N7 | 131.23 (19) |
N3—C2—N4 | 112.98 (18) | C25—C26—C21 | 120.19 (19) |
N3—C2—C1 | 122.85 (17) | N7—C26—C21 | 108.58 (18) |
N4—C2—C1 | 124.03 (18) | N2—C27—C28 | 116.69 (18) |
C4—C3—C8 | 120.7 (2) | N2—C27—H27A | 108.1 |
C4—C3—N3 | 130.4 (2) | C28—C27—H27A | 108.1 |
C8—C3—N3 | 108.90 (18) | N2—C27—H27B | 108.1 |
C5—C4—C3 | 117.0 (2) | C28—C27—H27B | 108.1 |
C5—C4—H4 | 121.5 | H27A—C27—H27B | 107.3 |
C3—C4—H4 | 121.5 | N10—C28—N9 | 112.32 (18) |
C4—C5—C6 | 122.1 (2) | N10—C28—C27 | 125.14 (18) |
C4—C5—H5 | 119.0 | N9—C28—C27 | 122.42 (18) |
C6—C5—H5 | 119.0 | N9—C29—C34 | 105.17 (17) |
C7—C6—C5 | 122.2 (2) | N9—C29—C30 | 132.7 (2) |
C7—C6—H6 | 118.9 | C34—C29—C30 | 122.1 (2) |
C5—C6—H6 | 118.9 | C31—C30—C29 | 116.4 (2) |
C6—C7—C8 | 116.5 (2) | C31—C30—H30 | 121.8 |
C6—C7—H7 | 121.7 | C29—C30—H30 | 121.8 |
C8—C7—H7 | 121.7 | C30—C31—C32 | 121.8 (2) |
N4—C8—C3 | 105.75 (18) | C30—C31—H31 | 119.1 |
N4—C8—C7 | 132.8 (2) | C32—C31—H31 | 119.1 |
C3—C8—C7 | 121.5 (2) | C33—C32—C31 | 122.0 (2) |
N1—C9—C10 | 111.66 (16) | C33—C32—H32 | 119.0 |
N1—C9—H9A | 109.3 | C31—C32—H32 | 119.0 |
C10—C9—H9A | 109.3 | C32—C33—C34 | 117.2 (2) |
N1—C9—H9B | 109.3 | C32—C33—H33 | 121.4 |
C10—C9—H9B | 109.3 | C34—C33—H33 | 121.4 |
H9A—C9—H9B | 107.9 | C29—C34—N10 | 110.07 (17) |
N5—C10—N6 | 112.84 (17) | C29—C34—C33 | 120.5 (2) |
N5—C10—C9 | 124.15 (17) | N10—C34—C33 | 129.5 (2) |
N6—C10—C9 | 123.00 (17) | C1—N1—C9 | 110.72 (16) |
N6—C11—C12 | 132.7 (2) | C1—N1—C17 | 111.94 (16) |
N6—C11—C16 | 105.43 (17) | C9—N1—C17 | 112.47 (16) |
C12—C11—C16 | 121.9 (2) | C1—N1—Mn1 | 105.12 (12) |
C13—C12—C11 | 116.3 (2) | C9—N1—Mn1 | 108.33 (11) |
C13—C12—H12 | 121.9 | C17—N1—Mn1 | 107.90 (12) |
C11—C12—H12 | 121.9 | C27—N2—C18 | 112.46 (16) |
C12—C13—C14 | 122.2 (2) | C27—N2—C19 | 112.10 (16) |
C12—C13—H13 | 118.9 | C18—N2—C19 | 111.78 (17) |
C14—C13—H13 | 118.9 | C27—N2—Mn1 | 105.26 (12) |
C15—C14—C13 | 121.4 (2) | C18—N2—Mn1 | 104.54 (11) |
C15—C14—H14 | 119.3 | C19—N2—Mn1 | 110.21 (12) |
C13—C14—H14 | 119.3 | C2—N3—C3 | 105.15 (16) |
C14—C15—C16 | 117.3 (2) | C2—N3—Mn1 | 113.98 (13) |
C14—C15—H15 | 121.4 | C3—N3—Mn1 | 138.25 (13) |
C16—C15—H15 | 121.4 | C2—N4—C8 | 107.21 (17) |
C15—C16—N5 | 130.39 (19) | C2—N4—H4A | 121.2 (17) |
C15—C16—C11 | 121.03 (19) | C8—N4—H4A | 131.3 (17) |
N5—C16—C11 | 108.57 (18) | C10—N5—C16 | 105.76 (16) |
N1—C17—C18 | 111.77 (17) | C10—N5—Mn1 | 115.66 (12) |
N1—C17—H17A | 109.3 | C16—N5—Mn1 | 137.62 (13) |
C18—C17—H17A | 109.3 | C10—N6—C11 | 107.40 (16) |
N1—C17—H17B | 109.3 | C10—N6—H6A | 124.5 (17) |
C18—C17—H17B | 109.3 | C11—N6—H6A | 128.1 (17) |
H17A—C17—H17B | 107.9 | C20—N7—C26 | 105.59 (16) |
N2—C18—C17 | 111.39 (17) | C20—N7—Mn1 | 118.21 (13) |
N2—C18—H18A | 109.4 | C26—N7—Mn1 | 133.69 (13) |
C17—C18—H18A | 109.4 | C20—N8—C21 | 107.65 (17) |
N2—C18—H18B | 109.4 | C20—N8—H8 | 124.6 (17) |
C17—C18—H18B | 109.4 | C21—N8—H8 | 127.0 (17) |
H18A—C18—H18B | 108.0 | C28—N9—C29 | 107.41 (17) |
N2—C19—C20 | 111.61 (17) | C28—N9—H9 | 129.4 (17) |
N2—C19—H19A | 109.3 | C29—N9—H9 | 123.1 (17) |
C20—C19—H19A | 109.3 | C28—N10—C34 | 105.03 (17) |
N2—C19—H19B | 109.3 | H3A—O3—H3B | 114.4 (18) |
N1—C1—C2—N3 | 22.5 (3) | N3—Mn1—N2—C27 | −157.38 (12) |
N1—C1—C2—N4 | −162.06 (19) | N1—Mn1—N2—C27 | −135.62 (13) |
C8—C3—C4—C5 | −1.2 (3) | Cl1—Mn1—N2—C27 | 39.81 (13) |
N3—C3—C4—C5 | 177.1 (2) | N5—Mn1—N2—C18 | 58.80 (12) |
C3—C4—C5—C6 | 0.6 (3) | N7—Mn1—N2—C18 | −112.34 (13) |
C4—C5—C6—C7 | 0.4 (4) | N3—Mn1—N2—C18 | −38.70 (17) |
C5—C6—C7—C8 | −0.8 (4) | N1—Mn1—N2—C18 | −16.95 (12) |
C4—C3—C8—N4 | 179.73 (19) | Cl1—Mn1—N2—C18 | 158.48 (11) |
N3—C3—C8—N4 | 1.1 (2) | N5—Mn1—N2—C19 | 179.06 (14) |
C4—C3—C8—C7 | 0.9 (3) | N7—Mn1—N2—C19 | 7.92 (14) |
N3—C3—C8—C7 | −177.77 (18) | N3—Mn1—N2—C19 | 81.56 (17) |
C6—C7—C8—N4 | −178.3 (2) | N1—Mn1—N2—C19 | 103.31 (14) |
C6—C7—C8—C3 | 0.1 (3) | Cl1—Mn1—N2—C19 | −81.26 (14) |
N1—C9—C10—N5 | 11.4 (3) | N4—C2—N3—C3 | −0.4 (2) |
N1—C9—C10—N6 | −170.01 (18) | C1—C2—N3—C3 | 175.43 (18) |
N6—C11—C12—C13 | 178.6 (3) | N4—C2—N3—Mn1 | −165.50 (13) |
C16—C11—C12—C13 | −1.5 (4) | C1—C2—N3—Mn1 | 10.3 (2) |
C11—C12—C13—C14 | 0.7 (4) | C4—C3—N3—C2 | −178.9 (2) |
C12—C13—C14—C15 | −0.2 (5) | C8—C3—N3—C2 | −0.4 (2) |
C13—C14—C15—C16 | 0.4 (4) | C4—C3—N3—Mn1 | −19.6 (3) |
C14—C15—C16—N5 | −179.9 (2) | C8—C3—N3—Mn1 | 158.89 (15) |
C14—C15—C16—C11 | −1.2 (3) | N5—Mn1—N3—C2 | −95.69 (14) |
N6—C11—C16—C15 | −178.22 (19) | N7—Mn1—N3—C2 | 64.83 (14) |
C12—C11—C16—C15 | 1.8 (3) | N1—Mn1—N3—C2 | −24.33 (13) |
N6—C11—C16—N5 | 0.8 (2) | Cl1—Mn1—N3—C2 | 160.76 (13) |
C12—C11—C16—N5 | −179.2 (2) | N2—Mn1—N3—C2 | −2.3 (2) |
N1—C17—C18—N2 | −64.5 (2) | N5—Mn1—N3—C3 | 106.22 (19) |
N2—C19—C20—N7 | −9.5 (3) | N7—Mn1—N3—C3 | −93.26 (19) |
N2—C19—C20—N8 | 172.27 (19) | N1—Mn1—N3—C3 | 177.6 (2) |
N8—C21—C22—C23 | 177.2 (2) | Cl1—Mn1—N3—C3 | 2.7 (2) |
C26—C21—C22—C23 | −0.5 (4) | N2—Mn1—N3—C3 | −160.41 (16) |
C21—C22—C23—C24 | 2.3 (4) | N3—C2—N4—C8 | 1.1 (2) |
C22—C23—C24—C25 | −2.1 (4) | C1—C2—N4—C8 | −174.68 (19) |
C23—C24—C25—C26 | 0.0 (4) | C3—C8—N4—C2 | −1.3 (2) |
C24—C25—C26—N7 | −177.3 (2) | C7—C8—N4—C2 | 177.4 (2) |
C24—C25—C26—C21 | 1.7 (3) | N6—C10—N5—C16 | −0.1 (2) |
N8—C21—C26—C25 | −179.8 (2) | C9—C10—N5—C16 | 178.61 (18) |
C22—C21—C26—C25 | −1.4 (3) | N6—C10—N5—Mn1 | −170.87 (13) |
N8—C21—C26—N7 | −0.6 (2) | C9—C10—N5—Mn1 | 7.8 (2) |
C22—C21—C26—N7 | 177.7 (2) | C15—C16—N5—C10 | 178.4 (2) |
N2—C27—C28—N10 | −78.5 (3) | C11—C16—N5—C10 | −0.4 (2) |
N2—C27—C28—N9 | 105.8 (2) | C15—C16—N5—Mn1 | −13.9 (4) |
N9—C29—C30—C31 | 179.0 (2) | C11—C16—N5—Mn1 | 167.21 (15) |
C34—C29—C30—C31 | 0.6 (3) | N7—Mn1—N5—C10 | −69.2 (2) |
C29—C30—C31—C32 | −0.3 (3) | N3—Mn1—N5—C10 | 54.70 (14) |
C30—C31—C32—C33 | −0.3 (4) | N1—Mn1—N5—C10 | −14.98 (13) |
C31—C32—C33—C34 | 0.7 (4) | Cl1—Mn1—N5—C10 | 161.82 (13) |
N9—C29—C34—N10 | −0.2 (2) | N2—Mn1—N5—C10 | −90.85 (14) |
C30—C29—C34—N10 | 178.56 (19) | N7—Mn1—N5—C16 | 123.9 (2) |
N9—C29—C34—C33 | −178.98 (19) | N3—Mn1—N5—C16 | −112.11 (19) |
C30—C29—C34—C33 | −0.2 (3) | N1—Mn1—N5—C16 | 178.2 (2) |
C32—C33—C34—C29 | −0.4 (3) | Cl1—Mn1—N5—C16 | −5.0 (2) |
C32—C33—C34—N10 | −178.9 (2) | N2—Mn1—N5—C16 | 102.34 (19) |
C2—C1—N1—C9 | 77.9 (2) | N5—C10—N6—C11 | 0.6 (2) |
C2—C1—N1—C17 | −155.78 (17) | C9—C10—N6—C11 | −178.14 (18) |
C2—C1—N1—Mn1 | −38.91 (18) | C12—C11—N6—C10 | 179.1 (3) |
C10—C9—N1—C1 | −136.64 (17) | C16—C11—N6—C10 | −0.8 (2) |
C10—C9—N1—C17 | 97.29 (19) | N8—C20—N7—C26 | 1.1 (2) |
C10—C9—N1—Mn1 | −21.87 (19) | C19—C20—N7—C26 | −177.2 (2) |
C18—C17—N1—C1 | 158.62 (18) | N8—C20—N7—Mn1 | −163.37 (14) |
C18—C17—N1—C9 | −76.0 (2) | C19—C20—N7—Mn1 | 18.3 (3) |
C18—C17—N1—Mn1 | 43.4 (2) | C25—C26—N7—C20 | 178.8 (2) |
N5—Mn1—N1—C1 | 138.30 (13) | C21—C26—N7—C20 | −0.3 (2) |
N7—Mn1—N1—C1 | −60.67 (12) | C25—C26—N7—Mn1 | −20.3 (4) |
N3—Mn1—N1—C1 | 34.40 (12) | C21—C26—N7—Mn1 | 160.69 (15) |
Cl1—Mn1—N1—C1 | 101.9 (5) | N5—Mn1—N7—C20 | −35.9 (3) |
N2—Mn1—N1—C1 | −132.95 (13) | N3—Mn1—N7—C20 | −160.38 (15) |
N5—Mn1—N1—C9 | 19.90 (12) | N1—Mn1—N7—C20 | −87.50 (15) |
N7—Mn1—N1—C9 | −179.07 (12) | Cl1—Mn1—N7—C20 | 94.09 (15) |
N3—Mn1—N1—C9 | −83.99 (13) | N2—Mn1—N7—C20 | −13.33 (15) |
Cl1—Mn1—N1—C9 | −16.4 (5) | N5—Mn1—N7—C26 | 165.01 (17) |
N2—Mn1—N1—C9 | 108.66 (13) | N3—Mn1—N7—C26 | 40.50 (19) |
N5—Mn1—N1—C17 | −102.10 (13) | N1—Mn1—N7—C26 | 113.38 (19) |
N7—Mn1—N1—C17 | 58.93 (13) | Cl1—Mn1—N7—C26 | −65.03 (19) |
N3—Mn1—N1—C17 | 154.01 (14) | N2—Mn1—N7—C26 | −172.4 (2) |
Cl1—Mn1—N1—C17 | −138.5 (4) | N7—C20—N8—C21 | −1.5 (3) |
N2—Mn1—N1—C17 | −13.35 (12) | C19—C20—N8—C21 | 176.9 (2) |
C28—C27—N2—C18 | 62.6 (2) | C22—C21—N8—C20 | −176.8 (3) |
C28—C27—N2—C19 | −64.3 (2) | C26—C21—N8—C20 | 1.2 (2) |
C28—C27—N2—Mn1 | 175.86 (15) | N10—C28—N9—C29 | 0.1 (2) |
C17—C18—N2—C27 | 159.79 (17) | C27—C28—N9—C29 | 176.31 (19) |
C17—C18—N2—C19 | −73.1 (2) | C34—C29—N9—C28 | 0.1 (2) |
C17—C18—N2—Mn1 | 46.13 (18) | C30—C29—N9—C28 | −178.5 (2) |
C20—C19—N2—C27 | −119.4 (2) | N9—C28—N10—C34 | −0.3 (2) |
C20—C19—N2—C18 | 113.2 (2) | C27—C28—N10—C34 | −176.32 (19) |
C20—C19—N2—Mn1 | −2.6 (2) | C29—C34—N10—C28 | 0.3 (2) |
N5—Mn1—N2—C27 | −59.88 (13) | C33—C34—N10—C28 | 178.9 (2) |
N7—Mn1—N2—C27 | 128.99 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···N10i | 0.84 (1) | 2.07 (1) | 2.884 (3) | 167 (3) |
N4—H4A···Cl2ii | 0.85 (1) | 2.31 (1) | 3.147 (2) | 169 (2) |
N8—H8···O3iii | 0.86 (1) | 1.92 (1) | 2.755 (3) | 164 (2) |
N9—H9···Cl1iv | 0.85 (1) | 2.49 (2) | 3.242 (2) | 149 (2) |
C19—H19B···Cl1iv | 0.97 | 2.69 | 3.607 (3) | 157 |
N6—H6A···Cl2 | 0.84 (1) | 2.45 (2) | 3.1920 (19) | 147 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z−1; (iv) −x+2, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | [MnCl(C34H32N10)]Cl·H2O |
Mr | 724.55 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 299 |
a, b, c (Å) | 9.790 (2), 12.657 (3), 16.039 (4) |
α, β, γ (°) | 76.380 (4), 84.743 (4), 77.753 (4) |
V (Å3) | 1885.8 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.53 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2001) |
Tmin, Tmax | 0.901, 0.949 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20876, 8156, 6487 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.127, 1.06 |
No. of reflections | 8156 |
No. of parameters | 453 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.41, −0.18 |
Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), PLATON.
N5—Mn1—N7 | 156.40 (6) | N3—Mn1—Cl1 | 105.02 (5) |
N5—Mn1—N3 | 98.35 (6) | N1—Mn1—Cl1 | 174.68 (4) |
N7—Mn1—N3 | 95.05 (6) | N5—Mn1—N2 | 85.00 (6) |
N5—Mn1—N1 | 74.97 (6) | N7—Mn1—N2 | 73.08 (6) |
N7—Mn1—N1 | 90.68 (6) | N3—Mn1—N2 | 145.62 (6) |
N3—Mn1—N1 | 72.89 (6) | N1—Mn1—N2 | 75.08 (6) |
N5—Mn1—Cl1 | 100.73 (4) | Cl1—Mn1—N2 | 107.93 (5) |
N7—Mn1—Cl1 | 94.39 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3B···N10i | 0.835 (10) | 2.065 (11) | 2.884 (3) | 167 (3) |
N4—H4A···Cl2ii | 0.851 (10) | 2.308 (11) | 3.147 (2) | 169 (2) |
N8—H8···O3iii | 0.855 (10) | 1.922 (12) | 2.755 (3) | 164 (2) |
N9—H9···Cl1iv | 0.847 (10) | 2.485 (15) | 3.242 (2) | 149 (2) |
C19—H19B···Cl1iv | 0.97 | 2.69 | 3.607 (3) | 157.4 |
N6—H6A···Cl2 | 0.843 (10) | 2.454 (16) | 3.1920 (19) | 147 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1; (iii) x, y+1, z−1; (iv) −x+2, −y+2, −z. |
Recently, studies of ligands containing polybenzimidazole groups and their metal coordination compounds have been widely carried out (Chen et al., 2004; Liao et al.,2001). In a continuation of our work, we report herein the crystal structure of the title compound (I).
In the molecular structure of (I) (Fig. 1) the MnII is coordinated by three benzimidazole N atoms, two amino N atoms of an edtb ligand and one chloride anion, forming a distorted octahedron coordination geometry. Unlike the related structure (Chen et al., 2004), in (I) there is an uncoordinated benzimidazole group extending away from the central Mn atom.
There are a number of N(or C)–H···Cl, N–H···O and O–H···N hydrogen bonds which stabilize the crystal structure (Table 2 & Fig. 2).