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In the title compound, [MnCl(C34H32N10)]Cl·H2O, the MnII ion is in a distorted octa­hedral coordination environment. The crystal structure is stabilized by extensive hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021034/lh2366sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021034/lh2366Isup2.hkl
Contains datablock I

CCDC reference: 650527

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.127
  • Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 274.00 A   3
Author Response: see experimental section

Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O3 - H3A ... ?
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.22 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Mn1 - Cl1 .. 5.68 su PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 66 CL1 -MN1 -N1 -C1 101.90 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 71 CL1 -MN1 -N1 -C9 -16.40 0.50 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 76 CL1 -MN1 -N1 -C17 -138.50 0.40 1.555 1.555 1.555 1.555
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of N2 = ... R PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1 (2) 2.04 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (I), showing 50% probability displacement ellipsoids and H atoms as small spheres.
[Figure 2] Fig. 2. Part of the crystal structure of (I), showing hydrogen bonds as dashed lines.
Chlorido[N,N,N',N'-tetrakis(benzimidazol-2-ylmethyl)ethane-1,2- diamine]manganese(II) chloride monohydrate top
Crystal data top
[MnCl(C34H32N10)]Cl·H2OZ = 2
Mr = 724.55F(000) = 750
Triclinic, P1Dx = 1.276 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.790 (2) ÅCell parameters from 8006 reflections
b = 12.657 (3) Åθ = 2.4–27.2°
c = 16.039 (4) ŵ = 0.53 mm1
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
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8156 independent reflections
Radiation source: fine focus sealed Siemens Mo tube6487 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
0.3° wide ω exposures scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1212
Tmin = 0.901, Tmax = 0.949k = 1616
20876 measured reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H 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 parametersΔρmax = 0.41 e Å3
7 restraintsΔρmin = 0.18 e Å3
Crystal data top
[MnCl(C34H32N10)]Cl·H2Oγ = 77.753 (4)°
Mr = 724.55V = 1885.8 (8) Å3
Triclinic, P1Z = 2
a = 9.790 (2) ÅMo Kα radiation
b = 12.657 (3) ŵ = 0.53 mm1
c = 16.039 (4) ÅT = 299 K
α = 76.380 (4)°0.20 × 0.10 × 0.10 mm
β = 84.743 (4)°
Data collection top
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 = 0.949Rint = 0.025
20876 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0457 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.41 e Å3
8156 reflectionsΔρmin = 0.18 e Å3
453 parameters
Special details top

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) top
xyzUiso*/Ueq
Mn10.87099 (3)0.97239 (2)0.217963 (17)0.03531 (10)
Cl11.11136 (6)0.95010 (5)0.16532 (4)0.06023 (17)
Cl20.55649 (7)0.70808 (6)0.54994 (4)0.06850 (19)
C10.6092 (2)1.08254 (18)0.31676 (14)0.0442 (5)
H1A0.53431.07850.36070.053*
H1B0.58011.14720.27130.053*
C20.7393 (2)1.09219 (16)0.35430 (12)0.0399 (4)
C30.9568 (2)1.07967 (16)0.37531 (12)0.0402 (4)
C41.1023 (2)1.0563 (2)0.37460 (14)0.0512 (5)
H41.15511.00730.34340.061*
C51.1646 (3)1.1088 (2)0.42214 (16)0.0602 (6)
H51.26171.09540.42240.072*
C61.0875 (3)1.1808 (2)0.46945 (16)0.0636 (7)
H61.13441.21470.50030.076*
C70.9446 (3)1.2040 (2)0.47242 (15)0.0577 (6)
H70.89321.25190.50500.069*
C80.8793 (2)1.15160 (17)0.42380 (13)0.0444 (5)
C90.6374 (2)0.88249 (17)0.35197 (13)0.0433 (5)
H9A0.54980.85790.35330.052*
H9B0.64400.90120.40650.052*
C100.7564 (2)0.79014 (16)0.34047 (12)0.0371 (4)
C110.8914 (2)0.62402 (17)0.36215 (14)0.0454 (5)
C120.9565 (3)0.5139 (2)0.38902 (18)0.0659 (7)
H120.91870.46560.43370.079*
C131.0806 (3)0.4800 (2)0.3457 (2)0.0751 (8)
H131.12710.40660.36140.090*
C141.1386 (3)0.5522 (2)0.2794 (2)0.0683 (7)
H141.22260.52590.25210.082*
C151.0743 (2)0.66171 (18)0.25345 (16)0.0537 (5)
H151.11280.70980.20890.064*
C160.9500 (2)0.69731 (16)0.29630 (13)0.0398 (4)
C170.5418 (2)0.98934 (19)0.21419 (14)0.0471 (5)
H17A0.52411.06450.17960.056*
H17B0.45330.97290.24050.056*
C180.6014 (2)0.90988 (18)0.15694 (13)0.0443 (5)
H18A0.62300.83500.19170.053*
H18B0.53210.91200.11680.053*
C190.6979 (3)1.03940 (18)0.03887 (14)0.0526 (5)
H19A0.59741.06120.03360.063*
H19B0.73891.02290.01510.063*
C200.7528 (2)1.13286 (16)0.05581 (12)0.0415 (4)
C210.8023 (2)1.29872 (18)0.03526 (14)0.0465 (5)
C220.8184 (3)1.4076 (2)0.00745 (17)0.0625 (6)
H220.79591.44780.04770.075*
C230.8689 (3)1.4538 (2)0.0644 (2)0.0710 (8)
H230.87771.52770.04820.085*
C240.9071 (3)1.3929 (2)0.14568 (19)0.0633 (6)
H240.94381.42640.18190.076*
C250.8922 (2)1.28452 (18)0.17394 (16)0.0527 (5)
H250.91801.24430.22850.063*
C260.8371 (2)1.23728 (16)0.11812 (13)0.0425 (4)
C270.8169 (2)0.84426 (19)0.07694 (14)0.0471 (5)
H27A0.84300.78390.12610.057*
H27B0.90240.86660.05030.057*
C280.7526 (2)0.80061 (16)0.01401 (13)0.0410 (4)
C290.7187 (2)0.76308 (17)0.10898 (13)0.0431 (4)
C300.7182 (3)0.7509 (2)0.19289 (14)0.0555 (6)
H300.77300.78570.23690.067*
C310.6319 (3)0.6843 (2)0.20722 (17)0.0619 (7)
H310.62820.67420.26250.074*
C320.5511 (3)0.6322 (2)0.14177 (19)0.0658 (7)
H320.49400.58840.15430.079*
C330.5523 (3)0.64310 (19)0.05903 (17)0.0554 (6)
H330.49820.60700.01520.067*
C340.6384 (2)0.71082 (16)0.04299 (13)0.0417 (4)
N10.63796 (16)0.98180 (13)0.28227 (10)0.0377 (3)
N20.72994 (18)0.93848 (13)0.10858 (10)0.0412 (4)
N30.86515 (17)1.04362 (13)0.33155 (10)0.0395 (4)
N40.7413 (2)1.15652 (15)0.40989 (12)0.0468 (4)
H4A0.6662 (16)1.1952 (18)0.4266 (15)0.056*
N50.86186 (16)0.80181 (13)0.28470 (10)0.0373 (3)
N60.76745 (19)0.68611 (14)0.38818 (11)0.0446 (4)
H6A0.709 (2)0.6652 (19)0.4270 (12)0.053*
N70.80471 (18)1.13265 (13)0.12867 (10)0.0427 (4)
N80.7508 (2)1.22867 (15)0.00237 (11)0.0490 (4)
H80.712 (2)1.245 (2)0.0505 (10)0.059*
N90.7908 (2)0.82004 (15)0.07105 (11)0.0469 (4)
H90.845 (2)0.8612 (17)0.0990 (14)0.056*
N100.66146 (19)0.73513 (14)0.03392 (11)0.0456 (4)
O30.5832 (2)0.3045 (2)0.85843 (11)0.0745 (5)
H3A0.586 (3)0.312 (3)0.8063 (7)0.112*
H3B0.5049 (19)0.299 (3)0.8824 (18)0.112*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.04063 (18)0.03138 (16)0.03312 (16)0.00702 (12)0.00128 (11)0.00574 (11)
Cl10.0523 (3)0.0513 (3)0.0703 (4)0.0121 (3)0.0189 (3)0.0064 (3)
Cl20.0570 (4)0.0882 (5)0.0553 (3)0.0074 (3)0.0099 (3)0.0170 (3)
C10.0394 (11)0.0460 (11)0.0481 (11)0.0003 (9)0.0046 (9)0.0185 (9)
C20.0452 (11)0.0369 (10)0.0366 (10)0.0053 (8)0.0031 (8)0.0084 (8)
C30.0464 (11)0.0397 (10)0.0345 (9)0.0139 (8)0.0067 (8)0.0017 (8)
C40.0468 (12)0.0569 (13)0.0478 (12)0.0118 (10)0.0042 (9)0.0051 (10)
C50.0531 (14)0.0727 (17)0.0561 (14)0.0267 (12)0.0152 (11)0.0009 (12)
C60.0824 (19)0.0700 (16)0.0481 (13)0.0398 (14)0.0201 (12)0.0034 (12)
C70.0789 (18)0.0573 (14)0.0452 (12)0.0247 (12)0.0061 (11)0.0163 (10)
C80.0563 (13)0.0393 (11)0.0389 (10)0.0149 (9)0.0054 (9)0.0048 (8)
C90.0391 (10)0.0445 (11)0.0432 (11)0.0063 (8)0.0037 (8)0.0075 (9)
C100.0390 (10)0.0377 (10)0.0356 (9)0.0104 (8)0.0039 (8)0.0068 (8)
C110.0505 (12)0.0365 (10)0.0476 (11)0.0100 (9)0.0074 (9)0.0028 (9)
C120.0762 (18)0.0393 (12)0.0729 (17)0.0086 (12)0.0054 (14)0.0040 (11)
C130.0788 (19)0.0382 (13)0.096 (2)0.0074 (12)0.0110 (16)0.0050 (13)
C140.0573 (15)0.0476 (14)0.093 (2)0.0070 (11)0.0019 (14)0.0183 (13)
C150.0504 (13)0.0423 (12)0.0657 (14)0.0062 (10)0.0041 (11)0.0116 (10)
C160.0417 (11)0.0338 (10)0.0437 (10)0.0061 (8)0.0065 (8)0.0077 (8)
C170.0404 (11)0.0544 (13)0.0483 (12)0.0034 (9)0.0109 (9)0.0173 (10)
C180.0443 (11)0.0480 (12)0.0447 (11)0.0096 (9)0.0098 (9)0.0147 (9)
C190.0736 (15)0.0485 (12)0.0380 (11)0.0147 (11)0.0132 (10)0.0077 (9)
C200.0458 (11)0.0396 (10)0.0364 (10)0.0058 (8)0.0017 (8)0.0055 (8)
C210.0452 (11)0.0431 (11)0.0471 (11)0.0076 (9)0.0034 (9)0.0021 (9)
C220.0679 (16)0.0460 (13)0.0659 (15)0.0157 (12)0.0068 (12)0.0078 (11)
C230.0720 (17)0.0419 (13)0.097 (2)0.0219 (12)0.0014 (15)0.0019 (13)
C240.0687 (16)0.0483 (13)0.0801 (18)0.0223 (12)0.0067 (13)0.0173 (12)
C250.0590 (14)0.0447 (12)0.0568 (13)0.0165 (10)0.0105 (11)0.0072 (10)
C260.0424 (11)0.0338 (10)0.0484 (11)0.0069 (8)0.0023 (9)0.0039 (8)
C270.0489 (12)0.0522 (12)0.0458 (11)0.0121 (10)0.0053 (9)0.0187 (9)
C280.0456 (11)0.0391 (10)0.0404 (10)0.0081 (9)0.0016 (8)0.0132 (8)
C290.0447 (11)0.0412 (11)0.0437 (11)0.0019 (9)0.0034 (9)0.0155 (9)
C300.0649 (15)0.0576 (14)0.0414 (11)0.0023 (11)0.0043 (10)0.0176 (10)
C310.0724 (16)0.0589 (15)0.0555 (14)0.0136 (12)0.0259 (13)0.0302 (12)
C320.0642 (16)0.0579 (15)0.0855 (19)0.0012 (12)0.0214 (14)0.0383 (14)
C330.0572 (14)0.0483 (13)0.0681 (15)0.0134 (10)0.0035 (11)0.0245 (11)
C340.0443 (11)0.0369 (10)0.0460 (11)0.0045 (8)0.0033 (8)0.0158 (8)
N10.0355 (8)0.0378 (8)0.0400 (8)0.0033 (6)0.0066 (6)0.0105 (7)
N20.0529 (10)0.0391 (9)0.0338 (8)0.0118 (7)0.0049 (7)0.0090 (7)
N30.0397 (9)0.0416 (9)0.0375 (8)0.0056 (7)0.0044 (7)0.0102 (7)
N40.0511 (11)0.0439 (10)0.0479 (10)0.0054 (8)0.0010 (8)0.0188 (8)
N50.0372 (8)0.0330 (8)0.0390 (8)0.0044 (6)0.0004 (7)0.0056 (6)
N60.0498 (10)0.0395 (9)0.0425 (9)0.0140 (8)0.0025 (8)0.0022 (7)
N70.0531 (10)0.0352 (9)0.0397 (9)0.0092 (7)0.0082 (7)0.0052 (7)
N80.0589 (11)0.0450 (10)0.0383 (9)0.0088 (8)0.0103 (8)0.0022 (8)
N90.0548 (11)0.0498 (10)0.0406 (9)0.0203 (8)0.0070 (8)0.0133 (8)
N100.0553 (10)0.0448 (10)0.0411 (9)0.0174 (8)0.0031 (8)0.0134 (7)
O30.0684 (12)0.1107 (16)0.0462 (9)0.0287 (11)0.0056 (8)0.0102 (10)
Geometric parameters (Å, º) top
Mn1—N52.1889 (16)C18—N21.482 (3)
Mn1—N72.1978 (17)C18—H18A0.9700
Mn1—N32.2063 (17)C18—H18B0.9700
Mn1—N12.4071 (17)C19—N21.484 (3)
Mn1—Cl12.4078 (8)C19—C201.487 (3)
Mn1—N22.4938 (17)C19—H19A0.9700
C1—N11.470 (3)C19—H19B0.9700
C1—C21.497 (3)C20—N71.315 (3)
C1—H1A0.9700C20—N81.342 (3)
C1—H1B0.9700C21—N81.379 (3)
C2—N31.316 (3)C21—C221.383 (3)
C2—N41.345 (3)C21—C261.404 (3)
C3—C41.392 (3)C22—C231.370 (4)
C3—C81.393 (3)C22—H220.9300
C3—N31.395 (2)C23—C241.388 (4)
C4—C51.375 (3)C23—H230.9300
C4—H40.9300C24—C251.375 (3)
C5—C61.380 (4)C24—H240.9300
C5—H50.9300C25—C261.388 (3)
C6—C71.366 (4)C25—H250.9300
C6—H60.9300C26—N71.395 (3)
C7—C81.404 (3)C27—N21.476 (3)
C7—H70.9300C27—C281.499 (3)
C8—N41.376 (3)C27—H27A0.9700
C9—N11.473 (3)C27—H27B0.9700
C9—C101.497 (3)C28—N101.312 (3)
C9—H9A0.9700C28—N91.360 (3)
C9—H9B0.9700C29—N91.374 (3)
C10—N51.312 (2)C29—C341.384 (3)
C10—N61.346 (2)C29—C301.391 (3)
C11—N61.386 (3)C30—C311.380 (4)
C11—C121.388 (3)C30—H300.9300
C11—C161.399 (3)C31—C321.381 (4)
C12—C131.381 (4)C31—H310.9300
C12—H120.9300C32—C331.367 (4)
C13—C141.393 (4)C32—H320.9300
C13—H130.9300C33—C341.401 (3)
C14—C151.377 (3)C33—H330.9300
C14—H140.9300C34—N101.388 (3)
C15—C161.384 (3)N4—H4A0.851 (10)
C15—H150.9300N6—H6A0.843 (10)
C16—N51.399 (2)N8—H80.855 (10)
C17—N11.479 (3)N9—H90.847 (10)
C17—C181.511 (3)O3—H3A0.819 (10)
C17—H17A0.9700O3—H3B0.835 (10)
C17—H17B0.9700
N5—Mn1—N7156.40 (6)C20—C19—H19B109.3
N5—Mn1—N398.35 (6)H19A—C19—H19B108.0
N7—Mn1—N395.05 (6)N7—C20—N8112.80 (18)
N5—Mn1—N174.97 (6)N7—C20—C19124.59 (18)
N7—Mn1—N190.68 (6)N8—C20—C19122.59 (18)
N3—Mn1—N172.89 (6)N8—C21—C22133.0 (2)
N5—Mn1—Cl1100.73 (4)N8—C21—C26105.36 (18)
N7—Mn1—Cl194.39 (5)C22—C21—C26121.6 (2)
N3—Mn1—Cl1105.02 (5)C23—C22—C21117.3 (2)
N1—Mn1—Cl1174.68 (4)C23—C22—H22121.4
N5—Mn1—N285.00 (6)C21—C22—H22121.4
N7—Mn1—N273.08 (6)C22—C23—C24121.6 (2)
N3—Mn1—N2145.62 (6)C22—C23—H23119.2
N1—Mn1—N275.08 (6)C24—C23—H23119.2
Cl1—Mn1—N2107.93 (5)C25—C24—C23121.7 (2)
N1—C1—C2108.90 (16)C25—C24—H24119.2
N1—C1—H1A109.9C23—C24—H24119.2
C2—C1—H1A109.9C24—C25—C26117.6 (2)
N1—C1—H1B109.9C24—C25—H25121.2
C2—C1—H1B109.9C26—C25—H25121.2
H1A—C1—H1B108.3C25—C26—N7131.23 (19)
N3—C2—N4112.98 (18)C25—C26—C21120.19 (19)
N3—C2—C1122.85 (17)N7—C26—C21108.58 (18)
N4—C2—C1124.03 (18)N2—C27—C28116.69 (18)
C4—C3—C8120.7 (2)N2—C27—H27A108.1
C4—C3—N3130.4 (2)C28—C27—H27A108.1
C8—C3—N3108.90 (18)N2—C27—H27B108.1
C5—C4—C3117.0 (2)C28—C27—H27B108.1
C5—C4—H4121.5H27A—C27—H27B107.3
C3—C4—H4121.5N10—C28—N9112.32 (18)
C4—C5—C6122.1 (2)N10—C28—C27125.14 (18)
C4—C5—H5119.0N9—C28—C27122.42 (18)
C6—C5—H5119.0N9—C29—C34105.17 (17)
C7—C6—C5122.2 (2)N9—C29—C30132.7 (2)
C7—C6—H6118.9C34—C29—C30122.1 (2)
C5—C6—H6118.9C31—C30—C29116.4 (2)
C6—C7—C8116.5 (2)C31—C30—H30121.8
C6—C7—H7121.7C29—C30—H30121.8
C8—C7—H7121.7C30—C31—C32121.8 (2)
N4—C8—C3105.75 (18)C30—C31—H31119.1
N4—C8—C7132.8 (2)C32—C31—H31119.1
C3—C8—C7121.5 (2)C33—C32—C31122.0 (2)
N1—C9—C10111.66 (16)C33—C32—H32119.0
N1—C9—H9A109.3C31—C32—H32119.0
C10—C9—H9A109.3C32—C33—C34117.2 (2)
N1—C9—H9B109.3C32—C33—H33121.4
C10—C9—H9B109.3C34—C33—H33121.4
H9A—C9—H9B107.9C29—C34—N10110.07 (17)
N5—C10—N6112.84 (17)C29—C34—C33120.5 (2)
N5—C10—C9124.15 (17)N10—C34—C33129.5 (2)
N6—C10—C9123.00 (17)C1—N1—C9110.72 (16)
N6—C11—C12132.7 (2)C1—N1—C17111.94 (16)
N6—C11—C16105.43 (17)C9—N1—C17112.47 (16)
C12—C11—C16121.9 (2)C1—N1—Mn1105.12 (12)
C13—C12—C11116.3 (2)C9—N1—Mn1108.33 (11)
C13—C12—H12121.9C17—N1—Mn1107.90 (12)
C11—C12—H12121.9C27—N2—C18112.46 (16)
C12—C13—C14122.2 (2)C27—N2—C19112.10 (16)
C12—C13—H13118.9C18—N2—C19111.78 (17)
C14—C13—H13118.9C27—N2—Mn1105.26 (12)
C15—C14—C13121.4 (2)C18—N2—Mn1104.54 (11)
C15—C14—H14119.3C19—N2—Mn1110.21 (12)
C13—C14—H14119.3C2—N3—C3105.15 (16)
C14—C15—C16117.3 (2)C2—N3—Mn1113.98 (13)
C14—C15—H15121.4C3—N3—Mn1138.25 (13)
C16—C15—H15121.4C2—N4—C8107.21 (17)
C15—C16—N5130.39 (19)C2—N4—H4A121.2 (17)
C15—C16—C11121.03 (19)C8—N4—H4A131.3 (17)
N5—C16—C11108.57 (18)C10—N5—C16105.76 (16)
N1—C17—C18111.77 (17)C10—N5—Mn1115.66 (12)
N1—C17—H17A109.3C16—N5—Mn1137.62 (13)
C18—C17—H17A109.3C10—N6—C11107.40 (16)
N1—C17—H17B109.3C10—N6—H6A124.5 (17)
C18—C17—H17B109.3C11—N6—H6A128.1 (17)
H17A—C17—H17B107.9C20—N7—C26105.59 (16)
N2—C18—C17111.39 (17)C20—N7—Mn1118.21 (13)
N2—C18—H18A109.4C26—N7—Mn1133.69 (13)
C17—C18—H18A109.4C20—N8—C21107.65 (17)
N2—C18—H18B109.4C20—N8—H8124.6 (17)
C17—C18—H18B109.4C21—N8—H8127.0 (17)
H18A—C18—H18B108.0C28—N9—C29107.41 (17)
N2—C19—C20111.61 (17)C28—N9—H9129.4 (17)
N2—C19—H19A109.3C29—N9—H9123.1 (17)
C20—C19—H19A109.3C28—N10—C34105.03 (17)
N2—C19—H19B109.3H3A—O3—H3B114.4 (18)
N1—C1—C2—N322.5 (3)N3—Mn1—N2—C27157.38 (12)
N1—C1—C2—N4162.06 (19)N1—Mn1—N2—C27135.62 (13)
C8—C3—C4—C51.2 (3)Cl1—Mn1—N2—C2739.81 (13)
N3—C3—C4—C5177.1 (2)N5—Mn1—N2—C1858.80 (12)
C3—C4—C5—C60.6 (3)N7—Mn1—N2—C18112.34 (13)
C4—C5—C6—C70.4 (4)N3—Mn1—N2—C1838.70 (17)
C5—C6—C7—C80.8 (4)N1—Mn1—N2—C1816.95 (12)
C4—C3—C8—N4179.73 (19)Cl1—Mn1—N2—C18158.48 (11)
N3—C3—C8—N41.1 (2)N5—Mn1—N2—C19179.06 (14)
C4—C3—C8—C70.9 (3)N7—Mn1—N2—C197.92 (14)
N3—C3—C8—C7177.77 (18)N3—Mn1—N2—C1981.56 (17)
C6—C7—C8—N4178.3 (2)N1—Mn1—N2—C19103.31 (14)
C6—C7—C8—C30.1 (3)Cl1—Mn1—N2—C1981.26 (14)
N1—C9—C10—N511.4 (3)N4—C2—N3—C30.4 (2)
N1—C9—C10—N6170.01 (18)C1—C2—N3—C3175.43 (18)
N6—C11—C12—C13178.6 (3)N4—C2—N3—Mn1165.50 (13)
C16—C11—C12—C131.5 (4)C1—C2—N3—Mn110.3 (2)
C11—C12—C13—C140.7 (4)C4—C3—N3—C2178.9 (2)
C12—C13—C14—C150.2 (5)C8—C3—N3—C20.4 (2)
C13—C14—C15—C160.4 (4)C4—C3—N3—Mn119.6 (3)
C14—C15—C16—N5179.9 (2)C8—C3—N3—Mn1158.89 (15)
C14—C15—C16—C111.2 (3)N5—Mn1—N3—C295.69 (14)
N6—C11—C16—C15178.22 (19)N7—Mn1—N3—C264.83 (14)
C12—C11—C16—C151.8 (3)N1—Mn1—N3—C224.33 (13)
N6—C11—C16—N50.8 (2)Cl1—Mn1—N3—C2160.76 (13)
C12—C11—C16—N5179.2 (2)N2—Mn1—N3—C22.3 (2)
N1—C17—C18—N264.5 (2)N5—Mn1—N3—C3106.22 (19)
N2—C19—C20—N79.5 (3)N7—Mn1—N3—C393.26 (19)
N2—C19—C20—N8172.27 (19)N1—Mn1—N3—C3177.6 (2)
N8—C21—C22—C23177.2 (2)Cl1—Mn1—N3—C32.7 (2)
C26—C21—C22—C230.5 (4)N2—Mn1—N3—C3160.41 (16)
C21—C22—C23—C242.3 (4)N3—C2—N4—C81.1 (2)
C22—C23—C24—C252.1 (4)C1—C2—N4—C8174.68 (19)
C23—C24—C25—C260.0 (4)C3—C8—N4—C21.3 (2)
C24—C25—C26—N7177.3 (2)C7—C8—N4—C2177.4 (2)
C24—C25—C26—C211.7 (3)N6—C10—N5—C160.1 (2)
N8—C21—C26—C25179.8 (2)C9—C10—N5—C16178.61 (18)
C22—C21—C26—C251.4 (3)N6—C10—N5—Mn1170.87 (13)
N8—C21—C26—N70.6 (2)C9—C10—N5—Mn17.8 (2)
C22—C21—C26—N7177.7 (2)C15—C16—N5—C10178.4 (2)
N2—C27—C28—N1078.5 (3)C11—C16—N5—C100.4 (2)
N2—C27—C28—N9105.8 (2)C15—C16—N5—Mn113.9 (4)
N9—C29—C30—C31179.0 (2)C11—C16—N5—Mn1167.21 (15)
C34—C29—C30—C310.6 (3)N7—Mn1—N5—C1069.2 (2)
C29—C30—C31—C320.3 (3)N3—Mn1—N5—C1054.70 (14)
C30—C31—C32—C330.3 (4)N1—Mn1—N5—C1014.98 (13)
C31—C32—C33—C340.7 (4)Cl1—Mn1—N5—C10161.82 (13)
N9—C29—C34—N100.2 (2)N2—Mn1—N5—C1090.85 (14)
C30—C29—C34—N10178.56 (19)N7—Mn1—N5—C16123.9 (2)
N9—C29—C34—C33178.98 (19)N3—Mn1—N5—C16112.11 (19)
C30—C29—C34—C330.2 (3)N1—Mn1—N5—C16178.2 (2)
C32—C33—C34—C290.4 (3)Cl1—Mn1—N5—C165.0 (2)
C32—C33—C34—N10178.9 (2)N2—Mn1—N5—C16102.34 (19)
C2—C1—N1—C977.9 (2)N5—C10—N6—C110.6 (2)
C2—C1—N1—C17155.78 (17)C9—C10—N6—C11178.14 (18)
C2—C1—N1—Mn138.91 (18)C12—C11—N6—C10179.1 (3)
C10—C9—N1—C1136.64 (17)C16—C11—N6—C100.8 (2)
C10—C9—N1—C1797.29 (19)N8—C20—N7—C261.1 (2)
C10—C9—N1—Mn121.87 (19)C19—C20—N7—C26177.2 (2)
C18—C17—N1—C1158.62 (18)N8—C20—N7—Mn1163.37 (14)
C18—C17—N1—C976.0 (2)C19—C20—N7—Mn118.3 (3)
C18—C17—N1—Mn143.4 (2)C25—C26—N7—C20178.8 (2)
N5—Mn1—N1—C1138.30 (13)C21—C26—N7—C200.3 (2)
N7—Mn1—N1—C160.67 (12)C25—C26—N7—Mn120.3 (4)
N3—Mn1—N1—C134.40 (12)C21—C26—N7—Mn1160.69 (15)
Cl1—Mn1—N1—C1101.9 (5)N5—Mn1—N7—C2035.9 (3)
N2—Mn1—N1—C1132.95 (13)N3—Mn1—N7—C20160.38 (15)
N5—Mn1—N1—C919.90 (12)N1—Mn1—N7—C2087.50 (15)
N7—Mn1—N1—C9179.07 (12)Cl1—Mn1—N7—C2094.09 (15)
N3—Mn1—N1—C983.99 (13)N2—Mn1—N7—C2013.33 (15)
Cl1—Mn1—N1—C916.4 (5)N5—Mn1—N7—C26165.01 (17)
N2—Mn1—N1—C9108.66 (13)N3—Mn1—N7—C2640.50 (19)
N5—Mn1—N1—C17102.10 (13)N1—Mn1—N7—C26113.38 (19)
N7—Mn1—N1—C1758.93 (13)Cl1—Mn1—N7—C2665.03 (19)
N3—Mn1—N1—C17154.01 (14)N2—Mn1—N7—C26172.4 (2)
Cl1—Mn1—N1—C17138.5 (4)N7—C20—N8—C211.5 (3)
N2—Mn1—N1—C1713.35 (12)C19—C20—N8—C21176.9 (2)
C28—C27—N2—C1862.6 (2)C22—C21—N8—C20176.8 (3)
C28—C27—N2—C1964.3 (2)C26—C21—N8—C201.2 (2)
C28—C27—N2—Mn1175.86 (15)N10—C28—N9—C290.1 (2)
C17—C18—N2—C27159.79 (17)C27—C28—N9—C29176.31 (19)
C17—C18—N2—C1973.1 (2)C34—C29—N9—C280.1 (2)
C17—C18—N2—Mn146.13 (18)C30—C29—N9—C28178.5 (2)
C20—C19—N2—C27119.4 (2)N9—C28—N10—C340.3 (2)
C20—C19—N2—C18113.2 (2)C27—C28—N10—C34176.32 (19)
C20—C19—N2—Mn12.6 (2)C29—C34—N10—C280.3 (2)
N5—Mn1—N2—C2759.88 (13)C33—C34—N10—C28178.9 (2)
N7—Mn1—N2—C27128.99 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···N10i0.84 (1)2.07 (1)2.884 (3)167 (3)
N4—H4A···Cl2ii0.85 (1)2.31 (1)3.147 (2)169 (2)
N8—H8···O3iii0.86 (1)1.92 (1)2.755 (3)164 (2)
N9—H9···Cl1iv0.85 (1)2.49 (2)3.242 (2)149 (2)
C19—H19B···Cl1iv0.972.693.607 (3)157
N6—H6A···Cl20.84 (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, z1; (iv) x+2, y+2, z.

Experimental details

Crystal data
Chemical formula[MnCl(C34H32N10)]Cl·H2O
Mr724.55
Crystal system, space groupTriclinic, 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)
V3)1885.8 (8)
Z2
Radiation typeMo Kα
µ (mm1)0.53
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.901, 0.949
No. of measured, independent and
observed [I > 2σ(I)] reflections
20876, 8156, 6487
Rint0.025
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.127, 1.06
No. of reflections8156
No. of parameters453
No. of restraints7
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Selected bond angles (º) top
N5—Mn1—N7156.40 (6)N3—Mn1—Cl1105.02 (5)
N5—Mn1—N398.35 (6)N1—Mn1—Cl1174.68 (4)
N7—Mn1—N395.05 (6)N5—Mn1—N285.00 (6)
N5—Mn1—N174.97 (6)N7—Mn1—N273.08 (6)
N7—Mn1—N190.68 (6)N3—Mn1—N2145.62 (6)
N3—Mn1—N172.89 (6)N1—Mn1—N275.08 (6)
N5—Mn1—Cl1100.73 (4)Cl1—Mn1—N2107.93 (5)
N7—Mn1—Cl194.39 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3B···N10i0.835 (10)2.065 (11)2.884 (3)167 (3)
N4—H4A···Cl2ii0.851 (10)2.308 (11)3.147 (2)169 (2)
N8—H8···O3iii0.855 (10)1.922 (12)2.755 (3)164 (2)
N9—H9···Cl1iv0.847 (10)2.485 (15)3.242 (2)149 (2)
C19—H19B···Cl1iv0.972.693.607 (3)157.4
N6—H6A···Cl20.843 (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, z1; (iv) x+2, y+2, z.
 

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