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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): m1178.
Published online 2008 August 16. doi:  10.1107/S1600536808025804
PMCID: PMC2960601

Perchlorato[N,N,N′,N′-tetra­kis(2-pyridyl­meth­yl)cyclo­hexane-1,2-diamine]manganese(II) perchlorate

Abstract

The asymmetric unit of the title compound, [Mn(ClO4)(C30H34N6)]ClO4, consists of a cationic [Mn(ClO4)(C30H34N6)]+ complex and a perchlorate anion. In the complex, the Mn2+ ion is seven-coordinated in an approximately penta­gonal–bipyramidal environment by six N atoms from the hexa­dentate N,N,N′,N′-tetra­kis(2-pyridylmeth­yl)­cyclo­hexane-1,2-diamine (tpdach) ligand and one O atom from a perchlorate anion. The complex displays inter­molecular π–π inter­actions between adjacent pyridine rings (centroid-to-centroid distance 4.133 Å). Moreover, there are weak intra- and inter­molecular C—H(...)O hydrogen bonds. The Cl atom and two O atoms of the perchlorate are disordered, with a site-occupancy factor of 0.59 (2) for the major component.

Related literature

For details of some other tpdach complexes, see: Hwang & Ha (2006 [triangle]); McCusker et al. (1993 [triangle]). For the synthesis of the ligand, see: Toftlund & Yde-Anderson (1981 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-m1178-scheme1.jpg

Experimental

Crystal data

  • [Mn(ClO4)(C30H34N6)]ClO4
  • M r = 732.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-m1178-efi1.jpg
  • a = 14.223 (5) Å
  • b = 14.121 (5) Å
  • c = 16.504 (6) Å
  • β = 105.987 (6)°
  • V = 3186.6 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.64 mm−1
  • T = 293 (2) K
  • 0.25 × 0.25 × 0.20 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.690, T max = 0.879
  • 9661 measured reflections
  • 5412 independent reflections
  • 4446 reflections with I > 2σ(I)
  • R int = 0.020

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.093
  • S = 0.96
  • 5412 reflections
  • 452 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.39 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1804 Friedel pairs
  • Flack parameter: 0.007 (16)

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: ORTEP-3 (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025804/zl2134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025804/zl2134Isup2.hkl

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

Acknowledgments

This work was supported by a Korea Research Foundation Grant funded by the Korean Government (MOEHRD) (KRF-2007-412-J02001).

supplementary crystallographic information

Comment

The crystal structure of the title compound consists of a cationic complex, [Mn(ClO4)(C30H34N6)]+, and a ClO4- anion (Fig. 1). In the cation, the Mn2+ ion is seven-coordinated by six N atoms from tpdach and one O atom from a ClO4- ligand in an approximately pentagonal bipyramidal structure, in which the N2, N3, N4, N6 and O1 atoms form the pentagonal plane with the N1 and N5 atoms at the apices. In the analogous Fe2+ compound [Fe(C30H34N6)](ClO4)2 the Fe ion is six-coordinated in a distorted octahedral environment (McCusker et al. 1993). The apical N1—Mn1—N5 bond angle is 176.0 (1)°, and the Mn1—N1 and Mn1—N5 bond lengths are nearly equivalent (2.294 (3) Å and 2.273 (3) Å, respectively) and shorter than the Mn1—N bonds for N2, N3, N4 and N6 in the equatorial plane (2.388 (3) Å to 2.422 (3) Å). Within the plane, the chelating angles lie in the range of 70.76 (9) to 74.13 (9)° and the O1—Mn1—N bond angles for N2 and N6 are 78.9 (1)° and 78.1 (1), respectively. The complex displays intermolecular π–π interactions between adjacent pyridine rings. The shortest distance between Cg1 (the centroid of six-membered ring N2–C11) and Cg2a (ring N6–C29, symmetry code a: 1/2 + x,-1/2 + y,z) is 4.133 Å, and the dihedral angle between the ring planes is 6.59°. The C10···C27a and C11···C27a distances are 3.469 Å and 3.491 Å, respectively. Moreover, there are intra- and intermolecular hydrogen bonds between the C and O atoms with d(C···O) = 3.006 Å to 3.436 Å (Fig. 2, Table 1).

Experimental

N,N,N',N'-Tetrakis(2-pyridylmethyl)cyclohexane-1,2-diamine (tpdach), C30H34N6, was synthesized according to a literature procedure (Toftlund & Yde-Anderson, 1981). Mn(ClO4)2.6H2O (0.61 g, 1.69 mmol) and tpdach (0.40 g, 0.84 mmol) in EtOH (10 ml) were stirred for 2 h at room temperature. The solvent was removed in vacuo, the residue recrystallized from acetone–ether and filtered, to give a dark yellow powder (0.44 g). Crystals suitable for X-ray analysis were obtained by slow evaporation from an acetone–ethyl acetate solution. MS (FAB): m/z 632, 634 (Mn(tpdach)(ClO4)+).

Refinement

H atoms were positioned geometrically and allowed to ride on their respective carrier atoms [C—H = 0.93 (aromatic CH), 0.97 (CH2) or 0.98 Å (CH) and Uiso(H) = 1.2Ueq(C)]. The ClO4- anions (particularly Cl1, O3 and O4) displayed relatively large displacement factors so that the anions appeared to be partially disordered. Atoms Cl1, O3 and O4 were thus modelled anisotropically as disordered over two sites, with a site occupancy factor of 0.59 (2) for the major component. Floating origin restraints were generated automatically by the program SHELXL97.

Figures

Fig. 1.
The structure of the title compound with the numbering scheme. Displacement ellipsoids are drawn at the 20% probability level. H atoms have been omitted for clarity, and only the major component of the disordered atoms Cl, O3 and O4 is shown.
Fig. 2.
View of the unit-cell contents of the title compound. Hydrogen-bond interactions are drawn as dashed lines.

Crystal data

[Mn(ClO4)(C30H34N6)]ClO4F000 = 1516
Mr = 732.47Dx = 1.527 Mg m3
Monoclinic, CcMo Kα radiation λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 3537 reflections
a = 14.223 (5) Åθ = 2.6–22.9º
b = 14.121 (5) ŵ = 0.64 mm1
c = 16.504 (6) ÅT = 293 (2) K
β = 105.987 (6)ºStick, yellow
V = 3186.6 (19) Å30.25 × 0.25 × 0.20 mm
Z = 4

Data collection

Bruker SMART 1000 CCD diffractometer5412 independent reflections
Radiation source: fine-focus sealed tube4446 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 293(2) Kθmax = 27.6º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2000)h = −11→18
Tmin = 0.690, Tmax = 0.879k = −18→18
9661 measured reflectionsl = −21→21

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039  w = 1/[σ2(Fo2) + (0.103P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.093(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.39 e Å3
5412 reflectionsΔρmin = −0.29 e Å3
452 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), with 1804 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.007 (16)
Secondary atom site location: difference Fourier map

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)
Mn10.15888 (5)0.33639 (3)0.36637 (4)0.03769 (12)
N10.2229 (2)0.47899 (19)0.42192 (18)0.0450 (7)
N20.2968 (2)0.2727 (2)0.32882 (19)0.0494 (7)
N30.2886 (2)0.30494 (17)0.49337 (17)0.0385 (6)
N40.0803 (2)0.27813 (17)0.46689 (15)0.0362 (6)
N50.0853 (2)0.19852 (19)0.31237 (16)0.0399 (6)
N60.0022 (2)0.4106 (2)0.34287 (18)0.0465 (7)
C10.1793 (3)0.5634 (2)0.3961 (3)0.0597 (10)
H10.12320.56410.35100.072*
C20.2147 (3)0.6482 (2)0.4339 (3)0.0583 (10)
H20.18310.70480.41440.070*
C30.2968 (3)0.6477 (2)0.5004 (2)0.0549 (9)
H30.32170.70370.52760.066*
C40.3421 (3)0.5623 (2)0.5264 (2)0.0483 (8)
H40.39840.56060.57130.058*
C50.3045 (2)0.4795 (2)0.4861 (2)0.0393 (7)
C60.3564 (3)0.3869 (2)0.5087 (2)0.0469 (8)
H6A0.40290.37900.47580.056*
H6B0.39280.38810.56770.056*
C70.3158 (3)0.2794 (3)0.2543 (2)0.0605 (11)
H70.26750.30390.20910.073*
C80.4026 (3)0.2522 (3)0.2405 (3)0.0668 (11)
H80.41290.25830.18740.080*
C90.4742 (3)0.2156 (3)0.3069 (3)0.0619 (10)
H90.53450.19780.30000.074*
C100.4550 (3)0.2060 (3)0.3832 (3)0.0567 (9)
H100.50200.18060.42880.068*
C110.3656 (3)0.2342 (2)0.3920 (2)0.0446 (8)
C120.3408 (3)0.2206 (2)0.4749 (2)0.0472 (8)
H12A0.30010.16500.47170.057*
H12B0.40040.21110.51990.057*
C130.2477 (2)0.2910 (2)0.5668 (2)0.0401 (7)
H130.23140.35400.58380.048*
C140.3198 (3)0.2466 (3)0.6443 (2)0.0504 (9)
H14A0.33820.18400.62990.060*
H14B0.37850.28500.66080.060*
C150.2752 (3)0.2392 (3)0.7173 (2)0.0556 (10)
H15A0.32240.21200.76580.067*
H15B0.25800.30180.73270.067*
C160.1864 (3)0.1786 (3)0.6929 (2)0.0541 (10)
H16A0.15890.17220.74030.065*
H16B0.20390.11590.67790.065*
C170.1106 (3)0.2223 (3)0.6182 (2)0.0491 (9)
H17A0.09040.28330.63440.059*
H17B0.05340.18170.60230.059*
C180.1528 (2)0.2349 (2)0.54187 (18)0.0381 (7)
H180.16860.17170.52510.046*
C190.0988 (3)0.1550 (3)0.2434 (2)0.0496 (8)
H190.13630.18520.21290.060*
C200.0597 (3)0.0692 (3)0.2171 (2)0.0612 (11)
H200.07070.04120.16940.073*
C210.0044 (4)0.0238 (3)0.2606 (3)0.0734 (14)
H21−0.0217−0.03580.24400.088*
C22−0.0122 (4)0.0680 (3)0.3298 (2)0.0645 (11)
H22−0.05050.03910.36010.077*
C230.0290 (3)0.1558 (2)0.35356 (19)0.0402 (7)
C240.0067 (3)0.2074 (2)0.4259 (2)0.0432 (8)
H24A−0.05600.23880.40540.052*
H24B0.00060.16130.46770.052*
C25−0.0532 (3)0.4527 (3)0.2737 (2)0.0533 (9)
H25−0.03130.45300.22550.064*
C26−0.1411 (3)0.4959 (3)0.2703 (3)0.0592 (10)
H26−0.17730.52510.22110.071*
C27−0.1740 (3)0.4950 (3)0.3403 (3)0.0617 (11)
H27−0.23320.52340.33970.074*
C28−0.1184 (3)0.4515 (3)0.4115 (3)0.0555 (9)
H28−0.14000.44950.45980.067*
C29−0.0304 (3)0.4106 (2)0.4119 (2)0.0432 (8)
C300.0319 (3)0.3630 (2)0.4887 (2)0.0441 (8)
H30A0.08120.40710.51950.053*
H30B−0.00830.34500.52500.053*
O10.1329 (2)0.3954 (2)0.23005 (16)0.0643 (8)
O20.0969 (4)0.5516 (2)0.1871 (3)0.1098 (14)
Cl1A0.1592 (6)0.4718 (3)0.1811 (5)0.0695 (14)0.589 (18)
O3A0.1337 (14)0.4370 (8)0.0960 (6)0.122 (5)0.589 (18)
O4A0.2592 (6)0.4953 (6)0.2141 (11)0.134 (5)0.589 (18)
Cl1B0.1171 (11)0.4580 (8)0.1590 (6)0.091 (3)0.411 (18)
O3B0.042 (2)0.4334 (16)0.0973 (10)0.214 (13)0.411 (18)
O4B0.2022 (18)0.4735 (14)0.1375 (18)0.147 (12)0.411 (18)
Cl20.16080 (10)0.07166 (10)0.01224 (8)0.0782 (3)
O50.1508 (5)0.1150 (3)−0.0657 (3)0.1315 (16)
O60.0759 (4)0.0230 (4)0.0224 (3)0.1293 (16)
O70.2066 (7)0.1294 (5)0.0740 (4)0.221 (4)
O80.2213 (5)−0.0077 (4)0.0100 (5)0.198 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0350 (2)0.0365 (2)0.0407 (2)−0.0010 (2)0.00912 (18)0.0005 (2)
N10.0405 (15)0.0371 (14)0.0532 (17)0.0025 (13)0.0059 (14)−0.0013 (12)
N20.0407 (17)0.0572 (17)0.0521 (17)0.0059 (15)0.0158 (14)0.0105 (14)
N30.0369 (15)0.0316 (12)0.0466 (15)0.0019 (12)0.0108 (12)0.0025 (11)
N40.0351 (14)0.0355 (13)0.0349 (13)0.0010 (11)0.0044 (11)−0.0026 (10)
N50.0391 (15)0.0414 (14)0.0392 (14)−0.0022 (13)0.0108 (13)−0.0024 (12)
N60.0385 (16)0.0507 (15)0.0478 (16)−0.0003 (13)0.0074 (14)0.0038 (13)
C10.049 (2)0.0463 (19)0.072 (3)0.0035 (18)−0.002 (2)0.0037 (17)
C20.051 (2)0.0386 (19)0.082 (3)0.0042 (17)0.014 (2)0.0030 (18)
C30.060 (2)0.0408 (18)0.065 (2)−0.0132 (18)0.019 (2)−0.0115 (17)
C40.042 (2)0.051 (2)0.049 (2)−0.0118 (17)0.0085 (16)−0.0028 (16)
C50.0375 (18)0.0406 (16)0.0423 (18)−0.0037 (14)0.0153 (15)0.0026 (14)
C60.0324 (18)0.0448 (18)0.059 (2)−0.0030 (15)0.0046 (16)0.0072 (16)
C70.045 (2)0.080 (3)0.056 (2)0.015 (2)0.0142 (19)0.017 (2)
C80.059 (3)0.081 (3)0.070 (3)0.012 (2)0.034 (2)0.017 (2)
C90.046 (2)0.067 (2)0.077 (3)0.015 (2)0.026 (2)0.015 (2)
C100.046 (2)0.060 (2)0.062 (2)0.0140 (19)0.0116 (19)0.0116 (19)
C110.0425 (19)0.0372 (16)0.055 (2)0.0008 (16)0.0143 (17)0.0022 (15)
C120.045 (2)0.0434 (17)0.055 (2)0.0059 (16)0.0163 (17)0.0098 (16)
C130.0408 (18)0.0341 (15)0.0421 (17)0.0045 (15)0.0059 (15)−0.0008 (13)
C140.049 (2)0.0505 (19)0.0447 (19)−0.0019 (17)0.0003 (16)0.0024 (16)
C150.068 (3)0.052 (2)0.0386 (18)0.008 (2)0.0013 (17)0.0047 (16)
C160.069 (3)0.059 (2)0.0304 (17)0.000 (2)0.0076 (17)0.0110 (16)
C170.050 (2)0.055 (2)0.0418 (18)−0.0016 (18)0.0128 (16)0.0034 (16)
C180.0410 (18)0.0382 (16)0.0342 (16)0.0002 (14)0.0088 (14)0.0016 (13)
C190.048 (2)0.057 (2)0.0443 (19)0.0036 (18)0.0127 (16)−0.0091 (16)
C200.069 (3)0.063 (2)0.046 (2)0.006 (2)0.007 (2)−0.0137 (18)
C210.112 (4)0.046 (2)0.058 (2)−0.016 (2)0.017 (3)−0.0156 (19)
C220.090 (3)0.054 (2)0.049 (2)−0.023 (2)0.018 (2)−0.0054 (18)
C230.0395 (18)0.0443 (17)0.0334 (16)−0.0040 (15)0.0042 (14)−0.0013 (13)
C240.0388 (19)0.0471 (19)0.0436 (18)−0.0075 (16)0.0111 (15)−0.0021 (14)
C250.048 (2)0.059 (2)0.049 (2)−0.0088 (19)0.0076 (18)0.0085 (17)
C260.050 (2)0.052 (2)0.064 (2)0.0024 (19)−0.005 (2)0.0071 (18)
C270.049 (2)0.053 (2)0.077 (3)0.0140 (19)0.007 (2)−0.005 (2)
C280.043 (2)0.062 (2)0.061 (2)0.0078 (19)0.0129 (18)−0.0063 (19)
C290.0392 (19)0.0437 (18)0.0454 (18)0.0006 (16)0.0096 (15)−0.0058 (15)
C300.042 (2)0.0504 (18)0.0384 (17)0.0046 (16)0.0093 (15)−0.0037 (14)
O10.0731 (19)0.0666 (17)0.0601 (15)0.0186 (15)0.0301 (15)0.0251 (13)
O20.150 (4)0.070 (2)0.134 (3)0.035 (2)0.079 (3)0.039 (2)
Cl1A0.074 (3)0.0625 (15)0.085 (3)0.0218 (18)0.045 (2)0.0324 (15)
O3A0.191 (15)0.126 (9)0.071 (5)0.033 (9)0.074 (8)0.024 (5)
O4A0.075 (5)0.094 (5)0.233 (13)−0.011 (4)0.045 (7)0.043 (7)
Cl1B0.088 (5)0.120 (5)0.082 (4)0.040 (4)0.050 (4)0.058 (4)
O3B0.21 (2)0.29 (2)0.089 (10)−0.086 (19)−0.047 (13)0.089 (12)
O4B0.16 (2)0.140 (16)0.21 (3)0.044 (14)0.16 (2)0.090 (17)
Cl20.0750 (8)0.0931 (8)0.0693 (7)0.0072 (7)0.0246 (6)0.0060 (6)
O50.187 (5)0.102 (3)0.096 (3)0.002 (3)0.022 (3)0.020 (2)
O60.103 (3)0.179 (4)0.121 (3)−0.022 (3)0.057 (3)−0.033 (3)
O70.325 (12)0.194 (6)0.124 (4)−0.119 (7)0.028 (5)−0.049 (4)
O80.176 (6)0.116 (4)0.366 (10)0.064 (4)0.184 (7)0.098 (5)

Geometric parameters (Å, °)

Mn1—N52.273 (3)C14—H14A0.9700
Mn1—N12.294 (3)C14—H14B0.9700
Mn1—O12.331 (3)C15—C161.487 (6)
Mn1—N42.388 (3)C15—H15A0.9700
Mn1—N22.390 (3)C15—H15B0.9700
Mn1—N62.396 (3)C16—C171.527 (5)
Mn1—N32.422 (3)C16—H16A0.9700
N1—C51.338 (4)C16—H16B0.9700
N1—C11.356 (4)C17—C181.548 (5)
N2—C111.334 (4)C17—H17A0.9700
N2—C71.334 (5)C17—H17B0.9700
N3—C121.478 (4)C18—H180.9800
N3—C61.483 (4)C19—C201.355 (5)
N3—C131.495 (4)C19—H190.9300
N4—C241.470 (4)C20—C211.364 (6)
N4—C301.475 (4)C20—H200.9300
N4—C181.505 (4)C21—C221.377 (6)
N5—C231.329 (4)C21—H210.9300
N5—C191.353 (4)C22—C231.381 (5)
N6—C251.335 (4)C22—H220.9300
N6—C291.342 (4)C23—C241.505 (5)
C1—C21.380 (5)C24—H24A0.9700
C1—H10.9300C24—H24B0.9700
C2—C31.365 (6)C25—C261.378 (6)
C2—H20.9300C25—H250.9300
C3—C41.378 (5)C26—C271.361 (6)
C3—H30.9300C26—H260.9300
C4—C51.378 (5)C27—C281.369 (5)
C4—H40.9300C27—H270.9300
C5—C61.497 (5)C28—C291.377 (5)
C6—H6A0.9700C28—H280.9300
C6—H6B0.9700C29—C301.491 (5)
C7—C81.371 (6)C30—H30A0.9700
C7—H70.9300C30—H30B0.9700
C8—C91.374 (6)O1—Cl1B1.437 (7)
C8—H80.9300O1—Cl1A1.457 (5)
C9—C101.367 (5)O2—Cl1A1.454 (7)
C9—H90.9300O2—Cl1B1.456 (11)
C10—C111.378 (5)Cl1A—O4A1.415 (11)
C10—H100.9300Cl1A—O3A1.437 (12)
C11—C121.517 (5)Cl1B—O3B1.30 (2)
C12—H12A0.9700Cl1B—O4B1.369 (16)
C12—H12B0.9700Cl2—O71.327 (5)
C13—C181.520 (5)Cl2—O51.395 (4)
C13—C141.536 (5)Cl2—O81.419 (5)
C13—H130.9800Cl2—O61.439 (5)
C14—C151.512 (5)
N5—Mn1—N1176.02 (11)C15—C14—C13111.2 (3)
N5—Mn1—O189.66 (10)C15—C14—H14A109.4
N1—Mn1—O190.69 (11)C13—C14—H14A109.4
N5—Mn1—N473.98 (9)C15—C14—H14B109.4
N1—Mn1—N4103.60 (10)C13—C14—H14B109.4
O1—Mn1—N4144.44 (10)H14A—C14—H14B108.0
N5—Mn1—N284.18 (10)C16—C15—C14109.6 (3)
N1—Mn1—N299.77 (11)C16—C15—H15A109.8
O1—Mn1—N278.89 (10)C14—C15—H15A109.8
N4—Mn1—N2128.73 (9)C16—C15—H15B109.8
N5—Mn1—N690.22 (10)C14—C15—H15B109.8
N1—Mn1—N685.98 (10)H15A—C15—H15B108.2
O1—Mn1—N678.13 (10)C15—C16—C17110.2 (3)
N4—Mn1—N670.76 (9)C15—C16—H16A109.6
N2—Mn1—N6156.36 (10)C17—C16—H16A109.6
N5—Mn1—N3109.95 (9)C15—C16—H16B109.6
N1—Mn1—N372.01 (9)C17—C16—H16B109.6
O1—Mn1—N3141.38 (10)H16A—C16—H16B108.1
N4—Mn1—N374.13 (9)C16—C17—C18111.0 (3)
N2—Mn1—N370.80 (10)C16—C17—H17A109.4
N6—Mn1—N3132.33 (10)C18—C17—H17A109.4
C5—N1—C1117.7 (3)C16—C17—H17B109.4
C5—N1—Mn1118.9 (2)C18—C17—H17B109.4
C1—N1—Mn1123.3 (2)H17A—C17—H17B108.0
C11—N2—C7117.3 (3)N4—C18—C13111.6 (2)
C11—N2—Mn1115.4 (2)N4—C18—C17112.6 (3)
C7—N2—Mn1127.0 (2)C13—C18—C17110.8 (3)
C12—N3—C6108.9 (3)N4—C18—H18107.2
C12—N3—C13113.0 (2)C13—C18—H18107.2
C6—N3—C13110.2 (2)C17—C18—H18107.2
C12—N3—Mn1106.0 (2)N5—C19—C20122.3 (4)
C6—N3—Mn1107.98 (18)N5—C19—H19118.8
C13—N3—Mn1110.59 (19)C20—C19—H19118.8
C24—N4—C30110.1 (3)C19—C20—C21119.8 (4)
C24—N4—C18110.1 (2)C19—C20—H20120.1
C30—N4—C18112.9 (2)C21—C20—H20120.1
C24—N4—Mn1108.93 (17)C20—C21—C22118.6 (4)
C30—N4—Mn1103.21 (19)C20—C21—H21120.7
C18—N4—Mn1111.38 (19)C22—C21—H21120.7
C23—N5—C19118.0 (3)C21—C22—C23119.2 (4)
C23—N5—Mn1117.7 (2)C21—C22—H22120.4
C19—N5—Mn1124.2 (2)C23—C22—H22120.4
C25—N6—C29117.7 (3)N5—C23—C22122.0 (3)
C25—N6—Mn1129.5 (2)N5—C23—C24118.3 (3)
C29—N6—Mn1112.7 (2)C22—C23—C24119.7 (3)
N1—C1—C2122.9 (4)N4—C24—C23114.5 (3)
N1—C1—H1118.5N4—C24—H24A108.6
C2—C1—H1118.5C23—C24—H24A108.6
C3—C2—C1118.9 (3)N4—C24—H24B108.6
C3—C2—H2120.6C23—C24—H24B108.6
C1—C2—H2120.6H24A—C24—H24B107.6
C2—C3—C4118.6 (3)N6—C25—C26123.1 (4)
C2—C3—H3120.7N6—C25—H25118.4
C4—C3—H3120.7C26—C25—H25118.4
C5—C4—C3120.4 (3)C27—C26—C25118.8 (4)
C5—C4—H4119.8C27—C26—H26120.6
C3—C4—H4119.8C25—C26—H26120.6
N1—C5—C4121.5 (3)C26—C27—C28118.7 (4)
N1—C5—C6116.9 (3)C26—C27—H27120.7
C4—C5—C6121.4 (3)C28—C27—H27120.7
N3—C6—C5112.7 (3)C27—C28—C29120.1 (4)
N3—C6—H6A109.0C27—C28—H28119.9
C5—C6—H6A109.0C29—C28—H28119.9
N3—C6—H6B109.0N6—C29—C28121.5 (3)
C5—C6—H6B109.0N6—C29—C30117.3 (3)
H6A—C6—H6B107.8C28—C29—C30121.2 (3)
N2—C7—C8123.6 (4)N4—C30—C29111.5 (3)
N2—C7—H7118.2N4—C30—H30A109.3
C8—C7—H7118.2C29—C30—H30A109.3
C7—C8—C9118.4 (4)N4—C30—H30B109.3
C7—C8—H8120.8C29—C30—H30B109.3
C9—C8—H8120.8H30A—C30—H30B108.0
C10—C9—C8118.7 (4)Cl1B—O1—Mn1162.9 (5)
C10—C9—H9120.7Cl1A—O1—Mn1143.4 (4)
C8—C9—H9120.7O4A—Cl1A—O3A114.4 (9)
C9—C10—C11119.5 (4)O4A—Cl1A—O2111.0 (6)
C9—C10—H10120.2O3A—Cl1A—O2109.7 (7)
C11—C10—H10120.2O4A—Cl1A—O1110.2 (5)
N2—C11—C10122.4 (3)O3A—Cl1A—O1104.7 (7)
N2—C11—C12117.0 (3)O2—Cl1A—O1106.4 (4)
C10—C11—C12120.6 (3)O3B—Cl1B—O4B115.7 (16)
N3—C12—C11109.8 (3)O3B—Cl1B—O1112.6 (11)
N3—C12—H12A109.7O4B—Cl1B—O1111.1 (11)
C11—C12—H12A109.7O3B—Cl1B—O2107.4 (13)
N3—C12—H12B109.7O4B—Cl1B—O2101.7 (13)
C11—C12—H12B109.7O1—Cl1B—O2107.4 (6)
H12A—C12—H12B108.2O7—Cl2—O5110.0 (3)
N3—C13—C18111.3 (2)O7—Cl2—O8109.4 (6)
N3—C13—C14114.1 (3)O5—Cl2—O8103.3 (4)
C18—C13—C14110.6 (3)O7—Cl2—O6117.0 (4)
N3—C13—H13106.8O5—Cl2—O6116.2 (3)
C18—C13—H13106.8O8—Cl2—O699.2 (3)
C14—C13—H13106.8
O1—Mn1—N1—C5−135.9 (3)C7—C8—C9—C101.5 (7)
N4—Mn1—N1—C577.0 (3)C8—C9—C10—C11−0.9 (6)
N2—Mn1—N1—C5−57.0 (3)C7—N2—C11—C103.0 (5)
N6—Mn1—N1—C5146.1 (3)Mn1—N2—C11—C10−171.1 (3)
N3—Mn1—N1—C59.0 (2)C7—N2—C11—C12−175.9 (3)
O1—Mn1—N1—C147.9 (3)Mn1—N2—C11—C129.9 (4)
N4—Mn1—N1—C1−99.2 (3)C9—C10—C11—N2−1.4 (6)
N2—Mn1—N1—C1126.7 (3)C9—C10—C11—C12177.5 (4)
N6—Mn1—N1—C1−30.2 (3)C6—N3—C12—C11−66.4 (3)
N3—Mn1—N1—C1−167.3 (3)C13—N3—C12—C11170.8 (3)
N5—Mn1—N2—C11−100.2 (2)Mn1—N3—C12—C1149.6 (3)
N1—Mn1—N2—C1180.2 (2)N2—C11—C12—N3−41.9 (4)
O1—Mn1—N2—C11169.0 (3)C10—C11—C12—N3139.1 (3)
N4—Mn1—N2—C11−36.2 (3)C12—N3—C13—C18−79.4 (3)
N6—Mn1—N2—C11−177.3 (2)C6—N3—C13—C18158.6 (3)
N3—Mn1—N2—C1113.3 (2)Mn1—N3—C13—C1839.3 (3)
N5—Mn1—N2—C786.3 (3)C12—N3—C13—C1446.8 (4)
N1—Mn1—N2—C7−93.3 (3)C6—N3—C13—C14−75.3 (3)
O1—Mn1—N2—C7−4.5 (3)Mn1—N3—C13—C14165.4 (2)
N4—Mn1—N2—C7150.3 (3)N3—C13—C14—C15177.1 (3)
N6—Mn1—N2—C79.2 (5)C18—C13—C14—C15−56.4 (4)
N3—Mn1—N2—C7−160.2 (3)C13—C14—C15—C1660.4 (4)
N5—Mn1—N3—C1243.0 (2)C14—C15—C16—C17−61.0 (4)
N1—Mn1—N3—C12−140.7 (2)C15—C16—C17—C1858.3 (4)
O1—Mn1—N3—C12−73.4 (2)C24—N4—C18—C13159.6 (2)
N4—Mn1—N3—C12108.9 (2)C30—N4—C18—C13−76.9 (3)
N2—Mn1—N3—C12−33.11 (19)Mn1—N4—C18—C1338.6 (3)
N6—Mn1—N3—C12152.61 (19)C24—N4—C18—C17−75.1 (3)
N5—Mn1—N3—C6159.5 (2)C30—N4—C18—C1748.3 (3)
N1—Mn1—N3—C6−24.1 (2)Mn1—N4—C18—C17163.9 (2)
O1—Mn1—N3—C643.2 (3)N3—C13—C18—N4−52.9 (3)
N4—Mn1—N3—C6−134.6 (2)C14—C13—C18—N4179.0 (3)
N2—Mn1—N3—C683.5 (2)N3—C13—C18—C17−179.2 (3)
N6—Mn1—N3—C6−90.8 (2)C14—C13—C18—C1752.7 (4)
N5—Mn1—N3—C13−79.9 (2)C16—C17—C18—N4−179.8 (3)
N1—Mn1—N3—C1396.5 (2)C16—C17—C18—C13−54.1 (4)
O1—Mn1—N3—C13163.77 (18)C23—N5—C19—C20−2.1 (5)
N4—Mn1—N3—C13−13.95 (18)Mn1—N5—C19—C20174.6 (3)
N2—Mn1—N3—C13−155.9 (2)N5—C19—C20—C210.2 (6)
N6—Mn1—N3—C1329.8 (2)C19—C20—C21—C221.4 (7)
N5—Mn1—N4—C24−17.8 (2)C20—C21—C22—C23−1.1 (7)
N1—Mn1—N4—C24158.9 (2)C19—N5—C23—C222.5 (5)
O1—Mn1—N4—C2447.9 (3)Mn1—N5—C23—C22−174.5 (3)
N2—Mn1—N4—C24−86.4 (2)C19—N5—C23—C24−174.9 (3)
N6—Mn1—N4—C2478.2 (2)Mn1—N5—C23—C248.1 (4)
N3—Mn1—N4—C24−134.6 (2)C21—C22—C23—N5−0.9 (6)
N5—Mn1—N4—C30−134.8 (2)C21—C22—C23—C24176.4 (4)
N1—Mn1—N4—C3041.9 (2)C30—N4—C24—C23140.4 (3)
O1—Mn1—N4—C30−69.1 (2)C18—N4—C24—C23−94.5 (3)
N2—Mn1—N4—C30156.64 (18)Mn1—N4—C24—C2327.9 (3)
N6—Mn1—N4—C30−38.81 (18)N5—C23—C24—N4−25.6 (4)
N3—Mn1—N4—C30108.42 (19)C22—C23—C24—N4157.0 (3)
N5—Mn1—N4—C18103.79 (19)C29—N6—C25—C260.2 (5)
N1—Mn1—N4—C18−79.47 (19)Mn1—N6—C25—C26−177.5 (3)
O1—Mn1—N4—C18169.45 (19)N6—C25—C26—C27−0.7 (6)
N2—Mn1—N4—C1835.2 (2)C25—C26—C27—C280.2 (6)
N6—Mn1—N4—C18−160.2 (2)C26—C27—C28—C290.7 (6)
N3—Mn1—N4—C18−12.99 (17)C25—N6—C29—C280.8 (5)
O1—Mn1—N5—C23−142.3 (2)Mn1—N6—C29—C28178.9 (3)
N4—Mn1—N5—C235.7 (2)C25—N6—C29—C30179.8 (3)
N2—Mn1—N5—C23138.8 (2)Mn1—N6—C29—C30−2.2 (4)
N6—Mn1—N5—C23−64.2 (2)C27—C28—C29—N6−1.3 (5)
N3—Mn1—N5—C2371.7 (3)C27—C28—C29—C30179.8 (3)
O1—Mn1—N5—C1940.9 (3)C24—N4—C30—C29−63.3 (3)
N4—Mn1—N5—C19−171.1 (3)C18—N4—C30—C29173.2 (3)
N2—Mn1—N5—C19−38.0 (3)Mn1—N4—C30—C2952.8 (3)
N6—Mn1—N5—C19119.0 (3)N6—C29—C30—N4−36.1 (4)
N3—Mn1—N5—C19−105.1 (3)C28—C29—C30—N4142.8 (3)
N5—Mn1—N6—C25−85.9 (3)N5—Mn1—O1—Cl1B153 (2)
N1—Mn1—N6—C2595.3 (3)N1—Mn1—O1—Cl1B−23 (2)
O1—Mn1—N6—C253.7 (3)N4—Mn1—O1—Cl1B91 (2)
N4—Mn1—N6—C25−158.8 (3)N2—Mn1—O1—Cl1B−123 (2)
N2—Mn1—N6—C25−10.0 (5)N6—Mn1—O1—Cl1B62 (2)
N3—Mn1—N6—C25156.4 (3)N3—Mn1—O1—Cl1B−85 (2)
N5—Mn1—N6—C2996.3 (2)N5—Mn1—O1—Cl1A−167.8 (5)
N1—Mn1—N6—C29−82.5 (2)N1—Mn1—O1—Cl1A16.2 (5)
O1—Mn1—N6—C29−174.0 (2)N4—Mn1—O1—Cl1A131.1 (5)
N4—Mn1—N6—C2923.4 (2)N2—Mn1—O1—Cl1A−83.6 (5)
N2—Mn1—N6—C29172.2 (2)N6—Mn1—O1—Cl1A101.9 (5)
N3—Mn1—N6—C29−21.4 (3)N3—Mn1—O1—Cl1A−45.1 (5)
C5—N1—C1—C2−1.0 (6)Cl1B—O2—Cl1A—O4A169.6 (13)
Mn1—N1—C1—C2175.3 (3)Cl1B—O2—Cl1A—O3A42.3 (12)
N1—C1—C2—C3−0.3 (7)Cl1B—O2—Cl1A—O1−70.5 (9)
C1—C2—C3—C41.0 (6)Cl1B—O1—Cl1A—O4A−167.6 (15)
C2—C3—C4—C5−0.4 (6)Mn1—O1—Cl1A—O4A38.2 (9)
C1—N1—C5—C41.6 (5)Cl1B—O1—Cl1A—O3A−44.2 (12)
Mn1—N1—C5—C4−174.9 (2)Mn1—O1—Cl1A—O3A161.6 (7)
C1—N1—C5—C6−174.8 (3)Cl1B—O1—Cl1A—O272.0 (12)
Mn1—N1—C5—C68.8 (4)Mn1—O1—Cl1A—O2−82.2 (8)
C3—C4—C5—N1−0.9 (5)Cl1A—O1—Cl1B—O3B169 (2)
C3—C4—C5—C6175.3 (3)Mn1—O1—Cl1B—O3B−129 (3)
C12—N3—C6—C5151.6 (3)Cl1A—O1—Cl1B—O4B37.8 (14)
C13—N3—C6—C5−83.9 (3)Mn1—O1—Cl1B—O4B100 (2)
Mn1—N3—C6—C537.0 (3)Cl1A—O1—Cl1B—O2−72.6 (15)
N1—C5—C6—N3−32.3 (4)Mn1—O1—Cl1B—O2−11 (3)
C4—C5—C6—N3151.4 (3)Cl1A—O2—Cl1B—O3B−164.7 (16)
C11—N2—C7—C8−2.4 (6)Cl1A—O2—Cl1B—O4B−42.8 (14)
Mn1—N2—C7—C8171.0 (3)Cl1A—O2—Cl1B—O174.0 (11)
N2—C7—C8—C90.2 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C7—H7···O10.932.413.006 (5)122
C17—H17A···O2i0.972.483.413 (5)161
C18—H18···O8ii0.982.473.436 (6)170
C20—H20···O60.932.463.347 (6)159
C25—H25···O10.932.463.038 (5)121
C25—H25···O20.932.513.199 (5)131
C28—H28···O8iii0.932.483.243 (6)139
C30—H30A···O3Ai0.972.553.434 (11)152

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, −y, z+1/2; (iii) x−1/2, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2134).

References

  • Bruker (2000). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Hwang, I.-C. & Ha, K. (2006). Z. Kristallogr. New Cryst. Struct.221, 468–470.
  • McCusker, J. K., Toftlund, H., Rheingold, A. L. & Hendrickson, D. N. (1993). J. Am. Chem. Soc.115, 1797–1804.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Toftlund, H. & Yde-Anderson, S. (1981). Acta Chem. Scand. A, 35, 575–585.

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