PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): m194–m195.
Published online 2009 January 14. doi:  10.1107/S1600536809000981
PMCID: PMC2968132

Aqua­(2,9-dimethyl-1,10-phenanthroline-κ2 N,N′)bis­(2-hydroxy­benzoato-κO)manganese(II) 2,9-dimethyl-1,10-phenanthroline hemisolvate

Abstract

In the asymmetric unit of the title complex, [Mn(C7H5O3)2(C14H12N2)(H2O)]·0.5C14H12N2, the MnII ion is coordinated by a bidentate 2,9-dimethyl-1,10-phenanthroline (dmphen) mol­ecule, one water mol­ecule and two monodentate 2-hydroxy­benzoate anions in a distorted trigonal-bipyramidal geometry. The OH group of the 2-hydroxy­benzoate anion is disordered over two positions with site-occupancy factors of 0.5. The asymmetric unit is completed with by an uncoordinated half-mol­ecule of dmphen, disordered about a crystallographic twofold axis. In the crystal structure, mol­ecules are linked into a two-dimensional framework by O—H(...)N, O—H(...)O and C—H(...)O hydrogen bonds. The packing of the structure is further stabilized by π–π stacking inter­actions involving dmphen mol­ecules, with centroid–centroid separations of 3.8027 (3) and 3.6319 (3) Å.

Related literature

For background to Mn- and phenanthroline-containing complexes, see: Rüttinger & Dismukes (1997 [triangle]); Wang et al. (1996 [triangle]); Wall et al. (1999 [triangle]); Naing et al. (1995 [triangle]). For related structures, see: Shen & Yuan (2004 [triangle]); Pan & Xu (2005 [triangle]); Su et al. (2005 [triangle]); Pan et al. (2006 [triangle]); Shen et al. (2007 [triangle]); Xuan et al. (2007 [triangle]); Zhao et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m194-scheme1.jpg

Experimental

Crystal data

  • [Mn(C7H5O3)2(C14H12N2)(H2O)]·0.5C14H12N2
  • M r = 659.56
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m194-efi7.jpg
  • a = 23.225 (2) Å
  • b = 19.6902 (17) Å
  • c = 14.0225 (12) Å
  • β = 94.342 (1)°
  • V = 6394.2 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.47 mm−1
  • T = 293 (2) K
  • 0.49 × 0.43 × 0.36 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2004 [triangle]) T min = 0.804, T max = 0.849
  • 23566 measured reflections
  • 5959 independent reflections
  • 4384 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.157
  • S = 1.02
  • 5959 reflections
  • 449 parameters
  • 152 restraints
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000981/bh2207sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000981/bh2207Isup2.hkl

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

Acknowledgments

Financial support from the Science Fund of Henan Province for Distinguished Young Scholars (No. 074100510005) is gratefully acknowledged.

supplementary crystallographic information

Comment

It is generally believed that manganese plays an important role in biological systems (Rüttinger & Dismukes, 1997). In addition, metal-phenanthroline complexes and their derivatives have attracted much attention during recent decades because of their peculiar features (Wang et al., 1996; Wall et al., 1999; Naing et al., 1995). A number of Mn(II) complexes have been synthesized and structures determined (Shen & Yuan, 2004; Pan & Xu, 2005; Su et al., 2005; Pan et al., 2006; Shen et al., 2007; Xuan et al., 2007; Zhao et al., 2007). The title complex, (I), was recently obtained from the reaction of manganese nitrate, sodium 2-hydroxybenzoate and dmphen in an ethanol/water mixture, and its crystal structure is reported here.

The structure of the title compound, (I), is shown in Fig. 1. The MnII ion is five-coordinated by two N atoms from a dmphen ligand, and three O atoms from two 2-hydroxybenzoate ligands and a water molecule. The [MnO3N2] unit presents a distorted trigonal bipyramidal geometry, with N2 and O1 atoms occupying the axial positions, with axial O1—Mn1—N2 angle being 169.01 (9)°. The corresponding bond lengths are listed in Table 1. The OH group in one 2-hydroxybenzoate ligand is disordered over two positions with equal site occupancy factors. The whole uncoordinated dmphen molecule present in the asymmetric unit is also disordered equally between two sites related by a twofold axis.

The intramolecular hydrogen bonds between the hydroxy group, water molecule and uncoordinated carboxyl O atoms stabilize the conformation of the complex. In the crystal structure, molecules are linked into a two-dimensional framework by O—H···N and C—H···O hydrogen bonds (Table 2, Fig. 2). A partially overlapped arrangement of neighboring parallel Mn1B-dmphen (symmetry code: x + 1/2, y + 1/2, z) and Mn1C-dmphen rings (symmetry code: -x + 1, -y + 1, -z + 1) is observed in the crystal structure (Fig. 3). The shorter face-to-face separation of 3.3894 (16) Å clearly indicates the existence of π–π stacking interactions between the dmphen ligands. Furthermore, the distance between the ring centroids X1A (C8B···C11B/N2B/C13B) of coordinated Mn1B-dmphen and X1D (C33C···C35C/C33D···C35D) of uncoordinated C35C-dmphen (symmetry code: x + 1/2, y + 1/2, z) is 3.6319 (3) Å. This value is identical to the van der Waals thickness of the π–π stacking interaction between the nearly parallel coordinated dmphen and uncoordinated dmphen [dihedral angle: 1.36 (6)°], although dmphen rings are well overlapped with respect to each other (Fig. 3). This combination of hydrogen bonds and π–π stacking interactions builds a three-dimensional network architecture in the crystal.

Experimental

2-hydroxybenzoic acid (0.0697 g, 0.5 mmol) and NaOH (0.0194 g, 0.5 mmol) were dissolved in distilled water (10 ml) and a 50% solution of Mn(NO3)2 (0.2103 g, 0.5 mmol) was added. This solution was added to a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N2.0.5H2O, 0.1089 g, 0.5 mmol) in ethanol (10 ml). The mixture was stirred at 323 K and then refluxed for 5 h, cooled to room temperature and filtered. Yellow single crystals of (I) appeared over a period of 8 d. by slow evaporation at room temperature.

Refinement

The OH group of a 2-hydroxybenzoate anion is disordered over two positions and site occupancy factors were fixed to 1/2. The whole uncoordinated dmphen is also disordered by symmetry, and its occupation factor in the asymmetric unit was fixed to 1/2. For this dmphen molecule (16 non-H atoms), displacement parameters were restrained: a rigid bond restraint was applied to connected atoms [DELU (Sheldrick, 2008)] and bonded atoms were restrained to have the same Uij components [SIMU (Sheldrick, 2008)]. Methyl H and hydroxyl H atoms were placed in calculated positions, with C—H = 0.96 and O—H = 0.82 Å, and refined with free torsion angles to fit the electron density; Uiso(H) = 1.5Ueq(carrier atom). Other H atoms were placed in calculated positions, with C—H = 0.93 Å, and refined using the riding-model approximation with Uiso(H) = 1.2Ueq(carrier C).

Figures

Fig. 1.
The molecular structure of the title complex with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The hydrogen bonds (dashed lines) in the crystal structure of (I). Displacement ellipsoids are at the 20% probability level.
Fig. 3.
The π–π interactions between the dmphen rings of neighboring molecules in the crystal structure of (I), with 10% probability displacement ellipsoids. H atoms have been omitted for clarity. symmetry codes: (Mn1B, C35C) x + 1/2, ...

Crystal data

[Mn(C7H5O3)2(C14H12N2)(H2O)]·0.5C14H12N2F(000) = 2736
Mr = 659.56Dx = 1.370 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 7104 reflections
a = 23.225 (2) Åθ = 2.5–23.7°
b = 19.6902 (17) ŵ = 0.47 mm1
c = 14.0225 (12) ÅT = 293 K
β = 94.342 (1)°Block, yellow
V = 6394.2 (10) Å30.49 × 0.43 × 0.36 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer5959 independent reflections
Radiation source: fine-focus sealed tube4384 reflections with I > 2σ(I)
graphiteRint = 0.022
[var phi] and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)h = −28→28
Tmin = 0.804, Tmax = 0.849k = −23→23
23566 measured reflectionsl = −16→16

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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0779P)2 + 6.8361P] where P = (Fo2 + 2Fc2)/3
5959 reflections(Δ/σ)max = 0.001
449 parametersΔρmax = 0.34 e Å3
152 restraintsΔρmin = −0.33 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Mn10.336181 (19)0.09320 (2)0.70559 (3)0.05897 (18)
O10.34065 (10)−0.01168 (11)0.6768 (2)0.0831 (7)
O20.43061 (12)−0.04509 (14)0.7166 (3)0.1290 (13)
O50.27211 (13)0.07614 (13)0.8014 (2)0.0973 (8)
O60.21336 (19)0.07237 (18)0.6732 (2)0.1386 (14)
O70.1036 (2)0.0548 (3)0.6931 (3)0.1689 (17)
H70.13280.06070.66470.253*
O80.42499 (11)0.08236 (12)0.7546 (3)0.1120 (11)
H1W0.43570.04370.74350.168*
H2W0.44770.11370.74510.168*
N10.32803 (11)0.15690 (14)0.57097 (16)0.0647 (6)
N20.34711 (10)0.20176 (11)0.75410 (16)0.0563 (6)
C10.3151 (2)0.0612 (2)0.4651 (3)0.1138 (15)
H1A0.35000.04020.49150.171*
H1B0.31020.05210.39770.171*
H1C0.28280.04310.49570.171*
C20.31853 (16)0.1361 (2)0.4812 (2)0.0828 (10)
C30.31289 (17)0.1831 (3)0.4035 (2)0.0924 (12)
H3A0.30730.16740.34090.111*
C40.31578 (18)0.2507 (2)0.4215 (3)0.0972 (12)
H4A0.31130.28130.37090.117*
C50.32514 (15)0.2746 (2)0.5132 (2)0.0789 (9)
C60.32921 (17)0.34444 (19)0.5369 (3)0.0901 (11)
H60.32470.37630.48790.108*
C70.33927 (18)0.36627 (19)0.6262 (3)0.0951 (12)
H7A0.34180.41260.63850.114*
C80.34610 (14)0.31949 (16)0.7028 (3)0.0744 (9)
C90.35821 (17)0.3382 (2)0.7977 (3)0.0914 (11)
H90.36180.38400.81320.110*
C100.36477 (17)0.2919 (2)0.8670 (3)0.0868 (11)
H100.37340.30540.93000.104*
C110.35866 (14)0.22276 (17)0.8445 (2)0.0685 (8)
C120.36389 (18)0.1703 (2)0.9209 (2)0.0926 (12)
H12A0.32620.15400.93300.139*
H12B0.38200.18980.97830.139*
H12C0.38690.13320.90070.139*
C130.34150 (12)0.24857 (14)0.6833 (2)0.0598 (7)
C140.33147 (13)0.22509 (15)0.5877 (2)0.0622 (7)
C150.37894 (15)−0.05680 (16)0.6906 (3)0.0752 (9)
C160.36092 (14)−0.12862 (14)0.6736 (2)0.0616 (7)
C170.30455 (15)−0.14487 (16)0.6432 (2)0.0712 (8)
H170.2770−0.11090.63250.085*0.50
O40.4564 (3)−0.1659 (4)0.7233 (5)0.1179 (19)*0.50
H4D0.4645−0.12780.70470.177*0.50
C180.2891 (2)−0.2119 (2)0.6277 (3)0.0975 (13)
H180.2514−0.22280.60630.117*
C190.3292 (3)−0.2622 (2)0.6438 (3)0.1088 (16)
H190.3182−0.30710.63340.131*
C200.3841 (3)−0.24798 (19)0.6744 (3)0.1033 (14)
H200.4107−0.28300.68490.124*
C210.40101 (18)−0.18138 (17)0.6903 (3)0.0817 (10)
H210.4388−0.17140.71230.098*0.50
O30.2628 (2)−0.0972 (3)0.6327 (4)0.0854 (13)*0.50
H3D0.2762−0.06020.64910.128*0.50
C220.22287 (19)0.06925 (16)0.7612 (3)0.0768 (9)
C230.17424 (14)0.05748 (13)0.8236 (2)0.0645 (8)
C240.1176 (2)0.0519 (2)0.7857 (4)0.1016 (13)
C250.0734 (2)0.0432 (3)0.8492 (6)0.132 (2)
H250.03510.03970.82530.158*
C260.0871 (3)0.0399 (3)0.9424 (6)0.137 (2)
H260.05750.03490.98310.165*
C270.1427 (3)0.0436 (2)0.9813 (4)0.1140 (17)
H270.15090.03951.04700.137*
C280.18578 (16)0.05344 (15)0.9226 (2)0.0727 (9)
H280.22360.05750.94880.087*
C290.4784 (4)0.1418 (3)0.5219 (3)0.161 (5)0.50
H29A0.51060.11260.53940.241*0.50
H29B0.47740.15170.45470.241*0.50
H29C0.44320.11950.53580.241*0.50
C300.4845 (3)0.2056 (3)0.5768 (3)0.125 (3)0.50
C310.4823 (2)0.2698 (3)0.5390 (2)0.145 (3)0.50
H310.47670.27530.47310.174*0.50
C320.4880 (3)0.3258 (3)0.5959 (3)0.143 (3)0.50
H320.48600.36900.56880.172*0.50
C330.4969 (2)0.31839 (18)0.6938 (3)0.124 (2)0.50
C340.49936 (18)0.25172 (16)0.7319 (2)0.0965 (18)0.50
C350.5041 (3)0.37274 (15)0.7589 (4)0.143 (3)0.50
H350.50240.41680.73490.171*0.50
N30.4929 (2)0.1958 (2)0.6702 (3)0.0967 (19)0.50
C29'0.5197 (4)0.0964 (2)0.9930 (4)0.124 (3)0.50
H29D0.52210.06800.93780.186*0.50
H29E0.48510.08591.02340.186*0.50
H29F0.55270.08841.03710.186*0.50
C30'0.5187 (2)0.1684 (2)0.9634 (3)0.104 (2)0.50
C31'0.52517 (19)0.2231 (3)1.0247 (2)0.115 (2)0.50
H31'0.53070.21591.09030.139*0.50
C32'0.5236 (2)0.2876 (2)0.9901 (3)0.131 (3)0.50
H32'0.52810.32401.03220.158*0.50
C33'0.5152 (2)0.29941 (17)0.8935 (3)0.114 (2)0.50
C34'0.50877 (17)0.24249 (15)0.8322 (2)0.0898 (19)0.50
C35'0.5130 (3)0.36443 (15)0.8510 (3)0.131 (3)0.50
H35'0.51800.40250.89000.157*0.50
N3'0.5108 (2)0.17597 (16)0.8701 (3)0.0930 (19)0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0702 (3)0.0426 (2)0.0647 (3)−0.00241 (19)0.0088 (2)0.00082 (18)
O10.0740 (14)0.0444 (11)0.129 (2)0.0033 (10)−0.0054 (13)−0.0120 (12)
O20.0761 (17)0.0733 (18)0.231 (4)0.0028 (13)−0.030 (2)−0.038 (2)
O50.0916 (19)0.0795 (17)0.125 (2)−0.0098 (14)0.0375 (17)0.0049 (15)
O60.223 (4)0.126 (3)0.0712 (19)0.038 (3)0.038 (2)0.0291 (17)
O70.183 (4)0.187 (4)0.125 (3)0.009 (4)−0.066 (3)−0.005 (3)
O80.0700 (15)0.0613 (14)0.202 (3)−0.0088 (11)−0.0083 (18)−0.0295 (17)
N10.0730 (16)0.0756 (17)0.0456 (13)−0.0130 (13)0.0055 (11)−0.0043 (11)
N20.0652 (14)0.0512 (13)0.0524 (13)0.0012 (10)0.0040 (10)−0.0015 (10)
C10.141 (4)0.116 (3)0.086 (3)−0.021 (3)0.012 (3)−0.041 (3)
C20.087 (2)0.102 (3)0.0592 (19)−0.017 (2)0.0081 (16)−0.0144 (18)
C30.097 (3)0.135 (4)0.0450 (18)−0.010 (3)0.0034 (17)−0.001 (2)
C40.103 (3)0.121 (4)0.067 (2)−0.014 (3)0.002 (2)0.023 (2)
C50.075 (2)0.092 (3)0.069 (2)−0.0074 (18)0.0006 (16)0.0210 (18)
C60.095 (3)0.064 (2)0.110 (3)0.0003 (19)0.003 (2)0.037 (2)
C70.107 (3)0.056 (2)0.121 (3)0.0011 (19)−0.001 (3)0.014 (2)
C80.074 (2)0.0536 (18)0.096 (3)0.0012 (15)0.0059 (18)0.0041 (17)
C90.099 (3)0.067 (2)0.107 (3)0.0013 (19)0.004 (2)−0.028 (2)
C100.098 (3)0.080 (2)0.082 (2)−0.002 (2)0.005 (2)−0.031 (2)
C110.0689 (19)0.072 (2)0.0648 (19)0.0012 (15)0.0073 (14)−0.0141 (15)
C120.110 (3)0.117 (3)0.0497 (18)−0.001 (2)−0.0023 (18)−0.0007 (19)
C130.0626 (17)0.0503 (15)0.0661 (18)0.0010 (13)0.0027 (13)0.0063 (13)
C140.0654 (18)0.0583 (17)0.0629 (18)−0.0053 (14)0.0034 (14)0.0127 (14)
C150.075 (2)0.0547 (18)0.095 (2)−0.0048 (16)0.0003 (18)−0.0109 (16)
C160.084 (2)0.0441 (15)0.0564 (16)−0.0013 (14)0.0062 (15)−0.0026 (12)
C170.087 (2)0.0599 (18)0.0681 (19)−0.0136 (16)0.0133 (16)−0.0041 (15)
C180.118 (3)0.071 (2)0.107 (3)−0.037 (2)0.026 (2)−0.016 (2)
C190.178 (5)0.050 (2)0.102 (3)−0.026 (3)0.038 (3)−0.006 (2)
C200.163 (5)0.050 (2)0.098 (3)0.022 (2)0.020 (3)0.0111 (19)
C210.104 (3)0.062 (2)0.078 (2)0.0064 (18)−0.0002 (19)−0.0021 (16)
C220.110 (3)0.0456 (16)0.077 (2)0.0060 (18)0.024 (2)0.0095 (15)
C230.078 (2)0.0359 (14)0.079 (2)−0.0028 (13)0.0055 (16)−0.0021 (13)
C240.106 (3)0.079 (3)0.116 (3)−0.002 (2)−0.020 (3)−0.014 (2)
C250.083 (3)0.112 (4)0.202 (6)−0.022 (3)0.017 (4)−0.034 (4)
C260.127 (5)0.091 (3)0.204 (7)−0.024 (3)0.078 (5)−0.037 (4)
C270.178 (5)0.072 (3)0.099 (3)−0.018 (3)0.061 (3)−0.014 (2)
C280.099 (2)0.0497 (17)0.072 (2)−0.0065 (16)0.0232 (18)−0.0021 (14)
C290.127 (10)0.212 (10)0.141 (9)−0.047 (10)−0.005 (9)−0.002 (8)
C300.086 (5)0.157 (6)0.134 (6)−0.016 (6)0.007 (5)0.050 (5)
C310.103 (6)0.176 (7)0.157 (7)0.002 (7)0.009 (6)0.069 (5)
C320.105 (6)0.146 (7)0.180 (7)0.013 (6)0.023 (6)0.067 (5)
C330.093 (4)0.097 (4)0.185 (6)0.013 (4)0.022 (6)0.041 (4)
C340.065 (3)0.079 (3)0.148 (5)0.006 (5)0.020 (4)0.030 (3)
C350.111 (5)0.085 (4)0.233 (7)0.002 (7)0.025 (6)0.016 (6)
N30.066 (4)0.110 (4)0.116 (5)−0.006 (4)0.017 (4)0.030 (4)
C29'0.109 (7)0.143 (7)0.119 (7)0.008 (7)0.005 (6)0.035 (6)
C30'0.079 (5)0.122 (5)0.111 (5)0.008 (4)0.015 (5)0.005 (4)
C31'0.082 (4)0.147 (6)0.120 (5)−0.008 (5)0.018 (4)−0.026 (4)
C32'0.093 (5)0.141 (5)0.163 (6)−0.011 (5)0.026 (5)−0.043 (5)
C33'0.077 (5)0.090 (4)0.179 (5)−0.001 (4)0.032 (5)−0.016 (4)
C34'0.061 (4)0.069 (3)0.142 (5)0.000 (3)0.023 (4)0.003 (3)
C35'0.100 (5)0.076 (4)0.220 (7)−0.011 (4)0.038 (7)−0.019 (5)
N3'0.075 (4)0.091 (4)0.114 (4)−0.002 (3)0.015 (4)0.005 (3)

Geometric parameters (Å, °)

Mn1—O52.105 (3)O4—H210.4385
Mn1—O12.108 (2)C18—C191.366 (6)
Mn1—O82.135 (3)C18—H180.9300
Mn1—N22.252 (2)C19—C201.344 (7)
Mn1—N12.262 (2)C19—H190.9300
O1—C151.262 (4)C20—C211.382 (5)
O2—C151.249 (4)C20—H200.9300
O5—C221.243 (5)C21—H210.9300
O6—C221.238 (4)O3—H170.4262
O7—C241.315 (6)O3—H3D0.8200
O7—H70.8200C22—C231.499 (5)
O8—H1W0.8200C23—C241.386 (5)
O8—H2W0.8288C23—C281.396 (5)
N1—C21.326 (4)C24—C251.418 (8)
N1—C141.364 (4)C25—C261.323 (8)
N2—C111.342 (4)C25—H250.9300
N2—C131.354 (4)C26—C271.366 (8)
C1—C21.494 (6)C26—H260.9300
C1—H1A0.9600C27—C281.357 (6)
C1—H1B0.9600C27—H270.9300
C1—H1C0.9600C28—H280.9300
C2—C31.428 (6)C29—C301.4759
C3—C41.356 (6)C29—H29A0.9600
C3—H3A0.9300C29—H29B0.9600
C4—C51.371 (5)C29—H29C0.9600
C4—H4A0.9300C30—N31.3240
C5—C61.415 (5)C30—C311.3702
C5—C141.429 (4)C31—C321.3611
C6—C71.329 (6)C31—H310.9300
C6—H60.9300C32—C331.3816
C7—C81.414 (5)C32—H320.9300
C7—H7A0.9300C33—C351.4076
C8—C91.389 (5)C33—C341.4164
C8—C131.425 (4)C34—N31.4017
C9—C101.333 (6)C34—C34'1.4192
C9—H90.9300C35—C35'1.3035
C10—C111.402 (5)C35—H350.9300
C10—H100.9300C29'—C30'1.4763
C11—C121.486 (5)C29'—H29D0.9600
C12—H12A0.9600C29'—H29E0.9600
C12—H12B0.9600C29'—H29F0.9600
C12—H12C0.9600C30'—N3'1.3159
C13—C141.420 (4)C30'—C31'1.3801
C15—C161.489 (4)C31'—C32'1.3576
C16—C171.383 (4)C31'—H31'0.9300
C16—C211.403 (5)C32'—C33'1.3740
C17—O31.350 (6)C32'—H32'0.9300
C17—C181.380 (5)C33'—C35'1.4111
C17—H170.9300C33'—C34'1.4130
O4—C211.368 (7)C34'—N3'1.4129
O4—H4D0.8200C35'—H35'0.9300
O1—Mn1—N2169.01 (9)C18—C17—H17119.6
O5—Mn1—O8119.39 (14)C16—C17—H17120.5
O5—Mn1—N1127.02 (11)C21—O4—H4D109.2
O8—Mn1—N1110.00 (12)H4D—O4—H21110.2
O5—Mn1—O190.77 (10)C19—C18—C17120.1 (4)
O1—Mn1—O884.46 (9)C19—C18—H18120.0
O5—Mn1—N291.58 (10)C17—C18—H18120.0
O8—Mn1—N285.04 (9)C20—C19—C18121.4 (4)
O1—Mn1—N1112.67 (10)C20—C19—H19119.3
N2—Mn1—N174.11 (9)C18—C19—H19119.3
C15—O1—Mn1134.8 (2)C19—C20—C21120.0 (4)
C22—O5—Mn1113.5 (3)C19—C20—H20120.0
C24—O7—H7109.5C21—C20—H20120.0
Mn1—O8—H1W109.3O4—C21—C20121.0 (5)
Mn1—O8—H2W119.0O4—C21—C16119.1 (4)
H1W—O8—H2W117.1C20—C21—C16119.9 (4)
C2—N1—C14118.0 (3)C20—C21—H21120.2
C2—N1—Mn1128.2 (2)C16—C21—H21119.9
C14—N1—Mn1113.69 (18)C17—O3—H3D109.4
C11—N2—C13119.0 (3)H17—O3—H3D106.6
C11—N2—Mn1126.0 (2)O6—C22—O5122.3 (4)
C13—N2—Mn1114.98 (18)O6—C22—C23120.3 (4)
C2—C1—H1A109.5O5—C22—C23117.4 (3)
C2—C1—H1B109.5C24—C23—C28118.9 (4)
H1A—C1—H1B109.5C24—C23—C22121.6 (4)
C2—C1—H1C109.5C28—C23—C22119.6 (3)
H1A—C1—H1C109.5O7—C24—C23122.2 (5)
H1B—C1—H1C109.5O7—C24—C25119.2 (5)
N1—C2—C3121.6 (4)C23—C24—C25118.6 (5)
N1—C2—C1116.8 (3)C26—C25—C24119.7 (5)
C3—C2—C1121.6 (3)C26—C25—H25120.1
C4—C3—C2119.6 (3)C24—C25—H25120.1
C4—C3—H3A120.2C25—C26—C27122.7 (5)
C2—C3—H3A120.2C25—C26—H26118.6
C3—C4—C5120.9 (4)C27—C26—H26118.6
C3—C4—H4A119.5C28—C27—C26119.0 (5)
C5—C4—H4A119.5C28—C27—H27120.5
C4—C5—C6123.8 (4)C26—C27—H27120.5
C4—C5—C14116.9 (4)C27—C28—C23121.1 (4)
C6—C5—C14119.3 (3)C27—C28—H28119.5
C7—C6—C5122.6 (3)C23—C28—H28119.5
C7—C6—H6118.7N3—C30—C31121.1
C5—C6—H6118.7N3—C30—C29113.1
C6—C7—C8120.4 (4)C31—C30—C29125.8
C6—C7—H7A119.8C32—C31—C30121.4
C8—C7—H7A119.8C32—C31—H31119.3
C9—C8—C7123.9 (4)C30—C31—H31119.3
C9—C8—C13116.8 (3)C31—C32—C33119.8
C7—C8—C13119.3 (3)C31—C32—H32120.1
C10—C9—C8121.4 (3)C33—C32—H32120.1
C10—C9—H9119.3C32—C33—C35124.4
C8—C9—H9119.3C32—C33—C34118.1
C9—C10—C11119.8 (3)C35—C33—C34117.5
C9—C10—H10120.1N3—C34—C33119.8
C11—C10—H10120.1N3—C34—C34'120.8
N2—C11—C10121.4 (3)C33—C34—C34'119.4
N2—C11—C12117.8 (3)C35'—C35—C33123.3
C10—C11—C12120.8 (3)C35'—C35—H35118.4
C11—C12—H12A109.5C33—C35—H35118.4
C11—C12—H12B109.5C30—N3—C34119.7
H12A—C12—H12B109.5N3'—C30'—C31'122.0
C11—C12—H12C109.5N3'—C30'—C29'112.8
H12A—C12—H12C109.5C31'—C30'—C29'125.2
H12B—C12—H12C109.5C32'—C31'—C30'120.6
N2—C13—C14118.0 (3)C32'—C31'—H31'119.7
N2—C13—C8121.6 (3)C30'—C31'—H31'119.7
C14—C13—C8120.3 (3)C31'—C32'—C33'120.6
N1—C14—C13119.1 (2)C31'—C32'—H32'119.7
N1—C14—C5123.0 (3)C33'—C32'—H32'119.7
C13—C14—C5117.9 (3)C32'—C33'—C35'124.6
O2—C15—O1124.4 (3)C32'—C33'—C34'117.7
O2—C15—C16118.3 (3)C35'—C33'—C34'117.7
O1—C15—C16117.3 (3)N3'—C34'—C33'120.5
C17—C16—C21118.8 (3)N3'—C34'—C34119.3
C17—C16—C15121.1 (3)C33'—C34'—C34120.2
C21—C16—C15120.1 (3)C35—C35'—C33'122.0
O3—C17—C18118.1 (4)C35—C35'—H35'119.0
O3—C17—C16121.9 (3)C33'—C35'—H35'119.0
C18—C17—C16119.9 (4)C30'—N3'—C34'118.5
O5—Mn1—O1—C15−115.4 (4)O1—C15—C16—C170.5 (5)
O8—Mn1—O1—C154.0 (4)O2—C15—C16—C212.4 (5)
N2—Mn1—O1—C15−13.1 (8)O1—C15—C16—C21−178.1 (3)
N1—Mn1—O1—C15113.4 (4)C21—C16—C17—O3174.9 (4)
O1—Mn1—O5—C22−81.1 (2)C15—C16—C17—O3−3.7 (5)
O8—Mn1—O5—C22−165.2 (2)C21—C16—C17—C18−1.6 (5)
N2—Mn1—O5—C22109.6 (2)C15—C16—C17—C18179.8 (3)
N1—Mn1—O5—C2238.4 (3)O3—C17—C18—C19−175.6 (4)
O5—Mn1—N1—C2−100.0 (3)C16—C17—C18—C191.0 (6)
O1—Mn1—N1—C29.4 (3)C17—C18—C19—C20−0.2 (7)
O8—Mn1—N1—C2101.8 (3)C18—C19—C20—C210.0 (7)
N2—Mn1—N1—C2−179.7 (3)C19—C20—C21—O4178.7 (5)
O5—Mn1—N1—C1477.4 (2)C19—C20—C21—C16−0.6 (6)
O1—Mn1—N1—C14−173.16 (19)C17—C16—C21—O4−177.9 (4)
O8—Mn1—N1—C14−80.8 (2)C15—C16—C21—O40.7 (6)
N2—Mn1—N1—C14−2.3 (2)C17—C16—C21—C201.4 (5)
O5—Mn1—N2—C1154.5 (3)C15—C16—C21—C20−180.0 (3)
O1—Mn1—N2—C11−47.8 (6)Mn1—O5—C22—O6−0.1 (4)
O8—Mn1—N2—C11−64.9 (3)Mn1—O5—C22—C23−179.5 (2)
N1—Mn1—N2—C11−177.3 (3)O6—C22—C23—C24−2.1 (5)
O5—Mn1—N2—C13−125.9 (2)O5—C22—C23—C24177.4 (3)
O1—Mn1—N2—C13131.8 (5)O6—C22—C23—C28179.4 (3)
O8—Mn1—N2—C13114.7 (2)O5—C22—C23—C28−1.2 (4)
N1—Mn1—N2—C132.30 (19)C28—C23—C24—O7−179.5 (4)
C14—N1—C2—C31.0 (5)C22—C23—C24—O71.9 (6)
Mn1—N1—C2—C3178.3 (3)C28—C23—C24—C250.7 (5)
C14—N1—C2—C1179.9 (3)C22—C23—C24—C25−177.8 (4)
Mn1—N1—C2—C1−2.8 (5)O7—C24—C25—C26179.7 (6)
N1—C2—C3—C4−1.7 (6)C23—C24—C25—C26−0.5 (7)
C1—C2—C3—C4179.4 (4)C24—C25—C26—C27−1.0 (9)
C2—C3—C4—C51.2 (6)C25—C26—C27—C282.4 (8)
C3—C4—C5—C6179.3 (4)C26—C27—C28—C23−2.1 (6)
C3—C4—C5—C14−0.1 (6)C24—C23—C28—C270.6 (5)
C4—C5—C6—C7−178.8 (4)C22—C23—C28—C27179.2 (3)
C14—C5—C6—C70.6 (6)N3—C30—C31—C32−0.6
C5—C6—C7—C8−0.4 (7)C29—C30—C31—C32179.5
C6—C7—C8—C9178.2 (4)C30—C31—C32—C330.6
C6—C7—C8—C13−0.6 (6)C31—C32—C33—C35179.2
C7—C8—C9—C10−179.3 (4)C31—C32—C33—C34−0.3
C13—C8—C9—C10−0.5 (6)C32—C33—C34—N30.0
C8—C9—C10—C11−0.8 (6)C35—C33—C34—N3−179.5
C13—N2—C11—C100.3 (4)C32—C33—C34—C34'179.6
Mn1—N2—C11—C10179.9 (2)C35—C33—C34—C34'0.1
C13—N2—C11—C12179.3 (3)C32—C33—C35—C35'−179.3
Mn1—N2—C11—C12−1.1 (4)C34—C33—C35—C35'0.2
C9—C10—C11—N21.0 (6)C31—C30—N3—C340.3
C9—C10—C11—C12−178.0 (4)C29—C30—N3—C34−179.8
C11—N2—C13—C14177.6 (3)C33—C34—N3—C300.0
Mn1—N2—C13—C14−2.0 (3)C34'—C34—N3—C30−179.6
C11—N2—C13—C8−1.6 (4)N3'—C30'—C31'—C32'0.1
Mn1—N2—C13—C8178.7 (2)C29'—C30'—C31'—C32'179.9
C9—C8—C13—N21.7 (5)C30'—C31'—C32'—C33'0.2
C7—C8—C13—N2−179.3 (3)C31'—C32'—C33'—C35'−180.0
C9—C8—C13—C14−177.5 (3)C31'—C32'—C33'—C34'−0.3
C7—C8—C13—C141.4 (5)C32'—C33'—C34'—N3'0.1
C2—N1—C14—C13179.9 (3)C35'—C33'—C34'—N3'179.8
Mn1—N1—C14—C132.2 (3)C32'—C33'—C34'—C34179.2
C2—N1—C14—C50.2 (5)C35'—C33'—C34'—C34−1.1
Mn1—N1—C14—C5−177.5 (2)N3—C34—C34'—N3'−0.9
N2—C13—C14—N1−0.1 (4)C33—C34—C34'—N3'179.5
C8—C13—C14—N1179.1 (3)N3—C34—C34'—C33'180.0
N2—C13—C14—C5179.5 (3)C33—C34—C34'—C33'0.4
C8—C13—C14—C5−1.2 (4)C33—C35—C35'—C33'−1.0
C4—C5—C14—N1−0.6 (5)C32'—C33'—C35'—C35−179.0
C6—C5—C14—N1179.9 (3)C34'—C33'—C35'—C351.4
C4—C5—C14—C13179.7 (3)C31'—C30'—N3'—C34'−0.2
C6—C5—C14—C130.2 (5)C29'—C30'—N3'—C34'179.9
Mn1—O1—C15—O2−10.6 (7)C33'—C34'—N3'—C30'0.1
Mn1—O1—C15—C16169.9 (2)C34—C34'—N3'—C30'−179.0
O2—C15—C16—C17−179.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H2W···N3'0.832.523.083 (5)127
O8—H2W···N30.832.233.026 (5)160
O8—H1W···O20.821.792.571 (3)159
O7—H7···O60.821.882.609 (6)147
O4—H4D···O20.821.822.453 (7)133
O3—H3D···O10.821.792.514 (5)146
C12—H12C···O80.962.503.309 (5)142
O8—H2W···N3i0.832.383.070 (4)141
O8—H2W···N3'i0.832.303.013 (6)145
C6—H6···O6ii0.932.573.450 (5)158

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2207).

References

  • Bruker (2004). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Naing, K., Takahashi, M., Taniguchi, M. & Yamagishi, A. (1995). Inorg. Chem.34, 350–356.
  • Pan, T.-T., Su, J.-R. & Xu, D.-J. (2006). Acta Cryst. E62, m1403–m1404.
  • Pan, T.-T. & Xu, D.-J. (2005). Acta Cryst. E61, m740–m742.
  • Rüttinger, W. & Dismukes, G. C. (1997). Chem. Rev.97, 1–24. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shen, Y.-L., Sun, S.-L. & Song, W.-D. (2007). Acta Cryst. E63, m1309–m1311.
  • Shen, X.-P. & Yuan, A.-H. (2004). Acta Cryst. E60, m1074–m1075.
  • Su, J.-R., Zhang, L. & Xu, D.-J. (2005). Acta Cryst. E61, m939–m941.
  • Wall, M., Linkletter, B., Williams, D., Lebuis, A.-M., Hynes, R. C. & Chin, J. (1999). J. Am. Chem. Soc.121, 4710–4711.
  • Wang, J., Cai, X., Rivas, G., Shiraishi, H., Farias, P. A. M. & Dontha, N. (1996). Anal. Chem.68, 2629–2634. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.
  • Xuan, X., Zhao, P. & Zhang, S. (2007). Acta Cryst. E63, m2813–m2814.
  • Zhao, P.-Z., Xuan, X.-P. & Wang, J.-G. (2007). Acta Cryst. E63, m2127.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography