metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Aqua­[1,3-bis­­(benzimidazol-2-yl)-2-oxa­propane]­di­ethano­lmanganese(II) dipicrate ethanol disolvate

aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
*Correspondence e-mail: wuhuilu@163.com

(Received 8 July 2010; accepted 30 July 2010; online 4 August 2010)

In the title complex, [Mn(C16H14N4O)(C2H5OH)2(H2O)](C6H2N3O7)2·2C2H5OH, the MnII ion is in a distorted octa­hedral coordination environment, defined by an MnN2O4 donor set. The 1,3-bis­(benz­imid­azol-2-yl)-2-oxapropane ligand is tridentate. In the crystal structure, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds link the components into a three-dimensional network. The O atoms of one of the nitro groups are disordered over two sets of sites with refined occupancies of 0.577 (11) and 0.423 (11).

Related literature

For the applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008[Chang, C. M., Kulkarni, M. V., Chen, C. H., Wang, C. & Sun, C. M. (2008). J. Comb. Chem. 10, 466-474.]); Harrell et al. (2004[Harrell, C. C., Kohli, P., Siwy, Z. & Martin, C. R. (2004). J. Am. Chem. Soc. 126, 15646-15647.]); Holland & Tolman (2000[Holland, P. L. & Tolman, W. B. (2000). J. Am. Chem. Soc. 122, 6331-6332.]).

[Scheme 1]

Experimental

Crystal data
  • [Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6O

  • Mr = 991.75

  • Monoclinic, P 21 /c

  • a = 10.0519 (3) Å

  • b = 24.8584 (8) Å

  • c = 18.0291 (7) Å

  • β = 98.504 (1)°

  • V = 4455.5 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.39 mm−1

  • T = 153 K

  • 0.39 × 0.25 × 0.22 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.864, Tmax = 0.920

  • 32660 measured reflections

  • 7806 independent reflections

  • 4707 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.074

  • wR(F2) = 0.255

  • S = 1.07

  • 7806 reflections

  • 603 parameters

  • 8 restraints

  • H-atom parameters constrained

  • Δρmax = 0.73 e Å−3

  • Δρmin = −0.97 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1W⋯O5i 0.93 1.99 2.758 (4) 139
O1—H1W⋯O6i 0.93 2.07 2.854 (4) 141
O1—H2W⋯O5 0.93 1.99 2.758 (4) 139
O1—H2W⋯O11 0.93 2.11 2.898 (4) 141
O2—H2⋯O20ii 0.95 1.76 2.659 (7) 157
O3—H3⋯O17iii 0.95 2.09 2.864 (4) 138
O3—H3⋯O18iii 0.95 2.37 3.289 (5) 163
N2—H2B⋯O12i 0.88 1.92 2.676 (4) 142
N2—H2B⋯O18i 0.88 2.25 2.973 (5) 140
N4—H4B⋯O15iv 0.88 2.10 2.907 (5) 152
N4—H4B⋯O16iv 0.88 2.38 3.161 (5) 148
O19—H19⋯O8 0.93 2.35 3.278 (13) 179
O20—H20⋯O19 0.93 1.88 2.807 (13) 179
Symmetry codes: (i) -x+1, -y+1, -z; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y, z; (iv) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2000[Bruker (2000).APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000).APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Bis-benzimidazoles are known to be strong chelating agents coordinating through both of the C=N group nitrogen atoms. In addition, as a typical multidentate ligand they have polymer-forming characteristics. In bioinorganic chemistry, they have been used extensively to help model the active sites of metalloproteins (Holland & Tolman, 2000). The benzimidazole ring system is present in clinically approved anthelmintics, antiulcers, antivirals, and antihistamines (Harrell, et al., 2004). Recently, there have been reports on benzimidazole derivatives exhibiting antitumor and antimicrobial properties and acting as thrombopoietin receptor agonists (Chang, et al., 2008).

We have attempted to prepare organic-inorganic hybrid materials with manganese salts using 1,3-bis(benzimidazol-2-yl)-2-oxapropane (OBB). Herein, we report the crystal structure of the title compound. The asymmetric unit of the title compound is shown in Fig. 1. The MnII ion is coordinated in a distorted octahedral coordination environment. The 1,3-bis(benzimidazol-2-yl)-2-oxapropane ligand acts as tridentate. In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds link the components of the structure into a three-dimensional network (Fig. 2).

Related literature top

For the applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008); Harrell et al. (2004); Holland & Tolman (2000).

Experimental top

To a stirred solution of 1,3-bis(benzimidazol-2-yl)-2-oxapropane (91.6 mg, 0.2 mmol) in hot ethanol (10 ml), Mn(C6H2N3O7)2 (102.9 mg, 0.2 mmol) in ethanol (5 ml) was added. A yellow crystalline product formed rapidly. The precipitate was filtered off, washed with ethanol and Et2O, and dried in vacuo. The dried precipitate was dissolved in DMF to form a yellow solution into which diethylether was allowed to diffuse at room temperature. The yellow crystals suitable for X-ray diffraction studies were obtained after one week (Yield, 72%).

Refinement top

All H atoms were placed in calculated positions and refined in a riding-model approximation with; C—H = 0.95-0.99 Å, N-H = 0.88Å, O-H = 0.93-0.95Å and Uiso(H) = 1.2 Ueq(C, N) or Uiso(H) = 1.5 Ueq(Cmethyl, O).

Structure description top

Bis-benzimidazoles are known to be strong chelating agents coordinating through both of the C=N group nitrogen atoms. In addition, as a typical multidentate ligand they have polymer-forming characteristics. In bioinorganic chemistry, they have been used extensively to help model the active sites of metalloproteins (Holland & Tolman, 2000). The benzimidazole ring system is present in clinically approved anthelmintics, antiulcers, antivirals, and antihistamines (Harrell, et al., 2004). Recently, there have been reports on benzimidazole derivatives exhibiting antitumor and antimicrobial properties and acting as thrombopoietin receptor agonists (Chang, et al., 2008).

We have attempted to prepare organic-inorganic hybrid materials with manganese salts using 1,3-bis(benzimidazol-2-yl)-2-oxapropane (OBB). Herein, we report the crystal structure of the title compound. The asymmetric unit of the title compound is shown in Fig. 1. The MnII ion is coordinated in a distorted octahedral coordination environment. The 1,3-bis(benzimidazol-2-yl)-2-oxapropane ligand acts as tridentate. In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds link the components of the structure into a three-dimensional network (Fig. 2).

For the applications of benzimidazole and bis-benzimidazole compounds, see: Chang et al. (2008); Harrell et al. (2004); Holland & Tolman (2000).

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of the title compound showing 30% ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure of the title compound showing hydrogen bonds as dashed lines. Only the H atoms involved in hydrogen bonds are shown.
Aqua[1,3-bis(benzimidazol-2-yl)-2-oxapropane]diethanolmanganese(II) dipicrate ethanol disolvate top
Crystal data top
[Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6OF(000) = 2060
Mr = 991.75Dx = 1.478 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8263 reflections
a = 10.0519 (3) Åθ = 3.2–25.5°
b = 24.8584 (8) ŵ = 0.39 mm1
c = 18.0291 (7) ÅT = 153 K
β = 98.504 (1)°Block, yellow
V = 4455.5 (3) Å30.39 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker SMART APEXII
diffractometer
7806 independent reflections
Radiation source: fine-focus sealed tube4707 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
ω scansθmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.864, Tmax = 0.920k = 2629
32660 measured reflectionsl = 2121
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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.255H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.1644P)2]
where P = (Fo2 + 2Fc2)/3
7806 reflections(Δ/σ)max = 0.003
603 parametersΔρmax = 0.73 e Å3
8 restraintsΔρmin = 0.97 e Å3
Crystal data top
[Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6OV = 4455.5 (3) Å3
Mr = 991.75Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.0519 (3) ŵ = 0.39 mm1
b = 24.8584 (8) ÅT = 153 K
c = 18.0291 (7) Å0.39 × 0.25 × 0.22 mm
β = 98.504 (1)°
Data collection top
Bruker SMART APEXII
diffractometer
7806 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4707 reflections with I > 2σ(I)
Tmin = 0.864, Tmax = 0.920Rint = 0.045
32660 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0748 restraints
wR(F2) = 0.255H-atom parameters constrained
S = 1.07Δρmax = 0.73 e Å3
7806 reflectionsΔρmin = 0.97 e Å3
603 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
Mn0.28926 (6)0.50170 (2)0.15226 (4)0.0402 (3)
O10.4637 (3)0.50371 (10)0.09714 (18)0.0451 (7)
H1W0.49670.53640.08260.068*
H2W0.50720.47150.09000.068*
O20.3980 (4)0.50978 (15)0.2620 (2)0.0687 (10)
H20.34590.50850.30180.082*
O30.1054 (4)0.49324 (12)0.2034 (2)0.0597 (9)
H30.06060.45960.19560.072*
O40.1588 (3)0.49524 (10)0.03089 (16)0.0380 (7)
N10.2345 (3)0.58284 (14)0.10970 (19)0.0407 (8)
N20.1547 (3)0.64007 (13)0.01947 (19)0.0401 (8)
H2B0.11840.65190.02490.048*
N30.2699 (3)0.41580 (13)0.11969 (19)0.0387 (8)
N40.2055 (3)0.35199 (13)0.03689 (19)0.0406 (8)
H4B0.17030.33670.00550.049*
C10.2462 (4)0.63501 (17)0.1386 (2)0.0410 (10)
C20.2999 (4)0.65352 (19)0.2102 (3)0.0485 (11)
H2A0.33190.62940.24970.058*
C30.3040 (5)0.70810 (19)0.2202 (3)0.0517 (12)
H3A0.34240.72200.26770.062*
C40.2539 (5)0.74418 (19)0.1633 (3)0.0516 (12)
H4A0.25830.78170.17330.062*
C50.1986 (4)0.72665 (17)0.0935 (3)0.0467 (11)
H5A0.16370.75100.05490.056*
C60.1962 (4)0.67122 (17)0.0824 (2)0.0419 (10)
C70.1802 (4)0.58830 (17)0.0388 (2)0.0393 (9)
C80.1595 (4)0.54227 (15)0.0147 (2)0.0391 (10)
H8A0.07300.54600.04850.047*
H8B0.23330.54050.04540.047*
C90.1768 (4)0.44668 (16)0.0084 (2)0.0408 (10)
H9A0.24850.45110.04010.049*
H9B0.09240.43650.04090.049*
C100.2155 (4)0.40456 (17)0.0506 (2)0.0387 (10)
C110.2612 (4)0.32574 (17)0.1022 (2)0.0414 (10)
C120.2816 (4)0.27105 (17)0.1189 (3)0.0480 (11)
H12A0.25260.24370.08330.058*
C130.3455 (4)0.2593 (2)0.1892 (3)0.0523 (12)
H13A0.36230.22280.20300.063*
C140.3872 (5)0.3002 (2)0.2416 (3)0.0539 (12)
H14A0.43230.29050.28980.065*
C150.3647 (4)0.35295 (18)0.2253 (2)0.0461 (11)
H15A0.39080.38000.26170.055*
C160.3016 (4)0.36626 (17)0.1529 (2)0.0392 (10)
C170.5414 (7)0.5170 (4)0.2839 (4)0.111 (3)
H17A0.58430.51870.23790.134*
H17B0.57750.48480.31250.134*
C180.5828 (9)0.5670 (4)0.3312 (6)0.158 (4)
H18A0.68090.56780.34450.237*
H18B0.54130.56590.37710.237*
H18C0.55270.59930.30240.237*
C190.0450 (6)0.5308 (2)0.2460 (4)0.0798 (18)
H19A0.07270.56740.23280.096*
H19B0.07940.52490.29980.096*
C200.1021 (6)0.5284 (3)0.2355 (4)0.099 (2)
H20A0.13650.55550.26740.148*
H20B0.13070.49260.24930.148*
H20C0.13750.53560.18280.148*
O50.5161 (3)0.41792 (12)0.00890 (15)0.0447 (7)
O60.3795 (4)0.40081 (15)0.1255 (2)0.0732 (11)
O70.3734 (4)0.32152 (15)0.1712 (2)0.0725 (11)
O80.5357 (7)0.16990 (18)0.0341 (4)0.126 (2)
O90.6222 (7)0.17536 (18)0.0825 (4)0.136 (2)
O100.7047 (3)0.34095 (14)0.1990 (2)0.0673 (10)
O110.6462 (4)0.41649 (13)0.1475 (2)0.0643 (9)
N50.4079 (4)0.35240 (16)0.1193 (2)0.0524 (10)
N60.5727 (7)0.1957 (2)0.0240 (4)0.102 (2)
N70.6505 (4)0.36722 (16)0.1451 (2)0.0509 (10)
C210.5280 (4)0.36791 (18)0.0124 (2)0.0419 (10)
C220.4763 (5)0.33195 (17)0.0490 (3)0.0465 (11)
C230.4907 (5)0.2772 (2)0.0454 (3)0.0614 (14)
H23A0.45600.25550.08720.074*
C240.5567 (5)0.25352 (19)0.0198 (3)0.0629 (14)
C250.6078 (5)0.28421 (19)0.0812 (3)0.0576 (13)
H25A0.65330.26760.12520.069*
C260.5921 (4)0.33915 (17)0.0778 (3)0.0458 (11)
N80.9544 (5)0.17124 (16)0.1081 (3)0.0783 (15)
N91.1077 (4)0.21015 (19)0.3675 (2)0.0564 (11)
O120.9230 (4)0.28313 (12)0.08169 (19)0.0605 (9)
O130.9718 (8)0.1816 (3)0.0434 (3)0.075 (3)*0.577 (11)
O140.9109 (8)0.1275 (2)0.1270 (4)0.081 (3)*0.577 (11)
O13A0.8804 (10)0.1802 (4)0.0484 (5)0.083 (4)*0.423 (11)
O14A0.9955 (13)0.1244 (3)0.1159 (7)0.097 (4)*0.423 (11)
O151.1017 (3)0.16073 (15)0.3786 (2)0.0662 (10)
O161.1480 (4)0.24173 (17)0.4180 (2)0.0685 (10)
O171.0423 (3)0.38875 (13)0.25535 (19)0.0590 (9)
O180.9626 (3)0.38007 (12)0.13932 (18)0.0517 (8)
C270.9682 (4)0.26778 (18)0.1456 (3)0.0481 (11)
C280.9854 (5)0.21100 (18)0.1660 (3)0.0523 (12)
C291.0283 (5)0.19286 (19)0.2356 (3)0.0538 (12)
H29A1.03400.15530.24530.065*
C301.0641 (4)0.22935 (19)0.2930 (3)0.0472 (11)
C311.0545 (4)0.28391 (18)0.2804 (3)0.0459 (11)
H31A1.07930.30850.32040.055*
C321.0087 (4)0.30245 (17)0.2095 (3)0.0429 (10)
N101.0031 (3)0.36034 (15)0.2009 (2)0.0456 (9)
O190.7129 (15)0.0593 (3)0.0039 (7)0.280 (6)
H190.66220.09060.01200.420*
C330.8305 (13)0.0560 (5)0.0371 (9)0.292 (14)
H33A0.84460.01900.05470.351*
H33B0.91030.06720.00160.351*
C340.8024 (13)0.0960 (5)0.1043 (6)0.169 (5)
H34A0.87830.09560.13270.253*
H34B0.79090.13240.08530.253*
H34C0.72020.08510.13720.253*
O200.7010 (7)0.0141 (3)0.1132 (3)0.141 (2)
H200.70560.00990.07420.211*
C350.6637 (14)0.0651 (4)0.0749 (6)0.173 (5)
H35A0.61850.08780.10870.208*
H35B0.59700.05730.03000.208*
C360.7723 (13)0.0961 (6)0.0511 (8)0.214 (6)
H36A0.73490.12710.02160.320*
H36B0.83290.10860.09540.320*
H36C0.82240.07350.02040.320*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn0.0467 (4)0.0440 (4)0.0288 (4)0.0027 (3)0.0021 (3)0.0021 (3)
O10.0509 (17)0.0410 (16)0.0441 (19)0.0022 (12)0.0094 (14)0.0005 (12)
O20.069 (2)0.097 (3)0.037 (2)0.0132 (19)0.0015 (17)0.0032 (18)
O30.072 (2)0.0499 (19)0.063 (2)0.0003 (15)0.0297 (19)0.0059 (15)
O40.0453 (16)0.0409 (16)0.0264 (15)0.0014 (12)0.0004 (12)0.0018 (11)
N10.046 (2)0.046 (2)0.029 (2)0.0010 (16)0.0013 (15)0.0035 (16)
N20.0444 (19)0.0419 (19)0.034 (2)0.0032 (16)0.0049 (15)0.0081 (16)
N30.0424 (18)0.0445 (19)0.0288 (19)0.0023 (16)0.0039 (15)0.0025 (15)
N40.049 (2)0.0394 (19)0.033 (2)0.0035 (16)0.0043 (16)0.0026 (15)
C10.040 (2)0.044 (2)0.040 (3)0.0014 (19)0.0064 (18)0.0005 (19)
C20.053 (3)0.055 (3)0.037 (3)0.001 (2)0.005 (2)0.001 (2)
C30.052 (3)0.055 (3)0.048 (3)0.006 (2)0.005 (2)0.012 (2)
C40.053 (3)0.046 (3)0.057 (3)0.005 (2)0.013 (2)0.005 (2)
C50.050 (3)0.041 (2)0.050 (3)0.003 (2)0.013 (2)0.004 (2)
C60.039 (2)0.047 (2)0.040 (3)0.0027 (19)0.0091 (19)0.000 (2)
C70.040 (2)0.044 (2)0.035 (2)0.0012 (18)0.0080 (18)0.0044 (19)
C80.047 (2)0.039 (2)0.030 (2)0.0014 (18)0.0031 (18)0.0055 (18)
C90.046 (2)0.045 (2)0.031 (2)0.0011 (19)0.0054 (18)0.0008 (19)
C100.041 (2)0.044 (2)0.031 (2)0.0023 (18)0.0054 (18)0.0025 (18)
C110.041 (2)0.049 (3)0.036 (2)0.0030 (19)0.0106 (19)0.0059 (19)
C120.053 (3)0.043 (2)0.049 (3)0.002 (2)0.012 (2)0.005 (2)
C130.054 (3)0.051 (3)0.055 (3)0.006 (2)0.016 (2)0.013 (2)
C140.055 (3)0.063 (3)0.044 (3)0.009 (2)0.009 (2)0.017 (2)
C150.052 (3)0.050 (3)0.035 (2)0.004 (2)0.004 (2)0.005 (2)
C160.042 (2)0.040 (2)0.036 (2)0.0058 (18)0.0070 (18)0.0012 (18)
C170.089 (5)0.165 (7)0.072 (5)0.017 (5)0.015 (4)0.028 (5)
C180.110 (7)0.207 (10)0.143 (9)0.032 (6)0.029 (6)0.047 (8)
C190.081 (4)0.074 (4)0.094 (5)0.004 (3)0.046 (4)0.025 (3)
C200.076 (4)0.118 (6)0.102 (6)0.016 (4)0.014 (4)0.016 (4)
O50.0531 (18)0.0412 (17)0.0388 (18)0.0014 (13)0.0033 (14)0.0009 (13)
O60.090 (3)0.060 (2)0.060 (2)0.010 (2)0.0173 (19)0.0121 (19)
O70.074 (2)0.077 (2)0.066 (3)0.0082 (19)0.0099 (19)0.038 (2)
O80.185 (6)0.047 (3)0.154 (6)0.004 (3)0.049 (4)0.016 (3)
O90.215 (7)0.048 (3)0.142 (5)0.018 (3)0.022 (5)0.026 (3)
O100.065 (2)0.073 (2)0.062 (2)0.0082 (17)0.0048 (18)0.0288 (19)
O110.081 (2)0.049 (2)0.054 (2)0.0006 (17)0.0159 (18)0.0049 (16)
N50.053 (2)0.052 (2)0.054 (3)0.0099 (19)0.0130 (19)0.015 (2)
N60.148 (6)0.040 (3)0.125 (6)0.006 (3)0.047 (5)0.003 (3)
N70.048 (2)0.055 (2)0.050 (3)0.0026 (19)0.0088 (18)0.015 (2)
C210.041 (2)0.043 (3)0.043 (3)0.0030 (19)0.0125 (19)0.0008 (19)
C220.050 (3)0.043 (3)0.050 (3)0.000 (2)0.017 (2)0.006 (2)
C230.068 (3)0.052 (3)0.072 (4)0.011 (2)0.033 (3)0.017 (3)
C240.071 (3)0.039 (3)0.086 (4)0.002 (2)0.033 (3)0.007 (3)
C250.058 (3)0.049 (3)0.071 (4)0.000 (2)0.026 (3)0.012 (3)
C260.044 (2)0.043 (2)0.054 (3)0.0011 (19)0.016 (2)0.003 (2)
N80.126 (4)0.042 (2)0.059 (3)0.009 (2)0.012 (3)0.017 (2)
N90.047 (2)0.070 (3)0.053 (3)0.011 (2)0.010 (2)0.027 (2)
O120.082 (2)0.0488 (18)0.046 (2)0.0060 (17)0.0055 (17)0.0109 (15)
O150.060 (2)0.078 (3)0.062 (2)0.0123 (18)0.0136 (17)0.0355 (19)
O160.074 (2)0.087 (3)0.043 (2)0.017 (2)0.0025 (18)0.011 (2)
O170.078 (2)0.0529 (19)0.043 (2)0.0001 (16)0.0018 (17)0.0019 (16)
O180.0632 (19)0.0477 (18)0.0436 (19)0.0062 (14)0.0056 (15)0.0143 (15)
C270.051 (3)0.049 (3)0.042 (3)0.001 (2)0.001 (2)0.014 (2)
C280.063 (3)0.045 (3)0.049 (3)0.007 (2)0.006 (2)0.007 (2)
C290.057 (3)0.048 (3)0.056 (3)0.001 (2)0.006 (2)0.019 (2)
C300.045 (2)0.055 (3)0.041 (3)0.004 (2)0.007 (2)0.015 (2)
C310.043 (2)0.055 (3)0.040 (3)0.008 (2)0.0060 (19)0.010 (2)
C320.040 (2)0.046 (2)0.044 (3)0.0045 (19)0.0096 (19)0.009 (2)
N100.044 (2)0.050 (2)0.043 (2)0.0028 (17)0.0068 (17)0.0086 (19)
O190.45 (2)0.109 (6)0.316 (15)0.045 (9)0.159 (14)0.037 (7)
C330.189 (13)0.151 (13)0.57 (4)0.059 (11)0.17 (2)0.138 (18)
C340.245 (14)0.125 (8)0.140 (10)0.038 (8)0.036 (9)0.005 (7)
O200.195 (7)0.160 (5)0.072 (4)0.043 (4)0.035 (4)0.030 (3)
C350.260 (15)0.138 (9)0.127 (9)0.058 (9)0.047 (9)0.050 (7)
C360.172 (11)0.272 (16)0.184 (13)0.080 (11)0.015 (9)0.025 (12)
Geometric parameters (Å, º) top
Mn—O22.123 (4)C19—H19B0.9900
Mn—O12.140 (3)C20—H20A0.9800
Mn—O32.194 (3)C20—H20B0.9800
Mn—N12.199 (3)C20—H20C0.9800
Mn—N32.215 (3)O5—C211.250 (5)
Mn—O42.384 (3)O6—N51.238 (5)
O1—H1W0.9300O7—N51.220 (5)
O1—H2W0.9301O8—N61.236 (8)
O2—C171.449 (8)O9—N61.209 (8)
O2—H20.9500O10—N71.229 (5)
O3—C191.404 (6)O11—N71.227 (5)
O3—H30.9500N5—C221.443 (6)
O4—C91.425 (5)N6—C241.448 (7)
O4—C81.429 (5)N7—C261.446 (6)
N1—C71.320 (5)C21—C261.447 (6)
N1—C11.396 (5)C21—C221.457 (6)
N2—C71.348 (5)C22—C231.370 (6)
N2—C61.386 (5)C23—C241.392 (8)
N2—H2B0.8800C23—H23A0.9500
N3—C101.314 (5)C24—C251.379 (7)
N3—C161.386 (5)C25—C261.375 (6)
N4—C101.331 (5)C25—H25A0.9500
N4—C111.389 (5)N8—O131.232 (5)
N4—H4B0.8800N8—O14A1.236 (5)
C1—C61.393 (6)N8—O13A1.236 (5)
C1—C21.401 (6)N8—O141.239 (5)
C2—C31.369 (6)N8—C281.437 (6)
C2—H2A0.9500N9—O161.224 (5)
C3—C41.400 (7)N9—O151.247 (5)
C3—H3A0.9500N9—C301.433 (6)
C4—C51.369 (6)O12—C271.235 (5)
C4—H4A0.9500O17—N101.226 (5)
C5—C61.392 (6)O18—N101.227 (4)
C5—H5A0.9500C27—C321.448 (6)
C7—C81.491 (6)C27—C281.462 (6)
C8—H8A0.9900C28—C291.344 (6)
C8—H8B0.9900C29—C301.383 (7)
C9—C101.502 (6)C29—H29A0.9500
C9—H9A0.9900C30—C311.376 (6)
C9—H9B0.9900C31—C321.373 (6)
C11—C161.381 (6)C31—H31A0.9500
C11—C121.401 (6)C32—N101.448 (6)
C12—C131.365 (7)O19—C331.404 (9)
C12—H12A0.9500O19—H190.9299
C13—C141.409 (7)C33—C341.560 (10)
C13—H13A0.9500C33—H33A0.9900
C14—C151.356 (6)C33—H33B0.9900
C14—H14A0.9500C34—H34A0.9800
C15—C161.403 (6)C34—H34B0.9800
C15—H15A0.9500C34—H34C0.9800
C17—C181.531 (11)O20—C351.466 (10)
C17—H17A0.9900O20—H200.9296
C17—H17B0.9900C35—C361.451 (14)
C18—H18A0.9800C35—H35A0.9900
C18—H18B0.9800C35—H35B0.9900
C18—H18C0.9800C36—H36A0.9800
C19—C201.464 (8)C36—H36B0.9800
C19—H19A0.9900C36—H36C0.9800
O2—Mn—O194.95 (14)C17—C18—H18C109.5
O2—Mn—O388.13 (15)H18A—C18—H18C109.5
O1—Mn—O3175.05 (11)H18B—C18—H18C109.5
O2—Mn—N1107.83 (13)O3—C19—C20114.3 (5)
O1—Mn—N189.80 (12)O3—C19—H19A108.7
O3—Mn—N192.95 (12)C20—C19—H19A108.7
O2—Mn—N3110.56 (13)O3—C19—H19B108.7
O1—Mn—N386.88 (11)C20—C19—H19B108.7
O3—Mn—N388.41 (12)H19A—C19—H19B107.6
N1—Mn—N3141.62 (13)C19—C20—H20A109.5
O2—Mn—O4177.23 (12)C19—C20—H20B109.5
O1—Mn—O487.29 (11)H20A—C20—H20B109.5
O3—Mn—O489.76 (12)C19—C20—H20C109.5
N1—Mn—O470.50 (11)H20A—C20—H20C109.5
N3—Mn—O471.15 (10)H20B—C20—H20C109.5
Mn—O1—H1W120.2O7—N5—O6120.5 (4)
Mn—O1—H2W118.7O7—N5—C22119.8 (4)
H1W—O1—H2W121.1O6—N5—C22119.7 (4)
C17—O2—Mn128.3 (4)O9—N6—O8123.8 (6)
C17—O2—H2115.8O9—N6—C24119.2 (7)
Mn—O2—H2115.8O8—N6—C24117.0 (7)
C19—O3—Mn128.7 (3)O11—N7—O10121.1 (4)
C19—O3—H3115.6O11—N7—C26120.0 (4)
Mn—O3—H3115.6O10—N7—C26118.9 (4)
C9—O4—C8113.3 (3)O5—C21—C26124.1 (4)
C9—O4—Mn114.9 (2)O5—C21—C22123.4 (4)
C8—O4—Mn115.1 (2)C26—C21—C22112.5 (4)
C7—N1—C1105.4 (3)C23—C22—N5115.1 (4)
C7—N1—Mn118.6 (3)C23—C22—C21123.4 (5)
C1—N1—Mn136.0 (3)N5—C22—C21121.4 (4)
C7—N2—C6107.4 (4)C22—C23—C24119.5 (5)
C7—N2—H2B126.3C22—C23—H23A120.2
C6—N2—H2B126.3C24—C23—H23A120.2
C10—N3—C16104.9 (3)C25—C24—C23121.2 (5)
C10—N3—Mn117.7 (3)C25—C24—N6118.9 (6)
C16—N3—Mn137.4 (3)C23—C24—N6119.9 (6)
C10—N4—C11107.1 (3)C26—C25—C24119.2 (5)
C10—N4—H4B126.4C26—C25—H25A120.4
C11—N4—H4B126.4C24—C25—H25A120.4
C6—C1—N1109.1 (4)C25—C26—N7114.4 (4)
C6—C1—C2120.4 (4)C25—C26—C21124.1 (5)
N1—C1—C2130.4 (4)N7—C26—C21121.5 (4)
C3—C2—C1116.6 (4)O13—N8—O14A102.2 (8)
C3—C2—H2A121.7O13—N8—O13A44.6 (5)
C1—C2—H2A121.7O14A—N8—O13A114.6 (8)
C2—C3—C4122.5 (5)O13—N8—O14123.2 (6)
C2—C3—H3A118.7O14A—N8—O1442.9 (5)
C4—C3—H3A118.7O13A—N8—O14101.8 (7)
C5—C4—C3121.5 (4)O13—N8—C28119.9 (5)
C5—C4—H4A119.2O14A—N8—C28122.2 (7)
C3—C4—H4A119.2O13A—N8—C28123.2 (6)
C4—C5—C6116.4 (4)O14—N8—C28116.9 (5)
C4—C5—H5A121.8O16—N9—O15122.1 (4)
C6—C5—H5A121.8O16—N9—C30120.3 (4)
N2—C6—C5131.9 (4)O15—N9—C30117.6 (5)
N2—C6—C1105.5 (4)O12—C27—C32125.4 (4)
C5—C6—C1122.5 (4)O12—C27—C28123.1 (4)
N1—C7—N2112.6 (4)C32—C27—C28111.5 (4)
N1—C7—C8123.0 (4)C29—C28—N8116.9 (4)
N2—C7—C8124.2 (4)C29—C28—C27124.6 (5)
O4—C8—C7105.5 (3)N8—C28—C27118.5 (4)
O4—C8—H8A110.6C28—C29—C30119.4 (4)
C7—C8—H8A110.6C28—C29—H29A120.3
O4—C8—H8B110.6C30—C29—H29A120.3
C7—C8—H8B110.6C31—C30—C29121.3 (4)
H8A—C8—H8B108.8C31—C30—N9119.1 (4)
O4—C9—C10106.1 (3)C29—C30—N9119.5 (4)
O4—C9—H9A110.5C32—C31—C30119.3 (4)
C10—C9—H9A110.5C32—C31—H31A120.3
O4—C9—H9B110.5C30—C31—H31A120.3
C10—C9—H9B110.5C31—C32—N10115.8 (4)
H9A—C9—H9B108.7C31—C32—C27123.9 (4)
N3—C10—N4113.2 (4)N10—C32—C27120.3 (4)
N3—C10—C9123.4 (4)O17—N10—O18121.2 (4)
N4—C10—C9123.3 (4)O17—N10—C32119.0 (4)
C16—C11—N4105.1 (4)O18—N10—C32119.8 (4)
C16—C11—C12123.1 (4)C33—O19—H19117.3
N4—C11—C12131.8 (4)O19—C33—C34103.1 (11)
C13—C12—C11116.2 (4)O19—C33—H33A111.1
C13—C12—H12A121.9C34—C33—H33A111.1
C11—C12—H12A121.9O19—C33—H33B111.1
C12—C13—C14121.4 (4)C34—C33—H33B111.1
C12—C13—H13A119.3H33A—C33—H33B109.1
C14—C13—H13A119.3C33—C34—H34A109.5
C15—C14—C13122.0 (4)C33—C34—H34B109.5
C15—C14—H14A119.0H34A—C34—H34B109.5
C13—C14—H14A119.0C33—C34—H34C109.5
C14—C15—C16117.9 (4)H34A—C34—H34C109.5
C14—C15—H15A121.1H34B—C34—H34C109.5
C16—C15—H15A121.1C35—O20—H20103.7
C11—C16—N3109.6 (4)C36—C35—O20116.6 (12)
C11—C16—C15119.5 (4)C36—C35—H35A108.2
N3—C16—C15130.9 (4)O20—C35—H35A108.2
O2—C17—C18115.4 (6)C36—C35—H35B108.2
O2—C17—H17A108.4O20—C35—H35B108.2
C18—C17—H17A108.4H35A—C35—H35B107.3
O2—C17—H17B108.4C35—C36—H36A109.5
C18—C17—H17B108.4C35—C36—H36B109.5
H17A—C17—H17B107.5H36A—C36—H36B109.5
C17—C18—H18A109.5C35—C36—H36C109.5
C17—C18—H18B109.5H36A—C36—H36C109.5
H18A—C18—H18B109.5H36B—C36—H36C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1W···O5i0.931.992.758 (4)139
O1—H1W···O6i0.932.072.854 (4)141
O1—H2W···O50.931.992.758 (4)139
O1—H2W···O110.932.112.898 (4)141
O2—H2···O20ii0.951.762.659 (7)157
O3—H3···O17iii0.952.092.864 (4)138
O3—H3···O18iii0.952.373.289 (5)163
N2—H2B···O12i0.881.922.676 (4)142
N2—H2B···O18i0.882.252.973 (5)140
N4—H4B···O15iv0.882.102.907 (5)152
N4—H4B···O16iv0.882.383.161 (5)148
O19—H19···O80.932.353.278 (13)179
O20—H20···O190.931.882.807 (13)179
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1/2, z+1/2; (iii) x1, y, z; (iv) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formula[Mn(C16H14N4O)(C2H6O)2(H2O)](C6H2N3O7)2·2C2H6O
Mr991.75
Crystal system, space groupMonoclinic, P21/c
Temperature (K)153
a, b, c (Å)10.0519 (3), 24.8584 (8), 18.0291 (7)
β (°) 98.504 (1)
V3)4455.5 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.39
Crystal size (mm)0.39 × 0.25 × 0.22
Data collection
DiffractometerBruker SMART APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.864, 0.920
No. of measured, independent and
observed [I > 2σ(I)] reflections
32660, 7806, 4707
Rint0.045
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.074, 0.255, 1.07
No. of reflections7806
No. of parameters603
No. of restraints8
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.73, 0.97

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1W···O5i0.931.992.758 (4)138.5
O1—H1W···O6i0.932.072.854 (4)140.6
O1—H2W···O50.931.992.758 (4)138.7
O1—H2W···O110.932.112.898 (4)141.1
O2—H2···O20ii0.951.762.659 (7)156.5
O3—H3···O17iii0.952.092.864 (4)137.9
O3—H3···O18iii0.952.373.289 (5)162.8
N2—H2B···O12i0.881.922.676 (4)142.4
N2—H2B···O18i0.882.252.973 (5)139.6
N4—H4B···O15iv0.882.102.907 (5)151.9
N4—H4B···O16iv0.882.383.161 (5)148.0
O19—H19···O80.932.353.278 (13)179.2
O20—H20···O190.931.882.807 (13)179.0
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1/2, z+1/2; (iii) x1, y, z; (iv) x1, y+1/2, z1/2.
 

Acknowledgements

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

References

First citationBruker (2000).APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChang, C. M., Kulkarni, M. V., Chen, C. H., Wang, C. & Sun, C. M. (2008). J. Comb. Chem. 10, 466–474.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHarrell, C. C., Kohli, P., Siwy, Z. & Martin, C. R. (2004). J. Am. Chem. Soc. 126, 15646–15647.  Web of Science CrossRef PubMed CAS Google Scholar
First citationHolland, P. L. & Tolman, W. B. (2000). J. Am. Chem. Soc. 122, 6331–6332.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds