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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 2| February 2011| Pages m186-m187

Tris(1,10-phenanthroline-κ2N,N′)zinc(II) chloride 2-phenyl-4-selenazole-5-car­box­yl­ate decahydrate

aCollege of Chemistry and Life Science, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
*Correspondence e-mail: sky53@zjnu.cn

(Received 21 December 2010; accepted 6 January 2011; online 15 January 2011)

The asymmetric unit of the title salt, [Zn(C12H8N2)3](C10H6NO2Se)Cl·10H2O, contains a [Zn(phen)3]2+ cation (phen is 1,10-phenanthroline), uncoordinated chloride and 2-phenyl-4-selenazole-5-carboxyl­ate anions and ten uncoord­in­ated water mol­ecules. The central ZnII ion is six-coordinated by six N atoms from three phen ligands in a distorted octa­hedral geometry. An extensive O—H⋯O, O—H⋯N and O—H⋯Cl hydrogen-bonding network stabilizes the crystal structure.

Related literature

For the synthesis of the organic ligand, 2-phenyl-4-selenazole-5-carboxylic acid, see: Zhao et al. (2010[Zhao, G.-L., Shi, X., Zhang, J. P., Liu, J.-F., Xian, H.-D. & Shao, L. X. (2010). Chem. Sci. China, 40, 1525-1535.]). For related structures, see: Srivastava & Robins (1983[Srivastava, P. C. & Robins, R. K. (1983). J. Med. Chem. 26, 445-448.]); Boritzki et al. (1985[Boritzki, T. J., Berry, D. A., Besserer, J. A., Cook, P. D., Fry, D. W., Leopold, W. R. & Jackson, R. C. (1985). Biochem. Pharmacol. 34, 1109-1114.]); Wang et al. (2006[Wang, X. L., Zhang, X. Y., Ma, Y. & Wang, E. B. (2006). J. Northeast Normal Univ. 38, 68-72.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(C12H8N2)3](C10H6NO2Se)Cl·10H2O

  • Mr = 1072.71

  • Triclinic, [P \overline 1]

  • a = 12.4837 (9) Å

  • b = 13.8935 (10) Å

  • c = 15.8221 (12) Å

  • α = 77.618 (4)°

  • β = 89.642 (4)°

  • γ = 63.375 (4)°

  • V = 2383.4 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 1.40 mm−1

  • T = 296 K

  • 0.64 × 0.35 × 0.17 mm

Data collection
  • Bruker APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.562, Tmax = 0.790

  • 33787 measured reflections

  • 8371 independent reflections

  • 6305 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.140

  • S = 1.06

  • 8371 reflections

  • 613 parameters

  • 30 restraints

  • H-atom parameters constrained

  • Δρmax = 0.81 e Å−3

  • Δρmin = −0.74 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1WA⋯O2Wi 0.85 2.05 2.898 (5) 179
O1W—H1WB⋯O9Wii 0.85 1.98 2.830 (6) 180
O4W—H4WA⋯N7ii 0.85 2.22 3.044 (5) 163
O4W—H4WA⋯O1ii 0.85 2.40 2.921 (7) 120
O5W—H5WA⋯O6Wiii 0.85 1.91 2.762 (6) 178
O6W—H6WA⋯Cl1iii 0.85 2.24 3.076 (5) 168
O7W—H7WB⋯Cl1iv 0.85 2.54 3.391 (5) 179
O8W—H8WB⋯O7Wv 0.85 1.97 2.817 (7) 180
O2W—H2WA⋯O9Wvi 0.85 1.96 2.806 (5) 179
O2W—H2WB⋯Cl1vii 0.85 2.28 3.129 (3) 180
O4W—H4WB⋯O1 0.85 1.98 2.809 (6) 166
O5W—H5WB⋯O3W 0.85 2.07 2.915 (6) 173
O6W—H6WB⋯O2 0.85 2.05 2.892 (6) 171
O7W—H7WA⋯Cl1 0.85 2.24 3.006 (5) 150
O8W—H8WA⋯O2 0.85 1.97 2.819 (5) 172
O9W—H9WA⋯O8W 0.85 2.05 2.864 (8) 161
O9W—H9WB⋯O10W 0.85 2.18 3.030 (8) 178
O10W—H10W⋯O4W 0.85 2.02 2.866 (8) 173
O10W—H10E⋯O2 0.85 2.08 2.925 (6) 171
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z+2; (v) x, y, z-1; (vi) x-1, y, z+1; (vii) x-1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). 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.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Derivatives of selenazole are important in chemistry and biochemistry due to their biological activity (Srivastava et al., 1983; Boritzki et al., 1985). Interested in this field, we have been engaged in a major effort directed toward the development of syntheses of new selenazole carboxylic acid and their transition metal complexes. We have reported our partial research results previously (Zhao et al., 2010). Herein, we describe the structure of the title ZnII complex.

The local coordination geometry around each Zn center (Fig. 1 and Fig. 2) is a slightly distorted octahedron defined by six nitrogen atoms from three different 1,10-phenanthroline (phen) ligands while the organic ligand 2-phenyl-4- selenazole carboxylic acid (HL) loses its one proton and changes to L which fail to coordinate to zinc atom.That is, the compound consists of [Zn(phen)3]2+ cations, two un-coordinating anions: Cl-and L and ten water molecules. The bonds between ZnII and N atoms from 1, 10-phenanthroline are 2.155 (3)Å - 2.185 (3)Å, which are similar to related compounds in the literatures (Wang et al. 2006). The three phen ligands around zinc is respectively plane,the four N atoms of phen form the equatorial plane, and N4 and N5 atoms occupy the apical positions.

The hydrogen bonds and π···π weak non-covalent interactions lend stability to the structure. The hydrogen bonds are listed in Table 2 and the stacking plot of this compound is shown in Fig. 3. Complex molecules are linked in a line through water molecules by hydrogen bonds and different lines are interlocked with benzene rings using π···π stacking.

Related literature top

For the synthesis of the organic ligand, 2-phenyl-4-selenazole carboxylic acid, see: Zhao et al. (2010). For related structures, see: Srivastava et al. (1983); Boritzki et al. (1985); Wang et al. (2006).

Experimental top

Reagents and solvents used were of commercially available quality and without purification before using. The compound (1) was obtained by adding ZnCl2 (0.136 g,1 mmol) to 2-phenyl-4-selenazole carboxylic acid (0.252 g,1 mmol),1,10- phenanthroline (0.396 g, 2 mmol) in ethanol solution. The mixture was stirred at room temperature for 8 h to obtain a colourless solution which was filtered and the filtrate kept for evaporating. colourless crystal of the title complex formed after 40 days.

Refinement top

The H atoms bonded to C atoms were positioned geometrically and refined using a riding model [aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C))]. Water H atoms bonded to O atoms were located in difference Fourier maps and refined with O—H distance restraints of 0.83 (2) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom- labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The coordination environment of the ZnII atom, showing the octahedral structurem.
[Figure 3] Fig. 3. The stacking plot of the title compound, showing H-bond interactions (dashed lines) and π···π stacking interactions.
Tris(1,10-phenanthroline-κ2N,N')zinc(II) chloride 2-phenyl-4-selenazole-5-carboxylate decahydrate top
Crystal data top
[Zn(C12H8N2)3](C10H6NO2Se)Cl·10H2OZ = 2
Mr = 1072.71F(000) = 1104
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.4837 (9) ÅCell parameters from 8933 reflections
b = 13.8935 (10) Åθ = 1.8–25.0°
c = 15.8221 (12) ŵ = 1.40 mm1
α = 77.618 (4)°T = 296 K
β = 89.642 (4)°Block, colourless
γ = 63.375 (4)°0.64 × 0.35 × 0.17 mm
V = 2383.4 (3) Å3
Data collection top
Bruker APEXII area-detector
diffractometer
8371 independent reflections
Radiation source: fine-focus sealed tube6305 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1414
Tmin = 0.562, Tmax = 0.790k = 1616
33787 measured reflectionsl = 1818
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0806P)2 + 0.8651P]
where P = (Fo2 + 2Fc2)/3
8371 reflections(Δ/σ)max < 0.001
613 parametersΔρmax = 0.81 e Å3
30 restraintsΔρmin = 0.74 e Å3
Crystal data top
[Zn(C12H8N2)3](C10H6NO2Se)Cl·10H2Oγ = 63.375 (4)°
Mr = 1072.71V = 2383.4 (3) Å3
Triclinic, P1Z = 2
a = 12.4837 (9) ÅMo Kα radiation
b = 13.8935 (10) ŵ = 1.40 mm1
c = 15.8221 (12) ÅT = 296 K
α = 77.618 (4)°0.64 × 0.35 × 0.17 mm
β = 89.642 (4)°
Data collection top
Bruker APEXII area-detector
diffractometer
8371 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
6305 reflections with I > 2σ(I)
Tmin = 0.562, Tmax = 0.790Rint = 0.038
33787 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04730 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.06Δρmax = 0.81 e Å3
8371 reflectionsΔρmin = 0.74 e Å3
613 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
Zn10.19692 (3)0.30045 (3)0.77746 (2)0.03857 (14)
Se10.43865 (4)0.23586 (4)0.49471 (3)0.07071 (17)
N10.1832 (3)0.4178 (2)0.85189 (18)0.0424 (7)
N30.1650 (2)0.2219 (2)0.68130 (18)0.0415 (7)
N40.1851 (2)0.4125 (2)0.65436 (17)0.0390 (6)
C430.5785 (3)0.1029 (3)0.5404 (2)0.0471 (9)
N20.0048 (3)0.3822 (2)0.79275 (18)0.0412 (7)
C180.1620 (3)0.3806 (3)0.5840 (2)0.0385 (8)
N50.2362 (3)0.1535 (3)0.87845 (18)0.0446 (7)
N60.3907 (3)0.2104 (2)0.78710 (18)0.0428 (7)
C290.3519 (3)0.0743 (3)0.8845 (2)0.0429 (8)
C170.1493 (3)0.2808 (3)0.5982 (2)0.0405 (8)
C50.0267 (3)0.4672 (3)0.8330 (2)0.0398 (8)
C330.4351 (3)0.1060 (3)0.8375 (2)0.0411 (8)
C40.1461 (3)0.5338 (3)0.8457 (2)0.0484 (9)
N70.6756 (3)0.1018 (3)0.5097 (2)0.0532 (8)
C210.1516 (3)0.4420 (3)0.4983 (2)0.0470 (9)
C160.1221 (3)0.2475 (3)0.5270 (2)0.0490 (9)
C400.5741 (3)0.0113 (3)0.6027 (2)0.0479 (9)
C360.4676 (3)0.2405 (4)0.7452 (3)0.0534 (10)
H36A0.43810.31180.71010.064*
C60.0684 (3)0.4867 (3)0.8636 (2)0.0420 (8)
C250.1598 (4)0.1265 (4)0.9235 (2)0.0565 (10)
H25A0.08060.18050.92090.068*
C130.1554 (3)0.1289 (3)0.6952 (3)0.0480 (9)
H13A0.16750.08750.75200.058*
C240.2010 (3)0.5024 (3)0.6411 (2)0.0505 (9)
H24A0.21700.52430.68910.061*
C320.5577 (3)0.0283 (3)0.8460 (2)0.0505 (9)
C10.0815 (3)0.3633 (3)0.7646 (2)0.0479 (9)
H1A0.06050.30520.73730.057*
C110.2502 (4)0.5211 (4)0.9210 (3)0.0649 (12)
H11A0.31440.53120.93920.078*
C280.3934 (4)0.0346 (3)0.9353 (2)0.0526 (9)
C120.2705 (4)0.4352 (3)0.8807 (2)0.0531 (9)
H12A0.34950.38790.87380.064*
C140.1281 (4)0.0904 (4)0.6283 (3)0.0623 (11)
H14A0.12190.02470.64080.075*
C30.2354 (3)0.5099 (4)0.8149 (3)0.0576 (10)
H3A0.31570.55150.82270.069*
C410.4668 (4)0.0119 (4)0.6252 (3)0.0572 (10)
H41A0.39440.07270.60000.069*
C310.5950 (4)0.0802 (4)0.8985 (3)0.0669 (12)
H31A0.67590.13160.90420.080*
O20.7391 (3)0.2748 (3)0.3355 (2)0.0776 (9)
C90.0390 (4)0.5745 (3)0.9049 (2)0.0515 (9)
C440.6545 (4)0.1973 (3)0.4470 (3)0.0531 (10)
C340.6337 (4)0.0650 (4)0.8007 (3)0.0630 (12)
H34A0.71540.01670.80450.076*
C200.1236 (3)0.4051 (4)0.4277 (2)0.0562 (10)
H20A0.11580.44550.37110.067*
C20.2036 (3)0.4265 (4)0.7740 (3)0.0564 (10)
H2A0.26190.41110.75240.068*
C260.1939 (5)0.0196 (4)0.9748 (3)0.0694 (13)
H26A0.13770.00351.00520.083*
C450.5393 (4)0.2780 (4)0.4290 (3)0.0664 (11)
H45A0.51440.34560.38900.080*
C460.7594 (4)0.2044 (4)0.4063 (4)0.0693 (12)
C300.5170 (5)0.1111 (4)0.9403 (3)0.0679 (12)
H30A0.54440.18340.97290.081*
C220.1704 (3)0.5354 (4)0.4878 (3)0.0565 (10)
H22A0.16630.57700.43230.068*
C350.5906 (4)0.1693 (4)0.7516 (3)0.0631 (11)
H35A0.64230.19350.72250.076*
C390.6816 (4)0.0817 (4)0.6421 (3)0.0593 (11)
H39A0.75530.08430.62850.071*
C230.1947 (4)0.5654 (4)0.5584 (3)0.0599 (10)
H23A0.20710.62770.55180.072*
C420.4650 (4)0.0758 (4)0.6844 (3)0.0633 (11)
H42A0.39170.07340.69910.076*
C150.1106 (4)0.1492 (4)0.5446 (3)0.0612 (11)
H15A0.09110.12460.49950.073*
C70.1715 (4)0.6205 (3)0.8894 (3)0.0625 (11)
H7A0.25060.66420.89870.075*
C190.1083 (3)0.3126 (4)0.4414 (3)0.0573 (11)
H19A0.08860.29150.39420.069*
C100.1353 (5)0.5901 (4)0.9334 (3)0.0633 (11)
H10A0.12060.64730.96060.076*
C270.3092 (5)0.0600 (4)0.9797 (3)0.0677 (12)
H27A0.33200.13141.01270.081*
C80.0838 (4)0.6399 (3)0.9172 (3)0.0651 (12)
H8A0.10320.69730.94510.078*
O10.8605 (3)0.1404 (4)0.4456 (3)0.1188 (16)
C370.5696 (5)0.1658 (4)0.7214 (3)0.0678 (12)
H37A0.56810.22550.76050.081*
C380.6784 (4)0.1683 (4)0.7005 (3)0.0672 (12)
H38A0.75010.22950.72650.081*
Cl10.57973 (16)0.37700 (19)0.91079 (13)0.1335 (7)
O3W0.8109 (3)0.2373 (3)0.6383 (2)0.0912 (11)
H3WA0.84720.20300.68900.137*
H3WB0.82050.20950.59420.137*
O1W0.9146 (4)0.1104 (3)0.8120 (3)0.1032 (12)
H1WA0.89670.14220.85410.155*
H1WB0.95910.04090.82880.155*
O4W1.0793 (4)0.0140 (4)0.3841 (3)0.1190 (15)
H4WA1.13900.01580.42280.178*
H4WB1.01990.04720.41130.178*
O5W0.5718 (4)0.4248 (4)0.5881 (3)0.1123 (13)
H5WA0.53470.45020.62980.168*
H5WB0.63840.36650.60410.168*
O6W0.5449 (4)0.4965 (4)0.2741 (3)0.1146 (14)
H6WA0.51820.52300.22060.172*
H6WB0.60670.43370.28850.172*
O7W0.4968 (4)0.3559 (4)1.0895 (3)0.1256 (16)
H7WA0.54540.35121.05090.188*
H7WB0.47760.42281.08990.188*
O8W0.7050 (5)0.1907 (4)0.1966 (3)0.1297 (16)
H8WA0.72070.21710.23580.195*
H8WB0.64210.24050.16420.195*
O9W0.9370 (6)0.1210 (4)0.1330 (3)0.160 (2)
H9WA0.86720.13090.14610.240*
H9WB0.94560.15090.17230.240*
O10W0.9719 (5)0.2306 (6)0.2694 (3)0.155 (2)
H10W1.00990.16560.30160.233*
H10E0.90870.23620.29300.233*
O2W0.1445 (3)0.2174 (2)0.95610 (18)0.0604 (7)
H2WA0.11920.18791.00960.091*
H2WB0.21940.26070.94380.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0347 (2)0.0370 (2)0.0420 (2)0.01497 (18)0.00388 (16)0.00878 (17)
Se10.0395 (2)0.0629 (3)0.0806 (3)0.0045 (2)0.0095 (2)0.0029 (2)
N10.0410 (16)0.0416 (17)0.0411 (15)0.0164 (14)0.0033 (13)0.0085 (13)
N30.0361 (15)0.0433 (18)0.0481 (17)0.0183 (14)0.0080 (13)0.0165 (14)
N40.0354 (15)0.0371 (16)0.0425 (15)0.0157 (13)0.0010 (12)0.0074 (13)
C430.0333 (18)0.049 (2)0.052 (2)0.0101 (17)0.0014 (16)0.0186 (18)
N20.0404 (16)0.0392 (17)0.0434 (16)0.0186 (14)0.0043 (13)0.0074 (13)
C180.0265 (16)0.041 (2)0.0422 (18)0.0105 (15)0.0058 (13)0.0100 (15)
N50.0433 (17)0.0469 (18)0.0429 (16)0.0221 (15)0.0024 (13)0.0058 (13)
N60.0393 (16)0.0419 (18)0.0472 (16)0.0190 (14)0.0048 (13)0.0098 (14)
C290.050 (2)0.042 (2)0.0384 (18)0.0218 (18)0.0036 (15)0.0111 (16)
C170.0262 (16)0.046 (2)0.046 (2)0.0111 (15)0.0071 (14)0.0174 (16)
C50.0414 (19)0.0333 (19)0.0374 (17)0.0126 (16)0.0058 (15)0.0039 (15)
C330.0406 (19)0.039 (2)0.0416 (18)0.0138 (16)0.0036 (15)0.0146 (16)
C40.047 (2)0.037 (2)0.046 (2)0.0092 (17)0.0084 (16)0.0028 (16)
N70.0403 (17)0.050 (2)0.068 (2)0.0178 (15)0.0035 (15)0.0182 (17)
C210.0305 (18)0.051 (2)0.045 (2)0.0086 (16)0.0049 (15)0.0067 (17)
C160.0325 (18)0.059 (3)0.055 (2)0.0146 (18)0.0052 (16)0.0284 (19)
C400.040 (2)0.051 (2)0.048 (2)0.0142 (18)0.0057 (16)0.0190 (18)
C360.046 (2)0.056 (3)0.061 (2)0.026 (2)0.0084 (18)0.0108 (19)
C60.053 (2)0.0327 (19)0.0343 (17)0.0168 (17)0.0033 (15)0.0026 (14)
C250.062 (3)0.063 (3)0.054 (2)0.038 (2)0.0082 (19)0.008 (2)
C130.044 (2)0.041 (2)0.063 (2)0.0216 (18)0.0098 (17)0.0150 (18)
C240.054 (2)0.048 (2)0.051 (2)0.027 (2)0.0037 (17)0.0061 (18)
C320.044 (2)0.046 (2)0.053 (2)0.0093 (18)0.0050 (17)0.0198 (18)
C10.041 (2)0.049 (2)0.055 (2)0.0230 (18)0.0069 (17)0.0091 (17)
C110.079 (3)0.067 (3)0.062 (3)0.046 (3)0.006 (2)0.012 (2)
C280.069 (3)0.041 (2)0.047 (2)0.026 (2)0.0056 (19)0.0085 (17)
C120.055 (2)0.057 (3)0.052 (2)0.030 (2)0.0011 (18)0.0116 (19)
C140.058 (3)0.058 (3)0.088 (3)0.035 (2)0.017 (2)0.034 (2)
C30.037 (2)0.052 (3)0.071 (3)0.0132 (18)0.0131 (18)0.005 (2)
C410.041 (2)0.061 (3)0.065 (3)0.017 (2)0.0060 (18)0.019 (2)
C310.062 (3)0.041 (2)0.075 (3)0.002 (2)0.017 (2)0.017 (2)
O20.075 (2)0.083 (2)0.080 (2)0.0430 (19)0.0178 (18)0.0158 (19)
C90.069 (3)0.033 (2)0.046 (2)0.0183 (19)0.0025 (18)0.0083 (16)
C440.049 (2)0.053 (3)0.061 (2)0.024 (2)0.0054 (18)0.020 (2)
C340.036 (2)0.071 (3)0.074 (3)0.011 (2)0.005 (2)0.032 (3)
C200.045 (2)0.066 (3)0.043 (2)0.012 (2)0.0055 (17)0.0138 (19)
C20.040 (2)0.059 (3)0.069 (3)0.026 (2)0.0050 (18)0.006 (2)
C260.090 (4)0.074 (3)0.060 (3)0.057 (3)0.007 (2)0.003 (2)
C450.057 (3)0.055 (3)0.076 (3)0.018 (2)0.008 (2)0.011 (2)
C460.060 (3)0.063 (3)0.095 (4)0.035 (3)0.009 (3)0.023 (3)
C300.090 (3)0.037 (2)0.063 (3)0.018 (2)0.016 (2)0.008 (2)
C220.048 (2)0.061 (3)0.049 (2)0.022 (2)0.0046 (18)0.0008 (19)
C350.043 (2)0.078 (3)0.073 (3)0.028 (2)0.017 (2)0.026 (3)
C390.041 (2)0.064 (3)0.058 (2)0.012 (2)0.0080 (18)0.013 (2)
C230.059 (3)0.049 (2)0.070 (3)0.029 (2)0.004 (2)0.003 (2)
C420.062 (3)0.065 (3)0.065 (3)0.029 (2)0.011 (2)0.018 (2)
C150.053 (2)0.068 (3)0.073 (3)0.027 (2)0.006 (2)0.036 (2)
C70.057 (3)0.045 (2)0.062 (3)0.004 (2)0.015 (2)0.009 (2)
C190.042 (2)0.075 (3)0.048 (2)0.014 (2)0.0008 (17)0.028 (2)
C100.089 (3)0.044 (2)0.058 (2)0.030 (2)0.002 (2)0.015 (2)
C270.097 (4)0.051 (3)0.056 (2)0.043 (3)0.013 (2)0.005 (2)
C80.078 (3)0.038 (2)0.060 (3)0.008 (2)0.008 (2)0.0154 (19)
O10.049 (2)0.100 (3)0.180 (4)0.034 (2)0.011 (2)0.020 (3)
C370.084 (3)0.063 (3)0.058 (3)0.033 (3)0.019 (2)0.017 (2)
C380.057 (3)0.057 (3)0.063 (3)0.009 (2)0.005 (2)0.005 (2)
Cl10.0872 (11)0.1591 (19)0.1237 (14)0.0427 (12)0.0137 (10)0.0052 (12)
O3W0.096 (3)0.092 (3)0.098 (3)0.048 (2)0.028 (2)0.035 (2)
O1W0.107 (3)0.078 (3)0.112 (3)0.030 (2)0.015 (2)0.025 (2)
O4W0.082 (3)0.157 (4)0.128 (3)0.056 (3)0.011 (2)0.051 (3)
O5W0.109 (3)0.104 (3)0.110 (3)0.034 (3)0.023 (3)0.033 (3)
O6W0.107 (3)0.090 (3)0.119 (3)0.029 (3)0.023 (3)0.008 (2)
O7W0.088 (3)0.120 (4)0.152 (4)0.031 (3)0.036 (3)0.037 (3)
O8W0.145 (4)0.154 (5)0.108 (3)0.076 (4)0.011 (3)0.047 (3)
O9W0.207 (6)0.100 (4)0.105 (3)0.013 (4)0.001 (4)0.020 (3)
O10W0.115 (4)0.222 (6)0.128 (4)0.096 (4)0.022 (3)0.003 (4)
O2W0.0598 (17)0.0520 (17)0.0704 (18)0.0283 (14)0.0021 (14)0.0102 (14)
Geometric parameters (Å, º) top
Zn1—N12.155 (3)C3—C21.351 (6)
Zn1—N62.156 (3)C3—H3A0.9300
Zn1—N52.163 (3)C41—C421.378 (6)
Zn1—N42.176 (3)C41—H41A0.9300
Zn1—N22.184 (3)C31—C301.348 (7)
Zn1—N32.185 (3)C31—H31A0.9300
Se1—C451.840 (5)O2—C461.260 (6)
Se1—C431.880 (4)C9—C101.405 (6)
N1—C121.320 (5)C9—C81.428 (6)
N1—C61.360 (5)C44—C451.353 (6)
N3—C131.323 (4)C44—C461.488 (6)
N3—C171.355 (4)C34—C351.348 (6)
N4—C241.323 (5)C34—H34A0.9300
N4—C181.360 (4)C20—C191.354 (6)
C43—N71.298 (5)C20—H20A0.9300
C43—C401.456 (6)C2—H2A0.9300
N2—C11.320 (4)C26—C271.356 (7)
N2—C51.363 (4)C26—H26A0.9300
C18—C211.410 (5)C45—H45A0.9300
C18—C171.435 (5)C46—O11.240 (6)
N5—C251.324 (5)C30—H30A0.9300
N5—C291.356 (5)C22—C231.354 (6)
N6—C361.330 (5)C22—H22A0.9300
N6—C331.355 (5)C35—H35A0.9300
C29—C281.408 (5)C39—C381.368 (6)
C29—C331.444 (5)C39—H39A0.9300
C17—C161.402 (5)C23—H23A0.9300
C5—C41.399 (5)C42—C371.358 (6)
C5—C61.439 (5)C42—H42A0.9300
C33—C321.408 (5)C15—H15A0.9300
C4—C31.414 (6)C7—C81.337 (6)
C4—C71.429 (6)C7—H7A0.9300
N7—C441.393 (5)C19—H19A0.9300
C21—C221.396 (6)C10—H10A0.9300
C21—C201.430 (5)C27—H27A0.9300
C16—C151.407 (6)C8—H8A0.9300
C16—C191.422 (6)C37—C381.382 (6)
C40—C411.380 (5)C37—H37A0.9300
C40—C391.403 (6)C38—H38A0.9300
C36—C351.395 (6)O3W—H3WA0.8496
C36—H36A0.9300O3W—H3WB0.8502
C6—C91.410 (5)O1W—H1WA0.8502
C25—C261.402 (6)O1W—H1WB0.8501
C25—H25A0.9300O4W—H4WA0.8501
C13—C141.390 (6)O4W—H4WB0.8500
C13—H13A0.9300O5W—H5WA0.8502
C24—C231.390 (6)O5W—H5WB0.8498
C24—H24A0.9300O6W—H6WA0.8503
C32—C341.393 (6)O6W—H6WB0.8500
C32—C311.420 (6)O7W—H7WA0.8500
C1—C21.403 (5)O7W—H7WB0.8502
C1—H1A0.9300O8W—H8WA0.8498
C11—C101.364 (7)O8W—H8WB0.8500
C11—C121.396 (6)O9W—H9WA0.8500
C11—H11A0.9300O9W—H9WB0.8499
C28—C271.394 (6)O10W—H10W0.8500
C28—C301.418 (6)O10W—H10E0.8500
C12—H12A0.9300O2W—H2WA0.8500
C14—C151.360 (6)O2W—H2WB0.8503
C14—H14A0.9300
N1—Zn1—N698.12 (11)N1—C12—C11123.3 (4)
N1—Zn1—N5102.04 (11)N1—C12—H12A118.3
N6—Zn1—N577.29 (11)C11—C12—H12A118.3
N1—Zn1—N492.98 (11)C15—C14—C13119.8 (4)
N6—Zn1—N493.51 (11)C15—C14—H14A120.1
N5—Zn1—N4163.28 (11)C13—C14—H14A120.1
N1—Zn1—N276.97 (11)C2—C3—C4119.8 (4)
N6—Zn1—N2169.86 (10)C2—C3—H3A120.1
N5—Zn1—N294.92 (11)C4—C3—H3A120.1
N4—Zn1—N295.59 (10)C42—C41—C40121.2 (4)
N1—Zn1—N3163.66 (11)C42—C41—H41A119.4
N6—Zn1—N395.37 (10)C40—C41—H41A119.4
N5—Zn1—N389.87 (11)C30—C31—C32122.1 (4)
N4—Zn1—N376.98 (11)C30—C31—H31A119.0
N2—Zn1—N391.04 (10)C32—C31—H31A119.0
C45—Se1—C4385.43 (19)C10—C9—C6116.7 (4)
C12—N1—C6117.7 (3)C10—C9—C8124.0 (4)
C12—N1—Zn1128.0 (3)C6—C9—C8119.2 (4)
C6—N1—Zn1114.1 (2)C45—C44—N7116.9 (4)
C13—N3—C17118.3 (3)C45—C44—C46124.9 (4)
C13—N3—Zn1128.1 (3)N7—C44—C46118.2 (4)
C17—N3—Zn1113.5 (2)C35—C34—C32121.1 (4)
C24—N4—C18118.4 (3)C35—C34—H34A119.5
C24—N4—Zn1128.3 (2)C32—C34—H34A119.5
C18—N4—Zn1113.2 (2)C19—C20—C21121.6 (4)
N7—C43—C40124.8 (3)C19—C20—H20A119.2
N7—C43—Se1113.4 (3)C21—C20—H20A119.2
C40—C43—Se1121.8 (3)C3—C2—C1119.1 (4)
C1—N2—C5118.0 (3)C3—C2—H2A120.4
C1—N2—Zn1128.6 (2)C1—C2—H2A120.4
C5—N2—Zn1113.3 (2)C27—C26—C25119.6 (4)
N4—C18—C21121.9 (3)C27—C26—H26A120.2
N4—C18—C17118.5 (3)C25—C26—H26A120.2
C21—C18—C17119.7 (3)C44—C45—Se1110.7 (3)
C25—N5—C29117.9 (3)C44—C45—H45A124.7
C25—N5—Zn1128.4 (3)Se1—C45—H45A124.7
C29—N5—Zn1112.9 (2)O1—C46—O2125.0 (5)
C36—N6—C33117.9 (3)O1—C46—C44116.9 (5)
C36—N6—Zn1128.7 (3)O2—C46—C44118.1 (4)
C33—N6—Zn1113.1 (2)C31—C30—C28120.8 (4)
N5—C29—C28123.0 (3)C31—C30—H30A119.6
N5—C29—C33117.3 (3)C28—C30—H30A119.6
C28—C29—C33119.7 (3)C23—C22—C21120.0 (4)
N3—C17—C16122.5 (3)C23—C22—H22A120.0
N3—C17—C18117.7 (3)C21—C22—H22A120.0
C16—C17—C18119.7 (3)C34—C35—C36119.0 (4)
N2—C5—C4122.6 (3)C34—C35—H35A120.5
N2—C5—C6117.4 (3)C36—C35—H35A120.5
C4—C5—C6120.0 (3)C38—C39—C40120.2 (4)
N6—C33—C32123.0 (3)C38—C39—H39A119.9
N6—C33—C29117.8 (3)C40—C39—H39A119.9
C32—C33—C29119.2 (3)C22—C23—C24119.5 (4)
C5—C4—C3117.3 (3)C22—C23—H23A120.3
C5—C4—C7119.1 (4)C24—C23—H23A120.3
C3—C4—C7123.6 (4)C37—C42—C41120.3 (4)
C43—N7—C44113.6 (3)C37—C42—H42A119.8
C22—C21—C18117.5 (3)C41—C42—H42A119.8
C22—C21—C20123.9 (4)C14—C15—C16119.2 (4)
C18—C21—C20118.6 (4)C14—C15—H15A120.4
C17—C16—C15117.4 (4)C16—C15—H15A120.4
C17—C16—C19119.6 (4)C8—C7—C4121.3 (4)
C15—C16—C19123.0 (4)C8—C7—H7A119.4
C41—C40—C39117.9 (4)C4—C7—H7A119.4
C41—C40—C43122.3 (4)C20—C19—C16120.7 (4)
C39—C40—C43119.8 (3)C20—C19—H19A119.7
N6—C36—C35122.6 (4)C16—C19—H19A119.7
N6—C36—H36A118.7C11—C10—C9119.8 (4)
C35—C36—H36A118.7C11—C10—H10A120.1
N1—C6—C9123.2 (3)C9—C10—H10A120.1
N1—C6—C5117.8 (3)C26—C27—C28119.8 (4)
C9—C6—C5119.0 (3)C26—C27—H27A120.1
N5—C25—C26122.5 (4)C28—C27—H27A120.1
N5—C25—H25A118.8C7—C8—C9121.4 (4)
C26—C25—H25A118.8C7—C8—H8A119.3
N3—C13—C14122.7 (4)C9—C8—H8A119.3
N3—C13—H13A118.6C42—C37—C38119.7 (4)
C14—C13—H13A118.6C42—C37—H37A120.2
N4—C24—C23122.8 (4)C38—C37—H37A120.2
N4—C24—H24A118.6C39—C38—C37120.6 (4)
C23—C24—H24A118.6C39—C38—H38A119.7
C34—C32—C33116.3 (4)C37—C38—H38A119.7
C34—C32—C31124.8 (4)H3WA—O3W—H3WB125.7
C33—C32—C31118.8 (4)H1WA—O1W—H1WB112.6
N2—C1—C2123.1 (4)H4WA—O4W—H4WB103.4
N2—C1—H1A118.4H5WA—O5W—H5WB114.4
C2—C1—H1A118.4H6WA—O6W—H6WB118.3
C10—C11—C12119.2 (4)H7WA—O7W—H7WB95.6
C10—C11—H11A120.4H8WA—O8W—H8WB109.3
C12—C11—H11A120.4H9WA—O9W—H9WB92.4
C27—C28—C29117.1 (4)H10W—O10W—H10E88.7
C27—C28—C30123.6 (4)H2WA—O2W—H2WB117.0
C29—C28—C30119.3 (4)
N6—Zn1—N1—C129.1 (3)N4—C18—C21—C20178.2 (3)
N5—Zn1—N1—C1287.8 (3)C17—C18—C21—C202.5 (5)
N4—Zn1—N1—C1284.9 (3)N3—C17—C16—C150.3 (5)
N2—Zn1—N1—C12179.9 (3)C18—C17—C16—C15179.9 (3)
N3—Zn1—N1—C12136.2 (4)N3—C17—C16—C19179.2 (3)
N6—Zn1—N1—C6176.4 (2)C18—C17—C16—C190.5 (5)
N5—Zn1—N1—C697.8 (2)N7—C43—C40—C41172.0 (4)
N4—Zn1—N1—C689.6 (2)Se1—C43—C40—C416.7 (5)
N2—Zn1—N1—C65.4 (2)N7—C43—C40—C398.1 (6)
N3—Zn1—N1—C638.2 (5)Se1—C43—C40—C39173.2 (3)
N1—Zn1—N3—C13126.9 (4)C33—N6—C36—C350.3 (5)
N6—Zn1—N3—C1387.5 (3)Zn1—N6—C36—C35173.8 (3)
N5—Zn1—N3—C1310.3 (3)C12—N1—C6—C90.2 (5)
N4—Zn1—N3—C13179.9 (3)Zn1—N1—C6—C9175.3 (3)
N2—Zn1—N3—C1384.6 (3)C12—N1—C6—C5179.4 (3)
N1—Zn1—N3—C1750.6 (5)Zn1—N1—C6—C55.5 (4)
N6—Zn1—N3—C1795.0 (2)N2—C5—C6—N11.3 (5)
N5—Zn1—N3—C17172.2 (2)C4—C5—C6—N1178.2 (3)
N4—Zn1—N3—C172.6 (2)N2—C5—C6—C9179.4 (3)
N2—Zn1—N3—C1792.9 (2)C4—C5—C6—C91.1 (5)
N1—Zn1—N4—C2416.8 (3)C29—N5—C25—C261.5 (6)
N6—Zn1—N4—C2481.5 (3)Zn1—N5—C25—C26167.0 (3)
N5—Zn1—N4—C24137.3 (4)C17—N3—C13—C141.1 (5)
N2—Zn1—N4—C2494.0 (3)Zn1—N3—C13—C14176.2 (3)
N3—Zn1—N4—C24176.2 (3)C18—N4—C24—C230.1 (5)
N1—Zn1—N4—C18165.4 (2)Zn1—N4—C24—C23177.9 (3)
N6—Zn1—N4—C1896.3 (2)N6—C33—C32—C341.4 (5)
N5—Zn1—N4—C1840.5 (5)C29—C33—C32—C34178.4 (3)
N2—Zn1—N4—C1888.2 (2)N6—C33—C32—C31178.2 (3)
N3—Zn1—N4—C181.6 (2)C29—C33—C32—C312.0 (5)
C45—Se1—C43—N71.8 (3)C5—N2—C1—C20.2 (5)
C45—Se1—C43—C40177.1 (3)Zn1—N2—C1—C2175.9 (3)
N1—Zn1—N2—C1179.0 (3)N5—C29—C28—C270.8 (5)
N6—Zn1—N2—C1117.1 (6)C33—C29—C28—C27179.5 (3)
N5—Zn1—N2—C177.7 (3)N5—C29—C28—C30177.8 (3)
N4—Zn1—N2—C189.3 (3)C33—C29—C28—C300.9 (5)
N3—Zn1—N2—C112.2 (3)C6—N1—C12—C111.0 (6)
N1—Zn1—N2—C54.8 (2)Zn1—N1—C12—C11173.4 (3)
N6—Zn1—N2—C566.7 (7)C10—C11—C12—N11.3 (6)
N5—Zn1—N2—C5106.0 (2)N3—C13—C14—C150.3 (6)
N4—Zn1—N2—C587.0 (2)C5—C4—C3—C20.9 (6)
N3—Zn1—N2—C5164.0 (2)C7—C4—C3—C2179.9 (4)
C24—N4—C18—C211.6 (5)C39—C40—C41—C420.1 (6)
Zn1—N4—C18—C21179.7 (2)C43—C40—C41—C42180.0 (4)
C24—N4—C18—C17177.7 (3)C34—C32—C31—C30179.5 (4)
Zn1—N4—C18—C170.4 (3)C33—C32—C31—C300.1 (6)
N1—Zn1—N5—C2583.7 (3)N1—C6—C9—C100.9 (5)
N6—Zn1—N5—C25179.5 (3)C5—C6—C9—C10179.9 (3)
N4—Zn1—N5—C25122.7 (4)N1—C6—C9—C8177.6 (3)
N2—Zn1—N5—C256.0 (3)C5—C6—C9—C81.6 (5)
N3—Zn1—N5—C2585.0 (3)C43—N7—C44—C452.2 (5)
N1—Zn1—N5—C29107.3 (2)C43—N7—C44—C46179.1 (3)
N6—Zn1—N5—C2911.6 (2)C33—C32—C34—C350.2 (6)
N4—Zn1—N5—C2946.2 (5)C31—C32—C34—C35179.5 (4)
N2—Zn1—N5—C29175.0 (2)C22—C21—C20—C19178.7 (4)
N3—Zn1—N5—C2984.0 (2)C18—C21—C20—C190.7 (5)
N1—Zn1—N6—C3675.9 (3)C4—C3—C2—C11.4 (6)
N5—Zn1—N6—C36176.5 (3)N2—C1—C2—C31.1 (6)
N4—Zn1—N6—C3617.6 (3)N5—C25—C26—C270.4 (7)
N2—Zn1—N6—C36136.1 (6)N7—C44—C45—Se10.7 (5)
N3—Zn1—N6—C3694.9 (3)C46—C44—C45—Se1179.3 (3)
N1—Zn1—N6—C33110.4 (2)C43—Se1—C45—C440.5 (3)
N5—Zn1—N6—C339.8 (2)C45—C44—C46—O1159.8 (5)
N4—Zn1—N6—C33156.1 (2)N7—C44—C46—O118.7 (6)
N2—Zn1—N6—C3350.1 (7)C45—C44—C46—O219.6 (7)
N3—Zn1—N6—C3378.9 (2)N7—C44—C46—O2161.9 (4)
C25—N5—C29—C280.8 (5)C32—C31—C30—C281.7 (6)
Zn1—N5—C29—C28169.4 (3)C27—C28—C30—C31177.3 (4)
C25—N5—C29—C33177.9 (3)C29—C28—C30—C311.2 (6)
Zn1—N5—C29—C3311.9 (4)C18—C21—C22—C231.6 (5)
C13—N3—C17—C160.8 (5)C20—C21—C22—C23179.0 (4)
Zn1—N3—C17—C16176.9 (2)C32—C34—C35—C361.2 (6)
C13—N3—C17—C18179.0 (3)N6—C36—C35—C341.5 (6)
Zn1—N3—C17—C183.3 (3)C41—C40—C39—C380.3 (6)
N4—C18—C17—N32.0 (4)C43—C40—C39—C38179.8 (4)
C21—C18—C17—N3177.3 (3)C21—C22—C23—C240.2 (6)
N4—C18—C17—C16178.2 (3)N4—C24—C23—C220.6 (6)
C21—C18—C17—C162.4 (5)C40—C41—C42—C370.6 (6)
C1—N2—C5—C40.3 (5)C13—C14—C15—C160.9 (6)
Zn1—N2—C5—C4177.0 (3)C17—C16—C15—C141.2 (5)
C1—N2—C5—C6179.8 (3)C19—C16—C15—C14178.4 (4)
Zn1—N2—C5—C63.5 (4)C5—C4—C7—C80.9 (6)
C36—N6—C33—C321.1 (5)C3—C4—C7—C8179.9 (4)
Zn1—N6—C33—C32173.3 (3)C21—C20—C19—C161.3 (6)
C36—N6—C33—C29178.6 (3)C17—C16—C19—C201.4 (5)
Zn1—N6—C33—C296.9 (4)C15—C16—C19—C20178.2 (4)
N5—C29—C33—N63.4 (4)C12—C11—C10—C90.5 (6)
C28—C29—C33—N6177.8 (3)C6—C9—C10—C110.5 (6)
N5—C29—C33—C32176.3 (3)C8—C9—C10—C11178.0 (4)
C28—C29—C33—C322.4 (5)C25—C26—C27—C281.3 (7)
N2—C5—C4—C30.0 (5)C29—C28—C27—C261.8 (6)
C6—C5—C4—C3179.4 (3)C30—C28—C27—C26176.8 (4)
N2—C5—C4—C7179.3 (3)C4—C7—C8—C90.4 (7)
C6—C5—C4—C70.2 (5)C10—C9—C8—C7179.3 (4)
C40—C43—N7—C44176.2 (3)C6—C9—C8—C70.9 (6)
Se1—C43—N7—C442.6 (4)C41—C42—C37—C381.1 (7)
N4—C18—C21—C222.4 (5)C40—C39—C38—C370.2 (7)
C17—C18—C21—C22176.9 (3)C42—C37—C38—C390.9 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2Wi0.852.052.898 (5)179
O1W—H1WB···O9Wii0.851.982.830 (6)180
O4W—H4WA···N7ii0.852.223.044 (5)163
O4W—H4WA···O1ii0.852.402.921 (7)120
O5W—H5WA···O6Wiii0.851.912.762 (6)178
O6W—H6WA···Cl1iii0.852.243.076 (5)168
O7W—H7WB···Cl1iv0.852.543.391 (5)179
O8W—H8WB···O7Wv0.851.972.817 (7)180
O2W—H2WA···O9Wvi0.851.962.806 (5)179
O2W—H2WB···Cl1vii0.852.283.129 (3)180
O4W—H4WB···O10.851.982.809 (6)166
O5W—H5WB···O3W0.852.072.915 (6)173
O6W—H6WB···O20.852.052.892 (6)171
O7W—H7WA···Cl10.852.243.006 (5)150
O8W—H8WA···O20.851.972.819 (5)172
O9W—H9WA···O8W0.852.052.864 (8)161
O9W—H9WB···O10W0.852.183.030 (8)178
O10W—H10W···O4W0.852.022.866 (8)173
O10W—H10E···O20.852.082.925 (6)171
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z+2; (v) x, y, z1; (vi) x1, y, z+1; (vii) x1, y, z.

Experimental details

Crystal data
Chemical formula[Zn(C12H8N2)3](C10H6NO2Se)Cl·10H2O
Mr1072.71
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)12.4837 (9), 13.8935 (10), 15.8221 (12)
α, β, γ (°)77.618 (4), 89.642 (4), 63.375 (4)
V3)2383.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)1.40
Crystal size (mm)0.64 × 0.35 × 0.17
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.562, 0.790
No. of measured, independent and
observed [I > 2σ(I)] reflections
33787, 8371, 6305
Rint0.038
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.140, 1.06
No. of reflections8371
No. of parameters613
No. of restraints30
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.81, 0.74

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1WA···O2Wi0.852.052.898 (5)179
O1W—H1WB···O9Wii0.851.982.830 (6)180
O4W—H4WA···N7ii0.852.223.044 (5)163
O4W—H4WA···O1ii0.852.402.921 (7)120
O5W—H5WA···O6Wiii0.851.912.762 (6)178
O6W—H6WA···Cl1iii0.852.243.076 (5)168
O7W—H7WB···Cl1iv0.852.543.391 (5)179.
O8W—H8WB···O7Wv0.851.972.817 (7)180
O2W—H2WA···O9Wvi0.851.962.806 (5)179
O2W—H2WB···Cl1vii0.852.283.129 (3)180
O4W—H4WB···O10.851.982.809 (6)166
O5W—H5WB···O3W0.852.072.915 (6)173
O6W—H6WB···O20.852.052.892 (6)171
O7W—H7WA···Cl10.852.243.006 (5)150
O8W—H8WA···O20.851.972.819 (5)172
O9W—H9WA···O8W0.852.052.864 (8)161
O9W—H9WB···O10W0.852.183.030 (8)178
O10W—H10W···O4W0.852.022.866 (8)173
O10W—H10E···O20.852.082.925 (6)171
Symmetry codes: (i) x+1, y, z; (ii) x+2, y, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y+1, z+2; (v) x, y, z1; (vi) x1, y, z+1; (vii) x1, y, z.
 

Acknowledgements

This project was supported by the Natural Science of Fundation of Zhejiang (Y4080256) and the Zhejiang students' science and technology innovation plan (young talent plan).

References

First citationBoritzki, T. J., Berry, D. A., Besserer, J. A., Cook, P. D., Fry, D. W., Leopold, W. R. & Jackson, R. C. (1985). Biochem. Pharmacol. 34, 1109–1114.  CrossRef CAS PubMed Web of Science Google Scholar
First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  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 citationSrivastava, P. C. & Robins, R. K. (1983). J. Med. Chem. 26, 445–448.  CrossRef CAS PubMed Web of Science Google Scholar
First citationWang, X. L., Zhang, X. Y., Ma, Y. & Wang, E. B. (2006). J. Northeast Normal Univ. 38, 68–72.  CAS Google Scholar
First citationZhao, G.-L., Shi, X., Zhang, J. P., Liu, J.-F., Xian, H.-D. & Shao, L. X. (2010). Chem. Sci. China, 40, 1525–1535.  Google Scholar

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Volume 67| Part 2| February 2011| Pages m186-m187
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