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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2853
https://doi.org/10.1107/S160053680904272X

Benzyl 3-(10-oxo-9,10-di­hydrophenanthren-9-yl­idene)di­thiocarbazate

Qiao-Ru Liu,a Song-Mao Chu,a Gan-Qing Zhao,a* Li-Hua Chena and Yong-Jun Hana

aSchool of Chemistry and Chemical Engineering, Pingdingshan University, Pingdingshan 467000, People's Republic of China
*Correspondence e-mail: zgq1118@163.com

(Received 24 September 2009; accepted 17 October 2009; online 28 October 2009)

In the title compound, C22H16N2OS2, the phenanthrene ring is nearly perpendicular to the phenyl ring, making a dihedral angle of 87.2 (2)°. Intra­molecular N—H⋯O inter­actions are present. In the crystal structure, the mol­ecules are linked through inter­molecular C—H⋯O inter­actions. The crystal structure is also stabilized by C—H⋯π inter­actions and weak π–π contacts [centroid-centroid distance = 3.36 (6) Å].

Related literature

For the biological properties of Schiff bases, see: Bhandari et al. (2008[Bhandari, S. V., Bothara, K. G., Raut, M. K., Patil, A. A., Sarkate, A. P. & Mokale, V. J. (2008). Bioorg. Med. Chem. 16, 1822-1831.]). Recently, some Schiff bases derived from the reaction of S-benzyl­dithio­carbazate with aldehydes or ketones have been reported, see: Ali et al. (2003a[Ali, M. A., Mirza, A. H., Nazimuddin, M., Ahmed, R., Gahan, L. R. & Bernhardt, P. V. (2003a). Polyhedron, 22, 1471-1479.],b[Ali, M. A., Mirza, A. H., Voo, C. W., Tan, A. L. & Bernhardt, P. V. (2003b). Polyhedron, 22, 3433-3438.]); How et al. (2007[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.]); Tarafder et al. (2008[Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.]); Zhou et al. (2002[Zhou, J. H., Wang, Y. X., Chen, X. T., Song, Y. L., Weng, L. H. & You, X. Z. (2002). Chin. J. Inorg. Chem. 5, 533-536.]). For the synthesis of S-benzyl­dithio­carbazate, see: Chew et al. (2004[Chew, K. B., Tarafder, M. T. H., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2004). Polyhedron, 23, 1385-1392.]). For the synthesis of the title compound, see: Ali et al. (2004[Ali, M. A., Mirza, A. H., Ravoof, T. B. S. A. & Bernhardt, P. V. (2004). Polyhedron, 23, 2031-2036.]).

[Scheme 1]

Experimental

Crystal data

  • C22H16N2OS2

  • Mr = 388.49

  • Monoclinic, P 21 /c

  • a = 14.4945 (19) Å

  • b = 5.6978 (7) Å

  • c = 22.816 (3) Å

  • β = 93.610 (2)°

  • V = 1880.6 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 296 K

  • 0.30 × 0.30 × 0.20 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.916, Tmax = 0.943

  • 9220 measured reflections

  • 3316 independent reflections

  • 2638 reflections with I > 2σ(I)

  • Rint = 0.022
Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.06

  • 3316 reflections

  • 244 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N2—H2⋯O1 0.86 1.89 2.560 (2) 134
C12—H12⋯O1i 0.93 2.42 3.239 (2) 147
C5—H5⋯Cg1ii 0.93 2.76 3.559 (2) 144
Symmetry codes: (i) -x, -y+3, -z; (ii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]. Cg1 is the centroid of the C2–C7 ring.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680904272X/hg2573sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680904272X/hg2573Isup2.hkl

checkCIF report


Comment top

Schiff bases are versatile compounds which possess excellent biologically properties (Bhandari et al.,2008). Recently, some Schiff bases derived from the reaction of S-benzyldithiocarbazate with aldehydes or ketones have been reported (Zhou et al., 2002; Ali et al., 2003a,b; How et al., 2007; Tarafder et al., 2008). We synthesized the title compound ((Fig. 1)) and report herein its crystal structure.

In the title compound, the bond lengths and angles are comparable to the values in the similar Schiff bases (Zhou et al., 2002). The phenanthrene ring (C1···C14) and dithiocarbazate (N1/N2/S1/S2/C15) fragments lie essentially in the same plane, with a mean deviation from the least-squares plane of 0.0385 Å. The phenanthrene ring (C1···C14) is nearly perpendicular to the phenyl ring (C17···C22) with a dihedral angle of 87.2°.

In the crystal structure, there are intramolecular N—H···O type hydrogen bonds (Table 1). The crystal structure is consolidated by intermolecular C—H···O [3.239 Å] (Fig. 2). It is also stabilized by C—H···Π interactions such as C5—H5···Π (3.642 Å) and C9—H9···Π (3.643 Å) involving phenanthrene ring and phenyl ring of the adjacent molecules respectively. In addition, π-π interactions between the adjacent phenanthrene rings (centroid-centroid distance = 3.36 (6) Å) may also stabilize the crystal packing.

Related literature top

For the biological properties of Schiff bases, see: Bhandari et al. (2008). Recently, some Schiff bases derived from the reaction of S-benzyldithiocarbazate with aldehydes or ketones have been reported, see: Ali et al. (2003a,b); How et al. (2007); Tarafder et al. (2008); Zhou et al. (2002). For the synthesis of S-benzyldithiocarbazate, see: Chew et al. (2004). For the synthesis of the title compound, see: Ali et al. (2004).

Experimental top

S-benzyldithiocarbazate was synthesized as described in the literature (Chew et al., 2004). The title compound was synthesized as described in the literature (Ali et al., 2004). To 9,10-phenanthrenequinone in 60 ml of absolute ethyl alcohol was added a solution of S-benzyldithiocarbazate (1.00 mmol) in 20 ml of absolute ethyl alcohol dropwise. The red-brown solution was refluxed for 5.0 h at 353 K. The resultant solution was filtered and left in air for a few days, yielding brown block-like crystals.

Refinement top

In (I), All H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (CH) and 0.97 Å (CH2) and Uiso(H) = 1.2Ueq(C), and with N—H = 0.86 Å (NH) and Uiso(H) = 1.2Ueq(N).

Structure description top

Schiff bases are versatile compounds which possess excellent biologically properties (Bhandari et al.,2008). Recently, some Schiff bases derived from the reaction of S-benzyldithiocarbazate with aldehydes or ketones have been reported (Zhou et al., 2002; Ali et al., 2003a,b; How et al., 2007; Tarafder et al., 2008). We synthesized the title compound ((Fig. 1)) and report herein its crystal structure.

In the title compound, the bond lengths and angles are comparable to the values in the similar Schiff bases (Zhou et al., 2002). The phenanthrene ring (C1···C14) and dithiocarbazate (N1/N2/S1/S2/C15) fragments lie essentially in the same plane, with a mean deviation from the least-squares plane of 0.0385 Å. The phenanthrene ring (C1···C14) is nearly perpendicular to the phenyl ring (C17···C22) with a dihedral angle of 87.2°.

In the crystal structure, there are intramolecular N—H···O type hydrogen bonds (Table 1). The crystal structure is consolidated by intermolecular C—H···O [3.239 Å] (Fig. 2). It is also stabilized by C—H···Π interactions such as C5—H5···Π (3.642 Å) and C9—H9···Π (3.643 Å) involving phenanthrene ring and phenyl ring of the adjacent molecules respectively. In addition, π-π interactions between the adjacent phenanthrene rings (centroid-centroid distance = 3.36 (6) Å) may also stabilize the crystal packing.

For the biological properties of Schiff bases, see: Bhandari et al. (2008). Recently, some Schiff bases derived from the reaction of S-benzyldithiocarbazate with aldehydes or ketones have been reported, see: Ali et al. (2003a,b); How et al. (2007); Tarafder et al. (2008); Zhou et al. (2002). For the synthesis of S-benzyldithiocarbazate, see: Chew et al. (2004). For the synthesis of the title compound, see: Ali et al. (2004).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. A view of the crystal packing along the b axis. Intermolecular Hydrogen bonds are shown as dashed lines.
Benzyl 3-(10-oxo-9,10-dihydrophenanthren-9-ylidene)dithiocarbazate top
Crystal data top
C22H16N2OS2F(000) = 808
Mr = 388.49Dx = 1.372 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3545 reflections
a = 14.4945 (19) Åθ = 2.2–27.1°
b = 5.6978 (7) ŵ = 0.30 mm−1
c = 22.816 (3) ÅT = 296 K
β = 93.610 (2)°Block, brown
V = 1880.6 (4) Å30.30 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3316 independent reflections
Radiation source: fine-focus sealed tube2638 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
phi and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −17→12
Tmin = 0.916, Tmax = 0.943k = −6→6
9220 measured reflectionsl = −27→27
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0436P)2 + 0.4502P]
where P = (Fo2 + 2Fc2)/3
3316 reflections(Δ/σ)max < 0.001
244 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C22H16N2OS2V = 1880.6 (4) Å3
Mr = 388.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.4945 (19) ŵ = 0.30 mm−1
b = 5.6978 (7) ÅT = 296 K
c = 22.816 (3) Å0.30 × 0.30 × 0.20 mm
β = 93.610 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3316 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2638 reflections with I > 2σ(I)
Tmin = 0.916, Tmax = 0.943Rint = 0.022
9220 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.06Δρmax = 0.16 e Å−3
3316 reflectionsΔρmin = −0.22 e Å−3
244 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
C10.12004 (12)0.9543 (3)0.10487 (7)0.0410 (4)
C20.07744 (12)0.7660 (3)0.13826 (7)0.0404 (4)
C30.13280 (14)0.6058 (3)0.17087 (8)0.0505 (5)
H30.19680.62030.17180.061*
C40.09428 (15)0.4277 (3)0.20145 (8)0.0570 (5)
H40.13200.32260.22300.068*
C5−0.00057 (15)0.4045 (3)0.20025 (8)0.0551 (5)
H5−0.02690.28370.22090.066*
C6−0.05593 (14)0.5600 (3)0.16850 (7)0.0496 (5)
H6−0.11980.54220.16790.060*
C7−0.01904 (12)0.7447 (3)0.13706 (7)0.0413 (4)
C8−0.07862 (12)0.9126 (3)0.10288 (7)0.0428 (4)
C9−0.17451 (14)0.8986 (4)0.10096 (9)0.0601 (5)
H9−0.20230.78010.12170.072*
C10−0.22943 (14)1.0568 (4)0.06899 (10)0.0663 (6)
H10−0.29341.04310.06840.080*
C11−0.19058 (14)1.2346 (4)0.03787 (9)0.0594 (5)
H11−0.22791.34110.01650.071*
C12−0.09620 (13)1.2524 (3)0.03891 (8)0.0496 (5)
H12−0.06931.37160.01790.059*
C13−0.04017 (12)1.0942 (3)0.07096 (7)0.0407 (4)
C140.06035 (12)1.1237 (3)0.07105 (7)0.0427 (4)
C150.34732 (13)1.1176 (4)0.07602 (8)0.0513 (5)
C160.51902 (14)0.9484 (5)0.11012 (11)0.0836 (8)
H16A0.53630.90370.07130.100*
H16B0.53101.11480.11540.100*
C170.57478 (13)0.8104 (4)0.15607 (10)0.0635 (6)
C180.61629 (15)0.6028 (5)0.14199 (11)0.0716 (6)
H180.60810.54330.10410.086*
C190.67014 (17)0.4821 (5)0.18405 (14)0.0816 (7)
H190.69840.34220.17430.098*
C200.68202 (17)0.5671 (6)0.23965 (13)0.0863 (8)
H200.71840.48510.26770.104*
C210.64071 (19)0.7725 (6)0.25452 (12)0.0867 (8)
H210.64890.83020.29260.104*
C220.58678 (16)0.8938 (5)0.21272 (12)0.0777 (7)
H220.55831.03290.22290.093*
N10.20996 (10)0.9575 (3)0.10711 (6)0.0466 (4)
N20.25374 (10)1.1215 (3)0.07714 (7)0.0524 (4)
H20.22251.22960.05860.063*
O10.09460 (9)1.2850 (2)0.04354 (6)0.0577 (4)
S10.39768 (3)0.88888 (10)0.11712 (2)0.06204 (18)
S20.39996 (4)1.31825 (12)0.03859 (3)0.0741 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0420 (10)0.0423 (10)0.0385 (9)−0.0001 (8)0.0004 (7)−0.0020 (7)
C20.0478 (10)0.0376 (10)0.0356 (8)0.0010 (8)0.0018 (7)−0.0025 (7)
C30.0527 (11)0.0492 (11)0.0495 (10)0.0071 (9)0.0025 (8)0.0036 (9)
C40.0754 (15)0.0458 (12)0.0496 (11)0.0112 (10)0.0018 (10)0.0057 (9)
C50.0771 (15)0.0438 (11)0.0445 (10)−0.0062 (10)0.0052 (10)0.0042 (8)
C60.0570 (11)0.0479 (11)0.0439 (10)−0.0082 (9)0.0034 (8)−0.0003 (8)
C70.0492 (11)0.0387 (10)0.0360 (8)−0.0024 (8)0.0016 (7)−0.0041 (7)
C80.0434 (10)0.0463 (11)0.0386 (9)−0.0028 (8)0.0016 (7)−0.0045 (8)
C90.0489 (12)0.0670 (14)0.0646 (12)−0.0066 (10)0.0040 (10)0.0138 (11)
C100.0422 (11)0.0809 (16)0.0754 (14)0.0002 (11)0.0008 (10)0.0102 (12)
C110.0511 (12)0.0635 (13)0.0625 (12)0.0100 (10)−0.0056 (9)0.0059 (10)
C120.0516 (11)0.0474 (11)0.0491 (10)0.0019 (9)−0.0015 (8)0.0040 (9)
C130.0439 (10)0.0404 (10)0.0374 (9)−0.0004 (8)−0.0002 (7)−0.0031 (7)
C140.0489 (10)0.0405 (10)0.0384 (9)−0.0010 (8)0.0000 (7)0.0014 (8)
C150.0449 (11)0.0611 (12)0.0479 (10)−0.0051 (9)0.0027 (8)0.0007 (9)
C160.0429 (12)0.112 (2)0.0963 (17)0.0000 (13)0.0097 (12)0.0408 (16)
C170.0373 (11)0.0768 (16)0.0769 (15)−0.0056 (11)0.0074 (10)0.0214 (12)
C180.0517 (13)0.0797 (17)0.0837 (16)−0.0092 (12)0.0081 (11)0.0086 (13)
C190.0622 (15)0.0702 (16)0.114 (2)0.0016 (13)0.0165 (15)0.0235 (16)
C200.0586 (15)0.099 (2)0.100 (2)−0.0074 (15)−0.0065 (14)0.0410 (18)
C210.0824 (18)0.098 (2)0.0784 (17)−0.0195 (17)−0.0051 (14)0.0110 (16)
C220.0680 (16)0.0705 (16)0.0959 (19)−0.0032 (13)0.0151 (14)0.0108 (14)
N10.0442 (9)0.0510 (9)0.0446 (8)−0.0017 (7)0.0026 (7)0.0025 (7)
N20.0441 (9)0.0563 (10)0.0567 (9)−0.0018 (8)0.0021 (7)0.0118 (8)
O10.0509 (8)0.0552 (8)0.0664 (8)−0.0035 (7)0.0000 (6)0.0211 (7)
S10.0432 (3)0.0684 (4)0.0752 (4)0.0020 (3)0.0088 (2)0.0171 (3)
S20.0586 (4)0.0827 (4)0.0809 (4)−0.0146 (3)0.0027 (3)0.0257 (3)
Geometric parameters (Å, º) top
C1—N11.301 (2)C12—H120.9300
C1—C21.474 (2)C13—C141.467 (2)
C1—C141.480 (2)C14—O11.235 (2)
C2—C31.398 (2)C15—N21.358 (2)
C2—C71.402 (2)C15—S21.6432 (19)
C3—C41.370 (3)C15—S11.739 (2)
C3—H30.9300C16—C171.505 (3)
C4—C51.380 (3)C16—S11.808 (2)
C4—H40.9300C16—H16A0.9700
C5—C61.371 (3)C16—H16B0.9700
C5—H50.9300C17—C181.374 (3)
C6—C71.399 (2)C17—C221.378 (3)
C6—H60.9300C18—C191.382 (3)
C7—C81.478 (2)C18—H180.9300
C8—C91.390 (3)C19—C201.359 (4)
C8—C131.401 (2)C19—H190.9300
C9—C101.380 (3)C20—C211.367 (4)
C9—H90.9300C20—H200.9300
C10—C111.378 (3)C21—C221.380 (3)
C10—H100.9300C21—H210.9300
C11—C121.371 (3)C22—H220.9300
C11—H110.9300N1—N21.341 (2)
C12—C131.390 (2)N2—H20.8600
N1—C1—C2116.18 (15)C12—C13—C14118.28 (16)
N1—C1—C14124.21 (16)C8—C13—C14120.78 (15)
C2—C1—C14119.60 (15)O1—C14—C13121.05 (16)
C3—C2—C7119.49 (16)O1—C14—C1120.66 (16)
C3—C2—C1120.34 (16)C13—C14—C1118.29 (15)
C7—C2—C1120.17 (15)N2—C15—S2119.68 (15)
C4—C3—C2121.05 (18)N2—C15—S1112.82 (14)
C4—C3—H3119.5S2—C15—S1127.49 (12)
C2—C3—H3119.5C17—C16—S1108.87 (15)
C3—C4—C5119.87 (18)C17—C16—H16A109.9
C3—C4—H4120.1S1—C16—H16A109.9
C5—C4—H4120.1C17—C16—H16B109.9
C6—C5—C4119.87 (18)S1—C16—H16B109.9
C6—C5—H5120.1H16A—C16—H16B108.3
C4—C5—H5120.1C18—C17—C22119.0 (2)
C5—C6—C7121.82 (18)C18—C17—C16120.7 (2)
C5—C6—H6119.1C22—C17—C16120.3 (2)
C7—C6—H6119.1C17—C18—C19120.2 (2)
C6—C7—C2117.90 (16)C17—C18—H18119.9
C6—C7—C8121.88 (16)C19—C18—H18119.9
C2—C7—C8120.22 (15)C20—C19—C18120.3 (3)
C9—C8—C13117.11 (17)C20—C19—H19119.9
C9—C8—C7121.96 (17)C18—C19—H19119.9
C13—C8—C7120.92 (15)C19—C20—C21120.3 (3)
C10—C9—C8121.44 (19)C19—C20—H20119.8
C10—C9—H9119.3C21—C20—H20119.8
C8—C9—H9119.3C20—C21—C22119.7 (3)
C11—C10—C9120.78 (19)C20—C21—H21120.2
C11—C10—H10119.6C22—C21—H21120.2
C9—C10—H10119.6C17—C22—C21120.5 (3)
C12—C11—C10119.03 (19)C17—C22—H22119.7
C12—C11—H11120.5C21—C22—H22119.7
C10—C11—H11120.5C1—N1—N2119.66 (15)
C11—C12—C13120.71 (18)N1—N2—C15120.22 (16)
C11—C12—H12119.6N1—N2—H2119.9
C13—C12—H12119.6C15—N2—H2119.9
C12—C13—C8120.93 (16)C15—S1—C16100.92 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.892.560 (2)134
C12—H12···O1i0.932.423.239 (2)147
C5—H5···Cg1ii0.932.763.559 (2)144
Symmetry codes: (i) −x, −y+3, −z; (ii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC22H16N2OS2
Mr388.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.4945 (19), 5.6978 (7), 22.816 (3)
β (°) 93.610 (2)
V (Å3)1880.6 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.30 × 0.30 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.916, 0.943
No. of measured, independent and
observed [I > 2σ(I)] reflections		9220, 3316, 2638
Rint0.022
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.098, 1.06
No. of reflections3316
No. of parameters244
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.22

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O10.861.892.560 (2)134
C12—H12···O1i0.932.423.239 (2)147
C5—H5···Cg1ii0.932.763.559 (2)144
Symmetry codes: (i) −x, −y+3, −z; (ii) −x, y−1/2, −z+1/2.
 

Acknowledgements

This research was supported by the National Sciences Foundation of China (No. 20877036) and the Top-class Foundation of Pingdingshan University (No. 2006045 and 2009001).

References

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2853
https://doi.org/10.1107/S160053680904272X
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