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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-Hy­dr­oxy-N′-[(E)-2-thienyl­methyl­­idene]-2-naphtho­hydrazide

aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: handongyin@163.com

(Received 10 December 2010; accepted 24 December 2010; online 8 January 2011)

The asymmetric unit of the title compound, C16H12N2O2S, contains three independent mol­ecules. Intra­molecular N—H⋯O hydrogen bonds in the three mol­ecules lead to very similar conformations: the thio­pene ring and naphthalene ring system in the three mol­ecules form dihedral angles of 10.3 (2), 9.1 (2) and 9.3 (3)°. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains propagating in [031].

Related literature

For related structures, see: Huang (2009[Huang, H.-T. (2009). Acta Cryst. E65, o892.]); Liang et al. (2008[Liang, Q.-F., Feng, H.-M. & Li, F.-Q. (2008). Acta Cryst. E64, o1008.]); Shafiq et al. (2009[Shafiq, Z., Yaqub, M., Tahir, M. N., Nawaz, M. H. & Iqbal, M. S. (2009). Acta Cryst. E65, o2845-o2846.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12N2O2S

  • Mr = 296.34

  • Orthorhombic, P n a 21

  • a = 19.8191 (16) Å

  • b = 6.2487 (5) Å

  • c = 33.947 (3) Å

  • V = 4204.1 (6) Å3

  • Z = 12

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 298 K

  • 0.41 × 0.17 × 0.06 mm

Data collection
  • Bruker SMART 1000 CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.909, Tmax = 0.986

  • 20887 measured reflections

  • 7258 independent reflections

  • 3449 reflections with I > 2σ(I)

  • Rint = 0.077

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 0.078

  • S = 0.97

  • 7258 reflections

  • 569 parameters

  • 11 restraints

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.24 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 3473 Friedel pairs

  • Flack parameter: 0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O6—H51⋯O2 0.82 2.03 2.771 (5) 149
N6—H54⋯O6 0.86 1.96 2.641 (5) 135
N2—H2A⋯O4 0.86 1.96 2.660 (5) 138
N4—H53⋯O5 0.86 1.90 2.614 (5) 139
O5—H50⋯O1 0.82 1.87 2.682 (5) 169
O4—H4⋯O3i 0.82 2.40 2.688 (5) 102
Symmetry code: (i) [-x+{\script{1\over 2}}, y-{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART 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


Comment top

In continuation of our research of organotin derivatives, the title compound (I) - a novel Schiff base - have been synthesized. Herewith we present its crystal structure.

In (I), there are three independent molecules in the asymmetric unit (Fig. 1). All the bond lengths and angles are normal and correspond to those observed in the related compounds (Huang (2009); Liang et al. (2008); Shafiq et al. (2009). Intramolecular N—H···O hydrogen bonds (Table 1) lead to very close conformations - the thiopene ring and naphthalene bicycle in three molecules form dihedral angles of 9.67 (27)°, 9.16 (29)° and 9.41 (26)°, respectively.

In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into chains propagated in direction [031].

Related literature top

For related structures, see: Huang (2009); Liang et al. (2008); Shafiq et al. (2009).

Experimental top

The methanol solution of thiophene(0.1 mol) was added dropwise to a solution of 3-hydroxyl-2-naphthohydrazide(0.1 mol) in mehtanol. Then the mixture was stirred at room temperature for 6 h, during which time a yellow precipitate can be observed. The mixture was filtrated and the obtained solid was recrystallized from methanol. Yield 80%. M.p. 245°C. Anal. Calcd (%) for C16H12N2O2S (Mr = 296.34): C, 64.84; H, 4.08; N, 9.45. Found (%): C, 64.82; H, 4.03; N, 9.49.

Refinement top

All H atoms were placed in geometrically idealized positions (C—H=0.93 Å, O—H=0.82 Å, N—H=0.86 Å) and refined using a riding model, with Uiso(H) = 1.2 Ueq(C, O, N).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. Three independent molecules of (I) showing the atomic numbering and 50% probability displacement ellipsoids. The hydrogen bonds are shown as dashed lines.
3-Hydroxy-N'-[(E)-2-thienylmethylidene]-2-naphthohydrazide top
Crystal data top
C16H12N2O2SDx = 1.405 Mg m3
Mr = 296.34Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 2181 reflections
a = 19.8191 (16) Åθ = 2.4–26.4°
b = 6.2487 (5) ŵ = 0.24 mm1
c = 33.947 (3) ÅT = 298 K
V = 4204.1 (6) Å3Block, yellow
Z = 120.41 × 0.17 × 0.06 mm
F(000) = 1848
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
7258 independent reflections
Radiation source: fine-focus sealed tube3449 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.077
phi and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.909, Tmax = 0.986k = 76
20887 measured reflectionsl = 4038
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0055P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
7258 reflectionsΔρmax = 0.28 e Å3
569 parametersΔρmin = 0.24 e Å3
11 restraintsAbsolute structure: Flack (1983), 3473 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (7)
Crystal data top
C16H12N2O2SV = 4204.1 (6) Å3
Mr = 296.34Z = 12
Orthorhombic, Pna21Mo Kα radiation
a = 19.8191 (16) ŵ = 0.24 mm1
b = 6.2487 (5) ÅT = 298 K
c = 33.947 (3) Å0.41 × 0.17 × 0.06 mm
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
7258 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3449 reflections with I > 2σ(I)
Tmin = 0.909, Tmax = 0.986Rint = 0.077
20887 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.078Δρmax = 0.28 e Å3
S = 0.97Δρmin = 0.24 e Å3
7258 reflectionsAbsolute structure: Flack (1983), 3473 Friedel pairs
569 parametersAbsolute structure parameter: 0.01 (7)
11 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C170.1250 (3)1.3649 (9)0.3320 (2)0.0772 (16)
H170.10411.47280.34650.093*
C180.1214 (3)1.3474 (9)0.2938 (2)0.0852 (18)
H180.09861.44770.27850.102*
C190.1535 (2)1.1707 (8)0.27682 (17)0.0632 (15)
H190.15331.13410.25030.076*
C200.1862 (3)1.0582 (9)0.30730 (18)0.0638 (14)
C210.2286 (3)0.8714 (9)0.30409 (19)0.0645 (17)
H210.23880.81800.27920.077*
C220.3225 (3)0.4907 (9)0.35439 (19)0.0496 (14)
C230.3623 (3)0.2970 (8)0.34149 (16)0.0469 (14)
C240.3623 (3)0.2105 (8)0.30317 (18)0.0533 (15)
C250.3998 (3)0.0317 (8)0.29514 (19)0.0615 (17)
H250.39890.02540.26980.074*
C260.4393 (3)0.0666 (9)0.32362 (19)0.0524 (16)
C270.4776 (3)0.2522 (10)0.3153 (2)0.076 (2)
H270.47690.31070.29010.091*
C280.5149 (3)0.3436 (11)0.3434 (2)0.084 (2)
H280.53970.46570.33750.101*
C290.5173 (3)0.2589 (13)0.3819 (2)0.092 (2)
H290.54300.32440.40140.111*
C300.4813 (3)0.0799 (11)0.3897 (2)0.078 (2)
H300.48360.02050.41480.094*
C310.4410 (3)0.0179 (10)0.36158 (19)0.0547 (16)
C320.4021 (3)0.1999 (9)0.36920 (17)0.0573 (16)
H320.40320.25790.39440.069*
C330.4184 (3)1.8592 (9)0.5359 (2)0.080 (2)
H330.43461.95530.55450.096*
C340.4305 (3)1.8749 (10)0.4964 (2)0.0744 (19)
H340.45721.97980.48480.089*
C350.3980 (2)1.7149 (9)0.47596 (17)0.0592 (16)
H350.39941.70440.44860.071*
C360.3635 (2)1.5730 (8)0.49900 (16)0.0495 (14)
C370.3271 (3)1.3905 (8)0.48448 (16)0.0524 (15)
H370.32611.35960.45770.063*
C380.2277 (3)0.9641 (9)0.51485 (17)0.0455 (15)
C390.1955 (2)0.7777 (8)0.49573 (14)0.0381 (13)
C400.2039 (2)0.7167 (8)0.45615 (16)0.0461 (14)
C410.1721 (3)0.5405 (9)0.44212 (16)0.0573 (16)
H410.17940.50060.41610.069*
C420.1280 (3)0.4142 (8)0.46550 (17)0.0492 (15)
C430.0939 (3)0.2328 (9)0.45136 (18)0.0686 (18)
H430.09900.19200.42520.082*
C440.0541 (3)0.1183 (9)0.47519 (19)0.0651 (17)
H440.03100.00030.46540.078*
C450.0470 (2)0.1750 (9)0.51481 (19)0.0633 (17)
H450.01960.09230.53110.076*
C460.0790 (3)0.3478 (8)0.53006 (16)0.0531 (15)
H460.07350.38490.55640.064*
C470.1208 (2)0.4700 (8)0.50523 (16)0.0447 (14)
C480.1555 (2)0.6543 (8)0.51967 (15)0.0448 (14)
H480.15080.69180.54600.054*
N30.2524 (2)0.7774 (8)0.33437 (14)0.0580 (14)
N40.2909 (2)0.5966 (7)0.32609 (14)0.0588 (13)
H530.29430.55280.30220.071*
N50.2959 (2)1.2714 (7)0.50920 (13)0.0537 (12)
N60.2642 (2)1.0966 (7)0.49271 (13)0.0504 (12)
H540.26801.07290.46790.061*
O20.31792 (19)0.5390 (6)0.38926 (11)0.0695 (12)
O30.21923 (17)1.0000 (5)0.55059 (11)0.0628 (10)
O50.32458 (17)0.3078 (5)0.27397 (10)0.0675 (11)
H500.31390.21880.25740.101*
O60.2452 (2)0.8363 (6)0.43242 (11)0.0657 (11)
H510.25650.76490.41330.099*
S20.17219 (9)1.1672 (3)0.35224 (5)0.0873 (5)
S30.36965 (8)1.6406 (3)0.54683 (5)0.0731 (5)
C10.1105 (3)0.8520 (9)0.1823 (2)0.078 (2)
H10.08870.94850.19880.094*
C20.1095 (3)0.8610 (10)0.1431 (2)0.077 (2)
H20.08540.96380.12910.093*
C30.1482 (2)0.7003 (8)0.12479 (16)0.0556 (16)
H30.15350.68640.09770.067*
C40.1772 (2)0.5665 (8)0.15220 (17)0.0543 (15)
C50.2184 (2)0.3795 (8)0.14311 (17)0.0520 (15)
H50.22780.34320.11710.062*
C60.3083 (3)0.0401 (8)0.18524 (19)0.0481 (15)
C70.3449 (2)0.2287 (8)0.16877 (15)0.0398 (13)
C80.3466 (2)0.2926 (8)0.12870 (17)0.0507 (16)
C90.3838 (3)0.4635 (8)0.11708 (17)0.0536 (15)
H90.38420.50120.09060.064*
C100.4212 (3)0.5836 (8)0.14371 (19)0.0493 (15)
C110.4587 (3)0.7676 (10)0.13163 (19)0.0676 (18)
H110.45960.80790.10530.081*
C120.4926 (3)0.8815 (9)0.1585 (2)0.0762 (19)
H120.51790.99940.15060.091*
C130.4904 (3)0.8241 (10)0.1989 (2)0.0767 (19)
H130.51350.90560.21740.092*
C140.4548 (3)0.6509 (9)0.21041 (18)0.0634 (18)
H140.45430.61340.23690.076*
C150.4193 (2)0.5292 (8)0.18397 (18)0.0463 (15)
C160.3803 (2)0.3475 (8)0.19406 (16)0.0495 (14)
H160.37920.30780.22050.059*
N20.27772 (19)0.0878 (6)0.15848 (14)0.0506 (12)
H2A0.28060.05980.13370.061*
O10.30712 (18)0.0019 (6)0.22020 (12)0.0651 (11)
S10.15723 (9)0.6402 (2)0.19813 (5)0.0774 (5)
N10.2415 (2)0.2660 (7)0.17149 (14)0.0509 (12)
O40.31007 (17)0.1791 (5)0.10045 (10)0.0603 (10)
H40.27140.22520.09950.090*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.069 (4)0.070 (4)0.093 (3)0.007 (3)0.021 (4)0.023 (3)
C180.099 (5)0.064 (4)0.093 (3)0.024 (3)0.009 (4)0.010 (3)
C190.066 (4)0.054 (4)0.070 (2)0.017 (3)0.009 (3)0.004 (3)
C200.059 (4)0.060 (4)0.072 (3)0.009 (2)0.007 (3)0.009 (3)
C210.069 (4)0.067 (5)0.058 (5)0.002 (3)0.001 (4)0.006 (4)
C220.047 (4)0.059 (4)0.043 (4)0.010 (3)0.003 (3)0.001 (4)
C230.046 (4)0.056 (4)0.038 (4)0.005 (3)0.007 (3)0.007 (3)
C240.050 (4)0.051 (4)0.059 (4)0.001 (3)0.004 (3)0.002 (3)
C250.065 (4)0.056 (4)0.063 (4)0.013 (3)0.007 (3)0.018 (3)
C260.044 (4)0.047 (4)0.067 (5)0.001 (3)0.005 (3)0.005 (3)
C270.070 (5)0.061 (4)0.097 (6)0.002 (3)0.012 (4)0.007 (4)
C280.065 (5)0.069 (5)0.118 (7)0.008 (4)0.013 (5)0.022 (5)
C290.073 (5)0.107 (7)0.097 (7)0.001 (5)0.002 (5)0.058 (6)
C300.066 (5)0.090 (6)0.077 (5)0.004 (4)0.011 (4)0.023 (4)
C310.047 (4)0.064 (4)0.053 (5)0.004 (3)0.000 (3)0.010 (4)
C320.056 (4)0.066 (4)0.051 (4)0.014 (3)0.003 (3)0.002 (3)
C330.056 (4)0.067 (4)0.118 (7)0.016 (3)0.017 (4)0.015 (5)
C340.070 (5)0.071 (5)0.082 (5)0.011 (4)0.009 (4)0.011 (4)
C350.059 (4)0.063 (4)0.057 (4)0.004 (3)0.000 (3)0.002 (4)
C360.044 (3)0.048 (4)0.056 (4)0.007 (3)0.002 (3)0.006 (3)
C370.059 (4)0.054 (4)0.045 (4)0.001 (3)0.005 (3)0.006 (3)
C380.043 (4)0.053 (4)0.041 (4)0.009 (3)0.002 (3)0.006 (3)
C390.043 (3)0.044 (3)0.028 (3)0.004 (2)0.002 (3)0.010 (3)
C400.043 (4)0.043 (4)0.052 (4)0.005 (3)0.007 (3)0.004 (3)
C410.061 (4)0.067 (4)0.044 (4)0.009 (3)0.006 (3)0.021 (3)
C420.044 (4)0.049 (4)0.055 (4)0.004 (3)0.006 (3)0.006 (3)
C430.065 (5)0.075 (5)0.065 (5)0.025 (3)0.003 (4)0.009 (4)
C440.061 (4)0.066 (5)0.069 (5)0.008 (3)0.006 (4)0.009 (4)
C450.051 (4)0.065 (5)0.073 (5)0.009 (3)0.008 (3)0.009 (4)
C460.063 (4)0.053 (4)0.043 (4)0.001 (3)0.001 (3)0.003 (3)
C470.041 (3)0.042 (3)0.051 (4)0.009 (3)0.004 (3)0.002 (3)
C480.057 (4)0.041 (3)0.037 (3)0.018 (3)0.000 (3)0.005 (3)
N30.058 (4)0.050 (3)0.066 (4)0.005 (3)0.012 (3)0.019 (3)
N40.073 (4)0.061 (4)0.042 (3)0.002 (3)0.008 (3)0.018 (3)
N50.058 (3)0.045 (3)0.058 (4)0.003 (2)0.004 (3)0.008 (3)
N60.064 (3)0.047 (3)0.040 (3)0.004 (2)0.005 (3)0.012 (2)
O20.090 (3)0.081 (3)0.037 (3)0.003 (2)0.006 (2)0.014 (2)
O30.074 (3)0.068 (3)0.047 (3)0.0139 (19)0.009 (2)0.011 (2)
O50.086 (3)0.064 (3)0.053 (3)0.020 (2)0.007 (2)0.018 (2)
O60.079 (3)0.072 (3)0.045 (3)0.016 (2)0.012 (2)0.017 (2)
S20.0958 (14)0.0883 (13)0.0779 (13)0.0070 (10)0.0068 (11)0.0152 (11)
S30.0846 (13)0.0801 (12)0.0545 (11)0.0074 (9)0.0003 (10)0.0064 (10)
C10.071 (5)0.061 (5)0.103 (7)0.009 (3)0.015 (4)0.018 (5)
C20.058 (4)0.057 (5)0.116 (7)0.006 (3)0.003 (4)0.002 (5)
C30.062 (4)0.055 (4)0.050 (4)0.001 (3)0.009 (3)0.008 (3)
C40.053 (4)0.040 (4)0.069 (5)0.000 (3)0.008 (3)0.006 (3)
C50.059 (4)0.044 (4)0.052 (4)0.001 (3)0.002 (3)0.002 (3)
C60.047 (4)0.043 (4)0.055 (4)0.006 (3)0.001 (3)0.002 (3)
C70.046 (3)0.041 (3)0.032 (4)0.000 (3)0.005 (3)0.003 (3)
C80.044 (4)0.052 (4)0.056 (4)0.008 (3)0.006 (3)0.004 (3)
C90.065 (4)0.046 (4)0.050 (4)0.011 (3)0.004 (3)0.016 (3)
C100.040 (4)0.044 (4)0.063 (5)0.001 (3)0.004 (3)0.002 (3)
C110.061 (4)0.069 (5)0.073 (5)0.006 (4)0.001 (4)0.003 (4)
C120.060 (5)0.070 (5)0.098 (6)0.012 (3)0.003 (5)0.012 (5)
C130.062 (5)0.066 (5)0.102 (6)0.003 (3)0.010 (4)0.014 (4)
C140.057 (4)0.053 (4)0.080 (5)0.014 (3)0.003 (3)0.009 (4)
C150.038 (4)0.043 (4)0.058 (5)0.003 (3)0.002 (3)0.003 (3)
C160.047 (3)0.057 (4)0.045 (4)0.007 (3)0.005 (3)0.008 (3)
N20.061 (3)0.049 (3)0.042 (3)0.002 (2)0.005 (3)0.009 (3)
O10.084 (3)0.065 (3)0.047 (3)0.014 (2)0.002 (2)0.011 (2)
S10.0790 (12)0.0771 (12)0.0762 (12)0.0032 (10)0.0082 (10)0.0121 (11)
N10.057 (3)0.039 (3)0.057 (3)0.007 (2)0.004 (3)0.003 (2)
O40.065 (3)0.069 (3)0.048 (3)0.010 (2)0.006 (2)0.012 (2)
Geometric parameters (Å, º) top
C17—C181.306 (8)C42—C471.400 (7)
C17—S21.695 (6)C43—C441.337 (7)
C17—H170.9300C43—H430.9300
C18—C191.398 (6)C44—C451.398 (7)
C18—H180.9300C44—H440.9300
C19—C201.409 (7)C45—C461.355 (6)
C19—H190.9300C45—H450.9300
C20—C211.442 (7)C46—C471.407 (6)
C20—S21.694 (6)C46—H460.9300
C21—N31.274 (6)C47—C481.427 (6)
C21—H210.9300C48—H480.9300
C22—O21.225 (6)N3—N41.392 (5)
C22—N41.323 (6)N4—H530.8600
C22—C231.510 (7)N5—N61.379 (5)
C23—C321.369 (6)N6—H540.8600
C23—C241.408 (7)O5—O12.682 (5)
C24—O51.382 (6)O5—H500.8199
C24—C251.370 (6)O6—H510.8200
C25—C261.387 (7)C1—C21.332 (7)
C25—H250.9300C1—S11.702 (6)
C26—C311.393 (7)C1—H10.9300
C26—C271.415 (7)C2—C31.409 (7)
C27—C281.336 (8)C2—H20.9300
C27—H270.9300C3—C41.376 (6)
C28—C291.409 (9)C3—H30.9300
C28—H280.9300C4—C51.459 (7)
C29—C301.353 (8)C4—S11.673 (6)
C29—H290.9300C5—N11.281 (6)
C30—C311.387 (7)C5—H50.9300
C30—H300.9300C6—O11.211 (6)
C31—C321.398 (6)C6—N21.353 (6)
C32—H320.9300C6—C71.493 (7)
C33—C341.365 (8)C7—C161.334 (6)
C33—S31.713 (6)C7—C81.418 (7)
C33—H330.9300C8—C91.356 (6)
C34—C351.376 (7)C8—O41.396 (5)
C34—H340.9300C9—C101.389 (7)
C35—C361.365 (6)C9—H90.9300
C35—H350.9300C10—C151.409 (7)
C36—C371.437 (6)C10—C111.430 (7)
C36—S31.682 (5)C11—C121.338 (7)
C37—N51.280 (6)C11—H110.9300
C37—H370.9300C12—C131.418 (8)
C38—O31.245 (6)C12—H120.9300
C38—N61.332 (6)C13—C141.350 (7)
C38—C391.478 (6)C13—H130.9300
C39—C481.373 (6)C14—C151.370 (7)
C39—C401.406 (6)C14—H140.9300
C40—C411.356 (6)C15—C161.415 (6)
C40—O61.370 (5)C16—H160.9300
C41—C421.420 (7)N2—N11.397 (5)
C41—H410.9300N2—H2A0.8600
C42—C431.404 (7)O4—H40.8200
C18—C17—S2111.8 (5)C45—C44—H44119.8
C18—C17—H17124.1C46—C45—C44121.5 (6)
S2—C17—H17124.1C46—C45—H45119.3
C17—C18—C19116.8 (6)C44—C45—H45119.3
C17—C18—H18121.6C45—C46—C47118.7 (5)
C19—C18—H18121.6C45—C46—H46120.7
C18—C19—C20107.5 (6)C47—C46—H46120.7
C18—C19—H19126.2C42—C47—C46120.1 (5)
C20—C19—H19126.2C42—C47—C48118.9 (5)
C19—C20—C21128.1 (6)C46—C47—C48121.0 (5)
C19—C20—S2112.6 (4)C39—C48—C47121.8 (5)
C21—C20—S2119.3 (5)C39—C48—H48119.1
N3—C21—C20121.8 (6)C47—C48—H48119.1
N3—C21—H21119.1C21—N3—N4114.5 (5)
C20—C21—H21119.1C22—N4—N3121.2 (5)
O2—C22—N4122.9 (5)C22—N4—H53119.4
O2—C22—C23121.1 (5)N3—N4—H53119.4
N4—C22—C23115.9 (5)C37—N5—N6114.5 (5)
C32—C23—C24117.7 (5)C38—N6—N5120.7 (4)
C32—C23—C22117.2 (5)C38—N6—H54119.6
C24—C23—C22125.1 (5)N5—N6—H54119.6
O5—C24—C25120.6 (5)C24—O5—O1103.9 (3)
O5—C24—C23119.6 (5)C24—O5—H50109.6
C25—C24—C23119.8 (6)O1—O5—H507.9
C24—C25—C26121.9 (6)C40—O6—H51109.5
C24—C25—H25119.0C17—S2—C2091.1 (3)
C26—C25—H25119.0C36—S3—C3391.8 (3)
C25—C26—C31119.4 (5)C2—C1—S1110.9 (5)
C25—C26—C27121.8 (6)C2—C1—H1124.6
C31—C26—C27118.9 (6)S1—C1—H1124.6
C28—C27—C26120.3 (7)C1—C2—C3113.7 (7)
C28—C27—H27119.9C1—C2—H2123.1
C26—C27—H27119.9C3—C2—H2123.1
C27—C28—C29121.4 (7)C4—C3—C2111.2 (6)
C27—C28—H28119.3C4—C3—H3124.4
C29—C28—H28119.3C2—C3—H3124.4
C30—C29—C28118.3 (7)C3—C4—C5125.3 (5)
C30—C29—H29120.8C3—C4—S1111.4 (4)
C28—C29—H29120.8C5—C4—S1123.3 (5)
C29—C30—C31122.2 (7)N1—C5—C4119.0 (5)
C29—C30—H30118.9N1—C5—H5120.5
C31—C30—H30118.9C4—C5—H5120.5
C30—C31—C26118.9 (6)O1—C6—N2122.2 (5)
C30—C31—C32123.3 (6)O1—C6—C7122.1 (5)
C26—C31—C32117.8 (6)N2—C6—C7115.6 (5)
C23—C32—C31123.4 (6)C16—C7—C8116.6 (5)
C23—C32—H32118.3C16—C7—C6117.0 (5)
C31—C32—H32118.3C8—C7—C6126.4 (5)
C34—C33—S3111.7 (5)C9—C8—O4118.8 (5)
C34—C33—H33124.2C9—C8—C7120.9 (5)
S3—C33—H33124.2O4—C8—C7120.2 (5)
C33—C34—C35111.1 (6)C8—C9—C10121.7 (5)
C33—C34—H34124.4C8—C9—H9119.1
C35—C34—H34124.4C10—C9—H9119.1
C36—C35—C34114.6 (6)C9—C10—C15119.1 (5)
C36—C35—H35122.7C9—C10—C11121.7 (6)
C34—C35—H35122.7C15—C10—C11119.1 (5)
C35—C36—C37124.8 (5)C12—C11—C10119.6 (6)
C35—C36—S3110.7 (4)C12—C11—H11120.2
C37—C36—S3124.5 (4)C10—C11—H11120.2
N5—C37—C36118.6 (5)C11—C12—C13120.6 (6)
N5—C37—H37120.7C11—C12—H12119.7
C36—C37—H37120.7C13—C12—H12119.7
O3—C38—N6120.7 (5)C14—C13—C12120.0 (6)
O3—C38—C39120.8 (5)C14—C13—H13120.0
N6—C38—C39118.5 (5)C12—C13—H13120.0
C48—C39—C40118.8 (5)C13—C14—C15121.6 (6)
C48—C39—C38115.6 (5)C13—C14—H14119.2
C40—C39—C38125.6 (5)C15—C14—H14119.2
C41—C40—O6121.0 (5)C14—C15—C10119.2 (5)
C41—C40—C39120.0 (5)C14—C15—C16124.5 (6)
O6—C40—C39119.0 (5)C10—C15—C16116.3 (5)
C40—C41—C42122.8 (5)C7—C16—C15125.3 (5)
C40—C41—H41118.6C7—C16—H16117.4
C42—C41—H41118.6C15—C16—H16117.4
C43—C42—C47118.8 (5)C6—N2—N1119.3 (5)
C43—C42—C41123.6 (5)C6—N2—H2A120.4
C47—C42—C41117.5 (5)N1—N2—H2A120.4
C44—C43—C42120.6 (6)C6—O1—O5143.8 (4)
C44—C43—H43119.7C4—S1—C192.8 (3)
C42—C43—H43119.7C5—N1—N2112.8 (5)
C43—C44—C45120.4 (6)C8—O4—H4109.5
C43—C44—H44119.8
S2—C17—C18—C192.5 (8)C38—C39—C48—C47179.6 (4)
C17—C18—C19—C203.3 (8)C42—C47—C48—C390.1 (7)
C18—C19—C20—C21176.7 (6)C46—C47—C48—C39178.8 (5)
C18—C19—C20—S22.7 (6)C20—C21—N3—N4178.5 (5)
C19—C20—C21—N3176.1 (6)O2—C22—N4—N32.8 (8)
S2—C20—C21—N34.5 (8)C23—C22—N4—N3179.8 (4)
O2—C22—C23—C3210.7 (8)C21—N3—N4—C22175.6 (5)
N4—C22—C23—C32172.2 (5)C36—C37—N5—N6178.1 (4)
O2—C22—C23—C24170.0 (5)O3—C38—N6—N53.0 (7)
N4—C22—C23—C247.1 (8)C39—C38—N6—N5179.2 (4)
C32—C23—C24—O5177.9 (5)C37—N5—N6—C38177.3 (5)
C22—C23—C24—O51.4 (8)C25—C24—O5—O121.7 (6)
C32—C23—C24—C251.7 (8)C23—C24—O5—O1158.7 (4)
C22—C23—C24—C25179.0 (5)C18—C17—S2—C200.6 (6)
O5—C24—C25—C26178.6 (5)C19—C20—S2—C171.3 (5)
C23—C24—C25—C261.0 (8)C21—C20—S2—C17178.1 (5)
C24—C25—C26—C310.0 (8)C35—C36—S3—C330.0 (4)
C24—C25—C26—C27179.5 (5)C37—C36—S3—C33179.9 (4)
C25—C26—C27—C28179.7 (6)C34—C33—S3—C361.4 (5)
C31—C26—C27—C280.2 (9)S1—C1—C2—C31.8 (8)
C26—C27—C28—C290.2 (10)C1—C2—C3—C41.5 (8)
C27—C28—C29—C300.6 (10)C2—C3—C4—C5177.8 (5)
C28—C29—C30—C311.9 (10)C2—C3—C4—S10.4 (6)
C29—C30—C31—C262.2 (9)C3—C4—C5—N1178.9 (5)
C29—C30—C31—C32178.4 (6)S1—C4—C5—N10.9 (7)
C25—C26—C31—C30179.1 (5)O1—C6—C7—C164.1 (8)
C27—C26—C31—C301.4 (8)N2—C6—C7—C16174.5 (5)
C25—C26—C31—C320.2 (8)O1—C6—C7—C8176.8 (5)
C27—C26—C31—C32179.3 (5)N2—C6—C7—C84.7 (7)
C24—C23—C32—C311.5 (8)C16—C7—C8—C91.4 (7)
C22—C23—C32—C31179.2 (5)C6—C7—C8—C9177.7 (5)
C30—C31—C32—C23179.9 (5)C16—C7—C8—O4179.0 (4)
C26—C31—C32—C230.5 (8)C6—C7—C8—O41.9 (8)
S3—C33—C34—C352.3 (7)O4—C8—C9—C10179.9 (5)
C33—C34—C35—C362.4 (8)C7—C8—C9—C100.5 (8)
C34—C35—C36—C37178.6 (5)C8—C9—C10—C151.3 (8)
C34—C35—C36—S31.4 (6)C8—C9—C10—C11178.1 (5)
C35—C36—C37—N5178.9 (5)C9—C10—C11—C12178.3 (5)
S3—C36—C37—N51.1 (7)C15—C10—C11—C121.6 (8)
O3—C38—C39—C481.5 (7)C10—C11—C12—C131.4 (9)
N6—C38—C39—C48176.4 (5)C11—C12—C13—C141.2 (9)
O3—C38—C39—C40177.1 (5)C12—C13—C14—C151.0 (9)
N6—C38—C39—C405.0 (7)C13—C14—C15—C101.2 (8)
C48—C39—C40—C410.8 (8)C13—C14—C15—C16179.2 (5)
C38—C39—C40—C41179.3 (5)C9—C10—C15—C14178.3 (5)
C48—C39—C40—O6178.4 (4)C11—C10—C15—C141.5 (8)
C38—C39—C40—O60.2 (7)C9—C10—C15—C162.1 (7)
O6—C40—C41—C42178.9 (5)C11—C10—C15—C16178.9 (4)
C39—C40—C41—C422.0 (8)C8—C7—C16—C150.6 (7)
C40—C41—C42—C43179.1 (5)C6—C7—C16—C15178.6 (5)
C40—C41—C42—C473.7 (8)C14—C15—C16—C7179.2 (5)
C47—C42—C43—C441.5 (9)C10—C15—C16—C71.2 (8)
C41—C42—C43—C44178.7 (6)O1—C6—N2—N12.4 (8)
C42—C43—C44—C451.4 (9)C7—C6—N2—N1179.1 (4)
C43—C44—C45—C461.0 (9)N2—C6—O1—O546.8 (9)
C44—C45—C46—C470.8 (8)C7—C6—O1—O5131.6 (5)
C43—C42—C47—C461.3 (7)C24—O5—O1—C6136.0 (7)
C41—C42—C47—C46178.6 (5)C3—C4—S1—C10.5 (4)
C43—C42—C47—C48180.0 (5)C5—C4—S1—C1178.8 (5)
C41—C42—C47—C482.7 (7)C2—C1—S1—C41.3 (5)
C45—C46—C47—C420.9 (7)C4—C5—N1—N2177.6 (4)
C45—C46—C47—C48179.6 (5)C6—N2—N1—C5176.4 (5)
C40—C39—C48—C471.7 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H51···O20.822.032.771 (5)149
N6—H54···O60.861.962.641 (5)135
N2—H2A···O40.861.962.660 (5)138
N4—H53···O50.861.902.614 (5)139
O5—H50···O10.821.872.682 (5)169
O4—H4···O3i0.822.402.688 (5)102
Symmetry code: (i) x+1/2, y3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H12N2O2S
Mr296.34
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)298
a, b, c (Å)19.8191 (16), 6.2487 (5), 33.947 (3)
V3)4204.1 (6)
Z12
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.41 × 0.17 × 0.06
Data collection
DiffractometerBruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.909, 0.986
No. of measured, independent and
observed [I > 2σ(I)] reflections
20887, 7258, 3449
Rint0.077
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.078, 0.97
No. of reflections7258
No. of parameters569
No. of restraints11
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.24
Absolute structureFlack (1983), 3473 Friedel pairs
Absolute structure parameter0.01 (7)

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H51···O20.822.032.771 (5)149
N6—H54···O60.861.962.641 (5)135
N2—H2A···O40.861.962.660 (5)138
N4—H53···O50.861.902.614 (5)139
O5—H50···O10.821.872.682 (5)169
O4—H4···O3i0.822.402.688 (5)102
Symmetry code: (i) x+1/2, y3/2, z1/2.
 

Acknowledgements

We acknowledge the National Natural Science Foundation of China (grant No. 20771053) and the Natural Science Foundation of Shandong Province (grant No. Y2008B48) for financial support.

References

First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHuang, H.-T. (2009). Acta Cryst. E65, o892.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLiang, Q.-F., Feng, H.-M. & Li, F.-Q. (2008). Acta Cryst. E64, o1008.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShafiq, Z., Yaqub, M., Tahir, M. N., Nawaz, M. H. & Iqbal, M. S. (2009). Acta Cryst. E65, o2845–o2846.  Web of Science CSD CrossRef IUCr Journals 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

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