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

Wu, Q.; Yin, H.; Wang, D.

doi:10.1107/S160053681005405X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o277

doi:10.1107/S160053681005405X

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

Qingkun Wu,^a Handong Yin ^a ^* and Daqi Wang ^a

^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 ); Liang et al. (2008 ); Shafiq et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₂S
M_r = 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 ) T_min = 0.909, T_max = 0.986
20887 measured reflections
7258 independent reflections
3449 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 3473 Friedel pairs
Flack parameter: 0.01 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681005405X/cv5019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681005405X/cv5019Isup2.hkl

checkCIF report

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.

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

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

C₁₆H₁₂N₂O₂S	D_x = 1.405 Mg m⁻³
M_r = 296.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 2181 reflections
a = 19.8191 (16) Å	θ = 2.4–26.4°
b = 6.2487 (5) Å	µ = 0.24 mm⁻¹
c = 33.947 (3) Å	T = 298 K
V = 4204.1 (6) Å³	Block, yellow
Z = 12	0.41 × 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 tube	3449 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
T_min = 0.909, T_max = 0.986	k = −7→6
20887 measured reflections	l = −40→38

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0055P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
7258 reflections	Δρ_max = 0.28 e Å⁻³
569 parameters	Δρ_min = −0.24 e Å⁻³
11 restraints	Absolute structure: Flack (1983), 3473 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (7)

Crystal data top

C₁₆H₁₂N₂O₂S	V = 4204.1 (6) Å³
M_r = 296.34	Z = 12
Orthorhombic, Pna2₁	Mo Kα radiation
a = 19.8191 (16) Å	µ = 0.24 mm⁻¹
b = 6.2487 (5) Å	T = 298 K
c = 33.947 (3) Å	0.41 × 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)
T_min = 0.909, T_max = 0.986	R_int = 0.077
20887 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.28 e Å⁻³
S = 0.97	Δρ_min = −0.24 e Å⁻³
7258 reflections	Absolute structure: Flack (1983), 3473 Friedel pairs
569 parameters	Absolute structure parameter: 0.01 (7)
11 restraints

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

	x	y	z	U_iso*/U_eq
C17	0.1250 (3)	1.3649 (9)	0.3320 (2)	0.0772 (16)
H17	0.1041	1.4728	0.3465	0.093*
C18	0.1214 (3)	1.3474 (9)	0.2938 (2)	0.0852 (18)
H18	0.0986	1.4477	0.2785	0.102*
C19	0.1535 (2)	1.1707 (8)	0.27682 (17)	0.0632 (15)
H19	0.1533	1.1341	0.2503	0.076*
C20	0.1862 (3)	1.0582 (9)	0.30730 (18)	0.0638 (14)
C21	0.2286 (3)	0.8714 (9)	0.30409 (19)	0.0645 (17)
H21	0.2388	0.8180	0.2792	0.077*
C22	0.3225 (3)	0.4907 (9)	0.35439 (19)	0.0496 (14)
C23	0.3623 (3)	0.2970 (8)	0.34149 (16)	0.0469 (14)
C24	0.3623 (3)	0.2105 (8)	0.30317 (18)	0.0533 (15)
C25	0.3998 (3)	0.0317 (8)	0.29514 (19)	0.0615 (17)
H25	0.3989	−0.0254	0.2698	0.074*
C26	0.4393 (3)	−0.0666 (9)	0.32362 (19)	0.0524 (16)
C27	0.4776 (3)	−0.2522 (10)	0.3153 (2)	0.076 (2)
H27	0.4769	−0.3107	0.2901	0.091*
C28	0.5149 (3)	−0.3436 (11)	0.3434 (2)	0.084 (2)
H28	0.5397	−0.4657	0.3375	0.101*
C29	0.5173 (3)	−0.2589 (13)	0.3819 (2)	0.092 (2)
H29	0.5430	−0.3244	0.4014	0.111*
C30	0.4813 (3)	−0.0799 (11)	0.3897 (2)	0.078 (2)
H30	0.4836	−0.0205	0.4148	0.094*
C31	0.4410 (3)	0.0179 (10)	0.36158 (19)	0.0547 (16)
C32	0.4021 (3)	0.1999 (9)	0.36920 (17)	0.0573 (16)
H32	0.4032	0.2579	0.3944	0.069*
C33	0.4184 (3)	1.8592 (9)	0.5359 (2)	0.080 (2)
H33	0.4346	1.9553	0.5545	0.096*
C34	0.4305 (3)	1.8749 (10)	0.4964 (2)	0.0744 (19)
H34	0.4572	1.9798	0.4848	0.089*
C35	0.3980 (2)	1.7149 (9)	0.47596 (17)	0.0592 (16)
H35	0.3994	1.7044	0.4486	0.071*
C36	0.3635 (2)	1.5730 (8)	0.49900 (16)	0.0495 (14)
C37	0.3271 (3)	1.3905 (8)	0.48448 (16)	0.0524 (15)
H37	0.3261	1.3596	0.4577	0.063*
C38	0.2277 (3)	0.9641 (9)	0.51485 (17)	0.0455 (15)
C39	0.1955 (2)	0.7777 (8)	0.49573 (14)	0.0381 (13)
C40	0.2039 (2)	0.7167 (8)	0.45615 (16)	0.0461 (14)
C41	0.1721 (3)	0.5405 (9)	0.44212 (16)	0.0573 (16)
H41	0.1794	0.5006	0.4161	0.069*
C42	0.1280 (3)	0.4142 (8)	0.46550 (17)	0.0492 (15)
C43	0.0939 (3)	0.2328 (9)	0.45136 (18)	0.0686 (18)
H43	0.0990	0.1920	0.4252	0.082*
C44	0.0541 (3)	0.1183 (9)	0.47519 (19)	0.0651 (17)
H44	0.0310	0.0003	0.4654	0.078*
C45	0.0470 (2)	0.1750 (9)	0.51481 (19)	0.0633 (17)
H45	0.0196	0.0923	0.5311	0.076*
C46	0.0790 (3)	0.3478 (8)	0.53006 (16)	0.0531 (15)
H46	0.0735	0.3849	0.5564	0.064*
C47	0.1208 (2)	0.4700 (8)	0.50523 (16)	0.0447 (14)
C48	0.1555 (2)	0.6543 (8)	0.51967 (15)	0.0448 (14)
H48	0.1508	0.6918	0.5460	0.054*
N3	0.2524 (2)	0.7774 (8)	0.33437 (14)	0.0580 (14)
N4	0.2909 (2)	0.5966 (7)	0.32609 (14)	0.0588 (13)
H53	0.2943	0.5528	0.3022	0.071*
N5	0.2959 (2)	1.2714 (7)	0.50920 (13)	0.0537 (12)
N6	0.2642 (2)	1.0966 (7)	0.49271 (13)	0.0504 (12)
H54	0.2680	1.0729	0.4679	0.061*
O2	0.31792 (19)	0.5390 (6)	0.38926 (11)	0.0695 (12)
O3	0.21923 (17)	1.0000 (5)	0.55059 (11)	0.0628 (10)
O5	0.32458 (17)	0.3078 (5)	0.27397 (10)	0.0675 (11)
H50	0.3139	0.2188	0.2574	0.101*
O6	0.2452 (2)	0.8363 (6)	0.43242 (11)	0.0657 (11)
H51	0.2565	0.7649	0.4133	0.099*
S2	0.17219 (9)	1.1672 (3)	0.35224 (5)	0.0873 (5)
S3	0.36965 (8)	1.6406 (3)	0.54683 (5)	0.0731 (5)
C1	0.1105 (3)	0.8520 (9)	0.1823 (2)	0.078 (2)
H1	0.0887	0.9485	0.1988	0.094*
C2	0.1095 (3)	0.8610 (10)	0.1431 (2)	0.077 (2)
H2	0.0854	0.9638	0.1291	0.093*
C3	0.1482 (2)	0.7003 (8)	0.12479 (16)	0.0556 (16)
H3	0.1535	0.6864	0.0977	0.067*
C4	0.1772 (2)	0.5665 (8)	0.15220 (17)	0.0543 (15)
C5	0.2184 (2)	0.3795 (8)	0.14311 (17)	0.0520 (15)
H5	0.2278	0.3432	0.1171	0.062*
C6	0.3083 (3)	−0.0401 (8)	0.18524 (19)	0.0481 (15)
C7	0.3449 (2)	−0.2287 (8)	0.16877 (15)	0.0398 (13)
C8	0.3466 (2)	−0.2926 (8)	0.12870 (17)	0.0507 (16)
C9	0.3838 (3)	−0.4635 (8)	0.11708 (17)	0.0536 (15)
H9	0.3842	−0.5012	0.0906	0.064*
C10	0.4212 (3)	−0.5836 (8)	0.14371 (19)	0.0493 (15)
C11	0.4587 (3)	−0.7676 (10)	0.13163 (19)	0.0676 (18)
H11	0.4596	−0.8079	0.1053	0.081*
C12	0.4926 (3)	−0.8815 (9)	0.1585 (2)	0.0762 (19)
H12	0.5179	−0.9994	0.1506	0.091*
C13	0.4904 (3)	−0.8241 (10)	0.1989 (2)	0.0767 (19)
H13	0.5135	−0.9056	0.2174	0.092*
C14	0.4548 (3)	−0.6509 (9)	0.21041 (18)	0.0634 (18)
H14	0.4543	−0.6134	0.2369	0.076*
C15	0.4193 (2)	−0.5292 (8)	0.18397 (18)	0.0463 (15)
C16	0.3803 (2)	−0.3475 (8)	0.19406 (16)	0.0495 (14)
H16	0.3792	−0.3078	0.2205	0.059*
N2	0.27772 (19)	0.0878 (6)	0.15848 (14)	0.0506 (12)
H2A	0.2806	0.0598	0.1337	0.061*
O1	0.30712 (18)	−0.0019 (6)	0.22020 (12)	0.0651 (11)
S1	0.15723 (9)	0.6402 (2)	0.19813 (5)	0.0774 (5)
N1	0.2415 (2)	0.2660 (7)	0.17149 (14)	0.0509 (12)
O4	0.31007 (17)	−0.1791 (5)	0.10045 (10)	0.0603 (10)
H4	0.2714	−0.2252	0.0995	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C17	0.069 (4)	0.070 (4)	0.093 (3)	0.007 (3)	0.021 (4)	−0.023 (3)
C18	0.099 (5)	0.064 (4)	0.093 (3)	0.024 (3)	0.009 (4)	−0.010 (3)
C19	0.066 (4)	0.054 (4)	0.070 (2)	0.017 (3)	0.009 (3)	−0.004 (3)
C20	0.059 (4)	0.060 (4)	0.072 (3)	0.009 (2)	0.007 (3)	−0.009 (3)
C21	0.069 (4)	0.067 (5)	0.058 (5)	−0.002 (3)	0.001 (4)	−0.006 (4)
C22	0.047 (4)	0.059 (4)	0.043 (4)	−0.010 (3)	0.003 (3)	−0.001 (4)
C23	0.046 (4)	0.056 (4)	0.038 (4)	−0.005 (3)	0.007 (3)	−0.007 (3)
C24	0.050 (4)	0.051 (4)	0.059 (4)	0.001 (3)	0.004 (3)	−0.002 (3)
C25	0.065 (4)	0.056 (4)	0.063 (4)	0.013 (3)	−0.007 (3)	−0.018 (3)
C26	0.044 (4)	0.047 (4)	0.067 (5)	0.001 (3)	0.005 (3)	0.005 (3)
C27	0.070 (5)	0.061 (4)	0.097 (6)	0.002 (3)	−0.012 (4)	0.007 (4)
C28	0.065 (5)	0.069 (5)	0.118 (7)	0.008 (4)	0.013 (5)	0.022 (5)
C29	0.073 (5)	0.107 (7)	0.097 (7)	0.001 (5)	−0.002 (5)	0.058 (6)
C30	0.066 (5)	0.090 (6)	0.077 (5)	−0.004 (4)	0.011 (4)	0.023 (4)
C31	0.047 (4)	0.064 (4)	0.053 (5)	−0.004 (3)	0.000 (3)	0.010 (4)
C32	0.056 (4)	0.066 (4)	0.051 (4)	−0.014 (3)	−0.003 (3)	0.002 (3)
C33	0.056 (4)	0.067 (4)	0.118 (7)	−0.016 (3)	−0.017 (4)	−0.015 (5)
C34	0.070 (5)	0.071 (5)	0.082 (5)	−0.011 (4)	−0.009 (4)	0.011 (4)
C35	0.059 (4)	0.063 (4)	0.057 (4)	−0.004 (3)	0.000 (3)	−0.002 (4)
C36	0.044 (3)	0.048 (4)	0.056 (4)	0.007 (3)	−0.002 (3)	0.006 (3)
C37	0.059 (4)	0.054 (4)	0.045 (4)	−0.001 (3)	0.005 (3)	−0.006 (3)
C38	0.043 (4)	0.053 (4)	0.041 (4)	0.009 (3)	−0.002 (3)	−0.006 (3)
C39	0.043 (3)	0.044 (3)	0.028 (3)	0.004 (2)	0.002 (3)	−0.010 (3)
C40	0.043 (4)	0.043 (4)	0.052 (4)	0.005 (3)	0.007 (3)	0.004 (3)
C41	0.061 (4)	0.067 (4)	0.044 (4)	−0.009 (3)	0.006 (3)	−0.021 (3)
C42	0.044 (4)	0.049 (4)	0.055 (4)	0.004 (3)	−0.006 (3)	−0.006 (3)
C43	0.065 (5)	0.075 (5)	0.065 (5)	−0.025 (3)	0.003 (4)	−0.009 (4)
C44	0.061 (4)	0.066 (5)	0.069 (5)	−0.008 (3)	−0.006 (4)	−0.009 (4)
C45	0.051 (4)	0.065 (5)	0.073 (5)	−0.009 (3)	0.008 (3)	0.009 (4)
C46	0.063 (4)	0.053 (4)	0.043 (4)	0.001 (3)	0.001 (3)	0.003 (3)
C47	0.041 (3)	0.042 (3)	0.051 (4)	0.009 (3)	−0.004 (3)	0.002 (3)
C48	0.057 (4)	0.041 (3)	0.037 (3)	0.018 (3)	0.000 (3)	−0.005 (3)
N3	0.058 (4)	0.050 (3)	0.066 (4)	−0.005 (3)	0.012 (3)	−0.019 (3)
N4	0.073 (4)	0.061 (4)	0.042 (3)	0.002 (3)	0.008 (3)	−0.018 (3)
N5	0.058 (3)	0.045 (3)	0.058 (4)	0.003 (2)	−0.004 (3)	−0.008 (3)
N6	0.064 (3)	0.047 (3)	0.040 (3)	−0.004 (2)	0.005 (3)	−0.012 (2)
O2	0.090 (3)	0.081 (3)	0.037 (3)	0.003 (2)	0.006 (2)	−0.014 (2)
O3	0.074 (3)	0.068 (3)	0.047 (3)	−0.0139 (19)	0.009 (2)	−0.011 (2)
O5	0.086 (3)	0.064 (3)	0.053 (3)	0.020 (2)	−0.007 (2)	−0.018 (2)
O6	0.079 (3)	0.072 (3)	0.045 (3)	−0.016 (2)	0.012 (2)	−0.017 (2)
S2	0.0958 (14)	0.0883 (13)	0.0779 (13)	0.0070 (10)	0.0068 (11)	−0.0152 (11)
S3	0.0846 (13)	0.0801 (12)	0.0545 (11)	−0.0074 (9)	−0.0003 (10)	−0.0064 (10)
C1	0.071 (5)	0.061 (5)	0.103 (7)	0.009 (3)	0.015 (4)	−0.018 (5)
C2	0.058 (4)	0.057 (5)	0.116 (7)	0.006 (3)	−0.003 (4)	−0.002 (5)
C3	0.062 (4)	0.055 (4)	0.050 (4)	−0.001 (3)	0.009 (3)	0.008 (3)
C4	0.053 (4)	0.040 (4)	0.069 (5)	0.000 (3)	0.008 (3)	−0.006 (3)
C5	0.059 (4)	0.044 (4)	0.052 (4)	−0.001 (3)	−0.002 (3)	−0.002 (3)
C6	0.047 (4)	0.043 (4)	0.055 (4)	−0.006 (3)	−0.001 (3)	−0.002 (3)
C7	0.046 (3)	0.041 (3)	0.032 (4)	0.000 (3)	−0.005 (3)	−0.003 (3)
C8	0.044 (4)	0.052 (4)	0.056 (4)	0.008 (3)	−0.006 (3)	0.004 (3)
C9	0.065 (4)	0.046 (4)	0.050 (4)	0.011 (3)	0.004 (3)	−0.016 (3)
C10	0.040 (4)	0.044 (4)	0.063 (5)	0.001 (3)	0.004 (3)	−0.002 (3)
C11	0.061 (4)	0.069 (5)	0.073 (5)	−0.006 (4)	0.001 (4)	−0.003 (4)
C12	0.060 (5)	0.070 (5)	0.098 (6)	0.012 (3)	−0.003 (5)	−0.012 (5)
C13	0.062 (5)	0.066 (5)	0.102 (6)	0.003 (3)	−0.010 (4)	0.014 (4)
C14	0.057 (4)	0.053 (4)	0.080 (5)	0.014 (3)	0.003 (3)	−0.009 (4)
C15	0.038 (4)	0.043 (4)	0.058 (5)	0.003 (3)	−0.002 (3)	0.003 (3)
C16	0.047 (3)	0.057 (4)	0.045 (4)	−0.007 (3)	−0.005 (3)	−0.008 (3)
N2	0.061 (3)	0.049 (3)	0.042 (3)	0.002 (2)	−0.005 (3)	−0.009 (3)
O1	0.084 (3)	0.065 (3)	0.047 (3)	0.014 (2)	−0.002 (2)	−0.011 (2)
S1	0.0790 (12)	0.0771 (12)	0.0762 (12)	0.0032 (10)	0.0082 (10)	−0.0121 (11)
N1	0.057 (3)	0.039 (3)	0.057 (3)	0.007 (2)	0.004 (3)	−0.003 (2)
O4	0.065 (3)	0.069 (3)	0.048 (3)	0.010 (2)	0.006 (2)	−0.012 (2)

Geometric parameters (Å, º) top

C17—C18	1.306 (8)	C42—C47	1.400 (7)
C17—S2	1.695 (6)	C43—C44	1.337 (7)
C17—H17	0.9300	C43—H43	0.9300
C18—C19	1.398 (6)	C44—C45	1.398 (7)
C18—H18	0.9300	C44—H44	0.9300
C19—C20	1.409 (7)	C45—C46	1.355 (6)
C19—H19	0.9300	C45—H45	0.9300
C20—C21	1.442 (7)	C46—C47	1.407 (6)
C20—S2	1.694 (6)	C46—H46	0.9300
C21—N3	1.274 (6)	C47—C48	1.427 (6)
C21—H21	0.9300	C48—H48	0.9300
C22—O2	1.225 (6)	N3—N4	1.392 (5)
C22—N4	1.323 (6)	N4—H53	0.8600
C22—C23	1.510 (7)	N5—N6	1.379 (5)
C23—C32	1.369 (6)	N6—H54	0.8600
C23—C24	1.408 (7)	O5—O1	2.682 (5)
C24—O5	1.382 (6)	O5—H50	0.8199
C24—C25	1.370 (6)	O6—H51	0.8200
C25—C26	1.387 (7)	C1—C2	1.332 (7)
C25—H25	0.9300	C1—S1	1.702 (6)
C26—C31	1.393 (7)	C1—H1	0.9300
C26—C27	1.415 (7)	C2—C3	1.409 (7)
C27—C28	1.336 (8)	C2—H2	0.9300
C27—H27	0.9300	C3—C4	1.376 (6)
C28—C29	1.409 (9)	C3—H3	0.9300
C28—H28	0.9300	C4—C5	1.459 (7)
C29—C30	1.353 (8)	C4—S1	1.673 (6)
C29—H29	0.9300	C5—N1	1.281 (6)
C30—C31	1.387 (7)	C5—H5	0.9300
C30—H30	0.9300	C6—O1	1.211 (6)
C31—C32	1.398 (6)	C6—N2	1.353 (6)
C32—H32	0.9300	C6—C7	1.493 (7)
C33—C34	1.365 (8)	C7—C16	1.334 (6)
C33—S3	1.713 (6)	C7—C8	1.418 (7)
C33—H33	0.9300	C8—C9	1.356 (6)
C34—C35	1.376 (7)	C8—O4	1.396 (5)
C34—H34	0.9300	C9—C10	1.389 (7)
C35—C36	1.365 (6)	C9—H9	0.9300
C35—H35	0.9300	C10—C15	1.409 (7)
C36—C37	1.437 (6)	C10—C11	1.430 (7)
C36—S3	1.682 (5)	C11—C12	1.338 (7)
C37—N5	1.280 (6)	C11—H11	0.9300
C37—H37	0.9300	C12—C13	1.418 (8)
C38—O3	1.245 (6)	C12—H12	0.9300
C38—N6	1.332 (6)	C13—C14	1.350 (7)
C38—C39	1.478 (6)	C13—H13	0.9300
C39—C48	1.373 (6)	C14—C15	1.370 (7)
C39—C40	1.406 (6)	C14—H14	0.9300
C40—C41	1.356 (6)	C15—C16	1.415 (6)
C40—O6	1.370 (5)	C16—H16	0.9300
C41—C42	1.420 (7)	N2—N1	1.397 (5)
C41—H41	0.9300	N2—H2A	0.8600
C42—C43	1.404 (7)	O4—H4	0.8200

C18—C17—S2	111.8 (5)	C45—C44—H44	119.8
C18—C17—H17	124.1	C46—C45—C44	121.5 (6)
S2—C17—H17	124.1	C46—C45—H45	119.3
C17—C18—C19	116.8 (6)	C44—C45—H45	119.3
C17—C18—H18	121.6	C45—C46—C47	118.7 (5)
C19—C18—H18	121.6	C45—C46—H46	120.7
C18—C19—C20	107.5 (6)	C47—C46—H46	120.7
C18—C19—H19	126.2	C42—C47—C46	120.1 (5)
C20—C19—H19	126.2	C42—C47—C48	118.9 (5)
C19—C20—C21	128.1 (6)	C46—C47—C48	121.0 (5)
C19—C20—S2	112.6 (4)	C39—C48—C47	121.8 (5)
C21—C20—S2	119.3 (5)	C39—C48—H48	119.1
N3—C21—C20	121.8 (6)	C47—C48—H48	119.1
N3—C21—H21	119.1	C21—N3—N4	114.5 (5)
C20—C21—H21	119.1	C22—N4—N3	121.2 (5)
O2—C22—N4	122.9 (5)	C22—N4—H53	119.4
O2—C22—C23	121.1 (5)	N3—N4—H53	119.4
N4—C22—C23	115.9 (5)	C37—N5—N6	114.5 (5)
C32—C23—C24	117.7 (5)	C38—N6—N5	120.7 (4)
C32—C23—C22	117.2 (5)	C38—N6—H54	119.6
C24—C23—C22	125.1 (5)	N5—N6—H54	119.6
O5—C24—C25	120.6 (5)	C24—O5—O1	103.9 (3)
O5—C24—C23	119.6 (5)	C24—O5—H50	109.6
C25—C24—C23	119.8 (6)	O1—O5—H50	7.9
C24—C25—C26	121.9 (6)	C40—O6—H51	109.5
C24—C25—H25	119.0	C17—S2—C20	91.1 (3)
C26—C25—H25	119.0	C36—S3—C33	91.8 (3)
C25—C26—C31	119.4 (5)	C2—C1—S1	110.9 (5)
C25—C26—C27	121.8 (6)	C2—C1—H1	124.6
C31—C26—C27	118.9 (6)	S1—C1—H1	124.6
C28—C27—C26	120.3 (7)	C1—C2—C3	113.7 (7)
C28—C27—H27	119.9	C1—C2—H2	123.1
C26—C27—H27	119.9	C3—C2—H2	123.1
C27—C28—C29	121.4 (7)	C4—C3—C2	111.2 (6)
C27—C28—H28	119.3	C4—C3—H3	124.4
C29—C28—H28	119.3	C2—C3—H3	124.4
C30—C29—C28	118.3 (7)	C3—C4—C5	125.3 (5)
C30—C29—H29	120.8	C3—C4—S1	111.4 (4)
C28—C29—H29	120.8	C5—C4—S1	123.3 (5)
C29—C30—C31	122.2 (7)	N1—C5—C4	119.0 (5)
C29—C30—H30	118.9	N1—C5—H5	120.5
C31—C30—H30	118.9	C4—C5—H5	120.5
C30—C31—C26	118.9 (6)	O1—C6—N2	122.2 (5)
C30—C31—C32	123.3 (6)	O1—C6—C7	122.1 (5)
C26—C31—C32	117.8 (6)	N2—C6—C7	115.6 (5)
C23—C32—C31	123.4 (6)	C16—C7—C8	116.6 (5)
C23—C32—H32	118.3	C16—C7—C6	117.0 (5)
C31—C32—H32	118.3	C8—C7—C6	126.4 (5)
C34—C33—S3	111.7 (5)	C9—C8—O4	118.8 (5)
C34—C33—H33	124.2	C9—C8—C7	120.9 (5)
S3—C33—H33	124.2	O4—C8—C7	120.2 (5)
C33—C34—C35	111.1 (6)	C8—C9—C10	121.7 (5)
C33—C34—H34	124.4	C8—C9—H9	119.1
C35—C34—H34	124.4	C10—C9—H9	119.1
C36—C35—C34	114.6 (6)	C9—C10—C15	119.1 (5)
C36—C35—H35	122.7	C9—C10—C11	121.7 (6)
C34—C35—H35	122.7	C15—C10—C11	119.1 (5)
C35—C36—C37	124.8 (5)	C12—C11—C10	119.6 (6)
C35—C36—S3	110.7 (4)	C12—C11—H11	120.2
C37—C36—S3	124.5 (4)	C10—C11—H11	120.2
N5—C37—C36	118.6 (5)	C11—C12—C13	120.6 (6)
N5—C37—H37	120.7	C11—C12—H12	119.7
C36—C37—H37	120.7	C13—C12—H12	119.7
O3—C38—N6	120.7 (5)	C14—C13—C12	120.0 (6)
O3—C38—C39	120.8 (5)	C14—C13—H13	120.0
N6—C38—C39	118.5 (5)	C12—C13—H13	120.0
C48—C39—C40	118.8 (5)	C13—C14—C15	121.6 (6)
C48—C39—C38	115.6 (5)	C13—C14—H14	119.2
C40—C39—C38	125.6 (5)	C15—C14—H14	119.2
C41—C40—O6	121.0 (5)	C14—C15—C10	119.2 (5)
C41—C40—C39	120.0 (5)	C14—C15—C16	124.5 (6)
O6—C40—C39	119.0 (5)	C10—C15—C16	116.3 (5)
C40—C41—C42	122.8 (5)	C7—C16—C15	125.3 (5)
C40—C41—H41	118.6	C7—C16—H16	117.4
C42—C41—H41	118.6	C15—C16—H16	117.4
C43—C42—C47	118.8 (5)	C6—N2—N1	119.3 (5)
C43—C42—C41	123.6 (5)	C6—N2—H2A	120.4
C47—C42—C41	117.5 (5)	N1—N2—H2A	120.4
C44—C43—C42	120.6 (6)	C6—O1—O5	143.8 (4)
C44—C43—H43	119.7	C4—S1—C1	92.8 (3)
C42—C43—H43	119.7	C5—N1—N2	112.8 (5)
C43—C44—C45	120.4 (6)	C8—O4—H4	109.5
C43—C44—H44	119.8

S2—C17—C18—C19	2.5 (8)	C38—C39—C48—C47	179.6 (4)
C17—C18—C19—C20	−3.3 (8)	C42—C47—C48—C39	−0.1 (7)
C18—C19—C20—C21	−176.7 (6)	C46—C47—C48—C39	−178.8 (5)
C18—C19—C20—S2	2.7 (6)	C20—C21—N3—N4	178.5 (5)
C19—C20—C21—N3	−176.1 (6)	O2—C22—N4—N3	2.8 (8)
S2—C20—C21—N3	4.5 (8)	C23—C22—N4—N3	179.8 (4)
O2—C22—C23—C32	−10.7 (8)	C21—N3—N4—C22	175.6 (5)
N4—C22—C23—C32	172.2 (5)	C36—C37—N5—N6	−178.1 (4)
O2—C22—C23—C24	170.0 (5)	O3—C38—N6—N5	3.0 (7)
N4—C22—C23—C24	−7.1 (8)	C39—C38—N6—N5	−179.2 (4)
C32—C23—C24—O5	−177.9 (5)	C37—N5—N6—C38	−177.3 (5)
C22—C23—C24—O5	1.4 (8)	C25—C24—O5—O1	21.7 (6)
C32—C23—C24—C25	1.7 (8)	C23—C24—O5—O1	−158.7 (4)
C22—C23—C24—C25	−179.0 (5)	C18—C17—S2—C20	−0.6 (6)
O5—C24—C25—C26	178.6 (5)	C19—C20—S2—C17	−1.3 (5)
C23—C24—C25—C26	−1.0 (8)	C21—C20—S2—C17	178.1 (5)
C24—C25—C26—C31	0.0 (8)	C35—C36—S3—C33	0.0 (4)
C24—C25—C26—C27	179.5 (5)	C37—C36—S3—C33	179.9 (4)
C25—C26—C27—C28	−179.7 (6)	C34—C33—S3—C36	−1.4 (5)
C31—C26—C27—C28	−0.2 (9)	S1—C1—C2—C3	−1.8 (8)
C26—C27—C28—C29	−0.2 (10)	C1—C2—C3—C4	1.5 (8)
C27—C28—C29—C30	−0.6 (10)	C2—C3—C4—C5	177.8 (5)
C28—C29—C30—C31	1.9 (10)	C2—C3—C4—S1	−0.4 (6)
C29—C30—C31—C26	−2.2 (9)	C3—C4—C5—N1	−178.9 (5)
C29—C30—C31—C32	178.4 (6)	S1—C4—C5—N1	−0.9 (7)
C25—C26—C31—C30	−179.1 (5)	O1—C6—C7—C16	−4.1 (8)
C27—C26—C31—C30	1.4 (8)	N2—C6—C7—C16	174.5 (5)
C25—C26—C31—C32	0.2 (8)	O1—C6—C7—C8	176.8 (5)
C27—C26—C31—C32	−179.3 (5)	N2—C6—C7—C8	−4.7 (7)
C24—C23—C32—C31	−1.5 (8)	C16—C7—C8—C9	−1.4 (7)
C22—C23—C32—C31	179.2 (5)	C6—C7—C8—C9	177.7 (5)
C30—C31—C32—C23	179.9 (5)	C16—C7—C8—O4	179.0 (4)
C26—C31—C32—C23	0.5 (8)	C6—C7—C8—O4	−1.9 (8)
S3—C33—C34—C35	2.3 (7)	O4—C8—C9—C10	−179.9 (5)
C33—C34—C35—C36	−2.4 (8)	C7—C8—C9—C10	0.5 (8)
C34—C35—C36—C37	−178.6 (5)	C8—C9—C10—C15	1.3 (8)
C34—C35—C36—S3	1.4 (6)	C8—C9—C10—C11	178.1 (5)
C35—C36—C37—N5	−178.9 (5)	C9—C10—C11—C12	−178.3 (5)
S3—C36—C37—N5	1.1 (7)	C15—C10—C11—C12	−1.6 (8)
O3—C38—C39—C48	1.5 (7)	C10—C11—C12—C13	1.4 (9)
N6—C38—C39—C48	−176.4 (5)	C11—C12—C13—C14	−1.2 (9)
O3—C38—C39—C40	−177.1 (5)	C12—C13—C14—C15	1.0 (9)
N6—C38—C39—C40	5.0 (7)	C13—C14—C15—C10	−1.2 (8)
C48—C39—C40—C41	0.8 (8)	C13—C14—C15—C16	179.2 (5)
C38—C39—C40—C41	179.3 (5)	C9—C10—C15—C14	178.3 (5)
C48—C39—C40—O6	−178.4 (4)	C11—C10—C15—C14	1.5 (8)
C38—C39—C40—O6	0.2 (7)	C9—C10—C15—C16	−2.1 (7)
O6—C40—C41—C42	−178.9 (5)	C11—C10—C15—C16	−178.9 (4)
C39—C40—C41—C42	2.0 (8)	C8—C7—C16—C15	0.6 (7)
C40—C41—C42—C43	179.1 (5)	C6—C7—C16—C15	−178.6 (5)
C40—C41—C42—C47	−3.7 (8)	C14—C15—C16—C7	−179.2 (5)
C47—C42—C43—C44	1.5 (9)	C10—C15—C16—C7	1.2 (8)
C41—C42—C43—C44	178.7 (6)	O1—C6—N2—N1	−2.4 (8)
C42—C43—C44—C45	−1.4 (9)	C7—C6—N2—N1	179.1 (4)
C43—C44—C45—C46	1.0 (9)	N2—C6—O1—O5	−46.8 (9)
C44—C45—C46—C47	−0.8 (8)	C7—C6—O1—O5	131.6 (5)
C43—C42—C47—C46	−1.3 (7)	C24—O5—O1—C6	−136.0 (7)
C41—C42—C47—C46	−178.6 (5)	C3—C4—S1—C1	−0.5 (4)
C43—C42—C47—C48	180.0 (5)	C5—C4—S1—C1	−178.8 (5)
C41—C42—C47—C48	2.7 (7)	C2—C1—S1—C4	1.3 (5)
C45—C46—C47—C42	0.9 (7)	C4—C5—N1—N2	177.6 (4)
C45—C46—C47—C48	179.6 (5)	C6—N2—N1—C5	176.4 (5)
C40—C39—C48—C47	−1.7 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+1/2, y−3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₂S
M_r	296.34
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	298
a, b, c (Å)	19.8191 (16), 6.2487 (5), 33.947 (3)
V (Å³)	4204.1 (6)
Z	12
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.41 × 0.17 × 0.06

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.909, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	20887, 7258, 3449
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.078, 0.97
No. of reflections	7258
No. of parameters	569
No. of restraints	11
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.24
Absolute structure	Flack (1983), 3473 Friedel pairs
Absolute structure parameter	0.01 (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···A	D—H	H···A	D···A	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+1/2, y−3/2, z−1/2.

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

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