N′-(3-Ethoxy-2-hydroxybenzylidene)­benzenesulfonohydrazide

Tai, X.-S.; Feng, Y.-M.; Kong, F.-Y.

doi:10.1107/S1600536808007988

organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Page o750

doi:10.1107/S1600536808007988

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N′-(3-Ethoxy-2-hydroxybenzylidene)benzenesulfonohydrazide

Xi-Shi Tai,^a ^* Yi-Min Feng ^a and Fan-Yuan Kong ^a

^aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: taixishi@lzu.edu.cn

(Received 15 March 2008; accepted 24 March 2008; online 29 March 2008)

There are two molecules in the asymmetric unit of the title compound, C₁₅H₁₆N₂O₄S, both of which are stabilized by an intramolecular O—H⋯N hydrogen bond. Intermolecular N—H⋯O hydrogen bonds lead to [101] chains of molecules in the crystal structure.

Related literature

For related literature, see: Tai et al. (2003 ).

Experimental

Crystal data

C₁₅H₁₆N₂O₄S
M_r = 320.36
Monoclinic, P 2₁ /c
a = 10.3149 (10) Å
b = 39.935 (3) Å
c = 7.9832 (8) Å
β = 105.773 (2)°
V = 3164.7 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 298 (2) K
0.48 × 0.45 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.900, T_max = 0.932
16316 measured reflections
5576 independent reflections
3515 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.160
S = 1.09
5576 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2	0.82	1.89	2.606 (5)	145
O5—H5⋯N4	0.82	1.87	2.591 (5)	146
N1—H1A⋯O5	0.90	2.14	2.948 (5)	149
N3—H3⋯O3ⁱ	0.90	2.11	2.912 (5)	147
Symmetry code: (i) x-1, y, z-1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 global, I. DOI: 10.1107/S1600536808007988/hb2710sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007988/hb2710Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of aroylhydrazone ligands (Tai et al., 2003), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

There are two molecules in the asymmetric unit of (I), both of which are stabilised by an intramolecular O-H···N hydrogen bond (Table 1). Then, intermolecular N-H···O hydrogen bonds lead to [101] chains of molecules in the crystal.

Related literature top

For related literature, see: Tai et al. (2003).

Experimental top

3-Ethoxysalicylaldehyde (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 3 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 78%). Colourless blocks of (I) were obtained by evaporation from a methanol solution after 3 days.

Computing details top

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

Figures top

Fig. 1. The C1-containing molecule in (I) showing 30% displacement ellipsoids for the non-hydrogen atoms. The intramolecular hydrogen bond is indicated by a double-dashed line.

N'-(3-Ethoxy-2-hydroxybenzylidene)benzenesulfonohydrazide top

Crystal data top

C₁₅H₁₆N₂O₄S	F(000) = 1344
M_r = 320.36	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3888 reflections
a = 10.3149 (10) Å	θ = 2.3–22.4°
b = 39.935 (3) Å	µ = 0.22 mm⁻¹
c = 7.9832 (8) Å	T = 298 K
β = 105.773 (2)°	Block, colourless
V = 3164.7 (5) Å³	0.48 × 0.45 × 0.32 mm
Z = 8

Data collection top

Bruker SMART CCD diffractometer	5576 independent reflections
Radiation source: fine-focus sealed tube	3515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→12
T_min = 0.900, T_max = 0.932	k = −47→47
16316 measured reflections	l = −8→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0121P)² + 7.6148P] where P = (F_o² + 2F_c²)/3
5576 reflections	(Δ/σ)_max < 0.001
399 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₅H₁₆N₂O₄S	V = 3164.7 (5) Å³
M_r = 320.36	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.3149 (10) Å	µ = 0.22 mm⁻¹
b = 39.935 (3) Å	T = 298 K
c = 7.9832 (8) Å	0.48 × 0.45 × 0.32 mm
β = 105.773 (2)°

Data collection top

Bruker SMART CCD diffractometer	5576 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3515 reflections with I > 2σ(I)
T_min = 0.900, T_max = 0.932	R_int = 0.047
16316 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.09	Δρ_max = 0.29 e Å⁻³
5576 reflections	Δρ_min = −0.41 e Å⁻³
399 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

	x	y	z	U_iso*/U_eq
N1	0.8862 (4)	0.15474 (10)	0.5062 (5)	0.0505 (10)
H1A	0.8190	0.1591	0.4102	0.061*
N2	0.8858 (4)	0.12091 (10)	0.5385 (5)	0.0457 (10)
N3	0.4135 (4)	0.16102 (10)	−0.1714 (5)	0.0555 (11)
H3	0.3271	0.1542	−0.2033	0.067*
N4	0.4452 (4)	0.16983 (10)	0.0019 (5)	0.0520 (10)
O1	1.0083 (3)	0.06423 (9)	0.6356 (5)	0.0632 (10)
H1	1.0025	0.0839	0.6056	0.095*
O2	0.9949 (4)	0.00231 (10)	0.7310 (5)	0.0795 (12)
O3	1.1327 (3)	0.16038 (9)	0.6246 (4)	0.0632 (10)
O4	0.9990 (4)	0.20311 (8)	0.4304 (5)	0.0704 (11)
O5	0.6248 (3)	0.18032 (8)	0.2945 (4)	0.0590 (9)
H5	0.5955	0.1729	0.1956	0.088*
O6	0.6879 (4)	0.20697 (10)	0.6006 (5)	0.0739 (11)
O7	0.6420 (3)	0.13862 (10)	−0.1276 (5)	0.0732 (11)
O8	0.4647 (3)	0.12903 (9)	−0.4027 (4)	0.0628 (10)
S1	1.02564 (12)	0.16900 (3)	0.47484 (16)	0.0488 (3)
S2	0.50608 (12)	0.13114 (4)	−0.21787 (17)	0.0560 (4)
C1	0.7737 (5)	0.10720 (13)	0.5375 (6)	0.0490 (12)
H1C	0.6947	0.1197	0.5077	0.059*
C2	0.7698 (5)	0.07232 (13)	0.5827 (6)	0.0490 (12)
C3	0.8843 (5)	0.05248 (13)	0.6323 (6)	0.0524 (13)
C4	0.8766 (6)	0.01893 (14)	0.6801 (7)	0.0643 (15)
C5	0.7519 (7)	0.00549 (16)	0.6748 (8)	0.084 (2)
H5A	0.7448	−0.0169	0.7023	0.100*
C6	0.6378 (7)	0.02532 (17)	0.6289 (9)	0.0834 (19)
H6	0.5550	0.0162	0.6301	0.100*
C7	0.6444 (5)	0.05806 (15)	0.5819 (7)	0.0646 (15)
H7	0.5664	0.0709	0.5494	0.078*
C8	0.9923 (7)	−0.03169 (15)	0.7840 (10)	0.094 (2)
H8A	0.9388	−0.0451	0.6888	0.113*
H8B	0.9529	−0.0333	0.8811	0.113*
C9	1.1336 (8)	−0.04390 (16)	0.8364 (10)	0.106 (2)
H9A	1.1737	−0.0407	0.7422	0.158*
H9B	1.1347	−0.0673	0.8644	0.158*
H9C	1.1839	−0.0316	0.9365	0.158*
C10	1.0519 (4)	0.14629 (11)	0.2984 (6)	0.0446 (11)
C11	0.9513 (5)	0.14558 (15)	0.1440 (7)	0.0672 (16)
H11	0.8698	0.1564	0.1344	0.081*
C12	0.9733 (7)	0.12869 (19)	0.0053 (8)	0.093 (2)
H12	0.9058	0.1279	−0.0991	0.111*
C13	1.0929 (7)	0.11296 (17)	0.0181 (8)	0.087 (2)
H13	1.1065	0.1014	−0.0770	0.104*
C14	1.1931 (6)	0.11413 (15)	0.1711 (8)	0.0729 (17)
H14	1.2752	0.1037	0.1791	0.087*
C15	1.1724 (5)	0.13063 (13)	0.3130 (7)	0.0567 (13)
H15	1.2397	0.1311	0.4177	0.068*
C16	0.3577 (5)	0.18495 (12)	0.0593 (7)	0.0536 (13)
H16	0.2712	0.1881	−0.0130	0.064*
C17	0.3915 (5)	0.19724 (11)	0.2357 (7)	0.0475 (12)
C18	0.5232 (5)	0.19556 (11)	0.3449 (6)	0.0487 (12)
C19	0.5557 (5)	0.20971 (12)	0.5107 (7)	0.0543 (13)
C20	0.4553 (6)	0.22539 (13)	0.5660 (8)	0.0709 (16)
H20	0.4764	0.2353	0.6754	0.085*
C21	0.3247 (6)	0.22661 (14)	0.4621 (9)	0.0739 (17)
H21	0.2576	0.2365	0.5031	0.089*
C22	0.2943 (5)	0.21326 (13)	0.2996 (8)	0.0651 (16)
H22	0.2064	0.2148	0.2290	0.078*
C23	0.7310 (7)	0.22377 (17)	0.7650 (9)	0.094 (2)
H23A	0.6864	0.2142	0.8464	0.113*
H23B	0.7086	0.2474	0.7510	0.113*
C24	0.8777 (8)	0.21949 (18)	0.8307 (9)	0.114 (3)
H24A	0.8991	0.1960	0.8392	0.171*
H24B	0.9086	0.2296	0.9437	0.171*
H24C	0.9211	0.2300	0.7523	0.171*
C25	0.4610 (5)	0.09376 (13)	−0.1326 (6)	0.0530 (13)
C26	0.3513 (5)	0.07603 (15)	−0.2264 (8)	0.0721 (17)
H26	0.3004	0.0840	−0.3335	0.087*
C27	0.3164 (6)	0.04625 (16)	−0.1614 (10)	0.0851 (19)
H27	0.2428	0.0340	−0.2254	0.102*
C28	0.3898 (8)	0.03494 (18)	−0.0040 (11)	0.091 (2)
H28	0.3668	0.0149	0.0397	0.109*
C29	0.4971 (9)	0.05293 (19)	0.0901 (9)	0.098 (2)
H29	0.5459	0.0452	0.1989	0.118*
C30	0.5346 (6)	0.08246 (16)	0.0265 (8)	0.0758 (17)
H30	0.6088	0.0945	0.0908	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.034 (2)	0.060 (3)	0.053 (3)	0.0022 (18)	0.0051 (18)	0.002 (2)
N2	0.042 (2)	0.055 (3)	0.040 (2)	−0.0004 (18)	0.0097 (18)	0.0001 (18)
N3	0.039 (2)	0.063 (3)	0.057 (3)	0.003 (2)	0.001 (2)	0.000 (2)
N4	0.042 (2)	0.056 (3)	0.052 (3)	0.002 (2)	0.003 (2)	0.001 (2)
O1	0.046 (2)	0.064 (2)	0.079 (3)	−0.0032 (17)	0.0152 (18)	0.0077 (19)
O2	0.084 (3)	0.061 (2)	0.094 (3)	−0.002 (2)	0.023 (2)	0.012 (2)
O3	0.0392 (18)	0.097 (3)	0.048 (2)	−0.0035 (18)	0.0020 (16)	−0.0088 (19)
O4	0.069 (2)	0.045 (2)	0.100 (3)	−0.0005 (18)	0.029 (2)	−0.001 (2)
O5	0.051 (2)	0.071 (2)	0.051 (2)	0.0181 (17)	0.0067 (17)	−0.0066 (17)
O6	0.075 (3)	0.082 (3)	0.057 (2)	0.013 (2)	0.005 (2)	−0.020 (2)
O7	0.0317 (18)	0.101 (3)	0.079 (3)	−0.0013 (19)	0.0015 (18)	−0.004 (2)
O8	0.054 (2)	0.087 (3)	0.045 (2)	0.0002 (19)	0.0093 (16)	0.0056 (18)
S1	0.0385 (6)	0.0533 (8)	0.0516 (8)	−0.0008 (6)	0.0072 (6)	−0.0018 (6)
S2	0.0374 (7)	0.0746 (9)	0.0517 (8)	0.0028 (6)	0.0049 (6)	0.0025 (7)
C1	0.037 (3)	0.069 (3)	0.041 (3)	0.003 (2)	0.009 (2)	0.000 (2)
C2	0.045 (3)	0.063 (3)	0.039 (3)	−0.012 (2)	0.012 (2)	−0.007 (2)
C3	0.055 (3)	0.062 (3)	0.043 (3)	−0.012 (3)	0.018 (2)	−0.005 (2)
C4	0.073 (4)	0.059 (4)	0.063 (4)	−0.008 (3)	0.021 (3)	0.000 (3)
C5	0.100 (5)	0.069 (4)	0.092 (5)	−0.036 (4)	0.044 (4)	−0.010 (4)
C6	0.067 (4)	0.094 (5)	0.094 (5)	−0.036 (4)	0.030 (4)	−0.016 (4)
C7	0.055 (3)	0.078 (4)	0.064 (4)	−0.017 (3)	0.021 (3)	−0.009 (3)
C8	0.123 (6)	0.057 (4)	0.113 (6)	0.000 (4)	0.050 (5)	0.006 (4)
C9	0.135 (7)	0.071 (5)	0.118 (6)	0.023 (4)	0.045 (5)	0.008 (4)
C10	0.041 (3)	0.049 (3)	0.042 (3)	−0.004 (2)	0.009 (2)	0.009 (2)
C11	0.048 (3)	0.092 (4)	0.056 (4)	0.006 (3)	0.004 (3)	0.000 (3)
C12	0.083 (5)	0.140 (6)	0.050 (4)	0.000 (5)	0.010 (3)	−0.020 (4)
C13	0.092 (5)	0.111 (6)	0.065 (4)	−0.007 (4)	0.034 (4)	−0.023 (4)
C14	0.059 (4)	0.079 (4)	0.086 (5)	0.003 (3)	0.028 (3)	−0.008 (4)
C15	0.045 (3)	0.070 (3)	0.051 (3)	0.002 (3)	0.008 (2)	0.003 (3)
C16	0.039 (3)	0.045 (3)	0.074 (4)	0.003 (2)	0.011 (3)	0.011 (3)
C17	0.042 (3)	0.037 (3)	0.066 (3)	−0.001 (2)	0.017 (2)	0.004 (2)
C18	0.051 (3)	0.040 (3)	0.058 (3)	0.008 (2)	0.019 (3)	0.003 (2)
C19	0.054 (3)	0.045 (3)	0.066 (4)	0.001 (2)	0.018 (3)	0.000 (3)
C20	0.091 (5)	0.054 (3)	0.078 (4)	0.002 (3)	0.041 (4)	−0.011 (3)
C21	0.078 (4)	0.056 (4)	0.104 (5)	0.000 (3)	0.052 (4)	−0.012 (3)
C22	0.048 (3)	0.050 (3)	0.103 (5)	−0.001 (2)	0.031 (3)	0.004 (3)
C23	0.092 (5)	0.099 (5)	0.082 (5)	0.009 (4)	0.008 (4)	−0.036 (4)
C24	0.133 (7)	0.104 (6)	0.084 (5)	−0.003 (5)	−0.007 (5)	−0.032 (4)
C25	0.042 (3)	0.068 (3)	0.047 (3)	0.017 (2)	0.010 (2)	0.006 (3)
C26	0.047 (3)	0.084 (4)	0.081 (4)	0.001 (3)	0.010 (3)	0.023 (3)
C27	0.064 (4)	0.079 (5)	0.116 (6)	0.002 (3)	0.030 (4)	0.018 (4)
C28	0.104 (6)	0.077 (5)	0.107 (6)	0.024 (4)	0.057 (5)	0.024 (4)
C29	0.136 (7)	0.093 (6)	0.063 (4)	0.038 (5)	0.024 (5)	0.024 (4)
C30	0.080 (4)	0.077 (4)	0.061 (4)	0.016 (3)	0.002 (3)	0.000 (3)

Geometric parameters (Å, º) top

N1—N2	1.375 (5)	C10—C15	1.368 (6)
N1—S1	1.628 (4)	C10—C11	1.379 (6)
N1—H1A	0.8996	C11—C12	1.367 (8)
N2—C1	1.278 (5)	C11—H11	0.9300
N3—N4	1.378 (5)	C12—C13	1.363 (8)
N3—S2	1.633 (4)	C12—H12	0.9300
N3—H3	0.8998	C13—C14	1.370 (8)
N4—C16	1.271 (6)	C13—H13	0.9300
O1—C3	1.355 (5)	C14—C15	1.376 (7)
O1—H1	0.8187	C14—H14	0.9300
O2—C4	1.351 (6)	C15—H15	0.9300
O2—C8	1.425 (6)	C16—C17	1.442 (7)
O3—S1	1.432 (3)	C16—H16	0.9300
O4—S1	1.416 (3)	C17—C22	1.398 (7)
O5—C18	1.364 (5)	C17—C18	1.402 (6)
O5—H5	0.8202	C18—C19	1.394 (7)
O6—C19	1.362 (6)	C19—C20	1.381 (7)
O6—C23	1.433 (6)	C20—C21	1.378 (8)
O7—S2	1.423 (3)	C20—H20	0.9300
O8—S2	1.422 (3)	C21—C22	1.358 (8)
S1—C10	1.757 (5)	C21—H21	0.9300
S2—C25	1.755 (5)	C22—H22	0.9300
C1—C2	1.442 (7)	C23—C24	1.470 (9)
C1—H1C	0.9300	C23—H23A	0.9700
C2—C3	1.388 (7)	C23—H23B	0.9700
C2—C7	1.411 (6)	C24—H24A	0.9600
C3—C4	1.401 (7)	C24—H24B	0.9600
C4—C5	1.384 (8)	C24—H24C	0.9600
C5—C6	1.383 (9)	C25—C30	1.368 (7)
C5—H5A	0.9300	C25—C26	1.372 (7)
C6—C7	1.367 (8)	C26—C27	1.384 (8)
C6—H6	0.9300	C26—H26	0.9300
C7—H7	0.9300	C27—C28	1.356 (9)
C8—C9	1.485 (9)	C27—H27	0.9300
C8—H8A	0.9700	C28—C29	1.362 (9)
C8—H8B	0.9700	C28—H28	0.9300
C9—H9A	0.9600	C29—C30	1.380 (9)
C9—H9B	0.9600	C29—H29	0.9300
C9—H9C	0.9600	C30—H30	0.9300

N2—N1—S1	114.8 (3)	C13—C12—C11	120.9 (6)
N2—N1—H1A	108.0	C13—C12—H12	119.6
S1—N1—H1A	108.0	C11—C12—H12	119.6
C1—N2—N1	118.0 (4)	C12—C13—C14	119.9 (6)
N4—N3—S2	114.9 (3)	C12—C13—H13	120.0
N4—N3—H3	107.9	C14—C13—H13	120.0
S2—N3—H3	108.1	C13—C14—C15	120.2 (6)
C16—N4—N3	119.0 (4)	C13—C14—H14	119.9
C3—O1—H1	109.4	C15—C14—H14	119.9
C4—O2—C8	118.0 (5)	C10—C15—C14	119.3 (5)
C18—O5—H5	109.5	C10—C15—H15	120.4
C19—O6—C23	117.5 (4)	C14—C15—H15	120.4
O4—S1—O3	119.6 (2)	N4—C16—C17	120.4 (4)
O4—S1—N1	104.8 (2)	N4—C16—H16	119.8
O3—S1—N1	107.5 (2)	C17—C16—H16	119.8
O4—S1—C10	110.9 (2)	C22—C17—C18	117.7 (5)
O3—S1—C10	107.1 (2)	C22—C17—C16	120.3 (5)
N1—S1—C10	106.1 (2)	C18—C17—C16	121.8 (4)
O8—S2—O7	121.0 (2)	O5—C18—C19	117.1 (4)
O8—S2—N3	104.5 (2)	O5—C18—C17	122.0 (4)
O7—S2—N3	106.7 (2)	C19—C18—C17	120.9 (5)
O8—S2—C25	108.4 (2)	O6—C19—C20	126.7 (5)
O7—S2—C25	108.1 (2)	O6—C19—C18	114.5 (4)
N3—S2—C25	107.5 (2)	C20—C19—C18	118.7 (5)
N2—C1—C2	120.0 (4)	C21—C20—C19	121.3 (6)
N2—C1—H1C	120.0	C21—C20—H20	119.4
C2—C1—H1C	120.0	C19—C20—H20	119.4
C3—C2—C7	118.6 (5)	C22—C21—C20	119.7 (5)
C3—C2—C1	122.9 (4)	C22—C21—H21	120.2
C7—C2—C1	118.5 (5)	C20—C21—H21	120.2
O1—C3—C2	122.2 (5)	C21—C22—C17	121.7 (5)
O1—C3—C4	116.7 (5)	C21—C22—H22	119.1
C2—C3—C4	121.1 (5)	C17—C22—H22	119.1
O2—C4—C5	125.1 (6)	O6—C23—C24	107.8 (5)
O2—C4—C3	116.0 (5)	O6—C23—H23A	110.1
C5—C4—C3	118.9 (6)	C24—C23—H23A	110.1
C6—C5—C4	120.2 (6)	O6—C23—H23B	110.1
C6—C5—H5A	119.9	C24—C23—H23B	110.1
C4—C5—H5A	119.9	H23A—C23—H23B	108.5
C7—C6—C5	121.2 (6)	C23—C24—H24A	109.5
C7—C6—H6	119.4	C23—C24—H24B	109.5
C5—C6—H6	119.4	H24A—C24—H24B	109.5
C6—C7—C2	119.9 (6)	C23—C24—H24C	109.5
C6—C7—H7	120.0	H24A—C24—H24C	109.5
C2—C7—H7	120.0	H24B—C24—H24C	109.5
O2—C8—C9	107.5 (5)	C30—C25—C26	120.3 (5)
O2—C8—H8A	110.2	C30—C25—S2	120.1 (4)
C9—C8—H8A	110.2	C26—C25—S2	119.6 (4)
O2—C8—H8B	110.2	C25—C26—C27	119.9 (6)
C9—C8—H8B	110.2	C25—C26—H26	120.0
H8A—C8—H8B	108.5	C27—C26—H26	120.0
C8—C9—H9A	109.5	C28—C27—C26	119.8 (7)
C8—C9—H9B	109.5	C28—C27—H27	120.1
H9A—C9—H9B	109.5	C26—C27—H27	120.1
C8—C9—H9C	109.5	C27—C28—C29	120.1 (7)
H9A—C9—H9C	109.5	C27—C28—H28	120.0
H9B—C9—H9C	109.5	C29—C28—H28	120.0
C15—C10—C11	120.8 (5)	C28—C29—C30	121.0 (6)
C15—C10—S1	120.1 (4)	C28—C29—H29	119.5
C11—C10—S1	119.0 (4)	C30—C29—H29	119.5
C12—C11—C10	118.9 (5)	C25—C30—C29	118.9 (6)
C12—C11—H11	120.5	C25—C30—H30	120.6
C10—C11—H11	120.5	C29—C30—H30	120.6

S1—N1—N2—C1	−169.4 (3)	C12—C13—C14—C15	1.2 (10)
S2—N3—N4—C16	−159.3 (4)	C11—C10—C15—C14	0.3 (8)
N2—N1—S1—O4	175.3 (3)	S1—C10—C15—C14	−177.3 (4)
N2—N1—S1—O3	−56.5 (4)	C13—C14—C15—C10	−1.1 (9)
N2—N1—S1—C10	57.8 (4)	N3—N4—C16—C17	−174.3 (4)
N4—N3—S2—O8	−174.1 (3)	N4—C16—C17—C22	−178.7 (4)
N4—N3—S2—O7	−44.9 (4)	N4—C16—C17—C18	5.4 (7)
N4—N3—S2—C25	70.9 (4)	C22—C17—C18—O5	179.7 (4)
N1—N2—C1—C2	−175.6 (4)	C16—C17—C18—O5	−4.3 (7)
N2—C1—C2—C3	1.6 (7)	C22—C17—C18—C19	−0.6 (7)
N2—C1—C2—C7	179.4 (4)	C16—C17—C18—C19	175.4 (4)
C7—C2—C3—O1	179.6 (4)	C23—O6—C19—C20	−4.3 (8)
C1—C2—C3—O1	−2.5 (7)	C23—O6—C19—C18	174.1 (5)
C7—C2—C3—C4	0.3 (7)	O5—C18—C19—O6	1.4 (6)
C1—C2—C3—C4	178.1 (5)	C17—C18—C19—O6	−178.4 (4)
C8—O2—C4—C5	−0.1 (9)	O5—C18—C19—C20	179.9 (4)
C8—O2—C4—C3	178.8 (5)	C17—C18—C19—C20	0.1 (7)
O1—C3—C4—O2	2.5 (7)	O6—C19—C20—C21	179.7 (5)
C2—C3—C4—O2	−178.1 (5)	C18—C19—C20—C21	1.4 (8)
O1—C3—C4—C5	−178.5 (5)	C19—C20—C21—C22	−2.5 (9)
C2—C3—C4—C5	0.9 (8)	C20—C21—C22—C17	2.1 (8)
O2—C4—C5—C6	176.7 (6)	C18—C17—C22—C21	−0.6 (7)
C3—C4—C5—C6	−2.2 (9)	C16—C17—C22—C21	−176.6 (5)
C4—C5—C6—C7	2.4 (10)	C19—O6—C23—C24	−175.7 (5)
C5—C6—C7—C2	−1.1 (9)	O8—S2—C25—C30	151.3 (4)
C3—C2—C7—C6	−0.2 (8)	O7—S2—C25—C30	18.6 (5)
C1—C2—C7—C6	−178.1 (5)	N3—S2—C25—C30	−96.3 (4)
C4—O2—C8—C9	−178.9 (5)	O8—S2—C25—C26	−28.9 (5)
O4—S1—C10—C15	119.0 (4)	O7—S2—C25—C26	−161.7 (4)
O3—S1—C10—C15	−13.1 (5)	N3—S2—C25—C26	83.5 (5)
N1—S1—C10—C15	−127.7 (4)	C30—C25—C26—C27	−1.3 (8)
O4—S1—C10—C11	−58.7 (5)	S2—C25—C26—C27	179.0 (5)
O3—S1—C10—C11	169.2 (4)	C25—C26—C27—C28	0.9 (9)
N1—S1—C10—C11	54.6 (5)	C26—C27—C28—C29	0.3 (10)
C15—C10—C11—C12	0.5 (8)	C27—C28—C29—C30	−1.2 (11)
S1—C10—C11—C12	178.2 (5)	C26—C25—C30—C29	0.4 (8)
C10—C11—C12—C13	−0.5 (10)	S2—C25—C30—C29	−179.8 (5)
C11—C12—C13—C14	−0.4 (11)	C28—C29—C30—C25	0.8 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2	0.82	1.89	2.606 (5)	145
O5—H5···N4	0.82	1.87	2.591 (5)	146
N1—H1A···O5	0.90	2.14	2.948 (5)	149
N3—H3···O3ⁱ	0.90	2.11	2.912 (5)	147

Symmetry code: (i) x−1, y, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₂O₄S
M_r	320.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.3149 (10), 39.935 (3), 7.9832 (8)
β (°)	105.773 (2)
V (Å³)	3164.7 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.48 × 0.45 × 0.32

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.900, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	16316, 5576, 3515
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.160, 1.09
No. of reflections	5576
No. of parameters	399
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.41

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
O1—H1···N2	0.82	1.89	2.606 (5)	145
O5—H5···N4	0.82	1.87	2.591 (5)	146
N1—H1A···O5	0.90	2.14	2.948 (5)	149
N3—H3···O3ⁱ	0.90	2.11	2.912 (5)	147

Symmetry code: (i) x−1, y, z−1.

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong, the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tai, X.-S., Yin, X.-H., Tan, M.-Y. & Li, Y.-Z. (2003). Acta Cryst. E59, o681–o682. Web of Science CSD CrossRef IUCr Journals Google Scholar