4-(Diethyl­amino)salicylaldehyde phenyl­sulfonyl­hydrazone

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

doi:10.1107/S1600536808010118

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o865

doi:10.1107/S1600536808010118

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4-(Diethylamino)salicylaldehyde phenylsulfonylhydrazone

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 12 April 2008; accepted 13 April 2008; online 18 April 2008)

In the title compound, C₁₇H₂₁N₃O₃S, the dihedral angle between the aromatic ring planes is 84.2 (2)°. The pendant ethyl groups of the –N(C₂H₅)₂ group are disordered over two sets of positions in a 0.84 (2):0.16 (2) ratio. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond, and intermolecular N—H⋯O bonds lead to [010] chains in the crystal structure.

Related literature

For related literature, see: Tai et al. (2008 ).

Experimental

Crystal data

C₁₇H₂₁N₃O₃S
M_r = 347.43
Orthorhombic, P b c n
a = 29.874 (3) Å
b = 7.5153 (12) Å
c = 15.4456 (19) Å
V = 3467.8 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 (2) K
0.43 × 0.38 × 0.04 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.916, T_max = 0.992
16321 measured reflections
3052 independent reflections
2061 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.175
S = 1.08
3052 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N2	0.82	1.92	2.637 (4)	146
N1—H1⋯O1ⁱ	0.90	2.06	2.944 (5)	169
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536808010118/hb2720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010118/hb2720Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of aroylhydrazones as potential ligands (Tai et al., 2008), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The dihedral angle between the aromatic ring planes is 84.2 (2)°. The pendant ethyl groups of the -N(C₂H₅)₂ grouping are disordered over two sets of positions in a 0.84 (2):0.16 (2) ratio. The molecular conformation is stabilised by an intramolecular O-H···N hydrogen bond and intermolecular N-H···O bonds lead to [010] chains in the crystal (Table 1).

Related literature top

For related literature, see: Tai et al. (2008).

Experimental top

3 mmol of p-(diethylamino)salicylaldehyde (3 mmol) was added to a solution of benzenesulfonyl hydrazide (3 mmol) in 10 ml of 95% ethanol. The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some ethanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 67%). Colourless plates of (I) were obtained by evaporation from a methanol solution after several 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 molecular structure of (I) showing 30% displacement ellipsoids for the non-hydrogen atoms. Only the major disorder component is shown and the hydrogen bond is indicated by a double-dashed line.

4-(Diethylamino)salicylaldehyde phenylsulfonylhydrazone top

Crystal data top

C₁₇H₂₁N₃O₃S	D_x = 1.331 Mg m⁻³
M_r = 347.43	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbcn	Cell parameters from 3546 reflections
a = 29.874 (3) Å	θ = 2.7–21.4°
b = 7.5153 (12) Å	µ = 0.21 mm⁻¹
c = 15.4456 (19) Å	T = 293 K
V = 3467.8 (8) Å³	Plate, colourless
Z = 8	0.43 × 0.38 × 0.04 mm
F(000) = 1472

Data collection top

Bruker SMART CCD diffractometer	3052 independent reflections
Radiation source: fine-focus sealed tube	2061 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −35→34
T_min = 0.916, T_max = 0.992	k = −8→7
16321 measured reflections	l = −18→14

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0453P)² + 7.4306P] where P = (F_o² + 2F_c²)/3
3052 reflections	(Δ/σ)_max = 0.001
258 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₂₁N₃O₃S	V = 3467.8 (8) Å³
M_r = 347.43	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 29.874 (3) Å	µ = 0.21 mm⁻¹
b = 7.5153 (12) Å	T = 293 K
c = 15.4456 (19) Å	0.43 × 0.38 × 0.04 mm

Data collection top

Bruker SMART CCD diffractometer	3052 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2061 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.992	R_int = 0.048
16321 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.08	Δρ_max = 0.44 e Å⁻³
3052 reflections	Δρ_min = −0.30 e Å⁻³
258 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	Occ. (<1)
N1	0.31274 (11)	0.2572 (5)	0.9493 (2)	0.0502 (9)
H1	0.2949	0.3499	0.9363	0.060*
N2	0.35710 (11)	0.3011 (5)	0.9253 (2)	0.0512 (9)
N3	0.54548 (13)	0.6991 (6)	0.8710 (3)	0.0794 (14)
O1	0.24926 (10)	0.0597 (4)	0.93219 (19)	0.0596 (8)
O2	0.32557 (10)	−0.0581 (4)	0.9110 (2)	0.0643 (9)
O3	0.44009 (10)	0.2276 (4)	0.8794 (2)	0.0773 (11)
H3	0.4137	0.2060	0.8893	0.116*
S1	0.29375 (3)	0.08000 (14)	0.89918 (7)	0.0481 (3)
C1	0.29054 (13)	0.1295 (5)	0.7887 (3)	0.0457 (10)
C2	0.32787 (15)	0.1092 (6)	0.7367 (3)	0.0602 (12)
H2	0.3547	0.0683	0.7601	0.072*
C3	0.32493 (18)	0.1505 (7)	0.6499 (3)	0.0727 (14)
H3A	0.3498	0.1363	0.6142	0.087*
C4	0.28604 (19)	0.2114 (7)	0.6164 (3)	0.0700 (14)
H4	0.2846	0.2396	0.5578	0.084*
C5	0.24886 (19)	0.2323 (7)	0.6664 (3)	0.0693 (14)
H5	0.2224	0.2744	0.6420	0.083*
C6	0.25055 (15)	0.1908 (6)	0.7535 (3)	0.0586 (12)
H6	0.2253	0.2037	0.7882	0.070*
C7	0.36859 (14)	0.4638 (6)	0.9325 (3)	0.0517 (11)
H7	0.3473	0.5476	0.9489	0.062*
C8	0.41362 (13)	0.5202 (6)	0.9160 (3)	0.0545 (11)
C9	0.44774 (14)	0.4048 (6)	0.8899 (3)	0.0572 (12)
C10	0.49056 (14)	0.4634 (6)	0.8754 (3)	0.0630 (13)
H10	0.5124	0.3820	0.8588	0.076*
C11	0.50227 (15)	0.6425 (6)	0.8849 (3)	0.0661 (13)
C12	0.46791 (15)	0.7606 (7)	0.9108 (4)	0.0725 (15)
H12	0.4742	0.8809	0.9179	0.087*
C13	0.42560 (15)	0.6996 (6)	0.9256 (3)	0.0670 (14)
H13	0.4038	0.7804	0.9427	0.080*
C14	0.5780 (8)	0.571 (4)	0.8341 (15)	0.095 (6)	0.84 (2)
H14A	0.5787	0.4677	0.8715	0.114*	0.84 (2)
H14B	0.5666	0.5327	0.7784	0.114*	0.84 (2)
C15	0.6231 (3)	0.6286 (18)	0.8217 (10)	0.114 (4)	0.84 (2)
H15A	0.6242	0.7137	0.7754	0.171*	0.84 (2)
H15B	0.6414	0.5280	0.8074	0.171*	0.84 (2)
H15C	0.6339	0.6826	0.8740	0.171*	0.84 (2)
C16	0.5597 (2)	0.8789 (15)	0.8999 (8)	0.076 (3)	0.84 (2)
H16A	0.5912	0.8770	0.9147	0.092*	0.84 (2)
H16B	0.5430	0.9123	0.9513	0.092*	0.84 (2)
C17	0.5517 (3)	1.012 (2)	0.8301 (10)	0.107 (4)	0.84 (2)
H17A	0.5649	0.9712	0.7772	0.161*	0.84 (2)
H17B	0.5650	1.1239	0.8463	0.161*	0.84 (2)
H17C	0.5201	1.0281	0.8220	0.161*	0.84 (2)
C14'	0.585 (4)	0.574 (18)	0.870 (7)	0.08 (2)	0.16 (2)
H14C	0.5748	0.4534	0.8813	0.098*	0.16 (2)
H14D	0.6063	0.6079	0.9134	0.098*	0.16 (2)
C15'	0.606 (2)	0.586 (8)	0.779 (5)	0.11 (2)	0.16 (2)
H15D	0.5939	0.6879	0.7496	0.170*	0.16 (2)
H15E	0.5985	0.4801	0.7472	0.170*	0.16 (2)
H15F	0.6375	0.5966	0.7846	0.170*	0.16 (2)
C16'	0.5486 (13)	0.875 (8)	0.826 (4)	0.082 (18)	0.16 (2)
H16C	0.5207	0.9021	0.7969	0.099*	0.16 (2)
H16D	0.5724	0.8723	0.7830	0.099*	0.16 (2)
C17'	0.5588 (15)	1.015 (10)	0.896 (4)	0.089 (19)	0.16 (2)
H17D	0.5320	1.0407	0.9280	0.133*	0.16 (2)
H17E	0.5694	1.1224	0.8689	0.133*	0.16 (2)
H17F	0.5813	0.9706	0.9346	0.133*	0.16 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0406 (19)	0.055 (2)	0.055 (2)	0.0017 (16)	−0.0002 (16)	−0.0013 (18)
N2	0.0378 (18)	0.057 (2)	0.059 (2)	0.0001 (16)	−0.0014 (16)	−0.0042 (18)
N3	0.053 (2)	0.065 (3)	0.120 (4)	−0.008 (2)	0.015 (2)	−0.019 (3)
O1	0.0506 (16)	0.061 (2)	0.067 (2)	−0.0052 (15)	0.0125 (15)	−0.0017 (16)
O2	0.0634 (19)	0.0535 (19)	0.076 (2)	0.0149 (15)	0.0025 (16)	0.0112 (17)
O3	0.0547 (19)	0.053 (2)	0.125 (3)	−0.0024 (16)	0.0098 (19)	−0.022 (2)
S1	0.0427 (6)	0.0449 (6)	0.0566 (7)	0.0016 (5)	0.0036 (5)	0.0027 (5)
C1	0.044 (2)	0.038 (2)	0.054 (3)	0.0016 (18)	−0.001 (2)	−0.0076 (19)
C2	0.047 (3)	0.069 (3)	0.065 (3)	0.007 (2)	0.002 (2)	0.002 (3)
C3	0.068 (3)	0.085 (4)	0.065 (4)	−0.003 (3)	0.006 (3)	−0.001 (3)
C4	0.087 (4)	0.066 (3)	0.057 (3)	−0.001 (3)	−0.006 (3)	0.000 (3)
C5	0.074 (3)	0.063 (3)	0.071 (3)	0.017 (3)	−0.020 (3)	−0.005 (3)
C6	0.049 (2)	0.062 (3)	0.065 (3)	0.009 (2)	−0.003 (2)	−0.007 (2)
C7	0.046 (2)	0.048 (3)	0.061 (3)	0.005 (2)	0.001 (2)	−0.003 (2)
C8	0.042 (2)	0.053 (3)	0.069 (3)	0.002 (2)	0.003 (2)	−0.003 (2)
C9	0.048 (2)	0.051 (3)	0.073 (3)	0.001 (2)	−0.002 (2)	−0.011 (2)
C10	0.043 (2)	0.055 (3)	0.090 (4)	0.003 (2)	0.008 (2)	−0.018 (3)
C11	0.045 (2)	0.068 (3)	0.085 (4)	−0.003 (2)	0.008 (2)	−0.009 (3)
C12	0.056 (3)	0.053 (3)	0.109 (4)	−0.003 (2)	0.014 (3)	−0.011 (3)
C13	0.050 (3)	0.054 (3)	0.098 (4)	0.005 (2)	0.011 (3)	−0.009 (3)
C14	0.060 (9)	0.096 (8)	0.129 (17)	−0.014 (7)	0.018 (10)	−0.045 (13)
C15	0.067 (6)	0.131 (9)	0.145 (11)	0.011 (6)	−0.007 (6)	−0.040 (7)
C16	0.052 (4)	0.075 (7)	0.101 (8)	−0.006 (3)	0.001 (4)	−0.019 (5)
C17	0.072 (6)	0.097 (10)	0.152 (11)	0.004 (5)	0.011 (7)	0.011 (9)
C14'	0.06 (4)	0.08 (4)	0.11 (7)	−0.01 (3)	0.00 (4)	−0.02 (5)
C15'	0.09 (4)	0.11 (4)	0.13 (6)	−0.01 (3)	0.00 (4)	−0.03 (4)
C16'	0.06 (2)	0.08 (4)	0.11 (5)	0.00 (2)	0.01 (2)	−0.02 (3)
C17'	0.06 (2)	0.08 (4)	0.13 (5)	0.00 (2)	0.00 (3)	−0.02 (4)

Geometric parameters (Å, º) top

N1—N2	1.415 (4)	C10—C11	1.398 (6)
N1—S1	1.642 (4)	C10—H10	0.9300
N1—H1	0.9000	C11—C12	1.415 (6)
N2—C7	1.275 (5)	C12—C13	1.363 (6)
N3—C11	1.376 (6)	C12—H12	0.9300
N3—C14	1.48 (3)	C13—H13	0.9300
N3—C16	1.485 (11)	C14—C15	1.42 (3)
N3—C16'	1.50 (6)	C14—H14A	0.9700
N3—C14'	1.50 (15)	C14—H14B	0.9700
O1—S1	1.432 (3)	C15—H15A	0.9600
O2—S1	1.419 (3)	C15—H15B	0.9600
O3—C9	1.361 (5)	C15—H15C	0.9600
O3—H3	0.8200	C16—C17	1.49 (2)
S1—C1	1.750 (4)	C16—H16A	0.9700
C1—C2	1.382 (6)	C16—H16B	0.9700
C1—C6	1.391 (6)	C17—H17A	0.9600
C2—C3	1.380 (7)	C17—H17B	0.9600
C2—H2	0.9300	C17—H17C	0.9600
C3—C4	1.351 (7)	C14'—C15'	1.53 (16)
C3—H3A	0.9300	C14'—H14C	0.9700
C4—C5	1.362 (7)	C14'—H14D	0.9700
C4—H4	0.9300	C15'—H15D	0.9600
C5—C6	1.383 (6)	C15'—H15E	0.9600
C5—H5	0.9300	C15'—H15F	0.9600
C6—H6	0.9300	C16'—C17'	1.54 (10)
C7—C8	1.433 (6)	C16'—H16C	0.9700
C7—H7	0.9300	C16'—H16D	0.9700
C8—C9	1.398 (6)	C17'—H17D	0.9600
C8—C13	1.403 (6)	C17'—H17E	0.9600
C9—C10	1.371 (6)	C17'—H17F	0.9600

N2—N1—S1	112.9 (3)	C9—C10—C11	121.7 (4)
N2—N1—H1	108.5	C9—C10—H10	119.1
S1—N1—H1	108.5	C11—C10—H10	119.1
C7—N2—N1	116.9 (4)	N3—C11—C10	121.1 (4)
C11—N3—C14	118.4 (10)	N3—C11—C12	122.0 (4)
C11—N3—C16	120.2 (5)	C10—C11—C12	116.9 (4)
C14—N3—C16	121.2 (10)	C13—C12—C11	120.6 (5)
C11—N3—C16'	113.9 (16)	C13—C12—H12	119.7
C14—N3—C16'	111 (2)	C11—C12—H12	119.7
C16—N3—C16'	47 (2)	C12—C13—C8	122.8 (4)
C11—N3—C14'	123 (5)	C12—C13—H13	118.6
C14—N3—C14'	23 (4)	C8—C13—H13	118.6
C16—N3—C14'	111 (4)	C15—C14—N3	118.4 (18)
C16'—N3—C14'	120 (6)	C15—C14—H14A	107.7
C9—O3—H3	109.5	N3—C14—H14A	107.7
O2—S1—O1	119.90 (19)	C15—C14—H14B	107.7
O2—S1—N1	107.52 (19)	N3—C14—H14B	107.7
O1—S1—N1	103.83 (18)	H14A—C14—H14B	107.1
O2—S1—C1	108.52 (19)	N3—C16—C17	110.4 (12)
O1—S1—C1	108.61 (19)	N3—C16—H16A	109.6
N1—S1—C1	107.86 (19)	C17—C16—H16A	109.6
C2—C1—C6	120.2 (4)	N3—C16—H16B	109.6
C2—C1—S1	119.9 (3)	C17—C16—H16B	109.6
C6—C1—S1	119.9 (3)	H16A—C16—H16B	108.1
C3—C2—C1	119.2 (4)	N3—C14'—C15'	107 (8)
C3—C2—H2	120.4	N3—C14'—H14C	110.3
C1—C2—H2	120.4	C15'—C14'—H14C	110.3
C4—C3—C2	120.2 (5)	N3—C14'—H14D	110.3
C4—C3—H3A	119.9	C15'—C14'—H14D	110.3
C2—C3—H3A	119.9	H14C—C14'—H14D	108.5
C3—C4—C5	121.6 (5)	C14'—C15'—H15D	109.5
C3—C4—H4	119.2	C14'—C15'—H15E	109.5
C5—C4—H4	119.2	H15D—C15'—H15E	109.5
C4—C5—C6	119.7 (5)	C14'—C15'—H15F	109.5
C4—C5—H5	120.1	H15D—C15'—H15F	109.5
C6—C5—H5	120.1	H15E—C15'—H15F	109.5
C5—C6—C1	119.1 (5)	N3—C16'—C17'	107 (6)
C5—C6—H6	120.5	N3—C16'—H16C	110.4
C1—C6—H6	120.5	C17'—C16'—H16C	110.4
N2—C7—C8	121.4 (4)	N3—C16'—H16D	110.4
N2—C7—H7	119.3	C17'—C16'—H16D	110.4
C8—C7—H7	119.3	H16C—C16'—H16D	108.6
C9—C8—C13	116.2 (4)	C16'—C17'—H17D	109.5
C9—C8—C7	123.5 (4)	C16'—C17'—H17E	109.5
C13—C8—C7	120.3 (4)	H17D—C17'—H17E	109.5
O3—C9—C10	116.9 (4)	C16'—C17'—H17F	109.5
O3—C9—C8	121.3 (4)	H17D—C17'—H17F	109.5
C10—C9—C8	121.9 (4)	H17E—C17'—H17F	109.5

S1—N1—N2—C7	153.6 (3)	C16'—N3—C11—C10	141 (3)
N2—N1—S1—O2	52.0 (3)	C14'—N3—C11—C10	−18 (4)
N2—N1—S1—O1	−179.9 (3)	C14—N3—C11—C12	−172.9 (12)
N2—N1—S1—C1	−64.8 (3)	C16—N3—C11—C12	12.5 (9)
O2—S1—C1—C2	−31.0 (4)	C16'—N3—C11—C12	−40 (3)
O1—S1—C1—C2	−162.8 (3)	C14'—N3—C11—C12	161 (4)
N1—S1—C1—C2	85.2 (4)	C9—C10—C11—N3	179.3 (5)
O2—S1—C1—C6	149.7 (3)	C9—C10—C11—C12	0.4 (8)
O1—S1—C1—C6	17.8 (4)	N3—C11—C12—C13	−178.8 (5)
N1—S1—C1—C6	−94.1 (4)	C10—C11—C12—C13	0.1 (8)
C6—C1—C2—C3	0.0 (7)	C11—C12—C13—C8	−0.2 (9)
S1—C1—C2—C3	−179.4 (4)	C9—C8—C13—C12	−0.1 (8)
C1—C2—C3—C4	0.6 (8)	C7—C8—C13—C12	179.9 (5)
C2—C3—C4—C5	−0.6 (8)	C11—N3—C14—C15	−178.5 (15)
C3—C4—C5—C6	0.0 (8)	C16—N3—C14—C15	−4 (2)
C4—C5—C6—C1	0.5 (7)	C16'—N3—C14—C15	48 (3)
C2—C1—C6—C5	−0.5 (7)	C14'—N3—C14—C15	−71 (15)
S1—C1—C6—C5	178.8 (4)	C11—N3—C16—C17	−89.7 (8)
N1—N2—C7—C8	175.4 (4)	C14—N3—C16—C17	95.8 (13)
N2—C7—C8—C9	1.0 (7)	C16'—N3—C16—C17	6 (2)
N2—C7—C8—C13	−179.0 (5)	C14'—N3—C16—C17	118 (5)
C13—C8—C9—O3	179.3 (5)	C11—N3—C14'—C15'	118 (7)
C7—C8—C9—O3	−0.8 (7)	C14—N3—C14'—C15'	32 (11)
C13—C8—C9—C10	0.6 (7)	C16—N3—C14'—C15'	−90 (6)
C7—C8—C9—C10	−179.4 (5)	C16'—N3—C14'—C15'	−39 (8)
O3—C9—C10—C11	−179.5 (5)	C11—N3—C16'—C17'	101 (3)
C8—C9—C10—C11	−0.8 (8)	C14—N3—C16'—C17'	−123 (2)
C14—N3—C11—C10	8.3 (13)	C16—N3—C16'—C17'	−9 (2)
C16—N3—C11—C10	−166.3 (7)	C14'—N3—C16'—C17'	−100 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N2	0.82	1.92	2.637 (4)	146
N1—H1···O1ⁱ	0.90	2.06	2.944 (5)	169

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃O₃S
M_r	347.43
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	29.874 (3), 7.5153 (12), 15.4456 (19)
V (Å³)	3467.8 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.43 × 0.38 × 0.04

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.916, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	16321, 3052, 2061
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.175, 1.08
No. of reflections	3052
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.30

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
O3—H3···N2	0.82	1.92	2.637 (4)	146
N1—H1···O1ⁱ	0.90	2.06	2.944 (5)	169

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

The authors thank the National Natural Science Foundation of China (20671073), the National Natural Science Foundation of Shandong (Y2007B60), and the Science and Technology Foundation of Weifang and Weifang University for research grants.

References

Bruker (2000). SMART, SAINT and SADABS. 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., Feng, Y.-M. & Kong, F.-Y. (2008). Acta Cryst. E64, o750. Web of Science CSD CrossRef IUCr Journals Google Scholar