N-Cyclo­hexyl-4-[(2-nitro­anilino)­meth­yl]thio­phene-2-sulfonamide

He, Y.; Tong, R.; Wu, J.; Jing, Z.; Shi, J.

doi:10.1107/S160053681103861X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2779

https://doi.org/10.1107/S160053681103861X

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N-Cyclohexyl-4-[(2-nitroanilino)methyl]thiophene-2-sulfonamide

Yu-xin He,^a Rong-sheng Tong,^b Jin-wei Wu,^a Zou Jing ^b and Jian-you Shi ^b ^*

^aBioengineering College, Xihua University, Chengdu, Sichuan 610039, People's Republic of China, and ^bSichuan Academy of Medical Sciences and, Sichuan Provincial People's Hospital, Chengdu, Sichuan 610072, People's Republic of China
^*Correspondence e-mail: shijianyoude@126.com

(Received 16 August 2011; accepted 20 September 2011; online 30 September 2011)

In the title compound, C₁₇H₂₁N₃O₄S₂, an intramolecular N—H⋯O hydrogen bond involving the proximate amine and nitro groups is observed. In the crystal, intermolecular N—H⋯O hydrogen bonds involving the amine and SO₂ groups occur. One of the notro O atoms is disordered over two conformations with occupancies of 0.578 (12) and 0.422 (12).

Related literature

For uses of thiophene-2-sulfonamides, see: Cuberes Altisen et al. (2007 ); Santhakumar & Tomaszewski (2006 ).

Experimental

Crystal data

C₁₇H₂₁N₃O₄S₂
M_r = 395.49
Monoclinic, P 2₁ /c
a = 7.4201 (2) Å
b = 27.8329 (7) Å
c = 10.1790 (3) Å
β = 118.440 (3)°
V = 1848.50 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 145 K
0.38 × 0.25 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.970, T_max = 1.0
8048 measured reflections
3772 independent reflections
3104 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.129
S = 1.01
3772 reflections
225 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.02 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.27	2.956 (3)	134
N2—H2⋯O2ⁱⁱ	0.81 (3)	2.36 (3)	2.979 (3)	135 (3)
N2—H2⋯O3	0.81 (3)	2.01 (3)	2.620 (4)	132 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681103861X/bv2190sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103861X/bv2190Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103861X/bv2190Isup3.cml

checkCIF report

Comment top

N-Cyclohexyl-4-((2-nitrophenylamino)methyl)thiophene-2-sulfonamide is potentially useful in the treatment of a condition mediated by the CB2 receptor (Cuberes Altisen, et al., 2007). In the title compound, C₁₇H₂₁N₃O₄S₂, there is an intramolecular N-H···O between the amine and nitro groups as well as N-H···O intermolecular hydrogen bonds involving the amine and SO₂ moieties. O4 is disordered over two conformations with occupancies of 0.578 (12) and 0.422 (12).

Related literature top

For uses of thiophene-2-sulfonamides, see: Cuberes Altisen et al. (2007); Santhakumar & Tomaszewski (2006).

Experimental top

A mixture of 4-((2-nitrophenylamino)methyl)thiophene-2-sulfonyl chloride (3.22 g, 0.01 mol), trimethylamine (0.885 g, 0.015 mol) and cyclohexanamine (0.99 g, 0.01 mol) in THF (150 mL) was heated to reflux for 3 h, then the solvent removed and the residue separated by silica gel column to obtain the target compound. Single crystals were obtained from the powder in CH₂Cl₂ and methanol after 3 days.

Structure description top

For uses of thiophene-2-sulfonamides, see: Cuberes Altisen et al. (2007); Santhakumar & Tomaszewski (2006).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

Fig. 1. The molecular structure of title compound. The intramolecular N-H···O hydrogen bond is shown by dashed lines.

N-Cyclohexyl-4-[(2-nitroanilino)methyl]thiophene-2-sulfonamide top

Crystal data top

C₁₇H₂₁N₃O₄S₂	F(000) = 832
M_r = 395.49	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 3479 reflections
a = 7.4201 (2) Å	θ = 2.9–29.1°
b = 27.8329 (7) Å	µ = 0.32 mm⁻¹
c = 10.1790 (3) Å	T = 145 K
β = 118.440 (3)°	Block, yellow
V = 1848.50 (10) Å³	0.38 × 0.25 × 0.15 mm
Z = 4

Data collection top

Agilent Xcalibur Eos diffractometer	3772 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 2.9°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −31→34
T_min = 0.970, T_max = 1.0	l = −12→10
8048 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0385P)² + 3.9868P] where P = (F_o² + 2F_c²)/3
3772 reflections	(Δ/σ)_max < 0.001
225 parameters	Δρ_max = 1.02 e Å⁻³
1 restraint	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₁₇H₂₁N₃O₄S₂	V = 1848.50 (10) Å³
M_r = 395.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4201 (2) Å	µ = 0.32 mm⁻¹
b = 27.8329 (7) Å	T = 145 K
c = 10.1790 (3) Å	0.38 × 0.25 × 0.15 mm
β = 118.440 (3)°

Data collection top

Agilent Xcalibur Eos diffractometer	3772 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3104 reflections with I > 2σ(I)
T_min = 0.970, T_max = 1.0	R_int = 0.021
8048 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.02 e Å⁻³
3772 reflections	Δρ_min = −0.68 e Å⁻³
225 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)
S1	−0.35683 (10)	0.25100 (2)	0.68116 (8)	0.02193 (18)
S2	0.04835 (11)	0.23017 (3)	0.69685 (8)	0.02609 (19)
O1	−0.4402 (3)	0.24711 (8)	0.7824 (2)	0.0303 (5)
O2	−0.3343 (3)	0.29724 (7)	0.6291 (2)	0.0321 (5)
O3	0.8016 (4)	0.10467 (11)	1.0716 (4)	0.0578 (8)
O4	0.8590 (14)	0.0450 (3)	0.9436 (13)	0.060 (2)	0.578 (12)
O4A	0.9294 (19)	0.0474 (5)	1.0238 (16)	0.060 (2)	0.422 (12)
N1	−0.4979 (4)	0.21961 (8)	0.5357 (3)	0.0237 (5)
H1	−0.5543	0.2332	0.4469	0.028*
N2	0.4249 (4)	0.11205 (9)	1.0276 (3)	0.0284 (6)
H2	0.538 (5)	0.1238 (12)	1.068 (4)	0.029 (9)*
N3	0.7563 (6)	0.06859 (12)	0.9914 (5)	0.0608 (11)
C1	−0.5341 (5)	0.16781 (10)	0.5495 (3)	0.0259 (6)
H1A	−0.5033	0.1617	0.6550	0.031*
C2	−0.3928 (5)	0.13607 (11)	0.5162 (3)	0.0331 (7)
H2B	−0.2481	0.1438	0.5867	0.040*
H2A	−0.4164	0.1425	0.4135	0.040*
C3	−0.4336 (6)	0.08302 (12)	0.5313 (4)	0.0461 (9)
H3A	−0.3467	0.0629	0.5038	0.055*
H3B	−0.3961	0.0760	0.6366	0.055*
C4	−0.6567 (7)	0.07034 (13)	0.4319 (4)	0.0552 (11)
H4B	−0.6799	0.0364	0.4491	0.066*
H4A	−0.6898	0.0737	0.3259	0.066*
C5	−0.7976 (6)	0.10240 (14)	0.4624 (4)	0.0510 (10)
H5B	−0.7766	0.0960	0.5645	0.061*
H5A	−0.9419	0.0947	0.3908	0.061*
C6	−0.7576 (5)	0.15573 (12)	0.4483 (4)	0.0348 (7)
H6A	−0.7938	0.1630	0.3434	0.042*
H6B	−0.8449	0.1757	0.4757	0.042*
C7	−0.1161 (4)	0.22402 (10)	0.7707 (3)	0.0204 (6)
C8	0.2109 (4)	0.18895 (11)	0.8212 (3)	0.0249 (6)
H8	0.3358	0.1792	0.8246	0.030*
C9	0.1434 (4)	0.17152 (10)	0.9146 (3)	0.0212 (6)
C10	−0.0482 (4)	0.19163 (10)	0.8847 (3)	0.0210 (6)
H10	−0.1204	0.1835	0.9376	0.025*
C11	0.2639 (4)	0.13708 (11)	1.0413 (3)	0.0256 (6)
H11B	0.3255	0.1552	1.1365	0.031*
H11A	0.1685	0.1131	1.0459	0.031*
C12	0.3906 (5)	0.07546 (11)	0.9310 (4)	0.0316 (7)
C13	0.1906 (8)	0.05721 (14)	0.8436 (5)	0.0589 (6)
H13	0.0794	0.0724	0.8485	0.071*
C14	0.1522 (8)	0.01803 (13)	0.7514 (5)	0.0589 (6)
H14	0.0160	0.0064	0.6951	0.071*
C15	0.3109 (8)	−0.00463 (14)	0.7402 (5)	0.0589 (6)
H15	0.2833	−0.0319	0.6774	0.071*
C16	0.5047 (8)	0.01209 (13)	0.8186 (5)	0.0589 (6)
H16	0.6129	−0.0034	0.8103	0.071*
C17	0.5473 (6)	0.05249 (12)	0.9128 (5)	0.0450 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0235 (3)	0.0198 (3)	0.0232 (4)	0.0021 (3)	0.0117 (3)	−0.0014 (3)
S2	0.0281 (4)	0.0275 (4)	0.0287 (4)	0.0020 (3)	0.0183 (3)	0.0070 (3)
O1	0.0291 (11)	0.0366 (12)	0.0302 (11)	0.0012 (9)	0.0182 (9)	−0.0082 (9)
O2	0.0316 (12)	0.0192 (10)	0.0380 (12)	0.0023 (9)	0.0106 (10)	0.0031 (9)
O3	0.0391 (15)	0.0464 (17)	0.096 (2)	0.0100 (13)	0.0383 (16)	0.0169 (16)
O4	0.050 (5)	0.057 (2)	0.095 (6)	0.017 (3)	0.052 (5)	0.011 (5)
O4A	0.050 (5)	0.057 (2)	0.095 (6)	0.017 (3)	0.052 (5)	0.011 (5)
N1	0.0280 (12)	0.0215 (12)	0.0181 (12)	0.0003 (10)	0.0082 (10)	0.0022 (9)
N2	0.0227 (13)	0.0229 (13)	0.0393 (15)	0.0004 (11)	0.0145 (12)	0.0007 (11)
N3	0.065 (2)	0.0361 (19)	0.119 (3)	0.0221 (17)	0.075 (2)	0.036 (2)
C1	0.0364 (16)	0.0231 (15)	0.0187 (14)	−0.0042 (12)	0.0135 (13)	0.0003 (11)
C2	0.0482 (19)	0.0268 (16)	0.0243 (15)	0.0024 (14)	0.0171 (15)	0.0002 (13)
C3	0.073 (3)	0.0254 (18)	0.0374 (19)	0.0041 (17)	0.0239 (19)	−0.0005 (15)
C4	0.092 (3)	0.0248 (18)	0.039 (2)	−0.017 (2)	0.024 (2)	−0.0056 (15)
C5	0.065 (3)	0.043 (2)	0.039 (2)	−0.027 (2)	0.0201 (19)	−0.0041 (17)
C6	0.0415 (18)	0.0339 (18)	0.0296 (17)	−0.0096 (15)	0.0176 (15)	−0.0042 (14)
C7	0.0225 (13)	0.0200 (14)	0.0219 (14)	−0.0017 (11)	0.0132 (11)	−0.0028 (11)
C8	0.0219 (14)	0.0269 (15)	0.0289 (15)	0.0006 (12)	0.0144 (12)	0.0016 (12)
C9	0.0224 (13)	0.0218 (14)	0.0197 (13)	−0.0038 (11)	0.0104 (11)	−0.0029 (11)
C10	0.0234 (14)	0.0227 (14)	0.0193 (13)	−0.0034 (11)	0.0122 (11)	−0.0018 (11)
C11	0.0239 (14)	0.0281 (16)	0.0248 (15)	0.0008 (12)	0.0117 (12)	0.0022 (12)
C12	0.0455 (18)	0.0206 (15)	0.0385 (18)	−0.0004 (14)	0.0281 (15)	0.0079 (13)
C13	0.1099 (19)	0.0302 (10)	0.0576 (13)	−0.0114 (11)	0.0569 (14)	−0.0012 (9)
C14	0.1099 (19)	0.0302 (10)	0.0576 (13)	−0.0114 (11)	0.0569 (14)	−0.0012 (9)
C15	0.1099 (19)	0.0302 (10)	0.0576 (13)	−0.0114 (11)	0.0569 (14)	−0.0012 (9)
C16	0.1099 (19)	0.0302 (10)	0.0576 (13)	−0.0114 (11)	0.0569 (14)	−0.0012 (9)
C17	0.075 (3)	0.0216 (16)	0.068 (3)	0.0064 (17)	0.058 (2)	0.0131 (16)

Geometric parameters (Å, º) top

S1—O1	1.436 (2)	C4—H4A	0.9900
S1—O2	1.431 (2)	C4—C5	1.515 (6)
S1—N1	1.605 (2)	C5—H5B	0.9900
S1—C7	1.742 (3)	C5—H5A	0.9900
S2—C7	1.720 (3)	C5—C6	1.534 (5)
S2—C8	1.708 (3)	C6—H6A	0.9900
O3—N3	1.235 (5)	C6—H6B	0.9900
O4—N3	1.265 (9)	C7—C10	1.362 (4)
O4A—N3	1.305 (12)	C8—H8	0.9500
N1—H1	0.8800	C8—C9	1.358 (4)
N1—C1	1.485 (4)	C9—C10	1.420 (4)
N2—H2	0.81 (3)	C9—C11	1.511 (4)
N2—C11	1.446 (4)	C10—H10	0.9500
N2—C12	1.353 (4)	C11—H11B	0.9900
N3—C17	1.437 (6)	C11—H11A	0.9900
C1—H1A	1.0000	C12—C13	1.412 (6)
C1—C2	1.528 (4)	C12—C17	1.414 (5)
C1—C6	1.515 (4)	C13—H13	0.9500
C2—H2B	0.9900	C13—C14	1.377 (5)
C2—H2A	0.9900	C14—H14	0.9500
C2—C3	1.530 (4)	C14—C15	1.387 (6)
C3—H3A	0.9900	C15—H15	0.9500
C3—H3B	0.9900	C15—C16	1.353 (6)
C3—C4	1.514 (6)	C16—H16	0.9500
C4—H4B	0.9900	C16—C17	1.412 (5)

S1—N1—H1	119.7	C4—C5—C6	111.5 (3)
S2—C7—S1	119.50 (16)	H4B—C4—H4A	108.0
S2—C8—H8	123.4	C5—C4—H4B	109.3
O1—S1—N1	107.83 (13)	C5—C4—H4A	109.3
O1—S1—C7	106.07 (13)	C5—C6—H6A	109.6
O2—S1—O1	119.95 (13)	C5—C6—H6B	109.6
O2—S1—N1	106.73 (13)	H5B—C5—H5A	108.0
O2—S1—C7	108.05 (13)	C6—C1—H1A	108.0
O3—N3—O4	130.6 (6)	C6—C1—C2	111.4 (3)
O3—N3—O4A	106.0 (7)	C6—C5—H5B	109.3
O3—N3—C17	120.2 (3)	C6—C5—H5A	109.3
O4—N3—O4A	33.1 (5)	H6A—C6—H6B	108.1
O4—N3—C17	108.2 (6)	C7—C10—C9	111.7 (2)
O4A—N3—C17	132.2 (7)	C7—C10—H10	124.1
N1—S1—C7	107.69 (13)	C8—S2—C7	90.39 (14)
N1—C1—H1A	108.0	C8—C9—C10	112.0 (3)
N1—C1—C2	111.5 (2)	C8—C9—C11	124.0 (3)
N1—C1—C6	109.9 (2)	C9—C8—S2	113.2 (2)
N2—C11—C9	113.8 (2)	C9—C8—H8	123.4
N2—C11—H11B	108.8	C9—C10—H10	124.1
N2—C11—H11A	108.8	C9—C11—H11B	108.8
N2—C12—C13	120.4 (3)	C9—C11—H11A	108.8
N2—C12—C17	123.6 (3)	C10—C7—S1	127.0 (2)
C1—N1—S1	120.60 (19)	C10—C7—S2	112.8 (2)
C1—N1—H1	119.7	C10—C9—C11	123.9 (2)
C1—C2—H2B	109.6	C11—N2—H2	117 (2)
C1—C2—H2A	109.6	H11B—C11—H11A	107.7
C1—C2—C3	110.3 (3)	C12—N2—H2	118 (2)
C1—C6—C5	110.4 (3)	C12—N2—C11	123.7 (3)
C1—C6—H6A	109.6	C12—C13—H13	119.0
C1—C6—H6B	109.6	C12—C17—N3	121.5 (3)
C2—C1—H1A	108.0	C13—C12—C17	115.9 (3)
C2—C3—H3A	109.4	C13—C14—H14	119.7
C2—C3—H3B	109.4	C13—C14—C15	120.5 (5)
H2B—C2—H2A	108.1	C14—C13—C12	121.9 (4)
C3—C2—H2B	109.6	C14—C13—H13	119.0
C3—C2—H2A	109.6	C14—C15—H15	120.0
C3—C4—H4B	109.3	C15—C14—H14	119.7
C3—C4—H4A	109.3	C15—C16—H16	119.8
C3—C4—C5	111.6 (3)	C15—C16—C17	120.4 (4)
H3A—C3—H3B	108.0	C16—C15—C14	120.0 (4)
C4—C3—C2	111.3 (3)	C16—C15—H15	120.0
C4—C3—H3A	109.4	C16—C17—N3	117.3 (4)
C4—C3—H3B	109.4	C16—C17—C12	121.1 (4)
C4—C5—H5B	109.3	C17—C16—H16	119.8
C4—C5—H5A	109.3

S1—N1—C1—C2	−98.5 (3)	C1—C2—C3—C4	55.9 (4)
S1—N1—C1—C6	137.5 (2)	C2—C1—C6—C5	56.5 (3)
S1—C7—C10—C9	170.7 (2)	C2—C3—C4—C5	−55.4 (4)
S2—C7—C10—C9	0.7 (3)	C3—C4—C5—C6	55.0 (4)
S2—C8—C9—C10	0.6 (3)	C4—C5—C6—C1	−55.3 (4)
S2—C8—C9—C11	−176.0 (2)	C6—C1—C2—C3	−56.9 (3)
O1—S1—N1—C1	−56.2 (2)	C7—S1—N1—C1	57.9 (2)
O1—S1—C7—S2	−169.60 (16)	C7—S2—C8—C9	−0.2 (2)
O1—S1—C7—C10	21.0 (3)	C8—S2—C7—S1	−171.17 (18)
O2—S1—N1—C1	173.7 (2)	C8—S2—C7—C10	−0.3 (2)
O2—S1—C7—S2	−39.8 (2)	C8—C9—C10—C7	−0.9 (3)
O2—S1—C7—C10	150.8 (3)	C8—C9—C11—N2	−18.9 (4)
O3—N3—C17—C12	−3.6 (5)	C10—C9—C11—N2	165.0 (3)
O3—N3—C17—C16	177.7 (3)	C11—N2—C12—C13	−4.6 (5)
O4—N3—C17—C12	−173.6 (5)	C11—N2—C12—C17	177.0 (3)
O4—N3—C17—C16	7.6 (6)	C11—C9—C10—C7	175.7 (3)
O4A—N3—C17—C12	159.5 (9)	C12—N2—C11—C9	−75.0 (4)
O4A—N3—C17—C16	−19.2 (10)	C12—C13—C14—C15	−0.8 (6)
N1—S1—C7—S2	75.17 (19)	C13—C12—C17—N3	177.9 (3)
N1—S1—C7—C10	−94.3 (3)	C13—C12—C17—C16	−3.4 (5)
N1—C1—C2—C3	−180.0 (2)	C13—C14—C15—C16	−0.9 (6)
N1—C1—C6—C5	−179.5 (3)	C14—C15—C16—C17	0.3 (6)
N2—C12—C13—C14	−175.7 (3)	C15—C16—C17—N3	−179.3 (3)
N2—C12—C17—N3	−3.6 (5)	C15—C16—C17—C12	1.9 (5)
N2—C12—C17—C16	175.1 (3)	C17—C12—C13—C14	2.9 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.27	2.956 (3)	134
N2—H2···O2ⁱⁱ	0.81 (3)	2.36 (3)	2.979 (3)	135 (3)
N2—H2···O3	0.81 (3)	2.01 (3)	2.620 (4)	132 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x+1, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁N₃O₄S₂
M_r	395.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	145
a, b, c (Å)	7.4201 (2), 27.8329 (7), 10.1790 (3)
β (°)	118.440 (3)
V (Å³)	1848.50 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.38 × 0.25 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.970, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	8048, 3772, 3104
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.129, 1.01
No. of reflections	3772
No. of parameters	225
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.02, −0.68

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.27	2.956 (3)	134.3
N2—H2···O2ⁱⁱ	0.81 (3)	2.36 (3)	2.979 (3)	135 (3)
N2—H2···O3	0.81 (3)	2.01 (3)	2.620 (4)	132 (3)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x+1, −y+1/2, z+1/2.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection. This work was supported by the Research Fund of the Key Laboratory of TCM Biotechnology, Xihua University.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Oxford, England. Google Scholar
Cuberes Altisen, R., Frigola Constansa, J. & Gutierrez Silva, B. (2007). US Patent Appl. US 20070066587 A1 20070322. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Santhakumar, V. & Tomaszewski, M. (2006). PCT Int. Appl. WO 2006052189 A1 20060518. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar