2-(N-Cyclo­hexyl­carbamo­yl)benzene­sulfonamide

Siddiqui, W.A.; Ashraf, A.; Siddiqui, H.L.; Akram, M.; Parvez, M.

doi:10.1107/S1600536812000633

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o370

doi:10.1107/S1600536812000633

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2-(N-Cyclohexylcarbamoyl)benzenesulfonamide

Waseeq Ahmad Siddiqui,^a ^* Adnan Ashraf,^a Hamid Latif Siddiqui,^b Muhammad Akram ^b and Masood Parvez ^c

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, ^bInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: waseeq786@gmail.com

(Received 28 December 2011; accepted 6 January 2012; online 14 January 2012)

The asymmetric unit of the title compound, C₁₃H₁₈N₂O₃S, contains two molecules with similar conformations. In both molecules, the cyclohexyl rings adopt chair conformations, with the attached N atom in an equatorial orientation and an intramolecular N—H⋯O hydrogen bond generates an S(7) ring. In the crystal, N—H⋯O hydrogen bonds link the molecules and a C—H⋯O hydrogen bond is also observed. The crystal studied was a racemic twin.

Related literature

For the biological activity of benzenesulfonamide derivatives, see: Petrov et al. (2006 ); Eatedal et al. (2002 ); Ahmad et al. (2010 ). For related structures, see: Siddiqui et al. (2007 , 2008 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₃H₁₈N₂O₃S
M_r = 282.35
Orthorhombic, P c a 2₁
a = 16.1869 (5) Å
b = 10.8467 (3) Å
c = 15.9353 (4) Å
V = 2797.83 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 173 K
0.20 × 0.14 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.954, T_max = 0.981
5929 measured reflections
5929 independent reflections
5451 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.110
S = 1.14
5929 reflections
362 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 )
Flack parameter: 0.52 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11N⋯O4ⁱ	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N⋯O6ⁱⁱ	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N⋯O2ⁱⁱⁱ	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3⋯O1^iv	0.95	2.54	3.254 (4)	132
N1—H12N⋯O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N⋯O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N⋯O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)
Symmetry codes: (i) x, y+1, z; (ii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-1, z-{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, -y+1, z]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812000633/hb6585sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000633/hb6585Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000633/hb6585Isup3.cml

checkCIF report

Comment top

Derivatives of benzenesulfonamide find wide spread applications for the synthesis of pharmaceutical products which have bactericidal properties, various bioactive agents, artificial fibers, dyes, plasticizers and high molecular weight substances (Petrov et al., 2006). Several pyrazole and oxadiazole derivatives have been reported to exhibit analgesic and anti-inflammatory activities and many drugs containing them are still in use in the market (Eatedal et al., 2002). In continuation of our research on the synthesis of biological active benzothiazine derivatives (Siddiqui et al., 2007) we report the synthesis and crystal structure of the title compound in this article.

There are two independent molecules in an asymmetric unit of the title compound, labeled as molecules A (Fig. 1) and B (Fig. 2) containing the S1 and S2 atoms, respectively. There are insignificant differences in the conformations of the two molecules, e.g., the torsion angles C6–C7–N2–C8 and C19–C20–N4–C21 in molecules A and B are 177.3 (3) and -179.2 (3)°, respectively. In both molecules, the cyclohexyl rings adopt chair conformations with puckering parameters (Cremer & Pople, 1975) in molecules A and B being Q = 0.564 (4) and 0.573 (4) Å, θ = 3.1 (4) and 2.3 (4) ° and ω = 273 (8) and 251 (8) °, respectively. The bond distances and angles in both molecules agree very well with the cortresponding bond distances and angles reported in a closely related compound (Siddiqui et al., 2007).

In the solid state, the molecules A and B are linked with each other via hydrogen bonds involving amino and O-atoms of the sulfonamide groups with N1···O4 = 2.935 (4) and N3···O2 = 2.943 (4) Å. The molecules A are linked into chains involving intermolecular interactions C3···O1 = 3.254 (4) Å. The molecules B do not show any such interactions. The molecules are stabilized by intramolecular interactions of the types N—H···O and C—H···O (Table 1 and Figure 3).

Related literature top

For the biological activity of benzenesulfonamide derivatives, see: Petrov et al. (2006); Eatedal et al. (2002). For related structures, see: Siddiqui et al. (2007, 2008). For ring puckering parameters, see: Cremer & Pople (1975). For related literature [on what subject?], see: Ahmad et al. (2010).

Experimental top

For the synthesis of the title compound, cyclohexylamine and saccharin were used as the starting materials following a reported procedure (Siddiqui et al., 2008). Crystals of the title compound suitable for X-ray crystallographic study were grown from methanol at room temperature; m.p. = 512 – 513 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecule A of the title compound with displacement ellipsoids plotted at 30% probability level.
	Fig. 2. The molecule B of the title compound with displacement ellipsoids plotted at 30% probability level.
	Fig. 3. The unit cell packing diagram of the title compound showing hydrogen bonding interactions drawn with dashed lines. Hydrogen atoms not involved in H-bonds have been excluded for clarity.

2-(N-Cyclohexylcarbamoyl)benzenesulfonamide top

Crystal data top

C₁₃H₁₈N₂O₃S	F(000) = 1200
M_r = 282.35	D_x = 1.341 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3423 reflections
a = 16.1869 (5) Å	θ = 1.0–27.5°
b = 10.8467 (3) Å	µ = 0.24 mm⁻¹
c = 15.9353 (4) Å	T = 173 K
V = 2797.83 (13) Å³	Prism, pale-yellow
Z = 8	0.20 × 0.14 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	5929 independent reflections
Radiation source: fine-focus sealed tube	5451 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 27.4°, θ_min = 2.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −20→20
T_min = 0.954, T_max = 0.981	k = −14→14
5929 measured reflections	l = −20→20

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)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.009P)² + 3.8318P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
5929 reflections	Δρ_max = 0.31 e Å⁻³
362 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.52 (8)

Crystal data top

C₁₃H₁₈N₂O₃S	V = 2797.83 (13) Å³
M_r = 282.35	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 16.1869 (5) Å	µ = 0.24 mm⁻¹
b = 10.8467 (3) Å	T = 173 K
c = 15.9353 (4) Å	0.20 × 0.14 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	5929 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	5451 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.981	R_int = 0.034
5929 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	Δρ_max = 0.31 e Å⁻³
S = 1.14	Δρ_min = −0.28 e Å⁻³
5929 reflections	Absolute structure: Flack (1983)
362 parameters	Absolute structure parameter: 0.52 (8)
1 restraint

Special details top

Experimental. IR (KBr, max, cm^-1) NH₂ & NH 3318, 3275; CO 1680; SO₂ 1320 and 1155; ¹H-NMR (300 MHz, Methanol -d4) δ: 1.30–1.75 (m, 10H, cyclohexyl), 3.35 (m, 1H, cyclohexyl-CH), 5.55 (s, 2H, NH₂), 7.73–8.13 (m, 4H, C₆H₄); ¹³C-NMR δ: 167.5, 137.5, 133.4, 131.9, 131.5, 127.7, 127.3, 45.7, 34.5, 27.3, 22.7

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
S1	0.34082 (5)	0.60650 (7)	0.55872 (6)	0.02820 (16)
S2	0.25588 (6)	−0.07073 (7)	0.31713 (6)	0.03103 (18)
O1	0.40724 (14)	0.5355 (2)	0.59198 (15)	0.0357 (6)
O2	0.31913 (17)	0.7220 (2)	0.59666 (17)	0.0440 (7)
O3	0.36076 (14)	0.3676 (2)	0.43341 (13)	0.0287 (5)
O4	0.27815 (17)	−0.1884 (2)	0.35130 (19)	0.0493 (7)
O5	0.20767 (16)	0.0130 (2)	0.36603 (16)	0.0394 (6)
O6	0.21853 (14)	0.1570 (2)	0.19541 (13)	0.0276 (5)
N1	0.3621 (2)	0.6352 (3)	0.46194 (19)	0.0330 (7)
H11N	0.327 (3)	0.690 (4)	0.437 (2)	0.040*
H12N	0.369 (3)	0.568 (4)	0.434 (3)	0.040*
N2	0.35953 (18)	0.2310 (2)	0.54146 (17)	0.0294 (6)
H2N	0.335 (2)	0.212 (4)	0.591 (3)	0.035*
N3	0.2057 (2)	−0.0976 (3)	0.2323 (2)	0.0355 (7)
H31N	0.201 (3)	−0.034 (4)	0.202 (3)	0.043*
H32N	0.222 (3)	−0.163 (4)	0.205 (3)	0.043*
N4	0.25528 (18)	0.3051 (2)	0.28838 (17)	0.0260 (6)
H4N	0.290 (2)	0.325 (3)	0.326 (2)	0.031*
C1	0.25169 (19)	0.5111 (3)	0.5624 (2)	0.0257 (6)
C2	0.1783 (2)	0.5611 (3)	0.5923 (2)	0.0353 (8)
H2	0.1768	0.6444	0.6106	0.042*
C3	0.1075 (2)	0.4899 (4)	0.5954 (3)	0.0407 (9)
H3	0.0571	0.5248	0.6146	0.049*
C4	0.1101 (2)	0.3689 (3)	0.5706 (3)	0.0392 (8)
H4	0.0613	0.3203	0.5722	0.047*
C5	0.1834 (2)	0.3174 (3)	0.5434 (2)	0.0339 (8)
H5	0.1846	0.2328	0.5280	0.041*
C6	0.2557 (2)	0.3867 (3)	0.53812 (19)	0.0269 (7)
C7	0.3311 (2)	0.3281 (3)	0.5007 (2)	0.0262 (7)
C8	0.4304 (2)	0.1578 (3)	0.5131 (2)	0.0295 (7)
H8	0.4268	0.1483	0.4508	0.035*
C9	0.4254 (2)	0.0303 (3)	0.5529 (3)	0.0418 (9)
H9A	0.3743	−0.0114	0.5340	0.050*
H9B	0.4227	0.0388	0.6147	0.050*
C10	0.5003 (3)	−0.0486 (4)	0.5294 (3)	0.0558 (12)
H10A	0.4980	−0.1273	0.5608	0.067*
H10B	0.4979	−0.0681	0.4688	0.067*
C11	0.5804 (3)	0.0149 (4)	0.5482 (3)	0.0551 (11)
H11A	0.6267	−0.0367	0.5279	0.066*
H11B	0.5864	0.0244	0.6097	0.066*
C12	0.5848 (3)	0.1414 (4)	0.5067 (3)	0.0455 (9)
H12A	0.5843	0.1317	0.4449	0.055*
H12B	0.6369	0.1828	0.5227	0.055*
C13	0.5111 (2)	0.2206 (3)	0.5341 (2)	0.0361 (8)
H13A	0.5140	0.2353	0.5953	0.043*
H13B	0.5136	0.3015	0.5054	0.043*
C14	0.34848 (19)	0.0091 (3)	0.2919 (2)	0.0239 (6)
C15	0.4234 (2)	−0.0517 (3)	0.3024 (2)	0.0346 (8)
H15	0.4241	−0.1355	0.3196	0.042*
C16	0.4974 (2)	0.0098 (3)	0.2877 (2)	0.0351 (8)
H16	0.5486	−0.0319	0.2942	0.042*
C17	0.4956 (2)	0.1325 (3)	0.2636 (2)	0.0327 (8)
H17	0.5459	0.1750	0.2532	0.039*
C18	0.4208 (2)	0.1936 (3)	0.2545 (2)	0.0296 (7)
H18	0.4206	0.2782	0.2392	0.035*
C19	0.34610 (19)	0.1327 (3)	0.26748 (18)	0.0227 (6)
C20	0.26705 (18)	0.1994 (3)	0.24848 (18)	0.0221 (6)
C21	0.1806 (2)	0.3805 (3)	0.2773 (2)	0.0264 (7)
H21	0.1713	0.3936	0.2159	0.032*
C22	0.1946 (2)	0.5054 (3)	0.3188 (2)	0.0324 (7)
H22A	0.2100	0.4929	0.3783	0.039*
H22B	0.2410	0.5479	0.2905	0.039*
C23	0.1177 (2)	0.5864 (3)	0.3142 (2)	0.0354 (8)
H23A	0.1275	0.6635	0.3460	0.042*
H23B	0.1069	0.6088	0.2550	0.042*
C24	0.0428 (2)	0.5213 (4)	0.3498 (3)	0.0426 (9)
H24A	−0.0066	0.5740	0.3426	0.051*
H24B	0.0509	0.5070	0.4106	0.051*
C25	0.0290 (2)	0.3983 (4)	0.3057 (3)	0.0459 (10)
H25A	−0.0192	0.3559	0.3309	0.055*
H25B	0.0170	0.4128	0.2456	0.055*
C26	0.1052 (2)	0.3169 (3)	0.3139 (3)	0.0346 (7)
H26A	0.1151	0.2982	0.3739	0.042*
H26B	0.0956	0.2381	0.2841	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0271 (4)	0.0283 (3)	0.0292 (4)	−0.0026 (3)	−0.0003 (3)	−0.0022 (3)
S2	0.0288 (4)	0.0271 (4)	0.0372 (4)	−0.0029 (4)	−0.0010 (4)	0.0083 (4)
O1	0.0255 (12)	0.0457 (14)	0.0359 (13)	−0.0016 (10)	−0.0031 (10)	0.0036 (11)
O2	0.0453 (15)	0.0363 (14)	0.0504 (16)	−0.0056 (12)	0.0067 (13)	−0.0126 (12)
O3	0.0335 (12)	0.0273 (11)	0.0253 (12)	0.0013 (9)	0.0015 (9)	0.0036 (9)
O4	0.0457 (16)	0.0363 (14)	0.0660 (19)	−0.0054 (12)	−0.0088 (14)	0.0238 (13)
O5	0.0355 (13)	0.0477 (15)	0.0351 (14)	−0.0036 (12)	0.0101 (11)	0.0036 (11)
O6	0.0307 (12)	0.0239 (11)	0.0282 (12)	0.0004 (9)	−0.0059 (9)	−0.0009 (9)
N1	0.0382 (17)	0.0278 (15)	0.0330 (16)	−0.0030 (13)	0.0030 (13)	0.0038 (12)
N2	0.0365 (16)	0.0249 (13)	0.0270 (15)	0.0062 (12)	0.0058 (12)	0.0034 (11)
N3	0.0340 (17)	0.0258 (15)	0.0467 (19)	−0.0033 (13)	−0.0067 (14)	0.0005 (13)
N4	0.0262 (13)	0.0235 (13)	0.0283 (14)	0.0039 (11)	−0.0071 (11)	−0.0022 (10)
C1	0.0236 (13)	0.0287 (14)	0.0247 (14)	−0.0002 (12)	0.0000 (13)	0.0030 (15)
C2	0.0307 (17)	0.0348 (18)	0.040 (2)	0.0048 (15)	0.0029 (15)	0.0011 (15)
C3	0.0252 (17)	0.052 (2)	0.045 (2)	0.0103 (16)	0.0064 (15)	0.0092 (17)
C4	0.0281 (17)	0.045 (2)	0.045 (2)	−0.0094 (15)	0.0008 (16)	0.0169 (18)
C5	0.0335 (18)	0.0302 (16)	0.038 (2)	−0.0062 (14)	−0.0009 (14)	0.0058 (14)
C6	0.0265 (15)	0.0297 (15)	0.0244 (16)	0.0004 (13)	−0.0024 (12)	0.0059 (12)
C7	0.0296 (17)	0.0225 (15)	0.0265 (16)	−0.0018 (13)	−0.0023 (13)	−0.0020 (12)
C8	0.0380 (19)	0.0266 (16)	0.0240 (16)	0.0057 (14)	0.0051 (13)	0.0027 (13)
C9	0.051 (2)	0.0281 (17)	0.046 (2)	0.0075 (15)	0.0052 (19)	0.0097 (17)
C10	0.075 (3)	0.035 (2)	0.057 (3)	0.024 (2)	0.013 (2)	0.0082 (19)
C11	0.054 (3)	0.060 (3)	0.051 (3)	0.033 (2)	0.009 (2)	0.007 (2)
C12	0.039 (2)	0.049 (2)	0.048 (2)	0.0136 (18)	0.0046 (18)	−0.0036 (19)
C13	0.0355 (19)	0.0340 (18)	0.0390 (19)	0.0084 (15)	0.0028 (15)	−0.0044 (15)
C14	0.0219 (14)	0.0214 (14)	0.0285 (16)	−0.0033 (12)	−0.0027 (12)	−0.0006 (11)
C15	0.0361 (19)	0.0261 (16)	0.042 (2)	0.0023 (14)	−0.0063 (15)	0.0001 (14)
C16	0.0244 (15)	0.0324 (17)	0.049 (2)	0.0046 (13)	−0.0031 (15)	−0.0066 (16)
C17	0.0232 (16)	0.0336 (17)	0.041 (2)	−0.0069 (14)	−0.0008 (14)	−0.0046 (15)
C18	0.0326 (17)	0.0268 (16)	0.0293 (17)	−0.0031 (14)	−0.0014 (14)	−0.0017 (13)
C19	0.0263 (15)	0.0217 (14)	0.0201 (14)	0.0024 (12)	−0.0011 (12)	−0.0033 (11)
C20	0.0233 (15)	0.0210 (14)	0.0221 (15)	−0.0002 (11)	0.0021 (12)	0.0014 (11)
C21	0.0276 (16)	0.0235 (15)	0.0282 (16)	0.0030 (12)	0.0007 (13)	−0.0014 (13)
C22	0.0349 (17)	0.0251 (16)	0.0372 (18)	0.0009 (13)	−0.0013 (15)	0.0000 (15)
C23	0.049 (2)	0.0245 (16)	0.0329 (18)	0.0110 (15)	0.0021 (17)	−0.0016 (15)
C24	0.045 (2)	0.039 (2)	0.043 (2)	0.0157 (17)	0.0108 (17)	0.0005 (17)
C25	0.0315 (19)	0.044 (2)	0.062 (3)	0.0031 (16)	0.0074 (18)	−0.0036 (19)
C26	0.0362 (19)	0.0271 (16)	0.0406 (19)	0.0022 (14)	0.0025 (16)	−0.0006 (15)

Geometric parameters (Å, º) top

S1—O1	1.425 (2)	C10—H10A	0.9900
S1—O2	1.434 (3)	C10—H10B	0.9900
S1—N1	1.610 (3)	C11—C12	1.525 (6)
S1—C1	1.777 (3)	C11—H11A	0.9900
S2—O5	1.428 (3)	C11—H11B	0.9900
S2—O4	1.434 (3)	C12—C13	1.534 (5)
S2—N3	1.604 (3)	C12—H12A	0.9900
S2—C14	1.777 (3)	C12—H12B	0.9900
O3—C7	1.252 (4)	C13—H13A	0.9900
O6—C20	1.242 (4)	C13—H13B	0.9900
N1—H11N	0.92 (4)	C14—C15	1.390 (4)
N1—H12N	0.86 (4)	C14—C19	1.397 (4)
N2—C7	1.320 (4)	C15—C16	1.390 (5)
N2—C8	1.467 (4)	C15—H15	0.9500
N2—H2N	0.91 (4)	C16—C17	1.385 (5)
N3—H31N	0.85 (4)	C16—H16	0.9500
N3—H32N	0.88 (4)	C17—C18	1.387 (5)
N4—C20	1.325 (4)	C17—H17	0.9500
N4—C21	1.470 (4)	C18—C19	1.393 (4)
N4—H4N	0.85 (4)	C18—H18	0.9500
C1—C2	1.390 (4)	C19—C20	1.501 (4)
C1—C6	1.405 (4)	C21—C26	1.518 (5)
C2—C3	1.382 (5)	C21—C22	1.525 (4)
C2—H2	0.9500	C21—H21	1.0000
C3—C4	1.371 (6)	C22—C23	1.525 (4)
C3—H3	0.9500	C22—H22A	0.9900
C4—C5	1.381 (5)	C22—H22B	0.9900
C4—H4	0.9500	C23—C24	1.513 (5)
C5—C6	1.393 (4)	C23—H23A	0.9900
C5—H5	0.9500	C23—H23B	0.9900
C6—C7	1.500 (4)	C24—C25	1.524 (5)
C8—C13	1.510 (5)	C24—H24A	0.9900
C8—C9	1.524 (4)	C24—H24B	0.9900
C8—H8	1.0000	C25—C26	1.521 (5)
C9—C10	1.531 (5)	C25—H25A	0.9900
C9—H9A	0.9900	C25—H25B	0.9900
C9—H9B	0.9900	C26—H26A	0.9900
C10—C11	1.498 (7)	C26—H26B	0.9900

O1—S1—O2	120.00 (16)	C11—C12—C13	110.1 (3)
O1—S1—N1	107.43 (16)	C11—C12—H12A	109.6
O2—S1—N1	106.70 (17)	C13—C12—H12A	109.6
O1—S1—C1	106.58 (14)	C11—C12—H12B	109.6
O2—S1—C1	107.23 (15)	C13—C12—H12B	109.6
N1—S1—C1	108.50 (16)	H12A—C12—H12B	108.1
O5—S2—O4	119.74 (18)	C8—C13—C12	110.9 (3)
O5—S2—N3	107.38 (17)	C8—C13—H13A	109.5
O4—S2—N3	106.62 (17)	C12—C13—H13A	109.5
O5—S2—C14	105.93 (15)	C8—C13—H13B	109.5
O4—S2—C14	107.90 (16)	C12—C13—H13B	109.5
N3—S2—C14	108.96 (17)	H13A—C13—H13B	108.0
S1—N1—H11N	114 (2)	C15—C14—C19	120.8 (3)
S1—N1—H12N	112 (3)	C15—C14—S2	118.6 (3)
H11N—N1—H12N	113 (4)	C19—C14—S2	120.5 (2)
C7—N2—C8	123.6 (3)	C16—C15—C14	120.3 (3)
C7—N2—H2N	117 (2)	C16—C15—H15	119.9
C8—N2—H2N	119 (2)	C14—C15—H15	119.9
S2—N3—H31N	112 (3)	C17—C16—C15	119.3 (3)
S2—N3—H32N	114 (3)	C17—C16—H16	120.4
H31N—N3—H32N	114 (4)	C15—C16—H16	120.4
C20—N4—C21	122.8 (3)	C16—C17—C18	120.4 (3)
C20—N4—H4N	118 (2)	C16—C17—H17	119.8
C21—N4—H4N	119 (2)	C18—C17—H17	119.8
C2—C1—C6	120.5 (3)	C17—C18—C19	121.0 (3)
C2—C1—S1	118.5 (2)	C17—C18—H18	119.5
C6—C1—S1	120.9 (2)	C19—C18—H18	119.5
C3—C2—C1	120.2 (3)	C18—C19—C14	118.2 (3)
C3—C2—H2	119.9	C18—C19—C20	118.8 (3)
C1—C2—H2	119.9	C14—C19—C20	122.8 (3)
C4—C3—C2	119.9 (3)	O6—C20—N4	123.8 (3)
C4—C3—H3	120.1	O6—C20—C19	119.9 (3)
C2—C3—H3	120.1	N4—C20—C19	116.3 (3)
C3—C4—C5	120.3 (3)	N4—C21—C26	111.3 (3)
C3—C4—H4	119.9	N4—C21—C22	108.6 (3)
C5—C4—H4	119.9	C26—C21—C22	110.9 (3)
C4—C5—C6	121.5 (3)	N4—C21—H21	108.6
C4—C5—H5	119.3	C26—C21—H21	108.6
C6—C5—H5	119.3	C22—C21—H21	108.6
C5—C6—C1	117.6 (3)	C23—C22—C21	111.7 (3)
C5—C6—C7	118.6 (3)	C23—C22—H22A	109.3
C1—C6—C7	123.6 (3)	C21—C22—H22A	109.3
O3—C7—N2	124.1 (3)	C23—C22—H22B	109.3
O3—C7—C6	120.5 (3)	C21—C22—H22B	109.3
N2—C7—C6	115.3 (3)	H22A—C22—H22B	107.9
N2—C8—C13	111.3 (3)	C24—C23—C22	111.5 (3)
N2—C8—C9	108.7 (3)	C24—C23—H23A	109.3
C13—C8—C9	111.3 (3)	C22—C23—H23A	109.3
N2—C8—H8	108.5	C24—C23—H23B	109.3
C13—C8—H8	108.5	C22—C23—H23B	109.3
C9—C8—H8	108.5	H23A—C23—H23B	108.0
C8—C9—C10	111.3 (3)	C23—C24—C25	110.7 (3)
C8—C9—H9A	109.4	C23—C24—H24A	109.5
C10—C9—H9A	109.4	C25—C24—H24A	109.5
C8—C9—H9B	109.4	C23—C24—H24B	109.5
C10—C9—H9B	109.4	C25—C24—H24B	109.5
H9A—C9—H9B	108.0	H24A—C24—H24B	108.1
C11—C10—C9	112.3 (3)	C26—C25—C24	110.5 (3)
C11—C10—H10A	109.1	C26—C25—H25A	109.6
C9—C10—H10A	109.1	C24—C25—H25A	109.6
C11—C10—H10B	109.1	C26—C25—H25B	109.6
C9—C10—H10B	109.1	C24—C25—H25B	109.6
H10A—C10—H10B	107.9	H25A—C25—H25B	108.1
C10—C11—C12	111.5 (3)	C21—C26—C25	110.8 (3)
C10—C11—H11A	109.3	C21—C26—H26A	109.5
C12—C11—H11A	109.3	C25—C26—H26A	109.5
C10—C11—H11B	109.3	C21—C26—H26B	109.5
C12—C11—H11B	109.3	C25—C26—H26B	109.5
H11A—C11—H11B	108.0	H26A—C26—H26B	108.1

O1—S1—C1—C2	134.7 (3)	O5—S2—C14—C15	133.5 (3)
O2—S1—C1—C2	5.0 (3)	O4—S2—C14—C15	4.1 (3)
N1—S1—C1—C2	−109.9 (3)	N3—S2—C14—C15	−111.3 (3)
O1—S1—C1—C6	−43.4 (3)	O5—S2—C14—C19	−42.3 (3)
O2—S1—C1—C6	−173.1 (3)	O4—S2—C14—C19	−171.7 (3)
N1—S1—C1—C6	72.0 (3)	N3—S2—C14—C19	72.9 (3)
C6—C1—C2—C3	−2.5 (6)	C19—C14—C15—C16	−0.7 (5)
S1—C1—C2—C3	179.4 (3)	S2—C14—C15—C16	−176.5 (3)
C1—C2—C3—C4	1.5 (6)	C14—C15—C16—C17	0.8 (5)
C2—C3—C4—C5	0.6 (6)	C15—C16—C17—C18	0.3 (5)
C3—C4—C5—C6	−1.7 (6)	C16—C17—C18—C19	−1.4 (5)
C4—C5—C6—C1	0.7 (5)	C17—C18—C19—C14	1.5 (5)
C4—C5—C6—C7	−174.5 (3)	C17—C18—C19—C20	−173.9 (3)
C2—C1—C6—C5	1.4 (5)	C15—C14—C19—C18	−0.5 (4)
S1—C1—C6—C5	179.4 (2)	S2—C14—C19—C18	175.3 (2)
C2—C1—C6—C7	176.4 (3)	C15—C14—C19—C20	174.8 (3)
S1—C1—C6—C7	−5.6 (5)	S2—C14—C19—C20	−9.5 (4)
C8—N2—C7—O3	0.7 (5)	C21—N4—C20—O6	3.6 (5)
C8—N2—C7—C6	177.3 (3)	C21—N4—C20—C19	−179.2 (3)
C5—C6—C7—O3	114.7 (3)	C18—C19—C20—O6	120.3 (3)
C1—C6—C7—O3	−60.2 (4)	C14—C19—C20—O6	−55.0 (4)
C5—C6—C7—N2	−62.1 (4)	C18—C19—C20—N4	−57.0 (4)
C1—C6—C7—N2	123.0 (3)	C14—C19—C20—N4	127.7 (3)
C7—N2—C8—C13	78.8 (4)	C20—N4—C21—C26	68.3 (4)
C7—N2—C8—C9	−158.2 (3)	C20—N4—C21—C22	−169.3 (3)
N2—C8—C9—C10	−177.0 (3)	N4—C21—C22—C23	−176.7 (3)
C13—C8—C9—C10	−54.0 (4)	C26—C21—C22—C23	−54.1 (4)
C8—C9—C10—C11	53.1 (5)	C21—C22—C23—C24	54.0 (4)
C9—C10—C11—C12	−54.6 (5)	C22—C23—C24—C25	−55.5 (4)
C10—C11—C12—C13	56.3 (5)	C23—C24—C25—C26	57.6 (4)
N2—C8—C13—C12	178.2 (3)	N4—C21—C26—C25	177.4 (3)
C9—C8—C13—C12	56.7 (4)	C22—C21—C26—C25	56.3 (4)
C11—C12—C13—C8	−57.4 (4)	C24—C25—C26—C21	−58.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O4ⁱ	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N···O6ⁱⁱ	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N···O2ⁱⁱⁱ	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3···O1^iv	0.95	2.54	3.254 (4)	132
N1—H12N···O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N···O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N···O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₈N₂O₃S
M_r	282.35
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	173
a, b, c (Å)	16.1869 (5), 10.8467 (3), 15.9353 (4)
V (Å³)	2797.83 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.20 × 0.14 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.954, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5929, 5929, 5451
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.110, 1.14
No. of reflections	5929
No. of parameters	362
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)	0.31, −0.28
Absolute structure	Flack (1983)
Absolute structure parameter	0.52 (8)

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11N···O4ⁱ	0.92 (4)	2.05 (4)	2.935 (4)	161 (4)
N2—H2N···O6ⁱⁱ	0.91 (4)	1.96 (4)	2.874 (4)	175 (4)
N3—H32N···O2ⁱⁱⁱ	0.88 (4)	2.23 (4)	2.943 (4)	138 (4)
C3—H3···O1^iv	0.95	2.54	3.254 (4)	132.2
N1—H12N···O3	0.86 (4)	2.18 (4)	2.938 (4)	146 (4)
N3—H31N···O6	0.85 (4)	2.09 (4)	2.831 (4)	145 (4)
N4—H4N···O3	0.85 (4)	2.11 (4)	2.952 (4)	171 (3)

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

Acknowledgements

WAS is grateful to the University of Sargodha, Sargodha, Pakistan, for providing research facilities.

References

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