N-{4-[(3,4-Dimethyl­phen­yl)sulfamo­yl]phen­yl}acetamide

Khan, I.U.; John, P.; Khizar, S.; Sharif, S.; Tiekink, E.R.T.

doi:10.1107/S1600536810029405

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 8| August 2010| Pages o2134-o2135

https://doi.org/10.1107/S1600536810029405

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N-{4-[(3,4-Dimethylphenyl)sulfamoyl]phenyl}acetamide

Islam Ullah Khan,^a ‡ Peter John,^a Saima Khizar,^a Shahzad Sharif ^a and Edward R. T. Tiekink ^b ^*

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 22 July 2010; accepted 23 July 2010; online 31 July 2010)

Two independent molecules comprise the asymmetric unit of the title compound, C₁₆H₁₈N₂O₃S. Small but significant twists about the (S)N—C and S—C bonds differentiate the molecules but the most obvious difference is found in the relative orientation of the meta-methyl groups, which lie on opposite sides of the molecules. Overall, both molecules adopt a U shape but with significant twisting evident, particularly in the second independent molecule [dihedral angles between benzene rings = 63.90 (13) and 35.78 (11)°]. In the crystal, N—H⋯O hydrogen bonds lead to supramolecular chains with a tubular topology propagating in [100] and C—H⋯O contacts cross-link the chains.

Related literature

For background to the antimicrobial activity of sulfonamides, see: Korolkovas, (1988 ); Mandell & Sande (1992 ). For related structures, see: John et al. (2010a ,b ).

Experimental

Crystal data

C₁₆H₁₈N₂O₃S
M_r = 318.40
Triclinic, $[P \overline 1]$
a = 8.4317 (3) Å
b = 13.6142 (5) Å
c = 15.1796 (5) Å
α = 71.340 (1)°
β = 77.136 (1)°
γ = 81.089 (1)°
V = 1602.83 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.27 × 0.11 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.817, T_max = 0.940
27476 measured reflections
7319 independent reflections
5632 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.152
S = 1.06
7319 reflections
415 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3ⁱ	0.86 (2)	2.07 (2)	2.909 (3)	164 (2)
N2—H2n⋯O4ⁱⁱ	0.88 (2)	2.08 (2)	2.931 (3)	163 (2)
N3—H3n⋯O1ⁱⁱⁱ	0.87 (2)	2.11 (2)	2.960 (3)	166 (2)
N4—H4n⋯O5ⁱⁱⁱ	0.87 (2)	2.18 (2)	3.036 (2)	170 (2)
C8—H8b⋯O6^iv	0.96	2.71	3.640 (3)	163
C6—H6⋯O6^iv	0.93	2.67	3.541 (3)	156
C16—H16c⋯O6^v	0.96	2.65	3.477 (3)	145
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y, z; (iv) x+1, y+1, z; (v) x, y+1, z.

Data collection: APEX2 (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: ORTEP-3 (Farrugia, 1997 ), DIAMOND (Brandenburg, 2006 ) and Qmol (Gans & Shalloway, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: https://doi.org/10.1107/S1600536810029405/hb5572sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029405/hb5572Isup2.hkl

checkCIF report

Comment top

Sulfonamides related to the title compound exhibit anti-microbial activity (Korolkovas, 1988; Mandell & Sande, 1992). In connection with on-going structural studies of sulfonamides containing acetamide residues (John et al., 2010a; John et al., 2010b), the crystal and molecular structure of the title compound, (I), was investigated.

Two independent molecules comprise the crystallographic asymmetric unit of (I). There are non-chemically significant differences between the two molecules with the first, Fig. 1, being almost super-imposable upon the second, Fig. 2, but with twists evident about the (S)N–C and S–C bonds, Fig. 3. About the former, the differences are quantified in the S1–N1–C1–C2 and S2–N3–C17–C22 torsion angles of -107.5 (2) and -93.8 (2) °, respectively. About the S–C bond, the twists are evident in the O1–S1–C9–C10 and O4–S2–C25–C26 torsion angles of -44.3 (2) and -25.36 (19) °, respectively. In each case, the acetamide group is co-planar with the benzene ring to which it is bonded [C12–N2–C15–O3 = 0.5 (4) ° and C28–N4–C31–O6 = -3.2 (4) °]. The major difference relates to the relative disposition of the meta-methyl group which effectively resides on opposite sides in the two molecules, Fig. 3. Within each molecule, the benzene molecules are orientated in the same direction and form dihedral angles of 63.90 (13) ° (first molecule) and 35.78 (11) ° so that overall the molecules have a U-shaped but with significant twisting, in particular for the second independent molecule.

The crystal packing is dominated by N–H···O hydrogen bonds whereby each of the amide-N atoms forms an interaction with a sulfamoyl-O atom, Table 1. The sulfamoyl-N–H forms an interaction with an amide-O in the case of N1 but with a sulfamoyl-O atom in the case of N4, Table 1. The result of the hydrogen bonding is the formation of a supramolecular chain along the a axis with a tubular topology, Fig. 4. Perhaps surprisingly, the hydrogen bonding scheme does not involve the amide-O6 atom, which lies to the periphery of the chain, Fig. 4. However, the O6 atom forms a very short intramolecular C–H···O contact [H···O = 2.22 Å] and forms three further C–H···O contacts less than 2.72 Å [shortest = 2.65 Å with H16cⁱ where i: x, -1 + y, z], thereby providing links between the supramolecular chains.

Related literature top

For background to the antimicrobial activity of sulfonamides, see: Korolkovas, (1988); Mandell & Sande (1992). For related structures, see: John et al. (2010a,b).

Experimental top

To 3,4-dimethyl aniline (242 mg, 2 mmol) in distilled water (10 ml) was added 4-acetamido benzene sulfonyl chloride (467 mg, 2 mmol) with stirring at room temperature while maintaining the pH of the reaction mixture at pH 8 using 3% sodium carbonate. The progress of the reaction was monitored by TLC. The precipitate formed was washed with water, dried and crystallized from a methanol/ethyl acetate mixture (50:50 V/V) to yield light-orange blocks of (I).

Structure description top

For background to the antimicrobial activity of sulfonamides, see: Korolkovas, (1988); Mandell & Sande (1992). For related structures, see: John et al. (2010a,b).

Computing details top

Data collection: APEX2 (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: ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the first independent molecule in (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 2. The molecular structure of the second independent molecule in (I) showing displacement ellipsoids at the 35% probability level.
	Fig. 3. Overlay diagram of the first independent molecule (shown in red) and the second independent molecule (shown in blue).
	Fig. 4. Linear supramolecular chain along [100] in (I) mediated by N–H···O hydrogen bonding, shown as orange dashed lines.

N-{4-[(3,4-Dimethylphenyl)sulfamoyl]phenyl}acetamide top

Crystal data top

C₁₆H₁₈N₂O₃S	Z = 4
M_r = 318.40	F(000) = 672
Triclinic, P1	D_x = 1.319 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4317 (3) Å	Cell parameters from 9916 reflections
b = 13.6142 (5) Å	θ = 2.5–28.2°
c = 15.1796 (5) Å	µ = 0.22 mm⁻¹
α = 71.340 (1)°	T = 293 K
β = 77.136 (1)°	Prism, light-orange
γ = 81.089 (1)°	0.27 × 0.11 × 0.08 mm
V = 1602.83 (10) Å³

Data collection top

Bruker APEXII CCD diffractometer	7319 independent reflections
Radiation source: fine-focus sealed tube	5632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.817, T_max = 0.940	k = −17→17
27476 measured reflections	l = −19→19

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.079P)² + 0.545P] where P = (F_o² + 2F_c²)/3
7319 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.34 e Å⁻³
4 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O₃S	γ = 81.089 (1)°
M_r = 318.40	V = 1602.83 (10) Å³
Triclinic, P1	Z = 4
a = 8.4317 (3) Å	Mo Kα radiation
b = 13.6142 (5) Å	µ = 0.22 mm⁻¹
c = 15.1796 (5) Å	T = 293 K
α = 71.340 (1)°	0.27 × 0.11 × 0.08 mm
β = 77.136 (1)°

Data collection top

Bruker APEXII CCD diffractometer	7319 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5632 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.940	R_int = 0.030
27476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.34 e Å⁻³
7319 reflections	Δρ_min = −0.39 e Å⁻³
415 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.98322 (6)	0.29377 (4)	0.73537 (4)	0.04718 (16)
O1	1.1132 (2)	0.28964 (14)	0.65701 (12)	0.0646 (5)
O2	0.9185 (2)	0.20011 (12)	0.79683 (13)	0.0621 (4)
O3	0.2213 (2)	0.51502 (15)	0.64850 (14)	0.0716 (5)
N1	1.0577 (2)	0.34788 (15)	0.79690 (13)	0.0490 (4)
H1N	1.105 (3)	0.4029 (13)	0.7617 (15)	0.059*
N2	0.4537 (2)	0.59093 (14)	0.57736 (14)	0.0516 (5)
H2N	0.488 (3)	0.6506 (12)	0.5403 (15)	0.062*
C1	0.9606 (3)	0.36318 (18)	0.88249 (15)	0.0479 (5)
C2	0.9398 (4)	0.2785 (2)	0.96293 (18)	0.0641 (6)
H2	0.9835	0.2122	0.9603	0.077*
C3	0.8541 (4)	0.2932 (2)	1.04648 (19)	0.0732 (8)
H3	0.8399	0.2361	1.1003	0.088*
C4	0.7889 (3)	0.3900 (2)	1.05273 (18)	0.0638 (6)
C5	0.8081 (3)	0.4762 (2)	0.97240 (19)	0.0595 (6)
C6	0.8955 (3)	0.46140 (19)	0.88680 (17)	0.0540 (5)
H6	0.9097	0.5181	0.8326	0.065*
C7	0.6971 (5)	0.4053 (3)	1.1468 (2)	0.0939 (10)
H7A	0.6751	0.3387	1.1917	0.141*
H7B	0.5959	0.4470	1.1376	0.141*
H7C	0.7625	0.4397	1.1700	0.141*
C8	0.7413 (4)	0.5840 (2)	0.9746 (2)	0.0844 (9)
H8A	0.6241	0.5881	0.9881	0.127*
H8B	0.7773	0.6328	0.9143	0.127*
H8C	0.7796	0.6003	1.0228	0.127*
C9	0.8222 (2)	0.37923 (16)	0.69024 (14)	0.0417 (4)
C10	0.8574 (3)	0.47298 (17)	0.62245 (17)	0.0524 (5)
H10	0.9649	0.4899	0.6015	0.063*
C11	0.7335 (3)	0.54057 (17)	0.58647 (17)	0.0522 (5)
H11	0.7574	0.6033	0.5407	0.063*
C12	0.5724 (2)	0.51646 (16)	0.61760 (15)	0.0433 (4)
C13	0.5385 (3)	0.42172 (19)	0.68438 (18)	0.0591 (6)
H13	0.4314	0.4040	0.7048	0.071*
C14	0.6637 (3)	0.35388 (18)	0.72046 (17)	0.0546 (6)
H14	0.6407	0.2905	0.7656	0.065*
C15	0.2910 (2)	0.58790 (17)	0.59298 (15)	0.0462 (5)
C16	0.2010 (3)	0.6818 (2)	0.53545 (18)	0.0591 (6)
H16A	0.1901	0.6702	0.4780	0.089*
H16B	0.2607	0.7415	0.5204	0.089*
H16C	0.0945	0.6939	0.5712	0.089*
S2	0.43431 (5)	0.11151 (4)	0.58705 (3)	0.03881 (14)
O4	0.42248 (18)	0.20348 (12)	0.50888 (10)	0.0522 (4)
O5	0.57822 (16)	0.04038 (12)	0.58419 (10)	0.0478 (3)
O6	−0.0669 (2)	−0.28130 (14)	0.73484 (17)	0.0821 (6)
N3	0.4199 (2)	0.15276 (13)	0.67873 (12)	0.0430 (4)
H3N	0.3329 (19)	0.1964 (15)	0.6800 (16)	0.052*
N4	−0.1488 (2)	−0.11535 (14)	0.65969 (13)	0.0449 (4)
H4N	−0.2356 (19)	−0.0768 (16)	0.6428 (16)	0.054*
C17	0.4346 (2)	0.07454 (16)	0.76766 (14)	0.0419 (4)
C18	0.5893 (3)	0.03908 (17)	0.78749 (14)	0.0467 (5)
H18	0.6796	0.0685	0.7452	0.056*
C19	0.6119 (3)	−0.03979 (19)	0.86957 (16)	0.0563 (6)
C20	0.4745 (4)	−0.08221 (18)	0.93320 (16)	0.0610 (6)
C21	0.3204 (4)	−0.0419 (2)	0.91310 (17)	0.0626 (6)
H21	0.2288	−0.0678	0.9566	0.075*
C22	0.2991 (3)	0.03525 (19)	0.83092 (16)	0.0540 (5)
H22	0.1948	0.0603	0.8185	0.065*
C23	0.7826 (4)	−0.0759 (3)	0.8881 (2)	0.0831 (10)
H23A	0.7900	−0.0700	0.9484	0.125*
H23B	0.8586	−0.0334	0.8393	0.125*
H23C	0.8081	−0.1472	0.8883	0.125*
C24	0.4914 (5)	−0.1688 (2)	1.02311 (19)	0.0908 (11)
H24A	0.3848	−0.1860	1.0587	0.136*
H24B	0.5491	−0.1466	1.0602	0.136*
H24C	0.5509	−0.2290	1.0076	0.136*
C25	0.2646 (2)	0.04302 (15)	0.60532 (13)	0.0374 (4)
C26	0.1210 (2)	0.09493 (15)	0.57695 (14)	0.0401 (4)
H26	0.1155	0.1660	0.5456	0.048*
C27	−0.0130 (2)	0.04060 (15)	0.59549 (14)	0.0414 (4)
H27	−0.1093	0.0752	0.5763	0.050*
C28	−0.0064 (2)	−0.06551 (15)	0.64266 (13)	0.0375 (4)
C29	0.1378 (3)	−0.11701 (17)	0.67113 (16)	0.0481 (5)
H29	0.1436	−0.1880	0.7027	0.058*
C30	0.2719 (2)	−0.06227 (16)	0.65223 (16)	0.0479 (5)
H30	0.3684	−0.0966	0.6713	0.058*
C31	−0.1732 (3)	−0.21692 (17)	0.70512 (16)	0.0500 (5)
C32	−0.3442 (3)	−0.2432 (2)	0.7171 (2)	0.0676 (7)
H32A	−0.3471	−0.3174	0.7390	0.101*
H32B	−0.3802	−0.2160	0.6575	0.101*
H32C	−0.4150	−0.2130	0.7624	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0455 (3)	0.0374 (3)	0.0539 (3)	0.0065 (2)	−0.0116 (2)	−0.0101 (2)
O1	0.0577 (9)	0.0618 (11)	0.0668 (11)	0.0172 (8)	−0.0044 (8)	−0.0239 (9)
O2	0.0679 (10)	0.0357 (8)	0.0770 (11)	−0.0009 (7)	−0.0216 (9)	−0.0051 (8)
O3	0.0444 (8)	0.0658 (11)	0.0858 (13)	−0.0150 (8)	−0.0131 (8)	0.0089 (10)
N1	0.0439 (9)	0.0468 (10)	0.0514 (10)	−0.0044 (7)	−0.0128 (8)	−0.0049 (8)
N2	0.0404 (9)	0.0415 (10)	0.0610 (11)	−0.0075 (7)	−0.0141 (8)	0.0059 (8)
C1	0.0462 (11)	0.0495 (12)	0.0479 (11)	−0.0076 (9)	−0.0156 (9)	−0.0079 (9)
C2	0.0833 (18)	0.0505 (14)	0.0547 (14)	−0.0087 (12)	−0.0202 (12)	−0.0041 (11)
C3	0.102 (2)	0.0596 (17)	0.0513 (14)	−0.0204 (15)	−0.0161 (14)	0.0007 (12)
C4	0.0640 (15)	0.0708 (17)	0.0557 (14)	−0.0198 (12)	−0.0127 (11)	−0.0101 (12)
C5	0.0582 (13)	0.0540 (14)	0.0721 (16)	−0.0057 (11)	−0.0218 (12)	−0.0196 (12)
C6	0.0547 (12)	0.0493 (13)	0.0562 (13)	−0.0065 (10)	−0.0187 (10)	−0.0065 (10)
C7	0.104 (3)	0.111 (3)	0.0642 (18)	−0.030 (2)	0.0025 (17)	−0.0253 (18)
C8	0.101 (2)	0.0665 (19)	0.088 (2)	0.0055 (16)	−0.0203 (18)	−0.0299 (16)
C9	0.0418 (10)	0.0380 (10)	0.0428 (10)	0.0009 (8)	−0.0108 (8)	−0.0085 (8)
C10	0.0392 (10)	0.0464 (12)	0.0626 (14)	−0.0084 (9)	−0.0101 (9)	−0.0015 (10)
C11	0.0431 (11)	0.0416 (12)	0.0596 (13)	−0.0102 (9)	−0.0114 (9)	0.0061 (10)
C12	0.0384 (9)	0.0402 (11)	0.0469 (11)	−0.0039 (8)	−0.0107 (8)	−0.0047 (9)
C13	0.0392 (10)	0.0521 (13)	0.0684 (15)	−0.0094 (9)	−0.0076 (10)	0.0073 (11)
C14	0.0486 (11)	0.0432 (12)	0.0557 (13)	−0.0061 (9)	−0.0064 (10)	0.0063 (10)
C15	0.0397 (10)	0.0475 (12)	0.0509 (12)	−0.0060 (8)	−0.0108 (8)	−0.0111 (10)
C16	0.0473 (12)	0.0582 (14)	0.0693 (15)	0.0021 (10)	−0.0215 (11)	−0.0114 (12)
S2	0.0337 (2)	0.0399 (3)	0.0370 (3)	−0.00307 (18)	−0.00693 (17)	−0.0032 (2)
O4	0.0509 (8)	0.0477 (9)	0.0472 (8)	−0.0108 (6)	−0.0123 (6)	0.0059 (7)
O5	0.0347 (7)	0.0563 (9)	0.0480 (8)	0.0032 (6)	−0.0056 (6)	−0.0141 (7)
O6	0.0568 (10)	0.0438 (10)	0.1222 (17)	−0.0065 (8)	−0.0184 (10)	0.0100 (10)
N3	0.0425 (9)	0.0375 (9)	0.0483 (9)	0.0003 (7)	−0.0121 (7)	−0.0109 (7)
N4	0.0395 (8)	0.0405 (10)	0.0530 (10)	−0.0030 (7)	−0.0140 (7)	−0.0083 (8)
C17	0.0471 (10)	0.0400 (11)	0.0396 (10)	−0.0025 (8)	−0.0088 (8)	−0.0134 (8)
C18	0.0494 (11)	0.0511 (12)	0.0402 (10)	0.0029 (9)	−0.0105 (8)	−0.0165 (9)
C19	0.0755 (15)	0.0512 (13)	0.0453 (12)	0.0171 (11)	−0.0212 (11)	−0.0224 (10)
C20	0.102 (2)	0.0404 (12)	0.0401 (11)	−0.0001 (12)	−0.0145 (12)	−0.0133 (10)
C21	0.0804 (17)	0.0556 (14)	0.0489 (13)	−0.0188 (13)	−0.0002 (12)	−0.0134 (11)
C22	0.0533 (12)	0.0550 (13)	0.0534 (13)	−0.0089 (10)	−0.0069 (10)	−0.0157 (11)
C23	0.089 (2)	0.100 (2)	0.0619 (16)	0.0414 (18)	−0.0383 (15)	−0.0322 (16)
C24	0.160 (3)	0.0508 (16)	0.0530 (15)	0.0002 (18)	−0.0255 (18)	−0.0038 (13)
C25	0.0364 (9)	0.0375 (10)	0.0358 (9)	−0.0003 (7)	−0.0069 (7)	−0.0085 (8)
C26	0.0414 (9)	0.0333 (10)	0.0414 (10)	0.0004 (7)	−0.0111 (8)	−0.0048 (8)
C27	0.0369 (9)	0.0387 (10)	0.0462 (11)	0.0024 (7)	−0.0134 (8)	−0.0081 (8)
C28	0.0389 (9)	0.0382 (10)	0.0348 (9)	−0.0016 (7)	−0.0074 (7)	−0.0103 (8)
C29	0.0466 (11)	0.0351 (10)	0.0569 (12)	−0.0011 (8)	−0.0154 (9)	−0.0032 (9)
C30	0.0388 (10)	0.0400 (11)	0.0587 (13)	0.0042 (8)	−0.0162 (9)	−0.0048 (9)
C31	0.0481 (11)	0.0446 (12)	0.0527 (12)	−0.0085 (9)	−0.0062 (9)	−0.0081 (10)
C32	0.0576 (14)	0.0593 (15)	0.0813 (18)	−0.0187 (12)	−0.0171 (12)	−0.0057 (13)

Geometric parameters (Å, º) top

S1—O2	1.4219 (17)	S2—O4	1.4315 (14)
S1—O1	1.4363 (17)	S2—O5	1.4322 (14)
S1—N1	1.629 (2)	S2—N3	1.6342 (18)
S1—C9	1.755 (2)	S2—C25	1.7510 (19)
O3—C15	1.210 (3)	O6—C31	1.208 (3)
N1—C1	1.431 (3)	N3—C17	1.444 (3)
N1—H1N	0.866 (10)	N3—H3N	0.870 (10)
N2—C15	1.344 (3)	N4—C31	1.358 (3)
N2—C12	1.402 (3)	N4—C28	1.404 (2)
N2—H2N	0.876 (10)	N4—H4N	0.870 (10)
C1—C6	1.381 (3)	C17—C22	1.374 (3)
C1—C2	1.385 (3)	C17—C18	1.382 (3)
C2—C3	1.371 (4)	C18—C19	1.388 (3)
C2—H2	0.9300	C18—H18	0.9300
C3—C4	1.371 (4)	C19—C20	1.400 (4)
C3—H3	0.9300	C19—C23	1.505 (4)
C4—C5	1.394 (4)	C20—C21	1.390 (4)
C4—C7	1.525 (4)	C20—C24	1.509 (3)
C5—C6	1.402 (4)	C21—C22	1.376 (3)
C5—C8	1.497 (4)	C21—H21	0.9300
C6—H6	0.9300	C22—H22	0.9300
C7—H7A	0.9600	C23—H23A	0.9600
C7—H7B	0.9600	C23—H23B	0.9600
C7—H7C	0.9600	C23—H23C	0.9600
C8—H8A	0.9600	C24—H24A	0.9600
C8—H8B	0.9600	C24—H24B	0.9600
C8—H8C	0.9600	C24—H24C	0.9600
C9—C14	1.372 (3)	C25—C30	1.380 (3)
C9—C10	1.385 (3)	C25—C26	1.386 (3)
C10—C11	1.368 (3)	C26—C27	1.374 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.389 (3)	C27—C28	1.391 (3)
C11—H11	0.9300	C27—H27	0.9300
C12—C13	1.386 (3)	C28—C29	1.390 (3)
C13—C14	1.378 (3)	C29—C30	1.377 (3)
C13—H13	0.9300	C29—H29	0.9300
C14—H14	0.9300	C30—H30	0.9300
C15—C16	1.501 (3)	C31—C32	1.497 (3)
C16—H16A	0.9600	C32—H32A	0.9600
C16—H16B	0.9600	C32—H32B	0.9600
C16—H16C	0.9600	C32—H32C	0.9600

O2—S1—O1	119.55 (11)	O4—S2—O5	119.22 (9)
O2—S1—N1	108.66 (10)	O4—S2—N3	105.44 (10)
O1—S1—N1	104.34 (11)	O5—S2—N3	107.14 (9)
O2—S1—C9	108.30 (10)	O4—S2—C25	108.13 (9)
O1—S1—C9	107.73 (10)	O5—S2—C25	108.38 (9)
N1—S1—C9	107.70 (10)	N3—S2—C25	108.06 (9)
C1—N1—S1	119.80 (14)	C17—N3—S2	116.87 (13)
C1—N1—H1N	111.8 (17)	C17—N3—H3N	115.2 (15)
S1—N1—H1N	112.1 (17)	S2—N3—H3N	107.0 (16)
C15—N2—C12	129.42 (18)	C31—N4—C28	128.34 (17)
C15—N2—H2N	114.2 (18)	C31—N4—H4N	114.1 (16)
C12—N2—H2N	116.2 (18)	C28—N4—H4N	117.4 (16)
C6—C1—C2	120.1 (2)	C22—C17—C18	120.5 (2)
C6—C1—N1	120.9 (2)	C22—C17—N3	121.19 (19)
C2—C1—N1	118.9 (2)	C18—C17—N3	118.32 (18)
C3—C2—C1	119.4 (3)	C17—C18—C19	121.0 (2)
C3—C2—H2	120.3	C17—C18—H18	119.5
C1—C2—H2	120.3	C19—C18—H18	119.5
C4—C3—C2	121.7 (2)	C18—C19—C20	118.8 (2)
C4—C3—H3	119.2	C18—C19—C23	119.1 (2)
C2—C3—H3	119.2	C20—C19—C23	122.1 (2)
C3—C4—C5	119.7 (2)	C21—C20—C19	118.8 (2)
C3—C4—C7	120.9 (3)	C21—C20—C24	120.0 (3)
C5—C4—C7	119.3 (3)	C19—C20—C24	121.2 (3)
C4—C5—C6	118.7 (2)	C22—C21—C20	122.1 (2)
C4—C5—C8	122.4 (3)	C22—C21—H21	119.0
C6—C5—C8	118.8 (2)	C20—C21—H21	119.0
C1—C6—C5	120.4 (2)	C17—C22—C21	118.8 (2)
C1—C6—H6	119.8	C17—C22—H22	120.6
C5—C6—H6	119.8	C21—C22—H22	120.6
C4—C7—H7A	109.5	C19—C23—H23A	109.5
C4—C7—H7B	109.5	C19—C23—H23B	109.5
H7A—C7—H7B	109.5	H23A—C23—H23B	109.5
C4—C7—H7C	109.5	C19—C23—H23C	109.5
H7A—C7—H7C	109.5	H23A—C23—H23C	109.5
H7B—C7—H7C	109.5	H23B—C23—H23C	109.5
C5—C8—H8A	109.5	C20—C24—H24A	109.5
C5—C8—H8B	109.5	C20—C24—H24B	109.5
H8A—C8—H8B	109.5	H24A—C24—H24B	109.5
C5—C8—H8C	109.5	C20—C24—H24C	109.5
H8A—C8—H8C	109.5	H24A—C24—H24C	109.5
H8B—C8—H8C	109.5	H24B—C24—H24C	109.5
C14—C9—C10	120.07 (18)	C30—C25—C26	120.04 (18)
C14—C9—S1	121.03 (16)	C30—C25—S2	119.56 (14)
C10—C9—S1	118.90 (15)	C26—C25—S2	120.33 (15)
C11—C10—C9	119.73 (19)	C27—C26—C25	119.47 (18)
C11—C10—H10	120.1	C27—C26—H26	120.3
C9—C10—H10	120.1	C25—C26—H26	120.3
C10—C11—C12	120.71 (19)	C26—C27—C28	120.75 (17)
C10—C11—H11	119.6	C26—C27—H27	119.6
C12—C11—H11	119.6	C28—C27—H27	119.6
C13—C12—C11	119.18 (19)	C29—C28—C27	119.49 (18)
C13—C12—N2	124.18 (18)	C29—C28—N4	123.14 (18)
C11—C12—N2	116.63 (18)	C27—C28—N4	117.37 (16)
C14—C13—C12	119.9 (2)	C30—C29—C28	119.55 (19)
C14—C13—H13	120.1	C30—C29—H29	120.2
C12—C13—H13	120.1	C28—C29—H29	120.2
C9—C14—C13	120.4 (2)	C29—C30—C25	120.70 (18)
C9—C14—H14	119.8	C29—C30—H30	119.6
C13—C14—H14	119.8	C25—C30—H30	119.6
O3—C15—N2	123.0 (2)	O6—C31—N4	123.2 (2)
O3—C15—C16	122.0 (2)	O6—C31—C32	122.2 (2)
N2—C15—C16	114.91 (19)	N4—C31—C32	114.7 (2)
C15—C16—H16A	109.5	C31—C32—H32A	109.5
C15—C16—H16B	109.5	C31—C32—H32B	109.5
H16A—C16—H16B	109.5	H32A—C32—H32B	109.5
C15—C16—H16C	109.5	C31—C32—H32C	109.5
H16A—C16—H16C	109.5	H32A—C32—H32C	109.5
H16B—C16—H16C	109.5	H32B—C32—H32C	109.5

O2—S1—N1—C1	−50.44 (18)	O4—S2—N3—C17	−177.69 (14)
O1—S1—N1—C1	−179.04 (16)	O5—S2—N3—C17	−49.72 (16)
C9—S1—N1—C1	66.66 (18)	C25—S2—N3—C17	66.87 (16)
S1—N1—C1—C6	−107.5 (2)	S2—N3—C17—C22	−93.8 (2)
S1—N1—C1—C2	75.9 (2)	S2—N3—C17—C18	85.6 (2)
C6—C1—C2—C3	0.1 (4)	C22—C17—C18—C19	2.7 (3)
N1—C1—C2—C3	176.6 (2)	N3—C17—C18—C19	−176.69 (19)
C1—C2—C3—C4	−0.4 (4)	C17—C18—C19—C20	−0.9 (3)
C2—C3—C4—C5	0.6 (4)	C17—C18—C19—C23	180.0 (2)
C2—C3—C4—C7	−178.7 (3)	C18—C19—C20—C21	−1.7 (3)
C3—C4—C5—C6	−0.5 (4)	C23—C19—C20—C21	177.3 (2)
C7—C4—C5—C6	178.8 (3)	C18—C19—C20—C24	179.4 (2)
C3—C4—C5—C8	−179.4 (3)	C23—C19—C20—C24	−1.6 (4)
C7—C4—C5—C8	−0.2 (4)	C19—C20—C21—C22	2.8 (4)
C2—C1—C6—C5	0.0 (3)	C24—C20—C21—C22	−178.3 (2)
N1—C1—C6—C5	−176.5 (2)	C18—C17—C22—C21	−1.7 (3)
C4—C5—C6—C1	0.2 (3)	N3—C17—C22—C21	177.7 (2)
C8—C5—C6—C1	179.2 (2)	C20—C21—C22—C17	−1.1 (4)
O2—S1—C9—C14	4.5 (2)	O4—S2—C25—C30	157.72 (17)
O1—S1—C9—C14	135.1 (2)	O5—S2—C25—C30	27.17 (19)
N1—S1—C9—C14	−112.9 (2)	N3—S2—C25—C30	−88.61 (18)
O2—S1—C9—C10	−174.89 (18)	O4—S2—C25—C26	−25.36 (19)
O1—S1—C9—C10	−44.3 (2)	O5—S2—C25—C26	−155.90 (16)
N1—S1—C9—C10	67.8 (2)	N3—S2—C25—C26	88.32 (17)
C14—C9—C10—C11	0.6 (4)	C30—C25—C26—C27	−0.3 (3)
S1—C9—C10—C11	−179.98 (19)	S2—C25—C26—C27	−177.26 (15)
C9—C10—C11—C12	0.4 (4)	C25—C26—C27—C28	0.3 (3)
C10—C11—C12—C13	−1.4 (4)	C26—C27—C28—C29	−0.1 (3)
C10—C11—C12—N2	179.4 (2)	C26—C27—C28—N4	179.47 (18)
C15—N2—C12—C13	−0.1 (4)	C31—N4—C28—C29	0.6 (3)
C15—N2—C12—C11	179.1 (2)	C31—N4—C28—C27	−178.9 (2)
C11—C12—C13—C14	1.4 (4)	C27—C28—C29—C30	0.0 (3)
N2—C12—C13—C14	−179.4 (2)	N4—C28—C29—C30	−179.6 (2)
C10—C9—C14—C13	−0.6 (4)	C28—C29—C30—C25	0.0 (3)
S1—C9—C14—C13	−180.0 (2)	C26—C25—C30—C29	0.2 (3)
C12—C13—C14—C9	−0.4 (4)	S2—C25—C30—C29	177.16 (17)
C12—N2—C15—O3	0.5 (4)	C28—N4—C31—O6	−3.2 (4)
C12—N2—C15—C16	−179.0 (2)	C28—N4—C31—C32	175.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3ⁱ	0.86 (2)	2.07 (2)	2.909 (3)	164 (2)
N2—H2n···O4ⁱⁱ	0.88 (2)	2.08 (2)	2.931 (3)	163 (2)
N3—H3n···O1ⁱⁱⁱ	0.87 (2)	2.11 (2)	2.960 (3)	166 (2)
N4—H4n···O5ⁱⁱⁱ	0.87 (2)	2.18 (2)	3.036 (2)	170 (2)
C8—H8b···O6^iv	0.96	2.71	3.640 (3)	163
C6—H6···O6^iv	0.93	2.67	3.541 (3)	156
C16—H16c···O6^v	0.96	2.65	3.477 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O₃S
M_r	318.40
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.4317 (3), 13.6142 (5), 15.1796 (5)
α, β, γ (°)	71.340 (1), 77.136 (1), 81.089 (1)
V (Å³)	1602.83 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.27 × 0.11 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.817, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	27476, 7319, 5632
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.152, 1.06
No. of reflections	7319
No. of parameters	415
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), DIAMOND (Brandenburg, 2006) and Qmol (Gans & Shalloway, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3ⁱ	0.86 (2)	2.07 (2)	2.909 (3)	164 (2)
N2—H2n···O4ⁱⁱ	0.88 (2)	2.08 (2)	2.931 (3)	162.6 (19)
N3—H3n···O1ⁱⁱⁱ	0.870 (19)	2.107 (19)	2.960 (3)	166 (2)
N4—H4n···O5ⁱⁱⁱ	0.869 (19)	2.18 (2)	3.036 (2)	169.5 (19)
C8—H8b···O6^iv	0.96	2.71	3.640 (3)	163
C6—H6···O6^iv	0.93	2.67	3.541 (3)	156
C16—H16c···O6^v	0.96	2.65	3.477 (3)	145

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

Footnotes

‡Additional correspondence author, e-mail: iuklodhi@yahoo.com.

Acknowledgements

We are grateful to Mr Munawar Hussain, Engineering Cell GC University, Lahore, for providing support services to the Materials Chemistry Laboratory.

References

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