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

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

doi:10.1107/S1600536810045708

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3152

https://doi.org/10.1107/S1600536810045708

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

Peter John,^a Saima Khizar,^a Islam Ullah Khan,^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 4 November 2010; accepted 7 November 2010; online 13 November 2010)

When viewed down the central S⋯N axis of the title compound, C₂₀H₂₆N₂O₃S, it is apparent that the molecule adopts a gauche conformation with all O atoms lying to one side of the central benzene ring; the carbonyl O atom is directed away from the central ring and the N-bound ethyl groups lie to one side of the molecule. Supramolecular helical chains aligned along the b axis and sustained by C—H⋯O contacts feature in the crystal packing. These are consolidated in the three-dimensional structure by C—H⋯π interactions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ). For related structures, see: Sharif et al. (2010 ); Khan et al. (2010 ).

Experimental

Crystal data

C₂₀H₂₆N₂O₃S
M_r = 374.51
Monoclinic, P 2₁ /c
a = 8.0882 (2) Å
b = 11.5978 (3) Å
c = 21.2717 (5) Å
β = 97.194 (1)°
V = 1979.69 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.28 × 0.14 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.692, T_max = 0.895
16612 measured reflections
4079 independent reflections
3325 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.122
S = 1.01
4079 reflections
240 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.54	3.455 (2)	170
C10—H10a⋯Cg1ⁱⁱ	0.96	2.93	3.728 (2)	142
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1.

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 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810045708/hg2743sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045708/hg2743Isup2.hkl

checkCIF report

Comment top

In connection with on-going structural studies of sulfonamides (Sharif et al., 2010; Khan et al., 2010), of interest owing to their biological properties (Korolkovas, 1988; Mandell & Sande, 1992), the title compound, (I), was investigated.

With reference to the central benzene ring in (I), Fig. 1, the S1 [deviation = -0.068 (1) Å] and N2 [-0.005 (1) Å] atoms are co-planar. Both sulfonamide-O atoms lie to the same side of the plane as does the carbonyl-O atom, which is directed away from the ring, with the remaining substituents lying to the other side. When viewed down the S1···N2 vector, both N-bound ethyl groups lie to the same side of the molecule. Similarly, when viewed down the S1···N2 vector, the molecule has a gauche conformation.

In the crystal packing, molecules are connected into a helical supramolecular chain along the b axis via C—H···O contacts occurring between benzene-H and sulfonamide-O atoms, Table 1 and Fig. 2. The chains are consolidated in the crystal packing by C—H···π interactions, Table 1 and Fig. 3.

Related literature top

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Sharif et al. (2010); Khan et al. (2010).

Experimental top

A mixture of N-{4-[(3,4-dimethylphenyl)sulfamoyl]phenyl}acetamide 100 mg (0.314 mmol) and sodium hydride 85 mg (0.78 mmol) in N,N-dimethylformamide (10 ml) was stirred at room temperature for 30 min. followed by addition of ethyl iodide 199 µl (0.785 mmol). Stirring was continued for a further 3 h and the contents were poured over crushed ice. The precipitate that formed was isolated, washed and crystallized from methanol solution by slow evaporation; M.pt. 472 K.

Structure description top

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For related structures, see: Sharif et al. (2010); Khan et al. (2010).

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) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.
	Fig. 2. A view of the helical supramolecular chain along the b axis in (I). The C—H···O contacts sustaining this chain are shown as orange dashed lines.
	Fig. 3. View in projection down the b axis of the unit-cell contents for (I). The C—H···O and C—H···π contacts are shown as orange and purple dashed lines, respectively.

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

Crystal data top

C₂₀H₂₆N₂O₃S	F(000) = 800
M_r = 374.51	D_x = 1.257 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7015 reflections
a = 8.0882 (2) Å	θ = 3.0–27.8°
b = 11.5978 (3) Å	µ = 0.19 mm⁻¹
c = 21.2717 (5) Å	T = 293 K
β = 97.194 (1)°	Block, colourless
V = 1979.69 (8) Å³	0.28 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4079 independent reflections
Radiation source: fine-focus sealed tube	3325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 26.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.692, T_max = 0.895	k = −14→11
16612 measured reflections	l = −26→26

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0713P)² + 0.4585P] where P = (F_o² + 2F_c²)/3
4079 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₂₆N₂O₃S	V = 1979.69 (8) Å³
M_r = 374.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0882 (2) Å	µ = 0.19 mm⁻¹
b = 11.5978 (3) Å	T = 293 K
c = 21.2717 (5) Å	0.28 × 0.14 × 0.08 mm
β = 97.194 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4079 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3325 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.895	R_int = 0.029
16612 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
4079 reflections	Δρ_min = −0.26 e Å⁻³
240 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	1.12740 (5)	0.72075 (4)	0.249229 (18)	0.03937 (14)
O1	1.07590 (16)	0.82013 (10)	0.28110 (6)	0.0509 (3)
O2	1.25922 (15)	0.73062 (12)	0.21059 (6)	0.0536 (3)
O3	0.27644 (17)	0.53664 (14)	0.04014 (7)	0.0694 (4)
N1	1.18549 (16)	0.62329 (11)	0.30379 (6)	0.0376 (3)
N2	0.52634 (17)	0.52003 (13)	0.09842 (7)	0.0475 (4)
C1	1.2726 (2)	0.52088 (16)	0.28259 (8)	0.0476 (4)
H1A	1.1913	0.4620	0.2683	0.057*
H1B	1.3306	0.5419	0.2470	0.057*
C2	1.3933 (3)	0.4738 (2)	0.33407 (12)	0.0874 (8)
H2A	1.4686	0.5337	0.3505	0.131*
H2B	1.4551	0.4123	0.3178	0.131*
H2C	1.3347	0.4450	0.3673	0.131*
C3	1.06969 (18)	0.60395 (13)	0.34975 (7)	0.0339 (3)
C4	1.06258 (19)	0.68223 (14)	0.39837 (7)	0.0389 (3)
H4	1.1336	0.7456	0.4015	0.047*
C5	0.9517 (2)	0.66828 (15)	0.44270 (7)	0.0422 (4)
C6	0.8482 (2)	0.57149 (16)	0.43848 (8)	0.0442 (4)
C7	0.8584 (2)	0.49348 (15)	0.39000 (8)	0.0488 (4)
H7	0.7902	0.4286	0.3873	0.059*
C8	0.9669 (2)	0.50905 (14)	0.34545 (8)	0.0440 (4)
H8	0.9704	0.4559	0.3129	0.053*
C9	0.9443 (3)	0.7571 (2)	0.49396 (9)	0.0631 (5)
H9A	1.0265	0.8155	0.4903	0.095*
H9B	0.9660	0.7207	0.5347	0.095*
H9C	0.8355	0.7916	0.4896	0.095*
C10	0.7272 (3)	0.5500 (2)	0.48570 (10)	0.0673 (6)
H10A	0.7868	0.5468	0.5276	0.101*
H10B	0.6708	0.4781	0.4761	0.101*
H10C	0.6471	0.6114	0.4834	0.101*
C11	0.95077 (19)	0.66426 (14)	0.20256 (7)	0.0377 (3)
C12	0.7959 (2)	0.68032 (16)	0.22264 (8)	0.0454 (4)
H12	0.7859	0.7231	0.2589	0.055*
C13	0.6567 (2)	0.63238 (16)	0.18843 (8)	0.0477 (4)
H13	0.5526	0.6421	0.2020	0.057*
C14	0.67146 (19)	0.56991 (14)	0.13400 (8)	0.0410 (4)
C15	0.8263 (2)	0.55379 (15)	0.11401 (8)	0.0435 (4)
H15	0.8359	0.5115	0.0775	0.052*
C16	0.96666 (19)	0.60077 (15)	0.14841 (7)	0.0422 (4)
H16	1.0710	0.5898	0.1353	0.051*
C17	0.5128 (2)	0.39364 (17)	0.09782 (10)	0.0592 (5)
H17A	0.6237	0.3608	0.1001	0.071*
H17B	0.4510	0.3697	0.0579	0.071*
C18	0.4287 (4)	0.3465 (2)	0.15098 (12)	0.0839 (7)
H18A	0.4904	0.3684	0.1907	0.126*
H18B	0.4241	0.2639	0.1480	0.126*
H18C	0.3177	0.3768	0.1484	0.126*
C19	0.4017 (2)	0.58325 (17)	0.06710 (8)	0.0485 (4)
C20	0.4223 (3)	0.71197 (17)	0.06548 (9)	0.0564 (5)
H20A	0.3588	0.7423	0.0280	0.085*
H20B	0.5379	0.7305	0.0652	0.085*
H20C	0.3834	0.7454	0.1022	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0372 (2)	0.0426 (3)	0.0387 (2)	−0.00274 (16)	0.00612 (16)	0.00737 (16)
O1	0.0619 (8)	0.0375 (6)	0.0527 (7)	0.0004 (6)	0.0049 (6)	0.0032 (5)
O2	0.0408 (6)	0.0717 (9)	0.0498 (7)	−0.0092 (6)	0.0114 (5)	0.0127 (6)
O3	0.0518 (8)	0.0747 (10)	0.0762 (9)	−0.0066 (7)	−0.0140 (7)	−0.0079 (8)
N1	0.0376 (7)	0.0394 (7)	0.0365 (6)	0.0037 (5)	0.0071 (5)	0.0036 (5)
N2	0.0397 (7)	0.0436 (8)	0.0584 (9)	0.0001 (6)	0.0028 (6)	−0.0044 (7)
C1	0.0457 (9)	0.0479 (10)	0.0514 (9)	0.0085 (8)	0.0142 (8)	0.0004 (8)
C2	0.0891 (17)	0.0869 (18)	0.0821 (16)	0.0473 (14)	−0.0048 (13)	0.0050 (14)
C3	0.0342 (7)	0.0354 (8)	0.0323 (7)	−0.0006 (6)	0.0043 (6)	0.0021 (6)
C4	0.0388 (8)	0.0380 (8)	0.0392 (8)	−0.0052 (7)	0.0018 (6)	−0.0018 (6)
C5	0.0413 (8)	0.0477 (9)	0.0367 (8)	0.0048 (7)	0.0021 (7)	−0.0035 (7)
C6	0.0393 (8)	0.0528 (10)	0.0416 (8)	0.0021 (7)	0.0086 (7)	0.0060 (7)
C7	0.0494 (10)	0.0434 (9)	0.0544 (10)	−0.0142 (8)	0.0095 (8)	0.0013 (8)
C8	0.0530 (10)	0.0379 (9)	0.0416 (8)	−0.0073 (7)	0.0082 (7)	−0.0068 (7)
C9	0.0642 (12)	0.0715 (13)	0.0544 (11)	0.0027 (10)	0.0107 (10)	−0.0209 (10)
C10	0.0596 (12)	0.0847 (16)	0.0622 (11)	−0.0031 (11)	0.0254 (10)	0.0073 (11)
C11	0.0340 (8)	0.0451 (9)	0.0343 (7)	0.0036 (7)	0.0061 (6)	0.0065 (7)
C12	0.0404 (9)	0.0559 (10)	0.0414 (8)	0.0047 (8)	0.0104 (7)	−0.0042 (8)
C13	0.0339 (8)	0.0619 (11)	0.0490 (9)	0.0029 (8)	0.0122 (7)	−0.0034 (8)
C14	0.0351 (8)	0.0438 (9)	0.0439 (8)	0.0014 (7)	0.0038 (7)	0.0027 (7)
C15	0.0428 (9)	0.0504 (10)	0.0380 (8)	0.0055 (7)	0.0080 (7)	−0.0016 (7)
C16	0.0344 (8)	0.0541 (10)	0.0396 (8)	0.0058 (7)	0.0110 (6)	0.0046 (7)
C17	0.0519 (11)	0.0488 (11)	0.0774 (13)	0.0015 (8)	0.0105 (9)	−0.0121 (10)
C18	0.112 (2)	0.0563 (13)	0.0870 (16)	−0.0039 (13)	0.0250 (15)	0.0065 (12)
C19	0.0429 (9)	0.0578 (11)	0.0445 (9)	0.0004 (8)	0.0043 (7)	−0.0042 (8)
C20	0.0589 (11)	0.0538 (11)	0.0549 (10)	0.0054 (9)	0.0002 (9)	0.0030 (9)

Geometric parameters (Å, º) top

S1—O1	1.4256 (13)	C9—H9A	0.9600
S1—O2	1.4301 (12)	C9—H9B	0.9600
S1—N1	1.6458 (13)	C9—H9C	0.9600
S1—C11	1.7608 (16)	C10—H10A	0.9600
O3—C19	1.226 (2)	C10—H10B	0.9600
N1—C3	1.4534 (18)	C10—H10C	0.9600
N1—C1	1.480 (2)	C11—C12	1.386 (2)
N2—C19	1.352 (2)	C11—C16	1.386 (2)
N2—C14	1.436 (2)	C12—C13	1.379 (2)
N2—C17	1.470 (2)	C12—H12	0.9300
C1—C2	1.478 (3)	C13—C14	1.384 (2)
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—C15	1.385 (2)
C2—H2A	0.9600	C15—C16	1.383 (2)
C2—H2B	0.9600	C15—H15	0.9300
C2—H2C	0.9600	C16—H16	0.9300
C3—C8	1.376 (2)	C17—C18	1.494 (3)
C3—C4	1.383 (2)	C17—H17A	0.9700
C4—C5	1.390 (2)	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.396 (2)	C18—H18B	0.9600
C5—C9	1.506 (2)	C18—H18C	0.9600
C6—C7	1.382 (2)	C19—C20	1.503 (3)
C6—C10	1.508 (2)	C20—H20A	0.9600
C7—C8	1.382 (2)	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600
C8—H8	0.9300

O1—S1—O2	119.46 (8)	H9B—C9—H9C	109.5
O1—S1—N1	107.13 (7)	C6—C10—H10A	109.5
O2—S1—N1	107.03 (7)	C6—C10—H10B	109.5
O1—S1—C11	107.71 (8)	H10A—C10—H10B	109.5
O2—S1—C11	108.45 (7)	C6—C10—H10C	109.5
N1—S1—C11	106.37 (7)	H10A—C10—H10C	109.5
C3—N1—C1	116.91 (12)	H10B—C10—H10C	109.5
C3—N1—S1	115.41 (10)	C12—C11—C16	120.59 (15)
C1—N1—S1	116.17 (10)	C12—C11—S1	118.50 (12)
C19—N2—C14	123.41 (15)	C16—C11—S1	120.86 (12)
C19—N2—C17	119.09 (15)	C13—C12—C11	119.53 (15)
C14—N2—C17	117.48 (15)	C13—C12—H12	120.2
C2—C1—N1	111.47 (16)	C11—C12—H12	120.2
C2—C1—H1A	109.3	C12—C13—C14	120.17 (15)
N1—C1—H1A	109.3	C12—C13—H13	119.9
C2—C1—H1B	109.3	C14—C13—H13	119.9
N1—C1—H1B	109.3	C15—C14—C13	120.26 (15)
H1A—C1—H1B	108.0	C15—C14—N2	119.64 (15)
C1—C2—H2A	109.5	C13—C14—N2	120.09 (14)
C1—C2—H2B	109.5	C16—C15—C14	119.88 (15)
H2A—C2—H2B	109.5	C16—C15—H15	120.1
C1—C2—H2C	109.5	C14—C15—H15	120.1
H2A—C2—H2C	109.5	C15—C16—C11	119.56 (14)
H2B—C2—H2C	109.5	C15—C16—H16	120.2
C8—C3—C4	119.57 (14)	C11—C16—H16	120.2
C8—C3—N1	120.92 (13)	N2—C17—C18	113.53 (17)
C4—C3—N1	119.50 (13)	N2—C17—H17A	108.9
C3—C4—C5	121.45 (14)	C18—C17—H17A	108.9
C3—C4—H4	119.3	N2—C17—H17B	108.9
C5—C4—H4	119.3	C18—C17—H17B	108.9
C4—C5—C6	118.84 (15)	H17A—C17—H17B	107.7
C4—C5—C9	119.93 (16)	C17—C18—H18A	109.5
C6—C5—C9	121.23 (16)	C17—C18—H18B	109.5
C7—C6—C5	118.90 (15)	H18A—C18—H18B	109.5
C7—C6—C10	119.53 (17)	C17—C18—H18C	109.5
C5—C6—C10	121.57 (16)	H18A—C18—H18C	109.5
C8—C7—C6	121.90 (15)	H18B—C18—H18C	109.5
C8—C7—H7	119.0	O3—C19—N2	120.85 (18)
C6—C7—H7	119.0	O3—C19—C20	120.99 (18)
C3—C8—C7	119.31 (15)	N2—C19—C20	118.16 (16)
C3—C8—H8	120.3	C19—C20—H20A	109.5
C7—C8—H8	120.3	C19—C20—H20B	109.5
C5—C9—H9A	109.5	H20A—C20—H20B	109.5
C5—C9—H9B	109.5	C19—C20—H20C	109.5
H9A—C9—H9B	109.5	H20A—C20—H20C	109.5
C5—C9—H9C	109.5	H20B—C20—H20C	109.5
H9A—C9—H9C	109.5

O1—S1—N1—C3	48.43 (12)	O2—S1—C11—C12	−159.96 (14)
O2—S1—N1—C3	177.67 (10)	N1—S1—C11—C12	85.22 (14)
C11—S1—N1—C3	−66.55 (12)	O1—S1—C11—C16	153.43 (13)
O1—S1—N1—C1	−169.22 (12)	O2—S1—C11—C16	22.83 (16)
O2—S1—N1—C1	−39.98 (14)	N1—S1—C11—C16	−91.99 (14)
C11—S1—N1—C1	75.80 (13)	C16—C11—C12—C13	0.2 (3)
C3—N1—C1—C2	−68.9 (2)	S1—C11—C12—C13	−177.06 (13)
S1—N1—C1—C2	149.37 (17)	C11—C12—C13—C14	−0.8 (3)
C1—N1—C3—C8	−39.7 (2)	C12—C13—C14—C15	0.9 (3)
S1—N1—C3—C8	102.32 (16)	C12—C13—C14—N2	180.00 (16)
C1—N1—C3—C4	140.40 (15)	C19—N2—C14—C15	−114.12 (19)
S1—N1—C3—C4	−77.54 (16)	C17—N2—C14—C15	67.4 (2)
C8—C3—C4—C5	−1.0 (2)	C19—N2—C14—C13	66.8 (2)
N1—C3—C4—C5	178.83 (13)	C17—N2—C14—C13	−111.71 (19)
C3—C4—C5—C6	1.4 (2)	C13—C14—C15—C16	−0.3 (3)
C3—C4—C5—C9	−178.33 (16)	N2—C14—C15—C16	−179.42 (15)
C4—C5—C6—C7	−0.7 (2)	C14—C15—C16—C11	−0.4 (3)
C9—C5—C6—C7	179.10 (17)	C12—C11—C16—C15	0.4 (2)
C4—C5—C6—C10	178.90 (16)	S1—C11—C16—C15	177.57 (13)
C9—C5—C6—C10	−1.3 (3)	C19—N2—C17—C18	−89.7 (2)
C5—C6—C7—C8	−0.5 (3)	C14—N2—C17—C18	88.9 (2)
C10—C6—C7—C8	179.92 (17)	C14—N2—C19—O3	−176.18 (16)
C4—C3—C8—C7	−0.2 (2)	C17—N2—C19—O3	2.3 (3)
N1—C3—C8—C7	179.99 (15)	C14—N2—C19—C20	4.7 (2)
C6—C7—C8—C3	0.9 (3)	C17—N2—C19—C20	−176.83 (17)
O1—S1—C11—C12	−29.36 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.54	3.455 (2)	170
C10—H10a···Cg1ⁱⁱ	0.96	2.93	3.728 (2)	142

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₆N₂O₃S
M_r	374.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0882 (2), 11.5978 (3), 21.2717 (5)
β (°)	97.194 (1)
V (Å³)	1979.69 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.28 × 0.14 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.692, 0.895
No. of measured, independent and observed [I > 2σ(I)] reflections	16612, 4079, 3325
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.122, 1.01
No. of reflections	4079
No. of parameters	240
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.54	3.455 (2)	170
C10—H10a···Cg1ⁱⁱ	0.96	2.93	3.728 (2)	142

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

Footnotes

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

Acknowledgements

The authors are grateful to the Higher Education Commission of Pakistan for financial support to purchase the diffractometer.

References

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