N-Benzyl-4-methyl-N-(4-methyl­phen­yl)benzene­sulfonamide

Faryal, K.; Farrukh, M.A.; Qureshi, F.A.; Ahmad, S.; Adnan, A.; Akkurt, M.

doi:10.1107/S1600536811028522

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2100

doi:10.1107/S1600536811028522

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N-Benzyl-4-methyl-N-(4-methylphenyl)benzenesulfonamide

Komal Faryal,^a Muhammad Akhyar Farrukh,^a ‡ Fahim Ashraf Qureshi,^a Saba Ahmad,^a Ahmad Adnan ^a and Mehmet Akkurt ^b ^*

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 14 July 2011; accepted 15 July 2011; online 23 July 2011)

In the title molecule, C₂₁H₂₁NO₂S, the phenyl ring makes the dihedral angles of 74.13 (11) and 80.16 (11)° with the two benzene rings, which are inclined at an angle of 43.73 (10)° with respect to each other. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds along the [010] direction. In addition, a weak C—H⋯π (arene) interaction is observed.

Related literature

For background and the biological and chemical importance of sulfonamides, see: Hung & Hwang (2007 ); Burkhart & Burkhart (2009 ); Griffiths-Jones et al. (2006 ). For related structures, see: Ahmad et al. (2011a ,b ).

Experimental

Crystal data

C₂₁H₂₁NO₂S
M_r = 351.46
Monoclinic, P 2₁ /c
a = 9.7089 (6) Å
b = 11.5973 (5) Å
c = 16.7661 (9) Å
β = 97.691 (2)°
V = 1870.83 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.85 × 0.13 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer
11456 measured reflections
4574 independent reflections
2964 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.133
S = 1.03
4574 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O2ⁱ	0.93	2.59	3.496 (2)	166
C14—H14B⋯Cg2ⁱⁱ	0.96	2.98	3.540 (2)	118
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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028522/si2365sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028522/si2365Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028522/si2365Isup3.cml

checkCIF report

Comment top

Sulfonamides are compounds of both biological and chemical importance which are widely used in veterinary medicine (Hung & Hwang, 2007). They were developed in the 1930's and were the first effective antimicrobial agent for systemic administration (Burkhart & Burkhart, 2009). Sulfonamides represent an important chemotype for medicinal chemistry. They are not only important in drugs with representation of the largest class of antimicrobial agents but also they form the starting point for many classes of drugs including diuretics, antidiabetic drugs, and antihypertensives (Griffiths-Jones et al., 2006). They have bacteriostatic properties and are effective systematic drug used for humans (Ahmad et al., 2011a).

As a contribution to a structural study of sulfonamide derivatives (Ahmad et al., 2011a, Ahmad et al., 2011b), we report here the title compound, N-benzyl-4-methyl-N-(4-methylphenyl)benzenesulfonamide, (I).

As shown in Fig. 1, the S1 atom in (I) has a distorted tetrahedral geometry. The largest deviation is in the angle O1—S1—O2 [120.09 (9)°]. The phenyl ring (C16–C21) forms the dihedral angles of 74.13 (11) and 80.16 (11)° with the two benzene rings (C1–C6 and C8–C13). The dihedral angle between the two benzene rings is 43.73 (10)°.

In the crystal structure of (I), neighbouring molecules are connected by intermolecular C–H···O hydrogen bonds (Table 1, Fig. 2) along the b axis. The structure is further stabilized by C–H···π (arene) interactions (Table 1).

Related literature top

For background and the biological and chemical importance of sulfonamides, see: Hung & Hwang (2007); Burkhart & Burkhart (2009); Griffiths-Jones et al. (2006). For related structures, see: Ahmad et al. (2011a,b).

Experimental top

5 mM of p-toluidine was dissolved in 20 ml of distilled water then 5 mM of benzyl chloride was added. The reaction mixture was stirred properly and 5 mM of p-toluenesulfonyl chloride was added. The mixture was stirred for about 1–2 h and the pH was maintained 8–10 using 3% solution of Na₂CO₃. The reaction was monitored by TLC. The product obtained was filtered and the precipitate was washed with distilled water, dried and recrystallized using methanol.

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 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecule of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. Crystal packing of (I) and the intermolecular C—H···O interactions between the molecules viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

N-Benzyl-4-methyl-N-(4-methylphenyl)benzenesulfonamide top

Crystal data top

C₂₁H₂₁NO₂S	F(000) = 744
M_r = 351.46	D_x = 1.248 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3286 reflections
a = 9.7089 (6) Å	θ = 2.5–24.9°
b = 11.5973 (5) Å	µ = 0.19 mm⁻¹
c = 16.7661 (9) Å	T = 296 K
β = 97.691 (2)°	Prism, colourless
V = 1870.83 (17) Å³	0.85 × 0.13 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2964 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 28.3°, θ_min = 2.9°
ϕ and ω scans	h = −11→12
11456 measured reflections	k = −14→9
4574 independent reflections	l = −22→22

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0588P)² + 0.2963P] where P = (F_o² + 2F_c²)/3
4574 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₁H₂₁NO₂S	V = 1870.83 (17) Å³
M_r = 351.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7089 (6) Å	µ = 0.19 mm⁻¹
b = 11.5973 (5) Å	T = 296 K
c = 16.7661 (9) Å	0.85 × 0.13 × 0.13 mm
β = 97.691 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2964 reflections with I > 2σ(I)
11456 measured reflections	R_int = 0.023
4574 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
4574 reflections	Δρ_min = −0.24 e Å⁻³
228 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.89447 (6)	0.62917 (4)	0.14182 (3)	0.0546 (2)
O1	0.98019 (17)	0.65672 (12)	0.08157 (8)	0.0726 (5)
O2	0.81350 (16)	0.71695 (11)	0.17304 (8)	0.0683 (5)
N1	0.99846 (16)	0.57740 (12)	0.21798 (9)	0.0519 (5)
C1	0.7808 (2)	0.51881 (16)	0.10313 (10)	0.0527 (6)
C2	0.6492 (2)	0.50937 (19)	0.12566 (13)	0.0687 (8)
C3	0.5614 (2)	0.4236 (2)	0.09295 (14)	0.0780 (9)
C4	0.6002 (3)	0.34620 (19)	0.03843 (13)	0.0733 (8)
C5	0.7323 (3)	0.3563 (2)	0.01758 (14)	0.0784 (9)
C6	0.8220 (2)	0.44090 (19)	0.04879 (12)	0.0697 (8)
C7	0.5014 (3)	0.2542 (2)	0.00171 (18)	0.1051 (12)
C8	0.94537 (19)	0.56548 (14)	0.29392 (10)	0.0477 (5)
C9	0.8894 (2)	0.46311 (15)	0.31576 (11)	0.0574 (6)
C10	0.8403 (2)	0.45394 (17)	0.38906 (12)	0.0610 (7)
C11	0.8447 (2)	0.54630 (18)	0.44177 (10)	0.0559 (6)
C12	0.9021 (2)	0.64773 (17)	0.41902 (11)	0.0610 (7)
C13	0.9533 (2)	0.65776 (16)	0.34641 (11)	0.0572 (6)
C14	0.7875 (2)	0.5353 (2)	0.52065 (12)	0.0747 (8)
C15	1.1138 (2)	0.50075 (16)	0.20267 (12)	0.0583 (7)
C16	1.2518 (2)	0.54652 (15)	0.23897 (11)	0.0501 (6)
C17	1.2928 (3)	0.65709 (18)	0.22271 (14)	0.0722 (8)
C18	1.4232 (3)	0.6972 (2)	0.25410 (17)	0.0871 (10)
C19	1.5127 (3)	0.6278 (3)	0.30155 (16)	0.0857 (10)
C20	1.4722 (3)	0.5193 (3)	0.31869 (16)	0.0839 (10)
C21	1.3433 (2)	0.47864 (18)	0.28786 (13)	0.0656 (8)
H2	0.62040	0.56070	0.16270	0.0820*
H3	0.47300	0.41800	0.10830	0.0940*
H5	0.76130	0.30410	−0.01880	0.0940*
H6	0.91030	0.44580	0.03340	0.0840*
H7A	0.52650	0.18140	0.02680	0.1580*
H7B	0.50670	0.24900	−0.05490	0.1580*
H7C	0.40830	0.27380	0.00990	0.1580*
H9	0.88460	0.40010	0.28120	0.0690*
H10	0.80330	0.38410	0.40340	0.0730*
H12	0.90650	0.71090	0.45340	0.0730*
H13	0.99310	0.72670	0.33280	0.0690*
H14A	0.82210	0.59730	0.55570	0.1120*
H14B	0.81600	0.46300	0.54530	0.1120*
H14C	0.68780	0.53870	0.51120	0.1120*
H15A	1.11300	0.49220	0.14510	0.0700*
H15B	1.09980	0.42510	0.22490	0.0700*
H17	1.23230	0.70510	0.19040	0.0870*
H18	1.44980	0.77180	0.24270	0.1040*
H19	1.60070	0.65430	0.32210	0.1030*
H20	1.53270	0.47210	0.35170	0.1010*
H21	1.31760	0.40420	0.30020	0.0790*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0717 (3)	0.0488 (3)	0.0443 (2)	0.0064 (2)	0.0110 (2)	0.0024 (2)
O1	0.0941 (11)	0.0714 (9)	0.0561 (8)	−0.0079 (8)	0.0235 (8)	0.0082 (7)
O2	0.0904 (11)	0.0539 (8)	0.0591 (8)	0.0215 (7)	0.0047 (8)	0.0001 (6)
N1	0.0557 (9)	0.0520 (8)	0.0482 (8)	0.0090 (7)	0.0078 (7)	−0.0024 (7)
C1	0.0624 (12)	0.0568 (10)	0.0387 (8)	0.0080 (9)	0.0062 (8)	0.0028 (8)
C2	0.0720 (15)	0.0785 (14)	0.0575 (12)	0.0078 (12)	0.0162 (11)	−0.0034 (10)
C3	0.0619 (14)	0.0962 (17)	0.0762 (15)	−0.0046 (13)	0.0099 (12)	0.0096 (14)
C4	0.0850 (17)	0.0733 (14)	0.0577 (12)	−0.0063 (13)	−0.0050 (12)	0.0072 (11)
C5	0.0938 (18)	0.0759 (15)	0.0663 (14)	−0.0070 (13)	0.0140 (13)	−0.0197 (11)
C6	0.0716 (14)	0.0768 (14)	0.0637 (12)	−0.0040 (12)	0.0205 (11)	−0.0152 (11)
C7	0.109 (2)	0.099 (2)	0.099 (2)	−0.0341 (17)	−0.0168 (17)	0.0030 (16)
C8	0.0517 (10)	0.0474 (9)	0.0421 (8)	0.0067 (8)	−0.0009 (8)	−0.0019 (7)
C9	0.0710 (13)	0.0470 (10)	0.0533 (10)	−0.0028 (9)	0.0047 (10)	−0.0074 (8)
C10	0.0676 (13)	0.0581 (11)	0.0573 (11)	−0.0048 (10)	0.0082 (10)	0.0045 (9)
C11	0.0520 (11)	0.0688 (12)	0.0447 (9)	0.0146 (10)	−0.0011 (8)	0.0039 (9)
C12	0.0743 (14)	0.0598 (12)	0.0472 (10)	0.0123 (10)	0.0015 (10)	−0.0097 (8)
C13	0.0732 (13)	0.0454 (10)	0.0516 (10)	0.0031 (9)	0.0032 (10)	−0.0030 (8)
C14	0.0734 (15)	0.0983 (17)	0.0530 (11)	0.0207 (13)	0.0112 (11)	0.0071 (11)
C15	0.0619 (13)	0.0487 (10)	0.0656 (12)	0.0056 (9)	0.0132 (10)	−0.0092 (9)
C16	0.0565 (11)	0.0463 (9)	0.0497 (9)	0.0024 (8)	0.0153 (9)	−0.0028 (8)
C17	0.0826 (17)	0.0550 (12)	0.0773 (14)	−0.0043 (11)	0.0041 (13)	0.0050 (10)
C18	0.093 (2)	0.0713 (15)	0.0988 (19)	−0.0289 (15)	0.0195 (17)	−0.0106 (14)
C19	0.0598 (15)	0.114 (2)	0.0833 (17)	−0.0113 (15)	0.0095 (13)	−0.0232 (16)
C20	0.0652 (16)	0.1031 (19)	0.0815 (16)	0.0104 (14)	0.0031 (13)	0.0043 (14)
C21	0.0638 (14)	0.0626 (12)	0.0725 (13)	0.0068 (11)	0.0168 (11)	0.0092 (10)

Geometric parameters (Å, º) top

S1—O1	1.4283 (16)	C18—C19	1.360 (4)
S1—O2	1.4278 (15)	C19—C20	1.360 (5)
S1—N1	1.6326 (16)	C20—C21	1.372 (4)
S1—C1	1.7565 (19)	C2—H2	0.9300
N1—C8	1.443 (2)	C3—H3	0.9300
N1—C15	1.479 (2)	C5—H5	0.9300
C1—C2	1.384 (3)	C6—H6	0.9300
C1—C6	1.380 (3)	C7—H7A	0.9600
C2—C3	1.375 (3)	C7—H7B	0.9600
C3—C4	1.369 (3)	C7—H7C	0.9600
C4—C5	1.379 (4)	C9—H9	0.9300
C4—C7	1.510 (4)	C10—H10	0.9300
C5—C6	1.369 (3)	C12—H12	0.9300
C8—C9	1.376 (2)	C13—H13	0.9300
C8—C13	1.381 (2)	C14—H14A	0.9600
C9—C10	1.381 (3)	C14—H14B	0.9600
C10—C11	1.386 (3)	C14—H14C	0.9600
C11—C12	1.377 (3)	C15—H15A	0.9700
C11—C14	1.507 (3)	C15—H15B	0.9700
C12—C13	1.380 (3)	C17—H17	0.9300
C15—C16	1.493 (3)	C18—H18	0.9300
C16—C17	1.381 (3)	C19—H19	0.9300
C16—C21	1.373 (3)	C20—H20	0.9300
C17—C18	1.385 (4)	C21—H21	0.9300

O1—S1—O2	120.09 (9)	C4—C3—H3	119.00
O1—S1—N1	106.11 (9)	C4—C5—H5	119.00
O1—S1—C1	107.37 (9)	C6—C5—H5	119.00
O2—S1—N1	106.78 (8)	C1—C6—H6	120.00
O2—S1—C1	107.78 (9)	C5—C6—H6	120.00
N1—S1—C1	108.25 (8)	C4—C7—H7A	109.00
S1—N1—C8	117.96 (12)	C4—C7—H7B	109.00
S1—N1—C15	119.26 (12)	C4—C7—H7C	109.00
C8—N1—C15	117.64 (14)	H7A—C7—H7B	110.00
S1—C1—C2	120.94 (15)	H7A—C7—H7C	110.00
S1—C1—C6	119.84 (15)	H7B—C7—H7C	109.00
C2—C1—C6	119.22 (18)	C8—C9—H9	120.00
C1—C2—C3	119.59 (19)	C10—C9—H9	120.00
C2—C3—C4	121.9 (2)	C9—C10—H10	119.00
C3—C4—C5	117.5 (2)	C11—C10—H10	119.00
C3—C4—C7	121.3 (2)	C11—C12—H12	119.00
C5—C4—C7	121.2 (2)	C13—C12—H12	119.00
C4—C5—C6	122.0 (2)	C8—C13—H13	120.00
C1—C6—C5	119.7 (2)	C12—C13—H13	120.00
N1—C8—C9	121.21 (15)	C11—C14—H14A	110.00
N1—C8—C13	119.47 (15)	C11—C14—H14B	109.00
C9—C8—C13	119.31 (16)	C11—C14—H14C	109.00
C8—C9—C10	119.95 (17)	H14A—C14—H14B	109.00
C9—C10—C11	121.56 (18)	H14A—C14—H14C	109.00
C10—C11—C12	117.56 (17)	H14B—C14—H14C	109.00
C10—C11—C14	120.72 (18)	N1—C15—H15A	109.00
C12—C11—C14	121.72 (18)	N1—C15—H15B	109.00
C11—C12—C13	121.55 (18)	C16—C15—H15A	109.00
C8—C13—C12	120.05 (17)	C16—C15—H15B	109.00
N1—C15—C16	112.00 (15)	H15A—C15—H15B	108.00
C15—C16—C17	121.09 (19)	C16—C17—H17	120.00
C15—C16—C21	120.87 (17)	C18—C17—H17	120.00
C17—C16—C21	118.0 (2)	C17—C18—H18	120.00
C16—C17—C18	120.7 (2)	C19—C18—H18	120.00
C17—C18—C19	120.2 (2)	C18—C19—H19	120.00
C18—C19—C20	119.4 (3)	C20—C19—H19	120.00
C19—C20—C21	120.9 (3)	C19—C20—H20	120.00
C16—C21—C20	120.8 (2)	C21—C20—H20	120.00
C1—C2—H2	120.00	C16—C21—H21	120.00
C3—C2—H2	120.00	C20—C21—H21	120.00
C2—C3—H3	119.00

O1—S1—N1—C8	166.82 (12)	C2—C3—C4—C5	0.6 (3)
O2—S1—N1—C8	37.62 (14)	C7—C4—C5—C6	178.4 (2)
C1—S1—N1—C8	−78.19 (14)	C3—C4—C5—C6	−0.9 (3)
O1—S1—N1—C15	−39.11 (15)	C4—C5—C6—C1	0.3 (3)
O2—S1—N1—C15	−168.32 (13)	N1—C8—C13—C12	179.59 (17)
C1—S1—N1—C15	75.88 (15)	N1—C8—C9—C10	179.53 (17)
O1—S1—C1—C2	−149.26 (16)	C13—C8—C9—C10	0.8 (3)
O2—S1—C1—C2	−18.57 (18)	C9—C8—C13—C12	−1.7 (3)
N1—S1—C1—C2	96.58 (17)	C8—C9—C10—C11	0.5 (3)
O1—S1—C1—C6	30.00 (18)	C9—C10—C11—C14	178.56 (18)
O2—S1—C1—C6	160.69 (15)	C9—C10—C11—C12	−1.0 (3)
N1—S1—C1—C6	−84.16 (17)	C10—C11—C12—C13	0.1 (3)
S1—N1—C8—C9	94.38 (18)	C14—C11—C12—C13	−179.43 (18)
C15—N1—C8—C9	−60.1 (2)	C11—C12—C13—C8	1.2 (3)
S1—N1—C15—C16	122.31 (15)	N1—C15—C16—C17	−53.5 (2)
C15—N1—C8—C13	118.60 (19)	N1—C15—C16—C21	128.29 (19)
S1—N1—C8—C13	−86.91 (19)	C15—C16—C17—C18	−177.4 (2)
C8—N1—C15—C16	−83.55 (19)	C21—C16—C17—C18	0.9 (3)
C6—C1—C2—C3	−0.7 (3)	C15—C16—C21—C20	177.5 (2)
S1—C1—C2—C3	178.54 (17)	C17—C16—C21—C20	−0.8 (3)
C2—C1—C6—C5	0.5 (3)	C16—C17—C18—C19	0.0 (4)
S1—C1—C6—C5	−178.78 (17)	C17—C18—C19—C20	−0.9 (4)
C1—C2—C3—C4	0.2 (3)	C18—C19—C20—C21	0.9 (4)
C2—C3—C4—C7	−178.6 (2)	C19—C20—C21—C16	−0.1 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2	0.93	2.60	2.938 (3)	102
C15—H15A···O1	0.97	2.46	2.894 (2)	107
C21—H21···O2ⁱ	0.93	2.59	3.496 (2)	166
C14—H14B···Cg2ⁱⁱ	0.96	2.98	3.540 (2)	118

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁NO₂S
M_r	351.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.7089 (6), 11.5973 (5), 16.7661 (9)
β (°)	97.691 (2)
V (Å³)	1870.83 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.85 × 0.13 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11456, 4574, 2964
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.133, 1.03
No. of reflections	4574
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C8–C13 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O2ⁱ	0.93	2.59	3.496 (2)	166
C14—H14B···Cg2ⁱⁱ	0.96	2.98	3.540 (2)	118

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

Footnotes

‡Additional correspondence author, e-mail: akhyar@gcu.edu.pk.

Acknowledgements

The authors are grateful to the Higher Education Commission (HEC), Pakistan, for providing funds for the single-crystal XRD facilities at GC University Lahore.

References

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