N-Benzyl-4-methyl-N-(4-methyl-phen-yl)benzene-sulfonamide.

In the title mol-ecule, C(21)H(21)NO(2)S, 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, mol-ecules are linked by inter-molecular C-H⋯O hydrogen bonds along the [010] direction. In addition, a weak C-H⋯π (arene) inter-action 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 = 351.46

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.133

S = 1.03

4574 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028522/si2365sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811028522/si2365Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21NO2S	F(000) = 744
Mr = 351.46	Dx = 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

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

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(Fo2) + (0.0588P)2 + 0.2963P] where P = (Fo2 + 2Fc2)/3
4574 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .