N-Benzyl-N-(2-meth-oxy-phen-yl)benzene-sulfonamide.

In the title mol-ecule, C(20)H(19)NO(3)S, the dihedral angle between the phenyl rings is 48.93 (18)°, and they make dihedral angles of 38.37 (17) and 86.50 (19)° with the benzene ring. A weak intra-molecular C-H⋯O inter-action might stabilize the mol-ecular conformation. In the crystal, weak π-π stacking inter-actions between the benzene rings [centroid-centroid distance = 3.774 (2) Å] may help to establish the packing.

Related literature

For background on the biological activity of sulfonamide derivatives, see: Ozbek et al. (2007 ▶); Parari et al. (2008 ▶). For the structures of some sulfonamide derivatives, see, for example: Asiri et al. (2009 ▶); Aziz-ur-Rehman et al. (2010 ▶).

Experimental

Crystal data

C20H19NO3S

M = 353.43

Monoclinic,

a = 10.0368 (3) Å

b = 9.0176 (3) Å

c = 20.4228 (7) Å

β = 103.424 (2)°

V = 1797.92 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.25 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

16779 measured reflections

4438 independent reflections

2560 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.202

S = 1.04

4438 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.20 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 datablocks global, I. DOI: 10.1107/S1600536810043369/hb5703sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043369/hb5703Isup2.hkl

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

C20H19NO3S	F(000) = 744
Mr = 353.43	Dx = 1.306 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3872 reflections
a = 10.0368 (3) Å	θ = 2.5–21.8°
b = 9.0176 (3) Å	µ = 0.20 mm−1
c = 20.4228 (7) Å	T = 296 K
β = 103.424 (2)°	Block, light violet
V = 1797.92 (10) Å3	0.25 × 0.13 × 0.09 mm
Z = 4

Bruker APEXII CCD diffractometer	2560 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.037
graphite	θmax = 28.4°, θmin = 3.3°
φ and ω scans	h = −13→13
16779 measured reflections	k = −12→9
4438 independent reflections	l = −27→25

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.202	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.1008P)2 + 0.2694P] where P = (Fo2 + 2Fc2)/3
4438 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.20 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	0.65180 (7)	0.44517 (7)	0.66852 (3)	0.0726 (2)
O1	0.5815 (3)	0.5433 (2)	0.70356 (11)	0.1098 (9)
O2	0.7233 (2)	0.5054 (2)	0.62194 (9)	0.0897 (7)
O3	0.6440 (2)	0.0515 (2)	0.65783 (15)	0.1138 (9)
N1	0.53841 (18)	0.3280 (2)	0.62738 (9)	0.0636 (6)
C1	0.7345 (3)	0.2992 (4)	0.78758 (13)	0.0981 (13)
C2	0.8243 (4)	0.2106 (5)	0.83247 (15)	0.1226 (18)
C3	0.9455 (4)	0.1657 (4)	0.81816 (18)	0.1143 (14)
C4	0.9776 (3)	0.2066 (4)	0.76011 (17)	0.0971 (11)
C5	0.8896 (3)	0.2937 (3)	0.71487 (14)	0.0798 (10)
C6	0.7687 (2)	0.3409 (3)	0.72877 (12)	0.0691 (8)
C7	0.5817 (2)	0.2371 (3)	0.57779 (13)	0.0704 (9)
C8	0.5683 (3)	0.2888 (3)	0.51265 (13)	0.0787 (10)
C9	0.6088 (4)	0.2160 (5)	0.4631 (2)	0.1162 (17)
C10	0.6693 (4)	0.0790 (7)	0.4816 (3)	0.146 (3)
C11	0.6818 (3)	0.0179 (4)	0.5442 (3)	0.1157 (16)
C12	0.6375 (3)	0.1012 (3)	0.5923 (2)	0.0933 (12)
C13	0.7184 (5)	−0.0828 (4)	0.6767 (4)	0.197 (3)
C14	0.4294 (3)	0.2778 (4)	0.65914 (14)	0.0898 (12)
C15	0.2919 (2)	0.2704 (2)	0.61222 (11)	0.0596 (7)
C16	0.2544 (3)	0.3576 (3)	0.55669 (14)	0.0846 (10)
C17	0.1251 (4)	0.3467 (6)	0.51567 (19)	0.1411 (19)
C18	0.0338 (4)	0.2513 (8)	0.5304 (2)	0.163 (3)
C19	0.0679 (4)	0.1656 (6)	0.5857 (2)	0.1312 (18)
C20	0.1961 (3)	0.1745 (3)	0.62612 (16)	0.0913 (12)
H1	0.65250	0.33020	0.79690	0.1180*
H2	0.80280	0.18120	0.87240	0.1470*
H3	1.00590	0.10670	0.84880	0.1370*
H4	1.05960	0.17550	0.75090	0.1170*
H5	0.91140	0.32100	0.67470	0.0960*
H8	0.52800	0.38130	0.50240	0.0940*
H9	0.59720	0.25430	0.41990	0.1390*
H10	0.70320	0.02610	0.44990	0.1750*
H11	0.71880	−0.07620	0.55410	0.1390*
H13A	0.66840	−0.16440	0.65250	0.2960*
H13B	0.73040	−0.09860	0.72420	0.2960*
H13C	0.80640	−0.07570	0.66590	0.2960*
H14A	0.42480	0.34480	0.69570	0.1080*
H14B	0.45290	0.18020	0.67840	0.1080*
H16	0.31660	0.42500	0.54640	0.1020*
H17	0.10080	0.40590	0.47750	0.1690*
H18	−0.05330	0.24440	0.50230	0.1960*
H19	0.00400	0.10060	0.59630	0.1570*
H20	0.21930	0.11420	0.66400	0.1090*

	U11	U22	U33	U12	U13	U23
S1	0.0824 (4)	0.0642 (4)	0.0690 (4)	0.0044 (3)	0.0130 (3)	−0.0103 (3)
O1	0.1269 (17)	0.0989 (15)	0.0955 (13)	0.0447 (12)	0.0092 (12)	−0.0309 (12)
O2	0.1001 (13)	0.0788 (12)	0.0880 (12)	−0.0271 (10)	0.0174 (11)	0.0054 (10)
O3	0.0902 (15)	0.0710 (13)	0.164 (2)	−0.0034 (10)	−0.0035 (15)	0.0263 (14)
N1	0.0586 (10)	0.0718 (12)	0.0640 (11)	0.0007 (9)	0.0216 (8)	−0.0025 (9)
C1	0.097 (2)	0.134 (3)	0.0643 (15)	0.0410 (19)	0.0209 (14)	−0.0038 (17)
C2	0.138 (3)	0.166 (4)	0.0667 (18)	0.056 (3)	0.0298 (19)	0.014 (2)
C3	0.105 (2)	0.141 (3)	0.085 (2)	0.048 (2)	−0.0021 (18)	−0.011 (2)
C4	0.0692 (17)	0.115 (2)	0.103 (2)	0.0134 (16)	0.0119 (16)	−0.021 (2)
C5	0.0717 (16)	0.0852 (18)	0.0841 (17)	−0.0051 (14)	0.0212 (14)	−0.0140 (15)
C6	0.0692 (14)	0.0724 (15)	0.0631 (13)	0.0051 (11)	0.0098 (11)	−0.0146 (11)
C7	0.0557 (12)	0.0657 (15)	0.0943 (18)	−0.0151 (11)	0.0269 (12)	−0.0128 (13)
C8	0.0878 (17)	0.0890 (18)	0.0696 (15)	−0.0247 (14)	0.0391 (13)	−0.0114 (14)
C9	0.110 (3)	0.142 (3)	0.116 (3)	−0.047 (2)	0.066 (2)	−0.053 (3)
C10	0.094 (3)	0.162 (5)	0.203 (5)	−0.054 (3)	0.078 (3)	−0.108 (4)
C11	0.0668 (17)	0.076 (2)	0.206 (4)	−0.0154 (15)	0.035 (2)	−0.056 (3)
C12	0.0590 (14)	0.0666 (17)	0.152 (3)	−0.0187 (13)	0.0200 (17)	−0.018 (2)
C13	0.128 (3)	0.080 (3)	0.363 (9)	0.005 (2)	0.014 (4)	0.065 (4)
C14	0.0643 (14)	0.134 (3)	0.0764 (16)	0.0061 (15)	0.0273 (13)	0.0290 (17)
C15	0.0608 (12)	0.0625 (13)	0.0620 (12)	0.0023 (10)	0.0277 (10)	−0.0041 (10)
C16	0.0710 (15)	0.096 (2)	0.0869 (18)	−0.0005 (14)	0.0187 (13)	0.0136 (16)
C17	0.081 (2)	0.231 (5)	0.101 (2)	−0.001 (3)	0.0002 (19)	0.045 (3)
C18	0.074 (2)	0.298 (8)	0.110 (3)	−0.043 (3)	0.006 (2)	−0.013 (4)
C19	0.095 (2)	0.179 (4)	0.133 (3)	−0.061 (3)	0.054 (2)	−0.037 (3)
C20	0.094 (2)	0.096 (2)	0.100 (2)	−0.0161 (16)	0.0556 (17)	−0.0029 (17)

S1—O1	1.424 (3)	C16—C17	1.375 (5)
S1—O2	1.426 (2)	C17—C18	1.341 (7)
S1—N1	1.6351 (19)	C18—C19	1.346 (7)
S1—C6	1.762 (2)	C19—C20	1.360 (5)
O3—C12	1.398 (5)	C1—H1	0.9300
O3—C13	1.428 (5)	C2—H2	0.9300
N1—C7	1.446 (3)	C3—H3	0.9300
N1—C14	1.467 (4)	C4—H4	0.9300
C1—C2	1.381 (5)	C5—H5	0.9300
C1—C6	1.376 (4)	C8—H8	0.9300
C2—C3	1.376 (6)	C9—H9	0.9300
C3—C4	1.350 (5)	C10—H10	0.9300
C4—C5	1.368 (4)	C11—H11	0.9300
C5—C6	1.376 (4)	C13—H13A	0.9600
C7—C8	1.386 (4)	C13—H13B	0.9600
C7—C12	1.351 (4)	C13—H13C	0.9600
C8—C9	1.346 (5)	C14—H14A	0.9700
C9—C10	1.390 (7)	C14—H14B	0.9700
C10—C11	1.371 (8)	C16—H16	0.9300
C11—C12	1.389 (6)	C17—H17	0.9300
C14—C15	1.488 (4)	C18—H18	0.9300
C15—C16	1.359 (3)	C19—H19	0.9300
C15—C20	1.371 (4)	C20—H20	0.9300
O1—S1—O2	118.92 (12)	C6—C1—H1	121.00
O1—S1—N1	107.03 (13)	C1—C2—H2	120.00
O1—S1—C6	107.94 (12)	C3—C2—H2	120.00
O2—S1—N1	107.55 (10)	C2—C3—H3	120.00
O2—S1—C6	108.22 (11)	C4—C3—H3	120.00
N1—S1—C6	106.57 (11)	C3—C4—H4	120.00
C12—O3—C13	115.8 (4)	C5—C4—H4	120.00
S1—N1—C7	116.09 (15)	C4—C5—H5	120.00
S1—N1—C14	118.28 (17)	C6—C5—H5	120.00
C7—N1—C14	120.7 (2)	C7—C8—H8	117.00
C2—C1—C6	118.8 (3)	C9—C8—H8	117.00
C1—C2—C3	120.1 (3)	C8—C9—H9	123.00
C2—C3—C4	120.6 (3)	C10—C9—H9	123.00
C3—C4—C5	120.1 (3)	C9—C10—H10	118.00
C4—C5—C6	120.0 (3)	C11—C10—H10	118.00
S1—C6—C1	119.66 (19)	C10—C11—H11	121.00
S1—C6—C5	119.81 (19)	C12—C11—H11	121.00
C1—C6—C5	120.4 (2)	O3—C13—H13A	109.00
N1—C7—C8	120.2 (2)	O3—C13—H13B	109.00
N1—C7—C12	122.5 (3)	O3—C13—H13C	109.00
C8—C7—C12	117.3 (3)	H13A—C13—H13B	110.00
C7—C8—C9	125.4 (3)	H13A—C13—H13C	109.00
C8—C9—C10	114.7 (4)	H13B—C13—H13C	110.00
C9—C10—C11	123.4 (5)	N1—C14—H14A	109.00
C10—C11—C12	117.9 (4)	N1—C14—H14B	109.00
O3—C12—C7	115.2 (3)	C15—C14—H14A	109.00
O3—C12—C11	123.5 (3)	C15—C14—H14B	109.00
C7—C12—C11	121.3 (4)	H14A—C14—H14B	108.00
N1—C14—C15	113.9 (2)	C15—C16—H16	120.00
C14—C15—C16	123.2 (2)	C17—C16—H16	120.00
C14—C15—C20	119.0 (2)	C16—C17—H17	120.00
C16—C15—C20	117.8 (2)	C18—C17—H17	120.00
C15—C16—C17	120.4 (3)	C17—C18—H18	120.00
C16—C17—C18	120.4 (4)	C19—C18—H18	120.00
C17—C18—C19	120.2 (4)	C18—C19—H19	120.00
C18—C19—C20	119.7 (4)	C20—C19—H19	120.00
C15—C20—C19	121.4 (3)	C15—C20—H20	119.00
C2—C1—H1	121.00	C19—C20—H20	119.00
O1—S1—N1—C7	168.04 (17)	C3—C4—C5—C6	0.6 (5)
O2—S1—N1—C7	39.19 (19)	C4—C5—C6—S1	−176.8 (2)
C6—S1—N1—C7	−76.67 (18)	C4—C5—C6—C1	−1.0 (4)
O1—S1—N1—C14	−36.5 (2)	C12—C7—C8—C9	−1.4 (5)
O2—S1—N1—C14	−165.4 (2)	N1—C7—C12—O3	3.1 (4)
C6—S1—N1—C14	78.8 (2)	N1—C7—C12—C11	−178.2 (3)
N1—S1—C6—C1	−79.3 (3)	N1—C7—C8—C9	177.9 (3)
O1—S1—C6—C1	35.3 (3)	C8—C7—C12—O3	−177.6 (2)
O2—S1—C6—C1	165.3 (2)	C8—C7—C12—C11	1.1 (4)
N1—S1—C6—C5	96.5 (2)	C7—C8—C9—C10	−0.6 (6)
O1—S1—C6—C5	−148.8 (2)	C8—C9—C10—C11	3.0 (7)
O2—S1—C6—C5	−18.9 (3)	C9—C10—C11—C12	−3.3 (7)
C13—O3—C12—C11	9.1 (5)	C10—C11—C12—O3	179.7 (3)
C13—O3—C12—C7	−172.2 (3)	C10—C11—C12—C7	1.1 (5)
C7—N1—C14—C15	−67.7 (3)	N1—C14—C15—C16	−27.6 (4)
C14—N1—C7—C12	−62.3 (3)	N1—C14—C15—C20	154.3 (2)
S1—N1—C7—C12	92.5 (3)	C14—C15—C16—C17	−179.2 (3)
C14—N1—C7—C8	118.5 (3)	C20—C15—C16—C17	−1.2 (4)
S1—N1—C14—C15	138.1 (2)	C14—C15—C20—C19	178.6 (3)
S1—N1—C7—C8	−86.7 (2)	C16—C15—C20—C19	0.4 (4)
C2—C1—C6—S1	176.5 (3)	C15—C16—C17—C18	0.9 (6)
C2—C1—C6—C5	0.6 (5)	C16—C17—C18—C19	0.2 (8)
C6—C1—C2—C3	0.1 (6)	C17—C18—C19—C20	−1.0 (8)
C1—C2—C3—C4	−0.5 (6)	C18—C19—C20—C15	0.7 (6)
C2—C3—C4—C5	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O3	0.97	2.36	2.972 (4)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O3	0.97	2.36	2.972 (4)	120