4-Methyl-N-{2-[(E)-3-oxo-3-phenyl-prop-1-en-1-yl]phen-yl}benzene-sulfonamide.

In the title compound, C22H19NO3S, the terminal phenyl and methyl-phenyl rings are twisted by 37.35 (12) and 49.08 (13)°, respectively, to the central benzene ring. In the crystal, mol-ecules are linked by classical N-H⋯O hydrogen bonds and weak C-H⋯O hydrogen bonds into a three-dimensional supra-molecular network.

Related literature

For applications of sulfonamides in the fields of chemistry, biology and pharmacology, see: Chohan et al. (2010 ▶); El-Sayed et al. (2011 ▶); Seri et al. (2000 ▶); Suparan et al. (2000 ▶). For related structures, see: Murugavel et al. (2012 ▶); Zhang et al. (2010 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C22H19NO3S

M = 377.44

Monoclinic,

a = 8.9356 (7) Å

b = 10.8873 (8) Å

c = 19.3122 (14) Å

β = 99.472 (2)°

V = 1853.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.20 mm−1

T = 200 K

0.19 × 0.12 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.964, T max = 0.988

13392 measured reflections

4589 independent reflections

2366 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.154

S = 1.01

4589 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814015311/xu5798sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015311/xu5798Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015311/xu5798Isup3.cml

CCDC reference: 1010977

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H19NO3S	F(000) = 792
Mr = 377.44	Dx = 1.353 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2689 reflections
a = 8.9356 (7) Å	θ = 2.4–26.1°
b = 10.8873 (8) Å	µ = 0.20 mm−1
c = 19.3122 (14) Å	T = 200 K
β = 99.472 (2)°	Rod, colorless
V = 1853.2 (2) Å3	0.19 × 0.12 × 0.06 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	4589 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
phi and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
Tmin = 0.964, Tmax = 0.988	k = −14→13
13392 measured reflections	l = −25→24

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0583P)2] where P = (Fo2 + 2Fc2)/3
4589 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.

	x	y	z	Uiso*/Ueq
C1	1.1405 (3)	0.4390 (2)	0.37034 (13)	0.0321 (6)
C2	1.1969 (3)	0.5180 (3)	0.32288 (13)	0.0340 (6)
C3	1.2509 (3)	0.6334 (3)	0.34430 (14)	0.0407 (7)
H3	1.2877	0.6861	0.3117	0.049*
C4	1.2520 (3)	0.6731 (3)	0.41228 (15)	0.0459 (8)
H4	1.2912	0.7518	0.4267	0.055*
C5	1.1952 (3)	0.5965 (3)	0.45938 (15)	0.0439 (8)
H5	1.1947	0.6233	0.5062	0.053*
C6	1.1398 (3)	0.4822 (3)	0.43849 (13)	0.0372 (7)
H6	1.1001	0.4314	0.4711	0.045*
C7	1.0964 (3)	0.3133 (2)	0.35017 (13)	0.0336 (6)
H7	1.1236	0.2853	0.3073	0.040*
C8	1.0229 (3)	0.2331 (2)	0.38424 (13)	0.0335 (6)
H8	0.9856	0.2581	0.4253	0.040*
C9	0.9987 (3)	0.1067 (2)	0.35913 (14)	0.0326 (6)
O1	1.0479 (2)	0.07285 (18)	0.30617 (10)	0.0461 (5)
C10	0.9149 (3)	0.0178 (2)	0.39676 (13)	0.0300 (6)
C11	0.8184 (3)	0.0538 (3)	0.44267 (13)	0.0355 (7)
H11	0.8081	0.1386	0.4526	0.043*
C12	0.7373 (3)	−0.0321 (3)	0.47403 (14)	0.0426 (7)
H12	0.6711	−0.0066	0.5050	0.051*
C13	0.7536 (4)	−0.1553 (3)	0.45992 (14)	0.0470 (8)
H13	0.6968	−0.2146	0.4807	0.056*
C14	0.8511 (4)	−0.1927 (3)	0.41609 (15)	0.0493 (8)
H14	0.8632	−0.2778	0.4076	0.059*
C15	0.9315 (3)	−0.1073 (3)	0.38437 (14)	0.0400 (7)
H15	0.9986	−0.1337	0.3540	0.048*
N1	1.2050 (2)	0.4787 (2)	0.25294 (10)	0.0350 (6)
H1	1.2927	0.4543	0.2427	0.042*
S1	1.05508 (8)	0.47777 (7)	0.19146 (4)	0.0388 (2)
O2	1.1089 (2)	0.43544 (17)	0.13014 (9)	0.0465 (5)
O3	0.9384 (2)	0.41316 (19)	0.21857 (10)	0.0520 (6)
C16	0.9960 (3)	0.6311 (3)	0.17777 (13)	0.0359 (7)
C17	0.8957 (3)	0.6821 (3)	0.21770 (14)	0.0464 (8)
H17	0.8601	0.6346	0.2529	0.056*
C18	0.8480 (3)	0.8018 (3)	0.20592 (16)	0.0533 (9)
H18	0.7802	0.8365	0.2336	0.064*
C19	0.8975 (3)	0.8729 (3)	0.15412 (16)	0.0455 (8)
C20	0.9965 (3)	0.8202 (3)	0.11462 (15)	0.0423 (7)
H20	1.0310	0.8672	0.0789	0.051*
C21	1.0464 (3)	0.7003 (3)	0.12619 (14)	0.0360 (7)
H21	1.1150	0.6658	0.0988	0.043*
C22	0.8426 (4)	1.0035 (3)	0.14254 (18)	0.0638 (10)
H22A	0.8766	1.0368	0.1006	0.096*
H22B	0.8840	1.0535	0.1834	0.096*
H22C	0.7315	1.0051	0.1361	0.096*

	U11	U22	U33	U12	U13	U23
C1	0.0322 (15)	0.0345 (16)	0.0305 (14)	0.0012 (12)	0.0077 (12)	0.0040 (12)
C2	0.0333 (16)	0.0384 (17)	0.0312 (14)	0.0015 (13)	0.0079 (12)	0.0065 (13)
C3	0.0464 (18)	0.0390 (18)	0.0379 (16)	−0.0060 (14)	0.0108 (14)	0.0105 (14)
C4	0.054 (2)	0.0364 (18)	0.0481 (18)	−0.0060 (15)	0.0094 (15)	0.0004 (15)
C5	0.054 (2)	0.0407 (18)	0.0376 (16)	−0.0011 (15)	0.0102 (14)	−0.0026 (14)
C6	0.0447 (18)	0.0358 (16)	0.0336 (15)	−0.0023 (14)	0.0144 (13)	0.0054 (13)
C7	0.0361 (16)	0.0382 (17)	0.0275 (14)	0.0048 (13)	0.0078 (12)	0.0029 (12)
C8	0.0359 (16)	0.0367 (16)	0.0296 (14)	0.0006 (12)	0.0103 (12)	0.0025 (12)
C9	0.0310 (15)	0.0357 (16)	0.0321 (14)	0.0045 (12)	0.0081 (12)	−0.0012 (13)
O1	0.0521 (13)	0.0464 (13)	0.0453 (12)	0.0009 (10)	0.0245 (10)	−0.0084 (10)
C10	0.0316 (15)	0.0308 (15)	0.0268 (13)	−0.0004 (12)	0.0024 (11)	0.0014 (12)
C11	0.0415 (17)	0.0350 (17)	0.0310 (14)	−0.0024 (13)	0.0085 (13)	0.0031 (12)
C12	0.0448 (18)	0.050 (2)	0.0348 (15)	−0.0050 (15)	0.0106 (13)	0.0025 (15)
C13	0.061 (2)	0.044 (2)	0.0353 (16)	−0.0149 (16)	0.0037 (15)	0.0074 (15)
C14	0.069 (2)	0.0337 (18)	0.0433 (18)	−0.0035 (16)	0.0036 (16)	0.0000 (14)
C15	0.0487 (19)	0.0356 (17)	0.0356 (15)	0.0025 (14)	0.0065 (14)	−0.0013 (13)
N1	0.0308 (13)	0.0458 (14)	0.0300 (11)	0.0047 (11)	0.0092 (10)	0.0054 (11)
S1	0.0408 (4)	0.0434 (5)	0.0324 (4)	−0.0028 (3)	0.0070 (3)	0.0039 (3)
O2	0.0667 (15)	0.0398 (12)	0.0338 (10)	0.0078 (10)	0.0112 (10)	−0.0038 (9)
O3	0.0428 (13)	0.0633 (15)	0.0489 (12)	−0.0159 (11)	0.0043 (10)	0.0154 (11)
C16	0.0346 (16)	0.0450 (18)	0.0279 (14)	−0.0004 (13)	0.0047 (12)	−0.0019 (13)
C17	0.0419 (18)	0.069 (2)	0.0302 (15)	0.0050 (16)	0.0111 (13)	−0.0014 (15)
C18	0.0402 (19)	0.072 (3)	0.0471 (19)	0.0184 (17)	0.0051 (15)	−0.0167 (18)
C19	0.0378 (18)	0.050 (2)	0.0449 (18)	0.0093 (15)	−0.0058 (14)	−0.0130 (16)
C20	0.0419 (18)	0.0417 (18)	0.0423 (17)	0.0013 (14)	0.0039 (14)	0.0037 (14)
C21	0.0328 (16)	0.0405 (17)	0.0355 (15)	0.0025 (13)	0.0078 (12)	−0.0018 (13)
C22	0.062 (2)	0.056 (2)	0.068 (2)	0.0236 (18)	−0.0084 (18)	−0.0161 (19)

C1—C6	1.399 (3)	C13—C14	1.373 (4)
C1—C2	1.409 (3)	C13—H13	0.9500
C1—C7	1.459 (4)	C14—C15	1.379 (4)
C2—C3	1.384 (4)	C14—H14	0.9500
C2—N1	1.430 (3)	C15—H15	0.9500
C3—C4	1.380 (4)	N1—S1	1.638 (2)
C3—H3	0.9500	N1—H1	0.8800
C4—C5	1.390 (4)	S1—O2	1.4259 (19)
C4—H4	0.9500	S1—O3	1.427 (2)
C5—C6	1.375 (4)	S1—C16	1.757 (3)
C5—H5	0.9500	C16—C21	1.382 (4)
C6—H6	0.9500	C16—C17	1.391 (4)
C7—C8	1.330 (3)	C17—C18	1.379 (4)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.463 (4)	C18—C19	1.393 (4)
C8—H8	0.9500	C18—H18	0.9500
C9—O1	1.234 (3)	C19—C20	1.384 (4)
C9—C10	1.484 (4)	C19—C22	1.509 (4)
C10—C11	1.391 (4)	C20—C21	1.386 (4)
C10—C15	1.395 (4)	C20—H20	0.9500
C11—C12	1.383 (4)	C21—H21	0.9500
C11—H11	0.9500	C22—H22A	0.9800
C12—C13	1.381 (4)	C22—H22B	0.9800
C12—H12	0.9500	C22—H22C	0.9800
C6—C1—C2	117.7 (2)	C13—C14—C15	120.3 (3)
C6—C1—C7	121.6 (2)	C13—C14—H14	119.9
C2—C1—C7	120.6 (2)	C15—C14—H14	119.9
C3—C2—C1	120.3 (2)	C14—C15—C10	120.3 (3)
C3—C2—N1	119.0 (2)	C14—C15—H15	119.9
C1—C2—N1	120.7 (2)	C10—C15—H15	119.9
C4—C3—C2	121.1 (3)	C2—N1—S1	121.59 (18)
C4—C3—H3	119.5	C2—N1—H1	119.2
C2—C3—H3	119.5	S1—N1—H1	119.2
C3—C4—C5	119.2 (3)	O2—S1—O3	120.81 (13)
C3—C4—H4	120.4	O2—S1—N1	104.87 (12)
C5—C4—H4	120.4	O3—S1—N1	107.27 (12)
C6—C5—C4	120.2 (3)	O2—S1—C16	108.42 (12)
C6—C5—H5	119.9	O3—S1—C16	107.69 (13)
C4—C5—H5	119.9	N1—S1—C16	107.05 (12)
C5—C6—C1	121.5 (3)	C21—C16—C17	119.9 (3)
C5—C6—H6	119.2	C21—C16—S1	120.1 (2)
C1—C6—H6	119.2	C17—C16—S1	120.1 (2)
C8—C7—C1	128.1 (2)	C18—C17—C16	119.7 (3)
C8—C7—H7	115.9	C18—C17—H17	120.1
C1—C7—H7	115.9	C16—C17—H17	120.1
C7—C8—C9	120.8 (2)	C17—C18—C19	121.2 (3)
C7—C8—H8	119.6	C17—C18—H18	119.4
C9—C8—H8	119.6	C19—C18—H18	119.4
O1—C9—C8	120.1 (2)	C20—C19—C18	118.2 (3)
O1—C9—C10	119.2 (2)	C20—C19—C22	122.0 (3)
C8—C9—C10	120.6 (2)	C18—C19—C22	119.7 (3)
C11—C10—C15	118.6 (2)	C19—C20—C21	121.3 (3)
C11—C10—C9	123.0 (2)	C19—C20—H20	119.4
C15—C10—C9	118.4 (2)	C21—C20—H20	119.4
C12—C11—C10	120.9 (3)	C16—C21—C20	119.7 (3)
C12—C11—H11	119.6	C16—C21—H21	120.1
C10—C11—H11	119.6	C20—C21—H21	120.1
C13—C12—C11	119.4 (3)	C19—C22—H22A	109.5
C13—C12—H12	120.3	C19—C22—H22B	109.5
C11—C12—H12	120.3	H22A—C22—H22B	109.5
C14—C13—C12	120.5 (3)	C19—C22—H22C	109.5
C14—C13—H13	119.8	H22A—C22—H22C	109.5
C12—C13—H13	119.8	H22B—C22—H22C	109.5
C6—C1—C2—C3	0.8 (4)	C13—C14—C15—C10	0.2 (4)
C7—C1—C2—C3	−174.3 (3)	C11—C10—C15—C14	1.3 (4)
C6—C1—C2—N1	178.2 (2)	C9—C10—C15—C14	−177.4 (3)
C7—C1—C2—N1	3.1 (4)	C3—C2—N1—S1	−103.3 (3)
C1—C2—C3—C4	0.6 (4)	C1—C2—N1—S1	79.2 (3)
N1—C2—C3—C4	−176.9 (3)	C2—N1—S1—O2	179.0 (2)
C2—C3—C4—C5	−1.2 (4)	C2—N1—S1—O3	−51.4 (2)
C3—C4—C5—C6	0.5 (5)	C2—N1—S1—C16	64.0 (2)
C4—C5—C6—C1	0.8 (5)	O2—S1—C16—C21	−19.3 (3)
C2—C1—C6—C5	−1.5 (4)	O3—S1—C16—C21	−151.6 (2)
C7—C1—C6—C5	173.6 (3)	N1—S1—C16—C21	93.3 (2)
C6—C1—C7—C8	15.1 (4)	O2—S1—C16—C17	159.2 (2)
C2—C1—C7—C8	−170.0 (3)	O3—S1—C16—C17	26.9 (3)
C1—C7—C8—C9	−174.9 (2)	N1—S1—C16—C17	−88.2 (2)
C7—C8—C9—O1	0.7 (4)	C21—C16—C17—C18	−0.5 (4)
C7—C8—C9—C10	−179.2 (2)	S1—C16—C17—C18	−179.0 (2)
O1—C9—C10—C11	−160.3 (2)	C16—C17—C18—C19	0.6 (5)
C8—C9—C10—C11	19.6 (4)	C17—C18—C19—C20	−0.2 (4)
O1—C9—C10—C15	18.4 (4)	C17—C18—C19—C22	179.8 (3)
C8—C9—C10—C15	−161.7 (2)	C18—C19—C20—C21	−0.3 (4)
C15—C10—C11—C12	−1.7 (4)	C22—C19—C20—C21	179.7 (3)
C9—C10—C11—C12	177.0 (2)	C17—C16—C21—C20	0.0 (4)
C10—C11—C12—C13	0.5 (4)	S1—C16—C21—C20	178.5 (2)
C11—C12—C13—C14	1.1 (4)	C19—C20—C21—C16	0.4 (4)
C12—C13—C14—C15	−1.5 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.88	2.24	2.839 (3)	125
C4—H4···O2i	0.95	2.51	3.272 (4)	137
C18—H18···O3ii	0.95	2.44	3.373 (3)	167
C22—H22B···O1iii	0.98	2.58	3.466 (4)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.88	2.24	2.839 (3)	125
C4—H4⋯O2i	0.95	2.51	3.272 (4)	137
C18—H18⋯O3ii	0.95	2.44	3.373 (3)	167
C22—H22B⋯O1iii	0.98	2.58	3.466 (4)	150

Symmetry codes: (i) ; (ii) ; (iii) .