(2Z)-2-{[N-(2-Formyl-phen-yl)-4-methyl-benzene-sulfonamido]-meth-yl}-3-(4-methyl-phen-yl)prop-2-ene-nitrile.

In the title compound, C(25)H(22)N(2)O(3)S, the sulfonyl-bound benzene ring forms dihedral angles of 36.8 (2) and 81.4 (2)°, respectively, with the formyl-benzene and methyl-benzene rings. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond, which generates an S(5) ring motif. The crystal packing is stabilized by C-H⋯O hydrogen bonds, which generate C(11) chains along the b axis. The crystal packing is further stabilized by π-π inter-actions [centroid-centroid distance = 3.927 (2) Å].

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Madhanraj et al. (2012 ▶); Aziz-ur-Rehman et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H22N2O3S

M = 430.51

Orthorhombic,

a = 8.9432 (5) Å

b = 10.3004 (6) Å

c = 24.9240 (15) Å

V = 2296.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 293 K

0.25 × 0.23 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.972

12317 measured reflections

4663 independent reflections

3385 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.117

S = 1.02

4663 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1990 Friedel pairs

Flack parameter: 0.19 (9)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia (1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010628/tk5066sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010628/tk5066Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010628/tk5066Isup3.cml

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

C25H22N2O3S	F(000) = 904
Mr = 430.51	Dx = 1.245 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4690 reflections
a = 8.9432 (5) Å	θ = 2.1–26.4°
b = 10.3004 (6) Å	µ = 0.17 mm−1
c = 24.9240 (15) Å	T = 293 K
V = 2296.0 (2) Å3	Block, colourless
Z = 4	0.25 × 0.23 × 0.17 mm

Bruker APEXII CCD diffractometer	4663 independent reflections
Radiation source: fine-focus sealed tube	3385 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 26.4°, θmin = 2.1°
ω scans	h = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→9
Tmin = 0.959, Tmax = 0.972	l = −30→31
12317 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.065P)2 + 0.0718P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4663 reflections	Δρmax = 0.19 e Å−3
282 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 1990 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.19 (9)

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
O1	0.3120 (4)	0.8483 (4)	0.6292 (2)	0.228 (2)
C14	0.2953 (8)	0.3803 (7)	0.98250 (18)	0.198 (3)
H14A	0.3992	0.3571	0.9812	0.297*
H14B	0.2363	0.3039	0.9886	0.297*
H14C	0.2791	0.4411	1.0111	0.297*
S1	0.12098 (6)	0.62642 (6)	0.77099 (3)	0.0654 (2)
C16	0.1285 (2)	0.3775 (2)	0.65770 (8)	0.0549 (5)
O3	−0.03436 (17)	0.60536 (19)	0.76309 (8)	0.0833 (5)
C17	0.1732 (3)	0.2664 (2)	0.63569 (9)	0.0576 (6)
H17	0.2346	0.2163	0.6576	0.069*
O2	0.1799 (2)	0.75371 (16)	0.76813 (9)	0.0884 (6)
N1	0.20652 (19)	0.54286 (17)	0.72366 (8)	0.0561 (5)
C24	0.0421 (3)	0.4723 (3)	0.62915 (11)	0.0734 (7)
C2	0.4743 (3)	0.4998 (2)	0.73721 (10)	0.0672 (7)
H2	0.4505	0.4303	0.7594	0.081*
C1	0.3624 (2)	0.5716 (2)	0.71374 (8)	0.0504 (5)
C3	0.6222 (3)	0.5311 (3)	0.72779 (13)	0.0800 (8)
H3	0.6976	0.4824	0.7438	0.096*
C6	0.3987 (3)	0.6749 (2)	0.68055 (10)	0.0597 (6)
C18	0.1425 (3)	0.2092 (2)	0.58296 (9)	0.0595 (6)
C4	0.6589 (3)	0.6330 (3)	0.69519 (11)	0.0744 (7)
H4	0.7587	0.6534	0.6889	0.089*
C15	0.1553 (3)	0.4077 (2)	0.71546 (9)	0.0628 (6)
H15A	0.0636	0.3940	0.7354	0.075*
H15B	0.2301	0.3486	0.7295	0.075*
C23	0.2278 (3)	0.1035 (3)	0.56710 (12)	0.0763 (7)
H23	0.3009	0.0713	0.5901	0.092*
C5	0.5495 (3)	0.7035 (3)	0.67231 (10)	0.0683 (7)
H5	0.5751	0.7732	0.6504	0.082*
C20	0.0073 (5)	0.1869 (3)	0.50109 (13)	0.1054 (11)
H20	−0.0705	0.2145	0.4791	0.126*
N2	−0.0240 (4)	0.5520 (3)	0.60771 (12)	0.1084 (9)
C8	0.1702 (3)	0.5580 (3)	0.83244 (10)	0.0652 (7)
C10	0.1288 (5)	0.4016 (4)	0.90171 (14)	0.1050 (10)
H10	0.0720	0.3334	0.9152	0.126*
C13	0.2949 (3)	0.6014 (4)	0.85973 (15)	0.1027 (11)
H13	0.3527	0.6688	0.8461	0.123*
C22	0.2061 (4)	0.0452 (3)	0.51797 (14)	0.0961 (10)
H22	0.2673	−0.0235	0.5077	0.115*
C19	0.0291 (4)	0.2479 (3)	0.54918 (12)	0.0904 (9)
H19	−0.0332	0.3160	0.5592	0.109*
C25	0.0719 (6)	0.0218 (5)	0.43028 (15)	0.1551 (19)
H25A	0.0117	0.0767	0.4079	0.233*
H25B	0.0219	−0.0597	0.4355	0.233*
H25C	0.1668	0.0071	0.4133	0.233*
C7	0.2845 (4)	0.7516 (3)	0.65304 (15)	0.1055 (12)
H7	0.1859	0.7232	0.6543	0.127*
C21	0.0960 (5)	0.0869 (3)	0.48418 (12)	0.0964 (10)
C9	0.0865 (3)	0.4586 (3)	0.85373 (12)	0.0816 (8)
H9	0.0014	0.4297	0.8359	0.098*
C11	0.2499 (5)	0.4419 (5)	0.92945 (15)	0.1210 (14)
C12	0.3324 (4)	0.5417 (6)	0.90856 (18)	0.1314 (17)
H12	0.4158	0.5709	0.9273	0.158*

	U11	U22	U33	U12	U13	U23
O1	0.130 (2)	0.192 (3)	0.363 (5)	−0.020 (2)	−0.038 (3)	0.212 (4)
C14	0.248 (7)	0.247 (6)	0.100 (3)	0.073 (6)	−0.044 (4)	0.005 (4)
S1	0.0426 (3)	0.0560 (3)	0.0975 (5)	0.0013 (3)	0.0086 (3)	−0.0120 (3)
C16	0.0484 (11)	0.0527 (12)	0.0636 (13)	−0.0027 (12)	0.0040 (11)	0.0009 (11)
O3	0.0409 (9)	0.0969 (13)	0.1122 (14)	0.0073 (9)	−0.0007 (9)	−0.0069 (12)
C17	0.0535 (13)	0.0545 (14)	0.0647 (14)	−0.0001 (11)	0.0035 (10)	0.0060 (12)
O2	0.0722 (11)	0.0487 (9)	0.1445 (16)	0.0002 (8)	0.0266 (11)	−0.0155 (12)
N1	0.0475 (10)	0.0491 (10)	0.0718 (12)	−0.0060 (8)	0.0032 (9)	−0.0044 (10)
C24	0.0756 (17)	0.0689 (18)	0.0757 (16)	0.0102 (15)	0.0020 (14)	−0.0112 (15)
C2	0.0635 (15)	0.0590 (14)	0.0792 (16)	0.0129 (11)	−0.0054 (13)	0.0094 (13)
C1	0.0453 (11)	0.0465 (11)	0.0595 (12)	0.0036 (9)	0.0008 (10)	−0.0049 (10)
C3	0.0534 (14)	0.0804 (17)	0.106 (2)	0.0212 (14)	−0.0092 (16)	−0.0056 (17)
C6	0.0544 (14)	0.0539 (13)	0.0707 (15)	−0.0020 (10)	−0.0005 (12)	0.0046 (12)
C18	0.0648 (15)	0.0526 (14)	0.0611 (14)	0.0018 (12)	0.0069 (12)	0.0049 (11)
C4	0.0455 (14)	0.0896 (19)	0.0881 (18)	−0.0005 (14)	0.0097 (13)	−0.0230 (17)
C15	0.0679 (15)	0.0540 (13)	0.0666 (14)	−0.0154 (11)	0.0049 (12)	−0.0052 (12)
C23	0.0712 (17)	0.0681 (17)	0.0895 (19)	0.0102 (14)	−0.0001 (14)	−0.0087 (16)
C5	0.0649 (17)	0.0665 (16)	0.0736 (16)	−0.0135 (13)	0.0092 (13)	−0.0028 (13)
C20	0.141 (3)	0.091 (2)	0.085 (2)	0.021 (2)	−0.032 (2)	−0.0105 (19)
N2	0.127 (2)	0.0856 (18)	0.112 (2)	0.0383 (18)	−0.0249 (18)	−0.0046 (16)
C8	0.0452 (12)	0.0717 (17)	0.0787 (16)	0.0009 (12)	0.0043 (11)	−0.0293 (14)
C10	0.134 (3)	0.097 (3)	0.084 (2)	−0.001 (3)	0.008 (2)	−0.0085 (19)
C13	0.0679 (18)	0.142 (3)	0.098 (2)	−0.026 (2)	0.0056 (17)	−0.043 (2)
C22	0.108 (2)	0.082 (2)	0.099 (2)	0.0099 (19)	0.018 (2)	−0.0267 (19)
C19	0.110 (2)	0.0745 (19)	0.086 (2)	0.0275 (18)	−0.0280 (17)	−0.0168 (16)
C25	0.223 (5)	0.151 (4)	0.092 (2)	−0.003 (4)	−0.014 (3)	−0.053 (3)
C7	0.082 (2)	0.084 (2)	0.150 (3)	−0.0029 (17)	−0.018 (2)	0.056 (2)
C21	0.132 (3)	0.086 (2)	0.0709 (18)	−0.006 (2)	0.005 (2)	−0.0170 (17)
C9	0.079 (2)	0.084 (2)	0.0825 (19)	−0.0122 (16)	0.0012 (14)	−0.0170 (17)
C11	0.119 (3)	0.159 (4)	0.085 (3)	0.027 (3)	−0.001 (2)	−0.029 (3)
C12	0.085 (3)	0.216 (5)	0.093 (3)	−0.002 (3)	−0.021 (2)	−0.056 (3)

O1—C7	1.185 (4)	C4—H4	0.9300
C14—C11	1.522 (6)	C15—H15A	0.9700
C14—H14A	0.9600	C15—H15B	0.9700
C14—H14B	0.9600	C23—C22	1.378 (4)
C14—H14C	0.9600	C23—H23	0.9300
S1—O2	1.4148 (18)	C5—H5	0.9300
S1—O3	1.4198 (17)	C20—C21	1.367 (5)
S1—N1	1.649 (2)	C20—C19	1.367 (4)
S1—C8	1.742 (3)	C20—H20	0.9300
C16—C17	1.331 (3)	C8—C9	1.375 (4)
C16—C24	1.434 (4)	C8—C13	1.381 (4)
C16—C15	1.492 (3)	C10—C11	1.351 (5)
C17—C18	1.466 (3)	C10—C9	1.385 (5)
C17—H17	0.9300	C10—H10	0.9300
N1—C1	1.447 (3)	C13—C12	1.404 (6)
N1—C15	1.479 (3)	C13—H13	0.9300
C24—N2	1.145 (3)	C22—C21	1.365 (5)
C2—C1	1.375 (3)	C22—H22	0.9300
C2—C3	1.381 (4)	C19—H19	0.9300
C2—H2	0.9300	C25—C21	1.517 (5)
C1—C6	1.386 (3)	C25—H25A	0.9600
C3—C4	1.367 (4)	C25—H25B	0.9600
C3—H3	0.9300	C25—H25C	0.9600
C6—C5	1.396 (4)	C7—H7	0.9300
C6—C7	1.462 (4)	C9—H9	0.9300
C18—C19	1.377 (4)	C11—C12	1.368 (6)
C18—C23	1.388 (3)	C12—H12	0.9300
C4—C5	1.345 (4)
C11—C14—H14A	109.5	C22—C23—C18	121.2 (3)
C11—C14—H14B	109.5	C22—C23—H23	119.4
H14A—C14—H14B	109.5	C18—C23—H23	119.4
C11—C14—H14C	109.5	C4—C5—C6	121.7 (3)
H14A—C14—H14C	109.5	C4—C5—H5	119.1
H14B—C14—H14C	109.5	C6—C5—H5	119.1
O2—S1—O3	119.94 (12)	C21—C20—C19	122.3 (3)
O2—S1—N1	105.95 (11)	C21—C20—H20	118.9
O3—S1—N1	105.96 (11)	C19—C20—H20	118.9
O2—S1—C8	108.98 (13)	C9—C8—C13	119.4 (3)
O3—S1—C8	107.90 (12)	C9—C8—S1	120.2 (2)
N1—S1—C8	107.49 (10)	C13—C8—S1	120.4 (3)
C17—C16—C24	122.9 (2)	C11—C10—C9	122.0 (4)
C17—C16—C15	121.9 (2)	C11—C10—H10	119.0
C24—C16—C15	115.0 (2)	C9—C10—H10	119.0
C16—C17—C18	131.2 (2)	C8—C13—C12	118.5 (4)
C16—C17—H17	114.4	C8—C13—H13	120.7
C18—C17—H17	114.4	C12—C13—H13	120.7
C1—N1—C15	117.84 (18)	C21—C22—C23	120.8 (3)
C1—N1—S1	117.57 (14)	C21—C22—H22	119.6
C15—N1—S1	116.52 (15)	C23—C22—H22	119.6
N2—C24—C16	177.1 (3)	C20—C19—C18	120.5 (3)
C1—C2—C3	119.9 (2)	C20—C19—H19	119.7
C1—C2—H2	120.0	C18—C19—H19	119.7
C3—C2—H2	120.0	C21—C25—H25A	109.5
C2—C1—C6	119.7 (2)	C21—C25—H25B	109.5
C2—C1—N1	121.3 (2)	H25A—C25—H25B	109.5
C6—C1—N1	118.99 (19)	C21—C25—H25C	109.5
C4—C3—C2	120.7 (2)	H25A—C25—H25C	109.5
C4—C3—H3	119.7	H25B—C25—H25C	109.5
C2—C3—H3	119.7	O1—C7—C6	123.0 (3)
C1—C6—C5	118.4 (2)	O1—C7—H7	118.5
C1—C6—C7	122.1 (2)	C6—C7—H7	118.5
C5—C6—C7	119.5 (3)	C22—C21—C20	117.8 (3)
C19—C18—C23	117.2 (2)	C22—C21—C25	120.6 (4)
C19—C18—C17	124.8 (2)	C20—C21—C25	121.6 (4)
C23—C18—C17	117.9 (2)	C8—C9—C10	120.0 (3)
C5—C4—C3	119.5 (2)	C8—C9—H9	120.0
C5—C4—H4	120.3	C10—C9—H9	120.0
C3—C4—H4	120.3	C10—C11—C12	118.0 (4)
N1—C15—C16	112.3 (2)	C10—C11—C14	122.0 (5)
N1—C15—H15A	109.1	C12—C11—C14	120.0 (5)
C16—C15—H15A	109.1	C11—C12—C13	122.0 (4)
N1—C15—H15B	109.1	C11—C12—H12	119.0
C16—C15—H15B	109.1	C13—C12—H12	119.0
H15A—C15—H15B	107.9
C24—C16—C17—C18	−4.5 (4)	C3—C4—C5—C6	−0.6 (4)
C15—C16—C17—C18	170.8 (2)	C1—C6—C5—C4	0.7 (4)
O2—S1—N1—C1	36.60 (19)	C7—C6—C5—C4	−177.6 (3)
O3—S1—N1—C1	165.03 (17)	O2—S1—C8—C9	156.4 (2)
C8—S1—N1—C1	−79.81 (18)	O3—S1—C8—C9	24.6 (2)
O2—S1—N1—C15	−175.28 (18)	N1—S1—C8—C9	−89.2 (2)
O3—S1—N1—C15	−46.8 (2)	O2—S1—C8—C13	−24.7 (3)
C8—S1—N1—C15	68.32 (19)	O3—S1—C8—C13	−156.5 (2)
C17—C16—C24—N2	−151 (6)	N1—S1—C8—C13	89.7 (2)
C15—C16—C24—N2	33 (7)	C9—C8—C13—C12	0.3 (5)
C3—C2—C1—C6	0.2 (4)	S1—C8—C13—C12	−178.7 (3)
C3—C2—C1—N1	−178.8 (2)	C18—C23—C22—C21	−2.5 (5)
C15—N1—C1—C2	−52.1 (3)	C21—C20—C19—C18	−0.5 (6)
S1—N1—C1—C2	95.6 (2)	C23—C18—C19—C20	−2.7 (5)
C15—N1—C1—C6	128.9 (2)	C17—C18—C19—C20	−178.7 (3)
S1—N1—C1—C6	−83.4 (2)	C1—C6—C7—O1	171.7 (4)
C1—C2—C3—C4	−0.1 (4)	C5—C6—C7—O1	−10.1 (6)
C2—C1—C6—C5	−0.5 (3)	C23—C22—C21—C20	−0.8 (5)
N1—C1—C6—C5	178.5 (2)	C23—C22—C21—C25	−179.6 (4)
C2—C1—C6—C7	177.8 (3)	C19—C20—C21—C22	2.3 (6)
N1—C1—C6—C7	−3.3 (4)	C19—C20—C21—C25	−179.0 (4)
C16—C17—C18—C19	−16.3 (4)	C13—C8—C9—C10	−1.0 (4)
C16—C17—C18—C23	167.7 (2)	S1—C8—C9—C10	177.9 (2)
C2—C3—C4—C5	0.3 (4)	C11—C10—C9—C8	1.2 (5)
C1—N1—C15—C16	−79.8 (3)	C9—C10—C11—C12	−0.5 (6)
S1—N1—C15—C16	132.11 (18)	C9—C10—C11—C14	179.3 (4)
C17—C16—C15—N1	136.8 (2)	C10—C11—C12—C13	−0.3 (6)
C24—C16—C15—N1	−47.5 (3)	C14—C11—C12—C13	179.9 (4)
C19—C18—C23—C22	4.2 (4)	C8—C13—C12—C11	0.4 (6)
C17—C18—C23—C22	−179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3	0.97	2.45	2.904 (3)	109
C23—H23···O1i	0.93	2.50	3.142 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O3	0.97	2.45	2.904 (3)	109
C23—H23⋯O1i	0.93	2.50	3.142 (4)	127

Symmetry code: (i) .