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

In the title compound, C(24)H(19)ClN(2)O(3)S, the sulfonyl-bound benzene ring forms dihedral angles of 38.1 (2) and 81.2 (1)°, respectively, with the formyl benzene and benzene rings. The mol-ecular conformation is stabilized by a weak 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(7) zigzag chains along [010] and R(3) (3)(19) ring motifs along [010]. The crystal packing is further stabilized by C-Cl⋯π inter-actions [Cl⋯centroid = 3.456 (2) Å and C-Cl⋯centroid = 173.4 (2)°].

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Ranjith et al. (2009 ▶); Aziz-ur-Rehman et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H19ClN2O3S

M = 450.92

Orthorhombic,

a = 8.9795 (5) Å

b = 10.1590 (5) Å

c = 25.1050 (13) Å

V = 2290.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.29 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 = 0.931, T max = 0.953

12721 measured reflections

4850 independent reflections

3396 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.111

S = 1.03

4850 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 2049 Friedel pairs

Flack parameter: 0.06 (8)

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/S160053681105241X/bt5740sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681105241X/bt5740Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681105241X/bt5740Isup3.cml

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

C24H19ClN2O3S	F(000) = 936
Mr = 450.92	Dx = 1.308 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4939 reflections
a = 8.9795 (5) Å	θ = 2.2–26.9°
b = 10.1590 (5) Å	µ = 0.29 mm−1
c = 25.1050 (13) Å	T = 293 K
V = 2290.1 (2) Å3	Block, yellow
Z = 4	0.25 × 0.23 × 0.17 mm

Bruker APEXII CCD diffractometer	4850 independent reflections
Radiation source: fine-focus sealed tube	3396 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 10.0 pixels mm-1	θmax = 26.9°, θmin = 2.2°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→10
Tmin = 0.931, Tmax = 0.953	l = −31→31
12721 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0529P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
4850 reflections	Δρmax = 0.22 e Å−3
281 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 2049 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.06 (8)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C11	0.7604 (6)	0.5498 (5)	0.07359 (14)	0.1160 (13)
C14	0.8095 (7)	0.6089 (6)	0.02121 (16)	0.201 (3)
H14A	0.7682	0.5588	−0.0077	0.301*
H14B	0.9162	0.6071	0.0190	0.301*
H14C	0.7754	0.6983	0.0190	0.301*
O1	0.8121 (4)	0.1434 (4)	0.3700 (2)	0.219 (2)
C1	0.8617 (3)	0.4264 (2)	0.28758 (8)	0.0479 (5)
C2	0.9741 (3)	0.4987 (2)	0.26417 (10)	0.0643 (6)
H2	0.9507	0.5693	0.2421	0.077*
C3	1.1211 (3)	0.4665 (3)	0.27345 (12)	0.0768 (7)
H3	1.1962	0.5159	0.2576	0.092*
C4	1.1574 (3)	0.3637 (3)	0.30530 (11)	0.0717 (7)
H4	1.2568	0.3427	0.3113	0.086*
C5	1.0479 (3)	0.2920 (3)	0.32827 (10)	0.0666 (7)
H5	1.0733	0.2215	0.3501	0.080*
C6	0.8986 (3)	0.3211 (2)	0.32010 (9)	0.0582 (6)
C7	0.7854 (4)	0.2419 (3)	0.34760 (14)	0.1041 (12)
H7	0.6874	0.2715	0.3472	0.125*
C8	0.6734 (3)	0.4380 (3)	0.16954 (10)	0.0628 (6)
C9	0.5954 (3)	0.5421 (3)	0.14801 (11)	0.0779 (8)
H9	0.5124	0.5756	0.1656	0.094*
C10	0.6406 (5)	0.5966 (4)	0.10032 (13)	0.1040 (11)
H10	0.5876	0.6671	0.0862	0.125*
C12	0.8370 (4)	0.4450 (5)	0.09478 (17)	0.1209 (15)
H12	0.9188	0.4113	0.0766	0.145*
C13	0.7949 (3)	0.3886 (4)	0.14272 (13)	0.0928 (10)
H13	0.8482	0.3181	0.1567	0.111*
C15	0.6569 (3)	0.5935 (2)	0.28573 (9)	0.0611 (6)
H15A	0.5668	0.6081	0.2653	0.073*
H15B	0.7326	0.6532	0.2724	0.073*
C16	0.6269 (3)	0.6244 (2)	0.34307 (8)	0.0537 (5)
C17	0.6670 (3)	0.7373 (2)	0.36505 (9)	0.0560 (6)
H17	0.7277	0.7897	0.3438	0.067*
C18	0.6318 (3)	0.7938 (2)	0.41719 (9)	0.0570 (6)
C19	0.5132 (3)	0.7545 (3)	0.44855 (11)	0.0837 (9)
H19	0.4505	0.6878	0.4368	0.100*
C20	0.4874 (5)	0.8130 (3)	0.49684 (12)	0.1036 (12)
H20	0.4072	0.7859	0.5176	0.124*
C21	0.5776 (5)	0.9097 (4)	0.51450 (12)	0.1022 (12)
C22	0.6900 (5)	0.9554 (3)	0.48410 (14)	0.1018 (11)
H22	0.7488	1.0250	0.4958	0.122*
C23	0.7163 (3)	0.8974 (3)	0.43569 (12)	0.0770 (8)
H23	0.7937	0.9291	0.4146	0.092*
C24	0.5434 (3)	0.5271 (3)	0.37117 (11)	0.0716 (7)
N1	0.7076 (2)	0.45611 (17)	0.27763 (8)	0.0551 (5)
N2	0.4797 (4)	0.4447 (3)	0.39244 (12)	0.1108 (10)
O2	0.6758 (2)	0.24175 (16)	0.23469 (9)	0.0834 (6)
O3	0.46666 (17)	0.39646 (19)	0.23817 (8)	0.0807 (5)
Cl1	0.5431 (2)	0.98128 (16)	0.57586 (4)	0.1878 (7)
S1	0.62059 (6)	0.37202 (6)	0.23103 (3)	0.06219 (18)

	U11	U22	U33	U12	U13	U23
C11	0.119 (3)	0.147 (4)	0.081 (2)	−0.033 (3)	0.009 (2)	−0.028 (2)
C14	0.248 (6)	0.258 (7)	0.096 (3)	−0.088 (6)	0.045 (3)	0.002 (4)
O1	0.125 (2)	0.181 (3)	0.353 (5)	0.015 (2)	0.035 (3)	0.203 (4)
C1	0.0432 (12)	0.0425 (11)	0.0580 (11)	−0.0027 (10)	−0.0012 (10)	−0.0052 (10)
C2	0.0609 (16)	0.0558 (14)	0.0762 (15)	−0.0082 (12)	0.0038 (13)	0.0108 (12)
C3	0.0523 (15)	0.0728 (17)	0.1051 (19)	−0.0189 (15)	0.0065 (16)	−0.0079 (17)
C4	0.0430 (14)	0.0819 (19)	0.0902 (17)	0.0019 (15)	−0.0090 (13)	−0.0203 (16)
C5	0.0646 (17)	0.0626 (16)	0.0725 (15)	0.0150 (15)	−0.0119 (13)	−0.0006 (13)
C6	0.0498 (14)	0.0530 (14)	0.0716 (13)	0.0016 (11)	0.0002 (11)	0.0059 (11)
C7	0.077 (2)	0.088 (2)	0.148 (3)	0.0056 (18)	0.0180 (19)	0.062 (2)
C8	0.0458 (13)	0.0663 (17)	0.0762 (15)	−0.0001 (12)	−0.0051 (11)	−0.0263 (13)
C9	0.079 (2)	0.0769 (19)	0.0783 (17)	0.0068 (16)	−0.0054 (14)	−0.0150 (15)
C10	0.137 (3)	0.089 (2)	0.086 (2)	−0.007 (2)	−0.014 (2)	−0.0118 (18)
C12	0.085 (3)	0.178 (5)	0.101 (3)	−0.005 (3)	0.020 (2)	−0.050 (3)
C13	0.0632 (18)	0.120 (3)	0.095 (2)	0.014 (2)	−0.0043 (16)	−0.038 (2)
C15	0.0680 (16)	0.0525 (13)	0.0626 (13)	0.0185 (12)	−0.0040 (11)	−0.0006 (11)
C16	0.0478 (12)	0.0512 (13)	0.0623 (12)	−0.0005 (13)	−0.0036 (11)	0.0016 (11)
C17	0.0517 (14)	0.0558 (14)	0.0604 (13)	−0.0009 (11)	−0.0002 (10)	0.0082 (12)
C18	0.0637 (15)	0.0499 (13)	0.0574 (12)	0.0003 (13)	−0.0082 (12)	0.0057 (10)
C19	0.100 (2)	0.074 (2)	0.0773 (17)	−0.0220 (18)	0.0195 (16)	−0.0119 (14)
C20	0.135 (3)	0.093 (2)	0.082 (2)	−0.012 (2)	0.037 (2)	−0.0069 (18)
C21	0.146 (4)	0.092 (3)	0.0687 (17)	0.012 (2)	−0.005 (2)	−0.0209 (17)
C22	0.119 (3)	0.082 (2)	0.105 (2)	−0.006 (2)	−0.021 (2)	−0.034 (2)
C23	0.0789 (18)	0.0617 (16)	0.0902 (19)	−0.0080 (15)	−0.0028 (15)	−0.0113 (15)
C24	0.0772 (18)	0.0632 (17)	0.0744 (15)	−0.0074 (16)	0.0024 (14)	−0.0077 (14)
N1	0.0479 (11)	0.0448 (10)	0.0727 (12)	0.0070 (9)	−0.0031 (9)	−0.0042 (9)
N2	0.134 (3)	0.0835 (19)	0.115 (2)	−0.0344 (19)	0.0280 (18)	−0.0016 (16)
O2	0.0650 (11)	0.0475 (10)	0.1378 (15)	−0.0014 (8)	−0.0240 (11)	−0.0125 (10)
O3	0.0386 (9)	0.0940 (14)	0.1095 (13)	−0.0011 (10)	0.0003 (9)	−0.0049 (11)
Cl1	0.2742 (18)	0.1942 (13)	0.0951 (7)	0.0109 (14)	0.0130 (9)	−0.0698 (8)
S1	0.0394 (3)	0.0540 (3)	0.0931 (4)	−0.0008 (3)	−0.0067 (3)	−0.0100 (3)

C11—C10	1.354 (5)	C12—C13	1.386 (5)
C11—C12	1.375 (6)	C12—H12	0.9300
C11—C14	1.511 (6)	C13—H13	0.9300
C14—H14A	0.9600	C15—N1	1.482 (3)
C14—H14B	0.9600	C15—C16	1.498 (3)
C14—H14C	0.9600	C15—H15A	0.9700
O1—C7	1.173 (4)	C15—H15B	0.9700
C1—C2	1.379 (3)	C16—C17	1.323 (3)
C1—C6	1.386 (3)	C16—C24	1.427 (4)
C1—N1	1.438 (3)	C17—C18	1.464 (3)
C2—C3	1.380 (4)	C17—H17	0.9300
C2—H2	0.9300	C18—C23	1.378 (4)
C3—C4	1.355 (4)	C18—C19	1.383 (4)
C3—H3	0.9300	C19—C20	1.370 (4)
C4—C5	1.353 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.348 (5)
C5—C6	1.388 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.348 (5)
C6—C7	1.468 (4)	C21—Cl1	1.731 (3)
C7—H7	0.9300	C22—C23	1.371 (4)
C8—C13	1.377 (4)	C22—H22	0.9300
C8—C9	1.379 (4)	C23—H23	0.9300
C8—S1	1.748 (3)	C24—N2	1.146 (4)
C9—C10	1.380 (4)	N1—S1	1.6459 (19)
C9—H9	0.9300	O2—S1	1.4161 (18)
C10—H10	0.9300	O3—S1	1.4157 (17)
C10—C11—C12	118.5 (4)	C8—C13—H13	120.3
C10—C11—C14	121.6 (5)	C12—C13—H13	120.3
C12—C11—C14	119.9 (5)	N1—C15—C16	112.58 (19)
C11—C14—H14A	109.5	N1—C15—H15A	109.1
C11—C14—H14B	109.5	C16—C15—H15A	109.1
H14A—C14—H14B	109.5	N1—C15—H15B	109.1
C11—C14—H14C	109.5	C16—C15—H15B	109.1
H14A—C14—H14C	109.5	H15A—C15—H15B	107.8
H14B—C14—H14C	109.5	C17—C16—C24	122.5 (2)
C2—C1—C6	119.2 (2)	C17—C16—C15	122.2 (2)
C2—C1—N1	121.2 (2)	C24—C16—C15	115.1 (2)
C6—C1—N1	119.6 (2)	C16—C17—C18	130.9 (2)
C1—C2—C3	120.1 (2)	C16—C17—H17	114.6
C1—C2—H2	120.0	C18—C17—H17	114.6
C3—C2—H2	120.0	C23—C18—C19	116.9 (2)
C4—C3—C2	120.9 (2)	C23—C18—C17	118.8 (2)
C4—C3—H3	119.6	C19—C18—C17	124.2 (2)
C2—C3—H3	119.6	C20—C19—C18	120.6 (3)
C5—C4—C3	119.4 (2)	C20—C19—H19	119.7
C5—C4—H4	120.3	C18—C19—H19	119.7
C3—C4—H4	120.3	C21—C20—C19	120.3 (3)
C4—C5—C6	121.7 (2)	C21—C20—H20	119.8
C4—C5—H5	119.2	C19—C20—H20	119.8
C6—C5—H5	119.2	C20—C21—C22	121.0 (3)
C1—C6—C5	118.8 (2)	C20—C21—Cl1	119.4 (3)
C1—C6—C7	122.3 (2)	C22—C21—Cl1	119.5 (3)
C5—C6—C7	118.9 (2)	C21—C22—C23	118.9 (3)
O1—C7—C6	123.5 (3)	C21—C22—H22	120.6
O1—C7—H7	118.3	C23—C22—H22	120.6
C6—C7—H7	118.3	C22—C23—C18	122.1 (3)
C13—C8—C9	119.4 (3)	C22—C23—H23	118.9
C13—C8—S1	120.5 (2)	C18—C23—H23	118.9
C9—C8—S1	120.1 (2)	N2—C24—C16	176.9 (3)
C8—C9—C10	119.9 (3)	C1—N1—C15	117.97 (18)
C8—C9—H9	120.1	C1—N1—S1	118.12 (14)
C10—C9—H9	120.1	C15—N1—S1	116.15 (15)
C11—C10—C9	121.5 (4)	O3—S1—O2	119.82 (12)
C11—C10—H10	119.2	O3—S1—N1	106.40 (11)
C9—C10—H10	119.2	O2—S1—N1	105.83 (10)
C11—C12—C13	121.3 (4)	O3—S1—C8	108.02 (12)
C11—C12—H12	119.3	O2—S1—C8	108.70 (13)
C13—C12—H12	119.3	N1—S1—C8	107.46 (11)
C8—C13—C12	119.4 (4)
C6—C1—C2—C3	−0.4 (4)	C17—C18—C19—C20	−179.6 (3)
N1—C1—C2—C3	−178.6 (2)	C18—C19—C20—C21	−0.1 (5)
C1—C2—C3—C4	0.2 (4)	C19—C20—C21—C22	3.4 (6)
C2—C3—C4—C5	0.0 (4)	C19—C20—C21—Cl1	−179.6 (3)
C3—C4—C5—C6	−0.1 (4)	C20—C21—C22—C23	−3.2 (6)
C2—C1—C6—C5	0.3 (3)	Cl1—C21—C22—C23	179.8 (3)
N1—C1—C6—C5	178.5 (2)	C21—C22—C23—C18	−0.2 (5)
C2—C1—C6—C7	178.2 (3)	C19—C18—C23—C22	3.3 (4)
N1—C1—C6—C7	−3.5 (4)	C17—C18—C23—C22	180.0 (3)
C4—C5—C6—C1	−0.1 (4)	C17—C16—C24—N2	−147 (6)
C4—C5—C6—C7	−178.1 (3)	C15—C16—C24—N2	37 (6)
C1—C6—C7—O1	170.6 (4)	C2—C1—N1—C15	−52.3 (3)
C5—C6—C7—O1	−11.5 (6)	C6—C1—N1—C15	129.5 (2)
C13—C8—C9—C10	−0.7 (4)	C2—C1—N1—S1	95.8 (2)
S1—C8—C9—C10	177.8 (2)	C6—C1—N1—S1	−82.4 (2)
C12—C11—C10—C9	0.4 (6)	C16—C15—N1—C1	−80.8 (3)
C14—C11—C10—C9	179.6 (4)	C16—C15—N1—S1	130.40 (19)
C8—C9—C10—C11	0.3 (5)	C1—N1—S1—O3	166.06 (17)
C10—C11—C12—C13	−0.8 (6)	C15—N1—S1—O3	−45.2 (2)
C14—C11—C12—C13	180.0 (4)	C1—N1—S1—O2	37.58 (19)
C9—C8—C13—C12	0.4 (4)	C15—N1—S1—O2	−173.70 (18)
S1—C8—C13—C12	−178.2 (3)	C1—N1—S1—C8	−78.43 (18)
C11—C12—C13—C8	0.4 (5)	C15—N1—S1—C8	70.29 (19)
N1—C15—C16—C17	138.6 (2)	C13—C8—S1—O3	−155.0 (2)
N1—C15—C16—C24	−45.5 (3)	C9—C8—S1—O3	26.5 (2)
C24—C16—C17—C18	−4.9 (4)	C13—C8—S1—O2	−23.5 (2)
C15—C16—C17—C18	170.8 (2)	C9—C8—S1—O2	157.92 (19)
C16—C17—C18—C23	164.1 (2)	C13—C8—S1—N1	90.6 (2)
C16—C17—C18—C19	−19.4 (4)	C9—C8—S1—N1	−88.0 (2)
C23—C18—C19—C20	−3.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O3	0.97	2.43	2.890 (3)	109
C3—H3···O2i	0.93	2.57	3.345 (3)	141.
C15—H15A···O2ii	0.97	2.57	3.385 (3)	142.
C23—H23···O1iii	0.93	2.45	3.114 (4)	128.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O3	0.97	2.43	2.890 (3)	109
C3—H3⋯O2i	0.93	2.57	3.345 (3)	141
C15—H15A⋯O2ii	0.97	2.57	3.385 (3)	142
C23—H23⋯O1iii	0.93	2.45	3.114 (4)	128

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