Methyl (Z)-2-{[N-(2-formyl-phen-yl)-4-methyl-benzene-sulfonamido]-meth-yl}-3-phenyl-prop-2-enoate.

In the title compound, C(25)H(23)NO(5)S, the sulfonyl-bound benzene ring forms dihedral angles of 37.2 (1) and 67.0 (1)°, respectively, with the formyl-phenyl and phenyl rings. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯π inter-action. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming a two-dimensional network in the (110) plane in which R(4) (4)(38) ring motifs are generated.

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 ▶). For the Thrope–Ingold effect, see: Bassindale (1984 ▶).

Experimental

Crystal data

C25H23NO5S

M = 449.50

Monoclinic,

a = 9.7475 (5) Å

b = 21.7053 (12) Å

c = 11.2643 (6) Å

β = 109.987 (2)°

V = 2239.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 293 K

0.23 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.971

28975 measured reflections

6991 independent reflections

4593 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.153

S = 0.99

6991 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.31 e Å−3

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/S1600536811050756/bt5721sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050756/bt5721Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811050756/bt5721Isup3.cml

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

C25H23NO5S	F(000) = 944
Mr = 449.50	Dx = 1.333 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7038 reflections
a = 9.7475 (5) Å	θ = 2.1–30.8°
b = 21.7053 (12) Å	µ = 0.18 mm−1
c = 11.2643 (6) Å	T = 293 K
β = 109.987 (2)°	Block, colourless
V = 2239.7 (2) Å3	0.23 × 0.21 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	6991 independent reflections
Radiation source: fine-focus sealed tube	4593 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 30.8°, θmin = 2.1°
ω scans	h = −13→14
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −31→31
Tmin = 0.959, Tmax = 0.971	l = −16→15
28975 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0773P)2 + 0.5464P] where P = (Fo2 + 2Fc2)/3
6991 reflections	(Δ/σ)max < 0.001
291 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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
C1	0.59422 (16)	0.13486 (7)	0.03835 (16)	0.0388 (3)
C2	0.58668 (19)	0.14617 (9)	−0.08453 (18)	0.0511 (4)
H2	0.5590	0.1848	−0.1206	0.061*
C3	0.6208 (2)	0.09931 (12)	−0.1534 (2)	0.0703 (6)
H3	0.6153	0.1067	−0.2362	0.084*
C4	0.6628 (2)	0.04221 (12)	−0.1010 (3)	0.0785 (8)
H4	0.6865	0.0113	−0.1478	0.094*
C5	0.6695 (2)	0.03105 (9)	0.0194 (3)	0.0689 (6)
H5	0.6980	−0.0077	0.0545	0.083*
C6	0.63450 (18)	0.07667 (8)	0.09133 (19)	0.0485 (4)
C7	0.6342 (2)	0.06179 (9)	0.2188 (2)	0.0643 (5)
H7	0.5862	0.0886	0.2558	0.077*
C8	0.76439 (16)	0.27383 (7)	0.14360 (16)	0.0407 (3)
C9	0.7236 (2)	0.33478 (8)	0.1488 (2)	0.0536 (4)
H9	0.6608	0.3452	0.1919	0.064*
C10	0.7762 (2)	0.37946 (9)	0.0900 (2)	0.0621 (5)
H10	0.7491	0.4203	0.0942	0.075*
C11	0.8691 (2)	0.36516 (9)	0.0245 (2)	0.0581 (5)
C12	0.9085 (2)	0.30403 (10)	0.0192 (2)	0.0580 (5)
H12	0.9704	0.2937	−0.0248	0.070*
C13	0.85695 (19)	0.25836 (8)	0.07857 (18)	0.0502 (4)
H13	0.8843	0.2176	0.0748	0.060*
C14	0.9305 (3)	0.41529 (12)	−0.0355 (3)	0.0846 (8)
H14A	0.8850	0.4538	−0.0294	0.127*
H14B	0.9117	0.4055	−0.1227	0.127*
H14C	1.0339	0.4184	0.0076	0.127*
C15	0.42926 (16)	0.22099 (7)	0.05346 (15)	0.0384 (3)
H15A	0.3777	0.2057	−0.0310	0.046*
H15B	0.4598	0.2629	0.0459	0.046*
C16	0.32755 (16)	0.22105 (7)	0.12797 (16)	0.0403 (3)
C17	0.29963 (18)	0.27004 (8)	0.18717 (17)	0.0463 (4)
H17	0.2376	0.2639	0.2331	0.056*
C18	0.35677 (19)	0.33301 (8)	0.18761 (18)	0.0467 (4)
C19	0.4342 (2)	0.36162 (9)	0.3013 (2)	0.0568 (5)
H19	0.4488	0.3411	0.3771	0.068*
C20	0.4895 (2)	0.42009 (11)	0.3023 (3)	0.0698 (6)
H20	0.5435	0.4384	0.3786	0.084*
C21	0.4654 (3)	0.45140 (10)	0.1912 (3)	0.0723 (6)
H21	0.5030	0.4909	0.1923	0.087*
C22	0.3860 (3)	0.42452 (10)	0.0785 (3)	0.0717 (6)
H22	0.3679	0.4461	0.0034	0.086*
C23	0.3326 (2)	0.36523 (9)	0.0762 (2)	0.0581 (5)
H23	0.2801	0.3470	−0.0006	0.070*
C24	0.25669 (18)	0.16079 (8)	0.13063 (19)	0.0492 (4)
C25	0.0837 (3)	0.10598 (10)	0.1935 (3)	0.0819 (8)
H25A	0.0173	0.0964	0.1106	0.123*
H25B	0.0302	0.1106	0.2504	0.123*
H25C	0.1534	0.0732	0.2225	0.123*
N1	0.56062 (13)	0.18221 (6)	0.11335 (12)	0.0362 (3)
O1	0.6918 (3)	0.01735 (8)	0.2780 (2)	0.1093 (7)
O2	0.81113 (13)	0.17074 (6)	0.26567 (12)	0.0525 (3)
O3	0.64184 (13)	0.24539 (6)	0.30692 (11)	0.0509 (3)
O4	0.28273 (17)	0.11474 (6)	0.08321 (18)	0.0714 (4)
O5	0.15907 (17)	0.16258 (6)	0.18906 (17)	0.0694 (4)
S1	0.69945 (4)	0.216238 (18)	0.22055 (4)	0.04001 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0321 (7)	0.0374 (7)	0.0488 (9)	0.0001 (5)	0.0164 (6)	−0.0058 (6)
C2	0.0459 (9)	0.0582 (10)	0.0512 (10)	−0.0033 (8)	0.0193 (8)	−0.0072 (8)
C3	0.0544 (11)	0.0992 (18)	0.0651 (13)	−0.0141 (11)	0.0303 (10)	−0.0337 (12)
C4	0.0581 (12)	0.0746 (15)	0.110 (2)	−0.0031 (11)	0.0379 (13)	−0.0465 (15)
C5	0.0499 (11)	0.0440 (10)	0.111 (2)	0.0040 (8)	0.0246 (11)	−0.0185 (11)
C6	0.0378 (8)	0.0379 (8)	0.0690 (12)	0.0009 (6)	0.0171 (8)	−0.0013 (8)
C7	0.0626 (12)	0.0452 (10)	0.0788 (14)	−0.0004 (9)	0.0162 (10)	0.0150 (9)
C8	0.0335 (7)	0.0407 (8)	0.0468 (9)	−0.0019 (6)	0.0123 (6)	−0.0067 (7)
C9	0.0521 (10)	0.0427 (9)	0.0728 (13)	−0.0015 (7)	0.0303 (9)	−0.0119 (8)
C10	0.0616 (12)	0.0396 (9)	0.0895 (16)	−0.0035 (8)	0.0315 (11)	−0.0069 (9)
C11	0.0521 (10)	0.0551 (11)	0.0669 (12)	−0.0117 (8)	0.0202 (9)	−0.0023 (9)
C12	0.0527 (10)	0.0645 (12)	0.0647 (12)	−0.0048 (9)	0.0303 (9)	−0.0067 (10)
C13	0.0466 (9)	0.0455 (9)	0.0621 (11)	0.0028 (7)	0.0232 (8)	−0.0065 (8)
C14	0.0802 (16)	0.0734 (15)	0.108 (2)	−0.0179 (13)	0.0418 (15)	0.0120 (14)
C15	0.0348 (7)	0.0372 (7)	0.0409 (8)	0.0073 (6)	0.0099 (6)	0.0012 (6)
C16	0.0320 (7)	0.0384 (8)	0.0479 (9)	0.0037 (6)	0.0106 (6)	0.0003 (6)
C17	0.0413 (8)	0.0454 (9)	0.0563 (10)	0.0028 (7)	0.0220 (7)	−0.0032 (7)
C18	0.0441 (9)	0.0404 (8)	0.0592 (11)	0.0060 (6)	0.0224 (8)	−0.0079 (7)
C19	0.0601 (11)	0.0573 (11)	0.0589 (11)	−0.0005 (9)	0.0280 (9)	−0.0122 (9)
C20	0.0659 (13)	0.0616 (13)	0.0867 (17)	−0.0097 (10)	0.0322 (12)	−0.0305 (12)
C21	0.0747 (14)	0.0401 (10)	0.112 (2)	−0.0009 (9)	0.0454 (14)	−0.0107 (12)
C22	0.0849 (16)	0.0465 (11)	0.0871 (16)	0.0119 (10)	0.0338 (13)	0.0097 (11)
C23	0.0604 (11)	0.0470 (10)	0.0646 (12)	0.0090 (8)	0.0186 (9)	−0.0022 (9)
C24	0.0366 (8)	0.0423 (9)	0.0684 (12)	0.0030 (6)	0.0176 (8)	0.0034 (8)
C25	0.0644 (14)	0.0548 (12)	0.143 (2)	−0.0024 (10)	0.0567 (15)	0.0158 (14)
N1	0.0321 (6)	0.0343 (6)	0.0406 (7)	0.0043 (5)	0.0102 (5)	−0.0014 (5)
O1	0.1367 (18)	0.0598 (10)	0.1075 (15)	0.0136 (11)	0.0111 (13)	0.0356 (10)
O2	0.0400 (6)	0.0564 (7)	0.0532 (7)	0.0107 (5)	0.0056 (5)	0.0064 (6)
O3	0.0482 (7)	0.0638 (8)	0.0410 (6)	−0.0001 (6)	0.0154 (5)	−0.0111 (6)
O4	0.0677 (9)	0.0446 (7)	0.1143 (13)	−0.0088 (6)	0.0471 (9)	−0.0177 (8)
O5	0.0643 (9)	0.0469 (7)	0.1163 (13)	0.0025 (6)	0.0558 (9)	0.0068 (8)
S1	0.03449 (19)	0.0436 (2)	0.0391 (2)	0.00304 (14)	0.00894 (15)	−0.00255 (15)

C1—C2	1.383 (3)	C15—N1	1.4875 (18)
C1—C6	1.395 (2)	C15—C16	1.502 (2)
C1—N1	1.4375 (19)	C15—H15A	0.9700
C2—C3	1.387 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—C17	1.332 (2)
C3—C4	1.374 (4)	C16—C24	1.484 (2)
C3—H3	0.9300	C17—C18	1.475 (2)
C4—C5	1.357 (4)	C17—H17	0.9300
C4—H4	0.9300	C18—C23	1.385 (3)
C5—C6	1.394 (3)	C18—C19	1.391 (3)
C5—H5	0.9300	C19—C20	1.377 (3)
C6—C7	1.473 (3)	C19—H19	0.9300
C7—O1	1.197 (2)	C20—C21	1.372 (4)
C7—H7	0.9300	C20—H20	0.9300
C8—C13	1.384 (2)	C21—C22	1.371 (4)
C8—C9	1.388 (2)	C21—H21	0.9300
C8—S1	1.7577 (17)	C22—C23	1.385 (3)
C9—C10	1.369 (3)	C22—H22	0.9300
C9—H9	0.9300	C23—H23	0.9300
C10—C11	1.385 (3)	C24—O4	1.201 (2)
C10—H10	0.9300	C24—O5	1.330 (2)
C11—C12	1.388 (3)	C25—O5	1.441 (2)
C11—C14	1.508 (3)	C25—H25A	0.9600
C12—C13	1.383 (3)	C25—H25B	0.9600
C12—H12	0.9300	C25—H25C	0.9600
C13—H13	0.9300	N1—S1	1.6485 (13)
C14—H14A	0.9600	O2—S1	1.4284 (12)
C14—H14B	0.9600	O3—S1	1.4268 (12)
C14—H14C	0.9600
C2—C1—C6	119.99 (16)	C16—C15—H15A	109.2
C2—C1—N1	121.11 (15)	N1—C15—H15B	109.2
C6—C1—N1	118.90 (15)	C16—C15—H15B	109.2
C1—C2—C3	119.3 (2)	H15A—C15—H15B	107.9
C1—C2—H2	120.4	C17—C16—C24	121.16 (16)
C3—C2—H2	120.4	C17—C16—C15	124.56 (15)
C4—C3—C2	121.0 (2)	C24—C16—C15	114.28 (14)
C4—C3—H3	119.5	C16—C17—C18	126.87 (16)
C2—C3—H3	119.5	C16—C17—H17	116.6
C5—C4—C3	119.7 (2)	C18—C17—H17	116.6
C5—C4—H4	120.1	C23—C18—C19	118.66 (18)
C3—C4—H4	120.1	C23—C18—C17	121.18 (17)
C4—C5—C6	121.1 (2)	C19—C18—C17	120.15 (18)
C4—C5—H5	119.5	C20—C19—C18	120.5 (2)
C6—C5—H5	119.5	C20—C19—H19	119.8
C5—C6—C1	118.9 (2)	C18—C19—H19	119.8
C5—C6—C7	119.56 (19)	C21—C20—C19	120.3 (2)
C1—C6—C7	121.45 (17)	C21—C20—H20	119.9
O1—C7—C6	124.2 (2)	C19—C20—H20	119.9
O1—C7—H7	117.9	C22—C21—C20	120.0 (2)
C6—C7—H7	117.9	C22—C21—H21	120.0
C13—C8—C9	120.10 (17)	C20—C21—H21	120.0
C13—C8—S1	119.88 (13)	C21—C22—C23	120.2 (2)
C9—C8—S1	120.02 (13)	C21—C22—H22	119.9
C10—C9—C8	119.64 (17)	C23—C22—H22	119.9
C10—C9—H9	120.2	C18—C23—C22	120.4 (2)
C8—C9—H9	120.2	C18—C23—H23	119.8
C9—C10—C11	121.36 (18)	C22—C23—H23	119.8
C9—C10—H10	119.3	O4—C24—O5	122.70 (17)
C11—C10—H10	119.3	O4—C24—C16	123.65 (17)
C10—C11—C12	118.55 (19)	O5—C24—C16	113.64 (15)
C10—C11—C14	120.6 (2)	O5—C25—H25A	109.5
C12—C11—C14	120.8 (2)	O5—C25—H25B	109.5
C13—C12—C11	120.84 (18)	H25A—C25—H25B	109.5
C13—C12—H12	119.6	O5—C25—H25C	109.5
C11—C12—H12	119.6	H25A—C25—H25C	109.5
C12—C13—C8	119.51 (17)	H25B—C25—H25C	109.5
C12—C13—H13	120.2	C1—N1—C15	118.14 (12)
C8—C13—H13	120.2	C1—N1—S1	117.12 (10)
C11—C14—H14A	109.5	C15—N1—S1	116.27 (10)
C11—C14—H14B	109.5	C24—O5—C25	116.87 (16)
H14A—C14—H14B	109.5	O3—S1—O2	119.58 (8)
C11—C14—H14C	109.5	O3—S1—N1	106.39 (7)
H14A—C14—H14C	109.5	O2—S1—N1	106.61 (7)
H14B—C14—H14C	109.5	O3—S1—C8	108.23 (8)
N1—C15—C16	112.16 (12)	O2—S1—C8	107.94 (8)
N1—C15—H15A	109.2	N1—S1—C8	107.53 (7)
C6—C1—C2—C3	−0.6 (2)	C18—C19—C20—C21	1.7 (3)
N1—C1—C2—C3	179.61 (15)	C19—C20—C21—C22	0.0 (3)
C1—C2—C3—C4	−0.4 (3)	C20—C21—C22—C23	−1.4 (4)
C2—C3—C4—C5	0.7 (3)	C19—C18—C23—C22	0.6 (3)
C3—C4—C5—C6	0.0 (3)	C17—C18—C23—C22	179.45 (18)
C4—C5—C6—C1	−1.0 (3)	C21—C22—C23—C18	1.1 (3)
C4—C5—C6—C7	176.2 (2)	C17—C16—C24—O4	−176.84 (19)
C2—C1—C6—C5	1.3 (2)	C15—C16—C24—O4	3.6 (3)
N1—C1—C6—C5	−178.91 (15)	C17—C16—C24—O5	4.2 (3)
C2—C1—C6—C7	−175.87 (17)	C15—C16—C24—O5	−175.38 (15)
N1—C1—C6—C7	3.9 (2)	C2—C1—N1—C15	44.2 (2)
C5—C6—C7—O1	17.0 (3)	C6—C1—N1—C15	−135.57 (15)
C1—C6—C7—O1	−165.9 (2)	C2—C1—N1—S1	−102.71 (15)
C13—C8—C9—C10	−0.5 (3)	C6—C1—N1—S1	77.50 (16)
S1—C8—C9—C10	179.12 (16)	C16—C15—N1—C1	125.78 (14)
C8—C9—C10—C11	0.4 (3)	C16—C15—N1—S1	−87.01 (14)
C9—C10—C11—C12	0.0 (3)	O4—C24—O5—C25	−0.1 (3)
C9—C10—C11—C14	−177.7 (2)	C16—C24—O5—C25	178.93 (19)
C10—C11—C12—C13	−0.3 (3)	C1—N1—S1—O3	−161.76 (11)
C14—C11—C12—C13	177.3 (2)	C15—N1—S1—O3	50.69 (13)
C11—C12—C13—C8	0.3 (3)	C1—N1—S1—O2	−33.10 (13)
C9—C8—C13—C12	0.1 (3)	C15—N1—S1—O2	179.35 (11)
S1—C8—C13—C12	−179.45 (14)	C1—N1—S1—C8	82.46 (12)
N1—C15—C16—C17	113.35 (17)	C15—N1—S1—C8	−65.09 (12)
N1—C15—C16—C24	−67.10 (17)	C13—C8—S1—O3	164.21 (13)
C24—C16—C17—C18	−177.05 (17)	C9—C8—S1—O3	−15.39 (17)
C15—C16—C17—C18	2.5 (3)	C13—C8—S1—O2	33.45 (16)
C16—C17—C18—C23	58.2 (3)	C9—C8—S1—O2	−146.15 (15)
C16—C17—C18—C19	−123.0 (2)	C13—C8—S1—N1	−81.23 (15)
C23—C18—C19—C20	−2.0 (3)	C9—C8—S1—N1	99.17 (15)
C17—C18—C19—C20	179.14 (17)

Cg is the centroid of the C18–C23 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···Cg	0.93	2.64	3.470 (2)	149.
C25—H25B···O2i	0.96	2.56	3.342 (3)	139.
C10—H10···O1ii	0.93	2.51	3.309 (3)	145.

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯Cg	0.93	2.64	3.470 (2)	149
C25—H25B⋯O2i	0.96	2.56	3.342 (3)	139
C10—H10⋯O1ii	0.93	2.51	3.309 (3)	145

Symmetry codes: (i) ; (ii) .