Methyl (Z)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-phenyl­prop-2-enoate

Madhanraj, R.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536811050756

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3511

https://doi.org/10.1107/S1600536811050756

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Methyl (Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-phenylprop-2-enoate

R. Madhanraj,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ‡

^aDepartment of Physics, Ranipettai Engineering College, Thenkadapathangal, Walaja 632 513, India, ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^cDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 21 November 2011; accepted 25 November 2011; online 30 November 2011)

In the title compound, C₂₅H₂₃NO₅S, the sulfonyl-bound benzene ring forms dihedral angles of 37.2 (1) and 67.0 (1)°, respectively, with the formylphenyl and phenyl rings. The molecular conformation is stabilized by an intramolecular C—H⋯π interaction. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming a two-dimensional network in the (110) plane in which R₄⁴(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_r = 449.50
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.153
S = 0.99
6991 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.31 e Å⁻³

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) x-1, y, z; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811050756/bt5721sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050756/bt5721Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050756/bt5721Isup3.cml

checkCIF report

Comment top

Sulfonamide drugs are widely used for the treatment of certain infections caused by Gram-positive and Gram-negative microorganisms, some fungi, and certain protozoa (Korolkovas, 1988, Mandell & Sande, 1992). In view of this biological importance, the crystal structure of the title compound has been determined and the results are presented here.

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The S1 atom shows a distorted tetrahedral geometry, with O2—S1—O3 [119.6 (1)°] and N1—S1—C8 [107.5 (1)°] angles deviating from ideal tetrahedral values, are attributed to the Thrope-Ingold effect (Bassindale, 1984). The sum of bond angles around N1 (351.5°) indicates that N1 is in sp² hybridization. The sulfonyl bound phenyl (C8–C13) ring forms dihedral angles of 37.2 (1)° and 67.0 (1)°, respectively, with the formyl phenyl (C1–C6) and phenyl (C18—C23) rings. The dihedral angle between formyl phenyl and phenyl rings is 45.9 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Ranjith et al., 2009; Aziz-ur-Rehman et al., 2010).

The molecular structure is stabilized by intramolecular C-H···π interaction between a sulfonyl bound phenyl H9 atom and a phenyl (C18–C23) ring with a C9—H9···Cg seperation of 2.64 Å.(Fig. 1 and Table 1; Cg is the centroid of the C18–C23 phenyl ring). In the crystal four molecules are linked by intermolecular C—H···O hydrogen bonds (Fig. 2, Table 1; Symmetry codes as given in Fig. 2), generating R₄⁴(38) ring motifs (Bernstein et al., 1995) to form a two dimensional network along [110]] directions.

Related literature top

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 top

A solution of N-(formylphenyl)(4-methylbenzene)sulfonamide (1 mmol, 0.28 g) and potassium carbonate (1.5 mmol, 0.21 g) in acetonitrile solvent was stirred for 15 minutes at room temperature. To this solution, (z)-methyl-2-(bromomethyl)-3-phenylprop-2-enoate (1.2 mmol, 0.30 g) was added dropwise till the addition is complete. After the completion of the reaction, as indicated by TLC, acetonitile was evaporated. ETOAc (15 ml) were added to the crude mass. The organic layer was dried over anhydrous sodium sulfate. Removal of solvent led to the crude product, which was purified through pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colourless solid (0.40 g, 88 % yield). Recrystallization was carried out using ethylacetate as solvent.

Structure description top

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).

Computing details top

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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with intramolecular C—H···π interactions shown as dashed lines. Displacement ellipsoids are drawn at the 30% probability levels. H atoms are presented as a small spheres of arbitrary radius. Cg is the centroid of the C18–C23 ring.
	Fig. 2. Part of the crystal structure showing C—H···O hydrogen bonds (dotted lines) , with R₄⁴(38) ring motifs. [Symmetry code: (i) -1+x, y, z; (ii) 3/2-x, 1/2+y, 1/2-z; (iii) 1/2-x, 1/2+y, 1/2-z].

Methyl (Z)-2-{[N-(2-formylphenyl)-4- methylbenzenesulfonamido]methyl}-3-phenylprop-2-enoate top

Crystal data top

C₂₅H₂₃NO₅S	F(000) = 944
M_r = 449.50	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0773P)² + 0.5464P] where P = (F_o² + 2F_c²)/3
6991 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₅H₂₃NO₅S	V = 2239.7 (2) Å³
M_r = 449.50	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7475 (5) Å	µ = 0.18 mm⁻¹
b = 21.7053 (12) Å	T = 293 K
c = 11.2643 (6) Å	0.23 × 0.21 × 0.16 mm
β = 109.987 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6991 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4593 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.971	R_int = 0.028
28975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 0.99	Δρ_max = 0.45 e Å⁻³
6991 reflections	Δρ_min = −0.31 e Å⁻³
291 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z; (ii) −x+3/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₃NO₅S
M_r	449.50
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.7475 (5), 21.7053 (12), 11.2643 (6)
β (°)	109.987 (2)
V (Å³)	2239.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.23 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	28975, 6991, 4593
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.153, 0.99
No. of reflections	6991
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.31

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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)	149.0
C25—H25B···O2ⁱ	0.96	2.56	3.342 (3)	139.0
C10—H10···O1ⁱⁱ	0.93	2.51	3.309 (3)	144.7

Symmetry codes: (i) x−1, y, z; (ii) −x+3/2, y+1/2, −z+1/2.

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Aziz-ur-Rehman, Tanveer, W., Akkurt, M., Sattar, A., Abbasi, M. A. & Khan, I. U. (2010). Acta Cryst. E66, o2980. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bassindale, A. (1984). The Third Dimension in Organic Chemistry, ch. 1, p. 11. New York: John Wiley and Sons. Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, U. S. A. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Korolkovas, A. (1988). Essentials of Medicinal Chemistry, 2nd ed., pp. 699–716. New York: Wiley. Google Scholar
Mandell, G. L. & Sande, M. A. (1992). In Goodman and Gilman, The Pharmacological Basis of Therapeutics 2, edited by A. Gilman, T. W. Rall, A. S. Nies & P. Taylor, 8th ed., pp. 1047–1057. Singapore: McGraw-Hill. Google Scholar
Ranjith, S., Sugumar, P., Sureshbabu, R., Mohanakrishnan, A. K. & Ponnuswamy, M. N. (2009). Acta Cryst. E65, o483. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl (Z)-2-{[N-(2-formyl­phen­yl)-4-methyl­benzene­sulfonamido]­meth­yl}-3-phenyl­prop-2-enoate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

Methyl (Z)-2-{[N-(2-formylphenyl)-4-methylbenzenesulfonamido]methyl}-3-phenylprop-2-enoate