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

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

doi:10.1107/S1600536812000864

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Pages o418-o419

doi:10.1107/S1600536812000864

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Methyl (2Z)-2-({N-[2-(hydroxymethyl)phenyl]-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 2 January 2012; accepted 9 January 2012; online 14 January 2012)

In the title compound, C₂₅H₂₅NO₅S, the O atom of the hydroxy group is disordered over two positions, with occupancies of 0.820 (2) and 0.180 (2). The sulfonyl-bound benzene ring forms dihedral angles of 31.8 (1) and 60.7 (1)°, respectively, with the hydroxymethylbenzene and phenyl rings. The molecular conformation is stabilized by an intramolecular O—H⋯O hydrogen bond, generating an S(8) ring motif. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ); Mandell & Sande (1992 ). For resonance effects of acrylate, see: Merlino (1971 ); Varghese et al. (1986 ). For related structures, see: Madhanraj et al. (2011 ); Aziz-ur-Rehman et al. (2010 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₅H₂₅NO₅S
M_r = 451.52
Triclinic, $[P \overline 1]$
a = 7.9528 (3) Å
b = 9.5396 (3) Å
c = 15.3299 (5) Å
α = 88.253 (2)°
β = 83.571 (1)°
γ = 76.215 (2)°
V = 1122.42 (7) Å³
Z = 2
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
25861 measured reflections
7132 independent reflections
5255 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.127
S = 1.05
7132 reflections
297 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C18–C23 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O2	0.82	2.23	2.958 (2)	147
C9—H9⋯Cg1	0.93	2.80	3.545 (2)	138
C5—H5⋯O4ⁱ	0.93	2.54	3.429 (2)	160
C14—H14C⋯O2ⁱⁱ	0.96	2.55	3.359 (2)	143
C12—H12⋯Cg1ⁱⁱⁱ	0.93	2.72	3.506 (2)	143
C20—H20⋯Cg2^iv	0.93	2.92	3.593 (2)	130
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) x, y+1, z; (iv) -x, -y+1, -z.

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: 10.1107/S1600536812000864/bt5779sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000864/bt5779Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000864/bt5779Isup3.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 O1 atom of the hydroxyl group is disordered over two positions with occupancies 0.820 (2):0.180 (2). The S1 atom shows a distorted tetrahedral geometry, with O2—S1—O3[120.0 (1)°] and N1—S1—C8[108.6 (1)°] angles deviating from ideal tetrahedral values. The significant difference in length of the C24—O5 = 1.329 (2) Å and C25—O5 = 1.442 (2) Å bonds is attributed to a partial contribution from the O^-–C = O⁺–C resonance structure of the O4═C24—O5—C25 group (Merlino, 1971). This feature, commonly observed in the carboxylic ester group of the substituents in various compounds gives average values of 1.340 Å and 1.447 Å respectively for these bonds (Varghese et al., 1986). The sum of bond angles around N1 (346°) indicates that N1 is in sp² hybridization. The sulfonyl-bound benzene (C8–C13) ring forms dihedral angles of 31.8 (1)° and 60.7 (1)°, respectively, with the hydroxymethyl benzene (C1–C6) and benzene (C18–C23) rings. The dihedral angle between hydroxymethyl benzene and benzene rings is 41.2 (1)°. The geometric parameters of the title molecule agrees well with those reported for similar structures (Madhanraj et al., 2011, Aziz-ur-Rehman et al., 2010).

The molecule is stabilized by an intramolecular O1A-H1A···O2 hydrogen bond generating an S(8) ring motif (Bernstein et al., 1995) and an intramolecular C-H···π interaction between a sulfonyl–bound benzene H atom and a benzene (C18–C23) ring with a C9—H9···Cg1 seperation of 2.80 Å (Table 1; Cg1 is the centroid of the C18–C23 benzene ring). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The molecules at x, y, z and 1-x, 1-y, 1-z are linked by C5—H5···O4 hydrogen bonds into cyclic centrosymmetric R₂²(18) dimers (Fig. 2). These dimers are linked by C14—H14C···O2 hydrogen bonds forming supramolecular tapes running along the [100] directions (Fig. 3). The crystal packing is further stabilized by C—H···π interactions, the first one between a sulfonyl–bound benzene H atom and the benzene ring (C18–C23) of an adjacent molecule, with a C12—H12···Cg1ⁱⁱⁱ seperation of 2.72 Å and the second one between a benzene H atom and the benzene ring (C8–C13) of a neighbouring molecule, with a C20—H20···Cg2^iv seperation of 2.92 Å ( Table 1 and Fig. 4; Cg1 and Cg2 are the centroids of the (C18–C23) benzene and (C8–C13) benzene rings, respectively. symmetry code as in Fig. 3).

Related literature top

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988); Mandell & Sande (1992). For resonance effects of acrylate, see: Merlino (1971); Varghese et al. (1986). For related structures, see: Madhanraj et al. (2011); Aziz-ur-Rehman et al. (2010). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of N-(2-(hydroxymethyl)phenyl)-(4-methylbenzene)sulfonamide (1 mmol, 0.277 g) and potassium carbonate (1.5 mmol, 0.207 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, 0.304 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) and water (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 (0.435 g, 96% yield). Recrystallization was carried out using ethylacetate as solvent.

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, showing 30% probability displacement ellipsoids. H atoms are presented as a small spheres of arbitrary radius. The disordered component is shown.
	Fig. 2. Part of the crystal structure of the title compound showing C—H···O intermolecular hydrogen bonds (dotted lines) generating R²₂(18) centrosymmetric dimer. [Symmetry code: (i) 1-x, 1-y, 1-z].
	Fig. 3. Supramolecular tape formation in (I) whereby centrosymmetrc R₂²(18) dimeric aggregates sustained by C—H···O (magenta dashed lines) contacts are linked via C—H···O contacts (cyan dashed lines) along [1 0 0].
	Fig. 4. A view of the C—H···π interactions, in the crystal structure of the title compound. Cg1 and Cg2 are the centroids of the (C18–C23) benzene and (C8–C13) benzene rings, respectively. [Symmetry code: (iii) x, 1+y, z; (iv) -x, 1-y, -z.]

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

Crystal data top

C₂₅H₂₅NO₅S	Z = 2
M_r = 451.52	F(000) = 476
Triclinic, P1	D_x = 1.336 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9528 (3) Å	Cell parameters from 7307 reflections
b = 9.5396 (3) Å	θ = 1.3–31.3°
c = 15.3299 (5) Å	µ = 0.18 mm⁻¹
α = 88.253 (2)°	T = 293 K
β = 83.571 (1)°	Block, colourless
γ = 76.215 (2)°	0.23 × 0.21 × 0.16 mm
V = 1122.42 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	7132 independent reflections
Radiation source: fine-focus sealed tube	5255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 31.3°, θ_min = 1.3°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
T_min = 0.959, T_max = 0.971	l = −21→22
25861 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0619P)² + 0.1756P] where P = (F_o² + 2F_c²)/3
7132 reflections	(Δ/σ)_max < 0.001
297 parameters	Δρ_max = 0.31 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₅H₂₅NO₅S	γ = 76.215 (2)°
M_r = 451.52	V = 1122.42 (7) Å³
Triclinic, P1	Z = 2
a = 7.9528 (3) Å	Mo Kα radiation
b = 9.5396 (3) Å	µ = 0.18 mm⁻¹
c = 15.3299 (5) Å	T = 293 K
α = 88.253 (2)°	0.23 × 0.21 × 0.16 mm
β = 83.571 (1)°

Data collection top

Bruker APEXII CCD diffractometer	7132 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5255 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.971	R_int = 0.027
25861 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
7132 reflections	Δρ_min = −0.31 e Å⁻³
297 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	Occ. (<1)
C1	0.20025 (16)	0.58467 (13)	0.36181 (8)	0.0327 (2)
C2	0.03176 (18)	0.65951 (14)	0.39145 (9)	0.0401 (3)
H2	−0.0629	0.6363	0.3699	0.048*
C3	0.0045 (2)	0.76791 (16)	0.45268 (10)	0.0511 (4)
H3	−0.1082	0.8175	0.4725	0.061*
C4	0.1448 (3)	0.80219 (17)	0.48427 (11)	0.0575 (4)
H4	0.1271	0.8762	0.5248	0.069*
C5	0.3121 (2)	0.72685 (16)	0.45592 (10)	0.0515 (4)
H5	0.4056	0.7507	0.4783	0.062*
C6	0.34408 (18)	0.61594 (14)	0.39460 (9)	0.0393 (3)
C8	0.04825 (17)	0.61769 (13)	0.16515 (8)	0.0343 (3)
C9	−0.05349 (19)	0.55105 (14)	0.12048 (9)	0.0410 (3)
H9	−0.0160	0.4536	0.1064	0.049*
C10	−0.2116 (2)	0.63118 (16)	0.09707 (10)	0.0469 (3)
H10	−0.2801	0.5867	0.0672	0.056*
C11	−0.26927 (19)	0.77612 (15)	0.11741 (10)	0.0443 (3)
C12	−0.1653 (2)	0.84054 (14)	0.16182 (10)	0.0460 (3)
H12	−0.2029	0.9380	0.1758	0.055*
C13	−0.0071 (2)	0.76351 (14)	0.18575 (9)	0.0423 (3)
H13	0.0615	0.8085	0.2152	0.051*
C14	−0.4407 (2)	0.8624 (2)	0.09128 (14)	0.0681 (5)
H14A	−0.4480	0.8451	0.0306	0.102*
H14B	−0.4493	0.9632	0.0997	0.102*
H14C	−0.5343	0.8338	0.1268	0.102*
C15	0.11357 (16)	0.36554 (12)	0.31857 (8)	0.0339 (2)
H15A	0.0152	0.3908	0.2843	0.041*
H15B	0.0683	0.3736	0.3801	0.041*
C16	0.20914 (16)	0.21190 (13)	0.29938 (8)	0.0350 (3)
C17	0.16244 (17)	0.12583 (14)	0.24467 (9)	0.0393 (3)
H17	0.2324	0.0328	0.2378	0.047*
C18	0.01129 (17)	0.16300 (13)	0.19390 (9)	0.0364 (3)
C19	0.0349 (2)	0.14001 (16)	0.10405 (10)	0.0459 (3)
H19	0.1452	0.0979	0.0768	0.055*
C20	−0.1044 (2)	0.17926 (17)	0.05454 (10)	0.0530 (4)
H20	−0.0870	0.1655	−0.0059	0.064*
C21	−0.2684 (2)	0.23862 (17)	0.09474 (11)	0.0528 (4)
H21	−0.3616	0.2661	0.0613	0.063*
C22	−0.29490 (19)	0.25740 (16)	0.18413 (11)	0.0482 (3)
H22	−0.4065	0.2948	0.2114	0.058*
C23	−0.15595 (18)	0.22084 (15)	0.23353 (9)	0.0403 (3)
H23	−0.1744	0.2350	0.2939	0.048*
C24	0.36113 (17)	0.15603 (14)	0.34979 (9)	0.0385 (3)
C25	0.6052 (2)	−0.03467 (18)	0.36773 (12)	0.0552 (4)
H25A	0.6903	0.0223	0.3604	0.083*
H25B	0.6568	−0.1303	0.3459	0.083*
H25C	0.5648	−0.0397	0.4289	0.083*
N1	0.22546 (13)	0.47007 (10)	0.29838 (7)	0.0317 (2)
O2	0.36596 (14)	0.61308 (12)	0.18924 (7)	0.0517 (3)
O3	0.29601 (13)	0.38840 (11)	0.14434 (6)	0.0463 (2)
O4	0.39010 (15)	0.21719 (12)	0.41165 (8)	0.0565 (3)
O5	0.46033 (14)	0.03080 (11)	0.31967 (7)	0.0522 (3)
S1	0.24992 (4)	0.51837 (3)	0.19400 (2)	0.03568 (9)
C7	0.52803 (19)	0.53288 (18)	0.36886 (11)	0.0509 (4)
H7A	0.5850	0.5067	0.4217	0.061*	0.820 (2)
H7B	0.5248	0.4441	0.3405	0.061*	0.820 (2)
H7C	0.5370	0.4333	0.3870	0.061*	0.180 (2)
H7D	0.5488	0.5337	0.3053	0.061*	0.180 (2)
O1A	0.62756 (19)	0.60607 (18)	0.31313 (10)	0.0630 (4)	0.820 (2)
H1A	0.5817	0.6274	0.2677	0.095*	0.820 (2)
O1B	0.6587 (8)	0.5806 (8)	0.4002 (4)	0.0630 (4)	0.180 (2)
H1B	0.6916	0.5313	0.4426	0.095*	0.180 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0352 (6)	0.0318 (5)	0.0329 (6)	−0.0103 (5)	−0.0073 (5)	0.0012 (4)
C2	0.0375 (7)	0.0411 (7)	0.0410 (7)	−0.0077 (5)	−0.0050 (5)	−0.0004 (5)
C3	0.0522 (9)	0.0453 (7)	0.0490 (8)	0.0005 (7)	−0.0006 (7)	−0.0060 (6)
C4	0.0780 (12)	0.0469 (8)	0.0479 (9)	−0.0131 (8)	−0.0075 (8)	−0.0130 (7)
C5	0.0619 (10)	0.0499 (8)	0.0506 (8)	−0.0235 (7)	−0.0166 (7)	−0.0052 (6)
C6	0.0404 (7)	0.0410 (6)	0.0412 (7)	−0.0157 (6)	−0.0117 (5)	0.0007 (5)
C8	0.0372 (6)	0.0345 (6)	0.0325 (6)	−0.0101 (5)	−0.0069 (5)	0.0034 (5)
C9	0.0461 (7)	0.0339 (6)	0.0444 (7)	−0.0090 (5)	−0.0124 (6)	−0.0010 (5)
C10	0.0471 (8)	0.0449 (7)	0.0533 (8)	−0.0144 (6)	−0.0185 (6)	0.0033 (6)
C11	0.0422 (7)	0.0425 (7)	0.0469 (8)	−0.0079 (6)	−0.0077 (6)	0.0134 (6)
C12	0.0571 (9)	0.0318 (6)	0.0468 (8)	−0.0062 (6)	−0.0066 (6)	0.0045 (5)
C13	0.0543 (8)	0.0351 (6)	0.0408 (7)	−0.0139 (6)	−0.0114 (6)	0.0013 (5)
C14	0.0516 (10)	0.0588 (10)	0.0901 (14)	−0.0034 (8)	−0.0194 (9)	0.0235 (9)
C15	0.0310 (6)	0.0329 (6)	0.0398 (6)	−0.0107 (5)	−0.0060 (5)	0.0000 (5)
C16	0.0316 (6)	0.0341 (6)	0.0408 (6)	−0.0093 (5)	−0.0079 (5)	0.0025 (5)
C17	0.0337 (6)	0.0343 (6)	0.0502 (8)	−0.0065 (5)	−0.0083 (5)	−0.0041 (5)
C18	0.0352 (6)	0.0316 (6)	0.0449 (7)	−0.0099 (5)	−0.0096 (5)	−0.0053 (5)
C19	0.0446 (8)	0.0464 (7)	0.0468 (8)	−0.0111 (6)	−0.0021 (6)	−0.0097 (6)
C20	0.0671 (10)	0.0552 (8)	0.0417 (8)	−0.0198 (8)	−0.0144 (7)	−0.0038 (6)
C21	0.0543 (9)	0.0470 (8)	0.0627 (10)	−0.0127 (7)	−0.0288 (8)	0.0006 (7)
C22	0.0341 (7)	0.0471 (7)	0.0645 (9)	−0.0079 (6)	−0.0120 (6)	−0.0089 (7)
C23	0.0368 (7)	0.0434 (7)	0.0430 (7)	−0.0122 (5)	−0.0061 (5)	−0.0076 (5)
C24	0.0355 (6)	0.0372 (6)	0.0448 (7)	−0.0107 (5)	−0.0099 (5)	0.0052 (5)
C25	0.0428 (8)	0.0558 (9)	0.0626 (10)	0.0017 (7)	−0.0180 (7)	0.0089 (7)
N1	0.0315 (5)	0.0334 (5)	0.0332 (5)	−0.0115 (4)	−0.0074 (4)	−0.0002 (4)
O2	0.0446 (6)	0.0671 (7)	0.0514 (6)	−0.0299 (5)	−0.0065 (5)	0.0116 (5)
O3	0.0406 (5)	0.0528 (6)	0.0407 (5)	−0.0009 (4)	−0.0032 (4)	−0.0082 (4)
O4	0.0584 (7)	0.0547 (6)	0.0587 (7)	−0.0063 (5)	−0.0291 (5)	−0.0066 (5)
O5	0.0452 (6)	0.0466 (5)	0.0611 (7)	0.0038 (5)	−0.0211 (5)	−0.0034 (5)
S1	0.03119 (16)	0.04236 (17)	0.03454 (16)	−0.01077 (12)	−0.00391 (11)	0.00105 (12)
C7	0.0365 (7)	0.0594 (9)	0.0609 (9)	−0.0160 (7)	−0.0129 (6)	−0.0015 (7)
O1A	0.0481 (8)	0.0859 (10)	0.0618 (9)	−0.0297 (7)	−0.0067 (6)	0.0066 (8)
O1B	0.0481 (8)	0.0859 (10)	0.0618 (9)	−0.0297 (7)	−0.0067 (6)	0.0066 (8)

Geometric parameters (Å, º) top

C1—C2	1.3926 (18)	C16—C24	1.4897 (17)
C1—C6	1.3966 (17)	C17—C18	1.4717 (18)
C1—N1	1.4484 (15)	C17—H17	0.9300
C2—C3	1.380 (2)	C18—C19	1.3863 (19)
C2—H2	0.9300	C18—C23	1.3900 (19)
C3—C4	1.375 (2)	C19—C20	1.385 (2)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.381 (2)	C20—C21	1.375 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.395 (2)	C21—C22	1.374 (2)
C5—H5	0.9300	C21—H21	0.9300
C6—C7	1.504 (2)	C22—C23	1.3799 (19)
C8—C9	1.3869 (18)	C22—H22	0.9300
C8—C13	1.3901 (18)	C23—H23	0.9300
C8—S1	1.7535 (13)	C24—O4	1.1998 (17)
C9—C10	1.3859 (19)	C24—O5	1.3288 (16)
C9—H9	0.9300	C25—O5	1.4419 (17)
C10—C11	1.383 (2)	C25—H25A	0.9600
C10—H10	0.9300	C25—H25B	0.9600
C11—C12	1.385 (2)	C25—H25C	0.9600
C11—C14	1.505 (2)	N1—S1	1.6548 (10)
C12—C13	1.379 (2)	O2—S1	1.4323 (10)
C12—H12	0.9300	O3—S1	1.4247 (10)
C13—H13	0.9300	C7—O1B	1.367 (4)
C14—H14A	0.9600	C7—O1A	1.385 (2)
C14—H14B	0.9600	C7—H7A	0.9700
C14—H14C	0.9600	C7—H7B	0.9700
C15—N1	1.4915 (15)	C7—H7C	0.9700
C15—C16	1.5025 (17)	C7—H7D	0.9700
C15—H15A	0.9700	O1A—H7D	1.0542
C15—H15B	0.9700	O1A—H1A	0.8200
C16—C17	1.3315 (18)	O1B—H1B	0.8200

C2—C1—C6	120.74 (12)	C20—C19—H19	119.8
C2—C1—N1	119.33 (11)	C18—C19—H19	119.8
C6—C1—N1	119.89 (11)	C21—C20—C19	120.00 (14)
C3—C2—C1	120.35 (13)	C21—C20—H20	120.0
C3—C2—H2	119.8	C19—C20—H20	120.0
C1—C2—H2	119.8	C22—C21—C20	120.15 (14)
C4—C3—C2	119.66 (14)	C22—C21—H21	119.9
C4—C3—H3	120.2	C20—C21—H21	119.9
C2—C3—H3	120.2	C21—C22—C23	120.04 (14)
C3—C4—C5	120.15 (14)	C21—C22—H22	120.0
C3—C4—H4	119.9	C23—C22—H22	120.0
C5—C4—H4	119.9	C22—C23—C18	120.64 (13)
C4—C5—C6	121.63 (15)	C22—C23—H23	119.7
C4—C5—H5	119.2	C18—C23—H23	119.7
C6—C5—H5	119.2	O4—C24—O5	123.50 (12)
C5—C6—C1	117.44 (13)	O4—C24—C16	123.47 (12)
C5—C6—C7	119.57 (13)	O5—C24—C16	113.03 (11)
C1—C6—C7	122.96 (12)	O5—C25—H25A	109.5
C9—C8—C13	120.41 (12)	O5—C25—H25B	109.5
C9—C8—S1	119.85 (10)	H25A—C25—H25B	109.5
C13—C8—S1	119.73 (10)	O5—C25—H25C	109.5
C10—C9—C8	119.29 (12)	H25A—C25—H25C	109.5
C10—C9—H9	120.4	H25B—C25—H25C	109.5
C8—C9—H9	120.4	C1—N1—C15	115.15 (10)
C11—C10—C9	121.12 (13)	C1—N1—S1	115.85 (8)
C11—C10—H10	119.4	C15—N1—S1	115.24 (8)
C9—C10—H10	119.4	C24—O5—C25	116.57 (12)
C10—C11—C12	118.59 (13)	O3—S1—O2	119.99 (7)
C10—C11—C14	120.71 (14)	O3—S1—N1	106.47 (6)
C12—C11—C14	120.69 (14)	O2—S1—N1	105.76 (6)
C13—C12—C11	121.53 (13)	O3—S1—C8	107.61 (6)
C13—C12—H12	119.2	O2—S1—C8	107.99 (6)
C11—C12—H12	119.2	N1—S1—C8	108.60 (6)
C12—C13—C8	119.05 (13)	O1B—C7—O1A	60.6 (3)
C12—C13—H13	120.5	O1B—C7—C6	117.5 (3)
C8—C13—H13	120.5	O1A—C7—C6	114.78 (14)
C11—C14—H14A	109.5	O1B—C7—H7A	49.6
C11—C14—H14B	109.5	O1A—C7—H7A	108.6
H14A—C14—H14B	109.5	C6—C7—H7A	108.6
C11—C14—H14C	109.5	O1B—C7—H7B	132.9
H14A—C14—H14C	109.5	O1A—C7—H7B	108.6
H14B—C14—H14C	109.5	C6—C7—H7B	108.6
N1—C15—C16	112.99 (10)	H7A—C7—H7B	107.5
N1—C15—H15A	109.0	O1B—C7—H7C	108.7
C16—C15—H15A	109.0	O1A—C7—H7C	135.8
N1—C15—H15B	109.0	C6—C7—H7C	108.0
C16—C15—H15B	109.0	H7A—C7—H7C	65.9
H15A—C15—H15B	107.8	H7B—C7—H7C	44.2
C17—C16—C24	120.28 (12)	O1B—C7—H7D	107.1
C17—C16—C15	124.55 (11)	O1A—C7—H7D	49.4
C24—C16—C15	115.12 (11)	C6—C7—H7D	107.9
C16—C17—C18	126.57 (12)	H7A—C7—H7D	143.1
C16—C17—H17	116.7	H7B—C7—H7D	64.9
C18—C17—H17	116.7	H7C—C7—H7D	107.2
C19—C18—C23	118.62 (12)	C7—O1A—H7D	44.3
C19—C18—C17	119.55 (12)	C7—O1A—H1A	109.5
C23—C18—C17	121.83 (12)	H7D—O1A—H1A	71.9
C20—C19—C18	120.50 (14)	C7—O1B—H1B	109.5

C6—C1—C2—C3	1.2 (2)	C21—C22—C23—C18	−0.9 (2)
N1—C1—C2—C3	179.20 (12)	C19—C18—C23—C22	−1.3 (2)
C1—C2—C3—C4	0.2 (2)	C17—C18—C23—C22	178.71 (13)
C2—C3—C4—C5	−1.1 (3)	C17—C16—C24—O4	−165.13 (15)
C3—C4—C5—C6	0.6 (3)	C15—C16—C24—O4	12.34 (19)
C4—C5—C6—C1	0.8 (2)	C17—C16—C24—O5	14.26 (19)
C4—C5—C6—C7	−177.31 (15)	C15—C16—C24—O5	−168.28 (11)
C2—C1—C6—C5	−1.67 (19)	C2—C1—N1—C15	−46.81 (15)
N1—C1—C6—C5	−179.64 (12)	C6—C1—N1—C15	131.19 (12)
C2—C1—C6—C7	176.36 (13)	C2—C1—N1—S1	91.87 (12)
N1—C1—C6—C7	−1.61 (19)	C6—C1—N1—S1	−90.13 (12)
C13—C8—C9—C10	−0.4 (2)	C16—C15—N1—C1	−139.33 (11)
S1—C8—C9—C10	−179.19 (11)	C16—C15—N1—S1	81.74 (11)
C8—C9—C10—C11	0.1 (2)	O4—C24—O5—C25	2.6 (2)
C9—C10—C11—C12	0.1 (2)	C16—C24—O5—C25	−176.78 (12)
C9—C10—C11—C14	179.67 (15)	C1—N1—S1—O3	172.29 (8)
C10—C11—C12—C13	0.0 (2)	C15—N1—S1—O3	−49.07 (10)
C14—C11—C12—C13	−179.51 (15)	C1—N1—S1—O2	43.60 (10)
C11—C12—C13—C8	−0.4 (2)	C15—N1—S1—O2	−177.76 (8)
C9—C8—C13—C12	0.6 (2)	C1—N1—S1—C8	−72.09 (10)
S1—C8—C13—C12	179.34 (11)	C15—N1—S1—C8	66.55 (9)
N1—C15—C16—C17	−122.13 (14)	C9—C8—S1—O3	15.29 (13)
N1—C15—C16—C24	60.53 (14)	C13—C8—S1—O3	−163.49 (11)
C24—C16—C17—C18	176.84 (13)	C9—C8—S1—O2	146.17 (11)
C15—C16—C17—C18	−0.4 (2)	C13—C8—S1—O2	−32.61 (13)
C16—C17—C18—C19	127.54 (16)	C9—C8—S1—N1	−99.59 (12)
C16—C17—C18—C23	−52.5 (2)	C13—C8—S1—N1	81.63 (12)
C23—C18—C19—C20	2.5 (2)	C5—C6—C7—O1B	−6.8 (4)
C17—C18—C19—C20	−177.55 (13)	C1—C6—C7—O1B	175.2 (4)
C18—C19—C20—C21	−1.4 (2)	C5—C6—C7—O1A	−75.15 (19)
C19—C20—C21—C22	−0.8 (2)	C1—C6—C7—O1A	106.87 (16)
C20—C21—C22—C23	2.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C18–C23 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2	0.82	2.23	2.958 (2)	147
C9—H9···Cg1	0.93	2.80	3.545 (2)	138
C5—H5···O4ⁱ	0.93	2.54	3.429 (2)	160
C14—H14C···O2ⁱⁱ	0.96	2.55	3.359 (2)	143
C12—H12···Cg1ⁱⁱⁱ	0.93	2.72	3.506 (2)	143
C20—H20···Cg2^iv	0.93	2.92	3.593 (2)	130

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₅NO₅S
M_r	451.52
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9528 (3), 9.5396 (3), 15.3299 (5)
α, β, γ (°)	88.253 (2), 83.571 (1), 76.215 (2)
V (Å³)	1122.42 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.23 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
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	25861, 7132, 5255
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.730

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.127, 1.05
No. of reflections	7132
No. of parameters	297
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −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

Cg1 and Cg2 are the centroids of the C18–C23 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2	0.82	2.23	2.958 (2)	147.0
C9—H9···Cg1	0.93	2.80	3.545 (2)	138.0
C5—H5···O4ⁱ	0.93	2.54	3.429 (2)	159.6
C14—H14C···O2ⁱⁱ	0.96	2.55	3.359 (2)	142.5
C12—H12···Cg1ⁱⁱⁱ	0.93	2.72	3.506 (2)	143.0
C20—H20···Cg2^iv	0.93	2.92	3.593 (2)	130.0

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) x, y+1, z; (iv) −x, −y+1, −z.

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
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Volume 68| Part 2| February 2012| Pages o418-o419

doi:10.1107/S1600536812000864

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

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