Ethyl 3-[2-(p-toluene­sulfonamido)phen­yl]acrylate

Jin, M.-F.; Zhu, B.-Y.

doi:10.1107/S1600536809034163

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2312

doi:10.1107/S1600536809034163

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Ethyl 3-[2-(p-toluenesulfonamido)phenyl]acrylate

Mei-Fang Jin ^a ^* and Bao-Yong Zhu ^b

^aDepartment of Chemical Engineering, Anyang Institute of Technology, 455000 Anyang, People's Republic of China, and ^bDepartment of Chemistry, Dezhou University, 253023 Dezhou, People's Republic of China
^*Correspondence e-mail: jmeifangns@163.com

(Received 22 August 2009; accepted 26 August 2009; online 5 September 2009)

In the title compound, C₁₈H₁₉NO₄S, the two benzene rings form a dihedral angle of 52.2 (7)°. The crystal struture is stabilized by N—H⋯O hydrogen bonds, which link the molecules into dimers.

Related literature

For functionalized carbon frameworks, see: Mukherjee et al. (2007 ). For sulfonamido compounds and their use in pharmaceuticals, see: Patchett et al. (1995 ). For a related structure, see: Senthil Kumaret al. (2006 ).

Experimental

Crystal data

C₁₈H₁₉NO₄S
M_r = 345.40
Triclinic, $[P \overline 1]$
a = 8.001 (4) Å
b = 10.245 (5) Å
c = 11.402 (5) Å
α = 81.182 (5)°
β = 70.895 (4)°
γ = 86.604 (5)°
V = 872.7 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 291 K
0.46 × 0.43 × 0.38 mm

Data collection

Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.91, T_max = 0.93
15343 measured reflections
3553 independent reflections
2784 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.147
S = 1.18
3553 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.92	2.01	2.920 (2)	172
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: CrysAlis Pro (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis Pro. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis Pro; data reduction: CrysAlis Pro; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and CAMERON (Pearce & Watkin, 1993 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034163/bg2295sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034163/bg2295Isup2.hkl

checkCIF report

Comment top

Electron-deficient olefin, particularly α,β-unsaturated carbonyl compound, was used as a fundamental material to construct functionalized carbon frameworks (Mukherjee et al., 2007). Sulfonamido is an important group in natural compounds and many pharmaceuticals (Patchett et al., 1995). We selected N-(2-formylphenyl)(4-methylbenzene)sulfonamide and (ethoxycarbonylmethylene)triphenylphosphorane to synthesize a new compound formulated as C₁₈H₁₉N₁O₄S₁ (I) with dimeric structures via hydrogen bonds.

The molecular structure of (I) is illustrated in Fig. 1. The geometry of the molecule is close to the related compound Ethyl 2-([N-(2- iodophenyl)phenylsulfonamido]methyl)-1-phenylsulfonyl-1H-indole-3- carboxylate (Senthil Kumar, et al., 2006). Bond lengths and angles (S1—O1 =1.427 (1) Å, S1—O2 = 1.431 (1) Å, O1-S1-O2 = 121.3 (1) °, O1-S1-N1 = 107.3 (9) °, O2S1N1 = 104.7 (1) °) involving the S atom of the phenylsufonyl group present in the molecule is similar to the distances (S1—O1 = 1.425 Å, S1—O2 = 1.429 Å) and angles (O1-S1-O2 = 120.4 (8) °, O1-S1-N1 = 106.9 (7) °, O2-S1-N1 = 106.7 (7) °)) that reported in the literature (Senthil Kumar, et al., 2006); the O—S—O, N—S—C and N—S—O angles deviate significantly from the ideal tetrahedral value (Table 1), which is consistent to the reported data in the literature (Senthil Kumar, et al., 2006). The phenyl rings (C2—>C7) and (C8—>C13) are planar to within 0.01 Å. The dihedral angle between the two phenyl rings is 52.3 (1) °.

The crystal struture is further stabilized by hydrogen bonding. As shown in Fig.2, a dimeric structure is formed via intermolecular hydrogen bonds N1—H2···O3ⁱ (i = 1 - x, 1 - y, -z) (Table 2).

Related literature top

For functionalized carbon framework, see: Mukherjee et al. (2007).

For sulfonamido compounds and their use in pharmaceuticals, see: Patchett et al. (1995). For a related structure, see: Senthil Kumar et al. (2006).

Experimental top

The mixture of N-(2-formylphenyl)(4-methylbenzene)sulfonamide (0.500 g, 1.82 mmol) and (ethoxycarbonylmethylene)triphenylphosphorane (0.700 g, 2.00 mmol) in dichloromethane (10 ml) was stirred at room temperature for 2 h (Scheme 2). After evaporation of the solvent, the title compound was obtained from the residue by chromatography. Single crystals suitable for X-ray analysis were obtained from ethyl acetate by slow evaporation.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2006); cell refinement: CrysAlis PRO (Oxford Diffraction, 2006); data reduction: CrysAlis PRO (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Pearce & Watkin, 1993); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoide are drawn at 30% probability level.
	Fig. 2. The dimeric structure of the title compound. Dotted lines indicate hydrogen bonds [Symmetry code: (i) = 1 - x, 1 - y, -z.]
	Fig. 3. The formation of the title compound.

Ethyl 3-[2-(p-toluenesulfonamido)phenyl]acrylate top

Crystal data top

C₁₈H₁₉NO₄S	Z = 2
M_r = 345.40	F(000) = 364
Triclinic, P1	D_x = 1.314 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.001 (4) Å	Cell parameters from 8607 reflections
b = 10.245 (5) Å	θ = 2.8–29.2°
c = 11.402 (5) Å	µ = 0.21 mm⁻¹
α = 81.182 (5)°	T = 291 K
β = 70.895 (4)°	Block, colourless
γ = 86.604 (5)°	0.46 × 0.43 × 0.38 mm
V = 872.7 (8) Å³

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	3553 independent reflections
Radiation source: fine-focus sealed tube	2784 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 15.9149 pixels mm^-1	θ_max = 26.4°, θ_min = 2.8°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→12
T_min = 0.91, T_max = 0.93	l = −14→14
15343 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0903P)²] where P = (F_o² + 2F_c²)/3
3553 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₈H₁₉NO₄S	γ = 86.604 (5)°
M_r = 345.40	V = 872.7 (8) Å³
Triclinic, P1	Z = 2
a = 8.001 (4) Å	Mo Kα radiation
b = 10.245 (5) Å	µ = 0.21 mm⁻¹
c = 11.402 (5) Å	T = 291 K
α = 81.182 (5)°	0.46 × 0.43 × 0.38 mm
β = 70.895 (4)°

Data collection top

Oxford Diffraction Gemini S Ultra diffractometer	3553 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2784 reflections with I > 2σ(I)
T_min = 0.91, T_max = 0.93	R_int = 0.020
15343 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.18	Δρ_max = 0.24 e Å⁻³
3553 reflections	Δρ_min = −0.28 e Å⁻³
219 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 > 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.

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

	x	y	z	U_iso*/U_eq
S1	0.72847 (6)	0.25225 (4)	0.25492 (5)	0.0646 (2)
O1	0.70944 (18)	0.19430 (14)	0.38058 (14)	0.0831 (5)
O2	0.86898 (18)	0.21412 (15)	0.15094 (16)	0.0947 (5)
O3	0.4015 (2)	0.67440 (14)	0.03433 (11)	0.0782 (4)
O4	0.2137 (2)	0.78869 (13)	0.17227 (12)	0.0891 (5)
N1	0.54807 (18)	0.22083 (13)	0.22784 (12)	0.0526 (4)
H1	0.5561	0.2476	0.1454	0.063*
C1	0.7190 (4)	0.8460 (2)	0.2182 (3)	0.1029 (8)
H1A	0.8038	0.8833	0.1408	0.154*
H1B	0.7451	0.8732	0.2872	0.154*
H1C	0.6024	0.8761	0.2198	0.154*
C2	0.7276 (3)	0.69829 (19)	0.22896 (18)	0.0662 (5)
C3	0.7857 (3)	0.6372 (2)	0.12236 (19)	0.0740 (6)
H3	0.8228	0.6888	0.0440	0.089*
C4	0.7895 (3)	0.5024 (2)	0.12980 (18)	0.0690 (5)
H4	0.8275	0.4629	0.0571	0.083*
C5	0.7361 (2)	0.42488 (17)	0.24668 (16)	0.0548 (4)
C6	0.6821 (2)	0.4838 (2)	0.35380 (17)	0.0640 (5)
H6	0.6484	0.4326	0.4324	0.077*
C7	0.6786 (3)	0.6198 (2)	0.34324 (19)	0.0706 (5)
H7	0.6419	0.6595	0.4158	0.085*
C8	0.3783 (2)	0.22505 (15)	0.32128 (13)	0.0459 (4)
C9	0.3306 (2)	0.11643 (16)	0.41448 (14)	0.0533 (4)
H9	0.4105	0.0470	0.4163	0.064*
C10	0.1657 (2)	0.11117 (18)	0.50398 (15)	0.0598 (5)
H10	0.1346	0.0386	0.5663	0.072*
C11	0.0473 (2)	0.21322 (19)	0.50108 (16)	0.0643 (5)
H11	−0.0647	0.2091	0.5609	0.077*
C12	0.0937 (2)	0.32127 (18)	0.41022 (16)	0.0578 (4)
H12	0.0122	0.3897	0.4095	0.069*
C13	0.2609 (2)	0.33082 (15)	0.31862 (13)	0.0461 (4)
C14	0.3083 (2)	0.44882 (16)	0.22402 (14)	0.0494 (4)
H14	0.4004	0.4398	0.1505	0.059*
C15	0.2336 (3)	0.56488 (18)	0.23341 (15)	0.0671 (5)
H15	0.1397	0.5761	0.3052	0.080*
C16	0.2919 (3)	0.67872 (17)	0.13510 (15)	0.0592 (5)
C17	0.2604 (4)	0.9087 (2)	0.08528 (19)	0.1009 (9)
H17A	0.3855	0.9073	0.0380	0.121*
H17B	0.1945	0.9160	0.0266	0.121*
C18	0.2205 (4)	1.0191 (2)	0.1528 (2)	0.0906 (7)
H18A	0.2421	1.0994	0.0947	0.136*
H18B	0.2941	1.0158	0.2049	0.136*
H18C	0.0985	1.0162	0.2042	0.136*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0528 (3)	0.0488 (3)	0.0846 (4)	0.0071 (2)	−0.0191 (2)	0.0037 (2)
O1	0.0854 (10)	0.0685 (9)	0.1021 (11)	−0.0082 (7)	−0.0561 (9)	0.0283 (8)
O2	0.0584 (8)	0.0700 (10)	0.1324 (13)	0.0181 (7)	−0.0011 (8)	−0.0179 (9)
O3	0.1002 (10)	0.0654 (9)	0.0459 (7)	0.0207 (7)	−0.0027 (7)	0.0068 (6)
O4	0.1339 (13)	0.0402 (7)	0.0584 (8)	0.0133 (7)	0.0093 (8)	0.0022 (6)
N1	0.0575 (8)	0.0454 (7)	0.0484 (7)	0.0050 (6)	−0.0125 (6)	0.0007 (6)
C1	0.153 (2)	0.0586 (13)	0.1080 (18)	−0.0072 (14)	−0.0580 (17)	−0.0062 (13)
C2	0.0749 (12)	0.0547 (11)	0.0725 (12)	−0.0066 (9)	−0.0297 (10)	−0.0035 (9)
C3	0.0894 (14)	0.0598 (12)	0.0637 (11)	−0.0128 (10)	−0.0193 (10)	0.0107 (9)
C4	0.0772 (13)	0.0585 (11)	0.0595 (11)	−0.0064 (9)	−0.0077 (9)	−0.0030 (9)
C5	0.0429 (9)	0.0537 (10)	0.0604 (10)	−0.0024 (7)	−0.0112 (7)	0.0031 (8)
C6	0.0629 (11)	0.0661 (12)	0.0553 (10)	−0.0075 (9)	−0.0140 (8)	0.0063 (9)
C7	0.0790 (13)	0.0664 (13)	0.0641 (11)	−0.0047 (10)	−0.0171 (10)	−0.0138 (9)
C8	0.0542 (9)	0.0409 (8)	0.0429 (8)	−0.0037 (7)	−0.0170 (7)	−0.0030 (6)
C9	0.0689 (11)	0.0417 (9)	0.0497 (9)	−0.0031 (8)	−0.0232 (8)	0.0023 (7)
C10	0.0731 (12)	0.0512 (10)	0.0521 (9)	−0.0173 (9)	−0.0202 (9)	0.0082 (7)
C11	0.0575 (10)	0.0652 (12)	0.0594 (10)	−0.0140 (9)	−0.0078 (8)	0.0042 (9)
C12	0.0506 (9)	0.0557 (10)	0.0614 (10)	−0.0013 (8)	−0.0151 (8)	0.0025 (8)
C13	0.0504 (9)	0.0438 (9)	0.0433 (8)	−0.0033 (7)	−0.0169 (7)	0.0008 (6)
C14	0.0536 (9)	0.0459 (9)	0.0429 (8)	0.0040 (7)	−0.0121 (7)	0.0013 (6)
C15	0.0839 (13)	0.0472 (10)	0.0487 (9)	0.0063 (9)	0.0029 (9)	0.0008 (8)
C16	0.0737 (12)	0.0467 (10)	0.0475 (9)	0.0056 (8)	−0.0093 (8)	−0.0025 (7)
C17	0.166 (2)	0.0426 (11)	0.0665 (13)	−0.0021 (13)	−0.0062 (14)	0.0073 (9)
C18	0.128 (2)	0.0522 (12)	0.0851 (15)	−0.0036 (12)	−0.0264 (14)	−0.0070 (11)

Geometric parameters (Å, º) top

S1—O1	1.4268 (15)	C7—H7	0.9300
S1—O2	1.4282 (15)	C8—C9	1.391 (2)
S1—N1	1.6308 (16)	C8—C13	1.395 (2)
S1—C5	1.760 (2)	C9—C10	1.377 (2)
O3—C16	1.201 (2)	C9—H9	0.9300
O4—C16	1.315 (2)	C10—C11	1.373 (3)
O4—C17	1.440 (2)	C10—H10	0.9300
N1—C8	1.429 (2)	C11—C12	1.372 (2)
N1—H1	0.9203	C11—H11	0.9300
C1—C2	1.499 (3)	C12—C13	1.400 (2)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.468 (2)
C1—H1C	0.9600	C14—C15	1.302 (2)
C2—C7	1.371 (3)	C14—H14	0.9300
C2—C3	1.383 (3)	C15—C16	1.468 (2)
C3—C4	1.371 (3)	C15—H15	0.9300
C3—H3	0.9300	C17—C18	1.427 (3)
C4—C5	1.390 (2)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.376 (3)	C18—H18A	0.9600
C6—C7	1.380 (3)	C18—H18B	0.9600
C6—H6	0.9300	C18—H18C	0.9600

O1—S1—O2	121.53 (10)	C10—C9—C8	120.32 (16)
O1—S1—N1	107.04 (8)	C10—C9—H9	119.8
O2—S1—N1	104.81 (9)	C8—C9—H9	119.8
O1—S1—C5	108.14 (9)	C11—C10—C9	119.93 (16)
O2—S1—C5	107.81 (8)	C11—C10—H10	120.0
N1—S1—C5	106.63 (7)	C9—C10—H10	120.0
C16—O4—C17	117.49 (15)	C12—C11—C10	120.17 (17)
C8—N1—S1	121.54 (11)	C12—C11—H11	119.9
C8—N1—H1	118.1	C10—C11—H11	119.9
S1—N1—H1	111.8	C11—C12—C13	121.51 (17)
C2—C1—H1A	109.5	C11—C12—H12	119.2
C2—C1—H1B	109.5	C13—C12—H12	119.2
H1A—C1—H1B	109.5	C8—C13—C12	117.60 (14)
C2—C1—H1C	109.5	C8—C13—C14	122.03 (14)
H1A—C1—H1C	109.5	C12—C13—C14	120.38 (15)
H1B—C1—H1C	109.5	C15—C14—C13	126.10 (15)
C7—C2—C3	118.06 (19)	C15—C14—H14	116.9
C7—C2—C1	121.61 (19)	C13—C14—H14	116.9
C3—C2—C1	120.33 (18)	C14—C15—C16	122.61 (16)
C4—C3—C2	121.34 (18)	C14—C15—H15	118.7
C4—C3—H3	119.3	C16—C15—H15	118.7
C2—C3—H3	119.3	O3—C16—O4	123.41 (17)
C3—C4—C5	119.55 (19)	O3—C16—C15	124.92 (17)
C3—C4—H4	120.2	O4—C16—C15	111.63 (15)
C5—C4—H4	120.2	C18—C17—O4	109.33 (17)
C6—C5—C4	119.91 (17)	C18—C17—H17A	109.8
C6—C5—S1	120.91 (13)	O4—C17—H17A	109.8
C4—C5—S1	119.11 (14)	C18—C17—H17B	109.8
C5—C6—C7	119.18 (17)	O4—C17—H17B	109.8
C5—C6—H6	120.4	H17A—C17—H17B	108.3
C7—C6—H6	120.4	C17—C18—H18A	109.5
C2—C7—C6	121.93 (18)	C17—C18—H18B	109.5
C2—C7—H7	119.0	H18A—C18—H18B	109.5
C6—C7—H7	119.0	C17—C18—H18C	109.5
C9—C8—C13	120.45 (15)	H18A—C18—H18C	109.5
C9—C8—N1	117.27 (15)	H18B—C18—H18C	109.5
C13—C8—N1	122.25 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.92	2.01	2.920 (2)	172

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₄S
M_r	345.40
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	8.001 (4), 10.245 (5), 11.402 (5)
α, β, γ (°)	81.182 (5), 70.895 (4), 86.604 (5)
V (Å³)	872.7 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.46 × 0.43 × 0.38

Data collection
Diffractometer	Oxford Diffraction Gemini S Ultra diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.91, 0.93
No. of measured, independent and observed [I > 2σ(I)] reflections	15343, 3553, 2784
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.147, 1.18
No. of reflections	3553
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: CrysAlis PRO (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Pearce & Watkin, 1993), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.92	2.01	2.920 (2)	171.6

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The authours thank the Anyang Institute of Technology, the Natural Science Foundation of Shandong (project code: Y 2007F 68), the Scientific Research Developmental Project of Shandong Provincial Education Department (project code: J07WC09) and the Scientific Developmental Project of Dezhou City (project code 050702) for support.

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