Ethyl 2-[N-(2-formyl-phen-yl)benzene-sulfonamido]acetate.

In the mol-ecule of the title compound, C(17)H(17)NO(5)S, the two aromatic rings are oriented at an angle of 30.13 (10)°. The ethyl acetate group assumes an extended conformation. Mol-ecules are linked into C(7) chains running along the a axis by inter-molecular C-H⋯O hydrogen bonds, and the chains are crosslinked via C-H⋯π inter-actions, with the sulfonyl-bound phenyl ring acting as an acceptor.

Related literature

For the activities of sulfonamides, see: Krishnaiah et al. (1995 ▶); Dupont et al. (1978 ▶); Sethu Sankar et al. (2002 ▶). For related literature, see: Bassindale (1984 ▶).

Experimental

Crystal data

C17H17NO5S

M = 347.38

Orthorhombic,

a = 11.3512 (6) Å

b = 11.7820 (6) Å

c = 12.8045 (6) Å

V = 1712.47 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 (2) K

0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.948, T max = 0.960

13978 measured reflections

5831 independent reflections

3738 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.02

5831 reflections

218 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), with 2533 Friedel pairs

Flack parameter: 0.04 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900292X/ci2739sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900292X/ci2739Isup2.hkl

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

C17H17NO5S	F(000) = 728
Mr = 347.38	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5831 reflections
a = 11.3512 (6) Å	θ = 2.4–31.9°
b = 11.7820 (6) Å	µ = 0.22 mm−1
c = 12.8045 (6) Å	T = 293 K
V = 1712.47 (15) Å3	Block, white
Z = 4	0.25 × 0.22 × 0.19 mm

Bruker APEXII CCD area-detector diffractometer	5831 independent reflections
Radiation source: fine-focus sealed tube	3738 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω and φ scans	θmax = 31.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.948, Tmax = 0.960	k = −17→14
13978 measured reflections	l = −19→17

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0543P)2 + 0.0353P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
5831 reflections	Δρmax = 0.29 e Å−3
218 parameters	Δρmin = −0.25 e Å−3
2 restraints	Absolute structure: Flack (1983), 2533 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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.

	x	y	z	Uiso*/Ueq
C1	0.6483 (2)	0.49883 (17)	0.57621 (17)	0.0725 (5)
H1	0.6643	0.5535	0.6266	0.087*
C2	0.7343 (2)	0.46784 (15)	0.50573 (16)	0.0599 (4)
H2	0.8076	0.5030	0.5079	0.072*
C3	0.71222 (15)	0.38413 (13)	0.43117 (13)	0.0455 (4)
C4	0.60095 (14)	0.33360 (13)	0.42953 (13)	0.0439 (4)
C5	0.51443 (18)	0.36705 (17)	0.49915 (16)	0.0601 (5)
H5	0.4401	0.3341	0.4965	0.072*
C6	0.5388 (2)	0.44896 (19)	0.57199 (17)	0.0749 (5)
H6	0.4807	0.4711	0.6190	0.090*
C7	0.80521 (16)	0.35124 (16)	0.35744 (16)	0.0541 (4)
H7	0.7922	0.2885	0.3149	0.065*
C8	0.38129 (14)	0.27847 (14)	0.23805 (13)	0.0441 (3)
C9	0.31891 (18)	0.18498 (16)	0.20531 (16)	0.0567 (5)
H9	0.3582	0.1211	0.1807	0.068*
C10	0.1974 (2)	0.18686 (19)	0.20932 (19)	0.0706 (6)
H10	0.1544	0.1243	0.1867	0.085*
C11	0.14047 (18)	0.2805 (2)	0.24649 (18)	0.0712 (6)
H11	0.0586	0.2811	0.2499	0.085*
C12	0.20264 (19)	0.37386 (19)	0.27891 (17)	0.0684 (6)
H12	0.1627	0.4371	0.3041	0.082*
C13	0.32368 (18)	0.37453 (15)	0.27450 (15)	0.0554 (4)
H13	0.3661	0.4381	0.2955	0.066*
C14	0.54399 (17)	0.13373 (14)	0.39808 (16)	0.0540 (4)
H14A	0.5015	0.0911	0.3453	0.065*
H14B	0.4919	0.1444	0.4573	0.065*
C15	0.65056 (17)	0.06720 (14)	0.43210 (14)	0.0493 (4)
C16	0.7056 (2)	−0.10263 (15)	0.51699 (17)	0.0665 (6)
H16A	0.7630	−0.0624	0.5592	0.080*
H16B	0.7459	−0.1367	0.4580	0.080*
C17	0.6456 (3)	−0.1912 (2)	0.5801 (3)	0.1116 (11)
H17A	0.6075	−0.1565	0.6389	0.167*
H17B	0.7026	−0.2453	0.6044	0.167*
H17C	0.5879	−0.2292	0.5378	0.167*
N1	0.57707 (12)	0.24388 (11)	0.35598 (11)	0.0472 (3)
O1	0.89698 (13)	0.40067 (14)	0.34903 (16)	0.0853 (5)
O2	0.58147 (12)	0.38549 (11)	0.21580 (11)	0.0643 (4)
O3	0.57026 (13)	0.18131 (14)	0.17302 (12)	0.0758 (4)
O4	0.75012 (13)	0.09354 (12)	0.41701 (15)	0.0768 (5)
O5	0.61509 (11)	−0.02585 (10)	0.48124 (11)	0.0592 (3)
S1	0.53632 (4)	0.27483 (4)	0.23629 (3)	0.04953 (12)

	U11	U22	U33	U12	U13	U23
C1	0.1104 (14)	0.0522 (10)	0.0549 (11)	0.0040 (10)	−0.0043 (10)	−0.0089 (9)
C2	0.0728 (13)	0.0477 (9)	0.0593 (10)	−0.0020 (9)	−0.0145 (8)	0.0032 (8)
C3	0.0469 (9)	0.0410 (8)	0.0484 (8)	0.0041 (7)	−0.0058 (7)	0.0073 (7)
C4	0.0445 (9)	0.0421 (8)	0.0451 (8)	0.0043 (7)	−0.0039 (7)	0.0069 (7)
C5	0.0544 (11)	0.0629 (11)	0.0629 (11)	0.0072 (9)	0.0080 (9)	0.0063 (9)
C6	0.0906 (13)	0.0731 (12)	0.0611 (11)	0.0163 (12)	0.0180 (13)	−0.0021 (10)
C7	0.0456 (10)	0.0544 (10)	0.0624 (11)	0.0023 (9)	−0.0015 (8)	0.0070 (8)
C8	0.0436 (8)	0.0493 (8)	0.0395 (7)	0.0012 (7)	−0.0038 (6)	−0.0011 (8)
C9	0.0585 (12)	0.0463 (9)	0.0653 (12)	0.0026 (9)	−0.0056 (9)	−0.0044 (8)
C10	0.0562 (12)	0.0676 (12)	0.0879 (15)	−0.0114 (11)	−0.0087 (11)	0.0002 (11)
C11	0.0472 (10)	0.0903 (16)	0.0763 (14)	0.0025 (11)	0.0026 (10)	−0.0014 (13)
C12	0.0615 (12)	0.0784 (14)	0.0653 (12)	0.0238 (11)	−0.0038 (10)	−0.0146 (11)
C13	0.0579 (11)	0.0552 (10)	0.0532 (9)	0.0078 (8)	−0.0074 (8)	−0.0093 (8)
C14	0.0459 (10)	0.0443 (8)	0.0719 (10)	−0.0015 (8)	−0.0038 (9)	0.0079 (8)
C15	0.0518 (10)	0.0414 (8)	0.0546 (9)	−0.0014 (8)	−0.0071 (8)	−0.0024 (8)
C16	0.0828 (15)	0.0493 (9)	0.0674 (12)	0.0114 (10)	−0.0237 (11)	0.0029 (9)
C17	0.133 (3)	0.0727 (16)	0.129 (3)	−0.0176 (16)	−0.048 (2)	0.0442 (17)
N1	0.0434 (7)	0.0416 (7)	0.0567 (8)	−0.0004 (6)	−0.0075 (6)	0.0048 (6)
O1	0.0493 (8)	0.0925 (11)	0.1142 (13)	−0.0147 (8)	0.0139 (8)	−0.0077 (10)
O2	0.0613 (8)	0.0729 (9)	0.0587 (7)	−0.0149 (7)	−0.0028 (6)	0.0174 (7)
O3	0.0589 (9)	0.0942 (11)	0.0743 (9)	0.0085 (8)	0.0091 (7)	−0.0305 (8)
O4	0.0472 (8)	0.0625 (8)	0.1207 (13)	0.0017 (7)	−0.0119 (8)	0.0208 (9)
O5	0.0664 (8)	0.0460 (6)	0.0652 (8)	0.0016 (6)	−0.0078 (6)	0.0095 (6)
S1	0.0434 (2)	0.0569 (2)	0.0483 (2)	0.0004 (2)	0.00160 (19)	−0.00257 (19)

C1—C6	1.376 (3)	C11—C12	1.371 (3)
C1—C2	1.378 (3)	C11—H11	0.93
C1—H1	0.93	C12—C13	1.375 (3)
C2—C3	1.395 (3)	C12—H12	0.93
C2—H2	0.93	C13—H13	0.93
C3—C4	1.396 (2)	C14—N1	1.455 (2)
C3—C7	1.468 (2)	C14—C15	1.506 (3)
C4—C5	1.384 (2)	C14—H14A	0.97
C4—N1	1.442 (2)	C14—H14B	0.97
C5—C6	1.370 (3)	C15—O4	1.188 (2)
C5—H5	0.93	C15—O5	1.327 (2)
C6—H6	0.93	C16—O5	1.443 (2)
C7—O1	1.198 (2)	C16—C17	1.486 (3)
C7—H7	0.93	C16—H16A	0.97
C8—C9	1.375 (2)	C16—H16B	0.97
C8—C13	1.388 (2)	C17—H17A	0.96
C8—S1	1.7605 (16)	C17—H17B	0.96
C9—C10	1.380 (3)	C17—H17C	0.96
C9—H9	0.93	N1—S1	1.6419 (14)
C10—C11	1.365 (3)	O2—S1	1.4253 (13)
C10—H10	0.93	O3—S1	1.4209 (15)
C6—C1—C2	120.05 (19)	C13—C12—H12	119.8
C6—C1—H1	120.0	C12—C13—C8	118.67 (18)
C2—C1—H1	120.0	C12—C13—H13	120.7
C1—C2—C3	120.5 (2)	C8—C13—H13	120.7
C1—C2—H2	119.7	N1—C14—C15	111.36 (15)
C3—C2—H2	119.7	N1—C14—H14A	109.4
C2—C3—C4	118.28 (17)	C15—C14—H14A	109.4
C2—C3—C7	119.84 (17)	N1—C14—H14B	109.4
C4—C3—C7	121.88 (16)	C15—C14—H14B	109.4
C5—C4—C3	120.73 (16)	H14A—C14—H14B	108.0
C5—C4—N1	119.76 (16)	O4—C15—O5	125.58 (17)
C3—C4—N1	119.50 (15)	O4—C15—C14	125.54 (16)
C6—C5—C4	119.74 (19)	O5—C15—C14	108.88 (15)
C6—C5—H5	120.1	O5—C16—C17	106.6 (2)
C4—C5—H5	120.1	O5—C16—H16A	110.4
C5—C6—C1	120.6 (2)	C17—C16—H16A	110.4
C5—C6—H6	119.7	O5—C16—H16B	110.4
C1—C6—H6	119.7	C17—C16—H16B	110.4
O1—C7—C3	123.7 (2)	H16A—C16—H16B	108.6
O1—C7—H7	118.2	C16—C17—H17A	109.5
C3—C7—H7	118.2	C16—C17—H17B	109.5
C9—C8—C13	120.88 (16)	H17A—C17—H17B	109.5
C9—C8—S1	119.43 (13)	C16—C17—H17C	109.5
C13—C8—S1	119.68 (14)	H17A—C17—H17C	109.5
C8—C9—C10	119.37 (18)	H17B—C17—H17C	109.5
C8—C9—H9	120.3	C4—N1—C14	117.44 (14)
C10—C9—H9	120.3	C4—N1—S1	119.99 (10)
C11—C10—C9	119.9 (2)	C14—N1—S1	118.12 (12)
C11—C10—H10	120.0	C15—O5—C16	116.89 (15)
C9—C10—H10	120.0	O3—S1—O2	120.46 (10)
C10—C11—C12	120.7 (2)	O3—S1—N1	106.47 (9)
C10—C11—H11	119.7	O2—S1—N1	105.88 (8)
C12—C11—H11	119.7	O3—S1—C8	107.29 (9)
C11—C12—C13	120.43 (19)	O2—S1—C8	109.85 (9)
C11—C12—H12	119.8	N1—S1—C8	105.97 (8)
C6—C1—C2—C3	−1.4 (3)	N1—C14—C15—O5	172.45 (14)
C1—C2—C3—C4	0.5 (3)	C5—C4—N1—C14	−59.0 (2)
C1—C2—C3—C7	−179.31 (18)	C3—C4—N1—C14	119.59 (16)
C2—C3—C4—C5	0.9 (2)	C5—C4—N1—S1	96.88 (17)
C7—C3—C4—C5	−179.28 (16)	C3—C4—N1—S1	−84.51 (17)
C2—C3—C4—N1	−177.66 (14)	C15—C14—N1—C4	−81.22 (19)
C7—C3—C4—N1	2.1 (2)	C15—C14—N1—S1	122.42 (14)
C3—C4—C5—C6	−1.4 (3)	O4—C15—O5—C16	−1.6 (3)
N1—C4—C5—C6	177.22 (17)	C14—C15—O5—C16	178.12 (15)
C4—C5—C6—C1	0.4 (3)	C17—C16—O5—C15	173.12 (19)
C2—C1—C6—C5	1.0 (3)	C4—N1—S1—O3	154.32 (14)
C2—C3—C7—O1	−8.5 (3)	C14—N1—S1—O3	−49.95 (15)
C4—C3—C7—O1	171.70 (19)	C4—N1—S1—O2	24.99 (16)
C13—C8—C9—C10	−0.3 (3)	C14—N1—S1—O2	−179.28 (13)
S1—C8—C9—C10	178.31 (17)	C4—N1—S1—C8	−91.66 (14)
C8—C9—C10—C11	−0.6 (3)	C14—N1—S1—C8	64.07 (15)
C9—C10—C11—C12	0.8 (3)	C9—C8—S1—O3	15.45 (17)
C10—C11—C12—C13	0.0 (3)	C13—C8—S1—O3	−165.94 (15)
C11—C12—C13—C8	−0.9 (3)	C9—C8—S1—O2	148.05 (15)
C9—C8—C13—C12	1.0 (3)	C13—C8—S1—O2	−33.34 (17)
S1—C8—C13—C12	−177.55 (16)	C9—C8—S1—N1	−98.00 (15)
N1—C14—C15—O4	−7.8 (3)	C13—C8—S1—N1	80.61 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.93	2.57	3.220 (2)	127
C16—H16B···Cg1ii	0.97	2.75	3.615 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.93	2.57	3.220 (2)	127
C16—H16B⋯Cg1ii	0.97	2.75	3.615 (2)	150

Symmetry codes: (i) ; (ii) .