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

In the title compound, C(17)H(17)NO(5)S, the N atom is sp(3)-hybridized and the S atom has a distorted tetra-hedral configuration. The dihedral angle between the two aromatic rings is 30.0 (1)°, and that between the ethyl acetate group and the formyl-phenyl ring is 77.4 (1)°. The mol-ecules are linked into chains along [100] by C-H⋯O hydrogen bonds and the chains are linked via C-H⋯π inter-actions.

Related literature

For the biological properties of sulfonamide derivatives, see: Brown (1971 ▶); Nieto et al. (2005 ▶); Pomarnacka & Kozlarska-Kedra (2003 ▶). For related structures, see: Cameron et al. (1975 ▶); Cotton & Stokley (1970 ▶); Usha et al. (2005 ▶); Zhu et al. (2008 ▶).

Experimental

Crystal data

C17H17NO5S

M = 347.38

Orthorhombic,

a = 11.3442 (5) Å

b = 11.7731 (6) Å

c = 12.7809 (6) Å

V = 1706.97 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.948, T max = 0.958

10886 measured reflections

4104 independent reflections

3294 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.092

S = 0.95

4104 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1714 Friedel pairs

Flack parameter: −0.05 (7)

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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004413/ci2763sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004413/ci2763Isup2.hkl

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

C17H17NO5S	F(000) = 728
Mr = 347.38	Dx = 1.352 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4197 reflections
a = 11.3442 (5) Å	θ = 2.4–28.2°
b = 11.7731 (6) Å	µ = 0.22 mm−1
c = 12.7809 (6) Å	T = 293 K
V = 1706.97 (14) Å3	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Bruker Kappa APEXII area-detector diffractometer	4104 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
graphite	Rint = 0.022
ω scans	θmax = 28.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→10
Tmin = 0.948, Tmax = 0.958	k = −13→15
10886 measured reflections	l = −17→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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0478P)2 + 0.2327P] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.001
4104 reflections	Δρmax = 0.31 e Å−3
218 parameters	Δρmin = −0.23 e Å−3
0 restraints	Absolute structure: Flack (1983), 1714 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (7)

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
S1	0.53613 (4)	0.77486 (4)	0.23609 (3)	0.04875 (13)
N1	0.57693 (13)	0.74419 (13)	0.35602 (12)	0.0458 (4)
O1	0.58109 (13)	0.88549 (13)	0.21568 (11)	0.0627 (4)
O2	0.56980 (14)	0.68125 (16)	0.17264 (13)	0.0734 (5)
O3	0.75001 (14)	0.59352 (14)	0.41673 (16)	0.0749 (5)
O4	0.61531 (12)	0.47431 (12)	0.48118 (11)	0.0576 (4)
O5	0.89664 (14)	0.90059 (16)	0.34906 (17)	0.0833 (6)
C1	0.38089 (15)	0.77875 (16)	0.23788 (14)	0.0433 (4)
C2	0.3190 (2)	0.68510 (18)	0.20483 (17)	0.0559 (5)
H2	0.3585	0.6215	0.1798	0.067*
C3	0.1975 (2)	0.6866 (2)	0.2093 (2)	0.0693 (6)
H3	0.1546	0.6237	0.1870	0.083*
C4	0.1400 (2)	0.7802 (2)	0.24649 (19)	0.0705 (6)
H4	0.0581	0.7806	0.2496	0.085*
C5	0.2021 (2)	0.8738 (2)	0.27923 (18)	0.0660 (6)
H5A	0.1622	0.9371	0.3046	0.079*
C6	0.32367 (19)	0.87418 (18)	0.27450 (16)	0.0547 (5)
H6	0.3663	0.9376	0.2956	0.066*
C7	0.60070 (16)	0.83376 (15)	0.42938 (14)	0.0430 (4)
C8	0.51433 (19)	0.86705 (19)	0.49933 (16)	0.0585 (5)
H8	0.4400	0.8338	0.4967	0.070*
C9	0.5382 (3)	0.9487 (2)	0.57219 (17)	0.0717 (6)
H9	0.4799	0.9708	0.6192	0.086*
C10	0.6472 (3)	0.9983 (2)	0.57653 (17)	0.0713 (7)
H10	0.6630	1.0529	0.6273	0.086*
C11	0.7342 (2)	0.96779 (17)	0.50592 (16)	0.0585 (5)
H11	0.8075	1.0030	0.5082	0.070*
C12	0.71158 (17)	0.88403 (15)	0.43139 (14)	0.0444 (4)
C13	0.80492 (18)	0.85128 (18)	0.35747 (16)	0.0525 (5)
H13	0.7919	0.7886	0.3148	0.063*
C14	0.54423 (19)	0.63341 (16)	0.39786 (16)	0.0529 (4)
H14A	0.5022	0.5908	0.3447	0.064*
H14B	0.4917	0.6437	0.4570	0.064*
C15	0.65033 (19)	0.56723 (17)	0.43213 (15)	0.0485 (4)
C16	0.7055 (2)	0.39708 (18)	0.51686 (18)	0.0642 (6)
H16A	0.7631	0.4372	0.5591	0.077*
H16B	0.7457	0.3630	0.4577	0.077*
C17	0.6461 (3)	0.3085 (2)	0.5799 (3)	0.1089 (12)
H17A	0.6111	0.3426	0.6406	0.163*
H17B	0.7027	0.2525	0.6012	0.163*
H17C	0.5858	0.2729	0.5386	0.163*

	U11	U22	U33	U12	U13	U23
S1	0.0432 (2)	0.0579 (3)	0.0451 (2)	0.0008 (2)	0.0015 (2)	−0.0029 (2)
N1	0.0426 (8)	0.0414 (8)	0.0535 (8)	0.0000 (7)	−0.0064 (6)	0.0046 (7)
O1	0.0607 (9)	0.0714 (10)	0.0559 (8)	−0.0149 (8)	−0.0027 (7)	0.0166 (7)
O2	0.0594 (10)	0.0918 (12)	0.0692 (9)	0.0096 (9)	0.0088 (7)	−0.0290 (9)
O3	0.0449 (9)	0.0622 (10)	0.1175 (14)	0.0016 (8)	−0.0120 (9)	0.0194 (9)
O4	0.0636 (9)	0.0468 (8)	0.0622 (8)	0.0010 (7)	−0.0076 (7)	0.0095 (7)
O5	0.0478 (9)	0.0929 (13)	0.1093 (14)	−0.0136 (9)	0.0124 (9)	−0.0077 (11)
C1	0.0411 (9)	0.0509 (10)	0.0380 (8)	0.0016 (8)	−0.0043 (7)	−0.0017 (9)
C2	0.0555 (13)	0.0491 (11)	0.0630 (12)	0.0033 (10)	−0.0050 (9)	−0.0037 (9)
C3	0.0548 (13)	0.0680 (14)	0.0852 (16)	−0.0116 (12)	−0.0057 (12)	−0.0013 (12)
C4	0.0466 (11)	0.0937 (18)	0.0712 (14)	0.0004 (13)	0.0025 (10)	0.0003 (14)
C5	0.0592 (13)	0.0776 (15)	0.0612 (13)	0.0218 (13)	−0.0023 (11)	−0.0129 (12)
C6	0.0576 (12)	0.0564 (12)	0.0502 (10)	0.0069 (10)	−0.0082 (9)	−0.0095 (9)
C7	0.0454 (10)	0.0408 (9)	0.0429 (9)	0.0049 (8)	−0.0035 (8)	0.0058 (8)
C8	0.0522 (12)	0.0656 (13)	0.0576 (11)	0.0071 (10)	0.0076 (9)	0.0062 (10)
C9	0.0859 (17)	0.0712 (14)	0.0579 (12)	0.0135 (15)	0.0170 (14)	−0.0028 (11)
C10	0.111 (2)	0.0521 (12)	0.0508 (12)	0.0063 (13)	−0.0067 (13)	−0.0087 (10)
C11	0.0719 (15)	0.0488 (11)	0.0547 (12)	−0.0025 (11)	−0.0150 (10)	0.0027 (9)
C12	0.0463 (10)	0.0420 (9)	0.0449 (9)	0.0045 (8)	−0.0050 (8)	0.0067 (8)
C13	0.0432 (11)	0.0538 (11)	0.0605 (12)	0.0035 (10)	−0.0014 (9)	0.0079 (9)
C14	0.0452 (11)	0.0452 (10)	0.0684 (11)	−0.0022 (10)	−0.0031 (10)	0.0073 (9)
C15	0.0523 (12)	0.0427 (10)	0.0505 (10)	−0.0004 (9)	−0.0091 (9)	−0.0037 (8)
C16	0.0804 (16)	0.0486 (11)	0.0635 (13)	0.0096 (11)	−0.0243 (11)	0.0018 (10)
C17	0.132 (3)	0.0725 (18)	0.122 (3)	−0.0193 (18)	−0.047 (2)	0.0430 (18)

S1—O1	1.4229 (15)	C7—C8	1.383 (3)
S1—O2	1.4206 (16)	C7—C12	1.390 (3)
S1—N1	1.6414 (15)	C8—C9	1.365 (3)
S1—C1	1.7618 (18)	C8—H8	0.93
N1—C7	1.437 (2)	C9—C10	1.370 (4)
N1—C14	1.458 (2)	C9—H9	0.93
O3—C15	1.189 (2)	C10—C11	1.385 (3)
O4—C15	1.322 (2)	C10—H10	0.93
O4—C16	1.443 (2)	C11—C12	1.395 (3)
O5—C13	1.196 (3)	C11—H11	0.93
C1—C6	1.379 (3)	C12—C13	1.471 (3)
C1—C2	1.374 (3)	C13—H13	0.93
C2—C3	1.380 (3)	C14—C15	1.499 (3)
C2—H2	0.93	C14—H14A	0.97
C3—C4	1.367 (3)	C14—H14B	0.97
C3—H3	0.93	C16—C17	1.480 (4)
C4—C5	1.373 (3)	C16—H16A	0.97
C4—H4	0.93	C16—H16B	0.97
C5—C6	1.381 (3)	C17—H17A	0.96
C5—H5A	0.93	C17—H17B	0.96
C6—H6	0.93	C17—H17C	0.96
O1—S1—O2	120.6 (1)	C8—C9—H9	119.8
O1—S1—N1	105.7 (1)	C10—C9—H9	119.8
O2—S1—N1	106.7 (1)	C9—C10—C11	120.4 (2)
O1—S1—C1	109.7 (1)	C9—C10—H10	119.8
O2—S1—C1	107.2 (1)	C11—C10—H10	119.8
N1—S1—C1	106.0 (1)	C10—C11—C12	119.8 (2)
C7—N1—C14	117.7 (2)	C10—C11—H11	120.1
C7—N1—S1	120.1 (1)	C12—C11—H11	120.1
C14—N1—S1	117.9 (1)	C7—C12—C11	118.69 (19)
C15—O4—C16	117.27 (16)	C7—C12—C13	121.86 (18)
C6—C1—C2	121.17 (18)	C11—C12—C13	119.45 (19)
C6—C1—S1	119.73 (15)	O5—C13—C12	123.8 (2)
C2—C1—S1	119.08 (15)	O5—C13—H13	118.1
C3—C2—C1	119.2 (2)	C12—C13—H13	118.1
C3—C2—H2	120.4	N1—C14—C15	111.6 (2)
C1—C2—H2	120.4	N1—C14—H14A	109.3
C2—C3—C4	120.1 (2)	C15—C14—H14A	109.3
C2—C3—H3	120.0	N1—C14—H14B	109.3
C4—C3—H3	120.0	C15—C14—H14B	109.3
C5—C4—C3	120.6 (2)	H14A—C14—H14B	108.0
C5—C4—H4	119.7	O3—C15—O4	125.4 (2)
C3—C4—H4	119.7	O3—C15—C14	125.5 (2)
C4—C5—C6	120.1 (2)	O4—C15—C14	109.11 (17)
C4—C5—H5A	120.0	O4—C16—C17	107.0 (2)
C6—C5—H5A	120.0	O4—C16—H16A	110.3
C1—C6—C5	118.9 (2)	C17—C16—H16A	110.3
C1—C6—H6	120.6	O4—C16—H16B	110.3
C5—C6—H6	120.6	C17—C16—H16B	110.3
C8—C7—C12	120.55 (19)	H16A—C16—H16B	108.6
C8—C7—N1	119.79 (18)	C16—C17—H17A	109.5
C12—C7—N1	119.63 (17)	C16—C17—H17B	109.5
C9—C8—C7	120.0 (2)	H17A—C17—H17B	109.5
C9—C8—H8	120.0	C16—C17—H17C	109.5
C7—C8—H8	120.0	H17A—C17—H17C	109.5
C8—C9—C10	120.5 (2)	H17B—C17—H17C	109.5
O1—S1—N1—C7	24.90 (17)	C14—N1—C7—C12	119.11 (18)
O2—S1—N1—C7	154.43 (15)	S1—N1—C7—C12	−84.75 (19)
C1—S1—N1—C7	−91.53 (15)	C12—C7—C8—C9	−1.0 (3)
O1—S1—N1—C14	−179.00 (14)	N1—C7—C8—C9	177.16 (19)
O2—S1—N1—C14	−49.47 (17)	C7—C8—C9—C10	0.1 (3)
C1—S1—N1—C14	64.58 (16)	C8—C9—C10—C11	1.1 (4)
O1—S1—C1—C6	−33.51 (18)	C9—C10—C11—C12	−1.5 (3)
O2—S1—C1—C6	−166.12 (17)	C8—C7—C12—C11	0.6 (3)
N1—S1—C1—C6	80.23 (17)	N1—C7—C12—C11	−177.55 (16)
O1—S1—C1—C2	148.00 (16)	C8—C7—C12—C13	−179.43 (17)
O2—S1—C1—C2	15.4 (2)	N1—C7—C12—C13	2.4 (3)
N1—S1—C1—C2	−98.26 (16)	C10—C11—C12—C7	0.6 (3)
C6—C1—C2—C3	−0.5 (3)	C10—C11—C12—C13	−179.32 (19)
S1—C1—C2—C3	177.94 (18)	C7—C12—C13—O5	171.5 (2)
C1—C2—C3—C4	−0.2 (3)	C11—C12—C13—O5	−8.5 (3)
C2—C3—C4—C5	0.3 (4)	C7—N1—C14—C15	−80.8 (2)
C3—C4—C5—C6	0.2 (4)	S1—N1—C14—C15	122.49 (16)
C2—C1—C6—C5	1.1 (3)	C16—O4—C15—O3	−1.5 (3)
S1—C1—C6—C5	−177.41 (17)	C16—O4—C15—C14	177.78 (17)
C4—C5—C6—C1	−0.9 (3)	N1—C14—C15—O3	−8.5 (3)
C14—N1—C7—C8	−59.1 (2)	N1—C14—C15—O4	172.19 (15)
S1—N1—C7—C8	97.09 (19)	C15—O4—C16—C17	173.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3i	0.93	2.57	3.218 (3)	127
C16—H16B···Cg1ii	0.97	2.73	3.605 (3)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3i	0.93	2.57	3.218 (3)	127
C16—H16B⋯Cg1ii	0.97	2.73	3.605 (3)	150

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of C1–C6 ring.