Propyl 2-(4-methyl-benzene-sulfonamido)-benzoate.

In the title compound, C(17)H(19)NO(4)S, the terminal ethyl group is disordered over two sets of sites, with refined site occupancies of 0.536 (7) and 0.464 (7). The dihedral angle between the two aromatic rings is 81.92 (12)°. The mol-ecular conformation is stabilized by intra-molecular N-H⋯O and C-H⋯O hydrogen bonds, which generate S(6) motifs. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶, 2012 ▶); Khan et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H19NO4S

M = 333.40

Monoclinic,

a = 16.206 (5) Å

b = 8.513 (2) Å

c = 12.021 (3) Å

β = 92.352 (2)°

V = 1657.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 296 K

0.34 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

15110 measured reflections

4039 independent reflections

2343 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.178

S = 0.95

4039 reflections

209 parameters

4 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015528/hg5208sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015528/hg5208Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015528/hg5208Isup3.cml

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

C17H19NO4S	F(000) = 704
Mr = 333.40	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4265 reflections
a = 16.206 (5) Å	θ = 2.5–23.7°
b = 8.513 (2) Å	µ = 0.22 mm−1
c = 12.021 (3) Å	T = 296 K
β = 92.352 (2)°	Needle, dark brown
V = 1657.0 (8) Å3	0.34 × 0.22 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.071
Graphite monochromator	θmax = 28.3°, θmin = 2.5°
φ and ω scans	h = −21→21
15110 measured reflections	k = −11→9
4039 independent reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.1068P)2] where P = (Fo2 + 2Fc2)/3
4039 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.41 e Å−3
4 restraints	Δρmin = −0.37 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	Occ. (<1)
S1	0.80026 (4)	0.16805 (7)	0.29221 (4)	0.0584 (2)
O1	0.77925 (11)	0.32859 (19)	0.31033 (16)	0.0767 (7)
O2	0.81365 (11)	0.06631 (19)	0.38522 (12)	0.0750 (7)
O3	0.64329 (12)	0.1994 (2)	0.03046 (17)	0.0869 (8)
O4	0.59833 (12)	0.0193 (2)	−0.09050 (17)	0.0942 (8)
N1	0.72438 (11)	0.1015 (2)	0.21272 (16)	0.0630 (7)
C1	1.10575 (19)	0.1688 (4)	0.0220 (3)	0.1018 (14)
C2	1.02933 (15)	0.1638 (3)	0.0893 (2)	0.0667 (9)
C3	0.96043 (17)	0.2539 (3)	0.0577 (2)	0.0722 (10)
C4	0.89084 (15)	0.2530 (3)	0.11718 (18)	0.0622 (8)
C5	0.88847 (13)	0.1625 (2)	0.21260 (16)	0.0501 (7)
C6	0.95491 (14)	0.0702 (3)	0.24444 (18)	0.0606 (8)
C7	1.02450 (15)	0.0731 (3)	0.1834 (2)	0.0718 (9)
C8	0.71875 (13)	−0.0507 (2)	0.16566 (19)	0.0558 (7)
C9	0.75079 (16)	−0.1809 (3)	0.2218 (2)	0.0696 (9)
C10	0.74210 (19)	−0.3271 (3)	0.1755 (3)	0.0821 (11)
C11	0.70270 (19)	−0.3495 (3)	0.0752 (3)	0.0795 (11)
C12	0.66964 (16)	−0.2228 (3)	0.0188 (2)	0.0763 (10)
C13	0.67714 (13)	−0.0703 (3)	0.0631 (2)	0.0594 (8)
C14	0.63951 (15)	0.0624 (4)	0.0015 (2)	0.0691 (10)
C15	0.5563 (2)	0.1421 (5)	−0.1561 (3)	0.1144 (14)
C16A	0.5014 (6)	0.0493 (10)	−0.2409 (6)	0.1144 (14)	0.536 (7)
C17A	0.4972 (7)	0.070 (2)	−0.3449 (9)	0.131 (4)	0.536 (7)
C16B	0.5434 (6)	0.0897 (12)	−0.2659 (7)	0.1144 (14)	0.464 (7)
C17B	0.4682 (7)	0.077 (3)	−0.3096 (12)	0.131 (4)	0.464 (7)
H1	0.68400	0.16460	0.19800	0.0760*
H7	1.06970	0.01200	0.20630	0.0860*
H5	0.84520	0.31260	0.09390	0.0750*
H6	0.96210	0.31630	−0.00570	0.0870*
H11	0.69810	−0.44980	0.04490	0.0950*
H12	0.77820	−0.16880	0.29080	0.0830*
H13	0.64190	−0.23790	−0.04960	0.0920*
H14A	1.09050	0.15610	−0.05550	0.1530*
H14B	1.14240	0.08550	0.04550	0.1530*
H14C	1.13300	0.26800	0.03320	0.1530*
H15A	0.59570	0.20750	−0.19340	0.1370*
H15B	0.52310	0.20800	−0.10950	0.1370*
H16A	0.51600	−0.06020	−0.22990	0.1370*	0.536 (7)
H16B	0.44540	0.06040	−0.21660	0.1370*	0.536 (7)
H17A	0.44610	0.02730	−0.37500	0.1970*	0.536 (7)
H17B	0.54260	0.01780	−0.37790	0.1970*	0.536 (7)
H17C	0.49940	0.18030	−0.36090	0.1970*	0.536 (7)
H8	0.95270	0.00630	0.30700	0.0730*
H10	0.76380	−0.41340	0.21400	0.0980*
H16C	0.57360	0.15980	−0.31310	0.1370*	0.464 (7)
H16D	0.56910	−0.01290	−0.27080	0.1370*	0.464 (7)
H17D	0.46750	0.00200	−0.36910	0.1970*	0.464 (7)
H17E	0.45030	0.17760	−0.33810	0.1970*	0.464 (7)
H17F	0.43160	0.04330	−0.25350	0.1970*	0.464 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0714 (4)	0.0507 (4)	0.0533 (3)	−0.0016 (3)	0.0056 (3)	−0.0040 (2)
O1	0.0920 (13)	0.0510 (11)	0.0879 (12)	0.0020 (8)	0.0141 (10)	−0.0185 (8)
O2	0.1016 (13)	0.0742 (12)	0.0496 (9)	−0.0102 (9)	0.0074 (9)	0.0070 (8)
O3	0.0933 (14)	0.0751 (14)	0.0913 (13)	0.0160 (10)	−0.0083 (11)	0.0078 (11)
O4	0.0951 (14)	0.1008 (16)	0.0846 (12)	−0.0095 (11)	−0.0226 (11)	0.0158 (11)
N1	0.0598 (11)	0.0503 (12)	0.0785 (13)	0.0065 (9)	−0.0010 (9)	−0.0059 (10)
C1	0.0773 (19)	0.131 (3)	0.099 (2)	−0.0341 (17)	0.0251 (17)	−0.043 (2)
C2	0.0646 (15)	0.0729 (17)	0.0628 (14)	−0.0159 (12)	0.0046 (11)	−0.0227 (13)
C3	0.0886 (19)	0.0786 (18)	0.0495 (12)	−0.0142 (14)	0.0033 (12)	0.0045 (12)
C4	0.0723 (15)	0.0624 (15)	0.0515 (12)	0.0043 (11)	−0.0038 (11)	0.0084 (10)
C5	0.0618 (12)	0.0434 (12)	0.0444 (10)	−0.0025 (9)	−0.0060 (9)	−0.0020 (8)
C6	0.0729 (15)	0.0562 (14)	0.0519 (12)	0.0057 (11)	−0.0061 (11)	0.0017 (10)
C7	0.0651 (15)	0.0727 (18)	0.0768 (16)	0.0088 (12)	−0.0077 (13)	−0.0115 (13)
C8	0.0532 (12)	0.0477 (13)	0.0668 (13)	−0.0045 (10)	0.0077 (10)	−0.0013 (10)
C9	0.0758 (16)	0.0529 (15)	0.0792 (16)	−0.0033 (12)	−0.0070 (13)	0.0034 (12)
C10	0.0897 (19)	0.0503 (16)	0.106 (2)	0.0007 (13)	0.0017 (17)	0.0060 (14)
C11	0.0877 (19)	0.0483 (16)	0.103 (2)	−0.0054 (13)	0.0099 (16)	−0.0103 (14)
C12	0.0714 (17)	0.0787 (19)	0.0791 (17)	−0.0157 (14)	0.0054 (13)	−0.0180 (15)
C13	0.0514 (12)	0.0585 (15)	0.0687 (14)	−0.0042 (10)	0.0088 (10)	−0.0021 (11)
C14	0.0604 (14)	0.0755 (19)	0.0714 (16)	−0.0047 (13)	0.0026 (12)	0.0028 (13)
C15	0.092 (2)	0.142 (3)	0.107 (2)	−0.0034 (17)	−0.0213 (17)	0.043 (2)
C16A	0.092 (2)	0.142 (3)	0.107 (2)	−0.0034 (17)	−0.0213 (17)	0.043 (2)
C17A	0.090 (7)	0.188 (6)	0.116 (7)	−0.010 (7)	0.012 (4)	0.050 (7)
C16B	0.092 (2)	0.142 (3)	0.107 (2)	−0.0034 (17)	−0.0213 (17)	0.043 (2)
C17B	0.090 (7)	0.188 (6)	0.116 (7)	−0.010 (7)	0.012 (4)	0.050 (7)

S1—O1	1.4273 (18)	C16A—C17A	1.262 (13)
S1—O2	1.4239 (17)	C16B—C17B	1.312 (15)
S1—N1	1.628 (2)	C1—H14A	0.9600
S1—C5	1.753 (2)	C1—H14B	0.9600
O3—C14	1.218 (4)	C1—H14C	0.9600
O4—C14	1.320 (3)	C3—H6	0.9300
O4—C15	1.461 (4)	C4—H5	0.9300
N1—C8	1.415 (3)	C6—H8	0.9300
N1—H1	0.8600	C7—H7	0.9300
C1—C2	1.507 (4)	C9—H12	0.9300
C2—C3	1.395 (4)	C10—H10	0.9300
C2—C7	1.375 (3)	C11—H11	0.9300
C3—C4	1.360 (4)	C12—H13	0.9300
C4—C5	1.384 (3)	C15—H15A	0.9700
C5—C6	1.375 (3)	C15—H15B	0.9700
C6—C7	1.371 (3)	C16A—H16A	0.9700
C8—C9	1.387 (3)	C16A—H16B	0.9700
C8—C13	1.391 (3)	C16B—H16C	0.9700
C9—C10	1.368 (4)	C16B—H16D	0.9700
C10—C11	1.355 (5)	C17A—H17C	0.9600
C11—C12	1.371 (4)	C17A—H17A	0.9600
C12—C13	1.407 (4)	C17A—H17B	0.9600
C13—C14	1.470 (4)	C17B—H17D	0.9600
C15—C16A	1.543 (9)	C17B—H17E	0.9600
C15—C16B	1.401 (9)	C17B—H17F	0.9600
O1—S1—O2	119.49 (11)	C4—C3—H6	119.00
O1—S1—N1	104.10 (10)	C3—C4—H5	120.00
O1—S1—C5	108.30 (10)	C5—C4—H5	120.00
O2—S1—N1	109.66 (10)	C5—C6—H8	120.00
O2—S1—C5	108.11 (10)	C7—C6—H8	120.00
N1—S1—C5	106.47 (10)	C2—C7—H7	119.00
C14—O4—C15	117.5 (2)	C6—C7—H7	119.00
S1—N1—C8	126.02 (15)	C8—C9—H12	120.00
C8—N1—H1	117.00	C10—C9—H12	120.00
S1—N1—H1	117.00	C9—C10—H10	119.00
C1—C2—C7	122.2 (2)	C11—C10—H10	119.00
C1—C2—C3	120.3 (2)	C10—C11—H11	120.00
C3—C2—C7	117.5 (2)	C12—C11—H11	120.00
C2—C3—C4	121.7 (2)	C11—C12—H13	120.00
C3—C4—C5	119.4 (2)	C13—C12—H13	120.00
C4—C5—C6	120.1 (2)	O4—C15—H15A	111.00
S1—C5—C4	119.24 (16)	O4—C15—H15B	111.00
S1—C5—C6	120.69 (15)	C16A—C15—H15A	111.00
C5—C6—C7	119.5 (2)	C16A—C15—H15B	111.00
C2—C7—C6	121.8 (2)	H15A—C15—H15B	109.00
N1—C8—C13	119.02 (19)	C16B—C15—H15A	80.00
N1—C8—C9	121.4 (2)	C16B—C15—H15B	132.00
C9—C8—C13	119.6 (2)	C15—C16A—H16A	106.00
C8—C9—C10	119.9 (2)	C15—C16A—H16B	106.00
C9—C10—C11	121.8 (3)	C17A—C16A—H16A	106.00
C10—C11—C12	119.3 (2)	C17A—C16A—H16B	106.00
C11—C12—C13	120.9 (2)	H16A—C16A—H16B	106.00
C12—C13—C14	119.4 (2)	C15—C16B—H16D	107.00
C8—C13—C12	118.5 (2)	C17B—C16B—H16C	107.00
C8—C13—C14	122.0 (2)	C17B—C16B—H16D	107.00
O4—C14—C13	113.2 (3)	H16C—C16B—H16D	107.00
O3—C14—O4	121.6 (3)	C15—C16B—H16C	107.00
O3—C14—C13	125.3 (2)	H17A—C17A—H17C	109.00
O4—C15—C16A	103.5 (4)	H17B—C17A—H17C	110.00
O4—C15—C16B	109.2 (5)	C16A—C17A—H17A	109.00
C15—C16A—C17A	126.1 (9)	C16A—C17A—H17B	110.00
C15—C16B—C17B	120.3 (10)	C16A—C17A—H17C	110.00
C2—C1—H14A	109.00	H17A—C17A—H17B	109.00
C2—C1—H14B	109.00	C16B—C17B—H17D	110.00
C2—C1—H14C	109.00	C16B—C17B—H17E	109.00
H14A—C1—H14B	110.00	C16B—C17B—H17F	110.00
H14A—C1—H14C	109.00	H17D—C17B—H17E	109.00
H14B—C1—H14C	109.00	H17D—C17B—H17F	110.00
C2—C3—H6	119.00	H17E—C17B—H17F	109.00
O1—S1—N1—C8	175.93 (18)	C3—C4—C5—S1	177.35 (18)
O2—S1—N1—C8	−55.1 (2)	C4—C5—C6—C7	2.5 (3)
C5—S1—N1—C8	61.6 (2)	S1—C5—C6—C7	−177.21 (18)
O1—S1—C5—C4	−48.9 (2)	C5—C6—C7—C2	−1.3 (4)
O2—S1—C5—C4	−179.66 (17)	N1—C8—C13—C14	0.6 (3)
N1—S1—C5—C4	62.58 (19)	C9—C8—C13—C12	−0.7 (3)
O1—S1—C5—C6	130.81 (18)	C9—C8—C13—C14	177.9 (2)
O2—S1—C5—C6	0.0 (2)	C13—C8—C9—C10	0.7 (4)
N1—S1—C5—C6	−117.76 (18)	N1—C8—C13—C12	−178.0 (2)
C15—O4—C14—O3	−0.8 (4)	N1—C8—C9—C10	178.0 (2)
C15—O4—C14—C13	178.1 (2)	C8—C9—C10—C11	0.0 (4)
C14—O4—C15—C16A	−168.8 (4)	C9—C10—C11—C12	−0.8 (5)
S1—N1—C8—C9	34.1 (3)	C10—C11—C12—C13	0.9 (4)
S1—N1—C8—C13	−148.64 (18)	C11—C12—C13—C14	−178.8 (2)
C3—C2—C7—C6	0.1 (4)	C11—C12—C13—C8	−0.1 (4)
C1—C2—C3—C4	−179.4 (3)	C8—C13—C14—O3	2.9 (4)
C1—C2—C7—C6	179.6 (3)	C8—C13—C14—O4	−175.9 (2)
C7—C2—C3—C4	0.1 (4)	C12—C13—C14—O3	−178.5 (2)
C2—C3—C4—C5	1.1 (4)	C12—C13—C14—O4	2.7 (3)
C3—C4—C5—C6	−2.3 (3)	O4—C15—C16A—C17A	−129.7 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	2.11	2.643 (3)	119
C6—H8···O2	0.93	2.53	2.902 (3)	104
C10—H10···O1i	0.93	2.49	3.391 (3)	163
C9—H12···O2	0.93	2.36	3.027 (3)	128
C12—H13···O4	0.93	2.35	2.681 (3)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	2.11	2.643 (3)	119
C10—H10⋯O1i	0.93	2.49	3.391 (3)	163
C9—H12⋯O2	0.93	2.36	3.027 (3)	128

Symmetry code: (i) .