Butyl 4-(4-methyl-benzene-sulfonamido)-benzoate.

In the title compound, C(18)H(21)NO(4)S, the aromatic rings are almost normal to each other, with a dihedral angle of 89.27 (18)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O inter-action, which generates an S(6) motif. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds lead to the formation of chains propagating along [010]. Neighbouring chains are linked via a C-H⋯π inter-action. The -CH(2)CH(2)CH(3) atoms of the butyl group are disordered over two sets of sites, with a refined site-occupancy ratio of 0.536 (16):0.464 (16).

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 ▶). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H21NO4S

M = 347.43

Monoclinic,

a = 17.8216 (13) Å

b = 8.2702 (6) Å

c = 11.9282 (8) Å

β = 91.001 (3)°

V = 1757.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.33 × 0.25 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer

13164 measured reflections

3557 independent reflections

2287 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.218

S = 1.05

3557 reflections

224 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 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/S1600536812015413/su2404sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015413/su2404Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015413/su2404Isup3.cml

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

C18H21NO4S	F(000) = 736
Mr = 347.43	Dx = 1.313 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2942 reflections
a = 17.8216 (13) Å	θ = 2.7–21.5°
b = 8.2702 (6) Å	µ = 0.21 mm−1
c = 11.9282 (8) Å	T = 296 K
β = 91.001 (3)°	Long block, light yellow
V = 1757.8 (2) Å3	0.33 × 0.25 × 0.21 mm
Z = 4

Bruker APEXII CCD diffractometer	2287 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.038
Graphite monochromator	θmax = 26.4°, θmin = 3.0°
φ and ω scans	h = −21→22
13164 measured reflections	k = −10→10
3557 independent reflections	l = −11→14

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.218	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1157P)2 + 0.8149P] where P = (Fo2 + 2Fc2)/3
3557 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.39 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	0.17821 (5)	−0.16383 (11)	0.79992 (7)	0.0561 (3)
O1	0.19456 (16)	−0.3261 (3)	0.8276 (2)	0.0672 (9)
O2	0.16764 (16)	−0.0474 (3)	0.88556 (19)	0.0707 (10)
O3	0.30722 (17)	0.6342 (3)	0.5914 (2)	0.0779 (10)
O4	0.36618 (16)	0.5025 (3)	0.4580 (2)	0.0732 (10)
N1	0.24647 (17)	−0.1059 (4)	0.7206 (2)	0.0618 (10)
C1	−0.0991 (3)	−0.1840 (7)	0.5042 (4)	0.0992 (19)
C2	−0.0300 (2)	−0.1785 (5)	0.5775 (3)	0.0666 (14)
C3	−0.0269 (2)	−0.0810 (5)	0.6726 (4)	0.0725 (17)
C4	0.0361 (2)	−0.0747 (5)	0.7391 (3)	0.0618 (12)
C5	0.09731 (19)	−0.1661 (4)	0.7132 (3)	0.0506 (10)
C6	0.0964 (2)	−0.2636 (4)	0.6183 (3)	0.0582 (12)
C7	0.0334 (2)	−0.2668 (5)	0.5514 (3)	0.0659 (16)
C8	0.25941 (18)	0.0499 (4)	0.6752 (3)	0.0515 (11)
C9	0.2412 (2)	0.1907 (4)	0.7308 (3)	0.0641 (14)
C10	0.2598 (2)	0.3388 (4)	0.6868 (3)	0.0625 (12)
C11	0.29879 (18)	0.3488 (4)	0.5867 (3)	0.0528 (11)
C12	0.3148 (2)	0.2070 (5)	0.5310 (3)	0.0618 (12)
C13	0.2953 (2)	0.0585 (4)	0.5737 (3)	0.0582 (12)
C14	0.3224 (2)	0.5084 (4)	0.5476 (3)	0.0573 (12)
C15	0.3938 (3)	0.6546 (6)	0.4172 (5)	0.102 (2)
C16A	0.4688 (9)	0.619 (2)	0.3570 (12)	0.152 (5)	0.536 (16)
C17A	0.4608 (8)	0.607 (2)	0.2481 (12)	0.152 (5)	0.536 (16)
C18A	0.5254 (9)	0.601 (2)	0.1612 (13)	0.152 (5)	0.536 (16)
C17B	0.5053 (7)	0.5832 (16)	0.3103 (10)	0.086 (3)	0.464 (16)
C18B	0.5446 (7)	0.5739 (17)	0.2028 (10)	0.086 (3)	0.464 (16)
C16B	0.4245 (7)	0.6307 (15)	0.2980 (10)	0.086 (3)	0.464 (16)
H1B	−0.10320	−0.28850	0.46960	0.1490*
H3	−0.06840	−0.01930	0.69120	0.0870*
H4	0.03750	−0.00810	0.80190	0.0740*
H1C	−0.09590	−0.10240	0.44720	0.1490*
H1	0.27880	−0.17900	0.70400	0.0740*
H1A	−0.14250	−0.16450	0.54880	0.1490*
H10	0.24620	0.43290	0.72400	0.0750*
H12	0.33930	0.21190	0.46280	0.0740*
H13	0.30630	−0.03550	0.53440	0.0700*
H15B	0.40420	0.72770	0.47910	0.1220*	0.536 (16)
H15D	0.35690	0.70440	0.36740	0.1220*	0.536 (16)
H16C	0.50410	0.70580	0.37400	0.1820*	0.536 (16)
H16D	0.49000	0.51960	0.38630	0.1820*	0.536 (16)
H17C	0.42890	0.69650	0.22530	0.1820*	0.536 (16)
H17D	0.43160	0.50960	0.23530	0.1820*	0.536 (16)
H18D	0.57300	0.60340	0.20010	0.2280*	0.536 (16)
H18E	0.52150	0.69330	0.11240	0.2280*	0.536 (16)
H18F	0.52130	0.50390	0.11780	0.2280*	0.536 (16)
H6	0.13810	−0.32570	0.60060	0.0700*
H7	0.03300	−0.32990	0.48680	0.0790*
H9	0.21610	0.18520	0.79840	0.0770*
H15A	0.43340	0.69440	0.46680	0.1220*	0.464 (16)
H15C	0.35360	0.73360	0.41540	0.1220*	0.464 (16)
H16A	0.39650	0.54670	0.25890	0.1030*	0.464 (16)
H16B	0.42000	0.73020	0.25530	0.1030*	0.464 (16)
H17A	0.53080	0.66120	0.35830	0.1030*	0.464 (16)
H17B	0.50830	0.47870	0.34710	0.1030*	0.464 (16)
H18A	0.50870	0.55730	0.14300	0.1280*	0.464 (16)
H18B	0.57940	0.48530	0.20490	0.1280*	0.464 (16)
H18C	0.57130	0.67290	0.19040	0.1280*	0.464 (16)

	U11	U22	U33	U12	U13	U23
S1	0.0664 (6)	0.0498 (5)	0.0523 (5)	−0.0032 (4)	0.0105 (4)	0.0025 (4)
O1	0.0839 (17)	0.0506 (15)	0.0674 (15)	−0.0016 (13)	0.0124 (13)	0.0131 (12)
O2	0.0923 (19)	0.0690 (17)	0.0512 (13)	−0.0142 (14)	0.0126 (13)	−0.0087 (12)
O3	0.102 (2)	0.0505 (16)	0.0821 (18)	−0.0024 (14)	0.0267 (16)	−0.0034 (14)
O4	0.0831 (18)	0.0614 (17)	0.0760 (17)	−0.0054 (13)	0.0292 (15)	0.0018 (13)
N1	0.0649 (18)	0.0483 (16)	0.0727 (19)	−0.0003 (14)	0.0159 (15)	0.0005 (14)
C1	0.079 (3)	0.122 (4)	0.096 (3)	−0.023 (3)	−0.016 (3)	0.043 (3)
C2	0.065 (2)	0.071 (3)	0.064 (2)	−0.010 (2)	0.0044 (18)	0.026 (2)
C3	0.069 (3)	0.069 (3)	0.080 (3)	0.014 (2)	0.014 (2)	0.013 (2)
C4	0.073 (2)	0.056 (2)	0.057 (2)	0.0118 (18)	0.0151 (18)	−0.0002 (17)
C5	0.0594 (19)	0.0450 (18)	0.0479 (17)	−0.0002 (15)	0.0139 (15)	0.0061 (14)
C6	0.061 (2)	0.060 (2)	0.054 (2)	0.0045 (17)	0.0137 (17)	−0.0102 (16)
C7	0.075 (3)	0.073 (3)	0.050 (2)	−0.005 (2)	0.0067 (19)	−0.0060 (18)
C8	0.0508 (18)	0.0503 (19)	0.0536 (18)	−0.0025 (15)	0.0047 (15)	0.0010 (15)
C9	0.078 (3)	0.054 (2)	0.061 (2)	−0.0025 (18)	0.0210 (19)	−0.0067 (17)
C10	0.070 (2)	0.052 (2)	0.066 (2)	0.0026 (17)	0.0158 (18)	−0.0109 (17)
C11	0.0501 (18)	0.054 (2)	0.0545 (18)	−0.0032 (15)	0.0042 (15)	−0.0006 (16)
C12	0.071 (2)	0.061 (2)	0.054 (2)	0.0027 (18)	0.0191 (17)	−0.0031 (17)
C13	0.066 (2)	0.050 (2)	0.059 (2)	−0.0004 (17)	0.0144 (17)	−0.0052 (16)
C14	0.057 (2)	0.054 (2)	0.061 (2)	0.0013 (16)	0.0057 (17)	−0.0010 (17)
C15	0.118 (4)	0.074 (3)	0.115 (4)	−0.012 (3)	0.056 (3)	0.015 (3)
C16A	0.107 (7)	0.237 (12)	0.113 (7)	0.056 (6)	0.042 (5)	0.048 (6)
C17A	0.107 (7)	0.237 (12)	0.113 (7)	0.056 (6)	0.042 (5)	0.048 (6)
C18A	0.107 (7)	0.237 (12)	0.113 (7)	0.056 (6)	0.042 (5)	0.048 (6)
C17B	0.062 (5)	0.104 (5)	0.091 (6)	−0.005 (3)	0.007 (3)	0.015 (4)
C18B	0.062 (5)	0.104 (5)	0.091 (6)	−0.005 (3)	0.007 (3)	0.015 (4)
C16B	0.062 (5)	0.104 (5)	0.091 (6)	−0.005 (3)	0.007 (3)	0.015 (4)

S1—O1	1.411 (3)	C1—H1A	0.9600
S1—O2	1.419 (3)	C1—H1B	0.9600
S1—N1	1.626 (3)	C1—H1C	0.9600
S1—C5	1.760 (4)	C3—H3	0.9300
O3—C14	1.197 (4)	C4—H4	0.9300
O4—C14	1.335 (4)	C6—H6	0.9300
O4—C15	1.439 (6)	C7—H7	0.9300
N1—C8	1.418 (5)	C9—H9	0.9300
N1—H1	0.8600	C10—H10	0.9300
C1—C2	1.499 (6)	C12—H12	0.9300
C2—C3	1.392 (6)	C13—H13	0.9300
C2—C7	1.385 (5)	C15—H15B	0.9700
C3—C4	1.364 (5)	C15—H15D	0.9700
C4—C5	1.367 (5)	C15—H15A	0.9700
C5—C6	1.390 (5)	C15—H15C	0.9700
C6—C7	1.366 (5)	C16A—H16C	0.9700
C8—C13	1.381 (5)	C16A—H16D	0.9700
C8—C9	1.382 (5)	C16B—H16B	0.9700
C9—C10	1.375 (5)	C16B—H16A	0.9700
C10—C11	1.394 (5)	C17A—H17D	0.9700
C11—C12	1.380 (5)	C17A—H17C	0.9700
C11—C14	1.464 (5)	C17B—H17A	0.9700
C12—C13	1.377 (5)	C17B—H17B	0.9700
C15—C16B	1.545 (13)	C18A—H18E	0.9600
C15—C16A	1.556 (17)	C18A—H18F	0.9600
C16A—C17A	1.31 (2)	C18A—H18D	0.9600
C16B—C17B	1.497 (18)	C18B—H18A	0.9600
C17A—C18A	1.56 (2)	C18B—H18B	0.9600
C17B—C18B	1.474 (17)	C18B—H18C	0.9600
O1—S1—O2	120.43 (15)	C6—C7—H7	119.00
O1—S1—N1	105.23 (17)	C8—C9—H9	120.00
O1—S1—C5	106.92 (16)	C10—C9—H9	120.00
O2—S1—N1	109.21 (16)	C9—C10—H10	120.00
O2—S1—C5	108.23 (17)	C11—C10—H10	120.00
N1—S1—C5	105.94 (15)	C11—C12—H12	119.00
C14—O4—C15	116.6 (3)	C13—C12—H12	119.00
S1—N1—C8	128.2 (3)	C8—C13—H13	120.00
C8—N1—H1	116.00	C12—C13—H13	120.00
S1—N1—H1	116.00	O4—C15—H15B	110.00
C3—C2—C7	117.9 (3)	O4—C15—H15D	110.00
C1—C2—C7	121.2 (4)	O4—C15—H15A	110.00
C1—C2—C3	120.9 (4)	O4—C15—H15C	110.00
C2—C3—C4	121.1 (4)	C16A—C15—H15B	108.00
C3—C4—C5	120.0 (4)	C16A—C15—H15D	112.00
S1—C5—C6	118.9 (3)	H15B—C15—H15D	109.00
S1—C5—C4	120.7 (3)	C16B—C15—H15A	110.00
C4—C5—C6	120.5 (3)	C16B—C15—H15C	110.00
C5—C6—C7	119.0 (3)	H15A—C15—H15C	108.00
C2—C7—C6	121.6 (3)	C15—C16A—H16C	109.00
N1—C8—C9	122.8 (3)	C15—C16A—H16D	109.00
N1—C8—C13	117.6 (3)	C17A—C16A—H16C	109.00
C9—C8—C13	119.6 (3)	C17A—C16A—H16D	109.00
C8—C9—C10	120.5 (3)	H16C—C16A—H16D	108.00
C9—C10—C11	120.4 (3)	H16A—C16B—H16B	109.00
C12—C11—C14	123.4 (3)	C15—C16B—H16A	110.00
C10—C11—C14	118.5 (3)	C15—C16B—H16B	110.00
C10—C11—C12	118.2 (3)	C17B—C16B—H16A	110.00
C11—C12—C13	121.6 (3)	C17B—C16B—H16B	110.00
C8—C13—C12	119.6 (3)	C18A—C17A—H17C	106.00
O3—C14—C11	125.2 (3)	C18A—C17A—H17D	106.00
O3—C14—O4	121.4 (3)	C16A—C17A—H17D	106.00
O4—C14—C11	113.4 (3)	C16A—C17A—H17C	106.00
O4—C15—C16B	109.2 (6)	H17C—C17A—H17D	106.00
O4—C15—C16A	107.0 (7)	C16B—C17B—H17A	109.00
C15—C16A—C17A	113.1 (12)	C16B—C17B—H17B	109.00
C15—C16B—C17B	107.4 (9)	H17A—C17B—H17B	108.00
C16A—C17A—C18A	126.3 (14)	C18B—C17B—H17B	109.00
C16B—C17B—C18B	113.5 (10)	C18B—C17B—H17A	109.00
C2—C1—H1A	109.00	C17A—C18A—H18F	110.00
C2—C1—H1B	109.00	C17A—C18A—H18E	109.00
C2—C1—H1C	109.00	H18E—C18A—H18F	110.00
H1A—C1—H1B	109.00	H18D—C18A—H18E	109.00
H1A—C1—H1C	109.00	H18D—C18A—H18F	110.00
H1B—C1—H1C	109.00	C17A—C18A—H18D	109.00
C2—C3—H3	120.00	C17B—C18B—H18A	109.00
C4—C3—H3	119.00	C17B—C18B—H18B	109.00
C3—C4—H4	120.00	C17B—C18B—H18C	110.00
C5—C4—H4	120.00	H18A—C18B—H18B	109.00
C5—C6—H6	120.00	H18A—C18B—H18C	109.00
C7—C6—H6	121.00	H18B—C18B—H18C	109.00
C2—C7—H7	119.00
O1—S1—N1—C8	−176.1 (3)	C3—C4—C5—C6	1.1 (6)
O2—S1—N1—C8	−45.5 (3)	S1—C5—C6—C7	179.4 (3)
C5—S1—N1—C8	70.9 (3)	C4—C5—C6—C7	−0.1 (5)
O1—S1—C5—C4	126.3 (3)	C5—C6—C7—C2	−1.6 (6)
O1—S1—C5—C6	−53.2 (3)	N1—C8—C9—C10	175.3 (3)
O2—S1—C5—C4	−4.8 (4)	C13—C8—C9—C10	−1.2 (5)
O2—S1—C5—C6	175.7 (3)	N1—C8—C13—C12	−174.5 (3)
N1—S1—C5—C4	−121.9 (3)	C9—C8—C13—C12	2.2 (5)
N1—S1—C5—C6	58.7 (3)	C8—C9—C10—C11	−1.4 (5)
C15—O4—C14—O3	−0.1 (5)	C9—C10—C11—C12	3.0 (5)
C15—O4—C14—C11	−177.9 (3)	C9—C10—C11—C14	−175.4 (3)
C14—O4—C15—C16A	153.3 (6)	C10—C11—C12—C13	−2.0 (5)
S1—N1—C8—C9	33.7 (5)	C14—C11—C12—C13	176.3 (3)
S1—N1—C8—C13	−149.7 (3)	C10—C11—C14—O3	−4.6 (5)
C1—C2—C3—C4	−179.5 (4)	C10—C11—C14—O4	173.1 (3)
C7—C2—C3—C4	−1.1 (6)	C12—C11—C14—O3	177.1 (4)
C1—C2—C7—C6	−179.4 (4)	C12—C11—C14—O4	−5.2 (5)
C3—C2—C7—C6	2.2 (6)	C11—C12—C13—C8	−0.6 (5)
C2—C3—C4—C5	−0.5 (6)	O4—C15—C16A—C17A	98.0 (13)
C3—C4—C5—S1	−178.3 (3)	C15—C16A—C17A—C18A	169.1 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.11	2.868 (4)	146
C4—H4···O2	0.93	2.53	2.908 (4)	105
C9—H9···O2	0.93	2.36	3.015 (4)	127
C10—H10···O1ii	0.93	2.53	3.453 (4)	173
C1—H1C···Cg1iii	0.96	2.76	3.639 (6)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.11	2.868 (4)	146
C9—H9⋯O2	0.93	2.36	3.015 (4)	127
C10—H10⋯O1ii	0.93	2.53	3.453 (4)	173
C1—H1C⋯Cg1iii	0.96	2.76	3.639 (6)	153

Symmetry codes: (i) ; (ii) ; (iii) .