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

The title mol-ecule, C(16)H(14)N(2)O(4)S, adopts an L-shaped conformation, with the central C-S-N-C torsion angle being -69.1 (3)°. The two benzene rings form a dihedral angle of 89.94 (15)°. The mol-ecular conformation may be influenced by a weak intra-molecular C-H⋯O hydrogen bond which generates an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O and weak C-H⋯O hydrogen bonds, forming chains propagating along the b axis. Weak C-H⋯N hydrogen bonds connect the chains into a two-dimensional network parallel to (011). The crystal studied was an inversion twin, the ratio of components being 0.7 (1):0.3 (1).

Related literature

For related structures, see: Mustafa et al. (2010 ▶, 2011 ▶, 2012a ▶,b ▶); Khan et al. (2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14N2O4S

M = 330.36

Monoclinic,

a = 5.9360 (3) Å

b = 8.1992 (4) Å

c = 15.9068 (8) Å

β = 91.222 (3)°

V = 774.02 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.28 × 0.23 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

6266 measured reflections

3077 independent reflections

2306 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 1.01

3077 reflections

210 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1248 Freidel pairs

Flack parameter: 0.30 (10)

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/S1600536812017126/lh5455sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017126/lh5455Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812017126/lh5455Isup3.cml

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

C16H14N2O4S	F(000) = 344
Mr = 330.36	Dx = 1.418 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2045 reflections
a = 5.9360 (3) Å	θ = 2.6–24.7°
b = 8.1992 (4) Å	µ = 0.23 mm−1
c = 15.9068 (8) Å	T = 296 K
β = 91.222 (3)°	Block, yellow
V = 774.02 (7) Å3	0.28 × 0.23 × 0.19 mm
Z = 2

Bruker APEXII CCD diffractometer	2306 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.027
Graphite monochromator	θmax = 27.1°, θmin = 1.3°
φ and ω scans	h = −7→7
6266 measured reflections	k = −8→10
3077 independent reflections	l = −20→15

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)] = 0.046	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0538P)2 + 0.0338P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3077 reflections	Δρmax = 0.20 e Å−3
210 parameters	Δρmin = −0.25 e Å−3
1 restraint	Absolute structure: Flack (1983), 1248 Freidel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.30 (10)

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
S1	0.58175 (11)	0.32017 (11)	0.30134 (5)	0.0453 (2)
O1	0.6354 (4)	0.4862 (3)	0.28356 (14)	0.0570 (8)
O2	0.7581 (3)	0.2041 (3)	0.31249 (15)	0.0597 (9)
O3	0.1129 (4)	−0.4816 (3)	0.16303 (18)	0.0630 (10)
O4	−0.1469 (4)	−0.3362 (3)	0.09421 (15)	0.0576 (8)
N1	0.4185 (4)	0.2648 (3)	0.22249 (17)	0.0505 (9)
N2	−0.6118 (7)	−0.3907 (7)	−0.0148 (3)	0.1056 (19)
C1	0.0250 (6)	0.3400 (6)	0.6140 (2)	0.0774 (14)
C2	0.1617 (5)	0.3314 (5)	0.53585 (18)	0.0512 (10)
C3	0.3637 (6)	0.2464 (4)	0.5345 (2)	0.0595 (12)
C4	0.4901 (5)	0.2381 (4)	0.4627 (2)	0.0515 (11)
C5	0.4149 (4)	0.3166 (4)	0.39131 (16)	0.0400 (8)
C6	0.2138 (5)	0.4021 (4)	0.3910 (2)	0.0487 (11)
C7	0.0899 (5)	0.4073 (4)	0.4624 (2)	0.0542 (11)
C8	0.3266 (5)	0.1077 (4)	0.20785 (18)	0.0422 (10)
C9	0.4346 (5)	−0.0359 (4)	0.2306 (2)	0.0538 (11)
C10	0.3380 (4)	−0.1827 (5)	0.20995 (18)	0.0508 (9)
C11	0.1348 (4)	−0.1913 (5)	0.16607 (16)	0.0416 (8)
C12	0.0272 (5)	−0.0468 (4)	0.1442 (2)	0.0466 (11)
C13	0.1211 (5)	0.0997 (4)	0.1656 (2)	0.0484 (11)
C14	0.0402 (5)	−0.3518 (4)	0.1432 (2)	0.0481 (11)
C15	−0.2527 (6)	−0.4841 (4)	0.0670 (2)	0.0621 (12)
C16	−0.4543 (8)	−0.4347 (5)	0.0209 (3)	0.0704 (17)
H1	0.38520	0.33880	0.18600	0.0610*
H1A	0.02430	0.45000	0.63460	0.1160*
H1B	0.08990	0.26940	0.65610	0.1160*
H1C	−0.12670	0.30610	0.60120	0.1160*
H3	0.41510	0.19380	0.58310	0.0710*
H4	0.62470	0.18000	0.46270	0.0620*
H6	0.16340	0.45560	0.34250	0.0590*
H7	−0.04630	0.46340	0.46160	0.0650*
H9	0.57210	−0.03270	0.25960	0.0640*
H10	0.41080	−0.27870	0.22580	0.0610*
H12	−0.10980	−0.04980	0.11480	0.0560*
H13	0.04560	0.19560	0.15150	0.0580*
H15A	−0.29080	−0.55120	0.11490	0.0740*
H15B	−0.15360	−0.54570	0.03110	0.0740*

	U11	U22	U33	U12	U13	U23
S1	0.0447 (3)	0.0424 (4)	0.0486 (4)	−0.0002 (4)	−0.0010 (3)	−0.0054 (4)
O1	0.0656 (14)	0.0481 (15)	0.0572 (15)	−0.0175 (12)	0.0007 (11)	0.0017 (11)
O2	0.0456 (12)	0.0650 (16)	0.0684 (17)	0.0109 (12)	−0.0035 (12)	−0.0136 (13)
O3	0.0728 (17)	0.0376 (14)	0.078 (2)	0.0009 (12)	−0.0101 (15)	0.0073 (13)
O4	0.0626 (13)	0.0432 (13)	0.0662 (16)	−0.0060 (11)	−0.0166 (11)	−0.0016 (12)
N1	0.0686 (16)	0.0394 (17)	0.0430 (16)	−0.0007 (12)	−0.0077 (13)	−0.0001 (11)
N2	0.080 (3)	0.147 (4)	0.089 (3)	−0.016 (3)	−0.017 (2)	−0.030 (3)
C1	0.081 (2)	0.087 (3)	0.065 (2)	−0.032 (3)	0.0211 (18)	−0.016 (3)
C2	0.0556 (16)	0.0490 (19)	0.0493 (18)	−0.0153 (19)	0.0056 (13)	−0.012 (2)
C3	0.069 (2)	0.060 (2)	0.049 (2)	−0.0071 (17)	−0.0092 (17)	0.0152 (16)
C4	0.0490 (16)	0.0492 (19)	0.056 (2)	0.0085 (15)	−0.0042 (16)	0.0071 (16)
C5	0.0401 (12)	0.0322 (13)	0.0473 (15)	0.0002 (17)	−0.0056 (11)	−0.0017 (18)
C6	0.0481 (17)	0.0507 (18)	0.047 (2)	0.0090 (16)	−0.0053 (15)	0.0056 (15)
C7	0.0441 (16)	0.0535 (19)	0.065 (2)	0.0053 (16)	0.0008 (16)	−0.0030 (18)
C8	0.0480 (16)	0.0437 (19)	0.0352 (17)	0.0022 (15)	0.0048 (13)	−0.0013 (14)
C9	0.0486 (17)	0.051 (2)	0.061 (2)	0.0068 (16)	−0.0147 (16)	−0.0020 (17)
C10	0.0517 (14)	0.0448 (17)	0.0554 (18)	0.011 (2)	−0.0074 (13)	0.002 (2)
C11	0.0458 (12)	0.0407 (16)	0.0383 (15)	0.0018 (18)	0.0024 (11)	0.0028 (17)
C12	0.0435 (17)	0.047 (2)	0.049 (2)	0.0035 (15)	−0.0040 (15)	−0.0004 (16)
C13	0.0458 (17)	0.044 (2)	0.055 (2)	0.0056 (16)	−0.0082 (17)	−0.0011 (18)
C14	0.0471 (17)	0.048 (2)	0.049 (2)	−0.0018 (17)	−0.0003 (16)	−0.0013 (18)
C15	0.072 (2)	0.057 (2)	0.057 (2)	−0.0181 (19)	−0.0040 (19)	−0.0070 (18)
C16	0.066 (3)	0.095 (3)	0.050 (3)	−0.018 (2)	−0.0030 (19)	−0.015 (2)

S1—O1	1.428 (3)	C9—C10	1.370 (5)
S1—O2	1.423 (2)	C10—C11	1.382 (3)
S1—N1	1.633 (3)	C11—C12	1.387 (5)
S1—C5	1.758 (3)	C11—C14	1.473 (5)
O3—C14	1.189 (4)	C12—C13	1.364 (5)
O4—C14	1.349 (4)	C15—C16	1.448 (6)
O4—C15	1.429 (4)	C1—H1A	0.9600
N1—C8	1.416 (4)	C1—H1B	0.9600
N2—C16	1.142 (7)	C1—H1C	0.9600
N1—H1	0.8600	C3—H3	0.9300
C1—C2	1.501 (4)	C4—H4	0.9300
C2—C7	1.383 (4)	C6—H6	0.9300
C2—C3	1.388 (5)	C7—H7	0.9300
C3—C4	1.382 (5)	C9—H9	0.9300
C4—C5	1.372 (4)	C10—H10	0.9300
C5—C6	1.384 (4)	C12—H12	0.9300
C6—C7	1.367 (4)	C13—H13	0.9300
C8—C9	1.385 (5)	C15—H15A	0.9700
C8—C13	1.382 (4)	C15—H15B	0.9700
O1—S1—O2	119.72 (14)	O3—C14—O4	121.9 (3)
O1—S1—N1	104.13 (14)	O4—C14—C11	111.3 (3)
O1—S1—C5	108.00 (15)	O4—C15—C16	105.6 (3)
O2—S1—N1	109.43 (14)	N2—C16—C15	177.8 (5)
O2—S1—C5	108.25 (14)	C2—C1—H1A	109.00
N1—S1—C5	106.57 (13)	C2—C1—H1B	109.00
C14—O4—C15	116.5 (3)	C2—C1—H1C	109.00
S1—N1—C8	126.8 (2)	H1A—C1—H1B	109.00
S1—N1—H1	117.00	H1A—C1—H1C	109.00
C8—N1—H1	117.00	H1B—C1—H1C	110.00
C3—C2—C7	117.6 (3)	C2—C3—H3	119.00
C1—C2—C3	121.3 (3)	C4—C3—H3	119.00
C1—C2—C7	121.1 (3)	C3—C4—H4	120.00
C2—C3—C4	121.5 (3)	C5—C4—H4	120.00
C3—C4—C5	119.2 (3)	C5—C6—H6	120.00
S1—C5—C6	119.3 (2)	C7—C6—H6	120.00
S1—C5—C4	120.2 (2)	C2—C7—H7	119.00
C4—C5—C6	120.4 (3)	C6—C7—H7	119.00
C5—C6—C7	119.5 (3)	C8—C9—H9	120.00
C2—C7—C6	121.8 (3)	C10—C9—H9	120.00
C9—C8—C13	119.1 (3)	C9—C10—H10	119.00
N1—C8—C13	117.1 (3)	C11—C10—H10	119.00
N1—C8—C9	123.8 (3)	C11—C12—H12	120.00
C8—C9—C10	119.7 (3)	C13—C12—H12	120.00
C9—C10—C11	121.5 (3)	C8—C13—H13	120.00
C12—C11—C14	122.0 (2)	C12—C13—H13	119.00
C10—C11—C12	118.4 (3)	O4—C15—H15A	111.00
C10—C11—C14	119.6 (3)	O4—C15—H15B	111.00
C11—C12—C13	120.4 (3)	C16—C15—H15A	111.00
C8—C13—C12	121.0 (3)	C16—C15—H15B	111.00
O3—C14—C11	126.9 (3)	H15A—C15—H15B	109.00
O1—S1—N1—C8	176.9 (2)	C3—C4—C5—C6	−0.5 (5)
O2—S1—N1—C8	47.8 (3)	C3—C4—C5—S1	175.5 (3)
C5—S1—N1—C8	−69.1 (3)	C4—C5—C6—C7	−0.2 (5)
O1—S1—C5—C4	−118.0 (3)	S1—C5—C6—C7	−176.3 (2)
O2—S1—C5—C4	13.0 (3)	C5—C6—C7—C2	1.1 (5)
N1—S1—C5—C4	130.6 (3)	N1—C8—C13—C12	175.8 (3)
O1—S1—C5—C6	58.1 (3)	C9—C8—C13—C12	−1.8 (5)
O2—S1—C5—C6	−171.0 (2)	N1—C8—C9—C10	−176.6 (3)
N1—S1—C5—C6	−53.3 (3)	C13—C8—C9—C10	0.9 (4)
C15—O4—C14—C11	179.3 (2)	C8—C9—C10—C11	0.5 (4)
C14—O4—C15—C16	176.3 (3)	C9—C10—C11—C12	−1.0 (4)
C15—O4—C14—O3	−0.3 (4)	C9—C10—C11—C14	178.3 (3)
S1—N1—C8—C9	−32.5 (4)	C10—C11—C14—O4	−174.3 (2)
S1—N1—C8—C13	150.0 (2)	C12—C11—C14—O3	−175.5 (3)
C1—C2—C7—C6	179.3 (3)	C12—C11—C14—O4	5.0 (4)
C1—C2—C3—C4	180.0 (3)	C10—C11—C14—O3	5.2 (5)
C3—C2—C7—C6	−1.1 (5)	C10—C11—C12—C13	0.1 (4)
C7—C2—C3—C4	0.3 (5)	C14—C11—C12—C13	−179.2 (3)
C2—C3—C4—C5	0.5 (5)	C11—C12—C13—C8	1.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.86	2.21	2.904 (3)	138
C1—H1A···O2ii	0.96	2.58	3.446 (5)	150
C9—H9···O2	0.93	2.38	3.025 (4)	126
C10—H10···O1iii	0.93	2.51	3.431 (4)	172
C12—H12···N2iv	0.93	2.62	3.426 (6)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.86	2.21	2.904 (3)	138
C1—H1A⋯O2ii	0.96	2.58	3.446 (5)	150
C9—H9⋯O2	0.93	2.38	3.025 (4)	126
C10—H10⋯O1iii	0.93	2.51	3.431 (4)	172
C12—H12⋯N2iv	0.93	2.62	3.426 (6)	146

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