Methyl 2-(4-acetamido-benzene-sulfon-amido)-benzoate.

The mol-ecule of the title compound, C(16)H(16)N(2)O(5)S, has the shape of the letter V but with a small twist; the dihedral angle formed between the benzene rings is 79.66 (9)°. The presence of an intra-molecular N-H⋯O hydrogen bond, leading to an S(6) ring, correlates with the near coplanarity of the carboxyl-ate ester group with the benzene ring to which it is connected. The acetamide residue is slightly twisted out of the plane of its benzene ring [C-C-N-C = 13.1 (3)°]. In the crystal, supra-molecular chains along the a axis are mediated by N-H⋯O hydrogen bonds. These are connected into layers via C-H⋯O inter-actions.

Related literature

For background to the pharmacological uses of sulfonamides, see: Korolkovas (1988 ▶); Mandell & Sande (1992 ▶). For related structures, see: Sharif et al. (2010 ▶); Khan et al. (2010 ▶).

Experimental

Crystal data

C16H16N2O5S

M = 348.37

Triclinic,

a = 8.2835 (2) Å

b = 9.3722 (3) Å

c = 10.8299 (3) Å

α = 85.537 (1)°

β = 88.614 (1)°

γ = 72.203 (1)°

V = 798.11 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.20 × 0.18 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

13593 measured reflections

3604 independent reflections

3122 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.07

3604 reflections

225 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAIn class="Chemical">NT (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 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009500/hb5817sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009500/hb5817Isup2.hkl

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

C16H16N2O5S	Z = 2
Mr = 348.37	F(000) = 364
Triclinic, P1	Dx = 1.450 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2835 (2) Å	Cell parameters from 7451 reflections
b = 9.3722 (3) Å	θ = 2.3–28.2°
c = 10.8299 (3) Å	µ = 0.23 mm−1
α = 85.537 (1)°	T = 293 K
β = 88.614 (1)°	Block, colourless
γ = 72.203 (1)°	0.20 × 0.18 × 0.09 mm
V = 798.11 (4) Å3

Bruker APEXII CCD diffractometer	3122 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −10→10
13593 measured reflections	k = −12→12
3604 independent reflections	l = −14→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0578P)2 + 0.1747P] where P = (Fo2 + 2Fc2)/3
3604 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.26 e Å−3
2 restraints	Δρmin = −0.27 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.42614 (5)	0.28976 (4)	0.83592 (3)	0.04378 (14)
O1	0.54431 (14)	0.14234 (13)	0.83938 (11)	0.0562 (3)
O2	0.47186 (15)	0.40243 (13)	0.89646 (11)	0.0544 (3)
O3	0.30254 (19)	0.61672 (14)	0.55728 (12)	0.0659 (4)
O4	0.17057 (17)	0.62717 (14)	0.37946 (11)	0.0620 (3)
O5	−0.13574 (18)	0.09502 (17)	1.23293 (14)	0.0808 (5)
N1	0.38913 (18)	0.36108 (15)	0.69410 (12)	0.0477 (3)
H1N	0.378 (2)	0.4554 (11)	0.6809 (18)	0.057*
N2	−0.21841 (17)	0.26393 (16)	1.06806 (13)	0.0534 (3)
H2N	−0.3050 (18)	0.3309 (17)	1.0351 (17)	0.064*
C1	0.32524 (18)	0.30069 (16)	0.59818 (13)	0.0423 (3)
C2	0.25586 (17)	0.39431 (17)	0.49240 (13)	0.0414 (3)
C3	0.1942 (2)	0.3327 (2)	0.39815 (15)	0.0544 (4)
H3	0.1487	0.3934	0.3276	0.065*
C4	0.1987 (3)	0.1845 (2)	0.40639 (18)	0.0653 (5)
H4	0.1569	0.1453	0.3424	0.078*
C5	0.2660 (3)	0.0955 (2)	0.51059 (19)	0.0678 (5)
H5	0.2690	−0.0048	0.5172	0.081*
C6	0.3289 (3)	0.15192 (19)	0.60507 (17)	0.0608 (5)
H6	0.3746	0.0893	0.6747	0.073*
C7	0.24751 (19)	0.55468 (18)	0.48195 (14)	0.0456 (3)
C8	0.1511 (3)	0.7859 (2)	0.3623 (2)	0.0703 (5)
H8A	0.0954	0.8348	0.4332	0.105*
H8B	0.0843	0.8281	0.2896	0.105*
H8C	0.2607	0.8003	0.3526	0.105*
C9	0.23368 (18)	0.27393 (16)	0.89638 (13)	0.0423 (3)
C10	0.2359 (2)	0.15891 (17)	0.98514 (15)	0.0482 (4)
H10	0.3379	0.0856	1.0056	0.058*
C11	0.0888 (2)	0.15200 (17)	1.04354 (15)	0.0497 (4)
H11	0.0915	0.0750	1.1038	0.060*
C12	−0.06421 (19)	0.26073 (17)	1.01202 (14)	0.0445 (3)
C13	−0.0658 (2)	0.37314 (19)	0.91947 (16)	0.0552 (4)
H13	−0.1682	0.4438	0.8958	0.066*
C14	0.0813 (2)	0.38105 (19)	0.86290 (15)	0.0531 (4)
H14	0.0790	0.4578	0.8024	0.064*
C15	−0.2473 (2)	0.18603 (18)	1.17324 (16)	0.0511 (4)
C16	−0.4303 (2)	0.2227 (2)	1.20973 (19)	0.0614 (4)
H16A	−0.4755	0.1470	1.1837	0.092*
H16B	−0.4925	0.3188	1.1708	0.092*
H16C	−0.4401	0.2258	1.2981	0.092*

	U11	U22	U33	U12	U13	U23
S1	0.0411 (2)	0.0446 (2)	0.0414 (2)	−0.00745 (15)	−0.01326 (14)	0.00368 (15)
O1	0.0458 (6)	0.0516 (6)	0.0599 (7)	−0.0004 (5)	−0.0059 (5)	0.0083 (5)
O2	0.0539 (6)	0.0594 (7)	0.0508 (6)	−0.0184 (5)	−0.0218 (5)	0.0008 (5)
O3	0.0896 (9)	0.0515 (7)	0.0588 (7)	−0.0249 (7)	−0.0269 (7)	0.0045 (6)
O4	0.0771 (8)	0.0539 (7)	0.0532 (7)	−0.0195 (6)	−0.0222 (6)	0.0127 (5)
O5	0.0625 (8)	0.0858 (10)	0.0740 (9)	−0.0021 (7)	−0.0046 (7)	0.0327 (8)
N1	0.0589 (8)	0.0433 (7)	0.0412 (6)	−0.0166 (6)	−0.0140 (6)	0.0035 (5)
N2	0.0406 (7)	0.0577 (8)	0.0547 (8)	−0.0074 (6)	−0.0118 (6)	0.0118 (6)
C1	0.0414 (7)	0.0455 (8)	0.0390 (7)	−0.0120 (6)	−0.0037 (6)	−0.0021 (6)
C2	0.0358 (7)	0.0489 (8)	0.0385 (7)	−0.0118 (6)	−0.0021 (5)	−0.0012 (6)
C3	0.0578 (9)	0.0642 (10)	0.0419 (8)	−0.0195 (8)	−0.0102 (7)	−0.0015 (7)
C4	0.0777 (12)	0.0718 (12)	0.0552 (10)	−0.0325 (10)	−0.0098 (9)	−0.0160 (9)
C5	0.0925 (14)	0.0533 (10)	0.0649 (11)	−0.0313 (10)	−0.0081 (10)	−0.0085 (8)
C6	0.0831 (13)	0.0480 (9)	0.0519 (9)	−0.0214 (9)	−0.0140 (9)	0.0021 (7)
C7	0.0423 (7)	0.0508 (8)	0.0412 (7)	−0.0114 (6)	−0.0055 (6)	0.0025 (6)
C8	0.0795 (13)	0.0520 (10)	0.0739 (12)	−0.0156 (9)	−0.0132 (10)	0.0151 (9)
C9	0.0414 (7)	0.0416 (7)	0.0395 (7)	−0.0060 (6)	−0.0121 (6)	−0.0003 (6)
C10	0.0416 (8)	0.0423 (8)	0.0523 (8)	−0.0018 (6)	−0.0128 (6)	0.0067 (6)
C11	0.0490 (8)	0.0429 (8)	0.0513 (8)	−0.0075 (7)	−0.0112 (7)	0.0086 (6)
C12	0.0421 (7)	0.0464 (8)	0.0421 (7)	−0.0091 (6)	−0.0121 (6)	0.0007 (6)
C13	0.0422 (8)	0.0577 (9)	0.0530 (9)	0.0001 (7)	−0.0135 (7)	0.0145 (7)
C14	0.0466 (8)	0.0538 (9)	0.0482 (8)	−0.0035 (7)	−0.0124 (7)	0.0157 (7)
C15	0.0518 (9)	0.0476 (8)	0.0523 (9)	−0.0137 (7)	−0.0066 (7)	0.0011 (7)
C16	0.0546 (10)	0.0624 (11)	0.0671 (11)	−0.0200 (8)	−0.0032 (8)	0.0051 (8)

S1—O1	1.4267 (11)	C5—C6	1.370 (3)
S1—O2	1.4328 (12)	C5—H5	0.9300
S1—N1	1.6241 (13)	C6—H6	0.9300
S1—C9	1.7525 (16)	C8—H8A	0.9600
O3—C7	1.2104 (19)	C8—H8B	0.9600
O4—C7	1.3237 (18)	C8—H8C	0.9600
O4—C8	1.444 (2)	C9—C10	1.383 (2)
O5—C15	1.208 (2)	C9—C14	1.387 (2)
N1—C1	1.4074 (19)	C10—C11	1.377 (2)
N1—H1n	0.861 (11)	C10—H10	0.9300
N2—C15	1.361 (2)	C11—C12	1.392 (2)
N2—C12	1.394 (2)	C11—H11	0.9300
N2—H2n	0.859 (16)	C12—C13	1.394 (2)
C1—C6	1.381 (2)	C13—C14	1.370 (2)
C1—C2	1.407 (2)	C13—H13	0.9300
C2—C3	1.391 (2)	C14—H14	0.9300
C2—C7	1.479 (2)	C15—C16	1.499 (2)
C3—C4	1.373 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.371 (3)	C16—H16C	0.9600
C4—H4	0.9300
O1—S1—O2	117.99 (7)	O4—C8—H8A	109.5
O1—S1—N1	110.76 (7)	O4—C8—H8B	109.5
O2—S1—N1	103.67 (7)	H8A—C8—H8B	109.5
O1—S1—C9	107.67 (7)	O4—C8—H8C	109.5
O2—S1—C9	109.45 (7)	H8A—C8—H8C	109.5
N1—S1—C9	106.78 (7)	H8B—C8—H8C	109.5
C7—O4—C8	116.93 (14)	C10—C9—C14	119.92 (15)
C1—N1—S1	126.68 (11)	C10—C9—S1	119.16 (11)
C1—N1—H1N	113.9 (13)	C14—C9—S1	120.77 (12)
S1—N1—H1N	116.7 (13)	C11—C10—C9	120.63 (14)
C15—N2—C12	128.75 (13)	C11—C10—H10	119.7
C15—N2—H2N	116.5 (14)	C9—C10—H10	119.7
C12—N2—H2N	114.4 (14)	C10—C11—C12	119.75 (14)
C6—C1—C2	119.11 (14)	C10—C11—H11	120.1
C6—C1—N1	121.77 (14)	C12—C11—H11	120.1
C2—C1—N1	119.12 (13)	C11—C12—N2	123.53 (14)
C3—C2—C1	118.39 (14)	C11—C12—C13	119.09 (15)
C3—C2—C7	120.74 (14)	N2—C12—C13	117.38 (13)
C1—C2—C7	120.86 (13)	C14—C13—C12	120.98 (14)
C4—C3—C2	121.80 (16)	C14—C13—H13	119.5
C4—C3—H3	119.1	C12—C13—H13	119.5
C2—C3—H3	119.1	C13—C14—C9	119.58 (14)
C5—C4—C3	118.83 (17)	C13—C14—H14	120.2
C5—C4—H4	120.6	C9—C14—H14	120.2
C3—C4—H4	120.6	O5—C15—N2	123.33 (16)
C6—C5—C4	121.09 (17)	O5—C15—C16	122.38 (16)
C6—C5—H5	119.5	N2—C15—C16	114.29 (14)
C4—C5—H5	119.5	C15—C16—H16A	109.5
C5—C6—C1	120.77 (17)	C15—C16—H16B	109.5
C5—C6—H6	119.6	H16A—C16—H16B	109.5
C1—C6—H6	119.6	C15—C16—H16C	109.5
O3—C7—O4	122.11 (15)	H16A—C16—H16C	109.5
O3—C7—C2	125.32 (14)	H16B—C16—H16C	109.5
O4—C7—C2	112.57 (13)
O1—S1—N1—C1	58.39 (15)	C1—C2—C7—O4	−176.68 (13)
O2—S1—N1—C1	−174.12 (13)	O1—S1—C9—C10	30.05 (15)
C9—S1—N1—C1	−58.57 (15)	O2—S1—C9—C10	−99.35 (14)
S1—N1—C1—C6	−17.9 (2)	N1—S1—C9—C10	149.04 (13)
S1—N1—C1—C2	162.13 (12)	O1—S1—C9—C14	−154.60 (13)
C6—C1—C2—C3	−0.3 (2)	O2—S1—C9—C14	75.99 (14)
N1—C1—C2—C3	179.62 (14)	N1—S1—C9—C14	−35.61 (15)
C6—C1—C2—C7	179.24 (15)	C14—C9—C10—C11	−1.9 (2)
N1—C1—C2—C7	−0.8 (2)	S1—C9—C10—C11	173.44 (12)
C1—C2—C3—C4	0.4 (2)	C9—C10—C11—C12	0.8 (2)
C7—C2—C3—C4	−179.21 (16)	C10—C11—C12—N2	−178.72 (15)
C2—C3—C4—C5	0.0 (3)	C10—C11—C12—C13	1.4 (2)
C3—C4—C5—C6	−0.4 (3)	C15—N2—C12—C11	13.1 (3)
C4—C5—C6—C1	0.4 (3)	C15—N2—C12—C13	−167.05 (17)
C2—C1—C6—C5	0.0 (3)	C11—C12—C13—C14	−2.5 (3)
N1—C1—C6—C5	180.00 (17)	N2—C12—C13—C14	177.67 (16)
C8—O4—C7—O3	−1.4 (2)	C12—C13—C14—C9	1.3 (3)
C8—O4—C7—C2	178.13 (15)	C10—C9—C14—C13	0.9 (3)
C3—C2—C7—O3	−177.58 (16)	S1—C9—C14—C13	−174.40 (13)
C1—C2—C7—O3	2.9 (2)	C12—N2—C15—O5	−2.5 (3)
C3—C2—C7—O4	2.9 (2)	C12—N2—C15—C16	177.36 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O3	0.861 (11)	1.902 (16)	2.6266 (18)	140.9 (17)
N2—H2n···O2i	0.859 (16)	2.311 (17)	3.0888 (19)	150.7 (15)
C10—H10···O1ii	0.93	2.57	3.330 (2)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O3	0.86 (1)	1.90 (2)	2.6266 (18)	141 (2)
N2—H2n⋯O2i	0.86 (2)	2.31 (2)	3.0888 (19)	151 (2)
C10—H10⋯O1ii	0.93	2.57	3.330 (2)	140

Symmetry codes: (i) ; (ii) .