4-[(5,5-Dimethyl-3-oxocyclo-hex-1-en-yl)amino]-benzene-sulfonamide.

In the title compound, C(14)H(18)N(2)O(3)S, the cyclo-hexene ring exhibits a distorted half-chair conformation and its mean plane makes a dihedral angle of 46.18 (8)° with the benzene ring. In the crystal, mol-ecules are linked via N-H⋯O, N-H⋯(O,O) and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to and the pharmacological activities of related compounds, see: Drews (2000 ▶); Supuran (2008 ▶); Supuran & Scozzafava (2000 ▶); Boyd (1988 ▶); Ghorab et al. (2007 ▶, 2009 ▶, 2011 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H18N2O3S

M = 294.36

Orthorhombic,

a = 11.0365 (3) Å

b = 13.4763 (3) Å

c = 20.0092 (6) Å

V = 2975.99 (14) Å3

Z = 8

Cu Kα radiation

μ = 2.02 mm−1

T = 296 K

0.73 × 0.40 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.322, T max = 0.839

10908 measured reflections

2829 independent reflections

2361 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.04

2829 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.48 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029996/is5161sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029996/is5161Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029996/is5161Isup3.cml

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

C14H18N2O3S	F(000) = 1248
Mr = 294.36	Dx = 1.314 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2253 reflections
a = 11.0365 (3) Å	θ = 4.4–70.1°
b = 13.4763 (3) Å	µ = 2.02 mm−1
c = 20.0092 (6) Å	T = 296 K
V = 2975.99 (14) Å3	Plate, colourless
Z = 8	0.73 × 0.40 × 0.09 mm

Bruker SMART APEXII CCD area-detector diffractometer	2829 independent reflections
Radiation source: fine-focus sealed tube	2361 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 72.0°, θmin = 4.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→13
Tmin = 0.322, Tmax = 0.839	k = −16→10
10908 measured reflections	l = −24→24

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0919P)2] where P = (Fo2 + 2Fc2)/3
2829 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.00703 (4)	0.12128 (3)	0.35905 (2)	0.04078 (17)
N1	0.30747 (13)	−0.19577 (10)	0.24788 (7)	0.0409 (3)
N2	−0.04392 (17)	0.09709 (12)	0.43487 (8)	0.0470 (4)
O1	0.06697 (14)	0.20885 (9)	0.36157 (7)	0.0578 (4)
O2	−0.11492 (13)	0.12253 (11)	0.31954 (8)	0.0628 (4)
O3	0.33684 (13)	−0.09069 (10)	0.02398 (6)	0.0542 (4)
C1	0.33333 (14)	−0.20944 (11)	0.18227 (8)	0.0371 (3)
C2	0.31006 (16)	−0.14052 (12)	0.13444 (8)	0.0411 (4)
H2A	0.2760	−0.0801	0.1467	0.049*
C3	0.33664 (15)	−0.15894 (12)	0.06597 (9)	0.0419 (4)
C4	0.36612 (17)	−0.26403 (13)	0.04640 (9)	0.0480 (4)
H4A	0.4044	−0.2642	0.0028	0.058*
H4B	0.2917	−0.3020	0.0432	0.058*
C5	0.45074 (16)	−0.31347 (13)	0.09715 (9)	0.0440 (4)
C6	0.39348 (16)	−0.30700 (12)	0.16681 (9)	0.0429 (4)
H6A	0.3338	−0.3594	0.1711	0.052*
H6B	0.4560	−0.3190	0.1999	0.052*
C7	0.4679 (2)	−0.42291 (16)	0.07882 (12)	0.0677 (6)
H7A	0.5099	−0.4277	0.0369	0.102*
H7B	0.3902	−0.4544	0.0751	0.102*
H7C	0.5145	−0.4553	0.1130	0.102*
C8	0.57395 (17)	−0.26183 (16)	0.09661 (12)	0.0615 (5)
H8A	0.6078	−0.2649	0.0525	0.092*
H8B	0.6273	−0.2945	0.1275	0.092*
H8C	0.5641	−0.1937	0.1096	0.092*
C9	0.23173 (14)	−0.12110 (11)	0.27412 (8)	0.0356 (3)
C10	0.12181 (15)	−0.09880 (12)	0.24388 (8)	0.0402 (4)
H10A	0.0975	−0.1328	0.2057	0.048*
C11	0.04870 (14)	−0.02559 (12)	0.27089 (8)	0.0392 (4)
H11A	−0.0248	−0.0100	0.2507	0.047*
C12	0.08487 (14)	0.02434 (11)	0.32787 (8)	0.0365 (3)
C13	0.19250 (15)	0.00026 (12)	0.35958 (8)	0.0400 (4)
H13A	0.2153	0.0332	0.3984	0.048*
C14	0.26572 (15)	−0.07305 (12)	0.33301 (8)	0.0401 (4)
H14A	0.3375	−0.0903	0.3544	0.048*
H1N1	0.3431 (18)	−0.2337 (16)	0.2774 (11)	0.058 (6)*
H1N2	0.024 (2)	0.1016 (15)	0.4588 (12)	0.053 (6)*
H2N2	−0.090 (2)	0.0441 (18)	0.4374 (12)	0.070 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0482 (3)	0.0360 (3)	0.0381 (3)	0.00670 (16)	0.00260 (16)	0.00170 (14)
N1	0.0455 (7)	0.0400 (7)	0.0372 (7)	0.0075 (6)	0.0036 (6)	0.0035 (6)
N2	0.0552 (10)	0.0451 (8)	0.0408 (8)	−0.0019 (7)	0.0078 (7)	−0.0014 (6)
O1	0.0801 (10)	0.0362 (6)	0.0572 (8)	−0.0043 (6)	0.0143 (7)	0.0014 (5)
O2	0.0568 (8)	0.0722 (9)	0.0595 (9)	0.0265 (7)	−0.0102 (7)	−0.0065 (7)
O3	0.0713 (9)	0.0505 (7)	0.0409 (7)	0.0019 (6)	0.0039 (6)	0.0088 (5)
C1	0.0363 (8)	0.0355 (8)	0.0394 (8)	−0.0015 (6)	0.0039 (6)	−0.0001 (6)
C2	0.0468 (9)	0.0351 (8)	0.0414 (8)	0.0041 (7)	0.0056 (7)	0.0007 (6)
C3	0.0419 (8)	0.0429 (9)	0.0408 (8)	−0.0026 (7)	0.0013 (7)	0.0026 (7)
C4	0.0592 (11)	0.0442 (9)	0.0408 (8)	−0.0062 (8)	−0.0010 (8)	−0.0059 (7)
C5	0.0474 (9)	0.0390 (8)	0.0456 (9)	0.0014 (7)	0.0044 (7)	−0.0092 (7)
C6	0.0458 (9)	0.0373 (8)	0.0457 (9)	0.0044 (7)	0.0046 (7)	0.0002 (7)
C7	0.0897 (16)	0.0462 (11)	0.0673 (13)	0.0112 (11)	0.0052 (12)	−0.0157 (10)
C8	0.0440 (10)	0.0679 (12)	0.0724 (13)	−0.0023 (9)	0.0105 (9)	−0.0133 (10)
C9	0.0369 (8)	0.0343 (8)	0.0357 (8)	−0.0009 (6)	0.0055 (6)	0.0031 (5)
C10	0.0407 (8)	0.0431 (8)	0.0368 (8)	−0.0027 (7)	−0.0003 (6)	−0.0054 (6)
C11	0.0358 (8)	0.0425 (8)	0.0392 (8)	0.0002 (7)	−0.0021 (6)	0.0007 (6)
C12	0.0382 (8)	0.0346 (7)	0.0366 (8)	−0.0002 (6)	0.0042 (6)	0.0002 (6)
C13	0.0398 (8)	0.0424 (8)	0.0379 (8)	−0.0020 (7)	−0.0023 (6)	−0.0043 (6)
C14	0.0358 (8)	0.0458 (9)	0.0386 (8)	0.0011 (7)	−0.0021 (6)	0.0004 (6)

S1—O2	1.4294 (15)	C5—C6	1.533 (2)
S1—O1	1.4360 (14)	C6—H6A	0.9700
S1—N2	1.6044 (15)	C6—H6B	0.9700
S1—C12	1.7677 (15)	C7—H7A	0.9600
N1—C1	1.356 (2)	C7—H7B	0.9600
N1—C9	1.410 (2)	C7—H7C	0.9600
N1—H1N1	0.88 (2)	C8—H8A	0.9600
N2—H1N2	0.89 (2)	C8—H8B	0.9600
N2—H2N2	0.88 (2)	C8—H8C	0.9600
O3—C3	1.246 (2)	C9—C10	1.389 (2)
C1—C2	1.358 (2)	C9—C14	1.396 (2)
C1—C6	1.505 (2)	C10—C11	1.384 (2)
C2—C3	1.423 (2)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.383 (2)
C3—C4	1.505 (2)	C11—H11A	0.9300
C4—C5	1.532 (2)	C12—C13	1.385 (2)
C4—H4A	0.9700	C13—C14	1.383 (2)
C4—H4B	0.9700	C13—H13A	0.9300
C5—C8	1.528 (3)	C14—H14A	0.9300
C5—C7	1.532 (2)
O2—S1—O1	118.92 (9)	C5—C6—H6A	108.6
O2—S1—N2	108.30 (10)	C1—C6—H6B	108.6
O1—S1—N2	106.15 (9)	C5—C6—H6B	108.6
O2—S1—C12	106.95 (8)	H6A—C6—H6B	107.6
O1—S1—C12	107.06 (8)	C5—C7—H7A	109.5
N2—S1—C12	109.21 (8)	C5—C7—H7B	109.5
C1—N1—C9	125.62 (14)	H7A—C7—H7B	109.5
C1—N1—H1N1	118.7 (14)	C5—C7—H7C	109.5
C9—N1—H1N1	115.6 (14)	H7A—C7—H7C	109.5
S1—N2—H1N2	106.5 (15)	H7B—C7—H7C	109.5
S1—N2—H2N2	111.5 (16)	C5—C8—H8A	109.5
H1N2—N2—H2N2	121 (2)	C5—C8—H8B	109.5
N1—C1—C2	123.34 (15)	H8A—C8—H8B	109.5
N1—C1—C6	114.23 (14)	C5—C8—H8C	109.5
C2—C1—C6	122.41 (15)	H8A—C8—H8C	109.5
C1—C2—C3	121.35 (15)	H8B—C8—H8C	109.5
C1—C2—H2A	119.3	C10—C9—C14	120.15 (14)
C3—C2—H2A	119.3	C10—C9—N1	120.67 (14)
O3—C3—C2	121.40 (16)	C14—C9—N1	119.09 (15)
O3—C3—C4	121.27 (16)	C11—C10—C9	119.55 (15)
C2—C3—C4	117.33 (15)	C11—C10—H10A	120.2
C3—C4—C5	111.63 (14)	C9—C10—H10A	120.2
C3—C4—H4A	109.3	C12—C11—C10	120.03 (15)
C5—C4—H4A	109.3	C12—C11—H11A	120.0
C3—C4—H4B	109.3	C10—C11—H11A	120.0
C5—C4—H4B	109.3	C11—C12—C13	120.75 (14)
H4A—C4—H4B	108.0	C11—C12—S1	119.01 (12)
C8—C5—C7	109.08 (17)	C13—C12—S1	120.24 (12)
C8—C5—C4	109.87 (17)	C14—C13—C12	119.51 (14)
C7—C5—C4	109.60 (16)	C14—C13—H13A	120.2
C8—C5—C6	110.33 (15)	C12—C13—H13A	120.2
C7—C5—C6	108.87 (15)	C13—C14—C9	119.93 (15)
C4—C5—C6	109.06 (14)	C13—C14—H14A	120.0
C1—C6—C5	114.73 (14)	C9—C14—H14A	120.0
C1—C6—H6A	108.6
C9—N1—C1—C2	14.4 (3)	C1—N1—C9—C14	−139.55 (17)
C9—N1—C1—C6	−167.16 (15)	C14—C9—C10—C11	2.8 (2)
N1—C1—C2—C3	−178.77 (15)	N1—C9—C10—C11	179.57 (14)
C6—C1—C2—C3	2.9 (3)	C9—C10—C11—C12	−0.4 (2)
C1—C2—C3—O3	−166.50 (17)	C10—C11—C12—C13	−1.7 (2)
C1—C2—C3—C4	12.7 (3)	C10—C11—C12—S1	177.15 (12)
O3—C3—C4—C5	136.43 (17)	O2—S1—C12—C11	5.87 (16)
C2—C3—C4—C5	−42.8 (2)	O1—S1—C12—C11	−122.63 (13)
C3—C4—C5—C8	−65.7 (2)	N2—S1—C12—C11	122.86 (14)
C3—C4—C5—C7	174.46 (16)	O2—S1—C12—C13	−175.28 (13)
C3—C4—C5—C6	55.35 (19)	O1—S1—C12—C13	56.22 (15)
N1—C1—C6—C5	−165.84 (15)	N2—S1—C12—C13	−58.29 (15)
C2—C1—C6—C5	12.6 (2)	C11—C12—C13—C14	1.4 (2)
C8—C5—C6—C1	79.9 (2)	S1—C12—C13—C14	−177.40 (12)
C7—C5—C6—C1	−160.42 (16)	C12—C13—C14—C9	1.0 (2)
C4—C5—C6—C1	−40.9 (2)	C10—C9—C14—C13	−3.1 (2)
C1—N1—C9—C10	43.7 (2)	N1—C9—C14—C13	−179.88 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.88 (2)	2.10 (2)	2.958 (2)	166 (2)
N2—H1N2···O3ii	0.89 (2)	2.02 (2)	2.900 (2)	169 (2)
N2—H2N2···O3iii	0.88 (2)	2.13 (2)	2.969 (2)	159 (2)
C6—H6A···O2iv	0.97	2.44	3.229 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.88 (2)	2.10 (2)	2.958 (2)	166 (2)
N2—H1N2⋯O3ii	0.89 (2)	2.02 (2)	2.900 (2)	169 (2)
N2—H2N2⋯O3iii	0.88 (2)	2.13 (2)	2.969 (2)	159 (2)
C6—H6A⋯O2iv	0.97	2.44	3.229 (2)	139

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