N-Butyl-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine-3-carboxamide 1,1-dioxide.

The title compound, C(14)H(18)N(2)O(4)S, contains hydrogen-bonded dimeric pairs of mol-ecules arranged around inversion centers, forming 14-membered rings with an R(2) (2)(14) motif. The structure is stabilized by extensive intra-molecular inter-actions. The thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by -0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008 ▶); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008 ▶); Bernstein et al. (1994 ▶); Gupta et al. (1993 ▶, 2002 ▶); Kojić-Prodić & Rużić-Toroš (1982 ▶); Lombardino (1971 ▶); Lombardino & Wiseman (1972 ▶); Rehman et al. (2005 ▶, 2006 ▶); Sianesi et al. (1973 ▶); Siddiqui et al. (2008 ▶); Zinnes et al. (1982 ▶); Drebushchak et al. (2006 ▶).

Experimental

Crystal data

C14H18N2O4S

M = 310.36

Monoclinic,

a = 10.233 (2) Å

b = 14.780 (4) Å

c = 10.365 (5) Å

β = 108.79 (2)°

V = 1484.1 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 173 (2) K

0.14 × 0.12 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.968, T max = 0.986

12380 measured reflections

3405 independent reflections

2646 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.100

S = 1.03

3405 reflections

198 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.43 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S160053680801670X/bh2176sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801670X/bh2176Isup2.hkl

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

C14H18N2O4S	F000 = 656
Mr = 310.36	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12380 reflections
a = 10.233 (2) Å	θ = 3.4–27.6º
b = 14.780 (4) Å	µ = 0.24 mm−1
c = 10.365 (5) Å	T = 173 (2) K
β = 108.79 (2)º	Prism, colorless
V = 1484.1 (9) Å3	0.14 × 0.12 × 0.06 mm
Z = 4

Nonius KappaCCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.041
T = 173(2) K	θmax = 27.6º
ω and φ scans	θmin = 3.4º
Absorption correction: Multi-scan(SORTAV; Blessing, 1997)	h = −13→13
Tmin = 0.968, Tmax = 0.986	k = −19→19
12380 measured reflections	l = −13→13

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.045P)2 + 0.606P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
3405 reflections	Δρmax = 0.30 e Å−3
198 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S1	0.53051 (4)	0.13868 (3)	0.96872 (5)	0.03033 (13)
O1	0.45310 (12)	0.12905 (9)	0.82760 (14)	0.0384 (3)
O2	0.46724 (13)	0.11547 (9)	1.06916 (15)	0.0400 (3)
O3	0.86081 (13)	0.22923 (9)	0.83438 (13)	0.0336 (3)
H3O	0.899 (2)	0.1799 (16)	0.816 (2)	0.050*
O4	0.92527 (12)	0.06200 (9)	0.82242 (13)	0.0356 (3)
N1	0.67274 (13)	0.07980 (9)	0.99855 (14)	0.0265 (3)
N2	0.78434 (15)	−0.04424 (10)	0.86553 (16)	0.0327 (3)
H2N	0.714 (2)	−0.0525 (14)	0.894 (2)	0.039*
C1	0.59359 (17)	0.24980 (11)	0.99677 (17)	0.0283 (4)
C2	0.53309 (18)	0.31325 (12)	1.05849 (19)	0.0342 (4)
H2	0.4587	0.2967	1.0897	0.041*
C3	0.58309 (19)	0.40116 (12)	1.07376 (19)	0.0359 (4)
H3	0.5430	0.4455	1.1159	0.043*
C4	0.69144 (19)	0.42436 (12)	1.02763 (18)	0.0349 (4)
H4	0.7235	0.4851	1.0363	0.042*
C5	0.75381 (17)	0.36033 (12)	0.96906 (18)	0.0309 (4)
H5	0.8289	0.3772	0.9392	0.037*
C6	0.70664 (17)	0.27103 (11)	0.95385 (17)	0.0276 (4)
C7	0.77716 (16)	0.19970 (12)	0.90287 (17)	0.0272 (4)
C8	0.76003 (16)	0.11021 (12)	0.92283 (17)	0.0269 (4)
C9	0.74832 (19)	0.05636 (13)	1.14249 (18)	0.0355 (4)
H9A	0.8206	0.0121	1.1457	0.043*
H9B	0.6839	0.0305	1.1848	0.043*
H9C	0.7905	0.1110	1.1921	0.043*
C10	0.82934 (17)	0.04054 (12)	0.86719 (17)	0.0288 (4)
C11	0.8470 (2)	−0.12047 (12)	0.8176 (2)	0.0385 (4)
H11A	0.9478	−0.1107	0.8430	0.046*
H11B	0.8091	−0.1238	0.7170	0.046*
C12	0.82004 (18)	−0.20820 (12)	0.8775 (2)	0.0335 (4)
H12A	0.7192	−0.2189	0.8486	0.040*
H12B	0.8537	−0.2034	0.9781	0.040*
C13	0.88952 (19)	−0.28900 (12)	0.83487 (19)	0.0339 (4)
H13A	0.8496	−0.2975	0.7351	0.041*
H13B	0.9892	−0.2761	0.8562	0.041*
C14	0.8724 (2)	−0.37560 (13)	0.9058 (2)	0.0405 (5)
H14A	0.9237	−0.4245	0.8799	0.049*
H14B	0.7743	−0.3916	0.8787	0.049*
H14C	0.9079	−0.3668	1.0048	0.049*

	U11	U22	U33	U12	U13	U23
S1	0.0252 (2)	0.0286 (2)	0.0417 (3)	−0.00243 (16)	0.01704 (18)	−0.00165 (18)
O1	0.0263 (6)	0.0414 (8)	0.0450 (8)	−0.0039 (5)	0.0078 (5)	−0.0038 (6)
O2	0.0400 (7)	0.0340 (7)	0.0597 (9)	−0.0031 (5)	0.0352 (7)	−0.0005 (6)
O3	0.0347 (7)	0.0328 (7)	0.0411 (7)	−0.0041 (5)	0.0232 (6)	0.0015 (6)
O4	0.0316 (6)	0.0379 (7)	0.0455 (8)	−0.0004 (5)	0.0239 (6)	0.0008 (6)
N1	0.0267 (7)	0.0273 (7)	0.0306 (8)	−0.0003 (5)	0.0160 (6)	0.0018 (6)
N2	0.0306 (8)	0.0311 (8)	0.0433 (9)	−0.0001 (6)	0.0215 (7)	−0.0031 (7)
C1	0.0269 (8)	0.0267 (8)	0.0330 (9)	0.0003 (6)	0.0121 (7)	0.0023 (7)
C2	0.0317 (9)	0.0342 (10)	0.0404 (10)	0.0042 (7)	0.0167 (8)	0.0028 (8)
C3	0.0400 (10)	0.0296 (9)	0.0393 (10)	0.0073 (8)	0.0142 (8)	0.0019 (8)
C4	0.0407 (10)	0.0269 (9)	0.0353 (10)	−0.0007 (7)	0.0097 (8)	0.0024 (7)
C5	0.0306 (9)	0.0309 (9)	0.0315 (9)	−0.0027 (7)	0.0104 (7)	0.0040 (7)
C6	0.0255 (8)	0.0307 (9)	0.0267 (8)	−0.0011 (7)	0.0087 (7)	0.0019 (7)
C7	0.0229 (8)	0.0338 (9)	0.0264 (8)	−0.0028 (6)	0.0098 (7)	0.0014 (7)
C8	0.0234 (8)	0.0318 (9)	0.0282 (9)	−0.0018 (6)	0.0122 (7)	0.0008 (7)
C9	0.0385 (10)	0.0390 (10)	0.0331 (10)	−0.0019 (8)	0.0171 (8)	0.0021 (8)
C10	0.0245 (8)	0.0345 (9)	0.0290 (9)	0.0006 (7)	0.0107 (7)	0.0003 (7)
C11	0.0432 (10)	0.0326 (10)	0.0502 (12)	0.0037 (8)	0.0294 (9)	−0.0028 (8)
C12	0.0324 (9)	0.0340 (10)	0.0398 (10)	0.0013 (7)	0.0194 (8)	−0.0026 (8)
C13	0.0329 (9)	0.0348 (10)	0.0367 (10)	0.0015 (7)	0.0152 (8)	−0.0036 (8)
C14	0.0365 (10)	0.0356 (10)	0.0486 (12)	−0.0003 (8)	0.0128 (9)	−0.0003 (9)

S1—O1	1.4286 (15)	C5—C6	1.397 (2)
S1—O2	1.4335 (14)	C5—H5	0.9500
S1—N1	1.6375 (14)	C6—C7	1.469 (2)
S1—C1	1.7543 (18)	C7—C8	1.359 (2)
O3—C7	1.349 (2)	C8—C10	1.470 (2)
O3—H3O	0.88 (2)	C9—H9A	0.9800
O4—C10	1.254 (2)	C9—H9B	0.9800
N1—C8	1.438 (2)	C9—H9C	0.9800
N1—C9	1.484 (2)	C11—C12	1.501 (3)
N2—C10	1.333 (2)	C11—H11A	0.9900
N2—C11	1.460 (2)	C11—H11B	0.9900
N2—H2N	0.87 (2)	C12—C13	1.526 (2)
C1—C2	1.388 (2)	C12—H12A	0.9900
C1—C6	1.402 (2)	C12—H12B	0.9900
C2—C3	1.387 (3)	C13—C14	1.514 (3)
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.385 (3)	C13—H13B	0.9900
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.386 (3)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
O1—S1—O2	119.25 (9)	C7—C8—C10	121.34 (15)
O1—S1—N1	107.84 (8)	N1—C8—C10	117.28 (14)
O2—S1—N1	108.51 (8)	N1—C9—H9A	109.5
O1—S1—C1	108.42 (8)	N1—C9—H9B	109.5
O2—S1—C1	109.38 (8)	H9A—C9—H9B	109.5
N1—S1—C1	102.07 (8)	N1—C9—H9C	109.5
C7—O3—H3O	104.4 (15)	H9A—C9—H9C	109.5
C8—N1—C9	114.06 (13)	H9B—C9—H9C	109.5
C8—N1—S1	113.67 (11)	O4—C10—N2	122.76 (16)
C9—N1—S1	117.24 (11)	O4—C10—C8	120.15 (15)
C10—N2—C11	122.83 (15)	N2—C10—C8	117.08 (15)
C10—N2—H2N	116.6 (14)	N2—C11—C12	111.55 (15)
C11—N2—H2N	120.6 (14)	N2—C11—H11A	109.3
C2—C1—C6	122.08 (16)	C12—C11—H11A	109.3
C2—C1—S1	120.92 (13)	N2—C11—H11B	109.3
C6—C1—S1	117.00 (13)	C12—C11—H11B	109.3
C3—C2—C1	118.85 (16)	H11A—C11—H11B	108.0
C3—C2—H2	120.6	C11—C12—C13	113.08 (14)
C1—C2—H2	120.6	C11—C12—H12A	109.0
C4—C3—C2	119.98 (17)	C13—C12—H12A	109.0
C4—C3—H3	120.0	C11—C12—H12B	109.0
C2—C3—H3	120.0	C13—C12—H12B	109.0
C3—C4—C5	121.00 (17)	H12A—C12—H12B	107.8
C3—C4—H4	119.5	C14—C13—C12	112.53 (15)
C5—C4—H4	119.5	C14—C13—H13A	109.1
C4—C5—C6	120.23 (16)	C12—C13—H13A	109.1
C4—C5—H5	119.9	C14—C13—H13B	109.1
C6—C5—H5	119.9	C12—C13—H13B	109.1
C5—C6—C1	117.78 (16)	H13A—C13—H13B	107.8
C5—C6—C7	121.80 (15)	C13—C14—H14A	109.5
C1—C6—C7	120.31 (15)	C13—C14—H14B	109.5
O3—C7—C8	122.01 (15)	H14A—C14—H14B	109.5
O3—C7—C6	115.20 (15)	C13—C14—H14C	109.5
C8—C7—C6	122.79 (15)	H14A—C14—H14C	109.5
C7—C8—N1	121.38 (14)	H14B—C14—H14C	109.5
O1—S1—N1—C8	61.67 (13)	S1—C1—C6—C7	−6.9 (2)
O2—S1—N1—C8	−167.86 (11)	C5—C6—C7—O3	−19.3 (2)
C1—S1—N1—C8	−52.42 (13)	C1—C6—C7—O3	164.56 (15)
O1—S1—N1—C9	−161.75 (12)	C5—C6—C7—C8	160.65 (16)
O2—S1—N1—C9	−31.28 (14)	C1—C6—C7—C8	−15.5 (2)
C1—S1—N1—C9	84.16 (13)	O3—C7—C8—N1	178.67 (14)
O1—S1—C1—C2	103.81 (15)	C6—C7—C8—N1	−1.3 (2)
O2—S1—C1—C2	−27.73 (17)	O3—C7—C8—C10	−1.7 (3)
N1—S1—C1—C2	−142.53 (15)	C6—C7—C8—C10	178.33 (15)
O1—S1—C1—C6	−76.03 (15)	C9—N1—C8—C7	−98.65 (19)
O2—S1—C1—C6	152.43 (13)	S1—N1—C8—C7	39.3 (2)
N1—S1—C1—C6	37.63 (15)	C9—N1—C8—C10	81.71 (18)
C6—C1—C2—C3	2.3 (3)	S1—N1—C8—C10	−140.30 (13)
S1—C1—C2—C3	−177.53 (14)	C11—N2—C10—O4	3.1 (3)
C1—C2—C3—C4	0.1 (3)	C11—N2—C10—C8	−177.77 (16)
C2—C3—C4—C5	−1.7 (3)	C7—C8—C10—O4	13.4 (3)
C3—C4—C5—C6	0.9 (3)	N1—C8—C10—O4	−166.94 (15)
C4—C5—C6—C1	1.4 (2)	C7—C8—C10—N2	−165.76 (16)
C4—C5—C6—C7	−174.82 (16)	N1—C8—C10—N2	13.9 (2)
C2—C1—C6—C5	−3.0 (3)	C10—N2—C11—C12	156.43 (17)
S1—C1—C6—C5	176.82 (13)	N2—C11—C12—C13	−177.35 (16)
C2—C1—C6—C7	173.25 (16)	C11—C12—C13—C14	174.83 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N···O2i	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N···N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B···O2	0.98	2.49	2.864 (2)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N⋯O2i	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N⋯N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B⋯O2	0.98	2.49	2.864 (2)	102

Symmetry code: (i) .