2-(3,5-Dimethyl-1,1-dioxo-2H-1λ(6),2,6-thia-diazin-4-yl)benzoic acid.

In the title mol-ecule, C(12)H(12)N(2)O(4)S, the S atom of the thia-diazine ring deviates by 0.5104 (4) Å from the mean plane of the other five atoms [largest deviation = 0.0623 (15) Å] giving a slightly distorted sofa conformation. The carb-oxy H atom was refined as disordered over two sets of sites with refined occupancies of 0.58 (2) and 0.48 (2). This corresponds to rotational disorder of the C=O and O-H groups about the attached C-C bond. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds connect the mol-ecules into chains along [110].

Related literature

The title compound is a phenyl acid thia­diazine derivative. For synthetic background and applications of 1,2,6-thia­diazine-1,1-dioxide derivatives, see: Wright (1964 ▶); Breining et al. (1995 ▶). For a related structure, see: Bhatt et al. (2012 ▶)

Experimental

Crystal data

C12H12N2O4S

M = 280.30

Monoclinic,

a = 10.5048 (14) Å

b = 10.4254 (13) Å

c = 11.1294 (14) Å

β = 92.772 (4)°

V = 1217.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.24 × 0.19 × 0.18 mm

Data collection

Bruker Kappa DUO APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.936, T max = 0.952

5724 measured reflections

3030 independent reflections

2573 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

3030 reflections

187 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037026/lh5507sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037026/lh5507Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037026/lh5507Isup3.cml

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

C12H12N2O4S	F(000) = 584
Mr = 280.30	Dx = 1.529 Mg m−3Dm = 0 Mg m−3Dm measured by not measured
Monoclinic, P21/n	Melting point: 523 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.5048 (14) Å	Cell parameters from 5724 reflections
b = 10.4254 (13) Å	θ = 2.6–28.4°
c = 11.1294 (14) Å	µ = 0.28 mm−1
β = 92.772 (4)°	T = 173 K
V = 1217.4 (3) Å3	0, colourless
Z = 4	0.24 × 0.19 × 0.18 mm

Bruker Kappa DUO APEXII diffractometer	3030 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
0.5° φ scans and ω scans	θmax = 28.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −12→14
Tmin = 0.936, Tmax = 0.952	k = −13→12
5724 measured 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.4988P] where P = (Fo2 + 2Fc2)/3
3030 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.37 e Å−3
3 restraints	Δρmin = −0.42 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	Occ. (<1)
S1	0.98957 (3)	0.13712 (4)	0.12970 (3)	0.02250 (12)
O1	1.01274 (12)	0.00736 (13)	0.16838 (11)	0.0344 (3)
O2	1.09339 (11)	0.20118 (15)	0.07866 (12)	0.0395 (3)
O3	0.39308 (11)	0.41036 (12)	0.06653 (11)	0.0311 (3)
O4	0.60472 (11)	0.39428 (13)	0.08005 (13)	0.0353 (3)
N1	0.87045 (12)	0.13786 (13)	0.02772 (11)	0.0231 (3)
N2	0.93605 (12)	0.21970 (13)	0.23740 (12)	0.0241 (3)
C1	0.65248 (16)	0.09799 (18)	−0.03955 (14)	0.0285 (3)
H1A	0.5677	0.0883	−0.0076	0.043*
H1B	0.6784	0.0168	−0.0754	0.043*
H1C	0.6500	0.1653	−0.1010	0.043*
C2	0.74610 (14)	0.13394 (14)	0.06012 (13)	0.0201 (3)
C3	0.71616 (13)	0.16832 (14)	0.17403 (13)	0.0192 (3)
C4	0.81280 (14)	0.22158 (14)	0.25478 (13)	0.0208 (3)
C5	0.77422 (16)	0.29238 (17)	0.36412 (15)	0.0293 (4)
H5A	0.8483	0.3374	0.4007	0.044*
H5B	0.7416	0.2314	0.4222	0.044*
H5C	0.7076	0.3547	0.3412	0.044*
C6	0.58294 (14)	0.15746 (14)	0.21603 (13)	0.0204 (3)
C7	0.48160 (14)	0.24135 (14)	0.18462 (13)	0.0206 (3)
C8	0.36101 (15)	0.21905 (16)	0.22911 (14)	0.0252 (3)
H8	0.2925	0.2749	0.2067	0.030*
C9	0.34023 (16)	0.11711 (17)	0.30514 (15)	0.0292 (4)
H9	0.2581	0.1035	0.3349	0.035*
C10	0.43933 (16)	0.03505 (17)	0.33774 (15)	0.0296 (4)
H10	0.4257	−0.0349	0.3903	0.036*
C11	0.55916 (16)	0.05546 (15)	0.29322 (14)	0.0263 (3)
H11	0.6267	−0.0015	0.3159	0.032*
C12	0.49362 (14)	0.35576 (14)	0.10521 (14)	0.0217 (3)
H4	0.606 (4)	0.469 (2)	0.028 (3)	0.030 (16)*	0.52 (8)
H3	0.406 (6)	0.491 (3)	0.025 (5)	0.06 (2)*	0.48 (8)
H1	0.892 (2)	0.113 (2)	−0.0528 (8)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01708 (18)	0.0281 (2)	0.02257 (19)	0.00231 (14)	0.00382 (13)	−0.00124 (14)
O1	0.0401 (7)	0.0339 (7)	0.0292 (6)	0.0161 (6)	0.0017 (5)	0.0019 (5)
O2	0.0237 (6)	0.0582 (9)	0.0374 (7)	−0.0106 (6)	0.0105 (5)	−0.0040 (6)
O3	0.0259 (6)	0.0294 (6)	0.0376 (7)	0.0023 (5)	−0.0030 (5)	0.0086 (5)
O4	0.0255 (6)	0.0308 (6)	0.0503 (8)	0.0038 (5)	0.0102 (5)	0.0165 (6)
N1	0.0207 (6)	0.0306 (7)	0.0182 (6)	0.0028 (5)	0.0029 (5)	−0.0019 (5)
N2	0.0201 (6)	0.0278 (7)	0.0246 (6)	0.0012 (5)	0.0017 (5)	−0.0048 (5)
C1	0.0275 (8)	0.0347 (9)	0.0231 (7)	−0.0019 (7)	−0.0012 (6)	−0.0041 (7)
C2	0.0201 (7)	0.0183 (7)	0.0219 (7)	0.0013 (5)	0.0018 (5)	0.0012 (6)
C3	0.0182 (6)	0.0178 (6)	0.0218 (7)	0.0022 (5)	0.0030 (5)	0.0010 (5)
C4	0.0228 (7)	0.0193 (7)	0.0204 (6)	0.0026 (6)	0.0026 (5)	0.0000 (5)
C5	0.0275 (8)	0.0350 (9)	0.0256 (7)	0.0028 (7)	0.0024 (6)	−0.0096 (7)
C6	0.0196 (7)	0.0211 (7)	0.0207 (6)	−0.0005 (6)	0.0035 (5)	−0.0006 (5)
C7	0.0191 (7)	0.0206 (7)	0.0222 (7)	−0.0010 (6)	0.0027 (5)	−0.0011 (6)
C8	0.0191 (7)	0.0281 (8)	0.0285 (7)	0.0005 (6)	0.0031 (6)	−0.0019 (6)
C9	0.0242 (8)	0.0326 (9)	0.0313 (8)	−0.0066 (7)	0.0081 (6)	−0.0011 (7)
C10	0.0338 (9)	0.0278 (8)	0.0279 (8)	−0.0048 (7)	0.0071 (6)	0.0039 (7)
C11	0.0277 (8)	0.0233 (8)	0.0281 (7)	0.0024 (6)	0.0038 (6)	0.0036 (6)
C12	0.0212 (7)	0.0202 (7)	0.0236 (7)	0.0012 (6)	0.0016 (5)	−0.0014 (6)

S1—O2	1.4206 (12)	C3—C6	1.5011 (19)
S1—O1	1.4368 (13)	C4—C5	1.496 (2)
S1—N2	1.5998 (13)	C5—H5A	0.9800
S1—N1	1.6483 (13)	C5—H5B	0.9800
O3—C12	1.2573 (19)	C5—H5C	0.9800
O3—H3	0.9699 (10)	C6—C11	1.397 (2)
O4—C12	1.2781 (18)	C6—C7	1.409 (2)
O4—H4	0.9699 (10)	C7—C8	1.402 (2)
N1—C2	1.3724 (19)	C7—C12	1.493 (2)
N1—H1	0.9698 (10)	C8—C9	1.382 (2)
N2—C4	1.3185 (19)	C8—H8	0.9500
C1—C2	1.494 (2)	C9—C10	1.382 (2)
C1—H1A	0.9800	C9—H9	0.9500
C1—H1B	0.9800	C10—C11	1.391 (2)
C1—H1C	0.9800	C10—H10	0.9500
C2—C3	1.369 (2)	C11—H11	0.9500
C3—C4	1.435 (2)
O2—S1—O1	116.12 (8)	C4—C5—H5A	109.5
O2—S1—N2	110.55 (8)	C4—C5—H5B	109.5
O1—S1—N2	110.05 (7)	H5A—C5—H5B	109.5
O2—S1—N1	107.12 (8)	C4—C5—H5C	109.5
O1—S1—N1	108.82 (8)	H5A—C5—H5C	109.5
N2—S1—N1	103.34 (7)	H5B—C5—H5C	109.5
C12—O3—H3	115 (4)	C11—C6—C7	118.02 (13)
C12—O4—H4	115 (2)	C11—C6—C3	116.49 (13)
C2—N1—S1	121.29 (10)	C7—C6—C3	125.49 (13)
C2—N1—H1	120.0 (14)	C8—C7—C6	119.63 (14)
S1—N1—H1	115.7 (14)	C8—C7—C12	116.44 (13)
C4—N2—S1	120.07 (11)	C6—C7—C12	123.94 (13)
C2—C1—H1A	109.5	C9—C8—C7	121.06 (15)
C2—C1—H1B	109.5	C9—C8—H8	119.5
H1A—C1—H1B	109.5	C7—C8—H8	119.5
C2—C1—H1C	109.5	C10—C9—C8	119.82 (15)
H1A—C1—H1C	109.5	C10—C9—H9	120.1
H1B—C1—H1C	109.5	C8—C9—H9	120.1
C3—C2—N1	119.99 (14)	C9—C10—C11	119.65 (15)
C3—C2—C1	125.51 (14)	C9—C10—H10	120.2
N1—C2—C1	114.40 (13)	C11—C10—H10	120.2
C2—C3—C4	119.62 (13)	C10—C11—C6	121.82 (15)
C2—C3—C6	121.88 (13)	C10—C11—H11	119.1
C4—C3—C6	118.44 (12)	C6—C11—H11	119.1
N2—C4—C3	124.92 (13)	O3—C12—O4	122.93 (14)
N2—C4—C5	115.67 (13)	O3—C12—C7	118.07 (13)
C3—C4—C5	119.29 (13)	O4—C12—C7	119.00 (13)
O2—S1—N1—C2	−152.60 (12)	C4—C3—C6—C11	−78.20 (18)
O1—S1—N1—C2	81.12 (13)	C2—C3—C6—C7	−75.8 (2)
N2—S1—N1—C2	−35.82 (14)	C4—C3—C6—C7	101.44 (18)
O2—S1—N2—C4	143.83 (13)	C11—C6—C7—C8	−1.2 (2)
O1—S1—N2—C4	−86.58 (14)	C3—C6—C7—C8	179.14 (14)
N1—S1—N2—C4	29.49 (14)	C11—C6—C7—C12	178.69 (14)
S1—N1—C2—C3	20.0 (2)	C3—C6—C7—C12	−0.9 (2)
S1—N1—C2—C1	−163.46 (12)	C6—C7—C8—C9	1.1 (2)
N1—C2—C3—C4	6.8 (2)	C12—C7—C8—C9	−178.81 (15)
C1—C2—C3—C4	−169.34 (15)	C7—C8—C9—C10	−0.3 (3)
N1—C2—C3—C6	−175.96 (13)	C8—C9—C10—C11	−0.3 (3)
C1—C2—C3—C6	7.9 (2)	C9—C10—C11—C6	0.2 (3)
S1—N2—C4—C3	−9.0 (2)	C7—C6—C11—C10	0.6 (2)
S1—N2—C4—C5	174.88 (12)	C3—C6—C11—C10	−179.72 (14)
C2—C3—C4—N2	−13.2 (2)	C8—C7—C12—O3	−12.3 (2)
C6—C3—C4—N2	169.49 (14)	C6—C7—C12—O3	167.81 (15)
C2—C3—C4—C5	162.84 (15)	C8—C7—C12—O4	167.35 (15)
C6—C3—C4—C5	−14.5 (2)	C6—C7—C12—O4	−12.6 (2)
C2—C3—C6—C11	104.52 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.97 (1)	2.09 (2)	2.9699 (18)	151 (2)
O4—H4···O3ii	0.97 (3)	1.64 (3)	2.6103 (19)	177 (3)
O3—H3···O4ii	0.97 (3)	1.67 (3)	2.6103 (19)	161 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.97 (1)	2.09 (2)	2.9699 (18)	151 (2)
O4—H4⋯O3ii	0.97 (3)	1.64 (3)	2.6103 (19)	177 (3)
O3—H3⋯O4ii	0.97 (3)	1.67 (3)	2.6103 (19)	161 (5)

Symmetry codes: (i) ; (ii) .