2-[7-Chloro-1,1-dioxo-2-(2,4,5-trifluoro-benz-yl)-3,4-dihydro-2H-1,2,4-benzothia-diazin-4-yl]acetic acid.

In the mol-ecule of the title compound, C(16)H(12)ClF(3)N(2)O(4)S, the thia-diazine ring adopts a half-chair conformation. The dihedral angle between the benzene ring of the benzothia-diazine ring system and trifluoro-phenyl group is 15.02 (7)°. In the crystal, centrosymmetrically related mol-ecules are linked into dimers via pairs of O-H⋯O hydrogen bonds, generating R(2) (2)(8) ring motifs. The dimers are further connected into a three-dimensional network by C-H⋯O hydrogen bonds.

Related literature

For the pharmacological properties of benzothia­diazine derivatives, see: Longman & Hamilton (1992 ▶); Buckheit et al. (1994 ▶); Yamada & Tang (1993 ▶); Phillips et al. (2002 ▶); Braghiroli et al. (2002 ▶); Pirotte et al. (1998 ▶); Francotte et al. (2007 ▶). For the biological properties and synthetic details of the title compound, see: Chen et al. (2010 ▶).

Experimental

Crystal data

C16H12ClF3N2O4S

M = 420.79

Monoclinic,

a = 9.3628 (2) Å

b = 12.3134 (2) Å

c = 15.5597 (3) Å

β = 105.996 (1)°

V = 1724.39 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 296 K

0.20 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

15140 measured reflections

4293 independent reflections

3302 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.131

S = 1.04

4293 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.73 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812014468/rz2722sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014468/rz2722Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014468/rz2722Isup3.cml

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

C16H12ClF3N2O4S	F(000) = 856
Mr = 420.79	Dx = 1.621 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4599 reflections
a = 9.3628 (2) Å	θ = 2.8–28.3°
b = 12.3134 (2) Å	µ = 0.40 mm−1
c = 15.5597 (3) Å	T = 296 K
β = 105.996 (1)°	Block, colourless
V = 1724.39 (6) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	3302 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −12→12
15140 measured reflections	k = −16→15
4293 independent reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0571P)2 + 1.0199P] where P = (Fo2 + 2Fc2)/3
4293 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.82 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
S1	0.45256 (6)	0.88685 (5)	0.08722 (3)	0.04077 (16)
Cl1	−0.00328 (10)	0.62773 (8)	0.09172 (6)	0.0872 (3)
C11	0.8849 (2)	0.89923 (18)	0.16523 (14)	0.0394 (5)
C5	0.3729 (2)	0.79827 (17)	0.14930 (12)	0.0350 (4)
N2	0.62050 (19)	0.90503 (15)	0.15259 (11)	0.0387 (4)
F2	1.26561 (18)	1.08588 (15)	0.23239 (13)	0.0768 (5)
O1	0.46125 (19)	0.83390 (17)	0.00742 (10)	0.0607 (5)
F3	1.0586 (2)	1.12091 (14)	0.07690 (12)	0.0729 (5)
C12	0.9947 (3)	0.88393 (19)	0.24347 (15)	0.0458 (5)
C6	0.2388 (2)	0.75123 (19)	0.10327 (14)	0.0449 (5)
H6	0.1985	0.7648	0.0426	0.054*
N1	0.5746 (2)	0.82433 (15)	0.28393 (11)	0.0392 (4)
F1	0.97529 (19)	0.80656 (14)	0.30117 (11)	0.0714 (5)
O2	0.37472 (19)	0.98763 (15)	0.07985 (13)	0.0597 (5)
C4	0.4382 (2)	0.77835 (16)	0.24064 (12)	0.0341 (4)
C7	0.6157 (2)	0.92240 (18)	0.24459 (13)	0.0400 (5)
H7A	0.7126	0.9466	0.2802	0.048*
H7B	0.5445	0.9792	0.2456	0.048*
C3	0.3601 (3)	0.70893 (18)	0.28347 (14)	0.0435 (5)
H3	0.3996	0.6932	0.3438	0.052*
C2	0.2264 (3)	0.66393 (19)	0.23789 (16)	0.0484 (5)
H2	0.1761	0.6192	0.2679	0.058*
C1	0.1662 (3)	0.6843 (2)	0.14823 (16)	0.0489 (5)
C9	0.5751 (3)	0.8936 (2)	0.43292 (13)	0.0447 (5)
C8	0.6382 (3)	0.8131 (2)	0.37949 (13)	0.0462 (5)
H8A	0.7449	0.8232	0.3935	0.055*
H8B	0.6200	0.7400	0.3972	0.055*
C19	0.7430 (2)	0.8351 (2)	0.14144 (16)	0.0468 (5)
H19A	0.7213	0.8102	0.0800	0.056*
H19B	0.7531	0.7720	0.1800	0.056*
C16	0.9087 (2)	0.98074 (19)	0.10813 (15)	0.0442 (5)
H16	0.8376	0.9939	0.0542	0.053*
C15	1.0367 (3)	1.0414 (2)	0.13140 (16)	0.0482 (5)
C14	1.1431 (3)	1.0230 (2)	0.21047 (18)	0.0506 (6)
C13	1.1245 (3)	0.9440 (2)	0.26747 (17)	0.0527 (6)
H13	1.1968	0.9307	0.3209	0.063*
O4	0.6474 (2)	0.89659 (17)	0.51717 (10)	0.0651 (6)
H4	0.6053	0.9380	0.5435	0.098*
O3	0.4682 (2)	0.95079 (17)	0.39943 (11)	0.0645 (6)

	U11	U22	U33	U12	U13	U23
S1	0.0349 (3)	0.0559 (3)	0.0303 (2)	−0.0079 (2)	0.00703 (18)	0.0092 (2)
Cl1	0.0666 (5)	0.1026 (7)	0.0868 (6)	−0.0466 (5)	0.0117 (4)	0.0042 (5)
C11	0.0321 (10)	0.0454 (12)	0.0418 (11)	0.0012 (9)	0.0122 (8)	−0.0088 (9)
C5	0.0337 (10)	0.0405 (11)	0.0317 (9)	−0.0010 (8)	0.0107 (7)	0.0047 (8)
N2	0.0305 (8)	0.0499 (10)	0.0360 (8)	−0.0045 (7)	0.0095 (7)	−0.0032 (7)
F2	0.0449 (9)	0.0762 (11)	0.1085 (14)	−0.0195 (8)	0.0196 (9)	−0.0269 (10)
O1	0.0554 (10)	0.0992 (15)	0.0291 (7)	−0.0253 (10)	0.0143 (7)	−0.0050 (8)
F3	0.0804 (12)	0.0682 (11)	0.0810 (11)	−0.0100 (9)	0.0403 (10)	0.0087 (8)
C12	0.0422 (12)	0.0479 (13)	0.0464 (12)	0.0040 (10)	0.0108 (9)	0.0000 (10)
C6	0.0404 (12)	0.0546 (14)	0.0376 (10)	−0.0088 (10)	0.0072 (9)	0.0050 (9)
N1	0.0435 (10)	0.0441 (10)	0.0272 (8)	0.0020 (8)	0.0052 (7)	−0.0012 (7)
F1	0.0715 (11)	0.0740 (11)	0.0638 (10)	0.0000 (9)	0.0101 (8)	0.0207 (8)
O2	0.0453 (10)	0.0598 (11)	0.0706 (11)	0.0027 (8)	0.0101 (8)	0.0289 (9)
C4	0.0403 (11)	0.0337 (10)	0.0292 (9)	0.0057 (8)	0.0110 (8)	0.0000 (7)
C7	0.0384 (11)	0.0444 (12)	0.0362 (10)	−0.0029 (9)	0.0084 (8)	−0.0067 (8)
C3	0.0597 (14)	0.0408 (12)	0.0341 (10)	0.0057 (10)	0.0195 (9)	0.0073 (8)
C2	0.0582 (14)	0.0397 (12)	0.0555 (13)	−0.0028 (11)	0.0295 (11)	0.0075 (10)
C1	0.0440 (13)	0.0486 (13)	0.0552 (13)	−0.0125 (10)	0.0154 (10)	0.0009 (10)
C9	0.0438 (12)	0.0551 (14)	0.0305 (9)	0.0077 (10)	0.0025 (8)	−0.0027 (9)
C8	0.0468 (12)	0.0566 (14)	0.0310 (10)	0.0132 (11)	0.0036 (8)	−0.0007 (9)
C19	0.0383 (12)	0.0501 (13)	0.0527 (13)	−0.0044 (10)	0.0138 (9)	−0.0133 (10)
C16	0.0386 (11)	0.0549 (14)	0.0402 (11)	0.0035 (10)	0.0124 (9)	−0.0059 (9)
C15	0.0477 (13)	0.0486 (13)	0.0544 (13)	0.0009 (10)	0.0243 (11)	−0.0043 (10)
C14	0.0335 (11)	0.0531 (14)	0.0666 (15)	−0.0051 (10)	0.0160 (10)	−0.0196 (12)
C13	0.0352 (12)	0.0634 (16)	0.0525 (13)	0.0073 (11)	0.0005 (9)	−0.0104 (12)
O4	0.0648 (12)	0.0852 (14)	0.0333 (8)	0.0296 (10)	−0.0066 (8)	−0.0137 (8)
O3	0.0606 (11)	0.0843 (14)	0.0379 (8)	0.0325 (10)	−0.0042 (7)	−0.0133 (8)

S1—O1	1.4245 (17)	C4—C3	1.407 (3)
S1—O2	1.4277 (19)	C7—H7A	0.9700
S1—N2	1.6357 (18)	C7—H7B	0.9700
S1—C5	1.7540 (19)	C3—C2	1.374 (3)
Cl1—C1	1.734 (2)	C3—H3	0.9300
C11—C12	1.373 (3)	C2—C1	1.376 (3)
C11—C16	1.398 (3)	C2—H2	0.9300
C11—C19	1.502 (3)	C9—O3	1.217 (3)
C5—C6	1.389 (3)	C9—O4	1.300 (2)
C5—C4	1.405 (3)	C9—C8	1.514 (3)
N2—C7	1.460 (2)	C8—H8A	0.9700
N2—C19	1.482 (3)	C8—H8B	0.9700
F2—C14	1.347 (3)	C19—H19A	0.9700
F3—C15	1.347 (3)	C19—H19B	0.9700
C12—F1	1.355 (3)	C16—C15	1.374 (3)
C12—C13	1.383 (3)	C16—H16	0.9300
C6—C1	1.376 (3)	C15—C14	1.372 (4)
C6—H6	0.9300	C14—C13	1.360 (4)
N1—C4	1.389 (3)	C13—H13	0.9300
N1—C8	1.448 (2)	O4—H4	0.8200
N1—C7	1.453 (3)
O1—S1—O2	118.58 (12)	C4—C3—H3	119.4
O1—S1—N2	109.19 (10)	C3—C2—C1	120.7 (2)
O2—S1—N2	108.23 (11)	C3—C2—H2	119.7
O1—S1—C5	109.30 (11)	C1—C2—H2	119.7
O2—S1—C5	107.43 (10)	C6—C1—C2	120.2 (2)
N2—S1—C5	102.98 (9)	C6—C1—Cl1	119.63 (19)
C12—C11—C16	116.8 (2)	C2—C1—Cl1	120.18 (18)
C12—C11—C19	122.8 (2)	O3—C9—O4	123.6 (2)
C16—C11—C19	120.4 (2)	O3—C9—C8	122.87 (19)
C6—C5—C4	121.91 (19)	O4—C9—C8	113.50 (19)
C6—C5—S1	115.88 (15)	N1—C8—C9	112.90 (18)
C4—C5—S1	122.18 (16)	N1—C8—H8A	109.0
C7—N2—C19	115.69 (18)	C9—C8—H8A	109.0
C7—N2—S1	110.23 (13)	N1—C8—H8B	109.0
C19—N2—S1	119.35 (14)	C9—C8—H8B	109.0
F1—C12—C11	118.7 (2)	H8A—C8—H8B	107.8
F1—C12—C13	117.7 (2)	N2—C19—C11	109.07 (18)
C11—C12—C13	123.6 (2)	N2—C19—H19A	109.9
C1—C6—C5	119.4 (2)	C11—C19—H19A	109.9
C1—C6—H6	120.3	N2—C19—H19B	109.9
C5—C6—H6	120.3	C11—C19—H19B	109.9
C4—N1—C8	121.46 (18)	H19A—C19—H19B	108.3
C4—N1—C7	116.70 (16)	C15—C16—C11	120.2 (2)
C8—N1—C7	115.48 (18)	C15—C16—H16	119.9
N1—C4—C5	120.34 (18)	C11—C16—H16	119.9
N1—C4—C3	123.12 (18)	F3—C15—C14	119.1 (2)
C5—C4—C3	116.53 (19)	F3—C15—C16	120.2 (2)
N1—C7—N2	112.00 (17)	C14—C15—C16	120.8 (2)
N1—C7—H7A	109.2	F2—C14—C13	120.0 (2)
N2—C7—H7A	109.2	F2—C14—C15	119.3 (2)
N1—C7—H7B	109.2	C13—C14—C15	120.7 (2)
N2—C7—H7B	109.2	C14—C13—C12	117.9 (2)
H7A—C7—H7B	107.9	C14—C13—H13	121.1
C2—C3—C4	121.29 (19)	C12—C13—H13	121.1
C2—C3—H3	119.4	C9—O4—H4	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3i	0.82	1.86	2.676 (2)	171
C3—H3···O1ii	0.93	2.47	3.391 (3)	169
C16—H16···O2iii	0.93	2.46	3.387 (2)	172
C13—H13···O3iv	0.93	2.51	3.307 (3)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3i	0.82	1.86	2.676 (2)	171
C3—H3⋯O1ii	0.93	2.47	3.391 (3)	169
C16—H16⋯O2iii	0.93	2.46	3.387 (2)	172
C13—H13⋯O3iv	0.93	2.51	3.307 (3)	144

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