2-[7-Chloro-1,1-dioxo-2-(2,4,5-trifluoro­benz­yl)-3,4-dihydro-2H-1,2,4-benzothia­diazin-4-yl]acetic acid

Yang, Y.; Guo, Y.; Zhu, C.

doi:10.1107/S1600536812014468

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1363

doi:10.1107/S1600536812014468

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2-[7-Chloro-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2,4-benzothiadiazin-4-yl]acetic acid

Yanchun Yang,^a Yuhua Guo ^b and Changjin Zhu ^a ^*

^aDepartment of Applied Chemistry, Beijing Institute of Technology, Zhongguancun South Street, 100081 Beijing, People's Republic of China, and ^bDepartment of Chemistry and Environmental Engineering, Anyang Institute of Technology, Henan 455000, People's Republic of China
^*Correspondence e-mail: zcj@bit.edu.cn

(Received 11 March 2012; accepted 3 April 2012; online 13 April 2012)

In the molecule of the title compound, C₁₆H₁₂ClF₃N₂O₄S, the thiadiazine ring adopts a half-chair conformation. The dihedral angle between the benzene ring of the benzothiadiazine ring system and trifluorophenyl group is 15.02 (7)°. In the crystal, centrosymmetrically related molecules are linked into dimers via pairs of O—H⋯O hydrogen bonds, generating R₂²(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_r = 420.79
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.131
S = 1.04
4293 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.82 e Å⁻³

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⋯O3^iv	0.93	2.51	3.307 (3)	144
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z; (iv) x+1, y, z.

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014468/rz2722sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812014468/rz2722Isup3.cml

checkCIF report

Comment top

Benzothiadiazine derivatives have attracted considerable attention because they are endowed with a large spectrum of properties. Since the 1950's, various pharmacological investigations of newly synthesized benzothiadiazines demonstrated interesting pharmacological activities and showed great potential for the development of new medications for treating diseases (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). The title compound, whose structure is reported herein, was synthesized and used as an aldose reductase inhibitor (Chen et al., 2010).

In the molecule of the title compound (Fig. 1), the thiadiazine ring (C7/N1/C4/C5/S1/N2) adopts a half-chair conformation, with puckering parameters Q_T = 0.5164 (19) Å, θ = 47.5 (2)° and ϕ = -25.9 (3)°. The deviation of the S1, N1 and N2 atoms from the plane of the benzene ring of the benzothiadiazin ring system are -0.0726 (6), 0.0305 (19) and 0.2655 (18) Å, respectively. The dihedral angle formed by the two six-membered aromatic rings C1–C6 and C11–C16 is 15.02 (7)°. In the crystal, centrosymmetrically related molecules interact to form dimers through pairs of O—H···O hydrogen bonds (Table 1) generating a R²₂(8) ring motif. The dimers are further linked into a three-dimensional network by intermolecular C—H···O hydrogen bonds (Table 1).

Related literature top

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 top

A mixture of methyl 2-(7-chloro-1,1-dioxido-2-(2,4,5-trifluorobenzyl)-2H-benzo[e][1,2,4]thiadiazin-4(3H)-yl)acetate (1 mmol), 1,4-dioxane (5 ml) and saturated aqueous sodium hydroxide (5 ml) was stirred at room temperature for 2 h. The alkaline suspension was adjusted to be acidic with 0.1 molar HCl and extracted with ethyl acetate (3 × 20 ml). The combined organic layers were dried over MgSO₄ and filtered. The filtrate was concentrated to dryness under reduced pressure. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution of the compound (yield: 76%).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with 30% probability displacement ellipsoids.

2-[7-Chloro-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H- 1,2,4-benzothiadiazin-4-yl]acetic acid top

Crystal data top

C₁₆H₁₂ClF₃N₂O₄S	F(000) = 856
M_r = 420.79	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0571P)² + 1.0199P] where P = (F_o² + 2F_c²)/3
4293 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

C₁₆H₁₂ClF₃N₂O₄S	V = 1724.39 (6) Å³
M_r = 420.79	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3628 (2) Å	µ = 0.40 mm⁻¹
b = 12.3134 (2) Å	T = 296 K
c = 15.5597 (3) Å	0.20 × 0.20 × 0.20 mm
β = 105.996 (1)°

Data collection top

Bruker APEXII CCD diffractometer	3302 reflections with I > 2σ(I)
15140 measured reflections	R_int = 0.027
4293 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.04	Δρ_max = 0.73 e Å⁻³
4293 reflections	Δρ_min = −0.82 e Å⁻³
245 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.93	2.51	3.307 (3)	144

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂ClF₃N₂O₄S
M_r	420.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.3628 (2), 12.3134 (2), 15.5597 (3)
β (°)	105.996 (1)
V (Å³)	1724.39 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15140, 4293, 3302
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.131, 1.04
No. of reflections	4293
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.82

Computer programs: APEX2 (Bruker, 2005), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3ⁱ	0.82	1.86	2.676 (2)	170.6
C3—H3···O1ⁱⁱ	0.93	2.47	3.391 (3)	169
C16—H16···O2ⁱⁱⁱ	0.93	2.46	3.387 (2)	172
C13—H13···O3^iv	0.93	2.51	3.307 (3)	144

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, −y+3/2, z+1/2; (iii) −x+1, −y+2, −z; (iv) x+1, y, z.

Acknowledgements

This work was supported by the Beijing Natural Science Foundation (No. 7102091) and the Research Fund for the Doctoral Program of Higher Education of China (No. 20111101110042).

References

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Volume 68| Part 5| May 2012| Page o1363

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-[7-Chloro-1,1-dioxo-2-(2,4,5-tri­fluoro­benz­yl)-3,4-di­hydro-2H-1,2,4-benzo­thia­diazin-4-yl]acetic acid

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-[7-Chloro-1,1-dioxo-2-(2,4,5-trifluorobenzyl)-3,4-dihydro-2H-1,2,4-benzothiadiazin-4-yl]acetic acid