Literature DB >> 21589389

3-(6-Bromo-4-oxo-4H-chromen-3-yl)-3,4-dihydro-2H-1,2,4-benzothia-diazine-1,1-dione.

Mariya Al-Rashida, Saeed Ahmad Nagra, Islam Ullah Khan, George Kostakis, Ghulam Abbas.   

Abstract

The mol-ecular structure of the title compound, C(16)H(11)BrN(2)O(4)S, is very similar to that of the previously reported fluoro analogue [al-Rashida et al. (2010 ▶). Acta Cryst. E66, o2707]. The mean planes of the bicyclic chromone system and the benzene ring of the benzothia-diazine derivative make a dihedral angle of 58.23 (8)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal, mol-ecules are linked into layers by N-H⋯O and C-H⋯O hydrogen bonds, generating an infinite two-dimensional network.

Entities:  

Year:  2010        PMID： 21589389      PMCID： PMC3011492          DOI： 10.1107/S1600536810044648

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to the importance of the 1,2,4-benzothia­diazine-1,1-dioxide ring system in pharmaceutical and medicinal chemistry, see: Zhu et al. (2005 ▶); Kamal et al. (2007a ▶). For a survey on the anti­microbial activity of benzothia­diazine derivatives, see: Di Bella et al. (1983) ▶; Kamal et al. (2007a ▶,b ▶). The sulfonamide group is an active pharmacophore, see: Weisman & Brown (1964) ▶. For related structures, see: al-Rashida et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C16H11BrN2O4S M = 407.24 Monoclinic, a = 7.0778 (4) Å b = 8.6070 (6) Å c = 25.6290 (16) Å β = 94.607 (3)° V = 1556.24 (17) Å3 Z = 4 Mo Kα radiation μ = 2.80 mm−1 T = 296 K 0.28 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.475, T max = 0.540 17309 measured reflections 3873 independent reflections 1969 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.103 S = 0.98 3873 reflections 223 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.50 e Å−3 Δρmin = −0.51 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810044648/zq2069sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044648/zq2069Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H11BrN2O4SF(000) = 816
Mr = 407.24Dx = 1.738 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2932 reflections
a = 7.0778 (4) Åθ = 3.1–22.1°
b = 8.6070 (6) ŵ = 2.80 mm−1
c = 25.6290 (16) ÅT = 296 K
β = 94.607 (3)°Needle, white
V = 1556.24 (17) Å30.28 × 0.28 × 0.22 mm
Z = 4
Bruker APEXII CCD area-detector diffractometer3873 independent reflections
Radiation source: fine-focus sealed tube1969 reflections with I > 2σ(I)
graphiteRint = 0.058
phi and ω scansθmax = 28.4°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −9→9
Tmin = 0.475, Tmax = 0.540k = −11→8
17309 measured reflectionsl = −34→34
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H atoms treated by a mixture of independent and constrained refinement
S = 0.98w = 1/[σ2(Fo2) + (0.0423P)2 + 0.1442P] where P = (Fo2 + 2Fc2)/3
3873 reflections(Δ/σ)max < 0.001
223 parametersΔρmax = 0.50 e Å−3
2 restraintsΔρmin = −0.51 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.
xyzUiso*/Ueq
S11.22103 (10)0.73566 (10)0.31055 (3)0.0337 (2)
O21.2394 (3)0.5717 (3)0.30708 (9)0.0463 (6)
O31.3885 (3)0.8294 (3)0.31425 (9)0.0465 (6)
N21.0884 (3)0.7953 (3)0.25943 (10)0.0287 (6)
H2A1.085 (4)0.893 (3)0.2592 (12)0.034*
N40.8018 (3)0.7790 (4)0.30189 (10)0.0371 (7)
H4A0.690 (4)0.780 (4)0.3005 (13)0.045*
Br1−0.00741 (5)0.67254 (5)0.060030 (16)0.06277 (19)
C50.3194 (4)0.7029 (4)0.13029 (13)0.0350 (8)
H50.26220.62780.14980.042*
C60.2305 (5)0.7577 (4)0.08503 (13)0.0403 (9)
C70.3086 (5)0.8725 (4)0.05590 (14)0.0455 (9)
H70.24290.90990.02560.055*
C80.4824 (5)0.9304 (4)0.07182 (13)0.0424 (9)
H80.53741.00680.05230.051*
C90.5766 (4)0.8743 (4)0.11749 (12)0.0324 (8)
O10.7509 (3)0.9378 (3)0.13110 (8)0.0398 (6)
C100.4984 (4)0.7614 (4)0.14695 (12)0.0287 (7)
C40.6000 (4)0.7086 (4)0.19593 (12)0.0286 (8)
O40.5369 (3)0.6116 (3)0.22456 (9)0.0395 (6)
C30.7845 (4)0.7819 (4)0.20758 (12)0.0272 (7)
C20.8469 (4)0.8871 (4)0.17524 (12)0.0347 (8)
H20.96650.92910.18380.042*
C110.8977 (4)0.7310 (4)0.25680 (12)0.0289 (7)
H110.90660.61740.25680.035*
C120.8888 (4)0.7966 (4)0.35104 (12)0.0295 (8)
C130.7836 (4)0.8366 (4)0.39290 (13)0.0372 (8)
H130.65310.84940.38710.045*
C140.8682 (5)0.8573 (4)0.44190 (14)0.0431 (9)
H140.79420.88250.46910.052*
C161.1691 (5)0.8056 (4)0.41215 (13)0.0402 (9)
H161.29990.79640.41830.048*
C151.0631 (5)0.8417 (4)0.45229 (14)0.0445 (9)
H151.11960.85570.48600.053*
C171.0843 (4)0.7823 (4)0.36172 (12)0.0291 (8)
U11U22U33U12U13U23
S10.0158 (4)0.0421 (6)0.0427 (5)0.0059 (4)−0.0002 (4)−0.0004 (4)
O20.0393 (14)0.0381 (15)0.0622 (17)0.0148 (11)0.0081 (12)0.0055 (12)
O30.0160 (11)0.0624 (17)0.0608 (16)−0.0034 (11)0.0001 (11)−0.0038 (13)
N20.0172 (13)0.0291 (15)0.0393 (16)−0.0005 (12)0.0005 (12)0.0016 (14)
N40.0121 (12)0.070 (2)0.0293 (16)0.0004 (14)0.0002 (13)−0.0041 (14)
Br10.0358 (2)0.0836 (4)0.0653 (3)−0.0100 (2)−0.01830 (19)−0.0107 (2)
C50.0287 (17)0.035 (2)0.040 (2)−0.0072 (15)−0.0010 (16)−0.0056 (17)
C60.0290 (19)0.049 (2)0.040 (2)0.0009 (17)−0.0140 (16)−0.0148 (18)
C70.051 (2)0.046 (2)0.037 (2)−0.0006 (19)−0.0116 (18)0.0050 (18)
C80.047 (2)0.042 (2)0.036 (2)−0.0048 (18)−0.0029 (18)0.0077 (17)
C90.0332 (18)0.032 (2)0.0313 (19)−0.0038 (15)−0.0044 (15)−0.0040 (16)
O10.0367 (13)0.0447 (15)0.0367 (14)−0.0182 (11)−0.0056 (11)0.0071 (11)
C100.0283 (17)0.0265 (19)0.0309 (18)−0.0002 (14)0.0009 (15)−0.0027 (15)
C40.0250 (17)0.0269 (19)0.0338 (19)−0.0007 (14)0.0014 (15)−0.0058 (16)
O40.0347 (13)0.0426 (14)0.0406 (14)−0.0153 (11)−0.0015 (11)0.0104 (12)
C30.0219 (16)0.0315 (19)0.0286 (17)−0.0038 (14)0.0034 (14)−0.0041 (15)
C20.0283 (18)0.040 (2)0.035 (2)−0.0090 (16)−0.0022 (16)−0.0028 (17)
C110.0171 (15)0.0334 (19)0.0361 (19)−0.0019 (14)0.0027 (14)−0.0035 (15)
C120.0190 (15)0.038 (2)0.0303 (18)0.0018 (14)−0.0024 (14)−0.0023 (15)
C130.0213 (16)0.052 (2)0.038 (2)0.0039 (16)0.0010 (15)−0.0052 (18)
C140.039 (2)0.051 (2)0.039 (2)0.0055 (17)0.0017 (17)−0.0085 (18)
C160.0257 (18)0.048 (2)0.044 (2)0.0029 (16)−0.0094 (17)−0.0032 (18)
C150.044 (2)0.054 (3)0.033 (2)0.0006 (18)−0.0092 (17)−0.0068 (18)
C170.0167 (15)0.0338 (19)0.0363 (19)0.0029 (13)−0.0010 (14)−0.0017 (15)
S1—O21.421 (2)C9—C101.375 (4)
S1—O31.431 (2)O1—C21.345 (4)
S1—N21.632 (3)C10—C41.468 (4)
S1—C171.738 (3)C4—O41.219 (3)
N2—C111.456 (4)C4—C31.459 (4)
N2—H2A0.84 (2)C3—C21.327 (4)
N4—C121.365 (4)C3—C111.504 (4)
N4—C111.446 (4)C2—H20.9300
N4—H4A0.79 (3)C11—H110.9800
Br1—C61.900 (3)C12—C131.398 (4)
C5—C61.359 (4)C12—C171.394 (4)
C5—C101.398 (4)C13—C141.359 (4)
C5—H50.9300C13—H130.9300
C6—C71.380 (5)C14—C151.391 (5)
C7—C81.359 (5)C14—H140.9300
C7—H70.9300C16—C151.357 (5)
C8—C91.387 (4)C16—C171.395 (4)
C8—H80.9300C16—H160.9300
C9—O11.368 (4)C15—H150.9300
O2—S1—O3119.01 (14)O4—C4—C10123.3 (3)
O2—S1—N2108.16 (14)C3—C4—C10114.2 (3)
O3—S1—N2107.20 (14)C2—C3—C4120.3 (3)
O2—S1—C17109.63 (15)C2—C3—C11122.8 (3)
O3—S1—C17109.16 (14)C4—C3—C11117.0 (3)
N2—S1—C17102.36 (14)C3—C2—O1125.2 (3)
C11—N2—S1112.9 (2)C3—C2—H2117.4
C11—N2—H2A111 (2)O1—C2—H2117.4
S1—N2—H2A109 (2)N4—C11—N2110.3 (2)
C12—N4—C11124.3 (2)N4—C11—C3109.6 (2)
C12—N4—H4A115 (3)N2—C11—C3111.0 (3)
C11—N4—H4A120 (3)N4—C11—H11108.6
C6—C5—C10118.8 (3)N2—C11—H11108.6
C6—C5—H5120.6C3—C11—H11108.6
C10—C5—H5120.6N4—C12—C13120.5 (3)
C5—C6—C7122.2 (3)N4—C12—C17122.6 (3)
C5—C6—Br1119.4 (3)C13—C12—C17116.9 (3)
C7—C6—Br1118.5 (2)C14—C13—C12121.3 (3)
C8—C7—C6119.5 (3)C14—C13—H13119.4
C8—C7—H7120.3C12—C13—H13119.4
C6—C7—H7120.3C13—C14—C15121.4 (3)
C7—C8—C9119.2 (3)C13—C14—H14119.3
C7—C8—H8120.4C15—C14—H14119.3
C9—C8—H8120.4C15—C16—C17120.8 (3)
O1—C9—C10122.5 (3)C15—C16—H16119.6
O1—C9—C8116.0 (3)C17—C16—H16119.6
C10—C9—C8121.5 (3)C16—C15—C14118.5 (3)
C2—O1—C9118.0 (2)C16—C15—H15120.7
C9—C10—C5118.8 (3)C14—C15—H15120.7
C9—C10—C4119.8 (3)C16—C17—C12121.0 (3)
C5—C10—C4121.3 (3)C16—C17—S1120.5 (2)
O4—C4—C3122.5 (3)C12—C17—S1118.4 (2)
O2—S1—N2—C1161.9 (2)C9—O1—C2—C3−1.5 (5)
O3—S1—N2—C11−168.6 (2)C12—N4—C11—N2−35.8 (4)
C17—S1—N2—C11−53.8 (2)C12—N4—C11—C3−158.3 (3)
C10—C5—C6—C7−2.0 (5)S1—N2—C11—N461.6 (3)
C10—C5—C6—Br1177.0 (2)S1—N2—C11—C3−176.8 (2)
C5—C6—C7—C81.9 (5)C2—C3—C11—N4114.2 (3)
Br1—C6—C7—C8−177.2 (3)C4—C3—C11—N4−66.5 (3)
C6—C7—C8—C9−0.9 (5)C2—C3—C11—N2−7.9 (4)
C7—C8—C9—O1179.9 (3)C4—C3—C11—N2171.4 (2)
C7—C8—C9—C100.1 (5)C11—N4—C12—C13−177.1 (3)
C10—C9—O1—C2−0.4 (4)C11—N4—C12—C175.6 (5)
C8—C9—O1—C2179.7 (3)N4—C12—C13—C14−178.8 (3)
O1—C9—C10—C5179.9 (3)C17—C12—C13—C14−1.4 (5)
C8—C9—C10—C5−0.2 (5)C12—C13—C14—C150.9 (5)
O1—C9—C10—C42.1 (5)C17—C16—C15—C14−1.0 (5)
C8—C9—C10—C4−178.0 (3)C13—C14—C15—C160.3 (5)
C6—C5—C10—C91.2 (5)C15—C16—C17—C120.5 (5)
C6—C5—C10—C4179.0 (3)C15—C16—C17—S1−179.9 (3)
C9—C10—C4—O4178.2 (3)N4—C12—C17—C16178.0 (3)
C5—C10—C4—O40.5 (5)C13—C12—C17—C160.6 (5)
C9—C10—C4—C3−2.0 (4)N4—C12—C17—S1−1.6 (4)
C5—C10—C4—C3−179.7 (3)C13—C12—C17—S1−179.0 (2)
O4—C4—C3—C2−179.9 (3)O2—S1—C17—C1689.7 (3)
C10—C4—C3—C20.3 (4)O3—S1—C17—C16−42.3 (3)
O4—C4—C3—C110.8 (4)N2—S1—C17—C16−155.7 (3)
C10—C4—C3—C11−179.0 (3)O2—S1—C17—C12−90.7 (3)
C4—C3—C2—O11.4 (5)O3—S1—C17—C12137.3 (3)
C11—C3—C2—O1−179.3 (3)N2—S1—C17—C1224.0 (3)
D—H···AD—HH···AD···AD—H···A
N4—H4A···O40.79 (3)2.59 (3)2.987 (3)113 (3)
N4—H4A···O3i0.79 (3)2.23 (3)2.999 (3)164 (3)
C13—H13···O3i0.932.54 (1)3.314 (4)141 (1)
N2—H2A···O20.84 (2)2.67 (3)3.222 (4)124 (2)
C2—H2···O20.932.41 (1)3.330 (4)169 (1)
N2—H2A···O40.84 (2)2.12 (3)2.903 (4)154 (3)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N4—H4A⋯O40.79 (3)2.59 (3)2.987 (3)113 (3)
N4—H4A⋯O3i0.79 (3)2.23 (3)2.999 (3)164 (3)
C13—H13⋯O3i0.932.54 (1)3.314 (4)141 (1)
N2—H2A⋯O20.84 (2)2.67 (3)3.222 (4)124 (2)
C2—H2⋯O20.932.41 (1)3.330 (4)169 (1)
N2—H2A⋯O40.84 (2)2.12 (3)2.903 (4)154 (3)

Symmetry code: (i) .

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