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

In the title compound, C(16)H(11)FN(2)O(4)S, the mean planes of the bicyclic chromone system and of the benzene ring of the benzothia-diazine derivative make a dihedral angle of 54.28 (5)°. 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.

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 a related structure, see: Mariya-al-Rashida et al. (2009 ▶);

Experimental

Crystal data

C16H11FN2O4S

M = 346.34

Orthorhombic,

a = 7.0739 (3) Å

b = 8.2861 (4) Å

c = 25.0456 (12) Å

V = 1468.05 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.31 × 0.06 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

9538 measured reflections

3453 independent reflections

1993 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.093

S = 0.97

3453 reflections

223 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.28 e Å−3

Absolute structure: Flack (1983 ▶), 1345 Friedel pairs

Flack parameter: 0.01 (9)

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/S1600536810038274/zq2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038274/zq2060Isup2.hkl

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

C16H11FN2O4S	F(000) = 712
Mr = 346.34	Dx = 1.567 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1626 reflections
a = 7.0739 (3) Å	θ = 3.3–22.0°
b = 8.2861 (4) Å	µ = 0.26 mm−1
c = 25.0456 (12) Å	T = 296 K
V = 1468.05 (12) Å3	Needle, orange
Z = 4	0.31 × 0.06 × 0.05 mm

Bruker APEXII CCD area-detector diffractometer	1993 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
graphite	θmax = 28.3°, θmin = 3.0°
phi and ω scans	h = −9→9
9538 measured reflections	k = −10→10
3453 independent reflections	l = −33→24

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0318P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
3453 reflections	Δρmax = 0.23 e Å−3
223 parameters	Δρmin = −0.28 e Å−3
3 restraints	Absolute structure: Flack (1983), 1345 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (9)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.05991 (10)	0.79823 (11)	0.18441 (3)	0.0371 (2)
O2	0.0424 (3)	0.9692 (3)	0.18575 (10)	0.0520 (6)
O3	−0.1066 (2)	0.7017 (3)	0.18043 (9)	0.0481 (6)
N4	0.4758 (3)	0.7352 (4)	0.19622 (11)	0.0431 (8)
H4A	0.593 (4)	0.736 (4)	0.2026 (12)	0.052*
N2	0.1714 (3)	0.7397 (3)	0.23806 (11)	0.0315 (7)
H2A	0.167 (4)	0.634 (4)	0.2387 (11)	0.038*
C17	0.2141 (4)	0.7419 (4)	0.13334 (13)	0.0342 (8)
C16	0.1469 (4)	0.7134 (5)	0.08251 (14)	0.0469 (9)
H16	0.0194	0.7295	0.0753	0.056*
C15	0.2643 (5)	0.6619 (4)	0.04245 (14)	0.0551 (10)
H15	0.2187	0.6446	0.0081	0.066*
C14	0.4523 (5)	0.6364 (5)	0.05458 (13)	0.0499 (10)
H14	0.5335	0.6002	0.0279	0.060*
C13	0.5222 (4)	0.6627 (4)	0.10455 (13)	0.0453 (10)
H13	0.6496	0.6440	0.1113	0.054*
C12	0.4050 (4)	0.7178 (4)	0.14604 (12)	0.0338 (8)
C11	0.3657 (4)	0.8018 (4)	0.24047 (12)	0.0334 (7)
H11	0.3629	0.9197	0.2374	0.040*
C3	0.4590 (4)	0.7558 (4)	0.29238 (12)	0.0323 (8)
C4	0.6462 (4)	0.8218 (4)	0.30203 (12)	0.0297 (7)
O4	0.7261 (3)	0.9080 (3)	0.26942 (8)	0.0382 (6)
C10	0.7285 (4)	0.7785 (4)	0.35354 (12)	0.0314 (7)
C5	0.9080 (4)	0.8345 (4)	0.36782 (12)	0.0396 (9)
H5	0.9778	0.8998	0.3449	0.048*
C6	0.9767 (5)	0.7904 (5)	0.41614 (15)	0.0516 (11)
F1	1.1503 (3)	0.8486 (3)	0.43125 (8)	0.0783 (8)
C7	0.8798 (5)	0.6941 (5)	0.45116 (15)	0.0598 (11)
H7	0.9314	0.6690	0.4843	0.072*
C8	0.7072 (5)	0.6355 (4)	0.43699 (13)	0.0539 (10)
H8	0.6406	0.5670	0.4596	0.065*
C9	0.6331 (4)	0.6803 (4)	0.38801 (13)	0.0401 (8)
O1	0.4555 (3)	0.6203 (3)	0.37625 (9)	0.0471 (6)
C2	0.3784 (4)	0.6620 (4)	0.32923 (13)	0.0429 (9)
H2	0.2584	0.6221	0.3217	0.051*

	U11	U22	U33	U12	U13	U23
S1	0.0215 (3)	0.0401 (5)	0.0498 (5)	0.0054 (4)	0.0011 (4)	0.0013 (5)
O2	0.0419 (12)	0.0430 (15)	0.0711 (17)	0.0132 (11)	0.0049 (13)	0.0072 (15)
O3	0.0186 (10)	0.0601 (16)	0.0658 (16)	−0.0026 (10)	−0.0003 (10)	−0.0045 (14)
N4	0.0170 (12)	0.075 (2)	0.0377 (18)	−0.0037 (14)	0.0000 (11)	−0.0042 (15)
N2	0.0221 (12)	0.0295 (17)	0.0430 (17)	−0.0023 (11)	0.0036 (11)	0.0033 (13)
C17	0.0262 (15)	0.038 (2)	0.039 (2)	0.0004 (14)	0.0012 (13)	0.0021 (16)
C16	0.0346 (16)	0.060 (3)	0.046 (2)	0.0012 (18)	−0.0116 (16)	0.007 (2)
C15	0.056 (2)	0.074 (3)	0.035 (2)	−0.007 (2)	−0.0062 (19)	0.000 (2)
C14	0.049 (2)	0.063 (3)	0.038 (2)	−0.001 (2)	0.0073 (18)	−0.005 (2)
C13	0.0280 (17)	0.063 (3)	0.044 (2)	−0.0004 (16)	0.0028 (15)	−0.002 (2)
C12	0.0215 (15)	0.041 (2)	0.039 (2)	−0.0034 (14)	−0.0012 (13)	−0.0002 (18)
C11	0.0238 (14)	0.038 (2)	0.0387 (19)	−0.0060 (15)	0.0045 (13)	0.0012 (17)
C3	0.0282 (14)	0.035 (2)	0.0341 (19)	−0.0021 (15)	0.0062 (14)	−0.0030 (16)
C4	0.0302 (15)	0.0255 (19)	0.0332 (19)	−0.0013 (14)	0.0044 (13)	−0.0031 (16)
O4	0.0351 (11)	0.0418 (15)	0.0376 (13)	−0.0113 (11)	0.0007 (10)	0.0056 (11)
C10	0.0374 (16)	0.026 (2)	0.0307 (18)	0.0027 (16)	0.0000 (14)	−0.0034 (16)
C5	0.0404 (19)	0.039 (2)	0.039 (2)	−0.0019 (15)	−0.0028 (15)	−0.0014 (17)
C6	0.046 (2)	0.060 (3)	0.048 (2)	0.000 (2)	−0.0181 (18)	−0.004 (2)
F1	0.0598 (13)	0.108 (2)	0.0671 (16)	−0.0153 (13)	−0.0323 (11)	0.0078 (14)
C7	0.077 (3)	0.062 (3)	0.041 (2)	−0.001 (2)	−0.016 (2)	0.006 (2)
C8	0.075 (3)	0.051 (3)	0.036 (2)	−0.003 (2)	0.0002 (19)	0.0075 (19)
C9	0.0470 (18)	0.036 (2)	0.038 (2)	−0.0005 (17)	0.0016 (17)	0.0016 (19)
O1	0.0512 (13)	0.0521 (16)	0.0381 (14)	−0.0150 (13)	−0.0022 (11)	0.0119 (12)
C2	0.0349 (16)	0.048 (3)	0.045 (2)	−0.0079 (16)	0.0031 (16)	−0.0028 (19)

S1—O2	1.422 (2)	C11—C3	1.507 (4)
S1—O3	1.427 (2)	C11—H11	0.9800
S1—N2	1.632 (3)	C3—C2	1.335 (4)
S1—C17	1.745 (3)	C3—C4	1.453 (4)
N4—C12	1.360 (4)	C4—O4	1.224 (3)
N4—C11	1.463 (4)	C4—C10	1.460 (4)
N4—H4A	0.85 (3)	C10—C9	1.364 (4)
N2—C11	1.469 (3)	C10—C5	1.398 (4)
N2—H2A	0.88 (3)	C5—C6	1.354 (4)
C17—C16	1.379 (4)	C5—H5	0.9300
C17—C12	1.402 (4)	C6—C7	1.370 (5)
C16—C15	1.370 (5)	C6—F1	1.373 (3)
C16—H16	0.9300	C7—C8	1.361 (5)
C15—C14	1.380 (4)	C7—H7	0.9300
C15—H15	0.9300	C8—C9	1.385 (4)
C14—C13	1.363 (4)	C8—H8	0.9300
C14—H14	0.9300	C9—O1	1.383 (4)
C13—C12	1.406 (4)	O1—C2	1.343 (3)
C13—H13	0.9300	C2—H2	0.9300
O2—S1—O3	119.19 (14)	N2—C11—C3	110.9 (2)
O2—S1—N2	108.60 (15)	N4—C11—H11	109.1
O3—S1—N2	106.84 (13)	N2—C11—H11	109.1
O2—S1—C17	109.76 (14)	C3—C11—H11	109.1
O3—S1—C17	108.36 (14)	C2—C3—C4	119.6 (3)
N2—S1—C17	102.83 (13)	C2—C3—C11	123.8 (3)
C12—N4—C11	122.9 (2)	C4—C3—C11	116.6 (3)
C12—N4—H4A	122 (2)	O4—C4—C3	122.0 (3)
C11—N4—H4A	112 (2)	O4—C4—C10	123.3 (3)
C11—N2—S1	112.4 (2)	C3—C4—C10	114.7 (3)
C11—N2—H2A	112.3 (19)	C9—C10—C5	119.0 (3)
S1—N2—H2A	107.2 (19)	C9—C10—C4	120.5 (3)
C16—C17—C12	121.1 (3)	C5—C10—C4	120.4 (3)
C16—C17—S1	120.5 (2)	C6—C5—C10	117.7 (3)
C12—C17—S1	118.3 (2)	C6—C5—H5	121.1
C15—C16—C17	121.4 (3)	C10—C5—H5	121.1
C15—C16—H16	119.3	C5—C6—C7	123.3 (3)
C17—C16—H16	119.3	C5—C6—F1	118.2 (4)
C16—C15—C14	118.0 (3)	C7—C6—F1	118.4 (3)
C16—C15—H15	121.0	C8—C7—C6	119.3 (3)
C14—C15—H15	121.0	C8—C7—H7	120.3
C13—C14—C15	121.8 (3)	C6—C7—H7	120.3
C13—C14—H14	119.1	C7—C8—C9	118.3 (3)
C15—C14—H14	119.1	C7—C8—H8	120.8
C14—C13—C12	121.1 (3)	C9—C8—H8	120.8
C14—C13—H13	119.4	C10—C9—O1	121.9 (3)
C12—C13—H13	119.4	C10—C9—C8	122.2 (3)
N4—C12—C17	123.3 (3)	O1—C9—C8	115.8 (3)
N4—C12—C13	120.0 (2)	C2—O1—C9	117.6 (3)
C17—C12—C13	116.5 (3)	C3—C2—O1	125.6 (3)
N4—C11—N2	109.6 (3)	C3—C2—H2	117.2
N4—C11—C3	109.0 (2)	O1—C2—H2	117.2

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···O3i	0.85 (3)	2.21 (3)	2.993 (3)	153 (3)
N4—H4A···O4	0.85 (3)	2.39 (3)	2.924 (3)	121 (3)
N2—H2A···O4ii	0.88 (3)	2.03 (3)	2.848 (3)	155 (3)
C2—H2···O2iii	0.93	2.48	3.399 (4)	168
C13—H13···O3i	0.93	2.49	3.258 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯O3i	0.85 (3)	2.21 (3)	2.993 (3)	153 (3)
N4—H4A⋯O4	0.85 (3)	2.39 (3)	2.924 (3)	121 (3)
N2—H2A⋯O4ii	0.88 (3)	2.03 (3)	2.848 (3)	155 (3)
C2—H2⋯O2iii	0.93	2.48	3.399 (4)	168
C13—H13⋯O3i	0.93	2.49	3.258 (3)	140

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