N'-[(E)-1-(4-Bromo-phen-yl)ethyl-idene]-4-hy-droxy-2-methyl-1,1-dioxo-2H-1,2-benzothia-zine-3-carbohydrazide.

The six-membered heterocycle in the title compound, C(18)H(16)BrN(3)O(4)S, adopts a sofa conformation. Intra-molecular N-H⋯N and O-H⋯O hydrogen bonds stabilize the mol-ecular conformation by forming a five- and a six-membered ring, respectively. The crystal packing is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general background, see: Zia-ur-Rehman et al. (2009 ▶). For synthesis details, see: Ahmad et al. (2011 ▶). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H16BrN3O4S

M = 450.31

Monoclinic,

a = 14.692 (2) Å

b = 16.562 (2) Å

c = 7.5254 (10) Å

β = 104.820 (1)°

V = 1770.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 173 K

0.48 × 0.36 × 0.11 mm

Data collection

Siemens SMART diffractometer equipped with a Bruker KappaCCD APEXII

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.383, T max = 0.773

21408 measured reflections

4490 independent reflections

3600 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.070

S = 1.03

4490 reflections

292 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and X-SEED (Barbour, 2001 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811035641/bt5633sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035641/bt5633Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035641/bt5633Isup3.cml

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

C18H16BrN3O4S	F(000) = 912
Mr = 450.31	Dx = 1.690 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6699 reflections
a = 14.692 (2) Å	θ = 2.9–28.6°
b = 16.562 (2) Å	µ = 2.47 mm−1
c = 7.5254 (10) Å	T = 173 K
β = 104.820 (1)°	Block, light yellow
V = 1770.2 (4) Å3	0.48 × 0.36 × 0.11 mm
Z = 4

Siemens SMART diffractometer equipped with a Bruker KappaCCD APEXII	4490 independent reflections
Radiation source: fine-focus sealed tube	3600 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.9°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→19
Tmin = 0.383, Tmax = 0.773	k = −22→22
21408 measured reflections	l = −10→10

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0314P)2 + 1.043P] where P = (Fo2 + 2Fc2)/3
4490 reflections	(Δ/σ)max = 0.001
292 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.74833 (13)	0.08528 (11)	0.1120 (2)	0.0143 (4)
C2	0.83074 (14)	0.10149 (12)	0.0597 (3)	0.0192 (4)
C3	0.87895 (14)	0.03747 (13)	0.0071 (3)	0.0214 (4)
C4	0.84550 (14)	−0.04104 (12)	0.0080 (3)	0.0191 (4)
C5	0.76259 (13)	−0.05643 (11)	0.0574 (3)	0.0153 (4)
C6	0.71272 (12)	0.00689 (11)	0.1115 (2)	0.0125 (3)
C7	0.62439 (12)	−0.00730 (10)	0.1649 (2)	0.0118 (3)
C8	0.58824 (12)	0.04814 (10)	0.2620 (2)	0.0126 (3)
C9	0.49476 (12)	0.03746 (10)	0.2936 (2)	0.0122 (3)
C10	0.35797 (12)	0.15959 (11)	0.5072 (2)	0.0126 (3)
C11	0.25982 (12)	0.16068 (11)	0.5279 (2)	0.0127 (3)
C12	0.19684 (13)	0.09850 (11)	0.4527 (2)	0.0143 (4)
C13	0.10540 (13)	0.09808 (12)	0.4725 (3)	0.0171 (4)
C14	0.07621 (12)	0.16057 (12)	0.5683 (3)	0.0168 (4)
C15	0.13608 (13)	0.22345 (12)	0.6414 (3)	0.0166 (4)
C16	0.22758 (13)	0.22328 (11)	0.6209 (2)	0.0146 (4)
C17	0.70484 (14)	0.11010 (12)	0.5184 (3)	0.0177 (4)
C18	0.42638 (14)	0.22228 (12)	0.6057 (3)	0.0179 (4)
N1	0.63983 (10)	0.12026 (9)	0.3325 (2)	0.0127 (3)
N2	0.46422 (11)	0.10249 (9)	0.3728 (2)	0.0132 (3)
N3	0.37590 (10)	0.10297 (9)	0.4031 (2)	0.0134 (3)
O1	0.58057 (9)	−0.07719 (8)	0.10541 (17)	0.0144 (3)
O2	0.74855 (9)	0.22587 (8)	0.26881 (19)	0.0195 (3)
O3	0.60735 (9)	0.18640 (8)	0.02540 (19)	0.0185 (3)
O4	0.44888 (9)	−0.02546 (7)	0.25045 (17)	0.0147 (3)
S1	0.68413 (3)	0.16496 (3)	0.17764 (6)	0.01416 (10)
Br1	−0.047586 (14)	0.160120 (14)	0.60056 (3)	0.02823 (7)
H1O	0.530 (2)	−0.0778 (16)	0.134 (4)	0.042*
H2	0.8547 (18)	0.1523 (15)	0.064 (3)	0.034*
H2N	0.5020 (19)	0.1414 (16)	0.401 (3)	0.034*
H3	0.9330 (18)	0.0479 (15)	−0.028 (3)	0.034*
H4	0.8796 (18)	−0.0832 (15)	−0.022 (3)	0.034*
H5	0.7398 (17)	−0.1094 (15)	0.056 (3)	0.034*
H12	0.2183 (17)	0.0564 (15)	0.385 (3)	0.034*
H13	0.0610 (17)	0.0546 (16)	0.420 (3)	0.034*
H15	0.1165 (17)	0.2691 (15)	0.707 (3)	0.034*
H16	0.2668 (18)	0.2657 (15)	0.667 (3)	0.034*
H17A	0.6686 (19)	0.0859 (16)	0.592 (4)	0.042*
H17B	0.758 (2)	0.0739 (16)	0.512 (4)	0.042*
H17C	0.727 (2)	0.1614 (16)	0.566 (4)	0.042*
H18A	0.488 (2)	0.2076 (17)	0.624 (4)	0.042*
H18B	0.4183 (18)	0.2313 (16)	0.732 (4)	0.042*
H18C	0.4163 (19)	0.2714 (17)	0.549 (4)	0.042*

	U11	U22	U33	U12	U13	U23
C1	0.0125 (8)	0.0151 (9)	0.0161 (9)	0.0036 (7)	0.0051 (7)	0.0024 (7)
C2	0.0163 (9)	0.0179 (10)	0.0260 (10)	−0.0013 (7)	0.0100 (8)	0.0032 (8)
C3	0.0145 (9)	0.0274 (11)	0.0252 (11)	0.0027 (8)	0.0101 (8)	0.0029 (8)
C4	0.0178 (10)	0.0220 (10)	0.0188 (10)	0.0065 (8)	0.0072 (8)	−0.0013 (8)
C5	0.0173 (9)	0.0162 (9)	0.0125 (9)	0.0020 (7)	0.0039 (7)	−0.0005 (7)
C6	0.0124 (8)	0.0136 (8)	0.0109 (8)	0.0026 (7)	0.0021 (7)	0.0014 (6)
C7	0.0115 (8)	0.0113 (8)	0.0120 (8)	−0.0003 (6)	0.0021 (7)	0.0026 (6)
C8	0.0119 (8)	0.0125 (8)	0.0135 (9)	−0.0008 (7)	0.0032 (7)	0.0011 (7)
C9	0.0131 (8)	0.0140 (8)	0.0093 (8)	0.0013 (7)	0.0025 (6)	0.0032 (6)
C10	0.0120 (8)	0.0143 (8)	0.0110 (8)	−0.0003 (7)	0.0023 (6)	0.0025 (7)
C11	0.0115 (8)	0.0159 (9)	0.0111 (8)	−0.0001 (7)	0.0034 (6)	0.0034 (7)
C12	0.0151 (9)	0.0131 (9)	0.0148 (9)	0.0004 (7)	0.0042 (7)	0.0012 (7)
C13	0.0138 (9)	0.0170 (9)	0.0200 (10)	−0.0018 (7)	0.0035 (7)	0.0005 (7)
C14	0.0099 (8)	0.0218 (9)	0.0196 (9)	0.0012 (7)	0.0055 (7)	0.0039 (7)
C15	0.0168 (9)	0.0188 (9)	0.0152 (9)	0.0020 (7)	0.0057 (7)	−0.0006 (7)
C16	0.0162 (9)	0.0148 (9)	0.0132 (9)	−0.0004 (7)	0.0045 (7)	−0.0004 (7)
C17	0.0179 (10)	0.0177 (10)	0.0171 (10)	−0.0017 (8)	0.0036 (8)	−0.0016 (7)
C18	0.0153 (9)	0.0185 (10)	0.0211 (10)	−0.0032 (7)	0.0067 (8)	−0.0036 (8)
N1	0.0127 (7)	0.0103 (7)	0.0166 (8)	−0.0011 (6)	0.0064 (6)	0.0000 (6)
N2	0.0103 (7)	0.0151 (8)	0.0150 (8)	−0.0007 (6)	0.0045 (6)	−0.0001 (6)
N3	0.0114 (7)	0.0164 (8)	0.0132 (7)	0.0008 (6)	0.0042 (6)	0.0024 (6)
O1	0.0136 (6)	0.0134 (6)	0.0163 (7)	−0.0016 (5)	0.0043 (5)	−0.0008 (5)
O2	0.0179 (7)	0.0126 (6)	0.0297 (8)	−0.0017 (5)	0.0093 (6)	0.0000 (5)
O3	0.0158 (7)	0.0167 (7)	0.0239 (7)	0.0040 (5)	0.0069 (6)	0.0058 (5)
O4	0.0141 (6)	0.0146 (6)	0.0160 (6)	−0.0021 (5)	0.0048 (5)	0.0004 (5)
S1	0.0124 (2)	0.0112 (2)	0.0204 (2)	0.00122 (16)	0.00694 (17)	0.00262 (17)
Br1	0.01334 (10)	0.03465 (13)	0.03960 (14)	0.00017 (8)	0.01204 (9)	−0.00172 (10)

C1—C2	1.392 (3)	C12—C13	1.389 (3)
C1—C6	1.399 (3)	C12—H12	0.96 (3)
C1—S1	1.7646 (18)	C13—C14	1.390 (3)
C2—C3	1.388 (3)	C13—H13	0.98 (3)
C2—H2	0.91 (2)	C14—C15	1.383 (3)
C3—C4	1.391 (3)	C14—Br1	1.8956 (18)
C3—H3	0.91 (3)	C15—C16	1.392 (3)
C4—C5	1.385 (3)	C15—H15	0.99 (3)
C4—H4	0.92 (3)	C16—H16	0.92 (3)
C5—C6	1.398 (2)	C17—N1	1.488 (2)
C5—H5	0.94 (3)	C17—H17A	0.95 (3)
C6—C7	1.472 (2)	C17—H17B	1.00 (3)
C7—O1	1.344 (2)	C17—H17C	0.95 (3)
C7—C8	1.363 (2)	C18—H18A	0.92 (3)
C8—N1	1.441 (2)	C18—H18B	1.00 (3)
C8—C9	1.463 (2)	C18—H18C	0.91 (3)
C9—O4	1.239 (2)	N1—S1	1.6488 (15)
C9—N2	1.361 (2)	N2—N3	1.374 (2)
C10—N3	1.291 (2)	N2—H2N	0.84 (3)
C10—C11	1.490 (2)	O1—H1O	0.82 (3)
C10—C18	1.502 (3)	O2—S1	1.4326 (14)
C11—C16	1.400 (3)	O3—S1	1.4318 (14)
C11—C12	1.403 (2)
C2—C1—C6	122.01 (17)	C12—C13—H13	121.4 (14)
C2—C1—S1	120.07 (14)	C14—C13—H13	119.5 (14)
C6—C1—S1	117.92 (13)	C15—C14—C13	121.17 (17)
C3—C2—C1	118.53 (18)	C15—C14—Br1	119.05 (14)
C3—C2—H2	119.8 (16)	C13—C14—Br1	119.79 (14)
C1—C2—H2	121.6 (16)	C14—C15—C16	119.24 (17)
C2—C3—C4	120.41 (18)	C14—C15—H15	122.6 (14)
C2—C3—H3	118.7 (16)	C16—C15—H15	118.2 (14)
C4—C3—H3	120.8 (16)	C15—C16—C11	121.13 (17)
C5—C4—C3	120.63 (18)	C15—C16—H16	119.1 (16)
C5—C4—H4	119.9 (15)	C11—C16—H16	119.7 (16)
C3—C4—H4	119.5 (15)	N1—C17—H17A	106.1 (16)
C4—C5—C6	120.16 (18)	N1—C17—H17B	110.2 (15)
C4—C5—H5	120.3 (15)	H17A—C17—H17B	110 (2)
C6—C5—H5	119.5 (15)	N1—C17—H17C	109.3 (16)
C5—C6—C1	118.24 (16)	H17A—C17—H17C	110 (2)
C5—C6—C7	121.59 (16)	H17B—C17—H17C	111 (2)
C1—C6—C7	120.17 (15)	C10—C18—H18A	113.8 (17)
O1—C7—C8	122.64 (16)	C10—C18—H18B	110.2 (15)
O1—C7—C6	115.28 (15)	H18A—C18—H18B	105 (2)
C8—C7—C6	122.03 (16)	C10—C18—H18C	112.1 (17)
C7—C8—N1	121.02 (15)	H18A—C18—H18C	110 (2)
C7—C8—C9	121.10 (16)	H18B—C18—H18C	106 (2)
N1—C8—C9	117.86 (15)	C8—N1—C17	113.77 (14)
O4—C9—N2	124.22 (16)	C8—N1—S1	112.18 (12)
O4—C9—C8	121.97 (16)	C17—N1—S1	116.15 (12)
N2—C9—C8	113.81 (15)	C9—N2—N3	120.56 (15)
N3—C10—C11	115.16 (16)	C9—N2—H2N	116.5 (18)
N3—C10—C18	125.93 (16)	N3—N2—H2N	123.0 (18)
C11—C10—C18	118.91 (16)	C10—N3—N2	116.92 (15)
C16—C11—C12	118.21 (16)	C7—O1—H1O	108.1 (19)
C16—C11—C10	121.45 (16)	O3—S1—O2	119.83 (8)
C12—C11—C10	120.34 (16)	O3—S1—N1	107.72 (8)
C13—C12—C11	121.10 (17)	O2—S1—N1	108.04 (8)
C13—C12—H12	120.6 (15)	O3—S1—C1	109.24 (9)
C11—C12—H12	118.3 (15)	O2—S1—C1	109.01 (8)
C12—C13—C14	119.14 (17)	N1—S1—C1	101.43 (8)
C6—C1—C2—C3	−0.5 (3)	C11—C12—C13—C14	0.1 (3)
S1—C1—C2—C3	−179.37 (15)	C12—C13—C14—C15	1.0 (3)
C1—C2—C3—C4	−0.4 (3)	C12—C13—C14—Br1	−178.89 (14)
C2—C3—C4—C5	1.4 (3)	C13—C14—C15—C16	−1.0 (3)
C3—C4—C5—C6	−1.6 (3)	Br1—C14—C15—C16	178.84 (14)
C4—C5—C6—C1	0.7 (3)	C14—C15—C16—C11	0.0 (3)
C4—C5—C6—C7	179.99 (17)	C12—C11—C16—C15	1.1 (3)
C2—C1—C6—C5	0.3 (3)	C10—C11—C16—C15	−179.30 (17)
S1—C1—C6—C5	179.21 (13)	C7—C8—N1—C17	−88.2 (2)
C2—C1—C6—C7	−178.95 (17)	C9—C8—N1—C17	93.45 (19)
S1—C1—C6—C7	−0.1 (2)	C7—C8—N1—S1	46.2 (2)
C5—C6—C7—O1	−19.8 (2)	C9—C8—N1—S1	−132.15 (14)
C1—C6—C7—O1	159.41 (16)	O4—C9—N2—N3	−2.8 (3)
C5—C6—C7—C8	162.47 (17)	C8—C9—N2—N3	176.94 (15)
C1—C6—C7—C8	−18.3 (3)	C11—C10—N3—N2	176.67 (14)
O1—C7—C8—N1	176.41 (15)	C18—C10—N3—N2	−3.4 (3)
C6—C7—C8—N1	−6.1 (3)	C9—N2—N3—C10	167.98 (16)
O1—C7—C8—C9	−5.3 (3)	C8—N1—S1—O3	60.35 (14)
C6—C7—C8—C9	172.21 (16)	C17—N1—S1—O3	−166.41 (13)
C7—C8—C9—O4	7.4 (3)	C8—N1—S1—O2	−168.87 (12)
N1—C8—C9—O4	−174.25 (15)	C17—N1—S1—O2	−35.63 (15)
C7—C8—C9—N2	−172.33 (16)	C8—N1—S1—C1	−54.33 (13)
N1—C8—C9—N2	6.0 (2)	C17—N1—S1—C1	78.91 (14)
N3—C10—C11—C16	−173.38 (16)	C2—C1—S1—O3	98.82 (17)
C18—C10—C11—C16	6.6 (3)	C6—C1—S1—O3	−80.10 (16)
N3—C10—C11—C12	6.2 (2)	C2—C1—S1—O2	−33.83 (18)
C18—C10—C11—C12	−173.73 (17)	C6—C1—S1—O2	147.26 (14)
C16—C11—C12—C13	−1.1 (3)	C2—C1—S1—N1	−147.64 (16)
C10—C11—C12—C13	179.26 (16)	C6—C1—S1—N1	33.45 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···O2i	0.95 (3)	2.38 (3)	3.275 (2)	158 (2)
C17—H17A···O4ii	0.95 (3)	2.54 (3)	3.479 (2)	171 (2)
N2—H2N···N1	0.84 (3)	2.24 (3)	2.690 (2)	114 (2)
O1—H1O···O4	0.82 (3)	1.86 (3)	2.5979 (18)	148 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯O2i	0.95 (3)	2.38 (3)	3.275 (2)	158 (2)
C17—H17A⋯O4ii	0.95 (3)	2.54 (3)	3.479 (2)	171 (2)
N2—H2N⋯N1	0.84 (3)	2.24 (3)	2.690 (2)	114 (2)
O1—H1O⋯O4	0.82 (3)	1.86 (3)	2.5979 (18)	148 (3)

Symmetry codes: (i) ; (ii) .