6-Bromo-4-[2-(4-fluoro­benzyl­idene)hydrazin-1-yl­idene]-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Khan, I.U.; Harrison, W.T.A.; Hussain, A.; Ashraf, H.

doi:10.1107/S1600536812037403

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2851

https://doi.org/10.1107/S1600536812037403

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6-Bromo-4-[2-(4-fluorobenzylidene)hydrazin-1-ylidene]-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a ^* Islam Ullah Khan,^b William T. A. Harrison,^c Ajaz Hussain ^a and Hina Ashraf ^b

^aDepartment of Chemistry, Government College University, Faisalabad 38040, Pakistan, ^bMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan, and ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 4 August 2012; accepted 30 August 2012; online 5 September 2012)

In the title compound, C₁₆H₁₃BrFN₃O₂S, the dihedral angle between the aromatic rings is 2.55 (19)° and the C=N—N=C torsion angle is 178.9 (3)°. The conformation of the thiazine ring is an envelope, with the S atom displaced by −0.811 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.042 Å). In the crystal, C—H⋯O interactions link the molecules and weak aromatic π–π stacking between the fluorobenzene and bromobenzene rings [centroid–centroid separation = 3.720 (2) Å and interplanar angle = 2.6 (2)°] is also observed.

Related literature

For the synthesis and for the biological activity of related materials, see: Shafiq, Zia-Ur-Rehman et al. (2011 ). For a related structure, see: Shafiq, Khan et al. (2011 )

Experimental

Crystal data

C₁₆H₁₃BrFN₃O₂S
M_r = 410.26
Triclinic, $[P \overline 1]$
a = 7.8996 (4) Å
b = 9.0070 (4) Å
c = 13.5057 (7) Å
α = 104.176 (3)°
β = 90.977 (3)°
γ = 113.466 (3)°
V = 847.51 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.57 mm⁻¹
T = 296 K
0.37 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.450, T_max = 0.715
17622 measured reflections
4186 independent reflections
2331 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.118
S = 0.99
4186 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O2ⁱ	0.97	2.56	3.397 (4)	145
C9—H9⋯O1ⁱⁱ	0.93	2.39	3.292 (4)	163
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x, y+1, z.

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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812037403/kj2209sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037403/kj2209Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812037403/kj2209Isup3.cml

checkCIF report

Related literature top

For the synthesis and for the biological activity of related materials, see: Shafiq, Zia-Ur-Rehman et al. (2011). For a related structure, see: Shafiq, Khan et al. (2011)

Experimental top

For the synthesis, see: Shafiq, Zia-Ur-Rehman et al. (2011). Yellow needles were recrystallized from ethylacetate under slow evaporation.

Structure description top

For the synthesis and for the biological activity of related materials, see: Shafiq, Zia-Ur-Rehman et al. (2011). For a related structure, see: Shafiq, Khan et al. (2011)

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids at the 50% probability level.

6-Bromo-4-[2-(4-fluorobenzylidene)hydrazin-1-ylidene]-1-methyl- 3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₆H₁₃BrFN₃O₂S	Z = 2
M_r = 410.26	F(000) = 412
Triclinic, P1	D_x = 1.608 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8996 (4) Å	Cell parameters from 4416 reflections
b = 9.0070 (4) Å	θ = 2.6–22.8°
c = 13.5057 (7) Å	µ = 2.57 mm⁻¹
α = 104.176 (3)°	T = 296 K
β = 90.977 (3)°	Needle, yellow
γ = 113.466 (3)°	0.37 × 0.16 × 0.14 mm
V = 847.51 (7) Å³

Data collection top

Bruker APEXII CCD diffractometer	4186 independent reflections
Radiation source: fine-focus sealed tube	2331 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.450, T_max = 0.715	k = −12→12
17622 measured reflections	l = −17→17

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0479P)² + 0.5245P] where P = (F_o² + 2F_c²)/3
4186 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

C₁₆H₁₃BrFN₃O₂S	γ = 113.466 (3)°
M_r = 410.26	V = 847.51 (7) Å³
Triclinic, P1	Z = 2
a = 7.8996 (4) Å	Mo Kα radiation
b = 9.0070 (4) Å	µ = 2.57 mm⁻¹
c = 13.5057 (7) Å	T = 296 K
α = 104.176 (3)°	0.37 × 0.16 × 0.14 mm
β = 90.977 (3)°

Data collection top

Bruker APEXII CCD diffractometer	4186 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2331 reflections with I > 2σ(I)
T_min = 0.450, T_max = 0.715	R_int = 0.038
17622 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 0.99	Δρ_max = 0.58 e Å⁻³
4186 reflections	Δρ_min = −0.78 e Å⁻³
218 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
C1	0.9739 (4)	0.8291 (4)	0.2392 (2)	0.0408 (7)
C2	1.0591 (5)	0.8914 (4)	0.3410 (2)	0.0515 (8)
H2	1.0804	0.8194	0.3734	0.062*
C3	1.1121 (5)	1.0568 (4)	0.3941 (2)	0.0535 (9)
H3	1.1720	1.0973	0.4612	0.064*
C4	1.0757 (5)	1.1622 (4)	0.3472 (2)	0.0512 (8)
C5	0.9894 (4)	1.1042 (4)	0.2476 (2)	0.0432 (7)
H5	0.9654	1.1771	0.2172	0.052*
C6	0.9377 (4)	0.9379 (3)	0.1919 (2)	0.0354 (6)
C7	0.8470 (4)	0.8820 (3)	0.0850 (2)	0.0345 (6)
C8	0.8201 (5)	0.7111 (3)	0.0194 (2)	0.0458 (8)
H8A	0.9351	0.7173	−0.0075	0.055*
H8B	0.7248	0.6743	−0.0384	0.055*
C9	0.6595 (4)	1.0158 (4)	−0.0800 (2)	0.0379 (7)
H9	0.6818	1.1194	−0.0344	0.045*
C10	0.5657 (4)	0.9726 (4)	−0.1840 (2)	0.0409 (7)
C11	0.5109 (5)	0.8138 (4)	−0.2507 (2)	0.0552 (9)
H11	0.5309	0.7307	−0.2296	0.066*
C12	0.4260 (5)	0.7788 (6)	−0.3493 (3)	0.0735 (12)
H12	0.3877	0.6722	−0.3948	0.088*
C13	0.3996 (5)	0.9026 (7)	−0.3781 (3)	0.0741 (13)
C14	0.4504 (5)	1.0597 (6)	−0.3152 (3)	0.0725 (12)
H14	0.4300	1.1416	−0.3377	0.087*
C15	0.5335 (5)	1.0944 (5)	−0.2165 (3)	0.0564 (9)
H15	0.5682	1.2009	−0.1713	0.068*
C16	0.9850 (6)	0.5539 (5)	0.2319 (3)	0.0817 (13)
H16A	1.1167	0.6067	0.2535	0.122*
H16B	0.9531	0.4469	0.1827	0.122*
H16C	0.9202	0.5378	0.2906	0.122*
S1	0.75433 (14)	0.56638 (10)	0.09239 (7)	0.0548 (3)
N1	0.9317 (4)	0.6609 (3)	0.1849 (2)	0.0542 (7)
N2	0.7961 (3)	0.9817 (3)	0.05209 (17)	0.0383 (6)
N3	0.7109 (3)	0.9153 (3)	−0.05055 (17)	0.0407 (6)
O1	0.7609 (4)	0.4128 (3)	0.0372 (2)	0.0824 (9)
O2	0.5862 (3)	0.5604 (3)	0.1320 (2)	0.0672 (7)
F1	0.3170 (4)	0.8672 (4)	−0.47568 (18)	0.1185 (11)
Br1	1.14956 (8)	1.39006 (5)	0.42019 (3)	0.0926 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0408 (18)	0.0441 (16)	0.0416 (17)	0.0197 (15)	0.0030 (14)	0.0151 (13)
C2	0.054 (2)	0.064 (2)	0.0436 (18)	0.0272 (18)	−0.0006 (15)	0.0233 (16)
C3	0.057 (2)	0.069 (2)	0.0319 (17)	0.0243 (18)	−0.0045 (15)	0.0115 (15)
C4	0.060 (2)	0.0507 (18)	0.0361 (17)	0.0231 (17)	−0.0059 (15)	0.0009 (14)
C5	0.0503 (19)	0.0433 (16)	0.0337 (15)	0.0197 (15)	−0.0039 (14)	0.0066 (13)
C6	0.0375 (17)	0.0377 (14)	0.0306 (14)	0.0149 (13)	0.0023 (12)	0.0099 (12)
C7	0.0352 (16)	0.0314 (13)	0.0329 (15)	0.0100 (13)	0.0015 (12)	0.0086 (11)
C8	0.056 (2)	0.0360 (15)	0.0395 (17)	0.0171 (15)	−0.0020 (15)	0.0041 (13)
C9	0.0393 (17)	0.0373 (15)	0.0335 (15)	0.0142 (13)	0.0010 (13)	0.0068 (12)
C10	0.0352 (17)	0.0536 (18)	0.0359 (16)	0.0182 (15)	0.0000 (13)	0.0164 (13)
C11	0.056 (2)	0.057 (2)	0.0431 (19)	0.0166 (18)	−0.0090 (16)	0.0091 (15)
C12	0.064 (3)	0.089 (3)	0.041 (2)	0.015 (2)	−0.0131 (18)	0.004 (2)
C13	0.050 (2)	0.129 (4)	0.043 (2)	0.031 (3)	−0.0069 (17)	0.034 (2)
C14	0.065 (3)	0.116 (4)	0.065 (3)	0.050 (3)	0.009 (2)	0.052 (3)
C15	0.054 (2)	0.075 (2)	0.052 (2)	0.0337 (19)	0.0086 (17)	0.0260 (18)
C16	0.102 (3)	0.059 (2)	0.096 (3)	0.042 (2)	−0.015 (3)	0.030 (2)
S1	0.0655 (6)	0.0316 (4)	0.0608 (5)	0.0150 (4)	−0.0081 (4)	0.0115 (4)
N1	0.0662 (19)	0.0447 (15)	0.0571 (17)	0.0273 (14)	−0.0093 (14)	0.0170 (13)
N2	0.0437 (15)	0.0375 (12)	0.0291 (12)	0.0151 (12)	−0.0052 (10)	0.0048 (10)
N3	0.0495 (15)	0.0401 (13)	0.0294 (12)	0.0173 (12)	−0.0045 (11)	0.0070 (10)
O1	0.113 (2)	0.0376 (13)	0.090 (2)	0.0338 (14)	−0.0166 (17)	0.0037 (12)
O2	0.0524 (16)	0.0561 (15)	0.0801 (18)	0.0050 (12)	0.0048 (13)	0.0266 (13)
F1	0.0919 (18)	0.199 (3)	0.0528 (14)	0.043 (2)	−0.0233 (13)	0.0460 (18)
Br1	0.1381 (5)	0.0639 (3)	0.0568 (3)	0.0455 (3)	−0.0405 (3)	−0.01902 (18)

Geometric parameters (Å, º) top

C1—C2	1.395 (4)	C10—C11	1.381 (4)
C1—C6	1.405 (4)	C10—C15	1.385 (4)
C1—N1	1.411 (4)	C11—C12	1.384 (5)
C2—C3	1.370 (5)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.355 (6)
C3—C4	1.375 (5)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.354 (6)
C4—C5	1.373 (4)	C13—F1	1.365 (4)
C4—Br1	1.887 (3)	C14—C15	1.382 (5)
C5—C6	1.388 (4)	C14—H14	0.9300
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.475 (4)	C16—N1	1.457 (4)
C7—N2	1.281 (3)	C16—H16A	0.9600
C7—C8	1.505 (4)	C16—H16B	0.9600
C8—S1	1.746 (3)	C16—H16C	0.9600
C8—H8A	0.9700	S1—O1	1.423 (3)
C8—H8B	0.9700	S1—O2	1.426 (3)
C9—N3	1.268 (3)	S1—N1	1.649 (3)
C9—C10	1.463 (4)	N2—N3	1.405 (3)
C9—H9	0.9300

C2—C1—C6	118.9 (3)	C10—C11—C12	119.8 (3)
C2—C1—N1	119.7 (3)	C10—C11—H11	120.1
C6—C1—N1	121.3 (3)	C12—C11—H11	120.1
C3—C2—C1	121.3 (3)	C13—C12—C11	118.8 (4)
C3—C2—H2	119.4	C13—C12—H12	120.6
C1—C2—H2	119.4	C11—C12—H12	120.6
C2—C3—C4	119.4 (3)	C14—C13—C12	123.5 (3)
C2—C3—H3	120.3	C14—C13—F1	118.2 (4)
C4—C3—H3	120.3	C12—C13—F1	118.4 (4)
C5—C4—C3	120.8 (3)	C13—C14—C15	117.8 (4)
C5—C4—Br1	119.9 (2)	C13—C14—H14	121.1
C3—C4—Br1	119.3 (2)	C15—C14—H14	121.1
C4—C5—C6	120.7 (3)	C14—C15—C10	120.8 (4)
C4—C5—H5	119.7	C14—C15—H15	119.6
C6—C5—H5	119.7	C10—C15—H15	119.6
C5—C6—C1	118.9 (3)	N1—C16—H16A	109.5
C5—C6—C7	118.7 (2)	N1—C16—H16B	109.5
C1—C6—C7	122.4 (2)	H16A—C16—H16B	109.5
N2—C7—C6	118.5 (2)	N1—C16—H16C	109.5
N2—C7—C8	123.1 (2)	H16A—C16—H16C	109.5
C6—C7—C8	118.4 (2)	H16B—C16—H16C	109.5
C7—C8—S1	110.0 (2)	O1—S1—O2	118.54 (17)
C7—C8—H8A	109.7	O1—S1—N1	107.04 (16)
S1—C8—H8A	109.7	O2—S1—N1	110.83 (16)
C7—C8—H8B	109.7	O1—S1—C8	110.49 (17)
S1—C8—H8B	109.7	O2—S1—C8	108.71 (16)
H8A—C8—H8B	108.2	N1—S1—C8	99.57 (14)
N3—C9—C10	121.5 (3)	C1—N1—C16	120.7 (3)
N3—C9—H9	119.2	C1—N1—S1	117.5 (2)
C10—C9—H9	119.2	C16—N1—S1	117.2 (2)
C11—C10—C15	119.4 (3)	C7—N2—N3	113.6 (2)
C11—C10—C9	121.5 (3)	C9—N3—N2	111.9 (2)
C15—C10—C9	119.1 (3)

C6—C1—C2—C3	−1.7 (5)	C11—C12—C13—C14	−0.7 (6)
N1—C1—C2—C3	176.1 (3)	C11—C12—C13—F1	179.5 (3)
C1—C2—C3—C4	1.9 (5)	C12—C13—C14—C15	0.0 (6)
C2—C3—C4—C5	−0.9 (5)	F1—C13—C14—C15	179.8 (3)
C2—C3—C4—Br1	−179.8 (3)	C13—C14—C15—C10	0.9 (6)
C3—C4—C5—C6	−0.3 (5)	C11—C10—C15—C14	−1.2 (5)
Br1—C4—C5—C6	178.6 (2)	C9—C10—C15—C14	178.1 (3)
C4—C5—C6—C1	0.4 (5)	C7—C8—S1—O1	−169.6 (2)
C4—C5—C6—C7	−179.4 (3)	C7—C8—S1—O2	58.7 (3)
C2—C1—C6—C5	0.6 (4)	C7—C8—S1—N1	−57.2 (2)
N1—C1—C6—C5	−177.2 (3)	C2—C1—N1—C16	−3.3 (5)
C2—C1—C6—C7	−179.6 (3)	C6—C1—N1—C16	174.5 (3)
N1—C1—C6—C7	2.6 (5)	C2—C1—N1—S1	152.0 (3)
C5—C6—C7—N2	−9.5 (4)	C6—C1—N1—S1	−30.2 (4)
C1—C6—C7—N2	170.6 (3)	O1—S1—N1—C1	169.3 (3)
C5—C6—C7—C8	170.0 (3)	O2—S1—N1—C1	−60.1 (3)
C1—C6—C7—C8	−9.8 (4)	C8—S1—N1—C1	54.3 (3)
N2—C7—C8—S1	−140.5 (3)	O1—S1—N1—C16	−34.5 (3)
C6—C7—C8—S1	40.0 (3)	O2—S1—N1—C16	96.1 (3)
N3—C9—C10—C11	7.3 (5)	C8—S1—N1—C16	−149.5 (3)
N3—C9—C10—C15	−171.9 (3)	C6—C7—N2—N3	−179.8 (2)
C15—C10—C11—C12	0.5 (5)	C8—C7—N2—N3	0.7 (4)
C9—C10—C11—C12	−178.7 (3)	C10—C9—N3—N2	−179.4 (3)
C10—C11—C12—C13	0.4 (6)	C7—N2—N3—C9	178.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2ⁱ	0.97	2.56	3.397 (4)	145
C9—H9···O1ⁱⁱ	0.93	2.39	3.292 (4)	163

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrFN₃O₂S
M_r	410.26
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.8996 (4), 9.0070 (4), 13.5057 (7)
α, β, γ (°)	104.176 (3), 90.977 (3), 113.466 (3)
V (Å³)	847.51 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.57
Crystal size (mm)	0.37 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.450, 0.715
No. of measured, independent and observed [I > 2σ(I)] reflections	17622, 4186, 2331
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.118, 0.99
No. of reflections	4186
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.78

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2ⁱ	0.97	2.56	3.397 (4)	145
C9—H9···O1ⁱⁱ	0.93	2.39	3.292 (4)	163

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z.

Acknowledgements

MS acknowledges the Higher Education Commission of Pakistan for financial support, GC University Lahore, Pakistan, for laboratory facilities during his PhD studies and Dr Michael Harmata for guidance during his stay at the Department of Chemistry, University of Missouri, USA.

References

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