Literature DB >> 21583256

6-Bromo-3,3-dichloro-1-methyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

Muhammad Shafiq, M Nawaz Tahir, Islam Ullah Khan, Muhammad Nadeem Arshad, Zeeshan Haider.

Abstract

The monomeric title compound, C(9)H(6)BrCl(2)NO(3)S, has an envelope-shaped n class="Chemical">thia-zine ring with the S atom 0.879 (9) Å out of the mean square plane of the envelope. The π-π distances between the centroids of the heterocyclic rings are 4.191 (5) and 4.110 (5) Å. The closest intermolecular inter-actions between the O atoms of the carbonyl and sulfonyl groups with Br and Cl atoms are 2.987 (7) and 2.992 (8) Å, respectively.

Entities: Chemical Disease Species

Year: 2009 PMID： 21583256 PMCID： PMC2969529 DOI： 10.1107/S1600536809019291

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

Related literature

For halogination (chlorination or bromination) of n class="Chemical">1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide, see: Shafiq et al. (2008 ▶); Shafiq, Tahir, Khan, Ahmad et al. (2009 ▶); Shafiq, Tahir, Khan, Arshad & Asghar (2009 ▶); Shafiq, Tahir, Khan, Arshad & Safdar (2009 ▶).

Experimental

Crystal data

C9H6BrCl2NO3S M = 359.02 Monoclinic, a = 7.0285 (9) Å b = 14.865 (2) Å c = 11.9739 (18) Å β = 92.418 (5)° V = 1249.9 (3) Å3 Z = 4 Mo Kα radiation μ = 3.88 mm−1 T = 296 K 0.26 × 0.14 × 0.12 mm

Data collection

Bruker Kappa-APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.529, T max = 0.626 11409 measured reflections 2317 independent reflections 1595 reflections with I > 2σ(I) R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.082 wR(F 2) = 0.249 S = 1.09 2317 reflections 155 parameters H-atom parameters constrained Δρmax = 2.07 e Å−3 Δρmin = −0.46 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (n class="Chemical">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 PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019291/ng2585sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019291/ng2585Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₉H₆BrCl₂NO₃S	F(000) = 704
M_r = 359.02	D_x = 1.908 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2317 reflections
a = 7.0285 (9) Å	θ = 2.7–25.5°
b = 14.865 (2) Å	µ = 3.88 mm⁻¹
c = 11.9739 (18) Å	T = 296 K
β = 92.418 (5)°	Needle, yellow
V = 1249.9 (3) Å³	0.26 × 0.14 × 0.12 mm
Z = 4

Bruker Kappa-APEXII CCD diffractometer	2317 independent reflections
Radiation source: fine-focus sealed tube	1595 reflections with I > 2σ(I)
graphite	R_int = 0.048
Detector resolution: 7.80 pixels mm^-1	θ_max = 25.5°, θ_min = 2.7°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→18
T_min = 0.529, T_max = 0.626	l = −14→14
11409 measured reflections

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.249	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1412P)² + 3.7083P] where P = (F_o² + 2F_c²)/3
2317 reflections	(Δ/σ)_max < 0.000
155 parameters	Δρ_max = 2.07 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	U_iso*/U_eq
Br1	0.74792 (15)	0.56286 (7)	0.70311 (9)	0.0672 (4)
Cl1	0.7616 (5)	0.06220 (15)	0.4704 (3)	0.0880 (13)
Cl2	0.4591 (4)	0.1801 (2)	0.3853 (3)	0.0812 (11)
S1	0.8566 (4)	0.20955 (15)	0.3260 (2)	0.0605 (9)
O1	1.0377 (10)	0.2088 (5)	0.3836 (7)	0.073 (3)
O2	0.8231 (13)	0.1591 (5)	0.2266 (7)	0.092 (3)
O3	0.7221 (14)	0.2086 (5)	0.6253 (6)	0.086 (3)
N1	0.7709 (10)	0.3103 (5)	0.3049 (5)	0.047 (3)
C1	0.7428 (11)	0.3339 (5)	0.5055 (7)	0.041 (2)
C2	0.7384 (11)	0.3928 (6)	0.5972 (7)	0.046 (3)
C3	0.7472 (11)	0.4837 (5)	0.5800 (7)	0.045 (3)
C4	0.7598 (12)	0.5177 (5)	0.4732 (8)	0.050 (3)
C5	0.7673 (12)	0.4611 (5)	0.3832 (7)	0.046 (3)
C6	0.7602 (10)	0.3681 (5)	0.3979 (6)	0.037 (2)
C7	0.7331 (16)	0.3430 (8)	0.1909 (7)	0.069 (4)
C8	0.7023 (14)	0.1722 (5)	0.4321 (8)	0.055 (3)
C9	0.7248 (12)	0.2370 (6)	0.5326 (7)	0.048 (3)
H2	0.72951	0.37007	0.66913	0.0547*
H4	0.76319	0.57957	0.46234	0.0596*
H5	0.77715	0.48484	0.31182	0.0551*
H7A	0.83703	0.38008	0.16917	0.1043*
H7B	0.71969	0.29273	0.14086	0.1043*
H7C	0.61767	0.37762	0.18786	0.1043*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0732 (8)	0.0623 (7)	0.0664 (7)	−0.0014 (4)	0.0073 (5)	−0.0331 (5)
Cl1	0.140 (3)	0.0300 (12)	0.094 (2)	0.0046 (13)	0.006 (2)	0.0024 (12)
Cl2	0.0585 (16)	0.098 (2)	0.086 (2)	−0.0217 (14)	−0.0094 (14)	−0.0057 (16)
S1	0.0730 (18)	0.0455 (13)	0.0641 (15)	0.0053 (11)	0.0174 (13)	−0.0116 (11)
O1	0.047 (4)	0.076 (5)	0.096 (5)	0.017 (3)	0.005 (4)	−0.008 (4)
O2	0.136 (7)	0.063 (5)	0.078 (5)	−0.002 (5)	0.028 (5)	−0.035 (4)
O3	0.164 (8)	0.048 (4)	0.046 (4)	0.001 (4)	0.006 (4)	0.012 (3)
N1	0.075 (5)	0.036 (4)	0.031 (4)	0.003 (3)	0.005 (3)	−0.002 (3)
C1	0.045 (4)	0.034 (4)	0.043 (4)	0.000 (3)	0.002 (3)	−0.001 (3)
C2	0.056 (5)	0.048 (5)	0.033 (4)	−0.002 (4)	0.001 (4)	−0.001 (4)
C3	0.051 (5)	0.034 (4)	0.049 (5)	0.000 (3)	−0.003 (4)	−0.014 (4)
C4	0.057 (5)	0.031 (4)	0.061 (6)	0.003 (4)	0.008 (4)	0.003 (4)
C5	0.068 (6)	0.034 (4)	0.037 (4)	0.001 (4)	0.005 (4)	0.001 (3)
C6	0.041 (4)	0.042 (4)	0.029 (4)	0.003 (3)	0.002 (3)	−0.001 (3)
C7	0.102 (8)	0.073 (7)	0.033 (5)	0.014 (6)	0.002 (5)	−0.001 (4)
C8	0.082 (7)	0.028 (4)	0.054 (5)	−0.006 (4)	0.002 (5)	−0.001 (4)
C9	0.059 (5)	0.041 (4)	0.044 (5)	0.000 (4)	−0.001 (4)	0.003 (4)

Br1—C3	1.886 (8)	C1—C9	1.483 (12)
Cl1—C8	1.744 (8)	C2—C3	1.369 (12)
Cl2—C8	1.780 (10)	C3—C4	1.381 (12)
S1—O1	1.422 (8)	C4—C5	1.370 (12)
S1—O2	1.418 (8)	C5—C6	1.395 (11)
S1—N1	1.630 (8)	C8—C9	1.544 (12)
S1—C8	1.793 (10)	C2—H2	0.9300
O3—C9	1.189 (11)	C4—H4	0.9300
N1—C6	1.411 (10)	C5—H5	0.9300
N1—C7	1.463 (11)	C7—H7A	0.9600
C1—C2	1.406 (12)	C7—H7B	0.9600
C1—C6	1.395 (11)	C7—H7C	0.9600

Br1···O3ⁱ	2.987 (7)	C3···C4ⁱⁱ	3.593 (12)
Br1···C5ⁱⁱ	3.741 (9)	C3···C4ⁱⁱⁱ	3.550 (12)
Br1···C5ⁱⁱⁱ	3.620 (9)	C3···C5ⁱⁱⁱ	3.519 (11)
Br1···H7Cⁱⁱ	3.0600	C4···O2^ix	3.219 (12)
Cl1···O1	3.125 (8)	C4···C3ⁱⁱ	3.593 (12)
Cl1···O2	3.300 (9)	C4···C3ⁱⁱⁱ	3.550 (12)
Cl1···O3	2.880 (8)	C4···C4ⁱⁱⁱ	3.451 (12)
Cl2···O1^iv	2.992 (8)	C5···Br1ⁱⁱ	3.741 (9)
Cl2···O2	3.266 (9)	C5···Br1ⁱⁱⁱ	3.620 (9)
Cl2···O3	3.377 (9)	C5···O2^ix	3.275 (11)
Cl2···N1	3.107 (8)	C5···C3ⁱⁱⁱ	3.519 (11)
Cl2···C6	3.505 (8)	C6···Cl2	3.505 (8)
Cl2···H2^v	3.0800	C5···H7C	2.8100
O1···Cl1	3.125 (8)	C5···H7A	2.8900
O1···Cl2^vi	2.992 (8)	C7···H5	2.5700
O1···C1	3.184 (11)	H2···O3	2.4600
O2···Cl1	3.300 (9)	H2···Cl2^x	3.0800
O2···Cl2	3.266 (9)	H4···O2^ix	2.6000
O2···C4^vii	3.219 (12)	H5···C7	2.5700
O2···C5^vii	3.275 (11)	H5···H7A	2.3600
O3···Cl2	3.377 (9)	H5···H7C	2.4200
O3···Cl1	2.880 (8)	H5···O2^ix	2.7200
O3···Br1^viii	2.987 (7)	H7A···C5	2.8900
O2···H7B	2.3400	H7A···H5	2.3600
O2···H5^vii	2.7200	H7B···O2	2.3400
O2···H4^vii	2.6000	H7C···C5	2.8100
O3···H2	2.4600	H7C···H5	2.4200
N1···Cl2	3.107 (8)	H7C···Br1ⁱⁱ	3.0600
C1···O1	3.184 (11)

O1—S1—O2	121.1 (5)	Cl1—C8—Cl2	111.1 (5)
O1—S1—N1	113.6 (4)	Cl1—C8—S1	109.4 (5)
O1—S1—C8	102.1 (5)	Cl1—C8—C9	111.4 (6)
O2—S1—N1	108.0 (4)	Cl2—C8—S1	111.0 (5)
O2—S1—C8	110.3 (5)	Cl2—C8—C9	105.6 (6)
N1—S1—C8	99.4 (4)	S1—C8—C9	108.3 (6)
S1—N1—C6	118.0 (5)	O3—C9—C1	123.7 (8)
S1—N1—C7	120.1 (6)	O3—C9—C8	120.1 (8)
C6—N1—C7	121.4 (7)	C1—C9—C8	116.2 (7)
C2—C1—C6	120.0 (7)	C1—C2—H2	120.00
C2—C1—C9	115.4 (7)	C3—C2—H2	120.00
C6—C1—C9	124.6 (7)	C3—C4—H4	120.00
C1—C2—C3	119.7 (8)	C5—C4—H4	120.00
Br1—C3—C2	119.8 (6)	C4—C5—H5	120.00
Br1—C3—C4	119.8 (6)	C6—C5—H5	120.00
C2—C3—C4	120.4 (8)	N1—C7—H7A	109.00
C3—C4—C5	120.6 (7)	N1—C7—H7B	109.00
C4—C5—C6	120.4 (7)	N1—C7—H7C	109.00
N1—C6—C1	121.1 (7)	H7A—C7—H7B	109.00
N1—C6—C5	120.0 (7)	H7A—C7—H7C	109.00
C1—C6—C5	118.9 (7)	H7B—C7—H7C	109.00

O1—S1—N1—C6	−52.8 (7)	C2—C1—C6—N1	178.0 (7)
O1—S1—N1—C7	118.5 (8)	C2—C1—C6—C5	−1.9 (11)
O2—S1—N1—C6	169.9 (6)	C9—C1—C6—N1	−3.0 (12)
O2—S1—N1—C7	−18.7 (9)	C9—C1—C6—C5	177.1 (8)
C8—S1—N1—C6	54.9 (7)	C2—C1—C9—O3	−5.9 (13)
C8—S1—N1—C7	−133.8 (7)	C2—C1—C9—C8	172.1 (7)
O1—S1—C8—Cl1	−64.1 (6)	C6—C1—C9—O3	175.1 (9)
O1—S1—C8—Cl2	173.0 (5)	C6—C1—C9—C8	−6.9 (12)
O1—S1—C8—C9	57.5 (7)	C1—C2—C3—Br1	−178.4 (6)
O2—S1—C8—Cl1	65.9 (6)	C1—C2—C3—C4	0.2 (12)
O2—S1—C8—Cl2	−57.0 (6)	Br1—C3—C4—C5	177.3 (6)
O2—S1—C8—C9	−172.5 (6)	C2—C3—C4—C5	−1.2 (12)
N1—S1—C8—Cl1	179.2 (5)	C3—C4—C5—C6	0.7 (13)
N1—S1—C8—Cl2	56.3 (5)	C4—C5—C6—N1	−179.1 (7)
N1—S1—C8—C9	−59.3 (6)	C4—C5—C6—C1	0.8 (12)
S1—N1—C6—C1	−27.0 (10)	Cl1—C8—C9—O3	−21.8 (12)
S1—N1—C6—C5	152.9 (6)	Cl1—C8—C9—C1	160.1 (6)
C7—N1—C6—C1	161.8 (8)	Cl2—C8—C9—O3	98.9 (9)
C7—N1—C6—C5	−18.3 (11)	Cl2—C8—C9—C1	−79.2 (8)
C6—C1—C2—C3	1.4 (12)	S1—C8—C9—O3	−142.1 (8)
C9—C1—C2—C3	−177.7 (7)	S1—C8—C9—C1	39.8 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O2	0.9600	2.3400	2.834 (14)	112.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O2	0.9600	2.3400	2.834 (14)	112.00

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2. 3,3-Dibromo-1-ethyl-1H-2,1-benzo-thiazin-4(3H)-one 2,2-dioxide.

Authors: Muhammad Shafiq; M Nawaz Tahir; Islam Ullah Khan; Saeed Ahmad; Waseeq Ahmad Siddiqui
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3. 6-Bromo-1-methyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

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Authors: Muhammad Shafiq; M Nawaz Tahir; Islam Ullah Khan; Saeed Ahmad; Muhammad Nadeem Arshad
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-01-31

5. 6-Bromo-1-ethyl-1H-2,1-benzothia-zin-4(3H)-one 2,2-dioxide.

Authors: Muhammad Shafiq; M Nawaz Tahir; Islam Ullah Khan; Muhammad Nadeem Arshad; Muhammad Safdar
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-01-28

6. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20