Methyl 2-(but-3-en­yl)-4-hy­droxy-1,1-dioxo-2H-1λ6,2-benzothia­zine-3-carboxyl­ate

Arshad, M.N.; Khan, I.U.; Zia-ur-Rehman, M.; Danish, M.; Holman, K.T.

doi:10.1107/S1600536812022908

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1926

doi:10.1107/S1600536812022908

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Methyl 2-(but-3-enyl)-4-hydroxy-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxylate

Muhammad Nadeem Arshad,^a ^* Islam Ullah Khan,^b Muhammad Zia-ur-Rehman,^c Muhammad Danish ^a and K. Travis Holman ^d

^aDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan, ^bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^cApplied Chemistry Research Centre PCSIR Laboratories Complex, Lahore 54600, Pakistan, and ^dDepartment of Chemistry, Georgetown University, 37th and `O' Streets NW Washington, DC 20057-1227, USA
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 17 May 2012; accepted 19 May 2012; online 31 May 2012)

In the title compound, C₁₄H₁₅NO₅S, the thiazine ring adopts a sofa conformation and an intramolecular O—H⋯O hydrogen bond forms an S(6) ring. In the crystal, molecules are linked viaC—H⋯O interactions.

Related literature

For the synthesis, see: Arshad et al. (2011b ); Zia-ur-Rehman, et al. (2006 ). For related structures, see: Arshad et al. (2011a , 2012 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₅NO₅S
M_r = 309.33
Orthorhombic, P b c n
a = 25.265 (8) Å
b = 8.929 (3) Å
c = 12.584 (4) Å
V = 2839.0 (15) Å³
Z = 8
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 100 K
0.41 × 0.36 × 0.19 mm

Data collection

Bruker SMART 1K diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.905, T_max = 0.954
22868 measured reflections
3445 independent reflections
2643 reflections with I > 2σ(I)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.109
S = 1.05
3445 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.52	3.269 (2)	136
O1—H1O⋯O4	0.84 (3)	1.81 (3)	2.577 (2)	151 (3)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ) and X-SEED (Barbour 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022908/bt5926sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022908/bt5926Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022908/bt5926Isup3.cml

checkCIF report

Comment top

Herein we report the crystal structure of the title compound in continuation of our research on the synthesis (Arshad et al., 2011b), biological activities (Zia-ur-Rehman et al., 2006) and crystal structures (Arshad et al., 2011a, 2012) of thiazine related heterocyles.

The title compound is the N-3-butenyl derivative of methyl-4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide. The planar methyl ester moiety (r.m.s deviation 0.008Å) is oriented at dihedral angles of 11.39 (10)° and 16.97 (11)° with respect to the thiazine (C1/C6/C7/C8/N1/S1) and benzene (C1/C2/C3/C4/C5/C6) rings. The thiazine ring adopts a sofa conformation and is inclined at 17.27 (12)° with respect to the benzene ring. A six membered (C7/O1/H1O/O4/C9/C8) ring with graph set notation S¹₁(6) (Bernstein et al., 1995) is formed through an O—H···O intramolecular hydrogen bond. The crystal structure is stabilized by weak C—H···O interactions (Tab. 1).

Related literature top

For the synthesis, see: Arshad et al. (2011b); Zia-ur-Rehman, et al. (2006). For related structures, see: Arshad et al. (2011a, 2012). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The synthesis of the titled compound has been published (Arshad et al., 2011a). The title compound was recrystallized from ethylacetate under slow evaporation of the solvent.

Computing details top

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

Figures top

Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability.

Methyl 2-(but-3-enyl)-4-hydroxy-1,1-dioxo-2H-1λ⁶,2- benzothiazine-3-carboxylate top

Crystal data top

C₁₄H₁₅NO₅S	F(000) = 1296
M_r = 309.33	D_x = 1.447 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4741 reflections
a = 25.265 (8) Å	θ = 2.4–27.3°
b = 8.929 (3) Å	µ = 0.25 mm⁻¹
c = 12.584 (4) Å	T = 100 K
V = 2839.0 (15) Å³	Block, colorless
Z = 8	0.41 × 0.36 × 0.19 mm

Data collection top

Bruker SMART 1K diffractometer	3445 independent reflections
Radiation source: fine-focus sealed tube	2643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.081
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −33→32
T_min = 0.905, T_max = 0.954	k = −11→11
22868 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0432P)² + 1.393P] where P = (F_o² + 2F_c²)/3
3445 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₄H₁₅NO₅S	V = 2839.0 (15) Å³
M_r = 309.33	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 25.265 (8) Å	µ = 0.25 mm⁻¹
b = 8.929 (3) Å	T = 100 K
c = 12.584 (4) Å	0.41 × 0.36 × 0.19 mm

Data collection top

Bruker SMART 1K diffractometer	3445 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2643 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.954	R_int = 0.081
22868 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.33 e Å⁻³
3445 reflections	Δρ_min = −0.52 e Å⁻³
194 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
S1	0.383769 (17)	0.36570 (5)	0.46460 (3)	0.01998 (13)
O1	0.28657 (5)	0.22258 (15)	0.20949 (10)	0.0233 (3)
O2	0.38708 (5)	0.20923 (14)	0.48963 (10)	0.0237 (3)
O3	0.41184 (5)	0.47125 (15)	0.52964 (10)	0.0252 (3)
O4	0.37180 (5)	0.18207 (15)	0.10068 (10)	0.0242 (3)
O5	0.44900 (5)	0.25535 (14)	0.17283 (10)	0.0218 (3)
N1	0.40302 (6)	0.38813 (17)	0.34120 (11)	0.0193 (3)
C1	0.31660 (7)	0.4152 (2)	0.45726 (14)	0.0206 (4)
C2	0.29195 (7)	0.4945 (2)	0.53786 (14)	0.0234 (4)
H2	0.3113	0.5258	0.5987	0.028*
C3	0.23838 (7)	0.5274 (2)	0.52817 (15)	0.0260 (4)
H3	0.2210	0.5839	0.5819	0.031*
C4	0.21024 (7)	0.4782 (2)	0.44037 (15)	0.0256 (4)
H4	0.1734	0.4989	0.4354	0.031*
C5	0.23497 (7)	0.3991 (2)	0.35976 (15)	0.0233 (4)
H5	0.2151	0.3656	0.3003	0.028*
C6	0.28911 (7)	0.36857 (19)	0.36578 (14)	0.0194 (4)
C7	0.31751 (7)	0.29795 (19)	0.27785 (14)	0.0198 (4)
C8	0.37096 (7)	0.3116 (2)	0.26458 (14)	0.0190 (4)
C9	0.39673 (7)	0.2439 (2)	0.17199 (14)	0.0202 (4)
C10	0.47565 (8)	0.1946 (2)	0.08044 (15)	0.0271 (4)
H10A	0.4664	0.0886	0.0725	0.041*
H10B	0.5140	0.2044	0.0894	0.041*
H10C	0.4645	0.2496	0.0169	0.041*
C11	0.42697 (7)	0.5340 (2)	0.30952 (15)	0.0228 (4)
H11A	0.4436	0.5221	0.2387	0.027*
H11B	0.4554	0.5591	0.3606	0.027*
C12	0.38804 (8)	0.6648 (2)	0.30478 (16)	0.0272 (4)
H12A	0.3576	0.6377	0.2591	0.033*
H12B	0.3745	0.6864	0.3770	0.033*
C13	0.41478 (8)	0.8014 (2)	0.26092 (17)	0.0316 (5)
H13	0.4245	0.8001	0.1880	0.038*
C14	0.42573 (8)	0.9223 (2)	0.31568 (17)	0.0306 (5)
H14A	0.4166	0.9276	0.3888	0.037*
H14B	0.4428	1.0045	0.2823	0.037*
H1O	0.3066 (11)	0.199 (3)	0.159 (2)	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0183 (2)	0.0232 (2)	0.0185 (2)	−0.00070 (17)	−0.00184 (16)	−0.00094 (17)
O1	0.0193 (6)	0.0285 (7)	0.0221 (7)	−0.0037 (5)	−0.0026 (5)	−0.0032 (5)
O2	0.0240 (7)	0.0246 (7)	0.0227 (7)	0.0010 (5)	−0.0039 (5)	0.0011 (5)
O3	0.0231 (7)	0.0310 (7)	0.0217 (7)	−0.0030 (5)	−0.0018 (5)	−0.0041 (6)
O4	0.0211 (6)	0.0284 (7)	0.0230 (7)	−0.0001 (5)	−0.0031 (5)	−0.0043 (6)
O5	0.0174 (6)	0.0261 (7)	0.0219 (6)	0.0018 (5)	−0.0002 (5)	−0.0021 (5)
N1	0.0171 (7)	0.0230 (8)	0.0178 (7)	−0.0020 (6)	−0.0010 (6)	−0.0018 (6)
C1	0.0194 (8)	0.0202 (9)	0.0221 (9)	−0.0026 (7)	0.0016 (7)	0.0027 (7)
C2	0.0250 (9)	0.0250 (10)	0.0201 (9)	−0.0023 (8)	0.0012 (7)	−0.0004 (7)
C3	0.0264 (9)	0.0256 (10)	0.0260 (10)	0.0012 (8)	0.0076 (7)	0.0014 (8)
C4	0.0193 (9)	0.0278 (10)	0.0297 (10)	0.0015 (7)	0.0036 (7)	0.0062 (8)
C5	0.0192 (9)	0.0267 (10)	0.0241 (9)	−0.0029 (7)	−0.0001 (7)	0.0043 (8)
C6	0.0189 (8)	0.0187 (9)	0.0205 (9)	−0.0026 (7)	0.0001 (7)	0.0028 (7)
C7	0.0200 (8)	0.0194 (9)	0.0198 (9)	−0.0010 (7)	−0.0022 (7)	0.0018 (7)
C8	0.0186 (8)	0.0194 (8)	0.0189 (9)	−0.0013 (7)	−0.0025 (7)	−0.0004 (7)
C9	0.0196 (9)	0.0196 (9)	0.0213 (9)	0.0006 (7)	−0.0008 (7)	0.0027 (7)
C10	0.0241 (9)	0.0319 (11)	0.0253 (10)	0.0034 (8)	0.0040 (8)	−0.0036 (8)
C11	0.0210 (9)	0.0243 (10)	0.0230 (9)	−0.0048 (7)	0.0010 (7)	−0.0020 (8)
C12	0.0281 (10)	0.0249 (10)	0.0286 (10)	−0.0031 (8)	−0.0032 (8)	−0.0006 (8)
C13	0.0398 (12)	0.0307 (11)	0.0242 (10)	−0.0041 (9)	−0.0020 (9)	0.0037 (9)
C14	0.0343 (11)	0.0261 (10)	0.0313 (11)	−0.0013 (8)	−0.0053 (8)	0.0042 (9)

Geometric parameters (Å, º) top

S1—O2	1.4346 (14)	C5—C6	1.397 (2)
S1—O3	1.4356 (13)	C5—H5	0.9500
S1—N1	1.6396 (16)	C6—C7	1.462 (2)
S1—C1	1.7561 (19)	C7—C8	1.366 (2)
O1—C7	1.343 (2)	C8—C9	1.465 (3)
O1—H1O	0.84 (3)	C10—H10A	0.9800
O4—C9	1.227 (2)	C10—H10B	0.9800
O5—C9	1.325 (2)	C10—H10C	0.9800
O5—C10	1.449 (2)	C11—C12	1.528 (3)
N1—C8	1.433 (2)	C11—H11A	0.9900
N1—C11	1.490 (2)	C11—H11B	0.9900
C1—C2	1.385 (3)	C12—C13	1.499 (3)
C1—C6	1.407 (2)	C12—H12A	0.9900
C2—C3	1.391 (3)	C12—H12B	0.9900
C2—H2	0.9500	C13—C14	1.310 (3)
C3—C4	1.386 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—H14A	0.9500
C4—C5	1.385 (3)	C14—H14B	0.9500
C4—H4	0.9500

O2—S1—O3	119.04 (8)	C8—C7—C6	122.63 (16)
O2—S1—N1	108.04 (8)	C7—C8—N1	121.29 (16)
O3—S1—N1	108.25 (8)	C7—C8—C9	119.96 (16)
O2—S1—C1	108.24 (8)	N1—C8—C9	118.73 (15)
O3—S1—C1	110.00 (8)	O4—C9—O5	123.51 (17)
N1—S1—C1	101.90 (8)	O4—C9—C8	122.61 (16)
C7—O1—H1O	104.9 (18)	O5—C9—C8	113.87 (15)
C9—O5—C10	115.33 (14)	O5—C10—H10A	109.5
C8—N1—C11	117.79 (14)	O5—C10—H10B	109.5
C8—N1—S1	114.29 (12)	H10A—C10—H10B	109.5
C11—N1—S1	118.72 (12)	O5—C10—H10C	109.5
C2—C1—C6	121.90 (17)	H10A—C10—H10C	109.5
C2—C1—S1	121.65 (14)	H10B—C10—H10C	109.5
C6—C1—S1	116.46 (13)	N1—C11—C12	114.66 (15)
C1—C2—C3	118.80 (17)	N1—C11—H11A	108.6
C1—C2—H2	120.6	C12—C11—H11A	108.6
C3—C2—H2	120.6	N1—C11—H11B	108.6
C4—C3—C2	120.14 (17)	C12—C11—H11B	108.6
C4—C3—H3	119.9	H11A—C11—H11B	107.6
C2—C3—H3	119.9	C13—C12—C11	110.25 (17)
C5—C4—C3	120.96 (17)	C13—C12—H12A	109.6
C5—C4—H4	119.5	C11—C12—H12A	109.6
C3—C4—H4	119.5	C13—C12—H12B	109.6
C4—C5—C6	120.12 (18)	C11—C12—H12B	109.6
C4—C5—H5	119.9	H12A—C12—H12B	108.1
C6—C5—H5	119.9	C14—C13—C12	124.9 (2)
C5—C6—C1	118.02 (17)	C14—C13—H13	117.6
C5—C6—C7	121.60 (16)	C12—C13—H13	117.6
C1—C6—C7	120.29 (16)	C13—C14—H14A	120.0
O1—C7—C8	122.81 (16)	C13—C14—H14B	120.0
O1—C7—C6	114.53 (15)	H14A—C14—H14B	120.0

O2—S1—N1—C8	61.69 (14)	C5—C6—C7—O1	−20.8 (2)
O3—S1—N1—C8	−168.15 (12)	C1—C6—C7—O1	162.66 (16)
C1—S1—N1—C8	−52.19 (14)	C5—C6—C7—C8	157.21 (18)
O2—S1—N1—C11	−152.15 (12)	C1—C6—C7—C8	−19.3 (3)
O3—S1—N1—C11	−21.99 (15)	O1—C7—C8—N1	−177.64 (15)
C1—S1—N1—C11	93.96 (14)	C6—C7—C8—N1	4.5 (3)
O2—S1—C1—C2	104.25 (16)	O1—C7—C8—C9	0.7 (3)
O3—S1—C1—C2	−27.34 (18)	C6—C7—C8—C9	−177.14 (16)
N1—S1—C1—C2	−142.01 (15)	C11—N1—C8—C7	−110.93 (19)
O2—S1—C1—C6	−75.07 (15)	S1—N1—C8—C7	35.6 (2)
O3—S1—C1—C6	153.34 (13)	C11—N1—C8—C9	70.7 (2)
N1—S1—C1—C6	38.67 (15)	S1—N1—C8—C9	−142.81 (14)
C6—C1—C2—C3	0.6 (3)	C10—O5—C9—O4	2.4 (3)
S1—C1—C2—C3	−178.67 (14)	C10—O5—C9—C8	−177.74 (15)
C1—C2—C3—C4	1.6 (3)	C7—C8—C9—O4	4.8 (3)
C2—C3—C4—C5	−1.7 (3)	N1—C8—C9—O4	−176.84 (16)
C3—C4—C5—C6	−0.3 (3)	C7—C8—C9—O5	−175.05 (16)
C4—C5—C6—C1	2.4 (3)	N1—C8—C9—O5	3.3 (2)
C4—C5—C6—C7	−174.17 (17)	C8—N1—C11—C12	74.1 (2)
C2—C1—C6—C5	−2.6 (3)	S1—N1—C11—C12	−70.88 (19)
S1—C1—C6—C5	176.72 (14)	N1—C11—C12—C13	−173.83 (15)
C2—C1—C6—C7	174.05 (17)	C11—C12—C13—C14	−111.0 (2)
S1—C1—C6—C7	−6.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.52	3.269 (2)	136
O1—H1O···O4	0.84 (3)	1.81 (3)	2.577 (2)	151 (3)

Symmetry code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₅NO₅S
M_r	309.33
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	25.265 (8), 8.929 (3), 12.584 (4)
V (Å³)	2839.0 (15)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.41 × 0.36 × 0.19

Data collection
Diffractometer	Bruker SMART 1K diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.905, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	22868, 3445, 2643
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.109, 1.05
No. of reflections	3445
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.52

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and X-SEED (Barbour 2001), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.52	3.269 (2)	136.2
O1—H1O···O4	0.84 (3)	1.81 (3)	2.577 (2)	151 (3)

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing fellowships to MNA (PIN # 042–120607-Ps2–183 and PIN # IRSIP-10-PS-2).

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