3-[Hy­droxy(3-meth­oxy­phen­yl)methyl­idene]-2-(2-oxo-2-phenyl­eth­yl)-3,4-dihydro-2H-1λ6,2-benzothia­zine-1,1,4-trione

Siddiqui, H.L.; Ahmad, M.; Gul, S.; Siddiqui, W.A.; Parvez, M.

doi:10.1107/S1600536812009002

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o978-o979

doi:10.1107/S1600536812009002

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3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)-3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione

Hamid Latif Siddiqui,^a ^* Matloob Ahmad,^b Salman Gul,^a Waseeq Ahmad Siddiqui ^c and Masood Parvez ^d

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bChemistry Department, Govt. College University, Faisalabad, Pakistan, ^cChemistry Department, University of Sargodha, Sargodha 40100, Pakistan, and ^dDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@hotmail.com

(Received 23 February 2012; accepted 29 February 2012; online 7 March 2012)

In the title molecule, C₂₄H₁₉NO₆S, the heterocyclic thiazine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothiazine unit and the methoxyphenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenylethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The molecular structure is consolidated by intramolecular O—H⋯O and C—H⋯N interactions, and the crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

Related literature

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007 ). For the biological activity of 1,2-benzothiazine derivatives, see: Lombardino & Wiseman (1972 ); Gupta et al. (1993 , 2002 ); Zia-ur-Rehman et al. (2006 ); Ahmad et al. (2010 ). For a related structure, see: Siddiqui et al. (2008 ).

Experimental

Crystal data

C₂₄H₁₉NO₆S
M_r = 449.46
Orthorhombic, P b c a
a = 17.9615 (5) Å
b = 11.2633 (3) Å
c = 19.5904 (6) Å
V = 3963.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 173 K
0.14 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.971, T_max = 0.984
8340 measured reflections
4543 independent reflections
3198 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.133
S = 1.10
4543 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1ⁱ	0.95	2.59	3.281 (4)	130
C11—H11⋯O1ⁱⁱ	0.95	2.53	3.371 (4)	148
C16—H16B⋯O6ⁱⁱⁱ	0.98	2.64	3.246 (4)	120
C24—H24⋯O5^iv	0.95	2.57	3.508 (4)	167
O4—H4O⋯O3	0.84	1.71	2.478 (3)	151
C15—H15⋯N1	0.95	2.38	2.972 (4)	120
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009002/pk2393sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009002/pk2393Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009002/pk2393Isup3.cml

checkCIF report

Comment top

The derivatives of 1,2-benzothiazine exhibit a wide range of biological activities, e.g., anti inflammatory (Lombardino & Wiseman, 1972), analgesic (Gupta et al., 2002), anti cancer (Gupta et al., 1993) and anti bacterial (Zia-ur-Rehman et al., 2006), etc. In continuation of our research on the synthesis of biologically active benzothiazine derivatives (Siddiqui et al., 2007; Ahmad et al., 2010), we herein report the synthesis and crystal structure of the title compound.

The bond distances and angles in the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in closely related compounds (Siddiqui et al., 2008). The heterocyclic thiazine ring adopts a half chair conformation with atoms N1 and S1 displaced by 0.497 (6) and 0.180 (6) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings C1–C6 and C10–C15 are almost co-planar with a dihedral angle between the mean planes of these rings being 5.9 (2)°; the benzene ring C19–C24 is oriented at 79.68 (11) and 81.01 (10)°, respectively, with respect to these benzene rings. While the molecular structure of the title compound is consolidated by intramolecular interactions: O4–H4O···O3 and C15–H15···N1, the crystal packing is stabilized by weak intermolecular C—H···O hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007). For the biological activity of 1,2-benzothiazine derivatives, see: Lombardino & Wiseman (1972); Gupta et al. (1993, 2002); Zia-ur-Rehman et al. (2006); Ahmad et al. (2010). For a related structure, see: Siddiqui et al. (2008).

Experimental top

A mixture of (4-hydroxy-1,1-dioxido-2H-1,2-benzothiazin-3-yl)(3-methoxyphenyl) methanone (5.0 g, 0.015 mol), K₂CO₃ (2.07 g, 0.015 mol) and phenacyl bromide (2.99 g, 0.015 mol) in acetonitrile (30 ml) was refluxed for 3 h. The contents of the flask were poured on ice cold HCl (5%, 30 ml). The precipitates of the title compound formed were collected and washed with ethanol. The crystals suitable for X-ray crystallographic analysis were grown from a solution of methanol.

Structure description top

For background information on the synthesis of related compounds, see: Siddiqui et al. (2007). For the biological activity of 1,2-benzothiazine derivatives, see: Lombardino & Wiseman (1972); Gupta et al. (1993, 2002); Zia-ur-Rehman et al. (2006); Ahmad et al. (2010). For a related structure, see: Siddiqui et al. (2008).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—-H···O hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen- bonding were omitted for clarity.

3-[Hydroxy(3-methoxyphenyl)methylidene]-2-(2-oxo-2-phenylethyl)- 3,4-dihydro-2H-1λ⁶,2-benzothiazine-1,1,4-trione top

Crystal data top

C₂₄H₁₉NO₆S	F(000) = 1872
M_r = 449.46	D_x = 1.507 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5006 reflections
a = 17.9615 (5) Å	θ = 1.0–27.5°
b = 11.2633 (3) Å	µ = 0.21 mm⁻¹
c = 19.5904 (6) Å	T = 173 K
V = 3963.3 (2) Å³	Prism, yellow
Z = 8	0.14 × 0.10 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	4543 independent reflections
Radiation source: fine-focus sealed tube	3198 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
ω and φ scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −23→23
T_min = 0.971, T_max = 0.984	k = −14→14
8340 measured reflections	l = −25→25

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + 10.1913P] where P = (F_o² + 2F_c²)/3
4543 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₂₄H₁₉NO₆S	V = 3963.3 (2) Å³
M_r = 449.46	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.9615 (5) Å	µ = 0.21 mm⁻¹
b = 11.2633 (3) Å	T = 173 K
c = 19.5904 (6) Å	0.14 × 0.10 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	4543 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3198 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.984	R_int = 0.059
8340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + 10.1913P] where P = (F_o² + 2F_c²)/3
4543 reflections	Δρ_max = 0.36 e Å⁻³
291 parameters	Δρ_min = −0.49 e Å⁻³

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	0.43448 (4)	0.23066 (7)	0.49448 (4)	0.02772 (19)
O1	0.42975 (13)	0.1891 (2)	0.42537 (11)	0.0321 (5)
O2	0.50593 (12)	0.2608 (2)	0.52165 (13)	0.0380 (6)
O3	0.19812 (12)	0.2130 (2)	0.52567 (12)	0.0334 (6)
O4	0.18789 (12)	0.3846 (2)	0.44712 (12)	0.0311 (5)
H4O	0.1754	0.3308	0.4745	0.047*
O5	0.20407 (13)	0.7401 (2)	0.31274 (12)	0.0350 (6)
O6	0.35370 (14)	0.3374 (2)	0.64057 (12)	0.0395 (6)
N1	0.38071 (14)	0.3469 (2)	0.50267 (13)	0.0248 (6)
C1	0.39090 (18)	0.1240 (3)	0.54646 (16)	0.0259 (7)
C2	0.4322 (2)	0.0323 (3)	0.57373 (17)	0.0358 (8)
H2	0.4841	0.0268	0.5650	0.043*
C3	0.3971 (2)	−0.0515 (3)	0.6140 (2)	0.0421 (9)
H3	0.4248	−0.1157	0.6325	0.051*
C4	0.3218 (2)	−0.0425 (3)	0.62739 (18)	0.0399 (9)
H4	0.2980	−0.0998	0.6555	0.048*
C5	0.2809 (2)	0.0502 (3)	0.59989 (17)	0.0325 (8)
H5	0.2292	0.0561	0.6096	0.039*
C6	0.31417 (18)	0.1342 (3)	0.55844 (16)	0.0264 (7)
C7	0.26845 (17)	0.2284 (3)	0.52620 (16)	0.0261 (7)
C8	0.30240 (16)	0.3262 (3)	0.49250 (16)	0.0231 (6)
C9	0.26011 (18)	0.3991 (3)	0.44929 (16)	0.0262 (7)
C10	0.28801 (17)	0.4937 (3)	0.40321 (16)	0.0256 (7)
C11	0.23700 (17)	0.5772 (3)	0.37964 (15)	0.0254 (7)
H11	0.1871	0.5756	0.3958	0.030*
C12	0.25855 (18)	0.6626 (3)	0.33282 (16)	0.0271 (7)
C13	0.33096 (19)	0.6660 (3)	0.30894 (17)	0.0331 (8)
H13	0.3459	0.7251	0.2772	0.040*
C14	0.3811 (2)	0.5824 (3)	0.33196 (19)	0.0386 (9)
H14	0.4307	0.5839	0.3152	0.046*
C15	0.36098 (19)	0.4962 (3)	0.37892 (18)	0.0343 (8)
H15	0.3964	0.4397	0.3944	0.041*
C16	0.2218 (2)	0.8229 (3)	0.25964 (18)	0.0384 (9)
H16A	0.1770	0.8679	0.2473	0.046*
H16B	0.2400	0.7797	0.2195	0.046*
H16C	0.2604	0.8776	0.2757	0.046*
C17	0.40483 (18)	0.4447 (3)	0.54746 (16)	0.0280 (7)
H17A	0.3794	0.5185	0.5330	0.034*
H17B	0.4590	0.4568	0.5414	0.034*
C18	0.38901 (17)	0.4240 (3)	0.62268 (17)	0.0269 (7)
C19	0.41875 (17)	0.5095 (3)	0.67386 (17)	0.0258 (7)
C20	0.45909 (18)	0.6100 (3)	0.65584 (17)	0.0286 (7)
H20	0.4641	0.6311	0.6091	0.034*
C21	0.49201 (19)	0.6796 (3)	0.70580 (18)	0.0334 (8)
H21	0.5206	0.7471	0.6932	0.040*
C22	0.4834 (2)	0.6511 (3)	0.77347 (18)	0.0359 (8)
H22	0.5068	0.6981	0.8075	0.043*
C23	0.4404 (2)	0.5534 (3)	0.79248 (18)	0.0362 (8)
H23	0.4326	0.5359	0.8394	0.043*
C24	0.40910 (18)	0.4825 (3)	0.74264 (17)	0.0299 (7)
H24	0.3808	0.4148	0.7554	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0271 (4)	0.0275 (4)	0.0285 (4)	0.0017 (3)	−0.0005 (3)	0.0012 (3)
O1	0.0348 (12)	0.0336 (12)	0.0277 (12)	0.0028 (11)	0.0035 (10)	−0.0028 (10)
O2	0.0287 (12)	0.0381 (13)	0.0473 (15)	0.0006 (11)	−0.0057 (11)	0.0028 (12)
O3	0.0288 (12)	0.0310 (12)	0.0403 (14)	−0.0025 (10)	0.0033 (10)	0.0038 (11)
O4	0.0265 (12)	0.0304 (12)	0.0364 (14)	−0.0029 (10)	0.0013 (10)	0.0082 (11)
O5	0.0405 (13)	0.0301 (12)	0.0344 (13)	0.0050 (11)	−0.0015 (11)	0.0086 (11)
O6	0.0571 (16)	0.0347 (13)	0.0266 (13)	−0.0163 (12)	0.0024 (12)	0.0024 (11)
N1	0.0243 (13)	0.0251 (13)	0.0251 (14)	0.0001 (11)	−0.0001 (11)	0.0012 (11)
C1	0.0338 (17)	0.0226 (15)	0.0215 (16)	−0.0026 (13)	−0.0043 (14)	0.0000 (13)
C2	0.044 (2)	0.0330 (18)	0.0306 (19)	0.0050 (17)	−0.0093 (16)	−0.0002 (15)
C3	0.055 (2)	0.0300 (19)	0.041 (2)	0.0033 (18)	−0.0148 (19)	0.0066 (17)
C4	0.060 (2)	0.0301 (18)	0.0298 (19)	−0.0086 (18)	−0.0089 (18)	0.0080 (16)
C5	0.0401 (19)	0.0301 (17)	0.0272 (18)	−0.0087 (15)	−0.0016 (15)	−0.0010 (14)
C6	0.0362 (18)	0.0205 (15)	0.0225 (16)	−0.0017 (13)	−0.0057 (14)	−0.0018 (13)
C7	0.0269 (16)	0.0242 (15)	0.0271 (17)	−0.0025 (13)	0.0007 (13)	−0.0045 (13)
C8	0.0244 (15)	0.0232 (14)	0.0217 (16)	−0.0002 (12)	0.0008 (13)	−0.0006 (13)
C9	0.0290 (17)	0.0252 (15)	0.0245 (16)	−0.0010 (13)	0.0012 (13)	−0.0056 (13)
C10	0.0298 (17)	0.0243 (15)	0.0226 (16)	−0.0006 (13)	−0.0020 (13)	−0.0016 (13)
C11	0.0271 (16)	0.0255 (15)	0.0234 (16)	−0.0030 (13)	−0.0001 (13)	−0.0045 (13)
C12	0.0315 (17)	0.0230 (15)	0.0268 (16)	0.0015 (14)	−0.0067 (14)	−0.0028 (13)
C13	0.0372 (19)	0.0336 (18)	0.0284 (18)	−0.0043 (16)	0.0039 (15)	0.0054 (15)
C14	0.0329 (18)	0.042 (2)	0.041 (2)	0.0014 (16)	0.0088 (17)	0.0093 (17)
C15	0.0319 (18)	0.0355 (18)	0.036 (2)	0.0035 (15)	0.0008 (15)	0.0071 (16)
C16	0.055 (2)	0.0279 (17)	0.032 (2)	0.0025 (17)	−0.0058 (17)	0.0035 (15)
C17	0.0265 (16)	0.0281 (16)	0.0294 (18)	−0.0049 (14)	0.0008 (14)	0.0001 (14)
C18	0.0262 (16)	0.0272 (16)	0.0274 (17)	−0.0004 (13)	0.0020 (14)	0.0033 (14)
C19	0.0216 (15)	0.0253 (15)	0.0305 (18)	0.0028 (13)	−0.0022 (13)	−0.0005 (13)
C20	0.0309 (17)	0.0276 (16)	0.0271 (17)	0.0010 (14)	0.0016 (14)	0.0027 (14)
C21	0.0349 (18)	0.0244 (16)	0.041 (2)	−0.0004 (14)	−0.0003 (16)	−0.0031 (15)
C22	0.0378 (19)	0.0350 (18)	0.035 (2)	0.0003 (16)	−0.0092 (16)	−0.0066 (16)
C23	0.040 (2)	0.044 (2)	0.0246 (17)	0.0019 (17)	−0.0032 (15)	−0.0015 (15)
C24	0.0279 (16)	0.0306 (16)	0.0312 (18)	0.0000 (14)	−0.0010 (14)	0.0048 (15)

Geometric parameters (Å, º) top

S1—O2	1.430 (2)	C10—C15	1.395 (4)
S1—O1	1.435 (2)	C11—C12	1.385 (4)
S1—N1	1.635 (3)	C11—H11	0.9500
S1—C1	1.759 (3)	C12—C13	1.383 (5)
O3—C7	1.275 (4)	C13—C14	1.379 (5)
O4—C9	1.308 (4)	C13—H13	0.9500
O4—H4O	0.8400	C14—C15	1.385 (5)
O5—C12	1.369 (4)	C14—H14	0.9500
O5—C16	1.432 (4)	C15—H15	0.9500
O6—C18	1.215 (4)	C16—H16A	0.9800
N1—C8	1.440 (4)	C16—H16B	0.9800
N1—C17	1.473 (4)	C16—H16C	0.9800
C1—C2	1.380 (4)	C17—C18	1.519 (4)
C1—C6	1.403 (4)	C17—H17A	0.9900
C2—C3	1.383 (5)	C17—H17B	0.9900
C2—H2	0.9500	C18—C19	1.489 (4)
C3—C4	1.381 (5)	C19—C20	1.389 (4)
C3—H3	0.9500	C19—C24	1.392 (4)
C4—C5	1.385 (5)	C20—C21	1.386 (5)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.383 (4)	C21—C22	1.373 (5)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.483 (4)	C22—C23	1.395 (5)
C7—C8	1.421 (4)	C22—H22	0.9500
C8—C9	1.403 (4)	C23—C24	1.381 (5)
C9—C10	1.483 (4)	C23—H23	0.9500
C10—C11	1.392 (4)	C24—H24	0.9500

O2—S1—O1	118.80 (15)	O5—C12—C11	115.7 (3)
O2—S1—N1	107.66 (14)	C13—C12—C11	120.4 (3)
O1—S1—N1	108.60 (14)	C14—C13—C12	119.0 (3)
O2—S1—C1	110.25 (15)	C14—C13—H13	120.5
O1—S1—C1	107.29 (14)	C12—C13—H13	120.5
N1—S1—C1	103.14 (14)	C13—C14—C15	121.7 (3)
C9—O4—H4O	109.5	C13—C14—H14	119.2
C12—O5—C16	117.7 (3)	C15—C14—H14	119.2
C8—N1—C17	119.4 (2)	C14—C15—C10	119.1 (3)
C8—N1—S1	115.7 (2)	C14—C15—H15	120.4
C17—N1—S1	118.9 (2)	C10—C15—H15	120.4
C2—C1—C6	121.7 (3)	O5—C16—H16A	109.5
C2—C1—S1	119.7 (3)	O5—C16—H16B	109.5
C6—C1—S1	118.6 (2)	H16A—C16—H16B	109.5
C1—C2—C3	119.1 (3)	O5—C16—H16C	109.5
C1—C2—H2	120.4	H16A—C16—H16C	109.5
C3—C2—H2	120.4	H16B—C16—H16C	109.5
C4—C3—C2	120.3 (3)	N1—C17—C18	114.1 (3)
C4—C3—H3	119.8	N1—C17—H17A	108.7
C2—C3—H3	119.8	C18—C17—H17A	108.7
C3—C4—C5	120.1 (3)	N1—C17—H17B	108.7
C3—C4—H4	120.0	C18—C17—H17B	108.7
C5—C4—H4	120.0	H17A—C17—H17B	107.6
C6—C5—C4	121.0 (3)	O6—C18—C19	120.8 (3)
C6—C5—H5	119.5	O6—C18—C17	120.0 (3)
C4—C5—H5	119.5	C19—C18—C17	119.2 (3)
C5—C6—C1	117.8 (3)	C20—C19—C24	119.3 (3)
C5—C6—C7	120.0 (3)	C20—C19—C18	122.9 (3)
C1—C6—C7	122.1 (3)	C24—C19—C18	117.7 (3)
O3—C7—C8	121.8 (3)	C21—C20—C19	120.2 (3)
O3—C7—C6	117.0 (3)	C21—C20—H20	119.9
C8—C7—C6	121.0 (3)	C19—C20—H20	119.9
C9—C8—C7	120.1 (3)	C22—C21—C20	120.1 (3)
C9—C8—N1	121.2 (3)	C22—C21—H21	120.0
C7—C8—N1	118.7 (3)	C20—C21—H21	120.0
O4—C9—C8	118.9 (3)	C21—C22—C23	120.3 (3)
O4—C9—C10	113.9 (3)	C21—C22—H22	119.8
C8—C9—C10	127.2 (3)	C23—C22—H22	119.8
C11—C10—C15	119.4 (3)	C24—C23—C22	119.5 (3)
C11—C10—C9	117.7 (3)	C24—C23—H23	120.2
C15—C10—C9	122.7 (3)	C22—C23—H23	120.2
C12—C11—C10	120.4 (3)	C23—C24—C19	120.5 (3)
C12—C11—H11	119.8	C23—C24—H24	119.8
C10—C11—H11	119.8	C19—C24—H24	119.8
O5—C12—C13	123.9 (3)

O2—S1—N1—C8	−166.6 (2)	N1—C8—C9—O4	−172.9 (3)
O1—S1—N1—C8	63.6 (2)	C7—C8—C9—C10	−171.0 (3)
C1—S1—N1—C8	−50.0 (3)	N1—C8—C9—C10	7.8 (5)
O2—S1—N1—C17	−13.9 (3)	O4—C9—C10—C11	18.6 (4)
O1—S1—N1—C17	−143.8 (2)	C8—C9—C10—C11	−162.1 (3)
C1—S1—N1—C17	102.6 (2)	O4—C9—C10—C15	−156.3 (3)
O2—S1—C1—C2	−40.4 (3)	C8—C9—C10—C15	23.0 (5)
O1—S1—C1—C2	90.4 (3)	C15—C10—C11—C12	−0.4 (5)
N1—S1—C1—C2	−155.1 (3)	C9—C10—C11—C12	−175.5 (3)
O2—S1—C1—C6	140.3 (2)	C16—O5—C12—C13	5.5 (5)
O1—S1—C1—C6	−88.9 (3)	C16—O5—C12—C11	−174.2 (3)
N1—S1—C1—C6	25.6 (3)	C10—C11—C12—O5	179.7 (3)
C6—C1—C2—C3	−0.1 (5)	C10—C11—C12—C13	0.0 (5)
S1—C1—C2—C3	−179.4 (3)	O5—C12—C13—C14	−179.1 (3)
C1—C2—C3—C4	−0.9 (5)	C11—C12—C13—C14	0.6 (5)
C2—C3—C4—C5	0.7 (6)	C12—C13—C14—C15	−0.8 (6)
C3—C4—C5—C6	0.5 (5)	C13—C14—C15—C10	0.4 (6)
C4—C5—C6—C1	−1.4 (5)	C11—C10—C15—C14	0.2 (5)
C4—C5—C6—C7	176.3 (3)	C9—C10—C15—C14	175.1 (3)
C2—C1—C6—C5	1.2 (5)	C8—N1—C17—C18	69.8 (4)
S1—C1—C6—C5	−179.5 (2)	S1—N1—C17—C18	−81.8 (3)
C2—C1—C6—C7	−176.4 (3)	N1—C17—C18—O6	−5.8 (4)
S1—C1—C6—C7	2.9 (4)	N1—C17—C18—C19	172.8 (3)
C5—C6—C7—O3	−15.2 (4)	O6—C18—C19—C20	−179.7 (3)
C1—C6—C7—O3	162.4 (3)	C17—C18—C19—C20	1.7 (5)
C5—C6—C7—C8	169.9 (3)	O6—C18—C19—C24	4.3 (5)
C1—C6—C7—C8	−12.5 (5)	C17—C18—C19—C24	−174.3 (3)
O3—C7—C8—C9	−9.3 (5)	C24—C19—C20—C21	2.7 (5)
C6—C7—C8—C9	165.3 (3)	C18—C19—C20—C21	−173.2 (3)
O3—C7—C8—N1	171.9 (3)	C19—C20—C21—C22	−1.5 (5)
C6—C7—C8—N1	−13.5 (4)	C20—C21—C22—C23	−1.3 (5)
C17—N1—C8—C9	76.6 (4)	C21—C22—C23—C24	2.8 (5)
S1—N1—C8—C9	−130.9 (3)	C22—C23—C24—C19	−1.6 (5)
C17—N1—C8—C7	−104.6 (3)	C20—C19—C24—C23	−1.2 (5)
S1—N1—C8—C7	47.9 (3)	C18—C19—C24—C23	175.0 (3)
C7—C8—C9—O4	8.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.95	2.59	3.281 (4)	130
C11—H11···O1ⁱⁱ	0.95	2.53	3.371 (4)	148
C16—H16B···O6ⁱⁱⁱ	0.98	2.64	3.246 (4)	120
C24—H24···O5^iv	0.95	2.57	3.508 (4)	167
O4—H4O···O3	0.84	1.71	2.478 (3)	151
C15—H15···N1	0.95	2.38	2.972 (4)	120
C17—H17B···O2	0.99	2.39	2.800 (4)	104

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, −y+1, z−1/2; (iv) −x+1/2, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉NO₆S
M_r	449.46
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	173
a, b, c (Å)	17.9615 (5), 11.2633 (3), 19.5904 (6)
V (Å³)	3963.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.14 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.971, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8340, 4543, 3198
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.133, 1.10
No. of reflections	4543
No. of parameters	291
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + 10.1913P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.49

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.95	2.59	3.281 (4)	129.9
C11—H11···O1ⁱⁱ	0.95	2.53	3.371 (4)	148.2
C16—H16B···O6ⁱⁱⁱ	0.98	2.64	3.246 (4)	120.3
C24—H24···O5^iv	0.95	2.57	3.508 (4)	167.3
O4—H4O···O3	0.84	1.71	2.478 (3)	150.5
C15—H15···N1	0.95	2.38	2.972 (4)	119.9

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, −y+1, z−1/2; (iv) −x+1/2, −y+1, z+1/2.

Acknowledgements

The authors are grateful to the Higher Education Commission, Pakistan, and the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

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