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

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

doi:10.1107/S160053681104966X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3445

https://doi.org/10.1107/S160053681104966X

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Methyl 4-hydroxy-1,1-dioxo-2-(2-phenylethyl)-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 (H. H. Campus), Gujrat 50700, 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 St NW, Washington, DC 20057, USA
^*Correspondence e-mail: mnachemist@hotmail.com

(Received 17 November 2011; accepted 21 November 2011; online 25 November 2011)

In the title compound, C₁₈H₁₇NO₅S, the thiazine ring adopts a half-chair conformation and the dihedral angle between the aromatic rings is 79.41 (6)°. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring. In the crystal, molecules are linked by weak C—H⋯O interactions resulting in infinite sheets along the b and c axes.

Related literature

For related structures, see: Arshad et al. (2011a ); Ahmad et al. (2010 ); Khalid et al. (2010 ). For further synthetic details, see: Arshad et al. (2011b ). For graph-set notation, see: Bernstein, et al. (1995 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₈H₁₇NO₅S
M_r = 359.39
Monoclinic, P 2₁ /c
a = 9.018 (2) Å
b = 19.026 (4) Å
c = 10.193 (2) Å
β = 106.441 (3)°
V = 1677.3 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 100 K
0.37 × 0.23 × 0.08 mm

Data collection

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.922, T_max = 0.982
19773 measured reflections
4066 independent reflections
2735 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.116
S = 1.01
4066 reflections
230 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.95	2.55	3.391 (3)	147
C17—H17⋯O2ⁱⁱ	0.95	2.53	3.205 (3)	128
C18—H18⋯O4ⁱⁱⁱ	0.95	2.49	3.308 (3)	145
O1—H1⋯O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x-1, y, z-1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: X-SEED (Barbour, 2001 ), WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681104966X/hb6520sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104966X/hb6520Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104966X/hb6520Isup3.cml

checkCIF report

Comment top

Benzothiazines molecules are well explored for their crystallographic studies (Arshad et al. 2011a), (Ahmad et al. 2010), (Khalid et al. 2010).

In the title compound, the nitrogen atom of methyl-4-hydroxy-2H-1, 2-benzothiazine-3-carboxylate 1,1-dioxide was alkylated with phenylethyl group. The thiazine ring (with root mean square deviation = 0.210Å) is oriented at dihedral angle of 13.12 (11)° with respect to the aromatic ring (C1—C6) and the S1 & N1 atoms showed deviations from the least square plane by 0.3121 (10)Å and -0.3310 (12)Å, respectively. The thiazine ring adopts a half chair conformation with puckering amplitude Q = 0.5160 (16)Å θ = 63.6 (2)°, φ = 26.3 (2)° (Cremer & Pople, 1975). The phenyl ring (C13—C17) is oriented at dihedral angle of 79.41 (6)° and 66.53 (5)° with respect to the aromatic (C1—C6) and thiazine rings respectively. The intramolecular O–H···O interaction observed and generates an almost planer S(6) ring (Bernstein, et al., 1995) with the r.m.s deviaton of 0.0131Å and produces dihedral angles of 16.02 (33)° & 15.87 (32)° with respect to the thiazine and aromatic (C1—C6) rings respectively.

Weak hydrogen bonding interactions of C—H···O type connect the molecules. The interaction C2—H2···O3 resulted in the formation of dimers which are further linked along b and c axes (Fig.2. Tab.1).

Related literature top

For related structures, see: Arshad et al. (2011a); Ahmad et al. (2010); Khalid et al. (2010). For further synthetic details, see: Arshad et al. (2011b). For graph-set notation, see: Bernstein, et al. (1995). For ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesised according to literature procedure (Arshad et al. 2011b) and crystalized in methanol under slow evaporation to yield colourless blocks.

Structure description top

Benzothiazines molecules are well explored for their crystallographic studies (Arshad et al. 2011a), (Ahmad et al. 2010), (Khalid et al. 2010).

For related structures, see: Arshad et al. (2011a); Ahmad et al. (2010); Khalid et al. (2010). For further synthetic details, see: Arshad et al. (2011b). For graph-set notation, see: Bernstein, et al. (1995). For ring conformations, see: Cremer & Pople (1975).

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); software used to prepare material for publication: X-SEED (Barbour, 2001), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The labeled ortep diagram of (I) for which thermal ellipsoids were drawn at 50% probability level.
	Fig. 2. Unit cell packing for (I) showing the hydrogen bondings using dashed lines.

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

Crystal data top

C₁₈H₁₇NO₅S	F(000) = 752
M_r = 359.39	D_x = 1.423 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2258 reflections
a = 9.018 (2) Å	θ = 2.3–22.9°
b = 19.026 (4) Å	µ = 0.22 mm⁻¹
c = 10.193 (2) Å	T = 100 K
β = 106.441 (3)°	Block, colorless
V = 1677.3 (7) Å³	0.37 × 0.23 × 0.08 mm
Z = 4

Data collection top

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector	4066 independent reflections
Radiation source: fine-focus sealed tube	2735 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
φ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.922, T_max = 0.982	k = −25→25
19773 measured reflections	l = −13→13

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0449P)² + 0.2677P] where P = (F_o² + 2F_c²)/3
4066 reflections	(Δ/σ)_max < 0.001
230 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

C₁₈H₁₇NO₅S	V = 1677.3 (7) Å³
M_r = 359.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.018 (2) Å	µ = 0.22 mm⁻¹
b = 19.026 (4) Å	T = 100 K
c = 10.193 (2) Å	0.37 × 0.23 × 0.08 mm
β = 106.441 (3)°

Data collection top

Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector	4066 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2735 reflections with I > 2σ(I)
T_min = 0.922, T_max = 0.982	R_int = 0.094
19773 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.38 e Å⁻³
4066 reflections	Δρ_min = −0.44 e Å⁻³
230 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.29319 (6)	0.07784 (3)	0.51969 (5)	0.01673 (14)
O3	0.30860 (16)	0.00885 (8)	0.46983 (15)	0.0214 (4)
O5	−0.10038 (17)	0.12689 (8)	0.61803 (15)	0.0231 (4)
O1	0.13070 (18)	0.28877 (8)	0.48807 (17)	0.0251 (4)
O4	−0.07394 (18)	0.24350 (9)	0.60086 (17)	0.0276 (4)
N1	0.10892 (18)	0.09548 (9)	0.48635 (17)	0.0154 (4)
O2	0.36535 (16)	0.09408 (8)	0.65995 (14)	0.0227 (4)
C1	0.3551 (2)	0.14133 (12)	0.4212 (2)	0.0170 (5)
C7	0.1578 (2)	0.22064 (12)	0.4703 (2)	0.0182 (5)
C8	0.0779 (2)	0.16750 (11)	0.5085 (2)	0.0177 (5)
C5	0.3377 (2)	0.26007 (12)	0.3379 (2)	0.0220 (5)
H5	0.2933	0.3057	0.3300	0.026*
C9	−0.0383 (2)	0.18329 (12)	0.5789 (2)	0.0207 (5)
C6	0.2849 (2)	0.20757 (11)	0.4087 (2)	0.0180 (5)
C2	0.4731 (2)	0.12640 (12)	0.3629 (2)	0.0214 (5)
H2	0.5193	0.0811	0.3720	0.026*
C17	−0.3703 (2)	0.07609 (13)	−0.0561 (2)	0.0235 (5)
H17	−0.4494	0.1074	−0.1035	0.028*
C18	−0.2463 (2)	0.10137 (12)	0.0471 (2)	0.0209 (5)
H18	−0.2404	0.1500	0.0694	0.025*
C11	−0.0022 (2)	0.05922 (11)	0.3704 (2)	0.0170 (5)
H11A	−0.1082	0.0670	0.3773	0.020*
H11B	0.0185	0.0081	0.3786	0.020*
C3	0.5220 (3)	0.17932 (13)	0.2911 (2)	0.0270 (6)
H3	0.6021	0.1701	0.2496	0.032*
C15	−0.2653 (3)	−0.03981 (13)	−0.0196 (2)	0.0247 (5)
H15	−0.2717	−0.0884	−0.0421	0.030*
C4	0.4549 (3)	0.24549 (13)	0.2793 (2)	0.0257 (5)
H4	0.4901	0.2813	0.2303	0.031*
C12	0.0052 (2)	0.08358 (12)	0.2302 (2)	0.0225 (5)
H12A	0.0047	0.1356	0.2273	0.027*
H12B	0.1029	0.0671	0.2146	0.027*
C14	−0.1420 (3)	−0.01493 (13)	0.0835 (2)	0.0249 (5)
H14	−0.0642	−0.0467	0.1314	0.030*
C13	−0.1300 (2)	0.05577 (12)	0.1181 (2)	0.0196 (5)
C16	−0.3799 (3)	0.00572 (13)	−0.0903 (2)	0.0239 (5)
H16	−0.4643	−0.0113	−0.1619	0.029*
C10	−0.2150 (3)	0.13972 (14)	0.6903 (3)	0.0314 (6)
H10A	−0.2992	0.1682	0.6329	0.047*
H10B	−0.1669	0.1649	0.7756	0.047*
H10C	−0.2564	0.0948	0.7111	0.047*
H1	0.057 (3)	0.2878 (14)	0.534 (3)	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0166 (2)	0.0155 (3)	0.0161 (3)	0.0009 (2)	0.0015 (2)	0.0007 (2)
O3	0.0204 (7)	0.0153 (8)	0.0269 (8)	0.0031 (6)	0.0042 (7)	−0.0005 (7)
O5	0.0245 (8)	0.0217 (9)	0.0271 (9)	−0.0026 (7)	0.0138 (7)	−0.0042 (7)
O1	0.0285 (9)	0.0147 (9)	0.0347 (10)	0.0009 (7)	0.0130 (8)	−0.0018 (7)
O4	0.0287 (9)	0.0193 (9)	0.0370 (10)	0.0027 (7)	0.0127 (8)	−0.0047 (7)
N1	0.0155 (8)	0.0138 (10)	0.0158 (9)	0.0005 (7)	0.0025 (7)	0.0009 (7)
O2	0.0237 (8)	0.0235 (9)	0.0171 (8)	−0.0012 (7)	−0.0005 (7)	0.0002 (7)
C1	0.0154 (9)	0.0186 (12)	0.0136 (10)	−0.0025 (9)	−0.0016 (8)	−0.0005 (9)
C7	0.0188 (10)	0.0161 (12)	0.0172 (11)	0.0004 (9)	0.0009 (9)	−0.0006 (9)
C8	0.0190 (10)	0.0174 (12)	0.0152 (10)	0.0025 (9)	0.0026 (9)	−0.0016 (9)
C5	0.0237 (11)	0.0182 (12)	0.0211 (12)	−0.0006 (9)	0.0018 (10)	0.0023 (9)
C9	0.0182 (10)	0.0210 (13)	0.0204 (11)	−0.0007 (9)	0.0015 (9)	−0.0017 (10)
C6	0.0175 (10)	0.0179 (12)	0.0158 (11)	−0.0035 (9)	0.0002 (9)	−0.0018 (9)
C2	0.0190 (10)	0.0219 (13)	0.0209 (11)	−0.0003 (9)	0.0020 (9)	−0.0029 (9)
C17	0.0217 (11)	0.0287 (14)	0.0186 (11)	0.0019 (10)	0.0035 (9)	0.0039 (10)
C18	0.0259 (11)	0.0193 (12)	0.0177 (11)	−0.0029 (10)	0.0067 (10)	−0.0004 (9)
C11	0.0162 (10)	0.0177 (12)	0.0160 (10)	−0.0016 (8)	0.0030 (9)	−0.0007 (8)
C3	0.0223 (11)	0.0353 (16)	0.0248 (12)	−0.0029 (10)	0.0089 (10)	−0.0019 (11)
C15	0.0301 (12)	0.0205 (13)	0.0243 (12)	0.0002 (10)	0.0089 (10)	−0.0030 (10)
C4	0.0256 (12)	0.0267 (14)	0.0245 (13)	−0.0067 (10)	0.0066 (10)	0.0046 (10)
C12	0.0227 (10)	0.0248 (13)	0.0182 (11)	−0.0036 (10)	0.0030 (9)	0.0031 (10)
C14	0.0243 (11)	0.0253 (14)	0.0234 (12)	0.0041 (10)	0.0040 (10)	0.0020 (10)
C13	0.0208 (11)	0.0247 (13)	0.0136 (10)	−0.0026 (9)	0.0053 (9)	0.0001 (9)
C16	0.0237 (11)	0.0287 (14)	0.0170 (11)	−0.0045 (10)	0.0017 (9)	−0.0036 (10)
C10	0.0303 (12)	0.0354 (16)	0.0360 (14)	−0.0049 (11)	0.0215 (12)	−0.0120 (12)

Geometric parameters (Å, º) top

S1—O2	1.4270 (15)	C17—C18	1.386 (3)
S1—O3	1.4285 (16)	C17—H17	0.9500
S1—N1	1.6339 (17)	C18—C13	1.395 (3)
S1—C1	1.760 (2)	C18—H18	0.9500
O5—C9	1.323 (3)	C11—C12	1.521 (3)
O5—C10	1.449 (3)	C11—H11A	0.9900
O1—C7	1.341 (3)	C11—H11B	0.9900
O1—H1	0.92 (3)	C3—C4	1.387 (3)
O4—C9	1.227 (3)	C3—H3	0.9500
N1—C8	1.429 (3)	C15—C14	1.379 (3)
N1—C11	1.485 (3)	C15—C16	1.384 (3)
C1—C2	1.387 (3)	C15—H15	0.9500
C1—C6	1.400 (3)	C4—H4	0.9500
C7—C8	1.361 (3)	C12—C13	1.511 (3)
C7—C6	1.475 (3)	C12—H12A	0.9900
C8—C9	1.459 (3)	C12—H12B	0.9900
C5—C4	1.382 (3)	C14—C13	1.387 (3)
C5—C6	1.392 (3)	C14—H14	0.9500
C5—H5	0.9500	C16—H16	0.9500
C2—C3	1.389 (3)	C10—H10A	0.9800
C2—H2	0.9500	C10—H10B	0.9800
C17—C16	1.380 (3)	C10—H10C	0.9800

O2—S1—O3	119.52 (9)	C13—C18—H18	119.9
O2—S1—N1	108.21 (9)	N1—C11—C12	114.02 (17)
O3—S1—N1	108.08 (9)	N1—C11—H11A	108.7
O2—S1—C1	107.13 (9)	C12—C11—H11A	108.7
O3—S1—C1	110.45 (10)	N1—C11—H11B	108.7
N1—S1—C1	102.04 (9)	C12—C11—H11B	108.7
C9—O5—C10	116.10 (18)	H11A—C11—H11B	107.6
C7—O1—H1	103.7 (17)	C4—C3—C2	120.5 (2)
C8—N1—C11	116.93 (16)	C4—C3—H3	119.7
C8—N1—S1	113.41 (13)	C2—C3—H3	119.7
C11—N1—S1	119.16 (14)	C14—C15—C16	120.3 (2)
C2—C1—C6	121.8 (2)	C14—C15—H15	119.9
C2—C1—S1	120.63 (17)	C16—C15—H15	119.9
C6—C1—S1	117.50 (16)	C5—C4—C3	120.9 (2)
O1—C7—C8	123.2 (2)	C5—C4—H4	119.6
O1—C7—C6	114.46 (19)	C3—C4—H4	119.6
C8—C7—C6	122.3 (2)	C13—C12—C11	111.30 (18)
C7—C8—N1	121.54 (19)	C13—C12—H12A	109.4
C7—C8—C9	120.0 (2)	C11—C12—H12A	109.4
N1—C8—C9	118.38 (19)	C13—C12—H12B	109.4
C4—C5—C6	119.7 (2)	C11—C12—H12B	109.4
C4—C5—H5	120.1	H12A—C12—H12B	108.0
C6—C5—H5	120.1	C15—C14—C13	121.0 (2)
O4—C9—O5	123.2 (2)	C15—C14—H14	119.5
O4—C9—C8	122.9 (2)	C13—C14—H14	119.5
O5—C9—C8	113.92 (19)	C14—C13—C18	118.5 (2)
C5—C6—C1	118.8 (2)	C14—C13—C12	121.3 (2)
C5—C6—C7	121.3 (2)	C18—C13—C12	120.1 (2)
C1—C6—C7	119.92 (19)	C17—C16—C15	119.4 (2)
C1—C2—C3	118.3 (2)	C17—C16—H16	120.3
C1—C2—H2	120.8	C15—C16—H16	120.3
C3—C2—H2	120.8	O5—C10—H10A	109.5
C16—C17—C18	120.5 (2)	O5—C10—H10B	109.5
C16—C17—H17	119.8	H10A—C10—H10B	109.5
C18—C17—H17	119.8	O5—C10—H10C	109.5
C17—C18—C13	120.3 (2)	H10A—C10—H10C	109.5
C17—C18—H18	119.9	H10B—C10—H10C	109.5

O2—S1—N1—C8	59.99 (16)	C4—C5—C6—C7	−178.7 (2)
O3—S1—N1—C8	−169.24 (14)	C2—C1—C6—C5	−1.3 (3)
C1—S1—N1—C8	−52.79 (16)	S1—C1—C6—C5	176.40 (16)
O2—S1—N1—C11	−156.23 (15)	C2—C1—C6—C7	178.87 (19)
O3—S1—N1—C11	−25.46 (18)	S1—C1—C6—C7	−3.5 (3)
C1—S1—N1—C11	90.99 (17)	O1—C7—C6—C5	−18.7 (3)
O2—S1—C1—C2	99.50 (18)	C8—C7—C6—C5	162.8 (2)
O3—S1—C1—C2	−32.19 (19)	O1—C7—C6—C1	161.14 (18)
N1—S1—C1—C2	−146.92 (17)	C8—C7—C6—C1	−17.4 (3)
O2—S1—C1—C6	−78.19 (17)	C6—C1—C2—C3	0.3 (3)
O3—S1—C1—C6	150.11 (15)	S1—C1—C2—C3	−177.31 (16)
N1—S1—C1—C6	35.39 (18)	C16—C17—C18—C13	−0.4 (3)
O1—C7—C8—N1	179.24 (18)	C8—N1—C11—C12	71.0 (2)
C6—C7—C8—N1	−2.4 (3)	S1—N1—C11—C12	−71.6 (2)
O1—C7—C8—C9	−3.3 (3)	C1—C2—C3—C4	0.5 (3)
C6—C7—C8—C9	175.06 (18)	C6—C5—C4—C3	−0.6 (3)
C11—N1—C8—C7	−103.1 (2)	C2—C3—C4—C5	−0.4 (3)
S1—N1—C8—C7	41.5 (2)	N1—C11—C12—C13	−168.72 (18)
C11—N1—C8—C9	79.4 (2)	C16—C15—C14—C13	−0.1 (3)
S1—N1—C8—C9	−136.00 (16)	C15—C14—C13—C18	0.5 (3)
C10—O5—C9—O4	−0.2 (3)	C15—C14—C13—C12	−179.6 (2)
C10—O5—C9—C8	179.15 (18)	C17—C18—C13—C14	−0.2 (3)
C7—C8—C9—O4	3.4 (3)	C17—C18—C13—C12	179.85 (19)
N1—C8—C9—O4	−179.04 (19)	C11—C12—C13—C14	−70.4 (3)
C7—C8—C9—O5	−175.93 (18)	C11—C12—C13—C18	109.5 (2)
N1—C8—C9—O5	1.6 (3)	C18—C17—C16—C15	0.8 (3)
C4—C5—C6—C1	1.4 (3)	C14—C15—C16—C17	−0.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.95	2.55	3.391 (3)	147
C17—H17···O2ⁱⁱ	0.95	2.53	3.205 (3)	128
C18—H18···O4ⁱⁱⁱ	0.95	2.49	3.308 (3)	145
O1—H1···O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇NO₅S
M_r	359.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.018 (2), 19.026 (4), 10.193 (2)
β (°)	106.441 (3)
V (Å³)	1677.3 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.37 × 0.23 × 0.08

Data collection
Diffractometer	Bruker SMART 1K diffractometer with a Bruker APEXII CCD detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.922, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	19773, 4066, 2735
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.116, 1.01
No. of reflections	4066
No. of parameters	230
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.44

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), 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
C2—H2···O3ⁱ	0.95	2.55	3.391 (3)	147
C17—H17···O2ⁱⁱ	0.95	2.53	3.205 (3)	128
C18—H18···O4ⁱⁱⁱ	0.95	2.49	3.308 (3)	145
O1—H1···O4	0.92 (3)	1.74 (3)	2.583 (2)	152 (3)

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

Acknowledgements

MNA acknowledges the HEC for providing a fellowship under the International Research Support Initiative Program (IRSIP).

References

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