Ethyl 2-[N-(2-Formyl­phen­yl)benzene­sulfonamido]acetate

Seshadri, P.R.; Balakrishnan, B.; Ilangovan, K.; Sureshbabu, R.; Mohanakrishnan, A.K.

doi:10.1107/S1600536809004413

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o530

doi:10.1107/S1600536809004413

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Ethyl 2-[N-(2-Formylphenyl)benzenesulfonamido]acetate

P. R. Seshadri,^a ^* B. Balakrishnan,^b K. Ilangovan,^c R. Sureshbabu ^d and A. K. Mohanakrishnan ^d

^aPG and Research Department of Physics, Agurchand Manmull Jain College, Chennai 600 114, India, ^bDepartment of Physics, P. T. Lee Chengalvaraya Naicker College of Engineering and Technology, Kancheepuram 631 502, India, ^cPG and Research Department of Physics, RKM Vivekananda College, Chennai 600 004, India, and ^dDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: seshadri_pr@yahoo.com

(Received 20 January 2009; accepted 6 February 2009; online 18 February 2009)

In the title compound, C₁₇H₁₇NO₅S, the N atom is sp³-hybridized and the S atom has a distorted tetrahedral configuration. The dihedral angle between the two aromatic rings is 30.0 (1)°, and that between the ethyl acetate group and the formylphenyl ring is 77.4 (1)°. The molecules are linked into chains along [100] by C—H⋯O hydrogen bonds and the chains are linked via C—H⋯π interactions.

Related literature

For the biological properties of sulfonamide derivatives, see: Brown (1971 ); Nieto et al. (2005 ); Pomarnacka & Kozlarska-Kedra (2003 ). For related structures, see: Cameron et al. (1975 ); Cotton & Stokley (1970 ); Usha et al. (2005 ); Zhu et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₇NO₅S
M_r = 347.38
Orthorhombic, P 2₁ 2₁ 2₁
a = 11.3442 (5) Å
b = 11.7731 (6) Å
c = 12.7809 (6) Å
V = 1706.97 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.948, T_max = 0.958
10886 measured reflections
4104 independent reflections
3294 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.092
S = 0.95
4104 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1714 Friedel pairs
Flack parameter: −0.05 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O3ⁱ	0.93	2.57	3.218 (3)	127
C16—H16B⋯Cg1ⁱⁱ	0.97	2.73	3.605 (3)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of C1–C6 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004413/ci2763sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004413/ci2763Isup2.hkl

checkCIF report

Comment top

Sulfonamide derivates are well known drugs and are used to control diseases caused by bacterial infections. The antibacterial action of this group of drugs is exerted by the complete inhibition of dihydropteroate synthase enzyme towards the p-amino benzonate (Brown, 1971). Benzene sulfonamide derivatives are known to exhibit anticancer and HIV activities (Pomarnacka & Kozlarska-Kedra, 2003) and antibacterial activities (Nieto et al., 2005). In view of this medicinal importance, the crystal structure determination of the title compound (Fig.1) was carried out and the results are presented here.

The angles around atom S1 deviate significantly from the regular tetrahedral value, with the largest deviation of 120.6 (1)° for O1—S1—O2 angle. This may be due to non-bonding interactions between S═O bonds (Cotton & Stokley, 1970). The sulfonyl oxygen O1 is syn-clinal and O2 is syn-periplanar to the phenyl ring. The dihedral angle between the best planes through the ethylacetate group (O3/O4/C14/C15/C16) and formyl phenyl ring (C7-C12) is 77.4 (1)°. The aldyhyde group is slightly twisted from the plane of the ring to which it is attached as evidenced by the torsion angle C11—C12—C13—O5 of -8.5 (3)°. The relative orientations of C/N/S and O/S/O planes is determined by the hybridization nature of atom N1. The angles between planes C14/N1/S1 and O1/S1/O2 and between C7/N1/S1 and O1/S1/O2 planes are 59° and 56°, respectively. These values are close to 58° reported for sp³ N atoms [87° for sp² N atoms] (Cameron et al., 1975). The geometrical parameters agree well with those reported for related sulfonamide structures (Usha et al., 2005; Zhu et al., 2008).

In addition to van der Waals interactions, the crystal structure is stabilized by C—H···O and C—H···π interactions (Table 1).

Related literature top

For the biological properties of sulfonamide derivatives, see: Brown (1971); Nieto et al. (2005); Pomarnacka & Kozlarska-Kedra (2003). For related structures, see: Cameron et al. (1975); Cotton & Stokley (1970); Usha et al. (2005); Zhu et al. (2008).

Experimental top

N-(2-Formylphenyl)benzene sulfonamide (1.7 g, 6.5 mmol) was dissolved in dimethyl acetamide (25 ml). To this potassium carbonate (2.25 g, 16.2 mmol) and ethyl bromoacetate (0.86 ml, 7.8 mmol) were added. The reaction mixture was stirred at room temperature for 4 h. It was then poured over curshed ice (100 g) cotaining 5 ml of concentrated HCl. The precipitated solid was filtered off and the title compound was recrystallized from methanol. Yield = 1 g (45%) and m.p = 381 K.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Ethyl 2-[N-(2-Formylphenyl)benzenesulfonamido]acetate top

Crystal data top

C₁₇H₁₇NO₅S	F(000) = 728
M_r = 347.38	D_x = 1.352 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4197 reflections
a = 11.3442 (5) Å	θ = 2.4–28.2°
b = 11.7731 (6) Å	µ = 0.22 mm⁻¹
c = 12.7809 (6) Å	T = 293 K
V = 1706.97 (14) Å³	Block, colourless
Z = 4	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4104 independent reflections
Radiation source: fine-focus sealed tube	3294 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 28.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −15→10
T_min = 0.948, T_max = 0.958	k = −13→15
10886 measured reflections	l = −17→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0478P)² + 0.2327P] where P = (F_o² + 2F_c²)/3
S = 0.95	(Δ/σ)_max = 0.001
4104 reflections	Δρ_max = 0.31 e Å⁻³
218 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1714 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.05 (7)

Crystal data top

C₁₇H₁₇NO₅S	V = 1706.97 (14) Å³
M_r = 347.38	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 11.3442 (5) Å	µ = 0.22 mm⁻¹
b = 11.7731 (6) Å	T = 293 K
c = 12.7809 (6) Å	0.25 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII area-detector diffractometer	4104 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3294 reflections with I > 2σ(I)
T_min = 0.948, T_max = 0.958	R_int = 0.022
10886 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.31 e Å⁻³
S = 0.95	Δρ_min = −0.23 e Å⁻³
4104 reflections	Absolute structure: Flack (1983), 1714 Friedel pairs
218 parameters	Absolute structure parameter: −0.05 (7)
0 restraints

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	0.53613 (4)	0.77486 (4)	0.23609 (3)	0.04875 (13)
N1	0.57693 (13)	0.74419 (13)	0.35602 (12)	0.0458 (4)
O1	0.58109 (13)	0.88549 (13)	0.21568 (11)	0.0627 (4)
O2	0.56980 (14)	0.68125 (16)	0.17264 (13)	0.0734 (5)
O3	0.75001 (14)	0.59352 (14)	0.41673 (16)	0.0749 (5)
O4	0.61531 (12)	0.47431 (12)	0.48118 (11)	0.0576 (4)
O5	0.89664 (14)	0.90059 (16)	0.34906 (17)	0.0833 (6)
C1	0.38089 (15)	0.77875 (16)	0.23788 (14)	0.0433 (4)
C2	0.3190 (2)	0.68510 (18)	0.20483 (17)	0.0559 (5)
H2	0.3585	0.6215	0.1798	0.067*
C3	0.1975 (2)	0.6866 (2)	0.2093 (2)	0.0693 (6)
H3	0.1546	0.6237	0.1870	0.083*
C4	0.1400 (2)	0.7802 (2)	0.24649 (19)	0.0705 (6)
H4	0.0581	0.7806	0.2496	0.085*
C5	0.2021 (2)	0.8738 (2)	0.27923 (18)	0.0660 (6)
H5A	0.1622	0.9371	0.3046	0.079*
C6	0.32367 (19)	0.87418 (18)	0.27450 (16)	0.0547 (5)
H6	0.3663	0.9376	0.2956	0.066*
C7	0.60070 (16)	0.83376 (15)	0.42938 (14)	0.0430 (4)
C8	0.51433 (19)	0.86705 (19)	0.49933 (16)	0.0585 (5)
H8	0.4400	0.8338	0.4967	0.070*
C9	0.5382 (3)	0.9487 (2)	0.57219 (17)	0.0717 (6)
H9	0.4799	0.9708	0.6192	0.086*
C10	0.6472 (3)	0.9983 (2)	0.57653 (17)	0.0713 (7)
H10	0.6630	1.0529	0.6273	0.086*
C11	0.7342 (2)	0.96779 (17)	0.50592 (16)	0.0585 (5)
H11	0.8075	1.0030	0.5082	0.070*
C12	0.71158 (17)	0.88403 (15)	0.43139 (14)	0.0444 (4)
C13	0.80492 (18)	0.85128 (18)	0.35747 (16)	0.0525 (5)
H13	0.7919	0.7886	0.3148	0.063*
C14	0.54423 (19)	0.63341 (16)	0.39786 (16)	0.0529 (4)
H14A	0.5022	0.5908	0.3447	0.064*
H14B	0.4917	0.6437	0.4570	0.064*
C15	0.65033 (19)	0.56723 (17)	0.43213 (15)	0.0485 (4)
C16	0.7055 (2)	0.39708 (18)	0.51686 (18)	0.0642 (6)
H16A	0.7631	0.4372	0.5591	0.077*
H16B	0.7457	0.3630	0.4577	0.077*
C17	0.6461 (3)	0.3085 (2)	0.5799 (3)	0.1089 (12)
H17A	0.6111	0.3426	0.6406	0.163*
H17B	0.7027	0.2525	0.6012	0.163*
H17C	0.5858	0.2729	0.5386	0.163*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0432 (2)	0.0579 (3)	0.0451 (2)	0.0008 (2)	0.0015 (2)	−0.0029 (2)
N1	0.0426 (8)	0.0414 (8)	0.0535 (8)	0.0000 (7)	−0.0064 (6)	0.0046 (7)
O1	0.0607 (9)	0.0714 (10)	0.0559 (8)	−0.0149 (8)	−0.0027 (7)	0.0166 (7)
O2	0.0594 (10)	0.0918 (12)	0.0692 (9)	0.0096 (9)	0.0088 (7)	−0.0290 (9)
O3	0.0449 (9)	0.0622 (10)	0.1175 (14)	0.0016 (8)	−0.0120 (9)	0.0194 (9)
O4	0.0636 (9)	0.0468 (8)	0.0622 (8)	0.0010 (7)	−0.0076 (7)	0.0095 (7)
O5	0.0478 (9)	0.0929 (13)	0.1093 (14)	−0.0136 (9)	0.0124 (9)	−0.0077 (11)
C1	0.0411 (9)	0.0509 (10)	0.0380 (8)	0.0016 (8)	−0.0043 (7)	−0.0017 (9)
C2	0.0555 (13)	0.0491 (11)	0.0630 (12)	0.0033 (10)	−0.0050 (9)	−0.0037 (9)
C3	0.0548 (13)	0.0680 (14)	0.0852 (16)	−0.0116 (12)	−0.0057 (12)	−0.0013 (12)
C4	0.0466 (11)	0.0937 (18)	0.0712 (14)	0.0004 (13)	0.0025 (10)	0.0003 (14)
C5	0.0592 (13)	0.0776 (15)	0.0612 (13)	0.0218 (13)	−0.0023 (11)	−0.0129 (12)
C6	0.0576 (12)	0.0564 (12)	0.0502 (10)	0.0069 (10)	−0.0082 (9)	−0.0095 (9)
C7	0.0454 (10)	0.0408 (9)	0.0429 (9)	0.0049 (8)	−0.0035 (8)	0.0058 (8)
C8	0.0522 (12)	0.0656 (13)	0.0576 (11)	0.0071 (10)	0.0076 (9)	0.0062 (10)
C9	0.0859 (17)	0.0712 (14)	0.0579 (12)	0.0135 (15)	0.0170 (14)	−0.0028 (11)
C10	0.111 (2)	0.0521 (12)	0.0508 (12)	0.0063 (13)	−0.0067 (13)	−0.0087 (10)
C11	0.0719 (15)	0.0488 (11)	0.0547 (12)	−0.0025 (11)	−0.0150 (10)	0.0027 (9)
C12	0.0463 (10)	0.0420 (9)	0.0449 (9)	0.0045 (8)	−0.0050 (8)	0.0067 (8)
C13	0.0432 (11)	0.0538 (11)	0.0605 (12)	0.0035 (10)	−0.0014 (9)	0.0079 (9)
C14	0.0452 (11)	0.0452 (10)	0.0684 (11)	−0.0022 (10)	−0.0031 (10)	0.0073 (9)
C15	0.0523 (12)	0.0427 (10)	0.0505 (10)	−0.0004 (9)	−0.0091 (9)	−0.0037 (8)
C16	0.0804 (16)	0.0486 (11)	0.0635 (13)	0.0096 (11)	−0.0243 (11)	0.0018 (10)
C17	0.132 (3)	0.0725 (18)	0.122 (3)	−0.0193 (18)	−0.047 (2)	0.0430 (18)

Geometric parameters (Å, º) top

S1—O1	1.4229 (15)	C7—C8	1.383 (3)
S1—O2	1.4206 (16)	C7—C12	1.390 (3)
S1—N1	1.6414 (15)	C8—C9	1.365 (3)
S1—C1	1.7618 (18)	C8—H8	0.93
N1—C7	1.437 (2)	C9—C10	1.370 (4)
N1—C14	1.458 (2)	C9—H9	0.93
O3—C15	1.189 (2)	C10—C11	1.385 (3)
O4—C15	1.322 (2)	C10—H10	0.93
O4—C16	1.443 (2)	C11—C12	1.395 (3)
O5—C13	1.196 (3)	C11—H11	0.93
C1—C6	1.379 (3)	C12—C13	1.471 (3)
C1—C2	1.374 (3)	C13—H13	0.93
C2—C3	1.380 (3)	C14—C15	1.499 (3)
C2—H2	0.93	C14—H14A	0.97
C3—C4	1.367 (3)	C14—H14B	0.97
C3—H3	0.93	C16—C17	1.480 (4)
C4—C5	1.373 (3)	C16—H16A	0.97
C4—H4	0.93	C16—H16B	0.97
C5—C6	1.381 (3)	C17—H17A	0.96
C5—H5A	0.93	C17—H17B	0.96
C6—H6	0.93	C17—H17C	0.96

O1—S1—O2	120.6 (1)	C8—C9—H9	119.8
O1—S1—N1	105.7 (1)	C10—C9—H9	119.8
O2—S1—N1	106.7 (1)	C9—C10—C11	120.4 (2)
O1—S1—C1	109.7 (1)	C9—C10—H10	119.8
O2—S1—C1	107.2 (1)	C11—C10—H10	119.8
N1—S1—C1	106.0 (1)	C10—C11—C12	119.8 (2)
C7—N1—C14	117.7 (2)	C10—C11—H11	120.1
C7—N1—S1	120.1 (1)	C12—C11—H11	120.1
C14—N1—S1	117.9 (1)	C7—C12—C11	118.69 (19)
C15—O4—C16	117.27 (16)	C7—C12—C13	121.86 (18)
C6—C1—C2	121.17 (18)	C11—C12—C13	119.45 (19)
C6—C1—S1	119.73 (15)	O5—C13—C12	123.8 (2)
C2—C1—S1	119.08 (15)	O5—C13—H13	118.1
C3—C2—C1	119.2 (2)	C12—C13—H13	118.1
C3—C2—H2	120.4	N1—C14—C15	111.6 (2)
C1—C2—H2	120.4	N1—C14—H14A	109.3
C2—C3—C4	120.1 (2)	C15—C14—H14A	109.3
C2—C3—H3	120.0	N1—C14—H14B	109.3
C4—C3—H3	120.0	C15—C14—H14B	109.3
C5—C4—C3	120.6 (2)	H14A—C14—H14B	108.0
C5—C4—H4	119.7	O3—C15—O4	125.4 (2)
C3—C4—H4	119.7	O3—C15—C14	125.5 (2)
C4—C5—C6	120.1 (2)	O4—C15—C14	109.11 (17)
C4—C5—H5A	120.0	O4—C16—C17	107.0 (2)
C6—C5—H5A	120.0	O4—C16—H16A	110.3
C1—C6—C5	118.9 (2)	C17—C16—H16A	110.3
C1—C6—H6	120.6	O4—C16—H16B	110.3
C5—C6—H6	120.6	C17—C16—H16B	110.3
C8—C7—C12	120.55 (19)	H16A—C16—H16B	108.6
C8—C7—N1	119.79 (18)	C16—C17—H17A	109.5
C12—C7—N1	119.63 (17)	C16—C17—H17B	109.5
C9—C8—C7	120.0 (2)	H17A—C17—H17B	109.5
C9—C8—H8	120.0	C16—C17—H17C	109.5
C7—C8—H8	120.0	H17A—C17—H17C	109.5
C8—C9—C10	120.5 (2)	H17B—C17—H17C	109.5

O1—S1—N1—C7	24.90 (17)	C14—N1—C7—C12	119.11 (18)
O2—S1—N1—C7	154.43 (15)	S1—N1—C7—C12	−84.75 (19)
C1—S1—N1—C7	−91.53 (15)	C12—C7—C8—C9	−1.0 (3)
O1—S1—N1—C14	−179.00 (14)	N1—C7—C8—C9	177.16 (19)
O2—S1—N1—C14	−49.47 (17)	C7—C8—C9—C10	0.1 (3)
C1—S1—N1—C14	64.58 (16)	C8—C9—C10—C11	1.1 (4)
O1—S1—C1—C6	−33.51 (18)	C9—C10—C11—C12	−1.5 (3)
O2—S1—C1—C6	−166.12 (17)	C8—C7—C12—C11	0.6 (3)
N1—S1—C1—C6	80.23 (17)	N1—C7—C12—C11	−177.55 (16)
O1—S1—C1—C2	148.00 (16)	C8—C7—C12—C13	−179.43 (17)
O2—S1—C1—C2	15.4 (2)	N1—C7—C12—C13	2.4 (3)
N1—S1—C1—C2	−98.26 (16)	C10—C11—C12—C7	0.6 (3)
C6—C1—C2—C3	−0.5 (3)	C10—C11—C12—C13	−179.32 (19)
S1—C1—C2—C3	177.94 (18)	C7—C12—C13—O5	171.5 (2)
C1—C2—C3—C4	−0.2 (3)	C11—C12—C13—O5	−8.5 (3)
C2—C3—C4—C5	0.3 (4)	C7—N1—C14—C15	−80.8 (2)
C3—C4—C5—C6	0.2 (4)	S1—N1—C14—C15	122.49 (16)
C2—C1—C6—C5	1.1 (3)	C16—O4—C15—O3	−1.5 (3)
S1—C1—C6—C5	−177.41 (17)	C16—O4—C15—C14	177.78 (17)
C4—C5—C6—C1	−0.9 (3)	N1—C14—C15—O3	−8.5 (3)
C14—N1—C7—C8	−59.1 (2)	N1—C14—C15—O4	172.19 (15)
S1—N1—C7—C8	97.09 (19)	C15—O4—C16—C17	173.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3ⁱ	0.93	2.57	3.218 (3)	127
C16—H16B···Cg1ⁱⁱ	0.97	2.73	3.605 (3)	150

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₅S
M_r	347.38
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	11.3442 (5), 11.7731 (6), 12.7809 (6)
V (Å³)	1706.97 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.948, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	10886, 4104, 3294
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.092, 0.95
No. of reflections	4104
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.23
Absolute structure	Flack (1983), 1714 Friedel pairs
Absolute structure parameter	−0.05 (7)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3ⁱ	0.93	2.57	3.218 (3)	127
C16—H16B···Cg1ⁱⁱ	0.97	2.73	3.605 (3)	150

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

BB and RS thank Dr Babu Varghese, SAIF, IIT-Madras, India, for his help with the data collection.

References

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