2-(N-Phenyl­methane­sulfonamido)­ethyl 1H-pyrrole-2-carboxyl­ate

Khan, S.T.; Yu, P.; Nelofar, A.; Ahmed, Z.; Chantrapromma, S.

doi:10.1107/S160053681101261X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1125-o1126

doi:10.1107/S160053681101261X

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2-(N-Phenylmethanesulfonamido)ethyl 1H-pyrrole-2-carboxylate

Salman Tariq Khan,^a ^* Peng Yu,^b Aisha Nelofar,^a Zaheer Ahmed ^c and Suchada Chantrapromma ^d ‡

^aPharmaceutical Research Centre, PCSIR Labs Complex, Karachi 75280, Pakistan, ^bDepartment of Pharmaceutical Engineering, Biotechnology College, Tianjin University of Science & Technology (TUST), Tianjin 300457, People's Republic of China, ^cFaculty of Sciences, Department of Home and Health Sciences, Allama Iqbal Open University, H-8, Islamabad, Pakistan, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: salmankhann@hotmail.com

(Received 24 March 2011; accepted 5 April 2011; online 13 April 2011)

In the title compound, C₁₄H₁₆N₂O₄S, the ethoxycarbonyl group is nearly planar, with an r.m.s. deviation of 0.0067 Å, and is almost coplanar with the pyrrole ring [dihedral angle = 5.81 (15)°], whereas it is inclined at a dihedral angle of 61.90 (13)° to the phenyl ring. The dihedral angle between the pyrrole and phenyl rings is 56.15 (13)°. In the crystal, centrosymmetrically related molecules are linked into dimers by pairs of N—H⋯O hydrogen bonds, forming rings of R₂²(10) graph-set motif. The dimers are further connected by weak intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions, forming layers parallel to the bc plane.

Related literature

For the pharmacological and biological activity of pyrrole-2-carboxylate derivatives and sulfonamides, see: Brienne et al. (1987 ); Burnham et al. (1998 ); Fan et al. (2008 ); Fu et al. (2002 ); Gupton et al. (1999 ); Manzanaro et al. (2006 ); Mayer et al. (2009 ); Yoshikawa et al. (1993 , 1998 ). For a related structure, see: Khan et al. (2010 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₆N₂O₄S
M_r = 308.36
Monoclinic, P 2₁ /c
a = 12.186 (2) Å
b = 5.6516 (11) Å
c = 22.160 (4) Å
β = 104.47 (3)°
V = 1477.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 153 K
0.32 × 0.08 × 0.06 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.928, T_max = 0.986
12044 measured reflections
3499 independent reflections
2726 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.152
S = 1.06
3499 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C5/N1 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.92 (4)	1.99 (4)	2.894 (3)	167 (3)
C6—H6B⋯O4ⁱⁱ	0.99	2.53	3.415 (3)	148
C7—H7A⋯O4ⁱⁱⁱ	0.99	2.55	3.406 (3)	145
C7—H7B⋯O1^iv	0.99	2.54	3.431 (3)	150
C6—H6A⋯Cg1^v	0.99	2.91	3.899 (3)	173
Symmetry codes: (i) -x, -y+2, -z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y-1, z; (v) -x, -y+1, -z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681101261X/rz2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681101261X/rz2576Isup2.hkl

checkCIF report

Comment top

Pyrrole-2-carboxylate based heterocyclic compounds, either naturally occurring or synthetic, have shown various pharmacological and biological activities such as anticancer (Burnham et al., 1998; Gupton et al., 1999; Fan et al., 2008), antidiabetic, aldose reductase inhibition (Mayer et al., 2009; Manzanaro et al., 2006) anti-inflammatory and analgesic activities (Fu et al., 2002). Likewise, compounds containing the sulfonamide moiety have their own biological importance as antifilarial (Brienne et al., 1987) anti-inflammatory, antipyretic, analgesic and antiallergy agents (Yoshikawa et al., 1993; Yoshikawa et al., 1998) The title compound was synthesized as an intermediate which will be used in search of new potent anti-inflammatory and/or analgesic agents. Its crystal structure analysis was undertaken in order to establish the conformation of the various groups.

Fig. 1 shows the molecular structure of the title compound, in which the ethylcarboxylate unit (C1/C2/O1/O2/C6/C7) is planar with r.m.s. of 0.0067 (2) Å. This unit is almost co-planar with the pyrrole ring whereas is inclined to the benzene ring with dihedral angles of 5.81 (15) and 61.90 (13)°, respectively. The dihedral angle between the pyrrole and benzene rings is 56.15 (13)°. The orientation of the methylsulfonamide group (C14/S1/O3/O3/N2) with respect to the ethylcarboxylate unit can be indicated by the torsion angles S1–N2–C7–C6 = 121.87 (18)° and C14–S1–N2–C7 = 72.67 (18)°. The bond lengths are in normal ranges (Allen et al., 1987) and comparable to those reported for a related structure (Khan et al., 2010).

In the crystal structure (Fig. 2), N—H···O hydrogen interactions (Table 1) link centrosymmetrically related molecules into dimers forming rings of R²₂(10) graph-set motif. The dimers are further arranged into layers parallel to the bc plane by weak intermolecular C—H···O hydrogen bonds and C—H···π interactions (Table 1).

Related literature top

For the pharmacological and biological activity of pyrrole-2-carboxylate derivatives and sulfonamides, see: Brienne et al. (1987); Burnham et al. (1998); Fan et al. (2008); Fu et al. (2002); Gupton et al. (1999); Manzanaro et al. (2006); Mayer et al. (2009); Yoshikawa et al. (1993, 1998). For a related structure, see: Khan et al. (2010). For standard bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by mixing 2-(phenylamino)ethyl-1H-pyrrole-2-carboxylate (1.0 g, 1.8 mmol), triethylamine (0.88 g, 8.8 mmol) and methanesulfonyl chloride (0.1 g, 8.8 mmol) in dichloromethane (6 ml) under nitrogen in sealed tube. The reaction mixture was stirred for 4 h at 273 K. The mixture was poured onto ice, and then sodium bicarbonate (10 ml, 10%) was added and the solution stirred for 10 minutes. The organic layer was separated and the aqueous layer was extracted with dichloromethane. The combined organic layers were dried over MgSO₄, filtered and concentrated, yielding the a white precipitate of the title compound. Colourless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from dichloromethane by the slow evaporation of the solvent at room temperature after several days.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound viewd along the b axis. C—H···O weak interactions are drawn as dashed lines.

2-(N-Phenylmethanesulfonamido)ethyl 1H-pyrrole-2-carboxylate top

Crystal data top

C₁₄H₁₆N₂O₄S	F(000) = 648
M_r = 308.36	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3499 reflections
a = 12.186 (2) Å	θ = 1.7–27.8°
b = 5.6516 (11) Å	µ = 0.24 mm⁻¹
c = 22.160 (4) Å	T = 153 K
β = 104.47 (3)°	Needle, colourless
V = 1477.8 (5) Å³	0.32 × 0.08 × 0.06 mm
Z = 4

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3499 independent reflections
Radiation source: rotating anode	2726 reflections with I > 2σ(I)
Multilayer monochromator	R_int = 0.050
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.8°, θ_min = 1.7°
ω and ϕ scans	h = −16→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −6→7
T_min = 0.928, T_max = 0.986	l = −28→29
12044 measured reflections

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.152	w = 1/[σ²(F_o²) + (0.0745P)² + 0.5129P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3499 reflections	Δρ_max = 0.43 e Å⁻³
196 parameters	Δρ_min = −0.50 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (3)

Crystal data top

C₁₄H₁₆N₂O₄S	V = 1477.8 (5) Å³
M_r = 308.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.186 (2) Å	µ = 0.24 mm⁻¹
b = 5.6516 (11) Å	T = 153 K
c = 22.160 (4) Å	0.32 × 0.08 × 0.06 mm
β = 104.47 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3499 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2726 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.986	R_int = 0.050
12044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.43 e Å⁻³
3499 reflections	Δρ_min = −0.50 e Å⁻³
196 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	0.19337 (5)	0.19937 (10)	0.28338 (2)	0.02406 (19)
N1	0.1780 (2)	0.9013 (4)	−0.01667 (10)	0.0354 (5)
N2	0.19052 (16)	0.2462 (3)	0.21007 (9)	0.0252 (4)
O1	0.01281 (16)	0.7777 (3)	0.04865 (9)	0.0394 (5)
O2	0.12012 (14)	0.4664 (3)	0.08930 (7)	0.0325 (4)
O3	0.29861 (14)	0.2895 (3)	0.32044 (7)	0.0301 (4)
O4	0.08904 (14)	0.2914 (3)	0.29278 (8)	0.0314 (4)
C1	0.0969 (2)	0.6576 (4)	0.05242 (10)	0.0295 (5)
C2	0.1832 (2)	0.7006 (4)	0.01917 (10)	0.0299 (5)
C3	0.2777 (2)	0.5733 (5)	0.01512 (11)	0.0371 (6)
H3	0.3024	0.4271	0.0351	0.045*
C4	0.3301 (3)	0.7006 (5)	−0.02406 (13)	0.0449 (7)
H4	0.3972	0.6562	−0.0356	0.054*
C5	0.2671 (2)	0.9020 (5)	−0.04295 (12)	0.0423 (7)
H5	0.2834	1.0208	−0.0698	0.051*
C6	0.0391 (2)	0.4147 (4)	0.12552 (11)	0.0304 (5)
H6A	−0.0368	0.3842	0.0977	0.036*
H6B	0.0333	0.5495	0.1531	0.036*
C7	0.08226 (19)	0.1984 (4)	0.16350 (11)	0.0280 (5)
H7A	0.0249	0.1447	0.1852	0.034*
H7B	0.0937	0.0696	0.1354	0.034*
C8	0.29508 (19)	0.2205 (4)	0.19055 (10)	0.0231 (5)
C9	0.37363 (19)	0.4032 (4)	0.20276 (10)	0.0263 (5)
H9	0.3599	0.5392	0.2250	0.032*
C10	0.4723 (2)	0.3868 (4)	0.18253 (11)	0.0308 (5)
H10	0.5267	0.5107	0.1913	0.037*
C11	0.4913 (2)	0.1904 (4)	0.14962 (11)	0.0329 (6)
H11	0.5583	0.1806	0.1352	0.040*
C12	0.4133 (2)	0.0074 (5)	0.13752 (11)	0.0341 (6)
H12	0.4270	−0.1277	0.1150	0.041*
C13	0.3151 (2)	0.0214 (4)	0.15835 (10)	0.0295 (5)
H13	0.2619	−0.1048	0.1506	0.035*
C14	0.1928 (2)	−0.1101 (4)	0.29289 (11)	0.0316 (5)
H14A	0.2586	−0.1786	0.2814	0.047*
H14B	0.1231	−0.1759	0.2660	0.047*
H14C	0.1962	−0.1478	0.3365	0.047*
H1	0.121 (3)	1.012 (6)	−0.0206 (16)	0.065 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0248 (3)	0.0244 (3)	0.0239 (3)	0.0005 (2)	0.0077 (2)	−0.0002 (2)
N1	0.0445 (14)	0.0324 (12)	0.0288 (10)	−0.0029 (10)	0.0081 (10)	0.0032 (9)
N2	0.0218 (10)	0.0319 (10)	0.0218 (9)	−0.0014 (8)	0.0049 (7)	0.0011 (8)
O1	0.0375 (11)	0.0365 (10)	0.0439 (11)	0.0065 (8)	0.0097 (8)	0.0104 (8)
O2	0.0333 (10)	0.0382 (10)	0.0274 (8)	0.0055 (7)	0.0099 (7)	0.0094 (7)
O3	0.0290 (9)	0.0368 (10)	0.0237 (8)	−0.0073 (7)	0.0049 (7)	−0.0051 (7)
O4	0.0298 (9)	0.0341 (10)	0.0338 (9)	0.0056 (7)	0.0146 (7)	0.0006 (7)
C1	0.0337 (13)	0.0299 (13)	0.0222 (11)	−0.0022 (10)	0.0016 (9)	−0.0010 (9)
C2	0.0358 (13)	0.0310 (13)	0.0208 (11)	−0.0030 (10)	0.0031 (9)	−0.0015 (9)
C3	0.0432 (15)	0.0391 (15)	0.0300 (12)	0.0058 (11)	0.0109 (11)	0.0060 (11)
C4	0.0486 (17)	0.0525 (18)	0.0385 (15)	0.0028 (13)	0.0202 (13)	0.0049 (13)
C5	0.0499 (17)	0.0450 (16)	0.0353 (14)	−0.0049 (13)	0.0168 (13)	0.0042 (12)
C6	0.0265 (12)	0.0386 (14)	0.0264 (11)	0.0009 (10)	0.0074 (9)	0.0034 (10)
C7	0.0253 (12)	0.0307 (13)	0.0266 (11)	−0.0040 (9)	0.0034 (9)	0.0004 (9)
C8	0.0249 (11)	0.0241 (11)	0.0204 (10)	0.0007 (8)	0.0057 (8)	0.0026 (8)
C9	0.0283 (12)	0.0226 (12)	0.0284 (11)	−0.0008 (9)	0.0079 (9)	0.0006 (9)
C10	0.0266 (12)	0.0324 (13)	0.0343 (12)	−0.0013 (9)	0.0093 (10)	0.0061 (10)
C11	0.0306 (13)	0.0407 (15)	0.0301 (12)	0.0070 (10)	0.0125 (10)	0.0082 (11)
C12	0.0395 (14)	0.0352 (14)	0.0295 (12)	0.0060 (11)	0.0124 (10)	−0.0014 (10)
C13	0.0346 (13)	0.0259 (12)	0.0282 (11)	−0.0022 (9)	0.0084 (10)	−0.0012 (9)
C14	0.0322 (13)	0.0274 (12)	0.0352 (13)	0.0017 (9)	0.0085 (10)	0.0053 (10)

Geometric parameters (Å, º) top

S1—O3	1.4325 (17)	C6—C7	1.503 (3)
S1—O4	1.4363 (17)	C6—H6A	0.9900
S1—N2	1.6376 (19)	C6—H6B	0.9900
S1—C14	1.762 (3)	C7—H7A	0.9900
N1—C5	1.354 (3)	C7—H7B	0.9900
N1—C2	1.377 (3)	C8—C13	1.386 (3)
N1—H1	0.92 (3)	C8—C9	1.388 (3)
N2—C8	1.452 (3)	C9—C10	1.387 (3)
N2—C7	1.483 (3)	C9—H9	0.9500
O1—C1	1.215 (3)	C10—C11	1.379 (4)
O2—C1	1.342 (3)	C10—H10	0.9500
O2—C6	1.450 (3)	C11—C12	1.384 (4)
C1—C2	1.447 (3)	C11—H11	0.9500
C2—C3	1.379 (3)	C12—C13	1.389 (3)
C3—C4	1.399 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.378 (4)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800

O3—S1—O4	119.10 (11)	C7—C6—H6B	110.4
O3—S1—N2	107.77 (10)	H6A—C6—H6B	108.6
O4—S1—N2	106.58 (10)	N2—C7—C6	111.57 (19)
O3—S1—C14	108.31 (11)	N2—C7—H7A	109.3
O4—S1—C14	108.16 (11)	C6—C7—H7A	109.3
N2—S1—C14	106.23 (11)	N2—C7—H7B	109.3
C5—N1—C2	108.9 (2)	C6—C7—H7B	109.3
C5—N1—H1	129 (2)	H7A—C7—H7B	108.0
C2—N1—H1	122 (2)	C13—C8—C9	120.2 (2)
C8—N2—C7	117.97 (18)	C13—C8—N2	121.0 (2)
C8—N2—S1	118.48 (15)	C9—C8—N2	118.8 (2)
C7—N2—S1	117.10 (15)	C10—C9—C8	119.9 (2)
C1—O2—C6	115.53 (18)	C10—C9—H9	120.0
O1—C1—O2	122.5 (2)	C8—C9—H9	120.0
O1—C1—C2	125.4 (2)	C11—C10—C9	119.9 (2)
O2—C1—C2	112.1 (2)	C11—C10—H10	120.1
N1—C2—C3	108.1 (2)	C9—C10—H10	120.1
N1—C2—C1	119.8 (2)	C10—C11—C12	120.4 (2)
C3—C2—C1	132.1 (2)	C10—C11—H11	119.8
C2—C3—C4	106.8 (2)	C12—C11—H11	119.8
C2—C3—H3	126.6	C11—C12—C13	120.0 (2)
C4—C3—H3	126.6	C11—C12—H12	120.0
C5—C4—C3	107.9 (2)	C13—C12—H12	120.0
C5—C4—H4	126.0	C8—C13—C12	119.6 (2)
C3—C4—H4	126.0	C8—C13—H13	120.2
N1—C5—C4	108.2 (2)	C12—C13—H13	120.2
N1—C5—H5	125.9	S1—C14—H14A	109.5
C4—C5—H5	125.9	S1—C14—H14B	109.5
O2—C6—C7	106.41 (18)	H14A—C14—H14B	109.5
O2—C6—H6A	110.4	S1—C14—H14C	109.5
C7—C6—H6A	110.4	H14A—C14—H14C	109.5
O2—C6—H6B	110.4	H14B—C14—H14C	109.5

O3—S1—N2—C8	37.3 (2)	C3—C4—C5—N1	−0.1 (3)
O4—S1—N2—C8	166.21 (16)	C1—O2—C6—C7	−179.25 (19)
C14—S1—N2—C8	−78.62 (19)	C8—N2—C7—C6	−86.7 (2)
O3—S1—N2—C7	−171.42 (16)	S1—N2—C7—C6	121.87 (18)
O4—S1—N2—C7	−42.50 (19)	O2—C6—C7—N2	65.8 (2)
C14—S1—N2—C7	72.67 (18)	C7—N2—C8—C13	−47.9 (3)
C6—O2—C1—O1	−1.2 (3)	S1—N2—C8—C13	103.1 (2)
C6—O2—C1—C2	178.48 (19)	C7—N2—C8—C9	129.8 (2)
C5—N1—C2—C3	0.0 (3)	S1—N2—C8—C9	−79.1 (2)
C5—N1—C2—C1	−179.9 (2)	C13—C8—C9—C10	0.2 (3)
O1—C1—C2—N1	5.3 (4)	N2—C8—C9—C10	−177.6 (2)
O2—C1—C2—N1	−174.4 (2)	C8—C9—C10—C11	0.8 (3)
O1—C1—C2—C3	−174.7 (3)	C9—C10—C11—C12	−1.1 (4)
O2—C1—C2—C3	5.7 (4)	C10—C11—C12—C13	0.2 (4)
N1—C2—C3—C4	0.0 (3)	C9—C8—C13—C12	−1.0 (3)
C1—C2—C3—C4	179.9 (3)	N2—C8—C13—C12	176.7 (2)
C2—C3—C4—C5	0.1 (3)	C11—C12—C13—C8	0.8 (4)
C2—N1—C5—C4	0.1 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C5/N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.92 (4)	1.99 (4)	2.894 (3)	167 (3)
C6—H6B···O4ⁱⁱ	0.99	2.53	3.415 (3)	148
C7—H7A···O4ⁱⁱⁱ	0.99	2.55	3.406 (3)	145
C7—H7B···O1^iv	0.99	2.54	3.431 (3)	150
C6—H6A···Cg1^v	0.99	2.91	3.899 (3)	173

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₂O₄S
M_r	308.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	153
a, b, c (Å)	12.186 (2), 5.6516 (11), 22.160 (4)
β (°)	104.47 (3)
V (Å³)	1477.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.32 × 0.08 × 0.06

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.928, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12044, 3499, 2726
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.152, 1.06
No. of reflections	3499
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.50

Computer programs: CrystalClear (Rigaku, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C5/N1 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.92 (4)	1.99 (4)	2.894 (3)	167 (3)
C6—H6B···O4ⁱⁱ	0.99	2.53	3.415 (3)	148
C7—H7A···O4ⁱⁱⁱ	0.99	2.55	3.406 (3)	145
C7—H7B···O1^iv	0.99	2.54	3.431 (3)	150
C6—H6A···Cg1^v	0.99	2.91	3.899 (3)	173

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

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

STK acknowledges funding from the Industrial Linkage Programme of the Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories. PY is grateful to Tianjin University of Science & Technology for a research grant (No. 2009 0431). SC thanks the Prince of Songkla University for generous support through the CMRU. STK also thanks Dr Song Haibin (State Key Laboratory of Elemento-Organic Chemistry, Nankai University) for the data collection.

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Volume 67| Part 5| May 2011| Pages o1125-o1126

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