2-(N-Phenyl-methane-sulfonamido)-ethyl 1H-pyrrole-2-carboxyl-ate.

In the title compound, C(14)H(16)N(2)O(4)S, the eth-oxy-carbonyl 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 mol-ecules are linked into dimers by pairs of N-H⋯O hydrogen bonds, forming rings of R(2) (2)(10) graph-set motif. The dimers are further connected by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions, 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 = 308.36

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.152

S = 1.06

3499 reflections

196 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.50 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H16N2O4S	F(000) = 648
Mr = 308.36	Dx = 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

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

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(Fo2) + (0.0745P)2 + 0.5129P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3499 reflections	Δρmax = 0.43 e Å−3
196 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···O1iv	0.99	2.54	3.431 (3)	150
C6—H6A···Cg1v	0.99	2.91	3.899 (3)	173

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⋯O1iv	0.99	2.54	3.431 (3)	150
C6—H6A⋯Cg1v	0.99	2.91	3.899 (3)	173

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .