(2R)-2-Benzene-sulfonamido-2-phenyl-ethanoic acid: a new monoclinic polymorph.

In the title compound, C(14)H(13)NO(4)S, a sulfonamide derivative of phenyl glycine, the aromatic rings are inclined at a dihedral angle of 28.03 (12)°. In the crystal, O-H⋯O hydrogen bonds link the molecules into chains propagating in [100] and a weak C-H⋯O interaction cross-links the chains in the c-axis direction. In the previously published polymorph, the dihedral angle between the aromatic rings is 45.52 (18)° and the structure is stabilized by three different types of ring motif.

Related literature

For related sulfonamide structures see: Arshad et al. (2008a ▶,b ▶, 2009 ▶).

Experimental

Crystal data

C14H13NO4S

M = 291.31

Monoclinic,

a = 8.2464 (8) Å

b = 5.3251 (4) Å

c = 15.3642 (15) Å

β = 100.384 (3)°

V = 663.64 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 296 K

0.34 × 0.19 × 0.11 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.918, T max = 0.972

7864 measured reflections

3174 independent reflections

2372 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.099

S = 1.01

3174 reflections

187 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983), 1360 Friedel pairs

Flack parameter: −0.04 (9)

Data collection: APEX2 (Bruker, 2007 ▶ ▶); cell refinement: SAINT (Bruker, 2007 ▶ ▶); 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 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903606X/hg2562sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903606X/hg2562Isup2.hkl

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

C14H13NO4S	F(000) = 304
Mr = 291.31	Dx = 1.458 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1972 reflections
a = 8.2464 (8) Å	θ = 2.5–23.4°
b = 5.3251 (4) Å	µ = 0.26 mm−1
c = 15.3642 (15) Å	T = 296 K
β = 100.384 (3)°	Needle, white
V = 663.64 (10) Å3	0.34 × 0.19 × 0.11 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	3174 independent reflections
Radiation source: fine-focus sealed tube	2372 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
Tmin = 0.918, Tmax = 0.972	k = −7→6
7864 measured reflections	l = −20→20

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.1295P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3174 reflections	Δρmax = 0.24 e Å−3
187 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 1360 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.04 (9)

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	0.53130 (7)	0.77328 (15)	0.29076 (4)	0.03965 (18)
O1	0.5315 (3)	1.0355 (4)	0.27187 (13)	0.0569 (6)
O2	0.3791 (2)	0.6402 (4)	0.28841 (13)	0.0560 (6)
O3	0.9213 (3)	0.3901 (5)	0.25951 (16)	0.0728 (7)
O4	1.0525 (2)	0.7469 (6)	0.23666 (16)	0.0700 (7)
H4O	1.137 (5)	0.660 (9)	0.249 (3)	0.105*
N1	0.6206 (3)	0.6352 (5)	0.21858 (15)	0.0396 (6)
H1N	0.615 (4)	0.482 (6)	0.223 (2)	0.047*
C1	0.6493 (3)	0.7278 (5)	0.39752 (16)	0.0334 (6)
C2	0.6187 (3)	0.5204 (5)	0.44644 (19)	0.0411 (6)
H2	0.5406	0.4020	0.4222	0.049*
C3	0.7045 (3)	0.4914 (6)	0.53080 (19)	0.0448 (7)
H3	0.6846	0.3519	0.5637	0.054*
C4	0.8199 (3)	0.6657 (6)	0.56754 (19)	0.0454 (7)
H4A	0.8754	0.6469	0.6255	0.054*
C5	0.8524 (4)	0.8670 (6)	0.5181 (2)	0.0499 (8)
H5	0.9327	0.9823	0.5422	0.060*
C6	0.7673 (3)	0.9015 (6)	0.43262 (18)	0.0423 (6)
H6	0.7893	1.0393	0.3995	0.051*
C7	0.7556 (3)	0.7445 (5)	0.09274 (15)	0.0334 (5)
C8	0.6714 (3)	0.5591 (6)	0.03958 (18)	0.0433 (7)
H8	0.6165	0.4334	0.0647	0.052*
C9	0.6688 (4)	0.5605 (6)	−0.0501 (2)	0.0518 (8)
H9	0.6131	0.4341	−0.0852	0.062*
C10	0.7472 (4)	0.7454 (7)	−0.08849 (19)	0.0540 (8)
H10	0.7440	0.7458	−0.1493	0.065*
C11	0.8301 (4)	0.9294 (7)	−0.0367 (2)	0.0601 (9)
H11	0.8839	1.0552	−0.0624	0.072*
C12	0.8347 (4)	0.9302 (6)	0.0532 (2)	0.0492 (7)
H12	0.8915	1.0566	0.0877	0.059*
C13	0.7667 (3)	0.7445 (6)	0.19245 (15)	0.0360 (6)
H13	0.7771	0.9186	0.2133	0.043*
C14	0.9209 (4)	0.6019 (6)	0.23465 (19)	0.0461 (7)

	U11	U22	U33	U12	U13	U23
S1	0.0295 (3)	0.0577 (4)	0.0306 (3)	0.0117 (3)	0.0025 (2)	−0.0032 (4)
O1	0.0695 (15)	0.0584 (14)	0.0409 (12)	0.0304 (11)	0.0050 (10)	0.0040 (10)
O2	0.0254 (9)	0.0997 (17)	0.0418 (12)	0.0027 (10)	0.0028 (8)	−0.0118 (11)
O3	0.0545 (14)	0.0755 (17)	0.0822 (18)	0.0204 (13)	−0.0038 (12)	0.0157 (14)
O4	0.0300 (10)	0.0916 (18)	0.0829 (17)	0.0032 (14)	−0.0042 (10)	−0.0082 (17)
N1	0.0373 (12)	0.0503 (13)	0.0324 (13)	0.0042 (11)	0.0096 (10)	−0.0076 (11)
C1	0.0263 (11)	0.0461 (17)	0.0274 (12)	0.0045 (12)	0.0038 (9)	−0.0056 (12)
C2	0.0339 (14)	0.0466 (16)	0.0425 (16)	−0.0035 (13)	0.0058 (12)	−0.0041 (13)
C3	0.0458 (16)	0.0509 (18)	0.0387 (16)	0.0017 (14)	0.0101 (13)	0.0087 (14)
C4	0.0434 (16)	0.0590 (19)	0.0317 (15)	0.0069 (14)	0.0013 (12)	−0.0001 (14)
C5	0.0445 (17)	0.0542 (18)	0.0465 (19)	−0.0095 (14)	−0.0036 (14)	−0.0098 (15)
C6	0.0412 (14)	0.0438 (14)	0.0405 (16)	−0.0008 (14)	0.0041 (12)	0.0043 (14)
C7	0.0277 (11)	0.0397 (15)	0.0324 (12)	0.0074 (12)	0.0041 (9)	−0.0005 (13)
C8	0.0457 (16)	0.0482 (16)	0.0344 (16)	−0.0072 (13)	0.0034 (13)	−0.0014 (13)
C9	0.0510 (18)	0.066 (2)	0.0370 (17)	−0.0071 (16)	0.0034 (14)	−0.0084 (16)
C10	0.0566 (16)	0.070 (2)	0.0360 (15)	0.0064 (19)	0.0107 (13)	0.0054 (17)
C11	0.064 (2)	0.066 (2)	0.056 (2)	−0.0083 (18)	0.0258 (17)	0.0109 (18)
C12	0.0486 (16)	0.0516 (18)	0.0479 (19)	−0.0066 (15)	0.0100 (14)	−0.0056 (15)
C13	0.0289 (11)	0.0439 (15)	0.0343 (13)	0.0034 (13)	0.0030 (9)	−0.0071 (13)
C14	0.0400 (16)	0.065 (2)	0.0310 (15)	0.0090 (15)	0.0002 (12)	−0.0056 (15)

S1—O1	1.426 (2)	C5—C6	1.385 (4)
S1—O2	1.436 (2)	C5—H5	0.9300
S1—N1	1.615 (2)	C6—H6	0.9300
S1—C1	1.766 (2)	C7—C12	1.384 (4)
O3—C14	1.191 (4)	C7—C8	1.385 (4)
O4—C14	1.328 (4)	C7—C13	1.518 (3)
O4—H4O	0.83 (4)	C8—C9	1.375 (4)
N1—C13	1.458 (3)	C8—H8	0.9300
N1—H1N	0.82 (3)	C9—C10	1.368 (4)
C1—C6	1.380 (4)	C9—H9	0.9300
C1—C2	1.384 (4)	C10—C11	1.365 (5)
C2—C3	1.369 (4)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.374 (4)
C3—C4	1.376 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.368 (4)	C13—C14	1.522 (4)
C4—H4A	0.9300	C13—H13	0.9800
O1—S1—O2	120.73 (14)	C12—C7—C8	118.4 (3)
O1—S1—N1	106.78 (13)	C12—C7—C13	119.7 (2)
O2—S1—N1	105.24 (13)	C8—C7—C13	121.9 (2)
O1—S1—C1	107.61 (13)	C9—C8—C7	120.2 (3)
O2—S1—C1	106.75 (12)	C9—C8—H8	119.9
N1—S1—C1	109.41 (12)	C7—C8—H8	119.9
C14—O4—H4O	109 (3)	C10—C9—C8	120.8 (3)
C13—N1—S1	120.6 (2)	C10—C9—H9	119.6
C13—N1—H1N	119 (2)	C8—C9—H9	119.6
S1—N1—H1N	111 (2)	C11—C10—C9	119.4 (3)
C6—C1—C2	120.5 (2)	C11—C10—H10	120.3
C6—C1—S1	120.2 (2)	C9—C10—H10	120.3
C2—C1—S1	119.33 (19)	C10—C11—C12	120.5 (3)
C3—C2—C1	119.4 (3)	C10—C11—H11	119.7
C3—C2—H2	120.3	C12—C11—H11	119.7
C1—C2—H2	120.3	C11—C12—C7	120.6 (3)
C2—C3—C4	120.9 (3)	C11—C12—H12	119.7
C2—C3—H3	119.6	C7—C12—H12	119.7
C4—C3—H3	119.6	N1—C13—C7	112.0 (2)
C5—C4—C3	119.4 (3)	N1—C13—C14	110.6 (2)
C5—C4—H4A	120.3	C7—C13—C14	108.9 (2)
C3—C4—H4A	120.3	N1—C13—H13	108.4
C4—C5—C6	120.9 (3)	C7—C13—H13	108.4
C4—C5—H5	119.5	C14—C13—H13	108.4
C6—C5—H5	119.5	O3—C14—O4	126.0 (3)
C1—C6—C5	118.9 (3)	O3—C14—C13	124.3 (3)
C1—C6—H6	120.6	O4—C14—C13	109.7 (3)
C5—C6—H6	120.6
O1—S1—N1—C13	40.7 (2)	C13—C7—C8—C9	−177.7 (3)
O2—S1—N1—C13	170.1 (2)	C7—C8—C9—C10	−0.8 (5)
C1—S1—N1—C13	−75.5 (2)	C8—C9—C10—C11	0.6 (5)
O1—S1—C1—C6	−23.6 (2)	C9—C10—C11—C12	−0.2 (5)
O2—S1—C1—C6	−154.5 (2)	C10—C11—C12—C7	0.1 (5)
N1—S1—C1—C6	92.1 (2)	C8—C7—C12—C11	−0.2 (4)
O1—S1—C1—C2	154.5 (2)	C13—C7—C12—C11	178.1 (3)
O2—S1—C1—C2	23.6 (2)	S1—N1—C13—C7	−133.6 (2)
N1—S1—C1—C2	−89.8 (2)	S1—N1—C13—C14	104.7 (2)
C6—C1—C2—C3	1.2 (4)	C12—C7—C13—N1	150.2 (2)
S1—C1—C2—C3	−176.9 (2)	C8—C7—C13—N1	−31.6 (4)
C1—C2—C3—C4	0.3 (4)	C12—C7—C13—C14	−87.1 (3)
C2—C3—C4—C5	−1.8 (4)	C8—C7—C13—C14	91.1 (3)
C3—C4—C5—C6	1.9 (5)	N1—C13—C14—O3	23.4 (4)
C2—C1—C6—C5	−1.1 (4)	C7—C13—C14—O3	−100.1 (3)
S1—C1—C6—C5	177.0 (2)	N1—C13—C14—O4	−158.5 (2)
C4—C5—C6—C1	−0.5 (4)	C7—C13—C14—O4	78.0 (3)
C12—C7—C8—C9	0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O2i	0.83 (4)	1.98 (4)	2.727 (3)	150 (5)
C4—H4A···O3ii	0.93	2.56	3.317 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O2i	0.83 (4)	1.98 (4)	2.727 (3)	150 (5)
C4—H4A⋯O3ii	0.93	2.56	3.317 (4)	139

Symmetry codes: (i) ; (ii) .