(2R)-2-Benzene­sulfonamido-2-phenyl­ethanoic acid: a new monoclinic polymorph

Khan, I.U.; Sharif, S.; Arshad, M.N.; Ejaz; Idrees, M.

doi:10.1107/S160053680903606X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2436

doi:10.1107/S160053680903606X

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(2R)-2-Benzenesulfonamido-2-phenylethanoic acid: a new monoclinic polymorph

Islam Ullah Khan,^a ^* Shahzad Sharif,^a Muhammad Nadeem Arshad,^a Ejaz ^a and Muhammad Idrees ^a

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore, Pakistan
^*Correspondence e-mail: iukhan.gcu@gmail.com

(Received 1 September 2009; accepted 7 September 2009; online 12 September 2009)

In the title compound, C₁₄H₁₃NO₄S, 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_r = 291.31
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.099
S = 1.01
3174 reflections
187 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983), 1360 Friedel pairs
Flack parameter: −0.04 (9)

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) x+1, y, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

We have already reported the crystal structures of sulfonamides (Arshad et al., 2008a, b), (Arshad et al., 2009). In continuation of our studies in this area, we report here a new polymorph of our previously published sulfonamide (Arshad et al., 2009a), derivative (II).

The title compound (I) crystallizes in the monoclinic space group P21. The molecule has a chiral center at C₁₃ with a slightly distorted tetrahedral geometry. The dihedral angles between the two aromatic ring are 28.03 (12)° in (I) and 45.52 (18)° in (II). The crystal structure of I has no complex intermolecular interactions like II. There are only two types of hydrogen bonding interaction of O–H—O making a polymeric chain along the a-axes and C–H—O which linked these polymeric chain along c-axes (Fig. 2 and Table 1).

Related literature top

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

Experimental top

Phenyl glycine (2 g, 13.2 mmol) was dissolved in distilled water (15 ml) in a round bottom flask (50 ml). The pH of the solution was maintained at 8–9 using 1M, Na₂CO₃ solution. Benzene sulfonyl chloride (2.32 g, 13.2 mmol) was then suspended to the solution, and stirred at room temperature until all the suspension had been disappeared. On completion of the reaction the pH was adjusted 1–2, using 1 M HCl with stirring. The precipitate formed was filtered off, washed with distilled water, dried and recrystalized in methanol.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. The labelled molecular structure diagram of the title compound with the 50% probability level of drawn thermal ellipsoids.
	Fig. 2. Unit cell packing diagram showing the intermolecular hydrogen bonding using dashed lines. The hydrogen atoms not involved in hydrogen bonding have been omitted.

(2R)-2-Benzenesulfonamido-2-phenylethanoic acid top

Crystal data top

C₁₄H₁₃NO₄S	F(000) = 304
M_r = 291.31	D_x = 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

Data collection top

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

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0379P)² + 0.1295P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3174 reflections	Δρ_max = 0.24 e Å⁻³
187 parameters	Δρ_min = −0.26 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1360 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.04 (9)

Crystal data top

C₁₄H₁₃NO₄S	V = 663.64 (10) Å³
M_r = 291.31	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.2464 (8) Å	µ = 0.26 mm⁻¹
b = 5.3251 (4) Å	T = 296 K
c = 15.3642 (15) Å	0.34 × 0.19 × 0.11 mm
β = 100.384 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3174 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2372 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.972	R_int = 0.034
7864 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	Δρ_max = 0.24 e Å⁻³
S = 1.01	Δρ_min = −0.26 e Å⁻³
3174 reflections	Absolute structure: Flack (1983), 1360 Friedel pairs
187 parameters	Absolute structure parameter: −0.04 (9)
1 restraint

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	0.53130 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) −x+2, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄S
M_r	291.31
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	8.2464 (8), 5.3251 (4), 15.3642 (15)
β (°)	100.384 (3)
V (Å³)	663.64 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.34 × 0.19 × 0.11

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.918, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	7864, 3174, 2372
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.099, 1.01
No. of reflections	3174
No. of parameters	187
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.26
Absolute structure	Flack (1983), 1360 Friedel pairs
Absolute structure parameter	−0.04 (9)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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
O4—H4O···O2ⁱ	0.83 (4)	1.98 (4)	2.727 (3)	150 (5)
C4—H4A···O3ⁱⁱ	0.9300	2.5600	3.317 (4)	139.00

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

Acknowledgements

MNA acknowledges the Higher Education Commission of Pakistan for providing a PhD Scholarship under the Indigenous 5000 PhD fellowship program (PIN 042-120607-PS2-183).

References

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