N-(2-Formyl-phen-yl)-4-toluene-sulfonamide: a second monoclinic polymorph.

The title compound, C(14)H(13)NO(3)S, (I), is a second monoclinic polymorph. The original polymorph, (II), was reported by Mahía et al. [Acta Cryst. (1999), C55, 2158-2160]. Polymorph (II) crystalllized in the space group P2(1)/c (Z = 4), whereas the title polymorph (I) occurs in the space group P2(1)/n (Z = 4). The dihedral angle between the two aromatic rings is 75.9 (1)° in (I) compared to 81.9 (1)° for (II). In both polymorphs, two S(6) rings are generated by intra-molecular N-H⋯O and C-H⋯O hydrogen bonds, resulting in similar mol-ecular geometries. However, the two polymorphs differ concerning their crystal packing. In (I), mol-ecules are linked into C(8) zigzag chains along the b axis by C-H⋯O hydrogen bonds, whereas in (II) mol-ecules are linked by C-H⋯O hydrogen bonds, forming C(7) chains along the b axis. The title polymorph is further stabilized by inter-molecular C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.814 (1) Å]. These inter-actions are not evident in polymorph (II).

Related literature

For biological applications of sulfonamides, see: Connor (1998 ▶); Berredjem et al. (2000 ▶); Lee & Lee (2002 ▶); Xiao & Timberlake (2000 ▶). For the first monoclinic polymorph, see: Mahía et al. (1999 ▶). For a related structure, see: Zhang et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H13NO3S

M = 275.31

Monoclinic,

a = 11.5409 (4) Å

b = 8.1345 (2) Å

c = 14.1115 (5) Å

β = 97.294 (2)°

V = 1314.06 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 293 K

0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.940, T max = 0.956

16047 measured reflections

4254 independent reflections

2678 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.155

S = 1.02

4254 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.40 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009403/im2360sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009403/im2360Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009403/im2360Isup3.cml

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

C14H13NO3S	F(000) = 576
Mr = 275.31	Dx = 1.392 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4561 reflections
a = 11.5409 (4) Å	θ = 2.2–32.0°
b = 8.1345 (2) Å	µ = 0.25 mm−1
c = 14.1115 (5) Å	T = 293 K
β = 97.294 (2)°	Block, pale yellow
V = 1314.06 (7) Å3	0.25 × 0.23 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	4254 independent reflections
Radiation source: fine-focus sealed tube	2678 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.0 pixels mm-1	θmax = 32.0°, θmin = 2.2°
ω scans	h = −15→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −11→12
Tmin = 0.940, Tmax = 0.956	l = −16→21
16047 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)] = 0.049	H-atom parameters constrained
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0735P)2 + 0.2545P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4254 reflections	Δρmax = 0.30 e Å−3
174 parameters	Δρmin = −0.40 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (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	0.52951 (5)	0.12891 (6)	0.23059 (3)	0.06087 (19)
C1	0.56496 (14)	0.25944 (19)	0.05828 (10)	0.0454 (4)
C6	0.51658 (14)	0.27675 (19)	−0.03793 (11)	0.0472 (4)
N1	0.50096 (14)	0.1677 (2)	0.11710 (10)	0.0566 (4)
H1	0.4372	0.1256	0.0892	0.068*
C5	0.57925 (17)	0.3623 (2)	−0.10019 (12)	0.0580 (4)
H5	0.5484	0.3721	−0.1641	0.070*
O1	0.33743 (12)	0.13376 (18)	−0.03182 (11)	0.0708 (4)
C8	0.49992 (15)	0.3098 (2)	0.29018 (11)	0.0497 (4)
C13	0.58899 (15)	0.4156 (2)	0.32385 (12)	0.0563 (4)
H13	0.6657	0.3916	0.3151	0.068*
C7	0.40286 (17)	0.2107 (2)	−0.07598 (13)	0.0608 (5)
H7	0.3780	0.2293	−0.1404	0.073*
C2	0.67100 (15)	0.3343 (2)	0.08926 (12)	0.0556 (4)
H2	0.7026	0.3273	0.1531	0.067*
O2	0.65042 (14)	0.0934 (2)	0.25269 (11)	0.0804 (5)
C11	0.45109 (18)	0.5950 (2)	0.38535 (13)	0.0614 (5)
C12	0.56359 (17)	0.5566 (3)	0.37043 (14)	0.0627 (5)
H12	0.6239	0.6281	0.3925	0.075*
C4	0.68487 (18)	0.4321 (3)	−0.06949 (15)	0.0640 (5)
H4	0.7262	0.4877	−0.1120	0.077*
C10	0.36292 (18)	0.4862 (3)	0.35138 (15)	0.0680 (5)
H10	0.2864	0.5098	0.3608	0.082*
O3	0.44396 (17)	0.0087 (2)	0.24676 (12)	0.0891 (5)
C3	0.72931 (17)	0.4190 (2)	0.02550 (15)	0.0612 (5)
H3	0.8004	0.4686	0.0470	0.073*
C9	0.38592 (17)	0.3451 (3)	0.30435 (14)	0.0626 (5)
H9	0.3257	0.2736	0.2821	0.075*
C14	0.4263 (3)	0.7500 (3)	0.43715 (17)	0.0867 (7)
H14A	0.4874	0.7685	0.4888	0.130*
H14B	0.3530	0.7394	0.4620	0.130*
H14C	0.4226	0.8412	0.3937	0.130*

	U11	U22	U33	U12	U13	U23
S1	0.0805 (4)	0.0561 (3)	0.0451 (2)	0.0081 (2)	0.0047 (2)	0.00904 (18)
C1	0.0500 (9)	0.0445 (8)	0.0410 (7)	0.0082 (7)	0.0029 (6)	−0.0031 (6)
C6	0.0532 (9)	0.0437 (8)	0.0427 (8)	0.0071 (7)	−0.0011 (6)	−0.0044 (6)
N1	0.0595 (9)	0.0669 (9)	0.0423 (7)	−0.0054 (7)	0.0017 (6)	0.0015 (6)
C5	0.0707 (12)	0.0595 (10)	0.0421 (8)	0.0054 (8)	0.0008 (8)	0.0025 (7)
O1	0.0607 (8)	0.0794 (10)	0.0696 (9)	−0.0118 (7)	−0.0021 (7)	−0.0111 (7)
C8	0.0514 (9)	0.0599 (9)	0.0378 (7)	0.0042 (7)	0.0054 (6)	0.0084 (7)
C13	0.0441 (9)	0.0767 (12)	0.0476 (9)	0.0044 (8)	0.0039 (7)	0.0005 (8)
C7	0.0642 (12)	0.0651 (11)	0.0489 (9)	0.0029 (9)	−0.0086 (8)	−0.0085 (8)
C2	0.0519 (10)	0.0678 (11)	0.0445 (8)	0.0046 (8)	−0.0039 (7)	−0.0020 (7)
O2	0.0930 (11)	0.0843 (10)	0.0605 (8)	0.0407 (8)	−0.0041 (7)	0.0065 (7)
C11	0.0777 (13)	0.0623 (11)	0.0476 (9)	0.0109 (9)	0.0218 (9)	0.0132 (8)
C12	0.0633 (11)	0.0707 (12)	0.0548 (10)	−0.0064 (9)	0.0098 (8)	−0.0037 (9)
C4	0.0695 (12)	0.0635 (11)	0.0608 (11)	−0.0013 (9)	0.0150 (9)	0.0072 (9)
C10	0.0535 (11)	0.0891 (15)	0.0649 (12)	0.0125 (10)	0.0210 (9)	0.0108 (10)
O3	0.1354 (14)	0.0640 (9)	0.0700 (10)	−0.0193 (9)	0.0206 (9)	0.0124 (7)
C3	0.0514 (10)	0.0642 (11)	0.0672 (12)	−0.0025 (8)	0.0043 (8)	−0.0027 (9)
C9	0.0498 (10)	0.0785 (13)	0.0606 (11)	−0.0063 (9)	0.0115 (8)	0.0067 (9)
C14	0.128 (2)	0.0684 (13)	0.0712 (14)	0.0182 (14)	0.0426 (14)	0.0085 (11)

S1—O2	1.4204 (16)	C7—H7	0.9300
S1—O3	1.4285 (16)	C2—C3	1.375 (3)
S1—N1	1.6245 (14)	C2—H2	0.9300
S1—C8	1.7500 (18)	C11—C12	1.377 (3)
C1—C2	1.387 (2)	C11—C10	1.387 (3)
C1—N1	1.395 (2)	C11—C14	1.503 (3)
C1—C6	1.408 (2)	C12—H12	0.9300
C6—C5	1.393 (2)	C4—C3	1.377 (3)
C6—C7	1.456 (3)	C4—H4	0.9300
N1—H1	0.8600	C10—C9	1.369 (3)
C5—C4	1.364 (3)	C10—H10	0.9300
C5—H5	0.9300	C3—H3	0.9300
O1—C7	1.212 (2)	C9—H9	0.9300
C8—C13	1.378 (3)	C14—H14A	0.9600
C8—C9	1.386 (3)	C14—H14B	0.9600
C13—C12	1.372 (3)	C14—H14C	0.9600
C13—H13	0.9300
O2—S1—O3	120.36 (11)	C3—C2—C1	119.95 (16)
O2—S1—N1	109.05 (9)	C3—C2—H2	120.0
O3—S1—N1	103.45 (9)	C1—C2—H2	120.0
O2—S1—C8	108.16 (9)	C12—C11—C10	117.85 (19)
O3—S1—C8	108.55 (9)	C12—C11—C14	120.4 (2)
N1—S1—C8	106.44 (8)	C10—C11—C14	121.76 (19)
C2—C1—N1	124.04 (14)	C13—C12—C11	121.71 (19)
C2—C1—C6	119.08 (15)	C13—C12—H12	119.1
N1—C1—C6	116.87 (15)	C11—C12—H12	119.1
C5—C6—C1	118.94 (15)	C5—C4—C3	118.96 (18)
C5—C6—C7	117.88 (15)	C5—C4—H4	120.5
C1—C6—C7	123.17 (16)	C3—C4—H4	120.5
C1—N1—S1	129.33 (12)	C9—C10—C11	121.57 (18)
C1—N1—H1	115.3	C9—C10—H10	119.2
S1—N1—H1	115.3	C11—C10—H10	119.2
C4—C5—C6	121.47 (16)	C2—C3—C4	121.53 (18)
C4—C5—H5	119.3	C2—C3—H3	119.2
C6—C5—H5	119.3	C4—C3—H3	119.2
C13—C8—C9	120.11 (18)	C10—C9—C8	119.3 (2)
C13—C8—S1	120.54 (13)	C10—C9—H9	120.3
C9—C8—S1	119.35 (15)	C8—C9—H9	120.3
C12—C13—C8	119.45 (17)	C11—C14—H14A	109.5
C12—C13—H13	120.3	C11—C14—H14B	109.5
C8—C13—H13	120.3	H14A—C14—H14B	109.5
O1—C7—C6	126.30 (17)	C11—C14—H14C	109.5
O1—C7—H7	116.9	H14A—C14—H14C	109.5
C6—C7—H7	116.9	H14B—C14—H14C	109.5
C2—C1—C6—C5	2.9 (2)	C9—C8—C13—C12	−0.8 (3)
N1—C1—C6—C5	−177.73 (15)	S1—C8—C13—C12	−179.94 (14)
C2—C1—C6—C7	−176.46 (16)	C5—C6—C7—O1	−179.95 (18)
N1—C1—C6—C7	2.9 (2)	C1—C6—C7—O1	−0.6 (3)
C2—C1—N1—S1	1.3 (3)	N1—C1—C2—C3	178.36 (16)
C6—C1—N1—S1	−178.02 (13)	C6—C1—C2—C3	−2.3 (3)
O2—S1—N1—C1	−41.57 (18)	C8—C13—C12—C11	0.6 (3)
O3—S1—N1—C1	−170.79 (16)	C10—C11—C12—C13	−0.2 (3)
C8—S1—N1—C1	74.91 (17)	C14—C11—C12—C13	179.64 (18)
C1—C6—C5—C4	−1.3 (3)	C6—C5—C4—C3	−0.9 (3)
C7—C6—C5—C4	178.06 (17)	C12—C11—C10—C9	−0.1 (3)
O2—S1—C8—C13	18.43 (17)	C14—C11—C10—C9	−179.92 (19)
O3—S1—C8—C13	150.58 (15)	C1—C2—C3—C4	0.1 (3)
N1—S1—C8—C13	−98.64 (15)	C5—C4—C3—C2	1.5 (3)
O2—S1—C8—C9	−160.77 (14)	C11—C10—C9—C8	−0.1 (3)
O3—S1—C8—C9	−28.61 (16)	C13—C8—C9—C10	0.5 (3)
N1—S1—C8—C9	82.16 (15)	S1—C8—C9—C10	179.68 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.94	2.655 (2)	140
C2—H2···O2	0.93	2.48	3.059 (2)	120
C14—H14C···O3i	0.96	2.52	3.439 (3)	161
C5—H5···Cg1ii	0.93	2.82	3.658 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.94	2.655 (2)	140
C2—H2⋯O2	0.93	2.48	3.059 (2)	120
C14—H14C⋯O3i	0.96	2.52	3.439 (3)	161
C5—H5⋯Cg1ii	0.93	2.82	3.658 (2)	150

Symmetry codes: (i) ; (ii) .