A new polymorph of N-(6-methyl­pyridin-2-yl)mesityl­ene­sulfon­amide

A new polymorph is reported of the pharmaceutically active sulfa­pyridine derivative, N-(6-methyl­pyridin-2-yl)mesityl­ene­sulfon­amide, in the zwitterionic form 2-methyl-6-{[(2,4,6-tri­­methyl­benzene)­sulfon­yl]aza­nid­yl}pyridin-1-ium, C₁₅H₁₈N₂O₂S. The observed dimorphism is solvent dependent. The phase described previously [Beloso, Castro, García-Vázquez, Pérez-Lourido, Romero & Sousa (2003). Z. Anorg. Allg. Chem. 629, 275-284] crystallizes from ethanol and several other organic solvents, whereas the new form described here is obtained as a phase-pure product from methanol. The mol­ecules in both dimorphic phases are very similar and adopt the conformation which is also predicted for an individual mol­ecule by force field calculations. However, the two forms differ in their packing and hydrogen bonding. Results from solvent-assisted grinding indicate that the new form is less stable than the previously published phase.

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2012 (Sheldrick, 2008).

2-Methyl-6-{[(2,4,6-trimethylbenzene)sulfonyl]azanidyl}pyridin-1-ium

Crystal data

C15H18N2O2S	Z = 2
Mr = 290.37	F(000) = 308
Triclinic, P1	Dx = 1.383 Mg m^−3
a = 7.9753 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1446 (11) Å	Cell parameters from 1269 reflections
c = 11.7776 (16) Å	θ = 2.7–25.4°
α = 86.829 (3)°	µ = 0.24 mm^−1
β = 81.600 (3)°	T = 100 K
γ = 67.124 (3)°	Block, colourless
V = 697.29 (16) Å^3	0.19 × 0.10 × 0.09 mm

Data collection

Bruker D8 diffractometer with APEX CCD detector	3195 independent reflections
Radiation source: Incoatec microsource	2527 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.043
ω scans	θmax = 27.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→10
Tmin = 0.957, Tmax = 0.979	k = −10→10
9103 measured reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0461P)^2 + 0.4133P] where P = (Fo^2 + 2Fc^2)/3
3195 reflections	(Δ/σ)max < 0.001
189 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.82705 (7)	0.55137 (6)	0.30180 (4)	0.01535 (14)
O1	0.92771 (19)	0.36086 (18)	0.31141 (12)	0.0192 (3)
O2	0.63729 (18)	0.60458 (19)	0.28521 (12)	0.0205 (3)
N1	0.8318 (2)	0.8557 (2)	0.53085 (14)	0.0159 (4)
H1N	0.902 (3)	0.772 (3)	0.570 (2)	0.020 (6)*
N2	0.8525 (2)	0.6346 (2)	0.41429 (14)	0.0168 (4)
C1	0.7867 (3)	0.8102 (3)	0.43271 (16)	0.0159 (4)
C2	0.7785 (3)	1.0257 (3)	0.56965 (17)	0.0173 (4)
C3	0.6797 (3)	1.1637 (3)	0.50479 (17)	0.0192 (4)
H3	0.6436	1.2834	0.5287	0.023*
C4	0.6325 (3)	1.1258 (3)	0.40230 (18)	0.0200 (4)
H4	0.5645	1.2213	0.3564	0.024*
C5	0.6820 (3)	0.9540 (3)	0.36666 (17)	0.0186 (4)
H5	0.6462	0.9314	0.2976	0.022*
C6	0.8320 (3)	1.0474 (3)	0.68275 (18)	0.0235 (5)
H6A	0.7837	1.1742	0.7024	0.035*
H6B	0.9662	0.9980	0.6778	0.035*
H6C	0.7811	0.9840	0.7422	0.035*
C7	0.9465 (3)	0.6237 (3)	0.18139 (16)	0.0147 (4)
C8	1.1358 (3)	0.5800 (3)	0.18110 (17)	0.0164 (4)
C9	1.2314 (3)	0.6356 (3)	0.08962 (17)	0.0171 (4)
H9	1.3583	0.6089	0.0904	0.021*
C10	1.1491 (3)	0.7289 (3)	−0.00333 (17)	0.0179 (4)
C11	0.9640 (3)	0.7663 (3)	−0.00193 (17)	0.0188 (4)
H11	0.9062	0.8285	−0.0652	0.023*
C12	0.8585 (3)	0.7172 (3)	0.08756 (17)	0.0170 (4)
C13	1.2450 (3)	0.4724 (3)	0.27382 (18)	0.0198 (4)
H13A	1.3601	0.4910	0.2691	0.030*
H13B	1.2725	0.3456	0.2630	0.030*
H13C	1.1731	0.5110	0.3493	0.030*
C14	1.2579 (3)	0.7826 (3)	−0.10316 (18)	0.0236 (5)
H14A	1.1801	0.8970	−0.1336	0.035*
H14B	1.3002	0.6915	−0.1633	0.035*
H14C	1.3643	0.7943	−0.0775	0.035*
C15	0.6587 (3)	0.7662 (3)	0.07493 (18)	0.0213 (5)
H15A	0.6326	0.8291	0.0022	0.032*
H15B	0.5807	0.8435	0.1388	0.032*
H15C	0.6334	0.6576	0.0756	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0155 (3)	0.0159 (3)	0.0150 (2)	−0.0066 (2)	−0.00188 (18)	0.00050 (18)
O1	0.0232 (8)	0.0151 (7)	0.0206 (8)	−0.0089 (6)	−0.0042 (6)	0.0029 (6)
O2	0.0148 (7)	0.0257 (8)	0.0215 (8)	−0.0088 (6)	−0.0014 (6)	−0.0003 (6)
N1	0.0155 (8)	0.0153 (9)	0.0164 (9)	−0.0057 (7)	−0.0022 (7)	0.0026 (7)
N2	0.0199 (9)	0.0156 (9)	0.0142 (8)	−0.0060 (7)	−0.0031 (7)	0.0005 (7)
C1	0.0132 (9)	0.0208 (10)	0.0136 (9)	−0.0077 (8)	0.0013 (7)	0.0004 (8)
C2	0.0142 (9)	0.0183 (10)	0.0182 (10)	−0.0059 (8)	0.0014 (8)	−0.0020 (8)
C3	0.0187 (10)	0.0166 (10)	0.0201 (10)	−0.0053 (8)	0.0009 (8)	−0.0011 (8)
C4	0.0170 (10)	0.0180 (11)	0.0207 (11)	−0.0032 (8)	−0.0012 (8)	0.0049 (8)
C5	0.0164 (10)	0.0217 (11)	0.0155 (10)	−0.0056 (8)	−0.0016 (8)	0.0013 (8)
C6	0.0269 (12)	0.0210 (11)	0.0228 (11)	−0.0084 (9)	−0.0054 (9)	−0.0016 (9)
C7	0.0171 (10)	0.0134 (10)	0.0139 (9)	−0.0065 (8)	−0.0010 (8)	−0.0008 (7)
C8	0.0183 (10)	0.0128 (10)	0.0179 (10)	−0.0054 (8)	−0.0022 (8)	−0.0026 (8)
C9	0.0137 (9)	0.0188 (10)	0.0195 (10)	−0.0069 (8)	−0.0008 (8)	−0.0028 (8)
C10	0.0231 (11)	0.0156 (10)	0.0157 (10)	−0.0087 (8)	−0.0004 (8)	−0.0021 (8)
C11	0.0227 (11)	0.0171 (10)	0.0153 (10)	−0.0056 (9)	−0.0051 (8)	0.0015 (8)
C12	0.0177 (10)	0.0154 (10)	0.0173 (10)	−0.0052 (8)	−0.0036 (8)	−0.0018 (8)
C13	0.0168 (10)	0.0198 (11)	0.0220 (11)	−0.0060 (9)	−0.0047 (8)	0.0037 (8)
C14	0.0267 (11)	0.0254 (12)	0.0207 (11)	−0.0139 (10)	0.0013 (9)	0.0004 (9)
C15	0.0206 (11)	0.0251 (12)	0.0178 (10)	−0.0074 (9)	−0.0064 (8)	0.0022 (9)

Geometric parameters (Å, º)

S1—O1	1.4504 (15)	C7—C12	1.418 (3)
S1—O2	1.4434 (14)	C8—C9	1.386 (3)
S1—N2	1.5940 (17)	C8—C13	1.516 (3)
S1—C7	1.793 (2)	C9—C10	1.392 (3)
N1—C2	1.365 (3)	C9—H9	0.9500
N1—C1	1.370 (3)	C10—C11	1.384 (3)
N1—H1N	0.86 (2)	C10—C14	1.506 (3)
N2—C1	1.336 (3)	C11—C12	1.391 (3)
C1—C5	1.415 (3)	C11—H11	0.9500
C2—C3	1.364 (3)	C12—C15	1.513 (3)
C2—C6	1.496 (3)	C13—H13A	0.9800
C3—C4	1.400 (3)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C4—C5	1.370 (3)	C14—H14A	0.9800
C4—H4	0.9500	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—H6A	0.9800	C15—H15A	0.9800
C6—H6B	0.9800	C15—H15B	0.9800
C6—H6C	0.9800	C15—H15C	0.9800
C7—C8	1.410 (3)
O1—S1—O2	115.15 (9)	C9—C8—C7	118.65 (18)
O1—S1—N2	105.04 (9)	C9—C8—C13	116.94 (17)
O2—S1—N2	113.34 (9)	C7—C8—C13	124.40 (18)
O1—S1—C7	106.20 (9)	C8—C9—C10	122.68 (18)
O2—S1—C7	109.16 (9)	C8—C9—H9	118.7
N2—S1—C7	107.44 (9)	C10—C9—H9	118.7
C2—N1—C1	124.98 (18)	C11—C10—C9	117.36 (18)
C2—N1—H1N	117.0 (15)	C11—C10—C14	121.18 (18)
C1—N1—H1N	118.0 (15)	C9—C10—C14	121.43 (18)
C1—N2—S1	122.42 (14)	C10—C11—C12	123.24 (19)
N2—C1—N1	113.68 (17)	C10—C11—H11	118.4
N2—C1—C5	130.48 (19)	C12—C11—H11	118.4
N1—C1—C5	115.83 (18)	C11—C12—C7	117.89 (18)
C3—C2—N1	118.79 (19)	C11—C12—C15	116.56 (18)
C3—C2—C6	124.28 (19)	C7—C12—C15	125.54 (18)
N1—C2—C6	116.93 (18)	C8—C13—H13A	109.5
C2—C3—C4	118.86 (19)	C8—C13—H13B	109.5
C2—C3—H3	120.6	H13A—C13—H13B	109.5
C4—C3—H3	120.6	C8—C13—H13C	109.5
C5—C4—C3	121.48 (19)	H13A—C13—H13C	109.5
C5—C4—H4	119.3	H13B—C13—H13C	109.5
C3—C4—H4	119.3	C10—C14—H14A	109.5
C4—C5—C1	119.99 (19)	C10—C14—H14B	109.5
C4—C5—H5	120.0	H14A—C14—H14B	109.5
C1—C5—H5	120.0	C10—C14—H14C	109.5
C2—C6—H6A	109.5	H14A—C14—H14C	109.5
C2—C6—H6B	109.5	H14B—C14—H14C	109.5
H6A—C6—H6B	109.5	C12—C15—H15A	109.5
C2—C6—H6C	109.5	C12—C15—H15B	109.5
H6A—C6—H6C	109.5	H15A—C15—H15B	109.5
H6B—C6—H6C	109.5	C12—C15—H15C	109.5
C8—C7—C12	120.14 (18)	H15A—C15—H15C	109.5
C8—C7—S1	117.37 (14)	H15B—C15—H15C	109.5
C12—C7—S1	122.46 (15)
O1—S1—N2—C1	176.23 (15)	O1—S1—C7—C12	124.46 (16)
O2—S1—N2—C1	−57.23 (18)	N2—S1—C7—C12	−123.54 (17)
C7—S1—N2—C1	63.45 (17)	C12—C7—C8—C9	2.2 (3)
S1—N2—C1—N1	−176.39 (13)	S1—C7—C8—C9	−179.41 (14)
S1—N2—C1—C5	2.4 (3)	C12—C7—C8—C13	−176.71 (18)
C2—N1—C1—N2	−178.80 (17)	S1—C7—C8—C13	1.7 (3)
C2—N1—C1—C5	2.2 (3)	C7—C8—C9—C10	−1.7 (3)
C1—N1—C2—C3	−3.1 (3)	C13—C8—C9—C10	177.32 (18)
C1—N1—C2—C6	176.22 (18)	C8—C9—C10—C11	0.2 (3)
N1—C2—C3—C4	1.6 (3)	C8—C9—C10—C14	−178.12 (18)
C6—C2—C3—C4	−177.67 (19)	C9—C10—C11—C12	0.8 (3)
C2—C3—C4—C5	0.5 (3)	C14—C10—C11—C12	179.10 (19)
C3—C4—C5—C1	−1.3 (3)	C10—C11—C12—C7	−0.3 (3)
N2—C1—C5—C4	−178.71 (19)	C10—C11—C12—C15	−179.20 (19)
N1—C1—C5—C4	0.0 (3)	C8—C7—C12—C11	−1.3 (3)
O1—S1—C7—C8	−53.92 (17)	S1—C7—C12—C11	−179.59 (14)
O2—S1—C7—C8	−178.64 (14)	C8—C7—C12—C15	177.58 (18)
N2—S1—C7—C8	58.08 (17)	S1—C7—C12—C15	−0.8 (3)
O2—S1—C7—C12	−0.26 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^i	0.86 (2)	2.05 (2)	2.879 (2)	161.9

Symmetry code: (i) −x+2, −y+1, −z+1.