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In the solid obtained from N-(6-methyl­pyridin-2-yl)mesitylenesulfonamide and acetic acid, the constituents inter­act via two N—H...O hydrogen bonds. The H atom situated in one of these short contacts is disordered over two positions: one of these positions is formally associated with an adduct of the neutral sul­fon­amide molecule and the neutral acetic acid molecule, and corresponds to a cocrystal, while the alternative site is associated with salt formation between a protonated sulfonamide molecule and deprotonated acetic acid molecule. Site-occupancy refinements and electron densities from difference Fourier maps suggest a trend with temperature, albeit of limited significance; the cocrystal is more relevant at 100 K, whereas the intensity data collected at room temperature match the description as cocrystal and salt equally well.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615012826/fn3199sup1.cif
Contains datablocks 1_at_100K, 1_at_200K, 1_at_293K, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012826/fn31991_at_100Ksup2.hkl
Contains datablock 1_at_100K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012826/fn31991_at_200Ksup3.hkl
Contains datablock 1_at_200K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229615012826/fn31991_at_293Ksup4.hkl
Contains datablock 1_at_293K

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229615012826/fn31991_at_100Ksup5.cml
Supplementary material

CCDC references: 1410295; 1410294; 1410293

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

(1_at_100K) 2,4,6-Trimethyl-N-(6-methylpyridin-2-yl)benzenesulfonamide; acetic acid top
Crystal data top
C15H18.37N2O2S·C2H3.63O2Z = 2
Mr = 350.42F(000) = 372
Triclinic, P1Dx = 1.338 Mg m3
a = 7.9551 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.8780 (8) ÅCell parameters from 4063 reflections
c = 13.9793 (12) Åθ = 2.7–29.9°
α = 101.2458 (12)°µ = 0.21 mm1
β = 90.5899 (12)°T = 100 K
γ = 115.4199 (10)°Block, colourless
V = 869.65 (13) Å30.32 × 0.23 × 0.22 mm
Data collection top
Bruker APEX CCD
diffractometer
4211 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus sourceRint = 0.027
ω scansθmax = 29.5°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1111
Tmin = 0.667, Tmax = 0.746k = 1212
12172 measured reflectionsl = 1919
4746 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.0603P)2 + 0.3142P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4746 reflectionsΔρmax = 0.45 e Å3
234 parametersΔρmin = 0.44 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.52490 (4)0.15765 (4)0.22346 (2)0.01542 (10)
O10.51631 (14)0.00817 (12)0.25208 (7)0.0196 (2)
O20.35314 (13)0.15864 (12)0.19261 (7)0.0199 (2)
N10.69825 (16)0.56838 (14)0.42558 (8)0.0171 (2)
N20.62855 (17)0.31180 (14)0.32041 (8)0.0172 (2)
H20.666 (3)0.282 (3)0.3686 (19)0.056 (7)*
C10.63794 (18)0.47477 (16)0.33374 (9)0.0153 (2)
C20.71512 (19)0.72987 (17)0.44860 (10)0.0193 (3)
C30.6695 (2)0.80161 (17)0.37911 (11)0.0211 (3)
H30.67950.91430.39610.025*
C40.6087 (2)0.70476 (18)0.28371 (11)0.0225 (3)
H40.57780.75200.23470.027*
C50.5929 (2)0.54059 (17)0.25966 (10)0.0206 (3)
H50.55250.47420.19450.025*
C60.7892 (2)0.82699 (19)0.55255 (11)0.0271 (3)
H6A0.72600.75360.59760.041*
H6B0.76590.92850.56570.041*
H6C0.92420.86220.56200.041*
C70.67861 (17)0.20362 (16)0.13053 (9)0.0148 (2)
C80.62153 (18)0.22380 (17)0.03947 (10)0.0169 (2)
C90.74838 (19)0.25246 (18)0.03085 (10)0.0203 (3)
H90.71210.26660.09220.024*
C100.9248 (2)0.26123 (19)0.01509 (11)0.0226 (3)
C110.97672 (19)0.24052 (19)0.07510 (10)0.0211 (3)
H111.09760.24670.08680.025*
C120.85743 (18)0.21099 (16)0.14879 (10)0.0169 (2)
C130.43349 (19)0.21388 (19)0.00909 (10)0.0210 (3)
H13A0.42610.21900.06010.032*
H13B0.41880.31010.04940.032*
H13C0.33370.10610.01840.032*
C141.0535 (2)0.2880 (3)0.09517 (12)0.0330 (4)
H14A1.01220.18110.14480.050*
H14B1.18150.32290.06700.050*
H14C1.05050.37730.12570.050*
C150.92899 (19)0.18510 (19)0.24173 (10)0.0206 (3)
H15A1.05660.19690.23660.031*
H15B0.84750.07050.25120.031*
H15C0.92930.27110.29770.031*
O30.79216 (18)0.47276 (13)0.57885 (8)0.0298 (3)
H1A0.756 (4)0.489 (4)0.529 (2)0.022 (6)*0.63 (3)
H1B0.737 (6)0.533 (6)0.472 (3)0.022 (6)*0.37 (3)
O40.75826 (18)0.22701 (14)0.48352 (8)0.0299 (3)
C160.79743 (19)0.32612 (17)0.56443 (10)0.0196 (3)
C170.8522 (2)0.28456 (19)0.65526 (11)0.0243 (3)
H17A0.74090.19990.67670.036*
H17B0.90860.38870.70730.036*
H17C0.94300.23780.64120.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01636 (16)0.01487 (16)0.01695 (17)0.00813 (12)0.00343 (11)0.00463 (12)
O10.0239 (5)0.0154 (4)0.0212 (5)0.0092 (4)0.0044 (4)0.0062 (4)
O20.0162 (5)0.0231 (5)0.0224 (5)0.0105 (4)0.0034 (4)0.0047 (4)
N10.0192 (5)0.0166 (5)0.0158 (5)0.0084 (4)0.0020 (4)0.0026 (4)
N20.0252 (6)0.0152 (5)0.0143 (5)0.0119 (4)0.0012 (4)0.0028 (4)
C10.0180 (6)0.0149 (6)0.0151 (6)0.0089 (5)0.0035 (4)0.0035 (4)
C20.0202 (6)0.0175 (6)0.0196 (6)0.0086 (5)0.0035 (5)0.0018 (5)
C30.0263 (7)0.0161 (6)0.0234 (7)0.0117 (5)0.0040 (5)0.0041 (5)
C40.0311 (7)0.0208 (6)0.0211 (7)0.0151 (6)0.0030 (5)0.0080 (5)
C50.0305 (7)0.0193 (6)0.0152 (6)0.0139 (6)0.0020 (5)0.0037 (5)
C60.0386 (8)0.0197 (7)0.0206 (7)0.0130 (6)0.0016 (6)0.0010 (5)
C70.0158 (6)0.0150 (6)0.0145 (6)0.0074 (5)0.0024 (4)0.0035 (4)
C80.0170 (6)0.0182 (6)0.0167 (6)0.0090 (5)0.0004 (5)0.0035 (5)
C90.0220 (7)0.0258 (7)0.0156 (6)0.0121 (5)0.0013 (5)0.0065 (5)
C100.0204 (7)0.0302 (7)0.0197 (7)0.0123 (6)0.0053 (5)0.0075 (6)
C110.0164 (6)0.0286 (7)0.0206 (7)0.0119 (5)0.0029 (5)0.0060 (5)
C120.0169 (6)0.0178 (6)0.0166 (6)0.0087 (5)0.0009 (5)0.0027 (5)
C130.0212 (6)0.0279 (7)0.0184 (6)0.0150 (6)0.0004 (5)0.0048 (5)
C140.0271 (8)0.0559 (11)0.0236 (8)0.0222 (8)0.0110 (6)0.0154 (7)
C150.0198 (6)0.0276 (7)0.0176 (6)0.0128 (5)0.0000 (5)0.0061 (5)
O30.0503 (7)0.0195 (5)0.0194 (5)0.0161 (5)0.0059 (5)0.0023 (4)
O40.0504 (7)0.0275 (6)0.0192 (5)0.0250 (5)0.0002 (5)0.0026 (4)
C160.0203 (6)0.0186 (6)0.0187 (6)0.0070 (5)0.0016 (5)0.0054 (5)
C170.0298 (7)0.0244 (7)0.0199 (7)0.0117 (6)0.0005 (5)0.0081 (5)
Geometric parameters (Å, º) top
S1—O11.4338 (9)C9—H90.9500
S1—O21.4327 (10)C9—C101.3843 (19)
S1—N21.6354 (12)C10—C111.393 (2)
S1—C71.7777 (13)C10—C141.5090 (19)
N1—C11.3408 (17)C11—H110.9500
N1—C21.3532 (17)C11—C121.3937 (18)
N1—H1B0.883 (19)C12—C151.5095 (18)
N2—H20.86 (3)C13—H13A0.9800
N2—C11.3912 (16)C13—H13B0.9800
C1—C51.3967 (18)C13—H13C0.9800
C2—C31.383 (2)C14—H14A0.9800
C2—C61.503 (2)C14—H14B0.9800
C3—H30.9500C14—H14C0.9800
C3—C41.391 (2)C15—H15A0.9800
C4—H40.9500C15—H15B0.9800
C4—C51.3797 (18)C15—H15C0.9800
C5—H50.9500O3—H1A0.81 (3)
C6—H6A0.9800O3—C161.2968 (17)
C6—H6B0.9800O4—C161.2328 (17)
C6—H6C0.9800C16—C171.4993 (19)
C7—C81.4162 (18)C17—H17A0.9800
C7—C121.4139 (17)C17—H17B0.9800
C8—C91.3954 (18)C17—H17C0.9800
C8—C131.5116 (18)
O1—S1—N2104.29 (6)C10—C9—C8122.86 (12)
O1—S1—C7108.54 (6)C10—C9—H9118.6
O2—S1—O1118.36 (6)C9—C10—C11118.17 (12)
O2—S1—N2109.03 (6)C9—C10—C14120.25 (13)
O2—S1—C7109.46 (6)C11—C10—C14121.56 (13)
N2—S1—C7106.46 (6)C10—C11—H11118.9
C1—N1—C2120.16 (12)C10—C11—C12122.25 (13)
C1—N1—H1B123 (3)C12—C11—H11118.9
C2—N1—H1B117 (3)C7—C12—C15125.03 (12)
S1—N2—H2115.1 (16)C11—C12—C7118.16 (12)
C1—N2—S1124.95 (10)C11—C12—C15116.79 (12)
C1—N2—H2119.4 (16)C8—C13—H13A109.5
N1—C1—N2113.99 (11)C8—C13—H13B109.5
N1—C1—C5121.44 (12)C8—C13—H13C109.5
N2—C1—C5124.56 (12)H13A—C13—H13B109.5
N1—C2—C3121.30 (13)H13A—C13—H13C109.5
N1—C2—C6116.45 (12)H13B—C13—H13C109.5
C3—C2—C6122.23 (12)C10—C14—H14A109.5
C2—C3—H3120.8C10—C14—H14B109.5
C2—C3—C4118.39 (12)C10—C14—H14C109.5
C4—C3—H3120.8H14A—C14—H14B109.5
C3—C4—H4119.7H14A—C14—H14C109.5
C5—C4—C3120.52 (13)H14B—C14—H14C109.5
C5—C4—H4119.7C12—C15—H15A109.5
C1—C5—H5120.9C12—C15—H15B109.5
C4—C5—C1118.17 (13)C12—C15—H15C109.5
C4—C5—H5120.9H15A—C15—H15B109.5
C2—C6—H6A109.5H15A—C15—H15C109.5
C2—C6—H6B109.5H15B—C15—H15C109.5
C2—C6—H6C109.5C16—O3—H1A112 (2)
H6A—C6—H6B109.5O3—C16—C17114.33 (12)
H6A—C6—H6C109.5O4—C16—O3123.41 (13)
H6B—C6—H6C109.5O4—C16—C17122.25 (13)
C8—C7—S1121.45 (10)C16—C17—H17A109.5
C12—C7—S1117.57 (9)C16—C17—H17B109.5
C12—C7—C8120.91 (11)C16—C17—H17C109.5
C7—C8—C13126.50 (12)H17A—C17—H17B109.5
C9—C8—C7117.65 (12)H17A—C17—H17C109.5
C9—C8—C13115.84 (12)H17B—C17—H17C109.5
C8—C9—H9118.6
S1—N2—C1—N1168.02 (9)C2—N1—C1—N2179.60 (11)
S1—N2—C1—C513.02 (19)C2—N1—C1—C50.61 (19)
S1—C7—C8—C9177.32 (10)C2—C3—C4—C50.6 (2)
S1—C7—C8—C131.32 (19)C3—C4—C5—C10.6 (2)
S1—C7—C12—C11177.63 (10)C6—C2—C3—C4177.56 (13)
S1—C7—C12—C150.85 (18)C7—S1—N2—C177.55 (12)
O1—S1—N2—C1167.78 (11)C7—C8—C9—C100.2 (2)
O1—S1—C7—C8126.42 (11)C8—C7—C12—C110.69 (19)
O1—S1—C7—C1250.50 (11)C8—C7—C12—C15177.78 (13)
O2—S1—N2—C140.44 (13)C8—C9—C10—C110.0 (2)
O2—S1—C7—C84.11 (13)C8—C9—C10—C14178.40 (14)
O2—S1—C7—C12178.97 (9)C9—C10—C11—C120.2 (2)
N1—C1—C5—C41.2 (2)C10—C11—C12—C70.6 (2)
N1—C2—C3—C41.2 (2)C10—C11—C12—C15178.04 (13)
N2—S1—C7—C8121.83 (11)C12—C7—C8—C90.51 (19)
N2—S1—C7—C1261.25 (11)C12—C7—C8—C13178.14 (12)
N2—C1—C5—C4179.94 (13)C13—C8—C9—C10178.61 (13)
C1—N1—C2—C30.6 (2)C14—C10—C11—C12178.18 (14)
C1—N1—C2—C6178.21 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1A···N10.81 (3)1.86 (3))2.6628 (17)170 (3)
N1—H1B···O30.88 (5)1.79 (4)2.6628 (17)171 (5)
N2—H2···O40.86 (3)1.99 (3)2.8493 (17)177 (2)
(1_at_200K) 2,4,6-Trimethyl-N-(6-methylpyridin-2-yl)benzenesulfonamide; acetic acid top
Crystal data top
C15H18.41N2O2S·C2H3.59O2Z = 2
Mr = 350.42F(000) = 372
Triclinic, P1Dx = 1.317 Mg m3
a = 7.9881 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9052 (13) ÅCell parameters from 2497 reflections
c = 14.053 (3) Åθ = 2.7–25.2°
α = 101.185 (3)°µ = 0.21 mm1
β = 90.964 (3)°T = 200 K
γ = 114.909 (2)°Block, colourless
V = 884.0 (3) Å30.32 × 0.23 × 0.22 mm
Data collection top
Bruker APEX CCD
diffractometer
4007 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus sourceRint = 0.037
ω scansθmax = 30.7°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1011
Tmin = 0.659, Tmax = 0.746k = 1212
13305 measured reflectionsl = 2019
5046 independent reflections
Refinement top
Refinement on F22 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148 w = 1/[σ2(Fo2) + (0.0706P)2 + 0.1843P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
5046 reflectionsΔρmax = 0.39 e Å3
234 parametersΔρmin = 0.35 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.52748 (5)0.16246 (5)0.22364 (3)0.02771 (13)
O10.51955 (18)0.01364 (15)0.25184 (9)0.0356 (3)
O20.35668 (17)0.16402 (16)0.19319 (10)0.0362 (3)
N10.6996 (2)0.57015 (18)0.42350 (10)0.0289 (3)
N20.6307 (2)0.31528 (18)0.31978 (11)0.0309 (3)
H20.667 (4)0.278 (4)0.3672 (18)0.088 (10)*
C10.6409 (2)0.4770 (2)0.33241 (12)0.0272 (3)
C20.7177 (2)0.7309 (2)0.44655 (13)0.0331 (4)
C30.6746 (3)0.8034 (2)0.37714 (14)0.0374 (4)
H30.68500.91580.39390.045*
C40.6160 (3)0.7080 (2)0.28255 (14)0.0403 (4)
H40.58710.75590.23350.048*
C50.5990 (3)0.5447 (2)0.25870 (13)0.0366 (4)
H50.55980.47950.19360.044*
C60.7877 (3)0.8255 (3)0.55062 (15)0.0486 (5)
H6A0.72370.75150.59450.073*
H6B0.76330.92620.56360.073*
H6C0.92160.86050.56160.073*
C70.6784 (2)0.2062 (2)0.13074 (11)0.0253 (3)
C80.6205 (2)0.2249 (2)0.03986 (12)0.0291 (3)
C90.7443 (3)0.2503 (2)0.03031 (13)0.0354 (4)
H90.70690.26300.09160.042*
C100.9195 (3)0.2579 (3)0.01488 (14)0.0380 (4)
C110.9726 (2)0.2397 (3)0.07525 (13)0.0363 (4)
H111.09280.24530.08700.044*
C120.8565 (2)0.2136 (2)0.14879 (12)0.0292 (3)
C130.4332 (3)0.2157 (3)0.00973 (14)0.0385 (4)
H13A0.42490.22060.05920.058*
H13B0.41840.31160.04980.058*
H13C0.33480.10900.01900.058*
C141.0460 (3)0.2821 (4)0.09495 (16)0.0580 (6)
H14A1.02940.17100.13260.087*
H14B1.17540.34790.06600.087*
H14C1.01520.34310.13820.087*
C150.9301 (3)0.1902 (3)0.24182 (13)0.0373 (4)
H15A1.05410.19490.23520.056*
H15B0.84640.07980.25420.056*
H15C0.93760.28080.29640.056*
O30.7853 (3)0.46836 (19)0.57647 (11)0.0546 (4)
H1A0.751 (5)0.487 (5)0.528 (3)0.043 (9)*0.59 (3)
H1B0.749 (7)0.535 (7)0.467 (3)0.043 (9)*0.41 (3)
O40.7520 (3)0.2254 (2)0.48283 (11)0.0549 (4)
C160.7900 (3)0.3237 (2)0.56335 (13)0.0350 (4)
C170.8418 (3)0.2804 (3)0.65372 (15)0.0443 (5)
H17A0.73070.19590.67360.066*
H17B0.89600.38300.70610.066*
H17C0.93270.23390.64050.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0295 (2)0.0268 (2)0.0303 (2)0.01453 (16)0.00649 (15)0.00846 (16)
O10.0451 (7)0.0268 (6)0.0378 (7)0.0164 (5)0.0089 (6)0.0116 (5)
O20.0288 (6)0.0432 (7)0.0393 (7)0.0179 (5)0.0064 (5)0.0093 (6)
N10.0339 (7)0.0286 (7)0.0261 (7)0.0154 (6)0.0047 (6)0.0057 (6)
N20.0446 (8)0.0281 (7)0.0263 (7)0.0213 (6)0.0041 (6)0.0066 (6)
C10.0326 (8)0.0272 (8)0.0265 (8)0.0163 (6)0.0080 (6)0.0083 (6)
C20.0376 (9)0.0293 (8)0.0329 (9)0.0159 (7)0.0057 (7)0.0048 (7)
C30.0483 (10)0.0281 (8)0.0404 (10)0.0200 (8)0.0070 (8)0.0095 (7)
C40.0583 (12)0.0362 (10)0.0372 (10)0.0277 (9)0.0064 (9)0.0149 (8)
C50.0539 (11)0.0337 (9)0.0280 (9)0.0240 (8)0.0045 (8)0.0082 (7)
C60.0711 (15)0.0350 (10)0.0363 (11)0.0234 (10)0.0009 (10)0.0001 (8)
C70.0260 (7)0.0267 (7)0.0249 (7)0.0130 (6)0.0033 (6)0.0056 (6)
C80.0283 (8)0.0326 (8)0.0291 (8)0.0158 (7)0.0007 (6)0.0071 (7)
C90.0368 (9)0.0471 (10)0.0272 (8)0.0217 (8)0.0027 (7)0.0111 (7)
C100.0342 (9)0.0524 (11)0.0313 (9)0.0207 (8)0.0081 (7)0.0130 (8)
C110.0275 (8)0.0519 (11)0.0333 (9)0.0204 (8)0.0043 (7)0.0105 (8)
C120.0284 (8)0.0334 (8)0.0268 (8)0.0148 (7)0.0004 (6)0.0058 (6)
C130.0375 (9)0.0541 (11)0.0331 (9)0.0285 (9)0.0008 (7)0.0102 (8)
C140.0459 (12)0.101 (2)0.0407 (12)0.0384 (13)0.0194 (9)0.0276 (13)
C150.0350 (9)0.0521 (11)0.0319 (9)0.0247 (8)0.0000 (7)0.0119 (8)
O30.0938 (13)0.0372 (8)0.0339 (8)0.0311 (8)0.0108 (8)0.0056 (6)
O40.0967 (12)0.0487 (9)0.0333 (7)0.0463 (9)0.0014 (8)0.0058 (6)
C160.0392 (9)0.0328 (9)0.0326 (9)0.0140 (7)0.0038 (7)0.0103 (7)
C170.0549 (12)0.0444 (11)0.0384 (10)0.0227 (9)0.0039 (9)0.0174 (9)
Geometric parameters (Å, º) top
S1—O21.4295 (13)C9—C101.384 (3)
S1—O11.4322 (12)C9—H90.9500
S1—N21.6314 (15)C10—C111.389 (3)
S1—C71.7790 (16)C10—C141.511 (3)
N1—C11.337 (2)C11—C121.388 (2)
N1—C21.349 (2)C11—H110.9500
N1—H1B0.89 (2)C12—C151.510 (2)
N2—C11.384 (2)C13—H13A0.9800
N2—H20.895 (17)C13—H13B0.9800
C1—C51.395 (2)C13—H13C0.9800
C2—C31.381 (3)C14—H14A0.9800
C2—C61.503 (3)C14—H14B0.9800
C3—C41.383 (3)C14—H14C0.9800
C3—H30.9500C15—H15A0.9800
C4—C51.375 (2)C15—H15B0.9800
C4—H40.9500C15—H15C0.9800
C5—H50.9500O3—C161.282 (2)
C6—H6A0.9800O3—H1A0.81 (4)
C6—H6B0.9800O4—C161.232 (2)
C6—H6C0.9800C16—C171.496 (3)
C7—C121.413 (2)C17—H17A0.9800
C7—C81.414 (2)C17—H17B0.9800
C8—C91.390 (2)C17—H17C0.9800
C8—C131.512 (2)
O2—S1—O1118.13 (8)C10—C9—H9118.5
O2—S1—N2109.05 (8)C8—C9—H9118.5
O1—S1—N2104.50 (8)C9—C10—C11117.89 (16)
O2—S1—C7109.51 (8)C9—C10—C14120.38 (17)
O1—S1—C7108.35 (7)C11—C10—C14121.72 (17)
N2—S1—C7106.66 (8)C12—C11—C10122.45 (16)
C1—N1—C2120.79 (15)C12—C11—H11118.8
C1—N1—H1B120 (3)C10—C11—H11118.8
C2—N1—H1B118 (3)C11—C12—C7118.30 (15)
C1—N2—S1124.89 (12)C11—C12—C15116.72 (15)
C1—N2—H2123 (2)C7—C12—C15124.97 (15)
S1—N2—H2111 (2)C8—C13—H13A109.5
N1—C1—N2114.16 (15)C8—C13—H13B109.5
N1—C1—C5120.73 (15)H13A—C13—H13B109.5
N2—C1—C5125.09 (16)C8—C13—H13C109.5
N1—C2—C3121.08 (17)H13A—C13—H13C109.5
N1—C2—C6116.58 (16)H13B—C13—H13C109.5
C3—C2—C6122.34 (17)C10—C14—H14A109.5
C2—C3—C4118.23 (17)C10—C14—H14B109.5
C2—C3—H3120.9H14A—C14—H14B109.5
C4—C3—H3120.9C10—C14—H14C109.5
C5—C4—C3120.78 (17)H14A—C14—H14C109.5
C5—C4—H4119.6H14B—C14—H14C109.5
C3—C4—H4119.6C12—C15—H15A109.5
C4—C5—C1118.37 (17)C12—C15—H15B109.5
C4—C5—H5120.8H15A—C15—H15B109.5
C1—C5—H5120.8C12—C15—H15C109.5
C2—C6—H6A109.5H15A—C15—H15C109.5
C2—C6—H6B109.5H15B—C15—H15C109.5
H6A—C6—H6B109.5C16—O3—H1A114 (3)
C2—C6—H6C109.5O4—C16—O3122.94 (18)
H6A—C6—H6C109.5O4—C16—C17121.99 (17)
H6B—C6—H6C109.5O3—C16—C17115.07 (17)
C12—C7—C8120.64 (15)C16—C17—H17A109.5
C12—C7—S1117.65 (12)C16—C17—H17B109.5
C8—C7—S1121.64 (12)H17A—C17—H17B109.5
C9—C8—C7117.74 (15)C16—C17—H17C109.5
C9—C8—C13115.93 (15)H17A—C17—H17C109.5
C7—C8—C13126.32 (15)H17B—C17—H17C109.5
C10—C9—C8122.99 (16)
O2—S1—N2—C141.20 (16)O1—S1—C7—C8125.73 (14)
O1—S1—N2—C1168.39 (14)N2—S1—C7—C8122.28 (14)
C7—S1—N2—C176.98 (16)C12—C7—C8—C90.1 (2)
C2—N1—C1—N2179.51 (15)S1—C7—C8—C9176.76 (13)
C2—N1—C1—C50.8 (3)C12—C7—C8—C13178.45 (16)
S1—N2—C1—N1167.58 (12)S1—C7—C8—C131.6 (2)
S1—N2—C1—C513.8 (3)C7—C8—C9—C100.0 (3)
C1—N1—C2—C30.6 (3)C13—C8—C9—C10178.55 (18)
C1—N1—C2—C6179.07 (16)C8—C9—C10—C110.2 (3)
N1—C2—C3—C41.4 (3)C8—C9—C10—C14178.7 (2)
C6—C2—C3—C4178.28 (19)C9—C10—C11—C120.4 (3)
C2—C3—C4—C50.8 (3)C14—C10—C11—C12178.5 (2)
C3—C4—C5—C10.6 (3)C10—C11—C12—C70.3 (3)
N1—C1—C5—C41.4 (3)C10—C11—C12—C15178.06 (18)
N2—C1—C5—C4179.92 (17)C8—C7—C12—C110.1 (2)
O2—S1—C7—C12178.69 (12)S1—C7—C12—C11177.03 (13)
O1—S1—C7—C1251.18 (15)C8—C7—C12—C15178.13 (17)
N2—S1—C7—C1260.82 (14)S1—C7—C12—C151.2 (2)
O2—S1—C7—C84.40 (16)
(1_at_293K) 2,4,6-Trimethyl-N-(6-methylpyridin-2-yl)benzenesulfonamide; acetic acid top
Crystal data top
C15H18.47N2O2S·C2H3.53O2Z = 2
Mr = 350.42F(000) = 372
Triclinic, P1Dx = 1.295 Mg m3
a = 8.0257 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9366 (11) ÅCell parameters from 1951 reflections
c = 14.1268 (17) Åθ = 2.7–22.6°
α = 101.0232 (19)°µ = 0.20 mm1
β = 91.2751 (19)°T = 293 K
γ = 114.5422 (17)°Block, colourless
V = 898.78 (19) Å30.32 × 0.23 × 0.22 mm
Data collection top
Bruker APEX CCD
diffractometer
3446 reflections with I > 2σ(I)
Radiation source: Incoatec microfocus sourceRint = 0.038
ω scansθmax = 29.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1010
Tmin = 0.646, Tmax = 0.746k = 1212
12970 measured reflectionsl = 1919
4735 independent reflections
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0792P)2 + 0.1929P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
4735 reflectionsΔρmax = 0.31 e Å3
234 parametersΔρmin = 0.27 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.53004 (7)0.16592 (6)0.22365 (4)0.04126 (17)
O10.5227 (2)0.01775 (18)0.25145 (11)0.0529 (4)
O20.3601 (2)0.1677 (2)0.19352 (12)0.0544 (4)
N10.7013 (2)0.5702 (2)0.42210 (12)0.0420 (4)
N20.6330 (3)0.3171 (2)0.31901 (13)0.0454 (4)
H20.660 (5)0.280 (4)0.364 (3)0.102 (11)*
C10.6434 (3)0.4783 (2)0.33131 (14)0.0397 (4)
C20.7195 (3)0.7303 (3)0.44506 (16)0.0477 (5)
C30.6794 (4)0.8032 (3)0.37584 (18)0.0544 (6)
H30.69070.91320.39190.065*
C40.6220 (4)0.7093 (3)0.28211 (18)0.0590 (6)
H40.59500.75690.23420.071*
C50.6040 (4)0.5472 (3)0.25831 (16)0.0533 (6)
H50.56640.48460.19480.064*
C60.7858 (4)0.8224 (3)0.54898 (19)0.0703 (8)
H6A0.72120.74990.59100.105*
H6B0.76280.92120.56130.105*
H6C0.91560.85490.56110.105*
C70.6787 (3)0.2086 (2)0.13086 (14)0.0372 (4)
C80.6195 (3)0.2260 (3)0.04025 (15)0.0424 (5)
C90.7410 (3)0.2493 (3)0.02973 (16)0.0511 (5)
H90.70360.26090.08960.061*
C100.9144 (3)0.2561 (3)0.01488 (17)0.0549 (6)
C110.9688 (3)0.2394 (3)0.07514 (16)0.0528 (6)
H111.08580.24440.08640.063*
C120.8555 (3)0.2154 (3)0.14859 (14)0.0417 (4)
C130.4332 (3)0.2173 (3)0.01027 (17)0.0561 (6)
H13A0.42430.22160.05700.084*
H13B0.41880.31090.04910.084*
H13C0.33800.11370.01960.084*
C141.0392 (4)0.2784 (5)0.0947 (2)0.0856 (10)
H14A1.02810.17020.12850.128*
H14B1.16460.34760.06700.128*
H14C1.00420.33170.13940.128*
C150.9316 (3)0.1949 (3)0.24165 (17)0.0558 (6)
H15A1.05250.19990.23510.084*
H15B0.85190.08800.25470.084*
H15C0.93880.28390.29430.084*
O30.7815 (3)0.4637 (2)0.57454 (14)0.0793 (7)
H1A0.746 (7)0.484 (7)0.527 (4)0.064 (12)*0.53 (4)
H1B0.735 (8)0.529 (7)0.468 (3)0.064 (12)*0.47 (4)
O40.7475 (3)0.2230 (2)0.48187 (13)0.0803 (6)
C160.7856 (3)0.3199 (3)0.56177 (17)0.0508 (5)
C170.8338 (4)0.2749 (3)0.65165 (19)0.0660 (7)
H17A0.72450.19370.67040.099*
H17B0.88700.37430.70290.099*
H17C0.92110.22760.63940.099*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0443 (3)0.0402 (3)0.0432 (3)0.0204 (2)0.0091 (2)0.0119 (2)
O10.0683 (10)0.0388 (8)0.0554 (9)0.0235 (7)0.0138 (8)0.0169 (7)
O20.0425 (8)0.0657 (10)0.0581 (10)0.0259 (7)0.0098 (7)0.0134 (8)
N10.0510 (10)0.0414 (9)0.0373 (9)0.0225 (8)0.0076 (7)0.0101 (7)
N20.0652 (12)0.0418 (9)0.0381 (9)0.0308 (9)0.0061 (8)0.0101 (7)
C10.0489 (11)0.0403 (10)0.0371 (10)0.0241 (9)0.0124 (8)0.0122 (8)
C20.0554 (12)0.0418 (11)0.0486 (12)0.0239 (10)0.0097 (10)0.0087 (9)
C30.0721 (15)0.0409 (11)0.0578 (14)0.0304 (11)0.0101 (12)0.0130 (10)
C40.0864 (18)0.0541 (14)0.0529 (14)0.0415 (13)0.0082 (12)0.0220 (11)
C50.0812 (16)0.0508 (12)0.0378 (11)0.0372 (12)0.0062 (11)0.0108 (9)
C60.102 (2)0.0508 (14)0.0534 (15)0.0341 (14)0.0008 (14)0.0000 (11)
C70.0396 (10)0.0395 (10)0.0357 (10)0.0201 (8)0.0039 (8)0.0084 (8)
C80.0419 (10)0.0495 (11)0.0396 (11)0.0236 (9)0.0002 (8)0.0092 (9)
C90.0532 (12)0.0686 (15)0.0368 (11)0.0301 (11)0.0022 (9)0.0147 (10)
C100.0496 (12)0.0748 (16)0.0460 (12)0.0302 (11)0.0111 (10)0.0172 (11)
C110.0403 (11)0.0763 (16)0.0484 (13)0.0306 (11)0.0051 (9)0.0154 (11)
C120.0409 (10)0.0499 (11)0.0364 (10)0.0224 (9)0.0001 (8)0.0079 (8)
C130.0523 (13)0.0803 (17)0.0475 (13)0.0401 (12)0.0028 (10)0.0141 (12)
C140.0729 (18)0.146 (3)0.0598 (17)0.059 (2)0.0294 (14)0.0398 (19)
C150.0538 (13)0.0781 (17)0.0460 (12)0.0370 (12)0.0003 (10)0.0179 (12)
O30.138 (2)0.0546 (11)0.0485 (11)0.0461 (12)0.0117 (12)0.0088 (9)
O40.1402 (19)0.0693 (12)0.0498 (10)0.0645 (13)0.0034 (11)0.0096 (9)
C160.0569 (13)0.0506 (12)0.0464 (12)0.0222 (10)0.0062 (10)0.0161 (10)
C170.0823 (18)0.0691 (17)0.0554 (15)0.0354 (14)0.0071 (13)0.0266 (13)
Geometric parameters (Å, º) top
S1—O21.4274 (16)C9—C101.377 (3)
S1—O11.4304 (15)C9—H90.9300
S1—N21.6278 (19)C10—C111.390 (3)
S1—C71.780 (2)C10—C141.512 (3)
N1—C11.338 (3)C11—C121.384 (3)
N1—C21.350 (3)C11—H110.9300
N1—H1B0.89 (2)C12—C151.512 (3)
N2—C11.384 (3)C13—H13A0.9600
N2—H20.83 (4)C13—H13B0.9600
C1—C51.390 (3)C13—H13C0.9600
C2—C31.374 (3)C14—H14A0.9600
C2—C61.502 (3)C14—H14B0.9600
C3—C41.377 (3)C14—H14C0.9600
C3—H30.9300C15—H15A0.9600
C4—C51.368 (3)C15—H15B0.9600
C4—H40.9300C15—H15C0.9600
C5—H50.9300O3—C161.278 (3)
C6—H6A0.9600O3—H1A0.80 (6)
C6—H6B0.9600O4—C161.228 (3)
C6—H6C0.9600C16—C171.492 (3)
C7—C121.409 (3)C17—H17A0.9600
C7—C81.414 (3)C17—H17B0.9600
C8—C91.388 (3)C17—H17C0.9600
C8—C131.511 (3)
O2—S1—O1117.90 (10)C10—C9—H9118.4
O2—S1—N2109.21 (10)C8—C9—H9118.4
O1—S1—N2104.59 (10)C9—C10—C11117.7 (2)
O2—S1—C7109.50 (9)C9—C10—C14120.7 (2)
O1—S1—C7108.25 (9)C11—C10—C14121.5 (2)
N2—S1—C7106.78 (10)C10—C11—C12122.5 (2)
C1—N1—C2120.79 (18)C10—C11—H11118.7
C1—N1—H1B121 (4)C12—C11—H11118.7
C2—N1—H1B118 (4)C11—C12—C7118.30 (18)
C1—N2—S1124.80 (16)C11—C12—C15116.53 (19)
C1—N2—H2123 (2)C7—C12—C15125.15 (19)
S1—N2—H2111 (2)C8—C13—H13A109.5
N1—C1—N2114.03 (18)C8—C13—H13B109.5
N1—C1—C5120.49 (19)H13A—C13—H13B109.5
N2—C1—C5125.46 (19)C8—C13—H13C109.5
N1—C2—C3120.9 (2)H13A—C13—H13C109.5
N1—C2—C6116.5 (2)H13B—C13—H13C109.5
C3—C2—C6122.6 (2)C10—C14—H14A109.5
C2—C3—C4118.3 (2)C10—C14—H14B109.5
C2—C3—H3120.8H14A—C14—H14B109.5
C4—C3—H3120.8C10—C14—H14C109.5
C5—C4—C3121.0 (2)H14A—C14—H14C109.5
C5—C4—H4119.5H14B—C14—H14C109.5
C3—C4—H4119.5C12—C15—H15A109.5
C4—C5—C1118.4 (2)C12—C15—H15B109.5
C4—C5—H5120.8H15A—C15—H15B109.5
C1—C5—H5120.8C12—C15—H15C109.5
C2—C6—H6A109.5H15A—C15—H15C109.5
C2—C6—H6B109.5H15B—C15—H15C109.5
H6A—C6—H6B109.5C16—O3—H1A115 (4)
C2—C6—H6C109.5O4—C16—O3122.7 (2)
H6A—C6—H6C109.5O4—C16—C17122.1 (2)
H6B—C6—H6C109.5O3—C16—C17115.2 (2)
C12—C7—C8120.59 (18)C16—C17—H17A109.5
C12—C7—S1117.65 (15)C16—C17—H17B109.5
C8—C7—S1121.67 (15)H17A—C17—H17B109.5
C9—C8—C7117.64 (18)C16—C17—H17C109.5
C9—C8—C13115.94 (19)H17A—C17—H17C109.5
C7—C8—C13126.40 (19)H17B—C17—H17C109.5
C10—C9—C8123.2 (2)
O2—S1—N2—C141.6 (2)O1—S1—C7—C8125.07 (17)
O1—S1—N2—C1168.71 (17)N2—S1—C7—C8122.81 (17)
C7—S1—N2—C176.68 (19)C12—C7—C8—C90.2 (3)
C2—N1—C1—N2179.58 (18)S1—C7—C8—C9176.28 (16)
C2—N1—C1—C51.2 (3)C12—C7—C8—C13178.5 (2)
S1—N2—C1—N1167.21 (15)S1—C7—C8—C132.0 (3)
S1—N2—C1—C514.5 (3)C7—C8—C9—C100.0 (3)
C1—N1—C2—C30.1 (3)C13—C8—C9—C10178.4 (2)
C1—N1—C2—C6179.9 (2)C8—C9—C10—C110.3 (4)
N1—C2—C3—C40.7 (4)C8—C9—C10—C14178.8 (2)
C6—C2—C3—C4179.1 (2)C9—C10—C11—C120.4 (4)
C2—C3—C4—C50.4 (4)C14—C10—C11—C12178.7 (2)
C3—C4—C5—C10.6 (4)C10—C11—C12—C70.2 (4)
N1—C1—C5—C41.4 (4)C10—C11—C12—C15178.5 (2)
N2—C1—C5—C4179.6 (2)C8—C7—C12—C110.1 (3)
O2—S1—C7—C12178.72 (15)S1—C7—C12—C11176.55 (17)
O1—S1—C7—C1251.52 (18)C8—C7—C12—C15178.7 (2)
N2—S1—C7—C1260.59 (17)S1—C7—C12—C152.1 (3)
O2—S1—C7—C84.7 (2)
IR frequencies (cm-1) in the carboxylate/carboxylic acid group top
(1)Sodium acetateAcetic acid
νas160515831717
νsym139014441384
Δ = νasνsym215139333
 

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