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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
CCDC references: 1410295; 1410294; 1410293
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·C2H3.63O2 | Z = 2 |
Mr = 350.42 | F(000) = 372 |
Triclinic, P1 | Dx = 1.338 Mg m−3 |
a = 7.9551 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.8780 (8) Å | Cell parameters from 4063 reflections |
c = 13.9793 (12) Å | θ = 2.7–29.9° |
α = 101.2458 (12)° | µ = 0.21 mm−1 |
β = 90.5899 (12)° | T = 100 K |
γ = 115.4199 (10)° | Block, colourless |
V = 869.65 (13) Å3 | 0.32 × 0.23 × 0.22 mm |
Data collection top
Bruker APEX CCD diffractometer | 4211 reflections with I > 2σ(I) |
Radiation source: Incoatec microfocus source | Rint = 0.027 |
ω scans | θmax = 29.5°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −11→11 |
Tmin = 0.667, Tmax = 0.746 | k = −12→12 |
12172 measured reflections | l = −19→19 |
4746 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H 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 reflections | Δρmax = 0.45 e Å−3 |
234 parameters | Δρmin = −0.44 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.52490 (4) | 0.15765 (4) | 0.22346 (2) | 0.01542 (10) | |
O1 | 0.51631 (14) | 0.00817 (12) | 0.25208 (7) | 0.0196 (2) | |
O2 | 0.35314 (13) | 0.15864 (12) | 0.19261 (7) | 0.0199 (2) | |
N1 | 0.69825 (16) | 0.56838 (14) | 0.42558 (8) | 0.0171 (2) | |
N2 | 0.62855 (17) | 0.31180 (14) | 0.32041 (8) | 0.0172 (2) | |
H2 | 0.666 (3) | 0.282 (3) | 0.3686 (19) | 0.056 (7)* | |
C1 | 0.63794 (18) | 0.47477 (16) | 0.33374 (9) | 0.0153 (2) | |
C2 | 0.71512 (19) | 0.72987 (17) | 0.44860 (10) | 0.0193 (3) | |
C3 | 0.6695 (2) | 0.80161 (17) | 0.37911 (11) | 0.0211 (3) | |
H3 | 0.6795 | 0.9143 | 0.3961 | 0.025* | |
C4 | 0.6087 (2) | 0.70476 (18) | 0.28371 (11) | 0.0225 (3) | |
H4 | 0.5778 | 0.7520 | 0.2347 | 0.027* | |
C5 | 0.5929 (2) | 0.54059 (17) | 0.25966 (10) | 0.0206 (3) | |
H5 | 0.5525 | 0.4742 | 0.1945 | 0.025* | |
C6 | 0.7892 (2) | 0.82699 (19) | 0.55255 (11) | 0.0271 (3) | |
H6A | 0.7260 | 0.7536 | 0.5976 | 0.041* | |
H6B | 0.7659 | 0.9285 | 0.5657 | 0.041* | |
H6C | 0.9242 | 0.8622 | 0.5620 | 0.041* | |
C7 | 0.67861 (17) | 0.20362 (16) | 0.13053 (9) | 0.0148 (2) | |
C8 | 0.62153 (18) | 0.22380 (17) | 0.03947 (10) | 0.0169 (2) | |
C9 | 0.74838 (19) | 0.25246 (18) | −0.03085 (10) | 0.0203 (3) | |
H9 | 0.7121 | 0.2666 | −0.0922 | 0.024* | |
C10 | 0.9248 (2) | 0.26123 (19) | −0.01509 (11) | 0.0226 (3) | |
C11 | 0.97672 (19) | 0.24052 (19) | 0.07510 (10) | 0.0211 (3) | |
H11 | 1.0976 | 0.2467 | 0.0868 | 0.025* | |
C12 | 0.85743 (18) | 0.21099 (16) | 0.14879 (10) | 0.0169 (2) | |
C13 | 0.43349 (19) | 0.21388 (19) | 0.00909 (10) | 0.0210 (3) | |
H13A | 0.4261 | 0.2190 | −0.0601 | 0.032* | |
H13B | 0.4188 | 0.3101 | 0.0494 | 0.032* | |
H13C | 0.3337 | 0.1061 | 0.0184 | 0.032* | |
C14 | 1.0535 (2) | 0.2880 (3) | −0.09517 (12) | 0.0330 (4) | |
H14A | 1.0122 | 0.1811 | −0.1448 | 0.050* | |
H14B | 1.1815 | 0.3229 | −0.0670 | 0.050* | |
H14C | 1.0505 | 0.3773 | −0.1257 | 0.050* | |
C15 | 0.92899 (19) | 0.18510 (19) | 0.24173 (10) | 0.0206 (3) | |
H15A | 1.0566 | 0.1969 | 0.2366 | 0.031* | |
H15B | 0.8475 | 0.0705 | 0.2512 | 0.031* | |
H15C | 0.9293 | 0.2711 | 0.2977 | 0.031* | |
O3 | 0.79216 (18) | 0.47276 (13) | 0.57885 (8) | 0.0298 (3) | |
H1A | 0.756 (4) | 0.489 (4) | 0.529 (2) | 0.022 (6)* | 0.63 (3) |
H1B | 0.737 (6) | 0.533 (6) | 0.472 (3) | 0.022 (6)* | 0.37 (3) |
O4 | 0.75826 (18) | 0.22701 (14) | 0.48352 (8) | 0.0299 (3) | |
C16 | 0.79743 (19) | 0.32612 (17) | 0.56443 (10) | 0.0196 (3) | |
C17 | 0.8522 (2) | 0.28456 (19) | 0.65526 (11) | 0.0243 (3) | |
H17A | 0.7409 | 0.1999 | 0.6767 | 0.036* | |
H17B | 0.9086 | 0.3887 | 0.7073 | 0.036* | |
H17C | 0.9430 | 0.2378 | 0.6412 | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.01636 (16) | 0.01487 (16) | 0.01695 (17) | 0.00813 (12) | 0.00343 (11) | 0.00463 (12) |
O1 | 0.0239 (5) | 0.0154 (4) | 0.0212 (5) | 0.0092 (4) | 0.0044 (4) | 0.0062 (4) |
O2 | 0.0162 (5) | 0.0231 (5) | 0.0224 (5) | 0.0105 (4) | 0.0034 (4) | 0.0047 (4) |
N1 | 0.0192 (5) | 0.0166 (5) | 0.0158 (5) | 0.0084 (4) | 0.0020 (4) | 0.0026 (4) |
N2 | 0.0252 (6) | 0.0152 (5) | 0.0143 (5) | 0.0119 (4) | 0.0012 (4) | 0.0028 (4) |
C1 | 0.0180 (6) | 0.0149 (6) | 0.0151 (6) | 0.0089 (5) | 0.0035 (4) | 0.0035 (4) |
C2 | 0.0202 (6) | 0.0175 (6) | 0.0196 (6) | 0.0086 (5) | 0.0035 (5) | 0.0018 (5) |
C3 | 0.0263 (7) | 0.0161 (6) | 0.0234 (7) | 0.0117 (5) | 0.0040 (5) | 0.0041 (5) |
C4 | 0.0311 (7) | 0.0208 (6) | 0.0211 (7) | 0.0151 (6) | 0.0030 (5) | 0.0080 (5) |
C5 | 0.0305 (7) | 0.0193 (6) | 0.0152 (6) | 0.0139 (6) | 0.0020 (5) | 0.0037 (5) |
C6 | 0.0386 (8) | 0.0197 (7) | 0.0206 (7) | 0.0130 (6) | −0.0016 (6) | −0.0010 (5) |
C7 | 0.0158 (6) | 0.0150 (6) | 0.0145 (6) | 0.0074 (5) | 0.0024 (4) | 0.0035 (4) |
C8 | 0.0170 (6) | 0.0182 (6) | 0.0167 (6) | 0.0090 (5) | 0.0004 (5) | 0.0035 (5) |
C9 | 0.0220 (7) | 0.0258 (7) | 0.0156 (6) | 0.0121 (5) | 0.0013 (5) | 0.0065 (5) |
C10 | 0.0204 (7) | 0.0302 (7) | 0.0197 (7) | 0.0123 (6) | 0.0053 (5) | 0.0075 (6) |
C11 | 0.0164 (6) | 0.0286 (7) | 0.0206 (7) | 0.0119 (5) | 0.0029 (5) | 0.0060 (5) |
C12 | 0.0169 (6) | 0.0178 (6) | 0.0166 (6) | 0.0087 (5) | 0.0009 (5) | 0.0027 (5) |
C13 | 0.0212 (6) | 0.0279 (7) | 0.0184 (6) | 0.0150 (6) | 0.0004 (5) | 0.0048 (5) |
C14 | 0.0271 (8) | 0.0559 (11) | 0.0236 (8) | 0.0222 (8) | 0.0110 (6) | 0.0154 (7) |
C15 | 0.0198 (6) | 0.0276 (7) | 0.0176 (6) | 0.0128 (5) | 0.0000 (5) | 0.0061 (5) |
O3 | 0.0503 (7) | 0.0195 (5) | 0.0194 (5) | 0.0161 (5) | −0.0059 (5) | 0.0023 (4) |
O4 | 0.0504 (7) | 0.0275 (6) | 0.0192 (5) | 0.0250 (5) | −0.0002 (5) | 0.0026 (4) |
C16 | 0.0203 (6) | 0.0186 (6) | 0.0187 (6) | 0.0070 (5) | 0.0016 (5) | 0.0054 (5) |
C17 | 0.0298 (7) | 0.0244 (7) | 0.0199 (7) | 0.0117 (6) | 0.0005 (5) | 0.0081 (5) |
Geometric parameters (Å, º) top
S1—O1 | 1.4338 (9) | C9—H9 | 0.9500 |
S1—O2 | 1.4327 (10) | C9—C10 | 1.3843 (19) |
S1—N2 | 1.6354 (12) | C10—C11 | 1.393 (2) |
S1—C7 | 1.7777 (13) | C10—C14 | 1.5090 (19) |
N1—C1 | 1.3408 (17) | C11—H11 | 0.9500 |
N1—C2 | 1.3532 (17) | C11—C12 | 1.3937 (18) |
N1—H1B | 0.883 (19) | C12—C15 | 1.5095 (18) |
N2—H2 | 0.86 (3) | C13—H13A | 0.9800 |
N2—C1 | 1.3912 (16) | C13—H13B | 0.9800 |
C1—C5 | 1.3967 (18) | C13—H13C | 0.9800 |
C2—C3 | 1.383 (2) | C14—H14A | 0.9800 |
C2—C6 | 1.503 (2) | C14—H14B | 0.9800 |
C3—H3 | 0.9500 | C14—H14C | 0.9800 |
C3—C4 | 1.391 (2) | C15—H15A | 0.9800 |
C4—H4 | 0.9500 | C15—H15B | 0.9800 |
C4—C5 | 1.3797 (18) | C15—H15C | 0.9800 |
C5—H5 | 0.9500 | O3—H1A | 0.81 (3) |
C6—H6A | 0.9800 | O3—C16 | 1.2968 (17) |
C6—H6B | 0.9800 | O4—C16 | 1.2328 (17) |
C6—H6C | 0.9800 | C16—C17 | 1.4993 (19) |
C7—C8 | 1.4162 (18) | C17—H17A | 0.9800 |
C7—C12 | 1.4139 (17) | C17—H17B | 0.9800 |
C8—C9 | 1.3954 (18) | C17—H17C | 0.9800 |
C8—C13 | 1.5116 (18) | | |
| | | |
O1—S1—N2 | 104.29 (6) | C10—C9—C8 | 122.86 (12) |
O1—S1—C7 | 108.54 (6) | C10—C9—H9 | 118.6 |
O2—S1—O1 | 118.36 (6) | C9—C10—C11 | 118.17 (12) |
O2—S1—N2 | 109.03 (6) | C9—C10—C14 | 120.25 (13) |
O2—S1—C7 | 109.46 (6) | C11—C10—C14 | 121.56 (13) |
N2—S1—C7 | 106.46 (6) | C10—C11—H11 | 118.9 |
C1—N1—C2 | 120.16 (12) | C10—C11—C12 | 122.25 (13) |
C1—N1—H1B | 123 (3) | C12—C11—H11 | 118.9 |
C2—N1—H1B | 117 (3) | C7—C12—C15 | 125.03 (12) |
S1—N2—H2 | 115.1 (16) | C11—C12—C7 | 118.16 (12) |
C1—N2—S1 | 124.95 (10) | C11—C12—C15 | 116.79 (12) |
C1—N2—H2 | 119.4 (16) | C8—C13—H13A | 109.5 |
N1—C1—N2 | 113.99 (11) | C8—C13—H13B | 109.5 |
N1—C1—C5 | 121.44 (12) | C8—C13—H13C | 109.5 |
N2—C1—C5 | 124.56 (12) | H13A—C13—H13B | 109.5 |
N1—C2—C3 | 121.30 (13) | H13A—C13—H13C | 109.5 |
N1—C2—C6 | 116.45 (12) | H13B—C13—H13C | 109.5 |
C3—C2—C6 | 122.23 (12) | C10—C14—H14A | 109.5 |
C2—C3—H3 | 120.8 | C10—C14—H14B | 109.5 |
C2—C3—C4 | 118.39 (12) | C10—C14—H14C | 109.5 |
C4—C3—H3 | 120.8 | H14A—C14—H14B | 109.5 |
C3—C4—H4 | 119.7 | H14A—C14—H14C | 109.5 |
C5—C4—C3 | 120.52 (13) | H14B—C14—H14C | 109.5 |
C5—C4—H4 | 119.7 | C12—C15—H15A | 109.5 |
C1—C5—H5 | 120.9 | C12—C15—H15B | 109.5 |
C4—C5—C1 | 118.17 (13) | C12—C15—H15C | 109.5 |
C4—C5—H5 | 120.9 | H15A—C15—H15B | 109.5 |
C2—C6—H6A | 109.5 | H15A—C15—H15C | 109.5 |
C2—C6—H6B | 109.5 | H15B—C15—H15C | 109.5 |
C2—C6—H6C | 109.5 | C16—O3—H1A | 112 (2) |
H6A—C6—H6B | 109.5 | O3—C16—C17 | 114.33 (12) |
H6A—C6—H6C | 109.5 | O4—C16—O3 | 123.41 (13) |
H6B—C6—H6C | 109.5 | O4—C16—C17 | 122.25 (13) |
C8—C7—S1 | 121.45 (10) | C16—C17—H17A | 109.5 |
C12—C7—S1 | 117.57 (9) | C16—C17—H17B | 109.5 |
C12—C7—C8 | 120.91 (11) | C16—C17—H17C | 109.5 |
C7—C8—C13 | 126.50 (12) | H17A—C17—H17B | 109.5 |
C9—C8—C7 | 117.65 (12) | H17A—C17—H17C | 109.5 |
C9—C8—C13 | 115.84 (12) | H17B—C17—H17C | 109.5 |
C8—C9—H9 | 118.6 | | |
| | | |
S1—N2—C1—N1 | 168.02 (9) | C2—N1—C1—N2 | 179.60 (11) |
S1—N2—C1—C5 | −13.02 (19) | C2—N1—C1—C5 | 0.61 (19) |
S1—C7—C8—C9 | −177.32 (10) | C2—C3—C4—C5 | 0.6 (2) |
S1—C7—C8—C13 | 1.32 (19) | C3—C4—C5—C1 | 0.6 (2) |
S1—C7—C12—C11 | 177.63 (10) | C6—C2—C3—C4 | 177.56 (13) |
S1—C7—C12—C15 | −0.85 (18) | C7—S1—N2—C1 | 77.55 (12) |
O1—S1—N2—C1 | −167.78 (11) | C7—C8—C9—C10 | 0.2 (2) |
O1—S1—C7—C8 | 126.42 (11) | C8—C7—C12—C11 | 0.69 (19) |
O1—S1—C7—C12 | −50.50 (11) | C8—C7—C12—C15 | −177.78 (13) |
O2—S1—N2—C1 | −40.44 (13) | C8—C9—C10—C11 | 0.0 (2) |
O2—S1—C7—C8 | −4.11 (13) | C8—C9—C10—C14 | 178.40 (14) |
O2—S1—C7—C12 | 178.97 (9) | C9—C10—C11—C12 | 0.2 (2) |
N1—C1—C5—C4 | −1.2 (2) | C10—C11—C12—C7 | −0.6 (2) |
N1—C2—C3—C4 | −1.2 (2) | C10—C11—C12—C15 | 178.04 (13) |
N2—S1—C7—C8 | −121.83 (11) | C12—C7—C8—C9 | −0.51 (19) |
N2—S1—C7—C12 | 61.25 (11) | C12—C7—C8—C13 | 178.14 (12) |
N2—C1—C5—C4 | 179.94 (13) | C13—C8—C9—C10 | −178.61 (13) |
C1—N1—C2—C3 | 0.6 (2) | C14—C10—C11—C12 | −178.18 (14) |
C1—N1—C2—C6 | −178.21 (12) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H1A···N1 | 0.81 (3) | 1.86 (3)) | 2.6628 (17) | 170 (3) |
N1—H1B···O3 | 0.88 (5) | 1.79 (4) | 2.6628 (17) | 171 (5) |
N2—H2···O4 | 0.86 (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·C2H3.59O2 | Z = 2 |
Mr = 350.42 | F(000) = 372 |
Triclinic, P1 | Dx = 1.317 Mg m−3 |
a = 7.9881 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9052 (13) Å | Cell parameters from 2497 reflections |
c = 14.053 (3) Å | θ = 2.7–25.2° |
α = 101.185 (3)° | µ = 0.21 mm−1 |
β = 90.964 (3)° | T = 200 K |
γ = 114.909 (2)° | Block, colourless |
V = 884.0 (3) Å3 | 0.32 × 0.23 × 0.22 mm |
Data collection top
Bruker APEX CCD diffractometer | 4007 reflections with I > 2σ(I) |
Radiation source: Incoatec microfocus source | Rint = 0.037 |
ω scans | θmax = 30.7°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −10→11 |
Tmin = 0.659, Tmax = 0.746 | k = −12→12 |
13305 measured reflections | l = −20→19 |
5046 independent reflections | |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H 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 reflections | Δρmax = 0.39 e Å−3 |
234 parameters | Δρmin = −0.35 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.52748 (5) | 0.16246 (5) | 0.22364 (3) | 0.02771 (13) | |
O1 | 0.51955 (18) | 0.01364 (15) | 0.25184 (9) | 0.0356 (3) | |
O2 | 0.35668 (17) | 0.16402 (16) | 0.19319 (10) | 0.0362 (3) | |
N1 | 0.6996 (2) | 0.57015 (18) | 0.42350 (10) | 0.0289 (3) | |
N2 | 0.6307 (2) | 0.31528 (18) | 0.31978 (11) | 0.0309 (3) | |
H2 | 0.667 (4) | 0.278 (4) | 0.3672 (18) | 0.088 (10)* | |
C1 | 0.6409 (2) | 0.4770 (2) | 0.33241 (12) | 0.0272 (3) | |
C2 | 0.7177 (2) | 0.7309 (2) | 0.44655 (13) | 0.0331 (4) | |
C3 | 0.6746 (3) | 0.8034 (2) | 0.37714 (14) | 0.0374 (4) | |
H3 | 0.6850 | 0.9158 | 0.3939 | 0.045* | |
C4 | 0.6160 (3) | 0.7080 (2) | 0.28255 (14) | 0.0403 (4) | |
H4 | 0.5871 | 0.7559 | 0.2335 | 0.048* | |
C5 | 0.5990 (3) | 0.5447 (2) | 0.25870 (13) | 0.0366 (4) | |
H5 | 0.5598 | 0.4795 | 0.1936 | 0.044* | |
C6 | 0.7877 (3) | 0.8255 (3) | 0.55062 (15) | 0.0486 (5) | |
H6A | 0.7237 | 0.7515 | 0.5945 | 0.073* | |
H6B | 0.7633 | 0.9262 | 0.5636 | 0.073* | |
H6C | 0.9216 | 0.8605 | 0.5616 | 0.073* | |
C7 | 0.6784 (2) | 0.2062 (2) | 0.13074 (11) | 0.0253 (3) | |
C8 | 0.6205 (2) | 0.2249 (2) | 0.03986 (12) | 0.0291 (3) | |
C9 | 0.7443 (3) | 0.2503 (2) | −0.03031 (13) | 0.0354 (4) | |
H9 | 0.7069 | 0.2630 | −0.0916 | 0.042* | |
C10 | 0.9195 (3) | 0.2579 (3) | −0.01488 (14) | 0.0380 (4) | |
C11 | 0.9726 (2) | 0.2397 (3) | 0.07525 (13) | 0.0363 (4) | |
H11 | 1.0928 | 0.2453 | 0.0870 | 0.044* | |
C12 | 0.8565 (2) | 0.2136 (2) | 0.14879 (12) | 0.0292 (3) | |
C13 | 0.4332 (3) | 0.2157 (3) | 0.00973 (14) | 0.0385 (4) | |
H13A | 0.4249 | 0.2206 | −0.0592 | 0.058* | |
H13B | 0.4184 | 0.3116 | 0.0498 | 0.058* | |
H13C | 0.3348 | 0.1090 | 0.0190 | 0.058* | |
C14 | 1.0460 (3) | 0.2821 (4) | −0.09495 (16) | 0.0580 (6) | |
H14A | 1.0294 | 0.1710 | −0.1326 | 0.087* | |
H14B | 1.1754 | 0.3479 | −0.0660 | 0.087* | |
H14C | 1.0152 | 0.3431 | −0.1382 | 0.087* | |
C15 | 0.9301 (3) | 0.1902 (3) | 0.24182 (13) | 0.0373 (4) | |
H15A | 1.0541 | 0.1949 | 0.2352 | 0.056* | |
H15B | 0.8464 | 0.0798 | 0.2542 | 0.056* | |
H15C | 0.9376 | 0.2808 | 0.2964 | 0.056* | |
O3 | 0.7853 (3) | 0.46836 (19) | 0.57647 (11) | 0.0546 (4) | |
H1A | 0.751 (5) | 0.487 (5) | 0.528 (3) | 0.043 (9)* | 0.59 (3) |
H1B | 0.749 (7) | 0.535 (7) | 0.467 (3) | 0.043 (9)* | 0.41 (3) |
O4 | 0.7520 (3) | 0.2254 (2) | 0.48283 (11) | 0.0549 (4) | |
C16 | 0.7900 (3) | 0.3237 (2) | 0.56335 (13) | 0.0350 (4) | |
C17 | 0.8418 (3) | 0.2804 (3) | 0.65372 (15) | 0.0443 (5) | |
H17A | 0.7307 | 0.1959 | 0.6736 | 0.066* | |
H17B | 0.8960 | 0.3830 | 0.7061 | 0.066* | |
H17C | 0.9327 | 0.2339 | 0.6405 | 0.066* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0295 (2) | 0.0268 (2) | 0.0303 (2) | 0.01453 (16) | 0.00649 (15) | 0.00846 (16) |
O1 | 0.0451 (7) | 0.0268 (6) | 0.0378 (7) | 0.0164 (5) | 0.0089 (6) | 0.0116 (5) |
O2 | 0.0288 (6) | 0.0432 (7) | 0.0393 (7) | 0.0179 (5) | 0.0064 (5) | 0.0093 (6) |
N1 | 0.0339 (7) | 0.0286 (7) | 0.0261 (7) | 0.0154 (6) | 0.0047 (6) | 0.0057 (6) |
N2 | 0.0446 (8) | 0.0281 (7) | 0.0263 (7) | 0.0213 (6) | 0.0041 (6) | 0.0066 (6) |
C1 | 0.0326 (8) | 0.0272 (8) | 0.0265 (8) | 0.0163 (6) | 0.0080 (6) | 0.0083 (6) |
C2 | 0.0376 (9) | 0.0293 (8) | 0.0329 (9) | 0.0159 (7) | 0.0057 (7) | 0.0048 (7) |
C3 | 0.0483 (10) | 0.0281 (8) | 0.0404 (10) | 0.0200 (8) | 0.0070 (8) | 0.0095 (7) |
C4 | 0.0583 (12) | 0.0362 (10) | 0.0372 (10) | 0.0277 (9) | 0.0064 (9) | 0.0149 (8) |
C5 | 0.0539 (11) | 0.0337 (9) | 0.0280 (9) | 0.0240 (8) | 0.0045 (8) | 0.0082 (7) |
C6 | 0.0711 (15) | 0.0350 (10) | 0.0363 (11) | 0.0234 (10) | −0.0009 (10) | −0.0001 (8) |
C7 | 0.0260 (7) | 0.0267 (7) | 0.0249 (7) | 0.0130 (6) | 0.0033 (6) | 0.0056 (6) |
C8 | 0.0283 (8) | 0.0326 (8) | 0.0291 (8) | 0.0158 (7) | 0.0007 (6) | 0.0071 (7) |
C9 | 0.0368 (9) | 0.0471 (10) | 0.0272 (8) | 0.0217 (8) | 0.0027 (7) | 0.0111 (7) |
C10 | 0.0342 (9) | 0.0524 (11) | 0.0313 (9) | 0.0207 (8) | 0.0081 (7) | 0.0130 (8) |
C11 | 0.0275 (8) | 0.0519 (11) | 0.0333 (9) | 0.0204 (8) | 0.0043 (7) | 0.0105 (8) |
C12 | 0.0284 (8) | 0.0334 (8) | 0.0268 (8) | 0.0148 (7) | 0.0004 (6) | 0.0058 (6) |
C13 | 0.0375 (9) | 0.0541 (11) | 0.0331 (9) | 0.0285 (9) | −0.0008 (7) | 0.0102 (8) |
C14 | 0.0459 (12) | 0.101 (2) | 0.0407 (12) | 0.0384 (13) | 0.0194 (9) | 0.0276 (13) |
C15 | 0.0350 (9) | 0.0521 (11) | 0.0319 (9) | 0.0247 (8) | 0.0000 (7) | 0.0119 (8) |
O3 | 0.0938 (13) | 0.0372 (8) | 0.0339 (8) | 0.0311 (8) | −0.0108 (8) | 0.0056 (6) |
O4 | 0.0967 (12) | 0.0487 (9) | 0.0333 (7) | 0.0463 (9) | 0.0014 (8) | 0.0058 (6) |
C16 | 0.0392 (9) | 0.0328 (9) | 0.0326 (9) | 0.0140 (7) | 0.0038 (7) | 0.0103 (7) |
C17 | 0.0549 (12) | 0.0444 (11) | 0.0384 (10) | 0.0227 (9) | 0.0039 (9) | 0.0174 (9) |
Geometric parameters (Å, º) top
S1—O2 | 1.4295 (13) | C9—C10 | 1.384 (3) |
S1—O1 | 1.4322 (12) | C9—H9 | 0.9500 |
S1—N2 | 1.6314 (15) | C10—C11 | 1.389 (3) |
S1—C7 | 1.7790 (16) | C10—C14 | 1.511 (3) |
N1—C1 | 1.337 (2) | C11—C12 | 1.388 (2) |
N1—C2 | 1.349 (2) | C11—H11 | 0.9500 |
N1—H1B | 0.89 (2) | C12—C15 | 1.510 (2) |
N2—C1 | 1.384 (2) | C13—H13A | 0.9800 |
N2—H2 | 0.895 (17) | C13—H13B | 0.9800 |
C1—C5 | 1.395 (2) | C13—H13C | 0.9800 |
C2—C3 | 1.381 (3) | C14—H14A | 0.9800 |
C2—C6 | 1.503 (3) | C14—H14B | 0.9800 |
C3—C4 | 1.383 (3) | C14—H14C | 0.9800 |
C3—H3 | 0.9500 | C15—H15A | 0.9800 |
C4—C5 | 1.375 (2) | C15—H15B | 0.9800 |
C4—H4 | 0.9500 | C15—H15C | 0.9800 |
C5—H5 | 0.9500 | O3—C16 | 1.282 (2) |
C6—H6A | 0.9800 | O3—H1A | 0.81 (4) |
C6—H6B | 0.9800 | O4—C16 | 1.232 (2) |
C6—H6C | 0.9800 | C16—C17 | 1.496 (3) |
C7—C12 | 1.413 (2) | C17—H17A | 0.9800 |
C7—C8 | 1.414 (2) | C17—H17B | 0.9800 |
C8—C9 | 1.390 (2) | C17—H17C | 0.9800 |
C8—C13 | 1.512 (2) | | |
| | | |
O2—S1—O1 | 118.13 (8) | C10—C9—H9 | 118.5 |
O2—S1—N2 | 109.05 (8) | C8—C9—H9 | 118.5 |
O1—S1—N2 | 104.50 (8) | C9—C10—C11 | 117.89 (16) |
O2—S1—C7 | 109.51 (8) | C9—C10—C14 | 120.38 (17) |
O1—S1—C7 | 108.35 (7) | C11—C10—C14 | 121.72 (17) |
N2—S1—C7 | 106.66 (8) | C12—C11—C10 | 122.45 (16) |
C1—N1—C2 | 120.79 (15) | C12—C11—H11 | 118.8 |
C1—N1—H1B | 120 (3) | C10—C11—H11 | 118.8 |
C2—N1—H1B | 118 (3) | C11—C12—C7 | 118.30 (15) |
C1—N2—S1 | 124.89 (12) | C11—C12—C15 | 116.72 (15) |
C1—N2—H2 | 123 (2) | C7—C12—C15 | 124.97 (15) |
S1—N2—H2 | 111 (2) | C8—C13—H13A | 109.5 |
N1—C1—N2 | 114.16 (15) | C8—C13—H13B | 109.5 |
N1—C1—C5 | 120.73 (15) | H13A—C13—H13B | 109.5 |
N2—C1—C5 | 125.09 (16) | C8—C13—H13C | 109.5 |
N1—C2—C3 | 121.08 (17) | H13A—C13—H13C | 109.5 |
N1—C2—C6 | 116.58 (16) | H13B—C13—H13C | 109.5 |
C3—C2—C6 | 122.34 (17) | C10—C14—H14A | 109.5 |
C2—C3—C4 | 118.23 (17) | C10—C14—H14B | 109.5 |
C2—C3—H3 | 120.9 | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 120.9 | C10—C14—H14C | 109.5 |
C5—C4—C3 | 120.78 (17) | H14A—C14—H14C | 109.5 |
C5—C4—H4 | 119.6 | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 119.6 | C12—C15—H15A | 109.5 |
C4—C5—C1 | 118.37 (17) | C12—C15—H15B | 109.5 |
C4—C5—H5 | 120.8 | H15A—C15—H15B | 109.5 |
C1—C5—H5 | 120.8 | C12—C15—H15C | 109.5 |
C2—C6—H6A | 109.5 | H15A—C15—H15C | 109.5 |
C2—C6—H6B | 109.5 | H15B—C15—H15C | 109.5 |
H6A—C6—H6B | 109.5 | C16—O3—H1A | 114 (3) |
C2—C6—H6C | 109.5 | O4—C16—O3 | 122.94 (18) |
H6A—C6—H6C | 109.5 | O4—C16—C17 | 121.99 (17) |
H6B—C6—H6C | 109.5 | O3—C16—C17 | 115.07 (17) |
C12—C7—C8 | 120.64 (15) | C16—C17—H17A | 109.5 |
C12—C7—S1 | 117.65 (12) | C16—C17—H17B | 109.5 |
C8—C7—S1 | 121.64 (12) | H17A—C17—H17B | 109.5 |
C9—C8—C7 | 117.74 (15) | C16—C17—H17C | 109.5 |
C9—C8—C13 | 115.93 (15) | H17A—C17—H17C | 109.5 |
C7—C8—C13 | 126.32 (15) | H17B—C17—H17C | 109.5 |
C10—C9—C8 | 122.99 (16) | | |
| | | |
O2—S1—N2—C1 | −41.20 (16) | O1—S1—C7—C8 | 125.73 (14) |
O1—S1—N2—C1 | −168.39 (14) | N2—S1—C7—C8 | −122.28 (14) |
C7—S1—N2—C1 | 76.98 (16) | C12—C7—C8—C9 | 0.1 (2) |
C2—N1—C1—N2 | 179.51 (15) | S1—C7—C8—C9 | −176.76 (13) |
C2—N1—C1—C5 | 0.8 (3) | C12—C7—C8—C13 | 178.45 (16) |
S1—N2—C1—N1 | 167.58 (12) | S1—C7—C8—C13 | 1.6 (2) |
S1—N2—C1—C5 | −13.8 (3) | C7—C8—C9—C10 | 0.0 (3) |
C1—N1—C2—C3 | 0.6 (3) | C13—C8—C9—C10 | −178.55 (18) |
C1—N1—C2—C6 | −179.07 (16) | C8—C9—C10—C11 | −0.2 (3) |
N1—C2—C3—C4 | −1.4 (3) | C8—C9—C10—C14 | 178.7 (2) |
C6—C2—C3—C4 | 178.28 (19) | C9—C10—C11—C12 | 0.4 (3) |
C2—C3—C4—C5 | 0.8 (3) | C14—C10—C11—C12 | −178.5 (2) |
C3—C4—C5—C1 | 0.6 (3) | C10—C11—C12—C7 | −0.3 (3) |
N1—C1—C5—C4 | −1.4 (3) | C10—C11—C12—C15 | 178.06 (18) |
N2—C1—C5—C4 | −179.92 (17) | C8—C7—C12—C11 | 0.1 (2) |
O2—S1—C7—C12 | 178.69 (12) | S1—C7—C12—C11 | 177.03 (13) |
O1—S1—C7—C12 | −51.18 (15) | C8—C7—C12—C15 | −178.13 (17) |
N2—S1—C7—C12 | 60.82 (14) | S1—C7—C12—C15 | −1.2 (2) |
O2—S1—C7—C8 | −4.40 (16) | | |
(1_at_293K) 2,4,6-Trimethyl-
N-(6-methylpyridin-2-yl)benzenesulfonamide; acetic acid
top
Crystal data top
C15H18.47N2O2S·C2H3.53O2 | Z = 2 |
Mr = 350.42 | F(000) = 372 |
Triclinic, P1 | Dx = 1.295 Mg m−3 |
a = 8.0257 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9366 (11) Å | Cell parameters from 1951 reflections |
c = 14.1268 (17) Å | θ = 2.7–22.6° |
α = 101.0232 (19)° | µ = 0.20 mm−1 |
β = 91.2751 (19)° | T = 293 K |
γ = 114.5422 (17)° | Block, colourless |
V = 898.78 (19) Å3 | 0.32 × 0.23 × 0.22 mm |
Data collection top
Bruker APEX CCD diffractometer | 3446 reflections with I > 2σ(I) |
Radiation source: Incoatec microfocus source | Rint = 0.038 |
ω scans | θmax = 29.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −10→10 |
Tmin = 0.646, Tmax = 0.746 | k = −12→12 |
12970 measured reflections | l = −19→19 |
4735 independent reflections | |
Refinement top
Refinement on F2 | 1 restraint |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.055 | H 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 reflections | Δρmax = 0.31 e Å−3 |
234 parameters | Δρmin = −0.27 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.53004 (7) | 0.16592 (6) | 0.22365 (4) | 0.04126 (17) | |
O1 | 0.5227 (2) | 0.01775 (18) | 0.25145 (11) | 0.0529 (4) | |
O2 | 0.3601 (2) | 0.1677 (2) | 0.19352 (12) | 0.0544 (4) | |
N1 | 0.7013 (2) | 0.5702 (2) | 0.42210 (12) | 0.0420 (4) | |
N2 | 0.6330 (3) | 0.3171 (2) | 0.31901 (13) | 0.0454 (4) | |
H2 | 0.660 (5) | 0.280 (4) | 0.364 (3) | 0.102 (11)* | |
C1 | 0.6434 (3) | 0.4783 (2) | 0.33131 (14) | 0.0397 (4) | |
C2 | 0.7195 (3) | 0.7303 (3) | 0.44506 (16) | 0.0477 (5) | |
C3 | 0.6794 (4) | 0.8032 (3) | 0.37584 (18) | 0.0544 (6) | |
H3 | 0.6907 | 0.9132 | 0.3919 | 0.065* | |
C4 | 0.6220 (4) | 0.7093 (3) | 0.28211 (18) | 0.0590 (6) | |
H4 | 0.5950 | 0.7569 | 0.2342 | 0.071* | |
C5 | 0.6040 (4) | 0.5472 (3) | 0.25831 (16) | 0.0533 (6) | |
H5 | 0.5664 | 0.4846 | 0.1948 | 0.064* | |
C6 | 0.7858 (4) | 0.8224 (3) | 0.54898 (19) | 0.0703 (8) | |
H6A | 0.7212 | 0.7499 | 0.5910 | 0.105* | |
H6B | 0.7628 | 0.9212 | 0.5613 | 0.105* | |
H6C | 0.9156 | 0.8549 | 0.5611 | 0.105* | |
C7 | 0.6787 (3) | 0.2086 (2) | 0.13086 (14) | 0.0372 (4) | |
C8 | 0.6195 (3) | 0.2260 (3) | 0.04025 (15) | 0.0424 (5) | |
C9 | 0.7410 (3) | 0.2493 (3) | −0.02973 (16) | 0.0511 (5) | |
H9 | 0.7036 | 0.2609 | −0.0896 | 0.061* | |
C10 | 0.9144 (3) | 0.2561 (3) | −0.01488 (17) | 0.0549 (6) | |
C11 | 0.9688 (3) | 0.2394 (3) | 0.07514 (16) | 0.0528 (6) | |
H11 | 1.0858 | 0.2444 | 0.0864 | 0.063* | |
C12 | 0.8555 (3) | 0.2154 (3) | 0.14859 (14) | 0.0417 (4) | |
C13 | 0.4332 (3) | 0.2173 (3) | 0.01027 (17) | 0.0561 (6) | |
H13A | 0.4243 | 0.2216 | −0.0570 | 0.084* | |
H13B | 0.4188 | 0.3109 | 0.0491 | 0.084* | |
H13C | 0.3380 | 0.1137 | 0.0196 | 0.084* | |
C14 | 1.0392 (4) | 0.2784 (5) | −0.0947 (2) | 0.0856 (10) | |
H14A | 1.0281 | 0.1702 | −0.1285 | 0.128* | |
H14B | 1.1646 | 0.3476 | −0.0670 | 0.128* | |
H14C | 1.0042 | 0.3317 | −0.1394 | 0.128* | |
C15 | 0.9316 (3) | 0.1949 (3) | 0.24165 (17) | 0.0558 (6) | |
H15A | 1.0525 | 0.1999 | 0.2351 | 0.084* | |
H15B | 0.8519 | 0.0880 | 0.2547 | 0.084* | |
H15C | 0.9388 | 0.2839 | 0.2943 | 0.084* | |
O3 | 0.7815 (3) | 0.4637 (2) | 0.57454 (14) | 0.0793 (7) | |
H1A | 0.746 (7) | 0.484 (7) | 0.527 (4) | 0.064 (12)* | 0.53 (4) |
H1B | 0.735 (8) | 0.529 (7) | 0.468 (3) | 0.064 (12)* | 0.47 (4) |
O4 | 0.7475 (3) | 0.2230 (2) | 0.48187 (13) | 0.0803 (6) | |
C16 | 0.7856 (3) | 0.3199 (3) | 0.56177 (17) | 0.0508 (5) | |
C17 | 0.8338 (4) | 0.2749 (3) | 0.65165 (19) | 0.0660 (7) | |
H17A | 0.7245 | 0.1937 | 0.6704 | 0.099* | |
H17B | 0.8870 | 0.3743 | 0.7029 | 0.099* | |
H17C | 0.9211 | 0.2276 | 0.6394 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0443 (3) | 0.0402 (3) | 0.0432 (3) | 0.0204 (2) | 0.0091 (2) | 0.0119 (2) |
O1 | 0.0683 (10) | 0.0388 (8) | 0.0554 (9) | 0.0235 (7) | 0.0138 (8) | 0.0169 (7) |
O2 | 0.0425 (8) | 0.0657 (10) | 0.0581 (10) | 0.0259 (7) | 0.0098 (7) | 0.0134 (8) |
N1 | 0.0510 (10) | 0.0414 (9) | 0.0373 (9) | 0.0225 (8) | 0.0076 (7) | 0.0101 (7) |
N2 | 0.0652 (12) | 0.0418 (9) | 0.0381 (9) | 0.0308 (9) | 0.0061 (8) | 0.0101 (7) |
C1 | 0.0489 (11) | 0.0403 (10) | 0.0371 (10) | 0.0241 (9) | 0.0124 (8) | 0.0122 (8) |
C2 | 0.0554 (12) | 0.0418 (11) | 0.0486 (12) | 0.0239 (10) | 0.0097 (10) | 0.0087 (9) |
C3 | 0.0721 (15) | 0.0409 (11) | 0.0578 (14) | 0.0304 (11) | 0.0101 (12) | 0.0130 (10) |
C4 | 0.0864 (18) | 0.0541 (14) | 0.0529 (14) | 0.0415 (13) | 0.0082 (12) | 0.0220 (11) |
C5 | 0.0812 (16) | 0.0508 (12) | 0.0378 (11) | 0.0372 (12) | 0.0062 (11) | 0.0108 (9) |
C6 | 0.102 (2) | 0.0508 (14) | 0.0534 (15) | 0.0341 (14) | 0.0008 (14) | 0.0000 (11) |
C7 | 0.0396 (10) | 0.0395 (10) | 0.0357 (10) | 0.0201 (8) | 0.0039 (8) | 0.0084 (8) |
C8 | 0.0419 (10) | 0.0495 (11) | 0.0396 (11) | 0.0236 (9) | −0.0002 (8) | 0.0092 (9) |
C9 | 0.0532 (12) | 0.0686 (15) | 0.0368 (11) | 0.0301 (11) | 0.0022 (9) | 0.0147 (10) |
C10 | 0.0496 (12) | 0.0748 (16) | 0.0460 (12) | 0.0302 (11) | 0.0111 (10) | 0.0172 (11) |
C11 | 0.0403 (11) | 0.0763 (16) | 0.0484 (13) | 0.0306 (11) | 0.0051 (9) | 0.0154 (11) |
C12 | 0.0409 (10) | 0.0499 (11) | 0.0364 (10) | 0.0224 (9) | 0.0001 (8) | 0.0079 (8) |
C13 | 0.0523 (13) | 0.0803 (17) | 0.0475 (13) | 0.0401 (12) | −0.0028 (10) | 0.0141 (12) |
C14 | 0.0729 (18) | 0.146 (3) | 0.0598 (17) | 0.059 (2) | 0.0294 (14) | 0.0398 (19) |
C15 | 0.0538 (13) | 0.0781 (17) | 0.0460 (12) | 0.0370 (12) | −0.0003 (10) | 0.0179 (12) |
O3 | 0.138 (2) | 0.0546 (11) | 0.0485 (11) | 0.0461 (12) | −0.0117 (12) | 0.0088 (9) |
O4 | 0.1402 (19) | 0.0693 (12) | 0.0498 (10) | 0.0645 (13) | 0.0034 (11) | 0.0096 (9) |
C16 | 0.0569 (13) | 0.0506 (12) | 0.0464 (12) | 0.0222 (10) | 0.0062 (10) | 0.0161 (10) |
C17 | 0.0823 (18) | 0.0691 (17) | 0.0554 (15) | 0.0354 (14) | 0.0071 (13) | 0.0266 (13) |
Geometric parameters (Å, º) top
S1—O2 | 1.4274 (16) | C9—C10 | 1.377 (3) |
S1—O1 | 1.4304 (15) | C9—H9 | 0.9300 |
S1—N2 | 1.6278 (19) | C10—C11 | 1.390 (3) |
S1—C7 | 1.780 (2) | C10—C14 | 1.512 (3) |
N1—C1 | 1.338 (3) | C11—C12 | 1.384 (3) |
N1—C2 | 1.350 (3) | C11—H11 | 0.9300 |
N1—H1B | 0.89 (2) | C12—C15 | 1.512 (3) |
N2—C1 | 1.384 (3) | C13—H13A | 0.9600 |
N2—H2 | 0.83 (4) | C13—H13B | 0.9600 |
C1—C5 | 1.390 (3) | C13—H13C | 0.9600 |
C2—C3 | 1.374 (3) | C14—H14A | 0.9600 |
C2—C6 | 1.502 (3) | C14—H14B | 0.9600 |
C3—C4 | 1.377 (3) | C14—H14C | 0.9600 |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.368 (3) | C15—H15B | 0.9600 |
C4—H4 | 0.9300 | C15—H15C | 0.9600 |
C5—H5 | 0.9300 | O3—C16 | 1.278 (3) |
C6—H6A | 0.9600 | O3—H1A | 0.80 (6) |
C6—H6B | 0.9600 | O4—C16 | 1.228 (3) |
C6—H6C | 0.9600 | C16—C17 | 1.492 (3) |
C7—C12 | 1.409 (3) | C17—H17A | 0.9600 |
C7—C8 | 1.414 (3) | C17—H17B | 0.9600 |
C8—C9 | 1.388 (3) | C17—H17C | 0.9600 |
C8—C13 | 1.511 (3) | | |
| | | |
O2—S1—O1 | 117.90 (10) | C10—C9—H9 | 118.4 |
O2—S1—N2 | 109.21 (10) | C8—C9—H9 | 118.4 |
O1—S1—N2 | 104.59 (10) | C9—C10—C11 | 117.7 (2) |
O2—S1—C7 | 109.50 (9) | C9—C10—C14 | 120.7 (2) |
O1—S1—C7 | 108.25 (9) | C11—C10—C14 | 121.5 (2) |
N2—S1—C7 | 106.78 (10) | C10—C11—C12 | 122.5 (2) |
C1—N1—C2 | 120.79 (18) | C10—C11—H11 | 118.7 |
C1—N1—H1B | 121 (4) | C12—C11—H11 | 118.7 |
C2—N1—H1B | 118 (4) | C11—C12—C7 | 118.30 (18) |
C1—N2—S1 | 124.80 (16) | C11—C12—C15 | 116.53 (19) |
C1—N2—H2 | 123 (2) | C7—C12—C15 | 125.15 (19) |
S1—N2—H2 | 111 (2) | C8—C13—H13A | 109.5 |
N1—C1—N2 | 114.03 (18) | C8—C13—H13B | 109.5 |
N1—C1—C5 | 120.49 (19) | H13A—C13—H13B | 109.5 |
N2—C1—C5 | 125.46 (19) | C8—C13—H13C | 109.5 |
N1—C2—C3 | 120.9 (2) | H13A—C13—H13C | 109.5 |
N1—C2—C6 | 116.5 (2) | H13B—C13—H13C | 109.5 |
C3—C2—C6 | 122.6 (2) | C10—C14—H14A | 109.5 |
C2—C3—C4 | 118.3 (2) | C10—C14—H14B | 109.5 |
C2—C3—H3 | 120.8 | H14A—C14—H14B | 109.5 |
C4—C3—H3 | 120.8 | C10—C14—H14C | 109.5 |
C5—C4—C3 | 121.0 (2) | H14A—C14—H14C | 109.5 |
C5—C4—H4 | 119.5 | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 119.5 | C12—C15—H15A | 109.5 |
C4—C5—C1 | 118.4 (2) | C12—C15—H15B | 109.5 |
C4—C5—H5 | 120.8 | H15A—C15—H15B | 109.5 |
C1—C5—H5 | 120.8 | C12—C15—H15C | 109.5 |
C2—C6—H6A | 109.5 | H15A—C15—H15C | 109.5 |
C2—C6—H6B | 109.5 | H15B—C15—H15C | 109.5 |
H6A—C6—H6B | 109.5 | C16—O3—H1A | 115 (4) |
C2—C6—H6C | 109.5 | O4—C16—O3 | 122.7 (2) |
H6A—C6—H6C | 109.5 | O4—C16—C17 | 122.1 (2) |
H6B—C6—H6C | 109.5 | O3—C16—C17 | 115.2 (2) |
C12—C7—C8 | 120.59 (18) | C16—C17—H17A | 109.5 |
C12—C7—S1 | 117.65 (15) | C16—C17—H17B | 109.5 |
C8—C7—S1 | 121.67 (15) | H17A—C17—H17B | 109.5 |
C9—C8—C7 | 117.64 (18) | C16—C17—H17C | 109.5 |
C9—C8—C13 | 115.94 (19) | H17A—C17—H17C | 109.5 |
C7—C8—C13 | 126.40 (19) | H17B—C17—H17C | 109.5 |
C10—C9—C8 | 123.2 (2) | | |
| | | |
O2—S1—N2—C1 | −41.6 (2) | O1—S1—C7—C8 | 125.07 (17) |
O1—S1—N2—C1 | −168.71 (17) | N2—S1—C7—C8 | −122.81 (17) |
C7—S1—N2—C1 | 76.68 (19) | C12—C7—C8—C9 | 0.2 (3) |
C2—N1—C1—N2 | 179.58 (18) | S1—C7—C8—C9 | −176.28 (16) |
C2—N1—C1—C5 | 1.2 (3) | C12—C7—C8—C13 | 178.5 (2) |
S1—N2—C1—N1 | 167.21 (15) | S1—C7—C8—C13 | 2.0 (3) |
S1—N2—C1—C5 | −14.5 (3) | C7—C8—C9—C10 | 0.0 (3) |
C1—N1—C2—C3 | −0.1 (3) | C13—C8—C9—C10 | −178.4 (2) |
C1—N1—C2—C6 | −179.9 (2) | C8—C9—C10—C11 | −0.3 (4) |
N1—C2—C3—C4 | −0.7 (4) | C8—C9—C10—C14 | 178.8 (2) |
C6—C2—C3—C4 | 179.1 (2) | C9—C10—C11—C12 | 0.4 (4) |
C2—C3—C4—C5 | 0.4 (4) | C14—C10—C11—C12 | −178.7 (2) |
C3—C4—C5—C1 | 0.6 (4) | C10—C11—C12—C7 | −0.2 (4) |
N1—C1—C5—C4 | −1.4 (4) | C10—C11—C12—C15 | 178.5 (2) |
N2—C1—C5—C4 | −179.6 (2) | C8—C7—C12—C11 | −0.1 (3) |
O2—S1—C7—C12 | 178.72 (15) | S1—C7—C12—C11 | 176.55 (17) |
O1—S1—C7—C12 | −51.52 (18) | C8—C7—C12—C15 | −178.7 (2) |
N2—S1—C7—C12 | 60.59 (17) | S1—C7—C12—C15 | −2.1 (3) |
O2—S1—C7—C8 | −4.7 (2) | | |
IR frequencies (cm-1) in the carboxylate/carboxylic acid group top | (1) | Sodium acetate | Acetic acid |
νas | 1605 | 1583 | 1717 |
νsym | 1390 | 1444 | 1384 |
Δ = νas – νsym | 215 | 139 | 333 |
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