Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520613024384/bi5003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613024384/bi50031sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613024384/bi50032sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520613024384/bi50033sup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520613024384/bi5003sup5.pdf |
CCDC references: 984997; 984998; 984999
Data collection: CAD-4 (Enraf-Nonius, 1993) for (1), (2); APEX2 (Bruker, 2008) for (3). Cell refinement: CAD-4 for (1), (2); APEX2 for (3). Data reduction: CAD-4 for (1), (2); APEX2 for (3). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
C14H15F3N2S | F(000) = 624 |
Mr = 300.34 | Dx = 1.391 Mg m−3 |
Monoclinic, P21/c | Melting point: 364 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.074 (8) Å | Cell parameters from 35 reflections |
b = 9.185 (5) Å | θ = 5–15° |
c = 12.652 (8) Å | µ = 0.25 mm−1 |
β = 109.33 (6)° | T = 298 K |
V = 1433.7 (15) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.20 × 0.15 mm |
Nonius CAD-4 diffractometer | Rint = 0.060 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.5° |
Graphite monochromator | h = 0→15 |
ω–\2q scans | k = −10→0 |
2627 measured reflections | l = −15→14 |
2514 independent reflections | 3 standard reflections every 200 reflections |
852 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 0.87 | w = 1/[σ2(Fo2) + (0.1222P)2] where P = (Fo2 + 2Fc2)/3 |
2514 reflections | (Δ/σ)max < 0.001 |
210 parameters | Δρmax = 0.44 e Å−3 |
12 restraints | Δρmin = −0.35 e Å−3 |
C14H15F3N2S | V = 1433.7 (15) Å3 |
Mr = 300.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.074 (8) Å | µ = 0.25 mm−1 |
b = 9.185 (5) Å | T = 298 K |
c = 12.652 (8) Å | 0.35 × 0.20 × 0.15 mm |
β = 109.33 (6)° |
Nonius CAD-4 diffractometer | Rint = 0.060 |
2627 measured reflections | 3 standard reflections every 200 reflections |
2514 independent reflections | intensity decay: none |
852 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.075 | 12 restraints |
wR(F2) = 0.221 | H-atom parameters constrained |
S = 0.87 | Δρmax = 0.44 e Å−3 |
2514 reflections | Δρmin = −0.35 e Å−3 |
210 parameters |
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 | Occ. (<1) | |
S1 | 0.56653 (12) | 0.3174 (2) | 0.51108 (15) | 0.0775 (7) | |
F1 | 0.0434 (16) | 0.166 (2) | 0.573 (3) | 0.103 (9) | 0.46 (5) |
F2 | 0.0584 (12) | 0.294 (4) | 0.4449 (11) | 0.135 (10) | 0.46 (5) |
F3 | 0.0797 (18) | 0.385 (3) | 0.601 (3) | 0.185 (16) | 0.46 (5) |
F1' | 0.0448 (14) | 0.1507 (13) | 0.521 (4) | 0.131 (9) | 0.54 (5) |
F2' | 0.0591 (15) | 0.364 (4) | 0.475 (3) | 0.242 (19) | 0.54 (5) |
F3' | 0.0757 (15) | 0.313 (6) | 0.6401 (19) | 0.253 (15) | 0.54 (5) |
N1 | 0.5501 (3) | 0.1450 (6) | 0.6764 (4) | 0.0659 (15) | |
N2 | 0.7223 (3) | 0.1656 (5) | 0.6649 (4) | 0.0545 (13) | |
C1 | 0.2181 (4) | 0.2400 (7) | 0.5837 (6) | 0.0640 (18) | |
C2 | 0.2573 (5) | 0.1588 (8) | 0.5137 (6) | 0.079 (2) | |
H2A | 0.2096 | 0.1230 | 0.4468 | 0.095* | |
C3 | 0.3679 (5) | 0.1299 (7) | 0.5423 (6) | 0.073 (2) | |
H3A | 0.3934 | 0.0764 | 0.4938 | 0.087* | |
C4 | 0.4405 (4) | 0.1803 (7) | 0.6430 (5) | 0.0588 (16) | |
C5 | 0.4002 (4) | 0.2656 (8) | 0.7123 (5) | 0.0679 (19) | |
H5A | 0.4473 | 0.3032 | 0.7789 | 0.081* | |
C6 | 0.2914 (5) | 0.2936 (8) | 0.6819 (6) | 0.073 (2) | |
H6A | 0.2660 | 0.3504 | 0.7287 | 0.088* | |
C7 | 0.0983 (5) | 0.2706 (7) | 0.5522 (7) | 0.088 (2) | |
C8 | 0.6124 (4) | 0.2024 (6) | 0.6246 (5) | 0.0527 (15) | |
C9 | 0.7849 (4) | 0.2160 (7) | 0.5920 (5) | 0.0662 (18) | |
H9A | 0.8569 | 0.1736 | 0.6178 | 0.079* | |
H9B | 0.7488 | 0.1840 | 0.5156 | 0.079* | |
C10 | 0.7931 (4) | 0.3754 (7) | 0.5951 (6) | 0.0636 (17) | |
H10A | 0.8388 | 0.4045 | 0.5510 | 0.076* | |
C11 | 0.6792 (5) | 0.4441 (8) | 0.5405 (6) | 0.076 (2) | |
H11A | 0.6771 | 0.4904 | 0.4709 | 0.091* | |
H11B | 0.6693 | 0.5196 | 0.5898 | 0.091* | |
C12 | 0.7783 (4) | 0.2044 (8) | 0.7815 (5) | 0.0683 (19) | |
H12A | 0.8485 | 0.1569 | 0.8072 | 0.082* | |
H12B | 0.7366 | 0.1699 | 0.8273 | 0.082* | |
C13 | 0.7935 (5) | 0.3649 (8) | 0.7956 (5) | 0.075 (2) | |
H13A | 0.8387 | 0.3863 | 0.8718 | 0.090* | |
H13B | 0.7237 | 0.4112 | 0.7825 | 0.090* | |
C14 | 0.8467 (5) | 0.4272 (8) | 0.7135 (6) | 0.073 (2) | |
H14A | 0.8434 | 0.5327 | 0.7150 | 0.088* | |
H14B | 0.9225 | 0.3992 | 0.7382 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0481 (9) | 0.1032 (15) | 0.0784 (12) | −0.0034 (10) | 0.0172 (7) | 0.0294 (11) |
F1 | 0.048 (7) | 0.102 (14) | 0.188 (18) | 0.001 (7) | 0.077 (10) | 0.052 (10) |
F2 | 0.046 (7) | 0.21 (2) | 0.133 (17) | 0.053 (10) | 0.009 (7) | 0.083 (13) |
F3 | 0.057 (10) | 0.141 (19) | 0.33 (4) | 0.026 (9) | 0.023 (19) | −0.083 (19) |
F1' | 0.032 (6) | 0.130 (12) | 0.23 (2) | −0.009 (6) | 0.034 (9) | 0.015 (11) |
F2' | 0.063 (10) | 0.16 (2) | 0.53 (5) | 0.061 (10) | 0.12 (2) | 0.21 (2) |
F3' | 0.064 (9) | 0.37 (4) | 0.36 (3) | 0.013 (18) | 0.122 (15) | −0.13 (3) |
N1 | 0.033 (2) | 0.091 (4) | 0.079 (4) | 0.006 (3) | 0.025 (2) | 0.023 (3) |
N2 | 0.039 (2) | 0.070 (3) | 0.066 (3) | 0.006 (2) | 0.031 (2) | 0.007 (3) |
C1 | 0.034 (3) | 0.071 (5) | 0.093 (5) | 0.002 (3) | 0.030 (3) | 0.019 (4) |
C2 | 0.045 (3) | 0.092 (5) | 0.094 (5) | −0.010 (4) | 0.013 (3) | −0.014 (5) |
C3 | 0.049 (3) | 0.076 (5) | 0.099 (5) | −0.009 (3) | 0.034 (4) | −0.027 (4) |
C4 | 0.042 (3) | 0.063 (4) | 0.078 (4) | 0.003 (3) | 0.030 (3) | 0.014 (4) |
C5 | 0.045 (3) | 0.110 (5) | 0.058 (4) | 0.007 (3) | 0.030 (3) | −0.002 (4) |
C6 | 0.056 (4) | 0.100 (6) | 0.080 (5) | 0.018 (4) | 0.046 (4) | 0.015 (4) |
C7 | 0.052 (4) | 0.086 (7) | 0.130 (8) | 0.004 (5) | 0.038 (5) | 0.019 (6) |
C8 | 0.035 (3) | 0.055 (4) | 0.069 (4) | 0.000 (3) | 0.018 (3) | −0.004 (3) |
C9 | 0.039 (3) | 0.098 (6) | 0.080 (4) | −0.007 (3) | 0.045 (3) | −0.013 (4) |
C10 | 0.049 (3) | 0.084 (5) | 0.076 (5) | −0.004 (3) | 0.045 (3) | 0.000 (4) |
C11 | 0.062 (4) | 0.077 (5) | 0.096 (5) | −0.007 (4) | 0.036 (4) | 0.018 (4) |
C12 | 0.041 (3) | 0.114 (6) | 0.057 (4) | 0.007 (3) | 0.025 (3) | 0.013 (4) |
C13 | 0.063 (4) | 0.103 (6) | 0.065 (4) | −0.016 (4) | 0.029 (3) | −0.020 (4) |
C14 | 0.053 (3) | 0.092 (5) | 0.088 (5) | −0.022 (3) | 0.041 (3) | −0.013 (4) |
S1—C8 | 1.723 (6) | C4—C5 | 1.402 (8) |
S1—C11 | 1.817 (6) | C5—C6 | 1.369 (7) |
F1—C7 | 1.281 (10) | C5—H5A | 0.9300 |
F2—C7 | 1.302 (10) | C6—H6A | 0.9300 |
F3—C7 | 1.282 (11) | C9—C10 | 1.468 (9) |
F1'—C7 | 1.295 (10) | C9—H9A | 0.9700 |
F2'—C7 | 1.271 (10) | C9—H9B | 0.9700 |
F3'—C7 | 1.300 (10) | C10—C14 | 1.505 (8) |
N1—C8 | 1.313 (7) | C10—C11 | 1.553 (8) |
N1—C4 | 1.391 (7) | C10—H10A | 0.9800 |
N2—C8 | 1.398 (6) | C11—H11A | 0.9700 |
N2—C12 | 1.458 (7) | C11—H11B | 0.9700 |
N2—C9 | 1.494 (7) | C12—C13 | 1.490 (9) |
C1—C2 | 1.380 (9) | C12—H12A | 0.9700 |
C1—C6 | 1.385 (9) | C12—H12B | 0.9700 |
C1—C7 | 1.509 (8) | C13—C14 | 1.538 (8) |
C2—C3 | 1.395 (8) | C13—H13A | 0.9700 |
C2—H2A | 0.9300 | C13—H13B | 0.9700 |
C3—C4 | 1.392 (8) | C14—H14A | 0.9700 |
C3—H3A | 0.9300 | C14—H14B | 0.9700 |
C8—S1—C11 | 100.8 (3) | N2—C8—S1 | 118.9 (4) |
C8—N1—C4 | 120.1 (5) | C10—C9—N2 | 110.0 (5) |
C8—N2—C12 | 114.9 (4) | C10—C9—H9A | 109.7 |
C8—N2—C9 | 114.0 (5) | N2—C9—H9A | 109.7 |
C12—N2—C9 | 110.8 (4) | C10—C9—H9B | 109.7 |
C2—C1—C6 | 118.3 (5) | N2—C9—H9B | 109.7 |
C2—C1—C7 | 120.4 (6) | H9A—C9—H9B | 108.2 |
C6—C1—C7 | 121.4 (6) | C9—C10—C14 | 110.4 (6) |
C1—C2—C3 | 120.7 (6) | C9—C10—C11 | 110.0 (5) |
C1—C2—H2A | 119.7 | C14—C10—C11 | 112.1 (5) |
C3—C2—H2A | 119.7 | C9—C10—H10A | 108.1 |
C4—C3—C2 | 120.6 (6) | C14—C10—H10A | 108.1 |
C4—C3—H3A | 119.7 | C11—C10—H10A | 108.1 |
C2—C3—H3A | 119.7 | C10—C11—S1 | 115.1 (5) |
N1—C4—C3 | 121.5 (6) | C10—C11—H11A | 108.5 |
N1—C4—C5 | 120.1 (6) | S1—C11—H11A | 108.5 |
C3—C4—C5 | 118.3 (5) | C10—C11—H11B | 108.5 |
C6—C5—C4 | 120.0 (6) | S1—C11—H11B | 108.5 |
C6—C5—H5A | 120.0 | H11A—C11—H11B | 107.5 |
C4—C5—H5A | 120.0 | N2—C12—C13 | 111.4 (5) |
C5—C6—C1 | 122.1 (6) | N2—C12—H12A | 109.3 |
C5—C6—H6A | 118.9 | C13—C12—H12A | 109.3 |
C1—C6—H6A | 118.9 | N2—C12—H12B | 109.3 |
F1—C7—F3 | 107.9 (9) | C13—C12—H12B | 109.3 |
F1—C7—F2 | 106.5 (9) | H12A—C12—H12B | 108.0 |
F3—C7—F2 | 106.8 (10) | C12—C13—C14 | 111.1 (5) |
F2'—C7—F1' | 107.7 (9) | C12—C13—H13A | 109.4 |
F2'—C7—F3' | 107.6 (9) | C14—C13—H13A | 109.4 |
F1'—C7—F3' | 105.0 (9) | C12—C13—H13B | 109.4 |
F2'—C7—C1 | 116.7 (10) | C14—C13—H13B | 109.4 |
F1—C7—C1 | 114.2 (11) | H13A—C13—H13B | 108.0 |
F3—C7—C1 | 111.8 (12) | C10—C14—C13 | 112.8 (5) |
F1'—C7—C1 | 109.3 (10) | C10—C14—H14A | 109.0 |
F3'—C7—C1 | 109.9 (10) | C13—C14—H14A | 109.0 |
F2—C7—C1 | 109.2 (9) | C10—C14—H14B | 109.0 |
N1—C8—N2 | 117.0 (5) | C13—C14—H14B | 109.0 |
N1—C8—S1 | 124.0 (4) | H14A—C14—H14B | 107.8 |
C6—C1—C2—C3 | 1.0 (10) | C6—C1—C7—F2 | 140.8 (18) |
C7—C1—C2—C3 | −179.9 (6) | C4—N1—C8—N2 | 178.1 (5) |
C1—C2—C3—C4 | 1.1 (11) | C4—N1—C8—S1 | −2.4 (8) |
C8—N1—C4—C3 | 71.2 (8) | C12—N2—C8—N1 | −59.3 (7) |
C8—N1—C4—C5 | −110.3 (7) | C9—N2—C8—N1 | 171.2 (5) |
C2—C3—C4—N1 | 175.9 (6) | C12—N2—C8—S1 | 121.1 (5) |
C2—C3—C4—C5 | −2.6 (10) | C9—N2—C8—S1 | −8.4 (7) |
N1—C4—C5—C6 | −176.5 (6) | C11—S1—C8—N1 | 142.4 (5) |
C3—C4—C5—C6 | 2.0 (9) | C11—S1—C8—N2 | −38.1 (5) |
C4—C5—C6—C1 | 0.1 (10) | C8—N2—C9—C10 | 68.6 (7) |
C2—C1—C6—C5 | −1.5 (10) | C12—N2—C9—C10 | −62.9 (7) |
C7—C1—C6—C5 | 179.3 (6) | N2—C9—C10—C14 | 58.0 (6) |
C2—C1—C7—F2' | −74 (3) | N2—C9—C10—C11 | −66.2 (7) |
C6—C1—C7—F2' | 105 (2) | C9—C10—C11—S1 | 10.4 (7) |
C2—C1—C7—F1 | 80.8 (19) | C14—C10—C11—S1 | −112.8 (6) |
C6—C1—C7—F1 | −100.1 (18) | C8—S1—C11—C10 | 36.3 (5) |
C2—C1—C7—F3 | −156 (2) | C8—N2—C12—C13 | −71.5 (6) |
C6—C1—C7—F3 | 23 (2) | C9—N2—C12—C13 | 59.6 (6) |
C2—C1—C7—F1' | 48 (2) | N2—C12—C13—C14 | −51.9 (6) |
C6—C1—C7—F1' | −133 (2) | C9—C10—C14—C13 | −51.8 (7) |
C2—C1—C7—F3' | 163 (3) | C11—C10—C14—C13 | 71.2 (7) |
C6—C1—C7—F3' | −18 (3) | C12—C13—C14—C10 | 48.4 (8) |
C2—C1—C7—F2 | −38 (2) |
C13H15FN2S | F(000) = 528 |
Mr = 250.33 | Dx = 1.312 Mg m−3 |
Monoclinic, P21/c | Melting point: 363 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.586 (1) Å | Cell parameters from 35 reflections |
b = 10.088 (2) Å | θ = 5–15° |
c = 16.566 (4) Å | µ = 0.25 mm−1 |
β = 91.41 (3)° | T = 293 K |
V = 1267.4 (4) Å3 | Block, colourless |
Z = 4 | 0.45 × 0.30 × 0.15 mm |
Nonius CAD-4 diffractometer | Rint = 0.018 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 2.4° |
Graphite monochromator | h = −10→10 |
ω–\2q scans | k = 0→14 |
3814 measured reflections | l = 0→23 |
3698 independent reflections | 3 standard reflections every 200 reflections |
2094 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0757P)2] where P = (Fo2 + 2Fc2)/3 |
3698 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C13H15FN2S | V = 1267.4 (4) Å3 |
Mr = 250.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.586 (1) Å | µ = 0.25 mm−1 |
b = 10.088 (2) Å | T = 293 K |
c = 16.566 (4) Å | 0.45 × 0.30 × 0.15 mm |
β = 91.41 (3)° |
Nonius CAD-4 diffractometer | Rint = 0.018 |
3814 measured reflections | 3 standard reflections every 200 reflections |
3698 independent reflections | intensity decay: none |
2094 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.27 e Å−3 |
3698 reflections | Δρmin = −0.25 e Å−3 |
154 parameters |
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 | 1.14718 (5) | 0.27372 (5) | 0.50016 (2) | 0.05899 (15) | |
F1 | 1.49014 (18) | 0.44604 (13) | 0.17884 (8) | 0.0973 (4) | |
N1 | 0.96747 (16) | 0.22477 (14) | 0.36082 (8) | 0.0548 (3) | |
N2 | 0.83473 (16) | 0.15279 (12) | 0.47580 (8) | 0.0528 (3) | |
C1 | 1.3612 (2) | 0.39195 (18) | 0.22469 (9) | 0.0630 (4) | |
C2 | 1.3985 (3) | 0.2779 (2) | 0.26612 (12) | 0.0724 (5) | |
H2A | 1.5084 | 0.2377 | 0.2630 | 0.087* | |
C3 | 1.2678 (2) | 0.22395 (18) | 0.31296 (11) | 0.0648 (4) | |
H3A | 1.2904 | 0.1462 | 0.3416 | 0.078* | |
C4 | 1.10529 (19) | 0.28343 (15) | 0.31780 (8) | 0.0472 (3) | |
C5 | 1.0731 (2) | 0.39711 (16) | 0.27303 (9) | 0.0553 (4) | |
H5A | 0.9625 | 0.4368 | 0.2743 | 0.066* | |
C6 | 1.2024 (2) | 0.45265 (16) | 0.22644 (9) | 0.0627 (4) | |
H6A | 1.1807 | 0.5298 | 0.1971 | 0.075* | |
C8 | 0.97345 (17) | 0.21325 (13) | 0.43688 (8) | 0.0430 (3) | |
C9 | 0.8515 (2) | 0.13495 (17) | 0.56284 (11) | 0.0649 (5) | |
H9A | 0.9601 | 0.0884 | 0.5762 | 0.078* | |
H9B | 0.7537 | 0.0824 | 0.5818 | 0.078* | |
C10 | 0.8520 (2) | 0.26987 (17) | 0.60370 (9) | 0.0602 (4) | |
H10A | 0.8518 | 0.2560 | 0.6623 | 0.072* | |
C11 | 1.0214 (2) | 0.34300 (19) | 0.58300 (10) | 0.0627 (4) | |
H11A | 1.0973 | 0.3452 | 0.6310 | 0.075* | |
H11B | 0.9912 | 0.4339 | 0.5695 | 0.075* | |
C12 | 0.66026 (19) | 0.20752 (18) | 0.45292 (12) | 0.0637 (4) | |
H12A | 0.5681 | 0.1506 | 0.4730 | 0.076* | |
H12B | 0.6475 | 0.2121 | 0.3946 | 0.076* | |
C13 | 0.64368 (19) | 0.34508 (17) | 0.48880 (10) | 0.0588 (4) | |
H13A | 0.5252 | 0.3781 | 0.4784 | 0.071* | |
H13B | 0.7253 | 0.4044 | 0.4628 | 0.071* | |
C14 | 0.6820 (2) | 0.34457 (19) | 0.57883 (10) | 0.0627 (4) | |
H14A | 0.5834 | 0.3042 | 0.6057 | 0.075* | |
H14B | 0.6916 | 0.4355 | 0.5975 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.04262 (19) | 0.0797 (3) | 0.0546 (2) | −0.00286 (18) | 0.00027 (14) | −0.00468 (19) |
F1 | 0.1085 (9) | 0.0946 (9) | 0.0910 (8) | −0.0154 (7) | 0.0453 (7) | 0.0185 (7) |
N1 | 0.0522 (7) | 0.0598 (8) | 0.0524 (7) | −0.0087 (6) | 0.0021 (5) | −0.0067 (6) |
N2 | 0.0480 (6) | 0.0403 (6) | 0.0709 (8) | −0.0035 (5) | 0.0149 (5) | −0.0020 (6) |
C1 | 0.0781 (11) | 0.0609 (10) | 0.0508 (8) | −0.0039 (9) | 0.0185 (7) | 0.0057 (7) |
C2 | 0.0672 (10) | 0.0840 (13) | 0.0671 (10) | 0.0183 (9) | 0.0231 (8) | 0.0168 (10) |
C3 | 0.0675 (9) | 0.0649 (10) | 0.0627 (9) | 0.0146 (8) | 0.0163 (7) | 0.0226 (8) |
C4 | 0.0539 (7) | 0.0494 (8) | 0.0384 (6) | −0.0025 (6) | 0.0007 (5) | −0.0051 (6) |
C5 | 0.0625 (8) | 0.0505 (8) | 0.0528 (8) | 0.0076 (7) | −0.0021 (6) | −0.0040 (7) |
C6 | 0.0888 (12) | 0.0452 (8) | 0.0542 (8) | 0.0014 (8) | 0.0032 (8) | 0.0057 (7) |
C8 | 0.0404 (6) | 0.0356 (6) | 0.0533 (7) | 0.0013 (5) | 0.0055 (5) | −0.0028 (5) |
C9 | 0.0704 (10) | 0.0496 (9) | 0.0757 (11) | 0.0080 (7) | 0.0264 (8) | 0.0201 (8) |
C10 | 0.0718 (10) | 0.0635 (10) | 0.0459 (8) | 0.0136 (8) | 0.0143 (7) | 0.0109 (7) |
C11 | 0.0653 (9) | 0.0732 (11) | 0.0495 (8) | 0.0065 (8) | −0.0017 (6) | −0.0064 (8) |
C12 | 0.0406 (7) | 0.0676 (11) | 0.0831 (11) | −0.0097 (7) | 0.0068 (7) | −0.0131 (9) |
C13 | 0.0444 (7) | 0.0587 (9) | 0.0734 (10) | 0.0069 (7) | 0.0039 (6) | 0.0008 (8) |
C14 | 0.0624 (9) | 0.0613 (10) | 0.0654 (9) | 0.0107 (8) | 0.0175 (7) | −0.0026 (8) |
S1—C8 | 1.7720 (15) | C6—H6A | 0.9300 |
S1—C11 | 1.8296 (17) | C9—C10 | 1.520 (3) |
F1—C1 | 1.3665 (18) | C9—H9A | 0.9700 |
N1—C8 | 1.2650 (19) | C9—H9B | 0.9700 |
N1—C4 | 1.4098 (19) | C10—C11 | 1.528 (2) |
N2—C8 | 1.3887 (17) | C10—C14 | 1.541 (2) |
N2—C9 | 1.455 (2) | C10—H10A | 0.9800 |
N2—C12 | 1.475 (2) | C11—H11A | 0.9700 |
C1—C2 | 1.365 (3) | C11—H11B | 0.9700 |
C1—C6 | 1.353 (2) | C12—C13 | 1.516 (3) |
C2—C3 | 1.385 (2) | C12—H12A | 0.9700 |
C2—H2A | 0.9300 | C12—H12B | 0.9700 |
C3—C4 | 1.375 (2) | C13—C14 | 1.512 (2) |
C3—H3A | 0.9300 | C13—H13A | 0.9700 |
C4—C5 | 1.384 (2) | C13—H13B | 0.9700 |
C5—C6 | 1.382 (2) | C14—H14A | 0.9700 |
C5—H5A | 0.9300 | C14—H14B | 0.9700 |
C8—S1—C11 | 100.43 (7) | H9A—C9—H9B | 108.3 |
C8—N1—C4 | 122.22 (12) | C9—C10—C11 | 108.99 (13) |
C8—N2—C9 | 117.76 (13) | C9—C10—C14 | 109.02 (15) |
C8—N2—C12 | 113.68 (13) | C11—C10—C14 | 113.99 (14) |
C9—N2—C12 | 110.89 (13) | C9—C10—H10A | 108.2 |
F1—C1—C2 | 118.29 (17) | C11—C10—H10A | 108.2 |
F1—C1—C6 | 118.77 (16) | C14—C10—H10A | 108.2 |
C2—C1—C6 | 122.94 (16) | C10—C11—S1 | 116.17 (12) |
C1—C2—C3 | 118.09 (17) | C10—C11—H11A | 108.2 |
C1—C2—H2A | 121.0 | S1—C11—H11A | 108.2 |
C3—C2—H2A | 121.0 | C10—C11—H11B | 108.2 |
C2—C3—C4 | 121.06 (15) | S1—C11—H11B | 108.2 |
C2—C3—H3A | 119.5 | H11A—C11—H11B | 107.4 |
C4—C3—H3A | 119.5 | N2—C12—C13 | 108.93 (13) |
C5—C4—C3 | 118.48 (14) | N2—C12—H12A | 109.9 |
C5—C4—N1 | 119.69 (14) | C13—C12—H12A | 109.9 |
C3—C4—N1 | 121.56 (14) | N2—C12—H12B | 109.9 |
C4—C5—C6 | 121.13 (15) | C13—C12—H12B | 109.9 |
C4—C5—H5A | 119.4 | H12A—C12—H12B | 108.3 |
C6—C5—H5A | 119.4 | C12—C13—C14 | 111.58 (15) |
C1—C6—C5 | 118.26 (15) | C12—C13—H13A | 109.3 |
C1—C6—H6A | 120.9 | C14—C13—H13A | 109.3 |
C5—C6—H6A | 120.9 | C12—C13—H13B | 109.3 |
N1—C8—N2 | 119.59 (13) | C14—C13—H13B | 109.3 |
N1—C8—S1 | 124.44 (11) | H13A—C13—H13B | 108.0 |
N2—C8—S1 | 115.95 (11) | C13—C14—C10 | 113.88 (13) |
N2—C9—C10 | 109.25 (12) | C13—C14—H14A | 108.8 |
N2—C9—H9A | 109.8 | C10—C14—H14A | 108.8 |
C10—C9—H9A | 109.8 | C13—C14—H14B | 108.8 |
N2—C9—H9B | 109.8 | C10—C14—H14B | 108.8 |
C10—C9—H9B | 109.8 | H14A—C14—H14B | 107.7 |
F1—C1—C2—C3 | 179.57 (17) | C12—N2—C8—S1 | 127.13 (12) |
C6—C1—C2—C3 | −1.1 (3) | C11—S1—C8—N1 | 138.02 (14) |
C1—C2—C3—C4 | −0.1 (3) | C11—S1—C8—N2 | −40.24 (13) |
C2—C3—C4—C5 | 1.7 (3) | C8—N2—C9—C10 | 66.46 (17) |
C2—C3—C4—N1 | 175.64 (17) | C12—N2—C9—C10 | −66.91 (17) |
C8—N1—C4—C5 | −118.20 (17) | N2—C9—C10—C11 | −67.89 (18) |
C8—N1—C4—C3 | 67.9 (2) | N2—C9—C10—C14 | 57.09 (17) |
C3—C4—C5—C6 | −2.1 (2) | C9—C10—C11—S1 | 13.87 (18) |
N1—C4—C5—C6 | −176.18 (13) | C14—C10—C11—S1 | −108.15 (15) |
F1—C1—C6—C5 | −179.98 (14) | C8—S1—C11—C10 | 34.13 (14) |
C2—C1—C6—C5 | 0.7 (3) | C8—N2—C12—C13 | −71.20 (18) |
C4—C5—C6—C1 | 0.9 (2) | C9—N2—C12—C13 | 64.18 (17) |
C4—N1—C8—N2 | −179.05 (13) | N2—C12—C13—C14 | −53.47 (18) |
C4—N1—C8—S1 | 2.7 (2) | C12—C13—C14—C10 | 48.0 (2) |
C9—N2—C8—N1 | 176.64 (14) | C9—C10—C14—C13 | −49.07 (19) |
C12—N2—C8—N1 | −51.23 (18) | C11—C10—C14—C13 | 72.9 (2) |
C9—N2—C8—S1 | −5.01 (16) |
C14H18N2S | Dx = 1.275 Mg m−3 |
Mr = 246.36 | Melting point: 348 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 9634 reflections |
a = 8.7377 (2) Å | θ = 3.8–25.0° |
b = 14.1088 (3) Å | µ = 0.23 mm−1 |
c = 20.8300 (5) Å | T = 100 K |
V = 2567.89 (10) Å3 | Block, colourless |
Z = 8 | 0.20 × 0.20 × 0.20 mm |
F(000) = 1056 |
Bruker Kappa APEX-II CCD diffractometer | 2265 independent reflections |
Radiation source: fine-focus sealed tube | 2100 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 25.0°, θmin = 3.8° |
Absorption correction: multi-scan SADABS (Bruker, 2008) | h = −10→10 |
Tmin = 0.932, Tmax = 0.955 | k = −16→16 |
38126 measured reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0376P)2 + 1.8178P] where P = (Fo2 + 2Fc2)/3 |
2265 reflections | (Δ/σ)max = 0.002 |
155 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C14H18N2S | V = 2567.89 (10) Å3 |
Mr = 246.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.7377 (2) Å | µ = 0.23 mm−1 |
b = 14.1088 (3) Å | T = 100 K |
c = 20.8300 (5) Å | 0.20 × 0.20 × 0.20 mm |
Bruker Kappa APEX-II CCD diffractometer | 2265 independent reflections |
Absorption correction: multi-scan SADABS (Bruker, 2008) | 2100 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.955 | Rint = 0.033 |
38126 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.085 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.51 e Å−3 |
2265 reflections | Δρmin = −0.19 e Å−3 |
155 parameters |
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 | 0.84809 (4) | 0.03355 (3) | 0.587973 (19) | 0.02182 (13) | |
N1 | 1.07226 (15) | 0.16743 (9) | 0.60206 (6) | 0.0223 (3) | |
N2 | 0.85825 (14) | 0.21315 (9) | 0.54478 (6) | 0.0201 (3) | |
C1 | 1.36591 (17) | −0.01997 (11) | 0.70237 (7) | 0.0220 (3) | |
C2 | 1.29254 (18) | −0.04956 (12) | 0.64613 (7) | 0.0237 (3) | |
H2A | 1.3099 | −0.1119 | 0.6304 | 0.028* | |
C3 | 1.19474 (18) | 0.01057 (12) | 0.61279 (7) | 0.0231 (3) | |
H3A | 1.1479 | −0.0107 | 0.5742 | 0.028* | |
C4 | 1.16451 (16) | 0.10184 (11) | 0.63523 (7) | 0.0210 (3) | |
C5 | 1.23839 (18) | 0.13171 (11) | 0.69139 (7) | 0.0237 (3) | |
H5A | 1.2208 | 0.1939 | 0.7073 | 0.028* | |
C6 | 1.33678 (17) | 0.07165 (12) | 0.72402 (7) | 0.0238 (3) | |
H6A | 1.3855 | 0.0935 | 0.7620 | 0.029* | |
C7 | 1.47929 (18) | −0.08305 (12) | 0.73623 (7) | 0.0273 (4) | |
H7A | 1.4788 | −0.0687 | 0.7823 | 0.041* | |
H7B | 1.5819 | −0.0719 | 0.7188 | 0.041* | |
H7C | 1.4509 | −0.1495 | 0.7296 | 0.041* | |
C8 | 0.94182 (17) | 0.14545 (10) | 0.57877 (7) | 0.0188 (3) | |
C9 | 0.71237 (18) | 0.18388 (11) | 0.51623 (7) | 0.0243 (3) | |
H9A | 0.7280 | 0.1268 | 0.4894 | 0.029* | |
H9B | 0.6724 | 0.2351 | 0.4884 | 0.029* | |
C10 | 0.59763 (18) | 0.16229 (11) | 0.56934 (8) | 0.0240 (3) | |
H10A | 0.4971 | 0.1458 | 0.5493 | 0.029* | |
C11 | 0.65509 (17) | 0.07612 (11) | 0.60859 (8) | 0.0246 (4) | |
H11A | 0.5820 | 0.0232 | 0.6026 | 0.029* | |
H11B | 0.6539 | 0.0933 | 0.6547 | 0.029* | |
C12 | 0.84231 (18) | 0.30482 (11) | 0.57798 (8) | 0.0236 (3) | |
H12A | 0.8042 | 0.3534 | 0.5477 | 0.028* | |
H12B | 0.9430 | 0.3257 | 0.5945 | 0.028* | |
C13 | 0.72977 (18) | 0.29317 (11) | 0.63354 (8) | 0.0247 (3) | |
H13A | 0.7113 | 0.3556 | 0.6538 | 0.030* | |
H13B | 0.7749 | 0.2508 | 0.6664 | 0.030* | |
C14 | 0.57725 (18) | 0.25165 (12) | 0.61055 (8) | 0.0260 (4) | |
H14A | 0.5221 | 0.3002 | 0.5852 | 0.031* | |
H14B | 0.5135 | 0.2359 | 0.6484 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0222 (2) | 0.0174 (2) | 0.0258 (2) | 0.00021 (14) | −0.00289 (15) | 0.00246 (15) |
N1 | 0.0196 (7) | 0.0243 (7) | 0.0230 (7) | −0.0010 (5) | 0.0034 (5) | 0.0046 (5) |
N2 | 0.0240 (7) | 0.0188 (6) | 0.0174 (6) | 0.0025 (5) | 0.0015 (5) | 0.0040 (5) |
C1 | 0.0166 (7) | 0.0321 (8) | 0.0173 (7) | −0.0012 (6) | 0.0032 (6) | 0.0039 (6) |
C2 | 0.0215 (8) | 0.0279 (8) | 0.0217 (8) | 0.0034 (6) | 0.0031 (6) | −0.0017 (6) |
C3 | 0.0201 (7) | 0.0328 (8) | 0.0164 (7) | 0.0022 (7) | 0.0008 (6) | −0.0019 (6) |
C4 | 0.0164 (7) | 0.0264 (8) | 0.0201 (7) | −0.0003 (6) | 0.0053 (6) | 0.0056 (6) |
C5 | 0.0213 (8) | 0.0250 (8) | 0.0247 (8) | −0.0040 (6) | 0.0032 (6) | −0.0024 (6) |
C6 | 0.0200 (7) | 0.0335 (9) | 0.0181 (7) | −0.0046 (7) | 0.0013 (6) | −0.0014 (7) |
C7 | 0.0246 (8) | 0.0349 (9) | 0.0224 (8) | 0.0006 (7) | −0.0007 (7) | 0.0046 (7) |
C8 | 0.0225 (8) | 0.0195 (7) | 0.0145 (7) | 0.0006 (6) | 0.0043 (6) | 0.0017 (6) |
C9 | 0.0309 (9) | 0.0238 (8) | 0.0182 (7) | 0.0061 (7) | −0.0066 (6) | 0.0006 (6) |
C10 | 0.0210 (8) | 0.0235 (8) | 0.0276 (8) | 0.0019 (6) | −0.0059 (7) | 0.0002 (6) |
C11 | 0.0192 (8) | 0.0237 (8) | 0.0308 (9) | −0.0025 (6) | −0.0008 (6) | 0.0018 (7) |
C12 | 0.0259 (8) | 0.0164 (7) | 0.0286 (8) | 0.0013 (6) | 0.0030 (7) | 0.0018 (6) |
C13 | 0.0286 (9) | 0.0211 (7) | 0.0243 (8) | 0.0020 (6) | 0.0023 (7) | −0.0016 (6) |
C14 | 0.0223 (8) | 0.0264 (8) | 0.0292 (8) | 0.0040 (7) | 0.0034 (7) | 0.0012 (7) |
S1—C8 | 1.7888 (15) | C7—H7B | 0.9800 |
S1—C11 | 1.8410 (16) | C7—H7C | 0.9800 |
N1—C8 | 1.277 (2) | C9—C10 | 1.524 (2) |
N1—C4 | 1.408 (2) | C9—H9A | 0.9900 |
N2—C8 | 1.3953 (19) | C9—H9B | 0.9900 |
N2—C9 | 1.466 (2) | C10—C14 | 1.535 (2) |
N2—C12 | 1.473 (2) | C10—C11 | 1.549 (2) |
C1—C6 | 1.393 (2) | C10—H10A | 1.0000 |
C1—C2 | 1.399 (2) | C11—H11A | 0.9900 |
C1—C7 | 1.507 (2) | C11—H11B | 0.9900 |
C2—C3 | 1.390 (2) | C12—C13 | 1.528 (2) |
C2—H2A | 0.9500 | C12—H12A | 0.9900 |
C3—C4 | 1.395 (2) | C12—H12B | 0.9900 |
C3—H3A | 0.9500 | C13—C14 | 1.533 (2) |
C4—C5 | 1.401 (2) | C13—H13A | 0.9900 |
C5—C6 | 1.385 (2) | C13—H13B | 0.9900 |
C5—H5A | 0.9500 | C14—H14A | 0.9900 |
C6—H6A | 0.9500 | C14—H14B | 0.9900 |
C7—H7A | 0.9800 | ||
C8—S1—C11 | 99.00 (7) | C10—C9—H9A | 109.8 |
C8—N1—C4 | 122.53 (13) | N2—C9—H9B | 109.8 |
C8—N2—C9 | 117.91 (12) | C10—C9—H9B | 109.8 |
C8—N2—C12 | 114.34 (12) | H9A—C9—H9B | 108.2 |
C9—N2—C12 | 110.83 (12) | C9—C10—C14 | 108.54 (13) |
C6—C1—C2 | 117.67 (14) | C9—C10—C11 | 109.08 (13) |
C6—C1—C7 | 121.13 (14) | C14—C10—C11 | 112.78 (13) |
C2—C1—C7 | 121.12 (14) | C9—C10—H10A | 108.8 |
C3—C2—C1 | 121.18 (15) | C14—C10—H10A | 108.8 |
C3—C2—H2A | 119.4 | C11—C10—H10A | 108.8 |
C1—C2—H2A | 119.4 | C10—C11—S1 | 115.47 (11) |
C2—C3—C4 | 120.82 (14) | C10—C11—H11A | 108.4 |
C2—C3—H3A | 119.6 | S1—C11—H11A | 108.4 |
C4—C3—H3A | 119.6 | C10—C11—H11B | 108.4 |
C3—C4—C5 | 118.05 (14) | S1—C11—H11B | 108.4 |
C3—C4—N1 | 123.39 (14) | H11A—C11—H11B | 107.5 |
C5—C4—N1 | 118.41 (14) | N2—C12—C13 | 108.79 (12) |
C6—C5—C4 | 120.77 (15) | N2—C12—H12A | 109.9 |
C6—C5—H5A | 119.6 | C13—C12—H12A | 109.9 |
C4—C5—H5A | 119.6 | N2—C12—H12B | 109.9 |
C5—C6—C1 | 121.49 (15) | C13—C12—H12B | 109.9 |
C5—C6—H6A | 119.3 | H12A—C12—H12B | 108.3 |
C1—C6—H6A | 119.3 | C12—C13—C14 | 111.35 (13) |
C1—C7—H7A | 109.5 | C12—C13—H13A | 109.4 |
C1—C7—H7B | 109.5 | C14—C13—H13A | 109.4 |
H7A—C7—H7B | 109.5 | C12—C13—H13B | 109.4 |
C1—C7—H7C | 109.5 | C14—C13—H13B | 109.4 |
H7A—C7—H7C | 109.5 | H13A—C13—H13B | 108.0 |
H7B—C7—H7C | 109.5 | C13—C14—C10 | 112.81 (13) |
N1—C8—N2 | 119.58 (13) | C13—C14—H14A | 109.0 |
N1—C8—S1 | 125.60 (12) | C10—C14—H14A | 109.0 |
N2—C8—S1 | 114.77 (11) | C13—C14—H14B | 109.0 |
N2—C9—C10 | 109.51 (12) | C10—C14—H14B | 109.0 |
N2—C9—H9A | 109.8 | H14A—C14—H14B | 107.8 |
C6—C1—C2—C3 | 0.4 (2) | C12—N2—C8—S1 | 127.93 (11) |
C7—C1—C2—C3 | −176.21 (15) | C11—S1—C8—N1 | 134.09 (14) |
C1—C2—C3—C4 | −1.3 (2) | C11—S1—C8—N2 | −43.56 (12) |
C2—C3—C4—C5 | 1.5 (2) | C8—N2—C9—C10 | 67.61 (16) |
C2—C3—C4—N1 | 176.94 (14) | C12—N2—C9—C10 | −66.85 (15) |
C8—N1—C4—C3 | 47.2 (2) | N2—C9—C10—C14 | 58.77 (16) |
C8—N1—C4—C5 | −137.39 (15) | N2—C9—C10—C11 | −64.46 (16) |
C3—C4—C5—C6 | −0.9 (2) | C9—C10—C11—S1 | 6.71 (17) |
N1—C4—C5—C6 | −176.58 (14) | C14—C10—C11—S1 | −113.95 (14) |
C4—C5—C6—C1 | 0.1 (2) | C8—S1—C11—C10 | 41.46 (13) |
C2—C1—C6—C5 | 0.2 (2) | C8—N2—C12—C13 | −72.88 (16) |
C7—C1—C6—C5 | 176.81 (14) | C9—N2—C12—C13 | 63.31 (16) |
C4—N1—C8—N2 | −178.11 (13) | N2—C12—C13—C14 | −54.07 (17) |
C4—N1—C8—S1 | 4.3 (2) | C12—C13—C14—C10 | 50.08 (18) |
C9—N2—C8—N1 | 177.19 (13) | C9—C10—C14—C13 | −51.43 (17) |
C12—N2—C8—N1 | −49.87 (18) | C11—C10—C14—C13 | 69.55 (17) |
C9—N2—C8—S1 | −5.01 (16) |
Experimental details
(1) | (2) | (3) | |
Crystal data | |||
Chemical formula | C14H15F3N2S | C13H15FN2S | C14H18N2S |
Mr | 300.34 | 250.33 | 246.36 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Orthorhombic, Pbca |
Temperature (K) | 298 | 293 | 100 |
a, b, c (Å) | 13.074 (8), 9.185 (5), 12.652 (8) | 7.586 (1), 10.088 (2), 16.566 (4) | 8.7377 (2), 14.1088 (3), 20.8300 (5) |
α, β, γ (°) | 90, 109.33 (6), 90 | 90, 91.41 (3), 90 | 90, 90, 90 |
V (Å3) | 1433.7 (15) | 1267.4 (4) | 2567.89 (10) |
Z | 4 | 4 | 8 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.25 | 0.25 | 0.23 |
Crystal size (mm) | 0.35 × 0.20 × 0.15 | 0.45 × 0.30 × 0.15 | 0.20 × 0.20 × 0.20 |
Data collection | |||
Diffractometer | Nonius CAD-4 diffractometer | Nonius CAD-4 diffractometer | Bruker Kappa APEX-II CCD diffractometer |
Absorption correction | – | – | Multi-scan SADABS (Bruker, 2008) |
Tmin, Tmax | – | – | 0.932, 0.955 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2627, 2514, 852 | 3814, 3698, 2094 | 38126, 2265, 2100 |
Rint | 0.060 | 0.018 | 0.033 |
(sin θ/λ)max (Å−1) | 0.595 | 0.703 | 0.595 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.075, 0.221, 0.87 | 0.040, 0.127, 0.98 | 0.033, 0.085, 1.08 |
No. of reflections | 2514 | 3698 | 2265 |
No. of parameters | 210 | 154 | 155 |
No. of restraints | 12 | 0 | 0 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.44, −0.35 | 0.27, −0.25 | 0.51, −0.19 |
Computer programs: CAD-4 (Enraf-Nonius, 1993), APEX2 (Bruker, 2008), CAD-4, APEX2, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXL97.
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