Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614001140/zb5033sup1.cif | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormAsup2.rtv | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormZsup3.rtv | |
Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052520614001140/zb5033FormXsup4.rtv |
CCDC references: 981714; 981715; 981716
Crystal data, data collection and structure refinement details are summarized in Table 1. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms.
For all compounds, data collection: XRD Commander; cell refinement: FOX 1.9.7.0; program(s) used to solve structure: FOX 1.9.7.0; program(s) used to refine structure: FullProf; molecular graphics: Mercury 3.1; software used to prepare material for publication: publCIF.
C12H17SN2+Cl− | V = 1360.67 (6) Å3 |
Mr = 256.79 | Z = 4 |
Monoclinic, P21/c | Dx = 1.254 Mg m−3 |
Hall symbol: -P 2ybc | Melting point: 442 K |
a = 11.5870 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.7174 (2) Å | T = 293 K |
c = 14.8813 (4) Å | white |
β = 115.1475 (13)° | cylinder, 20 × 0.5 mm |
Bruker D8 diffractometer | Data collection mode: reflection |
Radiation source: sealed X-ray tube | Scan method: step |
None monochromator | 2θmin = 3.00°, 2θmax = 90.00°, 2θstep = 0.01° |
Specimen mounting: plate holder |
Refinement on Inet | 165 parameters |
Least-squares matrix: full | 54 restraints |
Rp = 0.071 | 39 constraints |
Rwp = 0.091 | Hydrogen site location: inferred from neighbouring sites |
Rexp = 0.066 | H-atom parameters not refined |
RBragg = 0.037 | |
χ2 = 1.796 | (Δ/σ)max = 0.01 |
8701 data points | Background function: linear extrapolation |
Profile function: Pseudo Voigt | Preferred orientation correction: March–Dollase model G=0.9334(13) |
C12H17SN2+Cl− | β = 115.1475 (13)° |
Mr = 256.79 | V = 1360.67 (6) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 11.5870 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.7174 (2) Å | T = 293 K |
c = 14.8813 (4) Å | cylinder, 20 × 0.5 mm |
Bruker D8 diffractometer | Scan method: step |
Specimen mounting: plate holder | 2θmin = 3.00°, 2θmax = 90.00°, 2θstep = 0.01° |
Data collection mode: reflection |
Rp = 0.071 | 8701 data points |
Rwp = 0.091 | 165 parameters |
Rexp = 0.066 | 54 restraints |
RBragg = 0.037 | H-atom parameters not refined |
χ2 = 1.796 |
Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms. The preferred orientation was included in the Rietveld refinement using the March–Dollase model with direction [-102]. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.3208 (3) | 0.17637 (12) | 0.76667 (12) | 0.01267* | |
C2 | 0.48047 (12) | 0.12307 (12) | 0.85937 (12) | 0.01267* | |
C3 | 0.53247 (12) | 0.23867 (12) | 0.94357 (12) | 0.01267* | |
C4 | 0.54997 (12) | 0.39067 (12) | 0.90437 (12) | 0.01267* | |
N5 | 0.42787 (12) | 0.45487 (12) | 0.83247 (12) | 0.01267* | |
C6 | 0.33157 (12) | 0.37717 (12) | 0.76917 (12) | 0.01267* | |
N7 | 0.24067 (12) | 0.44947 (12) | 0.69507 (12) | 0.01267* | |
C8 | 0.1235 (6) | 0.37383 (13) | 0.62973 (13) | 0.01267* | |
C9 | 0.12363 (13) | 0.30523 (13) | 0.54333 (13) | 0.01267* | |
C10 | 0.01133 (13) | 0.23503 (13) | 0.47683 (13) | 0.01267* | |
C11 | −0.09567 (13) | 0.23433 (13) | 0.49703 (13) | 0.01267* | |
C12 | −0.09247 (13) | 0.30263 (13) | 0.58243 (13) | 0.01267* | |
C13 | 0.01903 (13) | 0.37383 (13) | 0.65143 (13) | 0.01267* | |
C14 | 0.02063 (13) | 0.44833 (13) | 0.74373 (13) | 0.01267* | |
C15 | 0.23913 (13) | 0.31243 (13) | 0.52123 (13) | 0.01267* | |
H21 | 0.4704 | 0.0274 | 0.8855 | 0.0152* | |
H22 | 0.5396 | 0.1131 | 0.8310 | 0.0152* | |
H31 | 0.6132 | 0.2045 | 0.9931 | 0.0152* | |
H32 | 0.4750 | 0.2501 | 0.9736 | 0.0152* | |
H41 | 0.5882 | 0.4609 | 0.9592 | 0.0152* | |
H42 | 0.6060 | 0.3789 | 0.8734 | 0.0152* | |
H10 | 0.0094 | 0.1894 | 0.4197 | 0.0152* | |
H11 | −0.1704 | 0.1880 | 0.4532 | 0.0152* | |
H12 | −0.1652 | 0.3028 | 0.5960 | 0.0152* | |
H141 | −0.0587 | 0.4374 | 0.7463 | 0.0152* | |
H142 | 0.0860 | 0.4029 | 0.8025 | 0.0152* | |
H143 | 0.0405 | 0.5562 | 0.7451 | 0.0152* | |
H151 | 0.2230 | 0.2623 | 0.4621 | 0.0152* | |
H152 | 0.3109 | 0.2659 | 0.5751 | 0.0152* | |
H153 | 0.2611 | 0.4182 | 0.5174 | 0.0152* | |
H51 | 0.4194 | 0.5641 | 0.8331 | 0.0152* | |
H71 | 0.2400 | 0.5593 | 0.6957 | 0.0152* | |
Cl16 | 0.3242 (3) | 0.7843 (4) | 0.7759 (2) | 0.01267* |
S1—C2 | 1.837 (3) | C2—H22 | 0.95 |
S1—C6 | 1.7542 (15) | C3—H31 | 0.96 |
N5—C4 | 1.474 (2) | C3—H32 | 0.95 |
N5—C6 | 1.303 (2) | C4—H41 | 0.96 |
N7—C6 | 1.317 (2) | C4—H42 | 0.95 |
N7—C8 | 1.450 (5) | C10—H10 | 0.93 |
C2—C3 | 1.519 (2) | C11—H11 | 0.93 |
C3—C4 | 1.4959 (17) | C12—H12 | 0.95 |
C8—C9 | 1.419 (4) | C14—H141 | 0.94 |
C8—C13 | 1.379 (7) | C14—H142 | 0.97 |
C9—C15 | 1.509 (2) | C14—H143 | 0.97 |
C9—C10 | 1.397 (2) | C15—H151 | 0.93 |
C10—C11 | 1.394 (2) | C15—H152 | 0.97 |
C11—C12 | 1.390 (2) | C15—H153 | 0.96 |
C12—C13 | 1.408 (2) | N5—H51 | 0.96 |
C13—C14 | 1.512 (2) | N7—H71 | 0.96 |
C2—H21 | 0.95 | ||
C2—S1—C6 | 101.34 (13) | C3—C2—H22 | 109.0 |
C4—N5—C6 | 126.18 (10) | H21—C2—H22 | 110.0 |
C6—N7—C8 | 122.11 (11) | C2—C3—H31 | 110.0 |
C4—N5—H51 | 116.0 | C2—C3—H32 | 110.0 |
C6—N5—H51 | 118.0 | C4—C3—H31 | 109.0 |
C6—N7—H71 | 118.0 | C4—C3—H32 | 109.0 |
C8—N7—H71 | 117.0 | H31—C3—H32 | 109.0 |
S1—C2—C3 | 111.82 (10) | N5—C4—H41 | 109.0 |
C2—C3—C4 | 109.75 (13) | N5—C4—H42 | 109.0 |
N5—C4—C3 | 111.84 (12) | C3—C4—H41 | 109.0 |
N5—C6—N7 | 119.40 (11) | C3—C4—H42 | 109.0 |
S1—C6—N5 | 124.43 (14) | H41—C4—H42 | 108.0 |
S1—C6—N7 | 115.80 (13) | C9—C10—H10 | 119.0 |
N7—C8—C13 | 120.5 (2) | C11—C10—H10 | 121.0 |
C9—C8—C13 | 123.5 (3) | C10—C11—H11 | 120.0 |
N7—C8—C9 | 116.0 (5) | C12—C11—H11 | 119.0 |
C8—C9—C10 | 117.9 (3) | C11—C12—H12 | 121.0 |
C8—C9—C15 | 121.5 (3) | C13—C12—H12 | 118.0 |
C10—C9—C15 | 120.60 (15) | C13—C14—H141 | 111.0 |
C9—C10—C11 | 119.67 (15) | C13—C14—H142 | 110.0 |
C10—C11—C12 | 120.98 (15) | C13—C14—H143 | 110.0 |
C11—C12—C13 | 121.04 (16) | H141—C14—H142 | 109.0 |
C8—C13—C14 | 122.65 (16) | H141—C14—H143 | 109.0 |
C12—C13—C14 | 120.34 (15) | H142—C14—H143 | 107.0 |
C8—C13—C12 | 117.01 (16) | C9—C15—H151 | 110.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 109.0 |
S1—C2—H22 | 112.0 | C9—C15—H153 | 109.0 |
C3—C2—H21 | 109.0 | H151—C15—H152 | 110.0 |
H151—C15—H153 | 110.0 | H152—C15—H153 | 107.0 |
C12H17N2S+Cl− | V = 1343.38 (10) Å3 |
Mr = 256.79 | Z = 4 |
Monoclinic, P21/n | Dx = 1.270 Mg m−3 |
Hall symbol: -P 2yn | Melting point: 415 K |
a = 12.4500 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.6223 (5) Å | T = 293 K |
c = 9.3622 (4) Å | white |
β = 97.410 (3)° | cylinder, 16 × 0.5 mm |
Bruker D8 diffractometer | Data collection mode: transmission |
Radiation source: sealed X-ray tube | Scan method: step |
None monochromator | 2θmin = 3.00°, 2θmax = 70.00°, 2θstep = 0.01° |
Specimen mounting: capillary |
Refinement on Inet | 134 parameters |
Least-squares matrix: full | 54 restraints |
Rp = 0.016 | 39 constraints |
Rwp = 0.021 | Hydrogen site location: inferred from neighbouring sites |
Rexp = 0.016 | H-atom parameters not refined |
RBragg = 0.001 | |
χ2 = 1.823 | (Δ/σ)max = 0.01 |
6701 data points | Background function: linear extrapolation |
Profile function: Pseudo Voigt |
C12H17N2S+Cl− | β = 97.410 (3)° |
Mr = 256.79 | V = 1343.38 (10) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 12.4500 (5) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 11.6223 (5) Å | T = 293 K |
c = 9.3622 (4) Å | cylinder, 16 × 0.5 mm |
Bruker D8 diffractometer | Scan method: step |
Specimen mounting: capillary | 2θmin = 3.00°, 2θmax = 70.00°, 2θstep = 0.01° |
Data collection mode: transmission |
Rp = 0.016 | 6701 data points |
Rwp = 0.021 | 134 parameters |
Rexp = 0.016 | 54 restraints |
RBragg = 0.001 | H-atom parameters not refined |
χ2 = 1.823 |
Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.67794 (12) | 0.69660 (12) | 0.21277 (12) | 0.01267* | |
C2 | 0.70430 (12) | 0.67525 (12) | 0.40519 (12) | 0.01267* | |
C3 | 0.82387 (12) | 0.66817 (12) | 0.45666 (12) | 0.01267* | |
C4 | 0.87003 (12) | 0.56467 (12) | 0.39442 (12) | 0.01267* | |
N5 | 0.85970 (12) | 0.56689 (12) | 0.23515 (12) | 0.01267* | |
C6 | 0.78293 (12) | 0.61983 (12) | 0.15206 (12) | 0.01267* | |
N7 | 0.78904 (12) | 0.62512 (12) | 0.01347 (12) | 0.01267* | |
C8 | 0.70104 (13) | 0.65692 (13) | −0.08795 (13) | 0.01267* | |
C9 | 0.70285 (13) | 0.77031 (13) | −0.14148 (13) | 0.01267* | |
C10 | 0.62273 (13) | 0.80367 (13) | −0.25229 (13) | 0.01267* | |
C11 | 0.54333 (13) | 0.72513 (13) | −0.30705 (13) | 0.01267* | |
C12 | 0.54249 (13) | 0.61376 (13) | −0.25306 (13) | 0.01267* | |
C13 | 0.62195 (13) | 0.57661 (13) | −0.14209 (13) | 0.01267* | |
C14 | 0.61948 (13) | 0.45536 (13) | −0.08409 (13) | 0.01267* | |
C15 | 0.78727 (13) | 0.85501 (13) | −0.07686 (13) | 0.01267* | |
Cl16 | 0.5210 (3) | 0.1114 (3) | 0.6757 (4) | 0.01267* | |
H21 | 0.6776 | 0.7443 | 0.4479 | 0.0152* | |
H23 | 0.6720 | 0.6111 | 0.4376 | 0.0152* | |
H31 | 0.8616 | 0.7378 | 0.4297 | 0.0152* | |
H32 | 0.8375 | 0.6659 | 0.5615 | 0.0152* | |
H41 | 0.9474 | 0.5624 | 0.4337 | 0.0152* | |
H42 | 0.8360 | 0.5014 | 0.4260 | 0.0152* | |
H10 | 0.6215 | 0.8786 | −0.2910 | 0.0152* | |
H11 | 0.4881 | 0.7471 | −0.3833 | 0.0152* | |
H12 | 0.4864 | 0.5609 | −0.2927 | 0.0152* | |
H141 | 0.5592 | 0.4139 | −0.1356 | 0.0152* | |
H142 | 0.6842 | 0.4163 | −0.0976 | 0.0152* | |
H143 | 0.6108 | 0.4569 | 0.0146 | 0.0152* | |
H151 | 0.7757 | 0.9257 | −0.1264 | 0.0152* | |
H152 | 0.8564 | 0.8254 | −0.0877 | 0.0152* | |
H153 | 0.7800 | 0.8644 | 0.0214 | 0.0152* | |
H51 | 0.9155 | 0.5296 | 0.1928 | 0.0152* | |
H71 | 0.8594 | 0.6125 | −0.0166 | 0.0152* |
S1—C2 | 1.8061 (16) | C13—C14 | 1.512 (2) |
S1—C6 | 1.738 (2) | C2—H21 | 0.97 |
N5—C4 | 1.4803 (16) | C2—H23 | 0.92 |
N5—C6 | 1.3059 (19) | C3—H31 | 0.98 |
N7—C6 | 1.3109 (16) | C3—H32 | 0.97 |
N7—C8 | 1.404 (2) | C4—H41 | 0.99 |
N5—H51 | 0.95 | C4—H42 | 0.92 |
N7—H71 | 0.97 | C10—H10 | 0.94 |
C2—C3 | 1.507 (2) | C11—H11 | 0.96 |
C3—C4 | 1.484 (2) | C12—H12 | 0.97 |
C8—C9 | 1.411 (2) | C14—H141 | 0.97 |
C8—C13 | 1.403 (2) | C14—H142 | 0.95 |
C9—C15 | 1.509 (2) | C14—H143 | 0.94 |
C9—C10 | 1.398 (2) | C15—H151 | 0.95 |
C10—C11 | 1.394 (2) | C15—H152 | 0.94 |
C11—C12 | 1.390 (2) | C15—H153 | 0.94 |
C12—C13 | 1.407 (2) | ||
C2—S1—C6 | 102.01 (9) | C3—C2—H23 | 108.0 |
C4—N5—C6 | 124.76 (13) | H21—C2—H23 | 110.0 |
C6—N7—C8 | 122.82 (14) | C2—C3—H31 | 111.0 |
C4—N5—H51 | 116.0 | C2—C3—H32 | 111.0 |
C6—N5—H51 | 119.0 | C4—C3—H31 | 110.0 |
C6—N7—H71 | 117.0 | C4—C3—H32 | 110.0 |
C8—N7—H71 | 120.0 | H31—C3—H32 | 105.0 |
S1—C2—C3 | 111.81 (10) | N5—C4—H41 | 109.0 |
C2—C3—C4 | 109.59 (11) | N5—C4—H42 | 111.0 |
N5—C4—C3 | 113.18 (11) | C3—C4—H41 | 107.0 |
N5—C6—N7 | 118.70 (14) | C3—C4—H42 | 108.0 |
S1—C6—N5 | 124.80 (10) | H41—C4—H42 | 109.0 |
S1—C6—N7 | 116.22 (12) | C9—C10—H10 | 121.0 |
N7—C8—C13 | 121.29 (13) | C11—C10—H10 | 119.0 |
C9—C8—C13 | 122.38 (13) | C10—C11—H11 | 120.0 |
N7—C8—C9 | 116.06 (14) | C12—C11—H11 | 119.0 |
C8—C9—C10 | 118.68 (14) | C11—C12—H12 | 119.0 |
C8—C9—C15 | 120.61 (12) | C13—C12—H12 | 119.0 |
C10—C9—C15 | 120.67 (13) | C13—C14—H141 | 110.0 |
C9—C10—C11 | 119.71 (14) | C13—C14—H142 | 110.0 |
C10—C11—C12 | 120.95 (13) | C13—C14—H143 | 110.0 |
C11—C12—C13 | 121.11 (14) | H141—C14—H142 | 108.0 |
C8—C13—C14 | 122.42 (13) | H141—C14—H143 | 109.0 |
C12—C13—C14 | 120.42 (13) | H142—C14—H143 | 110.0 |
C8—C13—C12 | 117.16 (13) | C9—C15—H151 | 108.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 108.0 |
S1—C2—H23 | 114.0 | C9—C15—H153 | 109.0 |
C3—C2—H21 | 107.0 | H151—C15—H152 | 110.0 |
H151—C15—H153 | 111.0 | H152—C15—H153 | 111.0 |
C12H17SN2+Cl− | V = 1369.8 (2) Å3 |
Mr = 256.79 | Z = 4 |
Monoclinic, P21/c | Dx = 1.245 Mg m−3 |
Hall symbol: -P 2yn | Melting point: 406 K |
a = 12.1155 (13) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.3857 (7) Å | T = 293 K |
c = 13.5322 (15) Å | white |
β = 94.921 (6)° | cylinder, 16 × 0.5 mm |
Bruker D8 diffractometer | Data collection mode: transmission |
Radiation source: sealed X-ray tube | Scan method: step |
None monochromator | 2θmin = 4.00°, 2θmax = 89.99°, 2θstep = 0.01° |
Specimen mounting: capillary |
Refinement on Inet | 159 parameters |
Least-squares matrix: full | 54 restraints |
Rp = 0.017 | 39 constraints |
Rwp = 0.023 | Hydrogen site location: inferred from neighbouring sites |
Rexp = 0.017 | H-atom parameters not refined |
RBragg = 0.011 | |
χ2 = 1.742 | (Δ/σ)max = 0.01 |
8411 data points | Background function: linear extrapolation |
Profile function: Pseudo Voigt |
C12H17SN2+Cl− | β = 94.921 (6)° |
Mr = 256.79 | V = 1369.8 (2) Å3 |
Monoclinic, P21/c | Z = 4 |
a = 12.1155 (13) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 8.3857 (7) Å | T = 293 K |
c = 13.5322 (15) Å | cylinder, 16 × 0.5 mm |
Bruker D8 diffractometer | Scan method: step |
Specimen mounting: capillary | 2θmin = 4.00°, 2θmax = 89.99°, 2θstep = 0.01° |
Data collection mode: transmission |
Rp = 0.017 | 8411 data points |
Rwp = 0.023 | 159 parameters |
Rexp = 0.017 | 54 restraints |
RBragg = 0.011 | H-atom parameters not refined |
χ2 = 1.742 |
Refinement. Atomic parameters for (S1, C2, C3, C4, N5, C6, N7) and (C8, C9, C10, C11, C12, C13, C14, C15) were refined as a rigid bodies. Final refinements were performed with hydrogen atoms. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.73892 (16) | 0.08908 (16) | 0.81021 (16) | 0.01267* | |
C2 | 0.63530 (16) | −0.06709 (16) | 0.79088 (16) | 0.01267* | |
C3 | 0.52198 (16) | 0.00420 (16) | 0.77192 (16) | 0.01267* | |
C4 | 0.49018 (16) | 0.09005 (16) | 0.86434 (16) | 0.01267* | |
N5 | 0.56661 (16) | 0.22178 (16) | 0.89455 (16) | 0.01267* | |
C6 | 0.67343 (16) | 0.22707 (16) | 0.88171 (16) | 0.01267* | |
N7 | 0.74423 (16) | 0.32069 (16) | 0.93573 (16) | 0.01267* | |
C8 | 0.85376 (18) | 0.33045 (18) | 0.91343 (18) | 0.01267* | |
C9 | 0.93004 (18) | 0.24377 (18) | 0.97637 (18) | 0.01267* | |
C10 | 1.04286 (18) | 0.26643 (18) | 0.96784 (18) | 0.01267* | |
C11 | 1.07732 (18) | 0.37322 (18) | 0.89819 (18) | 0.01267* | |
C12 | 1.00100 (18) | 0.45789 (18) | 0.83682 (18) | 0.01267* | |
C13 | 0.88669 (18) | 0.43798 (18) | 0.84267 (18) | 0.01267* | |
C14 | 0.80484 (18) | 0.53167 (18) | 0.77573 (18) | 0.01267* | |
C15 | 0.89081 (18) | 0.13328 (18) | 1.05365 (18) | 0.01267* | |
H21 | 0.6514 | −0.1204 | 0.7321 | 0.0152* | |
H22 | 0.6315 | −0.1451 | 0.8401 | 0.0152* | |
H31 | 0.4701 | −0.0807 | 0.7593 | 0.0152* | |
H32 | 0.5178 | 0.0740 | 0.7145 | 0.0152* | |
H41 | 0.4868 | 0.0113 | 0.9132 | 0.0152* | |
H42 | 0.4136 | 0.1284 | 0.8473 | 0.0152* | |
H10 | 1.0969 | 0.2098 | 1.0104 | 0.0152* | |
H11 | 1.1552 | 0.3892 | 0.8935 | 0.0152* | |
H12 | 1.0273 | 0.5316 | 0.7908 | 0.0152* | |
H141 | 0.8445 | 0.5985 | 0.7341 | 0.0152* | |
H142 | 0.7619 | 0.5972 | 0.8157 | 0.0152* | |
H143 | 0.7591 | 0.4610 | 0.7377 | 0.0152* | |
H151 | 0.9538 | 0.0855 | 1.0902 | 0.0152* | |
H152 | 0.8508 | 0.1931 | 1.0991 | 0.0152* | |
H153 | 0.8456 | 0.0540 | 1.0231 | 0.0152* | |
H71 | 0.7148 | 0.4123 | 0.9650 | 0.0152* | |
H51 | 0.5322 | 0.3069 | 0.9221 | 0.0152* | |
Cl16 | 0.3798 (9) | 0.1678 (9) | 0.5058 (4) | 0.01267* |
S1—C2 | 1.818 (2) | C13—C14 | 1.506 (3) |
S1—C6 | 1.743 (3) | C2—H21 | 0.95 |
N5—C4 | 1.476 (2) | C2—H22 | 0.94 |
N5—C6 | 1.321 (3) | C3—H31 | 0.96 |
N7—C6 | 1.334 (3) | C3—H32 | 0.97 |
N7—C8 | 1.388 (3) | C4—H41 | 0.94 |
N5—H51 | 0.92 | C4—H42 | 0.99 |
N7—H71 | 0.95 | C10—H10 | 0.96 |
C2—C3 | 1.499 (3) | C11—H11 | 0.96 |
C3—C4 | 1.521 (3) | C12—H12 | 0.95 |
C8—C9 | 1.405 (3) | C14—H141 | 0.95 |
C8—C13 | 1.398 (3) | C14—H142 | 0.96 |
C9—C15 | 1.504 (3) | C14—H143 | 0.93 |
C9—C10 | 1.395 (3) | C15—H151 | 0.96 |
C10—C11 | 1.390 (3) | C15—H152 | 0.96 |
C11—C12 | 1.385 (3) | C15—H153 | 0.93 |
C12—C13 | 1.404 (3) | ||
C2—S1—C6 | 102.51 (13) | C3—C2—H22 | 107.0 |
C4—N5—C6 | 125.93 (16) | H21—C2—H22 | 107.0 |
C6—N7—C8 | 119.83 (19) | C2—C3—H31 | 108.0 |
C4—N5—H51 | 113.0 | C2—C3—H32 | 111.0 |
C6—N5—H51 | 121.0 | C4—C3—H31 | 107.0 |
C6—N7—H71 | 117.0 | C4—C3—H32 | 112.0 |
C8—N7—H71 | 116.0 | H31—C3—H32 | 109.0 |
S1—C2—C3 | 110.39 (11) | N5—C4—H41 | 113.0 |
C2—C3—C4 | 109.93 (17) | N5—C4—H42 | 112.0 |
N5—C4—C3 | 112.63 (16) | C3—C4—H41 | 106.0 |
N5—C6—N7 | 122.61 (18) | C3—C4—H42 | 105.0 |
S1—C6—N5 | 123.27 (15) | H41—C4—H42 | 107.0 |
S1—C6—N7 | 113.15 (16) | C9—C10—H10 | 120.0 |
N7—C8—C13 | 121.41 (19) | C11—C10—H10 | 120.0 |
C9—C8—C13 | 122.5 (2) | C10—C11—H11 | 119.0 |
N7—C8—C9 | 115.41 (19) | C12—C11—H11 | 120.0 |
C8—C9—C10 | 118.55 (19) | C11—C12—H12 | 119.0 |
C8—C9—C15 | 120.64 (19) | C13—C12—H12 | 120.0 |
C10—C9—C15 | 120.78 (19) | C13—C14—H141 | 109.0 |
C9—C10—C11 | 119.8 (2) | C13—C14—H142 | 109.0 |
C10—C11—C12 | 120.9 (2) | C13—C14—H143 | 109.0 |
C11—C12—C13 | 121.10 (19) | H141—C14—H142 | 109.0 |
C8—C13—C14 | 122.46 (19) | H141—C14—H143 | 111.0 |
C12—C13—C14 | 120.40 (18) | H142—C14—H143 | 111.0 |
C8—C13—C12 | 117.14 (19) | C9—C15—H151 | 109.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 109.0 |
S1—C2—H22 | 118.0 | C9—C15—H153 | 110.0 |
C3—C2—H21 | 107.0 | H151—C15—H152 | 108.0 |
H151—C15—H153 | 110.0 | H152—C15—H153 | 110.0 |
Experimental details
(FormA) | (FormZ) | (FormX) | |
Crystal data | |||
Chemical formula | C12H17SN2+Cl− | C12H17N2S+Cl− | C12H17SN2+Cl− |
Mr | 256.79 | 256.79 | 256.79 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 293 | 293 | 293 |
a, b, c (Å) | 11.5870 (3), 8.7174 (2), 14.8813 (4) | 12.4500 (5), 11.6223 (5), 9.3622 (4) | 12.1155 (13), 8.3857 (7), 13.5322 (15) |
β (°) | 115.1475 (13) | 97.410 (3) | 94.921 (6) |
V (Å3) | 1360.67 (6) | 1343.38 (10) | 1369.8 (2) |
Z | 4 | 4 | 4 |
Radiation type | Cu Kα, λ = 1.54184 Å | Cu Kα, λ = 1.54184 Å | Cu Kα, λ = 1.54184 Å |
µ (mm−1) | – | ? | ? |
Specimen shape, size (mm) | Cylinder, 20 × 0.5 | Cylinder, 16 × 0.5 | Cylinder, 16 × 0.5 |
Data collection | |||
Diffractometer | Bruker D8 diffractometer | Bruker D8 diffractometer | Bruker D8 diffractometer |
Specimen mounting | Plate holder | Capillary | Capillary |
Data collection mode | Reflection | Transmission | Transmission |
Scan method | Step | Step | Step |
2θ values (°) | 2θmin = 3.00 2θmax = 90.00 2θstep = 0.01 | 2θmin = 3.00 2θmax = 70.00 2θstep = 0.01 | 2θmin = 4.00 2θmax = 89.99 2θstep = 0.01 |
Refinement | |||
R factors and goodness of fit | Rp = 0.071, Rwp = 0.091, Rexp = 0.066, RBragg = 0.037, χ2 = 1.796 | Rp = 0.016, Rwp = 0.021, Rexp = 0.016, RBragg = 0.001, χ2 = 1.823 | Rp = 0.017, Rwp = 0.023, Rexp = 0.017, RBragg = 0.011, χ2 = 1.742 |
No. of data points | 8701 | 6701 | 8411 |
No. of parameters | 165 | 134 | 159 |
No. of restraints | 54 | 54 | 54 |
H-atom treatment | H-atom parameters not refined | H-atom parameters not refined | H-atom parameters not refined |
Computer programs: XRD Commander, FOX 1.9.7.0, FullProf, Mercury 3.1, publCIF.
C2—S1—C6 | 101.34 (13) | C3—C2—H22 | 109.0 |
C4—N5—C6 | 126.18 (10) | H21—C2—H22 | 110.0 |
C6—N7—C8 | 122.11 (11) | C2—C3—H31 | 110.0 |
C4—N5—H51 | 116.0 | C2—C3—H32 | 110.0 |
C6—N5—H51 | 118.0 | C4—C3—H31 | 109.0 |
C6—N7—H71 | 118.0 | C4—C3—H32 | 109.0 |
C8—N7—H71 | 117.0 | H31—C3—H32 | 109.0 |
S1—C2—C3 | 111.82 (10) | N5—C4—H41 | 109.0 |
C2—C3—C4 | 109.75 (13) | N5—C4—H42 | 109.0 |
N5—C4—C3 | 111.84 (12) | C3—C4—H41 | 109.0 |
N5—C6—N7 | 119.40 (11) | C3—C4—H42 | 109.0 |
S1—C6—N5 | 124.43 (14) | H41—C4—H42 | 108.0 |
S1—C6—N7 | 115.80 (13) | C9—C10—H10 | 119.0 |
N7—C8—C13 | 120.5 (2) | C11—C10—H10 | 121.0 |
C9—C8—C13 | 123.5 (3) | C10—C11—H11 | 120.0 |
N7—C8—C9 | 116.0 (5) | C12—C11—H11 | 119.0 |
C8—C9—C10 | 117.9 (3) | C11—C12—H12 | 121.0 |
C8—C9—C15 | 121.5 (3) | C13—C12—H12 | 118.0 |
C10—C9—C15 | 120.60 (15) | C13—C14—H141 | 111.0 |
C9—C10—C11 | 119.67 (15) | C13—C14—H142 | 110.0 |
C10—C11—C12 | 120.98 (15) | C13—C14—H143 | 110.0 |
C11—C12—C13 | 121.04 (16) | H141—C14—H142 | 109.0 |
C8—C13—C14 | 122.65 (16) | H141—C14—H143 | 109.0 |
C12—C13—C14 | 120.34 (15) | H142—C14—H143 | 107.0 |
C8—C13—C12 | 117.01 (16) | C9—C15—H151 | 110.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 109.0 |
S1—C2—H22 | 112.0 | C9—C15—H153 | 109.0 |
C3—C2—H21 | 109.0 | H151—C15—H152 | 110.0 |
H151—C15—H153 | 110.0 | H152—C15—H153 | 107.0 |
C2—S1—C6 | 102.01 (9) | C3—C2—H23 | 108.0 |
C4—N5—C6 | 124.76 (13) | H21—C2—H23 | 110.0 |
C6—N7—C8 | 122.82 (14) | C2—C3—H31 | 111.0 |
C4—N5—H51 | 116.0 | C2—C3—H32 | 111.0 |
C6—N5—H51 | 119.0 | C4—C3—H31 | 110.0 |
C6—N7—H71 | 117.0 | C4—C3—H32 | 110.0 |
C8—N7—H71 | 120.0 | H31—C3—H32 | 105.0 |
S1—C2—C3 | 111.81 (10) | N5—C4—H41 | 109.0 |
C2—C3—C4 | 109.59 (11) | N5—C4—H42 | 111.0 |
N5—C4—C3 | 113.18 (11) | C3—C4—H41 | 107.0 |
N5—C6—N7 | 118.70 (14) | C3—C4—H42 | 108.0 |
S1—C6—N5 | 124.80 (10) | H41—C4—H42 | 109.0 |
S1—C6—N7 | 116.22 (12) | C9—C10—H10 | 121.0 |
N7—C8—C13 | 121.29 (13) | C11—C10—H10 | 119.0 |
C9—C8—C13 | 122.38 (13) | C10—C11—H11 | 120.0 |
N7—C8—C9 | 116.06 (14) | C12—C11—H11 | 119.0 |
C8—C9—C10 | 118.68 (14) | C11—C12—H12 | 119.0 |
C8—C9—C15 | 120.61 (12) | C13—C12—H12 | 119.0 |
C10—C9—C15 | 120.67 (13) | C13—C14—H141 | 110.0 |
C9—C10—C11 | 119.71 (14) | C13—C14—H142 | 110.0 |
C10—C11—C12 | 120.95 (13) | C13—C14—H143 | 110.0 |
C11—C12—C13 | 121.11 (14) | H141—C14—H142 | 108.0 |
C8—C13—C14 | 122.42 (13) | H141—C14—H143 | 109.0 |
C12—C13—C14 | 120.42 (13) | H142—C14—H143 | 110.0 |
C8—C13—C12 | 117.16 (13) | C9—C15—H151 | 108.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 108.0 |
S1—C2—H23 | 114.0 | C9—C15—H153 | 109.0 |
C3—C2—H21 | 107.0 | H151—C15—H152 | 110.0 |
H151—C15—H153 | 111.0 | H152—C15—H153 | 111.0 |
C2—S1—C6 | 102.51 (13) | C3—C2—H22 | 107.0 |
C4—N5—C6 | 125.93 (16) | H21—C2—H22 | 107.0 |
C6—N7—C8 | 119.83 (19) | C2—C3—H31 | 108.0 |
C4—N5—H51 | 113.0 | C2—C3—H32 | 111.0 |
C6—N5—H51 | 121.0 | C4—C3—H31 | 107.0 |
C6—N7—H71 | 117.0 | C4—C3—H32 | 112.0 |
C8—N7—H71 | 116.0 | H31—C3—H32 | 109.0 |
S1—C2—C3 | 110.39 (11) | N5—C4—H41 | 113.0 |
C2—C3—C4 | 109.93 (17) | N5—C4—H42 | 112.0 |
N5—C4—C3 | 112.63 (16) | C3—C4—H41 | 106.0 |
N5—C6—N7 | 122.61 (18) | C3—C4—H42 | 105.0 |
S1—C6—N5 | 123.27 (15) | H41—C4—H42 | 107.0 |
S1—C6—N7 | 113.15 (16) | C9—C10—H10 | 120.0 |
N7—C8—C13 | 121.41 (19) | C11—C10—H10 | 120.0 |
C9—C8—C13 | 122.5 (2) | C10—C11—H11 | 119.0 |
N7—C8—C9 | 115.41 (19) | C12—C11—H11 | 120.0 |
C8—C9—C10 | 118.55 (19) | C11—C12—H12 | 119.0 |
C8—C9—C15 | 120.64 (19) | C13—C12—H12 | 120.0 |
C10—C9—C15 | 120.78 (19) | C13—C14—H141 | 109.0 |
C9—C10—C11 | 119.8 (2) | C13—C14—H142 | 109.0 |
C10—C11—C12 | 120.9 (2) | C13—C14—H143 | 109.0 |
C11—C12—C13 | 121.10 (19) | H141—C14—H142 | 109.0 |
C8—C13—C14 | 122.46 (19) | H141—C14—H143 | 111.0 |
C12—C13—C14 | 120.40 (18) | H142—C14—H143 | 111.0 |
C8—C13—C12 | 117.14 (19) | C9—C15—H151 | 109.0 |
S1—C2—H21 | 106.0 | C9—C15—H152 | 109.0 |
S1—C2—H22 | 118.0 | C9—C15—H153 | 110.0 |
C3—C2—H21 | 107.0 | H151—C15—H152 | 108.0 |
H151—C15—H153 | 110.0 | H152—C15—H153 | 110.0 |