Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614006209/gw5030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614006209/gw5030Asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520614006209/gw5030Bsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614006209/gw5030sup4.pdf |
CCDC references: 949673; 949674
Crystal data, data collection and structure refinement details are summarized in Table 1.
For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C20H18ClF3N3O2S·Cl | Z = 2 |
Mr = 492.33 | F(000) = 504 |
Triclinic, P1 | Dx = 1.503 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.7005 (6) Å | Cell parameters from 10753 reflections |
b = 11.2405 (10) Å | θ = 2.0–28.5° |
c = 13.7322 (12) Å | µ = 0.44 mm−1 |
α = 111.249 (2)° | T = 100 K |
β = 90.907 (2)° | Block, colourless |
γ = 99.769 (2)° | 0.17 × 0.09 × 0.04 mm |
V = 1087.88 (16) Å3 |
Bruker KAPPA APEX II DUO diffractometer | 3549 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 28.5°, θmin = 1.6° |
Absorption correction: multi-scan SADABS | h = −9→10 |
Tmin = 0.929, Tmax = 0.983 | k = −15→14 |
10760 measured reflections | l = −8→18 |
5436 independent reflections |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0463P)2] where P = (Fo2 + 2Fc2)/3 |
5436 reflections | (Δ/σ)max < 0.001 |
294 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C20H18ClF3N3O2S·Cl | γ = 99.769 (2)° |
Mr = 492.33 | V = 1087.88 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.7005 (6) Å | Mo Kα radiation |
b = 11.2405 (10) Å | µ = 0.44 mm−1 |
c = 13.7322 (12) Å | T = 100 K |
α = 111.249 (2)° | 0.17 × 0.09 × 0.04 mm |
β = 90.907 (2)° |
Bruker KAPPA APEX II DUO diffractometer | 5436 independent reflections |
Absorption correction: multi-scan SADABS | 3549 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.983 | Rint = 0.037 |
10760 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.107 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.33 e Å−3 |
5436 reflections | Δρmin = −0.28 e Å−3 |
294 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 | ||
Cl1 | 0.71093 (9) | −0.10790 (6) | 0.58094 (5) | 0.04017 (17) | |
Cl2 | 0.95862 (7) | −0.25306 (6) | −0.23737 (5) | 0.03182 (15) | |
S1 | 0.90866 (9) | 0.70416 (6) | 0.28724 (5) | 0.03918 (17) | |
F1 | 1.1525 (2) | 0.68503 (18) | 0.16265 (15) | 0.0664 (5) | |
F2 | 1.1856 (2) | 0.59124 (18) | 0.27123 (16) | 0.0683 (5) | |
F3 | 0.9900 (2) | 0.50025 (16) | 0.14173 (13) | 0.0586 (5) | |
O1 | 0.6913 (2) | −0.22798 (15) | 0.04957 (13) | 0.0381 (4) | |
O2 | 0.4222 (2) | −0.29213 (18) | −0.03447 (15) | 0.0526 (5) | |
N1 | 0.6339 (2) | 0.13983 (18) | 0.21102 (15) | 0.0227 (4) | |
N2 | 0.3328 (2) | 0.08126 (18) | 0.17491 (15) | 0.0241 (4) | |
N3 | 0.4562 (2) | 0.29616 (18) | 0.26597 (15) | 0.0266 (4) | |
C1 | 0.7349 (4) | −0.3513 (2) | −0.0135 (2) | 0.0466 (7) | |
H1A | 0.6505 | −0.4204 | −0.0064 | 0.070* | |
H1B | 0.8512 | −0.3556 | 0.0097 | 0.070* | |
H1C | 0.7322 | −0.3598 | −0.0856 | 0.070* | |
C2 | 0.5269 (3) | −0.2111 (2) | 0.03164 (17) | 0.0286 (5) | |
C3 | 0.4997 (3) | −0.0830 (2) | 0.10345 (16) | 0.0239 (5) | |
C4 | 0.3444 (3) | −0.0428 (2) | 0.10522 (16) | 0.0240 (5) | |
C5 | 0.1744 (3) | −0.1141 (2) | 0.04042 (18) | 0.0315 (5) | |
H5A | 0.1858 | −0.2015 | −0.0008 | 0.047* | |
H5B | 0.1474 | −0.0708 | −0.0051 | 0.047* | |
H5C | 0.0810 | −0.1156 | 0.0857 | 0.047* | |
C6 | 0.6500 (3) | 0.0032 (2) | 0.18417 (16) | 0.0227 (5) | |
H6 | 0.7613 | −0.0087 | 0.1515 | 0.027* | |
C7 | 0.6600 (3) | −0.0275 (2) | 0.28398 (17) | 0.0234 (5) | |
C8 | 0.5486 (3) | −0.1308 (2) | 0.29594 (18) | 0.0288 (5) | |
H8 | 0.4633 | −0.1838 | 0.2422 | 0.035* | |
C9 | 0.5626 (3) | −0.1563 (2) | 0.38743 (19) | 0.0322 (5) | |
H9 | 0.4878 | −0.2261 | 0.3950 | 0.039* | |
C10 | 0.6887 (3) | −0.0767 (2) | 0.46638 (17) | 0.0282 (5) | |
C11 | 0.8002 (3) | 0.0274 (2) | 0.45679 (18) | 0.0320 (5) | |
H11 | 0.8836 | 0.0814 | 0.5114 | 0.038* | |
C12 | 0.7868 (3) | 0.0508 (2) | 0.36512 (17) | 0.0288 (5) | |
H12 | 0.8636 | 0.1198 | 0.3576 | 0.035* | |
C13 | 0.4782 (3) | 0.1746 (2) | 0.21888 (16) | 0.0225 (5) | |
C14 | 0.5967 (3) | 0.4010 (2) | 0.32548 (17) | 0.0245 (5) | |
C15 | 0.6749 (3) | 0.4871 (2) | 0.28188 (17) | 0.0266 (5) | |
H15 | 0.6390 | 0.4774 | 0.2140 | 0.032* | |
C16 | 0.8089 (3) | 0.5893 (2) | 0.34136 (19) | 0.0283 (5) | |
C17 | 0.8616 (3) | 0.6043 (2) | 0.44282 (19) | 0.0339 (6) | |
H17 | 0.9502 | 0.6733 | 0.4822 | 0.041* | |
C18 | 0.7822 (3) | 0.5164 (2) | 0.48560 (18) | 0.0344 (6) | |
H18 | 0.8180 | 0.5261 | 0.5535 | 0.041* | |
C19 | 0.6492 (3) | 0.4140 (2) | 0.42696 (18) | 0.0318 (5) | |
H19 | 0.5956 | 0.3545 | 0.4551 | 0.038* | |
C20 | 1.0644 (3) | 0.6148 (3) | 0.2136 (2) | 0.0447 (7) | |
H1 | 0.727 (3) | 0.195 (2) | 0.2307 (18) | 0.033 (7)* | |
H2 | 0.237 (4) | 0.109 (2) | 0.180 (2) | 0.044 (8)* | |
H3 | 0.355 (3) | 0.309 (2) | 0.2650 (19) | 0.039 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0472 (4) | 0.0505 (4) | 0.0318 (3) | 0.0162 (3) | 0.0084 (3) | 0.0225 (3) |
Cl2 | 0.0176 (3) | 0.0345 (3) | 0.0424 (3) | 0.0027 (2) | 0.0000 (2) | 0.0142 (3) |
S1 | 0.0402 (4) | 0.0221 (3) | 0.0512 (4) | 0.0000 (3) | 0.0034 (3) | 0.0114 (3) |
F1 | 0.0453 (10) | 0.0759 (13) | 0.0945 (14) | 0.0033 (9) | 0.0232 (10) | 0.0538 (11) |
F2 | 0.0374 (9) | 0.0848 (14) | 0.1007 (15) | 0.0139 (9) | 0.0032 (9) | 0.0545 (12) |
F3 | 0.0572 (11) | 0.0440 (10) | 0.0645 (11) | 0.0100 (8) | 0.0230 (9) | 0.0073 (9) |
O1 | 0.0307 (9) | 0.0327 (10) | 0.0411 (10) | 0.0112 (8) | 0.0002 (8) | 0.0001 (8) |
O2 | 0.0444 (11) | 0.0420 (11) | 0.0474 (11) | 0.0108 (9) | −0.0154 (9) | −0.0120 (9) |
N1 | 0.0146 (9) | 0.0195 (10) | 0.0317 (10) | −0.0012 (8) | −0.0016 (8) | 0.0087 (8) |
N2 | 0.0151 (9) | 0.0259 (10) | 0.0299 (10) | 0.0015 (8) | −0.0006 (8) | 0.0099 (8) |
N3 | 0.0158 (9) | 0.0234 (10) | 0.0388 (11) | 0.0021 (8) | −0.0001 (8) | 0.0101 (9) |
C1 | 0.0467 (16) | 0.0343 (15) | 0.0491 (16) | 0.0166 (13) | 0.0009 (13) | 0.0003 (13) |
C2 | 0.0305 (12) | 0.0311 (13) | 0.0227 (11) | 0.0060 (10) | 0.0010 (10) | 0.0082 (10) |
C3 | 0.0252 (11) | 0.0239 (12) | 0.0207 (10) | 0.0005 (9) | −0.0016 (9) | 0.0079 (9) |
C4 | 0.0238 (11) | 0.0244 (12) | 0.0230 (11) | 0.0004 (9) | −0.0009 (9) | 0.0099 (9) |
C5 | 0.0266 (12) | 0.0320 (13) | 0.0312 (12) | −0.0001 (10) | −0.0075 (10) | 0.0091 (10) |
C6 | 0.0178 (10) | 0.0233 (11) | 0.0257 (11) | 0.0026 (9) | 0.0006 (9) | 0.0080 (9) |
C7 | 0.0203 (10) | 0.0226 (11) | 0.0274 (11) | 0.0055 (9) | 0.0018 (9) | 0.0088 (9) |
C8 | 0.0250 (12) | 0.0282 (13) | 0.0305 (12) | 0.0002 (10) | −0.0031 (10) | 0.0102 (10) |
C9 | 0.0299 (12) | 0.0304 (13) | 0.0397 (13) | 0.0040 (10) | 0.0074 (11) | 0.0175 (11) |
C10 | 0.0309 (12) | 0.0326 (13) | 0.0258 (11) | 0.0132 (11) | 0.0047 (10) | 0.0131 (10) |
C11 | 0.0346 (13) | 0.0292 (13) | 0.0285 (12) | 0.0040 (11) | −0.0060 (10) | 0.0077 (10) |
C12 | 0.0272 (12) | 0.0238 (12) | 0.0324 (12) | −0.0032 (10) | −0.0057 (10) | 0.0107 (10) |
C13 | 0.0196 (10) | 0.0240 (12) | 0.0248 (11) | 0.0005 (9) | −0.0008 (9) | 0.0118 (9) |
C14 | 0.0176 (10) | 0.0209 (11) | 0.0306 (12) | 0.0048 (9) | 0.0009 (9) | 0.0040 (9) |
C15 | 0.0259 (12) | 0.0241 (12) | 0.0267 (11) | 0.0062 (10) | −0.0013 (9) | 0.0052 (9) |
C16 | 0.0245 (11) | 0.0200 (12) | 0.0367 (13) | 0.0026 (9) | 0.0019 (10) | 0.0070 (10) |
C17 | 0.0269 (12) | 0.0248 (13) | 0.0375 (14) | 0.0033 (10) | −0.0048 (11) | −0.0021 (11) |
C18 | 0.0302 (13) | 0.0415 (15) | 0.0274 (12) | 0.0071 (11) | −0.0015 (10) | 0.0078 (11) |
C19 | 0.0269 (12) | 0.0348 (14) | 0.0346 (13) | 0.0059 (10) | 0.0049 (10) | 0.0137 (11) |
C20 | 0.0293 (14) | 0.0458 (17) | 0.0664 (19) | 0.0013 (12) | 0.0061 (13) | 0.0318 (16) |
Cl1—C10 | 1.743 (2) | C5—H5A | 0.9600 |
S1—C20 | 1.784 (3) | C5—H5B | 0.9600 |
S1—C16 | 1.785 (2) | C5—H5C | 0.9600 |
F1—C20 | 1.344 (3) | C6—C7 | 1.533 (3) |
F2—C20 | 1.335 (3) | C6—H6 | 0.9800 |
F3—C20 | 1.330 (3) | C7—C8 | 1.384 (3) |
O1—C2 | 1.343 (3) | C7—C12 | 1.390 (3) |
O1—C1 | 1.442 (3) | C8—C9 | 1.393 (3) |
O2—C2 | 1.196 (3) | C8—H8 | 0.9300 |
N1—C13 | 1.317 (3) | C9—C10 | 1.374 (3) |
N1—C6 | 1.472 (3) | C9—H9 | 0.9300 |
N1—H1 | 0.83 (2) | C10—C11 | 1.378 (3) |
N2—C13 | 1.357 (3) | C11—C12 | 1.382 (3) |
N2—C4 | 1.395 (3) | C11—H11 | 0.9300 |
N2—H2 | 0.84 (3) | C12—H12 | 0.9300 |
N3—C13 | 1.325 (3) | C14—C15 | 1.376 (3) |
N3—C14 | 1.438 (3) | C14—C19 | 1.393 (3) |
N3—H3 | 0.82 (3) | C15—C16 | 1.394 (3) |
C1—H1A | 0.9600 | C15—H15 | 0.9300 |
C1—H1B | 0.9600 | C16—C17 | 1.387 (3) |
C1—H1C | 0.9600 | C17—C18 | 1.386 (3) |
C2—C3 | 1.473 (3) | C17—H17 | 0.9300 |
C3—C4 | 1.346 (3) | C18—C19 | 1.387 (3) |
C3—C6 | 1.519 (3) | C18—H18 | 0.9300 |
C4—C5 | 1.496 (3) | C19—H19 | 0.9300 |
C20—S1—C16 | 98.55 (11) | C7—C8—H8 | 119.6 |
C2—O1—C1 | 116.46 (18) | C9—C8—H8 | 119.6 |
C13—N1—C6 | 121.19 (18) | C10—C9—C8 | 118.9 (2) |
C13—N1—H1 | 121.3 (16) | C10—C9—H9 | 120.5 |
C6—N1—H1 | 116.7 (16) | C8—C9—H9 | 120.5 |
C13—N2—C4 | 122.11 (19) | C9—C10—C11 | 121.4 (2) |
C13—N2—H2 | 114.7 (18) | C9—C10—Cl1 | 119.79 (18) |
C4—N2—H2 | 121.4 (18) | C11—C10—Cl1 | 118.84 (17) |
C13—N3—C14 | 123.34 (18) | C10—C11—C12 | 119.3 (2) |
C13—N3—H3 | 116.8 (18) | C10—C11—H11 | 120.4 |
C14—N3—H3 | 119.6 (18) | C12—C11—H11 | 120.4 |
O1—C1—H1A | 109.5 | C11—C12—C7 | 120.8 (2) |
O1—C1—H1B | 109.5 | C11—C12—H12 | 119.6 |
H1A—C1—H1B | 109.5 | C7—C12—H12 | 119.6 |
O1—C1—H1C | 109.5 | N1—C13—N3 | 123.54 (19) |
H1A—C1—H1C | 109.5 | N1—C13—N2 | 118.3 (2) |
H1B—C1—H1C | 109.5 | N3—C13—N2 | 118.19 (19) |
O2—C2—O1 | 122.4 (2) | C15—C14—C19 | 121.4 (2) |
O2—C2—C3 | 127.2 (2) | C15—C14—N3 | 119.57 (19) |
O1—C2—C3 | 110.42 (18) | C19—C14—N3 | 119.1 (2) |
C4—C3—C2 | 122.93 (19) | C14—C15—C16 | 118.7 (2) |
C4—C3—C6 | 118.69 (19) | C14—C15—H15 | 120.6 |
C2—C3—C6 | 118.23 (18) | C16—C15—H15 | 120.6 |
C3—C4—N2 | 118.63 (19) | C17—C16—C15 | 120.6 (2) |
C3—C4—C5 | 128.6 (2) | C17—C16—S1 | 119.95 (18) |
N2—C4—C5 | 112.78 (19) | C15—C16—S1 | 119.42 (18) |
C4—C5—H5A | 109.5 | C18—C17—C16 | 120.0 (2) |
C4—C5—H5B | 109.5 | C18—C17—H17 | 120.0 |
H5A—C5—H5B | 109.5 | C16—C17—H17 | 120.0 |
C4—C5—H5C | 109.5 | C17—C18—C19 | 119.9 (2) |
H5A—C5—H5C | 109.5 | C17—C18—H18 | 120.1 |
H5B—C5—H5C | 109.5 | C19—C18—H18 | 120.1 |
N1—C6—C3 | 108.80 (16) | C18—C19—C14 | 119.4 (2) |
N1—C6—C7 | 110.11 (17) | C18—C19—H19 | 120.3 |
C3—C6—C7 | 114.37 (17) | C14—C19—H19 | 120.3 |
N1—C6—H6 | 107.8 | F3—C20—F2 | 106.4 (2) |
C3—C6—H6 | 107.8 | F3—C20—F1 | 107.3 (2) |
C7—C6—H6 | 107.8 | F2—C20—F1 | 106.7 (2) |
C8—C7—C12 | 118.82 (19) | F3—C20—S1 | 113.51 (18) |
C8—C7—C6 | 122.47 (18) | F2—C20—S1 | 114.5 (2) |
C12—C7—C6 | 118.71 (19) | F1—C20—S1 | 108.03 (19) |
C7—C8—C9 | 120.9 (2) | ||
C1—O1—C2—O2 | −1.7 (3) | Cl1—C10—C11—C12 | 178.23 (17) |
C1—O1—C2—C3 | 178.4 (2) | C10—C11—C12—C7 | 1.5 (3) |
O2—C2—C3—C4 | 2.6 (4) | C8—C7—C12—C11 | −0.9 (3) |
O1—C2—C3—C4 | −177.4 (2) | C6—C7—C12—C11 | 179.6 (2) |
O2—C2—C3—C6 | 178.0 (2) | C6—N1—C13—N3 | 163.4 (2) |
O1—C2—C3—C6 | −2.0 (3) | C6—N1—C13—N2 | −17.7 (3) |
C2—C3—C4—N2 | −178.94 (19) | C14—N3—C13—N1 | −8.4 (3) |
C6—C3—C4—N2 | 5.6 (3) | C14—N3—C13—N2 | 172.72 (19) |
C2—C3—C4—C5 | 0.8 (4) | C4—N2—C13—N1 | −13.0 (3) |
C6—C3—C4—C5 | −174.6 (2) | C4—N2—C13—N3 | 165.96 (19) |
C13—N2—C4—C3 | 18.7 (3) | C13—N3—C14—C15 | 102.6 (2) |
C13—N2—C4—C5 | −161.09 (19) | C13—N3—C14—C19 | −78.2 (3) |
C13—N1—C6—C3 | 37.9 (3) | C19—C14—C15—C16 | −0.2 (3) |
C13—N1—C6—C7 | −88.2 (2) | N3—C14—C15—C16 | 178.98 (19) |
C4—C3—C6—N1 | −30.9 (3) | C14—C15—C16—C17 | −0.4 (3) |
C2—C3—C6—N1 | 153.48 (19) | C14—C15—C16—S1 | −178.64 (16) |
C4—C3—C6—C7 | 92.7 (2) | C20—S1—C16—C17 | 98.8 (2) |
C2—C3—C6—C7 | −83.0 (2) | C20—S1—C16—C15 | −83.0 (2) |
N1—C6—C7—C8 | 127.0 (2) | C15—C16—C17—C18 | 0.7 (3) |
C3—C6—C7—C8 | 4.2 (3) | S1—C16—C17—C18 | 178.92 (18) |
N1—C6—C7—C12 | −53.5 (2) | C16—C17—C18—C19 | −0.4 (4) |
C3—C6—C7—C12 | −176.36 (19) | C17—C18—C19—C14 | −0.2 (3) |
C12—C7—C8—C9 | 0.0 (3) | C15—C14—C19—C18 | 0.5 (3) |
C6—C7—C8—C9 | 179.5 (2) | N3—C14—C19—C18 | −178.7 (2) |
C7—C8—C9—C10 | 0.3 (3) | C16—S1—C20—F3 | 59.4 (2) |
C8—C9—C10—C11 | 0.3 (3) | C16—S1—C20—F2 | −63.1 (2) |
C8—C9—C10—Cl1 | −179.12 (17) | C16—S1—C20—F1 | 178.19 (18) |
C9—C10—C11—C12 | −1.1 (3) |
C19H18BrClN3O2·Cl·H2O | F(000) = 992 |
Mr = 489.19 | Dx = 1.524 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 18016 reflections |
a = 14.8702 (11) Å | θ = 2.3–28.3° |
b = 8.0910 (5) Å | µ = 2.20 mm−1 |
c = 17.7304 (13) Å | T = 100 K |
β = 92.203 (2)° | Block, colourless |
V = 2131.7 (3) Å3 | 0.21 × 0.07 × 0.05 mm |
Z = 4 |
Bruker KAPPA APEX II DUO diffractometer | 3720 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 28.3°, θmin = 2.3° |
Absorption correction: multi-scan SADABS | h = −19→19 |
Tmin = 0.655, Tmax = 0.898 | k = −10→7 |
18022 measured reflections | l = −23→23 |
5301 independent reflections |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0316P)2 + 0.4954P] where P = (Fo2 + 2Fc2)/3 |
5301 reflections | (Δ/σ)max = 0.001 |
275 parameters | Δρmax = 0.52 e Å−3 |
1 restraint | Δρmin = −0.54 e Å−3 |
C19H18BrClN3O2·Cl·H2O | V = 2131.7 (3) Å3 |
Mr = 489.19 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.8702 (11) Å | µ = 2.20 mm−1 |
b = 8.0910 (5) Å | T = 100 K |
c = 17.7304 (13) Å | 0.21 × 0.07 × 0.05 mm |
β = 92.203 (2)° |
Bruker KAPPA APEX II DUO diffractometer | 5301 independent reflections |
Absorption correction: multi-scan SADABS | 3720 reflections with I > 2σ(I) |
Tmin = 0.655, Tmax = 0.898 | Rint = 0.045 |
18022 measured reflections |
R[F2 > 2σ(F2)] = 0.036 | 1 restraint |
wR(F2) = 0.083 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.52 e Å−3 |
5301 reflections | Δρmin = −0.54 e Å−3 |
275 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 | ||
Br1 | 0.773951 (16) | 0.63297 (3) | 0.147297 (16) | 0.04251 (9) | |
Cl1 | 0.06227 (5) | 0.19129 (10) | −0.00064 (5) | 0.0590 (2) | |
Cl2 | 0.40260 (5) | 0.88638 (9) | 0.09162 (4) | 0.0564 (2) | |
O1 | 0.09635 (11) | 0.8498 (2) | 0.22248 (10) | 0.0427 (4) | |
O2 | 0.07413 (11) | 0.7885 (2) | 0.34379 (11) | 0.0480 (5) | |
O3 | 0.39984 (16) | 0.3636 (2) | 0.45714 (12) | 0.0473 (5) | |
H3A | 0.399 (2) | 0.420 (4) | 0.4933 (19) | 0.064 (11)* | |
H3B | 0.462 (3) | 0.357 (4) | 0.444 (2) | 0.085 (12)* | |
N1 | 0.34522 (12) | 0.6485 (2) | 0.21693 (11) | 0.0289 (4) | |
H1 | 0.3761 (16) | 0.678 (3) | 0.1830 (14) | 0.032 (7)* | |
N2 | 0.33261 (13) | 0.5433 (2) | 0.33589 (11) | 0.0298 (4) | |
H2 | 0.3577 (17) | 0.487 (3) | 0.3710 (15) | 0.043 (8)* | |
N3 | 0.46614 (13) | 0.5114 (2) | 0.27450 (11) | 0.0325 (4) | |
H3 | 0.4917 (16) | 0.489 (3) | 0.3157 (11) | 0.048 (8)* | |
C1 | 0.01085 (18) | 0.9361 (4) | 0.22017 (19) | 0.0601 (8) | |
H1A | −0.0368 | 0.8588 | 0.2281 | 0.090* | |
H1B | 0.0014 | 0.9880 | 0.1718 | 0.090* | |
H1C | 0.0113 | 1.0188 | 0.2590 | 0.090* | |
C2 | 0.12018 (15) | 0.7798 (3) | 0.28921 (15) | 0.0340 (5) | |
C3 | 0.20736 (14) | 0.6928 (3) | 0.28405 (13) | 0.0288 (5) | |
C4 | 0.24858 (15) | 0.6200 (3) | 0.34420 (13) | 0.0293 (5) | |
C5 | 0.21731 (17) | 0.6084 (3) | 0.42329 (14) | 0.0416 (6) | |
H5A | 0.1580 | 0.6547 | 0.4255 | 0.062* | |
H5B | 0.2579 | 0.6685 | 0.4566 | 0.062* | |
H5C | 0.2160 | 0.4946 | 0.4385 | 0.062* | |
C6 | 0.24859 (14) | 0.6864 (3) | 0.20716 (13) | 0.0284 (5) | |
H6 | 0.2426 | 0.7962 | 0.1842 | 0.034* | |
C7 | 0.20316 (14) | 0.5618 (3) | 0.15361 (13) | 0.0291 (5) | |
C8 | 0.20346 (16) | 0.3944 (3) | 0.17155 (15) | 0.0375 (6) | |
H8 | 0.2322 | 0.3586 | 0.2161 | 0.045* | |
C9 | 0.16120 (17) | 0.2801 (3) | 0.12362 (16) | 0.0436 (6) | |
H9 | 0.1616 | 0.1683 | 0.1358 | 0.052* | |
C10 | 0.11888 (16) | 0.3347 (3) | 0.05803 (15) | 0.0397 (6) | |
C11 | 0.11840 (16) | 0.5000 (3) | 0.03763 (14) | 0.0405 (6) | |
H11 | 0.0907 | 0.5348 | −0.0075 | 0.049* | |
C12 | 0.16061 (16) | 0.6124 (3) | 0.08669 (13) | 0.0350 (5) | |
H12 | 0.1602 | 0.7241 | 0.0743 | 0.042* | |
C13 | 0.38142 (14) | 0.5682 (3) | 0.27474 (12) | 0.0267 (5) | |
C14 | 0.51794 (15) | 0.4971 (3) | 0.20867 (13) | 0.0286 (5) | |
C15 | 0.60471 (14) | 0.5620 (3) | 0.21006 (13) | 0.0296 (5) | |
H15 | 0.6279 | 0.6167 | 0.2526 | 0.036* | |
C16 | 0.65579 (15) | 0.5436 (3) | 0.14707 (13) | 0.0308 (5) | |
C17 | 0.62269 (17) | 0.4628 (3) | 0.08294 (14) | 0.0387 (6) | |
H17 | 0.6575 | 0.4530 | 0.0407 | 0.046* | |
C18 | 0.53701 (18) | 0.3972 (3) | 0.08290 (14) | 0.0403 (6) | |
H18 | 0.5144 | 0.3408 | 0.0406 | 0.048* | |
C19 | 0.48427 (16) | 0.4141 (3) | 0.14507 (14) | 0.0351 (5) | |
H19 | 0.4265 | 0.3701 | 0.1443 | 0.042* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.03396 (13) | 0.03986 (15) | 0.05443 (18) | 0.00419 (11) | 0.01104 (11) | 0.00159 (12) |
Cl1 | 0.0429 (4) | 0.0667 (5) | 0.0672 (5) | −0.0056 (3) | 0.0012 (3) | −0.0376 (4) |
Cl2 | 0.0544 (4) | 0.0838 (5) | 0.0300 (3) | −0.0335 (4) | −0.0096 (3) | 0.0209 (3) |
O1 | 0.0329 (9) | 0.0445 (10) | 0.0506 (11) | 0.0123 (8) | 0.0002 (8) | −0.0004 (8) |
O2 | 0.0362 (9) | 0.0518 (11) | 0.0571 (12) | 0.0027 (8) | 0.0166 (9) | 0.0002 (9) |
O3 | 0.0665 (14) | 0.0398 (11) | 0.0348 (11) | 0.0051 (10) | −0.0069 (10) | −0.0046 (9) |
N1 | 0.0236 (9) | 0.0345 (11) | 0.0287 (11) | −0.0040 (8) | 0.0039 (8) | 0.0074 (9) |
N2 | 0.0306 (10) | 0.0324 (11) | 0.0261 (11) | −0.0024 (8) | 0.0000 (8) | 0.0042 (8) |
N3 | 0.0290 (10) | 0.0414 (12) | 0.0267 (11) | 0.0029 (8) | −0.0038 (9) | 0.0031 (9) |
C1 | 0.0412 (15) | 0.0596 (18) | 0.080 (2) | 0.0218 (14) | 0.0036 (15) | 0.0065 (17) |
C2 | 0.0280 (11) | 0.0263 (12) | 0.0479 (16) | −0.0070 (9) | 0.0022 (11) | −0.0064 (11) |
C3 | 0.0275 (11) | 0.0248 (11) | 0.0343 (13) | −0.0064 (9) | 0.0037 (10) | −0.0023 (9) |
C4 | 0.0293 (11) | 0.0252 (11) | 0.0336 (13) | −0.0068 (9) | 0.0050 (10) | −0.0060 (10) |
C5 | 0.0424 (14) | 0.0482 (15) | 0.0346 (14) | −0.0055 (12) | 0.0083 (11) | −0.0037 (11) |
C6 | 0.0233 (10) | 0.0281 (11) | 0.0335 (13) | −0.0007 (9) | 0.0002 (9) | 0.0047 (9) |
C7 | 0.0234 (10) | 0.0311 (11) | 0.0331 (13) | −0.0013 (9) | 0.0062 (9) | 0.0004 (10) |
C8 | 0.0369 (13) | 0.0341 (13) | 0.0411 (14) | −0.0041 (10) | −0.0037 (11) | 0.0032 (11) |
C9 | 0.0402 (14) | 0.0333 (14) | 0.0575 (18) | −0.0049 (11) | 0.0026 (13) | −0.0052 (12) |
C10 | 0.0277 (12) | 0.0484 (16) | 0.0433 (15) | −0.0036 (11) | 0.0059 (11) | −0.0184 (12) |
C11 | 0.0346 (13) | 0.0529 (16) | 0.0337 (14) | 0.0045 (12) | −0.0015 (11) | −0.0076 (12) |
C12 | 0.0355 (12) | 0.0371 (13) | 0.0324 (13) | 0.0026 (10) | −0.0002 (10) | 0.0035 (10) |
C13 | 0.0274 (11) | 0.0254 (11) | 0.0272 (12) | −0.0046 (9) | −0.0011 (9) | 0.0005 (9) |
C14 | 0.0305 (11) | 0.0284 (11) | 0.0268 (12) | 0.0059 (9) | −0.0003 (9) | 0.0018 (9) |
C15 | 0.0302 (11) | 0.0284 (11) | 0.0299 (12) | 0.0058 (9) | −0.0039 (10) | −0.0034 (9) |
C16 | 0.0311 (11) | 0.0250 (11) | 0.0361 (13) | 0.0061 (9) | 0.0006 (10) | 0.0040 (10) |
C17 | 0.0498 (15) | 0.0348 (13) | 0.0319 (14) | 0.0131 (11) | 0.0049 (12) | −0.0010 (10) |
C18 | 0.0530 (16) | 0.0352 (14) | 0.0322 (14) | 0.0058 (11) | −0.0067 (12) | −0.0080 (10) |
C19 | 0.0351 (12) | 0.0318 (12) | 0.0379 (14) | −0.0017 (10) | −0.0063 (11) | −0.0024 (10) |
Br1—C16 | 1.900 (2) | C5—H5B | 0.9600 |
Cl1—C10 | 1.752 (2) | C5—H5C | 0.9600 |
O1—C2 | 1.347 (3) | C6—C7 | 1.525 (3) |
O1—C1 | 1.450 (3) | C6—H6 | 0.9800 |
O2—C2 | 1.209 (3) | C7—C12 | 1.385 (3) |
O3—H3A | 0.79 (3) | C7—C8 | 1.391 (3) |
O3—H3B | 0.96 (4) | C8—C9 | 1.390 (3) |
N1—C13 | 1.312 (3) | C8—H8 | 0.9300 |
N1—C6 | 1.473 (3) | C9—C10 | 1.374 (4) |
N1—H1 | 0.81 (2) | C9—H9 | 0.9300 |
N2—C13 | 1.343 (3) | C10—C11 | 1.386 (4) |
N2—C4 | 1.408 (3) | C11—C12 | 1.391 (3) |
N2—H2 | 0.85 (3) | C11—H11 | 0.9300 |
N3—C13 | 1.341 (3) | C12—H12 | 0.9300 |
N3—C14 | 1.428 (3) | C14—C19 | 1.389 (3) |
N3—H3 | 0.831 (16) | C14—C15 | 1.392 (3) |
C1—H1A | 0.9600 | C15—C16 | 1.383 (3) |
C1—H1B | 0.9600 | C15—H15 | 0.9300 |
C1—H1C | 0.9600 | C16—C17 | 1.385 (3) |
C2—C3 | 1.481 (3) | C17—C18 | 1.380 (4) |
C3—C4 | 1.345 (3) | C17—H17 | 0.9300 |
C3—C6 | 1.517 (3) | C18—C19 | 1.384 (4) |
C4—C5 | 1.497 (3) | C18—H18 | 0.9300 |
C5—H5A | 0.9600 | C19—H19 | 0.9300 |
C2—O1—C1 | 115.4 (2) | C12—C7—C6 | 121.0 (2) |
H3A—O3—H3B | 106 (3) | C8—C7—C6 | 120.3 (2) |
C13—N1—C6 | 124.34 (19) | C9—C8—C7 | 120.7 (2) |
C13—N1—H1 | 120.1 (17) | C9—C8—H8 | 119.7 |
C6—N1—H1 | 115.6 (17) | C7—C8—H8 | 119.7 |
C13—N2—C4 | 121.8 (2) | C10—C9—C8 | 119.1 (2) |
C13—N2—H2 | 116.0 (18) | C10—C9—H9 | 120.5 |
C4—N2—H2 | 121.9 (18) | C8—C9—H9 | 120.5 |
C13—N3—C14 | 124.52 (19) | C9—C10—C11 | 121.9 (2) |
C13—N3—H3 | 118.1 (19) | C9—C10—Cl1 | 118.9 (2) |
C14—N3—H3 | 117.3 (19) | C11—C10—Cl1 | 119.1 (2) |
O1—C1—H1A | 109.5 | C10—C11—C12 | 118.0 (2) |
O1—C1—H1B | 109.5 | C10—C11—H11 | 121.0 |
H1A—C1—H1B | 109.5 | C12—C11—H11 | 121.0 |
O1—C1—H1C | 109.5 | C7—C12—C11 | 121.5 (2) |
H1A—C1—H1C | 109.5 | C7—C12—H12 | 119.2 |
H1B—C1—H1C | 109.5 | C11—C12—H12 | 119.2 |
O2—C2—O1 | 122.7 (2) | N1—C13—N3 | 121.6 (2) |
O2—C2—C3 | 127.0 (2) | N1—C13—N2 | 119.2 (2) |
O1—C2—C3 | 110.3 (2) | N3—C13—N2 | 119.2 (2) |
C4—C3—C2 | 122.2 (2) | C19—C14—C15 | 120.1 (2) |
C4—C3—C6 | 120.7 (2) | C19—C14—N3 | 120.9 (2) |
C2—C3—C6 | 117.2 (2) | C15—C14—N3 | 118.9 (2) |
C3—C4—N2 | 119.3 (2) | C16—C15—C14 | 118.9 (2) |
C3—C4—C5 | 128.4 (2) | C16—C15—H15 | 120.6 |
N2—C4—C5 | 112.3 (2) | C14—C15—H15 | 120.6 |
C4—C5—H5A | 109.5 | C15—C16—C17 | 121.6 (2) |
C4—C5—H5B | 109.5 | C15—C16—Br1 | 119.61 (17) |
H5A—C5—H5B | 109.5 | C17—C16—Br1 | 118.73 (18) |
C4—C5—H5C | 109.5 | C18—C17—C16 | 118.7 (2) |
H5A—C5—H5C | 109.5 | C18—C17—H17 | 120.6 |
H5B—C5—H5C | 109.5 | C16—C17—H17 | 120.6 |
N1—C6—C3 | 109.13 (18) | C17—C18—C19 | 120.8 (2) |
N1—C6—C7 | 110.03 (17) | C17—C18—H18 | 119.6 |
C3—C6—C7 | 113.43 (17) | C19—C18—H18 | 119.6 |
N1—C6—H6 | 108.0 | C18—C19—C14 | 119.8 (2) |
C3—C6—H6 | 108.0 | C18—C19—H19 | 120.1 |
C7—C6—H6 | 108.0 | C14—C19—H19 | 120.1 |
C12—C7—C8 | 118.8 (2) | ||
C1—O1—C2—O2 | −0.4 (3) | C8—C9—C10—C11 | 1.1 (4) |
C1—O1—C2—C3 | 178.8 (2) | C8—C9—C10—Cl1 | −177.77 (19) |
O2—C2—C3—C4 | −4.5 (4) | C9—C10—C11—C12 | −1.5 (4) |
O1—C2—C3—C4 | 176.33 (19) | Cl1—C10—C11—C12 | 177.36 (18) |
O2—C2—C3—C6 | 174.6 (2) | C8—C7—C12—C11 | 0.1 (3) |
O1—C2—C3—C6 | −4.5 (3) | C6—C7—C12—C11 | −179.6 (2) |
C2—C3—C4—N2 | −178.26 (18) | C10—C11—C12—C7 | 0.9 (3) |
C6—C3—C4—N2 | 2.6 (3) | C6—N1—C13—N3 | 167.8 (2) |
C2—C3—C4—C5 | 1.2 (3) | C6—N1—C13—N2 | −12.6 (3) |
C6—C3—C4—C5 | −177.8 (2) | C14—N3—C13—N1 | −14.8 (3) |
C13—N2—C4—C3 | 13.7 (3) | C14—N3—C13—N2 | 165.6 (2) |
C13—N2—C4—C5 | −165.9 (2) | C4—N2—C13—N1 | −9.0 (3) |
C13—N1—C6—C3 | 25.8 (3) | C4—N2—C13—N3 | 170.58 (19) |
C13—N1—C6—C7 | −99.3 (2) | C13—N3—C14—C19 | −52.3 (3) |
C4—C3—C6—N1 | −20.0 (3) | C13—N3—C14—C15 | 130.3 (2) |
C2—C3—C6—N1 | 160.91 (18) | C19—C14—C15—C16 | 0.6 (3) |
C4—C3—C6—C7 | 103.1 (2) | N3—C14—C15—C16 | 178.05 (19) |
C2—C3—C6—C7 | −76.0 (2) | C14—C15—C16—C17 | 0.1 (3) |
N1—C6—C7—C12 | −119.6 (2) | C14—C15—C16—Br1 | 179.40 (15) |
C3—C6—C7—C12 | 117.9 (2) | C15—C16—C17—C18 | −1.0 (3) |
N1—C6—C7—C8 | 60.8 (3) | Br1—C16—C17—C18 | 179.67 (17) |
C3—C6—C7—C8 | −61.8 (3) | C16—C17—C18—C19 | 1.2 (3) |
C12—C7—C8—C9 | −0.6 (3) | C17—C18—C19—C14 | −0.5 (3) |
C6—C7—C8—C9 | 179.1 (2) | C15—C14—C19—C18 | −0.4 (3) |
C7—C8—C9—C10 | 0.0 (4) | N3—C14—C19—C18 | −177.8 (2) |
Experimental details
(A) | (B) | |
Crystal data | ||
Chemical formula | C20H18ClF3N3O2S·Cl | C19H18BrClN3O2·Cl·H2O |
Mr | 492.33 | 489.19 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c |
Temperature (K) | 100 | 100 |
a, b, c (Å) | 7.7005 (6), 11.2405 (10), 13.7322 (12) | 14.8702 (11), 8.0910 (5), 17.7304 (13) |
α, β, γ (°) | 111.249 (2), 90.907 (2), 99.769 (2) | 90, 92.203 (2), 90 |
V (Å3) | 1087.88 (16) | 2131.7 (3) |
Z | 2 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.44 | 2.20 |
Crystal size (mm) | 0.17 × 0.09 × 0.04 | 0.21 × 0.07 × 0.05 |
Data collection | ||
Diffractometer | Bruker KAPPA APEX II DUO diffractometer | Bruker KAPPA APEX II DUO diffractometer |
Absorption correction | Multi-scan SADABS | Multi-scan SADABS |
Tmin, Tmax | 0.929, 0.983 | 0.655, 0.898 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10760, 5436, 3549 | 18022, 5301, 3720 |
Rint | 0.037 | 0.045 |
(sin θ/λ)max (Å−1) | 0.671 | 0.668 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.107, 1.01 | 0.036, 0.083, 1.01 |
No. of reflections | 5436 | 5301 |
No. of parameters | 294 | 275 |
No. of restraints | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.28 | 0.52, −0.54 |
Computer programs: SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997).
Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register