Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061120/bt2628sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061120/bt2628Isup2.hkl |
CCDC reference: 673066
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.164
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C15
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 800 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C14 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C1 ..... S PLAT793_ALERT_1_G Check the Absolute Configuration of C3 ..... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared according to the method of Liu et al. (2007). The product was recrystallized from methanol and ethyl acetate (5:1, v/v) over 4 days at ambient temperature, giving colourless prismatic crystals.
H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using riding model with Uiso(H) = 1.2Ueq(carrier). H atom of N—H was located from difference map and refinded freely.
Data collection: SMART (Bruker, 1997'; cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. The molecular structure of the title compound drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius. |
C15H15ClF3NO3S | Z = 2 |
Mr = 381.79 | F(000) = 392 |
Triclinic, P1 | Dx = 1.390 Mg m−3 |
a = 7.9342 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.4940 (14) Å | Cell parameters from 1854 reflections |
c = 13.8971 (16) Å | θ = 2.8–25.1° |
α = 87.144 (8)° | µ = 0.37 mm−1 |
β = 85.696 (8)° | T = 294 K |
γ = 77.821 (8)° | Prism, colorless |
V = 912.4 (2) Å3 | 0.32 × 0.28 × 0.24 mm |
Bruker SMART CCD area-detector diffractometer | 3188 independent reflections |
Radiation source: fine-focus sealed tube | 2206 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→8 |
Tmin = 0.892, Tmax = 0.918 | k = −7→10 |
4678 measured reflections | l = −16→16 |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.074P)2 + 0.6746P] where P = (Fo2 + 2Fc2)/3 |
3188 reflections | (Δ/σ)max = 0.001 |
224 parameters | Δρmax = 0.88 e Å−3 |
0 restraints | Δρmin = −0.63 e Å−3 |
C15H15ClF3NO3S | γ = 77.821 (8)° |
Mr = 381.79 | V = 912.4 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.9342 (12) Å | Mo Kα radiation |
b = 8.4940 (14) Å | µ = 0.37 mm−1 |
c = 13.8971 (16) Å | T = 294 K |
α = 87.144 (8)° | 0.32 × 0.28 × 0.24 mm |
β = 85.696 (8)° |
Bruker SMART CCD area-detector diffractometer | 3188 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 2206 reflections with I > 2σ(I) |
Tmin = 0.892, Tmax = 0.918 | Rint = 0.018 |
4678 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.88 e Å−3 |
3188 reflections | Δρmin = −0.63 e Å−3 |
224 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 | ||
C14 | 0.7383 (5) | −0.2156 (4) | 0.6067 (2) | 0.0576 (9) | |
C15 | 0.6041 (6) | −0.2568 (5) | 0.5474 (3) | 0.0746 (11) | |
Cl1 | 0.93950 (17) | −0.33682 (19) | 0.58260 (10) | 0.1170 (6) | |
F1 | 0.6345 (4) | −0.2276 (4) | 0.45312 (18) | 0.1239 (11) | |
F2 | 0.5909 (5) | −0.4098 (4) | 0.5577 (2) | 0.1330 (12) | |
F3 | 0.4476 (4) | −0.1713 (4) | 0.5698 (2) | 0.1175 (10) | |
S1 | 0.23568 (10) | 0.41449 (12) | 1.12716 (6) | 0.0591 (3) | |
N1 | 0.5903 (3) | 0.1716 (3) | 0.94587 (19) | 0.0509 (7) | |
H1A | 0.681 (4) | 0.180 (4) | 0.972 (2) | 0.045 (9)* | |
O1 | 0.4775 (3) | 0.1059 (4) | 0.81065 (19) | 0.0813 (9) | |
O2 | 0.7451 (3) | 0.2882 (3) | 1.09510 (17) | 0.0642 (7) | |
O3 | 0.5618 (3) | 0.4482 (3) | 1.19945 (17) | 0.0664 (7) | |
C1 | 0.7882 (4) | 0.0441 (4) | 0.8196 (2) | 0.0515 (8) | |
H1 | 0.8686 | 0.0144 | 0.8708 | 0.062* | |
C2 | 0.8663 (4) | 0.1144 (4) | 0.7273 (2) | 0.0568 (9) | |
C3 | 0.8370 (4) | −0.0577 (4) | 0.7302 (2) | 0.0544 (8) | |
H3 | 0.9429 | −0.1407 | 0.7348 | 0.065* | |
C4 | 0.6038 (4) | 0.1073 (4) | 0.8559 (2) | 0.0523 (8) | |
C5 | 0.1460 (4) | 0.3306 (5) | 1.0390 (3) | 0.0616 (9) | |
H5 | 0.0275 | 0.3411 | 1.0357 | 0.074* | |
C6 | 0.2653 (4) | 0.2472 (4) | 0.9744 (3) | 0.0565 (9) | |
H6 | 0.2377 | 0.1958 | 0.9220 | 0.068* | |
C7 | 0.4381 (4) | 0.2480 (4) | 0.9970 (2) | 0.0448 (7) | |
C8 | 0.4426 (4) | 0.3336 (4) | 1.0790 (2) | 0.0464 (7) | |
C9 | 0.5988 (4) | 0.3520 (4) | 1.1234 (2) | 0.0494 (8) | |
C10 | 0.7086 (5) | 0.4736 (6) | 1.2501 (3) | 0.0818 (13) | |
H10A | 0.7623 | 0.3743 | 1.2814 | 0.123* | |
H10B | 0.6688 | 0.5537 | 1.2976 | 0.123* | |
H10C | 0.7909 | 0.5093 | 1.2046 | 0.123* | |
C11 | 1.0542 (5) | 0.1314 (6) | 0.7309 (3) | 0.0886 (14) | |
H11A | 1.1142 | 0.0467 | 0.7717 | 0.133* | |
H11B | 1.0566 | 0.2339 | 0.7564 | 0.133* | |
H11C | 1.1094 | 0.1243 | 0.6670 | 0.133* | |
C12 | 0.7536 (6) | 0.2431 (5) | 0.6678 (3) | 0.0771 (11) | |
H12A | 0.7961 | 0.2367 | 0.6013 | 0.116* | |
H12B | 0.7560 | 0.3474 | 0.6906 | 0.116* | |
H12C | 0.6370 | 0.2269 | 0.6737 | 0.116* | |
C13 | 0.7063 (4) | −0.1026 (4) | 0.6711 (2) | 0.0584 (9) | |
H13 | 0.5928 | −0.0461 | 0.6804 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C14 | 0.069 (2) | 0.053 (2) | 0.0512 (19) | −0.0107 (17) | −0.0092 (16) | −0.0099 (16) |
C15 | 0.098 (3) | 0.065 (3) | 0.068 (3) | −0.025 (2) | −0.024 (2) | −0.014 (2) |
Cl1 | 0.0915 (8) | 0.1380 (12) | 0.1102 (10) | 0.0219 (8) | −0.0186 (7) | −0.0751 (9) |
F1 | 0.140 (3) | 0.190 (3) | 0.0610 (16) | −0.068 (2) | −0.0300 (15) | −0.0095 (17) |
F2 | 0.191 (3) | 0.080 (2) | 0.152 (3) | −0.061 (2) | −0.072 (2) | −0.0102 (18) |
F3 | 0.0820 (18) | 0.145 (3) | 0.136 (2) | −0.0271 (18) | −0.0332 (17) | −0.054 (2) |
S1 | 0.0384 (4) | 0.0735 (6) | 0.0617 (6) | −0.0048 (4) | 0.0053 (4) | −0.0072 (4) |
N1 | 0.0363 (14) | 0.0666 (19) | 0.0516 (16) | −0.0110 (12) | −0.0062 (12) | −0.0134 (13) |
O1 | 0.0467 (14) | 0.124 (2) | 0.0735 (17) | −0.0060 (14) | −0.0139 (12) | −0.0396 (16) |
O2 | 0.0357 (12) | 0.0900 (18) | 0.0681 (15) | −0.0116 (11) | 0.0000 (10) | −0.0253 (13) |
O3 | 0.0479 (13) | 0.0865 (18) | 0.0653 (15) | −0.0075 (12) | −0.0066 (11) | −0.0309 (13) |
C1 | 0.0444 (17) | 0.061 (2) | 0.0494 (18) | −0.0067 (15) | −0.0102 (14) | −0.0120 (15) |
C2 | 0.0545 (19) | 0.065 (2) | 0.056 (2) | −0.0200 (17) | −0.0035 (15) | −0.0178 (17) |
C3 | 0.0475 (18) | 0.058 (2) | 0.056 (2) | −0.0029 (15) | −0.0073 (14) | −0.0193 (16) |
C4 | 0.0440 (17) | 0.062 (2) | 0.0528 (19) | −0.0110 (15) | −0.0080 (14) | −0.0126 (16) |
C5 | 0.0350 (16) | 0.079 (3) | 0.070 (2) | −0.0136 (16) | −0.0023 (15) | 0.0043 (19) |
C6 | 0.0402 (17) | 0.068 (2) | 0.065 (2) | −0.0162 (15) | −0.0086 (15) | −0.0029 (17) |
C7 | 0.0362 (15) | 0.0507 (18) | 0.0481 (17) | −0.0107 (13) | −0.0043 (12) | 0.0014 (14) |
C8 | 0.0357 (15) | 0.0545 (19) | 0.0479 (18) | −0.0083 (13) | 0.0019 (12) | −0.0019 (14) |
C9 | 0.0410 (17) | 0.060 (2) | 0.0483 (18) | −0.0140 (14) | 0.0003 (13) | −0.0051 (15) |
C10 | 0.061 (2) | 0.108 (3) | 0.082 (3) | −0.017 (2) | −0.017 (2) | −0.034 (2) |
C11 | 0.066 (3) | 0.130 (4) | 0.082 (3) | −0.046 (3) | 0.005 (2) | −0.028 (3) |
C12 | 0.095 (3) | 0.068 (3) | 0.072 (3) | −0.024 (2) | −0.011 (2) | −0.004 (2) |
C13 | 0.056 (2) | 0.057 (2) | 0.063 (2) | −0.0095 (16) | −0.0102 (16) | −0.0148 (17) |
C14—C13 | 1.317 (5) | C2—C3 | 1.526 (5) |
C14—C15 | 1.501 (5) | C2—C11 | 1.532 (5) |
C14—Cl1 | 1.726 (4) | C3—C13 | 1.491 (4) |
C15—F3 | 1.323 (5) | C3—H3 | 0.9800 |
C15—F2 | 1.326 (5) | C5—C6 | 1.363 (5) |
C15—F1 | 1.335 (5) | C5—H5 | 0.9300 |
S1—C5 | 1.716 (4) | C6—C7 | 1.430 (4) |
S1—C8 | 1.738 (3) | C6—H6 | 0.9300 |
N1—C4 | 1.377 (4) | C7—C8 | 1.389 (4) |
N1—C7 | 1.404 (4) | C8—C9 | 1.465 (4) |
N1—H1A | 0.85 (3) | C10—H10A | 0.9600 |
O1—C4 | 1.225 (4) | C10—H10B | 0.9600 |
O2—C9 | 1.218 (4) | C10—H10C | 0.9600 |
O3—C9 | 1.345 (4) | C11—H11A | 0.9600 |
O3—C10 | 1.464 (4) | C11—H11B | 0.9600 |
C1—C4 | 1.506 (4) | C11—H11C | 0.9600 |
C1—C3 | 1.528 (4) | C12—H12A | 0.9600 |
C1—C2 | 1.532 (5) | C12—H12B | 0.9600 |
C1—H1 | 0.9800 | C12—H12C | 0.9600 |
C2—C12 | 1.512 (5) | C13—H13 | 0.9300 |
C13—C14—C15 | 124.1 (4) | C6—C5—H5 | 123.3 |
C13—C14—Cl1 | 123.7 (3) | S1—C5—H5 | 123.3 |
C15—C14—Cl1 | 112.1 (3) | C5—C6—C7 | 111.9 (3) |
F3—C15—F2 | 105.7 (4) | C5—C6—H6 | 124.0 |
F3—C15—F1 | 105.5 (4) | C7—C6—H6 | 124.0 |
F2—C15—F1 | 106.7 (3) | C8—C7—N1 | 121.5 (3) |
F3—C15—C14 | 112.4 (3) | C8—C7—C6 | 112.2 (3) |
F2—C15—C14 | 113.5 (4) | N1—C7—C6 | 126.3 (3) |
F1—C15—C14 | 112.4 (4) | C7—C8—C9 | 125.8 (3) |
C5—S1—C8 | 91.01 (16) | C7—C8—S1 | 111.4 (2) |
C4—N1—C7 | 126.8 (3) | C9—C8—S1 | 122.7 (2) |
C4—N1—H1A | 120 (2) | O2—C9—O3 | 123.7 (3) |
C7—N1—H1A | 113 (2) | O2—C9—C8 | 124.3 (3) |
C9—O3—C10 | 116.6 (3) | O3—C9—C8 | 112.0 (3) |
C4—C1—C3 | 123.0 (3) | O3—C10—H10A | 109.5 |
C4—C1—C2 | 121.4 (3) | O3—C10—H10B | 109.5 |
C3—C1—C2 | 59.8 (2) | H10A—C10—H10B | 109.5 |
C4—C1—H1 | 114.0 | O3—C10—H10C | 109.5 |
C3—C1—H1 | 114.0 | H10A—C10—H10C | 109.5 |
C2—C1—H1 | 114.0 | H10B—C10—H10C | 109.5 |
C12—C2—C3 | 119.2 (3) | C2—C11—H11A | 109.5 |
C12—C2—C1 | 119.5 (3) | C2—C11—H11B | 109.5 |
C3—C2—C1 | 59.9 (2) | H11A—C11—H11B | 109.5 |
C12—C2—C11 | 115.6 (3) | C2—C11—H11C | 109.5 |
C3—C2—C11 | 115.9 (3) | H11A—C11—H11C | 109.5 |
C1—C2—C11 | 115.3 (3) | H11B—C11—H11C | 109.5 |
C13—C3—C2 | 121.1 (3) | C2—C12—H12A | 109.5 |
C13—C3—C1 | 122.9 (3) | C2—C12—H12B | 109.5 |
C2—C3—C1 | 60.2 (2) | H12A—C12—H12B | 109.5 |
C13—C3—H3 | 114.1 | C2—C12—H12C | 109.5 |
C2—C3—H3 | 114.1 | H12A—C12—H12C | 109.5 |
C1—C3—H3 | 114.1 | H12B—C12—H12C | 109.5 |
O1—C4—N1 | 122.5 (3) | C14—C13—C3 | 125.4 (3) |
O1—C4—C1 | 124.6 (3) | C14—C13—H13 | 117.3 |
N1—C4—C1 | 112.9 (3) | C3—C13—H13 | 117.3 |
C6—C5—S1 | 113.4 (2) | ||
C13—C14—C15—F3 | −2.7 (6) | C2—C1—C4—N1 | −118.3 (3) |
Cl1—C14—C15—F3 | 176.0 (3) | C8—S1—C5—C6 | −1.0 (3) |
C13—C14—C15—F2 | −122.6 (4) | S1—C5—C6—C7 | 0.8 (4) |
Cl1—C14—C15—F2 | 56.1 (5) | C4—N1—C7—C8 | −168.2 (3) |
C13—C14—C15—F1 | 116.2 (5) | C4—N1—C7—C6 | 12.8 (5) |
Cl1—C14—C15—F1 | −65.1 (4) | C5—C6—C7—C8 | −0.1 (4) |
C4—C1—C2—C12 | −3.8 (4) | C5—C6—C7—N1 | 179.0 (3) |
C3—C1—C2—C12 | 108.7 (3) | N1—C7—C8—C9 | −1.7 (5) |
C4—C1—C2—C3 | −112.5 (3) | C6—C7—C8—C9 | 177.4 (3) |
C4—C1—C2—C11 | 141.0 (3) | N1—C7—C8—S1 | −179.8 (2) |
C3—C1—C2—C11 | −106.5 (4) | C6—C7—C8—S1 | −0.7 (3) |
C12—C2—C3—C13 | 3.5 (5) | C5—S1—C8—C7 | 1.0 (3) |
C1—C2—C3—C13 | 112.7 (3) | C5—S1—C8—C9 | −177.2 (3) |
C11—C2—C3—C13 | −141.7 (3) | C10—O3—C9—O2 | −0.7 (5) |
C12—C2—C3—C1 | −109.2 (3) | C10—O3—C9—C8 | 179.3 (3) |
C11—C2—C3—C1 | 105.6 (3) | C7—C8—C9—O2 | −3.0 (5) |
C4—C1—C3—C13 | 0.3 (5) | S1—C8—C9—O2 | 175.0 (3) |
C2—C1—C3—C13 | −109.8 (4) | C7—C8—C9—O3 | 177.0 (3) |
C4—C1—C3—C2 | 110.0 (4) | S1—C8—C9—O3 | −5.0 (4) |
C7—N1—C4—O1 | −2.5 (6) | C15—C14—C13—C3 | −179.3 (3) |
C7—N1—C4—C1 | 176.1 (3) | Cl1—C14—C13—C3 | 2.2 (6) |
C3—C1—C4—O1 | −12.0 (6) | C2—C3—C13—C14 | 122.6 (4) |
C2—C1—C4—O1 | 60.2 (5) | C1—C3—C13—C14 | −164.9 (4) |
C3—C1—C4—N1 | 169.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.85 (3) | 2.12 (3) | 2.809 (3) | 138 (3) |
C5—H5···O2i | 0.93 | 2.45 | 3.307 (4) | 153 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C15H15ClF3NO3S |
Mr | 381.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 7.9342 (12), 8.4940 (14), 13.8971 (16) |
α, β, γ (°) | 87.144 (8), 85.696 (8), 77.821 (8) |
V (Å3) | 912.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.37 |
Crystal size (mm) | 0.32 × 0.28 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.892, 0.918 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4678, 3188, 2206 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.164, 1.03 |
No. of reflections | 3188 |
No. of parameters | 224 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.88, −0.63 |
Computer programs: SMART (Bruker, 1997', SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.85 (3) | 2.12 (3) | 2.809 (3) | 138 (3) |
C5—H5···O2i | 0.93 | 2.45 | 3.307 (4) | 153 |
Symmetry code: (i) x−1, y, z. |
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The title compound is known to possess insecticidal activity (Punja, 1981). The propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with two methyl substituents, on either side of this plane. The molecular conformation is stabilized by a N—H···O hydrogen bond and the crystal packing shows C—H···O hydrogen bonds.