Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055924/bt2582sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055924/bt2582Isup2.hkl |
CCDC reference: 672889
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.179
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 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 C4 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C6 = ... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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. (2006). 3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2- dimethylcyclopropanecarboxylic acid (0.97 g, 4.0 mmol) was dispersed in SOCl2 (15 ml), and a drop of anhydrous DMF was added. The mixture was heated to reflux for 2 h. SOCl2 was removed by rotoevapor. The crude product could be directly disolved in anhydrous toluene, mixed with 2,5-dimethylbenzenamine (0.50 g, 4.1 mmol). Triethylamine was dropped into the system, and a white fume was coming out. After 8 h stirring at room temperature, the reaction mixture was treated with hexane. Recrystallization of the product from methanol and a small amount of water (70:1) overnight at ambient temperature gave colorless rod like crystals.
H atoms were positioned geometrically with C—H = 0.93–0.98 Å and refined using a riding model with Uiso(H) = 1.2Ueq(C). The amino H atom was located from a difference map and freely refined.
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).
C17H19ClF3NO | Dx = 1.343 Mg m−3 |
Mr = 345.78 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 3270 reflections |
a = 16.445 (3) Å | θ = 2.5–22.5° |
b = 9.5147 (17) Å | µ = 0.26 mm−1 |
c = 21.856 (4) Å | T = 294 K |
V = 3419.9 (11) Å3 | Rod, colorless |
Z = 8 | 0.22 × 0.20 × 0.14 mm |
F(000) = 1440 |
Bruker SMART CCD area-detector diffractometer | 3027 independent reflections |
Radiation source: fine-focus sealed tube | 1746 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −18→19 |
Tmin = 0.946, Tmax = 0.965 | k = −11→10 |
16642 measured reflections | l = −26→25 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0743P)2 + 3.5628P] where P = (Fo2 + 2Fc2)/3 |
3027 reflections | (Δ/σ)max = 0.001 |
212 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
C17H19ClF3NO | V = 3419.9 (11) Å3 |
Mr = 345.78 | Z = 8 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 16.445 (3) Å | µ = 0.26 mm−1 |
b = 9.5147 (17) Å | T = 294 K |
c = 21.856 (4) Å | 0.22 × 0.20 × 0.14 mm |
Bruker SMART CCD area-detector diffractometer | 3027 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1746 reflections with I > 2σ(I) |
Tmin = 0.946, Tmax = 0.965 | Rint = 0.055 |
16642 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 0 restraints |
wR(F2) = 0.179 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.45 e Å−3 |
3027 reflections | Δρmin = −0.43 e Å−3 |
212 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 | 0.19174 (10) | 0.54485 (17) | 0.28229 (5) | 0.1191 (6) | |
F1 | 0.07036 (18) | 0.3181 (3) | 0.39600 (12) | 0.0933 (9) | |
F2 | 0.15906 (16) | 0.2580 (3) | 0.33078 (13) | 0.0954 (9) | |
F3 | 0.04769 (16) | 0.3457 (3) | 0.30072 (12) | 0.0953 (9) | |
O1 | 0.20727 (14) | 0.5688 (2) | 0.51113 (11) | 0.0520 (6) | |
N1 | 0.29927 (15) | 0.7368 (3) | 0.53797 (12) | 0.0448 (7) | |
H1 | 0.3173 | 0.8183 | 0.5277 | 0.054* | |
C1 | 0.1046 (2) | 0.3562 (4) | 0.34407 (18) | 0.0616 (10) | |
C2 | 0.1395 (2) | 0.5006 (4) | 0.34741 (15) | 0.0523 (9) | |
C3 | 0.1319 (2) | 0.5825 (4) | 0.39507 (15) | 0.0459 (8) | |
H3 | 0.1067 | 0.5441 | 0.4293 | 0.055* | |
C4 | 0.1591 (2) | 0.7286 (4) | 0.40009 (15) | 0.0487 (9) | |
H4 | 0.1720 | 0.7731 | 0.3609 | 0.058* | |
C5 | 0.1220 (2) | 0.8267 (4) | 0.44675 (16) | 0.0512 (9) | |
C6 | 0.21059 (19) | 0.7814 (3) | 0.45415 (14) | 0.0435 (8) | |
H6 | 0.2503 | 0.8540 | 0.4433 | 0.052* | |
C7 | 0.0588 (2) | 0.7747 (4) | 0.49090 (18) | 0.0637 (11) | |
H7A | 0.0560 | 0.8371 | 0.5253 | 0.096* | |
H7B | 0.0731 | 0.6822 | 0.5047 | 0.096* | |
H7C | 0.0068 | 0.7717 | 0.4709 | 0.096* | |
C8 | 0.1093 (3) | 0.9766 (4) | 0.4253 (2) | 0.0781 (13) | |
H8A | 0.0592 | 0.9829 | 0.4030 | 0.117* | |
H8B | 0.1536 | 1.0038 | 0.3992 | 0.117* | |
H8C | 0.1072 | 1.0381 | 0.4601 | 0.117* | |
C9 | 0.23767 (19) | 0.6849 (4) | 0.50305 (14) | 0.0410 (8) | |
C10 | 0.33751 (19) | 0.6729 (4) | 0.58929 (15) | 0.0456 (8) | |
C11 | 0.3313 (2) | 0.5296 (4) | 0.60035 (15) | 0.0488 (9) | |
H11 | 0.3029 | 0.4738 | 0.5727 | 0.059* | |
C12 | 0.3659 (2) | 0.4671 (4) | 0.65121 (17) | 0.0571 (10) | |
C13 | 0.4089 (3) | 0.5517 (5) | 0.6902 (2) | 0.0796 (13) | |
H13 | 0.4325 | 0.5129 | 0.7250 | 0.096* | |
C14 | 0.4178 (3) | 0.6923 (5) | 0.6789 (2) | 0.0810 (13) | |
H14 | 0.4488 | 0.7459 | 0.7058 | 0.097* | |
C15 | 0.3824 (2) | 0.7582 (4) | 0.62888 (17) | 0.0587 (10) | |
C16 | 0.3928 (3) | 0.9132 (4) | 0.6193 (2) | 0.0778 (13) | |
H16A | 0.4129 | 0.9301 | 0.5787 | 0.117* | |
H16B | 0.4308 | 0.9494 | 0.6486 | 0.117* | |
H16C | 0.3413 | 0.9593 | 0.6243 | 0.117* | |
C17 | 0.3556 (3) | 0.3115 (5) | 0.6628 (2) | 0.0791 (13) | |
H17A | 0.3987 | 0.2790 | 0.6889 | 0.119* | |
H17B | 0.3576 | 0.2618 | 0.6246 | 0.119* | |
H17C | 0.3042 | 0.2950 | 0.6823 | 0.119* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1729 (15) | 0.1255 (12) | 0.0590 (7) | −0.0545 (10) | 0.0390 (8) | −0.0235 (7) |
F1 | 0.129 (2) | 0.0727 (17) | 0.0780 (17) | −0.0332 (16) | 0.0157 (16) | −0.0098 (14) |
F2 | 0.0903 (19) | 0.0702 (17) | 0.126 (2) | 0.0183 (14) | −0.0112 (16) | −0.0312 (16) |
F3 | 0.0857 (18) | 0.105 (2) | 0.0954 (18) | −0.0110 (15) | −0.0415 (15) | −0.0257 (15) |
O1 | 0.0549 (15) | 0.0447 (14) | 0.0564 (15) | −0.0047 (11) | −0.0145 (11) | 0.0057 (12) |
N1 | 0.0439 (16) | 0.0439 (16) | 0.0465 (15) | −0.0038 (13) | −0.0052 (13) | −0.0002 (13) |
C1 | 0.059 (2) | 0.065 (3) | 0.061 (2) | 0.002 (2) | −0.009 (2) | −0.019 (2) |
C2 | 0.050 (2) | 0.064 (2) | 0.043 (2) | −0.0020 (18) | −0.0063 (16) | −0.0035 (18) |
C3 | 0.046 (2) | 0.051 (2) | 0.0409 (18) | 0.0008 (16) | −0.0068 (15) | −0.0007 (16) |
C4 | 0.053 (2) | 0.052 (2) | 0.0409 (18) | 0.0003 (17) | −0.0049 (16) | 0.0019 (16) |
C5 | 0.052 (2) | 0.048 (2) | 0.054 (2) | 0.0089 (17) | −0.0099 (18) | −0.0058 (17) |
C6 | 0.0458 (19) | 0.0408 (18) | 0.0439 (18) | −0.0038 (15) | −0.0015 (15) | 0.0024 (15) |
C7 | 0.043 (2) | 0.076 (3) | 0.072 (3) | 0.0070 (19) | −0.0031 (19) | −0.017 (2) |
C8 | 0.085 (3) | 0.053 (2) | 0.096 (3) | 0.017 (2) | −0.033 (3) | −0.001 (2) |
C9 | 0.0412 (19) | 0.041 (2) | 0.0408 (17) | 0.0035 (15) | 0.0006 (15) | −0.0031 (15) |
C10 | 0.0355 (18) | 0.057 (2) | 0.0437 (19) | 0.0046 (16) | −0.0036 (15) | −0.0055 (17) |
C11 | 0.0459 (19) | 0.052 (2) | 0.048 (2) | 0.0040 (17) | −0.0074 (16) | −0.0024 (17) |
C12 | 0.046 (2) | 0.070 (3) | 0.055 (2) | 0.0105 (18) | −0.0089 (18) | 0.003 (2) |
C13 | 0.077 (3) | 0.094 (4) | 0.068 (3) | 0.013 (3) | −0.032 (2) | 0.008 (3) |
C14 | 0.078 (3) | 0.086 (3) | 0.079 (3) | 0.003 (3) | −0.040 (3) | −0.014 (3) |
C15 | 0.052 (2) | 0.063 (3) | 0.061 (2) | 0.0004 (19) | −0.0147 (19) | −0.008 (2) |
C16 | 0.068 (3) | 0.068 (3) | 0.098 (3) | −0.009 (2) | −0.032 (2) | −0.014 (2) |
C17 | 0.084 (3) | 0.076 (3) | 0.077 (3) | 0.013 (2) | −0.016 (2) | 0.019 (2) |
Cl1—C2 | 1.715 (4) | C7—H7C | 0.9600 |
F1—C1 | 1.318 (4) | C8—H8A | 0.9600 |
F2—C1 | 1.326 (4) | C8—H8B | 0.9600 |
F3—C1 | 1.336 (4) | C8—H8C | 0.9600 |
O1—C9 | 1.226 (4) | C10—C11 | 1.389 (5) |
N1—C9 | 1.361 (4) | C10—C15 | 1.398 (5) |
N1—C10 | 1.422 (4) | C11—C12 | 1.383 (5) |
N1—H1 | 0.8600 | C11—H11 | 0.9300 |
C1—C2 | 1.490 (5) | C12—C13 | 1.370 (6) |
C2—C3 | 1.307 (4) | C12—C17 | 1.511 (6) |
C3—C4 | 1.464 (5) | C13—C14 | 1.369 (6) |
C3—H3 | 0.9300 | C13—H13 | 0.9300 |
C4—C5 | 1.511 (5) | C14—C15 | 1.388 (5) |
C4—C6 | 1.538 (4) | C14—H14 | 0.9300 |
C4—H4 | 0.9800 | C15—C16 | 1.499 (6) |
C5—C7 | 1.502 (5) | C16—H16A | 0.9600 |
C5—C8 | 1.516 (5) | C16—H16B | 0.9600 |
C5—C6 | 1.528 (4) | C16—H16C | 0.9600 |
C6—C9 | 1.478 (4) | C17—H17A | 0.9600 |
C6—H6 | 0.9800 | C17—H17B | 0.9600 |
C7—H7A | 0.9600 | C17—H17C | 0.9600 |
C7—H7B | 0.9600 | ||
C9—N1—C10 | 128.0 (3) | C5—C8—H8A | 109.5 |
C9—N1—H1 | 116.0 | C5—C8—H8B | 109.5 |
C10—N1—H1 | 116.0 | H8A—C8—H8B | 109.5 |
F1—C1—F2 | 106.5 (4) | C5—C8—H8C | 109.5 |
F1—C1—F3 | 106.9 (3) | H8A—C8—H8C | 109.5 |
F2—C1—F3 | 105.4 (3) | H8B—C8—H8C | 109.5 |
F1—C1—C2 | 112.1 (3) | O1—C9—N1 | 123.4 (3) |
F2—C1—C2 | 113.6 (3) | O1—C9—C6 | 122.8 (3) |
F3—C1—C2 | 111.9 (3) | N1—C9—C6 | 113.9 (3) |
C3—C2—C1 | 123.5 (3) | C11—C10—C15 | 120.1 (3) |
C3—C2—Cl1 | 124.2 (3) | C11—C10—N1 | 121.6 (3) |
C1—C2—Cl1 | 112.2 (3) | C15—C10—N1 | 118.3 (3) |
C2—C3—C4 | 126.6 (3) | C12—C11—C10 | 122.1 (3) |
C2—C3—H3 | 116.7 | C12—C11—H11 | 118.9 |
C4—C3—H3 | 116.7 | C10—C11—H11 | 118.9 |
C3—C4—C5 | 120.9 (3) | C13—C12—C11 | 117.4 (4) |
C3—C4—C6 | 122.4 (3) | C13—C12—C17 | 121.9 (4) |
C5—C4—C6 | 60.1 (2) | C11—C12—C17 | 120.7 (4) |
C3—C4—H4 | 114.3 | C14—C13—C12 | 121.1 (4) |
C5—C4—H4 | 114.3 | C14—C13—H13 | 119.4 |
C6—C4—H4 | 114.3 | C12—C13—H13 | 119.4 |
C7—C5—C4 | 120.6 (3) | C13—C14—C15 | 122.7 (4) |
C7—C5—C8 | 114.4 (3) | C13—C14—H14 | 118.7 |
C4—C5—C8 | 115.3 (3) | C15—C14—H14 | 118.7 |
C7—C5—C6 | 120.0 (3) | C14—C15—C10 | 116.5 (4) |
C4—C5—C6 | 60.8 (2) | C14—C15—C16 | 120.5 (4) |
C8—C5—C6 | 115.4 (3) | C10—C15—C16 | 123.0 (3) |
C9—C6—C5 | 122.6 (3) | C15—C16—H16A | 109.5 |
C9—C6—C4 | 121.2 (3) | C15—C16—H16B | 109.5 |
C5—C6—C4 | 59.1 (2) | H16A—C16—H16B | 109.5 |
C9—C6—H6 | 114.3 | C15—C16—H16C | 109.5 |
C5—C6—H6 | 114.3 | H16A—C16—H16C | 109.5 |
C4—C6—H6 | 114.3 | H16B—C16—H16C | 109.5 |
C5—C7—H7A | 109.5 | C12—C17—H17A | 109.5 |
C5—C7—H7B | 109.5 | C12—C17—H17B | 109.5 |
H7A—C7—H7B | 109.5 | H17A—C17—H17B | 109.5 |
C5—C7—H7C | 109.5 | C12—C17—H17C | 109.5 |
H7A—C7—H7C | 109.5 | H17A—C17—H17C | 109.5 |
H7B—C7—H7C | 109.5 | H17B—C17—H17C | 109.5 |
F1—C1—C2—C3 | −4.2 (5) | C3—C4—C6—C5 | −109.7 (4) |
F2—C1—C2—C3 | −125.0 (4) | C10—N1—C9—O1 | −2.0 (5) |
F3—C1—C2—C3 | 115.8 (4) | C10—N1—C9—C6 | 178.2 (3) |
F1—C1—C2—Cl1 | 174.7 (3) | C5—C6—C9—O1 | 54.5 (5) |
F2—C1—C2—Cl1 | 54.0 (4) | C4—C6—C9—O1 | −16.5 (5) |
F3—C1—C2—Cl1 | −65.2 (4) | C5—C6—C9—N1 | −125.7 (3) |
C1—C2—C3—C4 | −175.2 (3) | C4—C6—C9—N1 | 163.4 (3) |
Cl1—C2—C3—C4 | 6.0 (5) | C9—N1—C10—C11 | 18.3 (5) |
C2—C3—C4—C5 | 158.0 (3) | C9—N1—C10—C15 | −161.9 (3) |
C2—C3—C4—C6 | −129.9 (4) | C15—C10—C11—C12 | 2.5 (5) |
C3—C4—C5—C7 | 2.6 (5) | N1—C10—C11—C12 | −177.8 (3) |
C6—C4—C5—C7 | −109.5 (3) | C10—C11—C12—C13 | −1.6 (6) |
C3—C4—C5—C8 | −141.7 (3) | C10—C11—C12—C17 | 178.1 (3) |
C6—C4—C5—C8 | 106.2 (3) | C11—C12—C13—C14 | −0.5 (6) |
C3—C4—C5—C6 | 112.1 (3) | C17—C12—C13—C14 | 179.8 (4) |
C7—C5—C6—C9 | 1.1 (5) | C12—C13—C14—C15 | 1.9 (7) |
C4—C5—C6—C9 | −109.5 (3) | C13—C14—C15—C10 | −1.0 (7) |
C8—C5—C6—C9 | 144.4 (3) | C13—C14—C15—C16 | 178.8 (4) |
C7—C5—C6—C4 | 110.6 (4) | C11—C10—C15—C14 | −1.2 (5) |
C8—C5—C6—C4 | −106.1 (4) | N1—C10—C15—C14 | 179.1 (3) |
C3—C4—C6—C9 | 2.1 (5) | C11—C10—C15—C16 | 179.0 (4) |
C5—C4—C6—C9 | 111.8 (3) | N1—C10—C15—C16 | −0.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.44 | 3.214 (4) | 149 |
Symmetry code: (i) −x+1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C17H19ClF3NO |
Mr | 345.78 |
Crystal system, space group | Orthorhombic, Pbcn |
Temperature (K) | 294 |
a, b, c (Å) | 16.445 (3), 9.5147 (17), 21.856 (4) |
V (Å3) | 3419.9 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.22 × 0.20 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.946, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16642, 3027, 1746 |
Rint | 0.055 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.179, 1.01 |
No. of reflections | 3027 |
No. of parameters | 212 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.43 |
Computer programs: 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—H1···O1i | 0.86 | 2.44 | 3.214 (4) | 149.4 |
Symmetry code: (i) −x+1/2, y+1/2, z. |
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3-((E)-2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate for tefluthrin, a important insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). 2,5-dimethylbenzenamine containing pesticides have the advantage of low toxicity, high activity and low residues (Zhang, 2005). The title compound containing both these active parts may have some insecticide activity. The present X-ray crystal structure analysis was undertaken in order to study the stereochemistry and crystal packing of the title compound. The dihedral angles between the benzene moiety and the cycloprapane group is 66.7 (3)°. The crystal packing is stabilized by an N—H···O hydrogen bond.