


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314618000408/hb4201sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2414314618000408/hb4201Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314618000408/hb4201Isup3.cml |
CCDC reference: 1815173
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.139
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ...... 3.082 Check PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 4 Report
Alert level G PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 5 Report PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 1 Report PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records 1 Report PLAT186_ALERT_4_G The CIF-Embedded .res File Contains ISOR Records 1 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check PLAT242_ALERT_2_G Low 'MainMol' Ueq as Compared to Neighbors of C1 Check PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 19% Note PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 60 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 33 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 1 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 11 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and CHEMDRAW Ultra (Cambridge Soft, 2001).
C10H11F3N2O | Dx = 1.385 Mg m−3 |
Mr = 232.21 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, Pbca | Cell parameters from 2946 reflections |
a = 9.8152 (3) Å | θ = 3.9–73.8° |
b = 10.0783 (2) Å | µ = 1.10 mm−1 |
c = 22.5120 (7) Å | T = 293 K |
V = 2226.90 (11) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.23 × 0.10 mm |
F(000) = 960 |
Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer | 1708 reflections with I > 2σ(I) |
ω scans | Rint = 0.030 |
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014) | θmax = 74.0°, θmin = 3.9° |
Tmin = 0.940, Tmax = 0.974 | h = −11→7 |
7168 measured reflections | k = −12→10 |
2217 independent reflections | l = −28→25 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0878P)2 + 0.0492P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.139 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.16 e Å−3 |
2217 reflections | Δρmin = −0.17 e Å−3 |
176 parameters | Extinction correction: SHELXL2013 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
60 restraints | Extinction coefficient: 0.0102 (9) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Methyl C—H bonds were fixed at 0.96 Å, with displacement parameters 1.5 times Ueq(C), and were allowed to spin about the C—N bond. The N—H bond was fixed at 0.86 Å and aromatic C—H distances were set to 0.93 Å and their U(iso) set to 1.2 times the Ueq for the atoms to which they are bonded. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.5872 (3) | 0.0387 (3) | 0.72719 (10) | 0.1049 (8) | |
C2 | 0.49935 (19) | 0.02575 (19) | 0.67302 (8) | 0.0730 (5) | |
C3 | 0.5321 (2) | −0.06604 (19) | 0.62979 (9) | 0.0800 (5) | |
H3 | 0.6070 | −0.1214 | 0.6349 | 0.096* | |
C4 | 0.45445 (17) | −0.07598 (15) | 0.57921 (8) | 0.0678 (4) | |
H4 | 0.4774 | −0.1378 | 0.5502 | 0.081* | |
C5 | 0.34195 (14) | 0.00549 (12) | 0.57108 (6) | 0.0517 (3) | |
C6 | 0.30912 (16) | 0.09806 (14) | 0.61453 (7) | 0.0613 (4) | |
H6 | 0.2341 | 0.1533 | 0.6096 | 0.074* | |
C7 | 0.38819 (18) | 0.10778 (17) | 0.66514 (7) | 0.0707 (5) | |
H7 | 0.3664 | 0.1701 | 0.6941 | 0.085* | |
C8 | 0.20108 (14) | 0.08594 (11) | 0.48853 (6) | 0.0517 (3) | |
C9 | 0.0580 (2) | 0.15002 (18) | 0.40623 (10) | 0.0831 (5) | |
H9A | 0.0521 | 0.2304 | 0.4290 | 0.125* | |
H9B | −0.0320 | 0.1199 | 0.3964 | 0.125* | |
H9C | 0.1082 | 0.1665 | 0.3704 | 0.125* | |
C10 | 0.1105 (2) | −0.08604 (16) | 0.42132 (9) | 0.0778 (5) | |
H10A | 0.1922 | −0.1151 | 0.4019 | 0.117* | |
H10B | 0.0354 | −0.0912 | 0.3941 | 0.117* | |
H10C | 0.0928 | −0.1418 | 0.4550 | 0.117* | |
N1 | 0.26294 (13) | −0.01353 (10) | 0.51968 (5) | 0.0546 (3) | |
H1 | 0.2529 | −0.0934 | 0.5070 | 0.065* | |
N2 | 0.12717 (14) | 0.04922 (11) | 0.44086 (6) | 0.0622 (4) | |
O1 | 0.21290 (14) | 0.20262 (9) | 0.50340 (5) | 0.0728 (4) | |
F1 | 0.7132 (6) | 0.024 (2) | 0.7171 (3) | 0.169 (5) | 0.423 (12) |
F2 | 0.5686 (15) | 0.1449 (10) | 0.7571 (5) | 0.170 (5) | 0.423 (12) |
F3 | 0.5525 (14) | −0.0492 (11) | 0.7660 (4) | 0.164 (4) | 0.423 (12) |
F1A | 0.6752 (9) | 0.1385 (8) | 0.7205 (3) | 0.148 (3) | 0.577 (12) |
F3A | 0.6621 (13) | −0.0643 (6) | 0.7389 (4) | 0.179 (4) | 0.577 (12) |
F2A | 0.5211 (7) | 0.0711 (18) | 0.7739 (2) | 0.206 (6) | 0.577 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.108 (2) | 0.137 (2) | 0.0695 (13) | −0.0207 (16) | −0.0197 (12) | 0.0095 (13) |
C2 | 0.0724 (11) | 0.0874 (10) | 0.0592 (9) | −0.0186 (8) | −0.0063 (7) | 0.0109 (7) |
C3 | 0.0773 (11) | 0.0784 (10) | 0.0841 (12) | 0.0059 (8) | −0.0200 (9) | 0.0042 (8) |
C4 | 0.0750 (10) | 0.0551 (7) | 0.0734 (10) | 0.0061 (6) | −0.0107 (8) | −0.0048 (6) |
C5 | 0.0568 (8) | 0.0428 (5) | 0.0554 (7) | −0.0081 (5) | 0.0007 (6) | 0.0026 (5) |
C6 | 0.0601 (9) | 0.0642 (8) | 0.0597 (8) | −0.0048 (6) | 0.0068 (6) | −0.0068 (6) |
C7 | 0.0772 (11) | 0.0825 (10) | 0.0523 (8) | −0.0172 (8) | 0.0104 (7) | −0.0088 (7) |
C8 | 0.0574 (8) | 0.0389 (5) | 0.0587 (7) | −0.0017 (5) | 0.0043 (6) | 0.0007 (5) |
C9 | 0.0924 (13) | 0.0718 (10) | 0.0850 (12) | 0.0069 (8) | −0.0206 (10) | 0.0156 (8) |
C10 | 0.0931 (13) | 0.0589 (8) | 0.0814 (11) | −0.0074 (7) | −0.0245 (9) | −0.0080 (7) |
N1 | 0.0669 (7) | 0.0348 (5) | 0.0620 (7) | −0.0007 (4) | −0.0077 (5) | −0.0041 (4) |
N2 | 0.0704 (8) | 0.0499 (6) | 0.0664 (7) | 0.0012 (5) | −0.0119 (6) | 0.0021 (5) |
O1 | 0.1053 (10) | 0.0351 (5) | 0.0781 (7) | 0.0012 (4) | −0.0095 (6) | −0.0024 (4) |
F1 | 0.086 (3) | 0.322 (15) | 0.099 (4) | −0.005 (5) | −0.029 (2) | −0.024 (6) |
F2 | 0.213 (12) | 0.172 (6) | 0.124 (7) | 0.007 (5) | −0.083 (8) | −0.061 (5) |
F3 | 0.203 (9) | 0.210 (7) | 0.078 (4) | −0.017 (6) | −0.043 (4) | 0.056 (4) |
F1A | 0.148 (5) | 0.178 (5) | 0.116 (4) | −0.073 (4) | −0.067 (3) | 0.023 (3) |
F3A | 0.217 (8) | 0.168 (4) | 0.152 (6) | 0.037 (5) | −0.117 (6) | 0.009 (3) |
F2A | 0.140 (4) | 0.421 (18) | 0.0560 (18) | −0.029 (8) | −0.0078 (18) | −0.026 (5) |
C1—F1 | 1.267 (6) | C6—C7 | 1.382 (2) |
C1—F2 | 1.277 (7) | C6—H6 | 0.9300 |
C1—F2A | 1.277 (7) | C7—H7 | 0.9300 |
C1—F3 | 1.290 (7) | C8—O1 | 1.2281 (16) |
C1—F3A | 1.300 (6) | C8—N2 | 1.3471 (19) |
C1—F1A | 1.334 (5) | C8—N1 | 1.3658 (17) |
C1—C2 | 1.499 (3) | C9—N2 | 1.449 (2) |
C2—C7 | 1.380 (3) | C9—H9A | 0.9600 |
C2—C3 | 1.381 (3) | C9—H9B | 0.9600 |
C3—C4 | 1.374 (3) | C9—H9C | 0.9600 |
C3—H3 | 0.9300 | C10—N2 | 1.4417 (19) |
C4—C5 | 1.388 (2) | C10—H10A | 0.9600 |
C4—H4 | 0.9300 | C10—H10B | 0.9600 |
C5—C6 | 1.390 (2) | C10—H10C | 0.9600 |
C5—N1 | 1.4060 (18) | N1—H1 | 0.8600 |
F1—C1—F2 | 109.5 (6) | C5—C6—H6 | 120.1 |
F1—C1—F3 | 107.3 (7) | C2—C7—C6 | 120.49 (16) |
F2—C1—F3 | 100.4 (6) | C2—C7—H7 | 119.8 |
F2A—C1—F3A | 108.9 (6) | C6—C7—H7 | 119.8 |
F2A—C1—F1A | 103.3 (6) | O1—C8—N2 | 122.07 (12) |
F3A—C1—F1A | 105.0 (5) | O1—C8—N1 | 121.39 (13) |
F1—C1—C2 | 113.9 (3) | N2—C8—N1 | 116.54 (11) |
F2—C1—C2 | 114.9 (4) | N2—C9—H9A | 109.5 |
F2A—C1—C2 | 113.6 (4) | N2—C9—H9B | 109.5 |
F3—C1—C2 | 109.8 (4) | H9A—C9—H9B | 109.5 |
F3A—C1—C2 | 114.9 (3) | N2—C9—H9C | 109.5 |
F1A—C1—C2 | 110.3 (2) | H9A—C9—H9C | 109.5 |
C7—C2—C3 | 119.65 (16) | H9B—C9—H9C | 109.5 |
C7—C2—C1 | 120.4 (2) | N2—C10—H10A | 109.5 |
C3—C2—C1 | 119.9 (2) | N2—C10—H10B | 109.5 |
C4—C3—C2 | 120.26 (17) | H10A—C10—H10B | 109.5 |
C4—C3—H3 | 119.9 | N2—C10—H10C | 109.5 |
C2—C3—H3 | 119.9 | H10A—C10—H10C | 109.5 |
C3—C4—C5 | 120.50 (16) | H10B—C10—H10C | 109.5 |
C3—C4—H4 | 119.8 | C8—N1—C5 | 124.59 (10) |
C5—C4—H4 | 119.8 | C8—N1—H1 | 117.7 |
C4—C5—C6 | 119.25 (14) | C5—N1—H1 | 117.7 |
C4—C5—N1 | 117.81 (13) | C8—N2—C10 | 124.32 (12) |
C6—C5—N1 | 122.89 (13) | C8—N2—C9 | 119.22 (13) |
C7—C6—C5 | 119.85 (15) | C10—N2—C9 | 116.46 (14) |
C7—C6—H6 | 120.1 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.08 | 2.8939 (13) | 157 |
Symmetry code: (i) −x+1/2, y−1/2, z. |