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A total of 23 benzamides are obtained through a simple reaction between chloro-/bromo-/iodoaniline and trifluoromethylbenzoyl chloride and characterized using single-crystal X-ray diffraction. Crystal structures of three series of benzamides based on N-chlorophenyl–trifluoromethyl–benzamide (nine compounds), N-bromophenyl–trifluoromethyl–benzamide (six compounds), and N-iodophenyl–trifluoromethyl–benzamide (eight compounds) are prepared to analyse the halogen-mediated noncovalent interactions. The influences of Cl/Br/I and trifluoromethyl substituents on the respective interactions are examined in the presence of a strong N—H...O hydrogen bond. This exercise has resulted in the documentation of frequently occurring supramolecular synthons involving halogen atoms in the crystal packing of benzamide molecules in the solid state. In the present study, a detailed quantitative evaluation has been performed on the nature, energetics, electrostatic contributions, and topological properties of short and directional intermolecular interactions derived from the electron density on halogenated benzamides in the solid state. Besides these, the occurrence of three-, two- and one-dimensional isostructurality in halogen (Cl or Br or I) substituted benzamide analogues is also investigated. A `region of co-existence' involving halogen-based intermolecular interactions in the vicinity of the sum of the van der Waals radii has been identified. Thus, the nature of the halogen (effective size), type of interaction and the packing characteristics via presence of additional interactions establish the subtle, yet important, role of cooperativity in intermolecular interactions in crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618013422/aw5013sup1.cif
Contains datablocks global, PC22, PC23, PC24, PC32, PC33, PC34, PC42, PC43, PC44, PB23, PB24, PB32, PB34, PB43, PB44, PI22, PI23, PI24, PI32, PI33, PI34, PI43, PI44

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC22sup2.hkl
Contains datablock PC22

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC23sup3.hkl
Contains datablock PC23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC24sup4.hkl
Contains datablock PC24

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC32sup5.hkl
Contains datablock PC32

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC33sup6.hkl
Contains datablock PC33

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC34sup7.hkl
Contains datablock PC34

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC42sup8.hkl
Contains datablock PC42

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC43sup9.hkl
Contains datablock PC43

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PC44sup10.hkl
Contains datablock PC44

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB23sup11.hkl
Contains datablock PB23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB24sup12.hkl
Contains datablock PB24

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB32sup13.hkl
Contains datablock PB32

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB34sup14.hkl
Contains datablock PB34

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB43sup15.hkl
Contains datablock PB43

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PB44sup16.hkl
Contains datablock PB44

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI22sup17.hkl
Contains datablock PI22

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI23sup18.hkl
Contains datablock PI23

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI23sup19.hkl
Contains datablock PI24

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI32sup20.hkl
Contains datablock PI32

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI33sup21.hkl
Contains datablock PI33

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI34sup22.hkl
Contains datablock PI34

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI43sup23.hkl
Contains datablock PI43

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520618013422/aw5013PI44sup24.hkl
Contains datablock PI44

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618013422/aw5013sup25.pdf
Supplementary material

CCDC references: 1848733; 1848734; 1848735; 1848736; 1848737; 1848738; 1848739; 1848740; 1848741; 1848742; 1848743; 1848744; 1848745; 1848746; 1848747; 1848749; 1848751; 1848752; 1848753; 1848755; 1852038; 1852039; 1848750

Computing details top

For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT. Program(s) used to solve structure: SHELXS97 (Sheldrick 2008) for PC22, PC24, PC32, PC44, PB23, PB24, PB32, PB43, PB44, PI23, PI32, PI34, PI43; SHELXS97 (Sheldrick, 2008) for PC23, PC33, PC42, PB34, PI22, PI24, PI33, PI44; SHELXT 2014/4 (Sheldrick, 2014) for PC34, PC43. For all structures, program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(PC22) top
Crystal data top
C14H9ClF3NOF(000) = 608
Mr = 299.67Dx = 1.581 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.7568 (2) ÅCell parameters from 8335 reflections
b = 19.9611 (9) Åθ = 2.6–30.1°
c = 13.4063 (6) ŵ = 0.33 mm1
β = 98.457 (2)°T = 104 K
V = 1259.10 (10) Å3Plate
Z = 40.50 × 0.18 × 0.18 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2576 reflections with I > 2σ(I)
φ and ω scansRint = 0.025
Absorption correction: multi-scan
SADABS 2014/4
θmax = 27.5°, θmin = 2.6°
Tmin = 0.592, Tmax = 0.746h = 66
12750 measured reflectionsk = 2525
2877 independent reflectionsl = 1717
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079 w = 1/[σ2(Fo2) + (0.0379P)2 + 0.593P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2877 reflectionsΔρmax = 0.33 e Å3
185 parametersΔρmin = 0.25 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.30399 (7)0.01354 (2)0.61285 (2)0.02228 (10)
F10.11641 (19)0.36944 (4)0.52600 (6)0.0277 (2)
F20.16167 (17)0.29000 (4)0.63555 (6)0.02285 (18)
F30.48177 (17)0.30502 (4)0.53956 (7)0.0289 (2)
O10.41987 (18)0.16068 (5)0.59540 (7)0.0189 (2)
N10.0035 (2)0.11709 (5)0.62574 (8)0.0157 (2)
H10.177 (4)0.1204 (8)0.6091 (13)0.026 (4)*
C10.0014 (3)0.19106 (6)0.48425 (9)0.0142 (2)
C20.1738 (3)0.15263 (6)0.41394 (10)0.0183 (3)
H20.2048970.1067650.4277770.022*
C30.3038 (3)0.18050 (7)0.32381 (10)0.0218 (3)
H30.4235270.1537660.2766780.026*
C40.2588 (3)0.24725 (7)0.30268 (10)0.0214 (3)
H40.3418590.2659800.2400870.026*
C50.0915 (3)0.28671 (6)0.37351 (10)0.0187 (3)
H50.0650500.3328020.3598880.022*
C60.0375 (3)0.25922 (6)0.46422 (9)0.0149 (2)
C70.1608 (3)0.15588 (6)0.57472 (9)0.0143 (2)
C80.1010 (3)0.07140 (6)0.70315 (9)0.0148 (2)
C90.0272 (3)0.00864 (6)0.70642 (10)0.0167 (2)
C100.0646 (3)0.03713 (7)0.78242 (10)0.0220 (3)
H100.0288880.0790340.7847860.026*
C110.2939 (3)0.02103 (7)0.85471 (10)0.0247 (3)
H110.3610390.0523660.9060520.030*
C120.4253 (3)0.04092 (7)0.85207 (10)0.0227 (3)
H120.5827480.0517480.9016300.027*
C130.3285 (3)0.08711 (6)0.77758 (10)0.0188 (3)
H130.4175780.1296920.7772240.023*
C140.2001 (3)0.30516 (6)0.54093 (10)0.0180 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01961 (17)0.01946 (16)0.02583 (18)0.00396 (11)0.00314 (12)0.00043 (12)
F10.0372 (5)0.0144 (4)0.0298 (4)0.0000 (3)0.0006 (4)0.0020 (3)
F20.0264 (4)0.0253 (4)0.0161 (4)0.0024 (3)0.0005 (3)0.0029 (3)
F30.0154 (4)0.0330 (5)0.0384 (5)0.0072 (3)0.0043 (3)0.0084 (4)
O10.0099 (4)0.0232 (5)0.0229 (5)0.0008 (3)0.0000 (3)0.0036 (4)
N10.0094 (5)0.0174 (5)0.0190 (5)0.0010 (4)0.0020 (4)0.0034 (4)
C10.0104 (5)0.0173 (6)0.0149 (5)0.0022 (4)0.0018 (4)0.0003 (4)
C20.0175 (6)0.0163 (6)0.0201 (6)0.0008 (5)0.0008 (5)0.0007 (5)
C30.0208 (7)0.0238 (6)0.0187 (6)0.0017 (5)0.0043 (5)0.0036 (5)
C40.0229 (7)0.0252 (6)0.0150 (6)0.0057 (5)0.0009 (5)0.0020 (5)
C50.0197 (6)0.0178 (6)0.0189 (6)0.0025 (5)0.0035 (5)0.0027 (5)
C60.0118 (6)0.0170 (6)0.0162 (6)0.0008 (4)0.0034 (5)0.0005 (4)
C70.0134 (6)0.0134 (5)0.0157 (6)0.0020 (4)0.0004 (4)0.0013 (4)
C80.0134 (6)0.0168 (6)0.0143 (6)0.0037 (4)0.0025 (4)0.0012 (4)
C90.0149 (6)0.0185 (6)0.0164 (6)0.0018 (4)0.0010 (5)0.0012 (5)
C100.0266 (7)0.0182 (6)0.0222 (7)0.0024 (5)0.0066 (5)0.0039 (5)
C110.0309 (8)0.0254 (7)0.0173 (6)0.0092 (6)0.0024 (5)0.0065 (5)
C120.0209 (7)0.0305 (7)0.0151 (6)0.0055 (5)0.0023 (5)0.0001 (5)
C130.0168 (6)0.0204 (6)0.0184 (6)0.0012 (5)0.0001 (5)0.0010 (5)
C140.0168 (6)0.0171 (6)0.0202 (6)0.0010 (5)0.0032 (5)0.0010 (5)
Geometric parameters (Å, º) top
Cl1—C91.7370 (13)C4—C51.3903 (19)
F1—C141.3495 (15)C4—H40.9500
F2—C141.3425 (15)C5—C61.3917 (17)
F3—C141.3428 (15)C5—H50.9500
O1—C71.2266 (15)C6—C141.5042 (17)
N1—C71.3548 (17)C8—C131.3956 (17)
N1—C81.4157 (15)C8—C91.3967 (17)
N1—H10.827 (18)C9—C101.3903 (18)
C1—C21.3930 (17)C10—C111.386 (2)
C1—C61.4023 (17)C10—H100.9500
C1—C71.5061 (16)C11—C121.389 (2)
C2—C31.3900 (18)C11—H110.9500
C2—H20.9500C12—C131.3872 (18)
C3—C41.3854 (19)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8124.89 (11)C13—C8—C9118.39 (11)
C7—N1—H1116.5 (12)C13—C8—N1122.07 (11)
C8—N1—H1118.6 (12)C9—C8—N1119.54 (11)
C2—C1—C6118.86 (11)C10—C9—C8121.39 (12)
C2—C1—C7117.94 (11)C10—C9—Cl1119.00 (10)
C6—C1—C7123.04 (11)C8—C9—Cl1119.61 (9)
C3—C2—C1120.88 (12)C11—C10—C9119.35 (13)
C3—C2—H2119.6C11—C10—H10120.3
C1—C2—H2119.6C9—C10—H10120.3
C4—C3—C2120.02 (12)C10—C11—C12119.98 (12)
C4—C3—H3120.0C10—C11—H11120.0
C2—C3—H3120.0C12—C11—H11120.0
C3—C4—C5119.69 (12)C13—C12—C11120.48 (13)
C3—C4—H4120.2C13—C12—H12119.8
C5—C4—H4120.2C11—C12—H12119.8
C4—C5—C6120.53 (12)C12—C13—C8120.38 (12)
C4—C5—H5119.7C12—C13—H13119.8
C6—C5—H5119.7C8—C13—H13119.8
C5—C6—C1119.94 (11)F2—C14—F3106.69 (10)
C5—C6—C14118.25 (11)F2—C14—F1106.04 (10)
C1—C6—C14121.72 (11)F3—C14—F1105.85 (10)
O1—C7—N1124.44 (11)F2—C14—C6112.39 (10)
O1—C7—C1121.04 (11)F3—C14—C6113.76 (10)
N1—C7—C1114.43 (10)F1—C14—C6111.56 (10)
C6—C1—C2—C32.11 (19)C7—N1—C8—C9138.37 (13)
C7—C1—C2—C3173.31 (12)C13—C8—C9—C100.98 (19)
C1—C2—C3—C40.3 (2)N1—C8—C9—C10178.54 (12)
C2—C3—C4—C52.3 (2)C13—C8—C9—Cl1178.08 (10)
C3—C4—C5—C61.8 (2)N1—C8—C9—Cl12.40 (17)
C4—C5—C6—C10.63 (19)C8—C9—C10—C112.0 (2)
C4—C5—C6—C14176.00 (12)Cl1—C9—C10—C11177.02 (11)
C2—C1—C6—C52.56 (18)C9—C10—C11—C121.5 (2)
C7—C1—C6—C5172.61 (12)C10—C11—C12—C130.2 (2)
C2—C1—C6—C14173.94 (12)C11—C12—C13—C81.2 (2)
C7—C1—C6—C1410.89 (18)C9—C8—C13—C120.67 (19)
C8—N1—C7—O16.9 (2)N1—C8—C13—C12179.83 (12)
C8—N1—C7—C1169.78 (11)C5—C6—C14—F2140.71 (12)
C2—C1—C7—O1125.14 (13)C1—C6—C14—F235.85 (16)
C6—C1—C7—O150.07 (17)C5—C6—C14—F397.90 (14)
C2—C1—C7—N151.65 (15)C1—C6—C14—F385.54 (15)
C6—C1—C7—N1133.13 (12)C5—C6—C14—F121.75 (16)
C7—N1—C8—C1342.13 (18)C1—C6—C14—F1154.81 (11)
(PC23) top
Crystal data top
C14H9ClF3NOF(000) = 608
Mr = 299.67Dx = 1.535 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.8080 (9) ÅCell parameters from 7952 reflections
b = 9.7371 (18) Åθ = 4.7–30.2°
c = 27.708 (5) ŵ = 0.32 mm1
β = 91.735 (2)°T = 100 K
V = 1296.6 (4) Å3Plate
Z = 40.50 × 0.24 × 0.16 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2241 reflections with I > 2σ(I)
φ and ω scansRint = 0.025
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 4.4°
Tmin = 0.652, Tmax = 0.796h = 55
11184 measured reflectionsk = 1111
2400 independent reflectionsl = 3333
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.031H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0308P)2 + 0.7067P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2400 reflectionsΔρmax = 0.25 e Å3
213 parametersΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.34578 (8)0.41958 (4)0.04513 (2)0.02922 (13)
F1A0.0389 (8)0.0514 (7)0.2489 (2)0.100 (3)0.524 (7)
F2A0.4308 (7)0.0682 (5)0.22221 (13)0.0694 (12)0.524 (7)
F3A0.2956 (15)0.2212 (4)0.26908 (13)0.102 (3)0.524 (7)
F1B0.4307 (7)0.1573 (8)0.2449 (2)0.088 (3)0.476 (7)
F2B0.0469 (11)0.1915 (5)0.27730 (9)0.0719 (16)0.476 (7)
F3B0.0914 (16)0.0233 (5)0.2339 (2)0.095 (2)0.476 (7)
O10.40581 (19)0.19160 (11)0.05195 (4)0.0274 (3)
N10.0323 (2)0.23361 (12)0.02096 (4)0.0202 (3)
H10.198 (4)0.2471 (17)0.0286 (6)0.025 (4)*
C10.0597 (3)0.26405 (14)0.10619 (5)0.0205 (3)
C20.1304 (3)0.36989 (15)0.11262 (5)0.0256 (3)
H20.2041250.4183400.0853630.031*
C30.2130 (4)0.40511 (17)0.15859 (6)0.0334 (4)
H30.3408500.4782690.1627080.040*
C40.1091 (3)0.33362 (18)0.19851 (6)0.0328 (4)
H40.1664380.3569370.2299830.039*
C50.0796 (3)0.22766 (16)0.19208 (5)0.0296 (4)
C60.1678 (3)0.19372 (15)0.14630 (5)0.0257 (3)
H60.3011490.1229020.1423840.031*
C70.1622 (3)0.22585 (14)0.05726 (5)0.0198 (3)
C80.0163 (3)0.20954 (14)0.02849 (5)0.0197 (3)
C90.1228 (3)0.28966 (14)0.06345 (5)0.0218 (3)
C100.0861 (3)0.26916 (16)0.11230 (6)0.0295 (3)
H100.1833850.3243170.1355000.035*
C120.2333 (3)0.08646 (16)0.09280 (6)0.0316 (4)
H120.3565070.0166010.1029550.038*
C110.0946 (3)0.16707 (18)0.12702 (6)0.0335 (4)
H110.1229400.1525620.1604190.040*
C130.1945 (3)0.10661 (15)0.04399 (5)0.0245 (3)
H130.2896040.0500470.0209470.029*
C140.1867 (4)0.1472 (2)0.23480 (6)0.0428 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0306 (2)0.0271 (2)0.0300 (2)0.01241 (15)0.00245 (15)0.00326 (15)
F1A0.0382 (16)0.147 (6)0.112 (5)0.037 (2)0.013 (2)0.106 (4)
F2A0.066 (2)0.096 (3)0.0454 (18)0.0297 (19)0.0026 (13)0.0343 (17)
F3A0.187 (8)0.075 (2)0.039 (2)0.010 (3)0.057 (3)0.0065 (16)
F1B0.0285 (16)0.150 (6)0.084 (4)0.028 (2)0.0235 (18)0.082 (4)
F2B0.101 (4)0.093 (3)0.0218 (13)0.036 (2)0.0082 (15)0.0116 (14)
F3B0.197 (7)0.0340 (18)0.051 (2)0.022 (3)0.051 (3)0.0189 (17)
O10.0160 (5)0.0372 (6)0.0290 (6)0.0044 (4)0.0022 (4)0.0012 (5)
N10.0155 (6)0.0239 (6)0.0213 (6)0.0034 (5)0.0030 (5)0.0008 (5)
C10.0168 (6)0.0217 (7)0.0230 (7)0.0031 (5)0.0007 (5)0.0009 (6)
C20.0268 (7)0.0253 (7)0.0245 (7)0.0028 (6)0.0009 (6)0.0002 (6)
C30.0359 (9)0.0328 (9)0.0317 (9)0.0055 (7)0.0050 (7)0.0076 (7)
C40.0390 (9)0.0367 (9)0.0232 (8)0.0082 (7)0.0054 (7)0.0056 (7)
C50.0332 (8)0.0309 (8)0.0243 (8)0.0111 (7)0.0043 (6)0.0045 (6)
C60.0235 (7)0.0256 (8)0.0280 (8)0.0001 (6)0.0019 (6)0.0036 (6)
C70.0173 (7)0.0183 (7)0.0239 (7)0.0002 (5)0.0016 (5)0.0039 (5)
C80.0176 (6)0.0190 (7)0.0226 (7)0.0022 (5)0.0025 (5)0.0001 (5)
C90.0204 (7)0.0191 (7)0.0261 (7)0.0015 (5)0.0026 (5)0.0006 (6)
C100.0339 (8)0.0307 (8)0.0237 (8)0.0011 (7)0.0006 (6)0.0022 (6)
C120.0315 (8)0.0282 (8)0.0357 (9)0.0054 (7)0.0078 (7)0.0077 (7)
C110.0404 (9)0.0367 (9)0.0236 (8)0.0002 (7)0.0066 (7)0.0063 (7)
C130.0230 (7)0.0217 (7)0.0290 (8)0.0021 (6)0.0023 (6)0.0003 (6)
C140.0551 (12)0.0459 (11)0.0270 (9)0.0089 (9)0.0077 (8)0.0088 (8)
Geometric parameters (Å, º) top
Cl1—C91.7438 (14)C3—H30.9500
F1A—C141.243 (4)C4—C51.389 (2)
F2A—C141.454 (4)C4—H40.9500
F3A—C141.291 (3)C5—C61.390 (2)
F1B—C141.202 (3)C5—C141.498 (2)
F2B—C141.440 (3)C6—H60.9500
F3B—C141.290 (5)C8—C131.3947 (19)
O1—C71.2309 (17)C8—C91.398 (2)
N1—C71.3547 (18)C9—C101.384 (2)
N1—C81.4166 (18)C10—C111.389 (2)
N1—H10.840 (18)C10—H100.9500
C1—C61.392 (2)C12—C131.385 (2)
C1—C21.393 (2)C12—C111.386 (2)
C1—C71.5031 (19)C12—H120.9500
C2—C31.389 (2)C11—H110.9500
C2—H20.9500C13—H130.9500
C3—C41.387 (2)
C7—N1—C8125.35 (12)C10—C9—C8121.63 (13)
C7—N1—H1117.5 (11)C10—C9—Cl1119.13 (11)
C8—N1—H1117.0 (11)C8—C9—Cl1119.24 (11)
C6—C1—C2119.50 (13)C9—C10—C11119.30 (14)
C6—C1—C7118.26 (13)C9—C10—H10120.3
C2—C1—C7122.20 (13)C11—C10—H10120.3
C3—C2—C1120.48 (14)C13—C12—C11120.75 (14)
C3—C2—H2119.8C13—C12—H12119.6
C1—C2—H2119.8C11—C12—H12119.6
C4—C3—C2120.08 (15)C12—C11—C10119.77 (14)
C4—C3—H3120.0C12—C11—H11120.1
C2—C3—H3120.0C10—C11—H11120.1
C3—C4—C5119.44 (14)C12—C13—C8120.32 (14)
C3—C4—H4120.3C12—C13—H13119.8
C5—C4—H4120.3C8—C13—H13119.8
C4—C5—C6120.82 (14)F1B—C14—F3B115.1 (4)
C4—C5—C14119.85 (15)F1A—C14—F3A114.2 (4)
C6—C5—C14119.33 (16)F1B—C14—F2B105.1 (4)
C5—C6—C1119.66 (14)F3B—C14—F2B96.9 (3)
C5—C6—H6120.2F1A—C14—F2A98.7 (3)
C1—C6—H6120.2F3A—C14—F2A99.2 (3)
O1—C7—N1124.36 (13)F1B—C14—C5116.8 (2)
O1—C7—C1120.93 (12)F1A—C14—C5117.1 (3)
N1—C7—C1114.71 (12)F3B—C14—C5111.2 (3)
C13—C8—C9118.23 (13)F3A—C14—C5114.3 (2)
C13—C8—N1122.51 (13)F2B—C14—C5109.36 (19)
C9—C8—N1119.25 (12)F2A—C14—C5110.36 (18)
C6—C1—C2—C30.2 (2)N1—C8—C9—Cl11.49 (18)
C7—C1—C2—C3177.83 (14)C8—C9—C10—C110.4 (2)
C1—C2—C3—C40.9 (2)Cl1—C9—C10—C11179.06 (12)
C2—C3—C4—C50.6 (2)C13—C12—C11—C100.1 (3)
C3—C4—C5—C60.8 (2)C9—C10—C11—C120.6 (2)
C3—C4—C5—C14178.23 (15)C11—C12—C13—C80.6 (2)
C4—C5—C6—C11.9 (2)C9—C8—C13—C120.8 (2)
C14—C5—C6—C1177.16 (14)N1—C8—C13—C12179.49 (14)
C2—C1—C6—C51.6 (2)C4—C5—C14—F1B114.5 (5)
C7—C1—C6—C5179.29 (13)C6—C5—C14—F1B66.4 (5)
C8—N1—C7—O12.8 (2)C4—C5—C14—F1A83.2 (5)
C8—N1—C7—C1176.68 (12)C6—C5—C14—F1A95.9 (5)
C6—C1—C7—O135.6 (2)C4—C5—C14—F3B110.6 (4)
C2—C1—C7—O1142.08 (14)C6—C5—C14—F3B68.5 (4)
C6—C1—C7—N1144.89 (13)C4—C5—C14—F3A54.2 (5)
C2—C1—C7—N137.47 (19)C6—C5—C14—F3A126.7 (4)
C7—N1—C8—C1338.4 (2)C4—C5—C14—F2B4.7 (3)
C7—N1—C8—C9142.92 (14)C6—C5—C14—F2B174.4 (3)
C13—C8—C9—C100.3 (2)C4—C5—C14—F2A165.0 (3)
N1—C8—C9—C10179.04 (13)C6—C5—C14—F2A15.9 (3)
C13—C8—C9—Cl1179.74 (10)
(PC24) top
Crystal data top
C14H9ClF3NOZ = 2
Mr = 299.67F(000) = 304
Triclinic, P1Dx = 1.573 Mg m3
a = 4.8189 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.4501 (5) ÅCell parameters from 8370 reflections
c = 14.0283 (7) Åθ = 2.5–30.0°
α = 96.048 (2)°µ = 0.33 mm1
β = 93.400 (2)°T = 105 K
γ = 93.414 (2)°Plate
V = 632.77 (5) Å30.50 × 0.29 × 0.07 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2885 reflections with I > 2σ(I)
φ and ω scansRint = 0.024
Absorption correction: multi-scan
SADABS 2014/4
θmax = 28.3°, θmin = 2.9°
Tmin = 0.692, Tmax = 0.846h = 65
11863 measured reflectionsk = 1212
3145 independent reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.044P)2 + 0.5169P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3145 reflectionsΔρmax = 0.72 e Å3
185 parametersΔρmin = 0.68 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.68214 (7)0.43276 (3)0.58367 (2)0.01814 (10)
F10.8618 (3)0.3611 (2)0.05256 (9)0.0627 (5)
F20.4492 (2)0.33611 (15)0.01285 (7)0.0422 (3)
F30.6581 (5)0.15361 (16)0.06200 (10)0.0851 (7)
O11.3715 (2)0.18181 (11)0.38774 (7)0.0191 (2)
N10.9550 (2)0.23067 (12)0.44870 (8)0.0138 (2)
H10.789 (4)0.239 (2)0.4330 (14)0.024 (5)*
C11.0039 (3)0.23166 (14)0.27840 (10)0.0143 (3)
C20.8087 (3)0.33112 (15)0.26294 (10)0.0173 (3)
H20.7450520.3883850.3159910.021*
C30.7065 (3)0.34690 (16)0.17006 (11)0.0202 (3)
H30.5739030.4150470.1595180.024*
C40.7995 (3)0.26230 (16)0.09276 (10)0.0200 (3)
C50.9972 (3)0.16400 (16)0.10761 (11)0.0209 (3)
H51.0611190.1070060.0545050.025*
C61.1003 (3)0.14958 (16)0.20014 (10)0.0189 (3)
H61.2373020.0835270.2103430.023*
C71.1280 (3)0.21223 (14)0.37671 (10)0.0139 (2)
C81.0295 (3)0.22082 (14)0.54689 (9)0.0134 (2)
C90.9103 (3)0.30869 (14)0.61735 (10)0.0147 (3)
C100.9717 (3)0.30036 (16)0.71456 (10)0.0191 (3)
H100.8868700.3603240.7614810.023*
C111.1583 (3)0.20352 (16)0.74254 (11)0.0215 (3)
H111.2029400.1975310.8088130.026*
C121.2794 (3)0.11559 (16)0.67339 (11)0.0200 (3)
H121.4073490.0496530.6925800.024*
C131.2148 (3)0.12327 (14)0.57639 (10)0.0161 (3)
H131.2971930.0617640.5297100.019*
C140.6919 (4)0.2777 (2)0.00786 (11)0.0281 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01833 (17)0.01686 (17)0.01952 (17)0.00644 (12)0.00027 (12)0.00117 (12)
F10.0362 (7)0.1277 (14)0.0295 (6)0.0027 (7)0.0012 (5)0.0396 (8)
F20.0309 (6)0.0743 (9)0.0243 (5)0.0192 (5)0.0039 (4)0.0130 (5)
F30.1582 (18)0.0507 (8)0.0380 (7)0.0429 (10)0.0566 (9)0.0195 (6)
O10.0120 (4)0.0266 (5)0.0190 (5)0.0040 (4)0.0002 (4)0.0025 (4)
N10.0105 (5)0.0175 (5)0.0135 (5)0.0021 (4)0.0012 (4)0.0019 (4)
C10.0119 (6)0.0159 (6)0.0148 (6)0.0006 (5)0.0003 (5)0.0019 (5)
C20.0174 (6)0.0187 (6)0.0161 (6)0.0036 (5)0.0021 (5)0.0015 (5)
C30.0200 (7)0.0228 (7)0.0189 (7)0.0066 (5)0.0005 (5)0.0048 (5)
C40.0194 (7)0.0248 (7)0.0154 (6)0.0009 (5)0.0022 (5)0.0029 (5)
C50.0231 (7)0.0232 (7)0.0157 (6)0.0039 (6)0.0012 (5)0.0024 (5)
C60.0183 (6)0.0200 (7)0.0181 (7)0.0047 (5)0.0000 (5)0.0003 (5)
C70.0131 (6)0.0132 (6)0.0149 (6)0.0000 (5)0.0006 (5)0.0009 (5)
C80.0120 (6)0.0145 (6)0.0135 (6)0.0007 (5)0.0007 (5)0.0023 (5)
C90.0132 (6)0.0138 (6)0.0170 (6)0.0015 (5)0.0009 (5)0.0029 (5)
C100.0218 (7)0.0199 (7)0.0153 (6)0.0018 (5)0.0015 (5)0.0006 (5)
C110.0240 (7)0.0243 (7)0.0163 (6)0.0008 (6)0.0038 (5)0.0058 (6)
C120.0178 (6)0.0197 (7)0.0231 (7)0.0022 (5)0.0042 (5)0.0067 (5)
C130.0139 (6)0.0152 (6)0.0193 (7)0.0019 (5)0.0000 (5)0.0023 (5)
C140.0287 (8)0.0387 (9)0.0169 (7)0.0091 (7)0.0029 (6)0.0015 (6)
Geometric parameters (Å, º) top
Cl1—C91.7367 (14)C4—C51.392 (2)
F1—C141.331 (2)C4—C141.499 (2)
F2—C141.3239 (19)C5—C61.385 (2)
F3—C141.324 (2)C5—H50.9500
O1—C71.2296 (16)C6—H60.9500
N1—C71.3510 (17)C8—C91.3954 (19)
N1—C81.4166 (17)C8—C131.3976 (18)
N1—H10.83 (2)C9—C101.3895 (19)
C1—C21.3929 (19)C10—C111.390 (2)
C1—C61.3953 (19)C10—H100.9500
C1—C71.5038 (18)C11—C121.388 (2)
C2—C31.391 (2)C11—H110.9500
C2—H20.9500C12—C131.388 (2)
C3—C41.391 (2)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.02 (12)C9—C8—C13118.25 (12)
C7—N1—H1116.7 (14)C9—C8—N1119.47 (12)
C8—N1—H1117.8 (14)C13—C8—N1122.27 (12)
C2—C1—C6119.66 (13)C10—C9—C8121.52 (13)
C2—C1—C7122.77 (12)C10—C9—Cl1118.81 (11)
C6—C1—C7117.51 (12)C8—C9—Cl1119.68 (10)
C3—C2—C1120.22 (13)C9—C10—C11119.42 (13)
C3—C2—H2119.9C9—C10—H10120.3
C1—C2—H2119.9C11—C10—H10120.3
C4—C3—C2119.60 (13)C12—C11—C10119.82 (13)
C4—C3—H3120.2C12—C11—H11120.1
C2—C3—H3120.2C10—C11—H11120.1
C3—C4—C5120.47 (13)C11—C12—C13120.49 (13)
C3—C4—C14120.40 (14)C11—C12—H12119.8
C5—C4—C14119.12 (14)C13—C12—H12119.8
C6—C5—C4119.74 (13)C12—C13—C8120.50 (13)
C6—C5—H5120.1C12—C13—H13119.8
C4—C5—H5120.1C8—C13—H13119.8
C5—C6—C1120.29 (13)F2—C14—F3106.49 (16)
C5—C6—H6119.9F2—C14—F1104.76 (15)
C1—C6—H6119.9F3—C14—F1106.47 (17)
O1—C7—N1124.19 (13)F2—C14—C4113.63 (14)
O1—C7—C1120.34 (12)F3—C14—C4112.23 (15)
N1—C7—C1115.47 (12)F1—C14—C4112.65 (14)
C6—C1—C2—C31.1 (2)C13—C8—C9—C100.2 (2)
C7—C1—C2—C3178.33 (13)N1—C8—C9—C10178.38 (12)
C1—C2—C3—C40.3 (2)C13—C8—C9—Cl1179.25 (10)
C2—C3—C4—C51.1 (2)N1—C8—C9—Cl12.18 (18)
C2—C3—C4—C14179.98 (14)C8—C9—C10—C110.7 (2)
C3—C4—C5—C60.5 (2)Cl1—C9—C10—C11178.71 (11)
C14—C4—C5—C6179.39 (14)C9—C10—C11—C120.5 (2)
C4—C5—C6—C10.9 (2)C10—C11—C12—C130.2 (2)
C2—C1—C6—C51.7 (2)C11—C12—C13—C80.8 (2)
C7—C1—C6—C5179.09 (13)C9—C8—C13—C120.6 (2)
C8—N1—C7—O11.4 (2)N1—C8—C13—C12179.08 (12)
C8—N1—C7—C1178.48 (11)C3—C4—C14—F221.9 (2)
C2—C1—C7—O1145.14 (14)C5—C4—C14—F2159.22 (15)
C6—C1—C7—O132.13 (19)C3—C4—C14—F3142.79 (18)
C2—C1—C7—N134.77 (18)C5—C4—C14—F338.3 (2)
C6—C1—C7—N1147.96 (13)C3—C4—C14—F197.06 (19)
C7—N1—C8—C9145.91 (14)C5—C4—C14—F181.8 (2)
C7—N1—C8—C1335.6 (2)
(PC32) top
Crystal data top
C14H9ClF3NODx = 1.516 Mg m3
Mr = 299.67Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 5990 reflections
a = 7.7658 (6) Åθ = 2.8–30.0°
b = 19.1333 (13) ŵ = 0.32 mm1
c = 8.8369 (5) ÅT = 104 K
V = 1313.03 (15) Å3Plate
Z = 40.40 × 0.40 × 0.06 mm
F(000) = 608
Data collection top
Bruker APEX-II CCD
diffractometer
3099 reflections with I > 2σ(I)
φ and ω scansRint = 0.060
Absorption correction: multi-scan
SADABS 2014/4
θmax = 30.0°, θmin = 2.8°
Tmin = 0.632, Tmax = 0.796h = 1010
14300 measured reflectionsk = 2626
3609 independent reflectionsl = 1210
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.042 w = 1/[σ2(Fo2) + (0.0404P)2 + 0.4809P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.55 e Å3
3609 reflectionsΔρmin = 0.28 e Å3
185 parametersAbsolute structure: Flack x determined using 1139 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.02 (3)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.93285 (9)0.46683 (4)0.83195 (8)0.02405 (17)
F10.7021 (3)0.03059 (10)0.5070 (3)0.0411 (5)
F20.8187 (2)0.13129 (10)0.5409 (2)0.0322 (5)
F30.6053 (3)0.09908 (12)0.6792 (2)0.0363 (5)
O10.6058 (3)0.25747 (11)0.6312 (2)0.0219 (4)
N10.7630 (3)0.28718 (12)0.4226 (3)0.0159 (4)
H10.783 (4)0.2758 (18)0.332 (3)0.029 (9)*
C10.5375 (3)0.20103 (14)0.3995 (3)0.0130 (5)
C20.4267 (3)0.22715 (15)0.2909 (3)0.0169 (5)
H20.4243780.2759860.2715950.020*
C40.3246 (4)0.11160 (17)0.2355 (4)0.0241 (6)
H40.2502960.0812020.1810680.029*
C30.3186 (4)0.18310 (16)0.2097 (3)0.0219 (6)
H30.2410830.2017930.1369740.026*
C50.4390 (3)0.08455 (14)0.3404 (4)0.0225 (6)
H50.4454250.0354610.3554490.027*
C60.5443 (3)0.12881 (14)0.4239 (3)0.0158 (5)
C70.6405 (3)0.25117 (14)0.4965 (3)0.0141 (5)
C80.8888 (4)0.33104 (14)0.4917 (3)0.0161 (5)
C91.0558 (4)0.32816 (15)0.4353 (3)0.0199 (6)
H91.0822130.2985030.3523110.024*
C101.1841 (4)0.36882 (16)0.5009 (3)0.0223 (6)
H101.2978120.3671940.4614350.027*
C111.1477 (4)0.41186 (14)0.6238 (3)0.0209 (6)
H111.2357510.4387530.6704420.025*
C120.9806 (4)0.41445 (14)0.6759 (3)0.0173 (5)
C130.8468 (4)0.37543 (14)0.6114 (3)0.0163 (5)
H130.7320200.3790400.6477460.020*
C140.6664 (4)0.09815 (16)0.5372 (4)0.0241 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0312 (3)0.0202 (3)0.0208 (3)0.0059 (3)0.0076 (3)0.0084 (3)
F10.0499 (13)0.0231 (9)0.0504 (14)0.0158 (8)0.0045 (11)0.0057 (9)
F20.0199 (8)0.0411 (11)0.0355 (11)0.0030 (8)0.0073 (8)0.0101 (9)
F30.0394 (11)0.0490 (13)0.0204 (10)0.0085 (9)0.0024 (8)0.0142 (9)
O10.0234 (10)0.0334 (12)0.0090 (9)0.0070 (9)0.0019 (8)0.0039 (8)
N10.0205 (11)0.0203 (11)0.0069 (9)0.0034 (9)0.0000 (8)0.0025 (9)
C10.0112 (11)0.0175 (12)0.0103 (12)0.0013 (9)0.0021 (9)0.0010 (9)
C20.0181 (13)0.0176 (12)0.0148 (12)0.0002 (10)0.0007 (10)0.0003 (10)
C40.0187 (14)0.0271 (15)0.0267 (15)0.0071 (11)0.0007 (12)0.0073 (13)
C30.0174 (13)0.0293 (16)0.0190 (14)0.0000 (11)0.0058 (11)0.0032 (11)
C50.0229 (13)0.0164 (12)0.0281 (15)0.0022 (10)0.0075 (13)0.0009 (13)
C60.0152 (13)0.0175 (13)0.0147 (12)0.0002 (10)0.0033 (10)0.0033 (10)
C70.0137 (12)0.0177 (13)0.0109 (12)0.0017 (10)0.0012 (10)0.0004 (10)
C80.0223 (13)0.0139 (12)0.0122 (12)0.0029 (10)0.0044 (10)0.0025 (10)
C90.0218 (14)0.0225 (14)0.0154 (13)0.0043 (10)0.0013 (10)0.0006 (11)
C100.0208 (13)0.0260 (15)0.0201 (14)0.0083 (11)0.0011 (12)0.0002 (12)
C110.0255 (15)0.0178 (13)0.0193 (13)0.0066 (11)0.0023 (12)0.0012 (12)
C120.0288 (14)0.0100 (12)0.0131 (12)0.0020 (10)0.0044 (11)0.0001 (9)
C130.0208 (13)0.0165 (12)0.0115 (11)0.0001 (10)0.0010 (10)0.0024 (10)
C140.0277 (16)0.0217 (14)0.0230 (15)0.0056 (12)0.0037 (12)0.0048 (11)
Geometric parameters (Å, º) top
Cl1—C121.745 (3)C4—H40.9500
F1—C141.348 (4)C3—H30.9500
F2—C141.342 (4)C5—C61.389 (4)
F3—C141.342 (4)C5—H50.9500
O1—C71.227 (3)C6—C141.499 (4)
N1—C71.344 (4)C8—C91.391 (4)
N1—C81.425 (3)C8—C131.395 (4)
N1—H10.85 (2)C9—C101.390 (4)
C1—C21.382 (4)C9—H90.9500
C1—C61.400 (4)C10—C111.392 (4)
C1—C71.515 (4)C10—H100.9500
C2—C31.390 (4)C11—C121.378 (4)
C2—H20.9500C11—H110.9500
C4—C51.384 (5)C12—C131.401 (4)
C4—C31.388 (4)C13—H130.9500
C7—N1—C8125.4 (2)C9—C8—C13120.9 (3)
C7—N1—H1117 (2)C9—C8—N1117.6 (3)
C8—N1—H1116 (2)C13—C8—N1121.5 (3)
C2—C1—C6119.2 (2)C10—C9—C8119.8 (3)
C2—C1—C7119.5 (2)C10—C9—H9120.1
C6—C1—C7121.2 (2)C8—C9—H9120.1
C1—C2—C3121.0 (3)C9—C10—C11120.7 (3)
C1—C2—H2119.5C9—C10—H10119.6
C3—C2—H2119.5C11—C10—H10119.6
C5—C4—C3120.0 (3)C12—C11—C10118.3 (3)
C5—C4—H4120.0C12—C11—H11120.9
C3—C4—H4120.0C10—C11—H11120.9
C4—C3—C2119.5 (3)C11—C12—C13122.9 (3)
C4—C3—H3120.2C11—C12—Cl1119.0 (2)
C2—C3—H3120.2C13—C12—Cl1118.1 (2)
C4—C5—C6120.4 (3)C8—C13—C12117.4 (3)
C4—C5—H5119.8C8—C13—H13121.3
C6—C5—H5119.8C12—C13—H13121.3
C5—C6—C1119.8 (3)F3—C14—F2106.4 (3)
C5—C6—C14119.3 (3)F3—C14—F1105.7 (2)
C1—C6—C14120.9 (3)F2—C14—F1106.1 (2)
O1—C7—N1125.2 (3)F3—C14—C6113.3 (2)
O1—C7—C1119.7 (2)F2—C14—C6112.9 (2)
N1—C7—C1115.1 (2)F1—C14—C6111.9 (3)
C6—C1—C2—C32.1 (4)C7—N1—C8—C1341.0 (4)
C7—C1—C2—C3174.0 (2)C13—C8—C9—C101.4 (4)
C5—C4—C3—C20.6 (4)N1—C8—C9—C10178.6 (3)
C1—C2—C3—C41.4 (4)C8—C9—C10—C110.8 (4)
C3—C4—C5—C62.0 (5)C9—C10—C11—C121.7 (4)
C4—C5—C6—C11.4 (4)C10—C11—C12—C130.4 (4)
C4—C5—C6—C14179.8 (3)C10—C11—C12—Cl1178.8 (2)
C2—C1—C6—C50.7 (4)C9—C8—C13—C122.6 (4)
C7—C1—C6—C5175.3 (3)N1—C8—C13—C12177.5 (2)
C2—C1—C6—C14178.2 (2)C11—C12—C13—C81.7 (4)
C7—C1—C6—C145.8 (4)Cl1—C12—C13—C8176.8 (2)
C8—N1—C7—O19.5 (5)C5—C6—C14—F397.4 (3)
C8—N1—C7—C1172.3 (2)C1—C6—C14—F383.8 (3)
C2—C1—C7—O1109.9 (3)C5—C6—C14—F2141.6 (3)
C6—C1—C7—O166.1 (4)C1—C6—C14—F237.3 (4)
C2—C1—C7—N168.4 (3)C5—C6—C14—F122.0 (4)
C6—C1—C7—N1115.6 (3)C1—C6—C14—F1156.9 (3)
C7—N1—C8—C9139.1 (3)
(PC33) top
Crystal data top
C14H9ClF3NOF(000) = 608
Mr = 299.67Dx = 1.562 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 25.6147 (13) ÅCell parameters from 9996 reflections
b = 5.3354 (3) Åθ = 2.4–30.0°
c = 9.3918 (4) ŵ = 0.33 mm1
β = 96.775 (2)°T = 107 K
V = 1274.56 (11) Å3Plate
Z = 40.45 × 0.38 × 0.11 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2799 reflections with I > 2σ(I)
φ and ω scansRint = 0.030
Absorption correction: multi-scan
SADABS 2014/4
θmax = 28.7°, θmin = 3.2°
Tmin = 0.624, Tmax = 0.772h = 3434
22049 measured reflectionsk = 77
3282 independent reflectionsl = 1112
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0501P)2 + 0.9622P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
3282 reflectionsΔρmax = 0.52 e Å3
185 parametersΔρmin = 0.37 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.95500 (2)0.26109 (8)0.22000 (4)0.02608 (12)
F10.57545 (4)0.2058 (2)0.29306 (11)0.0388 (3)
F20.53553 (4)0.3109 (3)0.08899 (13)0.0434 (3)
F30.52809 (5)0.0600 (2)0.16741 (15)0.0492 (4)
O10.75556 (4)0.4164 (2)0.17882 (11)0.0188 (2)
N10.77546 (5)0.3084 (2)0.04345 (14)0.0177 (3)
H10.7656 (8)0.229 (4)0.122 (2)0.024 (5)*
C10.69807 (5)0.1323 (3)0.04065 (15)0.0157 (3)
C20.69619 (6)0.0811 (3)0.04568 (15)0.0183 (3)
H20.7258310.1259530.0921660.022*
C30.65116 (6)0.2281 (3)0.06391 (16)0.0201 (3)
H30.6502590.3737130.1223580.024*
C40.60735 (6)0.1637 (3)0.00280 (16)0.0200 (3)
H40.5764020.2632180.0106680.024*
C50.60946 (5)0.0482 (3)0.08943 (15)0.0164 (3)
C60.65452 (5)0.1949 (3)0.11014 (15)0.0157 (3)
H60.6557350.3372290.1712610.019*
C70.74555 (5)0.2984 (3)0.06615 (15)0.0156 (3)
C80.82552 (5)0.4247 (3)0.04069 (15)0.0170 (3)
C90.86079 (6)0.3108 (3)0.12302 (16)0.0179 (3)
H90.8510140.1648110.1776480.021*
C100.91031 (6)0.4147 (3)0.12357 (16)0.0190 (3)
C110.92550 (6)0.6301 (3)0.04754 (17)0.0221 (3)
H110.9595230.6995660.0501750.027*
C120.88965 (6)0.7423 (3)0.03276 (17)0.0230 (3)
H120.8993980.8905330.0853040.028*
C130.83974 (6)0.6415 (3)0.03769 (16)0.0207 (3)
H130.8157110.7192070.0935850.025*
C140.56217 (6)0.1263 (3)0.16033 (16)0.0207 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01711 (18)0.0307 (2)0.0320 (2)0.00115 (14)0.00940 (14)0.00026 (16)
F10.0232 (5)0.0692 (8)0.0243 (5)0.0055 (5)0.0045 (4)0.0172 (5)
F20.0291 (6)0.0631 (8)0.0408 (7)0.0236 (5)0.0157 (5)0.0214 (6)
F30.0416 (7)0.0455 (7)0.0680 (9)0.0215 (6)0.0379 (6)0.0166 (6)
O10.0182 (5)0.0248 (6)0.0137 (5)0.0010 (4)0.0028 (4)0.0011 (4)
N10.0158 (6)0.0230 (6)0.0146 (6)0.0031 (5)0.0033 (4)0.0019 (5)
C10.0152 (6)0.0175 (7)0.0144 (6)0.0010 (5)0.0024 (5)0.0034 (5)
C20.0196 (7)0.0193 (7)0.0168 (7)0.0033 (6)0.0055 (5)0.0023 (5)
C30.0248 (7)0.0171 (7)0.0184 (7)0.0001 (6)0.0026 (6)0.0013 (5)
C40.0195 (7)0.0209 (7)0.0195 (7)0.0042 (6)0.0024 (5)0.0013 (6)
C50.0157 (6)0.0204 (7)0.0136 (6)0.0000 (5)0.0035 (5)0.0031 (5)
C60.0166 (6)0.0178 (7)0.0131 (6)0.0002 (5)0.0027 (5)0.0009 (5)
C70.0150 (6)0.0178 (7)0.0142 (6)0.0026 (5)0.0020 (5)0.0023 (5)
C80.0159 (6)0.0193 (7)0.0159 (7)0.0021 (5)0.0022 (5)0.0031 (5)
C90.0165 (6)0.0194 (7)0.0178 (7)0.0012 (5)0.0023 (5)0.0003 (5)
C100.0161 (7)0.0228 (7)0.0185 (7)0.0013 (6)0.0033 (5)0.0045 (6)
C110.0183 (7)0.0245 (8)0.0232 (8)0.0056 (6)0.0007 (5)0.0046 (6)
C120.0257 (8)0.0217 (8)0.0211 (8)0.0060 (6)0.0008 (6)0.0007 (6)
C130.0225 (7)0.0206 (7)0.0196 (7)0.0009 (6)0.0049 (5)0.0003 (6)
C140.0153 (6)0.0286 (8)0.0191 (7)0.0021 (6)0.0048 (5)0.0018 (6)
Geometric parameters (Å, º) top
Cl1—C101.7454 (15)C4—C51.390 (2)
F1—C141.3227 (18)C4—H40.9500
F2—C141.3330 (19)C5—C61.389 (2)
F3—C141.3298 (19)C5—C141.5082 (19)
O1—C71.2318 (18)C6—H60.9500
N1—C71.3549 (18)C8—C91.396 (2)
N1—C81.4219 (18)C8—C131.396 (2)
N1—H10.86 (2)C9—C101.385 (2)
C1—C21.395 (2)C9—H90.9500
C1—C61.3978 (19)C10—C111.385 (2)
C1—C71.501 (2)C11—C121.390 (2)
C2—C31.389 (2)C11—H110.9500
C2—H20.9500C12—C131.393 (2)
C3—C41.391 (2)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8126.35 (13)C9—C8—C13120.46 (13)
C7—N1—H1119.9 (14)C9—C8—N1116.18 (13)
C8—N1—H1113.6 (14)C13—C8—N1123.36 (13)
C2—C1—C6119.47 (13)C10—C9—C8118.75 (14)
C2—C1—C7123.12 (13)C10—C9—H9120.6
C6—C1—C7117.40 (13)C8—C9—H9120.6
C3—C2—C1120.24 (13)C11—C10—C9122.14 (14)
C3—C2—H2119.9C11—C10—Cl1119.73 (11)
C1—C2—H2119.9C9—C10—Cl1118.11 (12)
C2—C3—C4120.49 (14)C10—C11—C12118.27 (14)
C2—C3—H3119.8C10—C11—H11120.9
C4—C3—H3119.8C12—C11—H11120.9
C5—C4—C3119.12 (14)C11—C12—C13121.30 (14)
C5—C4—H4120.4C11—C12—H12119.4
C3—C4—H4120.4C13—C12—H12119.4
C6—C5—C4120.96 (13)C12—C13—C8119.06 (14)
C6—C5—C14118.67 (13)C12—C13—H13120.5
C4—C5—C14120.35 (13)C8—C13—H13120.5
C5—C6—C1119.70 (13)F1—C14—F3106.86 (13)
C5—C6—H6120.2F1—C14—F2107.23 (14)
C1—C6—H6120.2F3—C14—F2106.11 (13)
O1—C7—N1123.61 (13)F1—C14—C5111.96 (12)
O1—C7—C1121.42 (13)F3—C14—C5112.43 (13)
N1—C7—C1114.96 (12)F2—C14—C5111.86 (12)
C6—C1—C2—C30.8 (2)C7—N1—C8—C1333.9 (2)
C7—C1—C2—C3179.46 (13)C13—C8—C9—C101.0 (2)
C1—C2—C3—C40.4 (2)N1—C8—C9—C10179.48 (13)
C2—C3—C4—C50.8 (2)C8—C9—C10—C111.3 (2)
C3—C4—C5—C60.1 (2)C8—C9—C10—Cl1176.89 (11)
C3—C4—C5—C14178.53 (14)C9—C10—C11—C120.7 (2)
C4—C5—C6—C11.4 (2)Cl1—C10—C11—C12177.47 (12)
C14—C5—C6—C1177.30 (13)C10—C11—C12—C130.2 (2)
C2—C1—C6—C51.7 (2)C11—C12—C13—C80.5 (2)
C7—C1—C6—C5179.58 (12)C9—C8—C13—C120.1 (2)
C8—N1—C7—O18.9 (2)N1—C8—C13—C12179.59 (14)
C8—N1—C7—C1171.58 (13)C6—C5—C14—F141.52 (19)
C2—C1—C7—O1150.27 (14)C4—C5—C14—F1139.80 (15)
C6—C1—C7—O128.4 (2)C6—C5—C14—F3161.84 (14)
C2—C1—C7—N130.2 (2)C4—C5—C14—F319.5 (2)
C6—C1—C7—N1151.19 (13)C6—C5—C14—F278.88 (18)
C7—N1—C8—C9146.62 (15)C4—C5—C14—F299.81 (17)
(PC34) top
Crystal data top
C14H9ClF3NOZ = 2
Mr = 299.67F(000) = 304
Triclinic, P1Dx = 1.570 Mg m3
a = 5.1563 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.7617 (12) ÅCell parameters from 5230 reflections
c = 11.9075 (13) Åθ = 2.8–28.6°
α = 99.948 (6)°µ = 0.33 mm1
β = 91.911 (7)°T = 100 K
γ = 102.379 (7)°Plate
V = 633.98 (12) Å30.50 × 0.10 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2011 reflections with I > 2σ(I)
φ and ω scansRint = 0.041
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 2.4°
Tmin = 0.632, Tmax = 0.746h = 66
7784 measured reflectionsk = 1313
2306 independent reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.140 w = 1/[σ2(Fo2) + (0.0407P)2 + 1.8174P]
where P = (Fo2 + 2Fc2)/3
S = 1.14(Δ/σ)max < 0.001
2306 reflectionsΔρmax = 0.49 e Å3
185 parametersΔρmin = 0.32 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.82299 (17)0.11494 (8)0.17703 (8)0.0212 (2)
F10.9535 (5)0.6791 (2)0.58869 (18)0.0384 (6)
F21.0338 (5)0.8443 (2)0.50582 (19)0.0351 (6)
F30.6310 (5)0.7522 (2)0.5274 (2)0.0405 (7)
O11.0581 (4)0.3513 (2)0.0446 (2)0.0177 (5)
N10.6046 (6)0.3095 (3)0.0226 (2)0.0140 (6)
H10.476 (9)0.333 (4)0.043 (4)0.027 (12)*
C10.8355 (6)0.4648 (3)0.1857 (3)0.0127 (7)
C20.6236 (6)0.4521 (3)0.2559 (3)0.0159 (7)
H20.4709760.3836270.2337470.019*
C30.6340 (7)0.5385 (3)0.3574 (3)0.0180 (7)
H30.4901020.5286110.4052920.022*
C40.8565 (7)0.6400 (3)0.3892 (3)0.0165 (7)
C51.0678 (7)0.6551 (3)0.3192 (3)0.0169 (7)
H51.2181390.7250410.3404630.020*
C61.0573 (6)0.5673 (3)0.2185 (3)0.0145 (7)
H61.2021720.5768130.1711270.017*
C70.8432 (6)0.3706 (3)0.0782 (3)0.0133 (7)
C80.5649 (6)0.2065 (3)0.0741 (3)0.0131 (7)
C90.3749 (6)0.2027 (3)0.1606 (3)0.0170 (7)
H90.2758110.2681940.1555310.020*
C100.3303 (7)0.1019 (3)0.2553 (3)0.0185 (7)
H100.2024980.0997590.3153160.022*
C110.4715 (7)0.0048 (3)0.2622 (3)0.0177 (7)
H110.4424000.0638740.3263940.021*
C120.6555 (6)0.0106 (3)0.1732 (3)0.0153 (7)
C130.7065 (6)0.1101 (3)0.0794 (3)0.0150 (7)
H130.8357950.1123640.0198560.018*
C140.8698 (7)0.7289 (4)0.5016 (3)0.0229 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0229 (4)0.0137 (4)0.0260 (5)0.0065 (3)0.0005 (3)0.0015 (3)
F10.0618 (17)0.0400 (14)0.0153 (11)0.0215 (12)0.0080 (11)0.0001 (10)
F20.0459 (14)0.0223 (11)0.0273 (12)0.0021 (10)0.0020 (11)0.0092 (9)
F30.0305 (13)0.0499 (15)0.0345 (13)0.0177 (11)0.0014 (10)0.0202 (11)
O10.0116 (11)0.0181 (12)0.0215 (13)0.0036 (9)0.0015 (9)0.0018 (10)
N10.0092 (13)0.0157 (14)0.0161 (14)0.0044 (11)0.0009 (11)0.0011 (11)
C10.0133 (15)0.0140 (15)0.0114 (15)0.0049 (12)0.0036 (12)0.0023 (12)
C20.0118 (15)0.0180 (16)0.0161 (16)0.0009 (13)0.0020 (13)0.0014 (13)
C30.0169 (17)0.0215 (17)0.0163 (17)0.0055 (14)0.0014 (13)0.0040 (14)
C40.0175 (16)0.0183 (16)0.0142 (16)0.0073 (13)0.0035 (13)0.0011 (13)
C50.0129 (16)0.0162 (16)0.0190 (17)0.0013 (13)0.0045 (13)0.0002 (13)
C60.0106 (15)0.0162 (16)0.0180 (16)0.0050 (13)0.0004 (13)0.0046 (13)
C70.0117 (15)0.0125 (15)0.0163 (16)0.0028 (12)0.0012 (13)0.0042 (13)
C80.0104 (15)0.0144 (15)0.0130 (16)0.0011 (12)0.0011 (12)0.0006 (12)
C90.0131 (16)0.0160 (16)0.0215 (18)0.0030 (13)0.0002 (13)0.0031 (14)
C100.0171 (17)0.0218 (17)0.0149 (16)0.0038 (14)0.0062 (13)0.0006 (13)
C110.0175 (17)0.0154 (16)0.0166 (17)0.0004 (13)0.0019 (13)0.0023 (13)
C120.0149 (16)0.0133 (15)0.0174 (16)0.0029 (13)0.0038 (13)0.0018 (13)
C130.0121 (15)0.0156 (16)0.0157 (16)0.0017 (13)0.0008 (13)0.0004 (13)
C140.0248 (19)0.0238 (18)0.0187 (18)0.0080 (15)0.0029 (15)0.0025 (15)
Geometric parameters (Å, º) top
Cl1—C121.748 (3)C4—C51.393 (5)
F1—C141.346 (4)C4—C141.495 (5)
F2—C141.336 (4)C5—C61.384 (5)
F3—C141.343 (4)C5—H50.9500
O1—C71.237 (4)C6—H60.9500
N1—C71.354 (4)C8—C131.385 (5)
N1—C81.429 (4)C8—C91.387 (5)
N1—H10.79 (5)C9—C101.398 (5)
C1—C21.395 (5)C9—H90.9500
C1—C61.399 (4)C10—C111.389 (5)
C1—C71.497 (4)C10—H100.9500
C2—C31.384 (5)C11—C121.382 (5)
C2—H20.9500C11—H110.9500
C3—C41.394 (5)C12—C131.383 (4)
C3—H30.9500C13—H130.9500
C7—N1—C8125.1 (3)C13—C8—C9120.8 (3)
C7—N1—H1119 (3)C13—C8—N1120.7 (3)
C8—N1—H1116 (3)C9—C8—N1118.5 (3)
C2—C1—C6119.1 (3)C8—C9—C10119.5 (3)
C2—C1—C7123.2 (3)C8—C9—H9120.3
C6—C1—C7117.7 (3)C10—C9—H9120.3
C3—C2—C1120.5 (3)C11—C10—C9120.5 (3)
C3—C2—H2119.7C11—C10—H10119.8
C1—C2—H2119.7C9—C10—H10119.8
C2—C3—C4119.8 (3)C12—C11—C10118.3 (3)
C2—C3—H3120.1C12—C11—H11120.9
C4—C3—H3120.1C10—C11—H11120.9
C5—C4—C3120.4 (3)C11—C12—C13122.5 (3)
C5—C4—C14120.5 (3)C11—C12—Cl1118.9 (2)
C3—C4—C14119.0 (3)C13—C12—Cl1118.5 (3)
C6—C5—C4119.5 (3)C12—C13—C8118.5 (3)
C6—C5—H5120.3C12—C13—H13120.8
C4—C5—H5120.3C8—C13—H13120.8
C5—C6—C1120.7 (3)F2—C14—F3106.4 (3)
C5—C6—H6119.6F2—C14—F1106.6 (3)
C1—C6—H6119.6F3—C14—F1105.7 (3)
O1—C7—N1123.4 (3)F2—C14—C4113.3 (3)
O1—C7—C1120.6 (3)F3—C14—C4112.3 (3)
N1—C7—C1116.1 (3)F1—C14—C4112.1 (3)
C6—C1—C2—C31.0 (5)C7—N1—C8—C9142.0 (3)
C7—C1—C2—C3176.6 (3)C13—C8—C9—C101.4 (5)
C1—C2—C3—C40.9 (5)N1—C8—C9—C10179.2 (3)
C2—C3—C4—C50.1 (5)C8—C9—C10—C111.1 (5)
C2—C3—C4—C14177.3 (3)C9—C10—C11—C120.2 (5)
C3—C4—C5—C60.9 (5)C10—C11—C12—C131.1 (5)
C14—C4—C5—C6176.4 (3)C10—C11—C12—Cl1176.8 (3)
C4—C5—C6—C10.7 (5)C11—C12—C13—C80.8 (5)
C2—C1—C6—C50.2 (5)Cl1—C12—C13—C8177.1 (2)
C7—C1—C6—C5177.5 (3)C9—C8—C13—C120.4 (5)
C8—N1—C7—O16.8 (5)N1—C8—C13—C12178.2 (3)
C8—N1—C7—C1172.8 (3)C5—C4—C14—F225.1 (5)
C2—C1—C7—O1150.0 (3)C3—C4—C14—F2157.5 (3)
C6—C1—C7—O127.6 (5)C5—C4—C14—F3145.7 (3)
C2—C1—C7—N129.6 (5)C3—C4—C14—F336.9 (5)
C6—C1—C7—N1152.8 (3)C5—C4—C14—F195.5 (4)
C7—N1—C8—C1340.1 (5)C3—C4—C14—F181.8 (4)
(PC42) top
Crystal data top
C14H9ClF3NOF(000) = 1216
Mr = 299.67Dx = 1.468 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.445 (2) ÅCell parameters from 6925 reflections
b = 15.275 (4) Åθ = 3.2–27.8°
c = 18.954 (5) ŵ = 0.31 mm1
β = 97.374 (2)°T = 100 K
V = 2712.1 (11) Å3Plate
Z = 80.50 × 0.15 × 0.09 mm
Data collection top
Bruker APEX-II CCD
diffractometer
4688 reflections with I > 2σ(I)
φ and ω scansRint = 0.037
Absorption correction: multi-scan
SADABS 2014/4
θmax = 27.1°, θmin = 3.2°
Tmin = 0.732, Tmax = 0.846h = 1212
23057 measured reflectionsk = 1819
5971 independent reflectionsl = 2324
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.041P)2 + 1.3716P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
5971 reflectionsΔρmax = 0.43 e Å3
369 parametersΔρmin = 0.46 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.34683 (7)0.11012 (4)0.71366 (3)0.06331 (19)
Cl20.75413 (7)0.59280 (5)0.28556 (3)0.0681 (2)
F10.12423 (18)0.24348 (11)0.33283 (9)0.0875 (5)
F20.3104 (3)0.27688 (11)0.28398 (8)0.1012 (7)
F30.32714 (15)0.19200 (8)0.37344 (6)0.0540 (3)
F40.67108 (13)0.26225 (9)0.66174 (7)0.0552 (3)
F50.87138 (16)0.23809 (9)0.72593 (6)0.0627 (4)
F60.86553 (14)0.31342 (8)0.63018 (7)0.0524 (3)
O10.14589 (12)0.21813 (9)0.49666 (7)0.0375 (3)
O20.64475 (12)0.27228 (9)0.50225 (7)0.0400 (3)
N10.37972 (15)0.21231 (10)0.54368 (8)0.0308 (3)
H10.465 (2)0.2304 (14)0.5371 (11)0.041 (6)*
N20.85904 (16)0.27257 (11)0.45904 (8)0.0338 (3)
H20.945 (2)0.2542 (14)0.4675 (11)0.040 (6)*
C10.29807 (16)0.33328 (11)0.46762 (9)0.0291 (4)
C20.32241 (19)0.40737 (13)0.50986 (11)0.0383 (4)
H2A0.3319010.4017790.5601660.046*
C30.3330 (2)0.48914 (13)0.47979 (13)0.0459 (5)
H30.3463810.5395510.5092480.055*
C40.3242 (2)0.49735 (14)0.40729 (13)0.0483 (5)
H40.3320490.5534730.3865400.058*
C50.3041 (2)0.42426 (14)0.36449 (12)0.0454 (5)
H50.3004300.4302460.3143950.054*
C60.28915 (19)0.34190 (12)0.39385 (10)0.0347 (4)
C70.26764 (17)0.24860 (12)0.50301 (9)0.0286 (4)
C80.36991 (17)0.13503 (12)0.58432 (9)0.0306 (4)
C90.47568 (18)0.07205 (13)0.58538 (9)0.0345 (4)
H90.5522200.0804840.5581010.041*
C100.4708 (2)0.00301 (14)0.62583 (10)0.0401 (4)
H100.5441200.0457700.6270700.048*
C110.3574 (2)0.01490 (14)0.66447 (10)0.0403 (5)
C120.2511 (2)0.04698 (16)0.66355 (9)0.0442 (5)
H120.1735140.0376120.6899570.053*
C130.25742 (19)0.12265 (15)0.62421 (9)0.0407 (5)
H130.1854300.1660650.6243370.049*
C140.2636 (3)0.26448 (15)0.34639 (11)0.0500 (5)
C150.81237 (16)0.16146 (12)0.54332 (9)0.0297 (4)
C160.82947 (19)0.08300 (13)0.50819 (11)0.0397 (4)
H160.8227530.0825580.4577490.048*
C170.85597 (19)0.00589 (13)0.54522 (13)0.0457 (5)
H170.8652950.0473160.5202810.055*
C180.8689 (2)0.00598 (13)0.61830 (13)0.0457 (5)
H180.8862550.0472660.6438500.055*
C190.85671 (19)0.08375 (13)0.65469 (11)0.0406 (4)
H190.8683960.0839290.7052260.049*
C200.82756 (17)0.16111 (12)0.61772 (9)0.0310 (4)
C210.76455 (17)0.24095 (12)0.50036 (9)0.0310 (4)
C220.83324 (18)0.34781 (13)0.41555 (9)0.0337 (4)
C230.93577 (18)0.41324 (13)0.41959 (10)0.0381 (4)
H231.0220920.4065690.4508700.046*
C240.9138 (2)0.48785 (15)0.37875 (10)0.0433 (5)
H240.9844430.5324160.3812480.052*
C250.7862 (2)0.49652 (15)0.33384 (10)0.0457 (5)
C260.6841 (2)0.43167 (17)0.32851 (10)0.0486 (5)
H260.5979300.4385910.2971290.058*
C270.7072 (2)0.35658 (15)0.36890 (10)0.0424 (5)
H270.6378240.3112190.3649640.051*
C280.8095 (2)0.24339 (13)0.65879 (10)0.0408 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0604 (3)0.0677 (4)0.0623 (4)0.0117 (3)0.0096 (3)0.0317 (3)
Cl20.0728 (4)0.0825 (5)0.0495 (3)0.0142 (3)0.0104 (3)0.0368 (3)
F10.0795 (11)0.0794 (11)0.0911 (12)0.0042 (9)0.0365 (9)0.0373 (9)
F20.212 (2)0.0591 (10)0.0398 (8)0.0036 (12)0.0440 (10)0.0031 (7)
F30.0793 (9)0.0353 (7)0.0481 (7)0.0094 (6)0.0104 (6)0.0075 (5)
F40.0518 (7)0.0596 (8)0.0548 (7)0.0105 (6)0.0097 (6)0.0214 (6)
F50.0835 (10)0.0615 (9)0.0373 (6)0.0040 (7)0.0152 (6)0.0118 (6)
F60.0641 (8)0.0318 (6)0.0588 (8)0.0069 (6)0.0015 (6)0.0071 (5)
O10.0235 (6)0.0413 (8)0.0460 (7)0.0002 (5)0.0014 (5)0.0061 (6)
O20.0236 (6)0.0545 (9)0.0430 (7)0.0061 (6)0.0092 (5)0.0083 (6)
N10.0212 (7)0.0397 (9)0.0314 (7)0.0020 (6)0.0025 (6)0.0038 (6)
N20.0213 (7)0.0467 (10)0.0338 (8)0.0034 (7)0.0053 (6)0.0034 (7)
C10.0203 (7)0.0312 (9)0.0351 (9)0.0042 (7)0.0009 (6)0.0036 (7)
C20.0272 (8)0.0388 (11)0.0475 (11)0.0026 (8)0.0001 (7)0.0101 (8)
C30.0315 (9)0.0311 (11)0.0734 (15)0.0028 (8)0.0003 (9)0.0115 (10)
C40.0316 (9)0.0297 (10)0.0836 (17)0.0049 (8)0.0066 (10)0.0100 (10)
C50.0411 (10)0.0440 (12)0.0513 (12)0.0075 (9)0.0068 (9)0.0138 (9)
C60.0339 (9)0.0333 (10)0.0371 (10)0.0054 (8)0.0046 (7)0.0009 (8)
C70.0243 (8)0.0328 (9)0.0284 (8)0.0040 (7)0.0025 (6)0.0035 (7)
C80.0246 (8)0.0414 (10)0.0251 (8)0.0004 (7)0.0002 (6)0.0029 (7)
C90.0230 (8)0.0431 (11)0.0379 (9)0.0019 (7)0.0055 (7)0.0046 (8)
C100.0318 (9)0.0421 (11)0.0458 (11)0.0011 (8)0.0027 (8)0.0085 (9)
C110.0373 (10)0.0506 (12)0.0317 (9)0.0086 (9)0.0013 (7)0.0126 (8)
C120.0327 (9)0.0723 (15)0.0283 (9)0.0022 (9)0.0072 (7)0.0120 (9)
C130.0321 (9)0.0622 (13)0.0286 (9)0.0096 (9)0.0071 (7)0.0072 (9)
C140.0711 (15)0.0443 (12)0.0330 (10)0.0069 (11)0.0007 (10)0.0020 (9)
C150.0177 (7)0.0338 (10)0.0380 (9)0.0031 (7)0.0055 (6)0.0054 (7)
C160.0267 (8)0.0433 (12)0.0509 (11)0.0040 (8)0.0122 (8)0.0160 (9)
C170.0302 (9)0.0322 (11)0.0779 (15)0.0042 (8)0.0190 (9)0.0166 (10)
C180.0317 (9)0.0296 (10)0.0777 (15)0.0008 (8)0.0148 (9)0.0078 (10)
C190.0317 (9)0.0416 (11)0.0487 (11)0.0002 (8)0.0064 (8)0.0049 (9)
C200.0252 (8)0.0304 (9)0.0369 (9)0.0016 (7)0.0015 (7)0.0027 (7)
C210.0232 (8)0.0406 (10)0.0291 (8)0.0017 (7)0.0030 (6)0.0037 (7)
C220.0267 (8)0.0490 (11)0.0262 (8)0.0052 (8)0.0073 (6)0.0027 (8)
C230.0251 (8)0.0519 (12)0.0378 (10)0.0047 (8)0.0061 (7)0.0068 (8)
C240.0366 (10)0.0528 (13)0.0427 (11)0.0026 (9)0.0134 (8)0.0092 (9)
C250.0450 (11)0.0646 (14)0.0293 (9)0.0113 (10)0.0115 (8)0.0170 (9)
C260.0379 (10)0.0795 (16)0.0273 (9)0.0063 (10)0.0005 (8)0.0126 (10)
C270.0325 (9)0.0650 (14)0.0291 (9)0.0011 (9)0.0021 (7)0.0041 (9)
C280.0462 (11)0.0399 (11)0.0337 (10)0.0007 (9)0.0045 (8)0.0058 (8)
Geometric parameters (Å, º) top
Cl1—C111.737 (2)C9—C101.383 (3)
Cl2—C251.738 (2)C9—H90.9500
F1—C141.347 (3)C10—C111.385 (3)
F2—C141.329 (3)C10—H100.9500
F3—C141.330 (2)C11—C121.377 (3)
F4—C281.347 (2)C12—C131.381 (3)
F5—C281.333 (2)C12—H120.9500
F6—C281.339 (2)C13—H130.9500
O1—C71.232 (2)C15—C161.391 (2)
O2—C211.233 (2)C15—C201.399 (2)
N1—C71.346 (2)C15—C211.499 (3)
N1—C81.419 (2)C16—C171.378 (3)
N1—H10.88 (2)C16—H160.9500
N2—C211.350 (2)C17—C181.375 (3)
N2—C221.417 (2)C17—H170.9500
N2—H20.85 (2)C18—C191.386 (3)
C1—C21.388 (2)C18—H180.9500
C1—C61.396 (3)C19—C201.384 (3)
C1—C71.502 (2)C19—H190.9500
C2—C31.382 (3)C20—C281.500 (3)
C2—H2A0.9500C22—C231.387 (3)
C3—C41.372 (3)C22—C271.395 (2)
C3—H30.9500C23—C241.378 (3)
C4—C51.379 (3)C23—H230.9500
C4—H40.9500C24—C251.389 (3)
C5—C61.390 (3)C24—H240.9500
C5—H50.9500C25—C261.378 (3)
C6—C141.487 (3)C26—C271.381 (3)
C8—C91.385 (3)C26—H260.9500
C8—C131.394 (2)C27—H270.9500
C7—N1—C8123.50 (15)F2—C14—C6112.24 (19)
C7—N1—H1117.4 (14)F3—C14—C6113.48 (17)
C8—N1—H1117.7 (14)F1—C14—C6112.56 (18)
C21—N2—C22123.40 (15)C16—C15—C20118.44 (17)
C21—N2—H2117.2 (14)C16—C15—C21118.91 (16)
C22—N2—H2117.6 (14)C20—C15—C21122.37 (15)
C2—C1—C6119.01 (17)C17—C16—C15121.17 (19)
C2—C1—C7118.13 (16)C17—C16—H16119.4
C6—C1—C7122.57 (16)C15—C16—H16119.4
C3—C2—C1120.95 (19)C18—C17—C16119.96 (18)
C3—C2—H2A119.5C18—C17—H17120.0
C1—C2—H2A119.5C16—C17—H17120.0
C4—C3—C2119.84 (19)C17—C18—C19120.00 (19)
C4—C3—H3120.1C17—C18—H18120.0
C2—C3—H3120.1C19—C18—H18120.0
C3—C4—C5120.1 (2)C20—C19—C18120.26 (19)
C3—C4—H4119.9C20—C19—H19119.9
C5—C4—H4119.9C18—C19—H19119.9
C4—C5—C6120.7 (2)C19—C20—C15120.12 (17)
C4—C5—H5119.7C19—C20—C28118.77 (17)
C6—C5—H5119.7C15—C20—C28121.09 (16)
C5—C6—C1119.36 (18)O2—C21—N2123.74 (17)
C5—C6—C14119.63 (18)O2—C21—C15120.81 (15)
C1—C6—C14121.01 (17)N2—C21—C15115.42 (14)
O1—C7—N1123.77 (16)C23—C22—C27119.92 (18)
O1—C7—C1120.76 (15)C23—C22—N2119.05 (16)
N1—C7—C1115.39 (14)C27—C22—N2121.03 (17)
C9—C8—C13119.77 (17)C24—C23—C22120.74 (17)
C9—C8—N1119.23 (15)C24—C23—H23119.6
C13—C8—N1120.99 (16)C22—C23—H23119.6
C10—C9—C8120.56 (16)C23—C24—C25118.6 (2)
C10—C9—H9119.7C23—C24—H24120.7
C8—C9—H9119.7C25—C24—H24120.7
C9—C10—C11119.00 (18)C26—C25—C24121.38 (19)
C9—C10—H10120.5C26—C25—Cl2119.77 (16)
C11—C10—H10120.5C24—C25—Cl2118.83 (18)
C12—C11—C10121.01 (18)C25—C26—C27119.80 (18)
C12—C11—Cl1119.29 (14)C25—C26—H26120.1
C10—C11—Cl1119.69 (16)C27—C26—H26120.1
C11—C12—C13119.96 (17)C26—C27—C22119.51 (19)
C11—C12—H12120.0C26—C27—H27120.2
C13—C12—H12120.0C22—C27—H27120.2
C12—C13—C8119.68 (18)F5—C28—F6106.73 (16)
C12—C13—H13120.2F5—C28—F4106.38 (16)
C8—C13—H13120.2F6—C28—F4106.38 (17)
F2—C14—F3106.06 (19)F5—C28—C20112.33 (17)
F2—C14—F1107.0 (2)F6—C28—C20112.48 (16)
F3—C14—F1104.88 (19)F4—C28—C20112.09 (15)
C6—C1—C2—C32.2 (3)C20—C15—C16—C172.2 (2)
C7—C1—C2—C3171.73 (16)C21—C15—C16—C17171.92 (15)
C1—C2—C3—C42.2 (3)C15—C16—C17—C181.4 (3)
C2—C3—C4—C50.3 (3)C16—C17—C18—C190.6 (3)
C3—C4—C5—C61.5 (3)C17—C18—C19—C201.8 (3)
C4—C5—C6—C11.5 (3)C18—C19—C20—C151.0 (3)
C4—C5—C6—C14178.33 (19)C18—C19—C20—C28177.69 (17)
C2—C1—C6—C50.3 (2)C16—C15—C20—C191.0 (2)
C7—C1—C6—C5173.30 (16)C21—C15—C20—C19172.88 (15)
C2—C1—C6—C14179.85 (17)C16—C15—C20—C28179.61 (16)
C7—C1—C6—C146.5 (3)C21—C15—C20—C285.7 (2)
C8—N1—C7—O10.5 (3)C22—N2—C21—O22.9 (3)
C8—N1—C7—C1176.43 (15)C22—N2—C21—C15179.14 (16)
C2—C1—C7—O1105.81 (19)C16—C15—C21—O2110.57 (19)
C6—C1—C7—O167.8 (2)C20—C15—C21—O263.3 (2)
C2—C1—C7—N171.2 (2)C16—C15—C21—N267.5 (2)
C6—C1—C7—N1115.13 (18)C20—C15—C21—N2118.70 (17)
C7—N1—C8—C9137.60 (17)C21—N2—C22—C23129.81 (18)
C7—N1—C8—C1343.8 (2)C21—N2—C22—C2750.4 (3)
C13—C8—C9—C100.1 (3)C27—C22—C23—C241.0 (3)
N1—C8—C9—C10178.48 (17)N2—C22—C23—C24179.24 (17)
C8—C9—C10—C110.9 (3)C22—C23—C24—C250.5 (3)
C9—C10—C11—C120.5 (3)C23—C24—C25—C261.4 (3)
C9—C10—C11—Cl1178.25 (15)C23—C24—C25—Cl2176.80 (15)
C10—C11—C12—C130.6 (3)C24—C25—C26—C270.6 (3)
Cl1—C11—C12—C13179.44 (15)Cl2—C25—C26—C27177.53 (16)
C11—C12—C13—C81.5 (3)C25—C26—C27—C220.9 (3)
C9—C8—C13—C121.1 (3)C23—C22—C27—C261.8 (3)
N1—C8—C13—C12179.65 (17)N2—C22—C27—C26178.49 (17)
C5—C6—C14—F223.9 (3)C19—C20—C28—F521.8 (2)
C1—C6—C14—F2156.22 (19)C15—C20—C28—F5159.54 (16)
C5—C6—C14—F3144.17 (19)C19—C20—C28—F6142.27 (17)
C1—C6—C14—F336.0 (3)C15—C20—C28—F639.1 (2)
C5—C6—C14—F196.9 (2)C19—C20—C28—F497.90 (19)
C1—C6—C14—F182.9 (2)C15—C20—C28—F480.7 (2)
(PC43) top
Crystal data top
C14H9ClF3NOF(000) = 608
Mr = 299.67Dx = 1.536 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.8325 (10) ÅCell parameters from 8230 reflections
b = 10.3856 (8) Åθ = 2.8–29.7°
c = 9.7379 (8) ŵ = 0.32 mm1
β = 93.059 (3)°T = 104 K
V = 1295.95 (18) Å3Plate
Z = 40.40 × 0.10 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3069 reflections with I > 2σ(I)
φ and ω scansRint = 0.053
Absorption correction: multi-scan
SADABS 2014/4
θmax = 30.1°, θmin = 2.5°
Tmin = 0.732, Tmax = 0.846h = 1817
22891 measured reflectionsk = 1414
3808 independent reflectionsl = 1313
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.6888P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
3808 reflectionsΔρmax = 0.41 e Å3
213 parametersΔρmin = 0.31 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.47179 (3)0.84113 (3)0.44523 (4)0.02897 (11)
F1A0.0221 (3)0.0274 (3)0.8219 (5)0.0627 (11)0.731 (16)
F2A0.0733 (4)0.1363 (7)0.8700 (7)0.0821 (19)0.731 (16)
F3A0.0479 (2)0.1476 (4)0.7131 (6)0.0624 (10)0.731 (16)
F1B0.0368 (8)0.0148 (14)0.8060 (13)0.083 (4)0.269 (16)
F2B0.0860 (10)0.083 (2)0.9013 (14)0.086 (4)0.269 (16)
F3B0.016 (2)0.1807 (17)0.7665 (19)0.099 (7)0.269 (16)
O10.28315 (8)0.29984 (10)0.70997 (10)0.0233 (2)
N10.28617 (9)0.31962 (11)0.47756 (12)0.0185 (2)
H10.2802 (14)0.2804 (19)0.4042 (19)0.026 (5)*
C10.21837 (10)0.12398 (12)0.57572 (13)0.0186 (3)
C20.24188 (13)0.03871 (13)0.47131 (14)0.0259 (3)
H20.2899970.0628950.4051000.031*
C30.19481 (15)0.08178 (14)0.46425 (16)0.0329 (4)
H30.2112180.1398830.3932210.039*
C40.12414 (14)0.11797 (14)0.55988 (17)0.0316 (3)
H40.0913810.1999570.5539520.038*
C50.10177 (11)0.03314 (14)0.66438 (16)0.0257 (3)
C60.14900 (11)0.08690 (13)0.67345 (14)0.0211 (3)
H60.1340240.1437220.7462650.025*
C70.26620 (10)0.25486 (12)0.59350 (13)0.0178 (2)
C80.32898 (10)0.44565 (12)0.47321 (13)0.0176 (2)
C90.39212 (10)0.47530 (13)0.36527 (13)0.0195 (3)
H90.4057190.4116460.2984850.023*
C100.43528 (11)0.59762 (13)0.35491 (14)0.0213 (3)
H100.4780280.6182960.2813190.026*
C120.35114 (11)0.66145 (13)0.56067 (14)0.0216 (3)
H120.3374930.7255480.6269490.026*
C110.41479 (11)0.68865 (13)0.45383 (14)0.0210 (3)
C130.30738 (11)0.53934 (12)0.56998 (14)0.0202 (3)
H130.2629090.5199590.6421320.024*
C140.02873 (14)0.07127 (17)0.7714 (2)0.0388 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0326 (2)0.02148 (17)0.0334 (2)0.00686 (13)0.00789 (15)0.00072 (13)
F1A0.078 (2)0.0400 (14)0.075 (2)0.0159 (15)0.0523 (17)0.0029 (14)
F2A0.0431 (17)0.124 (4)0.080 (3)0.013 (2)0.0130 (16)0.083 (3)
F3A0.0376 (13)0.0609 (15)0.089 (2)0.0250 (10)0.0073 (12)0.0120 (15)
F1B0.038 (4)0.143 (10)0.068 (5)0.053 (5)0.010 (3)0.057 (6)
F2B0.059 (4)0.158 (12)0.042 (4)0.039 (6)0.006 (3)0.047 (6)
F3B0.151 (13)0.071 (7)0.082 (8)0.086 (8)0.053 (9)0.026 (6)
O10.0374 (6)0.0201 (4)0.0125 (4)0.0032 (4)0.0025 (4)0.0000 (3)
N10.0281 (6)0.0156 (5)0.0120 (5)0.0002 (4)0.0018 (4)0.0007 (4)
C10.0244 (6)0.0150 (5)0.0162 (6)0.0012 (5)0.0018 (5)0.0019 (4)
C20.0416 (8)0.0184 (6)0.0178 (6)0.0021 (6)0.0027 (6)0.0014 (5)
C30.0564 (10)0.0166 (6)0.0253 (7)0.0008 (6)0.0018 (7)0.0024 (5)
C40.0424 (9)0.0183 (6)0.0329 (8)0.0046 (6)0.0081 (7)0.0032 (6)
C50.0242 (7)0.0225 (7)0.0299 (7)0.0021 (5)0.0031 (6)0.0069 (5)
C60.0225 (6)0.0199 (6)0.0209 (6)0.0008 (5)0.0003 (5)0.0020 (5)
C70.0222 (6)0.0161 (5)0.0152 (6)0.0020 (5)0.0020 (5)0.0008 (4)
C80.0215 (6)0.0164 (5)0.0150 (6)0.0012 (5)0.0012 (5)0.0021 (4)
C90.0242 (6)0.0212 (6)0.0133 (6)0.0020 (5)0.0020 (5)0.0001 (5)
C100.0231 (6)0.0246 (6)0.0165 (6)0.0003 (5)0.0034 (5)0.0033 (5)
C120.0272 (7)0.0182 (6)0.0196 (6)0.0017 (5)0.0033 (5)0.0013 (5)
C110.0225 (6)0.0179 (6)0.0226 (7)0.0015 (5)0.0014 (5)0.0028 (5)
C130.0257 (7)0.0177 (6)0.0176 (6)0.0012 (5)0.0055 (5)0.0008 (5)
C140.0320 (8)0.0330 (8)0.0520 (11)0.0067 (7)0.0071 (8)0.0127 (8)
Geometric parameters (Å, º) top
Cl1—C111.7483 (14)C3—H30.9500
F1A—C141.323 (4)C4—C51.388 (2)
F2A—C141.283 (4)C4—H40.9500
F3A—C141.363 (4)C5—C61.3869 (19)
F1B—C141.284 (11)C5—C141.492 (2)
F2B—C141.433 (13)C6—H60.9500
F3B—C141.276 (8)C8—C131.3927 (18)
O1—C71.2352 (16)C8—C91.3954 (18)
N1—C71.3504 (16)C9—C101.3916 (19)
N1—C81.4210 (16)C9—H90.9500
N1—H10.823 (19)C10—C111.3849 (19)
C1—C61.3917 (19)C10—H100.9500
C1—C21.3934 (19)C12—C111.3857 (19)
C1—C71.4977 (18)C12—C131.3919 (18)
C2—C31.390 (2)C12—H120.9500
C2—H20.9500C13—H130.9500
C3—C41.386 (2)
C7—N1—C8125.07 (11)C10—C9—C8120.36 (12)
C7—N1—H1117.8 (13)C10—C9—H9119.8
C8—N1—H1116.7 (13)C8—C9—H9119.8
C6—C1—C2119.63 (13)C11—C10—C9118.79 (12)
C6—C1—C7116.44 (12)C11—C10—H10120.6
C2—C1—C7123.90 (12)C9—C10—H10120.6
C3—C2—C1119.86 (14)C11—C12—C13119.39 (12)
C3—C2—H2120.1C11—C12—H12120.3
C1—C2—H2120.1C13—C12—H12120.3
C4—C3—C2120.61 (14)C10—C11—C12121.63 (12)
C4—C3—H3119.7C10—C11—Cl1119.31 (10)
C2—C3—H3119.7C12—C11—Cl1119.05 (11)
C3—C4—C5119.27 (14)C12—C13—C8119.79 (12)
C3—C4—H4120.4C12—C13—H13120.1
C5—C4—H4120.4C8—C13—H13120.1
C6—C5—C4120.70 (14)F3B—C14—F1B109.1 (9)
C6—C5—C14118.87 (15)F2A—C14—F1A109.7 (4)
C4—C5—C14120.40 (14)F2A—C14—F3A106.8 (3)
C5—C6—C1119.90 (13)F1A—C14—F3A104.3 (3)
C5—C6—H6120.1F3B—C14—F2B99.6 (9)
C1—C6—H6120.1F1B—C14—F2B98.1 (9)
O1—C7—N1123.19 (12)F3B—C14—C5120.8 (5)
O1—C7—C1120.03 (11)F2A—C14—C5113.0 (2)
N1—C7—C1116.76 (11)F1B—C14—C5116.3 (5)
C13—C8—C9120.01 (12)F1A—C14—C5113.23 (19)
C13—C8—N1122.15 (12)F3A—C14—C5109.2 (3)
C9—C8—N1117.82 (11)F2B—C14—C5109.1 (5)
C6—C1—C2—C31.0 (2)C8—C9—C10—C110.3 (2)
C7—C1—C2—C3178.95 (14)C9—C10—C11—C121.2 (2)
C1—C2—C3—C40.3 (2)C9—C10—C11—Cl1178.00 (10)
C2—C3—C4—C50.9 (2)C13—C12—C11—C100.7 (2)
C3—C4—C5—C60.2 (2)C13—C12—C11—Cl1178.55 (11)
C3—C4—C5—C14177.95 (15)C11—C12—C13—C80.8 (2)
C4—C5—C6—C11.0 (2)C9—C8—C13—C121.7 (2)
C14—C5—C6—C1179.24 (13)N1—C8—C13—C12179.80 (12)
C2—C1—C6—C51.6 (2)C6—C5—C14—F3B179.8 (18)
C7—C1—C6—C5179.75 (12)C4—C5—C14—F3B2.0 (18)
C8—N1—C7—O10.3 (2)C6—C5—C14—F2A94.3 (5)
C8—N1—C7—C1178.49 (12)C4—C5—C14—F2A83.9 (5)
C6—C1—C7—O131.87 (18)C6—C5—C14—F1B43.9 (8)
C2—C1—C7—O1146.16 (14)C4—C5—C14—F1B137.9 (8)
C6—C1—C7—N1146.40 (12)C6—C5—C14—F1A31.3 (3)
C2—C1—C7—N135.57 (19)C4—C5—C14—F1A150.5 (3)
C7—N1—C8—C1333.6 (2)C6—C5—C14—F3A147.0 (2)
C7—N1—C8—C9148.22 (13)C4—C5—C14—F3A34.8 (3)
C13—C8—C9—C101.1 (2)C6—C5—C14—F2B65.8 (9)
N1—C8—C9—C10179.32 (12)C4—C5—C14—F2B112.4 (9)
(PC44) top
Crystal data top
C14H9ClF3NOF(000) = 1216
Mr = 299.67Dx = 1.561 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.952 (3) ÅCell parameters from 7877 reflections
b = 5.2521 (7) Åθ = 2.4–29.7°
c = 28.760 (4) ŵ = 0.33 mm1
β = 94.966 (4)°T = 105 K
V = 2551.0 (6) Å3Rod
Z = 80.20 × 0.15 × 0.05 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3328 reflections with I > 2σ(I)
φ and ω scansRint = 0.062
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 2.8°
Tmin = 0.732, Tmax = 0.886h = 1920
27880 measured reflectionsk = 65
4740 independent reflectionsl = 3434
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0493P)2 + 1.8012P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4740 reflectionsΔρmax = 0.46 e Å3
369 parametersΔρmin = 0.29 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl11.04844 (4)0.08654 (14)0.39245 (2)0.02630 (19)
Cl20.45825 (4)0.75139 (14)0.10845 (2)0.02710 (19)
F10.67040 (11)0.2072 (4)0.01944 (5)0.0597 (6)
F20.56142 (11)0.2655 (5)0.01011 (6)0.0650 (7)
F30.61162 (12)0.1033 (4)0.00816 (6)0.0609 (6)
F40.88668 (10)0.5006 (4)0.51202 (5)0.0434 (5)
F50.84460 (10)0.8824 (3)0.51208 (5)0.0420 (5)
F60.94895 (10)0.7888 (5)0.47824 (6)0.0598 (6)
O10.81495 (10)0.5475 (3)0.20729 (5)0.0204 (4)
O20.68523 (10)0.2883 (3)0.29629 (5)0.0198 (4)
N10.83508 (12)0.1204 (4)0.21764 (7)0.0154 (5)
H10.8190 (15)0.033 (6)0.2074 (9)0.031 (8)*
N20.66492 (12)0.7152 (4)0.28583 (7)0.0162 (5)
H20.6811 (15)0.859 (6)0.2960 (8)0.023 (8)*
C10.76014 (14)0.2681 (5)0.14753 (8)0.0157 (5)
C20.77626 (14)0.0580 (5)0.12032 (8)0.0195 (6)
H2A0.8168540.0580010.1310170.023*
C30.73344 (15)0.0175 (5)0.07783 (8)0.0222 (6)
H30.7447560.1256800.0593600.027*
C40.67384 (15)0.1865 (5)0.06214 (8)0.0208 (6)
C50.65705 (15)0.3972 (5)0.08902 (8)0.0209 (6)
H50.6161210.5120500.0783500.025*
C60.70048 (14)0.4381 (5)0.13143 (8)0.0178 (6)
H60.6896440.5827220.1496770.021*
C70.80563 (14)0.3276 (5)0.19334 (8)0.0162 (6)
C80.88408 (14)0.1265 (5)0.26036 (8)0.0154 (5)
C90.87932 (14)0.0773 (5)0.29109 (8)0.0165 (5)
H90.8415150.2083750.2841400.020*
C100.92959 (14)0.0894 (5)0.33179 (8)0.0178 (6)
H100.9263680.2283860.3526900.021*
C110.98459 (14)0.1031 (5)0.34170 (8)0.0165 (6)
C120.98927 (14)0.3067 (5)0.31169 (8)0.0175 (6)
H121.0266960.4385310.3189640.021*
C130.93899 (14)0.3189 (5)0.27070 (8)0.0163 (6)
H130.9423300.4583040.2499210.020*
C140.62877 (16)0.1410 (6)0.01563 (9)0.0272 (7)
C150.73971 (14)0.5687 (5)0.35608 (8)0.0158 (5)
C160.72249 (15)0.7757 (5)0.38333 (8)0.0201 (6)
H160.6807810.8883790.3729690.024*
C170.76612 (15)0.8189 (5)0.42578 (8)0.0220 (6)
H170.7537640.9599960.4445000.026*
C180.82749 (14)0.6569 (5)0.44087 (8)0.0196 (6)
C190.84536 (14)0.4489 (5)0.41392 (8)0.0202 (6)
H190.8876940.3383460.4241940.024*
C200.80095 (14)0.4032 (5)0.37182 (8)0.0186 (6)
H200.8122530.2587510.3536430.022*
C210.69442 (14)0.5087 (5)0.31037 (8)0.0157 (5)
C220.61726 (14)0.7101 (5)0.24272 (8)0.0155 (5)
C230.62281 (14)0.9148 (5)0.21215 (8)0.0166 (5)
H230.6601631.0464660.2196900.020*
C240.57443 (14)0.9270 (5)0.17109 (8)0.0180 (6)
H240.5784921.0662860.1503510.022*
C250.51998 (14)0.7352 (5)0.16030 (8)0.0173 (6)
C260.51412 (14)0.5294 (5)0.18999 (8)0.0160 (5)
H260.4770220.3975370.1820810.019*
C270.56275 (13)0.5171 (5)0.23133 (8)0.0152 (5)
H270.5588000.3767740.2518540.018*
C280.87694 (17)0.7076 (6)0.48559 (9)0.0276 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0260 (4)0.0322 (4)0.0195 (3)0.0030 (3)0.0050 (3)0.0025 (3)
Cl20.0273 (4)0.0327 (4)0.0200 (3)0.0017 (3)0.0052 (3)0.0033 (3)
F10.0606 (13)0.1000 (18)0.0175 (8)0.0368 (12)0.0013 (8)0.0086 (10)
F20.0490 (12)0.0953 (18)0.0455 (11)0.0285 (12)0.0254 (9)0.0251 (11)
F30.0919 (16)0.0411 (13)0.0430 (11)0.0271 (11)0.0333 (10)0.0041 (9)
F40.0599 (12)0.0399 (11)0.0270 (9)0.0068 (9)0.0150 (8)0.0035 (8)
F50.0584 (12)0.0394 (11)0.0256 (9)0.0057 (9)0.0110 (8)0.0109 (8)
F60.0360 (11)0.1094 (19)0.0328 (10)0.0352 (11)0.0033 (8)0.0087 (10)
O10.0246 (10)0.0116 (11)0.0239 (9)0.0020 (8)0.0042 (8)0.0022 (7)
O20.0234 (10)0.0131 (11)0.0219 (9)0.0018 (8)0.0046 (8)0.0024 (7)
N10.0171 (11)0.0118 (12)0.0169 (11)0.0014 (9)0.0007 (9)0.0019 (9)
N20.0178 (12)0.0106 (12)0.0197 (11)0.0019 (9)0.0008 (9)0.0015 (9)
C10.0149 (13)0.0151 (14)0.0175 (12)0.0043 (11)0.0027 (10)0.0000 (11)
C20.0172 (13)0.0182 (15)0.0231 (13)0.0020 (11)0.0021 (11)0.0004 (11)
C30.0260 (15)0.0205 (15)0.0207 (13)0.0012 (12)0.0053 (11)0.0035 (11)
C40.0227 (14)0.0227 (16)0.0174 (13)0.0063 (12)0.0033 (11)0.0029 (11)
C50.0194 (14)0.0192 (15)0.0237 (13)0.0002 (12)0.0004 (11)0.0057 (11)
C60.0192 (13)0.0133 (14)0.0212 (13)0.0006 (11)0.0037 (10)0.0025 (10)
C70.0129 (13)0.0155 (15)0.0208 (13)0.0003 (11)0.0054 (10)0.0019 (11)
C80.0148 (13)0.0158 (14)0.0159 (12)0.0035 (11)0.0030 (10)0.0038 (10)
C90.0171 (13)0.0105 (14)0.0225 (13)0.0013 (11)0.0045 (10)0.0031 (10)
C100.0229 (14)0.0137 (14)0.0176 (12)0.0012 (12)0.0058 (10)0.0018 (10)
C110.0158 (13)0.0176 (15)0.0164 (12)0.0026 (11)0.0031 (10)0.0007 (10)
C120.0134 (13)0.0165 (14)0.0228 (13)0.0007 (11)0.0031 (10)0.0039 (11)
C130.0173 (13)0.0145 (14)0.0176 (12)0.0014 (11)0.0046 (10)0.0006 (10)
C140.0293 (16)0.0290 (18)0.0229 (14)0.0088 (14)0.0005 (12)0.0024 (12)
C150.0153 (13)0.0139 (14)0.0181 (12)0.0033 (11)0.0013 (10)0.0017 (10)
C160.0233 (14)0.0171 (15)0.0196 (13)0.0038 (12)0.0007 (11)0.0001 (11)
C170.0259 (15)0.0188 (15)0.0218 (14)0.0012 (12)0.0042 (11)0.0043 (11)
C180.0205 (14)0.0205 (15)0.0180 (13)0.0054 (12)0.0032 (11)0.0025 (11)
C190.0171 (13)0.0214 (16)0.0220 (13)0.0014 (12)0.0003 (11)0.0038 (11)
C200.0222 (14)0.0143 (14)0.0196 (13)0.0002 (11)0.0041 (11)0.0005 (10)
C210.0148 (13)0.0135 (14)0.0192 (12)0.0011 (11)0.0036 (10)0.0004 (11)
C220.0136 (13)0.0160 (14)0.0171 (12)0.0025 (11)0.0025 (10)0.0037 (10)
C230.0174 (13)0.0113 (14)0.0216 (13)0.0003 (11)0.0044 (10)0.0024 (10)
C240.0210 (14)0.0157 (14)0.0178 (12)0.0014 (12)0.0051 (10)0.0015 (11)
C250.0164 (13)0.0209 (15)0.0147 (12)0.0031 (11)0.0019 (10)0.0021 (11)
C260.0131 (13)0.0140 (14)0.0210 (13)0.0010 (10)0.0022 (10)0.0025 (10)
C270.0162 (13)0.0108 (13)0.0192 (12)0.0016 (10)0.0048 (10)0.0019 (10)
C280.0325 (17)0.0312 (18)0.0190 (14)0.0050 (14)0.0007 (12)0.0020 (13)
Geometric parameters (Å, º) top
Cl1—C111.742 (2)C9—C101.388 (3)
Cl2—C251.748 (2)C9—H90.9500
F1—C141.326 (3)C10—C111.388 (3)
F2—C141.314 (3)C10—H100.9500
F3—C141.329 (3)C11—C121.381 (3)
F4—C281.329 (3)C12—C131.395 (3)
F5—C281.340 (3)C12—H120.9500
F6—C281.327 (3)C13—H130.9500
O1—C71.228 (3)C15—C161.386 (3)
O2—C211.232 (3)C15—C201.399 (3)
N1—C71.364 (3)C15—C211.497 (3)
N1—C81.422 (3)C16—C171.390 (3)
N1—H10.89 (3)C16—H160.9500
N2—C211.365 (3)C17—C181.384 (4)
N2—C221.420 (3)C17—H170.9500
N2—H20.85 (3)C18—C191.388 (4)
C1—C21.393 (3)C18—C281.497 (3)
C1—C61.398 (3)C19—C201.390 (3)
C1—C71.501 (3)C19—H190.9500
C2—C31.383 (3)C20—H200.9500
C2—H2A0.9500C22—C271.391 (3)
C3—C41.390 (4)C22—C231.397 (3)
C3—H30.9500C23—C241.380 (3)
C4—C51.394 (4)C23—H230.9500
C4—C141.501 (3)C24—C251.383 (3)
C5—C61.386 (3)C24—H240.9500
C5—H50.9500C25—C261.386 (3)
C6—H60.9500C26—C271.389 (3)
C8—C131.388 (3)C26—H260.9500
C8—C91.395 (3)C27—H270.9500
C7—N1—C8125.8 (2)F2—C14—C4113.5 (2)
C7—N1—H1117.6 (17)F1—C14—C4111.9 (2)
C8—N1—H1116.4 (17)F3—C14—C4112.6 (2)
C21—N2—C22126.3 (2)C16—C15—C20119.4 (2)
C21—N2—H2116.0 (18)C16—C15—C21123.0 (2)
C22—N2—H2117.3 (18)C20—C15—C21117.6 (2)
C2—C1—C6119.4 (2)C15—C16—C17120.2 (2)
C2—C1—C7123.2 (2)C15—C16—H16119.9
C6—C1—C7117.4 (2)C17—C16—H16119.9
C3—C2—C1120.3 (2)C18—C17—C16120.2 (2)
C3—C2—H2A119.9C18—C17—H17119.9
C1—C2—H2A119.9C16—C17—H17119.9
C2—C3—C4120.0 (2)C17—C18—C19120.2 (2)
C2—C3—H3120.0C17—C18—C28120.7 (2)
C4—C3—H3120.0C19—C18—C28119.1 (2)
C3—C4—C5120.3 (2)C18—C19—C20119.6 (2)
C3—C4—C14119.2 (2)C18—C19—H19120.2
C5—C4—C14120.5 (2)C20—C19—H19120.2
C6—C5—C4119.5 (2)C19—C20—C15120.4 (2)
C6—C5—H5120.2C19—C20—H20119.8
C4—C5—H5120.2C15—C20—H20119.8
C5—C6—C1120.4 (2)O2—C21—N2123.1 (2)
C5—C6—H6119.8O2—C21—C15121.8 (2)
C1—C6—H6119.8N2—C21—C15115.1 (2)
O1—C7—N1123.5 (2)C27—C22—C23119.5 (2)
O1—C7—C1121.6 (2)C27—C22—N2122.4 (2)
N1—C7—C1114.9 (2)C23—C22—N2118.1 (2)
C13—C8—C9119.8 (2)C24—C23—C22120.5 (2)
C13—C8—N1122.1 (2)C24—C23—H23119.8
C9—C8—N1117.9 (2)C22—C23—H23119.8
C10—C9—C8120.3 (2)C23—C24—C25119.6 (2)
C10—C9—H9119.8C23—C24—H24120.2
C8—C9—H9119.8C25—C24—H24120.2
C11—C10—C9119.5 (2)C24—C25—C26120.8 (2)
C11—C10—H10120.3C24—C25—Cl2119.62 (19)
C9—C10—H10120.3C26—C25—Cl2119.60 (19)
C12—C11—C10120.6 (2)C25—C26—C27119.7 (2)
C12—C11—Cl1119.81 (19)C25—C26—H26120.2
C10—C11—Cl1119.54 (19)C27—C26—H26120.2
C11—C12—C13120.0 (2)C26—C27—C22120.0 (2)
C11—C12—H12120.0C26—C27—H27120.0
C13—C12—H12120.0C22—C27—H27120.0
C8—C13—C12119.8 (2)F6—C28—F4106.5 (2)
C8—C13—H13120.1F6—C28—F5107.3 (2)
C12—C13—H13120.1F4—C28—F5105.8 (2)
F2—C14—F1107.0 (2)F6—C28—C18112.0 (2)
F2—C14—F3106.6 (2)F4—C28—C18112.2 (2)
F1—C14—F3104.7 (2)F5—C28—C18112.6 (2)
C6—C1—C2—C30.2 (4)C20—C15—C16—C170.4 (4)
C7—C1—C2—C3178.3 (2)C21—C15—C16—C17179.1 (2)
C1—C2—C3—C40.2 (4)C15—C16—C17—C180.7 (4)
C2—C3—C4—C50.1 (4)C16—C17—C18—C190.7 (4)
C2—C3—C4—C14179.2 (2)C16—C17—C18—C28177.5 (2)
C3—C4—C5—C60.3 (4)C17—C18—C19—C200.4 (4)
C14—C4—C5—C6178.7 (2)C28—C18—C19—C20178.6 (2)
C4—C5—C6—C10.8 (4)C18—C19—C20—C151.4 (4)
C2—C1—C6—C50.7 (4)C16—C15—C20—C191.4 (4)
C7—C1—C6—C5178.9 (2)C21—C15—C20—C19179.8 (2)
C8—N1—C7—O14.1 (4)C22—N2—C21—O23.2 (4)
C8—N1—C7—C1175.9 (2)C22—N2—C21—C15177.1 (2)
C2—C1—C7—O1149.7 (2)C16—C15—C21—O2148.7 (2)
C6—C1—C7—O128.5 (3)C20—C15—C21—O230.0 (3)
C2—C1—C7—N130.4 (3)C16—C15—C21—N231.6 (3)
C6—C1—C7—N1151.5 (2)C20—C15—C21—N2149.7 (2)
C7—N1—C8—C1333.5 (3)C21—N2—C22—C2733.5 (4)
C7—N1—C8—C9150.5 (2)C21—N2—C22—C23150.1 (2)
C13—C8—C9—C100.4 (3)C27—C22—C23—C240.4 (3)
N1—C8—C9—C10175.7 (2)N2—C22—C23—C24176.1 (2)
C8—C9—C10—C110.1 (3)C22—C23—C24—C250.2 (4)
C9—C10—C11—C120.5 (4)C23—C24—C25—C260.8 (4)
C9—C10—C11—Cl1179.32 (18)C23—C24—C25—Cl2179.62 (18)
C10—C11—C12—C130.7 (4)C24—C25—C26—C270.8 (4)
Cl1—C11—C12—C13179.10 (18)Cl2—C25—C26—C27179.58 (18)
C9—C8—C13—C120.2 (3)C25—C26—C27—C220.3 (3)
N1—C8—C13—C12175.7 (2)C23—C22—C27—C260.3 (3)
C11—C12—C13—C80.4 (3)N2—C22—C27—C26176.0 (2)
C3—C4—C14—F2162.2 (2)C17—C18—C28—F6107.4 (3)
C5—C4—C14—F218.7 (4)C19—C18—C28—F670.8 (3)
C3—C4—C14—F176.7 (3)C17—C18—C28—F4132.9 (3)
C5—C4—C14—F1102.4 (3)C19—C18—C28—F448.9 (3)
C3—C4—C14—F341.0 (3)C17—C18—C28—F513.7 (4)
C5—C4—C14—F3140.0 (3)C19—C18—C28—F5168.1 (2)
(PB23) top
Crystal data top
C14H9BrF3NOF(000) = 680
Mr = 344.13Dx = 1.734 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.7992 (3) ÅCell parameters from 9972 reflections
b = 10.0208 (7) Åθ = 2.2–30.5°
c = 27.428 (2) ŵ = 3.15 mm1
β = 91.755 (2)°T = 100 K
V = 1318.47 (16) Å3Plate
Z = 40.21 × 0.16 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3558 reflections with I > 2σ(I)
φ and ω scansRint = 0.031
Absorption correction: multi-scan
SADABS 2014/4
θmax = 30.5°, θmin = 2.5°
Tmin = 0.457, Tmax = 0.704h = 66
28180 measured reflectionsk = 1414
4008 independent reflectionsl = 3939
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.0294P)2 + 0.8053P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.007
4008 reflectionsΔρmax = 0.50 e Å3
213 parametersΔρmin = 0.37 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.5804 (6)0.3439 (7)0.75200 (18)0.091 (3)0.512 (5)
F2A0.9044 (14)0.4796 (4)0.76602 (13)0.085 (2)0.512 (5)
F3A0.9703 (8)0.3162 (4)0.72128 (9)0.0645 (13)0.512 (5)
F1B0.9792 (7)0.4308 (6)0.7450 (2)0.095 (3)0.488 (5)
F3B0.5869 (8)0.4334 (4)0.77547 (12)0.0588 (11)0.488 (5)
F2B0.6950 (13)0.2746 (4)0.73073 (13)0.086 (2)0.488 (5)
Br11.34389 (3)0.07890 (2)1.04678 (2)0.02188 (5)
O10.5916 (2)0.31174 (11)0.94761 (4)0.0217 (2)
N11.0295 (2)0.27459 (12)0.97965 (4)0.0145 (2)
H11.196 (4)0.2635 (19)0.9721 (7)0.020 (4)*
C10.9421 (3)0.24304 (13)0.89356 (5)0.0153 (2)
C21.1314 (3)0.13949 (15)0.88779 (5)0.0200 (3)
H21.2034290.0931210.9156350.024*
C31.2158 (4)0.10338 (17)0.84162 (6)0.0274 (3)
H31.3423600.0314620.8378940.033*
C41.1149 (3)0.17257 (17)0.80092 (5)0.0264 (3)
H41.1734930.1490190.7692840.032*
C50.9279 (3)0.27641 (16)0.80688 (5)0.0236 (3)
C60.8370 (3)0.31078 (15)0.85268 (5)0.0203 (3)
H60.7039590.3800620.8561520.024*
C70.8370 (3)0.28013 (13)0.94261 (5)0.0151 (2)
C80.9744 (3)0.29759 (13)1.02944 (5)0.0143 (2)
C91.1030 (3)0.21833 (13)1.06533 (5)0.0162 (2)
C101.0573 (3)0.23758 (16)1.11438 (5)0.0234 (3)
H101.1475250.1826261.1382570.028*
C110.8774 (4)0.33845 (17)1.12822 (6)0.0279 (3)
H110.8421210.3522321.1617360.033*
C120.7499 (3)0.41880 (16)1.09309 (6)0.0257 (3)
H120.6278140.4879571.1027180.031*
C130.7981 (3)0.39950 (14)1.04398 (5)0.0192 (3)
H130.7108040.4559191.0202450.023*
C140.8240 (4)0.3535 (2)0.76328 (6)0.0366 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0210 (14)0.167 (6)0.083 (4)0.023 (2)0.0202 (17)0.095 (4)
F2A0.182 (6)0.0350 (16)0.0357 (18)0.018 (2)0.037 (2)0.0163 (13)
F3A0.086 (3)0.090 (3)0.0176 (11)0.036 (2)0.0048 (12)0.0104 (13)
F1B0.0328 (17)0.153 (7)0.098 (4)0.028 (3)0.008 (2)0.106 (5)
F3B0.067 (2)0.080 (3)0.0293 (15)0.0335 (19)0.0058 (13)0.0221 (15)
F2B0.143 (6)0.075 (2)0.0351 (18)0.010 (3)0.050 (3)0.0062 (16)
Br10.02176 (8)0.02048 (8)0.02343 (8)0.00966 (5)0.00117 (5)0.00318 (5)
O10.0107 (4)0.0321 (6)0.0224 (5)0.0037 (4)0.0012 (4)0.0013 (4)
N10.0102 (5)0.0187 (5)0.0148 (5)0.0033 (4)0.0023 (4)0.0005 (4)
C10.0125 (6)0.0178 (6)0.0155 (6)0.0004 (5)0.0000 (4)0.0007 (5)
C20.0206 (7)0.0211 (7)0.0184 (6)0.0046 (5)0.0001 (5)0.0001 (5)
C30.0306 (8)0.0289 (8)0.0228 (7)0.0074 (6)0.0039 (6)0.0063 (6)
C40.0316 (8)0.0302 (8)0.0177 (7)0.0051 (6)0.0033 (6)0.0047 (6)
C50.0278 (8)0.0255 (7)0.0172 (6)0.0062 (6)0.0048 (5)0.0035 (5)
C60.0190 (7)0.0220 (7)0.0197 (6)0.0019 (5)0.0023 (5)0.0031 (5)
C70.0133 (6)0.0150 (6)0.0169 (6)0.0014 (4)0.0010 (4)0.0034 (4)
C80.0127 (6)0.0149 (6)0.0154 (6)0.0003 (4)0.0018 (4)0.0000 (4)
C90.0147 (6)0.0154 (6)0.0187 (6)0.0028 (5)0.0009 (5)0.0003 (5)
C100.0274 (8)0.0252 (7)0.0177 (6)0.0028 (6)0.0003 (5)0.0013 (5)
C110.0340 (9)0.0322 (8)0.0176 (7)0.0038 (7)0.0059 (6)0.0045 (6)
C120.0273 (8)0.0247 (7)0.0254 (7)0.0069 (6)0.0070 (6)0.0066 (6)
C130.0178 (6)0.0180 (6)0.0219 (7)0.0043 (5)0.0027 (5)0.0000 (5)
C140.0491 (11)0.0399 (10)0.0203 (7)0.0022 (8)0.0061 (7)0.0073 (7)
Geometric parameters (Å, º) top
F1A—C141.204 (3)C3—H30.9500
F2A—C141.322 (4)C4—C51.387 (2)
F3A—C141.418 (3)C4—H40.9500
F1B—C141.195 (4)C5—C61.386 (2)
F3B—C141.439 (4)C5—C141.496 (2)
F2B—C141.331 (4)C6—H60.9500
Br1—C91.8929 (13)C8—C131.3922 (18)
O1—C71.2313 (16)C8—C91.3944 (18)
N1—C71.3531 (17)C9—C101.3831 (19)
N1—C81.4176 (16)C10—C111.390 (2)
N1—H10.840 (19)C10—H100.9500
C1—C21.3912 (19)C11—C121.384 (2)
C1—C61.3921 (18)C11—H110.9500
C1—C71.4982 (18)C12—C131.387 (2)
C2—C31.390 (2)C12—H120.9500
C2—H20.9500C13—H130.9500
C3—C41.389 (2)
C7—N1—C8124.99 (11)C10—C9—C8121.82 (13)
C7—N1—H1117.1 (13)C10—C9—Br1118.74 (10)
C8—N1—H1117.7 (13)C8—C9—Br1119.44 (10)
C2—C1—C6119.59 (13)C9—C10—C11119.05 (14)
C2—C1—C7121.75 (12)C9—C10—H10120.5
C6—C1—C7118.60 (12)C11—C10—H10120.5
C3—C2—C1120.50 (14)C12—C11—C10119.88 (14)
C3—C2—H2119.8C12—C11—H11120.1
C1—C2—H2119.8C10—C11—H11120.1
C4—C3—C2119.90 (15)C11—C12—C13120.75 (14)
C4—C3—H3120.0C11—C12—H12119.6
C2—C3—H3120.0C13—C12—H12119.6
C5—C4—C3119.39 (14)C12—C13—C8120.10 (13)
C5—C4—H4120.3C12—C13—H13119.9
C3—C4—H4120.3C8—C13—H13119.9
C6—C5—C4121.06 (14)F1A—C14—F2A111.7 (4)
C6—C5—C14119.32 (15)F1B—C14—F2B112.7 (4)
C4—C5—C14119.61 (15)F1A—C14—F3A105.7 (3)
C5—C6—C1119.52 (14)F2A—C14—F3A98.5 (3)
C5—C6—H6120.2F1B—C14—F3B104.1 (4)
C1—C6—H6120.2F2B—C14—F3B97.6 (3)
O1—C7—N1124.08 (12)F1B—C14—C5118.2 (2)
O1—C7—C1120.88 (12)F1A—C14—C5117.5 (2)
N1—C7—C1115.03 (11)F2A—C14—C5111.0 (2)
C13—C8—C9118.37 (12)F2B—C14—C5111.5 (2)
C13—C8—N1121.89 (12)F3A—C14—C5110.62 (19)
C9—C8—N1119.73 (12)F3B—C14—C5110.38 (18)
C6—C1—C2—C30.0 (2)N1—C8—C9—Br11.22 (18)
C7—C1—C2—C3177.11 (14)C8—C9—C10—C110.2 (2)
C1—C2—C3—C41.2 (2)Br1—C9—C10—C11179.04 (12)
C2—C3—C4—C50.7 (3)C9—C10—C11—C120.8 (3)
C3—C4—C5—C61.0 (2)C10—C11—C12—C130.3 (3)
C3—C4—C5—C14178.48 (16)C11—C12—C13—C80.7 (2)
C4—C5—C6—C12.2 (2)C9—C8—C13—C121.2 (2)
C14—C5—C6—C1177.29 (15)N1—C8—C13—C12179.94 (14)
C2—C1—C6—C51.7 (2)C6—C5—C14—F1B105.5 (5)
C7—C1—C6—C5178.87 (13)C4—C5—C14—F1B74.0 (5)
C8—N1—C7—O13.3 (2)C6—C5—C14—F1A66.9 (5)
C8—N1—C7—C1176.09 (12)C4—C5—C14—F1A113.6 (5)
C2—C1—C7—O1140.66 (14)C6—C5—C14—F2A63.4 (4)
C6—C1—C7—O136.5 (2)C4—C5—C14—F2A116.1 (4)
C2—C1—C7—N138.75 (19)C6—C5—C14—F2B121.5 (4)
C6—C1—C7—N1144.11 (13)C4—C5—C14—F2B59.0 (4)
C7—N1—C8—C1341.1 (2)C6—C5—C14—F3A171.6 (3)
C7—N1—C8—C9140.20 (14)C4—C5—C14—F3A7.9 (3)
C13—C8—C9—C100.8 (2)C6—C5—C14—F3B14.2 (3)
N1—C8—C9—C10179.55 (13)C4—C5—C14—F3B166.3 (3)
C13—C8—C9—Br1180.00 (10)
(PB24) top
Crystal data top
C14H9BrF3NOF(000) = 680
Mr = 344.13Dx = 1.739 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.8056 (2) ÅCell parameters from 5637 reflections
b = 27.8678 (10) Åθ = 2.9–29.3°
c = 9.8421 (4) ŵ = 3.16 mm1
β = 94.227 (3)°T = 100 K
V = 1314.48 (9) Å3Plate
Z = 40.32 × 0.24 × 0.13 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2227 reflections with I > 2σ(I)
φ and ω scansRint = 0.037
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 2.2°
Tmin = 0.512, Tmax = 0.652h = 55
10604 measured reflectionsk = 3333
2435 independent reflectionsl = 1111
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073 w = 1/[σ2(Fo2) + (0.0183P)2 + 2.2721P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
2435 reflectionsΔρmax = 0.42 e Å3
201 parametersΔρmin = 0.62 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.83208 (6)0.04414 (2)0.58176 (3)0.01617 (11)
F1A0.9662 (12)0.2501 (2)0.5747 (10)0.0374 (14)0.77 (2)
F2A0.5425 (12)0.2683 (2)0.5312 (11)0.0495 (18)0.77 (2)
F3A0.692 (3)0.2809 (2)0.7353 (8)0.081 (3)0.77 (2)
F1B0.960 (5)0.2533 (8)0.624 (2)0.0374 (14)0.23 (2)
F2B0.560 (5)0.2732 (9)0.586 (3)0.0495 (18)0.23 (2)
F3B0.852 (4)0.2701 (6)0.7548 (14)0.034 (4)0.23 (2)
O10.1090 (4)0.05494 (7)0.8079 (2)0.0179 (4)
N10.5344 (5)0.02318 (8)0.7721 (2)0.0112 (5)
H10.705 (4)0.0308 (12)0.761 (3)0.024 (9)*
C110.3640 (6)0.12293 (10)0.8386 (3)0.0196 (6)
H110.3264320.1558790.8539300.024*
C100.5409 (6)0.10978 (10)0.7397 (3)0.0179 (6)
H100.6243020.1334960.6865320.021*
C90.5939 (6)0.06162 (10)0.7198 (3)0.0130 (6)
C80.4735 (5)0.02570 (10)0.7950 (3)0.0110 (5)
C70.3511 (6)0.05959 (10)0.7770 (3)0.0111 (5)
C10.4577 (6)0.10824 (10)0.7405 (3)0.0122 (6)
C20.6445 (6)0.11450 (10)0.6402 (3)0.0159 (6)
H20.7130590.0873470.5947790.019*
C30.7305 (6)0.16003 (11)0.6065 (3)0.0211 (7)
H30.8575650.1642310.5378880.025*
C40.6301 (6)0.19963 (10)0.6735 (3)0.0213 (7)
C140.7186 (8)0.24914 (12)0.6366 (4)0.0352 (9)
C60.3576 (6)0.14825 (10)0.8057 (3)0.0186 (6)
H60.2275260.1442400.8730040.022*
C50.4454 (7)0.19375 (11)0.7736 (3)0.0213 (7)
H50.3793380.2208800.8200560.026*
C120.2418 (6)0.08793 (11)0.9149 (3)0.0178 (6)
H120.1194180.0970370.9819430.021*
C130.2971 (6)0.03981 (10)0.8942 (3)0.0155 (6)
H130.2142830.0162000.9479280.019*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01333 (17)0.01845 (16)0.01740 (16)0.00074 (12)0.00564 (11)0.00226 (12)
F1A0.0232 (12)0.0306 (14)0.059 (4)0.0059 (10)0.010 (3)0.024 (3)
F2A0.0307 (15)0.043 (2)0.075 (5)0.0030 (13)0.004 (3)0.045 (3)
F3A0.156 (9)0.019 (2)0.073 (3)0.030 (4)0.047 (5)0.009 (2)
F1B0.0232 (12)0.0306 (14)0.059 (4)0.0059 (10)0.010 (3)0.024 (3)
F2B0.0307 (15)0.043 (2)0.075 (5)0.0030 (13)0.004 (3)0.045 (3)
F3B0.049 (9)0.010 (6)0.045 (6)0.014 (5)0.002 (6)0.004 (4)
O10.0107 (10)0.0143 (10)0.0293 (11)0.0002 (8)0.0050 (9)0.0007 (8)
N10.0082 (12)0.0102 (11)0.0153 (11)0.0009 (9)0.0010 (9)0.0016 (9)
C110.0191 (16)0.0117 (14)0.0275 (16)0.0032 (12)0.0015 (13)0.0059 (12)
C100.0175 (15)0.0167 (14)0.0195 (15)0.0023 (12)0.0019 (12)0.0023 (12)
C90.0070 (13)0.0165 (14)0.0154 (14)0.0016 (11)0.0009 (11)0.0012 (11)
C80.0076 (13)0.0142 (13)0.0104 (13)0.0021 (11)0.0046 (10)0.0004 (11)
C70.0073 (13)0.0128 (13)0.0130 (13)0.0013 (10)0.0002 (11)0.0017 (10)
C10.0085 (13)0.0130 (14)0.0145 (13)0.0004 (11)0.0037 (11)0.0003 (11)
C20.0139 (15)0.0154 (14)0.0183 (14)0.0010 (11)0.0001 (12)0.0003 (11)
C30.0166 (15)0.0258 (17)0.0217 (15)0.0020 (13)0.0060 (12)0.0057 (13)
C40.0215 (16)0.0143 (15)0.0279 (16)0.0024 (12)0.0004 (13)0.0058 (13)
C140.043 (2)0.0201 (17)0.044 (2)0.0048 (16)0.0100 (19)0.0051 (16)
C60.0199 (16)0.0163 (15)0.0203 (15)0.0006 (12)0.0058 (12)0.0011 (12)
C50.0259 (17)0.0144 (15)0.0241 (16)0.0013 (12)0.0044 (13)0.0021 (12)
C120.0122 (14)0.0213 (15)0.0200 (15)0.0053 (12)0.0020 (12)0.0051 (12)
C130.0120 (14)0.0184 (15)0.0160 (14)0.0013 (11)0.0012 (11)0.0017 (11)
Geometric parameters (Å, º) top
Br1—C91.904 (3)C9—C81.395 (4)
F1A—C141.377 (8)C8—C131.396 (4)
F2A—C141.395 (10)C7—C11.503 (4)
F3A—C141.328 (6)C1—C61.390 (4)
F1B—C141.18 (2)C1—C21.393 (4)
F1B—F3B1.50 (3)C2—C31.383 (4)
F2B—C141.11 (2)C2—H20.9500
F3B—C141.413 (14)C3—C41.390 (4)
O1—C71.230 (3)C3—H30.9500
N1—C71.347 (4)C4—C51.384 (4)
N1—C81.415 (4)C4—C141.496 (4)
N1—H10.861 (18)C6—C51.380 (4)
C11—C101.388 (4)C6—H60.9500
C11—C121.388 (4)C5—H50.9500
C11—H110.9500C12—C131.385 (4)
C10—C91.383 (4)C12—H120.9500
C10—H100.9500C13—H130.9500
C14—F1B—F3B62.4 (15)C4—C3—H3120.2
C14—F3B—F1B47.8 (10)C5—C4—C3120.5 (3)
C7—N1—C8125.2 (2)C5—C4—C14119.4 (3)
C7—N1—H1117 (2)C3—C4—C14120.1 (3)
C8—N1—H1118 (2)F2B—C14—F1B123.1 (16)
C10—C11—C12120.0 (3)F3A—C14—F1A116.4 (9)
C10—C11—H11120.0F3A—C14—F2A101.7 (5)
C12—C11—H11120.0F1A—C14—F2A99.2 (6)
C9—C10—C11119.0 (3)F2B—C14—F3B112.1 (13)
C9—C10—H10120.5F1B—C14—F3B69.8 (18)
C11—C10—H10120.5F2B—C14—C4118.0 (13)
C10—C9—C8122.2 (3)F1B—C14—C4114.5 (11)
C10—C9—Br1118.4 (2)F3A—C14—C4113.1 (3)
C8—C9—Br1119.3 (2)F1A—C14—C4113.3 (4)
C9—C8—C13117.8 (3)F2A—C14—C4111.4 (4)
C9—C8—N1120.5 (2)F3B—C14—C4107.5 (6)
C13—C8—N1121.7 (2)C5—C6—C1120.6 (3)
O1—C7—N1124.2 (3)C5—C6—H6119.7
O1—C7—C1120.0 (2)C1—C6—H6119.7
N1—C7—C1115.8 (2)C6—C5—C4119.6 (3)
C6—C1—C2119.3 (3)C6—C5—H5120.2
C6—C1—C7118.5 (2)C4—C5—H5120.2
C2—C1—C7122.1 (2)C13—C12—C11120.5 (3)
C3—C2—C1120.3 (3)C13—C12—H12119.8
C3—C2—H2119.8C11—C12—H12119.8
C1—C2—H2119.8C12—C13—C8120.6 (3)
C2—C3—C4119.6 (3)C12—C13—H13119.7
C2—C3—H3120.2C8—C13—H13119.7
C12—C11—C10—C90.5 (5)F1B—F3B—C14—C4110.3 (12)
C11—C10—C9—C80.6 (5)C5—C4—C14—F2B67.3 (17)
C11—C10—C9—Br1178.9 (2)C3—C4—C14—F2B112.0 (17)
C10—C9—C8—C130.9 (4)C5—C4—C14—F1B135.8 (14)
Br1—C9—C8—C13179.2 (2)C3—C4—C14—F1B44.9 (14)
C10—C9—C8—N1179.6 (3)C5—C4—C14—F3A23.1 (9)
Br1—C9—C8—N12.0 (4)C3—C4—C14—F3A157.6 (9)
C7—N1—C8—C9143.4 (3)C5—C4—C14—F1A158.4 (5)
C7—N1—C8—C1337.9 (4)C3—C4—C14—F1A22.3 (6)
C8—N1—C7—O13.2 (4)C5—C4—C14—F2A90.7 (6)
C8—N1—C7—C1176.3 (2)C3—C4—C14—F2A88.6 (6)
O1—C7—C1—C633.6 (4)C5—C4—C14—F3B60.6 (10)
N1—C7—C1—C6146.9 (3)C3—C4—C14—F3B120.2 (10)
O1—C7—C1—C2143.9 (3)C2—C1—C6—C51.2 (5)
N1—C7—C1—C235.6 (4)C7—C1—C6—C5178.7 (3)
C6—C1—C2—C30.4 (4)C1—C6—C5—C41.4 (5)
C7—C1—C2—C3177.9 (3)C3—C4—C5—C60.9 (5)
C1—C2—C3—C40.2 (5)C14—C4—C5—C6178.4 (3)
C2—C3—C4—C50.1 (5)C10—C11—C12—C130.6 (4)
C2—C3—C4—C14179.2 (3)C11—C12—C13—C80.8 (4)
F3B—F1B—C14—F2B104 (2)C9—C8—C13—C121.0 (4)
F3B—F1B—C14—C4100.6 (12)N1—C8—C13—C12179.7 (3)
F1B—F3B—C14—F2B118.5 (17)
(PB32) top
Crystal data top
C14H9BrF3NODx = 1.716 Mg m3
Mr = 344.13Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 7931 reflections
a = 7.8062 (3) Åθ = 2.8–34.4°
b = 19.3000 (7) ŵ = 3.11 mm1
c = 8.8433 (3) ÅT = 100 K
V = 1332.33 (8) Å3Needle
Z = 40.34 × 0.15 × 0.13 mm
F(000) = 680
Data collection top
Bruker APEX-II CCD
diffractometer
2170 reflections with I > 2σ(I)
φ and ω scansRint = 0.032
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.0°, θmin = 2.8°
Tmin = 0.417, Tmax = 0.688h = 98
7418 measured reflectionsk = 2122
2239 independent reflectionsl = 1010
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057 w = 1/[σ2(Fo2) + (0.0237P)2 + 0.1506P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2239 reflectionsΔρmax = 0.64 e Å3
185 parametersΔρmin = 0.24 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.06621 (4)0.96805 (2)0.53181 (7)0.01863 (13)
F10.3000 (3)0.53012 (10)0.8649 (3)0.0397 (7)
F20.3967 (4)0.59822 (13)0.6928 (3)0.0363 (6)
F30.1839 (3)0.62966 (12)0.8313 (3)0.0316 (5)
O10.3933 (3)0.75529 (13)0.7431 (3)0.0212 (6)
N10.2360 (4)0.78380 (13)0.9515 (3)0.0154 (6)
H10.211 (4)0.7707 (15)1.047 (5)0.004 (8)*
C140.3358 (5)0.59697 (19)0.8348 (4)0.0250 (8)
C20.4557 (4)0.62757 (17)0.9485 (4)0.0160 (7)
C10.4620 (4)0.69910 (17)0.9742 (4)0.0141 (7)
C60.5718 (4)0.72505 (19)1.0828 (4)0.0156 (8)
H60.5733760.7734001.1028610.019*
C50.6802 (5)0.68125 (19)1.1630 (4)0.0218 (8)
H50.7576730.6996931.2353710.026*
C40.6744 (5)0.6107 (2)1.1367 (4)0.0247 (8)
H40.7483310.5806061.1911830.030*
C30.5615 (4)0.58368 (16)1.0316 (7)0.0218 (7)
H30.5560910.5350271.0159770.026*
C70.3596 (4)0.74863 (16)0.8775 (4)0.0155 (7)
C80.1099 (5)0.82671 (16)0.8824 (4)0.0150 (7)
C130.0554 (4)0.82287 (19)0.9391 (4)0.0184 (8)
H130.0809480.7931471.0217310.022*
C120.1830 (4)0.86287 (17)0.8740 (4)0.0180 (7)
H120.2961810.8604870.9132000.022*
C110.1492 (4)0.90623 (16)0.7529 (4)0.0171 (7)
H110.2376070.9329050.7074970.021*
C100.0175 (5)0.90954 (16)0.6999 (4)0.0151 (7)
C90.1490 (4)0.87115 (16)0.7643 (4)0.0136 (7)
H90.2632260.8752450.7282110.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0202 (2)0.01782 (18)0.01790 (18)0.00315 (10)0.00356 (18)0.00558 (16)
F10.0452 (18)0.0236 (13)0.0502 (17)0.0136 (8)0.0040 (14)0.0054 (10)
F20.0364 (14)0.0510 (15)0.0214 (12)0.0073 (12)0.0014 (11)0.0142 (12)
F30.0184 (11)0.0421 (13)0.0345 (13)0.0012 (9)0.0067 (10)0.0110 (11)
O10.0188 (13)0.0335 (14)0.0112 (13)0.0087 (11)0.0019 (11)0.0039 (11)
N10.0172 (16)0.0194 (15)0.0095 (15)0.0032 (11)0.0002 (13)0.0024 (13)
C140.027 (2)0.0253 (19)0.0226 (19)0.0020 (15)0.0005 (17)0.0047 (16)
C20.0134 (18)0.0197 (18)0.0147 (18)0.0010 (12)0.0055 (14)0.0009 (14)
C10.0106 (16)0.0194 (17)0.0121 (15)0.0011 (12)0.0031 (13)0.0043 (13)
C60.0140 (19)0.0185 (17)0.0144 (17)0.0011 (12)0.0013 (13)0.0012 (14)
C50.0159 (19)0.0279 (19)0.0216 (18)0.0000 (14)0.0024 (16)0.0030 (15)
C40.020 (2)0.028 (2)0.0266 (19)0.0064 (14)0.0002 (17)0.0105 (16)
C30.0199 (18)0.0172 (15)0.0283 (17)0.0032 (11)0.0054 (19)0.001 (2)
C70.0148 (19)0.0181 (16)0.0135 (17)0.0026 (13)0.0027 (16)0.0016 (14)
C80.0166 (18)0.0148 (16)0.0135 (17)0.0031 (12)0.0035 (15)0.0033 (13)
C130.020 (2)0.0199 (18)0.0150 (18)0.0011 (12)0.0034 (15)0.0005 (15)
C120.0139 (17)0.0209 (17)0.0193 (17)0.0046 (12)0.0014 (16)0.0000 (14)
C110.0139 (19)0.0186 (17)0.0189 (16)0.0055 (13)0.0029 (16)0.0019 (15)
C100.0211 (18)0.0105 (15)0.0135 (16)0.0018 (13)0.0011 (16)0.0005 (13)
C90.0110 (18)0.0172 (16)0.0126 (15)0.0008 (12)0.0002 (14)0.0045 (14)
Geometric parameters (Å, º) top
Br1—C101.905 (3)C5—C41.382 (5)
F1—C141.347 (4)C5—H50.9500
F2—C141.343 (5)C4—C31.383 (6)
F3—C141.343 (4)C4—H40.9500
O1—C71.223 (4)C3—H30.9500
N1—C71.349 (5)C8—C91.386 (5)
N1—C81.424 (4)C8—C131.387 (5)
N1—H10.90 (4)C13—C121.386 (5)
C14—C21.496 (5)C13—H130.9500
C2—C31.392 (6)C12—C111.385 (5)
C2—C11.400 (5)C12—H120.9500
C1—C61.381 (5)C11—C101.385 (6)
C1—C71.512 (5)C11—H110.9500
C6—C51.390 (5)C10—C91.388 (5)
C6—H60.9500C9—H90.9500
C7—N1—C8125.4 (3)C4—C3—C2120.2 (3)
C7—N1—H1118 (2)C4—C3—H3119.9
C8—N1—H1115 (2)C2—C3—H3119.9
F2—C14—F3106.4 (3)O1—C7—N1124.9 (3)
F2—C14—F1106.0 (3)O1—C7—C1120.2 (3)
F3—C14—F1105.8 (3)N1—C7—C1114.9 (3)
F2—C14—C2113.6 (3)C9—C8—C13120.7 (3)
F3—C14—C2112.5 (3)C9—C8—N1122.1 (3)
F1—C14—C2112.0 (3)C13—C8—N1117.2 (3)
C3—C2—C1119.6 (3)C12—C13—C8119.3 (3)
C3—C2—C14119.1 (3)C12—C13—H13120.4
C1—C2—C14121.4 (3)C8—C13—H13120.4
C6—C1—C2119.5 (3)C11—C12—C13121.4 (3)
C6—C1—C7119.5 (3)C11—C12—H12119.3
C2—C1—C7120.9 (3)C13—C12—H12119.3
C1—C6—C5120.8 (3)C10—C11—C12118.0 (3)
C1—C6—H6119.6C10—C11—H11121.0
C5—C6—H6119.6C12—C11—H11121.0
C4—C5—C6119.6 (3)C11—C10—C9122.1 (3)
C4—C5—H5120.2C11—C10—Br1118.6 (3)
C6—C5—H5120.2C9—C10—Br1119.3 (3)
C5—C4—C3120.3 (3)C8—C9—C10118.5 (3)
C5—C4—H4119.8C8—C9—H9120.8
C3—C4—H4119.8C10—C9—H9120.8
F2—C14—C2—C397.2 (4)C8—N1—C7—C1171.9 (3)
F3—C14—C2—C3141.9 (4)C6—C1—C7—O1109.9 (4)
F1—C14—C2—C322.9 (5)C2—C1—C7—O165.8 (5)
F2—C14—C2—C183.7 (4)C6—C1—C7—N169.0 (4)
F3—C14—C2—C137.3 (5)C2—C1—C7—N1115.4 (3)
F1—C14—C2—C1156.3 (3)C7—N1—C8—C941.3 (5)
C3—C2—C1—C60.7 (5)C7—N1—C8—C13139.3 (3)
C14—C2—C1—C6178.5 (3)C9—C8—C13—C121.5 (5)
C3—C2—C1—C7175.0 (4)N1—C8—C13—C12179.0 (3)
C14—C2—C1—C75.8 (5)C8—C13—C12—C110.4 (5)
C2—C1—C6—C52.2 (5)C13—C12—C11—C101.1 (5)
C7—C1—C6—C5173.5 (3)C12—C11—C10—C90.1 (5)
C1—C6—C5—C41.8 (5)C12—C11—C10—Br1179.3 (2)
C6—C5—C4—C30.1 (6)C13—C8—C9—C102.7 (5)
C5—C4—C3—C21.6 (7)N1—C8—C9—C10177.9 (3)
C1—C2—C3—C41.2 (6)C11—C10—C9—C81.9 (5)
C14—C2—C3—C4179.6 (4)Br1—C10—C9—C8177.4 (2)
C8—N1—C7—O19.3 (5)
(PB34) top
Crystal data top
C14H9BrF3NOF(000) = 340
Mr = 344.13Dx = 1.810 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 4.8588 (4) ÅCell parameters from 2029 reflections
b = 4.9939 (4) Åθ = 2.4–23.2°
c = 26.0286 (19) ŵ = 3.29 mm1
β = 91.448 (5)°T = 100 K
V = 631.37 (9) Å3Plate
Z = 20.28 × 0.25 × 0.13 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1757 reflections with I > 2σ(I)
φ and ω scansRint = 0.039
Absorption correction: multi-scan
SADABS 2014/4
θmax = 27.5°, θmin = 2.4°
Tmin = 0.486, Tmax = 0.758h = 66
4884 measured reflectionsk = 56
2296 independent reflectionsl = 3333
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0187P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max < 0.001
S = 0.99Δρmax = 0.82 e Å3
2296 reflectionsΔρmin = 1.01 e Å3
184 parametersAbsolute structure: Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.042 (14)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.10619 (14)0.1494 (2)0.45569 (2)0.0286 (2)
F10.0236 (8)0.2453 (7)0.07439 (13)0.0287 (12)
F20.1236 (7)0.6173 (11)0.03756 (12)0.0302 (11)
F30.3886 (8)0.2767 (8)0.02918 (13)0.0318 (12)
O10.9817 (10)0.9483 (10)0.24447 (17)0.0250 (13)
N11.0002 (12)0.5109 (11)0.2684 (2)0.0159 (13)
H10.949 (14)0.346 (7)0.264 (3)0.019*
C140.2356 (15)0.4098 (15)0.0629 (3)0.0211 (17)
C40.3987 (14)0.4912 (14)0.1093 (2)0.0158 (15)
C30.3835 (13)0.3520 (13)0.1550 (2)0.0192 (17)
H30.2574430.2074940.1575740.023*
C20.5478 (13)0.4193 (14)0.1966 (2)0.0157 (16)
H20.5358320.3202490.2275970.019*
C10.7317 (11)0.631 (2)0.1936 (2)0.0144 (14)
C80.9154 (13)0.7121 (14)0.2377 (2)0.0185 (18)
C71.1513 (14)0.5373 (12)0.3158 (2)0.0162 (17)
C131.3616 (13)0.7193 (12)0.3236 (2)0.0185 (18)
H131.4103760.8385070.2969090.022*
C121.5005 (13)0.7275 (13)0.3703 (2)0.022 (2)
H121.6472180.8510440.3755900.026*
C111.4274 (15)0.5559 (13)0.4098 (3)0.0230 (19)
H111.5215500.5629430.4421690.028*
C50.5767 (13)0.7069 (14)0.1059 (2)0.0172 (18)
H50.5856110.8067910.0749410.021*
C60.7413 (14)0.7757 (13)0.1480 (2)0.0219 (18)
H60.8628410.9239670.1456990.026*
C101.2199 (14)0.3784 (14)0.4014 (2)0.0200 (17)
C91.0790 (13)0.3624 (13)0.3548 (2)0.0163 (16)
H90.9360000.2348740.3494320.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0390 (4)0.0244 (4)0.0224 (3)0.0051 (5)0.0012 (2)0.0037 (5)
F10.032 (2)0.029 (3)0.025 (2)0.0117 (19)0.0039 (16)0.0003 (18)
F20.033 (2)0.029 (3)0.0281 (19)0.004 (3)0.0099 (15)0.010 (2)
F30.033 (3)0.039 (3)0.024 (2)0.0044 (19)0.0027 (19)0.0113 (18)
O10.035 (3)0.005 (3)0.034 (3)0.002 (2)0.009 (2)0.003 (2)
N10.021 (3)0.005 (3)0.021 (3)0.001 (3)0.004 (3)0.001 (3)
C140.020 (4)0.018 (5)0.025 (4)0.001 (3)0.000 (3)0.001 (3)
C40.018 (4)0.012 (4)0.017 (4)0.004 (3)0.002 (3)0.003 (3)
C30.020 (4)0.010 (4)0.027 (4)0.001 (3)0.002 (3)0.001 (3)
C20.018 (4)0.011 (4)0.019 (4)0.001 (3)0.002 (3)0.003 (3)
C10.016 (3)0.007 (4)0.021 (3)0.004 (4)0.002 (2)0.000 (4)
C80.023 (4)0.008 (6)0.024 (4)0.001 (3)0.003 (3)0.003 (3)
C70.023 (4)0.010 (4)0.016 (4)0.004 (3)0.000 (3)0.002 (3)
C130.028 (4)0.007 (5)0.021 (3)0.002 (3)0.001 (3)0.001 (3)
C120.014 (4)0.023 (6)0.028 (4)0.003 (3)0.003 (3)0.006 (3)
C110.027 (4)0.020 (5)0.021 (4)0.010 (3)0.011 (3)0.006 (3)
C50.026 (4)0.006 (6)0.020 (3)0.003 (3)0.001 (3)0.000 (3)
C60.024 (4)0.015 (5)0.027 (4)0.000 (3)0.000 (3)0.001 (3)
C100.031 (5)0.015 (5)0.014 (3)0.006 (4)0.002 (3)0.002 (3)
C90.018 (4)0.008 (4)0.023 (4)0.003 (3)0.000 (3)0.002 (3)
Geometric parameters (Å, º) top
Br1—C101.911 (6)C1—C61.391 (9)
F1—C141.357 (7)C1—C81.491 (9)
F2—C141.337 (8)C7—C131.379 (8)
F3—C141.341 (7)C7—C91.391 (8)
O1—C81.235 (8)C13—C121.375 (8)
N1—C81.342 (8)C13—H130.9500
N1—C71.426 (8)C12—C111.391 (8)
N1—H10.87 (2)C12—H120.9500
C14—C41.484 (9)C11—C101.356 (9)
C4—C31.381 (8)C11—H110.9500
C4—C51.385 (9)C5—C61.383 (8)
C3—C21.371 (8)C5—H50.9500
C3—H30.9500C6—H60.9500
C2—C11.389 (10)C10—C91.380 (8)
C2—H20.9500C9—H90.9500
C8—N1—C7126.1 (6)C13—C7—C9120.4 (6)
C8—N1—H1124 (5)C13—C7—N1123.6 (6)
C7—N1—H1110 (5)C9—C7—N1116.1 (6)
F2—C14—F3106.6 (5)C12—C13—C7119.7 (6)
F2—C14—F1106.1 (6)C12—C13—H13120.1
F3—C14—F1106.3 (5)C7—C13—H13120.1
F2—C14—C4113.0 (6)C13—C12—C11120.3 (6)
F3—C14—C4112.0 (6)C13—C12—H12119.8
F1—C14—C4112.3 (5)C11—C12—H12119.8
C3—C4—C5119.5 (6)C10—C11—C12119.1 (6)
C3—C4—C14121.5 (6)C10—C11—H11120.4
C5—C4—C14118.9 (6)C12—C11—H11120.4
C2—C3—C4120.9 (6)C6—C5—C4119.5 (6)
C2—C3—H3119.5C6—C5—H5120.3
C4—C3—H3119.5C4—C5—H5120.3
C3—C2—C1120.4 (6)C5—C6—C1121.1 (6)
C3—C2—H2119.8C5—C6—H6119.5
C1—C2—H2119.8C1—C6—H6119.5
C2—C1—C6118.5 (6)C11—C10—C9122.0 (6)
C2—C1—C8122.5 (6)C11—C10—Br1120.0 (5)
C6—C1—C8119.0 (7)C9—C10—Br1118.0 (5)
O1—C8—N1123.8 (6)C10—C9—C7118.4 (6)
O1—C8—C1121.2 (7)C10—C9—H9120.8
N1—C8—C1115.1 (7)C7—C9—H9120.8
F2—C14—C4—C3137.8 (6)C8—N1—C7—C1340.0 (10)
F3—C14—C4—C3101.7 (7)C8—N1—C7—C9141.3 (6)
F1—C14—C4—C317.8 (9)C9—C7—C13—C120.0 (9)
F2—C14—C4—C544.3 (8)N1—C7—C13—C12178.6 (6)
F3—C14—C4—C576.1 (8)C7—C13—C12—C110.9 (9)
F1—C14—C4—C5164.3 (6)C13—C12—C11—C100.8 (10)
C5—C4—C3—C21.9 (10)C3—C4—C5—C61.5 (9)
C14—C4—C3—C2176.0 (6)C14—C4—C5—C6176.4 (6)
C4—C3—C2—C10.6 (10)C4—C5—C6—C10.2 (10)
C3—C2—C1—C61.1 (10)C2—C1—C6—C51.5 (10)
C3—C2—C1—C8179.8 (6)C8—C1—C6—C5179.4 (6)
C7—N1—C8—O17.3 (11)C12—C11—C10—C90.1 (10)
C7—N1—C8—C1172.8 (5)C12—C11—C10—Br1177.7 (5)
C2—C1—C8—O1147.5 (7)C11—C10—C9—C71.0 (10)
C6—C1—C8—O131.5 (9)Br1—C10—C9—C7176.9 (5)
C2—C1—C8—N132.6 (9)C13—C7—C9—C100.9 (9)
C6—C1—C8—N1148.3 (6)N1—C7—C9—C10179.6 (6)
(PB43) top
Crystal data top
C14H9BrF3NOF(000) = 680
Mr = 344.13Dx = 1.726 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.018 (3) ÅCell parameters from 8180 reflections
b = 10.488 (2) Åθ = 2.7–30.8°
c = 9.7309 (19) ŵ = 3.13 mm1
β = 94.432 (14)°T = 100 K
V = 1324.6 (4) Å3Plate
Z = 40.28 × 0.13 × 0.10 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1948 reflections with I > 2σ(I)
φ and ω scansRint = 0.046
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 2.5°
Tmin = 0.487, Tmax = 0.731h = 1315
9729 measured reflectionsk = 1012
2453 independent reflectionsl = 1111
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.9094P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2453 reflectionsΔρmax = 0.82 e Å3
185 parametersΔρmin = 0.58 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.97461 (3)0.84030 (4)0.44456 (4)0.02757 (15)
F10.4742 (2)0.0196 (3)0.8148 (3)0.0741 (9)
F20.4596 (3)0.1556 (3)0.7203 (4)0.0940 (13)
F30.5783 (2)0.1254 (4)0.8778 (4)0.1189 (18)
O10.77241 (18)0.3007 (2)0.7125 (2)0.0230 (6)
N10.7783 (2)0.3168 (3)0.4809 (3)0.0182 (7)
H10.774 (2)0.275 (4)0.405 (4)0.020 (10)*
C10.7119 (2)0.1236 (3)0.5779 (3)0.0176 (8)
C20.7367 (3)0.0396 (4)0.4758 (3)0.0253 (8)
H20.7832560.0646940.4102930.030*
C30.6932 (3)0.0817 (4)0.4693 (4)0.0317 (10)
H30.7103380.1390580.3990520.038*
C40.6257 (3)0.1193 (4)0.5635 (4)0.0312 (10)
H40.5960820.2021590.5586450.037*
C50.6014 (3)0.0349 (4)0.6657 (4)0.0264 (9)
C60.6447 (2)0.0841 (4)0.6740 (4)0.0225 (8)
H60.6287020.1401310.7460230.027*
C70.7574 (2)0.2538 (3)0.5960 (3)0.0179 (7)
C80.8226 (2)0.4402 (3)0.4761 (3)0.0172 (7)
C90.8843 (2)0.4672 (4)0.3694 (3)0.0202 (8)
H90.8960900.4031720.3033630.024*
C100.9287 (3)0.5857 (4)0.3583 (3)0.0217 (8)
H100.9707670.6038830.2852820.026*
C110.9108 (3)0.6773 (3)0.4551 (3)0.0199 (8)
C120.8489 (3)0.6535 (3)0.5608 (3)0.0205 (8)
H120.8369580.7181740.6260070.025*
C130.8045 (3)0.5350 (3)0.5709 (3)0.0191 (8)
H130.7613580.5180170.6431630.023*
C140.5311 (3)0.0749 (4)0.7707 (5)0.0397 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0310 (2)0.0199 (2)0.0325 (2)0.00732 (16)0.00686 (15)0.00014 (17)
F10.080 (2)0.062 (2)0.088 (2)0.0032 (18)0.0535 (17)0.0146 (18)
F20.074 (2)0.084 (3)0.128 (3)0.054 (2)0.035 (2)0.015 (2)
F30.0523 (19)0.209 (5)0.098 (3)0.022 (2)0.0233 (18)0.125 (3)
O10.0350 (14)0.0191 (14)0.0149 (12)0.0025 (11)0.0021 (10)0.0001 (10)
N10.0273 (16)0.0154 (17)0.0121 (14)0.0003 (12)0.0022 (12)0.0022 (12)
C10.0218 (18)0.0146 (19)0.0157 (17)0.0004 (14)0.0021 (14)0.0020 (14)
C20.039 (2)0.018 (2)0.0194 (18)0.0027 (16)0.0026 (15)0.0029 (15)
C30.050 (3)0.019 (2)0.026 (2)0.0001 (18)0.0003 (18)0.0043 (17)
C40.039 (2)0.015 (2)0.038 (2)0.0057 (17)0.0092 (18)0.0050 (18)
C50.0203 (18)0.026 (2)0.031 (2)0.0016 (16)0.0044 (15)0.0073 (18)
C60.0214 (18)0.023 (2)0.0224 (18)0.0026 (15)0.0001 (14)0.0008 (16)
C70.0173 (17)0.019 (2)0.0172 (17)0.0056 (15)0.0001 (13)0.0021 (15)
C80.0187 (17)0.0156 (19)0.0170 (16)0.0011 (14)0.0012 (13)0.0025 (15)
C90.0239 (18)0.022 (2)0.0145 (16)0.0001 (15)0.0010 (13)0.0016 (15)
C100.0215 (18)0.025 (2)0.0191 (17)0.0006 (16)0.0046 (14)0.0014 (16)
C110.0212 (18)0.017 (2)0.0213 (18)0.0016 (14)0.0021 (14)0.0038 (15)
C120.0260 (18)0.017 (2)0.0188 (17)0.0030 (15)0.0029 (14)0.0035 (15)
C130.0255 (18)0.0146 (19)0.0177 (16)0.0027 (15)0.0042 (13)0.0011 (14)
C140.033 (2)0.031 (3)0.056 (3)0.005 (2)0.005 (2)0.013 (2)
Geometric parameters (Å, º) top
Br1—C111.907 (3)C4—C51.386 (5)
F1—C141.328 (5)C4—H40.9500
F2—C141.323 (5)C5—C61.369 (5)
F3—C141.283 (5)C5—C141.484 (6)
O1—C71.237 (4)C6—H60.9500
N1—C71.347 (4)C8—C131.389 (5)
N1—C81.419 (4)C8—C91.390 (5)
N1—H10.86 (4)C9—C101.378 (5)
C1—C21.385 (5)C9—H90.9500
C1—C61.392 (5)C10—C111.378 (5)
C1—C71.494 (5)C10—H100.9500
C2—C31.391 (5)C11—C121.377 (5)
C2—H20.9500C12—C131.377 (5)
C3—C41.377 (6)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.7 (3)C13—C8—C9119.2 (3)
C7—N1—H1117 (2)C13—C8—N1122.7 (3)
C8—N1—H1116 (2)C9—C8—N1118.1 (3)
C2—C1—C6119.1 (3)C10—C9—C8120.8 (3)
C2—C1—C7123.6 (3)C10—C9—H9119.6
C6—C1—C7117.2 (3)C8—C9—H9119.6
C1—C2—C3119.8 (4)C9—C10—C11118.8 (3)
C1—C2—H2120.1C9—C10—H10120.6
C3—C2—H2120.1C11—C10—H10120.6
C4—C3—C2120.7 (4)C12—C11—C10121.5 (3)
C4—C3—H3119.7C12—C11—Br1119.0 (3)
C2—C3—H3119.7C10—C11—Br1119.4 (3)
C3—C4—C5119.2 (4)C11—C12—C13119.4 (3)
C3—C4—H4120.4C11—C12—H12120.3
C5—C4—H4120.4C13—C12—H12120.3
C6—C5—C4120.6 (4)C12—C13—C8120.3 (3)
C6—C5—C14119.3 (4)C12—C13—H13119.9
C4—C5—C14120.0 (4)C8—C13—H13119.9
C5—C6—C1120.6 (3)F3—C14—F2108.4 (4)
C5—C6—H6119.7F3—C14—F1106.9 (4)
C1—C6—H6119.7F2—C14—F1101.7 (4)
O1—C7—N1122.6 (3)F3—C14—C5113.2 (3)
O1—C7—C1120.3 (3)F2—C14—C5112.3 (4)
N1—C7—C1117.0 (3)F1—C14—C5113.6 (4)
C6—C1—C2—C31.0 (5)C7—N1—C8—C9148.7 (3)
C7—C1—C2—C3177.8 (3)C13—C8—C9—C101.0 (5)
C1—C2—C3—C40.0 (5)N1—C8—C9—C10179.3 (3)
C2—C3—C4—C50.1 (5)C8—C9—C10—C110.0 (5)
C3—C4—C5—C60.7 (5)C9—C10—C11—C120.9 (5)
C3—C4—C5—C14178.2 (3)C9—C10—C11—Br1178.2 (2)
C4—C5—C6—C11.7 (5)C10—C11—C12—C130.6 (5)
C14—C5—C6—C1179.2 (3)Br1—C11—C12—C13178.5 (2)
C2—C1—C6—C51.8 (5)C11—C12—C13—C80.4 (5)
C7—C1—C6—C5178.8 (3)C9—C8—C13—C121.2 (5)
C8—N1—C7—O12.4 (5)N1—C8—C13—C12179.5 (3)
C8—N1—C7—C1179.2 (3)C6—C5—C14—F387.6 (5)
C2—C1—C7—O1146.9 (3)C4—C5—C14—F390.0 (5)
C6—C1—C7—O130.0 (4)C6—C5—C14—F2149.3 (4)
C2—C1—C7—N134.7 (4)C4—C5—C14—F233.1 (5)
C6—C1—C7—N1148.4 (3)C6—C5—C14—F134.5 (5)
C7—N1—C8—C1333.0 (5)C4—C5—C14—F1147.9 (4)
(PB44) top
Crystal data top
C14H9BrF3NOF(000) = 1360
Mr = 344.13Dx = 1.773 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 16.9434 (5) ÅCell parameters from 6753 reflections
b = 5.2417 (1) Åθ = 2.8–30.2°
c = 29.1410 (8) ŵ = 3.22 mm1
β = 94.775 (2)°T = 100 K
V = 2579.09 (12) Å3Needle
Z = 80.40 × 0.10 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3971 reflections with I > 2σ(I)
φ and ω scansRint = 0.038
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.0°, θmin = 1.4°
Tmin = 0.476, Tmax = 0.710h = 2020
21794 measured reflectionsk = 56
4543 independent reflectionsl = 3334
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.170 w = 1/[σ2(Fo2) + (0.0542P)2 + 27.2059P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.001
4543 reflectionsΔρmax = 2.70 e Å3
367 parametersΔρmin = 0.90 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br1A0.05020 (4)0.42865 (14)0.10486 (2)0.0204 (2)
Br2A0.54395 (4)0.74317 (13)0.39392 (2)0.0177 (2)
F10.3300 (3)0.2773 (12)0.51550 (14)0.0485 (16)
F20.4391 (3)0.2472 (11)0.48501 (17)0.0485 (15)
F30.3834 (4)0.6046 (10)0.49063 (18)0.0555 (16)
F40.0549 (3)0.7311 (15)0.02125 (17)0.071 (2)
F50.1599 (3)0.6297 (10)0.00970 (16)0.0436 (13)
F60.1220 (3)1.0154 (10)0.00966 (16)0.0455 (14)
O10.1848 (3)0.0420 (9)0.29234 (16)0.0168 (10)
O20.3146 (3)1.2151 (9)0.20439 (15)0.0150 (10)
N10.1652 (3)0.3839 (11)0.28213 (18)0.0113 (11)
H10.184 (4)0.545 (15)0.295 (2)0.014*
N20.3348 (3)0.7855 (10)0.21435 (19)0.0115 (11)
H20.324 (4)0.628 (6)0.207 (2)0.014*
C10.2395 (3)0.2381 (12)0.3514 (2)0.0102 (13)
C20.2231 (4)0.4466 (13)0.3774 (2)0.0149 (14)
H2A0.1827210.5630030.3666260.018*
C30.2660 (4)0.4870 (14)0.4197 (2)0.0184 (15)
H30.2547450.6307310.4379550.022*
C40.3252 (4)0.3162 (14)0.4353 (2)0.0155 (14)
C50.3418 (4)0.1067 (13)0.4089 (2)0.0168 (14)
H50.3827180.0081510.4194390.020*
C60.2987 (4)0.0648 (13)0.3672 (2)0.0142 (14)
H60.3091900.0809650.3492790.017*
C70.1942 (4)0.1800 (13)0.3059 (2)0.0140 (14)
C80.1166 (3)0.3811 (12)0.2400 (2)0.0101 (13)
C90.1219 (4)0.5860 (12)0.2103 (2)0.0120 (13)
H90.1592360.7179040.2177950.014*
C100.0729 (4)0.5997 (13)0.1698 (2)0.0137 (13)
H100.0770050.7387660.1492490.016*
C110.0178 (4)0.4070 (13)0.1598 (2)0.0139 (14)
C120.0120 (4)0.2052 (13)0.1895 (2)0.0115 (13)
H120.0262820.0755900.1823730.014*
C130.0614 (4)0.1893 (13)0.2296 (2)0.0128 (13)
H130.0575900.0487660.2498900.015*
C140.3698 (4)0.3570 (16)0.4812 (2)0.0245 (17)
C150.2606 (4)0.9385 (13)0.1450 (2)0.0129 (13)
C160.2782 (4)0.7312 (13)0.1182 (2)0.0132 (13)
H160.3193970.6170920.1286660.016*
C170.2356 (4)0.6896 (14)0.0758 (2)0.0186 (15)
H170.2479870.5485490.0572670.022*
C180.1751 (4)0.8554 (13)0.0610 (2)0.0163 (14)
C190.1571 (4)1.0625 (13)0.0881 (2)0.0161 (14)
H190.1153751.1754050.0779290.019*
C200.2001 (4)1.1037 (13)0.1298 (2)0.0139 (13)
H200.1880421.2458940.1481970.017*
C210.3056 (3)0.9967 (12)0.1904 (2)0.0097 (13)
C220.3818 (3)0.7892 (12)0.2568 (2)0.0102 (13)
C230.3752 (3)0.5860 (13)0.2865 (2)0.0116 (13)
H230.3376970.4548940.2788550.014*
C240.4233 (4)0.5724 (13)0.3275 (2)0.0130 (13)
H240.4184990.4327720.3478210.016*
C250.4780 (4)0.7627 (12)0.3385 (2)0.0110 (13)
C260.4848 (4)0.9717 (13)0.3090 (2)0.0136 (14)
H260.5219821.1033510.3170190.016*
C270.4366 (4)0.9846 (12)0.2679 (2)0.0111 (13)
H270.4409291.1246410.2476070.013*
C280.1268 (4)0.8125 (16)0.0158 (2)0.0240 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0156 (4)0.0307 (4)0.0139 (4)0.0024 (3)0.0047 (3)0.0025 (3)
Br2A0.0163 (4)0.0258 (4)0.0097 (3)0.0020 (3)0.0064 (2)0.0032 (3)
F10.048 (3)0.087 (4)0.009 (2)0.035 (3)0.002 (2)0.008 (2)
F20.039 (3)0.068 (4)0.033 (3)0.016 (3)0.023 (2)0.020 (3)
F30.088 (4)0.031 (3)0.041 (3)0.022 (3)0.034 (3)0.002 (2)
F40.033 (3)0.150 (7)0.028 (3)0.049 (4)0.007 (2)0.006 (3)
F50.061 (3)0.039 (3)0.027 (3)0.002 (3)0.021 (2)0.009 (2)
F60.068 (4)0.040 (3)0.024 (3)0.002 (3)0.020 (2)0.001 (2)
O10.020 (2)0.009 (2)0.020 (2)0.0002 (19)0.0037 (19)0.004 (2)
O20.018 (2)0.011 (3)0.014 (2)0.0001 (19)0.0036 (19)0.0027 (19)
N10.011 (3)0.011 (3)0.011 (3)0.003 (2)0.004 (2)0.002 (2)
N20.011 (3)0.009 (3)0.014 (3)0.001 (2)0.003 (2)0.004 (2)
C10.008 (3)0.012 (3)0.011 (3)0.003 (3)0.002 (2)0.003 (3)
C20.009 (3)0.015 (3)0.020 (3)0.001 (3)0.001 (3)0.000 (3)
C30.019 (3)0.016 (4)0.020 (4)0.000 (3)0.001 (3)0.002 (3)
C40.011 (3)0.026 (4)0.009 (3)0.003 (3)0.003 (2)0.002 (3)
C50.012 (3)0.018 (4)0.020 (3)0.002 (3)0.000 (3)0.005 (3)
C60.012 (3)0.014 (3)0.016 (3)0.001 (3)0.002 (3)0.000 (3)
C70.008 (3)0.017 (4)0.018 (3)0.003 (3)0.003 (3)0.002 (3)
C80.008 (3)0.012 (3)0.011 (3)0.000 (3)0.001 (2)0.002 (3)
C90.010 (3)0.010 (3)0.016 (3)0.003 (3)0.003 (2)0.002 (3)
C100.014 (3)0.013 (3)0.015 (3)0.002 (3)0.006 (3)0.003 (3)
C110.011 (3)0.018 (4)0.013 (3)0.002 (3)0.002 (2)0.000 (3)
C120.008 (3)0.014 (3)0.012 (3)0.002 (3)0.000 (2)0.000 (3)
C130.008 (3)0.020 (4)0.010 (3)0.001 (3)0.000 (2)0.000 (3)
C140.023 (4)0.035 (5)0.015 (4)0.013 (3)0.004 (3)0.000 (3)
C150.012 (3)0.018 (4)0.009 (3)0.003 (3)0.001 (2)0.002 (3)
C160.014 (3)0.015 (3)0.010 (3)0.003 (3)0.002 (2)0.001 (3)
C170.019 (3)0.023 (4)0.014 (3)0.001 (3)0.000 (3)0.006 (3)
C180.015 (3)0.020 (4)0.014 (3)0.007 (3)0.001 (3)0.004 (3)
C190.013 (3)0.018 (4)0.016 (3)0.001 (3)0.003 (3)0.006 (3)
C200.015 (3)0.014 (3)0.013 (3)0.001 (3)0.000 (3)0.000 (3)
C210.006 (3)0.011 (3)0.013 (3)0.002 (2)0.001 (2)0.001 (3)
C220.007 (3)0.015 (3)0.008 (3)0.004 (3)0.001 (2)0.002 (3)
C230.009 (3)0.015 (3)0.011 (3)0.000 (3)0.002 (2)0.003 (3)
C240.016 (3)0.015 (3)0.008 (3)0.003 (3)0.001 (2)0.002 (3)
C250.011 (3)0.013 (3)0.010 (3)0.006 (3)0.002 (2)0.001 (3)
C260.009 (3)0.012 (3)0.019 (3)0.000 (3)0.002 (3)0.002 (3)
C270.011 (3)0.008 (3)0.014 (3)0.002 (2)0.000 (2)0.002 (3)
C280.020 (4)0.039 (5)0.013 (3)0.008 (3)0.002 (3)0.007 (3)
Geometric parameters (Å, º) top
Br1A—C111.895 (6)C9—C101.387 (9)
Br2A—C251.889 (6)C9—H90.9500
F1—C141.320 (8)C10—C111.391 (9)
F2—C141.305 (9)C10—H100.9500
F3—C141.343 (10)C11—C121.376 (9)
F4—C281.313 (9)C12—C131.383 (9)
F5—C281.362 (9)C12—H120.9500
F6—C281.296 (9)C13—H130.9500
O1—C71.235 (8)C15—C161.386 (9)
O2—C211.221 (8)C15—C201.387 (9)
N1—C71.344 (9)C15—C211.501 (9)
N1—C81.420 (8)C16—C171.394 (9)
N1—H10.97 (8)C16—H160.9500
N2—C211.378 (8)C17—C181.386 (10)
N2—C221.414 (8)C17—H170.9500
N2—H20.87 (2)C18—C191.391 (10)
C1—C21.373 (9)C18—C281.508 (9)
C1—C61.402 (9)C19—C201.381 (9)
C1—C71.506 (9)C19—H190.9500
C2—C31.395 (9)C20—H200.9500
C2—H2A0.9500C22—C231.383 (9)
C3—C41.391 (10)C22—C271.403 (9)
C3—H30.9500C23—C241.390 (9)
C4—C51.382 (10)C23—H230.9500
C4—C141.496 (9)C24—C251.382 (9)
C5—C61.383 (9)C24—H240.9500
C5—H50.9500C25—C261.402 (9)
C6—H60.9500C26—C271.394 (9)
C8—C91.386 (9)C26—H260.9500
C8—C131.390 (9)C27—H270.9500
C7—N1—C8126.7 (6)F2—C14—C4113.5 (6)
C7—N1—H1114 (4)F1—C14—C4112.3 (6)
C8—N1—H1120 (4)F3—C14—C4112.8 (6)
C21—N2—C22125.8 (5)C16—C15—C20119.8 (6)
C21—N2—H2125 (5)C16—C15—C21122.7 (6)
C22—N2—H2109 (5)C20—C15—C21117.6 (6)
C2—C1—C6120.4 (6)C15—C16—C17120.2 (6)
C2—C1—C7122.4 (6)C15—C16—H16119.9
C6—C1—C7117.2 (6)C17—C16—H16119.9
C1—C2—C3119.7 (6)C18—C17—C16119.6 (6)
C1—C2—H2A120.2C18—C17—H17120.2
C3—C2—H2A120.2C16—C17—H17120.2
C4—C3—C2119.9 (6)C17—C18—C19120.3 (6)
C4—C3—H3120.1C17—C18—C28120.8 (6)
C2—C3—H3120.1C19—C18—C28118.9 (6)
C5—C4—C3120.3 (6)C20—C19—C18119.8 (6)
C5—C4—C14119.9 (6)C20—C19—H19120.1
C3—C4—C14119.7 (7)C18—C19—H19120.1
C4—C5—C6119.9 (6)C19—C20—C15120.4 (6)
C4—C5—H5120.1C19—C20—H20119.8
C6—C5—H5120.1C15—C20—H20119.8
C5—C6—C1119.8 (6)O2—C21—N2123.7 (6)
C5—C6—H6120.1O2—C21—C15121.6 (6)
C1—C6—H6120.1N2—C21—C15114.7 (5)
O1—C7—N1123.6 (6)C23—C22—C27120.2 (6)
O1—C7—C1121.0 (6)C23—C22—N2117.9 (6)
N1—C7—C1115.5 (6)C27—C22—N2121.7 (6)
C9—C8—C13120.1 (6)C22—C23—C24120.3 (6)
C9—C8—N1117.9 (6)C22—C23—H23119.8
C13—C8—N1121.8 (6)C24—C23—H23119.8
C8—C9—C10120.4 (6)C25—C24—C23119.8 (6)
C8—C9—H9119.8C25—C24—H24120.1
C10—C9—H9119.8C23—C24—H24120.1
C9—C10—C11119.1 (6)C24—C25—C26120.6 (6)
C9—C10—H10120.5C24—C25—Br2A119.8 (5)
C11—C10—H10120.5C26—C25—Br2A119.5 (5)
C12—C11—C10120.5 (6)C27—C26—C25119.4 (6)
C12—C11—Br1A120.5 (5)C27—C26—H26120.3
C10—C11—Br1A119.0 (5)C25—C26—H26120.3
C11—C12—C13120.6 (6)C26—C27—C22119.5 (6)
C11—C12—H12119.7C26—C27—H27120.2
C13—C12—H12119.7C22—C27—H27120.2
C12—C13—C8119.3 (6)F6—C28—F4108.8 (7)
C12—C13—H13120.3F6—C28—F5105.9 (6)
C8—C13—H13120.3F4—C28—F5105.4 (7)
F2—C14—F1108.0 (7)F6—C28—C18112.4 (6)
F2—C14—F3105.7 (6)F4—C28—C18112.6 (6)
F1—C14—F3103.9 (7)F5—C28—C18111.3 (6)
C6—C1—C2—C30.4 (9)C20—C15—C16—C170.5 (10)
C7—C1—C2—C3178.5 (6)C21—C15—C16—C17178.6 (6)
C1—C2—C3—C40.2 (10)C15—C16—C17—C180.7 (10)
C2—C3—C4—C50.0 (10)C16—C17—C18—C190.2 (10)
C2—C3—C4—C14178.7 (6)C16—C17—C18—C28178.7 (6)
C3—C4—C5—C60.8 (10)C17—C18—C19—C200.3 (10)
C14—C4—C5—C6177.9 (6)C28—C18—C19—C20179.3 (6)
C4—C5—C6—C11.4 (10)C18—C19—C20—C150.5 (10)
C2—C1—C6—C51.2 (9)C16—C15—C20—C190.1 (10)
C7—C1—C6—C5179.4 (6)C21—C15—C20—C19179.2 (6)
C8—N1—C7—O13.7 (10)C22—N2—C21—O23.0 (10)
C8—N1—C7—C1175.9 (5)C22—N2—C21—C15177.2 (5)
C2—C1—C7—O1149.7 (6)C16—C15—C21—O2149.0 (6)
C6—C1—C7—O128.5 (9)C20—C15—C21—O230.2 (9)
C2—C1—C7—N129.9 (8)C16—C15—C21—N231.2 (8)
C6—C1—C7—N1151.9 (6)C20—C15—C21—N2149.7 (6)
C7—N1—C8—C9150.8 (6)C21—N2—C22—C23149.4 (6)
C7—N1—C8—C1333.5 (9)C21—N2—C22—C2733.9 (9)
C13—C8—C9—C100.9 (9)C27—C22—C23—C240.4 (9)
N1—C8—C9—C10176.7 (6)N2—C22—C23—C24176.2 (5)
C8—C9—C10—C111.0 (9)C22—C23—C24—C250.2 (9)
C9—C10—C11—C120.2 (9)C23—C24—C25—C261.0 (9)
C9—C10—C11—Br1A179.0 (5)C23—C24—C25—Br2A179.5 (5)
C10—C11—C12—C130.6 (9)C24—C25—C26—C271.0 (9)
Br1A—C11—C12—C13179.8 (5)Br2A—C25—C26—C27179.4 (5)
C11—C12—C13—C80.7 (9)C25—C26—C27—C220.4 (9)
C9—C8—C13—C120.1 (9)C23—C22—C27—C260.3 (9)
N1—C8—C13—C12175.7 (6)N2—C22—C27—C26176.2 (6)
C5—C4—C14—F224.2 (10)C17—C18—C28—F6129.7 (7)
C3—C4—C14—F2157.1 (7)C19—C18—C28—F651.3 (9)
C5—C4—C14—F198.7 (8)C17—C18—C28—F4107.0 (8)
C3—C4—C14—F180.1 (9)C19—C18—C28—F472.0 (9)
C5—C4—C14—F3144.3 (7)C17—C18—C28—F511.1 (9)
C3—C4—C14—F336.9 (9)C19—C18—C28—F5169.9 (6)
(PI22) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.965 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.7974 (15) ÅCell parameters from 6946 reflections
b = 6.5752 (5) Åθ = 3.3–30.0°
c = 9.6889 (7) ŵ = 2.45 mm1
β = 93.899 (4)°T = 100 K
V = 1321.86 (17) Å3Block
Z = 40.40 × 0.30 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2275 reflections with I > 2σ(I)
φ and ω scansRint = 0.024
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.5°, θmin = 3.0°
Tmin = 0.433, Tmax = 0.672h = 2525
9320 measured reflectionsk = 76
2421 independent reflectionsl = 1111
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.019H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.046 w = 1/[σ2(Fo2) + (0.019P)2 + 0.841P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
2421 reflectionsΔρmax = 0.37 e Å3
185 parametersΔρmin = 0.43 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.41593 (2)0.71126 (2)0.01992 (2)0.01929 (7)
F10.12736 (7)0.9053 (2)0.23085 (14)0.0271 (3)
F20.09167 (8)0.6883 (2)0.37202 (14)0.0326 (4)
F30.03361 (8)0.7762 (3)0.19112 (17)0.0393 (4)
O10.24062 (8)0.6929 (2)0.34159 (14)0.0185 (4)
N10.27383 (9)0.7899 (3)0.13200 (17)0.0144 (4)
H10.2692 (13)0.779 (4)0.0454 (17)0.016 (7)*
C10.18814 (10)0.5464 (3)0.14031 (19)0.0140 (5)
C20.21008 (11)0.3906 (4)0.05926 (19)0.0155 (5)
H20.2547570.3810040.0453680.019*
C30.16800 (13)0.2492 (4)0.0016 (2)0.0197 (5)
H30.1838650.1419070.0555110.024*
C40.10255 (13)0.2640 (4)0.0161 (2)0.0215 (5)
H40.0734790.1668330.0254360.026*
C50.07984 (11)0.4203 (4)0.0942 (2)0.0191 (5)
H50.0349340.4309970.1053920.023*
C60.12176 (11)0.5621 (4)0.15674 (19)0.0155 (5)
C70.23586 (11)0.6842 (3)0.2148 (2)0.0142 (5)
C80.31863 (10)0.9402 (3)0.18238 (18)0.0136 (5)
C90.38230 (11)0.9412 (4)0.14658 (19)0.0151 (5)
C100.42449 (11)1.0924 (4)0.1954 (2)0.0191 (5)
H100.4678031.0924280.1699680.023*
C110.40337 (13)1.2431 (4)0.2813 (2)0.0221 (5)
H110.4322791.3461090.3154670.026*
C120.33988 (13)1.2436 (4)0.3175 (2)0.0193 (5)
H120.3254151.3467800.3766460.023*
C130.29777 (11)1.0943 (3)0.26767 (19)0.0164 (5)
H130.2542421.0965140.2916570.020*
C140.09438 (12)0.7328 (4)0.2378 (2)0.0211 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01580 (10)0.02337 (12)0.01910 (9)0.00098 (6)0.00418 (6)0.00406 (6)
F10.0307 (8)0.0185 (8)0.0329 (7)0.0031 (7)0.0087 (6)0.0006 (6)
F20.0482 (11)0.0314 (9)0.0202 (7)0.0015 (7)0.0162 (7)0.0008 (6)
F30.0164 (9)0.0524 (11)0.0490 (10)0.0134 (8)0.0005 (7)0.0160 (8)
O10.0200 (9)0.0268 (10)0.0088 (7)0.0036 (7)0.0010 (6)0.0002 (6)
N10.0135 (10)0.0219 (11)0.0077 (8)0.0038 (8)0.0006 (7)0.0001 (7)
C10.0161 (12)0.0178 (12)0.0081 (8)0.0009 (10)0.0001 (7)0.0044 (8)
C20.0144 (12)0.0202 (14)0.0119 (9)0.0013 (10)0.0007 (8)0.0021 (9)
C30.0258 (14)0.0175 (13)0.0155 (11)0.0009 (11)0.0007 (9)0.0010 (9)
C40.0234 (14)0.0204 (14)0.0201 (11)0.0082 (11)0.0040 (10)0.0025 (9)
C50.0139 (12)0.0233 (14)0.0201 (10)0.0042 (10)0.0007 (8)0.0048 (9)
C60.0146 (11)0.0199 (13)0.0121 (9)0.0013 (10)0.0014 (8)0.0052 (9)
C70.0122 (12)0.0166 (13)0.0138 (10)0.0035 (9)0.0012 (8)0.0003 (8)
C80.0157 (11)0.0158 (12)0.0091 (9)0.0019 (10)0.0010 (8)0.0047 (8)
C90.0166 (12)0.0177 (12)0.0111 (9)0.0000 (10)0.0013 (8)0.0026 (8)
C100.0152 (12)0.0210 (14)0.0210 (10)0.0032 (10)0.0012 (9)0.0047 (9)
C110.0239 (14)0.0173 (14)0.0243 (12)0.0065 (11)0.0030 (10)0.0002 (10)
C120.0246 (14)0.0157 (13)0.0176 (11)0.0025 (10)0.0000 (9)0.0006 (9)
C130.0162 (12)0.0195 (14)0.0132 (9)0.0003 (10)0.0002 (8)0.0025 (9)
C140.0140 (13)0.0289 (15)0.0205 (12)0.0003 (11)0.0023 (9)0.0038 (10)
Geometric parameters (Å, º) top
I1—C92.097 (2)C4—C51.379 (3)
F1—C141.329 (3)C4—H40.9500
F2—C141.338 (3)C5—C61.387 (3)
F3—C141.344 (3)C5—H50.9500
O1—C71.227 (3)C6—C141.504 (3)
N1—C71.355 (3)C8—C91.392 (3)
N1—C81.422 (3)C8—C131.395 (3)
N1—H10.841 (16)C9—C101.387 (3)
C1—C21.387 (3)C10—C111.385 (3)
C1—C61.404 (3)C10—H100.9500
C1—C71.493 (3)C11—C121.389 (4)
C2—C31.382 (3)C11—H110.9500
C2—H20.9500C12—C131.381 (3)
C3—C41.387 (4)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8123.23 (17)C9—C8—C13118.9 (2)
C7—N1—H1121.0 (18)C9—C8—N1122.01 (19)
C8—N1—H1115.4 (17)C13—C8—N1119.04 (19)
C2—C1—C6118.8 (2)C10—C9—C8120.6 (2)
C2—C1—C7119.25 (19)C10—C9—I1119.18 (16)
C6—C1—C7121.80 (19)C8—C9—I1120.23 (16)
C3—C2—C1121.1 (2)C11—C10—C9119.9 (2)
C3—C2—H2119.5C11—C10—H10120.0
C1—C2—H2119.5C9—C10—H10120.0
C2—C3—C4119.9 (2)C10—C11—C12119.9 (2)
C2—C3—H3120.1C10—C11—H11120.0
C4—C3—H3120.1C12—C11—H11120.0
C5—C4—C3119.7 (2)C13—C12—C11120.1 (2)
C5—C4—H4120.1C13—C12—H12120.0
C3—C4—H4120.1C11—C12—H12120.0
C4—C5—C6120.8 (2)C12—C13—C8120.5 (2)
C4—C5—H5119.6C12—C13—H13119.7
C6—C5—H5119.6C8—C13—H13119.7
C5—C6—C1119.7 (2)F1—C14—F2106.98 (19)
C5—C6—C14118.7 (2)F1—C14—F3106.2 (2)
C1—C6—C14121.6 (2)F2—C14—F3105.83 (19)
O1—C7—N1123.9 (2)F1—C14—C6113.27 (18)
O1—C7—C1121.16 (19)F2—C14—C6112.76 (19)
N1—C7—C1114.85 (17)F3—C14—C6111.3 (2)
C6—C1—C2—C31.8 (3)C7—N1—C8—C1350.9 (3)
C7—C1—C2—C3174.34 (19)C13—C8—C9—C100.3 (3)
C1—C2—C3—C41.1 (3)N1—C8—C9—C10178.77 (19)
C2—C3—C4—C50.1 (3)C13—C8—C9—I1179.50 (15)
C3—C4—C5—C60.7 (3)N1—C8—C9—I12.0 (3)
C4—C5—C6—C10.0 (3)C8—C9—C10—C110.4 (3)
C4—C5—C6—C14178.4 (2)I1—C9—C10—C11178.77 (16)
C2—C1—C6—C51.2 (3)C9—C10—C11—C120.5 (3)
C7—C1—C6—C5174.80 (19)C10—C11—C12—C130.2 (3)
C2—C1—C6—C14177.17 (19)C11—C12—C13—C80.9 (3)
C7—C1—C6—C146.8 (3)C9—C8—C13—C121.0 (3)
C8—N1—C7—O17.4 (4)N1—C8—C13—C12179.50 (19)
C8—N1—C7—C1174.9 (2)C5—C6—C14—F1146.6 (2)
C2—C1—C7—O1117.2 (2)C1—C6—C14—F131.8 (3)
C6—C1—C7—O158.8 (3)C5—C6—C14—F291.7 (3)
C2—C1—C7—N160.5 (3)C1—C6—C14—F289.9 (3)
C6—C1—C7—N1123.5 (2)C5—C6—C14—F327.0 (3)
C7—N1—C8—C9130.7 (2)C1—C6—C14—F3151.4 (2)
(PI23) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.894 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.0022 (10) ÅCell parameters from 9276 reflections
b = 4.7359 (4) Åθ = 2.3–30.2°
c = 26.562 (3) ŵ = 2.36 mm1
β = 97.636 (3)°T = 104 K
V = 1371.7 (2) Å3Plate
Z = 40.50 × 0.11 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2873 reflections with I > 2σ(I)
φ and ω scansRint = 0.047
Absorption correction: multi-scan
SADABS 2014/4
θmax = 28.3°, θmin = 3.1°
Tmin = 0.436, Tmax = 0.596h = 1314
9961 measured reflectionsk = 65
3401 independent reflectionsl = 3532
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0395P)2 + 1.7205P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3401 reflectionsΔρmax = 1.07 e Å3
195 parametersΔρmin = 1.17 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
I10.11142 (2)0.84711 (4)0.05425 (2)0.02933 (10)
F1A0.2045 (5)0.328 (3)0.2824 (2)0.129 (4)0.668 (4)
F2A0.3620 (7)0.5581 (11)0.2545 (2)0.075 (2)0.668 (4)
F3A0.3469 (7)0.1429 (9)0.2355 (2)0.074 (2)0.668 (4)
F1B0.3750 (12)0.339 (7)0.2389 (5)0.129 (4)0.332 (4)
F2B0.2076 (15)0.140 (2)0.2621 (5)0.075 (2)0.332 (4)
F3B0.2278 (15)0.540 (2)0.2851 (4)0.074 (2)0.332 (4)
O10.3035 (3)0.1009 (4)0.05184 (10)0.0352 (7)
N10.2806 (3)0.5374 (5)0.01811 (10)0.0191 (6)
H10.273 (4)0.710 (5)0.0283 (18)0.049 (13)*
C10.2194 (3)0.4642 (6)0.10749 (12)0.0213 (7)
C20.1232 (4)0.6557 (7)0.11296 (15)0.0311 (8)
H20.0911990.7232530.0837050.037*
C30.0731 (4)0.7494 (11)0.16070 (17)0.0444 (10)
H30.0056170.8761400.1642110.053*
C40.1222 (4)0.6569 (8)0.20341 (16)0.0382 (9)
H40.0894860.7226540.2362110.046*
C50.2192 (4)0.4682 (7)0.19778 (14)0.0300 (8)
C60.2660 (4)0.3689 (6)0.15065 (14)0.0287 (8)
H60.3305220.2341820.1474590.034*
C70.2718 (3)0.3504 (6)0.05695 (13)0.0224 (7)
C80.3248 (3)0.4781 (6)0.03297 (12)0.0191 (6)
C90.2686 (3)0.5984 (6)0.07217 (13)0.0200 (7)
C100.3122 (4)0.5489 (8)0.12232 (14)0.0293 (8)
H100.2732540.6339280.1483450.035*
C110.4135 (4)0.3742 (8)0.13499 (16)0.0360 (9)
H110.4437120.3384410.1695910.043*
C120.4696 (4)0.2530 (9)0.09658 (16)0.0364 (9)
H120.5385990.1332090.1049960.044*
C130.4264 (3)0.3046 (6)0.04613 (15)0.0260 (8)
H130.4662610.2210260.0202230.031*
C140.2742 (5)0.3751 (8)0.24387 (16)0.0419 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02713 (16)0.02917 (13)0.03330 (15)0.01031 (9)0.00989 (11)0.00373 (9)
F1A0.042 (3)0.300 (13)0.044 (3)0.014 (6)0.003 (3)0.086 (6)
F2A0.112 (5)0.053 (2)0.076 (4)0.019 (3)0.068 (4)0.010 (2)
F3A0.139 (6)0.048 (2)0.047 (3)0.030 (3)0.057 (3)0.0059 (18)
F1B0.042 (3)0.300 (13)0.044 (3)0.014 (6)0.003 (3)0.086 (6)
F2B0.112 (5)0.053 (2)0.076 (4)0.019 (3)0.068 (4)0.010 (2)
F3B0.139 (6)0.048 (2)0.047 (3)0.030 (3)0.057 (3)0.0059 (18)
O10.068 (2)0.0094 (9)0.0321 (14)0.0057 (11)0.0198 (15)0.0004 (9)
N10.0247 (15)0.0105 (10)0.0233 (13)0.0046 (10)0.0071 (12)0.0027 (10)
C10.0261 (18)0.0162 (13)0.0229 (16)0.0050 (13)0.0078 (15)0.0026 (12)
C20.026 (2)0.0428 (19)0.0242 (18)0.0060 (16)0.0020 (16)0.0086 (15)
C30.040 (3)0.058 (2)0.031 (2)0.016 (2)0.008 (2)0.007 (2)
C40.040 (2)0.049 (2)0.0241 (19)0.0024 (19)0.0025 (19)0.0044 (16)
C50.041 (2)0.0258 (15)0.0251 (18)0.0103 (16)0.0120 (17)0.0057 (13)
C60.043 (2)0.0185 (14)0.0281 (19)0.0007 (14)0.0153 (18)0.0032 (12)
C70.031 (2)0.0150 (13)0.0237 (16)0.0008 (13)0.0135 (16)0.0004 (11)
C80.0192 (16)0.0127 (12)0.0262 (16)0.0016 (12)0.0065 (14)0.0034 (11)
C90.0194 (17)0.0179 (13)0.0229 (16)0.0003 (12)0.0040 (14)0.0019 (11)
C100.031 (2)0.0330 (16)0.0246 (17)0.0048 (16)0.0071 (16)0.0019 (14)
C110.034 (2)0.045 (2)0.027 (2)0.0010 (18)0.0004 (18)0.0154 (16)
C120.029 (2)0.0371 (18)0.044 (2)0.0094 (17)0.0074 (19)0.0229 (18)
C130.0238 (19)0.0217 (15)0.0342 (19)0.0049 (13)0.0104 (17)0.0083 (13)
C140.064 (3)0.038 (2)0.027 (2)0.001 (2)0.018 (2)0.0011 (16)
Geometric parameters (Å, º) top
I1—C92.094 (3)C3—H30.9500
F1A—C141.215 (7)C4—C51.385 (6)
F2A—C141.355 (7)C4—H40.9500
F3A—C141.361 (7)C5—C61.372 (5)
F1B—C141.112 (14)C5—C141.502 (5)
F2B—C141.383 (12)C6—H60.9500
F3B—C141.387 (12)C8—C131.394 (5)
O1—C71.235 (3)C8—C91.401 (4)
N1—C71.353 (4)C9—C101.375 (5)
N1—C81.408 (4)C10—C111.393 (6)
N1—H10.864 (19)C10—H100.9500
C1—C21.387 (5)C11—C121.385 (6)
C1—C61.392 (4)C11—H110.9500
C1—C71.490 (5)C12—C131.383 (6)
C2—C31.386 (6)C12—H120.9500
C2—H20.9500C13—H130.9500
C3—C41.391 (6)
C7—N1—C8125.8 (3)C10—C9—C8121.3 (3)
C7—N1—H1113 (3)C10—C9—I1119.2 (2)
C8—N1—H1120 (3)C8—C9—I1119.5 (3)
C2—C1—C6119.0 (3)C9—C10—C11120.0 (3)
C2—C1—C7122.0 (3)C9—C10—H10120.0
C6—C1—C7119.0 (3)C11—C10—H10120.0
C3—C2—C1120.6 (3)C12—C11—C10119.3 (4)
C3—C2—H2119.7C12—C11—H11120.4
C1—C2—H2119.7C10—C11—H11120.4
C2—C3—C4119.7 (4)C13—C12—C11120.7 (4)
C2—C3—H3120.2C13—C12—H12119.6
C4—C3—H3120.2C11—C12—H12119.6
C5—C4—C3119.5 (4)C12—C13—C8120.5 (3)
C5—C4—H4120.2C12—C13—H13119.7
C3—C4—H4120.2C8—C13—H13119.7
C6—C5—C4120.7 (3)F1A—C14—F2A109.2 (6)
C6—C5—C14120.0 (4)F1A—C14—F3A106.4 (6)
C4—C5—C14119.3 (4)F2A—C14—F3A97.5 (5)
C5—C6—C1120.4 (3)F1B—C14—F2B113.1 (14)
C5—C6—H6119.8F1B—C14—F3B115.8 (14)
C1—C6—H6119.8F2B—C14—F3B93.1 (9)
O1—C7—N1123.5 (3)F1B—C14—C5116.8 (7)
O1—C7—C1121.0 (3)F1A—C14—C5117.6 (5)
N1—C7—C1115.5 (3)F2A—C14—C5110.9 (4)
C13—C8—C9118.2 (3)F3A—C14—C5113.3 (4)
C13—C8—N1121.5 (3)F2B—C14—C5105.7 (5)
C9—C8—N1120.3 (3)F3B—C14—C5109.5 (5)
C6—C1—C2—C30.5 (6)N1—C8—C9—I13.8 (4)
C7—C1—C2—C3177.4 (4)C8—C9—C10—C110.6 (5)
C1—C2—C3—C41.9 (7)I1—C9—C10—C11177.2 (3)
C2—C3—C4—C51.1 (7)C9—C10—C11—C120.3 (6)
C3—C4—C5—C61.0 (6)C10—C11—C12—C130.2 (6)
C3—C4—C5—C14178.3 (4)C11—C12—C13—C80.5 (6)
C4—C5—C6—C12.3 (5)C9—C8—C13—C120.2 (5)
C14—C5—C6—C1177.0 (3)N1—C8—C13—C12178.9 (3)
C2—C1—C6—C51.6 (5)C6—C5—C14—F1B35 (2)
C7—C1—C6—C5179.6 (3)C4—C5—C14—F1B144.3 (19)
C8—N1—C7—O10.7 (5)C6—C5—C14—F1A140.6 (8)
C8—N1—C7—C1178.8 (3)C4—C5—C14—F1A40.1 (9)
C2—C1—C7—O1141.1 (4)C6—C5—C14—F2A92.8 (5)
C6—C1—C7—O136.9 (5)C4—C5—C14—F2A86.6 (6)
C2—C1—C7—N138.5 (5)C6—C5—C14—F3A15.7 (7)
C6—C1—C7—N1143.5 (3)C4—C5—C14—F3A165.0 (5)
C7—N1—C8—C1340.4 (5)C6—C5—C14—F2B91.8 (8)
C7—N1—C8—C9140.9 (3)C4—C5—C14—F2B88.9 (8)
C13—C8—C9—C100.3 (5)C6—C5—C14—F3B169.1 (8)
N1—C8—C9—C10178.4 (3)C4—C5—C14—F3B10.2 (9)
C13—C8—C9—I1177.5 (2)
(PI24) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.937 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.5840 (16) ÅCell parameters from 3505 reflections
b = 7.1797 (5) Åθ = 3.0–27.9°
c = 9.1451 (7) ŵ = 2.42 mm1
β = 97.122 (4)°T = 100 K
V = 1341.10 (17) Å3Plate
Z = 40.40 × 0.20 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
1884 reflections with I > 2σ(I)
φ and ω scansRint = 0.031
Absorption correction: multi-scan
SADABS 2014/4
θmax = 25.0°, θmin = 3.0°
Tmin = 0.552, Tmax = 0.796h = 1524
5872 measured reflectionsk = 88
2238 independent reflectionsl = 109
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.0324P)2 + 4.3811P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
2238 reflectionsΔρmax = 0.82 e Å3
184 parametersΔρmin = 1.14 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.41038 (2)0.78861 (5)0.94315 (4)0.02273 (14)
F10.0510 (2)1.3634 (6)1.0365 (4)0.0603 (13)
F20.00029 (16)1.2753 (5)0.8321 (5)0.0451 (10)
F30.07676 (17)1.4743 (5)0.8363 (5)0.0468 (11)
O10.25009 (17)0.6045 (5)0.9884 (4)0.0170 (8)
N10.2688 (2)0.6838 (6)0.7570 (5)0.0144 (10)
H10.257 (3)0.756 (8)0.687 (6)0.017*
C10.1931 (2)0.8670 (7)0.8791 (5)0.0118 (11)
C20.2010 (3)1.0312 (7)0.8027 (6)0.0180 (12)
H20.2361331.0421570.7449030.022*
C30.1584 (3)1.1788 (7)0.8098 (6)0.0199 (13)
H30.1643021.2906390.7575450.024*
C40.1070 (3)1.1628 (7)0.8935 (6)0.0181 (12)
C50.0990 (3)1.0004 (7)0.9709 (6)0.0193 (13)
H50.0637840.9898061.0284850.023*
C60.1419 (2)0.8541 (7)0.9647 (6)0.0153 (12)
H60.1364540.7436991.0190890.018*
C70.2396 (2)0.7086 (7)0.8797 (6)0.0147 (11)
C80.3162 (2)0.5419 (7)0.7459 (6)0.0128 (11)
C90.2987 (3)0.3902 (7)0.6552 (6)0.0163 (12)
H90.2551350.3805970.6076510.020*
C100.3439 (3)0.2520 (7)0.6328 (7)0.0239 (14)
H100.3314860.1492960.5699600.029*
C110.4075 (3)0.2667 (7)0.7041 (6)0.0240 (14)
H110.4388140.1731590.6900040.029*
C120.4256 (3)0.4175 (7)0.7956 (6)0.0190 (12)
H120.4689670.4261980.8445670.023*
C130.3800 (3)0.5555 (7)0.8153 (6)0.0167 (12)
C140.0591 (3)1.3176 (8)0.8989 (7)0.0245 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0212 (2)0.0233 (2)0.0234 (2)0.00005 (17)0.00146 (15)0.00810 (17)
F10.085 (3)0.072 (3)0.024 (2)0.062 (3)0.005 (2)0.007 (2)
F20.0249 (19)0.030 (2)0.076 (3)0.0099 (16)0.0119 (19)0.0119 (19)
F30.044 (2)0.016 (2)0.084 (3)0.0120 (17)0.021 (2)0.0104 (19)
O10.025 (2)0.011 (2)0.016 (2)0.0051 (16)0.0057 (16)0.0015 (16)
N10.020 (2)0.013 (3)0.011 (3)0.0074 (19)0.0030 (19)0.0048 (19)
C10.013 (2)0.010 (3)0.012 (3)0.000 (2)0.001 (2)0.000 (2)
C20.021 (3)0.017 (3)0.017 (3)0.001 (2)0.006 (2)0.002 (2)
C30.029 (3)0.011 (3)0.020 (3)0.001 (2)0.005 (3)0.006 (2)
C40.019 (3)0.012 (3)0.022 (3)0.005 (2)0.001 (2)0.004 (2)
C50.020 (3)0.020 (3)0.019 (3)0.001 (2)0.006 (2)0.005 (2)
C60.018 (3)0.015 (3)0.013 (3)0.002 (2)0.001 (2)0.000 (2)
C70.014 (3)0.011 (3)0.018 (3)0.002 (2)0.001 (2)0.001 (2)
C80.019 (3)0.011 (3)0.010 (3)0.003 (2)0.005 (2)0.003 (2)
C90.023 (3)0.011 (3)0.017 (3)0.002 (2)0.009 (2)0.000 (2)
C100.035 (3)0.008 (3)0.031 (4)0.001 (2)0.015 (3)0.005 (2)
C110.028 (3)0.011 (3)0.036 (4)0.005 (2)0.016 (3)0.003 (2)
C120.018 (3)0.017 (3)0.024 (3)0.004 (2)0.006 (2)0.003 (2)
C130.022 (3)0.015 (3)0.014 (3)0.001 (2)0.006 (2)0.001 (2)
C140.030 (3)0.016 (3)0.028 (4)0.005 (3)0.004 (3)0.001 (3)
Geometric parameters (Å, º) top
I1—C132.092 (5)C4—C51.385 (8)
F1—C141.331 (7)C4—C141.491 (7)
F2—C141.322 (7)C5—C61.378 (7)
F3—C141.333 (6)C5—H50.9500
O1—C71.241 (6)C6—H60.9500
N1—C71.349 (6)C8—C91.389 (7)
N1—C81.422 (6)C8—C131.390 (7)
N1—H10.83 (6)C9—C101.392 (7)
C1—C21.390 (7)C9—H90.9500
C1—C61.393 (7)C10—C111.393 (8)
C1—C71.486 (7)C10—H100.9500
C2—C31.382 (7)C11—C121.390 (7)
C2—H20.9500C11—H110.9500
C3—C41.385 (7)C12—C131.391 (7)
C3—H30.9500C12—H120.9500
C7—N1—C8122.3 (4)C9—C8—C13119.2 (5)
C7—N1—H1116 (4)C9—C8—N1118.4 (5)
C8—N1—H1122 (4)C13—C8—N1122.3 (5)
C2—C1—C6118.9 (5)C8—C9—C10121.3 (5)
C2—C1—C7122.4 (4)C8—C9—H9119.4
C6—C1—C7118.6 (5)C10—C9—H9119.4
C3—C2—C1120.8 (5)C9—C10—C11118.9 (5)
C3—C2—H2119.6C9—C10—H10120.6
C1—C2—H2119.6C11—C10—H10120.6
C2—C3—C4119.7 (5)C12—C11—C10120.4 (5)
C2—C3—H3120.2C12—C11—H11119.8
C4—C3—H3120.2C10—C11—H11119.8
C5—C4—C3120.0 (5)C11—C12—C13119.9 (5)
C5—C4—C14119.3 (5)C11—C12—H12120.1
C3—C4—C14120.7 (5)C13—C12—H12120.1
C6—C5—C4120.2 (5)C8—C13—C12120.3 (5)
C6—C5—H5119.9C8—C13—I1120.7 (4)
C4—C5—H5119.9C12—C13—I1118.9 (4)
C5—C6—C1120.4 (5)F2—C14—F1106.2 (5)
C5—C6—H6119.8F2—C14—F3106.1 (5)
C1—C6—H6119.8F1—C14—F3105.7 (5)
O1—C7—N1122.4 (5)F2—C14—C4112.7 (5)
O1—C7—C1120.8 (4)F1—C14—C4112.1 (5)
N1—C7—C1116.8 (4)F3—C14—C4113.5 (5)
C6—C1—C2—C30.8 (8)C13—C8—C9—C100.0 (7)
C7—C1—C2—C3177.2 (5)N1—C8—C9—C10176.2 (5)
C1—C2—C3—C40.3 (8)C8—C9—C10—C110.5 (8)
C2—C3—C4—C50.7 (8)C9—C10—C11—C120.2 (8)
C2—C3—C4—C14177.9 (5)C10—C11—C12—C130.6 (8)
C3—C4—C5—C60.2 (8)C9—C8—C13—C120.8 (8)
C14—C4—C5—C6178.5 (5)N1—C8—C13—C12176.9 (5)
C4—C5—C6—C10.9 (8)C9—C8—C13—I1176.4 (4)
C2—C1—C6—C51.3 (8)N1—C8—C13—I10.4 (7)
C7—C1—C6—C5177.9 (5)C11—C12—C13—C81.1 (8)
C8—N1—C7—O13.1 (8)C11—C12—C13—I1176.2 (4)
C8—N1—C7—C1177.4 (4)C5—C4—C14—F267.6 (7)
C2—C1—C7—O1148.6 (5)C3—C4—C14—F2111.0 (6)
C6—C1—C7—O127.8 (7)C5—C4—C14—F152.1 (7)
C2—C1—C7—N131.9 (7)C3—C4—C14—F1129.2 (6)
C6—C1—C7—N1151.7 (5)C5—C4—C14—F3171.7 (5)
C7—N1—C8—C9108.6 (6)C3—C4—C14—F39.6 (8)
C7—N1—C8—C1375.3 (7)
(PI32) top
Crystal data top
C14H9F3INODx = 1.882 Mg m3
Mr = 391.12Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21Cell parameters from 7820 reflections
a = 7.9499 (4) Åθ = 2.8–27.3°
b = 19.6384 (10) ŵ = 2.35 mm1
c = 8.8397 (4) ÅT = 110 K
V = 1380.08 (12) Å3Plate
Z = 40.50 × 0.10 × 0.05 mm
F(000) = 752
Data collection top
Bruker APEX-II CCD
diffractometer
3706 reflections with I > 2σ(I)
φ and ω scansRint = 0.025
Absorption correction: multi-scan
SADABS 2014/4
θmax = 30.1°, θmin = 2.8°
Tmin = 0.513, Tmax = 0.729h = 1111
12915 measured reflectionsk = 2327
3913 independent reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.017 w = 1/[σ2(Fo2) + (0.0093P)2 + 0.1106P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.037(Δ/σ)max = 0.001
S = 1.09Δρmax = 0.54 e Å3
3913 reflectionsΔρmin = 0.31 e Å3
184 parametersAbsolute structure: Flack x determined using 1597 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraintAbsolute structure parameter: 0.011 (9)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.43314 (2)0.46752 (2)0.24777 (3)0.01618 (5)
F10.3102 (2)0.12538 (10)0.5534 (2)0.0329 (4)
F20.1924 (3)0.02807 (9)0.5875 (3)0.0423 (5)
F30.0997 (3)0.09569 (11)0.4156 (2)0.0385 (5)
O10.1093 (2)0.25026 (11)0.4680 (2)0.0219 (4)
N10.2660 (3)0.27656 (11)0.6765 (2)0.0151 (4)
H10.287 (4)0.2640 (15)0.782 (3)0.018*
C10.0403 (3)0.19491 (13)0.6977 (3)0.0135 (5)
C20.0674 (3)0.22098 (14)0.8070 (3)0.0157 (5)
H20.0673830.2683950.8283130.019*
C30.1757 (3)0.17763 (15)0.8857 (3)0.0222 (5)
H30.2514330.1958120.9583730.027*
C40.1730 (3)0.10857 (16)0.8583 (3)0.0250 (6)
H40.2472890.0792940.9117990.030*
C50.0623 (2)0.08169 (12)0.7529 (6)0.0227 (5)
H50.0586320.0339150.7364000.027*
C60.0432 (3)0.12452 (13)0.6714 (3)0.0166 (5)
C70.1428 (3)0.24329 (12)0.6025 (3)0.0144 (4)
C80.3907 (3)0.31811 (13)0.6080 (3)0.0143 (5)
C90.5535 (3)0.31334 (14)0.6653 (3)0.0169 (5)
H90.5773590.2834720.7470320.020*
C100.6812 (3)0.35265 (14)0.6018 (3)0.0181 (5)
H100.7922560.3493970.6408860.022*
C110.6482 (3)0.39656 (13)0.4822 (3)0.0161 (5)
H110.7356480.4229250.4381400.019*
C120.4843 (3)0.40101 (12)0.4284 (3)0.0136 (4)
C130.3538 (3)0.36289 (13)0.4904 (3)0.0131 (4)
H130.2421780.3673010.4533390.016*
C140.1614 (4)0.09382 (16)0.5569 (3)0.0258 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01555 (6)0.01550 (8)0.01750 (7)0.00168 (4)0.00087 (9)0.00499 (8)
F10.0210 (7)0.0418 (11)0.0360 (10)0.0020 (7)0.0080 (7)0.0115 (8)
F20.0498 (12)0.0231 (11)0.0540 (13)0.0144 (7)0.0065 (10)0.0082 (8)
F30.0416 (10)0.0514 (13)0.0223 (9)0.0078 (9)0.0016 (8)0.0152 (9)
O10.0229 (8)0.0322 (11)0.0105 (8)0.0107 (8)0.0028 (7)0.0046 (8)
N10.0168 (9)0.0191 (11)0.0094 (10)0.0033 (8)0.0003 (8)0.0021 (8)
C10.0126 (9)0.0180 (13)0.0099 (9)0.0016 (9)0.0026 (7)0.0027 (8)
C20.0167 (11)0.0163 (13)0.0139 (10)0.0001 (9)0.0007 (8)0.0018 (9)
C30.0179 (11)0.0303 (15)0.0185 (12)0.0001 (11)0.0049 (10)0.0050 (10)
C40.0200 (12)0.0281 (16)0.0268 (14)0.0068 (11)0.0023 (11)0.0098 (11)
C50.0229 (10)0.0163 (11)0.0287 (11)0.0037 (8)0.0057 (15)0.0019 (19)
C60.0148 (10)0.0184 (13)0.0167 (12)0.0003 (9)0.0026 (9)0.0012 (10)
C70.0149 (10)0.0167 (12)0.0115 (10)0.0004 (9)0.0020 (9)0.0003 (9)
C80.0157 (10)0.0163 (13)0.0109 (10)0.0028 (9)0.0020 (9)0.0011 (9)
C90.0185 (11)0.0196 (13)0.0127 (11)0.0031 (9)0.0019 (9)0.0034 (9)
C100.0151 (10)0.0220 (14)0.0170 (11)0.0044 (9)0.0040 (9)0.0022 (9)
C110.0154 (10)0.0158 (12)0.0170 (11)0.0041 (9)0.0010 (9)0.0008 (9)
C120.0161 (10)0.0125 (12)0.0124 (10)0.0024 (9)0.0008 (9)0.0006 (9)
C130.0141 (10)0.0146 (12)0.0105 (10)0.0002 (9)0.0003 (8)0.0016 (8)
C140.0292 (14)0.0240 (15)0.0242 (13)0.0050 (11)0.0005 (11)0.0070 (11)
Geometric parameters (Å, º) top
I1—C122.102 (2)C4—C51.386 (5)
F1—C141.336 (3)C4—H40.9500
F2—C141.342 (3)C5—C61.390 (4)
F3—C141.342 (3)C5—H50.9500
O1—C71.226 (3)C6—C141.506 (4)
N1—C71.347 (3)C8—C131.393 (3)
N1—C81.419 (3)C8—C91.393 (3)
N1—H10.98 (3)C9—C101.393 (3)
C1—C21.389 (3)C9—H90.9500
C1—C61.402 (4)C10—C111.390 (3)
C1—C71.509 (3)C10—H100.9500
C2—C31.396 (4)C11—C121.390 (3)
C2—H20.9500C11—H110.9500
C3—C41.378 (4)C12—C131.392 (3)
C3—H30.9500C13—H130.9500
C7—N1—C8125.4 (2)C13—C8—C9120.6 (2)
C7—N1—H1117.8 (18)C13—C8—N1122.3 (2)
C8—N1—H1115.4 (18)C9—C8—N1117.1 (2)
C2—C1—C6119.3 (2)C10—C9—C8119.6 (2)
C2—C1—C7119.3 (2)C10—C9—H9120.2
C6—C1—C7121.3 (2)C8—C9—H9120.2
C1—C2—C3120.1 (3)C11—C10—C9120.8 (2)
C1—C2—H2119.9C11—C10—H10119.6
C3—C2—H2119.9C9—C10—H10119.6
C4—C3—C2120.2 (2)C12—C11—C10118.4 (2)
C4—C3—H3119.9C12—C11—H11120.8
C2—C3—H3119.9C10—C11—H11120.8
C3—C4—C5120.2 (2)C11—C12—C13122.0 (2)
C3—C4—H4119.9C11—C12—I1118.70 (17)
C5—C4—H4119.9C13—C12—I1119.28 (17)
C4—C5—C6120.1 (2)C12—C13—C8118.5 (2)
C4—C5—H5119.9C12—C13—H13120.8
C6—C5—H5119.9C8—C13—H13120.8
C5—C6—C1120.0 (2)F1—C14—F2106.7 (2)
C5—C6—C14118.9 (3)F1—C14—F3106.8 (2)
C1—C6—C14121.1 (2)F2—C14—F3106.3 (2)
O1—C7—N1125.1 (2)F1—C14—C6112.5 (2)
O1—C7—C1119.6 (2)F2—C14—C6111.4 (2)
N1—C7—C1115.3 (2)F3—C14—C6112.7 (2)
C6—C1—C2—C32.3 (3)C7—N1—C8—C9140.0 (3)
C7—C1—C2—C3173.5 (2)C13—C8—C9—C101.4 (4)
C1—C2—C3—C41.8 (4)N1—C8—C9—C10179.6 (2)
C2—C3—C4—C50.3 (4)C8—C9—C10—C110.0 (4)
C3—C4—C5—C61.8 (5)C9—C10—C11—C120.8 (4)
C4—C5—C6—C11.2 (5)C10—C11—C12—C130.2 (4)
C4—C5—C6—C14179.6 (3)C10—C11—C12—I1179.83 (19)
C2—C1—C6—C50.8 (4)C11—C12—C13—C81.2 (4)
C7—C1—C6—C5175.0 (3)I1—C12—C13—C8178.77 (17)
C2—C1—C6—C14178.3 (2)C9—C8—C13—C122.0 (4)
C7—C1—C6—C145.9 (3)N1—C8—C13—C12179.1 (2)
C8—N1—C7—O18.7 (4)C5—C6—C14—F1142.6 (3)
C8—N1—C7—C1172.1 (2)C1—C6—C14—F136.5 (3)
C2—C1—C7—O1109.9 (3)C5—C6—C14—F222.9 (4)
C6—C1—C7—O165.9 (3)C1—C6—C14—F2156.3 (2)
C2—C1—C7—N169.4 (3)C5—C6—C14—F396.6 (3)
C6—C1—C7—N1114.8 (2)C1—C6—C14—F384.3 (3)
C7—N1—C8—C1341.1 (4)
(PI33) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.924 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 26.9793 (16) ÅCell parameters from 9167 reflections
b = 5.2899 (4) Åθ = 3.0–30.1°
c = 9.5068 (6) ŵ = 2.40 mm1
β = 95.747 (2)°T = 107 K
V = 1349.97 (16) Å3Plate
Z = 40.45 × 0.24 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3349 reflections with I > 2σ(I)
φ and ω scansRint = 0.030
Absorption correction: multi-scan
SADABS 2014/4
θmax = 29.1°, θmin = 3.0°
Tmin = 0.543, Tmax = 0.726h = 3636
25810 measured reflectionsk = 77
3608 independent reflectionsl = 1311
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.021H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.050 w = 1/[σ2(Fo2) + (0.0209P)2 + 1.1723P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
3608 reflectionsΔρmax = 0.72 e Å3
185 parametersΔρmin = 0.45 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.45193 (2)0.28115 (2)0.31304 (2)0.02261 (5)
F10.02629 (5)0.0664 (3)0.66390 (17)0.0474 (4)
F20.03423 (5)0.3094 (3)0.58937 (16)0.0425 (4)
F30.07066 (5)0.1984 (3)0.79042 (14)0.0362 (3)
O10.24363 (4)0.3883 (2)0.69236 (12)0.0193 (2)
N10.26407 (5)0.3076 (3)0.46986 (16)0.0157 (3)
H10.2560 (9)0.237 (4)0.398 (3)0.016 (5)*
C10.18920 (6)0.1230 (3)0.54513 (17)0.0142 (3)
C20.18758 (6)0.0863 (3)0.45547 (18)0.0171 (3)
H20.2160670.1305000.4096160.021*
C30.14448 (7)0.2303 (3)0.4330 (2)0.0193 (3)
H30.1437730.3739050.3728800.023*
C40.10220 (6)0.1652 (3)0.49835 (19)0.0191 (3)
H40.0725060.2617380.4817000.023*
C50.10411 (6)0.0429 (3)0.58816 (17)0.0164 (3)
C60.14731 (6)0.1862 (3)0.61310 (17)0.0157 (3)
H60.1483300.3261090.6759530.019*
C70.23459 (6)0.2842 (3)0.57640 (18)0.0144 (3)
C80.31084 (6)0.4336 (3)0.48033 (17)0.0152 (3)
C90.34800 (6)0.3315 (3)0.40522 (18)0.0163 (3)
H90.3416530.1853480.3482150.020*
C100.39445 (6)0.4477 (3)0.41532 (18)0.0176 (3)
C110.40422 (6)0.6656 (3)0.49535 (19)0.0204 (3)
H110.4360930.7434240.5010650.025*
C120.36638 (7)0.7666 (3)0.5666 (2)0.0210 (4)
H120.3724650.9166790.6204860.025*
C130.31974 (6)0.6529 (3)0.56090 (18)0.0185 (3)
H130.2943000.7233220.6110300.022*
C140.05874 (6)0.1215 (4)0.65816 (19)0.0197 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.01301 (6)0.02980 (7)0.02599 (8)0.00099 (4)0.00678 (4)0.00337 (4)
F10.0381 (7)0.0445 (8)0.0657 (10)0.0206 (6)0.0350 (7)0.0164 (7)
F20.0288 (7)0.0630 (9)0.0380 (8)0.0237 (6)0.0149 (6)0.0207 (7)
F30.0210 (6)0.0652 (9)0.0227 (6)0.0063 (6)0.0042 (5)0.0149 (6)
O10.0198 (6)0.0267 (6)0.0117 (6)0.0031 (5)0.0024 (4)0.0013 (5)
N10.0141 (6)0.0224 (7)0.0110 (7)0.0036 (5)0.0037 (5)0.0021 (5)
C10.0138 (7)0.0170 (7)0.0120 (7)0.0005 (6)0.0016 (5)0.0030 (6)
C20.0163 (7)0.0203 (8)0.0153 (8)0.0019 (6)0.0048 (6)0.0018 (6)
C30.0214 (9)0.0189 (8)0.0178 (9)0.0011 (6)0.0036 (7)0.0022 (6)
C40.0181 (8)0.0212 (8)0.0181 (8)0.0040 (6)0.0026 (6)0.0004 (6)
C50.0149 (7)0.0213 (8)0.0135 (8)0.0002 (6)0.0035 (6)0.0028 (6)
C60.0163 (7)0.0180 (8)0.0131 (8)0.0005 (6)0.0032 (6)0.0013 (6)
C70.0116 (7)0.0190 (7)0.0127 (7)0.0014 (6)0.0022 (6)0.0026 (6)
C80.0135 (7)0.0193 (7)0.0129 (7)0.0014 (6)0.0020 (6)0.0028 (6)
C90.0146 (7)0.0193 (8)0.0153 (8)0.0017 (6)0.0022 (6)0.0009 (6)
C100.0129 (7)0.0226 (8)0.0175 (8)0.0005 (6)0.0028 (6)0.0048 (6)
C110.0156 (8)0.0242 (9)0.0209 (9)0.0045 (6)0.0007 (6)0.0047 (7)
C120.0217 (9)0.0198 (8)0.0212 (9)0.0038 (6)0.0002 (7)0.0006 (6)
C130.0180 (8)0.0210 (8)0.0169 (8)0.0000 (6)0.0031 (6)0.0002 (6)
C140.0127 (7)0.0293 (9)0.0175 (8)0.0038 (7)0.0035 (6)0.0025 (7)
Geometric parameters (Å, º) top
I1—C102.1045 (17)C4—C51.391 (2)
F1—C141.329 (2)C4—H40.9500
F2—C141.329 (2)C5—C61.390 (2)
F3—C141.330 (2)C5—C141.509 (2)
O1—C71.235 (2)C6—H60.9500
N1—C71.355 (2)C8—C91.396 (2)
N1—C81.422 (2)C8—C131.398 (2)
N1—H10.79 (3)C9—C101.390 (2)
C1—C21.395 (2)C9—H90.9500
C1—C61.397 (2)C10—C111.392 (3)
C1—C71.497 (2)C11—C121.388 (3)
C2—C31.388 (2)C11—H110.9500
C2—H20.9500C12—C131.391 (2)
C3—C41.395 (2)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.02 (15)C9—C8—C13120.55 (15)
C7—N1—H1118.2 (17)C9—C8—N1117.43 (15)
C8—N1—H1116.6 (17)C13—C8—N1122.01 (15)
C2—C1—C6119.66 (15)C10—C9—C8118.83 (16)
C2—C1—C7123.23 (14)C10—C9—H9120.6
C6—C1—C7117.09 (15)C8—C9—H9120.6
C3—C2—C1120.24 (15)C9—C10—C11121.59 (16)
C3—C2—H2119.9C9—C10—I1118.94 (13)
C1—C2—H2119.9C11—C10—I1119.43 (12)
C2—C3—C4120.37 (16)C12—C11—C10118.53 (16)
C2—C3—H3119.8C12—C11—H11120.7
C4—C3—H3119.8C10—C11—H11120.7
C5—C4—C3119.13 (16)C11—C12—C13121.42 (17)
C5—C4—H4120.4C11—C12—H12119.3
C3—C4—H4120.4C13—C12—H12119.3
C6—C5—C4121.00 (15)C12—C13—C8119.05 (16)
C6—C5—C14118.52 (15)C12—C13—H13120.5
C4—C5—C14120.46 (15)C8—C13—H13120.5
C5—C6—C1119.58 (15)F2—C14—F1106.39 (16)
C5—C6—H6120.2F2—C14—F3107.31 (17)
C1—C6—H6120.2F1—C14—F3106.73 (15)
O1—C7—N1123.27 (15)F2—C14—C5112.01 (14)
O1—C7—C1121.05 (15)F1—C14—C5112.25 (16)
N1—C7—C1115.68 (15)F3—C14—C5111.80 (14)
C6—C1—C2—C30.4 (2)C7—N1—C8—C1336.7 (2)
C7—C1—C2—C3178.86 (15)C13—C8—C9—C101.9 (2)
C1—C2—C3—C40.9 (3)N1—C8—C9—C10178.84 (15)
C2—C3—C4—C51.2 (3)C8—C9—C10—C111.6 (3)
C3—C4—C5—C60.2 (3)C8—C9—C10—I1176.05 (12)
C3—C4—C5—C14178.76 (16)C9—C10—C11—C120.2 (3)
C4—C5—C6—C11.1 (2)I1—C10—C11—C12177.41 (13)
C14—C5—C6—C1177.50 (15)C10—C11—C12—C130.9 (3)
C2—C1—C6—C51.4 (2)C11—C12—C13—C80.6 (3)
C7—C1—C6—C5179.92 (14)C9—C8—C13—C120.8 (3)
C8—N1—C7—O15.9 (3)N1—C8—C13—C12179.97 (16)
C8—N1—C7—C1174.53 (15)C6—C5—C14—F280.4 (2)
C2—C1—C7—O1148.05 (17)C4—C5—C14—F298.2 (2)
C6—C1—C7—O130.4 (2)C6—C5—C14—F1159.96 (16)
C2—C1—C7—N132.4 (2)C4—C5—C14—F121.4 (2)
C6—C1—C7—N1149.19 (15)C6—C5—C14—F340.1 (2)
C7—N1—C8—C9144.00 (17)C4—C5—C14—F3141.33 (17)
(PI34) top
Crystal data top
C14H9F3INOF(000) = 376
Mr = 391.12Dx = 1.994 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 4.9085 (3) ÅCell parameters from 7377 reflections
b = 4.9644 (3) Åθ = 3.1–29.9°
c = 26.7593 (16) ŵ = 2.49 mm1
β = 92.549 (2)°T = 101 K
V = 651.42 (7) Å3Rod
Z = 20.40 × 0.40 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3117 reflections with I > 2σ(I)
φ and ω scansRint = 0.026
Absorption correction: multi-scan
SADABS 2014/4
θmax = 29.1°, θmin = 3.1°
Tmin = 0.512, Tmax = 0.722h = 66
8008 measured reflectionsk = 56
3193 independent reflectionsl = 3631
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.021 w = 1/[σ2(Fo2) + (0.0305P)2 + 0.018P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.053(Δ/σ)max = 0.003
S = 1.03Δρmax = 0.50 e Å3
3193 reflectionsΔρmin = 0.67 e Å3
185 parametersAbsolute structure: Refined as an inversion twin.
1 restraintAbsolute structure parameter: 0.01 (2)
Special details top

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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.63751 (3)0.75230 (9)0.95250 (2)0.02168 (7)
F10.4677 (4)0.6775 (4)0.57279 (8)0.0257 (5)
F20.3717 (4)0.3034 (4)0.53653 (8)0.0266 (5)
F30.1120 (4)0.6483 (5)0.52859 (8)0.0274 (5)
O10.5041 (5)0.0323 (5)0.73690 (10)0.0229 (5)
N10.5230 (5)0.4052 (5)0.76155 (10)0.0130 (5)
H10.490 (7)0.576 (10)0.7499 (18)0.016*
C10.2496 (5)0.2868 (8)0.68784 (11)0.0142 (6)
C20.0657 (5)0.4994 (6)0.69202 (12)0.0143 (6)
H20.0576010.5955580.7226190.017*
C30.1062 (5)0.5704 (7)0.65121 (12)0.0156 (6)
H30.2322080.7142840.6539240.019*
C40.0918 (5)0.4299 (6)0.60681 (12)0.0146 (6)
C50.0883 (5)0.2160 (8)0.60247 (12)0.0172 (7)
H50.0959890.1197500.5718790.021*
C60.2569 (6)0.1446 (7)0.64344 (13)0.0171 (6)
H60.3784480.0032110.6409310.021*
C70.4382 (5)0.2042 (6)0.73091 (11)0.0144 (7)
C80.6813 (5)0.3744 (6)0.80672 (11)0.0131 (5)
C90.6155 (6)0.5411 (6)0.84653 (12)0.0145 (5)
H90.4720310.6687470.8424680.017*
C100.7607 (6)0.5193 (6)0.89193 (13)0.0165 (6)
C110.9759 (6)0.3377 (7)0.89816 (13)0.0189 (6)
H111.0766770.3254630.9292160.023*
C121.0403 (6)0.1756 (7)0.85832 (14)0.0213 (7)
H121.1874150.0519720.8621900.026*
C130.8935 (5)0.1902 (6)0.81267 (12)0.0162 (7)
H130.9379880.0753040.7858300.019*
C140.2620 (6)0.5137 (7)0.56129 (12)0.0173 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03010 (11)0.02252 (12)0.01244 (10)0.00481 (10)0.00111 (6)0.00242 (10)
F10.0226 (8)0.0323 (14)0.0216 (11)0.0121 (7)0.0059 (7)0.0023 (8)
F20.0262 (8)0.0291 (16)0.0236 (10)0.0012 (8)0.0094 (7)0.0070 (9)
F30.0272 (9)0.0373 (12)0.0174 (10)0.0030 (8)0.0015 (7)0.0101 (9)
O10.0315 (12)0.0086 (12)0.0274 (15)0.0007 (9)0.0110 (10)0.0015 (10)
N10.0170 (10)0.0088 (12)0.0128 (12)0.0017 (9)0.0030 (9)0.0019 (10)
C10.0137 (9)0.0133 (19)0.0155 (12)0.0022 (11)0.0003 (8)0.0005 (12)
C20.0146 (11)0.0157 (15)0.0124 (14)0.0003 (10)0.0003 (10)0.0035 (11)
C30.0139 (11)0.0165 (14)0.0163 (15)0.0027 (10)0.0011 (10)0.0001 (11)
C40.0126 (11)0.0153 (14)0.0158 (15)0.0022 (10)0.0002 (10)0.0013 (11)
C50.0198 (11)0.018 (2)0.0138 (12)0.0023 (12)0.0000 (9)0.0048 (12)
C60.0184 (12)0.0143 (14)0.0185 (16)0.0028 (10)0.0014 (11)0.0025 (12)
C70.0157 (10)0.013 (2)0.0143 (13)0.0014 (9)0.0004 (9)0.0015 (10)
C80.0150 (12)0.0119 (13)0.0123 (14)0.0032 (10)0.0000 (10)0.0038 (11)
C90.0168 (12)0.0123 (14)0.0141 (14)0.0003 (10)0.0017 (10)0.0012 (10)
C100.0210 (13)0.0150 (15)0.0133 (14)0.0038 (11)0.0004 (10)0.0010 (11)
C110.0198 (12)0.0203 (16)0.0161 (15)0.0013 (10)0.0039 (11)0.0054 (11)
C120.0188 (12)0.0186 (17)0.0262 (17)0.0010 (10)0.0026 (12)0.0036 (12)
C130.0162 (11)0.0159 (19)0.0167 (14)0.0014 (9)0.0017 (10)0.0005 (10)
C140.0179 (12)0.0201 (16)0.0137 (15)0.0006 (11)0.0016 (11)0.0002 (12)
Geometric parameters (Å, º) top
I1—C102.102 (3)C4—C51.390 (4)
F1—C141.343 (4)C4—C141.505 (4)
F2—C141.337 (4)C5—C61.390 (4)
F3—C141.346 (4)C5—H50.9500
O1—C71.227 (4)C6—H60.9500
N1—C71.346 (4)C8—C131.390 (4)
N1—C81.416 (4)C8—C91.398 (4)
N1—H10.92 (5)C9—C101.385 (4)
C1—C61.384 (5)C9—H90.9500
C1—C21.396 (4)C10—C111.393 (4)
C1—C71.503 (4)C11—C121.384 (5)
C2—C31.395 (4)C11—H110.9500
C2—H20.9500C12—C131.392 (5)
C3—C41.382 (5)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.7 (2)C13—C8—C9120.0 (3)
C7—N1—H1116 (3)C13—C8—N1123.3 (3)
C8—N1—H1118 (3)C9—C8—N1116.7 (3)
C6—C1—C2119.7 (3)C10—C9—C8119.6 (3)
C6—C1—C7118.7 (3)C10—C9—H9120.2
C2—C1—C7121.5 (3)C8—C9—H9120.2
C3—C2—C1119.9 (3)C9—C10—C11120.9 (3)
C3—C2—H2120.1C9—C10—I1118.6 (2)
C1—C2—H2120.1C11—C10—I1120.4 (2)
C4—C3—C2119.6 (3)C12—C11—C10118.8 (3)
C4—C3—H3120.2C12—C11—H11120.6
C2—C3—H3120.2C10—C11—H11120.6
C3—C4—C5120.9 (3)C11—C12—C13121.3 (3)
C3—C4—C14120.6 (3)C11—C12—H12119.4
C5—C4—C14118.4 (3)C13—C12—H12119.4
C4—C5—C6119.2 (3)C8—C13—C12119.4 (3)
C4—C5—H5120.4C8—C13—H13120.3
C6—C5—H5120.4C12—C13—H13120.3
C1—C6—C5120.6 (3)F2—C14—F1107.2 (2)
C1—C6—H6119.7F2—C14—F3106.6 (3)
C5—C6—H6119.7F1—C14—F3106.7 (3)
O1—C7—N1123.9 (3)F2—C14—C4112.5 (3)
O1—C7—C1120.8 (3)F1—C14—C4112.2 (3)
N1—C7—C1115.3 (3)F3—C14—C4111.3 (2)
C6—C1—C2—C31.1 (5)C7—N1—C8—C9141.2 (3)
C7—C1—C2—C3180.0 (3)C13—C8—C9—C100.7 (4)
C1—C2—C3—C40.3 (5)N1—C8—C9—C10179.3 (3)
C2—C3—C4—C51.1 (5)C8—C9—C10—C111.5 (5)
C2—C3—C4—C14176.1 (3)C8—C9—C10—I1175.5 (2)
C3—C4—C5—C60.4 (5)C9—C10—C11—C121.0 (5)
C14—C4—C5—C6176.8 (3)I1—C10—C11—C12176.0 (2)
C2—C1—C6—C51.8 (5)C10—C11—C12—C130.4 (5)
C7—C1—C6—C5179.3 (3)C9—C8—C13—C120.6 (4)
C4—C5—C6—C11.0 (5)N1—C8—C13—C12179.3 (3)
C8—N1—C7—O15.0 (5)C11—C12—C13—C81.1 (5)
C8—N1—C7—C1174.2 (3)C3—C4—C14—F2138.0 (3)
C6—C1—C7—O132.1 (4)C5—C4—C14—F244.9 (4)
C2—C1—C7—O1146.8 (3)C3—C4—C14—F117.0 (4)
C6—C1—C7—N1148.6 (3)C5—C4—C14—F1165.8 (3)
C2—C1—C7—N132.5 (4)C3—C4—C14—F3102.5 (3)
C7—N1—C8—C1338.9 (4)C5—C4—C14—F374.7 (4)
(PI43) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.881 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.292 (3) ÅCell parameters from 9389 reflections
b = 10.708 (2) Åθ = 2.5–30.1°
c = 9.762 (2) ŵ = 2.35 mm1
β = 96.305 (7)°T = 101 K
V = 1381.1 (5) Å3Rod
Z = 40.16 × 0.14 × 0.06 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3447 reflections with I > 2σ(I)
φ and ω scansRint = 0.032
Absorption correction: multi-scan
SADABS 2014/4
θmax = 30.1°, θmin = 2.8°
Tmin = 0.612, Tmax = 0.782h = 1813
17090 measured reflectionsk = 1413
4036 independent reflectionsl = 1313
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.064 w = 1/[σ2(Fo2) + (0.028P)2 + 1.4462P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
4036 reflectionsΔρmax = 0.95 e Å3
185 parametersΔρmin = 0.68 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.02275 (2)0.33427 (2)0.05393 (2)0.02088 (6)
F10.53532 (18)0.6643 (2)0.2166 (3)0.0700 (7)
F20.52485 (17)0.49003 (19)0.3122 (2)0.0607 (6)
F30.41782 (17)0.6298 (3)0.3769 (3)0.0926 (10)
O10.24345 (13)0.20035 (14)0.21181 (15)0.0189 (3)
N10.23505 (15)0.18807 (16)0.01907 (18)0.0149 (3)
H10.242 (2)0.225 (3)0.096 (3)0.020 (7)*
C10.29753 (16)0.3778 (2)0.0781 (2)0.0149 (4)
C20.27060 (19)0.4600 (2)0.0222 (2)0.0200 (4)
H20.2261290.4333330.0862140.024*
C30.3087 (2)0.5811 (2)0.0288 (3)0.0263 (5)
H30.2901020.6370560.0971330.032*
C40.3741 (2)0.6203 (2)0.0645 (3)0.0264 (5)
H40.4003330.7028800.0599280.032*
C50.40082 (18)0.5377 (2)0.1645 (2)0.0209 (5)
C60.36256 (17)0.4176 (2)0.1721 (2)0.0172 (4)
H60.3805780.3620890.2413160.021*
C70.25622 (16)0.24768 (19)0.0961 (2)0.0140 (4)
C80.18883 (16)0.06846 (19)0.0231 (2)0.0144 (4)
C90.12665 (17)0.0464 (2)0.1266 (2)0.0166 (4)
H90.1154970.1110880.1898090.020*
C100.08085 (17)0.0691 (2)0.1382 (2)0.0178 (4)
H100.0394090.0844260.2097550.021*
C110.09676 (17)0.16159 (19)0.0435 (2)0.0164 (4)
C120.15895 (18)0.1414 (2)0.0592 (2)0.0180 (4)
H120.1696370.2062880.1224300.022*
C130.20577 (17)0.02622 (19)0.0698 (2)0.0171 (4)
H130.2489290.0121460.1395880.021*
C140.4682 (2)0.5797 (3)0.2685 (3)0.0321 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02406 (9)0.01396 (8)0.02540 (9)0.00505 (5)0.00626 (6)0.00014 (5)
F10.0547 (14)0.0639 (15)0.0956 (18)0.0396 (11)0.0272 (13)0.0077 (12)
F20.0681 (14)0.0498 (12)0.0729 (14)0.0002 (10)0.0473 (11)0.0123 (11)
F30.0425 (12)0.162 (3)0.0742 (16)0.0050 (15)0.0115 (11)0.0925 (18)
O10.0304 (9)0.0148 (7)0.0120 (7)0.0015 (6)0.0044 (6)0.0003 (6)
N10.0219 (9)0.0121 (8)0.0112 (8)0.0012 (7)0.0035 (7)0.0016 (6)
C10.0169 (10)0.0126 (9)0.0146 (9)0.0004 (8)0.0007 (8)0.0021 (7)
C20.0280 (12)0.0142 (10)0.0179 (10)0.0001 (8)0.0032 (9)0.0024 (8)
C30.0409 (15)0.0139 (10)0.0238 (11)0.0001 (10)0.0022 (10)0.0026 (9)
C40.0324 (14)0.0140 (10)0.0311 (13)0.0068 (10)0.0042 (10)0.0030 (9)
C50.0190 (11)0.0190 (10)0.0239 (11)0.0039 (8)0.0012 (9)0.0076 (9)
C60.0168 (10)0.0157 (9)0.0188 (10)0.0008 (8)0.0007 (8)0.0021 (8)
C70.0154 (10)0.0125 (9)0.0142 (9)0.0020 (7)0.0029 (7)0.0015 (7)
C80.0174 (10)0.0122 (9)0.0136 (9)0.0000 (7)0.0016 (8)0.0020 (7)
C90.0204 (11)0.0164 (10)0.0134 (9)0.0010 (8)0.0039 (8)0.0016 (8)
C100.0209 (11)0.0175 (10)0.0156 (10)0.0014 (8)0.0046 (8)0.0011 (8)
C110.0195 (10)0.0114 (9)0.0182 (10)0.0014 (8)0.0010 (8)0.0012 (8)
C120.0243 (11)0.0126 (9)0.0174 (10)0.0009 (8)0.0037 (9)0.0008 (8)
C130.0232 (11)0.0145 (10)0.0144 (9)0.0005 (8)0.0052 (8)0.0012 (7)
C140.0258 (13)0.0300 (13)0.0413 (15)0.0072 (11)0.0076 (11)0.0128 (12)
Geometric parameters (Å, º) top
I1—C112.102 (2)C4—C51.392 (4)
F1—C141.331 (3)C4—H40.9500
F2—C141.320 (4)C5—C61.383 (3)
F3—C141.304 (3)C5—C141.495 (3)
O1—C71.232 (3)C6—H60.9500
N1—C71.350 (3)C8—C91.394 (3)
N1—C81.423 (3)C8—C131.394 (3)
N1—H10.85 (3)C9—C101.388 (3)
C1—C21.393 (3)C9—H90.9500
C1—C61.394 (3)C10—C111.388 (3)
C1—C71.501 (3)C10—H100.9500
C2—C31.391 (3)C11—C121.384 (3)
C2—H20.9500C12—C131.391 (3)
C3—C41.390 (4)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.36 (18)C9—C8—C13119.92 (19)
C7—N1—H1120.4 (19)C9—C8—N1117.67 (19)
C8—N1—H1113.8 (19)C13—C8—N1122.39 (19)
C2—C1—C6119.7 (2)C10—C9—C8120.7 (2)
C2—C1—C7123.4 (2)C10—C9—H9119.7
C6—C1—C7116.87 (19)C8—C9—H9119.7
C3—C2—C1120.1 (2)C11—C10—C9118.8 (2)
C3—C2—H2120.0C11—C10—H10120.6
C1—C2—H2120.0C9—C10—H10120.6
C4—C3—C2120.1 (2)C12—C11—C10121.22 (19)
C4—C3—H3119.9C12—C11—I1119.48 (15)
C2—C3—H3119.9C10—C11—I1119.29 (16)
C3—C4—C5119.6 (2)C11—C12—C13120.0 (2)
C3—C4—H4120.2C11—C12—H12120.0
C5—C4—H4120.2C13—C12—H12120.0
C6—C5—C4120.5 (2)C12—C13—C8119.4 (2)
C6—C5—C14119.2 (2)C12—C13—H13120.3
C4—C5—C14120.2 (2)C8—C13—H13120.3
C5—C6—C1120.0 (2)F3—C14—F2107.3 (3)
C5—C6—H6120.0F3—C14—F1107.0 (3)
C1—C6—H6120.0F2—C14—F1103.6 (2)
O1—C7—N1123.3 (2)F3—C14—C5112.5 (2)
O1—C7—C1120.06 (18)F2—C14—C5113.9 (2)
N1—C7—C1116.65 (18)F1—C14—C5111.9 (2)
C6—C1—C2—C30.2 (3)C7—N1—C8—C1334.0 (3)
C7—C1—C2—C3177.2 (2)C13—C8—C9—C100.2 (3)
C1—C2—C3—C40.2 (4)N1—C8—C9—C10178.7 (2)
C2—C3—C4—C50.2 (4)C8—C9—C10—C111.1 (3)
C3—C4—C5—C60.3 (4)C9—C10—C11—C121.6 (3)
C3—C4—C5—C14177.9 (2)C9—C10—C11—I1177.22 (16)
C4—C5—C6—C10.7 (3)C10—C11—C12—C130.8 (3)
C14—C5—C6—C1178.4 (2)I1—C11—C12—C13177.99 (17)
C2—C1—C6—C50.7 (3)C11—C12—C13—C80.5 (3)
C7—C1—C6—C5177.85 (19)C9—C8—C13—C121.0 (3)
C8—N1—C7—O15.0 (3)N1—C8—C13—C12179.4 (2)
C8—N1—C7—C1175.24 (19)C6—C5—C14—F390.0 (3)
C2—C1—C7—O1147.4 (2)C4—C5—C14—F387.7 (3)
C6—C1—C7—O129.7 (3)C6—C5—C14—F232.4 (3)
C2—C1—C7—N132.8 (3)C4—C5—C14—F2149.9 (3)
C6—C1—C7—N1150.1 (2)C6—C5—C14—F1149.6 (2)
C7—N1—C8—C9147.6 (2)C4—C5—C14—F132.8 (3)
(PI44) top
Crystal data top
C14H9F3INOF(000) = 752
Mr = 391.12Dx = 1.944 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.7689 (14) ÅCell parameters from 9953 reflections
b = 5.2518 (5) Åθ = 2.4–30.0°
c = 17.2537 (17) ŵ = 2.43 mm1
β = 93.217 (3)°T = 107 K
V = 1336.1 (2) Å3Plate
Z = 40.45 × 0.24 × 0.08 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2340 reflections with I > 2σ(I)
φ and ω scansRint = 0.044
Absorption correction: multi-scan
SADABS 2014/4
θmax = 26.7°, θmin = 2.4°
Tmin = 0.493, Tmax = 0.736h = 1818
15394 measured reflectionsk = 65
2820 independent reflectionsl = 2121
Refinement top
Refinement on F21 restraint
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0206P)2 + 12.064P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max < 0.001
2820 reflectionsΔρmax = 1.86 e Å3
184 parametersΔρmin = 1.13 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I10.79295 (2)0.13136 (8)0.79197 (2)0.02572 (14)
F10.0163 (3)0.0043 (9)0.3785 (3)0.0507 (11)
F20.0384 (3)0.3433 (9)0.3157 (2)0.0491 (11)
F30.0270 (2)0.3638 (8)0.4208 (2)0.0409 (10)
O10.4110 (2)0.6257 (7)0.5670 (2)0.0206 (8)
N10.4285 (3)0.1977 (9)0.5851 (3)0.0213 (9)
H10.413 (4)0.041 (5)0.577 (4)0.026*
C10.2944 (3)0.3528 (10)0.5130 (3)0.0163 (10)
C20.2401 (4)0.1430 (11)0.5281 (3)0.0213 (11)
H20.2594490.0227990.5666890.026*
C30.1577 (4)0.1110 (11)0.4864 (3)0.0232 (11)
H30.1197480.0288510.4974270.028*
C40.1309 (3)0.2834 (11)0.4285 (3)0.0207 (11)
C50.1851 (4)0.4903 (11)0.4134 (3)0.0224 (11)
H50.1662030.6087360.3741460.027*
C60.2669 (4)0.5256 (11)0.4555 (3)0.0210 (11)
H60.3040780.6677290.4449760.025*
C70.3830 (3)0.4053 (11)0.5575 (3)0.0179 (10)
C80.5120 (3)0.2008 (11)0.6307 (3)0.0184 (10)
C90.5697 (3)0.0049 (10)0.6216 (3)0.0188 (10)
H90.5541370.1332560.5844570.023*
C100.6509 (3)0.0223 (10)0.6675 (3)0.0175 (10)
H100.6909460.1613710.6610020.021*
C110.6726 (3)0.1623 (11)0.7220 (3)0.0184 (10)
C120.6154 (3)0.3715 (10)0.7309 (3)0.0167 (10)
H120.6312250.5000900.7679870.020*
C130.5349 (3)0.3895 (10)0.6848 (3)0.0174 (10)
H130.4956630.5309690.6903710.021*
C140.0376 (4)0.2552 (14)0.3811 (4)0.0356 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.02269 (19)0.0323 (2)0.0215 (2)0.00182 (15)0.00413 (13)0.00035 (15)
F10.040 (2)0.038 (3)0.071 (3)0.0045 (19)0.023 (2)0.008 (2)
F20.0291 (19)0.067 (3)0.048 (2)0.0057 (19)0.0249 (17)0.007 (2)
F30.0231 (17)0.055 (3)0.044 (2)0.0039 (17)0.0033 (15)0.0142 (19)
O10.0227 (18)0.0115 (19)0.0268 (19)0.0064 (15)0.0049 (15)0.0042 (15)
N10.027 (2)0.018 (2)0.019 (2)0.0007 (19)0.0007 (17)0.0000 (18)
C10.015 (2)0.021 (3)0.014 (2)0.001 (2)0.0015 (17)0.0031 (19)
C20.022 (2)0.022 (3)0.020 (2)0.005 (2)0.0001 (19)0.005 (2)
C30.021 (2)0.020 (3)0.028 (3)0.003 (2)0.001 (2)0.001 (2)
C40.018 (2)0.022 (3)0.022 (2)0.002 (2)0.0018 (19)0.002 (2)
C50.028 (3)0.021 (3)0.019 (2)0.003 (2)0.001 (2)0.004 (2)
C60.024 (3)0.017 (3)0.022 (2)0.003 (2)0.002 (2)0.000 (2)
C70.022 (2)0.020 (3)0.012 (2)0.002 (2)0.0019 (18)0.0008 (19)
C80.020 (2)0.021 (3)0.015 (2)0.005 (2)0.0039 (18)0.003 (2)
C90.020 (2)0.015 (3)0.022 (2)0.006 (2)0.0002 (19)0.004 (2)
C100.019 (2)0.015 (3)0.018 (2)0.001 (2)0.0015 (18)0.001 (2)
C110.019 (2)0.019 (3)0.017 (2)0.001 (2)0.0001 (18)0.004 (2)
C120.024 (2)0.013 (3)0.014 (2)0.002 (2)0.0013 (18)0.0014 (19)
C130.023 (2)0.014 (3)0.016 (2)0.003 (2)0.0031 (18)0.0002 (19)
C140.028 (3)0.034 (4)0.047 (4)0.018 (3)0.017 (3)0.027 (3)
Geometric parameters (Å, º) top
I1—C112.098 (5)C4—C51.383 (8)
F1—C141.355 (8)C4—C141.569 (8)
F2—C141.221 (8)C5—C61.387 (7)
F3—C141.334 (7)C5—H50.9500
O1—C71.237 (7)C6—H60.9500
N1—C71.353 (7)C8—C131.389 (7)
N1—C81.427 (7)C8—C91.390 (8)
N1—H10.87 (2)C9—C101.403 (7)
C1—C61.388 (7)C9—H90.9500
C1—C21.395 (8)C10—C111.375 (7)
C1—C71.505 (7)C10—H100.9500
C2—C31.389 (7)C11—C121.400 (7)
C2—H20.9500C12—C131.397 (7)
C3—C41.390 (8)C12—H120.9500
C3—H30.9500C13—H130.9500
C7—N1—C8125.6 (5)C13—C8—C9120.2 (5)
C7—N1—H1126 (4)C13—C8—N1123.3 (5)
C8—N1—H1109 (4)C9—C8—N1116.5 (5)
C6—C1—C2120.1 (5)C8—C9—C10119.8 (5)
C6—C1—C7117.1 (5)C8—C9—H9120.1
C2—C1—C7122.8 (5)C10—C9—H9120.1
C3—C2—C1119.6 (5)C11—C10—C9119.9 (5)
C3—C2—H2120.2C11—C10—H10120.1
C1—C2—H2120.2C9—C10—H10120.1
C2—C3—C4120.0 (5)C10—C11—C12120.7 (5)
C2—C3—H3120.0C10—C11—I1119.7 (4)
C4—C3—H3120.0C12—C11—I1119.6 (4)
C5—C4—C3120.1 (5)C13—C12—C11119.4 (5)
C5—C4—C14118.5 (5)C13—C12—H12120.3
C3—C4—C14121.3 (5)C11—C12—H12120.3
C4—C5—C6120.2 (5)C8—C13—C12120.1 (5)
C4—C5—H5119.9C8—C13—H13120.0
C6—C5—H5119.9C12—C13—H13120.0
C5—C6—C1119.9 (5)F2—C14—F3110.9 (7)
C5—C6—H6120.1F2—C14—F1110.6 (5)
C1—C6—H6120.1F3—C14—F1105.2 (5)
O1—C7—N1123.5 (5)F2—C14—C4113.1 (5)
O1—C7—C1120.9 (5)F3—C14—C4108.9 (5)
N1—C7—C1115.6 (5)F1—C14—C4107.8 (6)
C6—C1—C2—C31.3 (8)C7—N1—C8—C9148.7 (5)
C7—C1—C2—C3178.0 (5)C13—C8—C9—C100.4 (8)
C1—C2—C3—C41.8 (8)N1—C8—C9—C10176.6 (5)
C2—C3—C4—C51.5 (8)C8—C9—C10—C110.9 (8)
C2—C3—C4—C14179.0 (5)C9—C10—C11—C121.6 (8)
C3—C4—C5—C60.6 (8)C9—C10—C11—I1178.8 (4)
C14—C4—C5—C6178.3 (5)C10—C11—C12—C131.2 (8)
C4—C5—C6—C10.1 (8)I1—C11—C12—C13179.3 (4)
C2—C1—C6—C50.5 (8)C9—C8—C13—C120.8 (8)
C7—C1—C6—C5178.9 (5)N1—C8—C13—C12175.9 (5)
C8—N1—C7—O12.3 (8)C11—C12—C13—C80.1 (7)
C8—N1—C7—C1177.9 (4)C5—C4—C14—F230.8 (8)
C6—C1—C7—O128.9 (7)C3—C4—C14—F2151.6 (6)
C2—C1—C7—O1150.4 (5)C5—C4—C14—F393.0 (7)
C6—C1—C7—N1150.8 (5)C3—C4—C14—F384.6 (7)
C2—C1—C7—N129.8 (7)C5—C4—C14—F1153.4 (5)
C7—N1—C8—C1334.5 (8)C3—C4—C14—F129.0 (7)
 

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