Role of halogen-involved intermolecular inter­actions and existence of isostructurality in the crystal packing of —CF₃ and halogen (Cl or Br or I) substituted benzamides

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.

Computing details

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)

Crystal data

C14H9ClF3NO	F(000) = 608
Mr = 299.67	Dx = 1.581 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.7568 (2) Å	Cell parameters from 8335 reflections
b = 19.9611 (9) Å	θ = 2.6–30.1°
c = 13.4063 (6) Å	µ = 0.33 mm^−1
β = 98.457 (2)°	T = 104 K
V = 1259.10 (10) Å^3	Plate
Z = 4	0.50 × 0.18 × 0.18 mm

Data collection

Bruker APEX-II CCD diffractometer	2576 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan SADABS 2014/4	θmax = 27.5°, θmin = 2.6°
Tmin = 0.592, Tmax = 0.746	h = −6→6
12750 measured reflections	k = −25→25
2877 independent reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.0379P)^2 + 0.593P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2877 reflections	Δρmax = 0.33 e Å^−3
185 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	−0.30399 (7)	−0.01354 (2)	0.61285 (2)	0.02228 (10)
F1	0.11641 (19)	0.36944 (4)	0.52600 (6)	0.0277 (2)
F2	0.16167 (17)	0.29000 (4)	0.63555 (6)	0.02285 (18)
F3	0.48177 (17)	0.30502 (4)	0.53956 (7)	0.0289 (2)
O1	0.41987 (18)	0.16068 (5)	0.59540 (7)	0.0189 (2)
N1	−0.0035 (2)	0.11709 (5)	0.62574 (8)	0.0157 (2)
H1	−0.177 (4)	0.1204 (8)	0.6091 (13)	0.026 (4)*
C1	0.0014 (3)	0.19106 (6)	0.48425 (9)	0.0142 (2)
C2	−0.1738 (3)	0.15263 (6)	0.41394 (10)	0.0183 (3)
H2	−0.204897	0.106765	0.427777	0.022*
C3	−0.3038 (3)	0.18050 (7)	0.32381 (10)	0.0218 (3)
H3	−0.423527	0.153766	0.276678	0.026*
C4	−0.2588 (3)	0.24725 (7)	0.30268 (10)	0.0214 (3)
H4	−0.341859	0.265980	0.240087	0.026*
C5	−0.0915 (3)	0.28671 (6)	0.37351 (10)	0.0187 (3)
H5	−0.065050	0.332802	0.359888	0.022*
C6	0.0375 (3)	0.25922 (6)	0.46422 (9)	0.0149 (2)
C7	0.1608 (3)	0.15588 (6)	0.57472 (9)	0.0143 (2)
C8	0.1010 (3)	0.07140 (6)	0.70315 (9)	0.0148 (2)
C9	−0.0272 (3)	0.00864 (6)	0.70642 (10)	0.0167 (2)
C10	0.0646 (3)	−0.03713 (7)	0.78242 (10)	0.0220 (3)
H10	−0.028888	−0.079034	0.784786	0.026*
C11	0.2939 (3)	−0.02103 (7)	0.85471 (10)	0.0247 (3)
H11	0.361039	−0.052366	0.906052	0.030*
C12	0.4253 (3)	0.04092 (7)	0.85207 (10)	0.0227 (3)
H12	0.582748	0.051748	0.901630	0.027*
C13	0.3285 (3)	0.08711 (6)	0.77758 (10)	0.0188 (3)
H13	0.417578	0.129692	0.777224	0.023*
C14	0.2001 (3)	0.30516 (6)	0.54093 (10)	0.0180 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01961 (17)	0.01946 (16)	0.02583 (18)	−0.00396 (11)	−0.00314 (12)	−0.00043 (12)
F1	0.0372 (5)	0.0144 (4)	0.0298 (4)	0.0000 (3)	−0.0006 (4)	−0.0020 (3)
F2	0.0264 (4)	0.0253 (4)	0.0161 (4)	−0.0024 (3)	0.0005 (3)	−0.0029 (3)
F3	0.0154 (4)	0.0330 (5)	0.0384 (5)	−0.0072 (3)	0.0043 (3)	−0.0084 (4)
O1	0.0099 (4)	0.0232 (5)	0.0229 (5)	0.0008 (3)	0.0000 (3)	0.0036 (4)
N1	0.0094 (5)	0.0174 (5)	0.0190 (5)	0.0010 (4)	−0.0020 (4)	0.0034 (4)
C1	0.0104 (5)	0.0173 (6)	0.0149 (5)	0.0022 (4)	0.0018 (4)	0.0003 (4)
C2	0.0175 (6)	0.0163 (6)	0.0201 (6)	0.0008 (5)	−0.0008 (5)	−0.0007 (5)
C3	0.0208 (7)	0.0238 (6)	0.0187 (6)	0.0017 (5)	−0.0043 (5)	−0.0036 (5)
C4	0.0229 (7)	0.0252 (6)	0.0150 (6)	0.0057 (5)	−0.0009 (5)	0.0020 (5)
C5	0.0197 (6)	0.0178 (6)	0.0189 (6)	0.0025 (5)	0.0035 (5)	0.0027 (5)
C6	0.0118 (6)	0.0170 (6)	0.0162 (6)	0.0008 (4)	0.0034 (5)	−0.0005 (4)
C7	0.0134 (6)	0.0134 (5)	0.0157 (6)	0.0020 (4)	0.0004 (4)	−0.0013 (4)
C8	0.0134 (6)	0.0168 (6)	0.0143 (6)	0.0037 (4)	0.0025 (4)	0.0012 (4)
C9	0.0149 (6)	0.0185 (6)	0.0164 (6)	0.0018 (4)	0.0010 (5)	−0.0012 (5)
C10	0.0266 (7)	0.0182 (6)	0.0222 (7)	0.0024 (5)	0.0066 (5)	0.0039 (5)
C11	0.0309 (8)	0.0254 (7)	0.0173 (6)	0.0092 (6)	0.0024 (5)	0.0065 (5)
C12	0.0209 (7)	0.0305 (7)	0.0151 (6)	0.0055 (5)	−0.0023 (5)	0.0001 (5)
C13	0.0168 (6)	0.0204 (6)	0.0184 (6)	0.0012 (5)	0.0001 (5)	−0.0010 (5)
C14	0.0168 (6)	0.0171 (6)	0.0202 (6)	−0.0010 (5)	0.0032 (5)	−0.0010 (5)

Geometric parameters (Å, º)

Cl1—C9	1.7370 (13)	C4—C5	1.3903 (19)
F1—C14	1.3495 (15)	C4—H4	0.9500
F2—C14	1.3425 (15)	C5—C6	1.3917 (17)
F3—C14	1.3428 (15)	C5—H5	0.9500
O1—C7	1.2266 (15)	C6—C14	1.5042 (17)
N1—C7	1.3548 (17)	C8—C13	1.3956 (17)
N1—C8	1.4157 (15)	C8—C9	1.3967 (17)
N1—H1	0.827 (18)	C9—C10	1.3903 (18)
C1—C2	1.3930 (17)	C10—C11	1.386 (2)
C1—C6	1.4023 (17)	C10—H10	0.9500
C1—C7	1.5061 (16)	C11—C12	1.389 (2)
C2—C3	1.3900 (18)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.3872 (18)
C3—C4	1.3854 (19)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	124.89 (11)	C13—C8—C9	118.39 (11)
C7—N1—H1	116.5 (12)	C13—C8—N1	122.07 (11)
C8—N1—H1	118.6 (12)	C9—C8—N1	119.54 (11)
C2—C1—C6	118.86 (11)	C10—C9—C8	121.39 (12)
C2—C1—C7	117.94 (11)	C10—C9—Cl1	119.00 (10)
C6—C1—C7	123.04 (11)	C8—C9—Cl1	119.61 (9)
C3—C2—C1	120.88 (12)	C11—C10—C9	119.35 (13)
C3—C2—H2	119.6	C11—C10—H10	120.3
C1—C2—H2	119.6	C9—C10—H10	120.3
C4—C3—C2	120.02 (12)	C10—C11—C12	119.98 (12)
C4—C3—H3	120.0	C10—C11—H11	120.0
C2—C3—H3	120.0	C12—C11—H11	120.0
C3—C4—C5	119.69 (12)	C13—C12—C11	120.48 (13)
C3—C4—H4	120.2	C13—C12—H12	119.8
C5—C4—H4	120.2	C11—C12—H12	119.8
C4—C5—C6	120.53 (12)	C12—C13—C8	120.38 (12)
C4—C5—H5	119.7	C12—C13—H13	119.8
C6—C5—H5	119.7	C8—C13—H13	119.8
C5—C6—C1	119.94 (11)	F2—C14—F3	106.69 (10)
C5—C6—C14	118.25 (11)	F2—C14—F1	106.04 (10)
C1—C6—C14	121.72 (11)	F3—C14—F1	105.85 (10)
O1—C7—N1	124.44 (11)	F2—C14—C6	112.39 (10)
O1—C7—C1	121.04 (11)	F3—C14—C6	113.76 (10)
N1—C7—C1	114.43 (10)	F1—C14—C6	111.56 (10)
C6—C1—C2—C3	2.11 (19)	C7—N1—C8—C9	−138.37 (13)
C7—C1—C2—C3	−173.31 (12)	C13—C8—C9—C10	0.98 (19)
C1—C2—C3—C4	0.3 (2)	N1—C8—C9—C10	−178.54 (12)
C2—C3—C4—C5	−2.3 (2)	C13—C8—C9—Cl1	−178.08 (10)
C3—C4—C5—C6	1.8 (2)	N1—C8—C9—Cl1	2.40 (17)
C4—C5—C6—C1	0.63 (19)	C8—C9—C10—C11	−2.0 (2)
C4—C5—C6—C14	−176.00 (12)	Cl1—C9—C10—C11	177.02 (11)
C2—C1—C6—C5	−2.56 (18)	C9—C10—C11—C12	1.5 (2)
C7—C1—C6—C5	172.61 (12)	C10—C11—C12—C13	0.2 (2)
C2—C1—C6—C14	173.94 (12)	C11—C12—C13—C8	−1.2 (2)
C7—C1—C6—C14	−10.89 (18)	C9—C8—C13—C12	0.67 (19)
C8—N1—C7—O1	−6.9 (2)	N1—C8—C13—C12	−179.83 (12)
C8—N1—C7—C1	169.78 (11)	C5—C6—C14—F2	140.71 (12)
C2—C1—C7—O1	125.14 (13)	C1—C6—C14—F2	−35.85 (16)
C6—C1—C7—O1	−50.07 (17)	C5—C6—C14—F3	−97.90 (14)
C2—C1—C7—N1	−51.65 (15)	C1—C6—C14—F3	85.54 (15)
C6—C1—C7—N1	133.13 (12)	C5—C6—C14—F1	21.75 (16)
C7—N1—C8—C13	42.13 (18)	C1—C6—C14—F1	−154.81 (11)

(PC23)

Crystal data

C14H9ClF3NO	F(000) = 608
Mr = 299.67	Dx = 1.535 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.8080 (9) Å	Cell parameters from 7952 reflections
b = 9.7371 (18) Å	θ = 4.7–30.2°
c = 27.708 (5) Å	µ = 0.32 mm^−1
β = 91.735 (2)°	T = 100 K
V = 1296.6 (4) Å^3	Plate
Z = 4	0.50 × 0.24 × 0.16 mm

Data collection

Bruker APEX-II CCD diffractometer	2241 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 4.4°
Tmin = 0.652, Tmax = 0.796	h = −5→5
11184 measured reflections	k = −11→11
2400 independent reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0308P)^2 + 0.7067P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2400 reflections	Δρmax = 0.25 e Å^−3
213 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	−0.34578 (8)	0.41958 (4)	−0.04513 (2)	0.02922 (13)
F1A	0.0389 (8)	0.0514 (7)	0.2489 (2)	0.100 (3)	0.524 (7)
F2A	0.4308 (7)	0.0682 (5)	0.22221 (13)	0.0694 (12)	0.524 (7)
F3A	0.2956 (15)	0.2212 (4)	0.26908 (13)	0.102 (3)	0.524 (7)
F1B	0.4307 (7)	0.1573 (8)	0.2449 (2)	0.088 (3)	0.476 (7)
F2B	0.0469 (11)	0.1915 (5)	0.27730 (9)	0.0719 (16)	0.476 (7)
F3B	0.0914 (16)	0.0233 (5)	0.2339 (2)	0.095 (2)	0.476 (7)
O1	0.40581 (19)	0.19160 (11)	0.05195 (4)	0.0274 (3)
N1	−0.0323 (2)	0.23361 (12)	0.02096 (4)	0.0202 (3)
H1	−0.198 (4)	0.2471 (17)	0.0286 (6)	0.025 (4)*
C1	0.0597 (3)	0.26405 (14)	0.10619 (5)	0.0205 (3)
C2	−0.1304 (3)	0.36989 (15)	0.11262 (5)	0.0256 (3)
H2	−0.204125	0.418340	0.085363	0.031*
C3	−0.2130 (4)	0.40511 (17)	0.15859 (6)	0.0334 (4)
H3	−0.340850	0.478269	0.162708	0.040*
C4	−0.1091 (3)	0.33362 (18)	0.19851 (6)	0.0328 (4)
H4	−0.166438	0.356937	0.229983	0.039*
C5	0.0796 (3)	0.22766 (16)	0.19208 (5)	0.0296 (4)
C6	0.1678 (3)	0.19372 (15)	0.14630 (5)	0.0257 (3)
H6	0.301149	0.122902	0.142384	0.031*
C7	0.1622 (3)	0.22585 (14)	0.05726 (5)	0.0198 (3)
C8	0.0163 (3)	0.20954 (14)	−0.02849 (5)	0.0197 (3)
C9	−0.1228 (3)	0.28966 (14)	−0.06345 (5)	0.0218 (3)
C10	−0.0861 (3)	0.26916 (16)	−0.11230 (6)	0.0295 (3)
H10	−0.183385	0.324317	−0.135500	0.035*
C12	0.2333 (3)	0.08646 (16)	−0.09280 (6)	0.0316 (4)
H12	0.356507	0.016601	−0.102955	0.038*
C11	0.0946 (3)	0.16707 (18)	−0.12702 (6)	0.0335 (4)
H11	0.122940	0.152562	−0.160419	0.040*
C13	0.1945 (3)	0.10661 (15)	−0.04399 (5)	0.0245 (3)
H13	0.289604	0.050047	−0.020947	0.029*
C14	0.1867 (4)	0.1472 (2)	0.23480 (6)	0.0428 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0306 (2)	0.0271 (2)	0.0300 (2)	0.01241 (15)	0.00245 (15)	0.00326 (15)
F1A	0.0382 (16)	0.147 (6)	0.112 (5)	−0.037 (2)	−0.013 (2)	0.106 (4)
F2A	0.066 (2)	0.096 (3)	0.0454 (18)	0.0297 (19)	−0.0026 (13)	0.0343 (17)
F3A	0.187 (8)	0.075 (2)	0.039 (2)	0.010 (3)	−0.057 (3)	−0.0065 (16)
F1B	0.0285 (16)	0.150 (6)	0.084 (4)	−0.028 (2)	−0.0235 (18)	0.082 (4)
F2B	0.101 (4)	0.093 (3)	0.0218 (13)	0.036 (2)	0.0082 (15)	0.0116 (14)
F3B	0.197 (7)	0.0340 (18)	0.051 (2)	−0.022 (3)	−0.051 (3)	0.0189 (17)
O1	0.0160 (5)	0.0372 (6)	0.0290 (6)	0.0044 (4)	0.0022 (4)	0.0012 (5)
N1	0.0155 (6)	0.0239 (6)	0.0213 (6)	0.0034 (5)	0.0030 (5)	0.0008 (5)
C1	0.0168 (6)	0.0217 (7)	0.0230 (7)	−0.0031 (5)	0.0007 (5)	0.0009 (6)
C2	0.0268 (7)	0.0253 (7)	0.0245 (7)	0.0028 (6)	−0.0009 (6)	0.0002 (6)
C3	0.0359 (9)	0.0328 (9)	0.0317 (9)	0.0055 (7)	0.0050 (7)	−0.0076 (7)
C4	0.0390 (9)	0.0367 (9)	0.0232 (8)	−0.0082 (7)	0.0054 (7)	−0.0056 (7)
C5	0.0332 (8)	0.0309 (8)	0.0243 (8)	−0.0111 (7)	−0.0043 (6)	0.0045 (6)
C6	0.0235 (7)	0.0256 (8)	0.0280 (8)	0.0001 (6)	−0.0019 (6)	0.0036 (6)
C7	0.0173 (7)	0.0183 (7)	0.0239 (7)	−0.0002 (5)	0.0016 (5)	0.0039 (5)
C8	0.0176 (6)	0.0190 (7)	0.0226 (7)	−0.0022 (5)	0.0025 (5)	−0.0001 (5)
C9	0.0204 (7)	0.0191 (7)	0.0261 (7)	0.0015 (5)	0.0026 (5)	−0.0006 (6)
C10	0.0339 (8)	0.0307 (8)	0.0237 (8)	0.0011 (7)	−0.0006 (6)	0.0022 (6)
C12	0.0315 (8)	0.0282 (8)	0.0357 (9)	0.0054 (7)	0.0078 (7)	−0.0077 (7)
C11	0.0404 (9)	0.0367 (9)	0.0236 (8)	0.0002 (7)	0.0066 (7)	−0.0063 (7)
C13	0.0230 (7)	0.0217 (7)	0.0290 (8)	0.0021 (6)	0.0023 (6)	−0.0003 (6)
C14	0.0551 (12)	0.0459 (11)	0.0270 (9)	−0.0089 (9)	−0.0077 (8)	0.0088 (8)

Geometric parameters (Å, º)

Cl1—C9	1.7438 (14)	C3—H3	0.9500
F1A—C14	1.243 (4)	C4—C5	1.389 (2)
F2A—C14	1.454 (4)	C4—H4	0.9500
F3A—C14	1.291 (3)	C5—C6	1.390 (2)
F1B—C14	1.202 (3)	C5—C14	1.498 (2)
F2B—C14	1.440 (3)	C6—H6	0.9500
F3B—C14	1.290 (5)	C8—C13	1.3947 (19)
O1—C7	1.2309 (17)	C8—C9	1.398 (2)
N1—C7	1.3547 (18)	C9—C10	1.384 (2)
N1—C8	1.4166 (18)	C10—C11	1.389 (2)
N1—H1	0.840 (18)	C10—H10	0.9500
C1—C6	1.392 (2)	C12—C13	1.385 (2)
C1—C2	1.393 (2)	C12—C11	1.386 (2)
C1—C7	1.5031 (19)	C12—H12	0.9500
C2—C3	1.389 (2)	C11—H11	0.9500
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.387 (2)
C7—N1—C8	125.35 (12)	C10—C9—C8	121.63 (13)
C7—N1—H1	117.5 (11)	C10—C9—Cl1	119.13 (11)
C8—N1—H1	117.0 (11)	C8—C9—Cl1	119.24 (11)
C6—C1—C2	119.50 (13)	C9—C10—C11	119.30 (14)
C6—C1—C7	118.26 (13)	C9—C10—H10	120.3
C2—C1—C7	122.20 (13)	C11—C10—H10	120.3
C3—C2—C1	120.48 (14)	C13—C12—C11	120.75 (14)
C3—C2—H2	119.8	C13—C12—H12	119.6
C1—C2—H2	119.8	C11—C12—H12	119.6
C4—C3—C2	120.08 (15)	C12—C11—C10	119.77 (14)
C4—C3—H3	120.0	C12—C11—H11	120.1
C2—C3—H3	120.0	C10—C11—H11	120.1
C3—C4—C5	119.44 (14)	C12—C13—C8	120.32 (14)
C3—C4—H4	120.3	C12—C13—H13	119.8
C5—C4—H4	120.3	C8—C13—H13	119.8
C4—C5—C6	120.82 (14)	F1B—C14—F3B	115.1 (4)
C4—C5—C14	119.85 (15)	F1A—C14—F3A	114.2 (4)
C6—C5—C14	119.33 (16)	F1B—C14—F2B	105.1 (4)
C5—C6—C1	119.66 (14)	F3B—C14—F2B	96.9 (3)
C5—C6—H6	120.2	F1A—C14—F2A	98.7 (3)
C1—C6—H6	120.2	F3A—C14—F2A	99.2 (3)
O1—C7—N1	124.36 (13)	F1B—C14—C5	116.8 (2)
O1—C7—C1	120.93 (12)	F1A—C14—C5	117.1 (3)
N1—C7—C1	114.71 (12)	F3B—C14—C5	111.2 (3)
C13—C8—C9	118.23 (13)	F3A—C14—C5	114.3 (2)
C13—C8—N1	122.51 (13)	F2B—C14—C5	109.36 (19)
C9—C8—N1	119.25 (12)	F2A—C14—C5	110.36 (18)
C6—C1—C2—C3	−0.2 (2)	N1—C8—C9—Cl1	1.49 (18)
C7—C1—C2—C3	−177.83 (14)	C8—C9—C10—C11	−0.4 (2)
C1—C2—C3—C4	−0.9 (2)	Cl1—C9—C10—C11	179.06 (12)
C2—C3—C4—C5	0.6 (2)	C13—C12—C11—C10	−0.1 (3)
C3—C4—C5—C6	0.8 (2)	C9—C10—C11—C12	0.6 (2)
C3—C4—C5—C14	−178.23 (15)	C11—C12—C13—C8	−0.6 (2)
C4—C5—C6—C1	−1.9 (2)	C9—C8—C13—C12	0.8 (2)
C14—C5—C6—C1	177.16 (14)	N1—C8—C13—C12	179.49 (14)
C2—C1—C6—C5	1.6 (2)	C4—C5—C14—F1B	−114.5 (5)
C7—C1—C6—C5	179.29 (13)	C6—C5—C14—F1B	66.4 (5)
C8—N1—C7—O1	−2.8 (2)	C4—C5—C14—F1A	83.2 (5)
C8—N1—C7—C1	176.68 (12)	C6—C5—C14—F1A	−95.9 (5)
C6—C1—C7—O1	−35.6 (2)	C4—C5—C14—F3B	110.6 (4)
C2—C1—C7—O1	142.08 (14)	C6—C5—C14—F3B	−68.5 (4)
C6—C1—C7—N1	144.89 (13)	C4—C5—C14—F3A	−54.2 (5)
C2—C1—C7—N1	−37.47 (19)	C6—C5—C14—F3A	126.7 (4)
C7—N1—C8—C13	38.4 (2)	C4—C5—C14—F2B	4.7 (3)
C7—N1—C8—C9	−142.92 (14)	C6—C5—C14—F2B	−174.4 (3)
C13—C8—C9—C10	−0.3 (2)	C4—C5—C14—F2A	−165.0 (3)
N1—C8—C9—C10	−179.04 (13)	C6—C5—C14—F2A	15.9 (3)
C13—C8—C9—Cl1	−179.74 (10)

(PC24)

Crystal data

C14H9ClF3NO	Z = 2
Mr = 299.67	F(000) = 304
Triclinic, P1	Dx = 1.573 Mg m^−3
a = 4.8189 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4501 (5) Å	Cell parameters from 8370 reflections
c = 14.0283 (7) Å	θ = 2.5–30.0°
α = 96.048 (2)°	µ = 0.33 mm^−1
β = 93.400 (2)°	T = 105 K
γ = 93.414 (2)°	Plate
V = 632.77 (5) Å^3	0.50 × 0.29 × 0.07 mm

Data collection

Bruker APEX-II CCD diffractometer	2885 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.024
Absorption correction: multi-scan SADABS 2014/4	θmax = 28.3°, θmin = 2.9°
Tmin = 0.692, Tmax = 0.846	h = −6→5
11863 measured reflections	k = −12→12
3145 independent reflections	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.096	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 0.5169P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3145 reflections	Δρmax = 0.72 e Å^−3
185 parameters	Δρmin = −0.68 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.68214 (7)	0.43276 (3)	0.58367 (2)	0.01814 (10)
F1	0.8618 (3)	0.3611 (2)	−0.05256 (9)	0.0627 (5)
F2	0.4492 (2)	0.33611 (15)	−0.01285 (7)	0.0422 (3)
F3	0.6581 (5)	0.15361 (16)	−0.06200 (10)	0.0851 (7)
O1	1.3715 (2)	0.18181 (11)	0.38774 (7)	0.0191 (2)
N1	0.9550 (2)	0.23067 (12)	0.44870 (8)	0.0138 (2)
H1	0.789 (4)	0.239 (2)	0.4330 (14)	0.024 (5)*
C1	1.0039 (3)	0.23166 (14)	0.27840 (10)	0.0143 (3)
C2	0.8087 (3)	0.33112 (15)	0.26294 (10)	0.0173 (3)
H2	0.745052	0.388385	0.315991	0.021*
C3	0.7065 (3)	0.34690 (16)	0.17006 (11)	0.0202 (3)
H3	0.573903	0.415047	0.159518	0.024*
C4	0.7995 (3)	0.26230 (16)	0.09276 (10)	0.0200 (3)
C5	0.9972 (3)	0.16400 (16)	0.10761 (11)	0.0209 (3)
H5	1.061119	0.107006	0.054505	0.025*
C6	1.1003 (3)	0.14958 (16)	0.20014 (10)	0.0189 (3)
H6	1.237302	0.083527	0.210343	0.023*
C7	1.1280 (3)	0.21223 (14)	0.37671 (10)	0.0139 (2)
C8	1.0295 (3)	0.22082 (14)	0.54689 (9)	0.0134 (2)
C9	0.9103 (3)	0.30869 (14)	0.61735 (10)	0.0147 (3)
C10	0.9717 (3)	0.30036 (16)	0.71456 (10)	0.0191 (3)
H10	0.886870	0.360324	0.761481	0.023*
C11	1.1583 (3)	0.20352 (16)	0.74254 (11)	0.0215 (3)
H11	1.202940	0.197531	0.808813	0.026*
C12	1.2794 (3)	0.11559 (16)	0.67339 (11)	0.0200 (3)
H12	1.407349	0.049653	0.692580	0.024*
C13	1.2148 (3)	0.12327 (14)	0.57639 (10)	0.0161 (3)
H13	1.297193	0.061764	0.529710	0.019*
C14	0.6919 (4)	0.2777 (2)	−0.00786 (11)	0.0281 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01833 (17)	0.01686 (17)	0.01952 (17)	0.00644 (12)	−0.00027 (12)	0.00117 (12)
F1	0.0362 (7)	0.1277 (14)	0.0295 (6)	−0.0027 (7)	0.0012 (5)	0.0396 (8)
F2	0.0309 (6)	0.0743 (9)	0.0243 (5)	0.0192 (5)	−0.0039 (4)	0.0130 (5)
F3	0.1582 (18)	0.0507 (8)	0.0380 (7)	0.0429 (10)	−0.0566 (9)	−0.0195 (6)
O1	0.0120 (4)	0.0266 (5)	0.0190 (5)	0.0040 (4)	0.0002 (4)	0.0025 (4)
N1	0.0105 (5)	0.0175 (5)	0.0135 (5)	0.0021 (4)	−0.0012 (4)	0.0019 (4)
C1	0.0119 (6)	0.0159 (6)	0.0148 (6)	−0.0006 (5)	0.0003 (5)	0.0019 (5)
C2	0.0174 (6)	0.0187 (6)	0.0161 (6)	0.0036 (5)	0.0021 (5)	0.0015 (5)
C3	0.0200 (7)	0.0228 (7)	0.0189 (7)	0.0066 (5)	−0.0005 (5)	0.0048 (5)
C4	0.0194 (7)	0.0248 (7)	0.0154 (6)	0.0009 (5)	−0.0022 (5)	0.0029 (5)
C5	0.0231 (7)	0.0232 (7)	0.0157 (6)	0.0039 (6)	0.0012 (5)	−0.0024 (5)
C6	0.0183 (6)	0.0200 (7)	0.0181 (7)	0.0047 (5)	0.0000 (5)	0.0003 (5)
C7	0.0131 (6)	0.0132 (6)	0.0149 (6)	0.0000 (5)	−0.0006 (5)	0.0009 (5)
C8	0.0120 (6)	0.0145 (6)	0.0135 (6)	−0.0007 (5)	−0.0007 (5)	0.0023 (5)
C9	0.0132 (6)	0.0138 (6)	0.0170 (6)	0.0015 (5)	−0.0009 (5)	0.0029 (5)
C10	0.0218 (7)	0.0199 (7)	0.0153 (6)	0.0018 (5)	0.0015 (5)	0.0006 (5)
C11	0.0240 (7)	0.0243 (7)	0.0163 (6)	0.0008 (6)	−0.0038 (5)	0.0058 (6)
C12	0.0178 (6)	0.0197 (7)	0.0231 (7)	0.0022 (5)	−0.0042 (5)	0.0067 (5)
C13	0.0139 (6)	0.0152 (6)	0.0193 (7)	0.0019 (5)	0.0000 (5)	0.0023 (5)
C14	0.0287 (8)	0.0387 (9)	0.0169 (7)	0.0091 (7)	−0.0029 (6)	0.0015 (6)

Geometric parameters (Å, º)

Cl1—C9	1.7367 (14)	C4—C5	1.392 (2)
F1—C14	1.331 (2)	C4—C14	1.499 (2)
F2—C14	1.3239 (19)	C5—C6	1.385 (2)
F3—C14	1.324 (2)	C5—H5	0.9500
O1—C7	1.2296 (16)	C6—H6	0.9500
N1—C7	1.3510 (17)	C8—C9	1.3954 (19)
N1—C8	1.4166 (17)	C8—C13	1.3976 (18)
N1—H1	0.83 (2)	C9—C10	1.3895 (19)
C1—C2	1.3929 (19)	C10—C11	1.390 (2)
C1—C6	1.3953 (19)	C10—H10	0.9500
C1—C7	1.5038 (18)	C11—C12	1.388 (2)
C2—C3	1.391 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.388 (2)
C3—C4	1.391 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.02 (12)	C9—C8—C13	118.25 (12)
C7—N1—H1	116.7 (14)	C9—C8—N1	119.47 (12)
C8—N1—H1	117.8 (14)	C13—C8—N1	122.27 (12)
C2—C1—C6	119.66 (13)	C10—C9—C8	121.52 (13)
C2—C1—C7	122.77 (12)	C10—C9—Cl1	118.81 (11)
C6—C1—C7	117.51 (12)	C8—C9—Cl1	119.68 (10)
C3—C2—C1	120.22 (13)	C9—C10—C11	119.42 (13)
C3—C2—H2	119.9	C9—C10—H10	120.3
C1—C2—H2	119.9	C11—C10—H10	120.3
C4—C3—C2	119.60 (13)	C12—C11—C10	119.82 (13)
C4—C3—H3	120.2	C12—C11—H11	120.1
C2—C3—H3	120.2	C10—C11—H11	120.1
C3—C4—C5	120.47 (13)	C11—C12—C13	120.49 (13)
C3—C4—C14	120.40 (14)	C11—C12—H12	119.8
C5—C4—C14	119.12 (14)	C13—C12—H12	119.8
C6—C5—C4	119.74 (13)	C12—C13—C8	120.50 (13)
C6—C5—H5	120.1	C12—C13—H13	119.8
C4—C5—H5	120.1	C8—C13—H13	119.8
C5—C6—C1	120.29 (13)	F2—C14—F3	106.49 (16)
C5—C6—H6	119.9	F2—C14—F1	104.76 (15)
C1—C6—H6	119.9	F3—C14—F1	106.47 (17)
O1—C7—N1	124.19 (13)	F2—C14—C4	113.63 (14)
O1—C7—C1	120.34 (12)	F3—C14—C4	112.23 (15)
N1—C7—C1	115.47 (12)	F1—C14—C4	112.65 (14)
C6—C1—C2—C3	1.1 (2)	C13—C8—C9—C10	−0.2 (2)
C7—C1—C2—C3	178.33 (13)	N1—C8—C9—C10	178.38 (12)
C1—C2—C3—C4	0.3 (2)	C13—C8—C9—Cl1	179.25 (10)
C2—C3—C4—C5	−1.1 (2)	N1—C8—C9—Cl1	−2.18 (18)
C2—C3—C4—C14	−179.98 (14)	C8—C9—C10—C11	0.7 (2)
C3—C4—C5—C6	0.5 (2)	Cl1—C9—C10—C11	−178.71 (11)
C14—C4—C5—C6	179.39 (14)	C9—C10—C11—C12	−0.5 (2)
C4—C5—C6—C1	0.9 (2)	C10—C11—C12—C13	−0.2 (2)
C2—C1—C6—C5	−1.7 (2)	C11—C12—C13—C8	0.8 (2)
C7—C1—C6—C5	−179.09 (13)	C9—C8—C13—C12	−0.6 (2)
C8—N1—C7—O1	1.4 (2)	N1—C8—C13—C12	−179.08 (12)
C8—N1—C7—C1	−178.48 (11)	C3—C4—C14—F2	−21.9 (2)
C2—C1—C7—O1	−145.14 (14)	C5—C4—C14—F2	159.22 (15)
C6—C1—C7—O1	32.13 (19)	C3—C4—C14—F3	−142.79 (18)
C2—C1—C7—N1	34.77 (18)	C5—C4—C14—F3	38.3 (2)
C6—C1—C7—N1	−147.96 (13)	C3—C4—C14—F1	97.06 (19)
C7—N1—C8—C9	145.91 (14)	C5—C4—C14—F1	−81.8 (2)
C7—N1—C8—C13	−35.6 (2)

(PC32)

Crystal data

C14H9ClF3NO	Dx = 1.516 Mg m^−3
Mr = 299.67	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 5990 reflections
a = 7.7658 (6) Å	θ = 2.8–30.0°
b = 19.1333 (13) Å	µ = 0.32 mm^−1
c = 8.8369 (5) Å	T = 104 K
V = 1313.03 (15) Å^3	Plate
Z = 4	0.40 × 0.40 × 0.06 mm
F(000) = 608

Data collection

Bruker APEX-II CCD diffractometer	3099 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.060
Absorption correction: multi-scan SADABS 2014/4	θmax = 30.0°, θmin = 2.8°
Tmin = 0.632, Tmax = 0.796	h = −10→10
14300 measured reflections	k = −26→26
3609 independent reflections	l = −12→10

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.042	w = 1/[σ^2(Fo^2) + (0.0404P)^2 + 0.4809P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.096	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.55 e Å^−3
3609 reflections	Δρmin = −0.28 e Å^−3
185 parameters	Absolute structure: Flack x determined using 1139 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: −0.02 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.93285 (9)	0.46683 (4)	0.83195 (8)	0.02405 (17)
F1	0.7021 (3)	0.03059 (10)	0.5070 (3)	0.0411 (5)
F2	0.8187 (2)	0.13129 (10)	0.5409 (2)	0.0322 (5)
F3	0.6053 (3)	0.09908 (12)	0.6792 (2)	0.0363 (5)
O1	0.6058 (3)	0.25747 (11)	0.6312 (2)	0.0219 (4)
N1	0.7630 (3)	0.28718 (12)	0.4226 (3)	0.0159 (4)
H1	0.783 (4)	0.2758 (18)	0.332 (3)	0.029 (9)*
C1	0.5375 (3)	0.20103 (14)	0.3995 (3)	0.0130 (5)
C2	0.4267 (3)	0.22715 (15)	0.2909 (3)	0.0169 (5)
H2	0.424378	0.275986	0.271595	0.020*
C4	0.3246 (4)	0.11160 (17)	0.2355 (4)	0.0241 (6)
H4	0.250296	0.081202	0.181068	0.029*
C3	0.3186 (4)	0.18310 (16)	0.2097 (3)	0.0219 (6)
H3	0.241083	0.201793	0.136974	0.026*
C5	0.4390 (3)	0.08455 (14)	0.3404 (4)	0.0225 (6)
H5	0.445425	0.035461	0.355449	0.027*
C6	0.5443 (3)	0.12881 (14)	0.4239 (3)	0.0158 (5)
C7	0.6405 (3)	0.25117 (14)	0.4965 (3)	0.0141 (5)
C8	0.8888 (4)	0.33104 (14)	0.4917 (3)	0.0161 (5)
C9	1.0558 (4)	0.32816 (15)	0.4353 (3)	0.0199 (6)
H9	1.082213	0.298503	0.352311	0.024*
C10	1.1841 (4)	0.36882 (16)	0.5009 (3)	0.0223 (6)
H10	1.297812	0.367194	0.461435	0.027*
C11	1.1477 (4)	0.41186 (14)	0.6238 (3)	0.0209 (6)
H11	1.235751	0.438753	0.670442	0.025*
C12	0.9806 (4)	0.41445 (14)	0.6759 (3)	0.0173 (5)
C13	0.8468 (4)	0.37543 (14)	0.6114 (3)	0.0163 (5)
H13	0.732020	0.379040	0.647746	0.020*
C14	0.6664 (4)	0.09815 (16)	0.5372 (4)	0.0241 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0312 (3)	0.0202 (3)	0.0208 (3)	0.0059 (3)	−0.0076 (3)	−0.0084 (3)
F1	0.0499 (13)	0.0231 (9)	0.0504 (14)	0.0158 (8)	−0.0045 (11)	0.0057 (9)
F2	0.0199 (8)	0.0411 (11)	0.0355 (11)	0.0030 (8)	−0.0073 (8)	0.0101 (9)
F3	0.0394 (11)	0.0490 (13)	0.0204 (10)	0.0085 (9)	0.0024 (8)	0.0142 (9)
O1	0.0234 (10)	0.0334 (12)	0.0090 (9)	−0.0070 (9)	0.0019 (8)	−0.0039 (8)
N1	0.0205 (11)	0.0203 (11)	0.0069 (9)	−0.0034 (9)	0.0000 (8)	−0.0025 (9)
C1	0.0112 (11)	0.0175 (12)	0.0103 (12)	−0.0013 (9)	0.0021 (9)	−0.0010 (9)
C2	0.0181 (13)	0.0176 (12)	0.0148 (12)	0.0002 (10)	−0.0007 (10)	−0.0003 (10)
C4	0.0187 (14)	0.0271 (15)	0.0267 (15)	−0.0071 (11)	−0.0007 (12)	−0.0073 (13)
C3	0.0174 (13)	0.0293 (16)	0.0190 (14)	0.0000 (11)	−0.0058 (11)	−0.0032 (11)
C5	0.0229 (13)	0.0164 (12)	0.0281 (15)	−0.0022 (10)	0.0075 (13)	−0.0009 (13)
C6	0.0152 (13)	0.0175 (13)	0.0147 (12)	0.0002 (10)	0.0033 (10)	0.0033 (10)
C7	0.0137 (12)	0.0177 (13)	0.0109 (12)	0.0017 (10)	−0.0012 (10)	−0.0004 (10)
C8	0.0223 (13)	0.0139 (12)	0.0122 (12)	−0.0029 (10)	−0.0044 (10)	0.0025 (10)
C9	0.0218 (14)	0.0225 (14)	0.0154 (13)	−0.0043 (10)	0.0013 (10)	−0.0006 (11)
C10	0.0208 (13)	0.0260 (15)	0.0201 (14)	−0.0083 (11)	0.0011 (12)	0.0002 (12)
C11	0.0255 (15)	0.0178 (13)	0.0193 (13)	−0.0066 (11)	−0.0023 (12)	0.0012 (12)
C12	0.0288 (14)	0.0100 (12)	0.0131 (12)	0.0020 (10)	−0.0044 (11)	−0.0001 (9)
C13	0.0208 (13)	0.0165 (12)	0.0115 (11)	0.0001 (10)	−0.0010 (10)	0.0024 (10)
C14	0.0277 (16)	0.0217 (14)	0.0230 (15)	0.0056 (12)	0.0037 (12)	0.0048 (11)

Geometric parameters (Å, º)

Cl1—C12	1.745 (3)	C4—H4	0.9500
F1—C14	1.348 (4)	C3—H3	0.9500
F2—C14	1.342 (4)	C5—C6	1.389 (4)
F3—C14	1.342 (4)	C5—H5	0.9500
O1—C7	1.227 (3)	C6—C14	1.499 (4)
N1—C7	1.344 (4)	C8—C9	1.391 (4)
N1—C8	1.425 (3)	C8—C13	1.395 (4)
N1—H1	0.85 (2)	C9—C10	1.390 (4)
C1—C2	1.382 (4)	C9—H9	0.9500
C1—C6	1.400 (4)	C10—C11	1.392 (4)
C1—C7	1.515 (4)	C10—H10	0.9500
C2—C3	1.390 (4)	C11—C12	1.378 (4)
C2—H2	0.9500	C11—H11	0.9500
C4—C5	1.384 (5)	C12—C13	1.401 (4)
C4—C3	1.388 (4)	C13—H13	0.9500
C7—N1—C8	125.4 (2)	C9—C8—C13	120.9 (3)
C7—N1—H1	117 (2)	C9—C8—N1	117.6 (3)
C8—N1—H1	116 (2)	C13—C8—N1	121.5 (3)
C2—C1—C6	119.2 (2)	C10—C9—C8	119.8 (3)
C2—C1—C7	119.5 (2)	C10—C9—H9	120.1
C6—C1—C7	121.2 (2)	C8—C9—H9	120.1
C1—C2—C3	121.0 (3)	C9—C10—C11	120.7 (3)
C1—C2—H2	119.5	C9—C10—H10	119.6
C3—C2—H2	119.5	C11—C10—H10	119.6
C5—C4—C3	120.0 (3)	C12—C11—C10	118.3 (3)
C5—C4—H4	120.0	C12—C11—H11	120.9
C3—C4—H4	120.0	C10—C11—H11	120.9
C4—C3—C2	119.5 (3)	C11—C12—C13	122.9 (3)
C4—C3—H3	120.2	C11—C12—Cl1	119.0 (2)
C2—C3—H3	120.2	C13—C12—Cl1	118.1 (2)
C4—C5—C6	120.4 (3)	C8—C13—C12	117.4 (3)
C4—C5—H5	119.8	C8—C13—H13	121.3
C6—C5—H5	119.8	C12—C13—H13	121.3
C5—C6—C1	119.8 (3)	F3—C14—F2	106.4 (3)
C5—C6—C14	119.3 (3)	F3—C14—F1	105.7 (2)
C1—C6—C14	120.9 (3)	F2—C14—F1	106.1 (2)
O1—C7—N1	125.2 (3)	F3—C14—C6	113.3 (2)
O1—C7—C1	119.7 (2)	F2—C14—C6	112.9 (2)
N1—C7—C1	115.1 (2)	F1—C14—C6	111.9 (3)
C6—C1—C2—C3	2.1 (4)	C7—N1—C8—C13	−41.0 (4)
C7—C1—C2—C3	−174.0 (2)	C13—C8—C9—C10	1.4 (4)
C5—C4—C3—C2	−0.6 (4)	N1—C8—C9—C10	−178.6 (3)
C1—C2—C3—C4	−1.4 (4)	C8—C9—C10—C11	0.8 (4)
C3—C4—C5—C6	2.0 (5)	C9—C10—C11—C12	−1.7 (4)
C4—C5—C6—C1	−1.4 (4)	C10—C11—C12—C13	0.4 (4)
C4—C5—C6—C14	179.8 (3)	C10—C11—C12—Cl1	178.8 (2)
C2—C1—C6—C5	−0.7 (4)	C9—C8—C13—C12	−2.6 (4)
C7—C1—C6—C5	175.3 (3)	N1—C8—C13—C12	177.5 (2)
C2—C1—C6—C14	178.2 (2)	C11—C12—C13—C8	1.7 (4)
C7—C1—C6—C14	−5.8 (4)	Cl1—C12—C13—C8	−176.8 (2)
C8—N1—C7—O1	9.5 (5)	C5—C6—C14—F3	−97.4 (3)
C8—N1—C7—C1	−172.3 (2)	C1—C6—C14—F3	83.8 (3)
C2—C1—C7—O1	109.9 (3)	C5—C6—C14—F2	141.6 (3)
C6—C1—C7—O1	−66.1 (4)	C1—C6—C14—F2	−37.3 (4)
C2—C1—C7—N1	−68.4 (3)	C5—C6—C14—F1	22.0 (4)
C6—C1—C7—N1	115.6 (3)	C1—C6—C14—F1	−156.9 (3)
C7—N1—C8—C9	139.1 (3)

(PC33)

Crystal data

C14H9ClF3NO	F(000) = 608
Mr = 299.67	Dx = 1.562 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 25.6147 (13) Å	Cell parameters from 9996 reflections
b = 5.3354 (3) Å	θ = 2.4–30.0°
c = 9.3918 (4) Å	µ = 0.33 mm^−1
β = 96.775 (2)°	T = 107 K
V = 1274.56 (11) Å^3	Plate
Z = 4	0.45 × 0.38 × 0.11 mm

Data collection

Bruker APEX-II CCD diffractometer	2799 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan SADABS 2014/4	θmax = 28.7°, θmin = 3.2°
Tmin = 0.624, Tmax = 0.772	h = −34→34
22049 measured reflections	k = −7→7
3282 independent reflections	l = −11→12

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.9622P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3282 reflections	Δρmax = 0.52 e Å^−3
185 parameters	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.95500 (2)	0.26109 (8)	−0.22000 (4)	0.02608 (12)
F1	0.57545 (4)	0.2058 (2)	0.29306 (11)	0.0388 (3)
F2	0.53553 (4)	0.3109 (3)	0.08899 (13)	0.0434 (3)
F3	0.52809 (5)	−0.0600 (2)	0.16741 (15)	0.0492 (4)
O1	0.75556 (4)	0.4164 (2)	0.17882 (11)	0.0188 (2)
N1	0.77546 (5)	0.3084 (2)	−0.04345 (14)	0.0177 (3)
H1	0.7656 (8)	0.229 (4)	−0.122 (2)	0.024 (5)*
C1	0.69807 (5)	0.1323 (3)	0.04065 (15)	0.0157 (3)
C2	0.69619 (6)	−0.0811 (3)	−0.04568 (15)	0.0183 (3)
H2	0.725831	−0.125953	−0.092166	0.022*
C3	0.65116 (6)	−0.2281 (3)	−0.06391 (16)	0.0201 (3)
H3	0.650259	−0.373713	−0.122358	0.024*
C4	0.60735 (6)	−0.1637 (3)	0.00280 (16)	0.0200 (3)
H4	0.576402	−0.263218	−0.010668	0.024*
C5	0.60946 (5)	0.0482 (3)	0.08943 (15)	0.0164 (3)
C6	0.65452 (5)	0.1949 (3)	0.11014 (15)	0.0157 (3)
H6	0.655735	0.337229	0.171261	0.019*
C7	0.74555 (5)	0.2984 (3)	0.06615 (15)	0.0156 (3)
C8	0.82552 (5)	0.4247 (3)	−0.04069 (15)	0.0170 (3)
C9	0.86079 (6)	0.3108 (3)	−0.12302 (16)	0.0179 (3)
H9	0.851014	0.164811	−0.177648	0.021*
C10	0.91031 (6)	0.4147 (3)	−0.12357 (16)	0.0190 (3)
C11	0.92550 (6)	0.6301 (3)	−0.04754 (17)	0.0221 (3)
H11	0.959523	0.699566	−0.050175	0.027*
C12	0.88965 (6)	0.7423 (3)	0.03276 (17)	0.0230 (3)
H12	0.899398	0.890533	0.085304	0.028*
C13	0.83974 (6)	0.6415 (3)	0.03769 (16)	0.0207 (3)
H13	0.815711	0.719207	0.093585	0.025*
C14	0.56217 (6)	0.1263 (3)	0.16033 (16)	0.0207 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01711 (18)	0.0307 (2)	0.0320 (2)	0.00115 (14)	0.00940 (14)	0.00026 (16)
F1	0.0232 (5)	0.0692 (8)	0.0243 (5)	0.0055 (5)	0.0045 (4)	−0.0172 (5)
F2	0.0291 (6)	0.0631 (8)	0.0408 (7)	0.0236 (5)	0.0157 (5)	0.0214 (6)
F3	0.0416 (7)	0.0455 (7)	0.0680 (9)	−0.0215 (6)	0.0379 (6)	−0.0166 (6)
O1	0.0182 (5)	0.0248 (6)	0.0137 (5)	−0.0010 (4)	0.0028 (4)	−0.0011 (4)
N1	0.0158 (6)	0.0230 (6)	0.0146 (6)	−0.0031 (5)	0.0033 (4)	−0.0019 (5)
C1	0.0152 (6)	0.0175 (7)	0.0144 (6)	0.0010 (5)	0.0024 (5)	0.0034 (5)
C2	0.0196 (7)	0.0193 (7)	0.0168 (7)	0.0033 (6)	0.0055 (5)	0.0023 (5)
C3	0.0248 (7)	0.0171 (7)	0.0184 (7)	−0.0001 (6)	0.0026 (6)	−0.0013 (5)
C4	0.0195 (7)	0.0209 (7)	0.0195 (7)	−0.0042 (6)	0.0024 (5)	0.0013 (6)
C5	0.0157 (6)	0.0204 (7)	0.0136 (6)	0.0000 (5)	0.0035 (5)	0.0031 (5)
C6	0.0166 (6)	0.0178 (7)	0.0131 (6)	0.0002 (5)	0.0027 (5)	0.0009 (5)
C7	0.0150 (6)	0.0178 (7)	0.0142 (6)	0.0026 (5)	0.0020 (5)	0.0023 (5)
C8	0.0159 (6)	0.0193 (7)	0.0159 (7)	−0.0021 (5)	0.0022 (5)	0.0031 (5)
C9	0.0165 (6)	0.0194 (7)	0.0178 (7)	−0.0012 (5)	0.0023 (5)	0.0003 (5)
C10	0.0161 (7)	0.0228 (7)	0.0185 (7)	0.0013 (6)	0.0033 (5)	0.0045 (6)
C11	0.0183 (7)	0.0245 (8)	0.0232 (8)	−0.0056 (6)	0.0007 (5)	0.0046 (6)
C12	0.0257 (8)	0.0217 (8)	0.0211 (8)	−0.0060 (6)	0.0008 (6)	−0.0007 (6)
C13	0.0225 (7)	0.0206 (7)	0.0196 (7)	−0.0009 (6)	0.0049 (5)	−0.0003 (6)
C14	0.0153 (6)	0.0286 (8)	0.0191 (7)	−0.0021 (6)	0.0048 (5)	0.0018 (6)

Geometric parameters (Å, º)

Cl1—C10	1.7454 (15)	C4—C5	1.390 (2)
F1—C14	1.3227 (18)	C4—H4	0.9500
F2—C14	1.3330 (19)	C5—C6	1.389 (2)
F3—C14	1.3298 (19)	C5—C14	1.5082 (19)
O1—C7	1.2318 (18)	C6—H6	0.9500
N1—C7	1.3549 (18)	C8—C9	1.396 (2)
N1—C8	1.4219 (18)	C8—C13	1.396 (2)
N1—H1	0.86 (2)	C9—C10	1.385 (2)
C1—C2	1.395 (2)	C9—H9	0.9500
C1—C6	1.3978 (19)	C10—C11	1.385 (2)
C1—C7	1.501 (2)	C11—C12	1.390 (2)
C2—C3	1.389 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.393 (2)
C3—C4	1.391 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	126.35 (13)	C9—C8—C13	120.46 (13)
C7—N1—H1	119.9 (14)	C9—C8—N1	116.18 (13)
C8—N1—H1	113.6 (14)	C13—C8—N1	123.36 (13)
C2—C1—C6	119.47 (13)	C10—C9—C8	118.75 (14)
C2—C1—C7	123.12 (13)	C10—C9—H9	120.6
C6—C1—C7	117.40 (13)	C8—C9—H9	120.6
C3—C2—C1	120.24 (13)	C11—C10—C9	122.14 (14)
C3—C2—H2	119.9	C11—C10—Cl1	119.73 (11)
C1—C2—H2	119.9	C9—C10—Cl1	118.11 (12)
C2—C3—C4	120.49 (14)	C10—C11—C12	118.27 (14)
C2—C3—H3	119.8	C10—C11—H11	120.9
C4—C3—H3	119.8	C12—C11—H11	120.9
C5—C4—C3	119.12 (14)	C11—C12—C13	121.30 (14)
C5—C4—H4	120.4	C11—C12—H12	119.4
C3—C4—H4	120.4	C13—C12—H12	119.4
C6—C5—C4	120.96 (13)	C12—C13—C8	119.06 (14)
C6—C5—C14	118.67 (13)	C12—C13—H13	120.5
C4—C5—C14	120.35 (13)	C8—C13—H13	120.5
C5—C6—C1	119.70 (13)	F1—C14—F3	106.86 (13)
C5—C6—H6	120.2	F1—C14—F2	107.23 (14)
C1—C6—H6	120.2	F3—C14—F2	106.11 (13)
O1—C7—N1	123.61 (13)	F1—C14—C5	111.96 (12)
O1—C7—C1	121.42 (13)	F3—C14—C5	112.43 (13)
N1—C7—C1	114.96 (12)	F2—C14—C5	111.86 (12)
C6—C1—C2—C3	0.8 (2)	C7—N1—C8—C13	−33.9 (2)
C7—C1—C2—C3	179.46 (13)	C13—C8—C9—C10	1.0 (2)
C1—C2—C3—C4	0.4 (2)	N1—C8—C9—C10	−179.48 (13)
C2—C3—C4—C5	−0.8 (2)	C8—C9—C10—C11	−1.3 (2)
C3—C4—C5—C6	−0.1 (2)	C8—C9—C10—Cl1	176.89 (11)
C3—C4—C5—C14	178.53 (14)	C9—C10—C11—C12	0.7 (2)
C4—C5—C6—C1	1.4 (2)	Cl1—C10—C11—C12	−177.47 (12)
C14—C5—C6—C1	−177.30 (13)	C10—C11—C12—C13	0.2 (2)
C2—C1—C6—C5	−1.7 (2)	C11—C12—C13—C8	−0.5 (2)
C7—C1—C6—C5	179.58 (12)	C9—C8—C13—C12	−0.1 (2)
C8—N1—C7—O1	8.9 (2)	N1—C8—C13—C12	−179.59 (14)
C8—N1—C7—C1	−171.58 (13)	C6—C5—C14—F1	−41.52 (19)
C2—C1—C7—O1	−150.27 (14)	C4—C5—C14—F1	139.80 (15)
C6—C1—C7—O1	28.4 (2)	C6—C5—C14—F3	−161.84 (14)
C2—C1—C7—N1	30.2 (2)	C4—C5—C14—F3	19.5 (2)
C6—C1—C7—N1	−151.19 (13)	C6—C5—C14—F2	78.88 (18)
C7—N1—C8—C9	146.62 (15)	C4—C5—C14—F2	−99.81 (17)

(PC34)

Crystal data

C14H9ClF3NO	Z = 2
Mr = 299.67	F(000) = 304
Triclinic, P1	Dx = 1.570 Mg m^−3
a = 5.1563 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.7617 (12) Å	Cell parameters from 5230 reflections
c = 11.9075 (13) Å	θ = 2.8–28.6°
α = 99.948 (6)°	µ = 0.33 mm^−1
β = 91.911 (7)°	T = 100 K
γ = 102.379 (7)°	Plate
V = 633.98 (12) Å^3	0.50 × 0.10 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	2011 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.041
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 2.4°
Tmin = 0.632, Tmax = 0.746	h = −6→6
7784 measured reflections	k = −13→13
2306 independent reflections	l = −14→14

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.055	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.140	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 1.8174P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max < 0.001
2306 reflections	Δρmax = 0.49 e Å^−3
185 parameters	Δρmin = −0.32 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.82299 (17)	−0.11494 (8)	−0.17703 (8)	0.0212 (2)
F1	0.9535 (5)	0.6791 (2)	0.58869 (18)	0.0384 (6)
F2	1.0338 (5)	0.8443 (2)	0.50582 (19)	0.0351 (6)
F3	0.6310 (5)	0.7522 (2)	0.5274 (2)	0.0405 (7)
O1	1.0581 (4)	0.3513 (2)	0.0446 (2)	0.0177 (5)
N1	0.6046 (6)	0.3095 (3)	0.0226 (2)	0.0140 (6)
H1	0.476 (9)	0.333 (4)	0.043 (4)	0.027 (12)*
C1	0.8355 (6)	0.4648 (3)	0.1857 (3)	0.0127 (7)
C2	0.6236 (6)	0.4521 (3)	0.2559 (3)	0.0159 (7)
H2	0.470976	0.383627	0.233747	0.019*
C3	0.6340 (7)	0.5385 (3)	0.3574 (3)	0.0180 (7)
H3	0.490102	0.528611	0.405292	0.022*
C4	0.8565 (7)	0.6400 (3)	0.3892 (3)	0.0165 (7)
C5	1.0678 (7)	0.6551 (3)	0.3192 (3)	0.0169 (7)
H5	1.218139	0.725041	0.340463	0.020*
C6	1.0573 (6)	0.5673 (3)	0.2185 (3)	0.0145 (7)
H6	1.202172	0.576813	0.171127	0.017*
C7	0.8432 (6)	0.3706 (3)	0.0782 (3)	0.0133 (7)
C8	0.5649 (6)	0.2065 (3)	−0.0741 (3)	0.0131 (7)
C9	0.3749 (6)	0.2027 (3)	−0.1606 (3)	0.0170 (7)
H9	0.275811	0.268194	−0.155531	0.020*
C10	0.3303 (7)	0.1019 (3)	−0.2553 (3)	0.0185 (7)
H10	0.202498	0.099759	−0.315316	0.022*
C11	0.4715 (7)	0.0048 (3)	−0.2622 (3)	0.0177 (7)
H11	0.442400	−0.063874	−0.326394	0.021*
C12	0.6555 (6)	0.0106 (3)	−0.1732 (3)	0.0153 (7)
C13	0.7065 (6)	0.1101 (3)	−0.0794 (3)	0.0150 (7)
H13	0.835795	0.112364	−0.019856	0.018*
C14	0.8698 (7)	0.7289 (4)	0.5016 (3)	0.0229 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0229 (4)	0.0137 (4)	0.0260 (5)	0.0065 (3)	−0.0005 (3)	−0.0015 (3)
F1	0.0618 (17)	0.0400 (14)	0.0153 (11)	0.0215 (12)	−0.0080 (11)	−0.0001 (10)
F2	0.0459 (14)	0.0223 (11)	0.0273 (12)	−0.0021 (10)	−0.0020 (11)	−0.0092 (9)
F3	0.0305 (13)	0.0499 (15)	0.0345 (13)	0.0177 (11)	−0.0014 (10)	−0.0202 (11)
O1	0.0116 (11)	0.0181 (12)	0.0215 (13)	0.0036 (9)	0.0015 (9)	−0.0018 (10)
N1	0.0092 (13)	0.0157 (14)	0.0161 (14)	0.0044 (11)	0.0009 (11)	−0.0011 (11)
C1	0.0133 (15)	0.0140 (15)	0.0114 (15)	0.0049 (12)	−0.0036 (12)	0.0023 (12)
C2	0.0118 (15)	0.0180 (16)	0.0161 (16)	0.0009 (13)	−0.0020 (13)	0.0014 (13)
C3	0.0169 (17)	0.0215 (17)	0.0163 (17)	0.0055 (14)	0.0014 (13)	0.0040 (14)
C4	0.0175 (16)	0.0183 (16)	0.0142 (16)	0.0073 (13)	−0.0035 (13)	0.0011 (13)
C5	0.0129 (16)	0.0162 (16)	0.0190 (17)	0.0013 (13)	−0.0045 (13)	−0.0002 (13)
C6	0.0106 (15)	0.0162 (16)	0.0180 (16)	0.0050 (13)	0.0004 (13)	0.0046 (13)
C7	0.0117 (15)	0.0125 (15)	0.0163 (16)	0.0028 (12)	0.0012 (13)	0.0042 (13)
C8	0.0104 (15)	0.0144 (15)	0.0130 (16)	0.0011 (12)	0.0011 (12)	0.0006 (12)
C9	0.0131 (16)	0.0160 (16)	0.0215 (18)	0.0030 (13)	0.0002 (13)	0.0031 (14)
C10	0.0171 (17)	0.0218 (17)	0.0149 (16)	0.0038 (14)	−0.0062 (13)	0.0006 (13)
C11	0.0175 (17)	0.0154 (16)	0.0166 (17)	0.0004 (13)	−0.0019 (13)	−0.0023 (13)
C12	0.0149 (16)	0.0133 (15)	0.0174 (16)	0.0029 (13)	0.0038 (13)	0.0018 (13)
C13	0.0121 (15)	0.0156 (16)	0.0157 (16)	0.0017 (13)	−0.0008 (13)	0.0004 (13)
C14	0.0248 (19)	0.0238 (18)	0.0187 (18)	0.0080 (15)	−0.0029 (15)	−0.0025 (15)

Geometric parameters (Å, º)

Cl1—C12	1.748 (3)	C4—C5	1.393 (5)
F1—C14	1.346 (4)	C4—C14	1.495 (5)
F2—C14	1.336 (4)	C5—C6	1.384 (5)
F3—C14	1.343 (4)	C5—H5	0.9500
O1—C7	1.237 (4)	C6—H6	0.9500
N1—C7	1.354 (4)	C8—C13	1.385 (5)
N1—C8	1.429 (4)	C8—C9	1.387 (5)
N1—H1	0.79 (5)	C9—C10	1.398 (5)
C1—C2	1.395 (5)	C9—H9	0.9500
C1—C6	1.399 (4)	C10—C11	1.389 (5)
C1—C7	1.497 (4)	C10—H10	0.9500
C2—C3	1.384 (5)	C11—C12	1.382 (5)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.394 (5)	C12—C13	1.383 (4)
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.1 (3)	C13—C8—C9	120.8 (3)
C7—N1—H1	119 (3)	C13—C8—N1	120.7 (3)
C8—N1—H1	116 (3)	C9—C8—N1	118.5 (3)
C2—C1—C6	119.1 (3)	C8—C9—C10	119.5 (3)
C2—C1—C7	123.2 (3)	C8—C9—H9	120.3
C6—C1—C7	117.7 (3)	C10—C9—H9	120.3
C3—C2—C1	120.5 (3)	C11—C10—C9	120.5 (3)
C3—C2—H2	119.7	C11—C10—H10	119.8
C1—C2—H2	119.7	C9—C10—H10	119.8
C2—C3—C4	119.8 (3)	C12—C11—C10	118.3 (3)
C2—C3—H3	120.1	C12—C11—H11	120.9
C4—C3—H3	120.1	C10—C11—H11	120.9
C5—C4—C3	120.4 (3)	C11—C12—C13	122.5 (3)
C5—C4—C14	120.5 (3)	C11—C12—Cl1	118.9 (2)
C3—C4—C14	119.0 (3)	C13—C12—Cl1	118.5 (3)
C6—C5—C4	119.5 (3)	C12—C13—C8	118.5 (3)
C6—C5—H5	120.3	C12—C13—H13	120.8
C4—C5—H5	120.3	C8—C13—H13	120.8
C5—C6—C1	120.7 (3)	F2—C14—F3	106.4 (3)
C5—C6—H6	119.6	F2—C14—F1	106.6 (3)
C1—C6—H6	119.6	F3—C14—F1	105.7 (3)
O1—C7—N1	123.4 (3)	F2—C14—C4	113.3 (3)
O1—C7—C1	120.6 (3)	F3—C14—C4	112.3 (3)
N1—C7—C1	116.1 (3)	F1—C14—C4	112.1 (3)
C6—C1—C2—C3	−1.0 (5)	C7—N1—C8—C9	−142.0 (3)
C7—C1—C2—C3	176.6 (3)	C13—C8—C9—C10	−1.4 (5)
C1—C2—C3—C4	0.9 (5)	N1—C8—C9—C10	−179.2 (3)
C2—C3—C4—C5	0.1 (5)	C8—C9—C10—C11	1.1 (5)
C2—C3—C4—C14	−177.3 (3)	C9—C10—C11—C12	0.2 (5)
C3—C4—C5—C6	−0.9 (5)	C10—C11—C12—C13	−1.1 (5)
C14—C4—C5—C6	176.4 (3)	C10—C11—C12—Cl1	176.8 (3)
C4—C5—C6—C1	0.7 (5)	C11—C12—C13—C8	0.8 (5)
C2—C1—C6—C5	0.2 (5)	Cl1—C12—C13—C8	−177.1 (2)
C7—C1—C6—C5	−177.5 (3)	C9—C8—C13—C12	0.4 (5)
C8—N1—C7—O1	6.8 (5)	N1—C8—C13—C12	178.2 (3)
C8—N1—C7—C1	−172.8 (3)	C5—C4—C14—F2	25.1 (5)
C2—C1—C7—O1	−150.0 (3)	C3—C4—C14—F2	−157.5 (3)
C6—C1—C7—O1	27.6 (5)	C5—C4—C14—F3	145.7 (3)
C2—C1—C7—N1	29.6 (5)	C3—C4—C14—F3	−36.9 (5)
C6—C1—C7—N1	−152.8 (3)	C5—C4—C14—F1	−95.5 (4)
C7—N1—C8—C13	40.1 (5)	C3—C4—C14—F1	81.8 (4)

(PC42)

Crystal data

C14H9ClF3NO	F(000) = 1216
Mr = 299.67	Dx = 1.468 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.445 (2) Å	Cell parameters from 6925 reflections
b = 15.275 (4) Å	θ = 3.2–27.8°
c = 18.954 (5) Å	µ = 0.31 mm^−1
β = 97.374 (2)°	T = 100 K
V = 2712.1 (11) Å^3	Plate
Z = 8	0.50 × 0.15 × 0.09 mm

Data collection

Bruker APEX-II CCD diffractometer	4688 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.037
Absorption correction: multi-scan SADABS 2014/4	θmax = 27.1°, θmin = 3.2°
Tmin = 0.732, Tmax = 0.846	h = −12→12
23057 measured reflections	k = −18→19
5971 independent reflections	l = −23→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 1.3716P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
5971 reflections	Δρmax = 0.43 e Å^−3
369 parameters	Δρmin = −0.46 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.34683 (7)	−0.11012 (4)	0.71366 (3)	0.06331 (19)
Cl2	0.75413 (7)	0.59280 (5)	0.28556 (3)	0.0681 (2)
F1	0.12423 (18)	0.24348 (11)	0.33283 (9)	0.0875 (5)
F2	0.3104 (3)	0.27688 (11)	0.28398 (8)	0.1012 (7)
F3	0.32714 (15)	0.19200 (8)	0.37344 (6)	0.0540 (3)
F4	0.67108 (13)	0.26225 (9)	0.66174 (7)	0.0552 (3)
F5	0.87138 (16)	0.23809 (9)	0.72593 (6)	0.0627 (4)
F6	0.86553 (14)	0.31342 (8)	0.63018 (7)	0.0524 (3)
O1	0.14589 (12)	0.21813 (9)	0.49666 (7)	0.0375 (3)
O2	0.64475 (12)	0.27228 (9)	0.50225 (7)	0.0400 (3)
N1	0.37972 (15)	0.21231 (10)	0.54368 (8)	0.0308 (3)
H1	0.465 (2)	0.2304 (14)	0.5371 (11)	0.041 (6)*
N2	0.85904 (16)	0.27257 (11)	0.45904 (8)	0.0338 (3)
H2	0.945 (2)	0.2542 (14)	0.4675 (11)	0.040 (6)*
C1	0.29807 (16)	0.33328 (11)	0.46762 (9)	0.0291 (4)
C2	0.32241 (19)	0.40737 (13)	0.50986 (11)	0.0383 (4)
H2A	0.331901	0.401779	0.560166	0.046*
C3	0.3330 (2)	0.48914 (13)	0.47979 (13)	0.0459 (5)
H3	0.346381	0.539551	0.509248	0.055*
C4	0.3242 (2)	0.49735 (14)	0.40729 (13)	0.0483 (5)
H4	0.332049	0.553473	0.386540	0.058*
C5	0.3041 (2)	0.42426 (14)	0.36449 (12)	0.0454 (5)
H5	0.300430	0.430246	0.314395	0.054*
C6	0.28915 (19)	0.34190 (12)	0.39385 (10)	0.0347 (4)
C7	0.26764 (17)	0.24860 (12)	0.50301 (9)	0.0286 (4)
C8	0.36991 (17)	0.13503 (12)	0.58432 (9)	0.0306 (4)
C9	0.47568 (18)	0.07205 (13)	0.58538 (9)	0.0345 (4)
H9	0.552220	0.080484	0.558101	0.041*
C10	0.4708 (2)	−0.00301 (14)	0.62583 (10)	0.0401 (4)
H10	0.544120	−0.045770	0.627070	0.048*
C11	0.3574 (2)	−0.01490 (14)	0.66447 (10)	0.0403 (5)
C12	0.2511 (2)	0.04698 (16)	0.66355 (9)	0.0442 (5)
H12	0.173514	0.037612	0.689957	0.053*
C13	0.25742 (19)	0.12265 (15)	0.62421 (9)	0.0407 (5)
H13	0.185430	0.166065	0.624337	0.049*
C14	0.2636 (3)	0.26448 (15)	0.34639 (11)	0.0500 (5)
C15	0.81237 (16)	0.16146 (12)	0.54332 (9)	0.0297 (4)
C16	0.82947 (19)	0.08300 (13)	0.50819 (11)	0.0397 (4)
H16	0.822753	0.082558	0.457749	0.048*
C17	0.85597 (19)	0.00589 (13)	0.54522 (13)	0.0457 (5)
H17	0.865295	−0.047316	0.520281	0.055*
C18	0.8689 (2)	0.00598 (13)	0.61830 (13)	0.0457 (5)
H18	0.886255	−0.047266	0.643850	0.055*
C19	0.85671 (19)	0.08375 (13)	0.65469 (11)	0.0406 (4)
H19	0.868396	0.083929	0.705226	0.049*
C20	0.82756 (17)	0.16111 (12)	0.61772 (9)	0.0310 (4)
C21	0.76455 (17)	0.24095 (12)	0.50036 (9)	0.0310 (4)
C22	0.83324 (18)	0.34781 (13)	0.41555 (9)	0.0337 (4)
C23	0.93577 (18)	0.41324 (13)	0.41959 (10)	0.0381 (4)
H23	1.022092	0.406569	0.450870	0.046*
C24	0.9138 (2)	0.48785 (15)	0.37875 (10)	0.0433 (5)
H24	0.984443	0.532416	0.381248	0.052*
C25	0.7862 (2)	0.49652 (15)	0.33384 (10)	0.0457 (5)
C26	0.6841 (2)	0.43167 (17)	0.32851 (10)	0.0486 (5)
H26	0.597930	0.438591	0.297129	0.058*
C27	0.7072 (2)	0.35658 (15)	0.36890 (10)	0.0424 (5)
H27	0.637824	0.311219	0.364964	0.051*
C28	0.8095 (2)	0.24339 (13)	0.65879 (10)	0.0408 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0604 (3)	0.0677 (4)	0.0623 (4)	−0.0117 (3)	0.0096 (3)	0.0317 (3)
Cl2	0.0728 (4)	0.0825 (5)	0.0495 (3)	0.0142 (3)	0.0104 (3)	0.0368 (3)
F1	0.0795 (11)	0.0794 (11)	0.0911 (12)	0.0042 (9)	−0.0365 (9)	−0.0373 (9)
F2	0.212 (2)	0.0591 (10)	0.0398 (8)	0.0036 (12)	0.0440 (10)	−0.0031 (7)
F3	0.0793 (9)	0.0353 (7)	0.0481 (7)	0.0094 (6)	0.0104 (6)	−0.0075 (5)
F4	0.0518 (7)	0.0596 (8)	0.0548 (7)	0.0105 (6)	0.0097 (6)	−0.0214 (6)
F5	0.0835 (10)	0.0615 (9)	0.0373 (6)	0.0040 (7)	−0.0152 (6)	−0.0118 (6)
F6	0.0641 (8)	0.0318 (6)	0.0588 (8)	−0.0069 (6)	−0.0015 (6)	−0.0071 (5)
O1	0.0235 (6)	0.0413 (8)	0.0460 (7)	−0.0002 (5)	−0.0014 (5)	0.0061 (6)
O2	0.0236 (6)	0.0545 (9)	0.0430 (7)	0.0061 (6)	0.0092 (5)	0.0083 (6)
N1	0.0212 (7)	0.0397 (9)	0.0314 (7)	0.0020 (6)	0.0025 (6)	0.0038 (6)
N2	0.0213 (7)	0.0467 (10)	0.0338 (8)	0.0034 (7)	0.0053 (6)	0.0034 (7)
C1	0.0203 (7)	0.0312 (9)	0.0351 (9)	0.0042 (7)	0.0009 (6)	−0.0036 (7)
C2	0.0272 (8)	0.0388 (11)	0.0475 (11)	0.0026 (8)	−0.0001 (7)	−0.0101 (8)
C3	0.0315 (9)	0.0311 (11)	0.0734 (15)	0.0028 (8)	0.0003 (9)	−0.0115 (10)
C4	0.0316 (9)	0.0297 (10)	0.0836 (17)	0.0049 (8)	0.0066 (10)	0.0100 (10)
C5	0.0411 (10)	0.0440 (12)	0.0513 (12)	0.0075 (9)	0.0068 (9)	0.0138 (9)
C6	0.0339 (9)	0.0333 (10)	0.0371 (10)	0.0054 (8)	0.0046 (7)	0.0009 (8)
C7	0.0243 (8)	0.0328 (9)	0.0284 (8)	0.0040 (7)	0.0025 (6)	−0.0035 (7)
C8	0.0246 (8)	0.0414 (10)	0.0251 (8)	0.0004 (7)	0.0002 (6)	0.0029 (7)
C9	0.0230 (8)	0.0431 (11)	0.0379 (9)	−0.0019 (7)	0.0055 (7)	0.0046 (8)
C10	0.0318 (9)	0.0421 (11)	0.0458 (11)	−0.0011 (8)	0.0027 (8)	0.0085 (9)
C11	0.0373 (10)	0.0506 (12)	0.0317 (9)	−0.0086 (9)	−0.0013 (7)	0.0126 (8)
C12	0.0327 (9)	0.0723 (15)	0.0283 (9)	−0.0022 (9)	0.0072 (7)	0.0120 (9)
C13	0.0321 (9)	0.0622 (13)	0.0286 (9)	0.0096 (9)	0.0071 (7)	0.0072 (9)
C14	0.0711 (15)	0.0443 (12)	0.0330 (10)	0.0069 (11)	0.0007 (10)	−0.0020 (9)
C15	0.0177 (7)	0.0338 (10)	0.0380 (9)	−0.0031 (7)	0.0055 (6)	−0.0054 (7)
C16	0.0267 (8)	0.0433 (12)	0.0509 (11)	−0.0040 (8)	0.0122 (8)	−0.0160 (9)
C17	0.0302 (9)	0.0322 (11)	0.0779 (15)	−0.0042 (8)	0.0190 (9)	−0.0166 (10)
C18	0.0317 (9)	0.0296 (10)	0.0777 (15)	−0.0008 (8)	0.0148 (9)	0.0078 (10)
C19	0.0317 (9)	0.0416 (11)	0.0487 (11)	−0.0002 (8)	0.0064 (8)	0.0049 (9)
C20	0.0252 (8)	0.0304 (9)	0.0369 (9)	−0.0016 (7)	0.0015 (7)	−0.0027 (7)
C21	0.0232 (8)	0.0406 (10)	0.0291 (8)	−0.0017 (7)	0.0030 (6)	−0.0037 (7)
C22	0.0267 (8)	0.0490 (11)	0.0262 (8)	0.0052 (8)	0.0073 (6)	0.0027 (8)
C23	0.0251 (8)	0.0519 (12)	0.0378 (10)	0.0047 (8)	0.0061 (7)	0.0068 (8)
C24	0.0366 (10)	0.0528 (13)	0.0427 (11)	0.0026 (9)	0.0134 (8)	0.0092 (9)
C25	0.0450 (11)	0.0646 (14)	0.0293 (9)	0.0113 (10)	0.0115 (8)	0.0170 (9)
C26	0.0379 (10)	0.0795 (16)	0.0273 (9)	0.0063 (10)	0.0005 (8)	0.0126 (10)
C27	0.0325 (9)	0.0650 (14)	0.0291 (9)	−0.0011 (9)	0.0021 (7)	0.0041 (9)
C28	0.0462 (11)	0.0399 (11)	0.0337 (10)	−0.0007 (9)	−0.0045 (8)	−0.0058 (8)

Geometric parameters (Å, º)

Cl1—C11	1.737 (2)	C9—C10	1.383 (3)
Cl2—C25	1.738 (2)	C9—H9	0.9500
F1—C14	1.347 (3)	C10—C11	1.385 (3)
F2—C14	1.329 (3)	C10—H10	0.9500
F3—C14	1.330 (2)	C11—C12	1.377 (3)
F4—C28	1.347 (2)	C12—C13	1.381 (3)
F5—C28	1.333 (2)	C12—H12	0.9500
F6—C28	1.339 (2)	C13—H13	0.9500
O1—C7	1.232 (2)	C15—C16	1.391 (2)
O2—C21	1.233 (2)	C15—C20	1.399 (2)
N1—C7	1.346 (2)	C15—C21	1.499 (3)
N1—C8	1.419 (2)	C16—C17	1.378 (3)
N1—H1	0.88 (2)	C16—H16	0.9500
N2—C21	1.350 (2)	C17—C18	1.375 (3)
N2—C22	1.417 (2)	C17—H17	0.9500
N2—H2	0.85 (2)	C18—C19	1.386 (3)
C1—C2	1.388 (2)	C18—H18	0.9500
C1—C6	1.396 (3)	C19—C20	1.384 (3)
C1—C7	1.502 (2)	C19—H19	0.9500
C2—C3	1.382 (3)	C20—C28	1.500 (3)
C2—H2A	0.9500	C22—C23	1.387 (3)
C3—C4	1.372 (3)	C22—C27	1.395 (2)
C3—H3	0.9500	C23—C24	1.378 (3)
C4—C5	1.379 (3)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.389 (3)
C5—C6	1.390 (3)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.378 (3)
C6—C14	1.487 (3)	C26—C27	1.381 (3)
C8—C9	1.385 (3)	C26—H26	0.9500
C8—C13	1.394 (2)	C27—H27	0.9500
C7—N1—C8	123.50 (15)	F2—C14—C6	112.24 (19)
C7—N1—H1	117.4 (14)	F3—C14—C6	113.48 (17)
C8—N1—H1	117.7 (14)	F1—C14—C6	112.56 (18)
C21—N2—C22	123.40 (15)	C16—C15—C20	118.44 (17)
C21—N2—H2	117.2 (14)	C16—C15—C21	118.91 (16)
C22—N2—H2	117.6 (14)	C20—C15—C21	122.37 (15)
C2—C1—C6	119.01 (17)	C17—C16—C15	121.17 (19)
C2—C1—C7	118.13 (16)	C17—C16—H16	119.4
C6—C1—C7	122.57 (16)	C15—C16—H16	119.4
C3—C2—C1	120.95 (19)	C18—C17—C16	119.96 (18)
C3—C2—H2A	119.5	C18—C17—H17	120.0
C1—C2—H2A	119.5	C16—C17—H17	120.0
C4—C3—C2	119.84 (19)	C17—C18—C19	120.00 (19)
C4—C3—H3	120.1	C17—C18—H18	120.0
C2—C3—H3	120.1	C19—C18—H18	120.0
C3—C4—C5	120.1 (2)	C20—C19—C18	120.26 (19)
C3—C4—H4	119.9	C20—C19—H19	119.9
C5—C4—H4	119.9	C18—C19—H19	119.9
C4—C5—C6	120.7 (2)	C19—C20—C15	120.12 (17)
C4—C5—H5	119.7	C19—C20—C28	118.77 (17)
C6—C5—H5	119.7	C15—C20—C28	121.09 (16)
C5—C6—C1	119.36 (18)	O2—C21—N2	123.74 (17)
C5—C6—C14	119.63 (18)	O2—C21—C15	120.81 (15)
C1—C6—C14	121.01 (17)	N2—C21—C15	115.42 (14)
O1—C7—N1	123.77 (16)	C23—C22—C27	119.92 (18)
O1—C7—C1	120.76 (15)	C23—C22—N2	119.05 (16)
N1—C7—C1	115.39 (14)	C27—C22—N2	121.03 (17)
C9—C8—C13	119.77 (17)	C24—C23—C22	120.74 (17)
C9—C8—N1	119.23 (15)	C24—C23—H23	119.6
C13—C8—N1	120.99 (16)	C22—C23—H23	119.6
C10—C9—C8	120.56 (16)	C23—C24—C25	118.6 (2)
C10—C9—H9	119.7	C23—C24—H24	120.7
C8—C9—H9	119.7	C25—C24—H24	120.7
C9—C10—C11	119.00 (18)	C26—C25—C24	121.38 (19)
C9—C10—H10	120.5	C26—C25—Cl2	119.77 (16)
C11—C10—H10	120.5	C24—C25—Cl2	118.83 (18)
C12—C11—C10	121.01 (18)	C25—C26—C27	119.80 (18)
C12—C11—Cl1	119.29 (14)	C25—C26—H26	120.1
C10—C11—Cl1	119.69 (16)	C27—C26—H26	120.1
C11—C12—C13	119.96 (17)	C26—C27—C22	119.51 (19)
C11—C12—H12	120.0	C26—C27—H27	120.2
C13—C12—H12	120.0	C22—C27—H27	120.2
C12—C13—C8	119.68 (18)	F5—C28—F6	106.73 (16)
C12—C13—H13	120.2	F5—C28—F4	106.38 (16)
C8—C13—H13	120.2	F6—C28—F4	106.38 (17)
F2—C14—F3	106.06 (19)	F5—C28—C20	112.33 (17)
F2—C14—F1	107.0 (2)	F6—C28—C20	112.48 (16)
F3—C14—F1	104.88 (19)	F4—C28—C20	112.09 (15)
C6—C1—C2—C3	2.2 (3)	C20—C15—C16—C17	2.2 (2)
C7—C1—C2—C3	−171.73 (16)	C21—C15—C16—C17	−171.92 (15)
C1—C2—C3—C4	−2.2 (3)	C15—C16—C17—C18	−1.4 (3)
C2—C3—C4—C5	0.3 (3)	C16—C17—C18—C19	−0.6 (3)
C3—C4—C5—C6	1.5 (3)	C17—C18—C19—C20	1.8 (3)
C4—C5—C6—C1	−1.5 (3)	C18—C19—C20—C15	−1.0 (3)
C4—C5—C6—C14	178.33 (19)	C18—C19—C20—C28	177.69 (17)
C2—C1—C6—C5	−0.3 (2)	C16—C15—C20—C19	−1.0 (2)
C7—C1—C6—C5	173.30 (16)	C21—C15—C20—C19	172.88 (15)
C2—C1—C6—C14	179.85 (17)	C16—C15—C20—C28	−179.61 (16)
C7—C1—C6—C14	−6.5 (3)	C21—C15—C20—C28	−5.7 (2)
C8—N1—C7—O1	−0.5 (3)	C22—N2—C21—O2	2.9 (3)
C8—N1—C7—C1	176.43 (15)	C22—N2—C21—C15	−179.14 (16)
C2—C1—C7—O1	105.81 (19)	C16—C15—C21—O2	110.57 (19)
C6—C1—C7—O1	−67.8 (2)	C20—C15—C21—O2	−63.3 (2)
C2—C1—C7—N1	−71.2 (2)	C16—C15—C21—N2	−67.5 (2)
C6—C1—C7—N1	115.13 (18)	C20—C15—C21—N2	118.70 (17)
C7—N1—C8—C9	137.60 (17)	C21—N2—C22—C23	129.81 (18)
C7—N1—C8—C13	−43.8 (2)	C21—N2—C22—C27	−50.4 (3)
C13—C8—C9—C10	−0.1 (3)	C27—C22—C23—C24	1.0 (3)
N1—C8—C9—C10	178.48 (17)	N2—C22—C23—C24	−179.24 (17)
C8—C9—C10—C11	0.9 (3)	C22—C23—C24—C25	0.5 (3)
C9—C10—C11—C12	−0.5 (3)	C23—C24—C25—C26	−1.4 (3)
C9—C10—C11—Cl1	178.25 (15)	C23—C24—C25—Cl2	176.80 (15)
C10—C11—C12—C13	−0.6 (3)	C24—C25—C26—C27	0.6 (3)
Cl1—C11—C12—C13	−179.44 (15)	Cl2—C25—C26—C27	−177.53 (16)
C11—C12—C13—C8	1.5 (3)	C25—C26—C27—C22	0.9 (3)
C9—C8—C13—C12	−1.1 (3)	C23—C22—C27—C26	−1.8 (3)
N1—C8—C13—C12	−179.65 (17)	N2—C22—C27—C26	178.49 (17)
C5—C6—C14—F2	23.9 (3)	C19—C20—C28—F5	21.8 (2)
C1—C6—C14—F2	−156.22 (19)	C15—C20—C28—F5	−159.54 (16)
C5—C6—C14—F3	144.17 (19)	C19—C20—C28—F6	142.27 (17)
C1—C6—C14—F3	−36.0 (3)	C15—C20—C28—F6	−39.1 (2)
C5—C6—C14—F1	−96.9 (2)	C19—C20—C28—F4	−97.90 (19)
C1—C6—C14—F1	82.9 (2)	C15—C20—C28—F4	80.7 (2)

(PC43)

Crystal data

C14H9ClF3NO	F(000) = 608
Mr = 299.67	Dx = 1.536 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8325 (10) Å	Cell parameters from 8230 reflections
b = 10.3856 (8) Å	θ = 2.8–29.7°
c = 9.7379 (8) Å	µ = 0.32 mm^−1
β = 93.059 (3)°	T = 104 K
V = 1295.95 (18) Å^3	Plate
Z = 4	0.40 × 0.10 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	3069 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.053
Absorption correction: multi-scan SADABS 2014/4	θmax = 30.1°, θmin = 2.5°
Tmin = 0.732, Tmax = 0.846	h = −18→17
22891 measured reflections	k = −14→14
3808 independent reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0502P)^2 + 0.6888P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3808 reflections	Δρmax = 0.41 e Å^−3
213 parameters	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.47179 (3)	0.84113 (3)	0.44523 (4)	0.02897 (11)
F1A	−0.0221 (3)	0.0274 (3)	0.8219 (5)	0.0627 (11)	0.731 (16)
F2A	0.0733 (4)	−0.1363 (7)	0.8700 (7)	0.0821 (19)	0.731 (16)
F3A	−0.0479 (2)	−0.1476 (4)	0.7131 (6)	0.0624 (10)	0.731 (16)
F1B	−0.0368 (8)	0.0148 (14)	0.8060 (13)	0.083 (4)	0.269 (16)
F2B	0.0860 (10)	−0.083 (2)	0.9013 (14)	0.086 (4)	0.269 (16)
F3B	−0.016 (2)	−0.1807 (17)	0.7665 (19)	0.099 (7)	0.269 (16)
O1	0.28315 (8)	0.29984 (10)	0.70997 (10)	0.0233 (2)
N1	0.28617 (9)	0.31962 (11)	0.47756 (12)	0.0185 (2)
H1	0.2802 (14)	0.2804 (19)	0.4042 (19)	0.026 (5)*
C1	0.21837 (10)	0.12398 (12)	0.57572 (13)	0.0186 (3)
C2	0.24188 (13)	0.03871 (13)	0.47131 (14)	0.0259 (3)
H2	0.289997	0.062895	0.405100	0.031*
C3	0.19481 (15)	−0.08178 (14)	0.46425 (16)	0.0329 (4)
H3	0.211218	−0.139883	0.393221	0.039*
C4	0.12414 (14)	−0.11797 (14)	0.55988 (17)	0.0316 (3)
H4	0.091381	−0.199957	0.553952	0.038*
C5	0.10177 (11)	−0.03314 (14)	0.66438 (16)	0.0257 (3)
C6	0.14900 (11)	0.08690 (13)	0.67345 (14)	0.0211 (3)
H6	0.134024	0.143722	0.746265	0.025*
C7	0.26620 (10)	0.25486 (12)	0.59350 (13)	0.0178 (2)
C8	0.32898 (10)	0.44565 (12)	0.47321 (13)	0.0176 (2)
C9	0.39212 (10)	0.47530 (13)	0.36527 (13)	0.0195 (3)
H9	0.405719	0.411646	0.298485	0.023*
C10	0.43528 (11)	0.59762 (13)	0.35491 (14)	0.0213 (3)
H10	0.478028	0.618296	0.281319	0.026*
C12	0.35114 (11)	0.66145 (13)	0.56067 (14)	0.0216 (3)
H12	0.337493	0.725548	0.626949	0.026*
C11	0.41479 (11)	0.68865 (13)	0.45383 (14)	0.0210 (3)
C13	0.30738 (11)	0.53934 (12)	0.56998 (14)	0.0202 (3)
H13	0.262909	0.519959	0.642132	0.024*
C14	0.02873 (14)	−0.07127 (17)	0.7714 (2)	0.0388 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0326 (2)	0.02148 (17)	0.0334 (2)	−0.00686 (13)	0.00789 (15)	0.00072 (13)
F1A	0.078 (2)	0.0400 (14)	0.075 (2)	−0.0159 (15)	0.0523 (17)	−0.0029 (14)
F2A	0.0431 (17)	0.124 (4)	0.080 (3)	0.013 (2)	0.0130 (16)	0.083 (3)
F3A	0.0376 (13)	0.0609 (15)	0.089 (2)	−0.0250 (10)	0.0073 (12)	0.0120 (15)
F1B	0.038 (4)	0.143 (10)	0.068 (5)	0.053 (5)	0.010 (3)	0.057 (6)
F2B	0.059 (4)	0.158 (12)	0.042 (4)	−0.039 (6)	0.006 (3)	0.047 (6)
F3B	0.151 (13)	0.071 (7)	0.082 (8)	−0.086 (8)	0.053 (9)	−0.026 (6)
O1	0.0374 (6)	0.0201 (4)	0.0125 (4)	−0.0032 (4)	0.0025 (4)	0.0000 (3)
N1	0.0281 (6)	0.0156 (5)	0.0120 (5)	0.0002 (4)	0.0018 (4)	−0.0007 (4)
C1	0.0244 (6)	0.0150 (5)	0.0162 (6)	0.0012 (5)	−0.0018 (5)	0.0019 (4)
C2	0.0416 (8)	0.0184 (6)	0.0178 (6)	0.0021 (6)	0.0027 (6)	0.0014 (5)
C3	0.0564 (10)	0.0166 (6)	0.0253 (7)	0.0008 (6)	−0.0018 (7)	−0.0024 (5)
C4	0.0424 (9)	0.0183 (6)	0.0329 (8)	−0.0046 (6)	−0.0081 (7)	0.0032 (6)
C5	0.0242 (7)	0.0225 (7)	0.0299 (7)	−0.0021 (5)	−0.0031 (6)	0.0069 (5)
C6	0.0225 (6)	0.0199 (6)	0.0209 (6)	0.0008 (5)	0.0003 (5)	0.0020 (5)
C7	0.0222 (6)	0.0161 (5)	0.0152 (6)	0.0020 (5)	0.0020 (5)	0.0008 (4)
C8	0.0215 (6)	0.0164 (5)	0.0150 (6)	0.0012 (5)	0.0012 (5)	0.0021 (4)
C9	0.0242 (6)	0.0212 (6)	0.0133 (6)	0.0020 (5)	0.0020 (5)	−0.0001 (5)
C10	0.0231 (6)	0.0246 (6)	0.0165 (6)	0.0003 (5)	0.0034 (5)	0.0033 (5)
C12	0.0272 (7)	0.0182 (6)	0.0196 (6)	0.0017 (5)	0.0033 (5)	−0.0013 (5)
C11	0.0225 (6)	0.0179 (6)	0.0226 (7)	−0.0015 (5)	0.0014 (5)	0.0028 (5)
C13	0.0257 (7)	0.0177 (6)	0.0176 (6)	0.0012 (5)	0.0055 (5)	0.0008 (5)
C14	0.0320 (8)	0.0330 (8)	0.0520 (11)	−0.0067 (7)	0.0071 (8)	0.0127 (8)

Geometric parameters (Å, º)

Cl1—C11	1.7483 (14)	C3—H3	0.9500
F1A—C14	1.323 (4)	C4—C5	1.388 (2)
F2A—C14	1.283 (4)	C4—H4	0.9500
F3A—C14	1.363 (4)	C5—C6	1.3869 (19)
F1B—C14	1.284 (11)	C5—C14	1.492 (2)
F2B—C14	1.433 (13)	C6—H6	0.9500
F3B—C14	1.276 (8)	C8—C13	1.3927 (18)
O1—C7	1.2352 (16)	C8—C9	1.3954 (18)
N1—C7	1.3504 (16)	C9—C10	1.3916 (19)
N1—C8	1.4210 (16)	C9—H9	0.9500
N1—H1	0.823 (19)	C10—C11	1.3849 (19)
C1—C6	1.3917 (19)	C10—H10	0.9500
C1—C2	1.3934 (19)	C12—C11	1.3857 (19)
C1—C7	1.4977 (18)	C12—C13	1.3919 (18)
C2—C3	1.390 (2)	C12—H12	0.9500
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.386 (2)
C7—N1—C8	125.07 (11)	C10—C9—C8	120.36 (12)
C7—N1—H1	117.8 (13)	C10—C9—H9	119.8
C8—N1—H1	116.7 (13)	C8—C9—H9	119.8
C6—C1—C2	119.63 (13)	C11—C10—C9	118.79 (12)
C6—C1—C7	116.44 (12)	C11—C10—H10	120.6
C2—C1—C7	123.90 (12)	C9—C10—H10	120.6
C3—C2—C1	119.86 (14)	C11—C12—C13	119.39 (12)
C3—C2—H2	120.1	C11—C12—H12	120.3
C1—C2—H2	120.1	C13—C12—H12	120.3
C4—C3—C2	120.61 (14)	C10—C11—C12	121.63 (12)
C4—C3—H3	119.7	C10—C11—Cl1	119.31 (10)
C2—C3—H3	119.7	C12—C11—Cl1	119.05 (11)
C3—C4—C5	119.27 (14)	C12—C13—C8	119.79 (12)
C3—C4—H4	120.4	C12—C13—H13	120.1
C5—C4—H4	120.4	C8—C13—H13	120.1
C6—C5—C4	120.70 (14)	F3B—C14—F1B	109.1 (9)
C6—C5—C14	118.87 (15)	F2A—C14—F1A	109.7 (4)
C4—C5—C14	120.40 (14)	F2A—C14—F3A	106.8 (3)
C5—C6—C1	119.90 (13)	F1A—C14—F3A	104.3 (3)
C5—C6—H6	120.1	F3B—C14—F2B	99.6 (9)
C1—C6—H6	120.1	F1B—C14—F2B	98.1 (9)
O1—C7—N1	123.19 (12)	F3B—C14—C5	120.8 (5)
O1—C7—C1	120.03 (11)	F2A—C14—C5	113.0 (2)
N1—C7—C1	116.76 (11)	F1B—C14—C5	116.3 (5)
C13—C8—C9	120.01 (12)	F1A—C14—C5	113.23 (19)
C13—C8—N1	122.15 (12)	F3A—C14—C5	109.2 (3)
C9—C8—N1	117.82 (11)	F2B—C14—C5	109.1 (5)
C6—C1—C2—C3	1.0 (2)	C8—C9—C10—C11	0.3 (2)
C7—C1—C2—C3	178.95 (14)	C9—C10—C11—C12	−1.2 (2)
C1—C2—C3—C4	0.3 (2)	C9—C10—C11—Cl1	178.00 (10)
C2—C3—C4—C5	−0.9 (2)	C13—C12—C11—C10	0.7 (2)
C3—C4—C5—C6	0.2 (2)	C13—C12—C11—Cl1	−178.55 (11)
C3—C4—C5—C14	−177.95 (15)	C11—C12—C13—C8	0.8 (2)
C4—C5—C6—C1	1.0 (2)	C9—C8—C13—C12	−1.7 (2)
C14—C5—C6—C1	179.24 (13)	N1—C8—C13—C12	−179.80 (12)
C2—C1—C6—C5	−1.6 (2)	C6—C5—C14—F3B	179.8 (18)
C7—C1—C6—C5	−179.75 (12)	C4—C5—C14—F3B	−2.0 (18)
C8—N1—C7—O1	0.3 (2)	C6—C5—C14—F2A	−94.3 (5)
C8—N1—C7—C1	178.49 (12)	C4—C5—C14—F2A	83.9 (5)
C6—C1—C7—O1	31.87 (18)	C6—C5—C14—F1B	43.9 (8)
C2—C1—C7—O1	−146.16 (14)	C4—C5—C14—F1B	−137.9 (8)
C6—C1—C7—N1	−146.40 (12)	C6—C5—C14—F1A	31.3 (3)
C2—C1—C7—N1	35.57 (19)	C4—C5—C14—F1A	−150.5 (3)
C7—N1—C8—C13	−33.6 (2)	C6—C5—C14—F3A	147.0 (2)
C7—N1—C8—C9	148.22 (13)	C4—C5—C14—F3A	−34.8 (3)
C13—C8—C9—C10	1.1 (2)	C6—C5—C14—F2B	−65.8 (9)
N1—C8—C9—C10	179.32 (12)	C4—C5—C14—F2B	112.4 (9)

(PC44)

Crystal data

C14H9ClF3NO	F(000) = 1216
Mr = 299.67	Dx = 1.561 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.952 (3) Å	Cell parameters from 7877 reflections
b = 5.2521 (7) Å	θ = 2.4–29.7°
c = 28.760 (4) Å	µ = 0.33 mm^−1
β = 94.966 (4)°	T = 105 K
V = 2551.0 (6) Å^3	Rod
Z = 8	0.20 × 0.15 × 0.05 mm

Data collection

Bruker APEX-II CCD diffractometer	3328 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.062
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 2.8°
Tmin = 0.732, Tmax = 0.886	h = −19→20
27880 measured reflections	k = −6→5
4740 independent reflections	l = −34→34

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 1.8012P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4740 reflections	Δρmax = 0.46 e Å^−3
369 parameters	Δρmin = −0.29 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.04844 (4)	0.08654 (14)	0.39245 (2)	0.02630 (19)
Cl2	0.45825 (4)	0.75139 (14)	0.10845 (2)	0.02710 (19)
F1	0.67040 (11)	0.2072 (4)	−0.01944 (5)	0.0597 (6)
F2	0.56142 (11)	0.2655 (5)	0.01011 (6)	0.0650 (7)
F3	0.61162 (12)	−0.1033 (4)	0.00816 (6)	0.0609 (6)
F4	0.88668 (10)	0.5006 (4)	0.51202 (5)	0.0434 (5)
F5	0.84460 (10)	0.8824 (3)	0.51208 (5)	0.0420 (5)
F6	0.94895 (10)	0.7888 (5)	0.47824 (6)	0.0598 (6)
O1	0.81495 (10)	0.5475 (3)	0.20729 (5)	0.0204 (4)
O2	0.68523 (10)	0.2883 (3)	0.29629 (5)	0.0198 (4)
N1	0.83508 (12)	0.1204 (4)	0.21764 (7)	0.0154 (5)
H1	0.8190 (15)	−0.033 (6)	0.2074 (9)	0.031 (8)*
N2	0.66492 (12)	0.7152 (4)	0.28583 (7)	0.0162 (5)
H2	0.6811 (15)	0.859 (6)	0.2960 (8)	0.023 (8)*
C1	0.76014 (14)	0.2681 (5)	0.14753 (8)	0.0157 (5)
C2	0.77626 (14)	0.0580 (5)	0.12032 (8)	0.0195 (6)
H2A	0.816854	−0.058001	0.131017	0.023*
C3	0.73344 (15)	0.0175 (5)	0.07783 (8)	0.0222 (6)
H3	0.744756	−0.125680	0.059360	0.027*
C4	0.67384 (15)	0.1865 (5)	0.06214 (8)	0.0208 (6)
C5	0.65705 (15)	0.3972 (5)	0.08902 (8)	0.0209 (6)
H5	0.616121	0.512050	0.078350	0.025*
C6	0.70048 (14)	0.4381 (5)	0.13143 (8)	0.0178 (6)
H6	0.689644	0.582722	0.149677	0.021*
C7	0.80563 (14)	0.3276 (5)	0.19334 (8)	0.0162 (6)
C8	0.88408 (14)	0.1265 (5)	0.26036 (8)	0.0154 (5)
C9	0.87932 (14)	−0.0773 (5)	0.29109 (8)	0.0165 (5)
H9	0.841515	−0.208375	0.284140	0.020*
C10	0.92959 (14)	−0.0894 (5)	0.33179 (8)	0.0178 (6)
H10	0.926368	−0.228386	0.352690	0.021*
C11	0.98459 (14)	0.1031 (5)	0.34170 (8)	0.0165 (6)
C12	0.98927 (14)	0.3067 (5)	0.31169 (8)	0.0175 (6)
H12	1.026696	0.438531	0.318964	0.021*
C13	0.93899 (14)	0.3189 (5)	0.27070 (8)	0.0163 (6)
H13	0.942330	0.458304	0.249921	0.020*
C14	0.62877 (16)	0.1410 (6)	0.01563 (9)	0.0272 (7)
C15	0.73971 (14)	0.5687 (5)	0.35608 (8)	0.0158 (5)
C16	0.72249 (15)	0.7757 (5)	0.38333 (8)	0.0201 (6)
H16	0.680781	0.888379	0.372969	0.024*
C17	0.76612 (15)	0.8189 (5)	0.42578 (8)	0.0220 (6)
H17	0.753764	0.959996	0.444500	0.026*
C18	0.82749 (14)	0.6569 (5)	0.44087 (8)	0.0196 (6)
C19	0.84536 (14)	0.4489 (5)	0.41392 (8)	0.0202 (6)
H19	0.887694	0.338346	0.424194	0.024*
C20	0.80095 (14)	0.4032 (5)	0.37182 (8)	0.0186 (6)
H20	0.812253	0.258751	0.353643	0.022*
C21	0.69442 (14)	0.5087 (5)	0.31037 (8)	0.0157 (5)
C22	0.61726 (14)	0.7101 (5)	0.24272 (8)	0.0155 (5)
C23	0.62281 (14)	0.9148 (5)	0.21215 (8)	0.0166 (5)
H23	0.660163	1.046466	0.219690	0.020*
C24	0.57443 (14)	0.9270 (5)	0.17109 (8)	0.0180 (6)
H24	0.578492	1.066286	0.150351	0.022*
C25	0.51998 (14)	0.7352 (5)	0.16030 (8)	0.0173 (6)
C26	0.51412 (14)	0.5294 (5)	0.18999 (8)	0.0160 (5)
H26	0.477022	0.397537	0.182081	0.019*
C27	0.56275 (13)	0.5171 (5)	0.23133 (8)	0.0152 (5)
H27	0.558800	0.376774	0.251854	0.018*
C28	0.87694 (17)	0.7076 (6)	0.48559 (9)	0.0276 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0260 (4)	0.0322 (4)	0.0195 (3)	−0.0030 (3)	−0.0050 (3)	0.0025 (3)
Cl2	0.0273 (4)	0.0327 (4)	0.0200 (3)	−0.0017 (3)	−0.0052 (3)	0.0033 (3)
F1	0.0606 (13)	0.1000 (18)	0.0175 (8)	−0.0368 (12)	−0.0013 (8)	0.0086 (10)
F2	0.0490 (12)	0.0953 (18)	0.0455 (11)	0.0285 (12)	−0.0254 (9)	−0.0251 (11)
F3	0.0919 (16)	0.0411 (13)	0.0430 (11)	−0.0271 (11)	−0.0333 (10)	0.0041 (9)
F4	0.0599 (12)	0.0399 (11)	0.0270 (9)	0.0068 (9)	−0.0150 (8)	0.0035 (8)
F5	0.0584 (12)	0.0394 (11)	0.0256 (9)	0.0057 (9)	−0.0110 (8)	−0.0109 (8)
F6	0.0360 (11)	0.1094 (19)	0.0328 (10)	−0.0352 (11)	−0.0033 (8)	−0.0087 (10)
O1	0.0246 (10)	0.0116 (11)	0.0239 (9)	0.0020 (8)	−0.0042 (8)	−0.0022 (7)
O2	0.0234 (10)	0.0131 (11)	0.0219 (9)	0.0018 (8)	−0.0046 (8)	−0.0024 (7)
N1	0.0171 (11)	0.0118 (12)	0.0169 (11)	−0.0014 (9)	−0.0007 (9)	−0.0019 (9)
N2	0.0178 (12)	0.0106 (12)	0.0197 (11)	−0.0019 (9)	−0.0008 (9)	−0.0015 (9)
C1	0.0149 (13)	0.0151 (14)	0.0175 (12)	−0.0043 (11)	0.0027 (10)	0.0000 (11)
C2	0.0172 (13)	0.0182 (15)	0.0231 (13)	0.0020 (11)	0.0021 (11)	−0.0004 (11)
C3	0.0260 (15)	0.0205 (15)	0.0207 (13)	−0.0012 (12)	0.0053 (11)	−0.0035 (11)
C4	0.0227 (14)	0.0227 (16)	0.0174 (13)	−0.0063 (12)	0.0033 (11)	0.0029 (11)
C5	0.0194 (14)	0.0192 (15)	0.0237 (13)	−0.0002 (12)	0.0004 (11)	0.0057 (11)
C6	0.0192 (13)	0.0133 (14)	0.0212 (13)	−0.0006 (11)	0.0037 (10)	−0.0025 (10)
C7	0.0129 (13)	0.0155 (15)	0.0208 (13)	0.0003 (11)	0.0054 (10)	0.0019 (11)
C8	0.0148 (13)	0.0158 (14)	0.0159 (12)	0.0035 (11)	0.0030 (10)	−0.0038 (10)
C9	0.0171 (13)	0.0105 (14)	0.0225 (13)	−0.0013 (11)	0.0045 (10)	−0.0031 (10)
C10	0.0229 (14)	0.0137 (14)	0.0176 (12)	0.0012 (12)	0.0058 (10)	0.0018 (10)
C11	0.0158 (13)	0.0176 (15)	0.0164 (12)	0.0026 (11)	0.0031 (10)	−0.0007 (10)
C12	0.0134 (13)	0.0165 (14)	0.0228 (13)	−0.0007 (11)	0.0031 (10)	−0.0039 (11)
C13	0.0173 (13)	0.0145 (14)	0.0176 (12)	0.0014 (11)	0.0046 (10)	0.0006 (10)
C14	0.0293 (16)	0.0290 (18)	0.0229 (14)	−0.0088 (14)	0.0005 (12)	0.0024 (12)
C15	0.0153 (13)	0.0139 (14)	0.0181 (12)	−0.0033 (11)	0.0013 (10)	0.0017 (10)
C16	0.0233 (14)	0.0171 (15)	0.0196 (13)	0.0038 (12)	0.0007 (11)	0.0001 (11)
C17	0.0259 (15)	0.0188 (15)	0.0218 (14)	−0.0012 (12)	0.0042 (11)	−0.0043 (11)
C18	0.0205 (14)	0.0205 (15)	0.0180 (13)	−0.0054 (12)	0.0032 (11)	0.0025 (11)
C19	0.0171 (13)	0.0214 (16)	0.0220 (13)	−0.0014 (12)	0.0003 (11)	0.0038 (11)
C20	0.0222 (14)	0.0143 (14)	0.0196 (13)	−0.0002 (11)	0.0041 (11)	0.0005 (10)
C21	0.0148 (13)	0.0135 (14)	0.0192 (12)	0.0011 (11)	0.0036 (10)	0.0004 (11)
C22	0.0136 (13)	0.0160 (14)	0.0171 (12)	0.0025 (11)	0.0025 (10)	−0.0037 (10)
C23	0.0174 (13)	0.0113 (14)	0.0216 (13)	0.0003 (11)	0.0044 (10)	−0.0024 (10)
C24	0.0210 (14)	0.0157 (14)	0.0178 (12)	0.0014 (12)	0.0051 (10)	0.0015 (11)
C25	0.0164 (13)	0.0209 (15)	0.0147 (12)	0.0031 (11)	0.0019 (10)	−0.0021 (11)
C26	0.0131 (13)	0.0140 (14)	0.0210 (13)	−0.0010 (10)	0.0022 (10)	−0.0025 (10)
C27	0.0162 (13)	0.0108 (13)	0.0192 (12)	0.0016 (10)	0.0048 (10)	0.0019 (10)
C28	0.0325 (17)	0.0312 (18)	0.0190 (14)	−0.0050 (14)	0.0007 (12)	−0.0020 (13)

Geometric parameters (Å, º)

Cl1—C11	1.742 (2)	C9—C10	1.388 (3)
Cl2—C25	1.748 (2)	C9—H9	0.9500
F1—C14	1.326 (3)	C10—C11	1.388 (3)
F2—C14	1.314 (3)	C10—H10	0.9500
F3—C14	1.329 (3)	C11—C12	1.381 (3)
F4—C28	1.329 (3)	C12—C13	1.395 (3)
F5—C28	1.340 (3)	C12—H12	0.9500
F6—C28	1.327 (3)	C13—H13	0.9500
O1—C7	1.228 (3)	C15—C16	1.386 (3)
O2—C21	1.232 (3)	C15—C20	1.399 (3)
N1—C7	1.364 (3)	C15—C21	1.497 (3)
N1—C8	1.422 (3)	C16—C17	1.390 (3)
N1—H1	0.89 (3)	C16—H16	0.9500
N2—C21	1.365 (3)	C17—C18	1.384 (4)
N2—C22	1.420 (3)	C17—H17	0.9500
N2—H2	0.85 (3)	C18—C19	1.388 (4)
C1—C2	1.393 (3)	C18—C28	1.497 (3)
C1—C6	1.398 (3)	C19—C20	1.390 (3)
C1—C7	1.501 (3)	C19—H19	0.9500
C2—C3	1.383 (3)	C20—H20	0.9500
C2—H2A	0.9500	C22—C27	1.391 (3)
C3—C4	1.390 (4)	C22—C23	1.397 (3)
C3—H3	0.9500	C23—C24	1.380 (3)
C4—C5	1.394 (4)	C23—H23	0.9500
C4—C14	1.501 (3)	C24—C25	1.383 (3)
C5—C6	1.386 (3)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.386 (3)
C6—H6	0.9500	C26—C27	1.389 (3)
C8—C13	1.388 (3)	C26—H26	0.9500
C8—C9	1.395 (3)	C27—H27	0.9500
C7—N1—C8	125.8 (2)	F2—C14—C4	113.5 (2)
C7—N1—H1	117.6 (17)	F1—C14—C4	111.9 (2)
C8—N1—H1	116.4 (17)	F3—C14—C4	112.6 (2)
C21—N2—C22	126.3 (2)	C16—C15—C20	119.4 (2)
C21—N2—H2	116.0 (18)	C16—C15—C21	123.0 (2)
C22—N2—H2	117.3 (18)	C20—C15—C21	117.6 (2)
C2—C1—C6	119.4 (2)	C15—C16—C17	120.2 (2)
C2—C1—C7	123.2 (2)	C15—C16—H16	119.9
C6—C1—C7	117.4 (2)	C17—C16—H16	119.9
C3—C2—C1	120.3 (2)	C18—C17—C16	120.2 (2)
C3—C2—H2A	119.9	C18—C17—H17	119.9
C1—C2—H2A	119.9	C16—C17—H17	119.9
C2—C3—C4	120.0 (2)	C17—C18—C19	120.2 (2)
C2—C3—H3	120.0	C17—C18—C28	120.7 (2)
C4—C3—H3	120.0	C19—C18—C28	119.1 (2)
C3—C4—C5	120.3 (2)	C18—C19—C20	119.6 (2)
C3—C4—C14	119.2 (2)	C18—C19—H19	120.2
C5—C4—C14	120.5 (2)	C20—C19—H19	120.2
C6—C5—C4	119.5 (2)	C19—C20—C15	120.4 (2)
C6—C5—H5	120.2	C19—C20—H20	119.8
C4—C5—H5	120.2	C15—C20—H20	119.8
C5—C6—C1	120.4 (2)	O2—C21—N2	123.1 (2)
C5—C6—H6	119.8	O2—C21—C15	121.8 (2)
C1—C6—H6	119.8	N2—C21—C15	115.1 (2)
O1—C7—N1	123.5 (2)	C27—C22—C23	119.5 (2)
O1—C7—C1	121.6 (2)	C27—C22—N2	122.4 (2)
N1—C7—C1	114.9 (2)	C23—C22—N2	118.1 (2)
C13—C8—C9	119.8 (2)	C24—C23—C22	120.5 (2)
C13—C8—N1	122.1 (2)	C24—C23—H23	119.8
C9—C8—N1	117.9 (2)	C22—C23—H23	119.8
C10—C9—C8	120.3 (2)	C23—C24—C25	119.6 (2)
C10—C9—H9	119.8	C23—C24—H24	120.2
C8—C9—H9	119.8	C25—C24—H24	120.2
C11—C10—C9	119.5 (2)	C24—C25—C26	120.8 (2)
C11—C10—H10	120.3	C24—C25—Cl2	119.62 (19)
C9—C10—H10	120.3	C26—C25—Cl2	119.60 (19)
C12—C11—C10	120.6 (2)	C25—C26—C27	119.7 (2)
C12—C11—Cl1	119.81 (19)	C25—C26—H26	120.2
C10—C11—Cl1	119.54 (19)	C27—C26—H26	120.2
C11—C12—C13	120.0 (2)	C26—C27—C22	120.0 (2)
C11—C12—H12	120.0	C26—C27—H27	120.0
C13—C12—H12	120.0	C22—C27—H27	120.0
C8—C13—C12	119.8 (2)	F6—C28—F4	106.5 (2)
C8—C13—H13	120.1	F6—C28—F5	107.3 (2)
C12—C13—H13	120.1	F4—C28—F5	105.8 (2)
F2—C14—F1	107.0 (2)	F6—C28—C18	112.0 (2)
F2—C14—F3	106.6 (2)	F4—C28—C18	112.2 (2)
F1—C14—F3	104.7 (2)	F5—C28—C18	112.6 (2)
C6—C1—C2—C3	−0.2 (4)	C20—C15—C16—C17	0.4 (4)
C7—C1—C2—C3	−178.3 (2)	C21—C15—C16—C17	179.1 (2)
C1—C2—C3—C4	−0.2 (4)	C15—C16—C17—C18	0.7 (4)
C2—C3—C4—C5	0.1 (4)	C16—C17—C18—C19	−0.7 (4)
C2—C3—C4—C14	179.2 (2)	C16—C17—C18—C28	177.5 (2)
C3—C4—C5—C6	0.3 (4)	C17—C18—C19—C20	−0.4 (4)
C14—C4—C5—C6	−178.7 (2)	C28—C18—C19—C20	−178.6 (2)
C4—C5—C6—C1	−0.8 (4)	C18—C19—C20—C15	1.4 (4)
C2—C1—C6—C5	0.7 (4)	C16—C15—C20—C19	−1.4 (4)
C7—C1—C6—C5	178.9 (2)	C21—C15—C20—C19	179.8 (2)
C8—N1—C7—O1	−4.1 (4)	C22—N2—C21—O2	3.2 (4)
C8—N1—C7—C1	175.9 (2)	C22—N2—C21—C15	−177.1 (2)
C2—C1—C7—O1	149.7 (2)	C16—C15—C21—O2	−148.7 (2)
C6—C1—C7—O1	−28.5 (3)	C20—C15—C21—O2	30.0 (3)
C2—C1—C7—N1	−30.4 (3)	C16—C15—C21—N2	31.6 (3)
C6—C1—C7—N1	151.5 (2)	C20—C15—C21—N2	−149.7 (2)
C7—N1—C8—C13	−33.5 (3)	C21—N2—C22—C27	33.5 (4)
C7—N1—C8—C9	150.5 (2)	C21—N2—C22—C23	−150.1 (2)
C13—C8—C9—C10	−0.4 (3)	C27—C22—C23—C24	0.4 (3)
N1—C8—C9—C10	175.7 (2)	N2—C22—C23—C24	−176.1 (2)
C8—C9—C10—C11	0.1 (3)	C22—C23—C24—C25	0.2 (4)
C9—C10—C11—C12	0.5 (4)	C23—C24—C25—C26	−0.8 (4)
C9—C10—C11—Cl1	−179.32 (18)	C23—C24—C25—Cl2	179.62 (18)
C10—C11—C12—C13	−0.7 (4)	C24—C25—C26—C27	0.8 (4)
Cl1—C11—C12—C13	179.10 (18)	Cl2—C25—C26—C27	−179.58 (18)
C9—C8—C13—C12	0.2 (3)	C25—C26—C27—C22	−0.3 (3)
N1—C8—C13—C12	−175.7 (2)	C23—C22—C27—C26	−0.3 (3)
C11—C12—C13—C8	0.4 (3)	N2—C22—C27—C26	176.0 (2)
C3—C4—C14—F2	162.2 (2)	C17—C18—C28—F6	−107.4 (3)
C5—C4—C14—F2	−18.7 (4)	C19—C18—C28—F6	70.8 (3)
C3—C4—C14—F1	−76.7 (3)	C17—C18—C28—F4	132.9 (3)
C5—C4—C14—F1	102.4 (3)	C19—C18—C28—F4	−48.9 (3)
C3—C4—C14—F3	41.0 (3)	C17—C18—C28—F5	13.7 (4)
C5—C4—C14—F3	−140.0 (3)	C19—C18—C28—F5	−168.1 (2)

(PB23)

Crystal data

C14H9BrF3NO	F(000) = 680
Mr = 344.13	Dx = 1.734 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.7992 (3) Å	Cell parameters from 9972 reflections
b = 10.0208 (7) Å	θ = 2.2–30.5°
c = 27.428 (2) Å	µ = 3.15 mm^−1
β = 91.755 (2)°	T = 100 K
V = 1318.47 (16) Å^3	Plate
Z = 4	0.21 × 0.16 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	3558 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan SADABS 2014/4	θmax = 30.5°, θmin = 2.5°
Tmin = 0.457, Tmax = 0.704	h = −6→6
28180 measured reflections	k = −14→14
4008 independent reflections	l = −39→39

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.062	w = 1/[σ^2(Fo^2) + (0.0294P)^2 + 0.8053P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.007
4008 reflections	Δρmax = 0.50 e Å^−3
213 parameters	Δρmin = −0.37 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1A	0.5804 (6)	0.3439 (7)	0.75200 (18)	0.091 (3)	0.512 (5)
F2A	0.9044 (14)	0.4796 (4)	0.76602 (13)	0.085 (2)	0.512 (5)
F3A	0.9703 (8)	0.3162 (4)	0.72128 (9)	0.0645 (13)	0.512 (5)
F1B	0.9792 (7)	0.4308 (6)	0.7450 (2)	0.095 (3)	0.488 (5)
F3B	0.5869 (8)	0.4334 (4)	0.77547 (12)	0.0588 (11)	0.488 (5)
F2B	0.6950 (13)	0.2746 (4)	0.73073 (13)	0.086 (2)	0.488 (5)
Br1	1.34389 (3)	0.07890 (2)	1.04678 (2)	0.02188 (5)
O1	0.5916 (2)	0.31174 (11)	0.94761 (4)	0.0217 (2)
N1	1.0295 (2)	0.27459 (12)	0.97965 (4)	0.0145 (2)
H1	1.196 (4)	0.2635 (19)	0.9721 (7)	0.020 (4)*
C1	0.9421 (3)	0.24304 (13)	0.89356 (5)	0.0153 (2)
C2	1.1314 (3)	0.13949 (15)	0.88779 (5)	0.0200 (3)
H2	1.203429	0.093121	0.915635	0.024*
C3	1.2158 (4)	0.10338 (17)	0.84162 (6)	0.0274 (3)
H3	1.342360	0.031462	0.837894	0.033*
C4	1.1149 (3)	0.17257 (17)	0.80092 (5)	0.0264 (3)
H4	1.173493	0.149019	0.769284	0.032*
C5	0.9279 (3)	0.27641 (16)	0.80688 (5)	0.0236 (3)
C6	0.8370 (3)	0.31078 (15)	0.85268 (5)	0.0203 (3)
H6	0.703959	0.380062	0.856152	0.024*
C7	0.8370 (3)	0.28013 (13)	0.94261 (5)	0.0151 (2)
C8	0.9744 (3)	0.29759 (13)	1.02944 (5)	0.0143 (2)
C9	1.1030 (3)	0.21833 (13)	1.06533 (5)	0.0162 (2)
C10	1.0573 (3)	0.23758 (16)	1.11438 (5)	0.0234 (3)
H10	1.147525	0.182626	1.138257	0.028*
C11	0.8774 (4)	0.33845 (17)	1.12822 (6)	0.0279 (3)
H11	0.842121	0.352232	1.161736	0.033*
C12	0.7499 (3)	0.41880 (16)	1.09309 (6)	0.0257 (3)
H12	0.627814	0.487957	1.102718	0.031*
C13	0.7981 (3)	0.39950 (14)	1.04398 (5)	0.0192 (3)
H13	0.710804	0.455919	1.020245	0.023*
C14	0.8240 (4)	0.3535 (2)	0.76328 (6)	0.0366 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.0210 (14)	0.167 (6)	0.083 (4)	−0.023 (2)	−0.0202 (17)	0.095 (4)
F2A	0.182 (6)	0.0350 (16)	0.0357 (18)	−0.018 (2)	−0.037 (2)	0.0163 (13)
F3A	0.086 (3)	0.090 (3)	0.0176 (11)	0.036 (2)	0.0048 (12)	0.0104 (13)
F1B	0.0328 (17)	0.153 (7)	0.098 (4)	−0.028 (3)	−0.008 (2)	0.106 (5)
F3B	0.067 (2)	0.080 (3)	0.0293 (15)	0.0335 (19)	−0.0058 (13)	0.0221 (15)
F2B	0.143 (6)	0.075 (2)	0.0351 (18)	0.010 (3)	−0.050 (3)	−0.0062 (16)
Br1	0.02176 (8)	0.02048 (8)	0.02343 (8)	0.00966 (5)	0.00117 (5)	0.00318 (5)
O1	0.0107 (4)	0.0321 (6)	0.0224 (5)	0.0037 (4)	0.0012 (4)	0.0013 (4)
N1	0.0102 (5)	0.0187 (5)	0.0148 (5)	0.0033 (4)	0.0023 (4)	0.0005 (4)
C1	0.0125 (6)	0.0178 (6)	0.0155 (6)	−0.0004 (5)	0.0000 (4)	0.0007 (5)
C2	0.0206 (7)	0.0211 (7)	0.0184 (6)	0.0046 (5)	−0.0001 (5)	0.0001 (5)
C3	0.0306 (8)	0.0289 (8)	0.0228 (7)	0.0074 (6)	0.0039 (6)	−0.0063 (6)
C4	0.0316 (8)	0.0302 (8)	0.0177 (7)	−0.0051 (6)	0.0033 (6)	−0.0047 (6)
C5	0.0278 (8)	0.0255 (7)	0.0172 (6)	−0.0062 (6)	−0.0048 (5)	0.0035 (5)
C6	0.0190 (7)	0.0220 (7)	0.0197 (6)	0.0019 (5)	−0.0023 (5)	0.0031 (5)
C7	0.0133 (6)	0.0150 (6)	0.0169 (6)	0.0014 (4)	0.0010 (4)	0.0034 (4)
C8	0.0127 (6)	0.0149 (6)	0.0154 (6)	0.0003 (4)	0.0018 (4)	0.0000 (4)
C9	0.0147 (6)	0.0154 (6)	0.0187 (6)	0.0028 (5)	0.0009 (5)	0.0003 (5)
C10	0.0274 (8)	0.0252 (7)	0.0177 (6)	0.0028 (6)	−0.0003 (5)	0.0013 (5)
C11	0.0340 (9)	0.0322 (8)	0.0176 (7)	0.0038 (7)	0.0059 (6)	−0.0045 (6)
C12	0.0273 (8)	0.0247 (7)	0.0254 (7)	0.0069 (6)	0.0070 (6)	−0.0066 (6)
C13	0.0178 (6)	0.0180 (6)	0.0219 (7)	0.0043 (5)	0.0027 (5)	0.0000 (5)
C14	0.0491 (11)	0.0399 (10)	0.0203 (7)	−0.0022 (8)	−0.0061 (7)	0.0073 (7)

Geometric parameters (Å, º)

F1A—C14	1.204 (3)	C3—H3	0.9500
F2A—C14	1.322 (4)	C4—C5	1.387 (2)
F3A—C14	1.418 (3)	C4—H4	0.9500
F1B—C14	1.195 (4)	C5—C6	1.386 (2)
F3B—C14	1.439 (4)	C5—C14	1.496 (2)
F2B—C14	1.331 (4)	C6—H6	0.9500
Br1—C9	1.8929 (13)	C8—C13	1.3922 (18)
O1—C7	1.2313 (16)	C8—C9	1.3944 (18)
N1—C7	1.3531 (17)	C9—C10	1.3831 (19)
N1—C8	1.4176 (16)	C10—C11	1.390 (2)
N1—H1	0.840 (19)	C10—H10	0.9500
C1—C2	1.3912 (19)	C11—C12	1.384 (2)
C1—C6	1.3921 (18)	C11—H11	0.9500
C1—C7	1.4982 (18)	C12—C13	1.387 (2)
C2—C3	1.390 (2)	C12—H12	0.9500
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.389 (2)
C7—N1—C8	124.99 (11)	C10—C9—C8	121.82 (13)
C7—N1—H1	117.1 (13)	C10—C9—Br1	118.74 (10)
C8—N1—H1	117.7 (13)	C8—C9—Br1	119.44 (10)
C2—C1—C6	119.59 (13)	C9—C10—C11	119.05 (14)
C2—C1—C7	121.75 (12)	C9—C10—H10	120.5
C6—C1—C7	118.60 (12)	C11—C10—H10	120.5
C3—C2—C1	120.50 (14)	C12—C11—C10	119.88 (14)
C3—C2—H2	119.8	C12—C11—H11	120.1
C1—C2—H2	119.8	C10—C11—H11	120.1
C4—C3—C2	119.90 (15)	C11—C12—C13	120.75 (14)
C4—C3—H3	120.0	C11—C12—H12	119.6
C2—C3—H3	120.0	C13—C12—H12	119.6
C5—C4—C3	119.39 (14)	C12—C13—C8	120.10 (13)
C5—C4—H4	120.3	C12—C13—H13	119.9
C3—C4—H4	120.3	C8—C13—H13	119.9
C6—C5—C4	121.06 (14)	F1A—C14—F2A	111.7 (4)
C6—C5—C14	119.32 (15)	F1B—C14—F2B	112.7 (4)
C4—C5—C14	119.61 (15)	F1A—C14—F3A	105.7 (3)
C5—C6—C1	119.52 (14)	F2A—C14—F3A	98.5 (3)
C5—C6—H6	120.2	F1B—C14—F3B	104.1 (4)
C1—C6—H6	120.2	F2B—C14—F3B	97.6 (3)
O1—C7—N1	124.08 (12)	F1B—C14—C5	118.2 (2)
O1—C7—C1	120.88 (12)	F1A—C14—C5	117.5 (2)
N1—C7—C1	115.03 (11)	F2A—C14—C5	111.0 (2)
C13—C8—C9	118.37 (12)	F2B—C14—C5	111.5 (2)
C13—C8—N1	121.89 (12)	F3A—C14—C5	110.62 (19)
C9—C8—N1	119.73 (12)	F3B—C14—C5	110.38 (18)
C6—C1—C2—C3	0.0 (2)	N1—C8—C9—Br1	−1.22 (18)
C7—C1—C2—C3	177.11 (14)	C8—C9—C10—C11	0.2 (2)
C1—C2—C3—C4	1.2 (2)	Br1—C9—C10—C11	−179.04 (12)
C2—C3—C4—C5	−0.7 (3)	C9—C10—C11—C12	−0.8 (3)
C3—C4—C5—C6	−1.0 (2)	C10—C11—C12—C13	0.3 (3)
C3—C4—C5—C14	178.48 (16)	C11—C12—C13—C8	0.7 (2)
C4—C5—C6—C1	2.2 (2)	C9—C8—C13—C12	−1.2 (2)
C14—C5—C6—C1	−177.29 (15)	N1—C8—C13—C12	−179.94 (14)
C2—C1—C6—C5	−1.7 (2)	C6—C5—C14—F1B	105.5 (5)
C7—C1—C6—C5	−178.87 (13)	C4—C5—C14—F1B	−74.0 (5)
C8—N1—C7—O1	3.3 (2)	C6—C5—C14—F1A	−66.9 (5)
C8—N1—C7—C1	−176.09 (12)	C4—C5—C14—F1A	113.6 (5)
C2—C1—C7—O1	−140.66 (14)	C6—C5—C14—F2A	63.4 (4)
C6—C1—C7—O1	36.5 (2)	C4—C5—C14—F2A	−116.1 (4)
C2—C1—C7—N1	38.75 (19)	C6—C5—C14—F2B	−121.5 (4)
C6—C1—C7—N1	−144.11 (13)	C4—C5—C14—F2B	59.0 (4)
C7—N1—C8—C13	−41.1 (2)	C6—C5—C14—F3A	171.6 (3)
C7—N1—C8—C9	140.20 (14)	C4—C5—C14—F3A	−7.9 (3)
C13—C8—C9—C10	0.8 (2)	C6—C5—C14—F3B	−14.2 (3)
N1—C8—C9—C10	179.55 (13)	C4—C5—C14—F3B	166.3 (3)
C13—C8—C9—Br1	180.00 (10)

(PB24)

Crystal data

C14H9BrF3NO	F(000) = 680
Mr = 344.13	Dx = 1.739 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.8056 (2) Å	Cell parameters from 5637 reflections
b = 27.8678 (10) Å	θ = 2.9–29.3°
c = 9.8421 (4) Å	µ = 3.16 mm^−1
β = 94.227 (3)°	T = 100 K
V = 1314.48 (9) Å^3	Plate
Z = 4	0.32 × 0.24 × 0.13 mm

Data collection

Bruker APEX-II CCD diffractometer	2227 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.037
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 2.2°
Tmin = 0.512, Tmax = 0.652	h = −5→5
10604 measured reflections	k = −33→33
2435 independent reflections	l = −11→11

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.073	w = 1/[σ^2(Fo^2) + (0.0183P)^2 + 2.2721P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
2435 reflections	Δρmax = 0.42 e Å^−3
201 parameters	Δρmin = −0.62 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Br1	0.83208 (6)	−0.04414 (2)	0.58176 (3)	0.01617 (11)
F1A	0.9662 (12)	0.2501 (2)	0.5747 (10)	0.0374 (14)	0.77 (2)
F2A	0.5425 (12)	0.2683 (2)	0.5312 (11)	0.0495 (18)	0.77 (2)
F3A	0.692 (3)	0.2809 (2)	0.7353 (8)	0.081 (3)	0.77 (2)
F1B	0.960 (5)	0.2533 (8)	0.624 (2)	0.0374 (14)	0.23 (2)
F2B	0.560 (5)	0.2732 (9)	0.586 (3)	0.0495 (18)	0.23 (2)
F3B	0.852 (4)	0.2701 (6)	0.7548 (14)	0.034 (4)	0.23 (2)
O1	0.1090 (4)	0.05494 (7)	0.8079 (2)	0.0179 (4)
N1	0.5344 (5)	0.02318 (8)	0.7721 (2)	0.0112 (5)
H1	0.705 (4)	0.0308 (12)	0.761 (3)	0.024 (9)*
C11	0.3640 (6)	−0.12293 (10)	0.8386 (3)	0.0196 (6)
H11	0.326432	−0.155879	0.853930	0.024*
C10	0.5409 (6)	−0.10978 (10)	0.7397 (3)	0.0179 (6)
H10	0.624302	−0.133496	0.686532	0.021*
C9	0.5939 (6)	−0.06162 (10)	0.7198 (3)	0.0130 (6)
C8	0.4735 (5)	−0.02570 (10)	0.7950 (3)	0.0110 (5)
C7	0.3511 (6)	0.05959 (10)	0.7770 (3)	0.0111 (5)
C1	0.4577 (6)	0.10824 (10)	0.7405 (3)	0.0122 (6)
C2	0.6445 (6)	0.11450 (10)	0.6402 (3)	0.0159 (6)
H2	0.713059	0.087347	0.594779	0.019*
C3	0.7305 (6)	0.16003 (11)	0.6065 (3)	0.0211 (7)
H3	0.857565	0.164231	0.537888	0.025*
C4	0.6301 (6)	0.19963 (10)	0.6735 (3)	0.0213 (7)
C14	0.7186 (8)	0.24914 (12)	0.6366 (4)	0.0352 (9)
C6	0.3576 (6)	0.14825 (10)	0.8057 (3)	0.0186 (6)
H6	0.227526	0.144240	0.873004	0.022*
C5	0.4454 (7)	0.19375 (11)	0.7736 (3)	0.0213 (7)
H5	0.379338	0.220880	0.820056	0.026*
C12	0.2418 (6)	−0.08793 (11)	0.9149 (3)	0.0178 (6)
H12	0.119418	−0.097037	0.981943	0.021*
C13	0.2971 (6)	−0.03981 (10)	0.8942 (3)	0.0155 (6)
H13	0.214283	−0.016200	0.947928	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.01333 (17)	0.01845 (16)	0.01740 (16)	−0.00074 (12)	0.00564 (11)	−0.00226 (12)
F1A	0.0232 (12)	0.0306 (14)	0.059 (4)	−0.0059 (10)	0.010 (3)	0.024 (3)
F2A	0.0307 (15)	0.043 (2)	0.075 (5)	0.0030 (13)	0.004 (3)	0.045 (3)
F3A	0.156 (9)	0.019 (2)	0.073 (3)	−0.030 (4)	0.047 (5)	−0.009 (2)
F1B	0.0232 (12)	0.0306 (14)	0.059 (4)	−0.0059 (10)	0.010 (3)	0.024 (3)
F2B	0.0307 (15)	0.043 (2)	0.075 (5)	0.0030 (13)	0.004 (3)	0.045 (3)
F3B	0.049 (9)	0.010 (6)	0.045 (6)	−0.014 (5)	0.002 (6)	−0.004 (4)
O1	0.0107 (10)	0.0143 (10)	0.0293 (11)	−0.0002 (8)	0.0050 (9)	0.0007 (8)
N1	0.0082 (12)	0.0102 (11)	0.0153 (11)	−0.0009 (9)	0.0010 (9)	0.0016 (9)
C11	0.0191 (16)	0.0117 (14)	0.0275 (16)	−0.0032 (12)	−0.0015 (13)	0.0059 (12)
C10	0.0175 (15)	0.0167 (14)	0.0195 (15)	0.0023 (12)	0.0019 (12)	−0.0023 (12)
C9	0.0070 (13)	0.0165 (14)	0.0154 (14)	−0.0016 (11)	0.0009 (11)	0.0012 (11)
C8	0.0076 (13)	0.0142 (13)	0.0104 (13)	−0.0021 (11)	−0.0046 (10)	0.0004 (11)
C7	0.0073 (13)	0.0128 (13)	0.0130 (13)	−0.0013 (10)	0.0002 (11)	−0.0017 (10)
C1	0.0085 (13)	0.0130 (14)	0.0145 (13)	−0.0004 (11)	−0.0037 (11)	−0.0003 (11)
C2	0.0139 (15)	0.0154 (14)	0.0183 (14)	0.0010 (11)	−0.0001 (12)	−0.0003 (11)
C3	0.0166 (15)	0.0258 (17)	0.0217 (15)	−0.0020 (13)	0.0060 (12)	0.0057 (13)
C4	0.0215 (16)	0.0143 (15)	0.0279 (16)	−0.0024 (12)	0.0004 (13)	0.0058 (13)
C14	0.043 (2)	0.0201 (17)	0.044 (2)	−0.0048 (16)	0.0100 (19)	0.0051 (16)
C6	0.0199 (16)	0.0163 (15)	0.0203 (15)	−0.0006 (12)	0.0058 (12)	−0.0011 (12)
C5	0.0259 (17)	0.0144 (15)	0.0241 (16)	0.0013 (12)	0.0044 (13)	−0.0021 (12)
C12	0.0122 (14)	0.0213 (15)	0.0200 (15)	−0.0053 (12)	0.0020 (12)	0.0051 (12)
C13	0.0120 (14)	0.0184 (15)	0.0160 (14)	−0.0013 (11)	0.0012 (11)	−0.0017 (11)

Geometric parameters (Å, º)

Br1—C9	1.904 (3)	C9—C8	1.395 (4)
F1A—C14	1.377 (8)	C8—C13	1.396 (4)
F2A—C14	1.395 (10)	C7—C1	1.503 (4)
F3A—C14	1.328 (6)	C1—C6	1.390 (4)
F1B—C14	1.18 (2)	C1—C2	1.393 (4)
F1B—F3B	1.50 (3)	C2—C3	1.383 (4)
F2B—C14	1.11 (2)	C2—H2	0.9500
F3B—C14	1.413 (14)	C3—C4	1.390 (4)
O1—C7	1.230 (3)	C3—H3	0.9500
N1—C7	1.347 (4)	C4—C5	1.384 (4)
N1—C8	1.415 (4)	C4—C14	1.496 (4)
N1—H1	0.861 (18)	C6—C5	1.380 (4)
C11—C10	1.388 (4)	C6—H6	0.9500
C11—C12	1.388 (4)	C5—H5	0.9500
C11—H11	0.9500	C12—C13	1.385 (4)
C10—C9	1.383 (4)	C12—H12	0.9500
C10—H10	0.9500	C13—H13	0.9500
C14—F1B—F3B	62.4 (15)	C4—C3—H3	120.2
C14—F3B—F1B	47.8 (10)	C5—C4—C3	120.5 (3)
C7—N1—C8	125.2 (2)	C5—C4—C14	119.4 (3)
C7—N1—H1	117 (2)	C3—C4—C14	120.1 (3)
C8—N1—H1	118 (2)	F2B—C14—F1B	123.1 (16)
C10—C11—C12	120.0 (3)	F3A—C14—F1A	116.4 (9)
C10—C11—H11	120.0	F3A—C14—F2A	101.7 (5)
C12—C11—H11	120.0	F1A—C14—F2A	99.2 (6)
C9—C10—C11	119.0 (3)	F2B—C14—F3B	112.1 (13)
C9—C10—H10	120.5	F1B—C14—F3B	69.8 (18)
C11—C10—H10	120.5	F2B—C14—C4	118.0 (13)
C10—C9—C8	122.2 (3)	F1B—C14—C4	114.5 (11)
C10—C9—Br1	118.4 (2)	F3A—C14—C4	113.1 (3)
C8—C9—Br1	119.3 (2)	F1A—C14—C4	113.3 (4)
C9—C8—C13	117.8 (3)	F2A—C14—C4	111.4 (4)
C9—C8—N1	120.5 (2)	F3B—C14—C4	107.5 (6)
C13—C8—N1	121.7 (2)	C5—C6—C1	120.6 (3)
O1—C7—N1	124.2 (3)	C5—C6—H6	119.7
O1—C7—C1	120.0 (2)	C1—C6—H6	119.7
N1—C7—C1	115.8 (2)	C6—C5—C4	119.6 (3)
C6—C1—C2	119.3 (3)	C6—C5—H5	120.2
C6—C1—C7	118.5 (2)	C4—C5—H5	120.2
C2—C1—C7	122.1 (2)	C13—C12—C11	120.5 (3)
C3—C2—C1	120.3 (3)	C13—C12—H12	119.8
C3—C2—H2	119.8	C11—C12—H12	119.8
C1—C2—H2	119.8	C12—C13—C8	120.6 (3)
C2—C3—C4	119.6 (3)	C12—C13—H13	119.7
C2—C3—H3	120.2	C8—C13—H13	119.7
C12—C11—C10—C9	0.5 (5)	F1B—F3B—C14—C4	110.3 (12)
C11—C10—C9—C8	−0.6 (5)	C5—C4—C14—F2B	−67.3 (17)
C11—C10—C9—Br1	−178.9 (2)	C3—C4—C14—F2B	112.0 (17)
C10—C9—C8—C13	0.9 (4)	C5—C4—C14—F1B	135.8 (14)
Br1—C9—C8—C13	179.2 (2)	C3—C4—C14—F1B	−44.9 (14)
C10—C9—C8—N1	179.6 (3)	C5—C4—C14—F3A	23.1 (9)
Br1—C9—C8—N1	−2.0 (4)	C3—C4—C14—F3A	−157.6 (9)
C7—N1—C8—C9	143.4 (3)	C5—C4—C14—F1A	158.4 (5)
C7—N1—C8—C13	−37.9 (4)	C3—C4—C14—F1A	−22.3 (6)
C8—N1—C7—O1	3.2 (4)	C5—C4—C14—F2A	−90.7 (6)
C8—N1—C7—C1	−176.3 (2)	C3—C4—C14—F2A	88.6 (6)
O1—C7—C1—C6	33.6 (4)	C5—C4—C14—F3B	60.6 (10)
N1—C7—C1—C6	−146.9 (3)	C3—C4—C14—F3B	−120.2 (10)
O1—C7—C1—C2	−143.9 (3)	C2—C1—C6—C5	−1.2 (5)
N1—C7—C1—C2	35.6 (4)	C7—C1—C6—C5	−178.7 (3)
C6—C1—C2—C3	0.4 (4)	C1—C6—C5—C4	1.4 (5)
C7—C1—C2—C3	177.9 (3)	C3—C4—C5—C6	−0.9 (5)
C1—C2—C3—C4	0.2 (5)	C14—C4—C5—C6	178.4 (3)
C2—C3—C4—C5	0.1 (5)	C10—C11—C12—C13	−0.6 (4)
C2—C3—C4—C14	−179.2 (3)	C11—C12—C13—C8	0.8 (4)
F3B—F1B—C14—F2B	104 (2)	C9—C8—C13—C12	−1.0 (4)
F3B—F1B—C14—C4	−100.6 (12)	N1—C8—C13—C12	−179.7 (3)
F1B—F3B—C14—F2B	−118.5 (17)

(PB32)

Crystal data

C14H9BrF3NO	Dx = 1.716 Mg m^−3
Mr = 344.13	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 7931 reflections
a = 7.8062 (3) Å	θ = 2.8–34.4°
b = 19.3000 (7) Å	µ = 3.11 mm^−1
c = 8.8433 (3) Å	T = 100 K
V = 1332.33 (8) Å^3	Needle
Z = 4	0.34 × 0.15 × 0.13 mm
F(000) = 680

Data collection

Bruker APEX-II CCD diffractometer	2170 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.0°, θmin = 2.8°
Tmin = 0.417, Tmax = 0.688	h = −9→8
7418 measured reflections	k = −21→22
2239 independent reflections	l = −10→10

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.022	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.057	w = 1/[σ^2(Fo^2) + (0.0237P)^2 + 0.1506P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2239 reflections	Δρmax = 0.64 e Å^−3
185 parameters	Δρmin = −0.24 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.06621 (4)	0.96805 (2)	0.53181 (7)	0.01863 (13)
F1	0.3000 (3)	0.53012 (10)	0.8649 (3)	0.0397 (7)
F2	0.3967 (4)	0.59822 (13)	0.6928 (3)	0.0363 (6)
F3	0.1839 (3)	0.62966 (12)	0.8313 (3)	0.0316 (5)
O1	0.3933 (3)	0.75529 (13)	0.7431 (3)	0.0212 (6)
N1	0.2360 (4)	0.78380 (13)	0.9515 (3)	0.0154 (6)
H1	0.211 (4)	0.7707 (15)	1.047 (5)	0.004 (8)*
C14	0.3358 (5)	0.59697 (19)	0.8348 (4)	0.0250 (8)
C2	0.4557 (4)	0.62757 (17)	0.9485 (4)	0.0160 (7)
C1	0.4620 (4)	0.69910 (17)	0.9742 (4)	0.0141 (7)
C6	0.5718 (4)	0.72505 (19)	1.0828 (4)	0.0156 (8)
H6	0.573376	0.773400	1.102861	0.019*
C5	0.6802 (5)	0.68125 (19)	1.1630 (4)	0.0218 (8)
H5	0.757673	0.699693	1.235371	0.026*
C4	0.6744 (5)	0.6107 (2)	1.1367 (4)	0.0247 (8)
H4	0.748331	0.580606	1.191183	0.030*
C3	0.5615 (4)	0.58368 (16)	1.0316 (7)	0.0218 (7)
H3	0.556091	0.535027	1.015977	0.026*
C7	0.3596 (4)	0.74863 (16)	0.8775 (4)	0.0155 (7)
C8	0.1099 (5)	0.82671 (16)	0.8824 (4)	0.0150 (7)
C13	−0.0554 (4)	0.82287 (19)	0.9391 (4)	0.0184 (8)
H13	−0.080948	0.793147	1.021731	0.022*
C12	−0.1830 (4)	0.86287 (17)	0.8740 (4)	0.0180 (7)
H12	−0.296181	0.860487	0.913200	0.022*
C11	−0.1492 (4)	0.90623 (16)	0.7529 (4)	0.0171 (7)
H11	−0.237607	0.932905	0.707497	0.021*
C10	0.0175 (5)	0.90954 (16)	0.6999 (4)	0.0151 (7)
C9	0.1490 (4)	0.87115 (16)	0.7643 (4)	0.0136 (7)
H9	0.263226	0.875245	0.728211	0.016*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0202 (2)	0.01782 (18)	0.01790 (18)	−0.00315 (10)	−0.00356 (18)	0.00558 (16)
F1	0.0452 (18)	0.0236 (13)	0.0502 (17)	−0.0136 (8)	−0.0040 (14)	−0.0054 (10)
F2	0.0364 (14)	0.0510 (15)	0.0214 (12)	−0.0073 (12)	0.0014 (11)	−0.0142 (12)
F3	0.0184 (11)	0.0421 (13)	0.0345 (13)	−0.0012 (9)	−0.0067 (10)	−0.0110 (11)
O1	0.0188 (13)	0.0335 (14)	0.0112 (13)	0.0087 (11)	0.0019 (11)	0.0039 (11)
N1	0.0172 (16)	0.0194 (15)	0.0095 (15)	0.0032 (11)	0.0002 (13)	0.0024 (13)
C14	0.027 (2)	0.0253 (19)	0.0226 (19)	−0.0020 (15)	−0.0005 (17)	−0.0047 (16)
C2	0.0134 (18)	0.0197 (18)	0.0147 (18)	−0.0010 (12)	0.0055 (14)	−0.0009 (14)
C1	0.0106 (16)	0.0194 (17)	0.0121 (15)	0.0011 (12)	0.0031 (13)	0.0043 (13)
C6	0.0140 (19)	0.0185 (17)	0.0144 (17)	0.0011 (12)	0.0013 (13)	0.0012 (14)
C5	0.0159 (19)	0.0279 (19)	0.0216 (18)	0.0000 (14)	−0.0024 (16)	0.0030 (15)
C4	0.020 (2)	0.028 (2)	0.0266 (19)	0.0064 (14)	0.0002 (17)	0.0105 (16)
C3	0.0199 (18)	0.0172 (15)	0.0283 (17)	0.0032 (11)	0.0054 (19)	0.001 (2)
C7	0.0148 (19)	0.0181 (16)	0.0135 (17)	−0.0026 (13)	−0.0027 (16)	−0.0016 (14)
C8	0.0166 (18)	0.0148 (16)	0.0135 (17)	0.0031 (12)	−0.0035 (15)	−0.0033 (13)
C13	0.020 (2)	0.0199 (18)	0.0150 (18)	0.0011 (12)	0.0034 (15)	0.0005 (15)
C12	0.0139 (17)	0.0209 (17)	0.0193 (17)	0.0046 (12)	0.0014 (16)	0.0000 (14)
C11	0.0139 (19)	0.0186 (17)	0.0189 (16)	0.0055 (13)	−0.0029 (16)	−0.0019 (15)
C10	0.0211 (18)	0.0105 (15)	0.0135 (16)	−0.0018 (13)	−0.0011 (16)	0.0005 (13)
C9	0.0110 (18)	0.0172 (16)	0.0126 (15)	0.0008 (12)	0.0002 (14)	−0.0045 (14)

Geometric parameters (Å, º)

Br1—C10	1.905 (3)	C5—C4	1.382 (5)
F1—C14	1.347 (4)	C5—H5	0.9500
F2—C14	1.343 (5)	C4—C3	1.383 (6)
F3—C14	1.343 (4)	C4—H4	0.9500
O1—C7	1.223 (4)	C3—H3	0.9500
N1—C7	1.349 (5)	C8—C9	1.386 (5)
N1—C8	1.424 (4)	C8—C13	1.387 (5)
N1—H1	0.90 (4)	C13—C12	1.386 (5)
C14—C2	1.496 (5)	C13—H13	0.9500
C2—C3	1.392 (6)	C12—C11	1.385 (5)
C2—C1	1.400 (5)	C12—H12	0.9500
C1—C6	1.381 (5)	C11—C10	1.385 (6)
C1—C7	1.512 (5)	C11—H11	0.9500
C6—C5	1.390 (5)	C10—C9	1.388 (5)
C6—H6	0.9500	C9—H9	0.9500
C7—N1—C8	125.4 (3)	C4—C3—C2	120.2 (3)
C7—N1—H1	118 (2)	C4—C3—H3	119.9
C8—N1—H1	115 (2)	C2—C3—H3	119.9
F2—C14—F3	106.4 (3)	O1—C7—N1	124.9 (3)
F2—C14—F1	106.0 (3)	O1—C7—C1	120.2 (3)
F3—C14—F1	105.8 (3)	N1—C7—C1	114.9 (3)
F2—C14—C2	113.6 (3)	C9—C8—C13	120.7 (3)
F3—C14—C2	112.5 (3)	C9—C8—N1	122.1 (3)
F1—C14—C2	112.0 (3)	C13—C8—N1	117.2 (3)
C3—C2—C1	119.6 (3)	C12—C13—C8	119.3 (3)
C3—C2—C14	119.1 (3)	C12—C13—H13	120.4
C1—C2—C14	121.4 (3)	C8—C13—H13	120.4
C6—C1—C2	119.5 (3)	C11—C12—C13	121.4 (3)
C6—C1—C7	119.5 (3)	C11—C12—H12	119.3
C2—C1—C7	120.9 (3)	C13—C12—H12	119.3
C1—C6—C5	120.8 (3)	C10—C11—C12	118.0 (3)
C1—C6—H6	119.6	C10—C11—H11	121.0
C5—C6—H6	119.6	C12—C11—H11	121.0
C4—C5—C6	119.6 (3)	C11—C10—C9	122.1 (3)
C4—C5—H5	120.2	C11—C10—Br1	118.6 (3)
C6—C5—H5	120.2	C9—C10—Br1	119.3 (3)
C5—C4—C3	120.3 (3)	C8—C9—C10	118.5 (3)
C5—C4—H4	119.8	C8—C9—H9	120.8
C3—C4—H4	119.8	C10—C9—H9	120.8
F2—C14—C2—C3	−97.2 (4)	C8—N1—C7—C1	−171.9 (3)
F3—C14—C2—C3	141.9 (4)	C6—C1—C7—O1	109.9 (4)
F1—C14—C2—C3	22.9 (5)	C2—C1—C7—O1	−65.8 (5)
F2—C14—C2—C1	83.7 (4)	C6—C1—C7—N1	−69.0 (4)
F3—C14—C2—C1	−37.3 (5)	C2—C1—C7—N1	115.4 (3)
F1—C14—C2—C1	−156.3 (3)	C7—N1—C8—C9	−41.3 (5)
C3—C2—C1—C6	−0.7 (5)	C7—N1—C8—C13	139.3 (3)
C14—C2—C1—C6	178.5 (3)	C9—C8—C13—C12	1.5 (5)
C3—C2—C1—C7	175.0 (4)	N1—C8—C13—C12	−179.0 (3)
C14—C2—C1—C7	−5.8 (5)	C8—C13—C12—C11	0.4 (5)
C2—C1—C6—C5	2.2 (5)	C13—C12—C11—C10	−1.1 (5)
C7—C1—C6—C5	−173.5 (3)	C12—C11—C10—C9	−0.1 (5)
C1—C6—C5—C4	−1.8 (5)	C12—C11—C10—Br1	179.3 (2)
C6—C5—C4—C3	−0.1 (6)	C13—C8—C9—C10	−2.7 (5)
C5—C4—C3—C2	1.6 (7)	N1—C8—C9—C10	177.9 (3)
C1—C2—C3—C4	−1.2 (6)	C11—C10—C9—C8	1.9 (5)
C14—C2—C3—C4	179.6 (4)	Br1—C10—C9—C8	−177.4 (2)
C8—N1—C7—O1	9.3 (5)

(PB34)

Crystal data

C14H9BrF3NO	F(000) = 340
Mr = 344.13	Dx = 1.810 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 4.8588 (4) Å	Cell parameters from 2029 reflections
b = 4.9939 (4) Å	θ = 2.4–23.2°
c = 26.0286 (19) Å	µ = 3.29 mm^−1
β = 91.448 (5)°	T = 100 K
V = 631.37 (9) Å^3	Plate
Z = 2	0.28 × 0.25 × 0.13 mm

Data collection

Bruker APEX-II CCD diffractometer	1757 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan SADABS 2014/4	θmax = 27.5°, θmin = 2.4°
Tmin = 0.486, Tmax = 0.758	h = −6→6
4884 measured reflections	k = −5→6
2296 independent reflections	l = −33→33

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0187P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max < 0.001
S = 0.99	Δρmax = 0.82 e Å^−3
2296 reflections	Δρmin = −1.01 e Å^−3
184 parameters	Absolute structure: Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraints	Absolute structure parameter: 0.042 (14)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	1.10619 (14)	0.1494 (2)	0.45569 (2)	0.0286 (2)
F1	0.0236 (8)	0.2453 (7)	0.07439 (13)	0.0287 (12)
F2	0.1236 (7)	0.6173 (11)	0.03756 (12)	0.0302 (11)
F3	0.3886 (8)	0.2767 (8)	0.02918 (13)	0.0318 (12)
O1	0.9817 (10)	0.9483 (10)	0.24447 (17)	0.0250 (13)
N1	1.0002 (12)	0.5109 (11)	0.2684 (2)	0.0159 (13)
H1	0.949 (14)	0.346 (7)	0.264 (3)	0.019*
C14	0.2356 (15)	0.4098 (15)	0.0629 (3)	0.0211 (17)
C4	0.3987 (14)	0.4912 (14)	0.1093 (2)	0.0158 (15)
C3	0.3835 (13)	0.3520 (13)	0.1550 (2)	0.0192 (17)
H3	0.257443	0.207494	0.157574	0.023*
C2	0.5478 (13)	0.4193 (14)	0.1966 (2)	0.0157 (16)
H2	0.535832	0.320249	0.227597	0.019*
C1	0.7317 (11)	0.631 (2)	0.1936 (2)	0.0144 (14)
C8	0.9154 (13)	0.7121 (14)	0.2377 (2)	0.0185 (18)
C7	1.1513 (14)	0.5373 (12)	0.3158 (2)	0.0162 (17)
C13	1.3616 (13)	0.7193 (12)	0.3236 (2)	0.0185 (18)
H13	1.410376	0.838507	0.296909	0.022*
C12	1.5005 (13)	0.7275 (13)	0.3703 (2)	0.022 (2)
H12	1.647218	0.851044	0.375590	0.026*
C11	1.4274 (15)	0.5559 (13)	0.4098 (3)	0.0230 (19)
H11	1.521550	0.562943	0.442169	0.028*
C5	0.5767 (13)	0.7069 (14)	0.1059 (2)	0.0172 (18)
H5	0.585611	0.806791	0.074941	0.021*
C6	0.7413 (14)	0.7757 (13)	0.1480 (2)	0.0219 (18)
H6	0.862841	0.923967	0.145699	0.026*
C10	1.2199 (14)	0.3784 (14)	0.4014 (2)	0.0200 (17)
C9	1.0790 (13)	0.3624 (13)	0.3548 (2)	0.0163 (16)
H9	0.936000	0.234874	0.349432	0.020*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0390 (4)	0.0244 (4)	0.0224 (3)	0.0051 (5)	0.0012 (2)	0.0037 (5)
F1	0.032 (2)	0.029 (3)	0.025 (2)	−0.0117 (19)	−0.0039 (16)	−0.0003 (18)
F2	0.033 (2)	0.029 (3)	0.0281 (19)	0.004 (3)	−0.0099 (15)	0.010 (2)
F3	0.033 (3)	0.039 (3)	0.024 (2)	0.0044 (19)	0.0027 (19)	−0.0113 (18)
O1	0.035 (3)	0.005 (3)	0.034 (3)	−0.002 (2)	−0.009 (2)	0.003 (2)
N1	0.021 (3)	0.005 (3)	0.021 (3)	0.001 (3)	−0.004 (3)	−0.001 (3)
C14	0.020 (4)	0.018 (5)	0.025 (4)	0.001 (3)	0.000 (3)	0.001 (3)
C4	0.018 (4)	0.012 (4)	0.017 (4)	0.004 (3)	0.002 (3)	−0.003 (3)
C3	0.020 (4)	0.010 (4)	0.027 (4)	0.001 (3)	0.002 (3)	−0.001 (3)
C2	0.018 (4)	0.011 (4)	0.019 (4)	−0.001 (3)	−0.002 (3)	0.003 (3)
C1	0.016 (3)	0.007 (4)	0.021 (3)	0.004 (4)	0.002 (2)	0.000 (4)
C8	0.023 (4)	0.008 (6)	0.024 (4)	−0.001 (3)	0.003 (3)	−0.003 (3)
C7	0.023 (4)	0.010 (4)	0.016 (4)	0.004 (3)	0.000 (3)	−0.002 (3)
C13	0.028 (4)	0.007 (5)	0.021 (3)	0.002 (3)	0.001 (3)	−0.001 (3)
C12	0.014 (4)	0.023 (6)	0.028 (4)	−0.003 (3)	−0.003 (3)	−0.006 (3)
C11	0.027 (4)	0.020 (5)	0.021 (4)	0.010 (3)	−0.011 (3)	−0.006 (3)
C5	0.026 (4)	0.006 (6)	0.020 (3)	0.003 (3)	−0.001 (3)	0.000 (3)
C6	0.024 (4)	0.015 (5)	0.027 (4)	0.000 (3)	0.000 (3)	0.001 (3)
C10	0.031 (5)	0.015 (5)	0.014 (3)	0.006 (4)	0.002 (3)	0.002 (3)
C9	0.018 (4)	0.008 (4)	0.023 (4)	−0.003 (3)	0.000 (3)	−0.002 (3)

Geometric parameters (Å, º)

Br1—C10	1.911 (6)	C1—C6	1.391 (9)
F1—C14	1.357 (7)	C1—C8	1.491 (9)
F2—C14	1.337 (8)	C7—C13	1.379 (8)
F3—C14	1.341 (7)	C7—C9	1.391 (8)
O1—C8	1.235 (8)	C13—C12	1.375 (8)
N1—C8	1.342 (8)	C13—H13	0.9500
N1—C7	1.426 (8)	C12—C11	1.391 (8)
N1—H1	0.87 (2)	C12—H12	0.9500
C14—C4	1.484 (9)	C11—C10	1.356 (9)
C4—C3	1.381 (8)	C11—H11	0.9500
C4—C5	1.385 (9)	C5—C6	1.383 (8)
C3—C2	1.371 (8)	C5—H5	0.9500
C3—H3	0.9500	C6—H6	0.9500
C2—C1	1.389 (10)	C10—C9	1.380 (8)
C2—H2	0.9500	C9—H9	0.9500
C8—N1—C7	126.1 (6)	C13—C7—C9	120.4 (6)
C8—N1—H1	124 (5)	C13—C7—N1	123.6 (6)
C7—N1—H1	110 (5)	C9—C7—N1	116.1 (6)
F2—C14—F3	106.6 (5)	C12—C13—C7	119.7 (6)
F2—C14—F1	106.1 (6)	C12—C13—H13	120.1
F3—C14—F1	106.3 (5)	C7—C13—H13	120.1
F2—C14—C4	113.0 (6)	C13—C12—C11	120.3 (6)
F3—C14—C4	112.0 (6)	C13—C12—H12	119.8
F1—C14—C4	112.3 (5)	C11—C12—H12	119.8
C3—C4—C5	119.5 (6)	C10—C11—C12	119.1 (6)
C3—C4—C14	121.5 (6)	C10—C11—H11	120.4
C5—C4—C14	118.9 (6)	C12—C11—H11	120.4
C2—C3—C4	120.9 (6)	C6—C5—C4	119.5 (6)
C2—C3—H3	119.5	C6—C5—H5	120.3
C4—C3—H3	119.5	C4—C5—H5	120.3
C3—C2—C1	120.4 (6)	C5—C6—C1	121.1 (6)
C3—C2—H2	119.8	C5—C6—H6	119.5
C1—C2—H2	119.8	C1—C6—H6	119.5
C2—C1—C6	118.5 (6)	C11—C10—C9	122.0 (6)
C2—C1—C8	122.5 (6)	C11—C10—Br1	120.0 (5)
C6—C1—C8	119.0 (7)	C9—C10—Br1	118.0 (5)
O1—C8—N1	123.8 (6)	C10—C9—C7	118.4 (6)
O1—C8—C1	121.2 (7)	C10—C9—H9	120.8
N1—C8—C1	115.1 (7)	C7—C9—H9	120.8
F2—C14—C4—C3	137.8 (6)	C8—N1—C7—C13	−40.0 (10)
F3—C14—C4—C3	−101.7 (7)	C8—N1—C7—C9	141.3 (6)
F1—C14—C4—C3	17.8 (9)	C9—C7—C13—C12	0.0 (9)
F2—C14—C4—C5	−44.3 (8)	N1—C7—C13—C12	−178.6 (6)
F3—C14—C4—C5	76.1 (8)	C7—C13—C12—C11	−0.9 (9)
F1—C14—C4—C5	−164.3 (6)	C13—C12—C11—C10	0.8 (10)
C5—C4—C3—C2	−1.9 (10)	C3—C4—C5—C6	1.5 (9)
C14—C4—C3—C2	176.0 (6)	C14—C4—C5—C6	−176.4 (6)
C4—C3—C2—C1	0.6 (10)	C4—C5—C6—C1	0.2 (10)
C3—C2—C1—C6	1.1 (10)	C2—C1—C6—C5	−1.5 (10)
C3—C2—C1—C8	−179.8 (6)	C8—C1—C6—C5	179.4 (6)
C7—N1—C8—O1	7.3 (11)	C12—C11—C10—C9	0.1 (10)
C7—N1—C8—C1	−172.8 (5)	C12—C11—C10—Br1	−177.7 (5)
C2—C1—C8—O1	−147.5 (7)	C11—C10—C9—C7	−1.0 (10)
C6—C1—C8—O1	31.5 (9)	Br1—C10—C9—C7	176.9 (5)
C2—C1—C8—N1	32.6 (9)	C13—C7—C9—C10	0.9 (9)
C6—C1—C8—N1	−148.3 (6)	N1—C7—C9—C10	179.6 (6)

(PB43)

Crystal data

C14H9BrF3NO	F(000) = 680
Mr = 344.13	Dx = 1.726 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.018 (3) Å	Cell parameters from 8180 reflections
b = 10.488 (2) Å	θ = 2.7–30.8°
c = 9.7309 (19) Å	µ = 3.13 mm^−1
β = 94.432 (14)°	T = 100 K
V = 1324.6 (4) Å^3	Plate
Z = 4	0.28 × 0.13 × 0.10 mm

Data collection

Bruker APEX-II CCD diffractometer	1948 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.046
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 2.5°
Tmin = 0.487, Tmax = 0.731	h = −13→15
9729 measured reflections	k = −10→12
2453 independent reflections	l = −11→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 0.9094P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2453 reflections	Δρmax = 0.82 e Å^−3
185 parameters	Δρmin = −0.58 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.97461 (3)	0.84030 (4)	0.44456 (4)	0.02757 (15)
F1	0.4742 (2)	0.0196 (3)	0.8148 (3)	0.0741 (9)
F2	0.4596 (3)	−0.1556 (3)	0.7203 (4)	0.0940 (13)
F3	0.5783 (2)	−0.1254 (4)	0.8778 (4)	0.1189 (18)
O1	0.77241 (18)	0.3007 (2)	0.7125 (2)	0.0230 (6)
N1	0.7783 (2)	0.3168 (3)	0.4809 (3)	0.0182 (7)
H1	0.774 (2)	0.275 (4)	0.405 (4)	0.020 (10)*
C1	0.7119 (2)	0.1236 (3)	0.5779 (3)	0.0176 (8)
C2	0.7367 (3)	0.0396 (4)	0.4758 (3)	0.0253 (8)
H2	0.783256	0.064694	0.410293	0.030*
C3	0.6932 (3)	−0.0817 (4)	0.4693 (4)	0.0317 (10)
H3	0.710338	−0.139058	0.399052	0.038*
C4	0.6257 (3)	−0.1193 (4)	0.5635 (4)	0.0312 (10)
H4	0.596082	−0.202159	0.558645	0.037*
C5	0.6014 (3)	−0.0349 (4)	0.6657 (4)	0.0264 (9)
C6	0.6447 (2)	0.0841 (4)	0.6740 (4)	0.0225 (8)
H6	0.628702	0.140131	0.746023	0.027*
C7	0.7574 (2)	0.2538 (3)	0.5960 (3)	0.0179 (7)
C8	0.8226 (2)	0.4402 (3)	0.4761 (3)	0.0172 (7)
C9	0.8843 (2)	0.4672 (4)	0.3694 (3)	0.0202 (8)
H9	0.896090	0.403172	0.303363	0.024*
C10	0.9287 (3)	0.5857 (4)	0.3583 (3)	0.0217 (8)
H10	0.970767	0.603883	0.285282	0.026*
C11	0.9108 (3)	0.6773 (3)	0.4551 (3)	0.0199 (8)
C12	0.8489 (3)	0.6535 (3)	0.5608 (3)	0.0205 (8)
H12	0.836958	0.718174	0.626007	0.025*
C13	0.8045 (3)	0.5350 (3)	0.5709 (3)	0.0191 (8)
H13	0.761358	0.518017	0.643163	0.023*
C14	0.5311 (3)	−0.0749 (4)	0.7707 (5)	0.0397 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0310 (2)	0.0199 (2)	0.0325 (2)	−0.00732 (16)	0.00686 (15)	−0.00014 (17)
F1	0.080 (2)	0.062 (2)	0.088 (2)	0.0032 (18)	0.0535 (17)	0.0146 (18)
F2	0.074 (2)	0.084 (3)	0.128 (3)	−0.054 (2)	0.035 (2)	−0.015 (2)
F3	0.0523 (19)	0.209 (5)	0.098 (3)	0.022 (2)	0.0233 (18)	0.125 (3)
O1	0.0350 (14)	0.0191 (14)	0.0149 (12)	−0.0025 (11)	0.0021 (10)	0.0001 (10)
N1	0.0273 (16)	0.0154 (17)	0.0121 (14)	−0.0003 (12)	0.0022 (12)	−0.0022 (12)
C1	0.0218 (18)	0.0146 (19)	0.0157 (17)	0.0004 (14)	−0.0021 (14)	0.0020 (14)
C2	0.039 (2)	0.018 (2)	0.0194 (18)	0.0027 (16)	0.0026 (15)	0.0029 (15)
C3	0.050 (3)	0.019 (2)	0.026 (2)	0.0001 (18)	−0.0003 (18)	−0.0043 (17)
C4	0.039 (2)	0.015 (2)	0.038 (2)	−0.0057 (17)	−0.0092 (18)	0.0050 (18)
C5	0.0203 (18)	0.026 (2)	0.031 (2)	−0.0016 (16)	−0.0044 (15)	0.0073 (18)
C6	0.0214 (18)	0.023 (2)	0.0224 (18)	0.0026 (15)	0.0001 (14)	0.0008 (16)
C7	0.0173 (17)	0.019 (2)	0.0172 (17)	0.0056 (15)	−0.0001 (13)	0.0021 (15)
C8	0.0187 (17)	0.0156 (19)	0.0170 (16)	0.0011 (14)	−0.0012 (13)	0.0025 (15)
C9	0.0239 (18)	0.022 (2)	0.0145 (16)	−0.0001 (15)	0.0010 (13)	−0.0016 (15)
C10	0.0215 (18)	0.025 (2)	0.0191 (17)	−0.0006 (16)	0.0046 (14)	0.0014 (16)
C11	0.0212 (18)	0.017 (2)	0.0213 (18)	−0.0016 (14)	−0.0021 (14)	0.0038 (15)
C12	0.0260 (18)	0.017 (2)	0.0188 (17)	0.0030 (15)	0.0029 (14)	−0.0035 (15)
C13	0.0255 (18)	0.0146 (19)	0.0177 (16)	0.0027 (15)	0.0042 (13)	0.0011 (14)
C14	0.033 (2)	0.031 (3)	0.056 (3)	−0.005 (2)	0.005 (2)	0.013 (2)

Geometric parameters (Å, º)

Br1—C11	1.907 (3)	C4—C5	1.386 (5)
F1—C14	1.328 (5)	C4—H4	0.9500
F2—C14	1.323 (5)	C5—C6	1.369 (5)
F3—C14	1.283 (5)	C5—C14	1.484 (6)
O1—C7	1.237 (4)	C6—H6	0.9500
N1—C7	1.347 (4)	C8—C13	1.389 (5)
N1—C8	1.419 (4)	C8—C9	1.390 (5)
N1—H1	0.86 (4)	C9—C10	1.378 (5)
C1—C2	1.385 (5)	C9—H9	0.9500
C1—C6	1.392 (5)	C10—C11	1.378 (5)
C1—C7	1.494 (5)	C10—H10	0.9500
C2—C3	1.391 (5)	C11—C12	1.377 (5)
C2—H2	0.9500	C12—C13	1.377 (5)
C3—C4	1.377 (6)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.7 (3)	C13—C8—C9	119.2 (3)
C7—N1—H1	117 (2)	C13—C8—N1	122.7 (3)
C8—N1—H1	116 (2)	C9—C8—N1	118.1 (3)
C2—C1—C6	119.1 (3)	C10—C9—C8	120.8 (3)
C2—C1—C7	123.6 (3)	C10—C9—H9	119.6
C6—C1—C7	117.2 (3)	C8—C9—H9	119.6
C1—C2—C3	119.8 (4)	C9—C10—C11	118.8 (3)
C1—C2—H2	120.1	C9—C10—H10	120.6
C3—C2—H2	120.1	C11—C10—H10	120.6
C4—C3—C2	120.7 (4)	C12—C11—C10	121.5 (3)
C4—C3—H3	119.7	C12—C11—Br1	119.0 (3)
C2—C3—H3	119.7	C10—C11—Br1	119.4 (3)
C3—C4—C5	119.2 (4)	C11—C12—C13	119.4 (3)
C3—C4—H4	120.4	C11—C12—H12	120.3
C5—C4—H4	120.4	C13—C12—H12	120.3
C6—C5—C4	120.6 (4)	C12—C13—C8	120.3 (3)
C6—C5—C14	119.3 (4)	C12—C13—H13	119.9
C4—C5—C14	120.0 (4)	C8—C13—H13	119.9
C5—C6—C1	120.6 (3)	F3—C14—F2	108.4 (4)
C5—C6—H6	119.7	F3—C14—F1	106.9 (4)
C1—C6—H6	119.7	F2—C14—F1	101.7 (4)
O1—C7—N1	122.6 (3)	F3—C14—C5	113.2 (3)
O1—C7—C1	120.3 (3)	F2—C14—C5	112.3 (4)
N1—C7—C1	117.0 (3)	F1—C14—C5	113.6 (4)
C6—C1—C2—C3	1.0 (5)	C7—N1—C8—C9	148.7 (3)
C7—C1—C2—C3	177.8 (3)	C13—C8—C9—C10	1.0 (5)
C1—C2—C3—C4	0.0 (5)	N1—C8—C9—C10	179.3 (3)
C2—C3—C4—C5	−0.1 (5)	C8—C9—C10—C11	0.0 (5)
C3—C4—C5—C6	−0.7 (5)	C9—C10—C11—C12	−0.9 (5)
C3—C4—C5—C14	−178.2 (3)	C9—C10—C11—Br1	178.2 (2)
C4—C5—C6—C1	1.7 (5)	C10—C11—C12—C13	0.6 (5)
C14—C5—C6—C1	179.2 (3)	Br1—C11—C12—C13	−178.5 (2)
C2—C1—C6—C5	−1.8 (5)	C11—C12—C13—C8	0.4 (5)
C7—C1—C6—C5	−178.8 (3)	C9—C8—C13—C12	−1.2 (5)
C8—N1—C7—O1	2.4 (5)	N1—C8—C13—C12	−179.5 (3)
C8—N1—C7—C1	−179.2 (3)	C6—C5—C14—F3	−87.6 (5)
C2—C1—C7—O1	−146.9 (3)	C4—C5—C14—F3	90.0 (5)
C6—C1—C7—O1	30.0 (4)	C6—C5—C14—F2	149.3 (4)
C2—C1—C7—N1	34.7 (4)	C4—C5—C14—F2	−33.1 (5)
C6—C1—C7—N1	−148.4 (3)	C6—C5—C14—F1	34.5 (5)
C7—N1—C8—C13	−33.0 (5)	C4—C5—C14—F1	−147.9 (4)

(PB44)

Crystal data

C14H9BrF3NO	F(000) = 1360
Mr = 344.13	Dx = 1.773 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 16.9434 (5) Å	Cell parameters from 6753 reflections
b = 5.2417 (1) Å	θ = 2.8–30.2°
c = 29.1410 (8) Å	µ = 3.22 mm^−1
β = 94.775 (2)°	T = 100 K
V = 2579.09 (12) Å^3	Needle
Z = 8	0.40 × 0.10 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	3971 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.038
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.0°, θmin = 1.4°
Tmin = 0.476, Tmax = 0.710	h = −20→20
21794 measured reflections	k = −5→6
4543 independent reflections	l = −33→34

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.170	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 27.2059P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max = 0.001
4543 reflections	Δρmax = 2.70 e Å^−3
367 parameters	Δρmin = −0.90 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1A	−0.05020 (4)	0.42865 (14)	0.10486 (2)	0.0204 (2)
Br2A	0.54395 (4)	0.74317 (13)	0.39392 (2)	0.0177 (2)
F1	0.3300 (3)	0.2773 (12)	0.51550 (14)	0.0485 (16)
F2	0.4391 (3)	0.2472 (11)	0.48501 (17)	0.0485 (15)
F3	0.3834 (4)	0.6046 (10)	0.49063 (18)	0.0555 (16)
F4	0.0549 (3)	0.7311 (15)	0.02125 (17)	0.071 (2)
F5	0.1599 (3)	0.6297 (10)	−0.00970 (16)	0.0436 (13)
F6	0.1220 (3)	1.0154 (10)	−0.00966 (16)	0.0455 (14)
O1	0.1848 (3)	−0.0420 (9)	0.29234 (16)	0.0168 (10)
O2	0.3146 (3)	1.2151 (9)	0.20439 (15)	0.0150 (10)
N1	0.1652 (3)	0.3839 (11)	0.28213 (18)	0.0113 (11)
H1	0.184 (4)	0.545 (15)	0.295 (2)	0.014*
N2	0.3348 (3)	0.7855 (10)	0.21435 (19)	0.0115 (11)
H2	0.324 (4)	0.628 (6)	0.207 (2)	0.014*
C1	0.2395 (3)	0.2381 (12)	0.3514 (2)	0.0102 (13)
C2	0.2231 (4)	0.4466 (13)	0.3774 (2)	0.0149 (14)
H2A	0.182721	0.563003	0.366626	0.018*
C3	0.2660 (4)	0.4870 (14)	0.4197 (2)	0.0184 (15)
H3	0.254745	0.630731	0.437955	0.022*
C4	0.3252 (4)	0.3162 (14)	0.4353 (2)	0.0155 (14)
C5	0.3418 (4)	0.1067 (13)	0.4089 (2)	0.0168 (14)
H5	0.382718	−0.008151	0.419439	0.020*
C6	0.2987 (4)	0.0648 (13)	0.3672 (2)	0.0142 (14)
H6	0.309190	−0.080965	0.349279	0.017*
C7	0.1942 (4)	0.1800 (13)	0.3059 (2)	0.0140 (14)
C8	0.1166 (3)	0.3811 (12)	0.2400 (2)	0.0101 (13)
C9	0.1219 (4)	0.5860 (12)	0.2103 (2)	0.0120 (13)
H9	0.159236	0.717904	0.217795	0.014*
C10	0.0729 (4)	0.5997 (13)	0.1698 (2)	0.0137 (13)
H10	0.077005	0.738766	0.149249	0.016*
C11	0.0178 (4)	0.4070 (13)	0.1598 (2)	0.0139 (14)
C12	0.0120 (4)	0.2052 (13)	0.1895 (2)	0.0115 (13)
H12	−0.026282	0.075590	0.182373	0.014*
C13	0.0614 (4)	0.1893 (13)	0.2296 (2)	0.0128 (13)
H13	0.057590	0.048766	0.249890	0.015*
C14	0.3698 (4)	0.3570 (16)	0.4812 (2)	0.0245 (17)
C15	0.2606 (4)	0.9385 (13)	0.1450 (2)	0.0129 (13)
C16	0.2782 (4)	0.7312 (13)	0.1182 (2)	0.0132 (13)
H16	0.319397	0.617092	0.128666	0.016*
C17	0.2356 (4)	0.6896 (14)	0.0758 (2)	0.0186 (15)
H17	0.247987	0.548549	0.057267	0.022*
C18	0.1751 (4)	0.8554 (13)	0.0610 (2)	0.0163 (14)
C19	0.1571 (4)	1.0625 (13)	0.0881 (2)	0.0161 (14)
H19	0.115375	1.175405	0.077929	0.019*
C20	0.2001 (4)	1.1037 (13)	0.1298 (2)	0.0139 (13)
H20	0.188042	1.245894	0.148197	0.017*
C21	0.3056 (3)	0.9967 (12)	0.1904 (2)	0.0097 (13)
C22	0.3818 (3)	0.7892 (12)	0.2568 (2)	0.0102 (13)
C23	0.3752 (3)	0.5860 (13)	0.2865 (2)	0.0116 (13)
H23	0.337697	0.454894	0.278855	0.014*
C24	0.4233 (4)	0.5724 (13)	0.3275 (2)	0.0130 (13)
H24	0.418499	0.432772	0.347821	0.016*
C25	0.4780 (4)	0.7627 (12)	0.3385 (2)	0.0110 (13)
C26	0.4848 (4)	0.9717 (13)	0.3090 (2)	0.0136 (14)
H26	0.521982	1.103351	0.317019	0.016*
C27	0.4366 (4)	0.9846 (12)	0.2679 (2)	0.0111 (13)
H27	0.440929	1.124641	0.247607	0.013*
C28	0.1268 (4)	0.8125 (16)	0.0158 (2)	0.0240 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1A	0.0156 (4)	0.0307 (4)	0.0139 (4)	−0.0024 (3)	−0.0047 (3)	0.0025 (3)
Br2A	0.0163 (4)	0.0258 (4)	0.0097 (3)	−0.0020 (3)	−0.0064 (2)	0.0032 (3)
F1	0.048 (3)	0.087 (4)	0.009 (2)	−0.035 (3)	−0.002 (2)	0.008 (2)
F2	0.039 (3)	0.068 (4)	0.033 (3)	0.016 (3)	−0.023 (2)	−0.020 (3)
F3	0.088 (4)	0.031 (3)	0.041 (3)	−0.022 (3)	−0.034 (3)	−0.002 (2)
F4	0.033 (3)	0.150 (7)	0.028 (3)	−0.049 (4)	−0.007 (2)	−0.006 (3)
F5	0.061 (3)	0.039 (3)	0.027 (3)	0.002 (3)	−0.021 (2)	−0.009 (2)
F6	0.068 (4)	0.040 (3)	0.024 (3)	0.002 (3)	−0.020 (2)	0.001 (2)
O1	0.020 (2)	0.009 (2)	0.020 (2)	0.0002 (19)	−0.0037 (19)	−0.004 (2)
O2	0.018 (2)	0.011 (3)	0.014 (2)	−0.0001 (19)	−0.0036 (19)	−0.0027 (19)
N1	0.011 (3)	0.011 (3)	0.011 (3)	−0.003 (2)	−0.004 (2)	−0.002 (2)
N2	0.011 (3)	0.009 (3)	0.014 (3)	0.001 (2)	−0.003 (2)	−0.004 (2)
C1	0.008 (3)	0.012 (3)	0.011 (3)	−0.003 (3)	0.002 (2)	0.003 (3)
C2	0.009 (3)	0.015 (3)	0.020 (3)	0.001 (3)	0.001 (3)	0.000 (3)
C3	0.019 (3)	0.016 (4)	0.020 (4)	0.000 (3)	0.001 (3)	−0.002 (3)
C4	0.011 (3)	0.026 (4)	0.009 (3)	−0.003 (3)	−0.003 (2)	0.002 (3)
C5	0.012 (3)	0.018 (4)	0.020 (3)	0.002 (3)	0.000 (3)	0.005 (3)
C6	0.012 (3)	0.014 (3)	0.016 (3)	0.001 (3)	0.002 (3)	0.000 (3)
C7	0.008 (3)	0.017 (4)	0.018 (3)	−0.003 (3)	0.003 (3)	−0.002 (3)
C8	0.008 (3)	0.012 (3)	0.011 (3)	0.000 (3)	0.001 (2)	−0.002 (3)
C9	0.010 (3)	0.010 (3)	0.016 (3)	−0.003 (3)	0.003 (2)	−0.002 (3)
C10	0.014 (3)	0.013 (3)	0.015 (3)	0.002 (3)	0.006 (3)	0.003 (3)
C11	0.011 (3)	0.018 (4)	0.013 (3)	0.002 (3)	0.002 (2)	0.000 (3)
C12	0.008 (3)	0.014 (3)	0.012 (3)	0.002 (3)	0.000 (2)	0.000 (3)
C13	0.008 (3)	0.020 (4)	0.010 (3)	0.001 (3)	0.000 (2)	0.000 (3)
C14	0.023 (4)	0.035 (5)	0.015 (4)	−0.013 (3)	−0.004 (3)	0.000 (3)
C15	0.012 (3)	0.018 (4)	0.009 (3)	−0.003 (3)	0.001 (2)	0.002 (3)
C16	0.014 (3)	0.015 (3)	0.010 (3)	0.003 (3)	−0.002 (2)	−0.001 (3)
C17	0.019 (3)	0.023 (4)	0.014 (3)	−0.001 (3)	0.000 (3)	−0.006 (3)
C18	0.015 (3)	0.020 (4)	0.014 (3)	−0.007 (3)	−0.001 (3)	0.004 (3)
C19	0.013 (3)	0.018 (4)	0.016 (3)	−0.001 (3)	−0.003 (3)	0.006 (3)
C20	0.015 (3)	0.014 (3)	0.013 (3)	−0.001 (3)	0.000 (3)	0.000 (3)
C21	0.006 (3)	0.011 (3)	0.013 (3)	0.002 (2)	0.001 (2)	0.001 (3)
C22	0.007 (3)	0.015 (3)	0.008 (3)	0.004 (3)	−0.001 (2)	−0.002 (3)
C23	0.009 (3)	0.015 (3)	0.011 (3)	0.000 (3)	0.002 (2)	−0.003 (3)
C24	0.016 (3)	0.015 (3)	0.008 (3)	0.003 (3)	0.001 (2)	−0.002 (3)
C25	0.011 (3)	0.013 (3)	0.010 (3)	0.006 (3)	0.002 (2)	−0.001 (3)
C26	0.009 (3)	0.012 (3)	0.019 (3)	0.000 (3)	0.002 (3)	−0.002 (3)
C27	0.011 (3)	0.008 (3)	0.014 (3)	0.002 (2)	0.000 (2)	0.002 (3)
C28	0.020 (4)	0.039 (5)	0.013 (3)	−0.008 (3)	0.002 (3)	−0.007 (3)

Geometric parameters (Å, º)

Br1A—C11	1.895 (6)	C9—C10	1.387 (9)
Br2A—C25	1.889 (6)	C9—H9	0.9500
F1—C14	1.320 (8)	C10—C11	1.391 (9)
F2—C14	1.305 (9)	C10—H10	0.9500
F3—C14	1.343 (10)	C11—C12	1.376 (9)
F4—C28	1.313 (9)	C12—C13	1.383 (9)
F5—C28	1.362 (9)	C12—H12	0.9500
F6—C28	1.296 (9)	C13—H13	0.9500
O1—C7	1.235 (8)	C15—C16	1.386 (9)
O2—C21	1.221 (8)	C15—C20	1.387 (9)
N1—C7	1.344 (9)	C15—C21	1.501 (9)
N1—C8	1.420 (8)	C16—C17	1.394 (9)
N1—H1	0.97 (8)	C16—H16	0.9500
N2—C21	1.378 (8)	C17—C18	1.386 (10)
N2—C22	1.414 (8)	C17—H17	0.9500
N2—H2	0.87 (2)	C18—C19	1.391 (10)
C1—C2	1.373 (9)	C18—C28	1.508 (9)
C1—C6	1.402 (9)	C19—C20	1.381 (9)
C1—C7	1.506 (9)	C19—H19	0.9500
C2—C3	1.395 (9)	C20—H20	0.9500
C2—H2A	0.9500	C22—C23	1.383 (9)
C3—C4	1.391 (10)	C22—C27	1.403 (9)
C3—H3	0.9500	C23—C24	1.390 (9)
C4—C5	1.382 (10)	C23—H23	0.9500
C4—C14	1.496 (9)	C24—C25	1.382 (9)
C5—C6	1.383 (9)	C24—H24	0.9500
C5—H5	0.9500	C25—C26	1.402 (9)
C6—H6	0.9500	C26—C27	1.394 (9)
C8—C9	1.386 (9)	C26—H26	0.9500
C8—C13	1.390 (9)	C27—H27	0.9500
C7—N1—C8	126.7 (6)	F2—C14—C4	113.5 (6)
C7—N1—H1	114 (4)	F1—C14—C4	112.3 (6)
C8—N1—H1	120 (4)	F3—C14—C4	112.8 (6)
C21—N2—C22	125.8 (5)	C16—C15—C20	119.8 (6)
C21—N2—H2	125 (5)	C16—C15—C21	122.7 (6)
C22—N2—H2	109 (5)	C20—C15—C21	117.6 (6)
C2—C1—C6	120.4 (6)	C15—C16—C17	120.2 (6)
C2—C1—C7	122.4 (6)	C15—C16—H16	119.9
C6—C1—C7	117.2 (6)	C17—C16—H16	119.9
C1—C2—C3	119.7 (6)	C18—C17—C16	119.6 (6)
C1—C2—H2A	120.2	C18—C17—H17	120.2
C3—C2—H2A	120.2	C16—C17—H17	120.2
C4—C3—C2	119.9 (6)	C17—C18—C19	120.3 (6)
C4—C3—H3	120.1	C17—C18—C28	120.8 (6)
C2—C3—H3	120.1	C19—C18—C28	118.9 (6)
C5—C4—C3	120.3 (6)	C20—C19—C18	119.8 (6)
C5—C4—C14	119.9 (6)	C20—C19—H19	120.1
C3—C4—C14	119.7 (7)	C18—C19—H19	120.1
C4—C5—C6	119.9 (6)	C19—C20—C15	120.4 (6)
C4—C5—H5	120.1	C19—C20—H20	119.8
C6—C5—H5	120.1	C15—C20—H20	119.8
C5—C6—C1	119.8 (6)	O2—C21—N2	123.7 (6)
C5—C6—H6	120.1	O2—C21—C15	121.6 (6)
C1—C6—H6	120.1	N2—C21—C15	114.7 (5)
O1—C7—N1	123.6 (6)	C23—C22—C27	120.2 (6)
O1—C7—C1	121.0 (6)	C23—C22—N2	117.9 (6)
N1—C7—C1	115.5 (6)	C27—C22—N2	121.7 (6)
C9—C8—C13	120.1 (6)	C22—C23—C24	120.3 (6)
C9—C8—N1	117.9 (6)	C22—C23—H23	119.8
C13—C8—N1	121.8 (6)	C24—C23—H23	119.8
C8—C9—C10	120.4 (6)	C25—C24—C23	119.8 (6)
C8—C9—H9	119.8	C25—C24—H24	120.1
C10—C9—H9	119.8	C23—C24—H24	120.1
C9—C10—C11	119.1 (6)	C24—C25—C26	120.6 (6)
C9—C10—H10	120.5	C24—C25—Br2A	119.8 (5)
C11—C10—H10	120.5	C26—C25—Br2A	119.5 (5)
C12—C11—C10	120.5 (6)	C27—C26—C25	119.4 (6)
C12—C11—Br1A	120.5 (5)	C27—C26—H26	120.3
C10—C11—Br1A	119.0 (5)	C25—C26—H26	120.3
C11—C12—C13	120.6 (6)	C26—C27—C22	119.5 (6)
C11—C12—H12	119.7	C26—C27—H27	120.2
C13—C12—H12	119.7	C22—C27—H27	120.2
C12—C13—C8	119.3 (6)	F6—C28—F4	108.8 (7)
C12—C13—H13	120.3	F6—C28—F5	105.9 (6)
C8—C13—H13	120.3	F4—C28—F5	105.4 (7)
F2—C14—F1	108.0 (7)	F6—C28—C18	112.4 (6)
F2—C14—F3	105.7 (6)	F4—C28—C18	112.6 (6)
F1—C14—F3	103.9 (7)	F5—C28—C18	111.3 (6)
C6—C1—C2—C3	0.4 (9)	C20—C15—C16—C17	0.5 (10)
C7—C1—C2—C3	178.5 (6)	C21—C15—C16—C17	−178.6 (6)
C1—C2—C3—C4	0.2 (10)	C15—C16—C17—C18	−0.7 (10)
C2—C3—C4—C5	0.0 (10)	C16—C17—C18—C19	0.2 (10)
C2—C3—C4—C14	−178.7 (6)	C16—C17—C18—C28	−178.7 (6)
C3—C4—C5—C6	−0.8 (10)	C17—C18—C19—C20	0.3 (10)
C14—C4—C5—C6	177.9 (6)	C28—C18—C19—C20	179.3 (6)
C4—C5—C6—C1	1.4 (10)	C18—C19—C20—C15	−0.5 (10)
C2—C1—C6—C5	−1.2 (9)	C16—C15—C20—C19	0.1 (10)
C7—C1—C6—C5	−179.4 (6)	C21—C15—C20—C19	179.2 (6)
C8—N1—C7—O1	3.7 (10)	C22—N2—C21—O2	−3.0 (10)
C8—N1—C7—C1	−175.9 (5)	C22—N2—C21—C15	177.2 (5)
C2—C1—C7—O1	−149.7 (6)	C16—C15—C21—O2	149.0 (6)
C6—C1—C7—O1	28.5 (9)	C20—C15—C21—O2	−30.2 (9)
C2—C1—C7—N1	29.9 (8)	C16—C15—C21—N2	−31.2 (8)
C6—C1—C7—N1	−151.9 (6)	C20—C15—C21—N2	149.7 (6)
C7—N1—C8—C9	−150.8 (6)	C21—N2—C22—C23	149.4 (6)
C7—N1—C8—C13	33.5 (9)	C21—N2—C22—C27	−33.9 (9)
C13—C8—C9—C10	−0.9 (9)	C27—C22—C23—C24	−0.4 (9)
N1—C8—C9—C10	−176.7 (6)	N2—C22—C23—C24	176.2 (5)
C8—C9—C10—C11	1.0 (9)	C22—C23—C24—C25	−0.2 (9)
C9—C10—C11—C12	−0.2 (9)	C23—C24—C25—C26	1.0 (9)
C9—C10—C11—Br1A	179.0 (5)	C23—C24—C25—Br2A	−179.5 (5)
C10—C11—C12—C13	−0.6 (9)	C24—C25—C26—C27	−1.0 (9)
Br1A—C11—C12—C13	−179.8 (5)	Br2A—C25—C26—C27	179.4 (5)
C11—C12—C13—C8	0.7 (9)	C25—C26—C27—C22	0.4 (9)
C9—C8—C13—C12	0.1 (9)	C23—C22—C27—C26	0.3 (9)
N1—C8—C13—C12	175.7 (6)	N2—C22—C27—C26	−176.2 (6)
C5—C4—C14—F2	24.2 (10)	C17—C18—C28—F6	−129.7 (7)
C3—C4—C14—F2	−157.1 (7)	C19—C18—C28—F6	51.3 (9)
C5—C4—C14—F1	−98.7 (8)	C17—C18—C28—F4	107.0 (8)
C3—C4—C14—F1	80.1 (9)	C19—C18—C28—F4	−72.0 (9)
C5—C4—C14—F3	144.3 (7)	C17—C18—C28—F5	−11.1 (9)
C3—C4—C14—F3	−36.9 (9)	C19—C18—C28—F5	169.9 (6)

(PI22)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.965 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.7974 (15) Å	Cell parameters from 6946 reflections
b = 6.5752 (5) Å	θ = 3.3–30.0°
c = 9.6889 (7) Å	µ = 2.45 mm^−1
β = 93.899 (4)°	T = 100 K
V = 1321.86 (17) Å^3	Block
Z = 4	0.40 × 0.30 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	2275 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.024
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.5°, θmin = 3.0°
Tmin = 0.433, Tmax = 0.672	h = −25→25
9320 measured reflections	k = −7→6
2421 independent reflections	l = −11→11

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.019	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.046	w = 1/[σ^2(Fo^2) + (0.019P)^2 + 0.841P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
2421 reflections	Δρmax = 0.37 e Å^−3
185 parameters	Δρmin = −0.43 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.41593 (2)	0.71126 (2)	0.01992 (2)	0.01929 (7)
F1	0.12736 (7)	0.9053 (2)	0.23085 (14)	0.0271 (3)
F2	0.09167 (8)	0.6883 (2)	0.37202 (14)	0.0326 (4)
F3	0.03361 (8)	0.7762 (3)	0.19112 (17)	0.0393 (4)
O1	0.24062 (8)	0.6929 (2)	0.34159 (14)	0.0185 (4)
N1	0.27383 (9)	0.7899 (3)	0.13200 (17)	0.0144 (4)
H1	0.2692 (13)	0.779 (4)	0.0454 (17)	0.016 (7)*
C1	0.18814 (10)	0.5464 (3)	0.14031 (19)	0.0140 (5)
C2	0.21008 (11)	0.3906 (4)	0.05926 (19)	0.0155 (5)
H2	0.254757	0.381004	0.045368	0.019*
C3	0.16800 (13)	0.2492 (4)	−0.0016 (2)	0.0197 (5)
H3	0.183865	0.141907	−0.055511	0.024*
C4	0.10255 (13)	0.2640 (4)	0.0161 (2)	0.0215 (5)
H4	0.073479	0.166833	−0.025436	0.026*
C5	0.07984 (11)	0.4203 (4)	0.0942 (2)	0.0191 (5)
H5	0.034934	0.430997	0.105392	0.023*
C6	0.12176 (11)	0.5621 (4)	0.15674 (19)	0.0155 (5)
C7	0.23586 (11)	0.6842 (3)	0.2148 (2)	0.0142 (5)
C8	0.31863 (10)	0.9402 (3)	0.18238 (18)	0.0136 (5)
C9	0.38230 (11)	0.9412 (4)	0.14658 (19)	0.0151 (5)
C10	0.42449 (11)	1.0924 (4)	0.1954 (2)	0.0191 (5)
H10	0.467803	1.092428	0.169968	0.023*
C11	0.40337 (13)	1.2431 (4)	0.2813 (2)	0.0221 (5)
H11	0.432279	1.346109	0.315467	0.026*
C12	0.33988 (13)	1.2436 (4)	0.3175 (2)	0.0193 (5)
H12	0.325415	1.346780	0.376646	0.023*
C13	0.29777 (11)	1.0943 (3)	0.26767 (19)	0.0164 (5)
H13	0.254242	1.096514	0.291657	0.020*
C14	0.09438 (12)	0.7328 (4)	0.2378 (2)	0.0211 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01580 (10)	0.02337 (12)	0.01910 (9)	−0.00098 (6)	0.00418 (6)	−0.00406 (6)
F1	0.0307 (8)	0.0185 (8)	0.0329 (7)	0.0031 (7)	0.0087 (6)	0.0006 (6)
F2	0.0482 (11)	0.0314 (9)	0.0202 (7)	0.0015 (7)	0.0162 (7)	−0.0008 (6)
F3	0.0164 (9)	0.0524 (11)	0.0490 (10)	0.0134 (8)	−0.0005 (7)	−0.0160 (8)
O1	0.0200 (9)	0.0268 (10)	0.0088 (7)	−0.0036 (7)	0.0010 (6)	0.0002 (6)
N1	0.0135 (10)	0.0219 (11)	0.0077 (8)	−0.0038 (8)	0.0006 (7)	−0.0001 (7)
C1	0.0161 (12)	0.0178 (12)	0.0081 (8)	−0.0009 (10)	0.0001 (7)	0.0044 (8)
C2	0.0144 (12)	0.0202 (14)	0.0119 (9)	0.0013 (10)	0.0007 (8)	0.0021 (9)
C3	0.0258 (14)	0.0175 (13)	0.0155 (11)	0.0009 (11)	0.0007 (9)	−0.0010 (9)
C4	0.0234 (14)	0.0204 (14)	0.0201 (11)	−0.0082 (11)	−0.0040 (10)	0.0025 (9)
C5	0.0139 (12)	0.0233 (14)	0.0201 (10)	−0.0042 (10)	0.0007 (8)	0.0048 (9)
C6	0.0146 (11)	0.0199 (13)	0.0121 (9)	0.0013 (10)	0.0014 (8)	0.0052 (9)
C7	0.0122 (12)	0.0166 (13)	0.0138 (10)	0.0035 (9)	0.0012 (8)	0.0003 (8)
C8	0.0157 (11)	0.0158 (12)	0.0091 (9)	−0.0019 (10)	−0.0010 (8)	0.0047 (8)
C9	0.0166 (12)	0.0177 (12)	0.0111 (9)	0.0000 (10)	0.0013 (8)	0.0026 (8)
C10	0.0152 (12)	0.0210 (14)	0.0210 (10)	−0.0032 (10)	0.0012 (9)	0.0047 (9)
C11	0.0239 (14)	0.0173 (14)	0.0243 (12)	−0.0065 (11)	−0.0030 (10)	0.0002 (10)
C12	0.0246 (14)	0.0157 (13)	0.0176 (11)	0.0025 (10)	0.0000 (9)	−0.0006 (9)
C13	0.0162 (12)	0.0195 (14)	0.0132 (9)	0.0003 (10)	−0.0002 (8)	0.0025 (9)
C14	0.0140 (13)	0.0289 (15)	0.0205 (12)	0.0003 (11)	0.0023 (9)	0.0038 (10)

Geometric parameters (Å, º)

I1—C9	2.097 (2)	C4—C5	1.379 (3)
F1—C14	1.329 (3)	C4—H4	0.9500
F2—C14	1.338 (3)	C5—C6	1.387 (3)
F3—C14	1.344 (3)	C5—H5	0.9500
O1—C7	1.227 (3)	C6—C14	1.504 (3)
N1—C7	1.355 (3)	C8—C9	1.392 (3)
N1—C8	1.422 (3)	C8—C13	1.395 (3)
N1—H1	0.841 (16)	C9—C10	1.387 (3)
C1—C2	1.387 (3)	C10—C11	1.385 (3)
C1—C6	1.404 (3)	C10—H10	0.9500
C1—C7	1.493 (3)	C11—C12	1.389 (4)
C2—C3	1.382 (3)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.381 (3)
C3—C4	1.387 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	123.23 (17)	C9—C8—C13	118.9 (2)
C7—N1—H1	121.0 (18)	C9—C8—N1	122.01 (19)
C8—N1—H1	115.4 (17)	C13—C8—N1	119.04 (19)
C2—C1—C6	118.8 (2)	C10—C9—C8	120.6 (2)
C2—C1—C7	119.25 (19)	C10—C9—I1	119.18 (16)
C6—C1—C7	121.80 (19)	C8—C9—I1	120.23 (16)
C3—C2—C1	121.1 (2)	C11—C10—C9	119.9 (2)
C3—C2—H2	119.5	C11—C10—H10	120.0
C1—C2—H2	119.5	C9—C10—H10	120.0
C2—C3—C4	119.9 (2)	C10—C11—C12	119.9 (2)
C2—C3—H3	120.1	C10—C11—H11	120.0
C4—C3—H3	120.1	C12—C11—H11	120.0
C5—C4—C3	119.7 (2)	C13—C12—C11	120.1 (2)
C5—C4—H4	120.1	C13—C12—H12	120.0
C3—C4—H4	120.1	C11—C12—H12	120.0
C4—C5—C6	120.8 (2)	C12—C13—C8	120.5 (2)
C4—C5—H5	119.6	C12—C13—H13	119.7
C6—C5—H5	119.6	C8—C13—H13	119.7
C5—C6—C1	119.7 (2)	F1—C14—F2	106.98 (19)
C5—C6—C14	118.7 (2)	F1—C14—F3	106.2 (2)
C1—C6—C14	121.6 (2)	F2—C14—F3	105.83 (19)
O1—C7—N1	123.9 (2)	F1—C14—C6	113.27 (18)
O1—C7—C1	121.16 (19)	F2—C14—C6	112.76 (19)
N1—C7—C1	114.85 (17)	F3—C14—C6	111.3 (2)
C6—C1—C2—C3	−1.8 (3)	C7—N1—C8—C13	−50.9 (3)
C7—C1—C2—C3	174.34 (19)	C13—C8—C9—C10	0.3 (3)
C1—C2—C3—C4	1.1 (3)	N1—C8—C9—C10	178.77 (19)
C2—C3—C4—C5	0.1 (3)	C13—C8—C9—I1	179.50 (15)
C3—C4—C5—C6	−0.7 (3)	N1—C8—C9—I1	−2.0 (3)
C4—C5—C6—C1	0.0 (3)	C8—C9—C10—C11	0.4 (3)
C4—C5—C6—C14	178.4 (2)	I1—C9—C10—C11	−178.77 (16)
C2—C1—C6—C5	1.2 (3)	C9—C10—C11—C12	−0.5 (3)
C7—C1—C6—C5	−174.80 (19)	C10—C11—C12—C13	−0.2 (3)
C2—C1—C6—C14	−177.17 (19)	C11—C12—C13—C8	0.9 (3)
C7—C1—C6—C14	6.8 (3)	C9—C8—C13—C12	−1.0 (3)
C8—N1—C7—O1	−7.4 (4)	N1—C8—C13—C12	−179.50 (19)
C8—N1—C7—C1	174.9 (2)	C5—C6—C14—F1	−146.6 (2)
C2—C1—C7—O1	−117.2 (2)	C1—C6—C14—F1	31.8 (3)
C6—C1—C7—O1	58.8 (3)	C5—C6—C14—F2	91.7 (3)
C2—C1—C7—N1	60.5 (3)	C1—C6—C14—F2	−89.9 (3)
C6—C1—C7—N1	−123.5 (2)	C5—C6—C14—F3	−27.0 (3)
C7—N1—C8—C9	130.7 (2)	C1—C6—C14—F3	151.4 (2)

(PI23)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.894 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.0022 (10) Å	Cell parameters from 9276 reflections
b = 4.7359 (4) Å	θ = 2.3–30.2°
c = 26.562 (3) Å	µ = 2.36 mm^−1
β = 97.636 (3)°	T = 104 K
V = 1371.7 (2) Å^3	Plate
Z = 4	0.50 × 0.11 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	2873 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.047
Absorption correction: multi-scan SADABS 2014/4	θmax = 28.3°, θmin = 3.1°
Tmin = 0.436, Tmax = 0.596	h = −13→14
9961 measured reflections	k = −6→5
3401 independent reflections	l = −35→32

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0395P)^2 + 1.7205P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3401 reflections	Δρmax = 1.07 e Å^−3
195 parameters	Δρmin = −1.17 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
I1	0.11142 (2)	0.84711 (4)	0.05425 (2)	0.02933 (10)
F1A	0.2045 (5)	0.328 (3)	−0.2824 (2)	0.129 (4)	0.668 (4)
F2A	0.3620 (7)	0.5581 (11)	−0.2545 (2)	0.075 (2)	0.668 (4)
F3A	0.3469 (7)	0.1429 (9)	−0.2355 (2)	0.074 (2)	0.668 (4)
F1B	0.3750 (12)	0.339 (7)	−0.2389 (5)	0.129 (4)	0.332 (4)
F2B	0.2076 (15)	0.140 (2)	−0.2621 (5)	0.075 (2)	0.332 (4)
F3B	0.2278 (15)	0.540 (2)	−0.2851 (4)	0.074 (2)	0.332 (4)
O1	0.3035 (3)	0.1009 (4)	−0.05184 (10)	0.0352 (7)
N1	0.2806 (3)	0.5374 (5)	−0.01811 (10)	0.0191 (6)
H1	0.273 (4)	0.710 (5)	−0.0283 (18)	0.049 (13)*
C1	0.2194 (3)	0.4642 (6)	−0.10749 (12)	0.0213 (7)
C2	0.1232 (4)	0.6557 (7)	−0.11296 (15)	0.0311 (8)
H2	0.091199	0.723253	−0.083705	0.037*
C3	0.0731 (4)	0.7494 (11)	−0.16070 (17)	0.0444 (10)
H3	0.005617	0.876140	−0.164211	0.053*
C4	0.1222 (4)	0.6569 (8)	−0.20341 (16)	0.0382 (9)
H4	0.089486	0.722654	−0.236211	0.046*
C5	0.2192 (4)	0.4682 (7)	−0.19778 (14)	0.0300 (8)
C6	0.2660 (4)	0.3689 (6)	−0.15065 (14)	0.0287 (8)
H6	0.330522	0.234182	−0.147459	0.034*
C7	0.2718 (3)	0.3504 (6)	−0.05695 (13)	0.0224 (7)
C8	0.3248 (3)	0.4781 (6)	0.03297 (12)	0.0191 (6)
C9	0.2686 (3)	0.5984 (6)	0.07217 (13)	0.0200 (7)
C10	0.3122 (4)	0.5489 (8)	0.12232 (14)	0.0293 (8)
H10	0.273254	0.633928	0.148345	0.035*
C11	0.4135 (4)	0.3742 (8)	0.13499 (16)	0.0360 (9)
H11	0.443712	0.338441	0.169591	0.043*
C12	0.4696 (4)	0.2530 (9)	0.09658 (16)	0.0364 (9)
H12	0.538599	0.133209	0.104996	0.044*
C13	0.4264 (3)	0.3046 (6)	0.04613 (15)	0.0260 (8)
H13	0.466261	0.221026	0.020223	0.031*
C14	0.2742 (5)	0.3751 (8)	−0.24387 (16)	0.0419 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02713 (16)	0.02917 (13)	0.03330 (15)	0.01031 (9)	0.00989 (11)	−0.00373 (9)
F1A	0.042 (3)	0.300 (13)	0.044 (3)	0.014 (6)	−0.003 (3)	−0.086 (6)
F2A	0.112 (5)	0.053 (2)	0.076 (4)	−0.019 (3)	0.068 (4)	−0.010 (2)
F3A	0.139 (6)	0.048 (2)	0.047 (3)	0.030 (3)	0.057 (3)	0.0059 (18)
F1B	0.042 (3)	0.300 (13)	0.044 (3)	0.014 (6)	−0.003 (3)	−0.086 (6)
F2B	0.112 (5)	0.053 (2)	0.076 (4)	−0.019 (3)	0.068 (4)	−0.010 (2)
F3B	0.139 (6)	0.048 (2)	0.047 (3)	0.030 (3)	0.057 (3)	0.0059 (18)
O1	0.068 (2)	0.0094 (9)	0.0321 (14)	0.0057 (11)	0.0198 (15)	0.0004 (9)
N1	0.0247 (15)	0.0105 (10)	0.0233 (13)	0.0046 (10)	0.0071 (12)	0.0027 (10)
C1	0.0261 (18)	0.0162 (13)	0.0229 (16)	−0.0050 (13)	0.0078 (15)	−0.0026 (12)
C2	0.026 (2)	0.0428 (19)	0.0242 (18)	0.0060 (16)	0.0020 (16)	−0.0086 (15)
C3	0.040 (3)	0.058 (2)	0.031 (2)	0.016 (2)	−0.008 (2)	−0.007 (2)
C4	0.040 (2)	0.049 (2)	0.0241 (19)	−0.0024 (19)	−0.0025 (19)	−0.0044 (16)
C5	0.041 (2)	0.0258 (15)	0.0251 (18)	−0.0103 (16)	0.0120 (17)	−0.0057 (13)
C6	0.043 (2)	0.0185 (14)	0.0281 (19)	−0.0007 (14)	0.0153 (18)	−0.0032 (12)
C7	0.031 (2)	0.0150 (13)	0.0237 (16)	0.0008 (13)	0.0135 (16)	0.0004 (11)
C8	0.0192 (16)	0.0127 (12)	0.0262 (16)	−0.0016 (12)	0.0065 (14)	0.0034 (11)
C9	0.0194 (17)	0.0179 (13)	0.0229 (16)	0.0003 (12)	0.0040 (14)	0.0019 (11)
C10	0.031 (2)	0.0330 (16)	0.0246 (17)	−0.0048 (16)	0.0071 (16)	0.0019 (14)
C11	0.034 (2)	0.045 (2)	0.027 (2)	−0.0010 (18)	0.0004 (18)	0.0154 (16)
C12	0.029 (2)	0.0371 (18)	0.044 (2)	0.0094 (17)	0.0074 (19)	0.0229 (18)
C13	0.0238 (19)	0.0217 (15)	0.0342 (19)	0.0049 (13)	0.0104 (17)	0.0083 (13)
C14	0.064 (3)	0.038 (2)	0.027 (2)	−0.001 (2)	0.018 (2)	−0.0011 (16)

Geometric parameters (Å, º)

I1—C9	2.094 (3)	C3—H3	0.9500
F1A—C14	1.215 (7)	C4—C5	1.385 (6)
F2A—C14	1.355 (7)	C4—H4	0.9500
F3A—C14	1.361 (7)	C5—C6	1.372 (5)
F1B—C14	1.112 (14)	C5—C14	1.502 (5)
F2B—C14	1.383 (12)	C6—H6	0.9500
F3B—C14	1.387 (12)	C8—C13	1.394 (5)
O1—C7	1.235 (3)	C8—C9	1.401 (4)
N1—C7	1.353 (4)	C9—C10	1.375 (5)
N1—C8	1.408 (4)	C10—C11	1.393 (6)
N1—H1	0.864 (19)	C10—H10	0.9500
C1—C2	1.387 (5)	C11—C12	1.385 (6)
C1—C6	1.392 (4)	C11—H11	0.9500
C1—C7	1.490 (5)	C12—C13	1.383 (6)
C2—C3	1.386 (6)	C12—H12	0.9500
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.391 (6)
C7—N1—C8	125.8 (3)	C10—C9—C8	121.3 (3)
C7—N1—H1	113 (3)	C10—C9—I1	119.2 (2)
C8—N1—H1	120 (3)	C8—C9—I1	119.5 (3)
C2—C1—C6	119.0 (3)	C9—C10—C11	120.0 (3)
C2—C1—C7	122.0 (3)	C9—C10—H10	120.0
C6—C1—C7	119.0 (3)	C11—C10—H10	120.0
C3—C2—C1	120.6 (3)	C12—C11—C10	119.3 (4)
C3—C2—H2	119.7	C12—C11—H11	120.4
C1—C2—H2	119.7	C10—C11—H11	120.4
C2—C3—C4	119.7 (4)	C13—C12—C11	120.7 (4)
C2—C3—H3	120.2	C13—C12—H12	119.6
C4—C3—H3	120.2	C11—C12—H12	119.6
C5—C4—C3	119.5 (4)	C12—C13—C8	120.5 (3)
C5—C4—H4	120.2	C12—C13—H13	119.7
C3—C4—H4	120.2	C8—C13—H13	119.7
C6—C5—C4	120.7 (3)	F1A—C14—F2A	109.2 (6)
C6—C5—C14	120.0 (4)	F1A—C14—F3A	106.4 (6)
C4—C5—C14	119.3 (4)	F2A—C14—F3A	97.5 (5)
C5—C6—C1	120.4 (3)	F1B—C14—F2B	113.1 (14)
C5—C6—H6	119.8	F1B—C14—F3B	115.8 (14)
C1—C6—H6	119.8	F2B—C14—F3B	93.1 (9)
O1—C7—N1	123.5 (3)	F1B—C14—C5	116.8 (7)
O1—C7—C1	121.0 (3)	F1A—C14—C5	117.6 (5)
N1—C7—C1	115.5 (3)	F2A—C14—C5	110.9 (4)
C13—C8—C9	118.2 (3)	F3A—C14—C5	113.3 (4)
C13—C8—N1	121.5 (3)	F2B—C14—C5	105.7 (5)
C9—C8—N1	120.3 (3)	F3B—C14—C5	109.5 (5)
C6—C1—C2—C3	0.5 (6)	N1—C8—C9—I1	3.8 (4)
C7—C1—C2—C3	−177.4 (4)	C8—C9—C10—C11	−0.6 (5)
C1—C2—C3—C4	−1.9 (7)	I1—C9—C10—C11	177.2 (3)
C2—C3—C4—C5	1.1 (7)	C9—C10—C11—C12	0.3 (6)
C3—C4—C5—C6	1.0 (6)	C10—C11—C12—C13	0.2 (6)
C3—C4—C5—C14	−178.3 (4)	C11—C12—C13—C8	−0.5 (6)
C4—C5—C6—C1	−2.3 (5)	C9—C8—C13—C12	0.2 (5)
C14—C5—C6—C1	177.0 (3)	N1—C8—C13—C12	178.9 (3)
C2—C1—C6—C5	1.6 (5)	C6—C5—C14—F1B	−35 (2)
C7—C1—C6—C5	179.6 (3)	C4—C5—C14—F1B	144.3 (19)
C8—N1—C7—O1	−0.7 (5)	C6—C5—C14—F1A	140.6 (8)
C8—N1—C7—C1	178.8 (3)	C4—C5—C14—F1A	−40.1 (9)
C2—C1—C7—O1	141.1 (4)	C6—C5—C14—F2A	−92.8 (5)
C6—C1—C7—O1	−36.9 (5)	C4—C5—C14—F2A	86.6 (6)
C2—C1—C7—N1	−38.5 (5)	C6—C5—C14—F3A	15.7 (7)
C6—C1—C7—N1	143.5 (3)	C4—C5—C14—F3A	−165.0 (5)
C7—N1—C8—C13	40.4 (5)	C6—C5—C14—F2B	91.8 (8)
C7—N1—C8—C9	−140.9 (3)	C4—C5—C14—F2B	−88.9 (8)
C13—C8—C9—C10	0.3 (5)	C6—C5—C14—F3B	−169.1 (8)
N1—C8—C9—C10	−178.4 (3)	C4—C5—C14—F3B	10.2 (9)
C13—C8—C9—I1	−177.5 (2)

(PI24)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.937 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 20.5840 (16) Å	Cell parameters from 3505 reflections
b = 7.1797 (5) Å	θ = 3.0–27.9°
c = 9.1451 (7) Å	µ = 2.42 mm^−1
β = 97.122 (4)°	T = 100 K
V = 1341.10 (17) Å^3	Plate
Z = 4	0.40 × 0.20 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	1884 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.031
Absorption correction: multi-scan SADABS 2014/4	θmax = 25.0°, θmin = 3.0°
Tmin = 0.552, Tmax = 0.796	h = −15→24
5872 measured reflections	k = −8→8
2238 independent reflections	l = −10→9

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0324P)^2 + 4.3811P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2238 reflections	Δρmax = 0.82 e Å^−3
184 parameters	Δρmin = −1.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.41038 (2)	0.78861 (5)	0.94315 (4)	0.02273 (14)
F1	0.0510 (2)	1.3634 (6)	1.0365 (4)	0.0603 (13)
F2	0.00029 (16)	1.2753 (5)	0.8321 (5)	0.0451 (10)
F3	0.07676 (17)	1.4743 (5)	0.8363 (5)	0.0468 (11)
O1	0.25009 (17)	0.6045 (5)	0.9884 (4)	0.0170 (8)
N1	0.2688 (2)	0.6838 (6)	0.7570 (5)	0.0144 (10)
H1	0.257 (3)	0.756 (8)	0.687 (6)	0.017*
C1	0.1931 (2)	0.8670 (7)	0.8791 (5)	0.0118 (11)
C2	0.2010 (3)	1.0312 (7)	0.8027 (6)	0.0180 (12)
H2	0.236133	1.042157	0.744903	0.022*
C3	0.1584 (3)	1.1788 (7)	0.8098 (6)	0.0199 (13)
H3	0.164302	1.290639	0.757545	0.024*
C4	0.1070 (3)	1.1628 (7)	0.8935 (6)	0.0181 (12)
C5	0.0990 (3)	1.0004 (7)	0.9709 (6)	0.0193 (13)
H5	0.063784	0.989806	1.028485	0.023*
C6	0.1419 (2)	0.8541 (7)	0.9647 (6)	0.0153 (12)
H6	0.136454	0.743699	1.019089	0.018*
C7	0.2396 (2)	0.7086 (7)	0.8797 (6)	0.0147 (11)
C8	0.3162 (2)	0.5419 (7)	0.7459 (6)	0.0128 (11)
C9	0.2987 (3)	0.3902 (7)	0.6552 (6)	0.0163 (12)
H9	0.255135	0.380597	0.607651	0.020*
C10	0.3439 (3)	0.2520 (7)	0.6328 (7)	0.0239 (14)
H10	0.331486	0.149296	0.569960	0.029*
C11	0.4075 (3)	0.2667 (7)	0.7041 (6)	0.0240 (14)
H11	0.438814	0.173159	0.690004	0.029*
C12	0.4256 (3)	0.4175 (7)	0.7956 (6)	0.0190 (12)
H12	0.468967	0.426198	0.844567	0.023*
C13	0.3800 (3)	0.5555 (7)	0.8153 (6)	0.0167 (12)
C14	0.0591 (3)	1.3176 (8)	0.8989 (7)	0.0245 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.0212 (2)	0.0233 (2)	0.0234 (2)	−0.00005 (17)	0.00146 (15)	−0.00810 (17)
F1	0.085 (3)	0.072 (3)	0.024 (2)	0.062 (3)	0.005 (2)	−0.007 (2)
F2	0.0249 (19)	0.030 (2)	0.076 (3)	0.0099 (16)	−0.0119 (19)	−0.0119 (19)
F3	0.044 (2)	0.016 (2)	0.084 (3)	0.0120 (17)	0.021 (2)	0.0104 (19)
O1	0.025 (2)	0.011 (2)	0.016 (2)	0.0051 (16)	0.0057 (16)	0.0015 (16)
N1	0.020 (2)	0.013 (3)	0.011 (3)	0.0074 (19)	0.0030 (19)	0.0048 (19)
C1	0.013 (2)	0.010 (3)	0.012 (3)	0.000 (2)	−0.001 (2)	0.000 (2)
C2	0.021 (3)	0.017 (3)	0.017 (3)	0.001 (2)	0.006 (2)	−0.002 (2)
C3	0.029 (3)	0.011 (3)	0.020 (3)	−0.001 (2)	0.005 (3)	0.006 (2)
C4	0.019 (3)	0.012 (3)	0.022 (3)	0.005 (2)	−0.001 (2)	−0.004 (2)
C5	0.020 (3)	0.020 (3)	0.019 (3)	0.001 (2)	0.006 (2)	−0.005 (2)
C6	0.018 (3)	0.015 (3)	0.013 (3)	−0.002 (2)	0.001 (2)	0.000 (2)
C7	0.014 (3)	0.011 (3)	0.018 (3)	−0.002 (2)	−0.001 (2)	−0.001 (2)
C8	0.019 (3)	0.011 (3)	0.010 (3)	0.003 (2)	0.005 (2)	0.003 (2)
C9	0.023 (3)	0.011 (3)	0.017 (3)	−0.002 (2)	0.009 (2)	0.000 (2)
C10	0.035 (3)	0.008 (3)	0.031 (4)	−0.001 (2)	0.015 (3)	−0.005 (2)
C11	0.028 (3)	0.011 (3)	0.036 (4)	0.005 (2)	0.016 (3)	−0.003 (2)
C12	0.018 (3)	0.017 (3)	0.024 (3)	0.004 (2)	0.006 (2)	0.003 (2)
C13	0.022 (3)	0.015 (3)	0.014 (3)	−0.001 (2)	0.006 (2)	0.001 (2)
C14	0.030 (3)	0.016 (3)	0.028 (4)	0.005 (3)	0.004 (3)	0.001 (3)

Geometric parameters (Å, º)

I1—C13	2.092 (5)	C4—C5	1.385 (8)
F1—C14	1.331 (7)	C4—C14	1.491 (7)
F2—C14	1.322 (7)	C5—C6	1.378 (7)
F3—C14	1.333 (6)	C5—H5	0.9500
O1—C7	1.241 (6)	C6—H6	0.9500
N1—C7	1.349 (6)	C8—C9	1.389 (7)
N1—C8	1.422 (6)	C8—C13	1.390 (7)
N1—H1	0.83 (6)	C9—C10	1.392 (7)
C1—C2	1.390 (7)	C9—H9	0.9500
C1—C6	1.393 (7)	C10—C11	1.393 (8)
C1—C7	1.486 (7)	C10—H10	0.9500
C2—C3	1.382 (7)	C11—C12	1.390 (7)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.385 (7)	C12—C13	1.391 (7)
C3—H3	0.9500	C12—H12	0.9500
C7—N1—C8	122.3 (4)	C9—C8—C13	119.2 (5)
C7—N1—H1	116 (4)	C9—C8—N1	118.4 (5)
C8—N1—H1	122 (4)	C13—C8—N1	122.3 (5)
C2—C1—C6	118.9 (5)	C8—C9—C10	121.3 (5)
C2—C1—C7	122.4 (4)	C8—C9—H9	119.4
C6—C1—C7	118.6 (5)	C10—C9—H9	119.4
C3—C2—C1	120.8 (5)	C9—C10—C11	118.9 (5)
C3—C2—H2	119.6	C9—C10—H10	120.6
C1—C2—H2	119.6	C11—C10—H10	120.6
C2—C3—C4	119.7 (5)	C12—C11—C10	120.4 (5)
C2—C3—H3	120.2	C12—C11—H11	119.8
C4—C3—H3	120.2	C10—C11—H11	119.8
C5—C4—C3	120.0 (5)	C11—C12—C13	119.9 (5)
C5—C4—C14	119.3 (5)	C11—C12—H12	120.1
C3—C4—C14	120.7 (5)	C13—C12—H12	120.1
C6—C5—C4	120.2 (5)	C8—C13—C12	120.3 (5)
C6—C5—H5	119.9	C8—C13—I1	120.7 (4)
C4—C5—H5	119.9	C12—C13—I1	118.9 (4)
C5—C6—C1	120.4 (5)	F2—C14—F1	106.2 (5)
C5—C6—H6	119.8	F2—C14—F3	106.1 (5)
C1—C6—H6	119.8	F1—C14—F3	105.7 (5)
O1—C7—N1	122.4 (5)	F2—C14—C4	112.7 (5)
O1—C7—C1	120.8 (4)	F1—C14—C4	112.1 (5)
N1—C7—C1	116.8 (4)	F3—C14—C4	113.5 (5)
C6—C1—C2—C3	−0.8 (8)	C13—C8—C9—C10	0.0 (7)
C7—C1—C2—C3	−177.2 (5)	N1—C8—C9—C10	176.2 (5)
C1—C2—C3—C4	−0.3 (8)	C8—C9—C10—C11	0.5 (8)
C2—C3—C4—C5	0.7 (8)	C9—C10—C11—C12	−0.2 (8)
C2—C3—C4—C14	−177.9 (5)	C10—C11—C12—C13	−0.6 (8)
C3—C4—C5—C6	−0.2 (8)	C9—C8—C13—C12	−0.8 (8)
C14—C4—C5—C6	178.5 (5)	N1—C8—C13—C12	−176.9 (5)
C4—C5—C6—C1	−0.9 (8)	C9—C8—C13—I1	176.4 (4)
C2—C1—C6—C5	1.3 (8)	N1—C8—C13—I1	0.4 (7)
C7—C1—C6—C5	177.9 (5)	C11—C12—C13—C8	1.1 (8)
C8—N1—C7—O1	−3.1 (8)	C11—C12—C13—I1	−176.2 (4)
C8—N1—C7—C1	177.4 (4)	C5—C4—C14—F2	−67.6 (7)
C2—C1—C7—O1	148.6 (5)	C3—C4—C14—F2	111.0 (6)
C6—C1—C7—O1	−27.8 (7)	C5—C4—C14—F1	52.1 (7)
C2—C1—C7—N1	−31.9 (7)	C3—C4—C14—F1	−129.2 (6)
C6—C1—C7—N1	151.7 (5)	C5—C4—C14—F3	171.7 (5)
C7—N1—C8—C9	108.6 (6)	C3—C4—C14—F3	−9.6 (8)
C7—N1—C8—C13	−75.3 (7)

(PI32)

Crystal data

C14H9F3INO	Dx = 1.882 Mg m^−3
Mr = 391.12	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca21	Cell parameters from 7820 reflections
a = 7.9499 (4) Å	θ = 2.8–27.3°
b = 19.6384 (10) Å	µ = 2.35 mm^−1
c = 8.8397 (4) Å	T = 110 K
V = 1380.08 (12) Å^3	Plate
Z = 4	0.50 × 0.10 × 0.05 mm
F(000) = 752

Data collection

Bruker APEX-II CCD diffractometer	3706 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.025
Absorption correction: multi-scan SADABS 2014/4	θmax = 30.1°, θmin = 2.8°
Tmin = 0.513, Tmax = 0.729	h = −11→11
12915 measured reflections	k = −23→27
3913 independent reflections	l = −12→12

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.017	w = 1/[σ^2(Fo^2) + (0.0093P)^2 + 0.1106P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.037	(Δ/σ)max = 0.001
S = 1.09	Δρmax = 0.54 e Å^−3
3913 reflections	Δρmin = −0.31 e Å^−3
184 parameters	Absolute structure: Flack x determined using 1597 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
1 restraint	Absolute structure parameter: −0.011 (9)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.43314 (2)	0.46752 (2)	0.24777 (3)	0.01618 (5)
F1	0.3102 (2)	0.12538 (10)	0.5534 (2)	0.0329 (4)
F2	0.1924 (3)	0.02807 (9)	0.5875 (3)	0.0423 (5)
F3	0.0997 (3)	0.09569 (11)	0.4156 (2)	0.0385 (5)
O1	0.1093 (2)	0.25026 (11)	0.4680 (2)	0.0219 (4)
N1	0.2660 (3)	0.27656 (11)	0.6765 (2)	0.0151 (4)
H1	0.287 (4)	0.2640 (15)	0.782 (3)	0.018*
C1	0.0403 (3)	0.19491 (13)	0.6977 (3)	0.0135 (5)
C2	−0.0674 (3)	0.22098 (14)	0.8070 (3)	0.0157 (5)
H2	−0.067383	0.268395	0.828313	0.019*
C3	−0.1757 (3)	0.17763 (15)	0.8857 (3)	0.0222 (5)
H3	−0.251433	0.195812	0.958373	0.027*
C4	−0.1730 (3)	0.10857 (16)	0.8583 (3)	0.0250 (6)
H4	−0.247289	0.079294	0.911799	0.030*
C5	−0.0623 (2)	0.08169 (12)	0.7529 (6)	0.0227 (5)
H5	−0.058632	0.033915	0.736400	0.027*
C6	0.0432 (3)	0.12452 (13)	0.6714 (3)	0.0166 (5)
C7	0.1428 (3)	0.24329 (12)	0.6025 (3)	0.0144 (4)
C8	0.3907 (3)	0.31811 (13)	0.6080 (3)	0.0143 (5)
C9	0.5535 (3)	0.31334 (14)	0.6653 (3)	0.0169 (5)
H9	0.577359	0.283472	0.747032	0.020*
C10	0.6812 (3)	0.35265 (14)	0.6018 (3)	0.0181 (5)
H10	0.792256	0.349397	0.640886	0.022*
C11	0.6482 (3)	0.39656 (13)	0.4822 (3)	0.0161 (5)
H11	0.735648	0.422925	0.438140	0.019*
C12	0.4843 (3)	0.40101 (12)	0.4284 (3)	0.0136 (4)
C13	0.3538 (3)	0.36289 (13)	0.4904 (3)	0.0131 (4)
H13	0.242178	0.367301	0.453339	0.016*
C14	0.1614 (4)	0.09382 (16)	0.5569 (3)	0.0258 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01555 (6)	0.01550 (8)	0.01750 (7)	0.00168 (4)	0.00087 (9)	0.00499 (8)
F1	0.0210 (7)	0.0418 (11)	0.0360 (10)	0.0020 (7)	0.0080 (7)	−0.0115 (8)
F2	0.0498 (12)	0.0231 (11)	0.0540 (13)	0.0144 (7)	0.0065 (10)	−0.0082 (8)
F3	0.0416 (10)	0.0514 (13)	0.0223 (9)	0.0078 (9)	−0.0016 (8)	−0.0152 (9)
O1	0.0229 (8)	0.0322 (11)	0.0105 (8)	−0.0107 (8)	−0.0028 (7)	0.0046 (8)
N1	0.0168 (9)	0.0191 (11)	0.0094 (10)	−0.0033 (8)	−0.0003 (8)	0.0021 (8)
C1	0.0126 (9)	0.0180 (13)	0.0099 (9)	−0.0016 (9)	−0.0026 (7)	0.0027 (8)
C2	0.0167 (11)	0.0163 (13)	0.0139 (10)	−0.0001 (9)	−0.0007 (8)	0.0018 (9)
C3	0.0179 (11)	0.0303 (15)	0.0185 (12)	−0.0001 (11)	0.0049 (10)	0.0050 (10)
C4	0.0200 (12)	0.0281 (16)	0.0268 (14)	−0.0068 (11)	0.0023 (11)	0.0098 (11)
C5	0.0229 (10)	0.0163 (11)	0.0287 (11)	−0.0037 (8)	−0.0057 (15)	0.0019 (19)
C6	0.0148 (10)	0.0184 (13)	0.0167 (12)	−0.0003 (9)	−0.0026 (9)	−0.0012 (10)
C7	0.0149 (10)	0.0167 (12)	0.0115 (10)	−0.0004 (9)	0.0020 (9)	−0.0003 (9)
C8	0.0157 (10)	0.0163 (13)	0.0109 (10)	−0.0028 (9)	0.0020 (9)	−0.0011 (9)
C9	0.0185 (11)	0.0196 (13)	0.0127 (11)	−0.0031 (9)	−0.0019 (9)	0.0034 (9)
C10	0.0151 (10)	0.0220 (14)	0.0170 (11)	−0.0044 (9)	−0.0040 (9)	0.0022 (9)
C11	0.0154 (10)	0.0158 (12)	0.0170 (11)	−0.0041 (9)	0.0010 (9)	−0.0008 (9)
C12	0.0161 (10)	0.0125 (12)	0.0124 (10)	0.0024 (9)	0.0008 (9)	0.0006 (9)
C13	0.0141 (10)	0.0146 (12)	0.0105 (10)	0.0002 (9)	0.0003 (8)	−0.0016 (8)
C14	0.0292 (14)	0.0240 (15)	0.0242 (13)	0.0050 (11)	−0.0005 (11)	−0.0070 (11)

Geometric parameters (Å, º)

I1—C12	2.102 (2)	C4—C5	1.386 (5)
F1—C14	1.336 (3)	C4—H4	0.9500
F2—C14	1.342 (3)	C5—C6	1.390 (4)
F3—C14	1.342 (3)	C5—H5	0.9500
O1—C7	1.226 (3)	C6—C14	1.506 (4)
N1—C7	1.347 (3)	C8—C13	1.393 (3)
N1—C8	1.419 (3)	C8—C9	1.393 (3)
N1—H1	0.98 (3)	C9—C10	1.393 (3)
C1—C2	1.389 (3)	C9—H9	0.9500
C1—C6	1.402 (4)	C10—C11	1.390 (3)
C1—C7	1.509 (3)	C10—H10	0.9500
C2—C3	1.396 (4)	C11—C12	1.390 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.378 (4)	C12—C13	1.392 (3)
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.4 (2)	C13—C8—C9	120.6 (2)
C7—N1—H1	117.8 (18)	C13—C8—N1	122.3 (2)
C8—N1—H1	115.4 (18)	C9—C8—N1	117.1 (2)
C2—C1—C6	119.3 (2)	C10—C9—C8	119.6 (2)
C2—C1—C7	119.3 (2)	C10—C9—H9	120.2
C6—C1—C7	121.3 (2)	C8—C9—H9	120.2
C1—C2—C3	120.1 (3)	C11—C10—C9	120.8 (2)
C1—C2—H2	119.9	C11—C10—H10	119.6
C3—C2—H2	119.9	C9—C10—H10	119.6
C4—C3—C2	120.2 (2)	C12—C11—C10	118.4 (2)
C4—C3—H3	119.9	C12—C11—H11	120.8
C2—C3—H3	119.9	C10—C11—H11	120.8
C3—C4—C5	120.2 (2)	C11—C12—C13	122.0 (2)
C3—C4—H4	119.9	C11—C12—I1	118.70 (17)
C5—C4—H4	119.9	C13—C12—I1	119.28 (17)
C4—C5—C6	120.1 (2)	C12—C13—C8	118.5 (2)
C4—C5—H5	119.9	C12—C13—H13	120.8
C6—C5—H5	119.9	C8—C13—H13	120.8
C5—C6—C1	120.0 (2)	F1—C14—F2	106.7 (2)
C5—C6—C14	118.9 (3)	F1—C14—F3	106.8 (2)
C1—C6—C14	121.1 (2)	F2—C14—F3	106.3 (2)
O1—C7—N1	125.1 (2)	F1—C14—C6	112.5 (2)
O1—C7—C1	119.6 (2)	F2—C14—C6	111.4 (2)
N1—C7—C1	115.3 (2)	F3—C14—C6	112.7 (2)
C6—C1—C2—C3	−2.3 (3)	C7—N1—C8—C9	−140.0 (3)
C7—C1—C2—C3	173.5 (2)	C13—C8—C9—C10	−1.4 (4)
C1—C2—C3—C4	1.8 (4)	N1—C8—C9—C10	179.6 (2)
C2—C3—C4—C5	0.3 (4)	C8—C9—C10—C11	0.0 (4)
C3—C4—C5—C6	−1.8 (5)	C9—C10—C11—C12	0.8 (4)
C4—C5—C6—C1	1.2 (5)	C10—C11—C12—C13	−0.2 (4)
C4—C5—C6—C14	−179.6 (3)	C10—C11—C12—I1	179.83 (19)
C2—C1—C6—C5	0.8 (4)	C11—C12—C13—C8	−1.2 (4)
C7—C1—C6—C5	−175.0 (3)	I1—C12—C13—C8	178.77 (17)
C2—C1—C6—C14	−178.3 (2)	C9—C8—C13—C12	2.0 (4)
C7—C1—C6—C14	5.9 (3)	N1—C8—C13—C12	−179.1 (2)
C8—N1—C7—O1	−8.7 (4)	C5—C6—C14—F1	−142.6 (3)
C8—N1—C7—C1	172.1 (2)	C1—C6—C14—F1	36.5 (3)
C2—C1—C7—O1	−109.9 (3)	C5—C6—C14—F2	−22.9 (4)
C6—C1—C7—O1	65.9 (3)	C1—C6—C14—F2	156.3 (2)
C2—C1—C7—N1	69.4 (3)	C5—C6—C14—F3	96.6 (3)
C6—C1—C7—N1	−114.8 (2)	C1—C6—C14—F3	−84.3 (3)
C7—N1—C8—C13	41.1 (4)

(PI33)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.924 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.9793 (16) Å	Cell parameters from 9167 reflections
b = 5.2899 (4) Å	θ = 3.0–30.1°
c = 9.5068 (6) Å	µ = 2.40 mm^−1
β = 95.747 (2)°	T = 107 K
V = 1349.97 (16) Å^3	Plate
Z = 4	0.45 × 0.24 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3349 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.030
Absorption correction: multi-scan SADABS 2014/4	θmax = 29.1°, θmin = 3.0°
Tmin = 0.543, Tmax = 0.726	h = −36→36
25810 measured reflections	k = −7→7
3608 independent reflections	l = −13→11

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.050	w = 1/[σ^2(Fo^2) + (0.0209P)^2 + 1.1723P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3608 reflections	Δρmax = 0.72 e Å^−3
185 parameters	Δρmin = −0.45 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.45193 (2)	0.28115 (2)	0.31304 (2)	0.02261 (5)
F1	0.02629 (5)	−0.0664 (3)	0.66390 (17)	0.0474 (4)
F2	0.03423 (5)	0.3094 (3)	0.58937 (16)	0.0425 (4)
F3	0.07066 (5)	0.1984 (3)	0.79042 (14)	0.0362 (3)
O1	0.24363 (4)	0.3883 (2)	0.69236 (12)	0.0193 (2)
N1	0.26407 (5)	0.3076 (3)	0.46986 (16)	0.0157 (3)
H1	0.2560 (9)	0.237 (4)	0.398 (3)	0.016 (5)*
C1	0.18920 (6)	0.1230 (3)	0.54513 (17)	0.0142 (3)
C2	0.18758 (6)	−0.0863 (3)	0.45547 (18)	0.0171 (3)
H2	0.216067	−0.130500	0.409616	0.021*
C3	0.14448 (7)	−0.2303 (3)	0.4330 (2)	0.0193 (3)
H3	0.143773	−0.373905	0.372880	0.023*
C4	0.10220 (6)	−0.1652 (3)	0.49835 (19)	0.0191 (3)
H4	0.072506	−0.261738	0.481700	0.023*
C5	0.10411 (6)	0.0429 (3)	0.58816 (17)	0.0164 (3)
C6	0.14731 (6)	0.1862 (3)	0.61310 (17)	0.0157 (3)
H6	0.148330	0.326109	0.675953	0.019*
C7	0.23459 (6)	0.2842 (3)	0.57640 (18)	0.0144 (3)
C8	0.31084 (6)	0.4336 (3)	0.48033 (17)	0.0152 (3)
C9	0.34800 (6)	0.3315 (3)	0.40522 (18)	0.0163 (3)
H9	0.341653	0.185348	0.348215	0.020*
C10	0.39445 (6)	0.4477 (3)	0.41532 (18)	0.0176 (3)
C11	0.40422 (6)	0.6656 (3)	0.49535 (19)	0.0204 (3)
H11	0.436093	0.743424	0.501065	0.025*
C12	0.36638 (7)	0.7666 (3)	0.5666 (2)	0.0210 (4)
H12	0.372465	0.916679	0.620486	0.025*
C13	0.31974 (6)	0.6529 (3)	0.56090 (18)	0.0185 (3)
H13	0.294300	0.723322	0.611030	0.022*
C14	0.05874 (6)	0.1215 (4)	0.65816 (19)	0.0197 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.01301 (6)	0.02980 (7)	0.02599 (8)	0.00099 (4)	0.00678 (4)	0.00337 (4)
F1	0.0381 (7)	0.0445 (8)	0.0657 (10)	−0.0206 (6)	0.0350 (7)	−0.0164 (7)
F2	0.0288 (7)	0.0630 (9)	0.0380 (8)	0.0237 (6)	0.0149 (6)	0.0207 (7)
F3	0.0210 (6)	0.0652 (9)	0.0227 (6)	0.0063 (6)	0.0042 (5)	−0.0149 (6)
O1	0.0198 (6)	0.0267 (6)	0.0117 (6)	−0.0031 (5)	0.0024 (4)	−0.0013 (5)
N1	0.0141 (6)	0.0224 (7)	0.0110 (7)	−0.0036 (5)	0.0037 (5)	−0.0021 (5)
C1	0.0138 (7)	0.0170 (7)	0.0120 (7)	−0.0005 (6)	0.0016 (5)	0.0030 (6)
C2	0.0163 (7)	0.0203 (8)	0.0153 (8)	0.0019 (6)	0.0048 (6)	0.0018 (6)
C3	0.0214 (9)	0.0189 (8)	0.0178 (9)	−0.0011 (6)	0.0036 (7)	−0.0022 (6)
C4	0.0181 (8)	0.0212 (8)	0.0181 (8)	−0.0040 (6)	0.0026 (6)	0.0004 (6)
C5	0.0149 (7)	0.0213 (8)	0.0135 (8)	−0.0002 (6)	0.0035 (6)	0.0028 (6)
C6	0.0163 (7)	0.0180 (8)	0.0131 (8)	−0.0005 (6)	0.0032 (6)	0.0013 (6)
C7	0.0116 (7)	0.0190 (7)	0.0127 (7)	0.0014 (6)	0.0022 (6)	0.0026 (6)
C8	0.0135 (7)	0.0193 (7)	0.0129 (7)	−0.0014 (6)	0.0020 (6)	0.0028 (6)
C9	0.0146 (7)	0.0193 (8)	0.0153 (8)	−0.0017 (6)	0.0022 (6)	0.0009 (6)
C10	0.0129 (7)	0.0226 (8)	0.0175 (8)	0.0005 (6)	0.0028 (6)	0.0048 (6)
C11	0.0156 (8)	0.0242 (9)	0.0209 (9)	−0.0045 (6)	−0.0007 (6)	0.0047 (7)
C12	0.0217 (9)	0.0198 (8)	0.0212 (9)	−0.0038 (6)	−0.0002 (7)	−0.0006 (6)
C13	0.0180 (8)	0.0210 (8)	0.0169 (8)	0.0000 (6)	0.0031 (6)	0.0002 (6)
C14	0.0127 (7)	0.0293 (9)	0.0175 (8)	−0.0038 (7)	0.0035 (6)	0.0025 (7)

Geometric parameters (Å, º)

I1—C10	2.1045 (17)	C4—C5	1.391 (2)
F1—C14	1.329 (2)	C4—H4	0.9500
F2—C14	1.329 (2)	C5—C6	1.390 (2)
F3—C14	1.330 (2)	C5—C14	1.509 (2)
O1—C7	1.235 (2)	C6—H6	0.9500
N1—C7	1.355 (2)	C8—C9	1.396 (2)
N1—C8	1.422 (2)	C8—C13	1.398 (2)
N1—H1	0.79 (3)	C9—C10	1.390 (2)
C1—C2	1.395 (2)	C9—H9	0.9500
C1—C6	1.397 (2)	C10—C11	1.392 (3)
C1—C7	1.497 (2)	C11—C12	1.388 (3)
C2—C3	1.388 (2)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.391 (2)
C3—C4	1.395 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.02 (15)	C9—C8—C13	120.55 (15)
C7—N1—H1	118.2 (17)	C9—C8—N1	117.43 (15)
C8—N1—H1	116.6 (17)	C13—C8—N1	122.01 (15)
C2—C1—C6	119.66 (15)	C10—C9—C8	118.83 (16)
C2—C1—C7	123.23 (14)	C10—C9—H9	120.6
C6—C1—C7	117.09 (15)	C8—C9—H9	120.6
C3—C2—C1	120.24 (15)	C9—C10—C11	121.59 (16)
C3—C2—H2	119.9	C9—C10—I1	118.94 (13)
C1—C2—H2	119.9	C11—C10—I1	119.43 (12)
C2—C3—C4	120.37 (16)	C12—C11—C10	118.53 (16)
C2—C3—H3	119.8	C12—C11—H11	120.7
C4—C3—H3	119.8	C10—C11—H11	120.7
C5—C4—C3	119.13 (16)	C11—C12—C13	121.42 (17)
C5—C4—H4	120.4	C11—C12—H12	119.3
C3—C4—H4	120.4	C13—C12—H12	119.3
C6—C5—C4	121.00 (15)	C12—C13—C8	119.05 (16)
C6—C5—C14	118.52 (15)	C12—C13—H13	120.5
C4—C5—C14	120.46 (15)	C8—C13—H13	120.5
C5—C6—C1	119.58 (15)	F2—C14—F1	106.39 (16)
C5—C6—H6	120.2	F2—C14—F3	107.31 (17)
C1—C6—H6	120.2	F1—C14—F3	106.73 (15)
O1—C7—N1	123.27 (15)	F2—C14—C5	112.01 (14)
O1—C7—C1	121.05 (15)	F1—C14—C5	112.25 (16)
N1—C7—C1	115.68 (15)	F3—C14—C5	111.80 (14)
C6—C1—C2—C3	0.4 (2)	C7—N1—C8—C13	−36.7 (2)
C7—C1—C2—C3	178.86 (15)	C13—C8—C9—C10	1.9 (2)
C1—C2—C3—C4	0.9 (3)	N1—C8—C9—C10	−178.84 (15)
C2—C3—C4—C5	−1.2 (3)	C8—C9—C10—C11	−1.6 (3)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—I1	176.05 (12)
C3—C4—C5—C14	178.76 (16)	C9—C10—C11—C12	0.2 (3)
C4—C5—C6—C1	1.1 (2)	I1—C10—C11—C12	−177.41 (13)
C14—C5—C6—C1	−177.50 (15)	C10—C11—C12—C13	0.9 (3)
C2—C1—C6—C5	−1.4 (2)	C11—C12—C13—C8	−0.6 (3)
C7—C1—C6—C5	−179.92 (14)	C9—C8—C13—C12	−0.8 (3)
C8—N1—C7—O1	5.9 (3)	N1—C8—C13—C12	179.97 (16)
C8—N1—C7—C1	−174.53 (15)	C6—C5—C14—F2	80.4 (2)
C2—C1—C7—O1	−148.05 (17)	C4—C5—C14—F2	−98.2 (2)
C6—C1—C7—O1	30.4 (2)	C6—C5—C14—F1	−159.96 (16)
C2—C1—C7—N1	32.4 (2)	C4—C5—C14—F1	21.4 (2)
C6—C1—C7—N1	−149.19 (15)	C6—C5—C14—F3	−40.1 (2)
C7—N1—C8—C9	144.00 (17)	C4—C5—C14—F3	141.33 (17)

(PI34)

Crystal data

C14H9F3INO	F(000) = 376
Mr = 391.12	Dx = 1.994 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 4.9085 (3) Å	Cell parameters from 7377 reflections
b = 4.9644 (3) Å	θ = 3.1–29.9°
c = 26.7593 (16) Å	µ = 2.49 mm^−1
β = 92.549 (2)°	T = 101 K
V = 651.42 (7) Å^3	Rod
Z = 2	0.40 × 0.40 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	3117 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan SADABS 2014/4	θmax = 29.1°, θmin = 3.1°
Tmin = 0.512, Tmax = 0.722	h = −6→6
8008 measured reflections	k = −5→6
3193 independent reflections	l = −36→31

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.021	w = 1/[σ^2(Fo^2) + (0.0305P)^2 + 0.018P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.053	(Δ/σ)max = 0.003
S = 1.03	Δρmax = 0.50 e Å^−3
3193 reflections	Δρmin = −0.67 e Å^−3
185 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 0.01 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.63751 (3)	0.75230 (9)	0.95250 (2)	0.02168 (7)
F1	−0.4677 (4)	0.6775 (4)	0.57279 (8)	0.0257 (5)
F2	−0.3717 (4)	0.3034 (4)	0.53653 (8)	0.0266 (5)
F3	−0.1120 (4)	0.6483 (5)	0.52859 (8)	0.0274 (5)
O1	0.5041 (5)	−0.0323 (5)	0.73690 (10)	0.0229 (5)
N1	0.5230 (5)	0.4052 (5)	0.76155 (10)	0.0130 (5)
H1	0.490 (7)	0.576 (10)	0.7499 (18)	0.016*
C1	0.2496 (5)	0.2868 (8)	0.68784 (11)	0.0142 (6)
C2	0.0657 (5)	0.4994 (6)	0.69202 (12)	0.0143 (6)
H2	0.057601	0.595558	0.722619	0.017*
C3	−0.1062 (5)	0.5704 (7)	0.65121 (12)	0.0156 (6)
H3	−0.232208	0.714284	0.653924	0.019*
C4	−0.0918 (5)	0.4299 (6)	0.60681 (12)	0.0146 (6)
C5	0.0883 (5)	0.2160 (8)	0.60247 (12)	0.0172 (7)
H5	0.095989	0.119750	0.571879	0.021*
C6	0.2569 (6)	0.1446 (7)	0.64344 (13)	0.0171 (6)
H6	0.378448	−0.003211	0.640931	0.021*
C7	0.4382 (5)	0.2042 (6)	0.73091 (11)	0.0144 (7)
C8	0.6813 (5)	0.3744 (6)	0.80672 (11)	0.0131 (5)
C9	0.6155 (6)	0.5411 (6)	0.84653 (12)	0.0145 (5)
H9	0.472031	0.668747	0.842468	0.017*
C10	0.7607 (6)	0.5193 (6)	0.89193 (13)	0.0165 (6)
C11	0.9759 (6)	0.3377 (7)	0.89816 (13)	0.0189 (6)
H11	1.076677	0.325463	0.929216	0.023*
C12	1.0403 (6)	0.1756 (7)	0.85832 (14)	0.0213 (7)
H12	1.187415	0.051972	0.862190	0.026*
C13	0.8935 (5)	0.1902 (6)	0.81267 (12)	0.0162 (7)
H13	0.937988	0.075304	0.785830	0.019*
C14	−0.2620 (6)	0.5137 (7)	0.56129 (12)	0.0173 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.03010 (11)	0.02252 (12)	0.01244 (10)	−0.00481 (10)	0.00111 (6)	−0.00242 (10)
F1	0.0226 (8)	0.0323 (14)	0.0216 (11)	0.0121 (7)	−0.0059 (7)	−0.0023 (8)
F2	0.0262 (8)	0.0291 (16)	0.0236 (10)	−0.0012 (8)	−0.0094 (7)	−0.0070 (9)
F3	0.0272 (9)	0.0373 (12)	0.0174 (10)	−0.0030 (8)	−0.0015 (7)	0.0101 (9)
O1	0.0315 (12)	0.0086 (12)	0.0274 (15)	0.0007 (9)	−0.0110 (10)	0.0015 (10)
N1	0.0170 (10)	0.0088 (12)	0.0128 (12)	0.0017 (9)	−0.0030 (9)	0.0019 (10)
C1	0.0137 (9)	0.0133 (19)	0.0155 (12)	−0.0022 (11)	−0.0003 (8)	0.0005 (12)
C2	0.0146 (11)	0.0157 (15)	0.0124 (14)	0.0003 (10)	−0.0003 (10)	−0.0035 (11)
C3	0.0139 (11)	0.0165 (14)	0.0163 (15)	0.0027 (10)	−0.0011 (10)	−0.0001 (11)
C4	0.0126 (11)	0.0153 (14)	0.0158 (15)	−0.0022 (10)	−0.0002 (10)	0.0013 (11)
C5	0.0198 (11)	0.018 (2)	0.0138 (12)	0.0023 (12)	0.0000 (9)	−0.0048 (12)
C6	0.0184 (12)	0.0143 (14)	0.0185 (16)	0.0028 (10)	−0.0014 (11)	−0.0025 (12)
C7	0.0157 (10)	0.013 (2)	0.0143 (13)	−0.0014 (9)	0.0004 (9)	0.0015 (10)
C8	0.0150 (12)	0.0119 (13)	0.0123 (14)	−0.0032 (10)	0.0000 (10)	0.0038 (11)
C9	0.0168 (12)	0.0123 (14)	0.0141 (14)	0.0003 (10)	−0.0017 (10)	0.0012 (10)
C10	0.0210 (13)	0.0150 (15)	0.0133 (14)	−0.0038 (11)	−0.0004 (10)	0.0010 (11)
C11	0.0198 (12)	0.0203 (16)	0.0161 (15)	−0.0013 (10)	−0.0039 (11)	0.0054 (11)
C12	0.0188 (12)	0.0186 (17)	0.0262 (17)	0.0010 (10)	−0.0026 (12)	0.0036 (12)
C13	0.0162 (11)	0.0159 (19)	0.0167 (14)	0.0014 (9)	0.0017 (10)	0.0005 (10)
C14	0.0179 (12)	0.0201 (16)	0.0137 (15)	0.0006 (11)	−0.0016 (11)	−0.0002 (12)

Geometric parameters (Å, º)

I1—C10	2.102 (3)	C4—C5	1.390 (4)
F1—C14	1.343 (4)	C4—C14	1.505 (4)
F2—C14	1.337 (4)	C5—C6	1.390 (4)
F3—C14	1.346 (4)	C5—H5	0.9500
O1—C7	1.227 (4)	C6—H6	0.9500
N1—C7	1.346 (4)	C8—C13	1.390 (4)
N1—C8	1.416 (4)	C8—C9	1.398 (4)
N1—H1	0.92 (5)	C9—C10	1.385 (4)
C1—C6	1.384 (5)	C9—H9	0.9500
C1—C2	1.396 (4)	C10—C11	1.393 (4)
C1—C7	1.503 (4)	C11—C12	1.384 (5)
C2—C3	1.395 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.392 (5)
C3—C4	1.382 (5)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.7 (2)	C13—C8—C9	120.0 (3)
C7—N1—H1	116 (3)	C13—C8—N1	123.3 (3)
C8—N1—H1	118 (3)	C9—C8—N1	116.7 (3)
C6—C1—C2	119.7 (3)	C10—C9—C8	119.6 (3)
C6—C1—C7	118.7 (3)	C10—C9—H9	120.2
C2—C1—C7	121.5 (3)	C8—C9—H9	120.2
C3—C2—C1	119.9 (3)	C9—C10—C11	120.9 (3)
C3—C2—H2	120.1	C9—C10—I1	118.6 (2)
C1—C2—H2	120.1	C11—C10—I1	120.4 (2)
C4—C3—C2	119.6 (3)	C12—C11—C10	118.8 (3)
C4—C3—H3	120.2	C12—C11—H11	120.6
C2—C3—H3	120.2	C10—C11—H11	120.6
C3—C4—C5	120.9 (3)	C11—C12—C13	121.3 (3)
C3—C4—C14	120.6 (3)	C11—C12—H12	119.4
C5—C4—C14	118.4 (3)	C13—C12—H12	119.4
C4—C5—C6	119.2 (3)	C8—C13—C12	119.4 (3)
C4—C5—H5	120.4	C8—C13—H13	120.3
C6—C5—H5	120.4	C12—C13—H13	120.3
C1—C6—C5	120.6 (3)	F2—C14—F1	107.2 (2)
C1—C6—H6	119.7	F2—C14—F3	106.6 (3)
C5—C6—H6	119.7	F1—C14—F3	106.7 (3)
O1—C7—N1	123.9 (3)	F2—C14—C4	112.5 (3)
O1—C7—C1	120.8 (3)	F1—C14—C4	112.2 (3)
N1—C7—C1	115.3 (3)	F3—C14—C4	111.3 (2)
C6—C1—C2—C3	−1.1 (5)	C7—N1—C8—C9	−141.2 (3)
C7—C1—C2—C3	180.0 (3)	C13—C8—C9—C10	−0.7 (4)
C1—C2—C3—C4	−0.3 (5)	N1—C8—C9—C10	179.3 (3)
C2—C3—C4—C5	1.1 (5)	C8—C9—C10—C11	1.5 (5)
C2—C3—C4—C14	−176.1 (3)	C8—C9—C10—I1	−175.5 (2)
C3—C4—C5—C6	−0.4 (5)	C9—C10—C11—C12	−1.0 (5)
C14—C4—C5—C6	176.8 (3)	I1—C10—C11—C12	176.0 (2)
C2—C1—C6—C5	1.8 (5)	C10—C11—C12—C13	−0.4 (5)
C7—C1—C6—C5	−179.3 (3)	C9—C8—C13—C12	−0.6 (4)
C4—C5—C6—C1	−1.0 (5)	N1—C8—C13—C12	179.3 (3)
C8—N1—C7—O1	−5.0 (5)	C11—C12—C13—C8	1.1 (5)
C8—N1—C7—C1	174.2 (3)	C3—C4—C14—F2	−138.0 (3)
C6—C1—C7—O1	−32.1 (4)	C5—C4—C14—F2	44.9 (4)
C2—C1—C7—O1	146.8 (3)	C3—C4—C14—F1	−17.0 (4)
C6—C1—C7—N1	148.6 (3)	C5—C4—C14—F1	165.8 (3)
C2—C1—C7—N1	−32.5 (4)	C3—C4—C14—F3	102.5 (3)
C7—N1—C8—C13	38.9 (4)	C5—C4—C14—F3	−74.7 (4)

(PI43)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.881 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.292 (3) Å	Cell parameters from 9389 reflections
b = 10.708 (2) Å	θ = 2.5–30.1°
c = 9.762 (2) Å	µ = 2.35 mm^−1
β = 96.305 (7)°	T = 101 K
V = 1381.1 (5) Å^3	Rod
Z = 4	0.16 × 0.14 × 0.06 mm

Data collection

Bruker APEX-II CCD diffractometer	3447 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan SADABS 2014/4	θmax = 30.1°, θmin = 2.8°
Tmin = 0.612, Tmax = 0.782	h = −18→13
17090 measured reflections	k = −14→13
4036 independent reflections	l = −13→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 1.4462P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4036 reflections	Δρmax = 0.95 e Å^−3
185 parameters	Δρmin = −0.68 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.02275 (2)	−0.33427 (2)	0.05393 (2)	0.02088 (6)
F1	0.53532 (18)	0.6643 (2)	−0.2166 (3)	0.0700 (7)
F2	0.52485 (17)	0.49003 (19)	−0.3122 (2)	0.0607 (6)
F3	0.41782 (17)	0.6298 (3)	−0.3769 (3)	0.0926 (10)
O1	0.24345 (13)	0.20035 (14)	−0.21181 (15)	0.0189 (3)
N1	0.23505 (15)	0.18807 (16)	0.01907 (18)	0.0149 (3)
H1	0.242 (2)	0.225 (3)	0.096 (3)	0.020 (7)*
C1	0.29753 (16)	0.3778 (2)	−0.0781 (2)	0.0149 (4)
C2	0.27060 (19)	0.4600 (2)	0.0222 (2)	0.0200 (4)
H2	0.226129	0.433333	0.086214	0.024*
C3	0.3087 (2)	0.5811 (2)	0.0288 (3)	0.0263 (5)
H3	0.290102	0.637056	0.097133	0.032*
C4	0.3741 (2)	0.6203 (2)	−0.0645 (3)	0.0264 (5)
H4	0.400333	0.702880	−0.059928	0.032*
C5	0.40082 (18)	0.5377 (2)	−0.1645 (2)	0.0209 (5)
C6	0.36256 (17)	0.4176 (2)	−0.1721 (2)	0.0172 (4)
H6	0.380578	0.362089	−0.241316	0.021*
C7	0.25622 (16)	0.24768 (19)	−0.0961 (2)	0.0140 (4)
C8	0.18883 (16)	0.06846 (19)	0.0231 (2)	0.0144 (4)
C9	0.12665 (17)	0.0464 (2)	0.1266 (2)	0.0166 (4)
H9	0.115497	0.111088	0.189809	0.020*
C10	0.08085 (17)	−0.0691 (2)	0.1382 (2)	0.0178 (4)
H10	0.039409	−0.084426	0.209755	0.021*
C11	0.09676 (17)	−0.16159 (19)	0.0435 (2)	0.0164 (4)
C12	0.15895 (18)	−0.1414 (2)	−0.0592 (2)	0.0180 (4)
H12	0.169637	−0.206288	−0.122430	0.022*
C13	0.20577 (17)	−0.02622 (19)	−0.0698 (2)	0.0171 (4)
H13	0.248929	−0.012146	−0.139588	0.021*
C14	0.4682 (2)	0.5797 (3)	−0.2685 (3)	0.0321 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02406 (9)	0.01396 (8)	0.02540 (9)	−0.00505 (5)	0.00626 (6)	−0.00014 (5)
F1	0.0547 (14)	0.0639 (15)	0.0956 (18)	−0.0396 (11)	0.0272 (13)	−0.0077 (12)
F2	0.0681 (14)	0.0498 (12)	0.0729 (14)	−0.0002 (10)	0.0473 (11)	0.0123 (11)
F3	0.0425 (12)	0.162 (3)	0.0742 (16)	0.0050 (15)	0.0115 (11)	0.0925 (18)
O1	0.0304 (9)	0.0148 (7)	0.0120 (7)	−0.0015 (6)	0.0044 (6)	−0.0003 (6)
N1	0.0219 (9)	0.0121 (8)	0.0112 (8)	−0.0012 (7)	0.0035 (7)	−0.0016 (6)
C1	0.0169 (10)	0.0126 (9)	0.0146 (9)	0.0004 (8)	−0.0007 (8)	0.0021 (7)
C2	0.0280 (12)	0.0142 (10)	0.0179 (10)	−0.0001 (8)	0.0032 (9)	0.0024 (8)
C3	0.0409 (15)	0.0139 (10)	0.0238 (11)	−0.0001 (10)	0.0022 (10)	−0.0026 (9)
C4	0.0324 (14)	0.0140 (10)	0.0311 (13)	−0.0068 (10)	−0.0042 (10)	0.0030 (9)
C5	0.0190 (11)	0.0190 (10)	0.0239 (11)	−0.0039 (8)	−0.0012 (9)	0.0076 (9)
C6	0.0168 (10)	0.0157 (9)	0.0188 (10)	0.0008 (8)	0.0007 (8)	0.0021 (8)
C7	0.0154 (10)	0.0125 (9)	0.0142 (9)	0.0020 (7)	0.0029 (7)	0.0015 (7)
C8	0.0174 (10)	0.0122 (9)	0.0136 (9)	0.0000 (7)	0.0016 (8)	0.0020 (7)
C9	0.0204 (11)	0.0164 (10)	0.0134 (9)	−0.0010 (8)	0.0039 (8)	−0.0016 (8)
C10	0.0209 (11)	0.0175 (10)	0.0156 (10)	−0.0014 (8)	0.0046 (8)	0.0011 (8)
C11	0.0195 (10)	0.0114 (9)	0.0182 (10)	−0.0014 (8)	0.0010 (8)	0.0012 (8)
C12	0.0243 (11)	0.0126 (9)	0.0174 (10)	0.0009 (8)	0.0037 (9)	−0.0008 (8)
C13	0.0232 (11)	0.0145 (10)	0.0144 (9)	0.0005 (8)	0.0052 (8)	0.0012 (7)
C14	0.0258 (13)	0.0300 (13)	0.0413 (15)	−0.0072 (11)	0.0076 (11)	0.0128 (12)

Geometric parameters (Å, º)

I1—C11	2.102 (2)	C4—C5	1.392 (4)
F1—C14	1.331 (3)	C4—H4	0.9500
F2—C14	1.320 (4)	C5—C6	1.383 (3)
F3—C14	1.304 (3)	C5—C14	1.495 (3)
O1—C7	1.232 (3)	C6—H6	0.9500
N1—C7	1.350 (3)	C8—C9	1.394 (3)
N1—C8	1.423 (3)	C8—C13	1.394 (3)
N1—H1	0.85 (3)	C9—C10	1.388 (3)
C1—C2	1.393 (3)	C9—H9	0.9500
C1—C6	1.394 (3)	C10—C11	1.388 (3)
C1—C7	1.501 (3)	C10—H10	0.9500
C2—C3	1.391 (3)	C11—C12	1.384 (3)
C2—H2	0.9500	C12—C13	1.391 (3)
C3—C4	1.390 (4)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.36 (18)	C9—C8—C13	119.92 (19)
C7—N1—H1	120.4 (19)	C9—C8—N1	117.67 (19)
C8—N1—H1	113.8 (19)	C13—C8—N1	122.39 (19)
C2—C1—C6	119.7 (2)	C10—C9—C8	120.7 (2)
C2—C1—C7	123.4 (2)	C10—C9—H9	119.7
C6—C1—C7	116.87 (19)	C8—C9—H9	119.7
C3—C2—C1	120.1 (2)	C11—C10—C9	118.8 (2)
C3—C2—H2	120.0	C11—C10—H10	120.6
C1—C2—H2	120.0	C9—C10—H10	120.6
C4—C3—C2	120.1 (2)	C12—C11—C10	121.22 (19)
C4—C3—H3	119.9	C12—C11—I1	119.48 (15)
C2—C3—H3	119.9	C10—C11—I1	119.29 (16)
C3—C4—C5	119.6 (2)	C11—C12—C13	120.0 (2)
C3—C4—H4	120.2	C11—C12—H12	120.0
C5—C4—H4	120.2	C13—C12—H12	120.0
C6—C5—C4	120.5 (2)	C12—C13—C8	119.4 (2)
C6—C5—C14	119.2 (2)	C12—C13—H13	120.3
C4—C5—C14	120.2 (2)	C8—C13—H13	120.3
C5—C6—C1	120.0 (2)	F3—C14—F2	107.3 (3)
C5—C6—H6	120.0	F3—C14—F1	107.0 (3)
C1—C6—H6	120.0	F2—C14—F1	103.6 (2)
O1—C7—N1	123.3 (2)	F3—C14—C5	112.5 (2)
O1—C7—C1	120.06 (18)	F2—C14—C5	113.9 (2)
N1—C7—C1	116.65 (18)	F1—C14—C5	111.9 (2)
C6—C1—C2—C3	−0.2 (3)	C7—N1—C8—C13	34.0 (3)
C7—C1—C2—C3	−177.2 (2)	C13—C8—C9—C10	−0.2 (3)
C1—C2—C3—C4	−0.2 (4)	N1—C8—C9—C10	−178.7 (2)
C2—C3—C4—C5	0.2 (4)	C8—C9—C10—C11	−1.1 (3)
C3—C4—C5—C6	0.3 (4)	C9—C10—C11—C12	1.6 (3)
C3—C4—C5—C14	177.9 (2)	C9—C10—C11—I1	−177.22 (16)
C4—C5—C6—C1	−0.7 (3)	C10—C11—C12—C13	−0.8 (3)
C14—C5—C6—C1	−178.4 (2)	I1—C11—C12—C13	177.99 (17)
C2—C1—C6—C5	0.7 (3)	C11—C12—C13—C8	−0.5 (3)
C7—C1—C6—C5	177.85 (19)	C9—C8—C13—C12	1.0 (3)
C8—N1—C7—O1	−5.0 (3)	N1—C8—C13—C12	179.4 (2)
C8—N1—C7—C1	175.24 (19)	C6—C5—C14—F3	90.0 (3)
C2—C1—C7—O1	147.4 (2)	C4—C5—C14—F3	−87.7 (3)
C6—C1—C7—O1	−29.7 (3)	C6—C5—C14—F2	−32.4 (3)
C2—C1—C7—N1	−32.8 (3)	C4—C5—C14—F2	149.9 (3)
C6—C1—C7—N1	150.1 (2)	C6—C5—C14—F1	−149.6 (2)
C7—N1—C8—C9	−147.6 (2)	C4—C5—C14—F1	32.8 (3)

(PI44)

Crystal data

C14H9F3INO	F(000) = 752
Mr = 391.12	Dx = 1.944 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7689 (14) Å	Cell parameters from 9953 reflections
b = 5.2518 (5) Å	θ = 2.4–30.0°
c = 17.2537 (17) Å	µ = 2.43 mm^−1
β = 93.217 (3)°	T = 107 K
V = 1336.1 (2) Å^3	Plate
Z = 4	0.45 × 0.24 × 0.08 mm

Data collection

Bruker APEX-II CCD diffractometer	2340 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.044
Absorption correction: multi-scan SADABS 2014/4	θmax = 26.7°, θmin = 2.4°
Tmin = 0.493, Tmax = 0.736	h = −18→18
15394 measured reflections	k = −6→5
2820 independent reflections	l = −21→21

Refinement

Refinement on F^2	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0206P)^2 + 12.064P] where P = (Fo^2 + 2Fc^2)/3
S = 1.20	(Δ/σ)max < 0.001
2820 reflections	Δρmax = 1.86 e Å^−3
184 parameters	Δρmin = −1.13 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
I1	0.79295 (2)	0.13136 (8)	0.79197 (2)	0.02572 (14)
F1	0.0163 (3)	0.0043 (9)	0.3785 (3)	0.0507 (11)
F2	0.0384 (3)	0.3433 (9)	0.3157 (2)	0.0491 (11)
F3	−0.0270 (2)	0.3638 (8)	0.4208 (2)	0.0409 (10)
O1	0.4110 (2)	0.6257 (7)	0.5670 (2)	0.0206 (8)
N1	0.4285 (3)	0.1977 (9)	0.5851 (3)	0.0213 (9)
H1	0.413 (4)	0.041 (5)	0.577 (4)	0.026*
C1	0.2944 (3)	0.3528 (10)	0.5130 (3)	0.0163 (10)
C2	0.2401 (4)	0.1430 (11)	0.5281 (3)	0.0213 (11)
H2	0.259449	0.022799	0.566689	0.026*
C3	0.1577 (4)	0.1110 (11)	0.4864 (3)	0.0232 (11)
H3	0.119748	−0.028851	0.497427	0.028*
C4	0.1309 (3)	0.2834 (11)	0.4285 (3)	0.0207 (11)
C5	0.1851 (4)	0.4903 (11)	0.4134 (3)	0.0224 (11)
H5	0.166203	0.608736	0.374146	0.027*
C6	0.2669 (4)	0.5256 (11)	0.4555 (3)	0.0210 (11)
H6	0.304078	0.667729	0.444976	0.025*
C7	0.3830 (3)	0.4053 (11)	0.5575 (3)	0.0179 (10)
C8	0.5120 (3)	0.2008 (11)	0.6307 (3)	0.0184 (10)
C9	0.5697 (3)	−0.0049 (10)	0.6216 (3)	0.0188 (10)
H9	0.554137	−0.133256	0.584457	0.023*
C10	0.6509 (3)	−0.0223 (10)	0.6675 (3)	0.0175 (10)
H10	0.690946	−0.161371	0.661002	0.021*
C11	0.6726 (3)	0.1623 (11)	0.7220 (3)	0.0184 (10)
C12	0.6154 (3)	0.3715 (10)	0.7309 (3)	0.0167 (10)
H12	0.631225	0.500090	0.767987	0.020*
C13	0.5349 (3)	0.3895 (10)	0.6848 (3)	0.0174 (10)
H13	0.495663	0.530969	0.690371	0.021*
C14	0.0376 (4)	0.2552 (14)	0.3811 (4)	0.0356 (16)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.02269 (19)	0.0323 (2)	0.0215 (2)	0.00182 (15)	−0.00413 (13)	0.00035 (15)
F1	0.040 (2)	0.038 (3)	0.071 (3)	−0.0045 (19)	−0.023 (2)	−0.008 (2)
F2	0.0291 (19)	0.067 (3)	0.048 (2)	−0.0057 (19)	−0.0249 (17)	0.007 (2)
F3	0.0231 (17)	0.055 (3)	0.044 (2)	0.0039 (17)	−0.0033 (15)	−0.0142 (19)
O1	0.0227 (18)	0.0115 (19)	0.0268 (19)	−0.0064 (15)	−0.0049 (15)	−0.0042 (15)
N1	0.027 (2)	0.018 (2)	0.019 (2)	0.0007 (19)	0.0007 (17)	0.0000 (18)
C1	0.015 (2)	0.021 (3)	0.014 (2)	−0.001 (2)	−0.0015 (17)	−0.0031 (19)
C2	0.022 (2)	0.022 (3)	0.020 (2)	0.005 (2)	−0.0001 (19)	0.005 (2)
C3	0.021 (2)	0.020 (3)	0.028 (3)	−0.003 (2)	0.001 (2)	0.001 (2)
C4	0.018 (2)	0.022 (3)	0.022 (2)	−0.002 (2)	−0.0018 (19)	−0.002 (2)
C5	0.028 (3)	0.021 (3)	0.019 (2)	0.003 (2)	0.001 (2)	0.004 (2)
C6	0.024 (3)	0.017 (3)	0.022 (2)	−0.003 (2)	0.002 (2)	0.000 (2)
C7	0.022 (2)	0.020 (3)	0.012 (2)	0.002 (2)	0.0019 (18)	0.0008 (19)
C8	0.020 (2)	0.021 (3)	0.015 (2)	−0.005 (2)	0.0039 (18)	0.003 (2)
C9	0.020 (2)	0.015 (3)	0.022 (2)	−0.006 (2)	−0.0002 (19)	−0.004 (2)
C10	0.019 (2)	0.015 (3)	0.018 (2)	0.001 (2)	−0.0015 (18)	0.001 (2)
C11	0.019 (2)	0.019 (3)	0.017 (2)	−0.001 (2)	−0.0001 (18)	0.004 (2)
C12	0.024 (2)	0.013 (3)	0.014 (2)	−0.002 (2)	−0.0013 (18)	−0.0014 (19)
C13	0.023 (2)	0.014 (3)	0.016 (2)	0.003 (2)	0.0031 (18)	−0.0002 (19)
C14	0.028 (3)	0.034 (4)	0.047 (4)	−0.018 (3)	0.017 (3)	−0.027 (3)

Geometric parameters (Å, º)

I1—C11	2.098 (5)	C4—C5	1.383 (8)
F1—C14	1.355 (8)	C4—C14	1.569 (8)
F2—C14	1.221 (8)	C5—C6	1.387 (7)
F3—C14	1.334 (7)	C5—H5	0.9500
O1—C7	1.237 (7)	C6—H6	0.9500
N1—C7	1.353 (7)	C8—C13	1.389 (7)
N1—C8	1.427 (7)	C8—C9	1.390 (8)
N1—H1	0.87 (2)	C9—C10	1.403 (7)
C1—C6	1.388 (7)	C9—H9	0.9500
C1—C2	1.395 (8)	C10—C11	1.375 (7)
C1—C7	1.505 (7)	C10—H10	0.9500
C2—C3	1.389 (7)	C11—C12	1.400 (7)
C2—H2	0.9500	C12—C13	1.397 (7)
C3—C4	1.390 (8)	C12—H12	0.9500
C3—H3	0.9500	C13—H13	0.9500
C7—N1—C8	125.6 (5)	C13—C8—C9	120.2 (5)
C7—N1—H1	126 (4)	C13—C8—N1	123.3 (5)
C8—N1—H1	109 (4)	C9—C8—N1	116.5 (5)
C6—C1—C2	120.1 (5)	C8—C9—C10	119.8 (5)
C6—C1—C7	117.1 (5)	C8—C9—H9	120.1
C2—C1—C7	122.8 (5)	C10—C9—H9	120.1
C3—C2—C1	119.6 (5)	C11—C10—C9	119.9 (5)
C3—C2—H2	120.2	C11—C10—H10	120.1
C1—C2—H2	120.2	C9—C10—H10	120.1
C2—C3—C4	120.0 (5)	C10—C11—C12	120.7 (5)
C2—C3—H3	120.0	C10—C11—I1	119.7 (4)
C4—C3—H3	120.0	C12—C11—I1	119.6 (4)
C5—C4—C3	120.1 (5)	C13—C12—C11	119.4 (5)
C5—C4—C14	118.5 (5)	C13—C12—H12	120.3
C3—C4—C14	121.3 (5)	C11—C12—H12	120.3
C4—C5—C6	120.2 (5)	C8—C13—C12	120.1 (5)
C4—C5—H5	119.9	C8—C13—H13	120.0
C6—C5—H5	119.9	C12—C13—H13	120.0
C5—C6—C1	119.9 (5)	F2—C14—F3	110.9 (7)
C5—C6—H6	120.1	F2—C14—F1	110.6 (5)
C1—C6—H6	120.1	F3—C14—F1	105.2 (5)
O1—C7—N1	123.5 (5)	F2—C14—C4	113.1 (5)
O1—C7—C1	120.9 (5)	F3—C14—C4	108.9 (5)
N1—C7—C1	115.6 (5)	F1—C14—C4	107.8 (6)
C6—C1—C2—C3	−1.3 (8)	C7—N1—C8—C9	−148.7 (5)
C7—C1—C2—C3	178.0 (5)	C13—C8—C9—C10	0.4 (8)
C1—C2—C3—C4	1.8 (8)	N1—C8—C9—C10	−176.6 (5)
C2—C3—C4—C5	−1.5 (8)	C8—C9—C10—C11	0.9 (8)
C2—C3—C4—C14	−179.0 (5)	C9—C10—C11—C12	−1.6 (8)
C3—C4—C5—C6	0.6 (8)	C9—C10—C11—I1	178.8 (4)
C14—C4—C5—C6	178.3 (5)	C10—C11—C12—C13	1.2 (8)
C4—C5—C6—C1	−0.1 (8)	I1—C11—C12—C13	−179.3 (4)
C2—C1—C6—C5	0.5 (8)	C9—C8—C13—C12	−0.8 (8)
C7—C1—C6—C5	−178.9 (5)	N1—C8—C13—C12	175.9 (5)
C8—N1—C7—O1	2.3 (8)	C11—C12—C13—C8	0.1 (7)
C8—N1—C7—C1	−177.9 (4)	C5—C4—C14—F2	30.8 (8)
C6—C1—C7—O1	28.9 (7)	C3—C4—C14—F2	−151.6 (6)
C2—C1—C7—O1	−150.4 (5)	C5—C4—C14—F3	−93.0 (7)
C6—C1—C7—N1	−150.8 (5)	C3—C4—C14—F3	84.6 (7)
C2—C1—C7—N1	29.8 (7)	C5—C4—C14—F1	153.4 (5)
C7—N1—C8—C13	34.5 (8)	C3—C4—C14—F1	−29.0 (7)