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In the title mol­ecule, C21H19ClF3NO2, the 5-chloro­phenyl and 4-methoxy­benzyl groups are twisted slightly with respect to the amine group [dihedral angles = −8.4 (2) and 13.6 (2)°] and with respect to each other [6.2 (7)°], forming a nearly planar arrangement. The crystal packing is stabilized by intra­molecular N—H...O hydrogen bonding between the amine H atom and the hydroxyl O atom. In addition, inter­molecular hydrogen bonding between the same amine H atom and an F atom, N—H...F, and between the meth­oxy O atom and the hydroxyl H atom, O—H...O, adds to this stability.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703749X/at2356sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680703749X/at2356Isup2.hkl
Contains datablock I

CCDC reference: 660208

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.068
  • Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found



Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.758 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.80 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.19 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT318_ALERT_2_C Check Hybridisation of N in Main Residue . ? PLAT414_ALERT_2_C Short Intra D-H..H-X H0A .. H13A .. 1.94 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.966 Tmax scaled 0.966 Tmin scaled 0.875 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 32.71 From the CIF: _reflns_number_total 6220 Count of symmetry unique reflns 3880 Completeness (_total/calc) 160.31% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2340 Fraction of Friedel pairs measured 0.603 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound is an intermediate in the preparation of efavirenz, an anti HIV drug. Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regime to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission. Efavirenz was approved by the Food and Drug Administration (FDA) in 1998, making it the 14t h approved antiretroviral drug. In recent years fluorinated compounds find much importance in the pharmaceutical field. Fluorinated compounds in general, fluorinated heterocycles in particular, are those focused on much in modern-day medicinal chemistry. Incorporation of a fluorine atom instead of hydrogen one can alter the course of the reaction as well as its biological activities. Further introduction of a fluorine atom as the CF3 group provides a more lipophilically and pharmacologically interesting compound compared to their non fluorinated analogues. The trifluoromethyl substituted compounds have been reported to possess biological activities as herbicides, fungicides and inhibitors for platelet aggregation. In view of the importance of the fluro derivatives, a crystal structure of the title compound, (I), is reported.

The mean planes of the 5-chlorophenyl and 4-methoxybenzyl groups are twisted slightly with the amine group [dihedral angles: N—C7—C8—C13 = -8.4 (2)°; C7—N—C6—C5 = 13.6 (2)°] and 6.2 (7)° with each other forming a nearly planar arrangement (Fig. 1).

Intramolecular hydrogen bonding occurs between the amine hydrogen, and the hydroxyl oxygen, N—H0A···O2, of the title molecule. In addition, intermolecular hydrogen bonding between the the same amine hydrogen and a fluorine atom, N—H0A···F2, as well as between the methoxy oxygen atom and hydroxyl hydrogen atom, O2—H2B···O1, adds to crystal packing stability (Fig. 2).

Related literature top

For related structures, see: Yathirajan, Sarojini et al. (2007); Yathirajan, Sreevidya et al. (2007). For related literature, see: Whittle et al. (1994); Ren et al. (2002); Jung et al. (2002); Küçükgüzel et al. (2000).

Experimental top

A pure sample of the title compound was obtained as a gift sample from Sequent Scientific Ltd., India and was crystallized from a mixture of (1:1) ethylacetate and toluene (m.p.: 427–429 K).

Refinement top

The H atoms were included in the riding model approximation with O—H = 0.83 Å, N—H = 0.87 Å and C—H = 0.94–0.98 Å, and with Uiso(H) = 1.19–1.49Ueq(C, O, N).

Structure description top

The title compound is an intermediate in the preparation of efavirenz, an anti HIV drug. Efavirenz is also used in combination with other antiretroviral agents as part of an expanded postexposure prophylaxis regime to prevent HIV transmission for those exposed to materials associated with a high risk for HIV transmission. Efavirenz was approved by the Food and Drug Administration (FDA) in 1998, making it the 14t h approved antiretroviral drug. In recent years fluorinated compounds find much importance in the pharmaceutical field. Fluorinated compounds in general, fluorinated heterocycles in particular, are those focused on much in modern-day medicinal chemistry. Incorporation of a fluorine atom instead of hydrogen one can alter the course of the reaction as well as its biological activities. Further introduction of a fluorine atom as the CF3 group provides a more lipophilically and pharmacologically interesting compound compared to their non fluorinated analogues. The trifluoromethyl substituted compounds have been reported to possess biological activities as herbicides, fungicides and inhibitors for platelet aggregation. In view of the importance of the fluro derivatives, a crystal structure of the title compound, (I), is reported.

The mean planes of the 5-chlorophenyl and 4-methoxybenzyl groups are twisted slightly with the amine group [dihedral angles: N—C7—C8—C13 = -8.4 (2)°; C7—N—C6—C5 = 13.6 (2)°] and 6.2 (7)° with each other forming a nearly planar arrangement (Fig. 1).

Intramolecular hydrogen bonding occurs between the amine hydrogen, and the hydroxyl oxygen, N—H0A···O2, of the title molecule. In addition, intermolecular hydrogen bonding between the the same amine hydrogen and a fluorine atom, N—H0A···F2, as well as between the methoxy oxygen atom and hydroxyl hydrogen atom, O2—H2B···O1, adds to crystal packing stability (Fig. 2).

For related structures, see: Yathirajan, Sarojini et al. (2007); Yathirajan, Sreevidya et al. (2007). For related literature, see: Whittle et al. (1994); Ren et al. (2002); Jung et al. (2002); Küçükgüzel et al. (2000).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound (I), showing atom labelling and 50% probability displacement ellipsoids. Dashed lines indicate N—H···O intramolecular hydrogen bonds.
[Figure 2] Fig. 2. Packing diagram of (I), viewed down the a axis. Dashed lines indicate O—H···O, and N—H···F intermolecular and N—H···O intramolecular hydrogen bonds.
2-{5-Chloro-2-[(4-methoxybenzyl)amino]phenyl}-4-cyclopropyl- 1,1,1-trifluorobut-3-yn-2-ol top
Crystal data top
C21H19ClF3NO2F(000) = 848
Mr = 409.82Dx = 1.450 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4798 reflections
a = 8.6400 (19) Åθ = 4.6–32.6°
b = 9.7671 (9) ŵ = 0.25 mm1
c = 22.240 (5) ÅT = 203 K
V = 1876.8 (6) Å3Plate, colourless
Z = 40.43 × 0.37 × 0.14 mm
Data collection top
Oxford Diffraction Gemini R
diffractometer
6220 independent reflections
Radiation source: fine-focus sealed tube2640 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 10.5081 pixels mm-1θmax = 32.7°, θmin = 4.8°
φ and ω scansh = 1212
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1314
Tmin = 0.906, Tmax = 1.000l = 3232
18057 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.069 w = 1/[σ2(Fo2) + (0.0312P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.76(Δ/σ)max = 0.016
6220 reflectionsΔρmax = 0.21 e Å3
254 parametersΔρmin = 0.22 e Å3
0 restraintsAbsolute structure: Flack (1983), with 3628 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
Crystal data top
C21H19ClF3NO2V = 1876.8 (6) Å3
Mr = 409.82Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.6400 (19) ŵ = 0.25 mm1
b = 9.7671 (9) ÅT = 203 K
c = 22.240 (5) Å0.43 × 0.37 × 0.14 mm
Data collection top
Oxford Diffraction Gemini R
diffractometer
6220 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2640 reflections with I > 2σ(I)
Tmin = 0.906, Tmax = 1.000Rint = 0.050
18057 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.069Δρmax = 0.21 e Å3
S = 0.76Δρmin = 0.22 e Å3
6220 reflectionsAbsolute structure: Flack (1983), with 3628 Friedel pairs
254 parametersAbsolute structure parameter: 0.02 (4)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl0.82991 (6)0.66081 (4)0.14333 (2)0.05311 (14)
F10.90703 (12)0.15349 (10)0.23407 (4)0.0495 (3)
F20.85448 (12)0.01133 (9)0.16359 (4)0.0507 (3)
F31.06136 (12)0.01341 (9)0.21520 (4)0.0485 (3)
O10.89852 (13)0.45246 (10)0.11680 (5)0.0395 (3)
O21.12304 (12)0.08094 (11)0.10175 (4)0.0355 (3)
H2B1.20160.04390.11580.053*
N0.86626 (16)0.10757 (13)0.03665 (5)0.0332 (3)
H0A0.90880.04110.05680.040*
C10.94820 (17)0.26983 (14)0.11402 (6)0.0260 (3)
C20.93451 (18)0.40036 (16)0.13820 (7)0.0306 (4)
H2A0.99130.42300.17290.037*
C30.8395 (2)0.49753 (14)0.11254 (7)0.0339 (4)
C40.7563 (2)0.46620 (17)0.06224 (8)0.0398 (4)
H4A0.69190.53250.04460.048*
C50.76666 (19)0.33727 (17)0.03738 (7)0.0360 (4)
H5A0.70830.31680.00290.043*
C60.86196 (18)0.23591 (15)0.06223 (6)0.0282 (4)
C70.8037 (2)0.07891 (15)0.02165 (7)0.0364 (4)
H7A0.85170.14050.05100.044*
H7B0.69240.09810.02120.044*
C80.82856 (19)0.06668 (15)0.04160 (7)0.0306 (4)
C90.7601 (2)0.10854 (17)0.09471 (8)0.0424 (4)
H9A0.69510.04730.11530.051*
C100.7839 (2)0.23590 (17)0.11818 (8)0.0434 (4)
H10A0.73570.26140.15440.052*
C110.87869 (18)0.32664 (16)0.08862 (7)0.0311 (4)
C120.9456 (2)0.29100 (16)0.03566 (8)0.0392 (4)
H12A1.00910.35350.01500.047*
C130.9191 (2)0.16095 (17)0.01221 (7)0.0390 (4)
H13A0.96430.13700.02480.047*
C141.0172 (2)0.54038 (17)0.09373 (9)0.0514 (5)
H14A1.01990.62440.11700.077*
H14B0.99560.56170.05200.077*
H14C1.11660.49460.09660.077*
C151.05879 (17)0.16978 (15)0.14503 (6)0.0274 (3)
C160.9694 (2)0.07957 (17)0.18995 (8)0.0345 (4)
C171.18271 (19)0.23895 (15)0.17881 (7)0.0311 (4)
C181.28762 (19)0.28546 (15)0.20665 (7)0.0342 (4)
C191.4148 (2)0.34007 (18)0.24111 (8)0.0411 (4)
H19A1.42280.30490.28270.049*
C201.4705 (3)0.4811 (2)0.23272 (10)0.0676 (7)
H20A1.41820.53780.20260.081*
H20B1.50660.53080.26830.081*
C211.5639 (3)0.3671 (2)0.21144 (10)0.0727 (7)
H21A1.65860.34530.23370.087*
H21B1.57030.35230.16790.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0663 (3)0.0375 (2)0.0555 (3)0.0118 (2)0.0040 (3)0.0080 (2)
F10.0513 (6)0.0649 (6)0.0323 (5)0.0004 (6)0.0132 (5)0.0022 (5)
F20.0472 (6)0.0591 (6)0.0459 (6)0.0258 (5)0.0090 (5)0.0130 (5)
F30.0560 (6)0.0459 (5)0.0435 (6)0.0030 (5)0.0096 (5)0.0180 (5)
O10.0334 (7)0.0377 (6)0.0475 (7)0.0026 (5)0.0007 (6)0.0050 (5)
O20.0313 (7)0.0436 (6)0.0318 (6)0.0099 (5)0.0045 (6)0.0058 (5)
N0.0399 (8)0.0319 (7)0.0279 (7)0.0000 (6)0.0098 (7)0.0025 (6)
C10.0241 (8)0.0308 (8)0.0231 (8)0.0018 (7)0.0014 (7)0.0032 (7)
C20.0271 (8)0.0395 (9)0.0253 (8)0.0024 (7)0.0023 (8)0.0011 (7)
C30.0369 (9)0.0301 (8)0.0346 (9)0.0007 (8)0.0026 (9)0.0014 (7)
C40.0395 (10)0.0391 (10)0.0408 (10)0.0071 (8)0.0050 (9)0.0071 (8)
C50.0354 (9)0.0442 (10)0.0283 (8)0.0001 (9)0.0076 (8)0.0031 (8)
C60.0253 (9)0.0327 (9)0.0267 (8)0.0027 (7)0.0000 (8)0.0040 (7)
C70.0432 (11)0.0394 (9)0.0267 (9)0.0005 (8)0.0059 (8)0.0035 (7)
C80.0297 (9)0.0359 (9)0.0263 (8)0.0044 (8)0.0014 (8)0.0011 (7)
C90.0461 (11)0.0441 (10)0.0370 (10)0.0112 (8)0.0180 (9)0.0045 (8)
C100.0467 (11)0.0488 (11)0.0347 (10)0.0033 (9)0.0119 (9)0.0059 (9)
C110.0258 (9)0.0333 (9)0.0342 (9)0.0062 (8)0.0019 (8)0.0013 (8)
C120.0432 (11)0.0382 (10)0.0361 (10)0.0038 (8)0.0113 (9)0.0066 (8)
C130.0497 (11)0.0368 (9)0.0306 (9)0.0082 (9)0.0137 (9)0.0004 (8)
C140.0415 (11)0.0500 (11)0.0628 (13)0.0093 (9)0.0033 (10)0.0051 (10)
C150.0267 (8)0.0306 (7)0.0248 (8)0.0001 (8)0.0003 (8)0.0030 (7)
C160.0368 (10)0.0356 (9)0.0312 (9)0.0032 (9)0.0025 (9)0.0044 (8)
C170.0275 (9)0.0320 (8)0.0337 (9)0.0003 (8)0.0023 (8)0.0037 (7)
C180.0304 (10)0.0337 (9)0.0386 (10)0.0016 (8)0.0010 (8)0.0005 (7)
C190.0359 (10)0.0465 (10)0.0408 (10)0.0044 (9)0.0069 (9)0.0017 (9)
C200.0816 (17)0.0393 (11)0.0818 (15)0.0179 (12)0.0386 (14)0.0011 (11)
C210.0464 (12)0.0994 (18)0.0723 (15)0.0318 (13)0.0111 (13)0.0185 (13)
Geometric parameters (Å, º) top
Cl—C31.7375 (15)C8—C91.383 (2)
F1—C161.3321 (18)C9—C101.365 (2)
F2—C161.3317 (19)C9—H9A0.9400
F3—C161.3311 (18)C10—C111.374 (2)
O1—C111.3901 (18)C10—H10A0.9400
O1—C141.4327 (19)C11—C121.357 (2)
O2—C151.4097 (16)C12—C131.392 (2)
O2—H2B0.8300C12—H12A0.9400
N—C61.3771 (18)C13—H13A0.9400
N—C71.4323 (18)C14—H14A0.9700
N—H0A0.8700C14—H14B0.9700
C1—C21.389 (2)C14—H14C0.9700
C1—C61.411 (2)C15—C171.472 (2)
C1—C151.531 (2)C15—C161.540 (2)
C2—C31.379 (2)C17—C181.188 (2)
C2—H2A0.9400C18—C191.442 (2)
C3—C41.365 (2)C19—C201.471 (3)
C4—C51.378 (2)C19—C211.471 (3)
C4—H4A0.9400C19—H19A0.9900
C5—C61.401 (2)C20—C211.454 (3)
C5—H5A0.9400C20—H20A0.9800
C7—C81.505 (2)C20—H20B0.9800
C7—H7A0.9800C21—H21A0.9800
C7—H7B0.9800C21—H21B0.9800
C8—C131.373 (2)
C11—O1—C14117.17 (13)C13—C12—H12A120.4
C15—O2—H2B109.5C8—C13—C12121.81 (15)
C6—N—C7122.80 (12)C8—C13—H13A119.1
C6—N—H0A118.6C12—C13—H13A119.1
C7—N—H0A118.6O1—C14—H14A109.5
C2—C1—C6119.12 (14)O1—C14—H14B109.5
C2—C1—C15117.70 (13)H14A—C14—H14B109.5
C6—C1—C15123.18 (13)O1—C14—H14C109.5
C3—C2—C1121.49 (14)H14A—C14—H14C109.5
C3—C2—H2A119.3H14B—C14—H14C109.5
C1—C2—H2A119.3O2—C15—C17110.16 (12)
C4—C3—C2119.92 (14)O2—C15—C1109.34 (11)
C4—C3—Cl120.25 (13)C17—C15—C1113.01 (12)
C2—C3—Cl119.81 (12)O2—C15—C16106.76 (12)
C3—C4—C5119.96 (15)C17—C15—C16107.23 (12)
C3—C4—H4A120.0C1—C15—C16110.14 (12)
C5—C4—H4A120.0F2—C16—F3106.82 (13)
C4—C5—C6121.71 (15)F2—C16—F1107.11 (14)
C4—C5—H5A119.1F3—C16—F1107.48 (13)
C6—C5—H5A119.1F2—C16—C15112.00 (13)
N—C6—C5119.73 (14)F3—C16—C15111.38 (14)
N—C6—C1122.46 (14)F1—C16—C15111.76 (13)
C5—C6—C1117.80 (14)C18—C17—C15175.12 (16)
N—C7—C8113.44 (13)C17—C18—C19179.06 (18)
N—C7—H7A108.9C18—C19—C20121.87 (15)
C8—C7—H7A108.9C18—C19—C21119.69 (15)
N—C7—H7B108.9C20—C19—C2159.26 (13)
C8—C7—H7B108.9C18—C19—H19A114.9
H7A—C7—H7B107.7C20—C19—H19A114.9
C13—C8—C9116.86 (14)C21—C19—H19A114.9
C13—C8—C7125.05 (15)C21—C20—C1960.39 (12)
C9—C8—C7118.05 (15)C21—C20—H20A117.7
C10—C9—C8122.13 (16)C19—C20—H20A117.7
C10—C9—H9A118.9C21—C20—H20B117.7
C8—C9—H9A118.9C19—C20—H20B117.7
C9—C10—C11119.65 (16)H20A—C20—H20B114.9
C9—C10—H10A120.2C20—C21—C1960.35 (14)
C11—C10—H10A120.2C20—C21—H21A117.7
C12—C11—C10120.23 (15)C19—C21—H21A117.7
C12—C11—O1124.44 (14)C20—C21—H21B117.7
C10—C11—O1115.33 (14)C19—C21—H21B117.7
C11—C12—C13119.28 (15)H21A—C21—H21B114.9
C11—C12—H12A120.4
C6—C1—C2—C30.4 (2)C14—O1—C11—C10168.93 (14)
C15—C1—C2—C3178.93 (13)C10—C11—C12—C131.0 (2)
C1—C2—C3—C40.0 (2)O1—C11—C12—C13178.99 (14)
C1—C2—C3—Cl178.38 (12)C9—C8—C13—C122.2 (2)
C2—C3—C4—C50.4 (2)C7—C8—C13—C12175.29 (16)
Cl—C3—C4—C5178.77 (13)C11—C12—C13—C80.9 (3)
C3—C4—C5—C60.3 (2)C2—C1—C15—O2148.07 (13)
C7—N—C6—C513.6 (2)C6—C1—C15—O231.26 (18)
C7—N—C6—C1167.77 (15)C2—C1—C15—C1724.99 (18)
C4—C5—C6—N178.61 (15)C6—C1—C15—C17154.34 (14)
C4—C5—C6—C10.1 (2)C2—C1—C15—C1694.91 (16)
C2—C1—C6—N178.20 (14)C6—C1—C15—C1685.76 (17)
C15—C1—C6—N2.5 (2)O2—C15—C16—F261.54 (16)
C2—C1—C6—C50.4 (2)C17—C15—C16—F2179.58 (13)
C15—C1—C6—C5178.89 (13)C1—C15—C16—F257.07 (17)
C6—N—C7—C8177.15 (14)O2—C15—C16—F358.03 (16)
N—C7—C8—C138.4 (2)C17—C15—C16—F360.02 (16)
N—C7—C8—C9174.05 (15)C1—C15—C16—F3176.64 (12)
C13—C8—C9—C101.8 (3)O2—C15—C16—F1178.27 (12)
C7—C8—C9—C10175.92 (16)C17—C15—C16—F160.23 (16)
C8—C9—C10—C110.0 (3)C1—C15—C16—F163.12 (16)
C9—C10—C11—C121.5 (2)C18—C19—C20—C21107.99 (19)
C9—C10—C11—O1178.54 (15)C18—C19—C21—C20111.60 (19)
C14—O1—C11—C1211.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O1i0.831.922.7114 (15)159
N—H0A···O20.872.142.6620 (17)118
N—H0A···F20.872.442.9773 (16)121
Symmetry code: (i) x+1/2, y1/2, z.

Experimental details

Crystal data
Chemical formulaC21H19ClF3NO2
Mr409.82
Crystal system, space groupOrthorhombic, P212121
Temperature (K)203
a, b, c (Å)8.6400 (19), 9.7671 (9), 22.240 (5)
V3)1876.8 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.25
Crystal size (mm)0.43 × 0.37 × 0.14
Data collection
DiffractometerOxford Diffraction Gemini R
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.906, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
18057, 6220, 2640
Rint0.050
(sin θ/λ)max1)0.760
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.069, 0.76
No. of reflections6220
No. of parameters254
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.22
Absolute structureFlack (1983), with 3628 Friedel pairs
Absolute structure parameter0.02 (4)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O1i0.831.922.7114 (15)158.6
N—H0A···O20.872.142.6620 (17)118.0
N—H0A···F20.872.442.9773 (16)120.6
Symmetry code: (i) x+1/2, y1/2, z.
 

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