(E)-3-(2-Chloro-3,3,3-trifluoro­prop-1-en­yl)-2,2-dimethyl-N,N-diphenyl­cyclo­propane­carboxamide

Yan, F.-Y.; Liu, D.-Q.

doi:10.1107/S1600536807060953

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o18

https://doi.org/10.1107/S1600536807060953

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(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N,N-diphenylcyclopropanecarboxamide

Fan-Yong Yan ^a ^* and Dong-Qing Liu ^a

^aSchool of Materials and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China
^*Correspondence e-mail: yfytju@yahoo.com

(Received 8 November 2007; accepted 20 November 2007; online 6 December 2007)

The title compound, C₂₁H₁₉ClF₃NO, was synthesized from 3-[(E)-2-chloro-3,3,3-trifluoroprop-1-enyl]-2,2-dimethylcyclopropanecarboxylic acid and diphenylamine. The propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The phenyl rings of the carboxamide are inclined at an angle of 84.6 (3)° to one another. The F atoms are disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.

Related literature

For the preparation of the title compound, see: Liu et al. (2006 ). For the insecticidal properties of related compounds, see: Punja (1981 ).

Experimental

Crystal data

C₂₁H₁₉ClF₃NO
M_r = 393.82
Monoclinic, P 2₁ /n
a = 9.247 (6) Å
b = 21.443 (14) Å
c = 10.025 (7) Å
β = 99.068 (11)°
V = 1963 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 294 (2) K
0.22 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.951, T_max = 0.960
11179 measured reflections
4030 independent reflections
2379 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.00
4030 reflections
274 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807060953/sj2421sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060953/sj2421Isup2.hkl

checkCIF report

Comment top

3-((E)-2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl cyclopropanecarboxylic acid is a very important intermediate in the preparation of tefluthrinan a useful insecticide controlling a wide range of soil insect pests in maize, sugar beet, and other crops (Punja, 1981). Diphenylamine is also a structure which has bioactivity. We reasoned that a structure containing both of these bioactive components may show enhanced insecticidal activity and prepared the title compound (I), whose structure is repoerted here Fig. 1.

The the propenyl and carboxamide substituents lie on the same side of the cyclopropane ring plane, with the two methyl substituents on either side of the plane. The benzene rings of the carboxamide are inclined at 95.4 (3)° to one another. The crystal packing of (I) is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Liu et al. (2006). For the insecticidal properties of related compounds, see: Punja (1981).

Experimental top

The title compound was prepared according to the method of Liu et al. (2006). The product was recrystallized from methanol and ethyl acetate (5:1, v/v) over 3 days at ambient temperature, giving colourless single crystals of (I).

Structure description top

For the preparation of the title compound, see: Liu et al. (2006). For the insecticidal properties of related compounds, see: Punja (1981).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids. H atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The crystal structure of (I), viewed along the a axis.

(E)-3-(2-Chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethyl-N,N- diphenylcyclopropanecarboxamide top

Crystal data top

C₂₁H₁₉ClF₃NO	F(000) = 816
M_r = 393.82	D_x = 1.333 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2995 reflections
a = 9.247 (6) Å	θ = 2.2–24.7°
b = 21.443 (14) Å	µ = 0.23 mm⁻¹
c = 10.025 (7) Å	T = 294 K
β = 99.068 (11)°	Prism, colourles
V = 1963 (2) Å³	0.22 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4030 independent reflections
Radiation source: fine-focus sealed tube	2379 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
φ and ω scans	θ_max = 26.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −11→10
T_min = 0.951, T_max = 0.960	k = −20→26
11179 measured reflections	l = −12→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0477P)² + 0.4369P] where P = (F_o² + 2F_c²)/3
4030 reflections	(Δ/σ)_max = 0.001
274 parameters	Δρ_max = 0.30 e Å⁻³
60 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₁H₁₉ClF₃NO	V = 1963 (2) Å³
M_r = 393.82	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.247 (6) Å	µ = 0.23 mm⁻¹
b = 21.443 (14) Å	T = 294 K
c = 10.025 (7) Å	0.22 × 0.20 × 0.18 mm
β = 99.068 (11)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4030 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2379 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.960	R_int = 0.034
11179 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	60 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	Δρ_max = 0.30 e Å⁻³
4030 reflections	Δρ_min = −0.32 e Å⁻³
274 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.52632 (8)	0.07861 (4)	0.13621 (8)	0.0975 (3)
F1	0.732 (2)	0.0017 (7)	0.0236 (16)	0.111 (4)	0.44 (3)
F2	0.9287 (12)	0.0254 (10)	0.1498 (12)	0.096 (3)	0.44 (3)
F3	0.823 (2)	0.0915 (7)	0.0041 (15)	0.122 (3)	0.44 (3)
F1'	0.7705 (16)	−0.0077 (4)	0.0400 (14)	0.103 (3)	0.56 (3)
F2'	0.9394 (7)	0.0532 (8)	0.1380 (10)	0.094 (2)	0.56 (3)
F3'	0.7669 (19)	0.0895 (6)	−0.0073 (10)	0.123 (3)	0.56 (3)
O1	1.00435 (15)	0.11409 (7)	0.53022 (16)	0.0659 (4)
N1	0.96418 (16)	0.19188 (7)	0.67253 (17)	0.0483 (4)
C1	0.7965 (3)	0.04904 (14)	0.0946 (3)	0.0799 (8)
C2	0.7085 (2)	0.06733 (10)	0.1994 (2)	0.0600 (6)
C3	0.7634 (2)	0.07596 (10)	0.3275 (2)	0.0560 (5)
H3	0.8630	0.0683	0.3528	0.067*
C4	0.6825 (2)	0.09642 (9)	0.4335 (2)	0.0542 (5)
H4	0.5822	0.1103	0.4003	0.065*
C5	0.7013 (2)	0.06512 (9)	0.5698 (2)	0.0535 (5)
C6	0.7573 (2)	0.13142 (9)	0.5584 (2)	0.0544 (5)
H6	0.6969	0.1637	0.5914	0.065*
C7	0.8048 (3)	0.01108 (11)	0.5998 (3)	0.0745 (7)
H7A	0.7580	−0.0264	0.5624	0.112*
H7B	0.8311	0.0065	0.6958	0.112*
H7C	0.8913	0.0186	0.5605	0.112*
C8	0.5658 (3)	0.06042 (12)	0.6365 (3)	0.0760 (7)
H8A	0.5011	0.0945	0.6071	0.114*
H8B	0.5935	0.0621	0.7328	0.114*
H8C	0.5168	0.0217	0.6117	0.114*
C9	0.9165 (2)	0.14478 (10)	0.5816 (2)	0.0522 (5)
C10	1.1194 (2)	0.19815 (9)	0.7161 (2)	0.0473 (5)
C11	1.2001 (2)	0.14777 (11)	0.7713 (2)	0.0565 (5)
H11	1.1545	0.1098	0.7811	0.068*
C12	1.3491 (3)	0.15412 (13)	0.8119 (2)	0.0683 (7)
H12	1.4040	0.1202	0.8489	0.082*
C13	1.4170 (3)	0.21036 (14)	0.7978 (3)	0.0739 (7)
H13	1.5177	0.2142	0.8236	0.089*
C14	1.3366 (3)	0.26020 (13)	0.7462 (3)	0.0740 (7)
H14	1.3822	0.2984	0.7387	0.089*
C15	1.1871 (2)	0.25455 (10)	0.7048 (2)	0.0621 (6)
H15	1.1326	0.2888	0.6693	0.074*
C16	0.8725 (2)	0.24001 (9)	0.7137 (2)	0.0444 (5)
C17	0.7857 (2)	0.27642 (9)	0.6197 (2)	0.0521 (5)
H17	0.7830	0.2689	0.5280	0.063*
C18	0.7031 (2)	0.32397 (10)	0.6614 (3)	0.0636 (6)
H18	0.6440	0.3480	0.5974	0.076*
C19	0.7068 (2)	0.33616 (11)	0.7943 (3)	0.0666 (7)
H19	0.6507	0.3684	0.8212	0.080*
C20	0.7929 (3)	0.30110 (12)	0.8887 (3)	0.0686 (7)
H20	0.7960	0.3098	0.9800	0.082*
C21	0.8759 (2)	0.25253 (11)	0.8494 (2)	0.0588 (6)
H21	0.9337	0.2284	0.9142	0.071*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0740 (4)	0.1102 (6)	0.0929 (5)	0.0004 (4)	−0.0339 (4)	0.0028 (4)
F1	0.105 (6)	0.125 (6)	0.095 (4)	−0.004 (4)	−0.010 (4)	−0.058 (5)
F2	0.079 (3)	0.134 (7)	0.074 (3)	0.000 (4)	0.005 (3)	−0.020 (5)
F3	0.135 (7)	0.135 (5)	0.104 (5)	−0.029 (5)	0.041 (5)	0.025 (4)
F1'	0.103 (5)	0.094 (3)	0.112 (5)	−0.001 (3)	0.013 (4)	−0.025 (3)
F2'	0.081 (2)	0.128 (6)	0.076 (3)	−0.022 (3)	0.0197 (18)	−0.023 (4)
F3'	0.140 (7)	0.161 (5)	0.070 (3)	−0.007 (4)	0.021 (4)	0.033 (3)
O1	0.0450 (8)	0.0741 (10)	0.0785 (11)	0.0020 (7)	0.0097 (7)	−0.0341 (9)
N1	0.0402 (8)	0.0436 (9)	0.0607 (10)	−0.0005 (7)	0.0063 (7)	−0.0123 (8)
C1	0.090 (2)	0.089 (2)	0.0554 (16)	−0.0193 (17)	−0.0049 (15)	−0.0049 (16)
C2	0.0611 (13)	0.0561 (13)	0.0569 (14)	−0.0085 (11)	−0.0086 (11)	0.0024 (11)
C3	0.0467 (11)	0.0594 (13)	0.0579 (14)	−0.0005 (10)	−0.0041 (10)	−0.0032 (11)
C4	0.0409 (10)	0.0512 (12)	0.0669 (14)	0.0016 (9)	−0.0023 (10)	−0.0055 (11)
C5	0.0501 (12)	0.0486 (12)	0.0617 (14)	−0.0026 (10)	0.0081 (10)	−0.0088 (11)
C6	0.0424 (11)	0.0460 (12)	0.0740 (15)	0.0006 (9)	0.0068 (10)	−0.0165 (10)
C7	0.0812 (17)	0.0595 (15)	0.0812 (17)	0.0102 (13)	0.0081 (13)	0.0081 (13)
C8	0.0708 (16)	0.0765 (17)	0.0849 (18)	−0.0165 (13)	0.0252 (13)	−0.0172 (14)
C9	0.0468 (11)	0.0495 (12)	0.0599 (13)	−0.0007 (10)	0.0071 (10)	−0.0109 (11)
C10	0.0410 (10)	0.0492 (12)	0.0520 (12)	0.0002 (9)	0.0080 (9)	−0.0095 (10)
C11	0.0550 (12)	0.0571 (13)	0.0557 (13)	0.0045 (11)	0.0039 (10)	−0.0044 (11)
C12	0.0585 (14)	0.0866 (18)	0.0575 (14)	0.0222 (13)	0.0017 (11)	−0.0091 (13)
C13	0.0442 (12)	0.102 (2)	0.0748 (17)	−0.0020 (14)	0.0063 (12)	−0.0263 (15)
C14	0.0519 (14)	0.0751 (17)	0.0971 (19)	−0.0140 (13)	0.0184 (13)	−0.0202 (15)
C15	0.0514 (12)	0.0518 (13)	0.0837 (16)	−0.0025 (10)	0.0128 (11)	−0.0073 (12)
C16	0.0417 (10)	0.0407 (11)	0.0521 (12)	−0.0068 (9)	0.0111 (9)	−0.0072 (9)
C17	0.0576 (12)	0.0478 (12)	0.0521 (12)	0.0015 (10)	0.0120 (10)	0.0005 (10)
C18	0.0583 (13)	0.0469 (13)	0.0854 (18)	0.0058 (11)	0.0109 (12)	0.0011 (12)
C19	0.0548 (13)	0.0531 (14)	0.097 (2)	−0.0060 (11)	0.0264 (13)	−0.0219 (14)
C20	0.0665 (15)	0.0822 (17)	0.0622 (15)	−0.0136 (14)	0.0256 (12)	−0.0277 (13)
C21	0.0568 (13)	0.0690 (15)	0.0508 (13)	−0.0025 (11)	0.0087 (10)	−0.0044 (11)

Geometric parameters (Å, º) top

Cl1—C2	1.721 (2)	C8—H8A	0.9600
F1—C1	1.324 (8)	C8—H8B	0.9600
F2—C1	1.357 (7)	C8—H8C	0.9600
F3—C1	1.334 (8)	C10—C15	1.375 (3)
F1'—C1	1.340 (7)	C10—C11	1.378 (3)
F2'—C1	1.328 (6)	C11—C12	1.381 (3)
F3'—C1	1.336 (7)	C11—H11	0.9300
O1—C9	1.221 (2)	C12—C13	1.377 (4)
N1—C9	1.385 (3)	C12—H12	0.9300
N1—C16	1.437 (2)	C13—C14	1.357 (4)
N1—C10	1.439 (2)	C13—H13	0.9300
C1—C2	1.480 (4)	C14—C15	1.385 (3)
C2—C3	1.317 (3)	C14—H14	0.9300
C3—C4	1.460 (3)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.380 (3)
C4—C5	1.508 (3)	C16—C21	1.382 (3)
C4—C6	1.529 (3)	C17—C18	1.378 (3)
C4—H4	0.9800	C17—H17	0.9300
C5—C7	1.502 (3)	C18—C19	1.353 (3)
C5—C8	1.514 (3)	C18—H18	0.9300
C5—C6	1.523 (3)	C19—C20	1.363 (3)
C6—C9	1.481 (3)	C19—H19	0.9300
C6—H6	0.9800	C20—C21	1.387 (3)
C7—H7A	0.9600	C20—H20	0.9300
C7—H7B	0.9600	C21—H21	0.9300
C7—H7C	0.9600

C9—N1—C16	124.86 (16)	C5—C8—H8A	109.5
C9—N1—C10	117.84 (16)	C5—C8—H8B	109.5
C16—N1—C10	116.81 (15)	H8A—C8—H8B	109.5
F1—C1—F3	105.7 (11)	C5—C8—H8C	109.5
F2'—C1—F3'	106.3 (6)	H8A—C8—H8C	109.5
F2'—C1—F1'	107.5 (6)	H8B—C8—H8C	109.5
F3'—C1—F1'	106.0 (8)	O1—C9—N1	120.42 (18)
F1—C1—F2	103.4 (8)	O1—C9—C6	122.70 (19)
F3—C1—F2	106.5 (7)	N1—C9—C6	116.76 (18)
F1—C1—C2	109.6 (8)	C15—C10—C11	119.9 (2)
F2'—C1—C2	112.3 (5)	C15—C10—N1	120.15 (18)
F3—C1—C2	118.7 (8)	C11—C10—N1	119.98 (18)
F3'—C1—C2	107.6 (7)	C10—C11—C12	119.6 (2)
F1'—C1—C2	116.6 (6)	C10—C11—H11	120.2
F2—C1—C2	111.7 (6)	C12—C11—H11	120.2
C3—C2—C1	124.0 (2)	C13—C12—C11	120.4 (2)
C3—C2—Cl1	122.9 (2)	C13—C12—H12	119.8
C1—C2—Cl1	113.06 (17)	C11—C12—H12	119.8
C2—C3—C4	126.0 (2)	C14—C13—C12	119.8 (2)
C2—C3—H3	117.0	C14—C13—H13	120.1
C4—C3—H3	117.0	C12—C13—H13	120.1
C3—C4—C5	121.75 (18)	C13—C14—C15	120.5 (2)
C3—C4—C6	121.70 (18)	C13—C14—H14	119.8
C5—C4—C6	60.22 (14)	C15—C14—H14	119.8
C3—C4—H4	114.2	C10—C15—C14	119.9 (2)
C5—C4—H4	114.2	C10—C15—H15	120.1
C6—C4—H4	114.2	C14—C15—H15	120.1
C7—C5—C4	120.27 (19)	C17—C16—C21	118.89 (19)
C7—C5—C8	113.9 (2)	C17—C16—N1	121.07 (18)
C4—C5—C8	116.37 (19)	C21—C16—N1	119.96 (18)
C7—C5—C6	121.44 (19)	C18—C17—C16	120.2 (2)
C4—C5—C6	60.57 (14)	C18—C17—H17	119.9
C8—C5—C6	114.21 (18)	C16—C17—H17	119.9
C9—C6—C5	120.64 (17)	C19—C18—C17	120.8 (2)
C9—C6—C4	122.29 (18)	C19—C18—H18	119.6
C5—C6—C4	59.21 (14)	C17—C18—H18	119.6
C9—C6—H6	114.5	C18—C19—C20	119.9 (2)
C5—C6—H6	114.5	C18—C19—H19	120.0
C4—C6—H6	114.5	C20—C19—H19	120.0
C5—C7—H7A	109.5	C19—C20—C21	120.4 (2)
C5—C7—H7B	109.5	C19—C20—H20	119.8
H7A—C7—H7B	109.5	C21—C20—H20	119.8
C5—C7—H7C	109.5	C16—C21—C20	119.8 (2)
H7A—C7—H7C	109.5	C16—C21—H21	120.1
H7B—C7—H7C	109.5	C20—C21—H21	120.1

F1—C1—C2—C3	131.3 (10)	C16—N1—C9—C6	−19.7 (3)
F2'—C1—C2—C3	−11.5 (9)	C10—N1—C9—C6	168.66 (18)
F3—C1—C2—C3	−107.2 (10)	C5—C6—C9—O1	47.4 (3)
F3'—C1—C2—C3	−128.0 (8)	C4—C6—C9—O1	−23.3 (3)
F1'—C1—C2—C3	113.2 (8)	C5—C6—C9—N1	−128.5 (2)
F2—C1—C2—C3	17.3 (11)	C4—C6—C9—N1	160.74 (19)
F1—C1—C2—Cl1	−50.5 (10)	C9—N1—C10—C15	126.5 (2)
F2'—C1—C2—Cl1	166.7 (8)	C16—N1—C10—C15	−45.8 (3)
F3—C1—C2—Cl1	70.9 (10)	C9—N1—C10—C11	−54.5 (3)
F3'—C1—C2—Cl1	50.2 (8)	C16—N1—C10—C11	133.2 (2)
F1'—C1—C2—Cl1	−68.6 (8)	C15—C10—C11—C12	−1.5 (3)
F2—C1—C2—Cl1	−164.5 (11)	N1—C10—C11—C12	179.52 (19)
C1—C2—C3—C4	177.4 (2)	C10—C11—C12—C13	0.2 (3)
Cl1—C2—C3—C4	−0.7 (3)	C11—C12—C13—C14	1.3 (4)
C2—C3—C4—C5	134.6 (2)	C12—C13—C14—C15	−1.4 (4)
C2—C3—C4—C6	−153.1 (2)	C11—C10—C15—C14	1.3 (3)
C3—C4—C5—C7	−0.4 (3)	N1—C10—C15—C14	−179.7 (2)
C6—C4—C5—C7	−111.4 (2)	C13—C14—C15—C10	0.2 (4)
C3—C4—C5—C8	−144.8 (2)	C9—N1—C16—C17	−53.0 (3)
C6—C4—C5—C8	104.2 (2)	C10—N1—C16—C17	118.7 (2)
C3—C4—C5—C6	111.0 (2)	C9—N1—C16—C21	130.3 (2)
C7—C5—C6—C9	−2.2 (3)	C10—N1—C16—C21	−58.1 (2)
C4—C5—C6—C9	−111.7 (2)	C21—C16—C17—C18	−0.6 (3)
C8—C5—C6—C9	140.5 (2)	N1—C16—C17—C18	−177.38 (17)
C7—C5—C6—C4	109.5 (2)	C16—C17—C18—C19	0.7 (3)
C8—C5—C6—C4	−107.8 (2)	C17—C18—C19—C20	−0.1 (3)
C3—C4—C6—C9	−2.1 (3)	C18—C19—C20—C21	−0.6 (3)
C5—C4—C6—C9	109.0 (2)	C17—C16—C21—C20	−0.1 (3)
C3—C4—C6—C5	−111.1 (2)	N1—C16—C21—C20	176.72 (18)
C16—N1—C9—O1	164.25 (19)	C19—C20—C21—C16	0.7 (3)
C10—N1—C9—O1	−7.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₁H₁₉ClF₃NO
M_r	393.82
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	9.247 (6), 21.443 (14), 10.025 (7)
β (°)	99.068 (11)
V (Å³)	1963 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.951, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	11179, 4030, 2379
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.00
No. of reflections	4030
No. of parameters	274
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Acknowledgements

This work was supported by the National Natural Science Foundation (No. 20376059)

References

Bruker (1997). SADABS, SMART, SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, D.-Q., Feng, Y.-Q., Liu, D.-W. & Zhang, S.-S. (2006). Acta Cryst. E62, o1747–o1748. Web of Science CSD CrossRef IUCr Journals Google Scholar
Punja, N. (1981). European Patent EP 0 031 199. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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