(1SR,3SR)-[(SR)-Cyano-(3-phenoxy-phen-yl)meth-yl] 3-[(Z)-2-chloro-3,3,3-trifluoro-prop-1-en-yl]-2,2-dimethyl-cyclo-propane-1-carboxyl-ate.

In the crystal of the title compound, C(23)H(19)ClF(3)NO(3), mol-ecules are linked by one C-H⋯O hydrogen bond and two C-H⋯π inter-actions into a three-dimensional network.

Related literature

For the insecticidal activity of the title compound, see: Anadón et al. (2006 ▶). For the synthesis, see: Whittle (1991 ▶).

Experimental

Crystal data

C23H19ClF3NO3

M = 449.84

Monoclinic,

a = 34.7685 (13) Å

b = 7.0159 (3) Å

c = 18.6075 (7) Å

β = 102.113 (1)°

V = 4437.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 298 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.927, T max = 0.957

18537 measured reflections

4361 independent reflections

2721 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.174

S = 1.03

4361 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034855/cs2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034855/cs2097Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C23H19ClF3NO3	F000 = 1856
Mr = 449.84	Dx = 1.347 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4557 reflections
a = 34.7685 (13) Å	θ = 2.2–23.4º
b = 7.0159 (3) Å	µ = 0.22 mm−1
c = 18.6075 (7) Å	T = 298 (2) K
β = 102.113 (1)º	Block, light blue
V = 4437.9 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker SMART APEX CCD area-detector diffractometer	4361 independent reflections
Radiation source: fine focus sealed Siemens Mo tube	2721 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 298(2) K	θmax = 26.0º
0.3° wide ω exposures scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −42→35
Tmin = 0.927, Tmax = 0.957	k = −8→8
18537 measured reflections	l = −22→22

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.1013P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4361 reflections	Δρmax = 0.31 e Å−3
282 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
C1	0.82508 (6)	0.7813 (3)	0.26163 (12)	0.0597 (5)
C2	0.82592 (6)	0.7796 (3)	0.33556 (12)	0.0629 (6)
H2	0.8430	0.6989	0.3667	0.076*
C3	0.80102 (8)	0.8999 (4)	0.36309 (14)	0.0784 (7)
H3	0.8010	0.8989	0.4131	0.094*
C4	0.77628 (9)	1.0207 (4)	0.31715 (18)	0.0913 (8)
H4	0.7599	1.1027	0.3361	0.110*
C5	0.77568 (8)	1.0206 (4)	0.24306 (17)	0.0874 (8)
H5	0.7586	1.1016	0.2120	0.105*
C6	0.80008 (7)	0.9018 (3)	0.21453 (13)	0.0737 (7)
H6	0.7998	0.9022	0.1645	0.088*
C7	0.87410 (7)	0.5401 (3)	0.27252 (10)	0.0620 (6)
C8	0.86173 (8)	0.3602 (4)	0.28285 (13)	0.0772 (7)
H8	0.8359	0.3238	0.2632	0.093*
C9	0.88769 (10)	0.2333 (4)	0.32258 (16)	0.0874 (8)
H9	0.8797	0.1089	0.3286	0.105*
C10	0.92547 (9)	0.2877 (3)	0.35373 (13)	0.0758 (7)
H10	0.9427	0.2007	0.3811	0.091*
C11	0.93796 (6)	0.4725 (3)	0.34439 (11)	0.0573 (5)
C12	0.91198 (6)	0.5985 (3)	0.30277 (10)	0.0559 (5)
H12	0.9199	0.7221	0.2951	0.067*
C13	0.97833 (6)	0.5304 (3)	0.38318 (12)	0.0702 (6)
H13	0.9814	0.4949	0.4350	0.084*
C14	0.98580 (8)	0.7324 (5)	0.3802 (2)	0.1129 (12)
C15	1.04198 (6)	0.3962 (3)	0.40121 (11)	0.0623 (6)
C16	1.06771 (6)	0.2730 (3)	0.36835 (11)	0.0636 (6)
H16	1.0583	0.2473	0.3158	0.076*
C17	1.09040 (6)	0.1102 (3)	0.41174 (12)	0.0649 (6)
C18	1.11249 (7)	0.2809 (3)	0.39356 (12)	0.0645 (6)
H18	1.1265	0.2579	0.3539	0.077*
C19	1.08716 (8)	0.0740 (4)	0.48990 (14)	0.0892 (8)
H19A	1.1095	0.0016	0.5145	0.134*
H19B	1.0635	0.0040	0.4904	0.134*
H19C	1.0864	0.1935	0.5147	0.134*
C20	1.09345 (9)	−0.0686 (4)	0.36638 (17)	0.0966 (9)
H20A	1.0969	−0.0324	0.3184	0.145*
H20B	1.0698	−0.1424	0.3619	0.145*
H20C	1.1156	−0.1434	0.3904	0.145*
C21	1.13247 (7)	0.4171 (3)	0.44884 (12)	0.0647 (6)
H21	1.1173	0.4799	0.4770	0.078*
C22	1.16996 (7)	0.4567 (3)	0.46149 (12)	0.0679 (6)
C23	1.18909 (8)	0.6047 (4)	0.51402 (15)	0.0848 (8)
Cl1	1.20240 (2)	0.34527 (17)	0.41744 (5)	0.1270 (4)
F1	1.21955 (6)	0.5406 (3)	0.56238 (9)	0.1209 (6)
F2	1.20212 (7)	0.7498 (3)	0.48102 (12)	0.1395 (8)
F3	1.16466 (6)	0.6767 (3)	0.55237 (11)	0.1256 (7)
N1	0.99126 (9)	0.8901 (5)	0.3787 (3)	0.183 (2)
O1	0.84875 (5)	0.6664 (3)	0.22854 (8)	0.0822 (5)
O2	1.00732 (4)	0.4254 (2)	0.35359 (7)	0.0663 (4)
O3	1.04889 (5)	0.4637 (3)	0.46189 (8)	0.0848 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0391 (11)	0.0637 (13)	0.0713 (13)	−0.0075 (10)	0.0002 (10)	0.0006 (10)
C2	0.0509 (13)	0.0650 (13)	0.0686 (13)	−0.0005 (11)	0.0028 (10)	0.0014 (10)
C3	0.0761 (18)	0.0697 (15)	0.0884 (16)	0.0005 (13)	0.0146 (14)	−0.0031 (13)
C4	0.0773 (19)	0.0685 (16)	0.128 (2)	0.0105 (14)	0.0213 (17)	−0.0024 (17)
C5	0.0674 (17)	0.0660 (16)	0.119 (2)	0.0060 (13)	−0.0019 (15)	0.0178 (15)
C6	0.0554 (14)	0.0761 (15)	0.0808 (14)	−0.0074 (13)	−0.0056 (12)	0.0131 (13)
C7	0.0586 (14)	0.0718 (15)	0.0553 (11)	0.0046 (11)	0.0112 (10)	−0.0011 (10)
C8	0.0673 (16)	0.0902 (19)	0.0738 (14)	−0.0221 (15)	0.0141 (12)	−0.0038 (13)
C9	0.108 (2)	0.0645 (16)	0.0941 (18)	−0.0241 (16)	0.0301 (17)	−0.0003 (14)
C10	0.0889 (19)	0.0599 (15)	0.0778 (14)	0.0141 (14)	0.0157 (14)	0.0110 (12)
C11	0.0534 (13)	0.0582 (13)	0.0603 (11)	0.0078 (10)	0.0123 (9)	−0.0030 (10)
C12	0.0518 (13)	0.0520 (11)	0.0639 (11)	0.0010 (10)	0.0120 (10)	0.0011 (9)
C13	0.0504 (14)	0.0838 (17)	0.0741 (13)	0.0169 (12)	0.0080 (11)	−0.0148 (12)
C14	0.0446 (15)	0.089 (2)	0.198 (4)	0.0039 (15)	0.0085 (18)	−0.043 (2)
C15	0.0502 (13)	0.0796 (15)	0.0567 (12)	0.0140 (11)	0.0105 (10)	0.0005 (11)
C16	0.0570 (14)	0.0797 (15)	0.0551 (11)	0.0162 (11)	0.0140 (10)	−0.0037 (10)
C17	0.0475 (12)	0.0663 (14)	0.0805 (14)	0.0074 (11)	0.0129 (10)	0.0040 (11)
C18	0.0540 (13)	0.0745 (15)	0.0702 (13)	0.0096 (11)	0.0245 (10)	−0.0003 (11)
C19	0.0715 (17)	0.100 (2)	0.0950 (17)	−0.0010 (14)	0.0155 (13)	0.0306 (15)
C20	0.0759 (19)	0.0710 (16)	0.141 (2)	0.0087 (14)	0.0185 (17)	−0.0167 (16)
C21	0.0573 (15)	0.0660 (14)	0.0759 (13)	0.0057 (11)	0.0256 (11)	0.0025 (11)
C22	0.0564 (15)	0.0767 (15)	0.0733 (13)	0.0060 (12)	0.0194 (11)	0.0116 (12)
C23	0.0679 (18)	0.0958 (19)	0.0901 (17)	−0.0137 (15)	0.0157 (15)	0.0084 (16)
Cl1	0.0578 (5)	0.2056 (10)	0.1202 (6)	0.0220 (5)	0.0247 (4)	−0.0386 (6)
F1	0.0990 (13)	0.1413 (15)	0.1050 (12)	−0.0063 (11)	−0.0183 (10)	0.0062 (11)
F2	0.1411 (17)	0.1298 (15)	0.1407 (15)	−0.0612 (13)	0.0139 (13)	0.0315 (12)
F3	0.1030 (14)	0.1286 (15)	0.1494 (15)	−0.0232 (11)	0.0360 (12)	−0.0558 (12)
N1	0.075 (2)	0.086 (2)	0.377 (6)	−0.0026 (17)	0.022 (3)	−0.054 (3)
O1	0.0645 (10)	0.1168 (14)	0.0603 (9)	0.0232 (10)	0.0019 (8)	0.0091 (9)
O2	0.0542 (9)	0.0836 (11)	0.0590 (8)	0.0222 (8)	0.0071 (7)	−0.0039 (7)
O3	0.0577 (10)	0.1282 (14)	0.0655 (9)	0.0242 (9)	0.0065 (7)	−0.0257 (9)

C1—C2	1.370 (3)	C13—H13	0.9800
C1—C6	1.385 (3)	C14—N1	1.124 (4)
C1—O1	1.386 (3)	C15—O3	1.201 (2)
C2—C3	1.382 (3)	C15—O2	1.353 (2)
C2—H2	0.9300	C15—C16	1.467 (3)
C3—C4	1.371 (4)	C16—C17	1.521 (3)
C3—H3	0.9300	C16—C18	1.530 (3)
C4—C5	1.374 (4)	C16—H16	0.9800
C4—H4	0.9300	C17—C18	1.499 (3)
C5—C6	1.373 (4)	C17—C19	1.504 (3)
C5—H5	0.9300	C17—C20	1.528 (3)
C6—H6	0.9300	C18—C21	1.468 (3)
C7—C8	1.360 (3)	C18—H18	0.9800
C7—C12	1.381 (3)	C19—H19A	0.9600
C7—O1	1.389 (3)	C19—H19B	0.9600
C8—C9	1.369 (4)	C19—H19C	0.9600
C8—H8	0.9300	C20—H20A	0.9600
C9—C10	1.374 (4)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.390 (3)	C21—C22	1.305 (3)
C10—H10	0.9300	C21—H21	0.9300
C11—C12	1.379 (3)	C22—C23	1.485 (4)
C11—C13	1.494 (3)	C22—Cl1	1.716 (2)
C12—H12	0.9300	C23—F1	1.317 (3)
C13—C14	1.444 (4)	C23—F2	1.317 (3)
C13—O2	1.448 (2)	C23—F3	1.319 (3)
C2—C1—C6	121.3 (2)	O2—C15—C16	110.69 (17)
C2—C1—O1	123.49 (19)	C15—C16—C17	121.01 (18)
C6—C1—O1	115.2 (2)	C15—C16—C18	121.43 (18)
C1—C2—C3	118.9 (2)	C17—C16—C18	58.87 (14)
C1—C2—H2	120.5	C15—C16—H16	114.7
C3—C2—H2	120.5	C17—C16—H16	114.7
C4—C3—C2	120.4 (2)	C18—C16—H16	114.7
C4—C3—H3	119.8	C18—C17—C19	119.9 (2)
C2—C3—H3	119.8	C18—C17—C16	60.88 (14)
C3—C4—C5	120.0 (3)	C19—C17—C16	120.3 (2)
C3—C4—H4	120.0	C18—C17—C20	115.7 (2)
C5—C4—H4	120.0	C19—C17—C20	115.1 (2)
C6—C5—C4	120.5 (2)	C16—C17—C20	114.3 (2)
C6—C5—H5	119.7	C21—C18—C17	123.46 (18)
C4—C5—H5	119.7	C21—C18—C16	122.67 (18)
C5—C6—C1	118.8 (2)	C17—C18—C16	60.26 (15)
C5—C6—H6	120.6	C21—C18—H18	113.5
C1—C6—H6	120.6	C17—C18—H18	113.5
C8—C7—C12	121.4 (2)	C16—C18—H18	113.5
C8—C7—O1	119.6 (2)	C17—C19—H19A	109.5
C12—C7—O1	119.0 (2)	C17—C19—H19B	109.5
C7—C8—C9	119.2 (2)	H19A—C19—H19B	109.5
C7—C8—H8	120.4	C17—C19—H19C	109.5
C9—C8—H8	120.4	H19A—C19—H19C	109.5
C8—C9—C10	120.7 (2)	H19B—C19—H19C	109.5
C8—C9—H9	119.6	C17—C20—H20A	109.5
C10—C9—H9	119.6	C17—C20—H20B	109.5
C9—C10—C11	120.2 (2)	H20A—C20—H20B	109.5
C9—C10—H10	119.9	C17—C20—H20C	109.5
C11—C10—H10	119.9	H20A—C20—H20C	109.5
C12—C11—C10	118.9 (2)	H20B—C20—H20C	109.5
C12—C11—C13	122.4 (2)	C22—C21—C18	124.9 (2)
C10—C11—C13	118.7 (2)	C22—C21—H21	117.5
C11—C12—C7	119.7 (2)	C18—C21—H21	117.5
C11—C12—H12	120.2	C21—C22—C23	124.1 (2)
C7—C12—H12	120.2	C21—C22—Cl1	123.29 (19)
C14—C13—O2	109.9 (2)	C23—C22—Cl1	112.62 (18)
C14—C13—C11	114.0 (2)	F1—C23—F2	106.1 (2)
O2—C13—C11	109.65 (17)	F1—C23—F3	106.1 (2)
C14—C13—H13	107.7	F2—C23—F3	106.3 (3)
O2—C13—H13	107.7	F1—C23—C22	113.3 (2)
C11—C13—H13	107.7	F2—C23—C22	112.6 (2)
N1—C14—C13	179.0 (4)	F3—C23—C22	111.9 (2)
O3—C15—O2	122.07 (19)	C1—O1—C7	118.18 (16)
O3—C15—C16	127.24 (19)	C15—O2—C13	115.04 (15)
C6—C1—C2—C3	0.5 (3)	C15—C16—C17—C20	142.7 (2)
O1—C1—C2—C3	−179.9 (2)	C18—C16—C17—C20	−107.0 (2)
C1—C2—C3—C4	−0.9 (4)	C19—C17—C18—C21	1.4 (3)
C2—C3—C4—C5	1.0 (4)	C16—C17—C18—C21	111.6 (2)
C3—C4—C5—C6	−0.8 (4)	C20—C17—C18—C21	−143.6 (2)
C4—C5—C6—C1	0.4 (4)	C19—C17—C18—C16	−110.2 (2)
C2—C1—C6—C5	−0.3 (3)	C20—C17—C18—C16	104.8 (2)
O1—C1—C6—C5	−179.9 (2)	C15—C16—C18—C21	−3.2 (3)
C12—C7—C8—C9	−1.6 (3)	C17—C16—C18—C21	−112.8 (2)
O1—C7—C8—C9	176.0 (2)	C15—C16—C18—C17	109.7 (2)
C7—C8—C9—C10	2.0 (4)	C17—C18—C21—C22	121.1 (3)
C8—C9—C10—C11	−0.8 (4)	C16—C18—C21—C22	−165.3 (2)
C9—C10—C11—C12	−0.8 (3)	C18—C21—C22—C23	175.5 (2)
C9—C10—C11—C13	175.9 (2)	C18—C21—C22—Cl1	−3.1 (3)
C10—C11—C12—C7	1.2 (3)	C21—C22—C23—F1	127.1 (3)
C13—C11—C12—C7	−175.40 (18)	Cl1—C22—C23—F1	−54.1 (3)
C8—C7—C12—C11	0.0 (3)	C21—C22—C23—F2	−112.6 (3)
O1—C7—C12—C11	−177.66 (17)	Cl1—C22—C23—F2	66.2 (3)
C12—C11—C13—C14	6.9 (3)	C21—C22—C23—F3	7.1 (3)
C10—C11—C13—C14	−169.7 (2)	Cl1—C22—C23—F3	−174.13 (19)
C12—C11—C13—O2	−116.8 (2)	C2—C1—O1—C7	1.3 (3)
C10—C11—C13—O2	66.6 (3)	C6—C1—O1—C7	−179.1 (2)
O3—C15—C16—C17	43.6 (4)	C8—C7—O1—C1	90.7 (2)
O2—C15—C16—C17	−135.4 (2)	C12—C7—O1—C1	−91.6 (2)
O3—C15—C16—C18	−26.5 (4)	O3—C15—O2—C13	−4.7 (3)
O2—C15—C16—C18	154.5 (2)	C16—C15—O2—C13	174.40 (18)
C15—C16—C17—C18	−110.3 (2)	C14—C13—O2—C15	82.4 (3)
C15—C16—C17—C19	−0.7 (3)	C11—C13—O2—C15	−151.59 (19)
C18—C16—C17—C19	109.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.98	2.39	3.218 (3)	142
C21—H21···O3	0.93	2.34	2.984 (3)	126
C19—H19C···O3	0.96	2.39	3.037 (3)	124
C21—H21···F3	0.93	2.37	2.716 (2)	102
C5—H5···Cg1ii	0.93	2.94	3.721 (1)	143 (1)
C9—H9···Cg1iii	0.93	?	3.768 (1)	134 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.98	2.39	3.218 (3)	142
C21—H21⋯O3	0.93	2.34	2.984 (3)	126
C19—H19C⋯O3	0.96	2.39	3.037 (3)	124
C5—H5⋯Cg1ii	0.93	2.94	3.721 (1)	143 (1)
C9—H9⋯Cg1iii	0.93	3.06	3.768 (1)	134 (1)

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C1–C6 ring.