2-{(E)-4-[4-(Trifluoro­meth­yl)phen­oxy]but-2-en­yloxy}phenyl N-methyl­carbamate

Ma, H.-J.; Xu, M.-H.; Zhang, J.-H.; Li, J.-H.; Ning, J.

doi:10.1107/S1600536813001347

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o326-o327

doi:10.1107/S1600536813001347

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2-{(E)-4-[4-(Trifluoromethyl)phenoxy]but-2-enyloxy}phenyl N-methylcarbamate

Hong-Ju Ma,^a Meng-Han Xu,^a Jian-Hua Zhang,^a Jian-Hong Li ^a and Jun Ning ^b ^*

^aCollege of Plant Science & Technology of Huazhong Agricultural University, Wuhan 430070, People's Republic of China, and ^bKey Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193, People's Republic of China
^*Correspondence e-mail: jning502@yahoo.com.cn

(Received 20 December 2012; accepted 14 January 2013; online 2 February 2013)

In the title compound, C₁₉H₁₈F₃NO₄, which was designed and synthesized as a dual-site inhibitor of insect AChE (acetylcholinesterase), the dihedral angle between the methylcarbamate group and the benzene ring is 72.47 (6)°. In the crystal, inversion dimers are linked by pairs of N—H⋯O hydrogen bonds.

Related literature

For background to multivalent ligand-receptor interactions and their pharmaceutical applications, see: Carlier et al. (1999 ); Hu et al. (2002 ); Kitov et al. (2000 ); Kopytek et al. (2000 ); Kryger et al. (1999 ); Lee & Lee (1995 ); Luedtke et al. (2003 ); Mammen et al. (1998 ); Pang et al. (1996 ). For agrochemical applications of the cluster effect, see: Ma et al. (2010 ); Zhao et al. (2008 , 2009 ). For the structure of AChE from Torpedo californica (TcAChe), see: Sussman et al. (1991 ); Harel et al. (1993 ).

Experimental

Crystal data

C₁₉H₁₈F₃NO₄
M_r = 381.34
Monoclinic, P 2₁ /c
a = 12.413 (3) Å
b = 9.3936 (19) Å
c = 16.202 (3) Å
β = 111.65 (3)°
V = 1755.9 (6) Å³
Z = 4
Cu Kα radiation
μ = 1.05 mm⁻¹
T = 173 K
0.47 × 0.30 × 0.25 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.639, T_max = 0.780
11613 measured reflections
3163 independent reflections
2615 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.107
S = 1.07
3163 reflections
274 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88	2.22	3.072 (2)	163
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: RAPID-AUTO (Rigaku 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001347/mw2102sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001347/mw2102Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001347/mw2102Isup3.cml

checkCIF report

Comment top

Multivalent ligand-receptor interactions, known as the cluster effect, are defined as specific simultaneous associations of multiple ligands present on a molecular construct that bind to multiple receptors presented on a biological entity (Mammen et al., 1998; Lee et al., 1995). In biological systems, multivalent ligands often possess increased functional affinity for their targets compared with that of monovalent ligands (Kitov et al., 2000; Kopytek et al., 2000; Luedtke et al., 2003). Acetylcholinesterase (AChE; EC 3.1.1.7) is a key enzyme in the nervous system, terminating nerve impulses by catalyzing the hydrolysis of the neurotransmitter acetylcholine. X-ray crystallographic structural analysis of the AChE from Torpedo californica (TcAChe) has demonstrated that the active site lies near the bottom of a deep, narrow gorge that reaches half way into the protein and that 14 aromatic residues line a substantial portion of the surface of the gorge (Sussman et al., 1991). This cavity was named the 'active site gorge' with peripheral sites existing at the gorge mouth and Trp279 being the main site (Harel et al., 1993). On the basis of the structure of AChE, many potential dual-site binding inhibitors of AChE have been synthesized (Pang et al., 1996; Carlier et al., 1999; Hu et al., 2002) and demonstrated in drugs in order to treat or alleviate Alzheimer's disease (Kryger et al., 1999). In the area of pesticide, dual- or multiple-site inhibitors of insect AChE were designed and synthesized in our research group (Zhao et al.., 2008; Zhao et al., 2009). Recently, we synthesized novel carbamate derivatives as potential dual-binding site acetylcholinesterase inhibitors (Ma et al., 2010). The crystal structure of the title compound (I) is shown in Fig. 1.

Related literature top

For background to multivalent ligand-receptor interactions and their pharmaceutical applications, see: Carlier et al. (1999); Hu et al. (2002); Kitov et al. (2000); Kopytek et al. (2000); Kryger et al. (1999); Lee & Lee (1995); Luedtke et al. (2003); Mammen et al. (1998); Pang et al. (1996). For agrochemical applications of the cluster effect, see: Ma et al. (2010); Zhao et al. (2008, 2009). For the structure of AChE from Torpedo californica (TcAChe), see: Sussman et al. (1991); Harel et al. (1993).

Experimental top

2-((E)-4-(4-(trifluoromethyl)phenoxy)but-2-enyloxy)phenyl methylcarbamate (0.2 g) was dissolved in 95% ethanol (50 ml) at room temperature. Colorless crystals of compound (I) were obtained through slow evaporation after two weeks.

Computing details top

Data collection: RAPID-AUTO (Rigaku 2001); cell refinement: RAPID-AUTO (Rigaku 2001); data reduction: RAPID-AUTO (Rigaku 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.

2-{(E)-4-[4-(Trifluoromethyl)phenoxy]but-2-enyloxy}phenyl N-methylcarbamate top

Crystal data top

C₁₉H₁₈F₃NO₄	F(000) = 792
M_r = 381.34	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 468 reflections
a = 12.413 (3) Å	θ = 2.2–68.3°
b = 9.3936 (19) Å	µ = 1.05 mm⁻¹
c = 16.202 (3) Å	T = 173 K
β = 111.65 (3)°	Block, colorless
V = 1755.9 (6) Å³	0.47 × 0.30 × 0.25 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3163 independent reflections
Radiation source: rotating anode	2615 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans at fixed χ = 45°	θ_max = 68.2°, θ_min = 3.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.639, T_max = 0.780	k = −11→10
11613 measured reflections	l = −18→19

Refinement top

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0381P)² + 0.8611P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3163 reflections	Δρ_max = 0.29 e Å⁻³
274 parameters	Δρ_min = −0.22 e Å⁻³
60 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0033 (3)

Crystal data top

C₁₉H₁₈F₃NO₄	V = 1755.9 (6) Å³
M_r = 381.34	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.413 (3) Å	µ = 1.05 mm⁻¹
b = 9.3936 (19) Å	T = 173 K
c = 16.202 (3) Å	0.47 × 0.30 × 0.25 mm
β = 111.65 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	3163 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2615 reflections with I > 2σ(I)
T_min = 0.639, T_max = 0.780	R_int = 0.033
11613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	60 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.07	Δρ_max = 0.29 e Å⁻³
3163 reflections	Δρ_min = −0.22 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)
F1	0.4769 (4)	−0.2372 (3)	0.2853 (4)	0.0698 (14)	0.710 (12)
F2	0.4529 (5)	−0.0522 (5)	0.2121 (3)	0.0731 (13)	0.710 (12)
F3	0.5816 (4)	−0.0554 (8)	0.3412 (5)	0.090 (2)	0.710 (12)
F1'	0.5251 (13)	−0.2132 (15)	0.3448 (14)	0.109 (5)	0.290 (12)
F2'	0.4491 (9)	−0.111 (2)	0.2122 (6)	0.111 (5)	0.290 (12)
F3'	0.5655 (11)	−0.0074 (18)	0.3219 (13)	0.092 (5)	0.290 (12)
O1	0.13692 (11)	0.11336 (15)	0.41856 (9)	0.0376 (4)
O2	−0.17712 (11)	0.32576 (15)	0.48990 (9)	0.0348 (3)
O3	0.02201 (12)	0.28785 (14)	0.67050 (9)	0.0367 (4)
O4	−0.03869 (11)	0.50607 (14)	0.60863 (9)	0.0313 (3)
N1	0.12414 (13)	0.41620 (18)	0.60530 (11)	0.0336 (4)
H1	0.1242	0.4945	0.5755	0.040*
C1	0.47480 (19)	−0.0960 (2)	0.29620 (17)	0.0477 (6)
C2	0.38579 (17)	−0.0443 (2)	0.32947 (14)	0.0360 (5)
C3	0.27526 (17)	−0.1023 (2)	0.29649 (13)	0.0360 (5)
H3	0.2584	−0.1773	0.2543	0.043*
C4	0.18957 (17)	−0.0526 (2)	0.32412 (13)	0.0332 (5)
H4	0.1141	−0.0930	0.3009	0.040*
C5	0.21432 (16)	0.0570 (2)	0.38617 (13)	0.0318 (4)
C6	0.32588 (18)	0.1133 (2)	0.42067 (15)	0.0422 (5)
H6	0.3437	0.1868	0.4640	0.051*
C7	0.41034 (18)	0.0630 (2)	0.39219 (15)	0.0439 (5)
H7	0.4862	0.1022	0.4158	0.053*
C8	0.01688 (16)	0.0769 (2)	0.37353 (13)	0.0354 (5)
H8A	0.0055	−0.0264	0.3792	0.043*
H8B	−0.0081	0.1005	0.3096	0.043*
C9	−0.05238 (17)	0.1595 (2)	0.41472 (13)	0.0329 (5)
H9	−0.0182	0.2416	0.4485	0.039*
C10	−0.15720 (18)	0.1256 (2)	0.40707 (14)	0.0381 (5)
H10	−0.1877	0.0412	0.3745	0.046*
C11	−0.23549 (17)	0.2024 (2)	0.44281 (13)	0.0337 (5)
H11A	−0.3074	0.2308	0.3935	0.040*
H11B	−0.2569	0.1392	0.4832	0.040*
C12	−0.22437 (16)	0.3914 (2)	0.54436 (12)	0.0300 (4)
C13	−0.33741 (17)	0.3764 (2)	0.53971 (13)	0.0354 (5)
H13	−0.3893	0.3149	0.4967	0.042*
C14	−0.37483 (18)	0.4512 (2)	0.59798 (14)	0.0394 (5)
H14	−0.4523	0.4402	0.5948	0.047*
C15	−0.30069 (18)	0.5415 (2)	0.66040 (14)	0.0392 (5)
H15	−0.3271	0.5922	0.7001	0.047*
C16	−0.18725 (17)	0.5581 (2)	0.66513 (13)	0.0347 (5)
H16	−0.1360	0.6209	0.7076	0.042*
C17	−0.14992 (16)	0.4832 (2)	0.60820 (12)	0.0296 (4)
C18	0.03597 (16)	0.3915 (2)	0.63119 (12)	0.0290 (4)
C19	0.22029 (18)	0.3175 (2)	0.62487 (16)	0.0446 (6)
H19A	0.2818	0.3611	0.6091	0.067*
H19B	0.1936	0.2300	0.5904	0.067*
H19C	0.2504	0.2947	0.6884	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.082 (2)	0.0421 (13)	0.117 (3)	0.0125 (13)	0.073 (2)	0.0034 (16)
F2	0.084 (3)	0.083 (2)	0.077 (2)	0.0261 (19)	0.059 (2)	0.019 (2)
F3	0.0276 (13)	0.136 (5)	0.100 (3)	−0.001 (2)	0.0170 (15)	−0.051 (3)
F1'	0.099 (7)	0.091 (7)	0.172 (12)	0.058 (6)	0.092 (8)	0.046 (7)
F2'	0.038 (4)	0.192 (13)	0.093 (7)	−0.003 (6)	0.011 (4)	−0.102 (8)
F3'	0.065 (7)	0.090 (7)	0.159 (11)	−0.039 (6)	0.087 (8)	−0.045 (7)
O1	0.0312 (7)	0.0435 (8)	0.0390 (8)	−0.0012 (6)	0.0141 (6)	−0.0093 (7)
O2	0.0333 (7)	0.0358 (8)	0.0412 (8)	−0.0074 (6)	0.0207 (6)	−0.0109 (6)
O3	0.0369 (8)	0.0314 (8)	0.0423 (8)	0.0002 (6)	0.0151 (6)	0.0082 (6)
O4	0.0279 (7)	0.0274 (7)	0.0399 (7)	0.0004 (6)	0.0139 (6)	0.0013 (6)
N1	0.0307 (8)	0.0351 (9)	0.0369 (9)	0.0017 (7)	0.0148 (7)	0.0039 (8)
C1	0.0362 (12)	0.0442 (13)	0.0672 (16)	0.0019 (11)	0.0243 (11)	0.0044 (13)
C2	0.0302 (10)	0.0354 (11)	0.0437 (11)	0.0024 (9)	0.0151 (9)	0.0051 (9)
C3	0.0347 (10)	0.0354 (11)	0.0385 (11)	−0.0001 (9)	0.0141 (9)	−0.0032 (9)
C4	0.0300 (10)	0.0346 (11)	0.0344 (10)	−0.0010 (8)	0.0111 (8)	−0.0010 (9)
C5	0.0302 (10)	0.0330 (10)	0.0327 (10)	0.0027 (8)	0.0121 (8)	0.0035 (8)
C6	0.0342 (11)	0.0405 (12)	0.0489 (12)	−0.0047 (10)	0.0118 (9)	−0.0112 (10)
C7	0.0285 (10)	0.0434 (12)	0.0573 (14)	−0.0043 (9)	0.0130 (10)	−0.0055 (11)
C8	0.0313 (10)	0.0384 (11)	0.0380 (11)	−0.0031 (9)	0.0145 (9)	−0.0050 (9)
C9	0.0347 (10)	0.0314 (10)	0.0335 (10)	−0.0015 (9)	0.0137 (8)	−0.0049 (8)
C10	0.0408 (11)	0.0331 (11)	0.0439 (12)	−0.0048 (9)	0.0200 (9)	−0.0095 (9)
C11	0.0334 (10)	0.0322 (10)	0.0367 (11)	−0.0048 (8)	0.0142 (8)	−0.0041 (8)
C12	0.0303 (10)	0.0313 (10)	0.0315 (10)	0.0019 (8)	0.0147 (8)	0.0007 (8)
C13	0.0297 (10)	0.0400 (12)	0.0382 (11)	−0.0026 (9)	0.0145 (9)	−0.0030 (9)
C14	0.0315 (10)	0.0457 (13)	0.0463 (12)	0.0046 (9)	0.0205 (9)	0.0035 (10)
C15	0.0408 (12)	0.0441 (12)	0.0378 (11)	0.0078 (10)	0.0206 (10)	0.0003 (10)
C16	0.0379 (11)	0.0333 (11)	0.0325 (10)	0.0025 (9)	0.0125 (9)	−0.0001 (9)
C17	0.0279 (9)	0.0291 (10)	0.0331 (10)	0.0013 (8)	0.0129 (8)	0.0029 (8)
C18	0.0271 (9)	0.0294 (10)	0.0284 (9)	−0.0008 (8)	0.0077 (8)	−0.0031 (8)
C19	0.0319 (11)	0.0475 (13)	0.0549 (13)	0.0068 (10)	0.0168 (10)	0.0000 (11)

Geometric parameters (Å, º) top

F1—C1	1.339 (3)	C6—H6	0.9500
F2—C1	1.351 (4)	C7—H7	0.9500
F3—C1	1.312 (5)	C8—C9	1.487 (3)
F1'—C1	1.363 (7)	C8—H8A	0.9900
F2'—C1	1.287 (8)	C8—H8B	0.9900
F3'—C1	1.337 (9)	C9—C10	1.300 (3)
O1—C5	1.361 (2)	C9—H9	0.9500
O1—C8	1.438 (2)	C10—C11	1.488 (3)
O2—C12	1.373 (2)	C10—H10	0.9500
O2—C11	1.429 (2)	C11—H11A	0.9900
O3—C18	1.210 (2)	C11—H11B	0.9900
O4—C18	1.379 (2)	C12—C13	1.384 (3)
O4—C17	1.395 (2)	C12—C17	1.401 (3)
N1—C18	1.329 (2)	C13—C14	1.387 (3)
N1—C19	1.451 (3)	C13—H13	0.9500
N1—H1	0.8800	C14—C15	1.379 (3)
C1—C2	1.479 (3)	C14—H14	0.9500
C2—C7	1.383 (3)	C15—C16	1.390 (3)
C2—C3	1.387 (3)	C15—H15	0.9500
C3—C4	1.379 (3)	C16—C17	1.369 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.392 (3)	C19—H19A	0.9800
C4—H4	0.9500	C19—H19B	0.9800
C5—C6	1.393 (3)	C19—H19C	0.9800
C6—C7	1.376 (3)

C5—O1—C8	117.30 (15)	H8A—C8—H8B	108.4
C12—O2—C11	117.06 (15)	C10—C9—C8	123.63 (19)
C18—O4—C17	116.65 (14)	C10—C9—H9	118.2
C18—N1—C19	121.73 (18)	C8—C9—H9	118.2
C18—N1—H1	119.1	C9—C10—C11	128.22 (19)
C19—N1—H1	119.1	C9—C10—H10	115.9
F2'—C1—F3'	104.5 (10)	C11—C10—H10	115.9
F3—C1—F1	107.3 (4)	O2—C11—C10	108.98 (16)
F3—C1—F2	104.9 (4)	O2—C11—H11A	109.9
F1—C1—F2	100.1 (3)	C10—C11—H11A	109.9
F2'—C1—F1'	113.7 (8)	O2—C11—H11B	109.9
F3'—C1—F1'	99.7 (8)	C10—C11—H11B	109.9
F2'—C1—C2	119.7 (6)	H11A—C11—H11B	108.3
F3—C1—C2	116.1 (4)	O2—C12—C13	125.72 (17)
F3'—C1—C2	109.8 (7)	O2—C12—C17	115.42 (16)
F1—C1—C2	115.2 (2)	C13—C12—C17	118.84 (18)
F2—C1—C2	111.6 (3)	C12—C13—C14	119.89 (19)
F1'—C1—C2	107.4 (5)	C12—C13—H13	120.1
C7—C2—C3	119.2 (2)	C14—C13—H13	120.1
C7—C2—C1	121.03 (19)	C15—C14—C13	120.68 (19)
C3—C2—C1	119.8 (2)	C15—C14—H14	119.7
C4—C3—C2	120.9 (2)	C13—C14—H14	119.7
C4—C3—H3	119.5	C14—C15—C16	119.8 (2)
C2—C3—H3	119.5	C14—C15—H15	120.1
C3—C4—C5	119.58 (19)	C16—C15—H15	120.1
C3—C4—H4	120.2	C17—C16—C15	119.53 (19)
C5—C4—H4	120.2	C17—C16—H16	120.2
O1—C5—C4	124.58 (18)	C15—C16—H16	120.2
O1—C5—C6	115.86 (18)	C16—C17—O4	119.88 (17)
C4—C5—C6	119.54 (19)	C16—C17—C12	121.22 (18)
C7—C6—C5	120.2 (2)	O4—C17—C12	118.71 (17)
C7—C6—H6	119.9	O3—C18—N1	126.96 (18)
C5—C6—H6	119.9	O3—C18—O4	123.69 (17)
C6—C7—C2	120.6 (2)	N1—C18—O4	109.33 (16)
C6—C7—H7	119.7	N1—C19—H19A	109.5
C2—C7—H7	119.7	N1—C19—H19B	109.5
O1—C8—C9	108.10 (16)	H19A—C19—H19B	109.5
O1—C8—H8A	110.1	N1—C19—H19C	109.5
C9—C8—H8A	110.1	H19A—C19—H19C	109.5
O1—C8—H8B	110.1	H19B—C19—H19C	109.5
C9—C8—H8B	110.1

F2'—C1—C2—C7	−132.8 (10)	C5—O1—C8—C9	−175.09 (16)
F3—C1—C2—C7	12.8 (5)	O1—C8—C9—C10	−160.9 (2)
F3'—C1—C2—C7	−11.9 (10)	C8—C9—C10—C11	−177.9 (2)
F1—C1—C2—C7	139.4 (4)	C12—O2—C11—C10	−165.39 (16)
F2—C1—C2—C7	−107.3 (3)	C9—C10—C11—O2	−0.2 (3)
F1'—C1—C2—C7	95.6 (11)	C11—O2—C12—C13	−19.5 (3)
F2'—C1—C2—C3	46.2 (10)	C11—O2—C12—C17	161.91 (17)
F3—C1—C2—C3	−168.2 (4)	O2—C12—C13—C14	−178.79 (18)
F3'—C1—C2—C3	167.0 (10)	C17—C12—C13—C14	−0.2 (3)
F1—C1—C2—C3	−41.6 (4)	C12—C13—C14—C15	0.4 (3)
F2—C1—C2—C3	71.7 (3)	C13—C14—C15—C16	0.1 (3)
F1'—C1—C2—C3	−85.4 (11)	C14—C15—C16—C17	−0.7 (3)
C7—C2—C3—C4	1.2 (3)	C15—C16—C17—O4	175.88 (17)
C1—C2—C3—C4	−177.75 (19)	C15—C16—C17—C12	0.8 (3)
C2—C3—C4—C5	−0.2 (3)	C18—O4—C17—C16	117.69 (19)
C8—O1—C5—C4	−12.6 (3)	C18—O4—C17—C12	−67.1 (2)
C8—O1—C5—C6	169.01 (18)	O2—C12—C17—C16	178.33 (17)
C3—C4—C5—O1	−179.48 (18)	C13—C12—C17—C16	−0.4 (3)
C3—C4—C5—C6	−1.1 (3)	O2—C12—C17—O4	3.2 (3)
O1—C5—C6—C7	179.85 (19)	C13—C12—C17—O4	−175.48 (17)
C4—C5—C6—C7	1.3 (3)	C19—N1—C18—O3	−1.9 (3)
C5—C6—C7—C2	−0.3 (3)	C19—N1—C18—O4	176.30 (17)
C3—C2—C7—C6	−1.0 (3)	C17—O4—C18—O3	−18.9 (3)
C1—C2—C7—C6	178.0 (2)	C17—O4—C18—N1	162.82 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.22	3.072 (2)	163

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈F₃NO₄
M_r	381.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	12.413 (3), 9.3936 (19), 16.202 (3)
β (°)	111.65 (3)
V (Å³)	1755.9 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.47 × 0.30 × 0.25

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.639, 0.780
No. of measured, independent and observed [I > 2σ(I)] reflections	11613, 3163, 2615
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.107, 1.07
No. of reflections	3163
No. of parameters	274
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.22

Computer programs: RAPID-AUTO (Rigaku 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.22	3.072 (2)	163

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

This work was partially supported by the National Natural Science Foundation of China (program No. 31201554), the China Postdoctoral Science Foundation (program No. 20110491174) and the Fundamental Research Funds for the Central Universities (program No. 2011QC086).

References

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Volume 69| Part 3| March 2013| Pages o326-o327

doi:10.1107/S1600536813001347

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{(E)-4-[4-(Tri­fluoro­meth­yl)phen­­oxy]but-2-en­yl­oxy}phenyl N-methyl­carbamate

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Experimental

Crystal data

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Refinement

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organic compounds

2-{(E)-4-[4-(Trifluoromethyl)phenoxy]but-2-enyloxy}phenyl N-methylcarbamate