(E)-2-(4-tert-But-ylphen-yl)-2-cyano-1-(3-methyl-1-vinyl-1H-pyrazol-5-yl)vinyl 2,2-dimethyl-propano-ate.

In the title compound, C(24)H(29)N(3)O(2), the dihedral angle between the benzene and pyrazole rings is 80.55 (7)°. The mol-ecule contains an acrylonitrile moiety and exists in an E conformation. Bioassay tests showed that the title compound exhibited higher acaricidal activity than its Z isomer.

Related literature

For background to acrylonitrile compounds, see: Boedec et al. (2008 ▶); Napolitano et al. (2001 ▶); Reggio et al. (1998 ▶). For further synthetic details, see: Kenzo et al. (2006 ▶); Yang et al. (2009 ▶).

Experimental

Crystal data

C24H29N3O2

M = 391.50

Orthorhombic,

a = 12.0056 (16) Å

b = 19.283 (3) Å

c = 20.183 (3) Å

V = 4672.5 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.38 × 0.36 × 0.32 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.973, T max = 0.978

22480 measured reflections

4118 independent reflections

2871 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.148

S = 1.05

4118 reflections

269 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.20 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052007/hb6506sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052007/hb6506Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052007/hb6506Isup3.cml

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

C24H29N3O2	Dx = 1.113 Mg m−3
Mr = 391.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 4156 reflections
a = 12.0056 (16) Å	θ = 2.6–20.4°
b = 19.283 (3) Å	µ = 0.07 mm−1
c = 20.183 (3) Å	T = 296 K
V = 4672.5 (11) Å3	Block, colorless
Z = 8	0.38 × 0.36 × 0.32 mm
F(000) = 1680

Bruker SMART CCD diffractometer	4118 independent reflections
Radiation source: fine-focus sealed tube	2871 reflections with I > 2σ(I)
graphite	Rint = 0.033
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −14→12
Tmin = 0.973, Tmax = 0.978	k = −22→22
22480 measured reflections	l = −21→24

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0633P)2 + 1.5443P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4118 reflections	Δρmax = 0.31 e Å−3
269 parameters	Δρmin = −0.20 e Å−3
0 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: 0.0021 (4)

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.

	x	y	z	Uiso*/Ueq
O1	1.01105 (11)	0.08044 (6)	0.73974 (7)	0.0513 (4)
O2	1.19100 (13)	0.05098 (8)	0.73607 (9)	0.0768 (5)
N1	0.97347 (15)	−0.00910 (9)	0.85788 (8)	0.0567 (5)
N2	1.00594 (16)	−0.05609 (9)	0.90444 (9)	0.0646 (5)
N3	0.8306 (2)	−0.13197 (10)	0.68953 (12)	0.0864 (7)
C1	0.8888 (3)	0.07058 (15)	0.93404 (14)	0.0988 (10)
H1A	0.9211	0.0479	0.9699	0.119*
H1B	0.8437	0.1091	0.9410	0.119*
C2	0.9067 (2)	0.04860 (12)	0.87455 (12)	0.0699 (7)
H2	0.8729	0.0726	0.8400	0.084*
C3	1.05513 (19)	−0.10678 (11)	0.87092 (11)	0.0593 (6)
C4	1.05432 (18)	−0.09274 (10)	0.80299 (11)	0.0576 (5)
H4	1.0837	−0.1202	0.7694	0.069*
C5	1.00186 (16)	−0.03077 (10)	0.79596 (10)	0.0500 (5)
C6	1.1022 (2)	−0.16827 (13)	0.90619 (13)	0.0807 (8)
H6A	1.1816	−0.1636	0.9094	0.121*
H6B	1.0844	−0.2097	0.8820	0.121*
H6C	1.0709	−0.1710	0.9499	0.121*
C7	0.97899 (16)	0.01082 (9)	0.73651 (9)	0.0485 (5)
C8	0.92256 (16)	−0.01145 (10)	0.68363 (10)	0.0494 (5)
C9	0.87266 (19)	−0.07898 (11)	0.68833 (11)	0.0601 (6)
C10	0.90092 (17)	0.02826 (10)	0.62182 (10)	0.0512 (5)
C11	0.79697 (18)	0.02586 (12)	0.59251 (11)	0.0616 (6)
H11	0.7419	−0.0023	0.6105	0.074*
C12	0.77404 (19)	0.06478 (12)	0.53681 (11)	0.0655 (6)
H12	0.7033	0.0624	0.5182	0.079*
C13	0.85333 (19)	0.10742 (11)	0.50771 (10)	0.0580 (5)
C14	0.9582 (2)	0.10713 (13)	0.53610 (11)	0.0702 (7)
H14	1.0142	0.1338	0.5172	0.084*
C15	0.98194 (19)	0.06812 (13)	0.59201 (11)	0.0660 (6)
H15	1.0535	0.0689	0.6096	0.079*
C16	0.8234 (2)	0.15167 (13)	0.44748 (11)	0.0702 (7)
C17	0.7940 (3)	0.10424 (16)	0.38919 (13)	0.1009 (10)
H17A	0.8573	0.0761	0.3781	0.151*
H17B	0.7735	0.1320	0.3516	0.151*
H17C	0.7327	0.0749	0.4013	0.151*
C18	0.7231 (3)	0.19699 (17)	0.46499 (16)	0.1115 (11)
H18A	0.6607	0.1680	0.4758	0.167*
H18B	0.7045	0.2258	0.4278	0.167*
H18C	0.7411	0.2257	0.5024	0.167*
C19	0.9185 (3)	0.19962 (16)	0.42640 (15)	0.1063 (11)
H19A	0.9387	0.2291	0.4628	0.160*
H19B	0.8949	0.2276	0.3896	0.160*
H19C	0.9817	0.1723	0.4135	0.160*
C20	1.12292 (17)	0.09525 (10)	0.74372 (10)	0.0518 (5)
C21	1.14310 (17)	0.17108 (10)	0.75803 (11)	0.0556 (5)
C22	1.0765 (3)	0.21582 (14)	0.7115 (2)	0.1206 (13)
H22A	1.0931	0.2637	0.7197	0.181*
H22B	0.9984	0.2078	0.7186	0.181*
H22C	1.0953	0.2045	0.6666	0.181*
C23	1.2642 (2)	0.18635 (16)	0.7505 (2)	0.1382 (17)
H23A	1.2859	0.1792	0.7052	0.207*
H23B	1.3064	0.1560	0.7787	0.207*
H23C	1.2783	0.2337	0.7627	0.207*
C24	1.1051 (4)	0.18545 (16)	0.82782 (17)	0.1350 (16)
H24A	1.1466	0.1570	0.8581	0.202*
H24B	1.0272	0.1750	0.8317	0.202*
H24C	1.1173	0.2335	0.8381	0.202*

	U11	U22	U33	U12	U13	U23
O1	0.0501 (8)	0.0407 (7)	0.0630 (9)	−0.0020 (6)	−0.0045 (6)	0.0059 (6)
O2	0.0561 (9)	0.0525 (9)	0.1218 (14)	0.0054 (8)	0.0108 (9)	−0.0098 (9)
N1	0.0695 (12)	0.0507 (10)	0.0500 (10)	0.0061 (9)	−0.0031 (8)	0.0059 (8)
N2	0.0793 (13)	0.0600 (11)	0.0544 (10)	0.0039 (10)	−0.0052 (9)	0.0125 (9)
N3	0.0908 (16)	0.0511 (12)	0.1174 (18)	−0.0115 (11)	−0.0258 (13)	0.0096 (12)
C1	0.145 (3)	0.0825 (19)	0.0688 (18)	0.0329 (19)	0.0055 (17)	0.0000 (14)
C2	0.0892 (18)	0.0611 (14)	0.0593 (14)	0.0129 (13)	0.0022 (12)	0.0055 (11)
C3	0.0642 (14)	0.0517 (12)	0.0620 (13)	0.0014 (11)	−0.0064 (11)	0.0130 (10)
C4	0.0654 (13)	0.0489 (12)	0.0587 (13)	0.0042 (10)	−0.0022 (10)	0.0059 (10)
C5	0.0534 (12)	0.0448 (11)	0.0519 (11)	−0.0020 (9)	−0.0034 (9)	0.0049 (9)
C6	0.0979 (19)	0.0665 (15)	0.0776 (16)	0.0142 (14)	−0.0088 (14)	0.0238 (13)
C7	0.0490 (11)	0.0411 (10)	0.0554 (12)	0.0007 (9)	0.0007 (9)	0.0054 (9)
C8	0.0504 (11)	0.0442 (11)	0.0537 (12)	0.0005 (9)	−0.0020 (9)	0.0029 (9)
C9	0.0648 (14)	0.0477 (13)	0.0676 (14)	0.0004 (11)	−0.0119 (11)	0.0053 (10)
C10	0.0547 (12)	0.0468 (11)	0.0522 (11)	0.0009 (9)	−0.0039 (9)	0.0014 (9)
C11	0.0564 (13)	0.0635 (13)	0.0649 (13)	−0.0116 (11)	−0.0075 (10)	0.0085 (11)
C12	0.0586 (14)	0.0743 (15)	0.0637 (14)	−0.0059 (12)	−0.0145 (11)	0.0092 (12)
C13	0.0682 (14)	0.0568 (12)	0.0491 (12)	−0.0019 (11)	−0.0072 (10)	0.0013 (10)
C14	0.0679 (15)	0.0834 (17)	0.0593 (14)	−0.0164 (13)	−0.0032 (11)	0.0163 (12)
C15	0.0520 (13)	0.0869 (17)	0.0591 (13)	−0.0097 (12)	−0.0073 (10)	0.0130 (12)
C16	0.0887 (18)	0.0700 (15)	0.0520 (13)	0.0016 (13)	−0.0084 (12)	0.0084 (11)
C17	0.139 (3)	0.106 (2)	0.0578 (15)	−0.004 (2)	−0.0199 (16)	0.0021 (15)
C18	0.133 (3)	0.107 (2)	0.095 (2)	0.043 (2)	−0.0074 (19)	0.0255 (18)
C19	0.132 (3)	0.103 (2)	0.083 (2)	−0.021 (2)	−0.0145 (18)	0.0406 (17)
C20	0.0504 (12)	0.0487 (11)	0.0562 (12)	−0.0004 (10)	0.0018 (9)	0.0025 (9)
C21	0.0500 (12)	0.0434 (11)	0.0734 (14)	−0.0003 (9)	0.0010 (10)	−0.0006 (10)
C22	0.124 (3)	0.0591 (16)	0.179 (3)	−0.0163 (17)	−0.050 (2)	0.0348 (19)
C23	0.0617 (18)	0.0661 (17)	0.287 (5)	−0.0136 (14)	0.013 (2)	−0.039 (3)
C24	0.229 (5)	0.0684 (18)	0.107 (3)	−0.036 (2)	0.047 (3)	−0.0325 (18)

O1—C20	1.375 (2)	C13—C16	1.528 (3)
O1—C7	1.398 (2)	C14—C15	1.386 (3)
O2—C20	1.192 (2)	C14—H14	0.9300
N1—C5	1.361 (2)	C15—H15	0.9300
N1—N2	1.362 (2)	C16—C18	1.529 (4)
N1—C2	1.412 (3)	C16—C19	1.530 (4)
N2—C3	1.327 (3)	C16—C17	1.531 (3)
N3—C9	1.140 (3)	C17—H17A	0.9600
C1—C2	1.291 (3)	C17—H17B	0.9600
C1—H1A	0.9300	C17—H17C	0.9600
C1—H1B	0.9300	C18—H18A	0.9600
C2—H2	0.9300	C18—H18B	0.9600
C3—C4	1.398 (3)	C18—H18C	0.9600
C3—C6	1.494 (3)	C19—H19A	0.9600
C4—C5	1.358 (3)	C19—H19B	0.9600
C4—H4	0.9300	C19—H19C	0.9600
C5—C7	1.469 (3)	C20—C21	1.510 (3)
C6—H6A	0.9600	C21—C23	1.491 (4)
C6—H6B	0.9600	C21—C22	1.505 (4)
C6—H6C	0.9600	C21—C24	1.506 (4)
C7—C8	1.335 (3)	C22—H22A	0.9600
C8—C9	1.436 (3)	C22—H22B	0.9600
C8—C10	1.487 (3)	C22—H22C	0.9600
C10—C15	1.378 (3)	C23—H23A	0.9600
C10—C11	1.382 (3)	C23—H23B	0.9600
C11—C12	1.379 (3)	C23—H23C	0.9600
C11—H11	0.9300	C24—H24A	0.9600
C12—C13	1.388 (3)	C24—H24B	0.9600
C12—H12	0.9300	C24—H24C	0.9600
C13—C14	1.383 (3)
C20—O1—C7	118.09 (15)	C13—C16—C18	108.7 (2)
C5—N1—N2	110.95 (17)	C13—C16—C19	112.5 (2)
C5—N1—C2	127.07 (18)	C18—C16—C19	107.9 (2)
N2—N1—C2	121.49 (18)	C13—C16—C17	109.4 (2)
C3—N2—N1	105.40 (17)	C18—C16—C17	109.7 (2)
C2—C1—H1A	120.0	C19—C16—C17	108.6 (2)
C2—C1—H1B	120.0	C16—C17—H17A	109.5
H1A—C1—H1B	120.0	C16—C17—H17B	109.5
C1—C2—N1	125.1 (2)	H17A—C17—H17B	109.5
C1—C2—H2	117.5	C16—C17—H17C	109.5
N1—C2—H2	117.5	H17A—C17—H17C	109.5
N2—C3—C4	110.75 (18)	H17B—C17—H17C	109.5
N2—C3—C6	120.7 (2)	C16—C18—H18A	109.5
C4—C3—C6	128.6 (2)	C16—C18—H18B	109.5
C5—C4—C3	106.02 (19)	H18A—C18—H18B	109.5
C5—C4—H4	127.0	C16—C18—H18C	109.5
C3—C4—H4	127.0	H18A—C18—H18C	109.5
C4—C5—N1	106.87 (17)	H18B—C18—H18C	109.5
C4—C5—C7	130.71 (19)	C16—C19—H19A	109.5
N1—C5—C7	122.39 (17)	C16—C19—H19B	109.5
C3—C6—H6A	109.5	H19A—C19—H19B	109.5
C3—C6—H6B	109.5	C16—C19—H19C	109.5
H6A—C6—H6B	109.5	H19A—C19—H19C	109.5
C3—C6—H6C	109.5	H19B—C19—H19C	109.5
H6A—C6—H6C	109.5	O2—C20—O1	120.89 (18)
H6B—C6—H6C	109.5	O2—C20—C21	127.47 (19)
C8—C7—O1	119.07 (17)	O1—C20—C21	111.64 (17)
C8—C7—C5	124.90 (18)	C23—C21—C22	110.0 (3)
O1—C7—C5	115.76 (16)	C23—C21—C24	110.8 (3)
C7—C8—C9	116.77 (18)	C22—C21—C24	108.5 (3)
C7—C8—C10	126.43 (18)	C23—C21—C20	109.14 (19)
C9—C8—C10	116.71 (17)	C22—C21—C20	110.5 (2)
N3—C9—C8	177.0 (2)	C24—C21—C20	107.96 (19)
C15—C10—C11	117.98 (19)	C21—C22—H22A	109.5
C15—C10—C8	122.03 (18)	C21—C22—H22B	109.5
C11—C10—C8	119.99 (18)	H22A—C22—H22B	109.5
C12—C11—C10	120.7 (2)	C21—C22—H22C	109.5
C12—C11—H11	119.6	H22A—C22—H22C	109.5
C10—C11—H11	119.6	H22B—C22—H22C	109.5
C11—C12—C13	122.0 (2)	C21—C23—H23A	109.5
C11—C12—H12	119.0	C21—C23—H23B	109.5
C13—C12—H12	119.0	H23A—C23—H23B	109.5
C14—C13—C12	116.5 (2)	C21—C23—H23C	109.5
C14—C13—C16	123.1 (2)	H23A—C23—H23C	109.5
C12—C13—C16	120.4 (2)	H23B—C23—H23C	109.5
C13—C14—C15	121.8 (2)	C21—C24—H24A	109.5
C13—C14—H14	119.1	C21—C24—H24B	109.5
C15—C14—H14	119.1	H24A—C24—H24B	109.5
C10—C15—C14	120.9 (2)	C21—C24—H24C	109.5
C10—C15—H15	119.6	H24A—C24—H24C	109.5
C14—C15—H15	119.6	H24B—C24—H24C	109.5
C5—N1—N2—C3	0.3 (2)	C9—C8—C10—C15	−141.2 (2)
C2—N1—N2—C3	172.7 (2)	C7—C8—C10—C11	−137.6 (2)
C5—N1—C2—C1	−174.3 (3)	C9—C8—C10—C11	38.7 (3)
N2—N1—C2—C1	14.6 (4)	C15—C10—C11—C12	−2.9 (3)
N1—N2—C3—C4	−0.1 (2)	C8—C10—C11—C12	177.1 (2)
N1—N2—C3—C6	179.9 (2)	C10—C11—C12—C13	0.3 (4)
N2—C3—C4—C5	−0.1 (3)	C11—C12—C13—C14	2.2 (4)
C6—C3—C4—C5	179.9 (2)	C11—C12—C13—C16	−177.8 (2)
C3—C4—C5—N1	0.3 (2)	C12—C13—C14—C15	−2.1 (4)
C3—C4—C5—C7	178.3 (2)	C16—C13—C14—C15	177.9 (2)
N2—N1—C5—C4	−0.4 (2)	C11—C10—C15—C14	3.0 (3)
C2—N1—C5—C4	−172.3 (2)	C8—C10—C15—C14	−177.0 (2)
N2—N1—C5—C7	−178.57 (18)	C13—C14—C15—C10	−0.5 (4)
C2—N1—C5—C7	9.5 (3)	C14—C13—C16—C18	−124.4 (3)
C20—O1—C7—C8	−119.5 (2)	C12—C13—C16—C18	55.6 (3)
C20—O1—C7—C5	66.1 (2)	C14—C13—C16—C19	−5.0 (3)
C4—C5—C7—C8	57.1 (3)	C12—C13—C16—C19	175.0 (2)
N1—C5—C7—C8	−125.2 (2)	C14—C13—C16—C17	115.8 (3)
C4—C5—C7—O1	−128.9 (2)	C12—C13—C16—C17	−64.1 (3)
N1—C5—C7—O1	48.7 (3)	C7—O1—C20—O2	9.5 (3)
O1—C7—C8—C9	−168.00 (18)	C7—O1—C20—C21	−170.71 (16)
C5—C7—C8—C9	5.8 (3)	O2—C20—C21—C23	9.3 (4)
O1—C7—C8—C10	8.3 (3)	O1—C20—C21—C23	−170.5 (2)
C5—C7—C8—C10	−177.90 (19)	O2—C20—C21—C22	130.3 (3)
C7—C8—C9—N3	170 (5)	O1—C20—C21—C22	−49.5 (3)
C10—C8—C9—N3	−7(5)	O2—C20—C21—C24	−111.2 (3)
C7—C8—C10—C15	42.4 (3)	O1—C20—C21—C24	69.0 (3)