(E)-2-(4-tert-But­ylphen­yl)-2-cyano-1-(3-methyl-1-vinyl-1H-pyrazol-5-yl)vinyl 2,2-dimethyl­propano­ate

Yang, G.; Wang, Y.; Yu, H.

doi:10.1107/S1600536811052007

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o64

doi:10.1107/S1600536811052007

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(E)-2-(4-tert-Butylphenyl)-2-cyano-1-(3-methyl-1-vinyl-1H-pyrazol-5-yl)vinyl 2,2-dimethylpropanoate

Guiqiu Yang,^a ^* Yang Wang ^a and Haibo Yu ^b

^aShenyang University of Chemical Technology, Shenyang 110142, People's Republic of China, and ^bAgrochemicals Division, Shenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
^*Correspondence e-mail: yangguiqiu@gmail.com

(Received 11 November 2011; accepted 2 December 2011; online 10 December 2011)

In the title compound, C₂₄H₂₉N₃O₂, the dihedral angle between the benzene and pyrazole rings is 80.55 (7)°. The molecule 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_r = 391.50
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.148
S = 1.05
4118 reflections
269 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811052007/hb6506sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811052007/hb6506Isup3.cml

checkCIF report

Comment top

Acrylonitrile compounds display a broad range of biological, medical and pharmacological properties (Napolitano et al., 2001, Boedec et al., 2008). There is a double bond in the molecule of the acrylonitrile compounds, and both geometric isomers referred to as the E– and Z-isomer can be present. The bioactivities of them often differ from each other (Reggio et al.,1998). In the process of preparation of the title compound, its geometric isomer product was also afforded, which showed obviously different acaricidal activity with the title compound. The bioassay tests showed that the title compound exhibited higher acaricidal activity than its isomer.

In order to confirm the geometry configuration, we report the crystal structure of the title compound (I) in this paper. The molecular structure of (I) is shown in Fig. 1. The the benzene and pyrazole rings in each of the ligands are not coplanar, the dihedral angle formed by the least-squares planes of the benzene and pyrazole rings being equal to 80.55 (7)°. The C(9)—C(8)—C(10)—C(11), O(1)—C(7)—C(8)—C(9), C(5)—C(7)—C(8)—C(9) and C(20)—O(1)—C(7)—C(5) torsion angles are 38.7 (3), -168.00 (2), 5.8 (3) and 66.1 (2)°, respectively. The crystal packing of (I) shows in Fig. 2. No significant interactions, such as hydrogen bonds or pi-pi stacking, are observed in (I).

Related literature top

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 top

The title compound was synthesized by 2-(4-(tert-butyl) phenyl)-3-(4-chloro-1-ethyl-3-methyl-1H-pyrazol-5-yl) -3-hydroxyacrylonitrile with pivaloyl chloride in THF (Kenzo et al., 2006, Yang et al., 2009). The crude products were purified by silica-gel column chromatography and then grown from heptane to afford colorless single crystals suitable for X-ray diffraction. To the mixture of 2-(4-(tert-butyl)phenyl)-3-(3-methyl-1-vinyl- 1H-pyrazol-5-yl)-3-hydroxyacrylonitrile (0.61 g, 2.0 mmol) and triethyl amine (0.24 g, 2.4 mmol) in THF (10 ml), pivaloyl chloride (0.29 g, 2.4 mmol) was added dropwise at roomtemperature and reacted for 1 h. After separation through silica gel column chromatography (fluent: ethyl acetate/petroleum ether=1/10), The title product compound was gained as a white solid (0.59 g, 75%).

Anal. Calcd for C₂₄H₂₉N₃O₂: C, 73.63; H, 7.47; N, 10.73. Found: C, 73.67; H, 7.50; N, 10.75. ¹H NMR(DMSO): 1.14 (s, 9H, CO (CH₃)₃), 1.33 (s, 9H, Ph-(CH₃)₃), 2.34 (s, 3H, CH₃), 4.92 (d, 1H, CH), 5.79 (d, 1H, CH), 6.56 (s, 1H, py), 7.07 (dd, 1H, CH), 7.45 (d, 2H, Ph), 7.48 (d, 2H, Ph).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of (I).

(E)-2-(4-tert-Butylphenyl)-2-cyano-1-(3-methyl-1-vinyl- 1H-pyrazol-5-yl)vinyl 2,2-dimethylpropanoate top

Crystal data top

C₂₄H₂₉N₃O₂	D_x = 1.113 Mg m⁻³
M_r = 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

Data collection top

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

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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0633P)² + 1.5443P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
4118 reflections	Δρ_max = 0.31 e Å⁻³
269 parameters	Δρ_min = −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)

Crystal data top

C₂₄H₂₉N₃O₂	V = 4672.5 (11) Å³
M_r = 391.50	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.0056 (16) Å	µ = 0.07 mm⁻¹
b = 19.283 (3) Å	T = 296 K
c = 20.183 (3) Å	0.38 × 0.36 × 0.32 mm

Data collection top

Bruker SMART CCD diffractometer	4118 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2871 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.978	R_int = 0.033
22480 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.05	Δρ_max = 0.31 e Å⁻³
4118 reflections	Δρ_min = −0.20 e Å⁻³
269 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₂₄H₂₉N₃O₂
M_r	391.50
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.0056 (16), 19.283 (3), 20.183 (3)
V (Å³)	4672.5 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.38 × 0.36 × 0.32

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.973, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	22480, 4118, 2871
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.148, 1.05
No. of reflections	4118
No. of parameters	269
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.20

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

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