(E)-2-(4-tert-Butyl­phen­yl)-1-(4-chloro-1-ethyl-3-methyl-1H-pyrazol-5-yl)-2-cyano­ethenyl 2,2-dimethyl­propano­ate

Xu, M.; Yu, H.; Li, B.

doi:10.1107/S1600536810048087

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3271

https://doi.org/10.1107/S1600536810048087

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(E)-2-(4-tert-Butylphenyl)-1-(4-chloro-1-ethyl-3-methyl-1H-pyrazol-5-yl)-2-cyanoethenyl 2,2-dimethylpropanoate

Man Xu,^a Haibo Yu ^b and Bin Li ^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: libin1@sinochem.com

(Received 16 November 2010; accepted 18 November 2010; online 24 November 2010)

In the title compound, C₂₄H₃₀ClN₃O₂, the dihedral angle between the aromatic rings is 30.78 (10)°.

Related literature

For further synthetic details, see: Kenzo et al. (2006 ); Yang et al. (2009 ).

Experimental

Crystal data

C₂₄H₃₀ClN₃O₂
M_r = 427.96
Monoclinic, P 2₁
a = 9.997 (2) Å
b = 9.563 (2) Å
c = 12.751 (3) Å
β = 95.008 (4)°
V = 1214.4 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.951, T_max = 0.965
6269 measured reflections
4137 independent reflections
3802 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.087
S = 1.04
4137 reflections
279 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.16 e Å⁻³
Absolute structure: Flack (1983 ), 1848 Friedel pairs
Flack parameter: 0.08 (5)

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: https://doi.org/10.1107/S1600536810048087/hb5743sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048087/hb5743Isup2.hkl

checkCIF report

Related literature top

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 (Kenzo et al., 2006) with pivaloyl chloride in THF. 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-(4-chloro- 1-ethyl-3-methyl-1H-pyrazol-5-yl)-3-hydroxyacrylonitrile (0.69 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 (Yang et al., 2009). After separation through silica gel column chromatography (fluent: ethyl acetate/petroleum ether=1/20), The title product compound was gained as a white solid (0.38 g, 44%).

Anal. Calcd for C₂₄H₃₀Cl₁N₃O₂: C, 67.35; H, 7.07; Cl, 8.28; N, 9.82; O, 7.48. Found: C, 67.33; H, 7.10; N, Cl, 8.25; N, 9.88; O, 7.44. ¹H NMR(DMSO): 1.2 (s, 9H, CO(CH₃)₃), 1.34 (s, 9H, Ph-(CH₃)₃), 1.55 (t, 3H, CH₃), 2.27 (s, 3H, CH₃), 4.21 (q, 2H, N—CH₂), 7.47 (d, 2H, Ph), 7.53 (d, 2H, Ph).

Structure description top

For further synthetic details, see: Kenzo et al. (2006); Yang et al. (2009).

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.

(E)-2-(4-tert-Butylphenyl)-1-(4-chloro-1-ethyl-3-methyl- 1H-pyrazol-5-yl)-2-cyanoethenyl 2,2-dimethylpropanoate top

Crystal data top

C₂₄H₃₀ClN₃O₂	F(000) = 456
M_r = 427.96	D_x = 1.170 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3335 reflections
a = 9.997 (2) Å	θ = 2.7–25.8°
b = 9.563 (2) Å	µ = 0.18 mm⁻¹
c = 12.751 (3) Å	T = 296 K
β = 95.008 (4)°	Block, colorless
V = 1214.4 (5) Å³	0.28 × 0.22 × 0.20 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	4137 independent reflections
Radiation source: fine-focus sealed tube	3802 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
phi and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→5
T_min = 0.951, T_max = 0.965	k = −10→11
6269 measured reflections	l = −15→15

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0478P)² + 0.1092P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4137 reflections	Δρ_max = 0.11 e Å⁻³
279 parameters	Δρ_min = −0.16 e Å⁻³
8 restraints	Absolute structure: Flack (1983), 1848 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (5)

Crystal data top

C₂₄H₃₀ClN₃O₂	V = 1214.4 (5) Å³
M_r = 427.96	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.997 (2) Å	µ = 0.18 mm⁻¹
b = 9.563 (2) Å	T = 296 K
c = 12.751 (3) Å	0.28 × 0.22 × 0.20 mm
β = 95.008 (4)°

Data collection top

Bruker SMART CCD diffractometer	4137 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3802 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.965	R_int = 0.016
6269 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.087	Δρ_max = 0.11 e Å⁻³
S = 1.04	Δρ_min = −0.16 e Å⁻³
4137 reflections	Absolute structure: Flack (1983), 1848 Friedel pairs
279 parameters	Absolute structure parameter: 0.08 (5)
8 restraints

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
Cl1	0.89003 (6)	1.14801 (5)	0.28949 (4)	0.06542 (17)
O1	0.69009 (13)	0.98017 (15)	0.09872 (9)	0.0502 (3)
O2	0.59667 (17)	0.80823 (19)	0.18582 (19)	0.0901 (6)
N1	0.92650 (17)	0.75296 (19)	0.23618 (12)	0.0542 (4)
N2	0.99429 (19)	0.7577 (2)	0.33256 (13)	0.0651 (5)
N3	1.1085 (2)	0.7957 (3)	0.01367 (16)	0.0828 (7)
C1	0.5204 (3)	1.1651 (3)	0.1878 (4)	0.1185 (13)
H1A	0.5849	1.1989	0.1423	0.178*
H1B	0.5618	1.1578	0.2584	0.178*
H1C	0.4461	1.2289	0.1863	0.178*
C2	0.4021 (3)	1.0314 (4)	0.0406 (2)	0.1012 (11)
H2A	0.4597	1.0792	−0.0040	0.152*
H2B	0.3194	1.0821	0.0420	0.152*
H2C	0.3838	0.9389	0.0138	0.152*
C3	0.3704 (3)	0.9628 (4)	0.2233 (2)	0.0981 (10)
H3A	0.2958	1.0256	0.2254	0.147*
H3B	0.4142	0.9521	0.2929	0.147*
H3C	0.3388	0.8734	0.1974	0.147*
C4	0.47022 (19)	1.0221 (2)	0.15022 (16)	0.0540 (5)
C5	0.58760 (19)	0.9229 (2)	0.15010 (15)	0.0497 (5)
C6	0.81200 (18)	0.91176 (19)	0.10034 (14)	0.0430 (4)
C7	0.88055 (17)	0.8811 (2)	0.20482 (13)	0.0440 (4)
C8	0.92091 (18)	0.9714 (2)	0.28560 (14)	0.0482 (4)
C9	0.9922 (2)	0.8913 (3)	0.36254 (15)	0.0586 (5)
C10	0.9045 (3)	0.6173 (2)	0.18532 (18)	0.0647 (6)
H10A	0.9902	0.5703	0.1831	0.078*
H10B	0.8672	0.6317	0.1133	0.078*
C11	0.8120 (3)	0.5253 (3)	0.2403 (2)	0.0935 (9)
H11A	0.8471	0.5125	0.3122	0.140*
H11B	0.8045	0.4362	0.2057	0.140*
H11C	0.7250	0.5682	0.2384	0.140*
C12	1.0620 (3)	0.9383 (4)	0.46551 (19)	0.0897 (9)
H12A	1.1091	0.8607	0.4992	0.135*
H12B	0.9968	0.9730	0.5101	0.135*
H12C	1.1247	1.0112	0.4531	0.135*
C13	0.86574 (18)	0.89023 (19)	0.00893 (13)	0.0427 (4)
C14	1.0008 (2)	0.8375 (2)	0.01452 (15)	0.0543 (5)
C15	0.80271 (17)	0.91367 (19)	−0.09958 (13)	0.0399 (4)
C16	0.71135 (19)	1.0205 (2)	−0.12567 (14)	0.0479 (4)
H16	0.6865	1.0812	−0.0738	0.058*
C17	0.6574 (2)	1.0365 (2)	−0.22854 (14)	0.0500 (4)
H17	0.5960	1.1081	−0.2443	0.060*
C18	0.69157 (18)	0.9496 (2)	−0.30907 (14)	0.0447 (4)
C19	0.78522 (18)	0.8452 (2)	−0.28222 (14)	0.0480 (4)
H19	0.8117	0.7858	−0.3344	0.058*
C20	0.83964 (18)	0.8279 (2)	−0.18000 (14)	0.0455 (4)
H20	0.9023	0.7574	−0.1646	0.055*
C21	0.6305 (2)	0.9735 (3)	−0.42226 (15)	0.0561 (5)
C22	0.6697 (3)	0.8575 (3)	−0.49666 (18)	0.0821 (8)
H22A	0.7654	0.8563	−0.4986	0.123*
H22B	0.6278	0.8746	−0.5661	0.123*
H22C	0.6402	0.7688	−0.4719	0.123*
C23	0.4769 (2)	0.9764 (4)	−0.42351 (19)	0.0783 (7)
H23A	0.4465	0.8918	−0.3927	0.117*
H23B	0.4380	0.9838	−0.4948	0.117*
H23C	0.4502	1.0553	−0.3838	0.117*
C24	0.6812 (3)	1.1146 (3)	−0.46001 (19)	0.0822 (8)
H24A	0.6507	1.1881	−0.4167	0.123*
H24B	0.6471	1.1298	−0.5318	0.123*
H24C	0.7776	1.1142	−0.4551	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0804 (4)	0.0545 (3)	0.0619 (3)	−0.0092 (3)	0.0091 (3)	−0.0059 (3)
O1	0.0546 (7)	0.0564 (8)	0.0402 (6)	0.0170 (6)	0.0082 (5)	0.0091 (6)
O2	0.0584 (9)	0.0596 (11)	0.1548 (18)	0.0126 (8)	0.0241 (10)	0.0312 (11)
N1	0.0626 (10)	0.0576 (11)	0.0410 (9)	0.0147 (8)	−0.0034 (7)	0.0008 (8)
N2	0.0675 (11)	0.0796 (14)	0.0456 (9)	0.0214 (10)	−0.0095 (8)	0.0045 (9)
N3	0.0511 (11)	0.1263 (19)	0.0710 (13)	0.0190 (12)	0.0066 (9)	0.0174 (13)
C1	0.0711 (17)	0.077 (2)	0.207 (4)	0.0204 (16)	0.009 (2)	−0.053 (2)
C2	0.0701 (16)	0.155 (3)	0.0763 (17)	0.0369 (19)	−0.0084 (13)	0.0102 (18)
C3	0.0764 (17)	0.121 (3)	0.102 (2)	0.0366 (17)	0.0362 (15)	0.0311 (19)
C4	0.0486 (10)	0.0575 (13)	0.0553 (11)	0.0138 (9)	0.0016 (8)	0.0002 (9)
C5	0.0475 (10)	0.0491 (12)	0.0516 (11)	0.0068 (8)	−0.0006 (8)	−0.0003 (9)
C6	0.0443 (9)	0.0452 (10)	0.0391 (9)	0.0031 (8)	0.0017 (7)	0.0025 (8)
C7	0.0426 (9)	0.0539 (11)	0.0355 (9)	0.0048 (8)	0.0042 (7)	0.0036 (8)
C8	0.0467 (10)	0.0565 (12)	0.0414 (10)	−0.0007 (9)	0.0042 (7)	−0.0012 (9)
C9	0.0513 (11)	0.0828 (16)	0.0402 (10)	0.0062 (11)	−0.0042 (8)	−0.0017 (10)
C10	0.0813 (15)	0.0554 (14)	0.0575 (12)	0.0162 (11)	0.0066 (10)	−0.0007 (10)
C11	0.125 (2)	0.075 (2)	0.0812 (17)	−0.0070 (17)	0.0135 (16)	0.0099 (14)
C12	0.0813 (17)	0.124 (3)	0.0584 (15)	0.0087 (16)	−0.0253 (12)	−0.0148 (15)
C13	0.0432 (8)	0.0458 (11)	0.0390 (9)	0.0012 (7)	0.0022 (7)	0.0026 (8)
C14	0.0452 (9)	0.0750 (14)	0.0428 (10)	0.0035 (9)	0.0043 (8)	0.0080 (9)
C15	0.0391 (9)	0.0426 (10)	0.0381 (9)	−0.0048 (7)	0.0047 (7)	0.0016 (8)
C16	0.0590 (11)	0.0455 (11)	0.0393 (9)	0.0045 (9)	0.0049 (8)	0.0006 (8)
C17	0.0603 (11)	0.0470 (11)	0.0426 (10)	0.0089 (9)	0.0039 (8)	0.0073 (8)
C18	0.0456 (9)	0.0498 (11)	0.0387 (9)	−0.0062 (8)	0.0035 (7)	0.0056 (7)
C19	0.0493 (10)	0.0575 (12)	0.0382 (10)	−0.0008 (9)	0.0090 (8)	−0.0047 (8)
C20	0.0416 (9)	0.0523 (11)	0.0431 (10)	0.0067 (8)	0.0061 (7)	0.0038 (8)
C21	0.0568 (11)	0.0720 (14)	0.0393 (10)	−0.0041 (10)	0.0024 (8)	0.0033 (10)
C22	0.0937 (18)	0.106 (2)	0.0452 (13)	0.0079 (16)	−0.0039 (12)	−0.0117 (13)
C23	0.0596 (13)	0.112 (2)	0.0608 (13)	−0.0039 (14)	−0.0105 (10)	0.0039 (14)
C24	0.0965 (18)	0.096 (2)	0.0527 (13)	−0.0131 (15)	−0.0027 (12)	0.0278 (13)

Geometric parameters (Å, º) top

Cl1—C8	1.718 (2)	C11—H11B	0.9600
O1—C5	1.377 (2)	C11—H11C	0.9600
O1—C6	1.382 (2)	C12—H12A	0.9600
O2—C5	1.187 (3)	C12—H12B	0.9600
N1—N2	1.351 (2)	C12—H12C	0.9600
N1—C7	1.356 (3)	C13—C14	1.437 (3)
N1—C10	1.459 (3)	C13—C15	1.486 (2)
N2—C9	1.334 (3)	C15—C20	1.388 (3)
N3—C14	1.149 (3)	C15—C16	1.391 (3)
C1—C4	1.519 (4)	C16—C17	1.382 (2)
C1—H1A	0.9600	C16—H16	0.9300
C1—H1B	0.9600	C17—C18	1.387 (3)
C1—H1C	0.9600	C17—H17	0.9300
C2—C4	1.503 (3)	C18—C19	1.391 (3)
C2—H2A	0.9600	C18—C21	1.534 (3)
C2—H2B	0.9600	C19—C20	1.378 (3)
C2—H2C	0.9600	C19—H19	0.9300
C3—C4	1.532 (3)	C20—H20	0.9300
C3—H3A	0.9600	C21—C22	1.533 (4)
C3—H3B	0.9600	C21—C24	1.534 (3)
C3—H3C	0.9600	C21—C23	1.534 (3)
C4—C5	1.509 (3)	C22—H22A	0.9600
C6—C13	1.341 (3)	C22—H22B	0.9600
C6—C7	1.473 (2)	C22—H22C	0.9600
C7—C8	1.378 (3)	C23—H23A	0.9600
C8—C9	1.391 (3)	C23—H23B	0.9600
C9—C12	1.501 (3)	C23—H23C	0.9600
C10—C11	1.495 (4)	C24—H24A	0.9600
C10—H10A	0.9700	C24—H24B	0.9600
C10—H10B	0.9700	C24—H24C	0.9600
C11—H11A	0.9600

C5—O1—C6	119.76 (15)	H11A—C11—H11C	109.5
N2—N1—C7	111.58 (17)	H11B—C11—H11C	109.5
N2—N1—C10	118.59 (18)	C9—C12—H12A	109.5
C7—N1—C10	129.66 (16)	C9—C12—H12B	109.5
C9—N2—N1	105.88 (17)	H12A—C12—H12B	109.5
C4—C1—H1A	109.5	C9—C12—H12C	109.5
C4—C1—H1B	109.5	H12A—C12—H12C	109.5
H1A—C1—H1B	109.5	H12B—C12—H12C	109.5
C4—C1—H1C	109.5	C6—C13—C14	117.17 (16)
H1A—C1—H1C	109.5	C6—C13—C15	128.05 (16)
H1B—C1—H1C	109.5	C14—C13—C15	114.78 (15)
C4—C2—H2A	109.5	N3—C14—C13	176.6 (2)
C4—C2—H2B	109.5	C20—C15—C16	117.94 (16)
H2A—C2—H2B	109.5	C20—C15—C13	118.69 (16)
C4—C2—H2C	109.5	C16—C15—C13	123.34 (16)
H2A—C2—H2C	109.5	C17—C16—C15	120.12 (17)
H2B—C2—H2C	109.5	C17—C16—H16	119.9
C4—C3—H3A	109.5	C15—C16—H16	119.9
C4—C3—H3B	109.5	C16—C17—C18	122.38 (17)
H3A—C3—H3B	109.5	C16—C17—H17	118.8
C4—C3—H3C	109.5	C18—C17—H17	118.8
H3A—C3—H3C	109.5	C17—C18—C19	116.85 (16)
H3B—C3—H3C	109.5	C17—C18—C21	120.26 (18)
C2—C4—C5	108.99 (18)	C19—C18—C21	122.86 (17)
C2—C4—C1	110.5 (3)	C20—C19—C18	121.39 (17)
C5—C4—C1	109.33 (18)	C20—C19—H19	119.3
C2—C4—C3	108.8 (2)	C18—C19—H19	119.3
C5—C4—C3	108.39 (19)	C19—C20—C15	121.29 (17)
C1—C4—C3	110.9 (2)	C19—C20—H20	119.4
O2—C5—O1	120.98 (18)	C15—C20—H20	119.4
O2—C5—C4	127.8 (2)	C22—C21—C24	109.5 (2)
O1—C5—C4	111.17 (17)	C22—C21—C18	111.85 (19)
C13—C6—O1	118.64 (15)	C24—C21—C18	108.12 (17)
C13—C6—C7	124.41 (16)	C22—C21—C23	108.4 (2)
O1—C6—C7	116.61 (15)	C24—C21—C23	109.8 (2)
N1—C7—C8	106.06 (16)	C18—C21—C23	109.15 (16)
N1—C7—C6	124.43 (17)	C21—C22—H22A	109.5
C8—C7—C6	129.32 (18)	C21—C22—H22B	109.5
C7—C8—C9	106.28 (19)	H22A—C22—H22B	109.5
C7—C8—Cl1	126.62 (15)	C21—C22—H22C	109.5
C9—C8—Cl1	127.10 (16)	H22A—C22—H22C	109.5
N2—C9—C8	110.19 (17)	H22B—C22—H22C	109.5
N2—C9—C12	121.3 (2)	C21—C23—H23A	109.5
C8—C9—C12	128.5 (2)	C21—C23—H23B	109.5
N1—C10—C11	113.0 (2)	H23A—C23—H23B	109.5
N1—C10—H10A	109.0	C21—C23—H23C	109.5
C11—C10—H10A	109.0	H23A—C23—H23C	109.5
N1—C10—H10B	109.0	H23B—C23—H23C	109.5
C11—C10—H10B	109.0	C21—C24—H24A	109.5
H10A—C10—H10B	107.8	C21—C24—H24B	109.5
C10—C11—H11A	109.5	H24A—C24—H24B	109.5
C10—C11—H11B	109.5	C21—C24—H24C	109.5
H11A—C11—H11B	109.5	H24A—C24—H24C	109.5
C10—C11—H11C	109.5	H24B—C24—H24C	109.5

C7—N1—N2—C9	−0.5 (2)	Cl1—C8—C9—C12	−1.7 (3)
C10—N1—N2—C9	−176.2 (2)	N2—N1—C10—C11	67.3 (3)
C6—O1—C5—O2	−8.6 (3)	C7—N1—C10—C11	−107.5 (3)
C6—O1—C5—C4	172.86 (15)	O1—C6—C13—C14	171.17 (17)
C2—C4—C5—O2	−107.5 (3)	C7—C6—C13—C14	−1.9 (3)
C1—C4—C5—O2	131.6 (3)	O1—C6—C13—C15	−9.1 (3)
C3—C4—C5—O2	10.7 (3)	C7—C6—C13—C15	177.85 (18)
C2—C4—C5—O1	70.9 (2)	C6—C13—C14—N3	−178 (100)
C1—C4—C5—O1	−49.9 (3)	C15—C13—C14—N3	2 (4)
C3—C4—C5—O1	−170.9 (2)	C6—C13—C15—C20	−148.6 (2)
C5—O1—C6—C13	129.59 (19)	C14—C13—C15—C20	31.2 (2)
C5—O1—C6—C7	−56.8 (2)	C6—C13—C15—C16	33.6 (3)
N2—N1—C7—C8	−0.2 (2)	C14—C13—C15—C16	−146.64 (19)
C10—N1—C7—C8	174.9 (2)	C20—C15—C16—C17	1.7 (3)
N2—N1—C7—C6	175.15 (17)	C13—C15—C16—C17	179.58 (17)
C10—N1—C7—C6	−9.7 (3)	C15—C16—C17—C18	−0.5 (3)
C13—C6—C7—N1	−58.8 (3)	C16—C17—C18—C19	−0.9 (3)
O1—C6—C7—N1	128.03 (19)	C16—C17—C18—C21	−178.96 (18)
C13—C6—C7—C8	115.5 (2)	C17—C18—C19—C20	1.0 (3)
O1—C6—C7—C8	−57.7 (3)	C21—C18—C19—C20	178.99 (17)
N1—C7—C8—C9	0.8 (2)	C18—C19—C20—C15	0.3 (3)
C6—C7—C8—C9	−174.29 (17)	C16—C15—C20—C19	−1.7 (3)
N1—C7—C8—Cl1	−179.68 (14)	C13—C15—C20—C19	−179.61 (17)
C6—C7—C8—Cl1	5.3 (3)	C17—C18—C21—C22	−174.0 (2)
N1—N2—C9—C8	1.0 (2)	C19—C18—C21—C22	8.1 (3)
N1—N2—C9—C12	−178.1 (2)	C17—C18—C21—C24	65.4 (2)
C7—C8—C9—N2	−1.1 (2)	C19—C18—C21—C24	−112.5 (2)
Cl1—C8—C9—N2	179.36 (16)	C17—C18—C21—C23	−54.0 (3)
C7—C8—C9—C12	177.9 (2)	C19—C18—C21—C23	128.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀ClN₃O₂
M_r	427.96
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.997 (2), 9.563 (2), 12.751 (3)
β (°)	95.008 (4)
V (Å³)	1214.4 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.28 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.951, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	6269, 4137, 3802
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.087, 1.04
No. of reflections	4137
No. of parameters	279
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.16
Absolute structure	Flack (1983), 1848 Friedel pairs
Absolute structure parameter	0.08 (5)

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

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kenzo, F., Yasuo, K., Norio, T., Hideaki, S., Masatoshi, O. & Koichi, N. (2006). US Patent 20060178523. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, P., Shen, D. L., Tan, C. X., Weng, J. Q., Lu, Q., Wei, Y. C. & Kong, X. L. (2009). Zhejiang Daxue Xuebao, 36, 183–185. CAS Google Scholar

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