Crystal structure of (E)-1-(4-chloro­phen­yl)ethanone O-de­hydro­abietyloxime

Zheng, J.-Q.; Cui, Y.-J.; Rao, X.-P.

doi:10.1107/S1600536814015888

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o899-o900

doi:10.1107/S1600536814015888

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Crystal structure of (E)-1-(4-chlorophenyl)ethanone O-dehydroabietyloxime

Jian-Qiang Zheng,^a Yan-Jie Cui ^a and Xiao-Ping Rao ^a ^*

^aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Key Lab. of Biomass Energy and Material, Jiangsu Province, National Engineering Lab. for Biomass Chemical Utilization, Key and Lab. on Forest Chemical Engineering, SFA, Nanjing, 210042, People's Republic of China
^*Correspondence e-mail: rxping2001@163.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 July 2014; accepted 8 July 2014; online 1 August 2014)

The title compound, C₂₈H₃₄ClNO₂ {systematic name: (E)-1-(4-chlorophenyl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carbonyl]oxime}, was synthesized from dehydroabietic acid. In the dehydroabietyl moiety, the central and terminal cyclohexane rings display chair and half-chair conformations, respectively, and a trans-ring junction. The C=N bond is in an E conformation and the C—O—N=C torsion angle is 148.1 (5)°. No directional interactions except van der Waals contacts occur in the crystal structure.

Keywords: crystal structure; dehydroabietic acid derivative; oxime.

CCDC reference: 1012686

1. Related literature

For the biological activity of dehydroabietic acid derivatives, see: Cui et al. (2013 ); Rao et al. (2008 ); Sepulveda et al. (2005 ). For the crystal structures of dehydroabietic acid derivatives, see: Rao et al. (2006 , 2009 ).

2. Experimental

2.1. Crystal data

C₂₈H₃₄ClNO₂
M_r = 452.01
Orthorhombic, P 2₁ 2₁ 2₁
a = 28.804 (6) Å
b = 6.1760 (12) Å
c = 13.922 (3) Å
V = 2476.6 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

2.2. Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.948, T_max = 0.982
5186 measured reflections
4554 independent reflections
2566 reflections with I > 2σ(I)
R_int = 0.099
3 standard reflections every 200 reflections intensity decay: 1%

2.3. Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.205
S = 1.00
4554 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1911 Friedel pairs
Absolute structure parameter: 0.05 (16)

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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

CCDC reference: 1012686

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814015888/hb7249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015888/hb7249Isup2.hkl

checkCIF report

Related literature top

For the biological activity of dehydroabietic acid derivatives, see: Cui et al. (2013); Rao et al. (2008); Sepulveda et al. (2005). For the crystal structures of dehydroabietic acid derivatives, see: Rao et al. (2006, 2009).

Experimental top

A solution of dehydroabietyl chloride in 15 ml CH₂Cl₂ solution were added dropwise to a solution of 60 mmol oxime and 60 mmol triethylamine in 40 ml CH₂Cl₂ solution within 30 min between the temperature 0–5 °C. The reaction mixture was allowed to stand at room temperature over 2 h and washed with water, then dried with anhydrous MgSO₄. The residue were purified by silica gel chromatography.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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. Molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

(E)-1-(4-Chlorophenyl)ethanone O-dehydroabietyloxime top

Crystal data top

C₂₈H₃₄ClNO₂	F(000) = 968
M_r = 452.01	D_x = 1.212 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 28.804 (6) Å	θ = 9–13°
b = 6.1760 (12) Å	µ = 0.18 mm⁻¹
c = 13.922 (3) Å	T = 293 K
V = 2476.6 (9) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2566 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.099
Graphite monochromator	θ_max = 25.4°, θ_min = 1.4°
ω/2θ scans	h = −34→34
Absorption correction: ψ scan (North et al., 1968)	k = 0→7
T_min = 0.948, T_max = 0.982	l = 0→16
5186 measured reflections	3 standard reflections every 200 reflections
4554 independent reflections	intensity decay: 1%

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)] = 0.069	H-atom parameters constrained
wR(F²) = 0.205	w = 1/[σ²(F_o²) + (0.1P)² + 0.3P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4554 reflections	Δρ_max = 0.18 e Å⁻³
289 parameters	Δρ_min = −0.23 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1911 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (16)

Crystal data top

C₂₈H₃₄ClNO₂	V = 2476.6 (9) Å³
M_r = 452.01	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 28.804 (6) Å	µ = 0.18 mm⁻¹
b = 6.1760 (12) Å	T = 293 K
c = 13.922 (3) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2566 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.099
T_min = 0.948, T_max = 0.982	3 standard reflections every 200 reflections
5186 measured reflections	intensity decay: 1%
4554 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	H-atom parameters constrained
wR(F²) = 0.205	Δρ_max = 0.18 e Å⁻³
S = 1.00	Δρ_min = −0.23 e Å⁻³
4554 reflections	Absolute structure: Flack (1983), 1911 Friedel pairs
289 parameters	Absolute structure parameter: 0.05 (16)
0 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
Cl	0.59358 (6)	0.1759 (3)	0.58245 (11)	0.0903 (6)
N	0.41858 (16)	0.1075 (8)	0.2777 (4)	0.0786 (15)
O1	0.34454 (14)	0.3392 (7)	0.2493 (3)	0.0917 (14)
C1	0.0874 (3)	0.9817 (14)	0.1786 (7)	0.143 (4)
H1A	0.0598	1.0654	0.1890	0.214*
H1B	0.1088	1.0637	0.1403	0.214*
H1C	0.1014	0.9479	0.2393	0.214*
O2	0.38242 (13)	0.0305 (7)	0.2150 (3)	0.0774 (12)
C2	0.0380 (2)	0.6446 (14)	0.1772 (5)	0.106 (2)
H2A	0.0303	0.5175	0.1409	0.159*
H2B	0.0109	0.7334	0.1844	0.159*
H2C	0.0492	0.6028	0.2394	0.159*
C3	0.07480 (18)	0.7692 (9)	0.1256 (4)	0.0707 (16)
H3A	0.0617	0.8110	0.0634	0.085*
C4	0.11734 (16)	0.6380 (9)	0.1050 (4)	0.0564 (13)
C5	0.13208 (17)	0.5982 (9)	0.0124 (4)	0.0574 (13)
H5A	0.1154	0.6568	−0.0386	0.069*
C6	0.17069 (17)	0.4744 (8)	−0.0067 (3)	0.0527 (12)
H6A	0.1799	0.4552	−0.0701	0.063*
C7	0.19647 (15)	0.3765 (8)	0.0666 (3)	0.0463 (11)
C8	0.18179 (17)	0.4124 (8)	0.1606 (3)	0.0525 (13)
C9	0.14295 (17)	0.5418 (9)	0.1772 (4)	0.0574 (13)
H9A	0.1338	0.5645	0.2404	0.069*
C10	0.23686 (16)	0.2213 (8)	0.0425 (3)	0.0480 (11)
C11	0.26936 (15)	0.2185 (8)	0.1322 (3)	0.0492 (11)
H11A	0.2772	0.3707	0.1440	0.059*
C12	0.24209 (17)	0.1469 (9)	0.2209 (3)	0.0560 (13)
H12A	0.2265	0.0108	0.2079	0.067*
H12B	0.2632	0.1252	0.2744	0.067*
C13	0.20670 (18)	0.3184 (11)	0.2463 (3)	0.0711 (16)
H13A	0.1839	0.2558	0.2895	0.085*
H13B	0.2222	0.4346	0.2805	0.085*
C14	0.26495 (17)	0.3094 (9)	−0.0430 (3)	0.0589 (13)
H14A	0.2462	0.3009	−0.1007	0.071*
H14B	0.2722	0.4606	−0.0317	0.071*
C15	0.30964 (17)	0.1850 (10)	−0.0586 (3)	0.0646 (14)
H15A	0.3024	0.0354	−0.0737	0.077*
H15B	0.3262	0.2463	−0.1129	0.077*
C16	0.34032 (18)	0.1924 (10)	0.0290 (3)	0.0631 (14)
H16A	0.3496	0.3412	0.0406	0.076*
H16B	0.3682	0.1091	0.0165	0.076*
C17	0.31646 (17)	0.1025 (7)	0.1202 (3)	0.0487 (11)
C18	0.21533 (19)	0.0064 (8)	0.0147 (4)	0.0611 (14)
H18A	0.1982	−0.0505	0.0682	0.092*
H18B	0.2394	−0.0936	−0.0029	0.092*
H18C	0.1948	0.0272	−0.0388	0.092*
C19	0.3132 (2)	−0.1455 (8)	0.1193 (4)	0.0704 (15)
H19A	0.3437	−0.2060	0.1118	0.106*
H19B	0.2939	−0.1909	0.0668	0.106*
H19C	0.2999	−0.1948	0.1787	0.106*
C20	0.34771 (18)	0.1739 (10)	0.2020 (4)	0.0627 (14)
C21	0.43576 (18)	−0.0547 (9)	0.3230 (4)	0.0562 (13)
C22	0.4184 (2)	−0.2817 (10)	0.3171 (5)	0.0831 (19)
H22A	0.3926	−0.2881	0.2734	0.125*
H22B	0.4085	−0.3287	0.3796	0.125*
H22C	0.4428	−0.3745	0.2945	0.125*
C23	0.47602 (16)	−0.0019 (9)	0.3849 (3)	0.0551 (12)
C24	0.4921 (2)	−0.1439 (10)	0.4542 (4)	0.0766 (17)
H24A	0.4777	−0.2780	0.4605	0.092*
C25	0.5287 (2)	−0.0937 (11)	0.5145 (4)	0.0809 (19)
H25A	0.5389	−0.1922	0.5604	0.097*
C26	0.54968 (19)	0.1069 (11)	0.5048 (4)	0.0647 (15)
C27	0.53477 (18)	0.2524 (11)	0.4368 (4)	0.0698 (16)
H27A	0.5491	0.3868	0.4314	0.084*
C28	0.49870 (18)	0.1988 (9)	0.3768 (4)	0.0653 (14)
H28A	0.4891	0.2968	0.3301	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0746 (9)	0.1184 (14)	0.0778 (10)	−0.0015 (10)	−0.0227 (8)	0.0008 (10)
N	0.069 (3)	0.072 (3)	0.095 (4)	−0.004 (3)	−0.039 (3)	−0.005 (3)
O1	0.080 (3)	0.081 (3)	0.113 (3)	0.019 (2)	−0.041 (3)	−0.049 (3)
C1	0.094 (5)	0.082 (5)	0.253 (11)	0.014 (5)	0.004 (6)	−0.073 (7)
O2	0.070 (2)	0.062 (2)	0.099 (3)	0.011 (2)	−0.036 (2)	−0.017 (2)
C2	0.069 (4)	0.109 (6)	0.139 (6)	0.014 (4)	0.026 (4)	0.023 (5)
C3	0.064 (3)	0.067 (4)	0.080 (4)	0.011 (3)	0.000 (3)	0.003 (3)
C4	0.050 (3)	0.062 (3)	0.057 (3)	−0.001 (3)	−0.004 (2)	−0.004 (3)
C5	0.054 (3)	0.064 (3)	0.054 (3)	0.001 (3)	−0.014 (2)	0.000 (3)
C6	0.060 (3)	0.059 (3)	0.039 (3)	0.003 (3)	−0.006 (2)	−0.005 (2)
C7	0.045 (2)	0.054 (3)	0.040 (3)	−0.001 (2)	−0.0046 (19)	−0.003 (2)
C8	0.052 (3)	0.066 (3)	0.040 (3)	0.011 (3)	−0.003 (2)	0.003 (2)
C9	0.056 (3)	0.073 (3)	0.044 (3)	0.001 (3)	0.001 (2)	−0.004 (3)
C10	0.055 (3)	0.052 (3)	0.038 (2)	−0.007 (2)	0.000 (2)	−0.002 (2)
C11	0.047 (2)	0.055 (3)	0.046 (3)	−0.003 (2)	−0.003 (2)	0.001 (2)
C12	0.062 (3)	0.059 (3)	0.046 (3)	0.005 (3)	−0.003 (2)	0.009 (2)
C13	0.071 (3)	0.099 (4)	0.044 (3)	0.021 (4)	0.006 (3)	0.009 (3)
C14	0.063 (3)	0.074 (3)	0.040 (3)	−0.002 (3)	0.001 (2)	0.005 (3)
C15	0.060 (3)	0.074 (4)	0.059 (3)	0.005 (3)	0.014 (3)	0.001 (3)
C16	0.057 (3)	0.070 (3)	0.063 (3)	−0.001 (3)	0.005 (3)	−0.007 (3)
C17	0.050 (3)	0.042 (3)	0.054 (3)	−0.006 (2)	−0.006 (2)	−0.005 (2)
C18	0.071 (3)	0.049 (3)	0.063 (3)	−0.013 (3)	−0.011 (3)	−0.008 (2)
C19	0.079 (4)	0.043 (3)	0.089 (4)	−0.002 (3)	−0.015 (3)	−0.010 (3)
C20	0.055 (3)	0.067 (4)	0.065 (3)	0.007 (3)	−0.009 (3)	−0.006 (3)
C21	0.055 (3)	0.062 (3)	0.052 (3)	0.002 (3)	0.000 (2)	0.001 (3)
C22	0.079 (4)	0.071 (4)	0.099 (5)	−0.021 (3)	−0.014 (3)	0.027 (3)
C23	0.049 (3)	0.064 (3)	0.053 (3)	0.004 (3)	0.004 (2)	0.003 (3)
C24	0.086 (4)	0.070 (4)	0.074 (4)	0.005 (4)	−0.017 (3)	0.012 (3)
C25	0.091 (5)	0.077 (4)	0.075 (4)	0.009 (4)	−0.025 (4)	0.015 (3)
C26	0.058 (3)	0.084 (4)	0.052 (3)	0.011 (3)	−0.003 (3)	0.002 (3)
C27	0.053 (3)	0.082 (4)	0.074 (4)	−0.011 (3)	−0.008 (3)	0.004 (3)
C28	0.061 (3)	0.065 (3)	0.070 (3)	−0.004 (3)	−0.008 (3)	0.020 (3)

Geometric parameters (Å, º) top

Cl—C26	1.717 (6)	C13—H13A	0.9700
N—C21	1.284 (7)	C13—H13B	0.9700
N—O2	1.441 (5)	C14—C15	1.515 (7)
O1—C20	1.218 (6)	C14—H14A	0.9700
C1—C3	1.549 (9)	C14—H14B	0.9700
C1—H1A	0.9600	C15—C16	1.507 (7)
C1—H1B	0.9600	C15—H15A	0.9700
C1—H1C	0.9600	C15—H15B	0.9700
O2—C20	1.348 (6)	C16—C17	1.547 (7)
C2—C3	1.493 (8)	C16—H16A	0.9700
C2—H2A	0.9600	C16—H16B	0.9700
C2—H2B	0.9600	C17—C20	1.517 (7)
C2—H2C	0.9600	C17—C19	1.535 (6)
C3—C4	1.497 (7)	C18—H18A	0.9600
C3—H3A	0.9800	C18—H18B	0.9600
C4—C5	1.379 (7)	C18—H18C	0.9600
C4—C9	1.381 (7)	C19—H19A	0.9600
C5—C6	1.376 (7)	C19—H19B	0.9600
C5—H5A	0.9300	C19—H19C	0.9600
C6—C7	1.399 (6)	C21—C23	1.481 (7)
C6—H6A	0.9300	C21—C22	1.491 (8)
C7—C8	1.393 (6)	C22—H22A	0.9600
C7—C10	1.544 (7)	C22—H22B	0.9600
C8—C9	1.394 (7)	C22—H22C	0.9600
C8—C13	1.509 (6)	C23—C24	1.383 (7)
C9—H9A	0.9300	C23—C28	1.406 (7)
C10—C18	1.515 (7)	C24—C25	1.383 (8)
C10—C14	1.538 (6)	C24—H24A	0.9300
C10—C11	1.561 (6)	C25—C26	1.385 (9)
C11—C12	1.528 (6)	C25—H25A	0.9300
C11—C17	1.543 (7)	C26—C27	1.374 (8)
C11—H11A	0.9800	C27—C28	1.374 (7)
C12—C13	1.512 (7)	C27—H27A	0.9300
C12—H12A	0.9700	C28—H28A	0.9300
C12—H12B	0.9700

C21—N—O2	108.6 (5)	C10—C14—H14A	109.2
C3—C1—H1A	109.5	C15—C14—H14B	109.2
C3—C1—H1B	109.5	C10—C14—H14B	109.2
H1A—C1—H1B	109.5	H14A—C14—H14B	107.9
C3—C1—H1C	109.5	C16—C15—C14	111.5 (4)
H1A—C1—H1C	109.5	C16—C15—H15A	109.3
H1B—C1—H1C	109.5	C14—C15—H15A	109.3
C20—O2—N	113.6 (4)	C16—C15—H15B	109.3
C3—C2—H2A	109.5	C14—C15—H15B	109.3
C3—C2—H2B	109.5	H15A—C15—H15B	108.0
H2A—C2—H2B	109.5	C15—C16—C17	113.1 (4)
C3—C2—H2C	109.5	C15—C16—H16A	108.9
H2A—C2—H2C	109.5	C17—C16—H16A	108.9
H2B—C2—H2C	109.5	C15—C16—H16B	108.9
C2—C3—C4	113.2 (5)	C17—C16—H16B	108.9
C2—C3—C1	112.0 (6)	H16A—C16—H16B	107.8
C4—C3—C1	111.0 (5)	C20—C17—C19	109.5 (4)
C2—C3—H3A	106.7	C20—C17—C11	107.8 (4)
C4—C3—H3A	106.7	C19—C17—C11	114.2 (4)
C1—C3—H3A	106.7	C20—C17—C16	104.4 (4)
C5—C4—C9	116.1 (5)	C19—C17—C16	112.2 (4)
C5—C4—C3	121.9 (5)	C11—C17—C16	108.2 (4)
C9—C4—C3	122.0 (5)	C10—C18—H18A	109.5
C6—C5—C4	121.9 (5)	C10—C18—H18B	109.5
C6—C5—H5A	119.0	H18A—C18—H18B	109.5
C4—C5—H5A	119.0	C10—C18—H18C	109.5
C5—C6—C7	121.9 (5)	H18A—C18—H18C	109.5
C5—C6—H6A	119.0	H18B—C18—H18C	109.5
C7—C6—H6A	119.0	C17—C19—H19A	109.5
C8—C7—C6	117.1 (4)	C17—C19—H19B	109.5
C8—C7—C10	122.1 (4)	H19A—C19—H19B	109.5
C6—C7—C10	120.7 (4)	C17—C19—H19C	109.5
C7—C8—C9	119.4 (4)	H19A—C19—H19C	109.5
C7—C8—C13	122.5 (4)	H19B—C19—H19C	109.5
C9—C8—C13	118.1 (4)	O1—C20—O2	122.3 (5)
C4—C9—C8	123.7 (5)	O1—C20—C17	127.2 (5)
C4—C9—H9A	118.2	O2—C20—C17	110.4 (5)
C8—C9—H9A	118.2	N—C21—C23	114.6 (5)
C18—C10—C14	109.1 (4)	N—C21—C22	125.3 (5)
C18—C10—C7	106.9 (4)	C23—C21—C22	120.2 (5)
C14—C10—C7	110.2 (4)	C21—C22—H22A	109.5
C18—C10—C11	116.1 (4)	C21—C22—H22B	109.5
C14—C10—C11	107.9 (4)	H22A—C22—H22B	109.5
C7—C10—C11	106.5 (3)	C21—C22—H22C	109.5
C12—C11—C17	113.9 (4)	H22A—C22—H22C	109.5
C12—C11—C10	109.9 (4)	H22B—C22—H22C	109.5
C17—C11—C10	116.5 (4)	C24—C23—C28	117.4 (5)
C12—C11—H11A	105.1	C24—C23—C21	121.9 (5)
C17—C11—H11A	105.1	C28—C23—C21	120.8 (5)
C10—C11—H11A	105.1	C25—C24—C23	122.4 (6)
C13—C12—C11	109.5 (4)	C25—C24—H24A	118.8
C13—C12—H12A	109.8	C23—C24—H24A	118.8
C11—C12—H12A	109.8	C24—C25—C26	118.3 (6)
C13—C12—H12B	109.8	C24—C25—H25A	120.8
C11—C12—H12B	109.8	C26—C25—H25A	120.8
H12A—C12—H12B	108.2	C27—C26—C25	121.0 (5)
C8—C13—C12	113.9 (4)	C27—C26—Cl	120.1 (5)
C8—C13—H13A	108.8	C25—C26—Cl	118.8 (5)
C12—C13—H13A	108.8	C28—C27—C26	119.9 (6)
C8—C13—H13B	108.8	C28—C27—H27A	120.1
C12—C13—H13B	108.8	C26—C27—H27A	120.1
H13A—C13—H13B	107.7	C27—C28—C23	121.0 (5)
C15—C14—C10	112.2 (4)	C27—C28—H28A	119.5
C15—C14—H14A	109.2	C23—C28—H28A	119.5

C21—N—O2—C20	148.1 (5)	C11—C10—C14—C15	54.1 (5)
C2—C3—C4—C5	118.1 (6)	C10—C14—C15—C16	−58.8 (6)
C1—C3—C4—C5	−115.0 (7)	C14—C15—C16—C17	57.7 (6)
C2—C3—C4—C9	−59.0 (7)	C12—C11—C17—C20	−67.0 (5)
C1—C3—C4—C9	68.0 (8)	C10—C11—C17—C20	163.4 (4)
C9—C4—C5—C6	−1.6 (7)	C12—C11—C17—C19	54.9 (6)
C3—C4—C5—C6	−178.8 (5)	C10—C11—C17—C19	−74.7 (5)
C4—C5—C6—C7	1.9 (8)	C12—C11—C17—C16	−179.3 (4)
C5—C6—C7—C8	−1.0 (7)	C10—C11—C17—C16	51.1 (5)
C5—C6—C7—C10	174.3 (4)	C15—C16—C17—C20	−166.7 (5)
C6—C7—C8—C9	−0.1 (7)	C15—C16—C17—C19	74.9 (6)
C10—C7—C8—C9	−175.3 (4)	C15—C16—C17—C11	−52.1 (6)
C6—C7—C8—C13	−179.4 (5)	N—O2—C20—O1	−9.4 (8)
C10—C7—C8—C13	5.4 (8)	N—O2—C20—C17	168.2 (4)
C5—C4—C9—C8	0.5 (8)	C19—C17—C20—O1	−147.7 (6)
C3—C4—C9—C8	177.7 (5)	C11—C17—C20—O1	−23.0 (8)
C7—C8—C9—C4	0.3 (8)	C16—C17—C20—O1	91.9 (7)
C13—C8—C9—C4	179.6 (5)	C19—C17—C20—O2	34.8 (6)
C8—C7—C10—C18	97.1 (5)	C11—C17—C20—O2	159.5 (4)
C6—C7—C10—C18	−77.9 (5)	C16—C17—C20—O2	−85.6 (5)
C8—C7—C10—C14	−144.4 (5)	O2—N—C21—C23	175.4 (4)
C6—C7—C10—C14	40.6 (6)	O2—N—C21—C22	−4.5 (8)
C8—C7—C10—C11	−27.6 (6)	N—C21—C23—C24	165.3 (5)
C6—C7—C10—C11	157.4 (4)	C22—C21—C23—C24	−14.8 (8)
C18—C10—C11—C12	−61.1 (5)	N—C21—C23—C28	−13.0 (7)
C14—C10—C11—C12	176.1 (4)	C22—C21—C23—C28	167.0 (5)
C7—C10—C11—C12	57.8 (5)	C28—C23—C24—C25	0.4 (8)
C18—C10—C11—C17	70.3 (5)	C21—C23—C24—C25	−177.9 (5)
C14—C10—C11—C17	−52.5 (5)	C23—C24—C25—C26	0.3 (9)
C7—C10—C11—C17	−170.8 (4)	C24—C25—C26—C27	−0.3 (9)
C17—C11—C12—C13	159.6 (4)	C24—C25—C26—Cl	177.3 (5)
C10—C11—C12—C13	−67.6 (5)	C25—C26—C27—C28	−0.5 (9)
C7—C8—C13—C12	−12.1 (8)	Cl—C26—C27—C28	−178.0 (4)
C9—C8—C13—C12	168.6 (5)	C26—C27—C28—C23	1.2 (8)
C11—C12—C13—C8	42.0 (6)	C24—C23—C28—C27	−1.2 (8)
C18—C10—C14—C15	−72.9 (5)	C21—C23—C28—C27	177.1 (5)
C7—C10—C14—C15	170.0 (4)

Experimental details

Crystal data
Chemical formula	C₂₈H₃₄ClNO₂
M_r	452.01
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	28.804 (6), 6.1760 (12), 13.922 (3)
V (Å³)	2476.6 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.948, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	5186, 4554, 2566
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.205, 1.00
No. of reflections	4554
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.23
Absolute structure	Flack (1983), 1911 Friedel pairs
Absolute structure parameter	0.05 (16)

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This research was financially supported by grants from the Natural Science Foundation of Jiangsu Province (BK2011112).

References

Cui, Y. J., Rao, X. P., Shang, S. B., Song, J. & Gao, Y. Q. (2013). Lett. Drug Des. Discov. 10, 102–110. CAS Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Rao, X.-P., Song, Z.-Q., Gong, Y., Yao, X.-J. & Shang, S.-B. (2006). Acta Cryst. E62, o3450–o3451. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Rao, X. P., Song, Z. Q., He, L. & Jia, W. H. (2008). Chem. Pharm. Bull. 56,1575–1578. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rao, X.-P., Song, Z.-Q. & Shang, S.-B. (2009). Acta Cryst. E65, o2402. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sepulveda, B., Astudillo, L., Rodriguez, J., Yanez, T., Theoduloz, C. & Schmeda, G. (2005). Pharm. Res. 52, 429–437. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar