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

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

doi:10.1107/S1600536814016882

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Page o948

doi:10.1107/S1600536814016882

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

Xiao-Ping Rao,^a ^* Yan-Jie Cui ^a and Jian-Qiang Zheng ^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 M. Lopez-Rodriguez, Universidad de La Laguna, Tenerife (Received 9 July 2014; accepted 22 July 2014; online 1 August 2014)

In the title compound, C₂₉H₃₇NO₃ {systematic name: (E)-1-(4-methoxyphenyl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carbonyl]oxime}, a new derivative of dehydroabietic acid, the two cyclohexane rings exhibit a trans-ring junction and are in chair and half-chair conformations. The C=N double bond exhibits an E conformation.

Keywords: crystal structure; oxime; dehydroabietic acid derivative; biological compounds.

CCDC reference: 1015316

1. Related literature

For the biological activity of related compounds, see: Cui et al. (2013 ); Li et al. (2008 ); Rao et al. (2008 ); Sepulveda et al. (2005 ); For the crystal structures of a related compound, see: Rao et al. (2009 ).

2. Experimental

2.1. Crystal data

C₂₉H₃₇NO₃
M_r = 447.60
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.1700 (12) Å
b = 11.051 (2) Å
c = 37.526 (8) Å
V = 2558.7 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 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 (CAD-4 Software; North et al., 1968 ) T_min = 0.978, T_max = 0.993
5399 measured reflections
4691 independent reflections
2211 reflections with I > 2σ(I)
R_int = 0.088
3 standard reflections every 200 reflections intensity decay: 1%

2.3. Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.183
S = 1.00
4691 reflections
298 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 e Å⁻³

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: 1015316

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814016882/lr2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814016882/lr2129Isup2.hkl

checkCIF report

Structural commentary top

Dehydroabietic acid is an important material for design and synthesis of biological compounds (Li et al., 2008; Rao et al., 2008; Sepulveda et al., 2005). As part of our ongoing project of dehydroabietic acid derivatives (Cui et al., 2013, Rao et al., 2009). we report herein the structure of the title compound. The structure of dehydroabietyl moiety in the title compound is comparable to that found for dehydroabietic acid and related compounds (Rao et al., 2009). There are three six-membered rings, which form planar, half-chair and chair conformations, respectively. the two cyclohexane rings are in trans ring junction with classic chair and half-chair conformations, respectively, Three chiral centers in the structure exhibit R–, S– and R– configurations, respectively. The C=N double bond is in E configuration.

Synthesis and crystallization top

60 mmol of Dehydroabietyl chloride in 15 ml CH₂Cl₂ were added dropwise to a 60 mmol (4-methoxyphenyl)ethanone oxime and 60 mmol triethylamine dissolved in 40 ml CH₂Cl₂ at a temperature 0–5°C. The reaction mixture was allowed to stand at room temperature for 2 h and then washed with water and dried over anhydrous MgSO₄. The residue was purified by silica gel chromatography.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms, and C—H = 0.97–0.98 Å and U_iso(H) = 1.2U_eq(C,N,H) for all other H atoms. Methyl groups were refined in orientation AFIX 137 of program SHELXL97.

Related literature top

For the biological activity of related compounds, see: Cui et al. (2013); Li et al. (2008); Rao et al. (2008); Sepulveda et al. (2005); For the crystal structures of a related compound, see: Rao et al. (2009).

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. The molecular structure of the title compound, hydrogen atoms are represented by small spheres of arbitrary radius and the displacement ellipsoids are at the 30% probability level.

(E)-1-(4-Methoxyphenyl)ethanone O-[(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carbonyl]oxime top

Crystal data top

C₂₉H₃₇NO₃	F(000) = 968
M_r = 447.60	D_x = 1.162 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.1700 (12) Å	θ = 9–13°
b = 11.051 (2) Å	µ = 0.07 mm⁻¹
c = 37.526 (8) Å	T = 293 K
V = 2558.7 (9) Å³	Block, white
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2211 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.088
Graphite monochromator	θ_max = 25.4°, θ_min = 1.1°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (CAD-4 Software; North et al., 1968)	k = 0→13
T_min = 0.978, T_max = 0.993	l = −45→45
5399 measured reflections	3 standard reflections every 200 reflections
4691 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.060P)²] where P = (F_o² + 2F_c²)/3
4691 reflections	(Δ/σ)_max < 0.001
298 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₉H₃₇NO₃	V = 2558.7 (9) Å³
M_r = 447.60	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.1700 (12) Å	µ = 0.07 mm⁻¹
b = 11.051 (2) Å	T = 293 K
c = 37.526 (8) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2211 reflections with I > 2σ(I)
Absorption correction: ψ scan (CAD-4 Software; North et al., 1968)	R_int = 0.088
T_min = 0.978, T_max = 0.993	3 standard reflections every 200 reflections
5399 measured reflections	intensity decay: 1%
4691 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	1 restraint
wR(F²) = 0.183	H-atom parameters constrained
S = 1.00	Δρ_max = 0.16 e Å⁻³
4691 reflections	Δρ_min = −0.17 e Å⁻³
298 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
N	0.1892 (7)	0.0800 (4)	0.03582 (11)	0.0798 (14)
O1	0.1751 (9)	−0.3034 (4)	−0.08665 (11)	0.1262 (18)
C1	0.3329 (16)	−0.3936 (6)	−0.0959 (2)	0.168 (4)
H1A	0.2748	−0.4457	−0.1140	0.252*
H1B	0.3680	−0.4407	−0.0751	0.252*
H1C	0.4616	−0.3549	−0.1047	0.252*
O2	0.2587 (6)	0.1742 (4)	0.06048 (9)	0.0806 (12)
C2	0.2309 (11)	−0.2209 (5)	−0.06054 (14)	0.0738 (16)
O3	−0.0806 (6)	0.1739 (4)	0.08121 (11)	0.1088 (16)
C3	0.4223 (10)	−0.2218 (5)	−0.04202 (14)	0.0784 (17)
H3A	0.5247	−0.2821	−0.0460	0.094*
C4	0.4604 (9)	−0.1316 (5)	−0.01735 (13)	0.0712 (16)
H4A	0.5918	−0.1306	−0.0052	0.085*
C5	0.3105 (8)	−0.0432 (5)	−0.01018 (12)	0.0590 (13)
C6	0.1146 (10)	−0.0433 (5)	−0.02848 (14)	0.0727 (16)
H6A	0.0097	0.0150	−0.0238	0.087*
C7	0.0789 (10)	−0.1324 (5)	−0.05395 (14)	0.0770 (16)
H7A	−0.0501	−0.1323	−0.0668	0.092*
C8	0.3520 (9)	0.0520 (6)	0.01648 (14)	0.0731 (16)
C9	0.5748 (10)	0.1086 (7)	0.01919 (18)	0.135 (3)
H9A	0.5759	0.1669	0.0381	0.202*
H9B	0.6099	0.1479	−0.0029	0.202*
H9C	0.6801	0.0468	0.0240	0.202*
C10	0.1024 (8)	0.2116 (5)	0.08260 (13)	0.0616 (13)
C11	0.1842 (8)	0.3063 (4)	0.10914 (12)	0.0548 (12)
C12	0.1060 (9)	0.4277 (5)	0.09359 (13)	0.0724 (16)
H12A	0.1925	0.4470	0.0728	0.087*
H12B	−0.0433	0.4191	0.0859	0.087*
C13	0.1212 (10)	0.5326 (4)	0.12026 (12)	0.0694 (15)
H13A	0.2719	0.5473	0.1262	0.083*
H13B	0.0627	0.6056	0.1096	0.083*
C14	−0.0049 (9)	0.5020 (4)	0.15382 (12)	0.0615 (14)
H14A	0.0084	0.5688	0.1704	0.074*
H14B	−0.1570	0.4940	0.1477	0.074*
C15	0.0682 (7)	0.3872 (4)	0.17213 (11)	0.0460 (11)
C16	0.0614 (7)	0.2829 (4)	0.14438 (11)	0.0501 (11)
H16A	−0.0913	0.2771	0.1374	0.060*
C17	−0.0814 (7)	0.3510 (4)	0.20262 (12)	0.0525 (12)
C18	−0.1403 (8)	0.2317 (5)	0.20981 (12)	0.0574 (13)
C19	−0.0723 (9)	0.1300 (4)	0.18619 (13)	0.0711 (15)
H19A	−0.1958	0.1046	0.1720	0.085*
H19B	−0.0292	0.0620	0.2009	0.085*
C20	0.1123 (8)	0.1615 (4)	0.16145 (13)	0.0659 (14)
H20A	0.1276	0.0998	0.1432	0.079*
H20B	0.2470	0.1664	0.1747	0.079*
C21	−0.1556 (9)	0.4395 (5)	0.22626 (13)	0.0650 (14)
H21A	−0.1182	0.5199	0.2222	0.078*
C22	−0.2828 (9)	0.4119 (5)	0.25553 (13)	0.0658 (14)
H22A	−0.3301	0.4733	0.2706	0.079*
C23	−0.3401 (9)	0.2922 (5)	0.26245 (13)	0.0623 (13)
C24	−0.2702 (9)	0.2063 (5)	0.23947 (13)	0.0696 (14)
H24A	−0.3104	0.1264	0.2436	0.084*
C25	0.4331 (8)	0.3015 (5)	0.11184 (15)	0.0794 (17)
H25A	0.4764	0.2251	0.1217	0.119*
H25B	0.4830	0.3658	0.1270	0.119*
H25C	0.4950	0.3106	0.0885	0.119*
C26	0.2970 (8)	0.4086 (4)	0.18935 (13)	0.0694 (15)
H26A	0.2883	0.4739	0.2062	0.104*
H26B	0.3996	0.4287	0.1710	0.104*
H26C	0.3430	0.3363	0.2013	0.104*
C27	−0.4765 (10)	0.2590 (5)	0.29540 (14)	0.0794 (17)
H27A	−0.4753	0.1706	0.2971	0.095*
C28	−0.3787 (12)	0.3065 (7)	0.32966 (14)	0.120 (3)
H28A	−0.4703	0.2851	0.3494	0.181*
H28B	−0.3660	0.3930	0.3283	0.181*
H28C	−0.2377	0.2716	0.3330	0.181*
C29	−0.7111 (11)	0.2963 (6)	0.29055 (18)	0.104 (2)
H29A	−0.7919	0.2758	0.3116	0.157*
H29B	−0.7712	0.2546	0.2704	0.157*
H29C	−0.7187	0.3820	0.2866	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.063 (3)	0.111 (4)	0.065 (3)	−0.009 (3)	0.001 (3)	−0.033 (3)
O1	0.185 (5)	0.093 (3)	0.101 (3)	0.023 (4)	−0.032 (4)	−0.031 (3)
C1	0.250 (11)	0.095 (5)	0.158 (7)	0.084 (7)	−0.017 (8)	−0.045 (5)
O2	0.063 (2)	0.115 (3)	0.064 (2)	−0.027 (2)	0.018 (2)	−0.035 (2)
C2	0.092 (4)	0.070 (4)	0.059 (3)	0.011 (4)	−0.003 (3)	0.000 (3)
O3	0.054 (2)	0.151 (4)	0.121 (3)	−0.029 (3)	0.003 (3)	−0.074 (3)
C3	0.094 (5)	0.074 (4)	0.067 (3)	0.024 (4)	0.005 (4)	0.006 (3)
C4	0.059 (3)	0.091 (4)	0.063 (3)	0.025 (3)	−0.006 (3)	−0.003 (3)
C5	0.052 (3)	0.077 (4)	0.048 (3)	0.000 (3)	−0.001 (3)	−0.003 (2)
C6	0.077 (4)	0.075 (4)	0.066 (3)	0.009 (3)	0.000 (3)	−0.012 (3)
C7	0.075 (4)	0.081 (4)	0.075 (4)	0.016 (4)	−0.011 (3)	−0.010 (3)
C8	0.058 (3)	0.112 (5)	0.049 (3)	−0.001 (3)	−0.001 (3)	−0.011 (3)
C9	0.062 (4)	0.216 (9)	0.127 (6)	−0.019 (5)	0.012 (4)	−0.075 (6)
C10	0.052 (3)	0.071 (3)	0.062 (3)	−0.003 (3)	0.002 (3)	−0.015 (3)
C11	0.040 (2)	0.072 (3)	0.053 (3)	−0.009 (3)	0.001 (2)	−0.014 (3)
C12	0.072 (4)	0.088 (4)	0.058 (3)	−0.017 (3)	−0.004 (3)	−0.002 (3)
C13	0.089 (4)	0.055 (3)	0.065 (3)	−0.005 (3)	0.014 (3)	0.006 (3)
C14	0.069 (3)	0.049 (3)	0.067 (3)	−0.005 (3)	0.007 (3)	−0.001 (2)
C15	0.045 (3)	0.040 (2)	0.053 (3)	−0.005 (2)	−0.005 (2)	0.003 (2)
C16	0.037 (3)	0.053 (3)	0.060 (3)	0.000 (2)	−0.005 (2)	−0.004 (2)
C17	0.049 (3)	0.053 (3)	0.055 (3)	0.006 (3)	−0.012 (2)	0.011 (2)
C18	0.050 (3)	0.074 (3)	0.049 (3)	0.003 (3)	−0.003 (2)	0.011 (2)
C19	0.077 (4)	0.063 (3)	0.073 (4)	−0.005 (3)	−0.004 (3)	0.000 (3)
C20	0.067 (4)	0.053 (3)	0.077 (3)	0.010 (3)	−0.009 (3)	−0.004 (3)
C21	0.068 (3)	0.065 (3)	0.062 (3)	0.004 (3)	−0.003 (3)	−0.005 (3)
C22	0.068 (3)	0.076 (3)	0.054 (3)	0.011 (3)	−0.004 (3)	−0.008 (3)
C23	0.065 (3)	0.067 (3)	0.055 (3)	−0.003 (3)	−0.003 (3)	0.008 (3)
C24	0.071 (4)	0.067 (3)	0.070 (3)	0.003 (3)	−0.007 (3)	0.010 (3)
C25	0.058 (3)	0.098 (4)	0.083 (4)	−0.013 (4)	−0.005 (3)	−0.008 (3)
C26	0.057 (3)	0.085 (4)	0.066 (3)	−0.026 (3)	−0.016 (3)	−0.008 (3)
C27	0.073 (4)	0.101 (4)	0.064 (4)	0.012 (4)	0.019 (3)	0.021 (3)
C28	0.136 (6)	0.166 (7)	0.059 (4)	0.012 (6)	0.003 (4)	0.011 (4)
C29	0.092 (5)	0.110 (5)	0.111 (5)	0.013 (4)	0.022 (4)	0.014 (4)

Geometric parameters (Å, º) top

N—C8	1.277 (6)	C15—C17	1.523 (6)
N—O2	1.458 (5)	C15—C16	1.555 (5)
O1—C2	1.382 (6)	C15—C26	1.571 (6)
O1—C1	1.436 (7)	C16—C20	1.519 (6)
C1—H1A	0.9600	C16—H16A	0.9800
C1—H1B	0.9600	C17—C18	1.393 (6)
C1—H1C	0.9600	C17—C21	1.398 (6)
O2—C10	1.338 (5)	C18—C24	1.400 (6)
C2—C3	1.370 (8)	C18—C19	1.492 (6)
C2—C7	1.377 (7)	C19—C20	1.510 (6)
O3—C10	1.204 (5)	C19—H19A	0.9700
C3—C4	1.381 (7)	C19—H19B	0.9700
C3—H3A	0.9300	C20—H20A	0.9700
C4—C5	1.371 (6)	C20—H20B	0.9700
C4—H4A	0.9300	C21—C22	1.384 (6)
C5—C6	1.390 (7)	C21—H21A	0.9300
C5—C8	1.475 (7)	C22—C23	1.394 (6)
C6—C7	1.390 (7)	C22—H22A	0.9300
C6—H6A	0.9300	C23—C24	1.353 (6)
C7—H7A	0.9300	C23—C27	1.540 (7)
C8—C9	1.514 (8)	C24—H24A	0.9300
C9—H9A	0.9600	C25—H25A	0.9600
C9—H9B	0.9600	C25—H25B	0.9600
C9—H9C	0.9600	C25—H25C	0.9600
C10—C11	1.530 (6)	C26—H26A	0.9600
C11—C12	1.540 (6)	C26—H26B	0.9600
C11—C16	1.546 (6)	C26—H26C	0.9600
C11—C25	1.540 (6)	C27—C29	1.516 (8)
C12—C13	1.535 (6)	C27—C28	1.514 (8)
C12—H12A	0.9700	C27—H27A	0.9800
C12—H12B	0.9700	C28—H28A	0.9600
C13—C14	1.519 (6)	C28—H28B	0.9600
C13—H13A	0.9700	C28—H28C	0.9600
C13—H13B	0.9700	C29—H29A	0.9600
C14—C15	1.511 (6)	C29—H29B	0.9600
C14—H14A	0.9700	C29—H29C	0.9600
C14—H14B	0.9700

C8—N—O2	107.6 (4)	C16—C15—C26	114.3 (4)
C2—O1—C1	117.4 (6)	C20—C16—C11	114.0 (4)
O1—C1—H1A	109.5	C20—C16—C15	111.5 (3)
O1—C1—H1B	109.5	C11—C16—C15	115.8 (4)
H1A—C1—H1B	109.5	C20—C16—H16A	104.7
O1—C1—H1C	109.5	C11—C16—H16A	104.7
H1A—C1—H1C	109.5	C15—C16—H16A	104.7
H1B—C1—H1C	109.5	C18—C17—C21	117.0 (5)
C10—O2—N	113.7 (4)	C18—C17—C15	123.5 (4)
C3—C2—C7	120.1 (5)	C21—C17—C15	119.4 (4)
C3—C2—O1	124.7 (6)	C17—C18—C24	119.6 (5)
C7—C2—O1	115.2 (6)	C17—C18—C19	121.6 (4)
C2—C3—C4	118.7 (5)	C24—C18—C19	118.8 (5)
C2—C3—H3A	120.6	C18—C19—C20	113.8 (4)
C4—C3—H3A	120.6	C18—C19—H19A	108.8
C5—C4—C3	122.1 (5)	C20—C19—H19A	108.8
C5—C4—H4A	119.0	C18—C19—H19B	108.8
C3—C4—H4A	119.0	C20—C19—H19B	108.8
C4—C5—C6	119.3 (5)	H19A—C19—H19B	107.7
C4—C5—C8	121.6 (5)	C19—C20—C16	107.9 (4)
C6—C5—C8	119.1 (5)	C19—C20—H20A	110.1
C7—C6—C5	118.5 (5)	C16—C20—H20A	110.1
C7—C6—H6A	120.7	C19—C20—H20B	110.1
C5—C6—H6A	120.7	C16—C20—H20B	110.1
C2—C7—C6	121.2 (5)	H20A—C20—H20B	108.4
C2—C7—H7A	119.4	C22—C21—C17	122.3 (5)
C6—C7—H7A	119.4	C22—C21—H21A	118.8
N—C8—C5	114.9 (5)	C17—C21—H21A	118.8
N—C8—C9	125.2 (5)	C23—C22—C21	120.1 (5)
C5—C8—C9	119.9 (5)	C23—C22—H22A	120.0
C8—C9—H9A	109.5	C21—C22—H22A	120.0
C8—C9—H9B	109.5	C24—C23—C22	117.8 (5)
H9A—C9—H9B	109.5	C24—C23—C27	121.3 (5)
C8—C9—H9C	109.5	C22—C23—C27	120.9 (5)
H9A—C9—H9C	109.5	C23—C24—C18	123.2 (5)
H9B—C9—H9C	109.5	C23—C24—H24A	118.4
O3—C10—O2	122.8 (5)	C18—C24—H24A	118.4
O3—C10—C11	125.0 (5)	C11—C25—H25A	109.5
O2—C10—C11	112.2 (4)	C11—C25—H25B	109.5
C10—C11—C12	104.2 (4)	H25A—C25—H25B	109.5
C10—C11—C16	106.3 (4)	C11—C25—H25C	109.5
C12—C11—C16	108.5 (4)	H25A—C25—H25C	109.5
C10—C11—C25	110.4 (4)	H25B—C25—H25C	109.5
C12—C11—C25	111.5 (4)	C15—C26—H26A	109.5
C16—C11—C25	115.3 (4)	C15—C26—H26B	109.5
C13—C12—C11	113.1 (4)	H26A—C26—H26B	109.5
C13—C12—H12A	109.0	C15—C26—H26C	109.5
C11—C12—H12A	109.0	H26A—C26—H26C	109.5
C13—C12—H12B	109.0	H26B—C26—H26C	109.5
C11—C12—H12B	109.0	C29—C27—C28	112.9 (6)
H12A—C12—H12B	107.8	C29—C27—C23	111.1 (5)
C14—C13—C12	110.0 (4)	C28—C27—C23	112.4 (5)
C14—C13—H13A	109.7	C29—C27—H27A	106.6
C12—C13—H13A	109.7	C28—C27—H27A	106.6
C14—C13—H13B	109.7	C23—C27—H27A	106.6
C12—C13—H13B	109.7	C27—C28—H28A	109.5
H13A—C13—H13B	108.2	C27—C28—H28B	109.5
C15—C14—C13	114.3 (4)	H28A—C28—H28B	109.5
C15—C14—H14A	108.7	C27—C28—H28C	109.5
C13—C14—H14A	108.7	H28A—C28—H28C	109.5
C15—C14—H14B	108.7	H28B—C28—H28C	109.5
C13—C14—H14B	108.7	C27—C29—H29A	109.5
H14A—C14—H14B	107.6	C27—C29—H29B	109.5
C14—C15—C17	112.4 (4)	H29A—C29—H29B	109.5
C14—C15—C16	108.0 (3)	C27—C29—H29C	109.5
C17—C15—C16	107.0 (3)	H29A—C29—H29C	109.5
C14—C15—C26	109.2 (4)	H29B—C29—H29C	109.5
C17—C15—C26	106.0 (4)

C8—N—O2—C10	−179.7 (5)	C10—C11—C16—C15	−163.9 (4)
C1—O1—C2—C3	−2.5 (9)	C12—C11—C16—C15	−52.3 (5)
C1—O1—C2—C7	176.8 (6)	C25—C11—C16—C15	73.5 (5)
C7—C2—C3—C4	−1.2 (9)	C14—C15—C16—C20	−174.6 (4)
O1—C2—C3—C4	178.0 (5)	C17—C15—C16—C20	−53.4 (5)
C2—C3—C4—C5	1.8 (9)	C26—C15—C16—C20	63.6 (5)
C3—C4—C5—C6	−0.7 (8)	C14—C15—C16—C11	52.7 (5)
C3—C4—C5—C8	179.4 (5)	C17—C15—C16—C11	174.0 (4)
C4—C5—C6—C7	−1.0 (8)	C26—C15—C16—C11	−69.1 (5)
C8—C5—C6—C7	179.0 (5)	C14—C15—C17—C18	140.3 (4)
C3—C2—C7—C6	−0.4 (9)	C16—C15—C17—C18	21.9 (6)
O1—C2—C7—C6	−179.7 (5)	C26—C15—C17—C18	−100.4 (5)
C5—C6—C7—C2	1.5 (9)	C14—C15—C17—C21	−43.6 (6)
O2—N—C8—C5	179.8 (4)	C16—C15—C17—C21	−162.0 (4)
O2—N—C8—C9	−0.2 (9)	C26—C15—C17—C21	75.7 (5)
C4—C5—C8—N	−140.2 (6)	C21—C17—C18—C24	0.7 (6)
C6—C5—C8—N	39.9 (8)	C15—C17—C18—C24	176.9 (4)
C4—C5—C8—C9	39.9 (9)	C21—C17—C18—C19	179.3 (4)
C6—C5—C8—C9	−140.1 (6)	C15—C17—C18—C19	−4.4 (7)
N—O2—C10—O3	−2.7 (8)	C17—C18—C19—C20	16.9 (6)
N—O2—C10—C11	177.4 (4)	C24—C18—C19—C20	−164.4 (4)
O3—C10—C11—C12	−79.2 (7)	C18—C19—C20—C16	−46.7 (5)
O2—C10—C11—C12	100.7 (5)	C11—C16—C20—C19	−158.6 (4)
O3—C10—C11—C16	35.3 (8)	C15—C16—C20—C19	67.9 (5)
O2—C10—C11—C16	−144.8 (4)	C18—C17—C21—C22	−0.3 (7)
O3—C10—C11—C25	161.0 (6)	C15—C17—C21—C22	−176.7 (4)
O2—C10—C11—C25	−19.1 (6)	C17—C21—C22—C23	0.4 (8)
C10—C11—C12—C13	165.9 (4)	C21—C22—C23—C24	−1.0 (8)
C16—C11—C12—C13	53.0 (5)	C21—C22—C23—C27	178.4 (5)
C25—C11—C12—C13	−75.0 (6)	C22—C23—C24—C18	1.4 (8)
C11—C12—C13—C14	−56.2 (6)	C27—C23—C24—C18	−178.0 (5)
C12—C13—C14—C15	57.6 (6)	C17—C18—C24—C23	−1.3 (7)
C13—C14—C15—C17	−172.2 (4)	C19—C18—C24—C23	180.0 (5)
C13—C14—C15—C16	−54.5 (5)	C24—C23—C27—C29	−106.9 (6)
C13—C14—C15—C26	70.4 (5)	C22—C23—C27—C29	73.8 (7)
C10—C11—C16—C20	64.7 (5)	C24—C23—C27—C28	125.5 (6)
C12—C11—C16—C20	176.2 (4)	C22—C23—C27—C28	−53.8 (7)
C25—C11—C16—C20	−58.0 (6)

Experimental details

Crystal data
Chemical formula	C₂₉H₃₇NO₃
M_r	447.60
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.1700 (12), 11.051 (2), 37.526 (8)
V (Å³)	2558.7 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (CAD-4 Software; North et al., 1968)
T_min, T_max	0.978, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5399, 4691, 2211
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.183, 1.00
No. of reflections	4691
No. of parameters	298
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

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 supported financially by grants from the Natural Science Foundation of Jiangsu Province (grant No. 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
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Li, F., He, L., Song, Z. Q., Yao, J. C., Rao, X. P. & Li, H. T. (2008). J. Pharm. Pharmacol. 60, 205–211. Web of Science CrossRef PubMed CAS 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., 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

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Volume 70| Part 9| September 2014| Page o948

doi:10.1107/S1600536814016882

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

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

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

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