Crystal structure of (4bS,8aR)-1-isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexa­hydro­phenanthren-2-yl acetate

The title compound, (4bS,8aR)-1-isopropyl-4 b,8,8-trimethyl-7-oxo-4 b,7,8,8a,9,10-hexa­hydro­phenanthren-2-yl acetate, was prepared by a direct acetyl­ation reaction of naturally occurring totarolenone. In the crystal, mol­ecules are linked to each other by C—H...O hydrogen bonds and C—H...π inter­actions, forming sheets parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.030
• wR factor = 0.077
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT213_ALERT_2_C Atom O1A             has ADP max/min Ratio .....        3.4 prolat
PLAT220_ALERT_2_C Non-Solvent  Resd 1  O   Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )         8% Note
PLAT791_ALERT_4_G Model has Chirality at C4B         (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G Model has Chirality at C8A         (Chiral SPGR)          R Verify
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg et al., 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(4bS,8aR)-1-Isopropyl-4b,8,8-trimethyl-7-oxo-4b,7,8,8a,9,10-hexahydrophenanthren-2-yl acetate

Crystal data

C22H28O3	F(000) = 368
Mr = 340.44	Dx = 1.164 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54178 Å
a = 7.4103 (2) Å	Cell parameters from 3909 reflections
b = 10.4681 (3) Å	θ = 3.5–74.5°
c = 12.8121 (3) Å	µ = 0.60 mm^−1
β = 102.235 (1)°	T = 100 K
V = 971.28 (4) Å^3	Block, colourless
Z = 2	0.41 × 0.30 × 0.18 mm

Data collection

D8 Venture CMOS area detector diffractometer	3852 reflections with I > 2σ(I)
Radiation source: microsource	Rint = 0.029
φ and ω scans	θmax = 74.5°, θmin = 3.5°
Absorption correction: numerical (SADABS; Bruker, 2012)	h = −9→9
	k = −13→13
17946 measured reflections	l = −16→15
3909 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.2106P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.077	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.16 e Å^−3
3909 reflections	Δρmin = −0.17 e Å^−3
252 parameters	Absolute structure: Flack x determined using 1757 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.02 (5)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O2	0.31864 (16)	−0.17015 (11)	0.35741 (9)	0.0169 (2)
O3	0.57128 (17)	−0.12685 (12)	0.48549 (10)	0.0228 (3)
C1	0.1762 (2)	0.03631 (15)	0.31947 (13)	0.0149 (3)
C2	0.3194 (2)	−0.04717 (15)	0.31317 (12)	0.0141 (3)
C3	0.4591 (2)	−0.01616 (16)	0.26178 (12)	0.0165 (3)
H3	0.5532	−0.0764	0.2575	0.020*
C4	0.4606 (2)	0.10335 (17)	0.21673 (12)	0.0160 (3)
H4	0.5571	0.1253	0.1817	0.019*
C4A	0.3228 (2)	0.19262 (15)	0.22171 (12)	0.0140 (3)
C4B	0.3352 (2)	0.32561 (16)	0.17177 (13)	0.0167 (3)
C5	0.3964 (3)	0.31576 (18)	0.06569 (14)	0.0242 (4)
H5	0.4747	0.2476	0.0544	0.029*
C7	0.2283 (3)	0.5140 (2)	−0.00216 (14)	0.0262 (4)
C8	0.1175 (3)	0.51452 (17)	0.08559 (13)	0.0217 (4)
C8A	0.1410 (2)	0.38675 (17)	0.14900 (12)	0.0166 (3)
H8A	0.0595	0.3243	0.1021	0.020*
C9	0.0693 (2)	0.39088 (17)	0.25247 (13)	0.0195 (3)
H9A	0.1618	0.4325	0.3095	0.023*
H9B	−0.0461	0.4415	0.2413	0.023*
C10	0.0326 (2)	0.25550 (16)	0.28606 (13)	0.0181 (3)
H10A	0.0204	0.2569	0.3615	0.022*
H10B	−0.0866	0.2260	0.2423	0.022*
C10A	0.1817 (2)	0.16011 (16)	0.27480 (12)	0.0143 (3)
C11	−0.0867 (3)	0.5279 (2)	0.02894 (17)	0.0308 (4)
H11A	−0.1038	0.6076	−0.0122	0.046*
H11B	−0.1639	0.5294	0.0823	0.046*
H11C	−0.1223	0.4554	−0.0194	0.046*
C12	0.1723 (4)	0.63433 (19)	0.15482 (19)	0.0409 (6)
H12A	0.1463	0.7108	0.1101	0.061*
H12B	0.3044	0.6310	0.1874	0.061*
H12C	0.1011	0.6374	0.2111	0.061*
C13	0.4868 (3)	0.40095 (19)	0.24898 (16)	0.0252 (4)
H13A	0.5014	0.4854	0.2188	0.038*
H13B	0.6039	0.3543	0.2592	0.038*
H13C	0.4511	0.4109	0.3180	0.038*
C14	0.0212 (2)	−0.00178 (18)	0.37495 (14)	0.0220 (4)
H14	−0.0789	0.0631	0.3538	0.026*
C15	0.0844 (3)	0.0071 (3)	0.49646 (16)	0.0347 (5)
H15A	0.1850	−0.0538	0.5209	0.052*
H15B	−0.0193	−0.0132	0.5300	0.052*
H15C	0.1280	0.0939	0.5163	0.052*
C16	−0.0662 (3)	−0.1325 (2)	0.3410 (2)	0.0352 (5)
H16A	−0.0992	−0.1373	0.2629	0.053*
H16B	−0.1774	−0.1433	0.3701	0.053*
H16C	0.0224	−0.2003	0.3685	0.053*
C17	0.4501 (2)	−0.19878 (16)	0.44565 (13)	0.0165 (3)
C18	0.4186 (3)	−0.32928 (18)	0.48463 (16)	0.0285 (4)
H18A	0.5095	−0.3469	0.5506	0.043*
H18B	0.4316	−0.3924	0.4302	0.043*
H18C	0.2939	−0.3344	0.4988	0.043*
C6	0.3407 (7)	0.4028 (4)	−0.0124 (3)	0.0322 (13)	0.793 (14)
H6	0.3774	0.3905	−0.0784	0.039*	0.793 (14)
C6A	0.4227 (16)	0.4506 (11)	0.0182 (8)	0.014 (3)	0.207 (14)
H6A	0.5335	0.4861	0.0047	0.017*	0.207 (14)
O1	0.222 (3)	0.6074 (7)	−0.0588 (15)	0.040 (3)	0.63 (7)
O1A	0.185 (3)	0.575 (6)	−0.084 (3)	0.059 (7)	0.37 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2	0.0188 (5)	0.0125 (5)	0.0173 (5)	−0.0001 (4)	−0.0009 (4)	0.0017 (4)
O3	0.0257 (6)	0.0197 (6)	0.0195 (6)	−0.0038 (5)	−0.0032 (5)	0.0020 (5)
C1	0.0147 (7)	0.0179 (8)	0.0122 (7)	0.0008 (6)	0.0026 (6)	0.0017 (6)
C2	0.0173 (8)	0.0117 (7)	0.0116 (7)	−0.0003 (6)	−0.0006 (6)	0.0008 (6)
C3	0.0167 (7)	0.0189 (8)	0.0139 (7)	0.0058 (6)	0.0028 (6)	−0.0016 (6)
C4	0.0153 (8)	0.0205 (8)	0.0131 (7)	0.0004 (6)	0.0050 (6)	−0.0002 (6)
C4A	0.0182 (8)	0.0139 (7)	0.0095 (7)	0.0002 (6)	0.0022 (6)	0.0000 (6)
C4B	0.0233 (8)	0.0145 (7)	0.0135 (7)	−0.0003 (6)	0.0067 (6)	0.0014 (6)
C5	0.0375 (10)	0.0191 (8)	0.0201 (8)	0.0019 (8)	0.0153 (7)	0.0021 (7)
C7	0.0286 (9)	0.0265 (9)	0.0229 (8)	−0.0030 (8)	0.0040 (7)	0.0099 (8)
C8	0.0302 (9)	0.0153 (8)	0.0193 (8)	0.0023 (7)	0.0043 (7)	0.0048 (7)
C8A	0.0248 (8)	0.0129 (7)	0.0124 (7)	0.0018 (6)	0.0043 (6)	0.0017 (6)
C9	0.0277 (9)	0.0150 (7)	0.0178 (8)	0.0080 (7)	0.0095 (6)	0.0019 (6)
C10	0.0223 (8)	0.0177 (8)	0.0166 (8)	0.0066 (6)	0.0093 (6)	0.0047 (6)
C10A	0.0173 (7)	0.0152 (7)	0.0105 (7)	0.0031 (6)	0.0030 (6)	0.0009 (5)
C11	0.0303 (10)	0.0309 (10)	0.0317 (10)	0.0100 (8)	0.0074 (8)	0.0162 (8)
C12	0.0713 (17)	0.0125 (9)	0.0354 (11)	0.0019 (9)	0.0030 (11)	0.0015 (8)
C13	0.0272 (9)	0.0194 (8)	0.0287 (9)	−0.0055 (7)	0.0053 (7)	0.0001 (7)
C14	0.0174 (8)	0.0239 (9)	0.0272 (9)	0.0060 (7)	0.0103 (7)	0.0119 (7)
C15	0.0367 (11)	0.0482 (12)	0.0249 (9)	0.0116 (10)	0.0192 (8)	0.0138 (9)
C16	0.0174 (8)	0.0298 (11)	0.0587 (13)	−0.0018 (8)	0.0084 (8)	0.0144 (10)
C17	0.0203 (8)	0.0149 (8)	0.0139 (7)	0.0044 (6)	0.0025 (6)	0.0001 (6)
C18	0.0363 (11)	0.0171 (9)	0.0273 (10)	−0.0016 (8)	−0.0037 (8)	0.0071 (7)
C6	0.048 (3)	0.0312 (18)	0.0220 (14)	0.0010 (19)	0.0181 (16)	0.0045 (13)
C6A	0.014 (5)	0.016 (5)	0.014 (4)	−0.010 (4)	0.004 (4)	0.001 (4)
O1	0.042 (5)	0.033 (3)	0.051 (4)	0.010 (2)	0.026 (3)	0.028 (2)
O1A	0.033 (5)	0.095 (17)	0.048 (8)	0.014 (7)	0.012 (5)	0.055 (9)

Geometric parameters (Å, º)

O2—C17	1.360 (2)	C9—H9A	0.9900
O2—C2	1.4071 (19)	C9—H9B	0.9900
O3—C17	1.200 (2)	C10—C10A	1.519 (2)
C1—C2	1.390 (2)	C10—H10A	0.9900
C1—C10A	1.421 (2)	C10—H10B	0.9900
C1—C14	1.526 (2)	C11—H11A	0.9800
C2—C3	1.378 (2)	C11—H11B	0.9800
C3—C4	1.379 (2)	C11—H11C	0.9800
C3—H3	0.9500	C12—H12A	0.9800
C4—C4A	1.396 (2)	C12—H12B	0.9800
C4—H4	0.9500	C12—H12C	0.9800
C4A—C10A	1.404 (2)	C13—H13A	0.9800
C4A—C4B	1.543 (2)	C13—H13B	0.9800
C4B—C5	1.525 (2)	C13—H13C	0.9800
C4B—C8A	1.545 (2)	C14—C15	1.531 (3)
C4B—C13	1.546 (2)	C14—C16	1.537 (3)
C5—C6	1.352 (3)	C14—H14	1.0000
C5—C6A	1.565 (11)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C7—O1	1.213 (10)	C15—H15C	0.9800
C7—O1A	1.215 (16)	C16—H16A	0.9800
C7—C6	1.453 (4)	C16—H16B	0.9800
C7—C8	1.526 (3)	C16—H16C	0.9800
C7—C6A	1.557 (9)	C17—C18	1.490 (2)
C8—C11	1.540 (3)	C18—H18A	0.9800
C8—C12	1.540 (3)	C18—H18B	0.9800
C8—C8A	1.556 (2)	C18—H18C	0.9800
C8A—C9	1.530 (2)	C6—H6	0.9500
C8A—H8A	1.0000	C6A—H6A	0.9500
C9—C10	1.522 (2)
C17—O2—C2	118.24 (12)	C4A—C10A—C1	120.28 (14)
C2—C1—C10A	117.54 (14)	C4A—C10A—C10	121.20 (14)
C2—C1—C14	121.45 (14)	C1—C10A—C10	118.53 (14)
C10A—C1—C14	120.98 (14)	C8—C11—H11A	109.5
C3—C2—C1	122.65 (15)	C8—C11—H11B	109.5
C3—C2—O2	118.38 (14)	H11A—C11—H11B	109.5
C1—C2—O2	118.92 (14)	C8—C11—H11C	109.5
C2—C3—C4	119.16 (15)	H11A—C11—H11C	109.5
C2—C3—H3	120.4	H11B—C11—H11C	109.5
C4—C3—H3	120.4	C8—C12—H12A	109.5
C3—C4—C4A	121.16 (15)	C8—C12—H12B	109.5
C3—C4—H4	119.4	H12A—C12—H12B	109.5
C4A—C4—H4	119.4	C8—C12—H12C	109.5
C4—C4A—C10A	119.13 (14)	H12A—C12—H12C	109.5
C4—C4A—C4B	118.45 (14)	H12B—C12—H12C	109.5
C10A—C4A—C4B	122.38 (14)	C4B—C13—H13A	109.5
C5—C4B—C4A	111.34 (13)	C4B—C13—H13B	109.5
C5—C4B—C8A	107.50 (13)	H13A—C13—H13B	109.5
C4A—C4B—C8A	108.47 (13)	C4B—C13—H13C	109.5
C5—C4B—C13	106.98 (14)	H13A—C13—H13C	109.5
C4A—C4B—C13	107.10 (13)	H13B—C13—H13C	109.5
C8A—C4B—C13	115.50 (14)	C1—C14—C15	111.07 (15)
C6—C5—C4B	120.85 (18)	C1—C14—C16	114.48 (16)
C4B—C5—C6A	111.8 (4)	C15—C14—C16	111.19 (17)
C6—C5—H5	119.6	C1—C14—H14	106.5
C4B—C5—H5	119.6	C15—C14—H14	106.5
O1—C7—C8	118.7 (5)	C16—C14—H14	106.5
O1A—C7—C8	123.5 (13)	C14—C15—H15A	109.5
C6—C7—C8	118.54 (17)	C14—C15—H15B	109.5
C8—C7—C6A	120.1 (3)	H15A—C15—H15B	109.5
C7—C8—C11	106.34 (15)	C14—C15—H15C	109.5
C7—C8—C12	108.06 (17)	H15A—C15—H15C	109.5
C11—C8—C12	108.06 (18)	H15B—C15—H15C	109.5
C7—C8—C8A	111.32 (15)	C14—C16—H16A	109.5
C11—C8—C8A	108.33 (15)	C14—C16—H16B	109.5
C12—C8—C8A	114.38 (14)	H16A—C16—H16B	109.5
C9—C8A—C4B	109.20 (13)	C14—C16—H16C	109.5
C9—C8A—C8	114.04 (14)	H16A—C16—H16C	109.5
C4B—C8A—C8	116.83 (14)	H16B—C16—H16C	109.5
C9—C8A—H8A	105.2	O3—C17—O2	123.70 (15)
C4B—C8A—H8A	105.2	O3—C17—C18	126.10 (15)
C8—C8A—H8A	105.2	O2—C17—C18	110.19 (14)
C10—C9—C8A	109.53 (14)	C17—C18—H18A	109.5
C10—C9—H9A	109.8	C17—C18—H18B	109.5
C8A—C9—H9A	109.8	H18A—C18—H18B	109.5
C10—C9—H9B	109.8	C17—C18—H18C	109.5
C8A—C9—H9B	109.8	H18A—C18—H18C	109.5
H9A—C9—H9B	108.2	H18B—C18—H18C	109.5
C10A—C10—C9	114.07 (14)	C5—C6—C7	124.3 (2)
C10A—C10—H10A	108.7	C5—C6—H6	117.9
C9—C10—H10A	108.7	C7—C6—H6	117.9
C10A—C10—H10B	108.7	C7—C6A—C5	105.2 (7)
C9—C10—H10B	108.7	C7—C6A—H6A	127.4
H10A—C10—H10B	107.6	C5—C6A—H6A	127.4

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.95	2.50	3.411 (10)	159
C4—H4···O1A^i	0.95	2.55	3.428 (17)	154
C10—H10B···O1A^ii	0.99	2.55	3.328 (17)	136
C13—H13C···O3^iii	0.98	2.59	3.530 (2)	161
C18—H18A···Cg1^iv	0.98	2.55	3.504 (2)	165

Symmetry codes: (i) −x+1, y−1/2, −z; (ii) −x, y−1/2, −z; (iii) −x+1, y+1/2, −z+1; (iv) −x+1, y−1/2, −z+1.