Patchouli alcohol: 4α,8aβ,9,9-tetra­methyl-3,4,4aβ,5,6β,7,8,8a-octa­hydro-1,6-methano­naphthalen-1β(2H)-ol

The title compound, C₁₅H₂₆O, commonly known as Patchouli alcohol or Patchoulol, is a tri­cyclo­[5.3.1.0^3,8]undecane. It crystallized in the enanti­omer-defining hexa­gonal space group P6₃. However, the absolute structure could not be determined [absolute structure parameter = 0.4 (10)]. In the crystal, three mol­ecules are linked by O—H...O hydrogen bonds, forming a trimer with an R³₃(6) ring motif. The crystal structure of patchouli alcohol determined by the crystalline inclusion method, using 1,1,6,6-tetra­phenyl­hexa-2,4-diyne-1,6-diol as host, has been reported [Tong et al., (2013). Nat. Prod. Res. 27, 32–36].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.068
• wR factor = 0.136
• Data-to-parameter ratio = 20.7

checkCIF/PLATON results

No syntax errors found



Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12
            Rint given   0.122
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.400
           From the CIF: _refine_ls_abs_structure_Flack_su    1.000
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00535 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .         40 Ang3
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.309 Check

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT020_ALERT_3_G The value of Rint is greater than 0.12 .........      0.122 Report
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      1.000 Report
PLAT791_ALERT_4_G The Model has Chirality at C1      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C2      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C5      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C11     (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C12     (Chiral SPGR)          R Verify
PLAT882_ALERT_1_G Missing datum for _diffrn_reflns_av_unetI/netI .     Please Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           4 Note
PLAT916_ALERT_2_G Hooft y and Flack x Parameter values differ by .       0.70 Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Note

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

   1 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
   5 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: RAPID-AUTO (Rigaku, 2015); cell refinement: RAPID-AUTO (Rigaku, 2015); data reduction: RAPID-AUTO (Rigaku, 2015); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 2015).

4α,8aβ,9,9-Tetramethyl-3,4,4aβ,5,6β,7,8,8a-octahydro-1,6-methanonaphthalen-1β(2H)-ol

Crystal data

C15H26O	Dx = 1.087 Mg m^−3
Mr = 222.37	Mo Kα radiation, λ = 0.71075 Å
Hexagonal, P63	Cell parameters from 6783 reflections
a = 16.2421 (10) Å	θ = 3.4–27.3°
c = 8.9182 (6) Å	µ = 0.07 mm^−1
V = 2037.5 (2) Å^3	T = 173 K
Z = 6	Block, colourless
F(000) = 744.00	0.30 × 0.25 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2046 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.122
ω scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	h = −19→21
Tmin = 0.562, Tmax = 0.994	k = −21→21
20092 measured reflections	l = −11→11
3098 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.068	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.0564P)^2 + 0.1619P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3098 reflections	Δρmax = 0.21 e Å^−3
150 parameters	Δρmin = −0.20 e Å^−3
1 restraint	Absolute structure: Flack x determined using 616 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.4 (10)
Secondary atom site location: difference Fourier map

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.

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
O1	0.72575 (15)	0.44897 (15)	0.5000 (3)	0.0397 (6)
H1	0.6664	0.4139	0.5015	0.048*
C1	0.7497 (2)	0.5470 (2)	0.4884 (4)	0.0311 (8)
C2	0.7078 (2)	0.5749 (2)	0.6226 (4)	0.0329 (9)
C3	0.6000 (3)	0.5307 (3)	0.6058 (4)	0.0410 (10)
H3A	0.5741	0.5439	0.6973	0.049*
H3B	0.5707	0.4609	0.5960	0.049*
C4	0.5733 (2)	0.5697 (3)	0.4689 (4)	0.0444 (10)
H4A	0.5486	0.6115	0.5016	0.053*
H4B	0.5233	0.5167	0.4097	0.053*
C5	0.6632 (2)	0.6261 (3)	0.3733 (4)	0.0358 (9)
H5	0.6462	0.6466	0.2780	0.043*
C6	0.7090 (2)	0.5646 (2)	0.3359 (4)	0.0331 (9)
C7	0.7248 (3)	0.5403 (3)	0.7738 (5)	0.0501 (11)
H7A	0.6855	0.4709	0.7795	0.060*
H7B	0.7076	0.5691	0.8557	0.060*
H7C	0.7920	0.5589	0.7825	0.060*
C8	0.7849 (3)	0.6133 (3)	0.2137 (5)	0.0471 (10)
H8A	0.7548	0.6181	0.1214	0.056*
H8B	0.8159	0.5758	0.1945	0.056*
H8C	0.8324	0.6772	0.2473	0.056*
C9	0.6332 (3)	0.4703 (3)	0.2642 (5)	0.0465 (10)
H9A	0.6633	0.4343	0.2299	0.056*
H9B	0.6041	0.4840	0.1787	0.056*
H9C	0.5842	0.4328	0.3386	0.056*
C10	0.7307 (3)	0.7139 (3)	0.4649 (5)	0.0392 (9)
H10A	0.7011	0.7536	0.4820	0.047*
H10B	0.7904	0.7523	0.4082	0.047*
C11	0.7535 (2)	0.6844 (2)	0.6179 (4)	0.0343 (9)
H11	0.7235	0.7034	0.6985	0.041*
C12	0.8608 (2)	0.7346 (2)	0.6484 (5)	0.0416 (10)
H12	0.8703	0.7108	0.7466	0.050*
C13	0.9093 (2)	0.7073 (2)	0.5281 (5)	0.0436 (10)
H13A	0.9760	0.7302	0.5582	0.052*
H13B	0.9104	0.7392	0.4329	0.052*
C14	0.8592 (2)	0.5994 (2)	0.5017 (5)	0.0393 (9)
H14A	0.8760	0.5704	0.5853	0.047*
H14B	0.8850	0.5878	0.4086	0.047*
C15	0.9055 (3)	0.8427 (3)	0.6610 (6)	0.0609 (13)
H15A	0.8956	0.8679	0.5671	0.073*
H15B	0.9738	0.8715	0.6802	0.073*
H15C	0.8756	0.8579	0.7438	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0311 (13)	0.0266 (12)	0.0585 (17)	0.0122 (10)	−0.0067 (14)	−0.0006 (13)
C1	0.0289 (18)	0.0265 (17)	0.037 (2)	0.0132 (14)	−0.0043 (18)	−0.0007 (17)
C2	0.034 (2)	0.032 (2)	0.029 (2)	0.0133 (17)	−0.0036 (17)	0.0032 (16)
C3	0.037 (2)	0.043 (2)	0.036 (2)	0.0150 (18)	0.0063 (18)	0.0003 (18)
C4	0.034 (2)	0.060 (2)	0.044 (3)	0.0272 (18)	−0.0012 (19)	−0.005 (2)
C5	0.038 (2)	0.051 (2)	0.029 (2)	0.0302 (19)	−0.0032 (16)	0.0029 (17)
C6	0.032 (2)	0.040 (2)	0.030 (2)	0.0197 (18)	−0.0013 (16)	0.0009 (16)
C7	0.058 (3)	0.043 (2)	0.037 (2)	0.016 (2)	−0.008 (2)	0.006 (2)
C8	0.051 (3)	0.056 (3)	0.038 (2)	0.029 (2)	0.0074 (19)	0.004 (2)
C9	0.048 (2)	0.056 (3)	0.037 (2)	0.026 (2)	−0.0090 (19)	−0.011 (2)
C10	0.046 (2)	0.042 (2)	0.040 (2)	0.0299 (18)	0.0003 (19)	0.0025 (19)
C11	0.040 (2)	0.0313 (19)	0.031 (2)	0.0180 (17)	−0.0012 (18)	−0.0007 (16)
C12	0.040 (2)	0.029 (2)	0.049 (3)	0.0117 (17)	−0.0101 (19)	−0.0030 (18)
C13	0.0272 (19)	0.035 (2)	0.066 (3)	0.0135 (17)	−0.0091 (19)	0.002 (2)
C14	0.0319 (19)	0.0338 (19)	0.055 (3)	0.0186 (16)	−0.008 (2)	0.003 (2)
C15	0.057 (3)	0.035 (2)	0.080 (4)	0.014 (2)	−0.004 (3)	−0.006 (2)

Geometric parameters (Å, º)

O1—C1	1.442 (4)	C8—H8A	0.9800
O1—H1	0.8400	C8—H8B	0.9800
C1—C14	1.546 (4)	C8—H8C	0.9800
C1—C2	1.552 (5)	C9—H9A	0.9800
C1—C6	1.599 (5)	C9—H9B	0.9800
C2—C3	1.531 (5)	C9—H9C	0.9800
C2—C7	1.538 (5)	C10—C11	1.551 (5)
C2—C11	1.547 (4)	C10—H10A	0.9900
C3—C4	1.534 (6)	C10—H10B	0.9900
C3—H3A	0.9900	C11—C12	1.536 (5)
C3—H3B	0.9900	C11—H11	1.0000
C4—C5	1.537 (5)	C12—C13	1.523 (6)
C4—H4A	0.9900	C12—C15	1.533 (5)
C4—H4B	0.9900	C12—H12	1.0000
C5—C10	1.530 (5)	C13—C14	1.537 (5)
C5—C6	1.552 (5)	C13—H13A	0.9900
C5—H5	1.0000	C13—H13B	0.9900
C6—C8	1.535 (5)	C14—H14A	0.9900
C6—C9	1.544 (5)	C14—H14B	0.9900
C7—H7A	0.9800	C15—H15A	0.9800
C7—H7B	0.9800	C15—H15B	0.9800
C7—H7C	0.9800	C15—H15C	0.9800
C1—O1—H1	109.5	C6—C8—H8C	109.5
O1—C1—C14	101.7 (2)	H8A—C8—H8C	109.5
O1—C1—C2	110.6 (3)	H8B—C8—H8C	109.5
C14—C1—C2	109.4 (3)	C6—C9—H9A	109.5
O1—C1—C6	110.6 (3)	C6—C9—H9B	109.5
C14—C1—C6	115.5 (3)	H9A—C9—H9B	109.5
C2—C1—C6	108.9 (2)	C6—C9—H9C	109.5
C3—C2—C7	106.7 (3)	H9A—C9—H9C	109.5
C3—C2—C11	108.4 (3)	H9B—C9—H9C	109.5
C7—C2—C11	111.9 (3)	C5—C10—C11	110.6 (3)
C3—C2—C1	110.7 (3)	C5—C10—H10A	109.5
C7—C2—C1	112.6 (3)	C11—C10—H10A	109.5
C11—C2—C1	106.6 (3)	C5—C10—H10B	109.5
C2—C3—C4	112.2 (3)	C11—C10—H10B	109.5
C2—C3—H3A	109.2	H10A—C10—H10B	108.1
C4—C3—H3A	109.2	C12—C11—C2	111.7 (3)
C2—C3—H3B	109.2	C12—C11—C10	112.0 (3)
C4—C3—H3B	109.2	C2—C11—C10	109.1 (3)
H3A—C3—H3B	107.9	C12—C11—H11	107.9
C3—C4—C5	107.9 (3)	C2—C11—H11	107.9
C3—C4—H4A	110.1	C10—C11—H11	107.9
C5—C4—H4A	110.1	C13—C12—C15	111.6 (3)
C3—C4—H4B	110.1	C13—C12—C11	109.6 (3)
C5—C4—H4B	110.1	C15—C12—C11	112.5 (3)
H4A—C4—H4B	108.4	C13—C12—H12	107.6
C10—C5—C4	106.5 (3)	C15—C12—H12	107.6
C10—C5—C6	111.3 (3)	C11—C12—H12	107.6
C4—C5—C6	110.7 (3)	C12—C13—C14	112.6 (3)
C10—C5—H5	109.4	C12—C13—H13A	109.1
C4—C5—H5	109.4	C14—C13—H13A	109.1
C6—C5—H5	109.4	C12—C13—H13B	109.1
C8—C6—C9	104.7 (3)	C14—C13—H13B	109.1
C8—C6—C5	109.9 (3)	H13A—C13—H13B	107.8
C9—C6—C5	109.0 (3)	C13—C14—C1	116.6 (3)
C8—C6—C1	113.6 (3)	C13—C14—H14A	108.2
C9—C6—C1	111.8 (3)	C1—C14—H14A	108.2
C5—C6—C1	107.8 (3)	C13—C14—H14B	108.2
C2—C7—H7A	109.5	C1—C14—H14B	108.2
C2—C7—H7B	109.5	H14A—C14—H14B	107.3
H7A—C7—H7B	109.5	C12—C15—H15A	109.5
C2—C7—H7C	109.5	C12—C15—H15B	109.5
H7A—C7—H7C	109.5	H15A—C15—H15B	109.5
H7B—C7—H7C	109.5	C12—C15—H15C	109.5
C6—C8—H8A	109.5	H15A—C15—H15C	109.5
C6—C8—H8B	109.5	H15B—C15—H15C	109.5
H8A—C8—H8B	109.5
O1—C1—C2—C3	−73.5 (3)	C14—C1—C6—C9	130.6 (3)
C14—C1—C2—C3	175.2 (3)	C2—C1—C6—C9	−105.9 (3)
C6—C1—C2—C3	48.1 (3)	O1—C1—C6—C5	135.6 (3)
O1—C1—C2—C7	45.7 (4)	C14—C1—C6—C5	−109.6 (3)
C14—C1—C2—C7	−65.5 (4)	C2—C1—C6—C5	13.9 (3)
C6—C1—C2—C7	167.4 (3)	C4—C5—C10—C11	58.4 (4)
O1—C1—C2—C11	168.8 (3)	C6—C5—C10—C11	−62.4 (4)
C14—C1—C2—C11	57.6 (3)	C3—C2—C11—C12	174.8 (3)
C6—C1—C2—C11	−69.5 (3)	C7—C2—C11—C12	57.5 (4)
C7—C2—C3—C4	172.5 (3)	C1—C2—C11—C12	−66.0 (4)
C11—C2—C3—C4	51.9 (4)	C3—C2—C11—C10	−60.8 (4)
C1—C2—C3—C4	−64.7 (4)	C7—C2—C11—C10	−178.1 (3)
C2—C3—C4—C5	11.4 (4)	C1—C2—C11—C10	58.4 (4)
C3—C4—C5—C10	−67.7 (4)	C5—C10—C11—C12	129.5 (3)
C3—C4—C5—C6	53.5 (4)	C5—C10—C11—C2	5.3 (4)
C10—C5—C6—C8	−74.0 (4)	C2—C11—C12—C13	61.3 (4)
C4—C5—C6—C8	167.7 (3)	C10—C11—C12—C13	−61.4 (4)
C10—C5—C6—C9	171.8 (3)	C2—C11—C12—C15	−173.8 (4)
C4—C5—C6—C9	53.5 (4)	C10—C11—C12—C15	63.4 (4)
C10—C5—C6—C1	50.3 (4)	C15—C12—C13—C14	−173.9 (3)
C4—C5—C6—C1	−68.0 (3)	C11—C12—C13—C14	−48.6 (4)
O1—C1—C6—C8	−102.3 (3)	C12—C13—C14—C1	45.6 (5)
C14—C1—C6—C8	12.4 (4)	O1—C1—C14—C13	−167.2 (4)
C2—C1—C6—C8	136.0 (3)	C2—C1—C14—C13	−50.2 (4)
O1—C1—C6—C9	15.8 (4)	C6—C1—C14—C13	73.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1^i	0.84	2.07	2.818 (3)	147

Symmetry code: (i) −y+1, x−y, z.