5,11,11-Trimethyl-16-oxatetra­cyclo­[6.6.2.0^1,10.0^2,7]hexa­deca-2,4,6-trien-4-ol

In the title compound, C₁₈H₂₄O₂, one of the cyclo­hexane rings adopts a chair conformation and the other adopts a boat conformation. Mol­ecules are linked by inter­molecular O—H...O hydrogen bonds, forming ribbons along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.084
• wR factor = 0.155
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C9     -   C10     ..       6.90 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C13    -   C14     ..       6.26 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.41
           From the CIF: _reflns_number_total               1772
           Count of symmetry unique reflns         1825
           Completeness (_total/calc)             97.10%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

---

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALE (Otwinowski & Minor, 1997); data reduction: SCALE; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5,11,11-Trimethyl-16-oxatetracyclo[6.6.2.0^1,10.0^2,7]hexadeca-2,4,6- trien-4-ol

Crystal data

C18H24O2	F(000) = 296
Mr = 272.37	Dx = 1.185 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4631 reflections
a = 6.1900 (12) Å	θ = 1.8–27.4°
b = 10.979 (2) Å	µ = 0.08 mm^−1
c = 11.622 (2) Å	T = 295 K
β = 104.88 (3)°	Block, colourless
V = 763.3 (3) Å^3	0.60 × 0.40 × 0.20 mm
Z = 2

Data collection

MAC DIP-2030K diffractometer	1770 reflections with I > 2σ(I)
Radiation source: rotate anode	Rint = 0.045
Graphite monochromator	θmax = 27.4°, θmin = 1.8°
Detector resolution: 0 pixels mm^-1	h = −7→7
ω scans	k = −14→14
4631 measured reflections	l = −14→14
1772 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0114P)^2 + 0.9069P] where P = (Fo^2 + 2Fc^2)/3
S = 1.16	(Δ/σ)max = 0.001
1772 reflections	Δρmax = 0.21 e Å^−3
182 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.198 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	−0.1939 (8)	0.0475 (4)	0.7964 (4)	0.0711 (13)
O2	0.4585 (7)	0.3534 (4)	1.1789 (4)	0.0685 (12)
H2A	0.3726	0.4093	1.1825	0.103*
C1	−0.2100 (11)	0.3952 (5)	0.7967 (5)	0.0599 (15)
H1A	−0.2950	0.3970	0.8561	0.072*
H1B	−0.0891	0.4536	0.8204	0.072*
C2	−0.3600 (11)	0.4336 (7)	0.6784 (5)	0.0767 (19)
H2B	−0.4069	0.5173	0.6838	0.092*
H2C	−0.4927	0.3829	0.6598	0.092*
C3	−0.2419 (11)	0.4230 (7)	0.5790 (6)	0.0739 (18)
H3A	−0.1132	0.4767	0.5965	0.089*
H3B	−0.3426	0.4505	0.5052	0.089*
C4	−0.1641 (11)	0.2936 (5)	0.5612 (5)	0.0602 (15)
C5	−0.0189 (9)	0.2480 (4)	0.6834 (4)	0.0458 (11)
H5A	0.1189	0.2961	0.6985	0.055*
C6	0.0582 (11)	0.1107 (5)	0.6815 (5)	0.0594 (15)
H6A	−0.0371	0.0686	0.6140	0.071*
H6B	0.2108	0.1073	0.6743	0.071*
C7	0.0428 (10)	0.0514 (5)	0.7954 (5)	0.0575 (14)
H7A	0.1029	−0.0316	0.7996	0.069*
C8	0.1689 (9)	0.1234 (5)	0.9004 (5)	0.0512 (13)
C9	0.0817 (9)	0.2408 (5)	0.9016 (5)	0.0540 (13)
C10	−0.1104 (8)	0.2676 (5)	0.7945 (4)	0.0450 (11)
C11	0.1752 (10)	0.3198 (5)	0.9955 (4)	0.0552 (14)
H11A	0.1152	0.3968	0.9997	0.066*
C12	0.3635 (9)	0.2793 (5)	1.0840 (5)	0.0514 (12)
C13	0.4628 (9)	0.1673 (6)	1.0781 (4)	0.0535 (13)
C14	0.3579 (10)	0.0889 (5)	0.9876 (5)	0.0589 (14)
H14A	0.4155	0.0110	0.9852	0.071*
C15	−0.3748 (11)	0.2168 (8)	0.5060 (6)	0.082 (2)
H15A	−0.4553	0.2530	0.4323	0.123*
H15B	−0.4688	0.2141	0.5600	0.123*
H15C	−0.3309	0.1355	0.4914	0.123*
C16	−0.0215 (12)	0.2964 (7)	0.4729 (5)	0.0758 (19)
H16A	0.1080	0.3462	0.5038	0.114*
H16B	−0.1068	0.3298	0.3988	0.114*
H16C	0.0248	0.2152	0.4602	0.114*
C17	−0.2855 (10)	0.1683 (6)	0.8014 (6)	0.0643 (16)
H17A	−0.3303	0.1776	0.8750	0.077*
H17B	−0.4171	0.1787	0.7356	0.077*
C18	0.6793 (11)	0.1319 (6)	1.1679 (6)	0.0733 (18)
H18A	0.7280	0.1978	1.2228	0.110*
H18B	0.7921	0.1147	1.1269	0.110*
H18C	0.6544	0.0607	1.2108	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.079 (3)	0.045 (2)	0.091 (3)	−0.018 (2)	0.024 (2)	0.008 (2)
O2	0.078 (3)	0.055 (3)	0.064 (2)	0.017 (2)	0.003 (2)	−0.004 (2)
C1	0.077 (4)	0.050 (3)	0.047 (3)	0.013 (3)	0.005 (3)	−0.006 (2)
C2	0.090 (5)	0.068 (4)	0.064 (4)	0.027 (4)	0.005 (3)	0.003 (3)
C3	0.077 (4)	0.067 (4)	0.067 (4)	0.015 (4)	0.000 (3)	0.008 (4)
C4	0.087 (4)	0.046 (3)	0.043 (3)	0.002 (3)	0.008 (3)	0.005 (2)
C5	0.056 (3)	0.037 (3)	0.045 (3)	−0.011 (2)	0.013 (2)	−0.002 (2)
C6	0.080 (4)	0.041 (3)	0.055 (3)	−0.005 (3)	0.013 (3)	−0.011 (2)
C7	0.075 (4)	0.043 (3)	0.054 (3)	−0.008 (3)	0.014 (3)	−0.013 (3)
C8	0.067 (3)	0.045 (3)	0.048 (3)	0.002 (3)	0.026 (2)	0.005 (2)
C9	0.062 (3)	0.044 (3)	0.062 (3)	0.002 (3)	0.027 (3)	0.001 (3)
C10	0.054 (3)	0.039 (3)	0.038 (2)	−0.004 (2)	0.004 (2)	−0.005 (2)
C11	0.078 (4)	0.035 (3)	0.047 (3)	0.004 (2)	0.005 (3)	−0.004 (2)
C12	0.060 (3)	0.040 (3)	0.054 (3)	−0.001 (2)	0.014 (2)	−0.010 (2)
C13	0.065 (3)	0.062 (3)	0.033 (2)	0.004 (3)	0.011 (2)	−0.002 (2)
C14	0.079 (4)	0.042 (3)	0.060 (3)	0.010 (3)	0.026 (3)	0.015 (3)
C15	0.081 (4)	0.093 (6)	0.061 (4)	−0.012 (4)	0.000 (3)	−0.006 (4)
C16	0.094 (4)	0.078 (5)	0.057 (4)	−0.004 (4)	0.021 (3)	0.006 (3)
C17	0.057 (3)	0.071 (4)	0.070 (4)	−0.013 (3)	0.027 (3)	0.000 (3)
C18	0.075 (4)	0.062 (4)	0.079 (4)	0.018 (3)	0.011 (3)	0.005 (3)

Geometric parameters (Å, º)

O1—C17	1.450 (8)	C7—H7A	0.9800
O1—C7	1.469 (7)	C8—C14	1.390 (8)
O2—C12	1.376 (6)	C8—C9	1.399 (8)
O2—H2A	0.8200	C9—C11	1.398 (7)
C1—C2	1.507 (7)	C9—C10	1.513 (7)
C1—C10	1.534 (7)	C10—C17	1.553 (7)
C1—H1A	0.9700	C11—C12	1.413 (7)
C1—H1B	0.9700	C11—H11A	0.9300
C2—C3	1.523 (9)	C12—C13	1.384 (8)
C2—H2B	0.9700	C13—C14	1.385 (8)
C2—H2C	0.9700	C13—C18	1.523 (8)
C3—C4	1.531 (9)	C14—H14A	0.9300
C3—H3A	0.9700	C15—H15A	0.9600
C3—H3B	0.9700	C15—H15B	0.9600
C4—C16	1.516 (9)	C15—H15C	0.9600
C4—C15	1.547 (8)	C16—H16A	0.9600
C4—C5	1.555 (7)	C16—H16B	0.9600
C5—C10	1.552 (6)	C16—H16C	0.9600
C5—C6	1.583 (8)	C17—H17A	0.9700
C5—H5A	0.9800	C17—H17B	0.9700
C6—C7	1.500 (8)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C7—C8	1.495 (7)
C17—O1—C7	112.0 (4)	C9—C8—C7	112.0 (5)
C12—O2—H2A	109.5	C11—C9—C8	119.7 (5)
C2—C1—C10	113.4 (5)	C11—C9—C10	127.1 (5)
C2—C1—H1A	108.9	C8—C9—C10	113.2 (5)
C10—C1—H1A	108.9	C9—C10—C5	106.3 (4)
C2—C1—H1B	108.9	C9—C10—C1	113.5 (4)
C10—C1—H1B	108.9	C5—C10—C1	112.0 (4)
H1A—C1—H1B	107.7	C9—C10—C17	103.4 (4)
C1—C2—C3	111.5 (5)	C5—C10—C17	110.7 (4)
C1—C2—H2B	109.3	C1—C10—C17	110.6 (5)
C3—C2—H2B	109.3	C9—C11—C12	118.2 (5)
C1—C2—H2C	109.3	C9—C11—H11A	120.9
C3—C2—H2C	109.3	C12—C11—H11A	120.9
H2B—C2—H2C	108.0	C13—C12—O2	117.4 (5)
C2—C3—C4	113.7 (6)	C13—C12—C11	122.5 (5)
C2—C3—H3A	108.8	O2—C12—C11	120.1 (5)
C4—C3—H3A	108.8	C12—C13—C14	117.5 (5)
C2—C3—H3B	108.8	C12—C13—C18	121.1 (5)
C4—C3—H3B	108.8	C14—C13—C18	121.3 (6)
H3A—C3—H3B	107.7	C8—C14—C13	121.8 (5)
C16—C4—C3	109.3 (6)	C8—C14—H14A	119.1
C16—C4—C15	107.8 (5)	C13—C14—H14A	119.1
C3—C4—C15	107.5 (6)	C4—C15—H15A	109.5
C16—C4—C5	108.9 (5)	C4—C15—H15B	109.5
C3—C4—C5	107.7 (5)	H15A—C15—H15B	109.5
C15—C4—C5	115.5 (5)	C4—C15—H15C	109.5
C10—C5—C4	117.8 (4)	H15A—C15—H15C	109.5
C10—C5—C6	108.6 (4)	H15B—C15—H15C	109.5
C4—C5—C6	113.5 (4)	C4—C16—H16A	109.5
C10—C5—H5A	105.2	C4—C16—H16B	109.5
C4—C5—H5A	105.2	H16A—C16—H16B	109.5
C6—C5—H5A	105.2	C4—C16—H16C	109.5
C7—C6—C5	108.3 (5)	H16A—C16—H16C	109.5
C7—C6—H6A	110.0	H16B—C16—H16C	109.5
C5—C6—H6A	110.0	O1—C17—C10	110.8 (4)
C7—C6—H6B	110.0	O1—C17—H17A	109.5
C5—C6—H6B	110.0	C10—C17—H17A	109.5
H6A—C6—H6B	108.4	O1—C17—H17B	109.5
O1—C7—C8	108.7 (4)	C10—C17—H17B	109.5
O1—C7—C6	108.0 (5)	H17A—C17—H17B	108.1
C8—C7—C6	110.6 (5)	C13—C18—H18A	109.5
O1—C7—H7A	109.8	C13—C18—H18B	109.5
C8—C7—H7A	109.8	H18A—C18—H18B	109.5
C6—C7—H7A	109.8	C13—C18—H18C	109.5
C14—C8—C9	119.9 (5)	H18A—C18—H18C	109.5
C14—C8—C7	128.0 (5)	H18B—C18—H18C	109.5
C10—C1—C2—C3	−54.0 (8)	C8—C9—C10—C1	178.7 (5)
C1—C2—C3—C4	60.0 (8)	C11—C9—C10—C17	−121.8 (6)
C2—C3—C4—C16	−172.1 (5)	C8—C9—C10—C17	58.9 (5)
C2—C3—C4—C15	71.1 (7)	C4—C5—C10—C9	−168.0 (5)
C2—C3—C4—C5	−54.0 (7)	C6—C5—C10—C9	61.1 (5)
C16—C4—C5—C10	165.2 (5)	C4—C5—C10—C1	−43.6 (6)
C3—C4—C5—C10	46.8 (7)	C6—C5—C10—C1	−174.5 (5)
C15—C4—C5—C10	−73.3 (6)	C4—C5—C10—C17	80.3 (6)
C16—C4—C5—C6	−66.2 (6)	C6—C5—C10—C17	−50.5 (6)
C3—C4—C5—C6	175.4 (5)	C2—C1—C10—C9	165.8 (5)
C15—C4—C5—C6	55.2 (7)	C2—C1—C10—C5	45.5 (7)
C10—C5—C6—C7	−6.9 (6)	C2—C1—C10—C17	−78.5 (7)
C4—C5—C6—C7	−140.0 (5)	C8—C9—C11—C12	2.9 (8)
C17—O1—C7—C8	54.5 (6)	C10—C9—C11—C12	−176.3 (5)
C17—O1—C7—C6	−65.6 (6)	C9—C11—C12—C13	2.8 (8)
C5—C6—C7—O1	65.5 (6)	C9—C11—C12—O2	−179.0 (5)
C5—C6—C7—C8	−53.4 (6)	O2—C12—C13—C14	175.2 (5)
O1—C7—C8—C14	126.4 (6)	C11—C12—C13—C14	−6.4 (8)
C6—C7—C8—C14	−115.1 (6)	O2—C12—C13—C18	−4.7 (8)
O1—C7—C8—C9	−56.7 (6)	C11—C12—C13—C18	173.6 (6)
C6—C7—C8—C9	61.7 (6)	C9—C8—C14—C13	0.9 (8)
C14—C8—C9—C11	−4.7 (8)	C7—C8—C14—C13	177.5 (6)
C7—C8—C9—C11	178.1 (5)	C12—C13—C14—C8	4.6 (8)
C14—C8—C9—C10	174.6 (5)	C18—C13—C14—C8	−175.5 (5)
C7—C8—C9—C10	−2.5 (6)	C7—O1—C17—C10	4.3 (7)
C11—C9—C10—C5	121.5 (6)	C9—C10—C17—O1	−59.6 (6)
C8—C9—C10—C5	−57.8 (5)	C5—C10—C17—O1	53.9 (6)
C11—C9—C10—C1	−2.0 (8)	C1—C10—C17—O1	178.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1^i	0.82	1.93	2.750 (6)	174

Symmetry code: (i) −x, y+1/2, −z+2.