rac-(2aS,2a¹R,3aR,3a¹S,5aS,6aR)-2a-Allyl-2,4-di­chloro-2a,2a¹,3a¹,5a,6,6a-hexa­hydro-3aH-3-oxadi­cyclo­penta­[cd,gh]penta­len-3a-ol

The title racemic triquinane, C₁₄H₁₄Cl₂O₂, is composed of four five-membered rings, one of which is a tetra­hydro­furan ring to which an allyl group on one side and a hydroxyl group on the other side are attached. The core of the triquinane unit has a cis–syn–cis configuration. In the crystal, the mol­ecules are linked by pairwise O—H...O hydrogen bonds, generating inversion dimers featuring R²₂(8) loops.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.048
• wR factor = 0.107
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00494 Ang.
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.479 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.594          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.004 Degree
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C5          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C6          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C7          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C11         (Centro SPGR)          S Verify
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        46% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   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

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

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Computing details

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: ShelXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

rac-(2aS,2a¹R,3aR,3a¹S,5aS,6aR)-2a-Allyl-2,4-dichloro-2a,2a¹,3a¹,5a,6,6a-hexahydro-3aH-3-oxadicyclopenta[cd,gh]pentalen-3a-ol

Crystal data

C14H14Cl2O2	Z = 2
Mr = 285.15	F(000) = 296
Triclinic, P1	Dx = 1.482 Mg m^−3
a = 7.2687 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3648 (11) Å	Cell parameters from 3239 reflections
c = 11.7460 (18) Å	θ = 2.7–25.0°
α = 80.448 (4)°	µ = 0.50 mm^−1
β = 83.441 (4)°	T = 150 K
γ = 65.285 (4)°	Plate, clear light colourless
V = 638.96 (16) Å^3	0.32 × 0.29 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	1662 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.106
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θmax = 25.0°, θmin = 2.7°
Tmin = 0.655, Tmax = 0.746	h = −8→8
19764 measured reflections	k = −9→9
2241 independent reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H-atom parameters constrained
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.0235P)^2 + 1.1376P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
2241 reflections	Δρmax = 0.27 e Å^−3
164 parameters	Δρmin = −0.33 e Å^−3
0 restraints

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
Cl1	0.06076 (13)	0.17026 (12)	0.42861 (8)	0.0269 (3)
Cl2	−0.06759 (13)	0.53279 (13)	0.15245 (8)	0.0328 (3)
O1	0.1461 (3)	0.5253 (3)	0.37821 (19)	0.0191 (5)
O2	0.2783 (3)	0.3694 (3)	0.55085 (19)	0.0221 (6)
H2	0.157708	0.391949	0.574798	0.033*
C1	0.2966 (5)	0.3622 (4)	0.4322 (3)	0.0185 (8)
C11	0.2225 (5)	0.5758 (4)	0.2653 (3)	0.0192 (8)
C3	0.4551 (5)	0.0894 (4)	0.3551 (3)	0.0209 (8)
H3	0.474728	−0.022512	0.335419	0.025*
C10	0.1821 (5)	0.4890 (4)	0.1739 (3)	0.0194 (8)
C6	0.4571 (5)	0.4848 (4)	0.2673 (3)	0.0179 (7)
H6	0.518199	0.572267	0.266037	0.021*
C2	0.2846 (5)	0.1995 (4)	0.4009 (3)	0.0198 (8)
C9	0.3446 (5)	0.3828 (4)	0.1197 (3)	0.0211 (8)
H9	0.342144	0.317963	0.061141	0.025*
C4	0.6154 (5)	0.1623 (4)	0.3377 (3)	0.0203 (8)
H4	0.732882	0.086130	0.386498	0.024*
C7	0.5363 (5)	0.3772 (4)	0.1626 (3)	0.0206 (8)
H7	0.604311	0.435233	0.101481	0.025*
C8	0.6874 (5)	0.1927 (5)	0.2120 (3)	0.0240 (8)
H8A	0.688215	0.100747	0.168389	0.029*
H8B	0.826068	0.188696	0.207430	0.029*
C5	0.5042 (5)	0.3485 (4)	0.3779 (3)	0.0195 (8)
H5	0.584893	0.371253	0.431830	0.023*
C13	0.1802 (5)	0.8510 (5)	0.1251 (3)	0.0270 (9)
H13	0.152010	0.810452	0.061014	0.032*
C12	0.1281 (5)	0.7775 (4)	0.2438 (3)	0.0253 (8)
H12A	−0.021149	0.820022	0.254500	0.030*
H12B	0.174476	0.823785	0.301924	0.030*
C14	0.2611 (6)	0.9658 (5)	0.1035 (4)	0.0399 (11)
H14A	0.291514	1.009520	0.165285	0.048*
H14B	0.289666	1.006095	0.025767	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0202 (5)	0.0279 (5)	0.0360 (6)	−0.0142 (4)	−0.0005 (4)	−0.0023 (4)
Cl2	0.0145 (5)	0.0479 (6)	0.0353 (6)	−0.0122 (4)	−0.0051 (4)	−0.0026 (5)
O1	0.0093 (12)	0.0173 (12)	0.0240 (14)	0.0000 (10)	0.0021 (10)	−0.0013 (10)
O2	0.0154 (13)	0.0278 (14)	0.0207 (14)	−0.0065 (11)	0.0014 (10)	−0.0045 (11)
C1	0.0109 (17)	0.0171 (18)	0.023 (2)	−0.0020 (14)	0.0003 (14)	−0.0012 (15)
C11	0.0128 (18)	0.0183 (18)	0.022 (2)	−0.0031 (15)	0.0037 (14)	−0.0039 (15)
C3	0.0184 (19)	0.0157 (18)	0.027 (2)	−0.0049 (15)	−0.0040 (15)	−0.0026 (15)
C10	0.0112 (18)	0.0185 (18)	0.028 (2)	−0.0057 (15)	−0.0039 (15)	0.0008 (15)
C6	0.0095 (17)	0.0166 (18)	0.026 (2)	−0.0038 (14)	0.0024 (14)	−0.0049 (15)
C2	0.0189 (19)	0.0156 (18)	0.024 (2)	−0.0074 (16)	−0.0053 (15)	0.0039 (15)
C9	0.023 (2)	0.0166 (18)	0.022 (2)	−0.0073 (16)	−0.0035 (16)	−0.0008 (15)
C4	0.0108 (18)	0.0173 (18)	0.026 (2)	0.0015 (15)	−0.0040 (14)	−0.0026 (15)
C7	0.0134 (18)	0.0202 (18)	0.025 (2)	−0.0049 (15)	0.0038 (14)	−0.0021 (15)
C8	0.0125 (18)	0.024 (2)	0.030 (2)	−0.0022 (16)	−0.0001 (15)	−0.0045 (16)
C5	0.0116 (17)	0.0228 (19)	0.025 (2)	−0.0075 (15)	−0.0002 (14)	−0.0042 (15)
C13	0.026 (2)	0.0174 (19)	0.032 (2)	−0.0030 (16)	−0.0035 (16)	−0.0018 (16)
C12	0.019 (2)	0.0178 (19)	0.031 (2)	−0.0016 (16)	0.0050 (16)	−0.0032 (16)
C14	0.056 (3)	0.043 (3)	0.032 (2)	−0.033 (2)	−0.002 (2)	−0.0005 (19)

Geometric parameters (Å, º)

Cl1—C2	1.731 (3)	C3—C4	1.506 (5)
Cl2—C10	1.734 (3)	C10—C9	1.315 (5)
O1—C1	1.444 (4)	C6—C7	1.557 (5)
O1—C11	1.445 (4)	C6—C5	1.545 (5)
O2—C1	1.394 (4)	C9—C7	1.515 (5)
C1—C2	1.506 (5)	C4—C8	1.526 (5)
C1—C5	1.536 (4)	C4—C5	1.552 (5)
C11—C10	1.508 (5)	C7—C8	1.534 (5)
C11—C6	1.550 (4)	C13—C12	1.501 (5)
C11—C12	1.520 (5)	C13—C14	1.300 (5)
C3—C2	1.316 (5)
C1—O1—C11	110.0 (2)	C5—C6—C11	105.6 (3)
O1—C1—C2	112.9 (3)	C5—C6—C7	106.9 (3)
O1—C1—C5	107.0 (3)	C1—C2—Cl1	119.8 (2)
O2—C1—O1	107.8 (3)	C3—C2—Cl1	126.3 (3)
O2—C1—C2	113.5 (3)	C3—C2—C1	113.9 (3)
O2—C1—C5	113.0 (3)	C10—C9—C7	111.3 (3)
C2—C1—C5	102.5 (3)	C3—C4—C8	114.6 (3)
O1—C11—C10	111.4 (3)	C3—C4—C5	103.4 (3)
O1—C11—C6	106.4 (2)	C8—C4—C5	106.3 (3)
O1—C11—C12	106.8 (3)	C9—C7—C6	103.2 (3)
C10—C11—C6	101.7 (3)	C9—C7—C8	115.4 (3)
C10—C11—C12	113.9 (3)	C8—C7—C6	105.4 (3)
C12—C11—C6	116.5 (3)	C4—C8—C7	105.9 (3)
C2—C3—C4	111.8 (3)	C1—C5—C6	105.2 (3)
C11—C10—Cl2	118.3 (2)	C1—C5—C4	107.3 (3)
C9—C10—Cl2	126.5 (3)	C6—C5—C4	106.6 (3)
C9—C10—C11	115.1 (3)	C14—C13—C12	125.0 (4)
C11—C6—C7	107.5 (3)	C13—C12—C11	113.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.84	2.06	2.893 (3)	173

Symmetry code: (i) −x, −y+1, −z+1.