Crystal structure of (1R,2S,4R,7R,8S,9R)-3,3-dichloro-8,9-epoxy-4,8,12,12-tetramethyltricyclo[5.5.0.0(2,4)]dodecane.

The title compound, C16H24Cl2O, is built up from two fused six- and seven-membered rings which bear a di-chloro-cyclo-propane group and an ep-oxy group, respectively. In the mol-ecule, the six-membered ring adopts an envelope configuration with the C atom linking the ep-oxy ring at the flap, while the seven-membered ring adopts a boat-sofa conformation.

Related literature

For applications of epoxides, see: Qu et al. (2009 ▸); Taylor et al. (1991 ▸); Mori (1989 ▸); Paddon-Jones et al. (1997 ▸); Yang (2004 ▸); Vollhardt & Schore (1996 ▸); Trost et al. (1983 ▸). For related structures, see: Chiaroni et al. (1992 ▸, 1995 ▸, 1996a ▸,b ▸,c ▸); Sbai et al. (2002 ▸); Benharref et al. (2010 ▸); Oukhrib et al. (2013 ▸); Bimoussa et al. (2014 ▸). For puckering parameters and ring conformation, see: Boessenkool & Boeyens (1980 ▸).

Experimental

Crystal data

C16H24Cl2O

M = 303.25

Monoclinic,

a = 8.7706 (5) Å

b = 10.5467 (4) Å

c = 9.1639 (5) Å

β = 115.710 (7)°

V = 763.75 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 180 K

0.40 × 0.34 × 0.08 mm

Data collection

Agilent Xcalibur, Eos, Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014 ▸) T min = 0.901, T max = 1.000

7805 measured reflections

2945 independent reflections

2868 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.076

S = 1.05

2945 reflections

176 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack x determined using 1242 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: −0.02 (2)

Data collection: CrysAlis PRO (Agilent, 2014 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸) and ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S205698901501244X/xu5855sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901501244X/xu5855Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901501244X/xu5855Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901501244X/xu5855fig1.tif

Displacement ellipsoid plot of the title compound.

CCDC reference: 1409393

Additional supporting information: crystallographic information; 3D view; checkCIF report

C16H24Cl2O	F(000) = 324
Mr = 303.25	Dx = 1.319 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 8.7706 (5) Å	Cell parameters from 4267 reflections
b = 10.5467 (4) Å	θ = 4.3–29.3°
c = 9.1639 (5) Å	µ = 0.42 mm−1
β = 115.710 (7)°	T = 180 K
V = 763.75 (8) Å3	Box, colourless
Z = 2	0.40 × 0.34 × 0.08 mm

Agilent Xcalibur, Eos, Gemini ultra diffractometer	2945 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2868 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
Detector resolution: 16.1978 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −13→12
Tmin = 0.901, Tmax = 1.000	l = −11→11
7805 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1659P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.44 e Å−3
2945 reflections	Δρmin = −0.18 e Å−3
176 parameters	Absolute structure: Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.02 (2)

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.

	x	y	z	Uiso*/Ueq
C1	0.6765 (3)	1.0011 (2)	0.7612 (3)	0.0150 (5)
H1	0.5811	0.9485	0.6832	0.018*
C2	0.7132 (3)	1.0959 (2)	0.6554 (3)	0.0161 (5)
H2	0.7162	1.1866	0.6885	0.019*
C3	0.6463 (3)	1.0746 (2)	0.4760 (3)	0.0184 (5)
C4	0.8324 (3)	1.0632 (2)	0.5788 (3)	0.0183 (5)
C5	0.9157 (3)	0.9334 (3)	0.6122 (3)	0.0238 (5)
H5A	1.0399	0.9457	0.6641	0.029*
H5B	0.8860	0.8909	0.5070	0.029*
C6	0.8699 (3)	0.8432 (3)	0.7196 (3)	0.0222 (5)
H6A	0.7739	0.7896	0.6480	0.027*
H6B	0.9675	0.7863	0.7775	0.027*
C7	0.8220 (3)	0.9058 (2)	0.8456 (3)	0.0175 (5)
H7	0.7706	0.8360	0.8832	0.021*
C8	0.9699 (3)	0.9526 (3)	0.9984 (3)	0.0200 (5)
C9	0.9417 (3)	0.9677 (3)	1.1444 (3)	0.0234 (6)
H9	1.0197	1.0302	1.2236	0.028*
C10	0.7742 (3)	0.9537 (3)	1.1534 (3)	0.0266 (6)
H10A	0.7722	1.0173	1.2319	0.032*
H10B	0.7739	0.8692	1.2003	0.032*
C11	0.6069 (3)	0.9666 (3)	0.9990 (3)	0.0230 (6)
H11A	0.5167	0.9896	1.0317	0.028*
H11B	0.5778	0.8825	0.9461	0.028*
C12	0.6043 (3)	1.0642 (2)	0.8722 (3)	0.0189 (5)
C13	0.9439 (4)	1.1678 (3)	0.5645 (3)	0.0287 (6)
H13A	0.9746	1.1479	0.4762	0.043*
H13B	1.0468	1.1748	0.6664	0.043*
H13C	0.8823	1.2485	0.5416	0.043*
C14	1.1115 (3)	1.0267 (3)	0.9879 (3)	0.0278 (6)
H14A	1.1956	1.0487	1.0972	0.042*
H14B	1.0661	1.1045	0.9255	0.042*
H14C	1.1651	0.9752	0.9342	0.042*
C15	0.6951 (3)	1.1861 (2)	0.9559 (3)	0.0222 (5)
H15A	0.6600	1.2559	0.8774	0.033*
H15B	0.8178	1.1740	0.9988	0.033*
H15C	0.6658	1.2065	1.0449	0.033*
C16	0.4186 (3)	1.0978 (3)	0.7640 (3)	0.0294 (6)
H16A	0.3545	1.0200	0.7184	0.044*
H16B	0.4125	1.1533	0.6760	0.044*
H16C	0.3704	1.1415	0.8287	0.044*
O1	1.0269 (3)	0.85597 (19)	1.1245 (2)	0.0275 (4)
Cl1	0.52452 (8)	0.93841 (6)	0.38605 (7)	0.02818 (17)
Cl2	0.56482 (9)	1.20376 (6)	0.34222 (7)	0.03117 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0159 (11)	0.0142 (11)	0.0135 (10)	−0.0016 (9)	0.0052 (9)	−0.0003 (9)
C2	0.0194 (12)	0.0136 (12)	0.0158 (11)	0.0011 (10)	0.0082 (9)	0.0008 (9)
C3	0.0220 (12)	0.0154 (11)	0.0155 (11)	0.0027 (10)	0.0060 (9)	0.0039 (9)
C4	0.0182 (12)	0.0205 (12)	0.0169 (11)	0.0013 (10)	0.0083 (9)	0.0011 (9)
C5	0.0258 (12)	0.0274 (14)	0.0212 (11)	0.0085 (12)	0.0130 (9)	0.0008 (12)
C6	0.0277 (14)	0.0172 (12)	0.0200 (11)	0.0075 (11)	0.0090 (10)	0.0018 (9)
C7	0.0223 (12)	0.0133 (12)	0.0173 (11)	0.0008 (9)	0.0089 (10)	0.0007 (9)
C8	0.0215 (12)	0.0190 (12)	0.0158 (10)	0.0055 (11)	0.0047 (9)	0.0038 (10)
C9	0.0276 (13)	0.0234 (14)	0.0155 (11)	0.0049 (11)	0.0060 (10)	0.0011 (10)
C10	0.0348 (14)	0.0279 (14)	0.0203 (11)	0.0043 (13)	0.0150 (11)	0.0035 (11)
C11	0.0285 (13)	0.0240 (14)	0.0216 (11)	−0.0017 (11)	0.0158 (10)	0.0012 (10)
C12	0.0198 (12)	0.0208 (13)	0.0183 (11)	−0.0004 (10)	0.0102 (9)	−0.0002 (10)
C13	0.0301 (14)	0.0327 (16)	0.0284 (13)	−0.0062 (13)	0.0175 (11)	−0.0007 (12)
C14	0.0215 (13)	0.0320 (15)	0.0251 (13)	−0.0017 (12)	0.0057 (11)	0.0026 (12)
C15	0.0309 (13)	0.0175 (13)	0.0213 (11)	0.0026 (11)	0.0142 (10)	−0.0009 (11)
C16	0.0222 (14)	0.0384 (16)	0.0296 (13)	0.0054 (13)	0.0132 (11)	0.0021 (13)
O1	0.0334 (11)	0.0271 (11)	0.0197 (9)	0.0117 (9)	0.0094 (8)	0.0075 (8)
Cl1	0.0305 (3)	0.0301 (3)	0.0191 (3)	−0.0081 (3)	0.0062 (2)	−0.0044 (3)
Cl2	0.0418 (4)	0.0283 (3)	0.0250 (3)	0.0152 (3)	0.0159 (3)	0.0122 (3)

C1—C2	1.521 (3)	C9—O1	1.449 (3)
C1—C7	1.542 (3)	C9—C10	1.513 (4)
C1—C12	1.561 (3)	C9—H9	1.0000
C1—H1	1.0000	C10—C11	1.540 (4)
C2—C3	1.503 (3)	C10—H10A	0.9900
C2—C4	1.530 (3)	C10—H10B	0.9900
C2—H2	1.0000	C11—C12	1.545 (3)
C3—C4	1.494 (4)	C11—H11A	0.9900
C3—Cl2	1.764 (2)	C11—H11B	0.9900
C3—Cl1	1.766 (3)	C12—C15	1.532 (4)
C4—C13	1.517 (4)	C12—C16	1.536 (4)
C4—C5	1.519 (4)	C13—H13A	0.9800
C5—C6	1.542 (4)	C13—H13B	0.9800
C5—H5A	0.9900	C13—H13C	0.9800
C5—H5B	0.9900	C14—H14A	0.9800
C6—C7	1.538 (3)	C14—H14B	0.9800
C6—H6A	0.9900	C14—H14C	0.9800
C6—H6B	0.9900	C15—H15A	0.9800
C7—C8	1.520 (3)	C15—H15B	0.9800
C7—H7	1.0000	C15—H15C	0.9800
C8—O1	1.457 (3)	C16—H16A	0.9800
C8—C9	1.471 (3)	C16—H16B	0.9800
C8—C14	1.505 (4)	C16—H16C	0.9800
C2—C1—C7	112.96 (19)	O1—C9—C10	119.6 (2)
C2—C1—C12	113.1 (2)	C8—C9—C10	126.1 (2)
C7—C1—C12	115.62 (19)	O1—C9—H9	113.6
C2—C1—H1	104.6	C8—C9—H9	113.6
C7—C1—H1	104.6	C10—C9—H9	113.6
C12—C1—H1	104.6	C9—C10—C11	120.1 (2)
C3—C2—C1	120.6 (2)	C9—C10—H10A	107.3
C3—C2—C4	59.00 (16)	C11—C10—H10A	107.3
C1—C2—C4	121.3 (2)	C9—C10—H10B	107.3
C3—C2—H2	114.9	C11—C10—H10B	107.3
C1—C2—H2	114.9	H10A—C10—H10B	106.9
C4—C2—H2	114.9	C10—C11—C12	116.6 (2)
C4—C3—C2	61.39 (16)	C10—C11—H11A	108.2
C4—C3—Cl2	120.18 (19)	C12—C11—H11A	108.2
C2—C3—Cl2	119.53 (18)	C10—C11—H11B	108.2
C4—C3—Cl1	120.21 (18)	C12—C11—H11B	108.2
C2—C3—Cl1	120.14 (18)	H11A—C11—H11B	107.3
Cl2—C3—Cl1	108.85 (13)	C15—C12—C16	107.7 (2)
C3—C4—C13	117.1 (2)	C15—C12—C11	110.4 (2)
C3—C4—C5	119.9 (2)	C16—C12—C11	107.7 (2)
C13—C4—C5	113.6 (2)	C15—C12—C1	114.5 (2)
C3—C4—C2	59.62 (16)	C16—C12—C1	107.1 (2)
C13—C4—C2	118.0 (2)	C11—C12—C1	109.2 (2)
C5—C4—C2	118.4 (2)	C4—C13—H13A	109.5
C4—C5—C6	116.7 (2)	C4—C13—H13B	109.5
C4—C5—H5A	108.1	H13A—C13—H13B	109.5
C6—C5—H5A	108.1	C4—C13—H13C	109.5
C4—C5—H5B	108.1	H13A—C13—H13C	109.5
C6—C5—H5B	108.1	H13B—C13—H13C	109.5
H5A—C5—H5B	107.3	C8—C14—H14A	109.5
C7—C6—C5	116.5 (2)	C8—C14—H14B	109.5
C7—C6—H6A	108.2	H14A—C14—H14B	109.5
C5—C6—H6A	108.2	C8—C14—H14C	109.5
C7—C6—H6B	108.2	H14A—C14—H14C	109.5
C5—C6—H6B	108.2	H14B—C14—H14C	109.5
H6A—C6—H6B	107.3	C12—C15—H15A	109.5
C8—C7—C6	115.4 (2)	C12—C15—H15B	109.5
C8—C7—C1	116.08 (19)	H15A—C15—H15B	109.5
C6—C7—C1	109.83 (19)	C12—C15—H15C	109.5
C8—C7—H7	104.7	H15A—C15—H15C	109.5
C6—C7—H7	104.7	H15B—C15—H15C	109.5
C1—C7—H7	104.7	C12—C16—H16A	109.5
O1—C8—C9	59.31 (15)	C12—C16—H16B	109.5
O1—C8—C14	113.9 (2)	H16A—C16—H16B	109.5
C9—C8—C14	118.1 (2)	C12—C16—H16C	109.5
O1—C8—C7	111.4 (2)	H16A—C16—H16C	109.5
C9—C8—C7	117.4 (2)	H16B—C16—H16C	109.5
C14—C8—C7	120.5 (2)	C9—O1—C8	60.82 (15)
O1—C9—C8	59.88 (15)