(1S,3R,6S,7R)-3,7-Dichloro-trans-himachalane

The mol­ecule of the title compound, C₁₅H₂₆Cl₂, is built up from two fused six-membered and seven-membered rings. The six-membered ring has a perfect chair conformation, whereas the seven-membered ring displays a twist-chair conformation. A weak C—H...Cl hydrogen-bonding inter­action links the mol­ecule into a chain parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.090
• Data-to-parameter ratio = 29.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.93
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.77 mm

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.928
            Tmax scaled      0.928 Tmin scaled      0.757
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           32.20
           From the CIF: _reflns_number_total               4979
           Count of symmetry unique reflns         3029
           Completeness (_total/calc)            164.38%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1950
           Fraction of Friedel pairs measured     0.644
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1S,3R,6S,7R)-3,7-Dichloro-trans-himachalane

Crystal data

C15H26Cl2	F(000) = 600
Mr = 277.26	Dx = 1.221 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5072 reflections
a = 6.0259 (4) Å	θ = 2.7–32.1°
b = 15.6356 (9) Å	µ = 0.41 mm^−1
c = 16.0117 (11) Å	T = 180 K
V = 1508.60 (17) Å^3	Needle, colorless
Z = 4	0.77 × 0.28 × 0.18 mm

Data collection

Oxford Diffraction CCD Xcalibur diffractometer	4979 independent reflections
Radiation source: fine-focus sealed tube	4123 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 8.2632 pixels mm^-1	θmax = 32.2°, θmin = 2.9°
ω and φ scans	h = −8→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −22→23
Tmin = 0.816, Tmax = 1.0	l = −21→23
16088 measured 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)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0553P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4601 reflections	Δρmax = 0.29 e Å^−3
158 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1963 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

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. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3) (p.p.m.): 1.61, 1.63 (3H12, 3H13, 2 s), 0.85, 0.97 (3H14, 3H15, 2 s); 13 C NMR (CDCl3) (p.p.m.): 43.8 (C-1), 51.1 (C-2), 72.7 (C-3), 46.2 (C-4), 33.1 (C-5), 44.1 (C-6), 76.9 (C-7), 35.7 (C-8), 21.5 (C-9), 34.6 (C-10), 36.3 (C-11), 41.5 (C-12), 40.7 (C-13), 22.5 (C-14), 26.5 (C-15).

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

	x	y	z	Uiso*/Ueq
C1	0.4376 (2)	0.00470 (8)	0.54846 (7)	0.0183 (2)
H1	0.2720	0.0034	0.5448	0.022*
C2	0.4958 (2)	0.05331 (8)	0.62985 (8)	0.0210 (2)
H2A	0.4383	0.0199	0.6777	0.025*
H2B	0.6594	0.0553	0.6352	0.025*
C3	0.4075 (2)	0.14424 (8)	0.63694 (9)	0.0228 (2)
C4	0.4732 (3)	0.19491 (9)	0.56003 (9)	0.0263 (3)
H4A	0.3956	0.2507	0.5609	0.032*
H4B	0.6348	0.2063	0.5620	0.032*
C5	0.4186 (3)	0.14916 (9)	0.47923 (9)	0.0267 (3)
H5A	0.4731	0.1840	0.4319	0.032*
H5B	0.2553	0.1447	0.4740	0.032*
C6	0.5201 (2)	0.05845 (9)	0.47274 (8)	0.0208 (3)
H6	0.6838	0.0655	0.4803	0.025*
C7	0.4864 (3)	0.02318 (10)	0.38266 (8)	0.0264 (3)
C8	0.6097 (3)	−0.06061 (10)	0.36414 (10)	0.0329 (3)
H81	0.6152	−0.0670	0.3027	0.039*
H82	0.7646	−0.0530	0.3834	0.039*
C9	0.5278 (3)	−0.14502 (11)	0.39947 (10)	0.0373 (4)
H91	0.6563	−0.1844	0.4021	0.045*
H92	0.4215	−0.1695	0.3589	0.045*
C10	0.4161 (3)	−0.14574 (9)	0.48528 (9)	0.0315 (3)
H101	0.4121	−0.2058	0.5048	0.038*
H102	0.2602	−0.1274	0.4774	0.038*
C11	0.5156 (3)	−0.09102 (9)	0.55648 (9)	0.0250 (3)
C12	0.4811 (3)	0.18776 (10)	0.71715 (10)	0.0340 (4)
H121	0.4299	0.1543	0.7652	0.051*
H122	0.4174	0.2454	0.7198	0.051*
H123	0.6434	0.1916	0.7182	0.051*
C13	0.5603 (3)	0.08826 (13)	0.31648 (10)	0.0429 (4)
H131	0.7157	0.1038	0.3261	0.064*
H132	0.4674	0.1396	0.3204	0.064*
H133	0.5448	0.0630	0.2608	0.064*
C14	0.4182 (3)	−0.12981 (9)	0.63686 (11)	0.0387 (4)
H141	0.4430	−0.1918	0.6370	0.058*
H142	0.2585	−0.1182	0.6392	0.058*
H143	0.4910	−0.1042	0.6855	0.058*
C15	0.7694 (3)	−0.09965 (11)	0.56065 (11)	0.0362 (4)
H151	0.8248	−0.0705	0.6107	0.054*
H152	0.8356	−0.0736	0.5109	0.054*
H153	0.8097	−0.1603	0.5631	0.054*
Cl3	0.10164 (6)	0.13898 (2)	0.64072 (3)	0.03430 (10)
Cl7	0.18821 (6)	0.00626 (3)	0.36419 (3)	0.03478 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0172 (6)	0.0184 (5)	0.0193 (5)	0.0016 (5)	−0.0016 (4)	0.0001 (5)
C2	0.0231 (6)	0.0194 (5)	0.0206 (6)	0.0016 (5)	−0.0019 (6)	0.0000 (5)
C3	0.0214 (6)	0.0211 (5)	0.0260 (6)	0.0000 (5)	0.0020 (6)	−0.0011 (6)
C4	0.0298 (8)	0.0193 (6)	0.0297 (7)	−0.0025 (6)	0.0026 (6)	0.0016 (5)
C5	0.0327 (8)	0.0220 (6)	0.0252 (7)	0.0031 (6)	0.0012 (6)	0.0073 (5)
C6	0.0173 (6)	0.0254 (6)	0.0197 (6)	−0.0003 (5)	−0.0001 (5)	0.0026 (5)
C7	0.0193 (6)	0.0389 (8)	0.0211 (6)	−0.0005 (6)	0.0010 (5)	0.0018 (5)
C8	0.0271 (7)	0.0462 (8)	0.0254 (7)	0.0042 (7)	0.0023 (7)	−0.0084 (7)
C9	0.0426 (9)	0.0363 (8)	0.0328 (8)	0.0079 (8)	−0.0060 (7)	−0.0125 (7)
C10	0.0368 (8)	0.0237 (7)	0.0341 (8)	−0.0001 (7)	−0.0066 (6)	−0.0053 (6)
C11	0.0321 (8)	0.0180 (6)	0.0248 (6)	0.0025 (5)	−0.0047 (6)	−0.0018 (5)
C12	0.0422 (10)	0.0290 (8)	0.0309 (8)	0.0026 (7)	−0.0032 (7)	−0.0092 (6)
C13	0.0504 (11)	0.0565 (11)	0.0217 (7)	−0.0051 (9)	0.0077 (7)	0.0087 (7)
C14	0.0639 (11)	0.0226 (6)	0.0298 (7)	−0.0018 (7)	−0.0052 (9)	0.0081 (6)
C15	0.0360 (9)	0.0327 (8)	0.0399 (9)	0.0139 (7)	−0.0127 (7)	−0.0083 (7)
Cl3	0.02332 (16)	0.03535 (18)	0.0442 (2)	0.00334 (14)	0.00712 (17)	−0.00121 (17)
Cl7	0.02419 (16)	0.0494 (2)	0.03075 (17)	0.00076 (16)	−0.00922 (14)	−0.00253 (18)

Geometric parameters (Å, º)

C1—C2	1.5489 (17)	C8—H81	0.9900
C1—C6	1.5566 (18)	C8—H82	0.9900
C1—C11	1.5739 (19)	C9—C10	1.530 (2)
C1—H1	1.0000	C9—H91	0.9900
C2—C3	1.5224 (17)	C9—H92	0.9900
C2—H2A	0.9900	C10—C11	1.547 (2)
C2—H2B	0.9900	C10—H101	0.9900
C3—C4	1.5170 (19)	C10—H102	0.9900
C3—C12	1.520 (2)	C11—C15	1.537 (2)
C3—Cl3	1.8459 (14)	C11—C14	1.539 (2)
C4—C5	1.515 (2)	C12—H121	0.9800
C4—H4A	0.9900	C12—H122	0.9800
C4—H4B	0.9900	C12—H123	0.9800
C5—C6	1.5481 (19)	C13—H131	0.9800
C5—H5A	0.9900	C13—H132	0.9800
C5—H5B	0.9900	C13—H133	0.9800
C6—C7	1.5573 (19)	C14—H141	0.9800
C6—H6	1.0000	C14—H142	0.9800
C7—C8	1.535 (2)	C14—H143	0.9800
C7—C13	1.535 (2)	C15—H151	0.9800
C7—Cl7	1.8403 (15)	C15—H152	0.9800
C8—C9	1.518 (2)	C15—H153	0.9800
C2—C1—C6	108.55 (10)	C9—C8—H82	107.1
C2—C1—C11	109.29 (10)	C7—C8—H82	107.1
C6—C1—C11	118.80 (11)	H81—C8—H82	106.8
C2—C1—H1	106.5	C8—C9—C10	118.94 (13)
C6—C1—H1	106.5	C8—C9—H91	107.6
C11—C1—H1	106.5	C10—C9—H91	107.6
C3—C2—C1	116.23 (11)	C8—C9—H92	107.6
C3—C2—H2A	108.2	C10—C9—H92	107.6
C1—C2—H2A	108.2	H91—C9—H92	107.0
C3—C2—H2B	108.2	C9—C10—C11	119.15 (14)
C1—C2—H2B	108.2	C9—C10—H101	107.5
H2A—C2—H2B	107.4	C11—C10—H101	107.5
C4—C3—C12	112.09 (11)	C9—C10—H102	107.5
C4—C3—C2	109.63 (11)	C11—C10—H102	107.5
C12—C3—C2	112.29 (12)	H101—C10—H102	107.0
C4—C3—Cl3	108.09 (10)	C15—C11—C14	107.99 (14)
C12—C3—Cl3	106.47 (10)	C15—C11—C10	111.68 (13)
C2—C3—Cl3	108.05 (9)	C14—C11—C10	104.50 (12)
C5—C4—C3	112.95 (12)	C15—C11—C1	112.60 (12)
C5—C4—H4A	109.0	C14—C11—C1	109.21 (12)
C3—C4—H4A	109.0	C10—C11—C1	110.49 (11)
C5—C4—H4B	109.0	C3—C12—H121	109.5
C3—C4—H4B	109.0	C3—C12—H122	109.5
H4A—C4—H4B	107.8	H121—C12—H122	109.5
C4—C5—C6	113.84 (12)	C3—C12—H123	109.5
C4—C5—H5A	108.8	H121—C12—H123	109.5
C6—C5—H5A	108.8	H122—C12—H123	109.5
C4—C5—H5B	108.8	C7—C13—H131	109.5
C6—C5—H5B	108.8	C7—C13—H132	109.5
H5A—C5—H5B	107.7	H131—C13—H132	109.5
C5—C6—C1	108.44 (11)	C7—C13—H133	109.5
C5—C6—C7	109.58 (11)	H131—C13—H133	109.5
C1—C6—C7	119.25 (11)	H132—C13—H133	109.5
C5—C6—H6	106.3	C11—C14—H141	109.5
C1—C6—H6	106.3	C11—C14—H142	109.5
C7—C6—H6	106.3	H141—C14—H142	109.5
C8—C7—C13	106.99 (13)	C11—C14—H143	109.5
C8—C7—C6	114.72 (12)	H141—C14—H143	109.5
C13—C7—C6	111.52 (13)	H142—C14—H143	109.5
C8—C7—Cl7	108.58 (10)	C11—C15—H151	109.5
C13—C7—Cl7	105.51 (11)	C11—C15—H152	109.5
C6—C7—Cl7	109.08 (10)	H151—C15—H152	109.5
C9—C8—C7	120.86 (13)	C11—C15—H153	109.5
C9—C8—H81	107.1	H151—C15—H153	109.5
C7—C8—H81	107.1	H152—C15—H153	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H82···Cl7^i	0.99	2.73	3.6397 (16)	152

Symmetry code: (i) x+1, y, z.