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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008409/om2105sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008409/om2105Isup2.hkl
Contains datablock I

CCDC reference: 640438

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

Computing details top

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 top
Crystal data top
C15H26Cl2F(000) = 600
Mr = 277.26Dx = 1.221 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5072 reflections
a = 6.0259 (4) Åθ = 2.7–32.1°
b = 15.6356 (9) ŵ = 0.41 mm1
c = 16.0117 (11) ÅT = 180 K
V = 1508.60 (17) Å3Needle, colorless
Z = 40.77 × 0.28 × 0.18 mm
Data collection top
Oxford Diffraction CCD Xcalibur
diffractometer
4979 independent reflections
Radiation source: fine-focus sealed tube4123 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
Detector resolution: 8.2632 pixels mm-1θmax = 32.2°, θmin = 2.9°
ω and φ scansh = 88
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2006)
k = 2223
Tmin = 0.816, Tmax = 1.0l = 2123
16088 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0553P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4601 reflectionsΔρmax = 0.29 e Å3
158 parametersΔρmin = 0.30 e Å3
0 restraintsAbsolute structure: Flack (1983), 1963 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.4376 (2)0.00470 (8)0.54846 (7)0.0183 (2)
H10.27200.00340.54480.022*
C20.4958 (2)0.05331 (8)0.62985 (8)0.0210 (2)
H2A0.43830.01990.67770.025*
H2B0.65940.05530.63520.025*
C30.4075 (2)0.14424 (8)0.63694 (9)0.0228 (2)
C40.4732 (3)0.19491 (9)0.56003 (9)0.0263 (3)
H4A0.39560.25070.56090.032*
H4B0.63480.20630.56200.032*
C50.4186 (3)0.14916 (9)0.47923 (9)0.0267 (3)
H5A0.47310.18400.43190.032*
H5B0.25530.14470.47400.032*
C60.5201 (2)0.05845 (9)0.47274 (8)0.0208 (3)
H60.68380.06550.48030.025*
C70.4864 (3)0.02318 (10)0.38266 (8)0.0264 (3)
C80.6097 (3)0.06061 (10)0.36414 (10)0.0329 (3)
H810.61520.06700.30270.039*
H820.76460.05300.38340.039*
C90.5278 (3)0.14502 (11)0.39947 (10)0.0373 (4)
H910.65630.18440.40210.045*
H920.42150.16950.35890.045*
C100.4161 (3)0.14574 (9)0.48528 (9)0.0315 (3)
H1010.41210.20580.50480.038*
H1020.26020.12740.47740.038*
C110.5156 (3)0.09102 (9)0.55648 (9)0.0250 (3)
C120.4811 (3)0.18776 (10)0.71715 (10)0.0340 (4)
H1210.42990.15430.76520.051*
H1220.41740.24540.71980.051*
H1230.64340.19160.71820.051*
C130.5603 (3)0.08826 (13)0.31648 (10)0.0429 (4)
H1310.71570.10380.32610.064*
H1320.46740.13960.32040.064*
H1330.54480.06300.26080.064*
C140.4182 (3)0.12981 (9)0.63686 (11)0.0387 (4)
H1410.44300.19180.63700.058*
H1420.25850.11820.63920.058*
H1430.49100.10420.68550.058*
C150.7694 (3)0.09965 (11)0.56065 (11)0.0362 (4)
H1510.82480.07050.61070.054*
H1520.83560.07360.51090.054*
H1530.80970.16030.56310.054*
Cl30.10164 (6)0.13898 (2)0.64072 (3)0.03430 (10)
Cl70.18821 (6)0.00626 (3)0.36419 (3)0.03478 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0172 (6)0.0184 (5)0.0193 (5)0.0016 (5)0.0016 (4)0.0001 (5)
C20.0231 (6)0.0194 (5)0.0206 (6)0.0016 (5)0.0019 (6)0.0000 (5)
C30.0214 (6)0.0211 (5)0.0260 (6)0.0000 (5)0.0020 (6)0.0011 (6)
C40.0298 (8)0.0193 (6)0.0297 (7)0.0025 (6)0.0026 (6)0.0016 (5)
C50.0327 (8)0.0220 (6)0.0252 (7)0.0031 (6)0.0012 (6)0.0073 (5)
C60.0173 (6)0.0254 (6)0.0197 (6)0.0003 (5)0.0001 (5)0.0026 (5)
C70.0193 (6)0.0389 (8)0.0211 (6)0.0005 (6)0.0010 (5)0.0018 (5)
C80.0271 (7)0.0462 (8)0.0254 (7)0.0042 (7)0.0023 (7)0.0084 (7)
C90.0426 (9)0.0363 (8)0.0328 (8)0.0079 (8)0.0060 (7)0.0125 (7)
C100.0368 (8)0.0237 (7)0.0341 (8)0.0001 (7)0.0066 (6)0.0053 (6)
C110.0321 (8)0.0180 (6)0.0248 (6)0.0025 (5)0.0047 (6)0.0018 (5)
C120.0422 (10)0.0290 (8)0.0309 (8)0.0026 (7)0.0032 (7)0.0092 (6)
C130.0504 (11)0.0565 (11)0.0217 (7)0.0051 (9)0.0077 (7)0.0087 (7)
C140.0639 (11)0.0226 (6)0.0298 (7)0.0018 (7)0.0052 (9)0.0081 (6)
C150.0360 (9)0.0327 (8)0.0399 (9)0.0139 (7)0.0127 (7)0.0083 (7)
Cl30.02332 (16)0.03535 (18)0.0442 (2)0.00334 (14)0.00712 (17)0.00121 (17)
Cl70.02419 (16)0.0494 (2)0.03075 (17)0.00076 (16)0.00922 (14)0.00253 (18)
Geometric parameters (Å, º) top
C1—C21.5489 (17)C8—H810.9900
C1—C61.5566 (18)C8—H820.9900
C1—C111.5739 (19)C9—C101.530 (2)
C1—H11.0000C9—H910.9900
C2—C31.5224 (17)C9—H920.9900
C2—H2A0.9900C10—C111.547 (2)
C2—H2B0.9900C10—H1010.9900
C3—C41.5170 (19)C10—H1020.9900
C3—C121.520 (2)C11—C151.537 (2)
C3—Cl31.8459 (14)C11—C141.539 (2)
C4—C51.515 (2)C12—H1210.9800
C4—H4A0.9900C12—H1220.9800
C4—H4B0.9900C12—H1230.9800
C5—C61.5481 (19)C13—H1310.9800
C5—H5A0.9900C13—H1320.9800
C5—H5B0.9900C13—H1330.9800
C6—C71.5573 (19)C14—H1410.9800
C6—H61.0000C14—H1420.9800
C7—C81.535 (2)C14—H1430.9800
C7—C131.535 (2)C15—H1510.9800
C7—Cl71.8403 (15)C15—H1520.9800
C8—C91.518 (2)C15—H1530.9800
C2—C1—C6108.55 (10)C9—C8—H82107.1
C2—C1—C11109.29 (10)C7—C8—H82107.1
C6—C1—C11118.80 (11)H81—C8—H82106.8
C2—C1—H1106.5C8—C9—C10118.94 (13)
C6—C1—H1106.5C8—C9—H91107.6
C11—C1—H1106.5C10—C9—H91107.6
C3—C2—C1116.23 (11)C8—C9—H92107.6
C3—C2—H2A108.2C10—C9—H92107.6
C1—C2—H2A108.2H91—C9—H92107.0
C3—C2—H2B108.2C9—C10—C11119.15 (14)
C1—C2—H2B108.2C9—C10—H101107.5
H2A—C2—H2B107.4C11—C10—H101107.5
C4—C3—C12112.09 (11)C9—C10—H102107.5
C4—C3—C2109.63 (11)C11—C10—H102107.5
C12—C3—C2112.29 (12)H101—C10—H102107.0
C4—C3—Cl3108.09 (10)C15—C11—C14107.99 (14)
C12—C3—Cl3106.47 (10)C15—C11—C10111.68 (13)
C2—C3—Cl3108.05 (9)C14—C11—C10104.50 (12)
C5—C4—C3112.95 (12)C15—C11—C1112.60 (12)
C5—C4—H4A109.0C14—C11—C1109.21 (12)
C3—C4—H4A109.0C10—C11—C1110.49 (11)
C5—C4—H4B109.0C3—C12—H121109.5
C3—C4—H4B109.0C3—C12—H122109.5
H4A—C4—H4B107.8H121—C12—H122109.5
C4—C5—C6113.84 (12)C3—C12—H123109.5
C4—C5—H5A108.8H121—C12—H123109.5
C6—C5—H5A108.8H122—C12—H123109.5
C4—C5—H5B108.8C7—C13—H131109.5
C6—C5—H5B108.8C7—C13—H132109.5
H5A—C5—H5B107.7H131—C13—H132109.5
C5—C6—C1108.44 (11)C7—C13—H133109.5
C5—C6—C7109.58 (11)H131—C13—H133109.5
C1—C6—C7119.25 (11)H132—C13—H133109.5
C5—C6—H6106.3C11—C14—H141109.5
C1—C6—H6106.3C11—C14—H142109.5
C7—C6—H6106.3H141—C14—H142109.5
C8—C7—C13106.99 (13)C11—C14—H143109.5
C8—C7—C6114.72 (12)H141—C14—H143109.5
C13—C7—C6111.52 (13)H142—C14—H143109.5
C8—C7—Cl7108.58 (10)C11—C15—H151109.5
C13—C7—Cl7105.51 (11)C11—C15—H152109.5
C6—C7—Cl7109.08 (10)H151—C15—H152109.5
C9—C8—C7120.86 (13)C11—C15—H153109.5
C9—C8—H81107.1H151—C15—H153109.5
C7—C8—H81107.1H152—C15—H153109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H82···Cl7i0.992.733.6397 (16)152
Symmetry code: (i) x+1, y, z.
 

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