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Iso­propylcyclo­hexane, C9H18, which is a liquid under ambient conditions, tends to form a glass on cooling. Laser-assisted zone refinement of the frozen solid yielded a crystalline solid, although the sample was not single. The crystal was not really a twin in the usual sense of the term, but the consequences of the multiplicity of the sample could be modelled with a combination of domains generated by twofold rotations about the reciprocal lattice [1k0] directions, where k = 9-12.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007274/bt6117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007274/bt6117Isup2.hkl
Contains datablock I

CCDC reference: 189386

Key indicators

  • Powder X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.061
  • wR factor = 0.237
  • Data-to-parameter ratio = 13.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
REFI_020 Alert A _refine_ls_extinction_coef is missing Extinction coefficient applied in corrections.
Amber Alert Alert Level B:
ABSTM_02 Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.554 1.000 Tmin' and Tmax expected: 0.948 0.979 RR' = 0.572 Please check that your absorption correction is appropriate. CELLV_02 Alert B The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 4 Calculated cell volume su = 8.21 Cell volume su given = 14.00
Yellow Alert Alert Level C:
CRYSR_01 Alert C _exptl_crystal_size_rad not in the CIF when expected. REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.30 From the CIF: _reflns_number_total 1950 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2140 Completeness (_total/calc) 91.12% Alert C: < 95% complete PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.002(9) .... 2.22 s.u-Ratio C1 -H11 1.555 1.555 PLAT_731 Alert C Bond Calc 1.01(2), Rep 1.005(9) .... 2.22 s.u-Ratio C2 -H21 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.000(9) .... 2.22 s.u-Ratio C2 -H22 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(3), Rep 1.001(9) .... 3.33 s.u-Ratio C3 -H32 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.000(9) .... 2.22 s.u-Ratio C4 -H42 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.000(9) .... 2.22 s.u-Ratio C5 -H51 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.001(9) .... 2.22 s.u-Ratio C5 -H52 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.001(9) .... 2.22 s.u-Ratio C6 -H61 1.555 1.555 PLAT_731 Alert C Bond Calc 1.01(2), Rep 1.003(9) .... 2.22 s.u-Ratio C7 -H71 1.555 1.555 PLAT_731 Alert C Bond Calc 1.004(19), Rep 1.004(9) .... 2.11 s.u-Ratio C8 -H82 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.002(9) .... 2.22 s.u-Ratio C8 -H83 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 1.002(9) .... 2.22 s.u-Ratio C9 -H92 1.555 1.555 PLAT_731 Alert C Bond Calc 1.00(2), Rep 0.997(9) .... 2.22 s.u-Ratio C9 -H93 1.555 1.555
1 Alert Level A = Potentially serious problem
2 Alert Level B = Potential problem
15 Alert Level C = Please check

Computing details top

Data collection: SMART (Siemens, 1993); cell refinement: SAINT; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2002); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Isopropyl cyclohexane top
Crystal data top
C9H18Dx = 0.968 Mg m3
Mr = 126.24Melting point: 183 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 15.689 (8) ÅCell parameters from 1016 reflections
b = 5.298 (3) Åθ = 2–27°
c = 10.641 (6) ŵ = 0.05 mm1
β = 101.79 (1)°T = 150 K
V = 865.9 (14) Å3Cylinder, colourless
Z = 41.00 × 0.40 × 0.40 mm
F(000) = 288.086
Data collection top
Bruker SMART APEX
diffractometer equipped with an Oxford Cryosystems low- temperature device and an OHCD laser-assisted crystallisation device (Scientific Consulting, Essen, Germany).
1069 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.04
φ and ω scansθmax = 28.3°, θmin = 1.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 2019
Tmin = 0.554, Tmax = 1k = 06
5107 measured reflectionsl = 014
1950 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullSee text
R[F2 > 2σ(F2)] = 0.061 Method = Tukey and Prince (Carruthers et al., 1979) W = [weight] * [1-(ΔF/6*σ(F))2]2 using a four-term Chebychev polynomial with parameters 69.3 109. 54.8 14.3
wR(F2) = 0.237(Δ/σ)max = 0.003
S = 1.04Δρmax = 0.28 e Å3
1950 reflectionsΔρmin = 0.16 e Å3
142 parametersExtinction correction: The extinction parameter refined to less than 3σ and it was thereafter fixed at 0.
Primary atom site location: structure-invariant direct methods
Special details top

Refinement. A multi-domain twin model may be constructed in CRYSTALS with the following instruction list. Note that the first matrix given is the unit matrix since this refers to domain 1. The twintol parameter in the λist 6 instruction refers to the overlap criterion in Å-2. The λist 16 instruction restrains the sum of the twin element scale factors to unity and applied shift-limiting restraints. The refinement directives are given in the λist 12 instruction. The number of elements and initial starting values for the scale factors were also added to the atom list (λist 5). Full details of these instructions are given in the CRYSTALS manual.

λist 25 READ NELEM =8 MATRIX 1 0 0 0 1 0 0 0 1 MATRIX -0.997 0.222 0.001 0.026 0.997 0.008 0.000 0.000 - 1.000 MATRIX -0.998 0.200 0.001 0.024 0.998 0.007 0.000 0.000 - 1.000 MATRIX -0.998 0.182 0.001 0.022 0.998 0.007 0.000 0.000 - 1.000 MATRIX -0.998 0.167 0.000 0.020 0.998 0.006 0.000 0.000 - 1.000 MATRIX 1.011 0.168 0.503 0.020 - 0.998 0.005 - 0.049 - 0.004 - 1.012 MATRIX -1.012 0.000 - 0.503 0.000 - 1.000 0.000 0.049 0.000 1.012 MATRIX -0.996 0.250 0.001 0.030 0.996 0.009 0.000 0.000 - 1.000 e nd ΛIST 6 READ TYPE=TWIN MATRIX TWINTOL=0.005 END ΛIST 16 SUM 0.001 ELEMENT SCALES LIMIT 0.1 ELEMENT SCALES DIST 0.0, 0.01 = MEAN C(1) TO H(11), C(7) TO H(71) CONT C(6) TO H(61), C(6) TO H(62) CONT C(5) TO H(51), C(5) TO H(52) CONT C(4) TO H(42), C(4) TO H(41) CONT C(3) TO H(32), C(3) TO H(31) CONT C(2) TO H(21), C(2) TO H(22) CONT C(8) TO H(82), C(8) TO H(83), C(8) TO H(81) CONT C(9) TO H(92), C(9) TO H(91), C(9) TO H(93) END #LIST 12 FULL X'S,U'S CONT H(11,X'S) UNTIL LAST CONT ELEMENT SCALES EQUIV H(11,U[ISO]) UNTIL H(71) EQUIV H(81,U[ISO]) UNTIL LAST END

Simpler two-component twin-refinements can be set-up via a GUI.

There has been some recent discussion on the internet on the subject of how details of a twin-refinement could be incorporated into a crystallographic information file. A few weeks before he was tragically killed in a car accident, Sparks suggested a list of items that might be included; these can be found at https://www.iucr.org/iucr-top/lists/strchem/. We have attempted to incorporate these suggestions into this cif (see below). We have given the twin laws both as matrices (items _edchem_twin_law_element_11 and so on) and as symmtery operations and directions for each domain of the crystal (_edchem_twin_law_direction and _edchem_twin_law_operation). The twin law assumes that reflection indices are written as column vectors; this is the convention used in CRYSTALS and SHELXL (Sheldrick, 2001b), although other refinement programs (JANA for example, Petricek et al., 2000) adopt a row-vector convention. This information is added as a comment. The refined twin scale factor and the overlap criterion for splitting reflections over several twin domains are also given.

All data were used in refinement. The unweighted R-factors are based on F, are based on data with I > 2σ(I); the final difference map max. and min. were calculated using the same criterion. Weighted R-factors are quoted with respect to F2. A break-down of completeness and intensity statistics as a function of resolution shells is given below (Sheldrick, 2001a)

Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) R(σ)

Inf - 2.20 110 113 97.3 2.79 61.6 24.61 0.0295 0.0268 2.20 - 1.70 113 115 98.3 3.10 21.6 22.75 0.0266 0.0266 1.70 - 1.45 134 137 97.8 3.15 8.1 16.34 0.0413 0.0383 1.45 - 1.30 120 122 98.4 2.94 11.2 14.82 0.0548 0.0393 1.30 - 1.20 131 131 100.0 2.80 8.1 13.86 0.0555 0.0473 1.20 - 1.10 167 169 98.8 2.62 5.0 11.06 0.0620 0.0664 1.10 - 1.00 247 250 98.8 2.38 4.3 8.51 0.0777 0.0813 1.00 - 0.95 170 171 99.4 2.22 2.4 5.43 0.0983 0.1459 0.95 - 0.90 187 190 98.4 2.14 2.2 4.27 0.1274 0.1735 0.90 - 0.85 252 260 96.9 1.97 1.4 3.03 0.1793 0.2799 0.85 - 0.80 299 318 94.0 1.86 1.6 2.94 0.1797 0.2853 0.80 - 0.75 219 395 55.4 0.89 1.2 1.82 0.2879 0.5100 0.75 - 0.75 1 3 33.3 0.33 0.5 0.55 1.8096 —————————————————————————— 0.85 - 0.75 519 716 72.5 1.32 1.4 2.46 0.2035 0.3642 Inf - 0.75 2150 2374 90.6 2.15 7.7 8.73 0.0486 0.0625

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.74308 (12)0.1145 (4)0.21441 (17)0.0240
C20.79254 (13)0.1385 (4)0.35565 (18)0.0271
C30.89170 (14)0.1154 (4)0.3679 (2)0.0310
C40.91580 (15)0.1330 (4)0.3091 (2)0.0338
C50.86718 (15)0.1598 (5)0.1688 (2)0.0341
C60.76813 (14)0.1361 (4)0.1572 (2)0.0296
C70.64318 (13)0.1536 (4)0.19960 (19)0.0271
C80.59604 (15)0.0737 (5)0.2446 (2)0.0346
C90.59998 (15)0.2256 (5)0.0609 (2)0.0358
H110.7637 (18)0.256 (4)0.166 (2)0.044 (2)*
H210.7777 (18)0.306 (3)0.390 (3)0.044 (2)*
H220.7717 (17)0.003 (4)0.407 (2)0.044 (2)*
H310.9243 (16)0.128 (5)0.4585 (12)0.044 (2)*
H320.9128 (19)0.260 (4)0.322 (3)0.044 (2)*
H410.9803 (7)0.140 (5)0.316 (3)0.044 (2)*
H420.8994 (18)0.278 (4)0.360 (2)0.044 (2)*
H510.8887 (17)0.022 (4)0.119 (2)0.044 (2)*
H520.8829 (18)0.328 (3)0.137 (3)0.044 (2)*
H610.7505 (18)0.277 (4)0.209 (2)0.044 (2)*
H620.7360 (16)0.155 (5)0.0660 (12)0.044 (2)*
H710.6357 (18)0.304 (4)0.254 (2)0.044 (2)*
H810.5346 (9)0.021 (5)0.242 (2)0.043 (3)*
H820.6259 (16)0.141 (5)0.3306 (15)0.043 (3)*
H830.5928 (19)0.222 (4)0.186 (2)0.043 (3)*
H910.5363 (8)0.268 (5)0.045 (3)0.043 (3)*
H920.6285 (17)0.381 (4)0.035 (3)0.043 (3)*
H930.6051 (18)0.081 (4)0.003 (2)0.043 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0300 (9)0.025 (1)0.0174 (9)0.0004 (7)0.0056 (7)0.0007 (7)
C20.034 (1)0.030 (1)0.0180 (9)0.0002 (8)0.0061 (7)0.0028 (7)
C30.0336 (11)0.0338 (11)0.024 (1)0.0006 (8)0.0025 (7)0.0025 (8)
C40.033 (1)0.0392 (12)0.0287 (11)0.0056 (9)0.0049 (8)0.0002 (9)
C50.0362 (11)0.0400 (12)0.027 (1)0.0067 (9)0.0085 (8)0.0070 (9)
C60.0351 (11)0.0303 (11)0.024 (1)0.0014 (8)0.0061 (8)0.0064 (8)
C70.031 (1)0.029 (1)0.022 (1)0.0003 (8)0.0070 (7)0.0016 (7)
C80.034 (1)0.0374 (12)0.0338 (11)0.0037 (9)0.0113 (8)0.0017 (9)
C90.0377 (11)0.0428 (13)0.025 (1)0.005 (1)0.0024 (8)0.0040 (9)
Geometric parameters (Å, º) top
C1—C21.549 (3)C5—H511.000 (9)
C1—C61.545 (3)C5—H521.001 (9)
C1—C71.557 (3)C6—H611.001 (9)
C1—H111.002 (9)C6—H621.004 (9)
C2—C31.539 (3)C7—C81.540 (3)
C2—H211.005 (9)C7—C91.541 (3)
C2—H221.000 (9)C7—H711.003 (9)
C3—C41.537 (3)C8—H810.999 (9)
C3—H310.997 (9)C8—H821.004 (9)
C3—H321.001 (9)C8—H831.002 (9)
C4—C51.538 (3)C9—H911.004 (9)
C4—H411.001 (9)C9—H921.002 (9)
C4—H421.000 (9)C9—H930.997 (9)
C5—C61.539 (3)
C2—C1—C6109.59 (16)C4—C5—H52107.7 (17)
C2—C1—C7112.44 (15)C6—C5—H52111.1 (16)
C6—C1—C7113.98 (16)H51—C5—H52110 (2)
C2—C1—H11107.0 (17)C1—C6—C5111.88 (17)
C6—C1—H11107.6 (17)C1—C6—H61107.4 (16)
C7—C1—H11105.9 (17)C5—C6—H61106.5 (17)
C1—C2—C3111.88 (16)C1—C6—H62110.4 (16)
C1—C2—H21108.6 (16)C5—C6—H62111.6 (16)
C3—C2—H21110.2 (16)H61—C6—H62109 (2)
C1—C2—H22108.6 (16)C1—C7—C8113.71 (17)
C3—C2—H22109.5 (16)C1—C7—C9111.52 (16)
H21—C2—H22108 (2)C8—C7—C9110.26 (17)
C2—C3—C4111.22 (17)C1—C7—H71106.3 (16)
C2—C3—H31112.7 (16)C8—C7—H71108.8 (17)
C4—C3—H31109.4 (16)C9—C7—H71105.8 (16)
C2—C3—H32109.2 (18)C7—C8—H81107.2 (17)
C4—C3—H32108.7 (17)C7—C8—H82113.4 (17)
H31—C3—H32105 (2)H81—C8—H82113 (2)
C3—C4—C5111.08 (18)C7—C8—H83112.8 (17)
C3—C4—H41109.5 (16)H81—C8—H83106 (2)
C5—C4—H41110.9 (17)H82—C8—H83104 (2)
C3—C4—H42109.1 (16)C7—C9—H91116.2 (16)
C5—C4—H42108.7 (17)C7—C9—H92109.5 (17)
H41—C4—H42108 (2)H91—C9—H92105 (2)
C4—C5—C6111.24 (17)C7—C9—H93109.2 (16)
C4—C5—H51107.0 (16)H91—C9—H93106 (2)
C6—C5—H51110.1 (16)H92—C9—H93111 (2)
 

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