Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007274/bt6117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007274/bt6117Isup2.hkl |
CCDC reference: 189386
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.
C9H18 | Dx = 0.968 Mg m−3 |
Mr = 126.24 | Melting point: 183 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.689 (8) Å | Cell parameters from 1016 reflections |
b = 5.298 (3) Å | θ = 2–27° |
c = 10.641 (6) Å | µ = 0.05 mm−1 |
β = 101.79 (1)° | T = 150 K |
V = 865.9 (14) Å3 | Cylinder, colourless |
Z = 4 | 1.00 × 0.40 × 0.40 mm |
F(000) = 288.086 |
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 monochromator | Rint = 0.04 |
φ and ω scans | θmax = 28.3°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) | h = −20→19 |
Tmin = 0.554, Tmax = 1 | k = 0→6 |
5107 measured reflections | l = 0→14 |
1950 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | See 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 = 1.04 | Δρmax = 0.28 e Å−3 |
1950 reflections | Δρmin = −0.16 e Å−3 |
142 parameters | Extinction correction: The extinction parameter refined to less than 3σ and it was thereafter fixed at 0. |
Primary atom site location: structure-invariant direct methods |
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 |
x | y | z | Uiso*/Ueq | ||
C1 | 0.74308 (12) | −0.1145 (4) | 0.21441 (17) | 0.0240 | |
C2 | 0.79254 (13) | −0.1385 (4) | 0.35565 (18) | 0.0271 | |
C3 | 0.89170 (14) | −0.1154 (4) | 0.3679 (2) | 0.0310 | |
C4 | 0.91580 (15) | 0.1330 (4) | 0.3091 (2) | 0.0338 | |
C5 | 0.86718 (15) | 0.1598 (5) | 0.1688 (2) | 0.0341 | |
C6 | 0.76813 (14) | 0.1361 (4) | 0.1572 (2) | 0.0296 | |
C7 | 0.64318 (13) | −0.1536 (4) | 0.19960 (19) | 0.0271 | |
C8 | 0.59604 (15) | 0.0737 (5) | 0.2446 (2) | 0.0346 | |
C9 | 0.59998 (15) | −0.2256 (5) | 0.0609 (2) | 0.0358 | |
H11 | 0.7637 (18) | −0.256 (4) | 0.166 (2) | 0.044 (2)* | |
H21 | 0.7777 (18) | −0.306 (3) | 0.390 (3) | 0.044 (2)* | |
H22 | 0.7717 (17) | −0.003 (4) | 0.407 (2) | 0.044 (2)* | |
H31 | 0.9243 (16) | −0.128 (5) | 0.4585 (12) | 0.044 (2)* | |
H32 | 0.9128 (19) | −0.260 (4) | 0.322 (3) | 0.044 (2)* | |
H41 | 0.9803 (7) | 0.140 (5) | 0.316 (3) | 0.044 (2)* | |
H42 | 0.8994 (18) | 0.278 (4) | 0.360 (2) | 0.044 (2)* | |
H51 | 0.8887 (17) | 0.022 (4) | 0.119 (2) | 0.044 (2)* | |
H52 | 0.8829 (18) | 0.328 (3) | 0.137 (3) | 0.044 (2)* | |
H61 | 0.7505 (18) | 0.277 (4) | 0.209 (2) | 0.044 (2)* | |
H62 | 0.7360 (16) | 0.155 (5) | 0.0660 (12) | 0.044 (2)* | |
H71 | 0.6357 (18) | −0.304 (4) | 0.254 (2) | 0.044 (2)* | |
H81 | 0.5346 (9) | 0.021 (5) | 0.242 (2) | 0.043 (3)* | |
H82 | 0.6259 (16) | 0.141 (5) | 0.3306 (15) | 0.043 (3)* | |
H83 | 0.5928 (19) | 0.222 (4) | 0.186 (2) | 0.043 (3)* | |
H91 | 0.5363 (8) | −0.268 (5) | 0.045 (3) | 0.043 (3)* | |
H92 | 0.6285 (17) | −0.381 (4) | 0.035 (3) | 0.043 (3)* | |
H93 | 0.6051 (18) | −0.081 (4) | 0.003 (2) | 0.043 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0300 (9) | 0.025 (1) | 0.0174 (9) | 0.0004 (7) | 0.0056 (7) | 0.0007 (7) |
C2 | 0.034 (1) | 0.030 (1) | 0.0180 (9) | −0.0002 (8) | 0.0061 (7) | 0.0028 (7) |
C3 | 0.0336 (11) | 0.0338 (11) | 0.024 (1) | 0.0006 (8) | 0.0025 (7) | 0.0025 (8) |
C4 | 0.033 (1) | 0.0392 (12) | 0.0287 (11) | −0.0056 (9) | 0.0049 (8) | 0.0002 (9) |
C5 | 0.0362 (11) | 0.0400 (12) | 0.027 (1) | −0.0067 (9) | 0.0085 (8) | 0.0070 (9) |
C6 | 0.0351 (11) | 0.0303 (11) | 0.024 (1) | −0.0014 (8) | 0.0061 (8) | 0.0064 (8) |
C7 | 0.031 (1) | 0.029 (1) | 0.022 (1) | 0.0003 (8) | 0.0070 (7) | 0.0016 (7) |
C8 | 0.034 (1) | 0.0374 (12) | 0.0338 (11) | 0.0037 (9) | 0.0113 (8) | −0.0017 (9) |
C9 | 0.0377 (11) | 0.0428 (13) | 0.025 (1) | −0.005 (1) | 0.0024 (8) | −0.0040 (9) |
C1—C2 | 1.549 (3) | C5—H51 | 1.000 (9) |
C1—C6 | 1.545 (3) | C5—H52 | 1.001 (9) |
C1—C7 | 1.557 (3) | C6—H61 | 1.001 (9) |
C1—H11 | 1.002 (9) | C6—H62 | 1.004 (9) |
C2—C3 | 1.539 (3) | C7—C8 | 1.540 (3) |
C2—H21 | 1.005 (9) | C7—C9 | 1.541 (3) |
C2—H22 | 1.000 (9) | C7—H71 | 1.003 (9) |
C3—C4 | 1.537 (3) | C8—H81 | 0.999 (9) |
C3—H31 | 0.997 (9) | C8—H82 | 1.004 (9) |
C3—H32 | 1.001 (9) | C8—H83 | 1.002 (9) |
C4—C5 | 1.538 (3) | C9—H91 | 1.004 (9) |
C4—H41 | 1.001 (9) | C9—H92 | 1.002 (9) |
C4—H42 | 1.000 (9) | C9—H93 | 0.997 (9) |
C5—C6 | 1.539 (3) | ||
C2—C1—C6 | 109.59 (16) | C4—C5—H52 | 107.7 (17) |
C2—C1—C7 | 112.44 (15) | C6—C5—H52 | 111.1 (16) |
C6—C1—C7 | 113.98 (16) | H51—C5—H52 | 110 (2) |
C2—C1—H11 | 107.0 (17) | C1—C6—C5 | 111.88 (17) |
C6—C1—H11 | 107.6 (17) | C1—C6—H61 | 107.4 (16) |
C7—C1—H11 | 105.9 (17) | C5—C6—H61 | 106.5 (17) |
C1—C2—C3 | 111.88 (16) | C1—C6—H62 | 110.4 (16) |
C1—C2—H21 | 108.6 (16) | C5—C6—H62 | 111.6 (16) |
C3—C2—H21 | 110.2 (16) | H61—C6—H62 | 109 (2) |
C1—C2—H22 | 108.6 (16) | C1—C7—C8 | 113.71 (17) |
C3—C2—H22 | 109.5 (16) | C1—C7—C9 | 111.52 (16) |
H21—C2—H22 | 108 (2) | C8—C7—C9 | 110.26 (17) |
C2—C3—C4 | 111.22 (17) | C1—C7—H71 | 106.3 (16) |
C2—C3—H31 | 112.7 (16) | C8—C7—H71 | 108.8 (17) |
C4—C3—H31 | 109.4 (16) | C9—C7—H71 | 105.8 (16) |
C2—C3—H32 | 109.2 (18) | C7—C8—H81 | 107.2 (17) |
C4—C3—H32 | 108.7 (17) | C7—C8—H82 | 113.4 (17) |
H31—C3—H32 | 105 (2) | H81—C8—H82 | 113 (2) |
C3—C4—C5 | 111.08 (18) | C7—C8—H83 | 112.8 (17) |
C3—C4—H41 | 109.5 (16) | H81—C8—H83 | 106 (2) |
C5—C4—H41 | 110.9 (17) | H82—C8—H83 | 104 (2) |
C3—C4—H42 | 109.1 (16) | C7—C9—H91 | 116.2 (16) |
C5—C4—H42 | 108.7 (17) | C7—C9—H92 | 109.5 (17) |
H41—C4—H42 | 108 (2) | H91—C9—H92 | 105 (2) |
C4—C5—C6 | 111.24 (17) | C7—C9—H93 | 109.2 (16) |
C4—C5—H51 | 107.0 (16) | H91—C9—H93 | 106 (2) |
C6—C5—H51 | 110.1 (16) | H92—C9—H93 | 111 (2) |