Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803028095/om6200sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803028095/om6200IIsup2.hkl |
CCDC reference: 232153
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.006 Å
- R factor = 0.038
- wR factor = 0.117
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G 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 25.60 From the CIF: _reflns_number_total 1489 Count of symmetry unique reflns 1506 Completeness (_total/calc) 98.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: PROCESS in TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Burla et al., 1989); program(s) used to refine structure: LS in TEXSAN and SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: TEXSAN, SHELXL97, and PLATON (Spek, 2003).
C20H16 | F(000) = 272 |
Mr = 256.33 | Dx = 1.175 Mg m−3 |
Monoclinic, P21 | Melting point = 397–398 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71069 Å |
a = 9.8828 (19) Å | Cell parameters from 25 reflections |
b = 5.8836 (17) Å | θ = 10.1–13.5° |
c = 12.5231 (12) Å | µ = 0.07 mm−1 |
β = 95.684 (10)° | T = 296 K |
V = 724.6 (3) Å3 | Elongated prism, colorless |
Z = 2 | 0.38 × 0.18 × 0.15 mm |
Rigaku AFC-5S diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 25.6°, θmin = 2.1° |
Graphite monochromator | h = 0→11 |
ω scans | k = 0→7 |
1577 measured reflections | l = −15→15 |
1489 independent reflections | 3 standard reflections every 100 reflections |
881 reflections with I > 2σ(I) | intensity decay: 0.0% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0538P)2 + 0.0314P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
1489 reflections | Δρmax = 0.14 e Å−3 |
182 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | Absolute structure: The absolute configuration could not be determined because of the lack of heavy atoms |
Primary atom site location: structure-invariant direct methods |
x | y | z | Uiso*/Ueq | ||
C1 | 0.1649 (3) | 0.4220 (8) | 0.5056 (3) | 0.0605 (10) | |
C2 | 0.1640 (4) | 0.5755 (9) | 0.5899 (3) | 0.0713 (12) | |
C3 | 0.2468 (4) | 0.7645 (9) | 0.5952 (3) | 0.0732 (13) | |
C4 | 0.3309 (4) | 0.8089 (8) | 0.5167 (3) | 0.0637 (10) | |
C4A | 0.3321 (3) | 0.6553 (7) | 0.4321 (3) | 0.0512 (9) | |
C4B | 0.4104 (3) | 0.6559 (7) | 0.3387 (3) | 0.0541 (9) | |
C5 | 0.5077 (4) | 0.8060 (9) | 0.3092 (3) | 0.0720 (12) | |
C6 | 0.5649 (4) | 0.7653 (11) | 0.2154 (4) | 0.0884 (16) | |
C7 | 0.5289 (4) | 0.5781 (11) | 0.1527 (3) | 0.0845 (15) | |
C8 | 0.4332 (4) | 0.4238 (9) | 0.1824 (3) | 0.0700 (12) | |
C8A | 0.3741 (3) | 0.4643 (7) | 0.2766 (3) | 0.0514 (9) | |
C9 | 0.2690 (3) | 0.3235 (7) | 0.3282 (2) | 0.0492 (8) | |
C9A | 0.2491 (3) | 0.4623 (7) | 0.4268 (2) | 0.0506 (9) | |
C10 | 0.1420 (3) | 0.2760 (7) | 0.2535 (2) | 0.0480 (9) | |
C11 | 0.1257 (4) | 0.0722 (7) | 0.1998 (3) | 0.0596 (10) | |
C12 | 0.0116 (4) | 0.0296 (7) | 0.1286 (3) | 0.0645 (11) | |
C13 | −0.0881 (4) | 0.1898 (8) | 0.1081 (3) | 0.0605 (11) | |
C14 | −0.0728 (4) | 0.3942 (8) | 0.1617 (3) | 0.0601 (11) | |
C15 | 0.0412 (3) | 0.4366 (7) | 0.2337 (3) | 0.0540 (9) | |
C16 | −0.2119 (4) | 0.1435 (11) | 0.0304 (3) | 0.0862 (15) | |
H1 | 0.1095 | 0.2940 | 0.5027 | 0.073* | |
H2 | 0.1068 | 0.5504 | 0.6433 | 0.086* | |
H3 | 0.2458 | 0.8636 | 0.6530 | 0.088* | |
H4 | 0.3854 | 0.9380 | 0.5198 | 0.076* | |
H5 | 0.5337 | 0.9312 | 0.3517 | 0.086* | |
H6 | 0.6293 | 0.8662 | 0.1938 | 0.106* | |
H7 | 0.5694 | 0.5550 | 0.0896 | 0.101* | |
H8 | 0.4093 | 0.2969 | 0.1403 | 0.084* | |
H9 | 0.3105 | 0.1780 | 0.3511 | 0.059* | |
H11 | 0.1923 | −0.0392 | 0.2115 | 0.071* | |
H12 | 0.0029 | −0.1105 | 0.0941 | 0.077* | |
H14 | −0.1395 | 0.5053 | 0.1497 | 0.072* | |
H15 | 0.0493 | 0.5757 | 0.2689 | 0.065* | |
H16A | −0.1935 | 0.0189 | −0.0155 | 0.129* | |
H16B | −0.2334 | 0.2764 | −0.0124 | 0.129* | |
H16C | −0.2875 | 0.1058 | 0.0697 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.055 (2) | 0.077 (3) | 0.0493 (19) | −0.002 (2) | 0.0021 (17) | 0.002 (2) |
C2 | 0.061 (2) | 0.099 (4) | 0.055 (2) | 0.010 (3) | 0.0080 (19) | −0.005 (3) |
C3 | 0.074 (3) | 0.085 (3) | 0.060 (2) | 0.012 (3) | −0.002 (2) | −0.021 (2) |
C4 | 0.059 (2) | 0.056 (2) | 0.072 (2) | 0.001 (2) | −0.0126 (19) | −0.008 (2) |
C4A | 0.0475 (19) | 0.052 (2) | 0.0518 (19) | 0.002 (2) | −0.0068 (15) | −0.0009 (19) |
C4B | 0.0374 (17) | 0.063 (2) | 0.060 (2) | 0.004 (2) | −0.0043 (16) | 0.011 (2) |
C5 | 0.053 (2) | 0.079 (3) | 0.084 (3) | −0.006 (3) | 0.001 (2) | 0.017 (3) |
C6 | 0.056 (3) | 0.108 (5) | 0.103 (3) | −0.006 (3) | 0.014 (3) | 0.036 (4) |
C7 | 0.061 (3) | 0.126 (5) | 0.069 (3) | 0.012 (3) | 0.016 (2) | 0.021 (3) |
C8 | 0.057 (2) | 0.095 (3) | 0.059 (2) | 0.013 (3) | 0.0064 (17) | 0.002 (3) |
C8A | 0.0412 (18) | 0.062 (3) | 0.0491 (18) | 0.0100 (19) | −0.0038 (14) | 0.0052 (19) |
C9 | 0.0502 (18) | 0.047 (2) | 0.0496 (18) | 0.0062 (18) | 0.0003 (14) | 0.0024 (18) |
C9A | 0.0455 (17) | 0.060 (2) | 0.0449 (18) | 0.007 (2) | −0.0026 (15) | −0.0021 (19) |
C10 | 0.0546 (19) | 0.049 (2) | 0.0402 (17) | 0.0025 (19) | 0.0052 (15) | −0.0001 (18) |
C11 | 0.065 (2) | 0.053 (2) | 0.060 (2) | 0.008 (2) | −0.0004 (19) | −0.007 (2) |
C12 | 0.082 (3) | 0.057 (3) | 0.054 (2) | −0.011 (2) | 0.002 (2) | −0.014 (2) |
C13 | 0.061 (2) | 0.076 (3) | 0.044 (2) | −0.014 (2) | 0.0057 (17) | 0.005 (2) |
C14 | 0.050 (2) | 0.069 (3) | 0.061 (2) | 0.007 (2) | 0.0017 (17) | 0.007 (2) |
C15 | 0.059 (2) | 0.044 (2) | 0.057 (2) | −0.001 (2) | −0.0009 (16) | −0.002 (2) |
C16 | 0.072 (3) | 0.121 (4) | 0.062 (2) | −0.027 (3) | −0.0059 (19) | −0.001 (3) |
C1—C9A | 1.373 (5) | C13—C14 | 1.378 (6) |
C1—C2 | 1.389 (6) | C13—C16 | 1.511 (5) |
C2—C3 | 1.378 (6) | C14—C15 | 1.393 (5) |
C3—C4 | 1.374 (6) | C1—H1 | 0.9300 |
C4—C4A | 1.393 (5) | C2—H2 | 0.9300 |
C4A—C9A | 1.399 (5) | C3—H3 | 0.9300 |
C4A—C4B | 1.465 (5) | C4—H4 | 0.9300 |
C4B—C5 | 1.382 (5) | C5—H5 | 0.9300 |
C4B—C8A | 1.396 (5) | C6—H6 | 0.9300 |
C5—C6 | 1.374 (6) | C7—H7 | 0.9300 |
C6—C7 | 1.379 (7) | C8—H8 | 0.9300 |
C7—C8 | 1.389 (7) | C9—H9 | 0.9800 |
C8—C8A | 1.389 (5) | C11—H11 | 0.9300 |
C8A—C9 | 1.521 (5) | C12—H12 | 0.9300 |
C9—C9A | 1.510 (5) | C14—H14 | 0.9300 |
C9—C10 | 1.516 (4) | C15—H15 | 0.9300 |
C10—C11 | 1.377 (5) | C16—H16A | 0.9600 |
C10—C15 | 1.377 (5) | C16—H16B | 0.9600 |
C11—C12 | 1.389 (5) | C16—H16C | 0.9600 |
C12—C13 | 1.370 (6) | ||
C9A—C1—C2 | 118.9 (4) | C9A—C1—H1 | 120.5 |
C3—C2—C1 | 120.8 (4) | C2—C1—H1 | 120.5 |
C4—C3—C2 | 121.1 (4) | C3—C2—H2 | 119.6 |
C3—C4—C4A | 118.2 (4) | C1—C2—H2 | 119.6 |
C4—C4A—C9A | 120.9 (3) | C4—C3—H3 | 119.4 |
C4—C4A—C4B | 130.6 (4) | C2—C3—H3 | 119.4 |
C9A—C4A—C4B | 108.5 (3) | C3—C4—H4 | 120.9 |
C5—C4B—C8A | 120.9 (4) | C4A—C4—H4 | 120.9 |
C5—C4B—C4A | 130.7 (4) | C6—C5—H5 | 120.9 |
C8A—C4B—C4A | 108.4 (3) | C4B—C5—H5 | 120.9 |
C6—C5—C4B | 118.3 (5) | C5—C6—H6 | 119.3 |
C5—C6—C7 | 121.4 (4) | C7—C6—H6 | 119.3 |
C6—C7—C8 | 120.9 (4) | C6—C7—H7 | 119.5 |
C8A—C8—C7 | 118.1 (5) | C8—C7—H7 | 119.5 |
C8—C8A—C4B | 120.4 (4) | C8A—C8—H8 | 121.0 |
C8—C8A—C9 | 129.0 (4) | C7—C8—H8 | 121.0 |
C4B—C8A—C9 | 110.6 (3) | C9A—C9—H9 | 108.5 |
C9A—C9—C10 | 115.9 (3) | C10—C9—H9 | 108.5 |
C9A—C9—C8A | 101.7 (3) | C8A—C9—H9 | 108.5 |
C10—C9—C8A | 113.4 (3) | C10—C11—H11 | 119.4 |
C1—C9A—C4A | 120.0 (3) | C12—C11—H11 | 119.4 |
C1—C9A—C9 | 129.2 (3) | C13—C12—H12 | 119.4 |
C4A—C9A—C9 | 110.8 (3) | C11—C12—H12 | 119.4 |
C11—C10—C15 | 117.5 (3) | C13—C14—H14 | 119.5 |
C11—C10—C9 | 120.8 (3) | C15—C14—H14 | 119.5 |
C15—C10—C9 | 121.7 (3) | C10—C15—H15 | 119.4 |
C10—C11—C12 | 121.3 (4) | C14—C15—H15 | 119.4 |
C13—C12—C11 | 121.3 (4) | C13—C16—H16A | 109.5 |
C12—C13—C14 | 117.9 (3) | C13—C16—H16B | 109.5 |
C12—C13—C16 | 121.2 (4) | H16A—C16—H16B | 109.5 |
C14—C13—C16 | 120.9 (4) | C13—C16—H16C | 109.5 |
C13—C14—C15 | 120.9 (4) | H16A—C16—H16C | 109.5 |
C10—C15—C14 | 121.2 (4) | H16B—C16—H16C | 109.5 |
C9A—C1—C2—C3 | −0.6 (6) | C2—C1—C9A—C4A | 0.1 (5) |
C1—C2—C3—C4 | 1.2 (6) | C2—C1—C9A—C9 | 179.9 (4) |
C2—C3—C4—C4A | −1.2 (6) | C4—C4A—C9A—C1 | −0.1 (5) |
C3—C4—C4A—C9A | 0.6 (5) | C4B—C4A—C9A—C1 | 180.0 (3) |
C3—C4—C4A—C4B | −179.4 (4) | C4—C4A—C9A—C9 | −179.9 (3) |
C4—C4A—C4B—C5 | 1.7 (6) | C4B—C4A—C9A—C9 | 0.1 (4) |
C9A—C4A—C4B—C5 | −178.3 (4) | C10—C9—C9A—C1 | 56.2 (5) |
C4—C4A—C4B—C8A | −179.5 (4) | C8A—C9—C9A—C1 | 179.6 (3) |
C9A—C4A—C4B—C8A | 0.4 (4) | C10—C9—C9A—C4A | −124.0 (3) |
C8A—C4B—C5—C6 | 1.9 (5) | C8A—C9—C9A—C4A | −0.6 (4) |
C4A—C4B—C5—C6 | −179.5 (4) | C9A—C9—C10—C11 | −144.4 (3) |
C4B—C5—C6—C7 | −1.2 (6) | C8A—C9—C10—C11 | 98.5 (4) |
C5—C6—C7—C8 | 0.0 (7) | C9A—C9—C10—C15 | 37.9 (5) |
C6—C7—C8—C8A | 0.4 (6) | C8A—C9—C10—C15 | −79.2 (4) |
C7—C8—C8A—C4B | 0.3 (5) | C15—C10—C11—C12 | −0.2 (5) |
C7—C8—C8A—C9 | −179.2 (4) | C9—C10—C11—C12 | −177.9 (3) |
C5—C4B—C8A—C8 | −1.4 (5) | C10—C11—C12—C13 | 0.8 (6) |
C4A—C4B—C8A—C8 | 179.7 (3) | C11—C12—C13—C14 | −0.9 (6) |
C5—C4B—C8A—C9 | 178.1 (3) | C11—C12—C13—C16 | 179.9 (3) |
C4A—C4B—C8A—C9 | −0.8 (4) | C12—C13—C14—C15 | 0.6 (5) |
C8—C8A—C9—C9A | −179.7 (3) | C16—C13—C14—C15 | 179.8 (3) |
C4B—C8A—C9—C9A | 0.8 (3) | C11—C10—C15—C14 | −0.2 (5) |
C8—C8A—C9—C10 | −54.5 (5) | C9—C10—C15—C14 | 177.5 (3) |
C4B—C8A—C9—C10 | 126.0 (3) | C13—C14—C15—C10 | 0.0 (5) |
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