The structural changes in a crystal of 9-methylanthracene (1) during the [4 + 4] photodimerization were monitored by means of X-ray diffraction. This is the first example in the literature of such a study of a [4 + 4] photodimerization. The results obtained were compared with data for the [2 + 2] photodimerization. The shape of the product molecules and their preferred packing can explain the crystal disintegration. This was the reason that the reaction was monitored only to 28% completion. As far as could be determined the reaction proceeds with a constant rate. The cell volume increases at the beginning of the transformation and decreases afterwards. The product molecules do not assume a fixed position in the crystal during the photo-reaction, but move in a smooth way that includes a rotational component. The movements of the reactant are much smaller. Movements of molecules characterized by a rotational component were also observed in the case of the [2 + 2] photodimerization of 5-benzylidene-2-benzylcyclopentanone and 5-benzylidene-2-(4-chlorobenzyl)-cyclopentanone. The distance between the reacting atoms of the adjacent monomer molecules of (1) decreases with the degree of reaction completion, but more slowly than in the case of the [2 + 2] photodimerizations cited above. The orientation of the neighbouring monomer molecules changes during the phototransformation so that the monomer pair resembles the dimer product.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768103023255/bk0138sup1.cif Contains datablocks 0D, 3D, 4D, 6D, 8D, 11D, 15D, 18D, 24D, 26D, 28D, 100D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk01380Dsup2.hkl Contains datablock 0%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk01383Dsup3.hkl Contains datablock 3%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk01384Dsup4.hkl Contains datablock 4%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk01386Dsup5.hkl Contains datablock 6%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk01388Dsup6.hkl Contains datablock 8%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013811Dsup7.hkl Contains datablock 11%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013815Dsup8.hkl Contains datablock 15%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013818Dsup9.hkl Contains datablock 18%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013824Dsup10.hkl Contains datablock 24%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013826Dsup11.hkl Contains datablock 26%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk013828Dsup12.hkl Contains datablock 28%D |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768103023255/bk0138100Dsup13.hkl Contains datablock 100%D |
CCDC references: 227661; 227662; 227663; 227664; 227665; 227666; 227667; 227668; 227669; 227670; 227671; 227672
For all compounds, data collection: Kuma KM4CCD software 2000; cell refinement: Kuma KM4CCD software 2000; data reduction: Kuma KM4CCD software 2000; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 1997; software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.233 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8859 (13) Å | Cell parameters from 500 reflections |
b = 14.594 (2) Å | θ = 4–22° |
c = 8.0395 (11) Å | µ = 0.07 mm−1 |
β = 96.505 (14)° | T = 293 K |
V = 1035.9 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1262 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 26.0°, θmin = 4.3° |
ω scans | h = −10→10 |
3393 measured reflections | k = −18→16 |
1938 independent reflections | l = −9→5 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | All H-atom parameters refined |
wR(F2) = 0.204 | Calculated w = 1/[σ2(Fo2) + (0.1171P)2 + 0.0477P] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
1938 reflections | Δρmax = 0.22 e Å−3 |
185 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.032 (12) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1009 (3) | 0.57943 (14) | 0.3038 (3) | 0.0641 (6) | |
C2 | 0.2497 (3) | 0.59727 (17) | 0.3397 (3) | 0.0762 (7) | |
C3 | 0.3316 (3) | 0.64095 (18) | 0.2223 (3) | 0.0761 (7) | |
C4 | 0.2611 (2) | 0.66448 (15) | 0.0724 (3) | 0.0639 (6) | |
C5 | −0.1959 (3) | 0.68064 (13) | −0.3295 (3) | 0.0604 (6) | |
C6 | −0.3457 (3) | 0.66953 (15) | −0.3674 (3) | 0.0714 (7) | |
C7 | −0.4329 (3) | 0.63021 (16) | −0.2501 (3) | 0.0709 (7) | |
C8 | −0.3658 (2) | 0.60228 (14) | −0.0992 (3) | 0.0607 (6) | |
C9 | −0.1350 (2) | 0.58685 (12) | 0.1057 (2) | 0.0486 (5) | |
C10 | 0.0323 (2) | 0.67012 (12) | −0.1287 (2) | 0.0516 (5) | |
C11 | 0.0196 (2) | 0.60296 (12) | 0.1462 (2) | 0.0479 (5) | |
C12 | 0.1050 (2) | 0.64636 (12) | 0.0266 (2) | 0.0500 (5) | |
C13 | −0.1208 (2) | 0.65419 (11) | −0.1715 (2) | 0.0476 (5) | |
C14 | −0.2076 (2) | 0.61278 (11) | −0.0516 (2) | 0.0457 (5) | |
C15 | −0.2250 (3) | 0.5431 (2) | 0.2326 (3) | 0.0729 (7) | |
H1 | 0.039 (2) | 0.5478 (16) | 0.400 (3) | 0.086 (7)* | |
H2 | 0.308 (3) | 0.5794 (17) | 0.448 (4) | 0.095 (8)* | |
H3 | 0.444 (3) | 0.6548 (15) | 0.252 (3) | 0.081 (7)* | |
H4 | 0.314 (3) | 0.6943 (16) | −0.018 (3) | 0.080 (7)* | |
H5 | −0.132 (2) | 0.7084 (13) | −0.409 (3) | 0.060 (5)* | |
H6 | −0.397 (3) | 0.6884 (16) | −0.476 (3) | 0.085 (7)* | |
H7 | −0.556 (3) | 0.6233 (17) | −0.281 (3) | 0.096 (8)* | |
H8 | −0.433 (2) | 0.5754 (16) | −0.016 (3) | 0.076 (6)* | |
H10 | 0.092 (2) | 0.7007 (13) | −0.214 (3) | 0.056 (5)* | |
H15A | −0.245 (4) | 0.582 (3) | 0.310 (6) | 0.156 (14)* | |
H15B | −0.322 (5) | 0.516 (3) | 0.180 (6) | 0.188 (17)* | |
H15C | −0.168 (4) | 0.493 (2) | 0.293 (4) | 0.128 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0766 (15) | 0.0622 (12) | 0.0519 (12) | 0.0040 (10) | 0.0001 (10) | 0.0040 (9) |
C2 | 0.0766 (17) | 0.0821 (15) | 0.0647 (15) | 0.0065 (12) | −0.0146 (12) | −0.0004 (12) |
C3 | 0.0562 (15) | 0.0836 (16) | 0.0851 (18) | 0.0042 (11) | −0.0065 (12) | −0.0070 (13) |
C4 | 0.0529 (13) | 0.0692 (13) | 0.0700 (15) | −0.0008 (9) | 0.0092 (10) | −0.0006 (11) |
C5 | 0.0793 (16) | 0.0527 (11) | 0.0485 (12) | −0.0040 (9) | 0.0043 (10) | 0.0042 (9) |
C6 | 0.0798 (17) | 0.0681 (13) | 0.0607 (14) | −0.0002 (11) | −0.0155 (12) | 0.0006 (11) |
C7 | 0.0612 (15) | 0.0747 (14) | 0.0735 (15) | −0.0053 (10) | −0.0073 (11) | −0.0046 (11) |
C8 | 0.0549 (13) | 0.0614 (12) | 0.0655 (14) | −0.0076 (9) | 0.0061 (10) | −0.0051 (10) |
C9 | 0.0563 (12) | 0.0451 (9) | 0.0458 (10) | −0.0020 (7) | 0.0122 (8) | −0.0019 (7) |
C10 | 0.0571 (13) | 0.0496 (10) | 0.0497 (11) | −0.0025 (8) | 0.0125 (9) | 0.0045 (8) |
C11 | 0.0546 (12) | 0.0444 (9) | 0.0447 (10) | 0.0026 (7) | 0.0051 (8) | −0.0035 (7) |
C12 | 0.0507 (11) | 0.0481 (10) | 0.0521 (11) | 0.0008 (7) | 0.0092 (8) | −0.0037 (8) |
C13 | 0.0575 (12) | 0.0404 (9) | 0.0449 (11) | −0.0004 (7) | 0.0054 (8) | −0.0026 (7) |
C14 | 0.0505 (11) | 0.0409 (9) | 0.0463 (11) | −0.0025 (7) | 0.0077 (8) | −0.0048 (7) |
C15 | 0.0798 (18) | 0.0811 (16) | 0.0609 (14) | −0.0067 (13) | 0.0217 (12) | 0.0094 (13) |
Geometric parameters (Å, º) top
C1—C2 | 1.347 (3) | C7—H7 | 1.10 (3) |
C1—C11 | 1.428 (3) | C8—C14 | 1.422 (3) |
C1—H1 | 1.10 (2) | C8—H8 | 1.03 (2) |
C2—C3 | 1.408 (4) | C9—C11 | 1.396 (3) |
C2—H2 | 1.00 (3) | C9—C14 | 1.405 (3) |
C3—C4 | 1.338 (3) | C9—C15 | 1.508 (3) |
C3—H3 | 1.02 (2) | C10—C12 | 1.384 (3) |
C4—C12 | 1.419 (3) | C10—C13 | 1.385 (3) |
C4—H4 | 1.00 (2) | C10—H10 | 1.02 (2) |
C5—C6 | 1.342 (3) | C11—C12 | 1.438 (3) |
C5—C13 | 1.419 (3) | C13—C14 | 1.435 (2) |
C5—H5 | 0.99 (2) | C15—H15A | 0.88 (5) |
C6—C7 | 1.409 (3) | C15—H15B | 0.99 (5) |
C6—H6 | 0.97 (3) | C15—H15C | 0.99 (4) |
C7—C8 | 1.353 (3) | | |
| | | |
C2—C1—C11 | 122.0 (2) | C11—C9—C14 | 120.27 (16) |
C2—C1—H1 | 119.2 (12) | C11—C9—C15 | 119.81 (19) |
C11—C1—H1 | 118.8 (13) | C14—C9—C15 | 119.91 (19) |
C1—C2—C3 | 120.9 (2) | C12—C10—C13 | 121.86 (17) |
C1—C2—H2 | 122.3 (15) | C12—C10—H10 | 119.5 (11) |
C3—C2—H2 | 116.8 (15) | C13—C10—H10 | 118.7 (11) |
C4—C3—C2 | 119.7 (2) | C9—C11—C1 | 123.53 (18) |
C4—C3—H3 | 120.6 (14) | C9—C11—C12 | 119.91 (17) |
C2—C3—H3 | 119.8 (14) | C1—C11—C12 | 116.55 (19) |
C3—C4—C12 | 122.0 (2) | C10—C12—C4 | 122.05 (18) |
C3—C4—H4 | 123.5 (13) | C10—C12—C11 | 119.05 (18) |
C12—C4—H4 | 114.5 (13) | C4—C12—C11 | 118.89 (19) |
C6—C5—C13 | 121.6 (2) | C10—C13—C5 | 121.73 (18) |
C6—C5—H5 | 122.1 (11) | C10—C13—C14 | 119.45 (17) |
C13—C5—H5 | 116.2 (12) | C5—C13—C14 | 118.78 (18) |
C5—C6—C7 | 120.3 (2) | C9—C14—C8 | 123.49 (17) |
C5—C6—H6 | 121.1 (14) | C9—C14—C13 | 119.43 (17) |
C7—C6—H6 | 118.7 (14) | C8—C14—C13 | 117.06 (17) |
C8—C7—C6 | 120.2 (2) | C9—C15—H15A | 112 (2) |
C8—C7—H7 | 120.3 (14) | C9—C15—H15B | 112 (3) |
C6—C7—H7 | 119.5 (14) | H15A—C15—H15B | 109 (3) |
C7—C8—C14 | 122.1 (2) | C9—C15—H15C | 111.5 (18) |
C7—C8—H8 | 117.9 (12) | H15A—C15—H15C | 105 (3) |
C14—C8—H8 | 119.9 (12) | H15B—C15—H15C | 107 (3) |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.232 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8804 (14) Å | Cell parameters from 500 reflections |
b = 14.593 (3) Å | θ = 4–22° |
c = 8.0508 (14) Å | µ = 0.07 mm−1 |
β = 96.460 (16)° | T = 293 K |
V = 1036.7 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1231 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3403 measured reflections | k = −18→16 |
1938 independent reflections | l = −9→5 |
Refinement top
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)] = 0.068 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.238 | Calculated w = 1/[σ2(Fo2) + (0.1495P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.12 | (Δ/σ)max < 0.001 |
1938 reflections | Δρmax = 0.31 e Å−3 |
198 parameters | Δρmin = −0.21 e Å−3 |
184 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.015 (12) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1009 (3) | 0.42021 (16) | 0.3037 (3) | 0.0650 (7) | 0.971 (3) |
H1M | 1.0493 | 0.4485 | 0.3840 | 0.078* | 0.971 (3) |
C2M | 1.2503 (3) | 0.40254 (18) | 0.3396 (3) | 0.0758 (7) | 0.971 (3) |
H2M | 1.2996 | 0.4193 | 0.4432 | 0.091* | 0.971 (3) |
C3M | 1.3322 (3) | 0.35933 (19) | 0.2228 (4) | 0.0767 (8) | 0.971 (3) |
H3M | 1.4350 | 0.3473 | 0.2491 | 0.092* | 0.971 (3) |
C4M | 1.2616 (3) | 0.33536 (17) | 0.0724 (4) | 0.0647 (7) | 0.971 (3) |
H4M | 1.3166 | 0.3060 | −0.0037 | 0.078* | 0.971 (3) |
C5M | 0.8047 (3) | 0.31924 (14) | −0.3287 (3) | 0.0594 (6) | 0.971 (3) |
H5M | 0.8610 | 0.2935 | −0.4075 | 0.071* | 0.971 (3) |
C6M | 0.6542 (3) | 0.33036 (16) | −0.3671 (3) | 0.0721 (7) | 0.971 (3) |
H6M | 0.6077 | 0.3120 | −0.4710 | 0.087* | 0.971 (3) |
C7M | 0.5677 (3) | 0.36962 (17) | −0.2502 (3) | 0.0727 (7) | 0.971 (3) |
H7M | 0.4636 | 0.3765 | −0.2764 | 0.087* | 0.971 (3) |
C8M | 0.6347 (3) | 0.39746 (17) | −0.1000 (3) | 0.0608 (6) | 0.971 (3) |
H8M | 0.5753 | 0.4244 | −0.0254 | 0.073* | 0.971 (3) |
C9M | 0.8654 (2) | 0.41317 (13) | 0.1060 (2) | 0.0487 (6) | 0.971 (3) |
C10M | 1.0328 (2) | 0.33010 (13) | −0.1277 (2) | 0.0517 (6) | 0.971 (3) |
H10M | 1.0885 | 0.3027 | −0.2054 | 0.062* | 0.971 (3) |
C11M | 1.0199 (2) | 0.39673 (13) | 0.1465 (3) | 0.0479 (6) | 0.971 (3) |
C12M | 1.1055 (2) | 0.35368 (13) | 0.0268 (3) | 0.0499 (6) | 0.971 (3) |
C13M | 0.8796 (2) | 0.34578 (12) | −0.1711 (2) | 0.0482 (6) | 0.971 (3) |
C14M | 0.7923 (2) | 0.38714 (13) | −0.0515 (2) | 0.0457 (5) | 0.971 (3) |
C15M | 0.7744 (3) | 0.45683 (16) | 0.2320 (3) | 0.0711 (7) | 0.971 (3) |
H15A | 0.6710 | 0.4635 | 0.1841 | 0.107* | 0.971 (3) |
H15B | 0.8158 | 0.5160 | 0.2626 | 0.107* | 0.971 (3) |
H15C | 0.7784 | 0.4188 | 0.3297 | 0.107* | 0.971 (3) |
C1D | 1.097 (6) | 0.398 (4) | 0.366 (4) | 0.086 (16)* | 0.029 (3) |
C2D | 1.232 (6) | 0.353 (5) | 0.413 (5) | 0.083 (19)* | 0.029 (3) |
C3D | 1.323 (6) | 0.333 (5) | 0.289 (6) | 0.09 (2)* | 0.029 (3) |
C4D | 1.284 (5) | 0.356 (5) | 0.122 (6) | 0.053 (15)* | 0.029 (3) |
C5D | 0.865 (5) | 0.357 (4) | −0.283 (5) | 0.056 (15)* | 0.029 (3) |
C6D | 0.710 (6) | 0.342 (5) | −0.317 (7) | 0.10 (3)* | 0.029 (3) |
C7D | 0.618 (5) | 0.363 (6) | −0.196 (7) | 0.08 (2)* | 0.029 (3) |
C8D | 0.676 (4) | 0.401 (5) | −0.044 (7) | 0.052 (19)* | 0.029 (3) |
C9D | 0.903 (3) | 0.4656 (19) | 0.146 (4) | 0.069 (10)* | 0.029 (3) |
C10D | 1.086 (3) | 0.4264 (19) | −0.100 (4) | 0.061 (15)* | 0.029 (3) |
C11D | 1.058 (4) | 0.423 (3) | 0.199 (4) | 0.024 (8)* | 0.029 (3) |
C12D | 1.149 (4) | 0.403 (3) | 0.076 (4) | 0.077 (18)* | 0.029 (3) |
C13D | 0.922 (4) | 0.395 (3) | −0.131 (4) | 0.065 (16)* | 0.029 (3) |
C14D | 0.830 (3) | 0.413 (3) | −0.002 (4) | 0.028 (9)* | 0.029 (3) |
C15D | 0.830 (5) | 0.466 (3) | 0.312 (5) | 0.046 (13)* | 0.029 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.0792 (16) | 0.0628 (13) | 0.0517 (14) | −0.0032 (11) | 0.0019 (11) | −0.0047 (10) |
C2M | 0.0759 (17) | 0.0808 (16) | 0.0659 (16) | −0.0061 (12) | −0.0133 (12) | 0.0010 (12) |
C3M | 0.0552 (15) | 0.0847 (18) | 0.087 (2) | −0.0050 (11) | −0.0069 (13) | 0.0105 (15) |
C4M | 0.0523 (14) | 0.0712 (15) | 0.0713 (16) | −0.0010 (10) | 0.0096 (11) | −0.0004 (12) |
C5M | 0.0786 (16) | 0.0520 (12) | 0.0470 (12) | 0.0027 (10) | 0.0043 (10) | −0.0060 (9) |
C6M | 0.0821 (18) | 0.0679 (14) | 0.0608 (15) | −0.0001 (12) | −0.0166 (12) | −0.0013 (11) |
C7M | 0.0606 (15) | 0.0772 (16) | 0.0763 (17) | 0.0063 (12) | −0.0093 (13) | 0.0052 (13) |
C8M | 0.0550 (14) | 0.0612 (14) | 0.0657 (16) | 0.0072 (10) | 0.0051 (12) | 0.0034 (12) |
C9M | 0.0571 (12) | 0.0446 (10) | 0.0459 (12) | −0.0009 (8) | 0.0123 (8) | 0.0010 (8) |
C10M | 0.0580 (13) | 0.0496 (11) | 0.0491 (12) | 0.0026 (8) | 0.0137 (9) | −0.0041 (8) |
C11M | 0.0545 (13) | 0.0437 (10) | 0.0450 (12) | −0.0045 (8) | 0.0035 (9) | 0.0020 (8) |
C12M | 0.0497 (12) | 0.0468 (10) | 0.0539 (12) | −0.0023 (8) | 0.0093 (9) | 0.0030 (8) |
C13M | 0.0586 (13) | 0.0405 (10) | 0.0458 (12) | 0.0002 (8) | 0.0069 (9) | 0.0025 (8) |
C14M | 0.0520 (12) | 0.0395 (10) | 0.0460 (12) | 0.0016 (8) | 0.0071 (9) | 0.0029 (8) |
C15M | 0.0768 (16) | 0.0802 (15) | 0.0585 (15) | 0.0053 (12) | 0.0175 (12) | −0.0090 (11) |
Geometric parameters (Å, º) top
C1M—C2M | 1.351 (3) | C1D—C11D | 1.394 (18) |
C1M—C11M | 1.426 (3) | C2D—C3D | 1.384 (19) |
C2M—C3M | 1.402 (4) | C3D—C4D | 1.388 (19) |
C3M—C4M | 1.345 (4) | C4D—C12D | 1.391 (18) |
C4M—C12M | 1.419 (3) | C5D—C6D | 1.388 (19) |
C5M—C6M | 1.347 (3) | C5D—C13D | 1.391 (18) |
C5M—C13M | 1.418 (3) | C6D—C7D | 1.380 (19) |
C6M—C7M | 1.402 (3) | C7D—C8D | 1.382 (19) |
C7M—C8M | 1.349 (4) | C8D—C14D | 1.389 (18) |
C8M—C14M | 1.418 (3) | C9D—C14D | 1.500 (17) |
C9M—C11M | 1.395 (3) | C9D—C11D | 1.525 (17) |
C9M—C14M | 1.410 (3) | C9D—C15D | 1.548 (18) |
C9M—C15M | 1.508 (3) | C9D—C10Di | 1.624 (18) |
C10M—C12M | 1.380 (3) | C10D—C12D | 1.503 (17) |
C10M—C13M | 1.385 (3) | C10D—C13D | 1.517 (17) |
C11M—C12M | 1.437 (3) | C10D—C9Di | 1.624 (18) |
C13M—C14M | 1.435 (3) | C11D—C12D | 1.389 (17) |
C1D—C2D | 1.386 (19) | C13D—C14D | 1.415 (17) |
| | | |
C2M—C1M—C11M | 122.0 (2) | C3D—C4D—C12D | 120 (2) |
C1M—C2M—C3M | 120.9 (2) | C6D—C5D—C13D | 119 (2) |
C4M—C3M—C2M | 119.7 (2) | C7D—C6D—C5D | 119 (2) |
C3M—C4M—C12M | 121.8 (2) | C6D—C7D—C8D | 121 (2) |
C6M—C5M—C13M | 121.7 (2) | C7D—C8D—C14D | 122 (2) |
C5M—C6M—C7M | 120.0 (2) | C14D—C9D—C11D | 108.0 (19) |
C8M—C7M—C6M | 120.3 (2) | C14D—C9D—C15D | 121 (2) |
C7M—C8M—C14M | 122.5 (2) | C11D—C9D—C15D | 102.1 (19) |
C11M—C9M—C14M | 120.33 (18) | C14D—C9D—C10Di | 110 (2) |
C11M—C9M—C15M | 120.20 (19) | C11D—C9D—C10Di | 112 (2) |
C14M—C9M—C15M | 119.46 (18) | C15D—C9D—C10Di | 103 (2) |
C12M—C10M—C13M | 122.19 (18) | C12D—C10D—C13D | 110 (2) |
C9M—C11M—C1M | 123.43 (19) | C12D—C10D—C9Di | 114 (2) |
C9M—C11M—C12M | 119.95 (19) | C13D—C10D—C9Di | 110 (2) |
C1M—C11M—C12M | 116.62 (19) | C12D—C11D—C1D | 122 (2) |
C10M—C12M—C4M | 122.1 (2) | C12D—C11D—C9D | 118.0 (18) |
C10M—C12M—C11M | 118.98 (19) | C1D—C11D—C9D | 120 (2) |
C4M—C12M—C11M | 119.0 (2) | C11D—C12D—C4D | 118 (2) |
C10M—C13M—C5M | 121.91 (18) | C11D—C12D—C10D | 116.1 (19) |
C10M—C13M—C14M | 119.34 (18) | C4D—C12D—C10D | 126 (2) |
C5M—C13M—C14M | 118.72 (19) | C5D—C13D—C14D | 122 (2) |
C9M—C14M—C8M | 123.99 (18) | C5D—C13D—C10D | 121 (2) |
C9M—C14M—C13M | 119.20 (18) | C14D—C13D—C10D | 116.7 (19) |
C8M—C14M—C13M | 116.80 (19) | C8D—C14D—C13D | 116 (2) |
C2D—C1D—C11D | 120 (2) | C8D—C14D—C9D | 126 (2) |
C3D—C2D—C1D | 117 (2) | C13D—C14D—C9D | 116.5 (18) |
C2D—C3D—C4D | 123 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8789 (13) Å | Cell parameters from 500 reflections |
b = 14.592 (2) Å | θ = 4–22° |
c = 8.0602 (12) Å | µ = 0.07 mm−1 |
β = 96.480 (16)° | T = 293 K |
V = 1037.6 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1214 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3396 measured reflections | k = −18→16 |
1937 independent reflections | l = −9→5 |
Refinement top
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)] = 0.069 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.238 | Calculated w = 1/[σ2(Fo2) + (0.146P)2 + 0.0231P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1937 reflections | Δρmax = 0.31 e Å−3 |
198 parameters | Δρmin = −0.18 e Å−3 |
184 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.007 (10) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1014 (3) | 0.42008 (17) | 0.3037 (3) | 0.0660 (7) | 0.956 (3) |
H1M | 1.0498 | 0.4483 | 0.3839 | 0.079* | 0.956 (3) |
C2M | 1.2509 (3) | 0.40255 (19) | 0.3401 (3) | 0.0770 (8) | 0.956 (3) |
H2M | 1.3001 | 0.4195 | 0.4435 | 0.092* | 0.956 (3) |
C3M | 1.3324 (3) | 0.3590 (2) | 0.2235 (5) | 0.0789 (8) | 0.956 (3) |
H3M | 1.4350 | 0.3464 | 0.2501 | 0.095* | 0.956 (3) |
C4M | 1.2620 (3) | 0.33538 (18) | 0.0731 (4) | 0.0651 (7) | 0.956 (3) |
H4M | 1.3172 | 0.3063 | −0.0031 | 0.078* | 0.956 (3) |
C5M | 0.8056 (3) | 0.31908 (15) | −0.3281 (3) | 0.0600 (7) | 0.956 (3) |
H5M | 0.8620 | 0.2935 | −0.4069 | 0.072* | 0.956 (3) |
C6M | 0.6549 (3) | 0.33015 (17) | −0.3665 (3) | 0.0734 (8) | 0.956 (3) |
H6M | 0.6083 | 0.3115 | −0.4702 | 0.088* | 0.956 (3) |
C7M | 0.5685 (3) | 0.36974 (18) | −0.2500 (3) | 0.0726 (8) | 0.956 (3) |
H7M | 0.4645 | 0.3769 | −0.2766 | 0.087* | 0.956 (3) |
C8M | 0.6349 (3) | 0.39742 (18) | −0.1001 (3) | 0.0609 (7) | 0.956 (3) |
H8M | 0.5753 | 0.4242 | −0.0256 | 0.073* | 0.956 (3) |
C9M | 0.8654 (2) | 0.41280 (13) | 0.1056 (2) | 0.0496 (6) | 0.956 (3) |
C10M | 1.0336 (2) | 0.33006 (14) | −0.1274 (3) | 0.0528 (6) | 0.956 (3) |
H10M | 1.0896 | 0.3030 | −0.2051 | 0.063* | 0.956 (3) |
C11M | 1.0198 (2) | 0.39684 (14) | 0.1462 (3) | 0.0484 (6) | 0.956 (3) |
C12M | 1.1061 (2) | 0.35357 (14) | 0.0275 (3) | 0.0512 (6) | 0.956 (3) |
C13M | 0.8803 (2) | 0.34550 (12) | −0.1705 (2) | 0.0492 (6) | 0.956 (3) |
C14M | 0.7926 (2) | 0.38715 (14) | −0.0517 (3) | 0.0465 (6) | 0.956 (3) |
C15M | 0.7740 (3) | 0.45678 (18) | 0.2318 (3) | 0.0703 (7) | 0.956 (3) |
H15A | 0.6706 | 0.4635 | 0.1838 | 0.105* | 0.956 (3) |
H15B | 0.8155 | 0.5160 | 0.2621 | 0.105* | 0.956 (3) |
H15C | 0.7779 | 0.4188 | 0.3294 | 0.105* | 0.956 (3) |
C1D | 1.084 (4) | 0.395 (3) | 0.366 (4) | 0.079 (14)* | 0.044 (3) |
C2D | 1.225 (4) | 0.358 (3) | 0.417 (4) | 0.071 (13)* | 0.044 (3) |
C3D | 1.324 (4) | 0.345 (3) | 0.299 (5) | 0.09 (2)* | 0.044 (3) |
C4D | 1.289 (4) | 0.367 (3) | 0.131 (5) | 0.056 (12)* | 0.044 (3) |
C5D | 0.875 (4) | 0.358 (3) | −0.289 (4) | 0.056 (11)* | 0.044 (3) |
C6D | 0.724 (4) | 0.335 (4) | −0.328 (5) | 0.10 (2)* | 0.044 (3) |
C7D | 0.626 (4) | 0.353 (4) | −0.210 (6) | 0.10 (2)* | 0.044 (3) |
C8D | 0.678 (3) | 0.392 (4) | −0.059 (5) | 0.044 (14)* | 0.044 (3) |
C9D | 0.896 (3) | 0.4638 (16) | 0.140 (3) | 0.065 (9)* | 0.044 (3) |
C10D | 1.089 (3) | 0.4282 (16) | −0.096 (3) | 0.049 (10)* | 0.044 (3) |
C11D | 1.048 (3) | 0.418 (2) | 0.198 (3) | 0.029 (8)* | 0.044 (3) |
C12D | 1.147 (3) | 0.404 (3) | 0.080 (3) | 0.071 (13)* | 0.044 (3) |
C13D | 0.925 (3) | 0.400 (2) | −0.139 (3) | 0.059 (11)* | 0.044 (3) |
C14D | 0.828 (3) | 0.414 (2) | −0.013 (3) | 0.036 (9)* | 0.044 (3) |
C15D | 0.826 (4) | 0.466 (3) | 0.307 (4) | 0.053 (11)* | 0.044 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.0810 (18) | 0.0653 (15) | 0.0506 (15) | −0.0024 (12) | 0.0027 (11) | −0.0042 (11) |
C2M | 0.0765 (18) | 0.0810 (17) | 0.0684 (17) | −0.0050 (13) | −0.0138 (13) | −0.0013 (13) |
C3M | 0.0574 (17) | 0.0866 (19) | 0.089 (2) | −0.0033 (13) | −0.0059 (14) | 0.0112 (16) |
C4M | 0.0535 (15) | 0.0702 (15) | 0.0717 (16) | 0.0002 (11) | 0.0078 (11) | −0.0021 (13) |
C5M | 0.0799 (18) | 0.0521 (13) | 0.0474 (13) | 0.0037 (11) | 0.0047 (11) | −0.0059 (9) |
C6M | 0.0819 (19) | 0.0671 (15) | 0.0656 (16) | −0.0001 (13) | −0.0156 (13) | −0.0016 (12) |
C7M | 0.0614 (16) | 0.0756 (17) | 0.0772 (17) | 0.0058 (13) | −0.0080 (13) | 0.0051 (13) |
C8M | 0.0566 (15) | 0.0611 (15) | 0.0647 (16) | 0.0089 (12) | 0.0047 (13) | 0.0054 (12) |
C9M | 0.0578 (13) | 0.0459 (11) | 0.0468 (12) | 0.0005 (9) | 0.0135 (9) | 0.0013 (8) |
C10M | 0.0576 (14) | 0.0513 (11) | 0.0516 (13) | 0.0022 (9) | 0.0153 (9) | −0.0047 (9) |
C11M | 0.0564 (14) | 0.0440 (11) | 0.0446 (12) | −0.0026 (9) | 0.0046 (9) | 0.0023 (9) |
C12M | 0.0517 (13) | 0.0473 (11) | 0.0556 (13) | −0.0018 (8) | 0.0103 (9) | 0.0017 (9) |
C13M | 0.0615 (14) | 0.0398 (10) | 0.0471 (13) | 0.0008 (8) | 0.0089 (9) | 0.0030 (8) |
C14M | 0.0514 (13) | 0.0411 (11) | 0.0474 (12) | 0.0021 (9) | 0.0069 (9) | 0.0034 (9) |
C15M | 0.0764 (16) | 0.0787 (16) | 0.0574 (15) | 0.0064 (12) | 0.0146 (12) | −0.0076 (12) |
Geometric parameters (Å, º) top
C1M—C2M | 1.351 (3) | C1D—C11D | 1.397 (17) |
C1M—C11M | 1.430 (3) | C2D—C3D | 1.380 (19) |
C2M—C3M | 1.402 (4) | C3D—C4D | 1.392 (18) |
C3M—C4M | 1.345 (4) | C4D—C12D | 1.395 (18) |
C4M—C12M | 1.417 (3) | C5D—C6D | 1.384 (19) |
C5M—C6M | 1.349 (4) | C5D—C13D | 1.384 (17) |
C5M—C13M | 1.418 (3) | C6D—C7D | 1.382 (19) |
C6M—C7M | 1.402 (4) | C7D—C8D | 1.379 (19) |
C7M—C8M | 1.345 (4) | C8D—C14D | 1.380 (18) |
C8M—C14M | 1.418 (3) | C9D—C14D | 1.496 (16) |
C9M—C11M | 1.393 (3) | C9D—C11D | 1.531 (17) |
C9M—C14M | 1.407 (3) | C9D—C15D | 1.551 (18) |
C9M—C15M | 1.513 (3) | C9D—C10Di | 1.623 (17) |
C10M—C12M | 1.381 (3) | C10D—C12D | 1.500 (17) |
C10M—C13M | 1.385 (3) | C10D—C13D | 1.516 (17) |
C11M—C12M | 1.438 (3) | C10D—C9Di | 1.623 (17) |
C13M—C14M | 1.436 (3) | C11D—C12D | 1.383 (17) |
C1D—C2D | 1.387 (18) | C13D—C14D | 1.418 (17) |
| | | |
C2M—C1M—C11M | 122.4 (2) | C3D—C4D—C12D | 118 (2) |
C1M—C2M—C3M | 120.6 (2) | C6D—C5D—C13D | 121 (2) |
C4M—C3M—C2M | 119.8 (2) | C7D—C6D—C5D | 118 (2) |
C3M—C4M—C12M | 121.8 (2) | C8D—C7D—C6D | 121 (2) |
C6M—C5M—C13M | 121.7 (2) | C7D—C8D—C14D | 123 (2) |
C5M—C6M—C7M | 119.9 (2) | C14D—C9D—C11D | 107.5 (18) |
C8M—C7M—C6M | 120.6 (3) | C14D—C9D—C15D | 124 (2) |
C7M—C8M—C14M | 122.3 (2) | C11D—C9D—C15D | 99.6 (17) |
C11M—C9M—C14M | 120.47 (19) | C14D—C9D—C10Di | 109.4 (18) |
C11M—C9M—C15M | 120.1 (2) | C11D—C9D—C10Di | 113.3 (18) |
C14M—C9M—C15M | 119.45 (19) | C15D—C9D—C10Di | 102.6 (18) |
C12M—C10M—C13M | 122.05 (18) | C12D—C10D—C13D | 111.3 (18) |
C9M—C11M—C1M | 123.8 (2) | C12D—C10D—C9Di | 114 (2) |
C9M—C11M—C12M | 120.1 (2) | C13D—C10D—C9Di | 108.8 (19) |
C1M—C11M—C12M | 116.1 (2) | C12D—C11D—C1D | 122.2 (18) |
C10M—C12M—C4M | 122.0 (2) | C12D—C11D—C9D | 117.5 (17) |
C10M—C12M—C11M | 118.8 (2) | C1D—C11D—C9D | 120.3 (19) |
C4M—C12M—C11M | 119.2 (2) | C11D—C12D—C4D | 119.0 (18) |
C10M—C13M—C5M | 121.84 (19) | C11D—C12D—C10D | 116.2 (18) |
C10M—C13M—C14M | 119.58 (19) | C4D—C12D—C10D | 125 (2) |
C5M—C13M—C14M | 118.6 (2) | C5D—C13D—C14D | 122.1 (18) |
C9M—C14M—C8M | 123.96 (19) | C5D—C13D—C10D | 121.4 (19) |
C9M—C14M—C13M | 118.99 (19) | C14D—C13D—C10D | 116.5 (17) |
C8M—C14M—C13M | 117.0 (2) | C8D—C14D—C13D | 114.9 (19) |
C2D—C1D—C11D | 119 (2) | C8D—C14D—C9D | 128 (2) |
C3D—C2D—C1D | 118 (2) | C13D—C14D—C9D | 115.9 (17) |
C2D—C3D—C4D | 124 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.230 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8738 (13) Å | Cell parameters from 500 reflections |
b = 14.593 (2) Å | θ = 4–22° |
c = 8.0674 (12) Å | µ = 0.07 mm−1 |
β = 96.465 (15)° | T = 293 K |
V = 1038.0 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1205 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3401 measured reflections | k = −18→16 |
1940 independent reflections | l = −9→5 |
Refinement top
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)] = 0.071 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.245 | Calculated w = 1/[σ2(Fo2) + (0.1343P)2 + 0.1501P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1940 reflections | Δρmax = 0.26 e Å−3 |
198 parameters | Δρmin = −0.21 e Å−3 |
184 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (10) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1012 (3) | 0.42020 (19) | 0.3035 (4) | 0.0656 (8) | 0.936 (3) |
H1M | 1.0493 | 0.4487 | 0.3831 | 0.079* | 0.936 (3) |
C2M | 1.2508 (4) | 0.4026 (2) | 0.3405 (4) | 0.0779 (9) | 0.936 (3) |
H2M | 1.2996 | 0.4194 | 0.4441 | 0.093* | 0.936 (3) |
C3M | 1.3327 (3) | 0.3595 (2) | 0.2245 (5) | 0.0799 (10) | 0.936 (3) |
H3M | 1.4354 | 0.3472 | 0.2512 | 0.096* | 0.936 (3) |
C4M | 1.2622 (3) | 0.3357 (2) | 0.0734 (4) | 0.0663 (8) | 0.936 (3) |
H4M | 1.3177 | 0.3067 | −0.0026 | 0.080* | 0.936 (3) |
C5M | 0.8063 (4) | 0.31899 (18) | −0.3282 (3) | 0.0618 (8) | 0.936 (3) |
H5M | 0.8625 | 0.2933 | −0.4069 | 0.074* | 0.936 (3) |
C6M | 0.6551 (4) | 0.3303 (2) | −0.3660 (4) | 0.0744 (9) | 0.936 (3) |
H6M | 0.6083 | 0.3119 | −0.4696 | 0.089* | 0.936 (3) |
C7M | 0.5687 (4) | 0.3696 (2) | −0.2496 (4) | 0.0724 (9) | 0.936 (3) |
H7M | 0.4647 | 0.3766 | −0.2763 | 0.087* | 0.936 (3) |
C8M | 0.6341 (4) | 0.3973 (2) | −0.1004 (4) | 0.0625 (9) | 0.936 (3) |
H8M | 0.5742 | 0.4242 | −0.0263 | 0.075* | 0.936 (3) |
C9M | 0.8651 (3) | 0.41276 (15) | 0.1056 (3) | 0.0497 (6) | 0.936 (3) |
C10M | 1.0333 (3) | 0.32984 (16) | −0.1271 (3) | 0.0533 (7) | 0.936 (3) |
H10M | 1.0890 | 0.3022 | −0.2044 | 0.064* | 0.936 (3) |
C11M | 1.0201 (3) | 0.39652 (16) | 0.1465 (3) | 0.0483 (7) | 0.936 (3) |
C12M | 1.1063 (3) | 0.35362 (16) | 0.0276 (3) | 0.0509 (6) | 0.936 (3) |
C13M | 0.8809 (3) | 0.34567 (14) | −0.1703 (3) | 0.0493 (6) | 0.936 (3) |
C14M | 0.7928 (3) | 0.38698 (17) | −0.0514 (3) | 0.0466 (6) | 0.936 (3) |
C15M | 0.7733 (3) | 0.4566 (2) | 0.2312 (4) | 0.0702 (9) | 0.936 (3) |
H15A | 0.6699 | 0.4632 | 0.1830 | 0.105* | 0.936 (3) |
H15B | 0.8146 | 0.5159 | 0.2616 | 0.105* | 0.936 (3) |
H15C | 0.7770 | 0.4186 | 0.3287 | 0.105* | 0.936 (3) |
C1D | 1.077 (4) | 0.398 (3) | 0.365 (3) | 0.078 (12)* | 0.064 (3) |
C2D | 1.216 (4) | 0.359 (3) | 0.422 (4) | 0.095 (13)* | 0.064 (3) |
C3D | 1.316 (4) | 0.342 (3) | 0.305 (4) | 0.103 (18)* | 0.064 (3) |
C4D | 1.283 (3) | 0.361 (3) | 0.136 (4) | 0.052 (10)* | 0.064 (3) |
C5D | 0.881 (4) | 0.352 (3) | −0.287 (4) | 0.078 (12)* | 0.064 (3) |
C6D | 0.731 (4) | 0.327 (3) | −0.332 (4) | 0.060 (14)* | 0.064 (3) |
C7D | 0.631 (4) | 0.348 (3) | −0.218 (5) | 0.088 (16)* | 0.064 (3) |
C8D | 0.677 (3) | 0.394 (3) | −0.071 (5) | 0.052 (14)* | 0.064 (3) |
C9D | 0.891 (2) | 0.4639 (15) | 0.133 (3) | 0.069 (8)* | 0.064 (3) |
C10D | 1.090 (3) | 0.4274 (15) | −0.095 (3) | 0.066 (10)* | 0.064 (3) |
C11D | 1.044 (3) | 0.4212 (19) | 0.197 (3) | 0.036 (5)* | 0.064 (3) |
C12D | 1.143 (3) | 0.403 (3) | 0.082 (3) | 0.080 (12)* | 0.064 (3) |
C13D | 0.928 (3) | 0.398 (2) | −0.141 (3) | 0.069 (10)* | 0.064 (3) |
C14D | 0.827 (3) | 0.413 (2) | −0.018 (3) | 0.041 (5)* | 0.064 (3) |
C15D | 0.812 (4) | 0.463 (3) | 0.294 (4) | 0.076 (14)* | 0.064 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.079 (2) | 0.0644 (16) | 0.0522 (17) | −0.0023 (14) | 0.0026 (13) | −0.0035 (13) |
C2M | 0.078 (2) | 0.083 (2) | 0.0682 (19) | −0.0066 (15) | −0.0135 (15) | −0.0019 (15) |
C3M | 0.0571 (19) | 0.088 (2) | 0.090 (3) | −0.0065 (15) | −0.0105 (17) | 0.0113 (19) |
C4M | 0.0533 (17) | 0.0722 (18) | 0.073 (2) | 0.0003 (12) | 0.0075 (13) | −0.0030 (16) |
C5M | 0.078 (2) | 0.0565 (16) | 0.0507 (15) | 0.0040 (14) | 0.0051 (13) | −0.0054 (11) |
C6M | 0.083 (2) | 0.0703 (18) | 0.0641 (19) | −0.0001 (15) | −0.0166 (16) | −0.0004 (14) |
C7M | 0.0572 (18) | 0.0772 (19) | 0.080 (2) | 0.0070 (15) | −0.0068 (14) | 0.0035 (15) |
C8M | 0.0514 (18) | 0.0638 (18) | 0.072 (2) | 0.0085 (15) | 0.0047 (15) | 0.0057 (14) |
C9M | 0.0562 (15) | 0.0464 (13) | 0.0482 (14) | 0.0006 (10) | 0.0132 (10) | 0.0020 (9) |
C10M | 0.0575 (16) | 0.0502 (13) | 0.0545 (15) | 0.0022 (10) | 0.0162 (11) | −0.0044 (10) |
C11M | 0.0553 (15) | 0.0440 (12) | 0.0449 (13) | −0.0038 (10) | 0.0018 (10) | 0.0009 (10) |
C12M | 0.0492 (14) | 0.0477 (12) | 0.0563 (14) | −0.0012 (9) | 0.0078 (10) | 0.0041 (10) |
C13M | 0.0611 (16) | 0.0405 (12) | 0.0465 (14) | 0.0025 (10) | 0.0071 (10) | 0.0032 (9) |
C14M | 0.0507 (15) | 0.0418 (13) | 0.0474 (14) | 0.0008 (10) | 0.0060 (10) | 0.0028 (10) |
C15M | 0.0731 (19) | 0.0802 (19) | 0.0585 (18) | 0.0050 (14) | 0.0133 (14) | −0.0088 (15) |
Geometric parameters (Å, º) top
C1M—C2M | 1.352 (4) | C1D—C11D | 1.394 (17) |
C1M—C11M | 1.427 (4) | C2D—C3D | 1.385 (18) |
C2M—C3M | 1.398 (4) | C3D—C4D | 1.394 (18) |
C3M—C4M | 1.351 (4) | C4D—C12D | 1.401 (17) |
C4M—C12M | 1.415 (3) | C5D—C6D | 1.382 (18) |
C5M—C6M | 1.352 (4) | C5D—C13D | 1.384 (17) |
C5M—C13M | 1.422 (3) | C6D—C7D | 1.382 (19) |
C6M—C7M | 1.400 (4) | C7D—C8D | 1.381 (18) |
C7M—C8M | 1.338 (4) | C8D—C14D | 1.379 (17) |
C8M—C14M | 1.428 (4) | C9D—C14D | 1.489 (16) |
C9M—C11M | 1.398 (3) | C9D—C11D | 1.531 (16) |
C9M—C14M | 1.405 (3) | C9D—C15D | 1.547 (18) |
C9M—C15M | 1.512 (3) | C9D—C10Di | 1.627 (17) |
C10M—C13M | 1.378 (3) | C10D—C12D | 1.497 (16) |
C10M—C12M | 1.384 (3) | C10D—C13D | 1.510 (17) |
C11M—C12M | 1.436 (3) | C10D—C9Di | 1.627 (17) |
C13M—C14M | 1.436 (3) | C11D—C12D | 1.379 (17) |
C1D—C2D | 1.386 (18) | C13D—C14D | 1.427 (17) |
| | | |
C2M—C1M—C11M | 122.3 (3) | C3D—C4D—C12D | 118 (2) |
C1M—C2M—C3M | 120.6 (3) | C6D—C5D—C13D | 122 (2) |
C4M—C3M—C2M | 119.8 (3) | C7D—C6D—C5D | 116 (2) |
C3M—C4M—C12M | 121.8 (3) | C8D—C7D—C6D | 122 (2) |
C6M—C5M—C13M | 121.2 (3) | C14D—C8D—C7D | 123 (2) |
C5M—C6M—C7M | 120.2 (3) | C14D—C9D—C11D | 108.6 (17) |
C8M—C7M—C6M | 120.8 (3) | C14D—C9D—C15D | 121 (2) |
C7M—C8M—C14M | 122.1 (3) | C11D—C9D—C15D | 100.6 (18) |
C11M—C9M—C14M | 120.3 (2) | C14D—C9D—C10Di | 111.7 (17) |
C11M—C9M—C15M | 120.2 (2) | C11D—C9D—C10Di | 110.9 (17) |
C14M—C9M—C15M | 119.5 (2) | C15D—C9D—C10Di | 103.5 (19) |
C13M—C10M—C12M | 122.2 (2) | C12D—C10D—C13D | 110.7 (18) |
C9M—C11M—C1M | 123.5 (2) | C12D—C10D—C9Di | 112.9 (19) |
C9M—C11M—C12M | 120.0 (2) | C13D—C10D—C9Di | 110.2 (18) |
C1M—C11M—C12M | 116.4 (2) | C12D—C11D—C1D | 122.0 (18) |
C10M—C12M—C4M | 122.3 (2) | C12D—C11D—C9D | 117.5 (16) |
C10M—C12M—C11M | 118.7 (2) | C1D—C11D—C9D | 120.5 (18) |
C4M—C12M—C11M | 119.0 (2) | C11D—C12D—C4D | 118.9 (17) |
C10M—C13M—C5M | 121.7 (2) | C11D—C12D—C10D | 116.2 (17) |
C10M—C13M—C14M | 119.6 (2) | C4D—C12D—C10D | 125 (2) |
C5M—C13M—C14M | 118.7 (2) | C5D—C13D—C14D | 121.1 (18) |
C9M—C14M—C8M | 123.9 (2) | C5D—C13D—C10D | 122.3 (19) |
C9M—C14M—C13M | 119.2 (2) | C14D—C13D—C10D | 116.4 (17) |
C8M—C14M—C13M | 117.0 (2) | C8D—C14D—C13D | 114.5 (18) |
C2D—C1D—C11D | 120 (2) | C8D—C14D—C9D | 128.5 (19) |
C3D—C2D—C1D | 118 (2) | C13D—C14D—C9D | 115.6 (16) |
C2D—C3D—C4D | 123 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.229 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8718 (13) Å | Cell parameters from 500 reflections |
b = 14.587 (2) Å | θ = 4–22° |
c = 8.0776 (12) Å | µ = 0.07 mm−1 |
β = 96.489 (15)° | T = 293 K |
V = 1038.6 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1171 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 26.0°, θmin = 4.3° |
ω scans | h = −10→10 |
3389 measured reflections | k = −17→16 |
1942 independent reflections | l = −9→5 |
Refinement top
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)] = 0.074 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.265 | Calculated w = 1/[σ2(Fo2) + (0.1577P)2 + 0.0018P] where P = (Fo2 + 2Fc2)/3 |
S = 1.15 | (Δ/σ)max < 0.001 |
1942 reflections | Δρmax = 0.32 e Å−3 |
198 parameters | Δρmin = −0.19 e Å−3 |
172 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.009 (12) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1010 (3) | 0.42003 (19) | 0.3035 (4) | 0.0675 (8) | 0.918 (4) |
H1M | 1.0489 | 0.4484 | 0.3831 | 0.081* | 0.918 (4) |
C2M | 1.2510 (4) | 0.4025 (2) | 0.3407 (4) | 0.0798 (9) | 0.918 (4) |
H2M | 1.2998 | 0.4192 | 0.4443 | 0.096* | 0.918 (4) |
C3M | 1.3331 (3) | 0.3595 (2) | 0.2247 (5) | 0.0829 (10) | 0.918 (4) |
H3M | 1.4358 | 0.3472 | 0.2516 | 0.099* | 0.918 (4) |
C4M | 1.2629 (3) | 0.3358 (2) | 0.0733 (5) | 0.0683 (9) | 0.918 (4) |
H4M | 1.3186 | 0.3071 | −0.0028 | 0.082* | 0.918 (4) |
C5M | 0.8059 (4) | 0.31914 (18) | −0.3275 (3) | 0.0638 (8) | 0.918 (4) |
H5M | 0.8623 | 0.2938 | −0.4064 | 0.077* | 0.918 (4) |
C6M | 0.6551 (4) | 0.33010 (19) | −0.3656 (4) | 0.0776 (9) | 0.918 (4) |
H6M | 0.6085 | 0.3114 | −0.4690 | 0.093* | 0.918 (4) |
C7M | 0.5688 (4) | 0.3694 (2) | −0.2500 (4) | 0.0745 (9) | 0.918 (4) |
H7M | 0.4648 | 0.3765 | −0.2772 | 0.089* | 0.918 (4) |
C8M | 0.6335 (4) | 0.3970 (3) | −0.1009 (4) | 0.0643 (9) | 0.918 (4) |
H8M | 0.5734 | 0.4237 | −0.0270 | 0.077* | 0.918 (4) |
C9M | 0.8650 (3) | 0.41288 (16) | 0.1055 (3) | 0.0524 (7) | 0.918 (4) |
C10M | 1.0337 (3) | 0.32980 (15) | −0.1268 (3) | 0.0552 (7) | 0.918 (4) |
H10M | 1.0895 | 0.3025 | −0.2041 | 0.066* | 0.918 (4) |
C11M | 1.0202 (3) | 0.39649 (19) | 0.1464 (4) | 0.0508 (7) | 0.918 (4) |
C12M | 1.1067 (3) | 0.35351 (17) | 0.0277 (3) | 0.0531 (7) | 0.918 (4) |
C13M | 0.8808 (3) | 0.34536 (14) | −0.1700 (3) | 0.0517 (7) | 0.918 (4) |
C14M | 0.7930 (3) | 0.38686 (18) | −0.0518 (3) | 0.0481 (7) | 0.918 (4) |
C15M | 0.7723 (3) | 0.4564 (2) | 0.2302 (4) | 0.0720 (9) | 0.918 (4) |
H15A | 0.6690 | 0.4628 | 0.1814 | 0.108* | 0.918 (4) |
H15B | 0.8132 | 0.5157 | 0.2611 | 0.108* | 0.918 (4) |
H15C | 0.7757 | 0.4183 | 0.3275 | 0.108* | 0.918 (4) |
C1D | 1.070 (3) | 0.396 (2) | 0.363 (3) | 0.086 (11)* | 0.082 (4) |
C2D | 1.209 (3) | 0.359 (2) | 0.421 (3) | 0.076 (8)* | 0.082 (4) |
C3D | 1.313 (3) | 0.342 (2) | 0.309 (4) | 0.108 (15)* | 0.082 (4) |
C4D | 1.280 (3) | 0.360 (2) | 0.139 (4) | 0.058 (9)* | 0.082 (4) |
C5D | 0.881 (3) | 0.349 (2) | −0.283 (3) | 0.077 (10)* | 0.082 (4) |
C6D | 0.730 (4) | 0.327 (2) | −0.329 (4) | 0.095 (19)* | 0.082 (4) |
C7D | 0.629 (3) | 0.352 (3) | −0.220 (4) | 0.082 (13)* | 0.082 (4) |
C8D | 0.676 (3) | 0.399 (3) | −0.075 (4) | 0.044 (7)* | 0.082 (4) |
C9D | 0.889 (2) | 0.4669 (13) | 0.133 (2) | 0.080 (8)* | 0.082 (4) |
C10D | 1.090 (2) | 0.4249 (13) | −0.094 (2) | 0.064 (7)* | 0.082 (4) |
C11D | 1.040 (2) | 0.4197 (16) | 0.194 (3) | 0.035 (7)* | 0.082 (4) |
C12D | 1.141 (2) | 0.400 (2) | 0.082 (2) | 0.071 (9)* | 0.082 (4) |
C13D | 0.926 (2) | 0.3969 (19) | −0.137 (3) | 0.072 (9)* | 0.082 (4) |
C14D | 0.824 (2) | 0.4161 (16) | −0.019 (3) | 0.038 (7)* | 0.082 (4) |
C15D | 0.810 (4) | 0.466 (3) | 0.294 (3) | 0.080 (12)* | 0.082 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.080 (2) | 0.0650 (16) | 0.0561 (17) | −0.0014 (14) | 0.0034 (14) | −0.0055 (13) |
C2M | 0.079 (2) | 0.082 (2) | 0.073 (2) | −0.0066 (15) | −0.0125 (15) | −0.0027 (15) |
C3M | 0.0582 (19) | 0.093 (2) | 0.093 (3) | −0.0028 (15) | −0.0102 (18) | 0.0063 (19) |
C4M | 0.0576 (18) | 0.0734 (19) | 0.074 (2) | 0.0010 (12) | 0.0083 (13) | −0.0016 (16) |
C5M | 0.082 (2) | 0.0556 (15) | 0.0534 (16) | 0.0042 (14) | 0.0059 (13) | −0.0062 (11) |
C6M | 0.087 (2) | 0.0690 (17) | 0.0703 (19) | 0.0021 (15) | −0.0171 (17) | −0.0004 (14) |
C7M | 0.0608 (19) | 0.0753 (19) | 0.084 (2) | 0.0072 (15) | −0.0075 (15) | 0.0053 (15) |
C8M | 0.0529 (19) | 0.0654 (17) | 0.074 (2) | 0.0061 (16) | 0.0040 (15) | 0.0047 (14) |
C9M | 0.0575 (15) | 0.0515 (13) | 0.0499 (14) | 0.0007 (10) | 0.0137 (10) | 0.0021 (10) |
C10M | 0.0602 (16) | 0.0517 (13) | 0.0562 (15) | 0.0025 (10) | 0.0173 (11) | −0.0056 (10) |
C11M | 0.0571 (17) | 0.0452 (13) | 0.0496 (15) | −0.0033 (10) | 0.0040 (11) | 0.0002 (12) |
C12M | 0.0524 (15) | 0.0513 (13) | 0.0564 (15) | −0.0008 (10) | 0.0099 (10) | 0.0022 (10) |
C13M | 0.0653 (16) | 0.0420 (12) | 0.0481 (15) | 0.0023 (10) | 0.0081 (11) | 0.0036 (9) |
C14M | 0.0528 (16) | 0.0419 (13) | 0.0502 (14) | 0.0010 (11) | 0.0080 (11) | 0.0019 (11) |
C15M | 0.0745 (19) | 0.0816 (19) | 0.0612 (18) | 0.0057 (14) | 0.0131 (15) | −0.0099 (15) |
Geometric parameters (Å, º) top
C1M—C2M | 1.356 (4) | C1D—C11D | 1.399 (17) |
C1M—C11M | 1.427 (4) | C2D—C3D | 1.381 (18) |
C2M—C3M | 1.398 (4) | C3D—C4D | 1.395 (18) |
C3M—C4M | 1.353 (5) | C4D—C12D | 1.397 (17) |
C4M—C12M | 1.417 (3) | C5D—C6D | 1.383 (18) |
C5M—C6M | 1.348 (5) | C5D—C13D | 1.387 (17) |
C5M—C13M | 1.420 (4) | C6D—C7D | 1.375 (19) |
C6M—C7M | 1.396 (4) | C7D—C8D | 1.378 (18) |
C7M—C8M | 1.336 (4) | C8D—C14D | 1.364 (17) |
C8M—C14M | 1.434 (4) | C9D—C14D | 1.496 (16) |
C9M—C11M | 1.400 (3) | C9D—C11D | 1.533 (16) |
C9M—C14M | 1.408 (4) | C9D—C15D | 1.546 (17) |
C9M—C15M | 1.511 (3) | C9D—C10Di | 1.624 (17) |
C10M—C13M | 1.381 (3) | C10D—C12D | 1.489 (16) |
C10M—C12M | 1.383 (3) | C10D—C13D | 1.511 (16) |
C11M—C12M | 1.438 (4) | C10D—C9Di | 1.624 (17) |
C13M—C14M | 1.433 (3) | C11D—C12D | 1.378 (16) |
C1D—C2D | 1.384 (18) | C13D—C14D | 1.420 (16) |
| | | |
C2M—C1M—C11M | 122.3 (3) | C3D—C4D—C12D | 119 (2) |
C1M—C2M—C3M | 120.6 (3) | C6D—C5D—C13D | 122 (2) |
C4M—C3M—C2M | 119.9 (3) | C7D—C6D—C5D | 116 (2) |
C3M—C4M—C12M | 121.6 (3) | C6D—C7D—C8D | 122 (2) |
C6M—C5M—C13M | 121.6 (3) | C14D—C8D—C7D | 124 (2) |
C5M—C6M—C7M | 120.1 (3) | C14D—C9D—C11D | 106.6 (15) |
C8M—C7M—C6M | 121.0 (3) | C14D—C9D—C15D | 120.8 (19) |
C7M—C8M—C14M | 121.9 (3) | C11D—C9D—C15D | 100.8 (16) |
C11M—C9M—C14M | 120.1 (2) | C14D—C9D—C10Di | 111.3 (15) |
C11M—C9M—C15M | 120.6 (2) | C11D—C9D—C10Di | 112.8 (15) |
C14M—C9M—C15M | 119.3 (2) | C15D—C9D—C10Di | 104.3 (17) |
C13M—C10M—C12M | 122.2 (2) | C12D—C10D—C13D | 109.3 (15) |
C9M—C11M—C1M | 123.4 (3) | C12D—C10D—C9Di | 113.3 (16) |
C9M—C11M—C12M | 120.1 (3) | C13D—C10D—C9Di | 110.1 (16) |
C1M—C11M—C12M | 116.5 (2) | C12D—C11D—C1D | 121.3 (16) |
C10M—C12M—C4M | 122.2 (2) | C12D—C11D—C9D | 119.4 (15) |
C10M—C12M—C11M | 118.7 (2) | C1D—C11D—C9D | 119.3 (16) |
C4M—C12M—C11M | 119.1 (3) | C11D—C12D—C4D | 119.1 (16) |
C10M—C13M—C5M | 122.0 (2) | C11D—C12D—C10D | 115.5 (15) |
C10M—C13M—C14M | 119.5 (2) | C4D—C12D—C10D | 125.4 (17) |
C5M—C13M—C14M | 118.5 (2) | C5D—C13D—C14D | 121.3 (16) |
C9M—C14M—C13M | 119.4 (2) | C5D—C13D—C10D | 120.8 (17) |
C9M—C14M—C8M | 123.7 (2) | C14D—C13D—C10D | 117.9 (15) |
C13M—C14M—C8M | 116.9 (3) | C8D—C14D—C13D | 114.1 (17) |
C2D—C1D—C11D | 119.8 (19) | C8D—C14D—C9D | 129.4 (17) |
C3D—C2D—C1D | 119 (2) | C13D—C14D—C9D | 115.5 (15) |
C2D—C3D—C4D | 122 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8652 (13) Å | Cell parameters from 500 reflections |
b = 14.573 (2) Å | θ = 4–22° |
c = 8.0993 (13) Å | µ = 0.07 mm−1 |
β = 96.499 (16)° | T = 293 K |
V = 1039.6 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1108 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3390 measured reflections | k = −17→16 |
1944 independent reflections | l = −9→5 |
Refinement top
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)] = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.287 | Calculated w = 1/[σ2(Fo2) + (0.1521P)2 + 0.2205P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
1944 reflections | Δρmax = 0.25 e Å−3 |
198 parameters | Δρmin = −0.19 e Å−3 |
160 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.010 (12) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1008 (4) | 0.4200 (2) | 0.3035 (5) | 0.0704 (10) | 0.890 (5) |
H1M | 1.0483 | 0.4485 | 0.3825 | 0.084* | 0.890 (5) |
C2M | 1.2514 (5) | 0.4025 (3) | 0.3412 (5) | 0.0833 (12) | 0.890 (5) |
H2M | 1.3000 | 0.4191 | 0.4447 | 0.100* | 0.890 (5) |
C3M | 1.3334 (4) | 0.3599 (3) | 0.2256 (7) | 0.0846 (12) | 0.890 (5) |
H3M | 1.4364 | 0.3480 | 0.2526 | 0.102* | 0.890 (5) |
C4M | 1.2635 (4) | 0.3356 (3) | 0.0733 (6) | 0.0703 (10) | 0.890 (5) |
H4M | 1.3194 | 0.3066 | −0.0020 | 0.084* | 0.890 (5) |
C5M | 0.8073 (5) | 0.3191 (2) | −0.3272 (4) | 0.0646 (9) | 0.890 (5) |
H5M | 0.8639 | 0.2938 | −0.4057 | 0.078* | 0.890 (5) |
C6M | 0.6563 (5) | 0.3303 (2) | −0.3649 (5) | 0.0784 (11) | 0.890 (5) |
H6M | 0.6098 | 0.3119 | −0.4683 | 0.094* | 0.890 (5) |
C7M | 0.5693 (5) | 0.3693 (3) | −0.2494 (5) | 0.0761 (11) | 0.890 (5) |
H7M | 0.4651 | 0.3760 | −0.2763 | 0.091* | 0.890 (5) |
C8M | 0.6342 (5) | 0.3971 (3) | −0.1007 (6) | 0.0667 (11) | 0.890 (5) |
H8M | 0.5742 | 0.4241 | −0.0272 | 0.080* | 0.890 (5) |
C9M | 0.8652 (3) | 0.4127 (2) | 0.1050 (4) | 0.0536 (8) | 0.890 (5) |
C10M | 1.0345 (3) | 0.3298 (2) | −0.1259 (3) | 0.0571 (8) | 0.890 (5) |
H10M | 1.0903 | 0.3023 | −0.2029 | 0.068* | 0.890 (5) |
C11M | 1.0205 (3) | 0.3961 (2) | 0.1467 (4) | 0.0521 (8) | 0.890 (5) |
C12M | 1.1076 (3) | 0.3537 (2) | 0.0279 (4) | 0.0543 (8) | 0.890 (5) |
C13M | 0.8816 (3) | 0.34548 (18) | −0.1694 (3) | 0.0524 (8) | 0.890 (5) |
C14M | 0.7932 (4) | 0.3866 (2) | −0.0517 (4) | 0.0501 (8) | 0.890 (5) |
C15M | 0.7713 (5) | 0.4566 (3) | 0.2290 (6) | 0.0765 (13) | 0.890 (5) |
H15A | 0.6682 | 0.4629 | 0.1798 | 0.115* | 0.890 (5) |
H15B | 0.8120 | 0.5160 | 0.2597 | 0.115* | 0.890 (5) |
H15C | 0.7744 | 0.4186 | 0.3262 | 0.115* | 0.890 (5) |
C1D | 1.070 (3) | 0.398 (2) | 0.361 (3) | 0.097 (11)* | 0.110 (5) |
C2D | 1.207 (3) | 0.359 (2) | 0.421 (3) | 0.105 (11)* | 0.110 (5) |
C3D | 1.311 (3) | 0.340 (2) | 0.310 (3) | 0.099 (12)* | 0.110 (5) |
C4D | 1.280 (3) | 0.359 (2) | 0.141 (3) | 0.059 (8)* | 0.110 (5) |
C5D | 0.883 (3) | 0.3506 (19) | −0.286 (3) | 0.077 (9)* | 0.110 (5) |
C6D | 0.732 (3) | 0.326 (2) | −0.331 (4) | 0.079 (14)* | 0.110 (5) |
C7D | 0.631 (3) | 0.348 (3) | −0.222 (4) | 0.100 (13)* | 0.110 (5) |
C8D | 0.674 (3) | 0.395 (3) | −0.077 (4) | 0.061 (9)* | 0.110 (5) |
C9D | 0.886 (2) | 0.4659 (13) | 0.128 (2) | 0.078 (7)* | 0.110 (5) |
C10D | 1.0925 (19) | 0.4251 (12) | −0.094 (2) | 0.060 (6)* | 0.110 (5) |
C11D | 1.038 (2) | 0.4228 (15) | 0.194 (2) | 0.040 (7)* | 0.110 (5) |
C12D | 1.139 (2) | 0.400 (2) | 0.084 (2) | 0.083 (9)* | 0.110 (5) |
C13D | 0.930 (2) | 0.3976 (17) | −0.140 (2) | 0.068 (7)* | 0.110 (5) |
C14D | 0.823 (2) | 0.4152 (16) | −0.025 (2) | 0.043 (8)* | 0.110 (5) |
C15D | 0.794 (4) | 0.460 (3) | 0.279 (4) | 0.078 (13)* | 0.110 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.081 (2) | 0.070 (2) | 0.060 (2) | −0.0021 (17) | 0.0023 (18) | −0.0025 (16) |
C2M | 0.083 (3) | 0.085 (2) | 0.076 (3) | −0.005 (2) | −0.0127 (19) | −0.0019 (19) |
C3M | 0.058 (2) | 0.091 (3) | 0.100 (3) | −0.0046 (18) | −0.010 (2) | 0.009 (2) |
C4M | 0.058 (2) | 0.074 (2) | 0.079 (3) | 0.0001 (15) | 0.0072 (16) | −0.004 (2) |
C5M | 0.077 (3) | 0.058 (2) | 0.058 (2) | 0.0032 (18) | 0.0063 (17) | −0.0048 (14) |
C6M | 0.089 (3) | 0.072 (2) | 0.069 (2) | 0.0016 (19) | −0.015 (2) | 0.0003 (17) |
C7M | 0.061 (2) | 0.078 (2) | 0.086 (3) | 0.0080 (19) | −0.0048 (18) | 0.0041 (19) |
C8M | 0.056 (2) | 0.065 (2) | 0.079 (3) | 0.008 (2) | 0.0045 (19) | 0.0064 (18) |
C9M | 0.0559 (18) | 0.0528 (17) | 0.0539 (18) | 0.0012 (12) | 0.0137 (12) | 0.0027 (12) |
C10M | 0.0623 (19) | 0.0551 (16) | 0.0558 (18) | 0.0012 (13) | 0.0155 (13) | −0.0050 (13) |
C11M | 0.060 (2) | 0.0436 (16) | 0.0513 (18) | −0.0033 (13) | 0.0019 (13) | 0.0010 (14) |
C12M | 0.0493 (17) | 0.0534 (16) | 0.0608 (18) | −0.0023 (12) | 0.0091 (12) | 0.0023 (13) |
C13M | 0.0624 (19) | 0.0450 (15) | 0.0499 (18) | 0.0013 (12) | 0.0069 (13) | 0.0029 (11) |
C14M | 0.054 (2) | 0.0442 (18) | 0.0523 (18) | −0.0007 (14) | 0.0073 (13) | 0.0006 (14) |
C15M | 0.084 (3) | 0.085 (3) | 0.061 (3) | 0.006 (2) | 0.015 (2) | −0.007 (2) |
Geometric parameters (Å, º) top
C1M—C2M | 1.360 (5) | C1D—C11D | 1.394 (17) |
C1M—C11M | 1.427 (5) | C2D—C3D | 1.389 (18) |
C2M—C3M | 1.394 (6) | C3D—C4D | 1.394 (18) |
C3M—C4M | 1.363 (6) | C4D—C12D | 1.411 (17) |
C4M—C12M | 1.415 (4) | C5D—C13D | 1.389 (17) |
C5M—C6M | 1.348 (6) | C5D—C6D | 1.397 (18) |
C5M—C13M | 1.423 (4) | C6D—C7D | 1.371 (18) |
C6M—C7M | 1.399 (5) | C7D—C8D | 1.377 (18) |
C7M—C8M | 1.337 (5) | C8D—C14D | 1.377 (17) |
C8M—C14M | 1.428 (5) | C9D—C14D | 1.498 (16) |
C9M—C11M | 1.401 (4) | C9D—C11D | 1.530 (16) |
C9M—C14M | 1.407 (4) | C9D—C15D | 1.541 (17) |
C9M—C15M | 1.517 (5) | C9D—C10Di | 1.628 (16) |
C10M—C13M | 1.380 (4) | C10D—C12D | 1.493 (16) |
C10M—C12M | 1.382 (4) | C10D—C13D | 1.505 (16) |
C11M—C12M | 1.439 (4) | C10D—C9Di | 1.628 (16) |
C13M—C14M | 1.432 (4) | C11D—C12D | 1.376 (16) |
C1D—C2D | 1.387 (18) | C13D—C14D | 1.419 (16) |
| | | |
C2M—C1M—C11M | 122.2 (3) | C3D—C4D—C12D | 118.5 (19) |
C1M—C2M—C3M | 120.4 (3) | C13D—C5D—C6D | 122.2 (19) |
C4M—C3M—C2M | 120.3 (4) | C7D—C6D—C5D | 117 (2) |
C3M—C4M—C12M | 121.2 (4) | C6D—C7D—C8D | 122 (2) |
C6M—C5M—C13M | 121.2 (3) | C7D—C8D—C14D | 122 (2) |
C5M—C6M—C7M | 120.4 (3) | C14D—C9D—C11D | 108.5 (15) |
C8M—C7M—C6M | 120.8 (4) | C14D—C9D—C15D | 116.7 (19) |
C7M—C8M—C14M | 121.9 (4) | C11D—C9D—C15D | 103.0 (18) |
C11M—C9M—C14M | 120.2 (3) | C14D—C9D—C10Di | 112.2 (15) |
C11M—C9M—C15M | 120.7 (3) | C11D—C9D—C10Di | 110.1 (14) |
C14M—C9M—C15M | 119.0 (3) | C15D—C9D—C10Di | 105.9 (18) |
C13M—C10M—C12M | 122.3 (3) | C12D—C10D—C13D | 109.1 (15) |
C9M—C11M—C1M | 123.3 (3) | C12D—C10D—C9Di | 112.1 (15) |
C9M—C11M—C12M | 120.0 (3) | C13D—C10D—C9Di | 110.2 (15) |
C1M—C11M—C12M | 116.7 (3) | C12D—C11D—C1D | 120.0 (16) |
C10M—C12M—C4M | 122.2 (3) | C12D—C11D—C9D | 119.0 (15) |
C10M—C12M—C11M | 118.6 (3) | C1D—C11D—C9D | 120.8 (16) |
C4M—C12M—C11M | 119.2 (3) | C11D—C12D—C4D | 120.1 (16) |
C10M—C13M—C5M | 121.7 (3) | C11D—C12D—C10D | 116.1 (15) |
C10M—C13M—C14M | 119.7 (3) | C4D—C12D—C10D | 123.8 (17) |
C5M—C13M—C14M | 118.6 (3) | C5D—C13D—C14D | 119.6 (15) |
C9M—C14M—C8M | 123.7 (3) | C5D—C13D—C10D | 121.5 (16) |
C9M—C14M—C13M | 119.2 (3) | C14D—C13D—C10D | 118.7 (14) |
C8M—C14M—C13M | 117.2 (3) | C8D—C14D—C13D | 116.9 (17) |
C2D—C1D—C11D | 121 (2) | C8D—C14D—C9D | 127.7 (17) |
C1D—C2D—C3D | 118 (2) | C13D—C14D—C9D | 114.9 (14) |
C2D—C3D—C4D | 122 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8574 (16) Å | Cell parameters from 500 reflections |
b = 14.556 (3) Å | θ = 4–22° |
c = 8.1209 (15) Å | µ = 0.07 mm−1 |
β = 96.58 (2)° | T = 293 K |
V = 1040.1 (3) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1044 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3414 measured reflections | k = −17→16 |
1942 independent reflections | l = −10→5 |
Refinement top
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)] = 0.095 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.352 | Calculated w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.21 | (Δ/σ)max < 0.001 |
1942 reflections | Δρmax = 0.36 e Å−3 |
198 parameters | Δρmin = −0.19 e Å−3 |
154 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.04 (3) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1021 (5) | 0.4198 (3) | 0.3038 (6) | 0.0763 (12) | 0.849 (6) |
H1M | 1.0496 | 0.4478 | 0.3832 | 0.092* | 0.849 (6) |
C2M | 1.2519 (5) | 0.4027 (3) | 0.3411 (6) | 0.0928 (14) | 0.849 (6) |
H2M | 1.3007 | 0.4196 | 0.4441 | 0.111* | 0.849 (6) |
C3M | 1.3347 (5) | 0.3595 (3) | 0.2256 (8) | 0.0903 (15) | 0.849 (6) |
H3M | 1.4376 | 0.3474 | 0.2528 | 0.108* | 0.849 (6) |
C4M | 1.2652 (4) | 0.3357 (3) | 0.0756 (6) | 0.0752 (12) | 0.849 (6) |
H4M | 1.3214 | 0.3069 | 0.0004 | 0.090* | 0.849 (6) |
C5M | 0.8066 (6) | 0.3188 (2) | −0.3259 (5) | 0.0706 (11) | 0.849 (6) |
H5M | 0.8628 | 0.2930 | −0.4042 | 0.085* | 0.849 (6) |
C6M | 0.6564 (6) | 0.3298 (3) | −0.3640 (5) | 0.0833 (13) | 0.849 (6) |
H6M | 0.6101 | 0.3115 | −0.4673 | 0.100* | 0.849 (6) |
C7M | 0.5695 (6) | 0.3686 (3) | −0.2494 (6) | 0.0826 (13) | 0.849 (6) |
H7M | 0.4650 | 0.3745 | −0.2761 | 0.099* | 0.849 (6) |
C8M | 0.6340 (6) | 0.3974 (4) | −0.1019 (7) | 0.0715 (15) | 0.849 (6) |
H8M | 0.5739 | 0.4254 | −0.0297 | 0.086* | 0.849 (6) |
C9M | 0.8654 (4) | 0.4125 (2) | 0.1046 (4) | 0.0589 (10) | 0.849 (6) |
C10M | 1.0362 (4) | 0.3297 (2) | −0.1255 (4) | 0.0629 (10) | 0.849 (6) |
H10M | 1.0928 | 0.3025 | −0.2019 | 0.076* | 0.849 (6) |
C11M | 1.0207 (4) | 0.3966 (3) | 0.1463 (5) | 0.0578 (10) | 0.849 (6) |
C12M | 1.1079 (4) | 0.3534 (2) | 0.0291 (4) | 0.0589 (10) | 0.849 (6) |
C13M | 0.8823 (4) | 0.3452 (2) | −0.1698 (4) | 0.0586 (10) | 0.849 (6) |
C14M | 0.7933 (4) | 0.3862 (3) | −0.0517 (5) | 0.0554 (10) | 0.849 (6) |
C15M | 0.7706 (6) | 0.4562 (4) | 0.2285 (8) | 0.0811 (16) | 0.849 (6) |
H15A | 0.6674 | 0.4625 | 0.1790 | 0.122* | 0.849 (6) |
H15B | 0.8111 | 0.5157 | 0.2596 | 0.122* | 0.849 (6) |
H15C | 0.7736 | 0.4180 | 0.3252 | 0.122* | 0.849 (6) |
C1D | 1.063 (3) | 0.3957 (19) | 0.364 (3) | 0.111 (10)* | 0.151 (6) |
C2D | 1.201 (3) | 0.3567 (17) | 0.424 (3) | 0.109 (9)* | 0.151 (6) |
C3D | 1.309 (3) | 0.3405 (19) | 0.317 (3) | 0.111 (10)* | 0.151 (6) |
C4D | 1.280 (3) | 0.364 (2) | 0.149 (3) | 0.077 (9)* | 0.151 (6) |
C5D | 0.881 (2) | 0.3525 (16) | −0.289 (3) | 0.078 (7)* | 0.151 (6) |
C6D | 0.730 (3) | 0.330 (2) | −0.334 (4) | 0.112 (17)* | 0.151 (6) |
C7D | 0.628 (3) | 0.352 (3) | −0.224 (4) | 0.122 (15)* | 0.151 (6) |
C8D | 0.675 (3) | 0.394 (2) | −0.074 (3) | 0.061 (9)* | 0.151 (6) |
C9D | 0.8845 (18) | 0.4678 (11) | 0.129 (2) | 0.079 (7)* | 0.151 (6) |
C10D | 1.0911 (17) | 0.4241 (10) | −0.0888 (18) | 0.066 (5)* | 0.151 (6) |
C11D | 1.034 (2) | 0.4218 (15) | 0.199 (2) | 0.064 (8)* | 0.151 (6) |
C12D | 1.135 (2) | 0.4006 (15) | 0.089 (2) | 0.076 (6)* | 0.151 (6) |
C13D | 0.9273 (18) | 0.3968 (15) | −0.141 (2) | 0.084 (7)* | 0.151 (6) |
C14D | 0.824 (2) | 0.4140 (13) | −0.023 (2) | 0.052 (7)* | 0.151 (6) |
C15D | 0.786 (4) | 0.466 (3) | 0.273 (4) | 0.107 (17)* | 0.151 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.085 (3) | 0.072 (2) | 0.070 (3) | −0.0004 (19) | 0.001 (2) | −0.0041 (18) |
C2M | 0.092 (3) | 0.089 (3) | 0.091 (3) | −0.004 (2) | −0.016 (2) | 0.000 (2) |
C3M | 0.065 (3) | 0.098 (3) | 0.104 (4) | −0.002 (2) | −0.008 (3) | 0.005 (3) |
C4M | 0.065 (3) | 0.080 (3) | 0.079 (3) | 0.0016 (17) | 0.0050 (19) | −0.005 (2) |
C5M | 0.089 (3) | 0.059 (2) | 0.063 (2) | 0.004 (2) | 0.007 (2) | −0.0053 (16) |
C6M | 0.096 (4) | 0.074 (2) | 0.074 (3) | 0.003 (2) | −0.015 (2) | −0.0027 (19) |
C7M | 0.073 (3) | 0.080 (3) | 0.092 (3) | 0.003 (2) | −0.005 (2) | 0.004 (2) |
C8M | 0.060 (3) | 0.070 (3) | 0.083 (3) | 0.009 (2) | 0.004 (2) | 0.008 (2) |
C9M | 0.061 (2) | 0.059 (2) | 0.059 (2) | 0.0014 (14) | 0.0158 (15) | 0.0017 (14) |
C10M | 0.068 (2) | 0.0571 (18) | 0.066 (2) | 0.0010 (14) | 0.0193 (16) | −0.0060 (15) |
C11M | 0.067 (3) | 0.0503 (19) | 0.055 (2) | −0.0016 (14) | 0.0056 (16) | 0.0019 (17) |
C12M | 0.0523 (19) | 0.0575 (19) | 0.068 (2) | −0.0042 (13) | 0.0105 (15) | 0.0024 (15) |
C13M | 0.069 (2) | 0.0513 (18) | 0.055 (2) | 0.0005 (14) | 0.0079 (16) | 0.0041 (14) |
C14M | 0.060 (2) | 0.048 (2) | 0.059 (2) | 0.0006 (17) | 0.0091 (15) | −0.0003 (16) |
C15M | 0.087 (3) | 0.090 (3) | 0.069 (3) | 0.005 (2) | 0.018 (2) | −0.009 (2) |
Geometric parameters (Å, º) top
C1M—C2M | 1.351 (6) | C1D—C11D | 1.386 (17) |
C1M—C11M | 1.435 (5) | C2D—C3D | 1.388 (18) |
C2M—C3M | 1.403 (6) | C3D—C4D | 1.396 (18) |
C3M—C4M | 1.346 (7) | C4D—C12D | 1.420 (16) |
C4M—C12M | 1.425 (5) | C5D—C6D | 1.387 (18) |
C5M—C6M | 1.340 (8) | C5D—C13D | 1.389 (16) |
C5M—C13M | 1.417 (5) | C6D—C7D | 1.375 (18) |
C6M—C7M | 1.394 (6) | C7D—C8D | 1.385 (18) |
C7M—C8M | 1.334 (6) | C8D—C14D | 1.373 (17) |
C8M—C14M | 1.432 (6) | C9D—C14D | 1.507 (15) |
C9M—C11M | 1.398 (4) | C9D—C11D | 1.536 (15) |
C9M—C14M | 1.407 (5) | C9D—C15D | 1.538 (17) |
C9M—C15M | 1.522 (5) | C9D—C10Di | 1.627 (16) |
C10M—C12M | 1.384 (5) | C10D—C12D | 1.493 (15) |
C10M—C13M | 1.388 (4) | C10D—C13D | 1.516 (15) |
C11M—C12M | 1.437 (5) | C10D—C9Di | 1.627 (16) |
C13M—C14M | 1.439 (5) | C11D—C12D | 1.372 (16) |
C1D—C2D | 1.381 (17) | C13D—C14D | 1.416 (16) |
| | | |
C2M—C1M—C11M | 122.4 (4) | C3D—C4D—C12D | 119.0 (17) |
C1M—C2M—C3M | 120.5 (4) | C6D—C5D—C13D | 120.9 (18) |
C4M—C3M—C2M | 120.1 (4) | C7D—C6D—C5D | 118 (2) |
C3M—C4M—C12M | 121.7 (4) | C6D—C7D—C8D | 121 (2) |
C6M—C5M—C13M | 122.0 (4) | C14D—C8D—C7D | 123 (2) |
C5M—C6M—C7M | 120.3 (4) | C14D—C9D—C11D | 106.7 (14) |
C8M—C7M—C6M | 120.9 (5) | C14D—C9D—C15D | 115.8 (18) |
C7M—C8M—C14M | 121.8 (5) | C11D—C9D—C15D | 104.4 (18) |
C11M—C9M—C14M | 120.4 (3) | C14D—C9D—C10Di | 112.4 (13) |
C11M—C9M—C15M | 120.7 (4) | C11D—C9D—C10Di | 111.6 (13) |
C14M—C9M—C15M | 118.9 (4) | C15D—C9D—C10Di | 105.8 (17) |
C12M—C10M—C13M | 122.0 (3) | C12D—C10D—C13D | 110.3 (13) |
C9M—C11M—C1M | 123.8 (4) | C12D—C10D—C9Di | 112.9 (13) |
C9M—C11M—C12M | 120.1 (3) | C13D—C10D—C9Di | 110.0 (13) |
C1M—C11M—C12M | 116.1 (3) | C12D—C11D—C1D | 120.3 (15) |
C10M—C12M—C4M | 121.9 (3) | C12D—C11D—C9D | 117.2 (14) |
C10M—C12M—C11M | 118.9 (3) | C1D—C11D—C9D | 122.4 (15) |
C4M—C12M—C11M | 119.1 (4) | C11D—C12D—C4D | 119.4 (14) |
C10M—C13M—C5M | 122.5 (3) | C11D—C12D—C10D | 117.4 (13) |
C10M—C13M—C14M | 119.4 (3) | C4D—C12D—C10D | 123.1 (15) |
C5M—C13M—C14M | 118.0 (3) | C5D—C13D—C14D | 121.4 (14) |
C9M—C14M—C8M | 123.8 (3) | C5D—C13D—C10D | 122.6 (14) |
C9M—C14M—C13M | 119.2 (3) | C14D—C13D—C10D | 115.9 (13) |
C8M—C14M—C13M | 117.0 (4) | C8D—C14D—C13D | 115.6 (16) |
C2D—C1D—C11D | 120.8 (19) | C8D—C14D—C9D | 126.6 (15) |
C1D—C2D—C3D | 119.5 (19) | C13D—C14D—C9D | 116.7 (13) |
C2D—C3D—C4D | 120.4 (19) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8470 (16) Å | Cell parameters from 500 reflections |
b = 14.539 (3) Å | θ = 4–22° |
c = 8.1361 (16) Å | µ = 0.07 mm−1 |
β = 96.67 (2)° | T = 293 K |
V = 1039.4 (4) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 1027 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 26.0°, θmin = 4.6° |
ω scans | h = −10→10 |
3380 measured reflections | k = −17→16 |
1947 independent reflections | l = −10→5 |
Refinement top
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)] = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.375 | Calculated w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.27 | (Δ/σ)max = 0.002 |
1947 reflections | Δρmax = 0.35 e Å−3 |
198 parameters | Δρmin = −0.20 e Å−3 |
148 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.03 (3) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1023 (5) | 0.4193 (3) | 0.3043 (6) | 0.0779 (13) | 0.821 (6) |
H1M | 1.0492 | 0.4464 | 0.3838 | 0.093* | 0.821 (6) |
C2M | 1.2519 (6) | 0.4028 (3) | 0.3419 (7) | 0.0956 (16) | 0.821 (6) |
H2M | 1.3004 | 0.4200 | 0.4449 | 0.115* | 0.821 (6) |
C3M | 1.3358 (5) | 0.3597 (4) | 0.2264 (9) | 0.0936 (17) | 0.821 (6) |
H3M | 1.4390 | 0.3481 | 0.2538 | 0.112* | 0.821 (6) |
C4M | 1.2665 (5) | 0.3353 (3) | 0.0764 (7) | 0.0798 (13) | 0.821 (6) |
H4M | 1.3226 | 0.3060 | 0.0020 | 0.096* | 0.821 (6) |
C5M | 0.8077 (7) | 0.3191 (3) | −0.3259 (5) | 0.0729 (13) | 0.821 (6) |
H5M | 0.8643 | 0.2943 | −0.4046 | 0.087* | 0.821 (6) |
C6M | 0.6565 (7) | 0.3294 (3) | −0.3631 (6) | 0.0853 (15) | 0.821 (6) |
H6M | 0.6099 | 0.3101 | −0.4657 | 0.102* | 0.821 (6) |
C7M | 0.5688 (7) | 0.3688 (3) | −0.2499 (7) | 0.0839 (15) | 0.821 (6) |
H7M | 0.4643 | 0.3750 | −0.2775 | 0.101* | 0.821 (6) |
C8M | 0.6338 (8) | 0.3978 (4) | −0.1012 (8) | 0.0744 (18) | 0.821 (6) |
H8M | 0.5739 | 0.4260 | −0.0292 | 0.089* | 0.821 (6) |
C9M | 0.8655 (4) | 0.4124 (3) | 0.1037 (5) | 0.0623 (11) | 0.821 (6) |
C10M | 1.0361 (4) | 0.3295 (2) | −0.1253 (4) | 0.0645 (11) | 0.821 (6) |
H10M | 1.0928 | 0.3021 | −0.2014 | 0.077* | 0.821 (6) |
C11M | 1.0214 (4) | 0.3966 (3) | 0.1464 (6) | 0.0596 (11) | 0.821 (6) |
C12M | 1.1079 (4) | 0.3536 (3) | 0.0291 (5) | 0.0624 (11) | 0.821 (6) |
C13M | 0.8828 (4) | 0.3450 (2) | −0.1692 (5) | 0.0610 (11) | 0.821 (6) |
C14M | 0.7933 (5) | 0.3862 (3) | −0.0514 (5) | 0.0581 (11) | 0.821 (6) |
C15M | 0.7739 (10) | 0.4557 (7) | 0.2310 (11) | 0.090 (3) | 0.821 (6) |
H15A | 0.6699 | 0.4626 | 0.1840 | 0.135* | 0.821 (6) |
H15B | 0.8157 | 0.5149 | 0.2626 | 0.135* | 0.821 (6) |
H15C | 0.7784 | 0.4168 | 0.3268 | 0.135* | 0.821 (6) |
C1D | 1.058 (3) | 0.3936 (18) | 0.362 (3) | 0.120 (11)* | 0.179 (6) |
C2D | 1.198 (2) | 0.3563 (16) | 0.422 (3) | 0.108 (8)* | 0.179 (6) |
C3D | 1.309 (3) | 0.3431 (18) | 0.316 (3) | 0.118 (10)* | 0.179 (6) |
C4D | 1.283 (2) | 0.3650 (15) | 0.149 (3) | 0.064 (6)* | 0.179 (6) |
C5D | 0.889 (2) | 0.3530 (16) | −0.290 (2) | 0.092 (7)* | 0.179 (6) |
C6D | 0.736 (3) | 0.329 (2) | −0.335 (4) | 0.113 (16)* | 0.179 (6) |
C7D | 0.631 (3) | 0.349 (2) | −0.229 (3) | 0.111 (11)* | 0.179 (6) |
C8D | 0.674 (3) | 0.391 (2) | −0.078 (3) | 0.075 (11)* | 0.179 (6) |
C9D | 0.8829 (17) | 0.4676 (10) | 0.1253 (18) | 0.076 (6)* | 0.179 (6) |
C10D | 1.0927 (16) | 0.4240 (9) | −0.0861 (17) | 0.068 (5)* | 0.179 (6) |
C11D | 1.030 (2) | 0.4225 (16) | 0.199 (2) | 0.083 (9)* | 0.179 (6) |
C12D | 1.136 (2) | 0.4013 (15) | 0.092 (2) | 0.085 (7)* | 0.179 (6) |
C13D | 0.9305 (17) | 0.3974 (14) | −0.141 (2) | 0.083 (6)* | 0.179 (6) |
C14D | 0.8219 (19) | 0.4167 (13) | −0.032 (2) | 0.060 (7)* | 0.179 (6) |
C15D | 0.760 (4) | 0.466 (3) | 0.244 (5) | 0.104 (15)* | 0.179 (6) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.081 (3) | 0.075 (3) | 0.076 (3) | 0.000 (2) | 0.003 (2) | −0.004 (2) |
C2M | 0.099 (4) | 0.089 (3) | 0.093 (4) | −0.003 (3) | −0.011 (3) | −0.003 (3) |
C3M | 0.067 (3) | 0.104 (4) | 0.104 (5) | −0.003 (2) | −0.013 (3) | 0.008 (3) |
C4M | 0.070 (3) | 0.080 (3) | 0.088 (3) | −0.001 (2) | 0.004 (2) | −0.008 (3) |
C5M | 0.089 (4) | 0.064 (3) | 0.065 (3) | 0.004 (2) | 0.009 (2) | −0.0047 (18) |
C6M | 0.100 (4) | 0.077 (3) | 0.074 (3) | 0.002 (2) | −0.013 (3) | −0.002 (2) |
C7M | 0.068 (3) | 0.080 (3) | 0.101 (4) | 0.005 (2) | 0.001 (3) | 0.008 (2) |
C8M | 0.065 (3) | 0.072 (3) | 0.085 (4) | 0.013 (3) | 0.004 (3) | 0.009 (2) |
C9M | 0.063 (2) | 0.058 (2) | 0.069 (3) | 0.0003 (16) | 0.0201 (18) | 0.0022 (16) |
C10M | 0.071 (3) | 0.060 (2) | 0.065 (2) | 0.0005 (16) | 0.0185 (18) | −0.0057 (16) |
C11M | 0.068 (3) | 0.054 (2) | 0.058 (2) | −0.0022 (16) | 0.0083 (18) | 0.0026 (19) |
C12M | 0.055 (2) | 0.060 (2) | 0.073 (3) | −0.0020 (15) | 0.0118 (17) | 0.0049 (18) |
C13M | 0.069 (2) | 0.053 (2) | 0.062 (2) | 0.0010 (16) | 0.0099 (18) | 0.0066 (15) |
C14M | 0.064 (3) | 0.048 (2) | 0.063 (2) | −0.0006 (19) | 0.0103 (17) | −0.0004 (17) |
C15M | 0.096 (4) | 0.093 (4) | 0.086 (4) | 0.011 (3) | 0.027 (3) | −0.005 (3) |
Geometric parameters (Å, º) top
C1M—C2M | 1.345 (6) | C1D—C2D | 1.386 (17) |
C1M—C11M | 1.434 (6) | C2D—C3D | 1.399 (17) |
C2M—C3M | 1.410 (7) | C3D—C4D | 1.391 (17) |
C3M—C4M | 1.348 (7) | C4D—C12D | 1.433 (16) |
C4M—C12M | 1.436 (5) | C5D—C13D | 1.385 (16) |
C5M—C6M | 1.346 (8) | C5D—C6D | 1.401 (18) |
C5M—C13M | 1.419 (6) | C6D—C7D | 1.372 (18) |
C6M—C7M | 1.394 (6) | C7D—C8D | 1.381 (18) |
C7M—C8M | 1.346 (7) | C8D—C14D | 1.373 (17) |
C8M—C14M | 1.432 (7) | C9D—C11D | 1.519 (15) |
C9M—C14M | 1.399 (6) | C9D—C14D | 1.520 (15) |
C9M—C11M | 1.402 (5) | C9D—C15D | 1.535 (17) |
C9M—C15M | 1.524 (7) | C9D—C10Di | 1.627 (15) |
C10M—C13M | 1.381 (5) | C10D—C12D | 1.492 (15) |
C10M—C12M | 1.385 (5) | C10D—C13D | 1.503 (15) |
C11M—C12M | 1.434 (6) | C10D—C9Di | 1.627 (15) |
C13M—C14M | 1.442 (5) | C11D—C12D | 1.381 (16) |
C1D—C11D | 1.384 (17) | C13D—C14D | 1.408 (15) |
| | | |
C2M—C1M—C11M | 122.6 (4) | C3D—C4D—C12D | 116.1 (15) |
C1M—C2M—C3M | 120.5 (5) | C13D—C5D—C6D | 119.8 (17) |
C4M—C3M—C2M | 120.1 (5) | C7D—C6D—C5D | 119 (2) |
C3M—C4M—C12M | 121.4 (5) | C6D—C7D—C8D | 121 (2) |
C6M—C5M—C13M | 121.5 (4) | C14D—C8D—C7D | 121 (2) |
C5M—C6M—C7M | 120.8 (4) | C11D—C9D—C14D | 109.0 (14) |
C8M—C7M—C6M | 120.7 (5) | C11D—C9D—C15D | 112 (2) |
C7M—C8M—C14M | 121.4 (5) | C14D—C9D—C15D | 108 (2) |
C14M—C9M—C11M | 120.8 (3) | C11D—C9D—C10Di | 111.6 (13) |
C14M—C9M—C15M | 120.2 (5) | C14D—C9D—C10Di | 110.4 (12) |
C11M—C9M—C15M | 119.0 (5) | C15D—C9D—C10Di | 105.2 (19) |
C13M—C10M—C12M | 121.7 (3) | C12D—C10D—C13D | 110.8 (12) |
C9M—C11M—C12M | 119.5 (4) | C12D—C10D—C9Di | 112.3 (12) |
C9M—C11M—C1M | 124.0 (4) | C13D—C10D—C9Di | 109.6 (12) |
C12M—C11M—C1M | 116.6 (3) | C12D—C11D—C1D | 118.5 (15) |
C10M—C12M—C11M | 119.4 (3) | C12D—C11D—C9D | 117.3 (14) |
C10M—C12M—C4M | 121.8 (4) | C1D—C11D—C9D | 123.9 (15) |
C11M—C12M—C4M | 118.8 (4) | C11D—C12D—C4D | 122.4 (14) |
C10M—C13M—C5M | 122.2 (4) | C11D—C12D—C10D | 116.7 (13) |
C10M—C13M—C14M | 119.7 (3) | C4D—C12D—C10D | 120.9 (14) |
C5M—C13M—C14M | 118.2 (4) | C5D—C13D—C14D | 120.7 (14) |
C9M—C14M—C8M | 123.7 (4) | C5D—C13D—C10D | 121.7 (14) |
C9M—C14M—C13M | 118.9 (4) | C14D—C13D—C10D | 117.5 (13) |
C8M—C14M—C13M | 117.4 (4) | C8D—C14D—C13D | 118.2 (15) |
C11D—C1D—C2D | 120.8 (18) | C8D—C14D—C9D | 126.7 (15) |
C1D—C2D—C3D | 119.7 (18) | C13D—C14D—C9D | 115.1 (13) |
C4D—C3D—C2D | 121.8 (18) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.230 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8359 (17) Å | Cell parameters from 500 reflections |
b = 14.519 (3) Å | θ = 4–22° |
c = 8.1512 (19) Å | µ = 0.07 mm−1 |
β = 96.74 (2)° | T = 293 K |
V = 1038.5 (4) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 953 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 25.0°, θmin = 4.3° |
ω scans | h = −10→10 |
3122 measured reflections | k = −17→16 |
1752 independent reflections | l = −9→4 |
Refinement top
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)] = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.385 | Calculated w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.34 | (Δ/σ)max < 0.001 |
1752 reflections | Δρmax = 0.38 e Å−3 |
198 parameters | Δρmin = −0.20 e Å−3 |
166 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.07 (4) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1026 (7) | 0.4203 (4) | 0.3034 (8) | 0.0803 (16) | 0.765 (7) |
H1M | 1.0498 | 0.4490 | 0.3814 | 0.096* | 0.765 (7) |
C2M | 1.2529 (7) | 0.4029 (4) | 0.3422 (8) | 0.0952 (18) | 0.765 (7) |
H2M | 1.3014 | 0.4194 | 0.4455 | 0.114* | 0.765 (7) |
C3M | 1.3359 (6) | 0.3600 (5) | 0.2269 (10) | 0.095 (2) | 0.765 (7) |
H3M | 1.4393 | 0.3483 | 0.2537 | 0.115* | 0.765 (7) |
C4M | 1.2654 (6) | 0.3355 (4) | 0.0765 (9) | 0.0822 (16) | 0.765 (7) |
H4M | 1.3214 | 0.3059 | 0.0023 | 0.099* | 0.765 (7) |
C5M | 0.8085 (8) | 0.3190 (3) | −0.3253 (6) | 0.0713 (14) | 0.765 (7) |
H5M | 0.8649 | 0.2935 | −0.4033 | 0.086* | 0.765 (7) |
C6M | 0.6563 (8) | 0.3305 (4) | −0.3628 (7) | 0.0868 (17) | 0.765 (7) |
H6M | 0.6096 | 0.3118 | −0.4655 | 0.104* | 0.765 (7) |
C7M | 0.5692 (7) | 0.3697 (4) | −0.2507 (8) | 0.0840 (17) | 0.765 (7) |
H7M | 0.4647 | 0.3764 | −0.2784 | 0.101* | 0.765 (7) |
C8M | 0.6346 (9) | 0.3981 (5) | −0.1022 (9) | 0.076 (2) | 0.765 (7) |
H8M | 0.5747 | 0.4265 | −0.0305 | 0.091* | 0.765 (7) |
C9M | 0.8658 (5) | 0.4122 (3) | 0.1042 (5) | 0.0619 (13) | 0.765 (7) |
C10M | 1.0361 (5) | 0.3300 (3) | −0.1239 (5) | 0.0655 (13) | 0.765 (7) |
H10M | 1.0929 | 0.3027 | −0.1998 | 0.079* | 0.765 (7) |
C11M | 1.0213 (5) | 0.3960 (4) | 0.1458 (7) | 0.0613 (14) | 0.765 (7) |
C12M | 1.1090 (5) | 0.3536 (3) | 0.0293 (6) | 0.0621 (13) | 0.765 (7) |
C13M | 0.8827 (5) | 0.3450 (3) | −0.1696 (6) | 0.0616 (13) | 0.765 (7) |
C14M | 0.7931 (5) | 0.3859 (4) | −0.0516 (6) | 0.0576 (13) | 0.765 (7) |
C15M | 0.7763 (11) | 0.4536 (7) | 0.2329 (13) | 0.097 (3) | 0.765 (7) |
H15A | 0.6718 | 0.4610 | 0.1873 | 0.145* | 0.765 (7) |
H15B | 0.8184 | 0.5126 | 0.2661 | 0.145* | 0.765 (7) |
H15C | 0.7818 | 0.4136 | 0.3272 | 0.145* | 0.765 (7) |
C1D | 1.061 (2) | 0.3978 (14) | 0.359 (2) | 0.107 (8)* | 0.235 (7) |
H1D | 0.9878 | 0.4080 | 0.4308 | 0.129* | 0.235 (7) |
C2D | 1.199 (2) | 0.3601 (15) | 0.421 (3) | 0.129 (8)* | 0.235 (7) |
H2D | 1.2195 | 0.3461 | 0.5331 | 0.155* | 0.235 (7) |
C3D | 1.305 (3) | 0.3435 (16) | 0.314 (3) | 0.126 (10)* | 0.235 (7) |
H3D | 1.3987 | 0.3180 | 0.3561 | 0.152* | 0.235 (7) |
C4D | 1.279 (2) | 0.3633 (17) | 0.146 (3) | 0.092 (8)* | 0.235 (7) |
H4D | 1.3527 | 0.3532 | 0.0753 | 0.110* | 0.235 (7) |
C5D | 0.884 (2) | 0.3492 (14) | −0.289 (2) | 0.095 (7)* | 0.235 (7) |
H5D | 0.9553 | 0.3345 | −0.3594 | 0.114* | 0.235 (7) |
C6D | 0.733 (3) | 0.3238 (16) | −0.331 (3) | 0.104 (12)* | 0.235 (7) |
H6D | 0.7030 | 0.2928 | −0.4293 | 0.125* | 0.235 (7) |
C7D | 0.629 (3) | 0.3454 (16) | −0.225 (3) | 0.101 (8)* | 0.235 (7) |
H7D | 0.5273 | 0.3301 | −0.2536 | 0.122* | 0.235 (7) |
C8D | 0.672 (3) | 0.389 (2) | −0.077 (3) | 0.096 (13)* | 0.235 (7) |
H8D | 0.5994 | 0.4003 | −0.0049 | 0.116* | 0.235 (7) |
C9D | 0.8816 (16) | 0.4674 (10) | 0.1210 (18) | 0.091 (5)* | 0.235 (7) |
C10D | 1.0929 (15) | 0.4244 (9) | −0.0869 (17) | 0.083 (5)* | 0.235 (7) |
H10D | 1.1599 | 0.3895 | −0.1518 | 0.100* | 0.235 (7) |
C11D | 1.0267 (19) | 0.4211 (14) | 0.194 (2) | 0.083 (8)* | 0.235 (7) |
C12D | 1.1336 (19) | 0.3999 (14) | 0.0890 (19) | 0.094 (6)* | 0.235 (7) |
C13D | 0.9293 (16) | 0.3957 (13) | −0.1438 (19) | 0.089 (6)* | 0.235 (7) |
C14D | 0.8203 (19) | 0.4165 (13) | −0.033 (2) | 0.073 (7)* | 0.235 (7) |
C15D | 0.752 (3) | 0.469 (2) | 0.233 (4) | 0.076 (9)* | 0.235 (7) |
H15D | 0.7305 | 0.4076 | 0.2654 | 0.114* | 0.235 (7) |
H15E | 0.6626 | 0.4958 | 0.1732 | 0.114* | 0.235 (7) |
H15F | 0.7833 | 0.5057 | 0.3292 | 0.114* | 0.235 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.088 (4) | 0.075 (3) | 0.077 (4) | −0.002 (3) | 0.009 (3) | 0.000 (2) |
C2M | 0.093 (4) | 0.088 (4) | 0.098 (4) | 0.000 (3) | −0.015 (3) | −0.003 (3) |
C3M | 0.067 (3) | 0.100 (4) | 0.113 (6) | −0.004 (3) | −0.012 (4) | 0.008 (4) |
C4M | 0.072 (4) | 0.080 (3) | 0.094 (4) | 0.001 (2) | 0.006 (3) | −0.007 (3) |
C5M | 0.074 (4) | 0.070 (3) | 0.069 (3) | 0.001 (3) | 0.004 (2) | −0.013 (2) |
C6M | 0.101 (5) | 0.075 (3) | 0.078 (4) | 0.006 (3) | −0.013 (3) | −0.003 (3) |
C7M | 0.068 (3) | 0.077 (3) | 0.104 (4) | 0.013 (3) | −0.003 (3) | 0.005 (3) |
C8M | 0.068 (3) | 0.075 (4) | 0.083 (4) | 0.016 (3) | 0.006 (3) | 0.010 (3) |
C9M | 0.063 (3) | 0.059 (3) | 0.066 (3) | 0.0007 (19) | 0.016 (2) | 0.0018 (19) |
C10M | 0.073 (3) | 0.059 (2) | 0.066 (3) | 0.0042 (19) | 0.020 (2) | −0.0047 (19) |
C11M | 0.066 (3) | 0.055 (3) | 0.061 (3) | −0.0037 (19) | 0.003 (2) | −0.001 (2) |
C12M | 0.053 (3) | 0.059 (2) | 0.075 (3) | −0.0029 (17) | 0.0093 (19) | −0.001 (2) |
C13M | 0.066 (3) | 0.051 (2) | 0.068 (3) | 0.0035 (19) | 0.011 (2) | 0.0074 (18) |
C14M | 0.064 (3) | 0.047 (3) | 0.063 (3) | −0.004 (2) | 0.011 (2) | −0.001 (2) |
C15M | 0.093 (5) | 0.093 (5) | 0.108 (6) | 0.025 (4) | 0.029 (4) | −0.002 (3) |
Geometric parameters (Å, º) top
C1M—C2M | 1.352 (7) | C1D—C11D | 1.385 (16) |
C1M—C11M | 1.440 (7) | C2D—C3D | 1.378 (17) |
C2M—C3M | 1.404 (8) | C3D—C4D | 1.395 (17) |
C3M—C4M | 1.355 (9) | C4D—C12D | 1.419 (16) |
C4M—C12M | 1.415 (6) | C5D—C13D | 1.380 (16) |
C5M—C6M | 1.354 (9) | C5D—C6D | 1.385 (17) |
C5M—C13M | 1.410 (7) | C6D—C7D | 1.369 (17) |
C6M—C7M | 1.384 (7) | C7D—C8D | 1.378 (17) |
C7M—C8M | 1.343 (8) | C8D—C14D | 1.376 (17) |
C8M—C14M | 1.424 (9) | C9D—C14D | 1.505 (15) |
C9M—C11M | 1.397 (6) | C9D—C11D | 1.508 (15) |
C9M—C14M | 1.407 (7) | C9D—C15D | 1.542 (16) |
C9M—C15M | 1.511 (8) | C9D—C10Di | 1.616 (15) |
C10M—C12M | 1.380 (6) | C10D—C12D | 1.480 (14) |
C10M—C13M | 1.380 (6) | C10D—C13D | 1.524 (14) |
C11M—C12M | 1.433 (7) | C10D—C9Di | 1.616 (15) |
C13M—C14M | 1.443 (6) | C11D—C12D | 1.383 (15) |
C1D—C2D | 1.378 (17) | C13D—C14D | 1.424 (15) |
| | | |
C2M—C1M—C11M | 122.4 (5) | C3D—C4D—C12D | 116.1 (16) |
C1M—C2M—C3M | 120.1 (5) | C13D—C5D—C6D | 121.3 (17) |
C4M—C3M—C2M | 120.1 (5) | C7D—C6D—C5D | 118.5 (19) |
C3M—C4M—C12M | 121.8 (5) | C6D—C7D—C8D | 121.7 (19) |
C6M—C5M—C13M | 121.0 (5) | C14D—C8D—C7D | 120.7 (19) |
C5M—C6M—C7M | 121.1 (5) | C14D—C9D—C11D | 108.6 (13) |
C8M—C7M—C6M | 120.5 (6) | C14D—C9D—C15D | 106.5 (15) |
C7M—C8M—C14M | 121.9 (6) | C11D—C9D—C15D | 115.4 (16) |
C11M—C9M—C14M | 120.3 (4) | C14D—C9D—C10Di | 112.1 (12) |
C11M—C9M—C15M | 118.6 (6) | C11D—C9D—C10Di | 111.9 (12) |
C14M—C9M—C15M | 121.0 (6) | C15D—C9D—C10Di | 102.2 (14) |
C12M—C10M—C13M | 123.0 (4) | C12D—C10D—C13D | 110.0 (12) |
C9M—C11M—C12M | 120.3 (5) | C12D—C10D—C9Di | 112.2 (12) |
C9M—C11M—C1M | 123.3 (5) | C13D—C10D—C9Di | 111.1 (12) |
C12M—C11M—C1M | 116.4 (4) | C12D—C11D—C1D | 117.5 (14) |
C10M—C12M—C4M | 122.5 (4) | C12D—C11D—C9D | 117.6 (13) |
C10M—C12M—C11M | 118.4 (4) | C1D—C11D—C9D | 124.9 (14) |
C4M—C12M—C11M | 119.1 (5) | C11D—C12D—C4D | 122.6 (14) |
C10M—C13M—C5M | 122.6 (4) | C11D—C12D—C10D | 116.3 (13) |
C10M—C13M—C14M | 118.9 (4) | C4D—C12D—C10D | 121.0 (14) |
C5M—C13M—C14M | 118.5 (4) | C5D—C13D—C14D | 119.5 (13) |
C9M—C14M—C8M | 123.9 (4) | C5D—C13D—C10D | 124.5 (13) |
C9M—C14M—C13M | 119.1 (4) | C14D—C13D—C10D | 116.0 (12) |
C8M—C14M—C13M | 117.1 (5) | C8D—C14D—C13D | 118.2 (15) |
C2D—C1D—C11D | 122.4 (17) | C8D—C14D—C9D | 126.4 (14) |
C1D—C2D—C3D | 118.6 (18) | C13D—C14D—C9D | 115.4 (12) |
C2D—C3D—C4D | 122.6 (19) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.830 (2) Å | Cell parameters from 500 reflections |
b = 14.486 (4) Å | θ = 4–22° |
c = 8.169 (2) Å | µ = 0.07 mm−1 |
β = 96.75 (3)° | T = 293 K |
V = 1037.7 (4) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 896 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.056 |
Graphite monochromator | θmax = 25.0°, θmin = 4.3° |
ω scans | h = −9→10 |
3104 measured reflections | k = −17→16 |
1750 independent reflections | l = −9→4 |
Refinement top
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)] = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.425 | Calculated w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.42 | (Δ/σ)max < 0.001 |
1750 reflections | Δρmax = 0.37 e Å−3 |
198 parameters | Δρmin = −0.21 e Å−3 |
142 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.14 (7) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1030 (7) | 0.4198 (4) | 0.3043 (9) | 0.0836 (18) | 0.744 (8) |
H1M | 1.0496 | 0.4478 | 0.3826 | 0.100* | 0.744 (8) |
C2M | 1.2554 (8) | 0.4026 (5) | 0.3442 (9) | 0.101 (2) | 0.744 (8) |
H2M | 1.3044 | 0.4193 | 0.4469 | 0.122* | 0.744 (8) |
C3M | 1.3367 (8) | 0.3592 (5) | 0.2279 (12) | 0.106 (2) | 0.744 (8) |
H3M | 1.4399 | 0.3465 | 0.2541 | 0.127* | 0.744 (8) |
C4M | 1.2652 (7) | 0.3359 (4) | 0.0778 (10) | 0.089 (2) | 0.744 (8) |
H4M | 1.3211 | 0.3071 | 0.0028 | 0.107* | 0.744 (8) |
C5M | 0.8111 (10) | 0.3192 (4) | −0.3233 (8) | 0.0812 (19) | 0.744 (8) |
H5M | 0.8684 | 0.2943 | −0.4012 | 0.097* | 0.744 (8) |
C6M | 0.6577 (9) | 0.3299 (4) | −0.3620 (8) | 0.092 (2) | 0.744 (8) |
H6M | 0.6110 | 0.3108 | −0.4643 | 0.110* | 0.744 (8) |
C7M | 0.5707 (9) | 0.3694 (5) | −0.2492 (10) | 0.095 (2) | 0.744 (8) |
H7M | 0.4660 | 0.3758 | −0.2767 | 0.113* | 0.744 (8) |
C8M | 0.6349 (10) | 0.3982 (6) | −0.1023 (11) | 0.080 (3) | 0.744 (8) |
H8M | 0.5751 | 0.4272 | −0.0312 | 0.096* | 0.744 (8) |
C9M | 0.8657 (5) | 0.4122 (4) | 0.1037 (7) | 0.0683 (16) | 0.744 (8) |
C10M | 1.0372 (6) | 0.3298 (3) | −0.1227 (6) | 0.0735 (17) | 0.744 (8) |
H10M | 1.0942 | 0.3025 | −0.1984 | 0.088* | 0.744 (8) |
C11M | 1.0225 (6) | 0.3967 (4) | 0.1474 (8) | 0.0647 (16) | 0.744 (8) |
C12M | 1.1102 (5) | 0.3535 (4) | 0.0315 (7) | 0.0670 (15) | 0.744 (8) |
C13M | 0.8841 (6) | 0.3448 (3) | −0.1683 (6) | 0.0669 (15) | 0.744 (8) |
C14M | 0.7939 (7) | 0.3854 (5) | −0.0519 (7) | 0.0649 (17) | 0.744 (8) |
C15M | 0.7718 (14) | 0.4561 (9) | 0.2286 (16) | 0.094 (4) | 0.744 (8) |
H15A | 0.6680 | 0.4628 | 0.1800 | 0.141* | 0.744 (8) |
H15B | 0.8130 | 0.5157 | 0.2598 | 0.141* | 0.744 (8) |
H15C | 0.7753 | 0.4174 | 0.3244 | 0.141* | 0.744 (8) |
C1D | 1.063 (2) | 0.3990 (15) | 0.364 (2) | 0.114 (9)* | 0.256 (8) |
H1D | 0.9911 | 0.4106 | 0.4365 | 0.137* | 0.256 (8) |
C2D | 1.202 (2) | 0.3607 (16) | 0.422 (3) | 0.140 (9)* | 0.256 (8) |
H2D | 1.2240 | 0.3456 | 0.5333 | 0.168* | 0.256 (8) |
C3D | 1.308 (3) | 0.3451 (17) | 0.316 (3) | 0.128 (10)* | 0.256 (8) |
H3D | 1.4016 | 0.3197 | 0.3572 | 0.154* | 0.256 (8) |
C4D | 1.282 (2) | 0.3656 (18) | 0.148 (3) | 0.096 (9)* | 0.256 (8) |
H4D | 1.3552 | 0.3553 | 0.0775 | 0.115* | 0.256 (8) |
C5D | 0.887 (2) | 0.3482 (15) | −0.287 (2) | 0.107 (8)* | 0.256 (8) |
H5D | 0.9604 | 0.3338 | −0.3558 | 0.128* | 0.256 (8) |
C6D | 0.738 (3) | 0.3229 (17) | −0.332 (3) | 0.105 (11)* | 0.256 (8) |
H6D | 0.7092 | 0.2917 | −0.4304 | 0.126* | 0.256 (8) |
C7D | 0.632 (3) | 0.3451 (18) | −0.228 (3) | 0.116 (10)* | 0.256 (8) |
H7D | 0.5299 | 0.3292 | −0.2573 | 0.140* | 0.256 (8) |
C8D | 0.673 (3) | 0.391 (2) | −0.080 (4) | 0.102 (14)* | 0.256 (8) |
H8D | 0.5984 | 0.4040 | −0.0121 | 0.122* | 0.256 (8) |
C9D | 0.8815 (17) | 0.4671 (10) | 0.1247 (18) | 0.093 (6)* | 0.256 (8) |
C10D | 1.0932 (16) | 0.4253 (9) | −0.0860 (17) | 0.089 (5)* | 0.256 (8) |
H10D | 1.1601 | 0.3897 | −0.1499 | 0.107* | 0.256 (8) |
C11D | 1.028 (2) | 0.4204 (16) | 0.198 (2) | 0.102 (11)* | 0.256 (8) |
C12D | 1.137 (2) | 0.4029 (14) | 0.0918 (19) | 0.099 (7)* | 0.256 (8) |
C13D | 0.9309 (17) | 0.3946 (13) | −0.1402 (19) | 0.094 (6)* | 0.256 (8) |
C14D | 0.8217 (19) | 0.4168 (13) | −0.032 (2) | 0.074 (7)* | 0.256 (8) |
C15D | 0.761 (5) | 0.461 (3) | 0.245 (5) | 0.123 (19)* | 0.256 (8) |
H15D | 0.7458 | 0.3977 | 0.2737 | 0.184* | 0.256 (8) |
H15E | 0.6662 | 0.4864 | 0.1945 | 0.184* | 0.256 (8) |
H15F | 0.7945 | 0.4954 | 0.3434 | 0.184* | 0.256 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.089 (4) | 0.079 (4) | 0.082 (4) | 0.002 (3) | 0.012 (4) | 0.000 (3) |
C2M | 0.103 (5) | 0.096 (4) | 0.100 (5) | 0.008 (4) | −0.006 (4) | 0.001 (4) |
C3M | 0.083 (5) | 0.105 (5) | 0.124 (7) | 0.000 (4) | −0.009 (5) | 0.019 (5) |
C4M | 0.076 (4) | 0.082 (4) | 0.108 (5) | −0.004 (3) | 0.004 (3) | −0.015 (4) |
C5M | 0.083 (5) | 0.078 (4) | 0.082 (4) | 0.008 (4) | 0.009 (3) | −0.008 (3) |
C6M | 0.099 (5) | 0.083 (4) | 0.087 (4) | 0.011 (3) | −0.015 (4) | −0.005 (3) |
C7M | 0.071 (4) | 0.081 (4) | 0.131 (6) | 0.013 (3) | 0.004 (4) | 0.008 (4) |
C8M | 0.061 (4) | 0.079 (4) | 0.098 (6) | 0.016 (4) | 0.005 (4) | 0.009 (4) |
C9M | 0.063 (3) | 0.068 (3) | 0.077 (4) | 0.001 (2) | 0.022 (2) | 0.001 (2) |
C10M | 0.083 (4) | 0.065 (3) | 0.077 (4) | 0.001 (2) | 0.025 (3) | −0.009 (2) |
C11M | 0.068 (4) | 0.059 (3) | 0.065 (3) | −0.002 (2) | 0.003 (2) | 0.002 (3) |
C12M | 0.050 (3) | 0.066 (3) | 0.086 (4) | −0.003 (2) | 0.012 (2) | 0.000 (3) |
C13M | 0.064 (3) | 0.063 (3) | 0.074 (4) | 0.000 (2) | 0.013 (3) | 0.004 (2) |
C14M | 0.069 (4) | 0.054 (3) | 0.073 (4) | −0.005 (3) | 0.012 (2) | −0.002 (3) |
C15M | 0.089 (6) | 0.099 (6) | 0.097 (6) | 0.010 (3) | 0.022 (4) | −0.001 (4) |
Geometric parameters (Å, º) top
C1M—C2M | 1.370 (8) | C1D—C11D | 1.392 (16) |
C1M—C11M | 1.430 (8) | C2D—C3D | 1.367 (17) |
C2M—C3M | 1.404 (9) | C3D—C4D | 1.395 (17) |
C3M—C4M | 1.354 (10) | C4D—C12D | 1.411 (16) |
C4M—C12M | 1.400 (7) | C5D—C6D | 1.380 (17) |
C5M—C6M | 1.364 (10) | C5D—C13D | 1.388 (16) |
C5M—C13M | 1.402 (8) | C6D—C7D | 1.375 (18) |
C6M—C7M | 1.390 (9) | C7D—C8D | 1.386 (18) |
C7M—C8M | 1.333 (9) | C8D—C14D | 1.380 (17) |
C8M—C14M | 1.427 (10) | C9D—C14D | 1.514 (15) |
C9M—C11M | 1.406 (6) | C9D—C11D | 1.522 (15) |
C9M—C14M | 1.407 (8) | C9D—C15D | 1.538 (17) |
C9M—C15M | 1.527 (10) | C9D—C10Di | 1.611 (15) |
C10M—C13M | 1.377 (7) | C10D—C12D | 1.495 (15) |
C10M—C12M | 1.389 (7) | C10D—C13D | 1.515 (15) |
C11M—C12M | 1.436 (8) | C10D—C9Di | 1.611 (15) |
C13M—C14M | 1.437 (7) | C11D—C12D | 1.389 (16) |
C1D—C2D | 1.386 (17) | C13D—C14D | 1.419 (15) |
| | | |
C2M—C1M—C11M | 122.8 (6) | C3D—C4D—C12D | 116.2 (16) |
C1M—C2M—C3M | 119.1 (6) | C6D—C5D—C13D | 121.4 (18) |
C4M—C3M—C2M | 120.2 (6) | C7D—C6D—C5D | 118 (2) |
C3M—C4M—C12M | 122.4 (6) | C6D—C7D—C8D | 121.4 (19) |
C6M—C5M—C13M | 121.2 (6) | C14D—C8D—C7D | 122 (2) |
C5M—C6M—C7M | 120.3 (6) | C14D—C9D—C11D | 108.3 (14) |
C8M—C7M—C6M | 121.1 (7) | C14D—C9D—C15D | 108 (2) |
C7M—C8M—C14M | 121.3 (7) | C11D—C9D—C15D | 110 (2) |
C11M—C9M—C14M | 120.8 (5) | C14D—C9D—C10Di | 110.0 (12) |
C11M—C9M—C15M | 119.5 (7) | C11D—C9D—C10Di | 112.1 (13) |
C14M—C9M—C15M | 119.7 (7) | C15D—C9D—C10Di | 107.7 (19) |
C13M—C10M—C12M | 122.9 (4) | C12D—C10D—C13D | 110.5 (12) |
C9M—C11M—C1M | 124.1 (6) | C12D—C10D—C9Di | 112.0 (12) |
C9M—C11M—C12M | 119.5 (6) | C13D—C10D—C9Di | 112.0 (13) |
C1M—C11M—C12M | 116.3 (5) | C12D—C11D—C1D | 118.8 (15) |
C10M—C12M—C4M | 122.3 (5) | C12D—C11D—C9D | 117.2 (14) |
C10M—C12M—C11M | 118.5 (4) | C1D—C11D—C9D | 123.9 (14) |
C4M—C12M—C11M | 119.2 (5) | C11D—C12D—C4D | 122.1 (14) |
C10M—C13M—C5M | 122.4 (5) | C11D—C12D—C10D | 116.4 (13) |
C10M—C13M—C14M | 119.3 (5) | C4D—C12D—C10D | 121.5 (14) |
C5M—C13M—C14M | 118.3 (5) | C5D—C13D—C14D | 120.4 (14) |
C9M—C14M—C8M | 123.3 (5) | C5D—C13D—C10D | 123.5 (14) |
C9M—C14M—C13M | 119.0 (5) | C14D—C13D—C10D | 116.1 (12) |
C8M—C14M—C13M | 117.7 (6) | C8D—C14D—C13D | 117.1 (15) |
C2D—C1D—C11D | 120.4 (18) | C8D—C14D—C9D | 126.8 (15) |
C3D—C2D—C1D | 119.7 (19) | C13D—C14D—C9D | 116.1 (13) |
C2D—C3D—C4D | 122.8 (19) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C15H12 | F(000) = 408 |
Mr = 192.25 | Dx = 1.231 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.819 (2) Å | Cell parameters from 500 reflections |
b = 14.474 (4) Å | θ = 4–22° |
c = 8.183 (3) Å | µ = 0.07 mm−1 |
β = 96.84 (3)° | T = 293 K |
V = 1037.1 (5) Å3 | , pale yellow |
Z = 4 | 0.50 × 0.35 × 0.20 mm |
Data collection top
Kuma KM4CCD diffractometer | 865 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.058 |
Graphite monochromator | θmax = 25.0°, θmin = 4.6° |
ω scans | h = −9→10 |
3123 measured reflections | k = −17→16 |
1751 independent reflections | l = −9→4 |
Refinement top
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)] = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.435 | Calculated w = 1/[σ2(Fo2) + (0.2P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.44 | (Δ/σ)max = 0.001 |
1751 reflections | Δρmax = 0.39 e Å−3 |
198 parameters | Δρmin = −0.20 e Å−3 |
142 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.12 (6) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1M | 1.1018 (8) | 0.4205 (5) | 0.3044 (9) | 0.085 (2) | 0.724 (8) |
H1M | 1.0478 | 0.4484 | 0.3820 | 0.102* | 0.724 (8) |
C2M | 1.2548 (9) | 0.4034 (5) | 0.3446 (10) | 0.103 (2) | 0.724 (8) |
H2M | 1.3034 | 0.4214 | 0.4468 | 0.124* | 0.724 (8) |
C3M | 1.3380 (9) | 0.3588 (6) | 0.2310 (13) | 0.106 (3) | 0.724 (8) |
H3M | 1.4408 | 0.3450 | 0.2591 | 0.128* | 0.724 (8) |
C4M | 1.2663 (7) | 0.3357 (5) | 0.0788 (11) | 0.093 (2) | 0.724 (8) |
H4M | 1.3225 | 0.3073 | 0.0038 | 0.111* | 0.724 (8) |
C5M | 0.8117 (10) | 0.3190 (5) | −0.3229 (8) | 0.082 (2) | 0.724 (8) |
H5M | 0.8691 | 0.2943 | −0.4006 | 0.099* | 0.724 (8) |
C6M | 0.6584 (10) | 0.3298 (5) | −0.3612 (8) | 0.096 (2) | 0.724 (8) |
H6M | 0.6118 | 0.3105 | −0.4634 | 0.115* | 0.724 (8) |
C7M | 0.5706 (10) | 0.3694 (5) | −0.2499 (11) | 0.097 (2) | 0.724 (8) |
H7M | 0.4658 | 0.3751 | −0.2788 | 0.116* | 0.724 (8) |
C8M | 0.6328 (10) | 0.3997 (6) | −0.1011 (12) | 0.089 (3) | 0.724 (8) |
H8M | 0.5729 | 0.4292 | −0.0307 | 0.107* | 0.724 (8) |
C9M | 0.8662 (6) | 0.4116 (4) | 0.1050 (7) | 0.0684 (16) | 0.724 (8) |
C10M | 1.0374 (6) | 0.3298 (4) | −0.1216 (7) | 0.0768 (18) | 0.724 (8) |
H10M | 1.0948 | 0.3025 | −0.1968 | 0.092* | 0.724 (8) |
C11M | 1.0221 (6) | 0.3967 (5) | 0.1467 (9) | 0.0702 (19) | 0.724 (8) |
C12M | 1.1101 (5) | 0.3537 (4) | 0.0321 (7) | 0.0705 (16) | 0.724 (8) |
C13M | 0.8841 (6) | 0.3446 (4) | −0.1680 (7) | 0.0703 (17) | 0.724 (8) |
C14M | 0.7936 (7) | 0.3855 (5) | −0.0529 (8) | 0.0690 (19) | 0.724 (8) |
C15M | 0.7621 (11) | 0.4545 (7) | 0.2180 (11) | 0.104 (3) | 0.724 (8) |
H15A | 0.6606 | 0.4592 | 0.1615 | 0.156* | 0.724 (8) |
H15B | 0.7989 | 0.5151 | 0.2502 | 0.156* | 0.724 (8) |
H15C | 0.7609 | 0.4166 | 0.3141 | 0.156* | 0.724 (8) |
C1D | 1.061 (2) | 0.3980 (15) | 0.363 (2) | 0.121 (9)* | 0.276 (8) |
H1D | 0.9883 | 0.4094 | 0.4339 | 0.145* | 0.276 (8) |
C2D | 1.200 (2) | 0.3599 (15) | 0.422 (3) | 0.146 (9)* | 0.276 (8) |
H2D | 1.2219 | 0.3453 | 0.5326 | 0.175* | 0.276 (8) |
C3D | 1.306 (3) | 0.3437 (17) | 0.316 (3) | 0.130 (10)* | 0.276 (8) |
H3D | 1.3988 | 0.3172 | 0.3577 | 0.156* | 0.276 (8) |
C4D | 1.283 (2) | 0.3649 (16) | 0.149 (3) | 0.092 (8)* | 0.276 (8) |
H4D | 1.3578 | 0.3563 | 0.0792 | 0.110* | 0.276 (8) |
C5D | 0.891 (2) | 0.3483 (14) | −0.289 (2) | 0.109 (8)* | 0.276 (8) |
H5D | 0.9656 | 0.3332 | −0.3555 | 0.131* | 0.276 (8) |
C6D | 0.740 (3) | 0.3242 (17) | −0.335 (3) | 0.110 (12)* | 0.276 (8) |
H6D | 0.7123 | 0.2938 | −0.4340 | 0.132* | 0.276 (8) |
C7D | 0.632 (3) | 0.3457 (18) | −0.232 (3) | 0.123 (10)* | 0.276 (8) |
H7D | 0.5299 | 0.3319 | −0.2648 | 0.147* | 0.276 (8) |
C8D | 0.674 (2) | 0.3873 (17) | −0.083 (3) | 0.079 (8)* | 0.276 (8) |
H8D | 0.5992 | 0.3970 | −0.0131 | 0.095* | 0.276 (8) |
C9D | 0.8816 (16) | 0.4670 (10) | 0.1228 (16) | 0.088 (5)* | 0.276 (8) |
C10D | 1.0937 (16) | 0.4251 (9) | −0.0842 (17) | 0.093 (5)* | 0.276 (8) |
H10D | 1.1608 | 0.3899 | −0.1485 | 0.111* | 0.276 (8) |
C11D | 1.029 (2) | 0.4193 (16) | 0.197 (2) | 0.093 (10)* | 0.276 (8) |
C12D | 1.1369 (19) | 0.4004 (13) | 0.0925 (19) | 0.095 (6)* | 0.276 (8) |
C13D | 0.9309 (16) | 0.3953 (13) | −0.1416 (18) | 0.093 (6)* | 0.276 (8) |
C14D | 0.8208 (19) | 0.4152 (12) | −0.032 (2) | 0.069 (7)* | 0.276 (8) |
C15D | 0.784 (2) | 0.4657 (15) | 0.265 (2) | 0.068 (6)* | 0.276 (8) |
H15D | 0.7674 | 0.4030 | 0.2967 | 0.103* | 0.276 (8) |
H15E | 0.6878 | 0.4949 | 0.2317 | 0.103* | 0.276 (8) |
H15F | 0.8362 | 0.4985 | 0.3576 | 0.103* | 0.276 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1M | 0.091 (5) | 0.086 (4) | 0.078 (5) | 0.004 (3) | 0.006 (4) | 0.002 (3) |
C2M | 0.108 (6) | 0.096 (5) | 0.099 (5) | −0.002 (4) | −0.011 (4) | −0.007 (4) |
C3M | 0.084 (5) | 0.108 (6) | 0.122 (8) | −0.003 (4) | −0.007 (6) | 0.011 (5) |
C4M | 0.077 (4) | 0.085 (4) | 0.114 (6) | −0.006 (3) | 0.004 (4) | −0.023 (4) |
C5M | 0.079 (6) | 0.076 (4) | 0.090 (5) | 0.005 (4) | 0.006 (4) | −0.009 (3) |
C6M | 0.104 (6) | 0.089 (4) | 0.088 (5) | 0.009 (4) | −0.014 (4) | −0.006 (3) |
C7M | 0.075 (5) | 0.085 (5) | 0.129 (7) | 0.008 (4) | 0.007 (4) | 0.005 (4) |
C8M | 0.065 (5) | 0.092 (5) | 0.109 (7) | 0.020 (4) | 0.004 (4) | 0.014 (4) |
C9M | 0.065 (3) | 0.069 (4) | 0.075 (4) | −0.002 (2) | 0.025 (3) | −0.004 (2) |
C10M | 0.084 (4) | 0.073 (3) | 0.077 (4) | −0.003 (3) | 0.024 (3) | −0.011 (3) |
C11M | 0.073 (5) | 0.069 (4) | 0.068 (4) | −0.006 (3) | 0.010 (3) | 0.001 (4) |
C12M | 0.055 (3) | 0.073 (3) | 0.084 (4) | −0.007 (2) | 0.010 (3) | −0.005 (3) |
C13M | 0.068 (4) | 0.065 (3) | 0.078 (4) | 0.002 (3) | 0.013 (3) | 0.006 (3) |
C14M | 0.073 (5) | 0.057 (4) | 0.078 (4) | −0.010 (3) | 0.010 (3) | −0.009 (3) |
C15M | 0.112 (6) | 0.120 (6) | 0.079 (6) | 0.006 (4) | 0.007 (5) | −0.023 (5) |
Geometric parameters (Å, º) top
C1M—C2M | 1.373 (9) | C1D—C11D | 1.389 (16) |
C1M—C11M | 1.435 (9) | C2D—C3D | 1.367 (17) |
C2M—C3M | 1.409 (10) | C3D—C4D | 1.394 (17) |
C3M—C4M | 1.369 (10) | C4D—C12D | 1.411 (16) |
C4M—C12M | 1.409 (7) | C5D—C6D | 1.384 (17) |
C5M—C6M | 1.360 (11) | C5D—C13D | 1.389 (16) |
C5M—C13M | 1.399 (8) | C6D—C7D | 1.379 (18) |
C6M—C7M | 1.387 (9) | C7D—C8D | 1.375 (17) |
C7M—C8M | 1.348 (9) | C8D—C14D | 1.375 (16) |
C8M—C14M | 1.441 (10) | C9D—C14D | 1.512 (15) |
C9M—C11M | 1.394 (7) | C9D—C11D | 1.529 (15) |
C9M—C14M | 1.422 (8) | C9D—C15D | 1.530 (16) |
C9M—C15M | 1.512 (9) | C9D—C10Di | 1.612 (15) |
C10M—C13M | 1.377 (7) | C10D—C12D | 1.495 (14) |
C10M—C12M | 1.386 (8) | C10D—C13D | 1.519 (14) |
C11M—C12M | 1.429 (9) | C10D—C9Di | 1.612 (15) |
C13M—C14M | 1.433 (7) | C11D—C12D | 1.379 (16) |
C1D—C2D | 1.382 (17) | C13D—C14D | 1.429 (15) |
| | | |
C2M—C1M—C11M | 122.3 (6) | C3D—C4D—C12D | 115.0 (16) |
C1M—C2M—C3M | 119.9 (7) | C6D—C5D—C13D | 119.7 (18) |
C4M—C3M—C2M | 119.4 (7) | C7D—C6D—C5D | 119 (2) |
C3M—C4M—C12M | 122.2 (7) | C8D—C7D—C6D | 120.6 (19) |
C6M—C5M—C13M | 120.8 (6) | C7D—C8D—C14D | 122.8 (19) |
C5M—C6M—C7M | 120.9 (6) | C14D—C9D—C11D | 107.8 (13) |
C8M—C7M—C6M | 121.9 (8) | C14D—C9D—C15D | 117.1 (13) |
C7M—C8M—C14M | 118.8 (7) | C11D—C9D—C15D | 102.8 (12) |
C11M—C9M—C14M | 120.4 (5) | C14D—C9D—C10Di | 111.1 (11) |
C11M—C9M—C15M | 124.5 (6) | C11D—C9D—C10Di | 112.7 (13) |
C14M—C9M—C15M | 115.1 (6) | C15D—C9D—C10Di | 105.2 (12) |
C13M—C10M—C12M | 122.9 (5) | C12D—C10D—C13D | 110.7 (12) |
C9M—C11M—C12M | 120.2 (6) | C12D—C10D—C9Di | 113.4 (12) |
C9M—C11M—C1M | 123.1 (6) | C13D—C10D—C9Di | 111.0 (12) |
C12M—C11M—C1M | 116.7 (5) | C12D—C11D—C1D | 119.0 (14) |
C10M—C12M—C4M | 122.1 (5) | C12D—C11D—C9D | 117.6 (14) |
C10M—C12M—C11M | 118.4 (5) | C1D—C11D—C9D | 123.3 (14) |
C4M—C12M—C11M | 119.5 (6) | C11D—C12D—C4D | 122.8 (14) |
C10M—C13M—C5M | 122.4 (6) | C11D—C12D—C10D | 115.8 (13) |
C10M—C13M—C14M | 119.2 (5) | C4D—C12D—C10D | 121.3 (14) |
C5M—C13M—C14M | 118.4 (6) | C5D—C13D—C14D | 121.5 (14) |
C9M—C14M—C13M | 118.8 (5) | C5D—C13D—C10D | 122.6 (14) |
C9M—C14M—C8M | 122.2 (6) | C14D—C13D—C10D | 115.9 (12) |
C13M—C14M—C8M | 119.1 (6) | C8D—C14D—C13D | 115.9 (14) |
C2D—C1D—C11D | 120.0 (18) | C8D—C14D—C9D | 128.9 (14) |
C3D—C2D—C1D | 119.6 (19) | C13D—C14D—C9D | 115.2 (12) |
C2D—C3D—C4D | 123.5 (19) | | |
Symmetry code: (i) −x+2, −y+1, −z. |
Crystal data top
C30H24 | F(000) = 408 |
Mr = 384.49 | Dx = 1.289 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7650 (13) Å | Cell parameters from 958 reflections |
b = 13.6035 (19) Å | θ = 4–22° |
c = 8.1177 (10) Å | µ = 0.07 mm−1 |
β = 113.308 (15)° | T = 293 K |
V = 990.3 (2) Å3 | , colorless |
Z = 2 | 0.32 × 0.15 × 0.12 mm |
Data collection top
Kuma KM4CCD diffractometer | 1000 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 26.0°, θmin = 4.5° |
ω scans | h = −12→12 |
3166 measured reflections | k = −15→13 |
1695 independent reflections | l = −10→5 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.078 | All H-atom parameters refined |
wR(F2) = 0.250 | Calculated w = 1/[σ2(Fo2) + (0.1425P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
1695 reflections | Δρmax = 0.25 e Å−3 |
185 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.07 (2) |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.8047 (4) | 0.7058 (3) | 0.8646 (5) | 0.0541 (11) | |
C2 | 0.6630 (5) | 0.7154 (4) | 0.8620 (5) | 0.0609 (12) | |
C3 | 0.6103 (5) | 0.6494 (3) | 0.9502 (5) | 0.0593 (12) | |
C4 | 0.7014 (4) | 0.5734 (3) | 1.0462 (5) | 0.0533 (11) | |
C5 | 1.1869 (4) | 0.5029 (3) | 1.4312 (5) | 0.0533 (10) | |
C6 | 1.3251 (5) | 0.5458 (4) | 1.5166 (5) | 0.0628 (12) | |
C7 | 1.3788 (5) | 0.6100 (3) | 1.4270 (5) | 0.0588 (11) | |
C8 | 1.2928 (4) | 0.6330 (3) | 1.2481 (5) | 0.0501 (10) | |
C9 | 1.0533 (4) | 0.6119 (3) | 0.9665 (4) | 0.0427 (9) | |
C10 | 0.9481 (4) | 0.4824 (3) | 1.1568 (4) | 0.0447 (10) | |
C11 | 0.8968 (4) | 0.6299 (3) | 0.9582 (4) | 0.0453 (9) | |
C12 | 0.8445 (4) | 0.5638 (3) | 1.0519 (4) | 0.0442 (9) | |
C13 | 1.1006 (4) | 0.5257 (3) | 1.2545 (4) | 0.0440 (9) | |
C14 | 1.1540 (4) | 0.5918 (3) | 1.1613 (4) | 0.0435 (9) | |
C15 | 1.1099 (5) | 0.6978 (3) | 0.8890 (6) | 0.0577 (11) | |
H1 | 0.838 (5) | 0.753 (4) | 0.805 (6) | 0.078 (14)* | |
H2 | 0.595 (5) | 0.771 (3) | 0.783 (5) | 0.065 (11)* | |
H3 | 0.505 (5) | 0.658 (3) | 0.951 (6) | 0.082 (13)* | |
H4 | 0.671 (5) | 0.520 (3) | 1.114 (6) | 0.077 (13)* | |
H5 | 1.137 (4) | 0.450 (3) | 1.486 (5) | 0.060 (10)* | |
H6 | 1.392 (5) | 0.532 (3) | 1.637 (6) | 0.069 (12)* | |
H7 | 1.481 (5) | 0.644 (3) | 1.488 (6) | 0.073 (12)* | |
H8 | 1.326 (4) | 0.685 (3) | 1.177 (5) | 0.049 (9)* | |
H10 | 0.910 (4) | 0.453 (3) | 1.250 (4) | 0.048 (9)* | |
H15A | 1.039 (4) | 0.708 (3) | 0.758 (6) | 0.063 (11)* | |
H15B | 1.230 (5) | 0.682 (4) | 0.901 (6) | 0.085 (14)* | |
H15C | 1.121 (5) | 0.761 (4) | 0.962 (7) | 0.091 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.058 (2) | 0.054 (3) | 0.047 (2) | 0.009 (2) | 0.0164 (18) | 0.0016 (18) |
C2 | 0.063 (2) | 0.061 (3) | 0.052 (2) | 0.017 (2) | 0.0151 (19) | −0.002 (2) |
C3 | 0.051 (2) | 0.069 (3) | 0.053 (2) | 0.008 (2) | 0.0153 (18) | −0.012 (2) |
C4 | 0.053 (2) | 0.059 (3) | 0.051 (2) | −0.005 (2) | 0.0245 (18) | −0.0119 (18) |
C5 | 0.058 (2) | 0.056 (3) | 0.0435 (19) | 0.001 (2) | 0.0176 (17) | −0.0036 (17) |
C6 | 0.059 (2) | 0.078 (3) | 0.0396 (19) | 0.002 (2) | 0.0073 (18) | −0.007 (2) |
C7 | 0.054 (2) | 0.064 (3) | 0.054 (2) | −0.002 (2) | 0.0172 (18) | −0.009 (2) |
C8 | 0.0477 (19) | 0.052 (3) | 0.0478 (19) | 0.0009 (18) | 0.0164 (16) | −0.0036 (17) |
C9 | 0.0485 (19) | 0.041 (2) | 0.0379 (16) | −0.0045 (17) | 0.0165 (14) | 0.0008 (14) |
C10 | 0.055 (2) | 0.045 (2) | 0.0369 (17) | −0.0045 (17) | 0.0210 (15) | 0.0000 (14) |
C11 | 0.0458 (19) | 0.048 (2) | 0.0392 (17) | −0.0002 (17) | 0.0141 (15) | −0.0035 (15) |
C12 | 0.0482 (18) | 0.046 (2) | 0.0373 (16) | 0.0005 (17) | 0.0156 (14) | −0.0060 (14) |
C13 | 0.0535 (19) | 0.043 (2) | 0.0352 (17) | −0.0029 (17) | 0.0168 (15) | −0.0045 (14) |
C14 | 0.0486 (19) | 0.041 (2) | 0.0397 (17) | −0.0020 (16) | 0.0163 (15) | −0.0067 (15) |
C15 | 0.067 (3) | 0.050 (3) | 0.058 (2) | −0.005 (2) | 0.027 (2) | 0.007 (2) |
Geometric parameters (Å, º) top
C1—C2 | 1.382 (6) | C8—C14 | 1.376 (5) |
C1—C11 | 1.384 (5) | C8—H8 | 1.04 (4) |
C1—H1 | 0.93 (5) | C9—C14 | 1.521 (5) |
C2—C3 | 1.369 (6) | C9—C11 | 1.522 (5) |
C2—H2 | 1.04 (5) | C9—C15 | 1.531 (5) |
C3—C4 | 1.385 (6) | C9—C10i | 1.625 (5) |
C3—H3 | 1.04 (4) | C10—C13 | 1.503 (5) |
C4—C12 | 1.386 (5) | C10—C12 | 1.514 (5) |
C4—H4 | 1.02 (5) | C10—C9i | 1.625 (5) |
C5—C6 | 1.379 (6) | C10—H10 | 1.05 (3) |
C5—C13 | 1.381 (5) | C11—C12 | 1.398 (5) |
C5—H5 | 1.06 (4) | C13—C14 | 1.401 (5) |
C6—C7 | 1.367 (6) | C15—H15A | 1.02 (4) |
C6—H6 | 0.95 (4) | C15—H15B | 1.16 (5) |
C7—C8 | 1.395 (5) | C15—H15C | 1.02 (6) |
C7—H7 | 1.03 (5) | | |
| | | |
C2—C1—C11 | 120.5 (4) | C14—C9—C10i | 110.0 (3) |
C2—C1—H1 | 119 (3) | C11—C9—C10i | 109.6 (3) |
C11—C1—H1 | 120 (3) | C15—C9—C10i | 105.4 (3) |
C3—C2—C1 | 120.8 (4) | C13—C10—C12 | 108.3 (3) |
C3—C2—H2 | 121 (2) | C13—C10—C9i | 113.5 (3) |
C1—C2—H2 | 118 (2) | C12—C10—C9i | 112.9 (3) |
C2—C3—C4 | 119.5 (4) | C13—C10—H10 | 109.4 (18) |
C2—C3—H3 | 120 (3) | C12—C10—H10 | 109.8 (19) |
C4—C3—H3 | 120 (3) | C9i—C10—H10 | 103 (2) |
C3—C4—C12 | 120.3 (4) | C1—C11—C12 | 118.7 (3) |
C3—C4—H4 | 125 (2) | C1—C11—C9 | 124.6 (3) |
C12—C4—H4 | 115 (2) | C12—C11—C9 | 116.7 (3) |
C6—C5—C13 | 120.1 (4) | C4—C12—C11 | 120.1 (4) |
C6—C5—H5 | 127 (2) | C4—C12—C10 | 121.9 (3) |
C13—C5—H5 | 113 (2) | C11—C12—C10 | 118.0 (3) |
C7—C6—C5 | 120.5 (4) | C5—C13—C14 | 120.0 (3) |
C7—C6—H6 | 115 (2) | C5—C13—C10 | 122.0 (3) |
C5—C6—H6 | 125 (3) | C14—C13—C10 | 118.0 (3) |
C6—C7—C8 | 119.9 (4) | C8—C14—C13 | 119.1 (3) |
C6—C7—H7 | 122 (2) | C8—C14—C9 | 124.0 (3) |
C8—C7—H7 | 118 (2) | C13—C14—C9 | 116.8 (3) |
C14—C8—C7 | 120.4 (4) | C9—C15—H15A | 109 (2) |
C14—C8—H8 | 117 (2) | C9—C15—H15B | 110 (2) |
C7—C8—H8 | 123 (2) | H15A—C15—H15B | 111 (3) |
C14—C9—C11 | 107.5 (2) | C9—C15—H15C | 112 (3) |
C14—C9—C15 | 112.0 (3) | H15A—C15—H15C | 112 (4) |
C11—C9—C15 | 112.3 (3) | H15B—C15—H15C | 104 (4) |
Symmetry code: (i) −x+2, −y+1, −z+2. |