Monitoring structural transformations in crystals. 6. The [4 + 4] photodimerization of 9-methyl­anthracene

Turowska-Tyrk, I.; Trzop, E.

doi:10.1107/S0108768103023255

Monitoring structural transformations in crystals. 6. The [4 + 4] photodimerization of 9-methylanthracene

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.

Keywords: photoreactions in crystals; monitoring structural changes; X-ray structure analysis.

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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

Computing details top

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).

(0D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.023
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1171P)² + 0.0477P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
1938 reflections	Δρ_max = 0.22 e Å⁻³
185 parameters	Δρ_min = −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	U_iso*/U_eq
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)

(3D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.024
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1495P)²] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
1938 reflections	Δρ_max = 0.31 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(4D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.025
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.146P)² + 0.0231P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
1937 reflections	Δρ_max = 0.31 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(6D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.028
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1343P)² + 0.1501P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
1940 reflections	Δρ_max = 0.26 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(8D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.028
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1577P)² + 0.0018P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
1942 reflections	Δρ_max = 0.32 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(11D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.029
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1521P)² + 0.2205P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max = 0.001
1944 reflections	Δρ_max = 0.25 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(15D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.035
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.21	(Δ/σ)_max < 0.001
1942 reflections	Δρ_max = 0.36 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(18D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.039
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.27	(Δ/σ)_max = 0.002
1947 reflections	Δρ_max = 0.35 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(24D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.045
Graphite monochromator	θ_max = 25.0°, θ_min = 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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.34	(Δ/σ)_max < 0.001
1752 reflections	Δρ_max = 0.38 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(26D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.056
Graphite monochromator	θ_max = 25.0°, θ_min = 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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.42	(Δ/σ)_max < 0.001
1750 reflections	Δρ_max = 0.37 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(28D) top

Crystal data top

C₁₅H₁₂	F(000) = 408
M_r = 192.25	D_x = 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	R_int = 0.058
Graphite monochromator	θ_max = 25.0°, θ_min = 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(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
S = 1.44	(Δ/σ)_max = 0.001
1751 reflections	Δρ_max = 0.39 e Å⁻³
198 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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.

(100D) top

Crystal data top

C₃₀H₂₄	F(000) = 408
M_r = 384.49	D_x = 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	R_int = 0.071
Graphite monochromator	θ_max = 26.0°, θ_min = 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(F_o²) + (0.1425P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
1695 reflections	Δρ_max = 0.25 e Å⁻³
185 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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.

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Monitoring structural transformations in crystals. 6. The [4 + 4] photodimerization of 9-methyl­anthracene

Supporting information

Monitoring structural transformations in crystals. 6. The [4 + 4] photodimerization of 9-methylanthracene