The role of free space in photochemical reactions in crystals at high pressure – the case of 9-methyl­anthracene

The influence of pressure on the course of [4+4] photodimerization in crystals of 9-methyl­anthracene is presented. The studies were performed at 0.1 and 0.4 GPa. As a result of the reaction at high pressure, crystals of the pure product were obtained, which allowed for monitoring of the reaction until its completion. The initial increase in the unit-cell volume caused by the reaction under ambient conditions was reduced at high pressure due to the decrease in the void volume. Despite the smaller size of the void volume at high pressure, dimer molecules formed during the reaction changed the orientation of the monomer molecules in the crystal structure. The size of the voids above the terminal rings of the monomers correlates with the position of the terminal rings in the dimer. The reaction rate increased at high pressure, indicating that the decrease in the distance between adjacent monomers caused by pressure dominates over the decrease in the void volume. This distance is statistically constant as the reaction progresses, contrary to the reaction at ambient pressure.

Computing details

For all structures, data collection: CrysAlis PRO (Agilent Technologies, 2014); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014/7 (Sheldrick, 2015).

(0.1GPa_0hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.276 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7976 (3) Å	Cell parameters from 1733 reflections
b = 14.331 (7) Å	θ = 5.6–24.7°
c = 7.9860 (3) Å	µ = 0.07 mm^−1
β = 96.276 (3)°	T = 298 K
V = 1000.8 (5) Å^3	Block, colourless
Z = 4	0.28 × 0.25 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	622 independent reflections
Radiation source: fine-focus sealed tube	439 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.6°, θmin = 5.6°
φ– and ω scans	h = −10→10
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −4→4
Tmin = 0.02, Tmax = 1.00	l = −9→9
4976 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.264	w = 1/[σ^2(Fo^2) + (0.1385P)^2 + 0.8295P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max < 0.001
622 reflections	Δρmax = 0.14 e Å^−3
86 parameters	Δρmin = −0.14 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.1020 (5)	0.5795 (9)	0.3066 (6)	0.0565 (16)*
H1	0.0502	0.5501	0.3874	0.068*
C2	0.2534 (6)	0.5990 (10)	0.3414 (6)	0.069 (9)
H2	0.3030	0.5833	0.4465	0.083*
C3	0.3361 (6)	0.6420 (11)	0.2240 (7)	0.086 (10)
H3	0.4394	0.6549	0.2513	0.103*
C4	0.2665 (5)	0.6648 (9)	0.0710 (6)	0.0550 (16)*
H4	0.3226	0.6933	−0.0069	0.066*
C5	−0.1931 (5)	0.6803 (10)	−0.3335 (6)	0.0541 (16)*
H5	−0.1355	0.7051	−0.4138	0.065*
C6	−0.3462 (6)	0.6691 (10)	−0.3717 (6)	0.082 (9)
H6	−0.3933	0.6874	−0.4765	0.099*
C7	−0.4336 (5)	0.6295 (10)	−0.2512 (7)	0.082 (9)
H7	−0.5386	0.6226	−0.2775	0.098*
C8	−0.3680 (5)	0.6017 (9)	−0.0996 (6)	0.0532 (16)*
H8	−0.4283	0.5750	−0.0238	0.064*
C9	−0.1361 (4)	0.5848 (9)	0.1071 (5)	0.0461 (15)*
C10	0.0364 (5)	0.6685 (9)	−0.1316 (5)	0.0463 (15)*
H10	0.0944	0.6932	−0.2116	0.056*
C11	0.0224 (5)	0.6034 (9)	0.1483 (5)	0.0452 (14)*
C12	0.1078 (5)	0.6461 (8)	0.0264 (5)	0.0455 (14)*
C13	−0.1196 (5)	0.6550 (8)	−0.1739 (5)	0.0452 (14)*
C14	−0.2074 (5)	0.6122 (9)	−0.0525 (5)	0.0447 (14)*
C15	−0.2254 (5)	0.5429 (9)	0.2380 (6)	0.100 (9)
H15A	−0.1576	0.5289	0.3373	0.150*
H15B	−0.3018	0.5864	0.2656	0.150*
H15C	−0.2740	0.4865	0.1948	0.150*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.069 (3)	0.08 (3)	0.055 (3)	0.024 (5)	−0.008 (2)	0.001 (5)
C3	0.048 (3)	0.13 (3)	0.074 (4)	0.004 (5)	−0.001 (2)	−0.007 (6)
C6	0.067 (3)	0.12 (3)	0.054 (3)	0.000 (5)	−0.007 (2)	−0.003 (5)
C7	0.050 (3)	0.13 (3)	0.066 (3)	0.000 (5)	−0.002 (2)	−0.007 (5)
C15	0.056 (3)	0.20 (3)	0.050 (3)	−0.017 (5)	0.0186 (19)	0.004 (5)

Geometric parameters (Å, º)

C1—C2	1.360 (8)	C7—H7	0.9300
C1—C11	1.419 (7)	C8—C14	1.430 (6)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.391 (12)	C9—C14	1.413 (8)
C2—H2	0.9300	C9—C11	1.422 (7)
C3—C4	1.346 (8)	C9—C15	1.500 (9)
C3—H3	0.9300	C10—C12	1.384 (7)
C4—C12	1.428 (7)	C10—C13	1.391 (6)
C4—H4	0.9300	C10—H10	0.9300
C5—C6	1.358 (7)	C11—C12	1.430 (9)
C5—C13	1.412 (7)	C13—C14	1.440 (9)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.415 (10)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.344 (9)
C2—C1—C11	120.6 (6)	C14—C9—C11	118.9 (6)
C2—C1—H1	119.7	C14—C9—C15	121.7 (4)
C11—C1—H1	119.7	C11—C9—C15	119.3 (4)
C1—C2—C3	121.7 (5)	C12—C10—C13	121.7 (5)
C1—C2—H2	119.1	C12—C10—H10	119.1
C3—C2—H2	119.1	C13—C10—H10	119.1
C4—C3—C2	120.0 (5)	C1—C11—C9	122.5 (6)
C4—C3—H3	120.0	C1—C11—C12	117.7 (4)
C2—C3—H3	120.0	C9—C11—C12	119.8 (5)
C3—C4—C12	121.1 (6)	C10—C12—C4	121.2 (6)
C3—C4—H4	119.5	C10—C12—C11	120.0 (4)
C12—C4—H4	119.5	C4—C12—C11	118.8 (5)
C6—C5—C13	121.2 (6)	C10—C13—C5	121.7 (6)
C6—C5—H5	119.4	C10—C13—C14	118.9 (5)
C13—C5—H5	119.4	C5—C13—C14	119.4 (4)
C5—C6—C7	119.6 (5)	C9—C14—C8	122.4 (6)
C5—C6—H6	120.2	C9—C14—C13	120.5 (4)
C7—C6—H6	120.2	C8—C14—C13	117.0 (5)
C8—C7—C6	121.3 (5)	C9—C15—H15A	109.5
C8—C7—H7	119.3	C9—C15—H15B	109.5
C6—C7—H7	119.3	H15A—C15—H15B	109.5
C7—C8—C14	121.4 (6)	C9—C15—H15C	109.5
C7—C8—H8	119.3	H15A—C15—H15C	109.5
C14—C8—H8	119.3	H15B—C15—H15C	109.5

(0.1GPa_5.5hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.276 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7885 (4) Å	Cell parameters from 1213 reflections
b = 14.260 (8) Å	θ = 5.5–22.1°
c = 8.0361 (4) Å	µ = 0.07 mm^−1
β = 96.465 (4)°	T = 298 K
V = 1000.7 (6) Å^3	Block, colourless
Z = 4	0.28 × 0.25 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	570 independent reflections
Radiation source: fine-focus sealed tube	374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.4°, θmin = 5.6°
φ– and ω scans	h = −10→10
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −4→4
Tmin = 0.49, Tmax = 1.00	l = −9→9
4514 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.089	H-atom parameters constrained
wR(F^2) = 0.249	w = 1/[σ^2(Fo^2) + (0.1025P)^2 + 1.0585P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
570 reflections	Δρmax = 0.14 e Å^−3
69 parameters	Δρmin = −0.11 e Å^−3
77 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11M	1.0226 (3)	0.3983 (7)	0.1469 (5)	0.0543 (11)*	0.884 (7)
C1M	1.1035 (4)	0.4198 (7)	0.3064 (5)	0.063 (2)*	0.884 (7)
H1M	1.0422	0.4553	0.4002	0.075*	0.884 (7)
C2M	1.2535 (4)	0.4002 (8)	0.3433 (5)	0.070 (2)*	0.884 (7)
H2M	1.3099	0.4134	0.4557	0.084*	0.884 (7)
C3M	1.3375 (3)	0.3580 (8)	0.2242 (6)	0.068 (2)*	0.884 (7)
H3M	1.4514	0.3447	0.2539	0.081*	0.884 (7)
C4M	1.2674 (4)	0.3363 (7)	0.0726 (5)	0.0601 (19)*	0.884 (7)
H4M	1.3202	0.3048	−0.0167	0.072*	0.884 (7)
C12M	1.1093 (4)	0.3540 (7)	0.0272 (4)	0.0543 (11)*	0.884 (7)
C14M	0.7927 (4)	0.3862 (7)	−0.0514 (5)	0.0543 (11)*	0.884 (7)
C8M	0.6327 (4)	0.3964 (7)	−0.0991 (5)	0.062 (2)*	0.884 (7)
H8M	0.5647	0.4265	−0.0178	0.074*	0.884 (7)
C7M	0.5662 (3)	0.3709 (8)	−0.2524 (5)	0.071 (2)*	0.884 (7)
H7M	0.4427	0.3818	−0.2870	0.085*	0.884 (7)
C6M	0.6550 (4)	0.3312 (8)	−0.3699 (5)	0.070 (2)*	0.884 (7)
H6M	0.6042	0.3127	−0.4790	0.084*	0.884 (7)
C5M	0.8063 (5)	0.3196 (8)	−0.3312 (5)	0.063 (2)*	0.884 (7)
H5M	0.8716	0.2925	−0.4110	0.076*	0.884 (7)
C13M	0.8818 (3)	0.3471 (8)	−0.1733 (5)	0.0543 (11)*	0.884 (7)
C9M	0.8650 (6)	0.4131 (11)	0.1063 (7)	0.0543 (11)*	0.884 (7)
C10M	1.0371 (6)	0.3306 (12)	−0.1292 (6)	0.0543 (11)*	0.884 (7)
H10M	1.0940	0.3031	−0.2070	0.065*	0.884 (7)
C15M	0.7721 (9)	0.4551 (12)	0.2354 (9)	0.076 (6)	0.884 (7)
H15A	0.6670	0.4606	0.1886	0.114*	0.884 (7)
H15B	0.7786	0.4152	0.3322	0.114*	0.884 (7)
H15C	0.8117	0.5160	0.2672	0.114*	0.884 (7)
C11D	1.026 (2)	0.417 (2)	0.197 (3)	0.061 (6)*	0.116 (7)
C1D	1.066 (3)	0.396 (3)	0.365 (3)	0.060 (12)*	0.116 (7)
H1D	0.9977	0.4072	0.4431	0.072*	0.116 (7)
C2D	1.210 (3)	0.361 (4)	0.419 (3)	0.067 (7)*	0.116 (7)
H2D	1.2327	0.3419	0.5449	0.081*	0.116 (7)
C3D	1.315 (3)	0.345 (4)	0.308 (4)	0.057 (6)*	0.116 (7)
H3D	1.4231	0.3205	0.3504	0.069*	0.116 (7)
C4D	1.277 (3)	0.367 (4)	0.141 (3)	0.070 (13)*	0.116 (7)
H4D	1.3473	0.3559	0.0487	0.084*	0.116 (7)
C12D	1.135 (2)	0.403 (3)	0.085 (2)	0.061 (6)*	0.116 (7)
C14D	0.817 (3)	0.420 (2)	−0.040 (3)	0.061 (6)*	0.116 (7)
C8D	0.665 (3)	0.400 (4)	−0.087 (4)	0.071 (9)*	0.116 (7)
H8D	0.5886	0.4182	−0.0034	0.085*	0.116 (7)
C7D	0.619 (3)	0.362 (5)	−0.244 (4)	0.081 (6)*	0.116 (7)
H7D	0.5031	0.3492	−0.2762	0.097*	0.116 (7)
C6D	0.725 (4)	0.344 (5)	−0.353 (4)	0.078 (6)*	0.116 (7)
H6D	0.6838	0.3158	−0.4557	0.093*	0.116 (7)
C5D	0.878 (3)	0.363 (4)	−0.307 (3)	0.069 (13)*	0.116 (7)
H5D	0.9695	0.3486	−0.3788	0.083*	0.116 (7)
C13D	0.925 (2)	0.401 (3)	−0.152 (3)	0.061 (6)*	0.116 (7)
C9D	0.877 (3)	0.4622 (15)	0.128 (3)	0.061 (6)*	0.116 (7)
C10D	1.090 (3)	0.4260 (17)	−0.097 (3)	0.061 (6)*	0.116 (7)
H10D	1.1544	0.3890	−0.1640	0.073*	0.116 (7)
C15D	0.752 (6)	0.461 (5)	0.248 (7)	0.087 (12)*	0.116 (7)
H15D	0.6616	0.4909	0.1947	0.131*	0.116 (7)
H15E	0.7293	0.3974	0.2746	0.131*	0.116 (7)
H15F	0.7881	0.4943	0.3485	0.131*	0.116 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15M	0.068 (4)	0.10 (2)	0.063 (4)	0.003 (6)	0.018 (3)	−0.017 (6)

Geometric parameters (Å, º)

C11M—C9M	1.403 (6)	C11D—C12D	1.3982
C11M—C1M	1.4276	C11D—C9D	1.511 (16)
C11M—C12M	1.4380	C1D—C2D	1.3819
C1M—C2M	1.3469	C2D—C3D	1.3688
C2M—C3M	1.4079	C3D—C4D	1.3852
C3M—C4M	1.3385	C4D—C12D	1.3862
C4M—C12M	1.4191	C12D—C10D	1.506 (16)
C12M—C10M	1.384 (7)	C14D—C8D	1.3760
C14M—C9M	1.406 (7)	C14D—C13D	1.4011
C14M—C8M	1.4224	C14D—C9D	1.521 (16)
C14M—C13M	1.4345	C8D—C7D	1.3950
C8M—C7M	1.3527	C7D—C6D	1.3667
C7M—C6M	1.4087	C6D—C5D	1.3792
C6M—C5M	1.3417	C5D—C13D	1.3808
C5M—C13M	1.4193	C13D—C10D	1.510 (16)
C13M—C10M	1.391 (6)	C9D—C15D	1.533 (19)
C9M—C15M	1.514 (10)	C9D—C10D^i	1.647 (19)
C11D—C1D	1.3836	C10D—C9D^i	1.647 (19)
C9M—C11M—C1M	123.7 (4)	C2D—C1D—C11D	120.5
C9M—C11M—C12M	119.6 (4)	C3D—C2D—C1D	120.8
C1M—C11M—C12M	116.6	C2D—C3D—C4D	119.5
C2M—C1M—C11M	122.0	C3D—C4D—C12D	120.3
C1M—C2M—C3M	120.9	C4D—C12D—C11D	120.1
C4M—C3M—C2M	119.7	C4D—C12D—C10D	121.7 (14)
C3M—C4M—C12M	122.0	C11D—C12D—C10D	118.2 (14)
C10M—C12M—C4M	121.7 (4)	C8D—C14D—C13D	119.1
C10M—C12M—C11M	119.4 (4)	C8D—C14D—C9D	123.6 (14)
C4M—C12M—C11M	118.9	C13D—C14D—C9D	117.3 (14)
C9M—C14M—C8M	123.2 (4)	C14D—C8D—C7D	120.4
C9M—C14M—C13M	119.7 (4)	C6D—C7D—C8D	119.9
C8M—C14M—C13M	117.1	C7D—C6D—C5D	120.5
C7M—C8M—C14M	122.1	C6D—C5D—C13D	120.1
C8M—C7M—C6M	120.2	C5D—C13D—C14D	120.0
C5M—C6M—C7M	120.3	C5D—C13D—C10D	122.5 (15)
C6M—C5M—C13M	121.6	C14D—C13D—C10D	117.5 (15)
C10M—C13M—C5M	121.9 (4)	C11D—C9D—C14D	110.8 (16)
C10M—C13M—C14M	119.2 (4)	C11D—C9D—C15D	115 (3)
C5M—C13M—C14M	118.8	C14D—C9D—C15D	111 (2)
C11M—C9M—C14M	120.2 (6)	C11D—C9D—C10D^i	107.7 (18)
C11M—C9M—C15M	119.7 (5)	C14D—C9D—C10D^i	107.4 (18)
C14M—C9M—C15M	120.1 (5)	C15D—C9D—C10D^i	105 (2)
C12M—C10M—C13M	121.8 (6)	C12D—C10D—C13D	111.7 (16)
C1D—C11D—C12D	118.7	C12D—C10D—C9D^i	109 (2)
C1D—C11D—C9D	124.2 (13)	C13D—C10D—C9D^i	112 (2)
C12D—C11D—C9D	116.8 (13)

Symmetry code: (i) −x+2, −y+1, −z.

(0.1GPa_15hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.281 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.672 (7) Å	Cell parameters from 495 reflections
b = 14.14 (12) Å	θ = 5.4–19.9°
c = 8.197 (10) Å	µ = 0.07 mm^−1
β = 97.39 (8)°	T = 298 K
V = 997 (9) Å^3	Block, colourless
Z = 4	0.28 × 0.25 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	612 independent reflections
Radiation source: fine-focus sealed tube	205 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.112
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.4°, θmin = 5.5°
φ– and ω scans	h = −10→10
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −5→4
Tmin = 0.56, Tmax = 1.00	l = −9→9
4444 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.155	H-atom parameters constrained
wR(F^2) = 0.482	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.30	(Δ/σ)max < 0.001
612 reflections	Δρmax = 0.18 e Å^−3
52 parameters	Δρmin = −0.11 e Å^−3
65 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11M	1.0195 (8)	0.3982 (14)	0.1490 (11)	0.115 (3)*	0.664 (11)
C1M	1.0991 (10)	0.4195 (14)	0.3082 (11)	0.132 (4)*	0.664 (11)
H1M	1.0345	0.4540	0.3986	0.158*	0.664 (11)
C2M	1.2516 (10)	0.4011 (16)	0.3489 (12)	0.143 (4)*	0.664 (11)
H2M	1.3071	0.4141	0.4610	0.172*	0.664 (11)
C3M	1.3397 (8)	0.3603 (16)	0.2343 (13)	0.143 (4)*	0.664 (11)
H3M	1.4554	0.3478	0.2669	0.172*	0.664 (11)
C4M	1.2709 (9)	0.3388 (15)	0.0833 (12)	0.132 (4)*	0.664 (11)
H4M	1.3266	0.3081	−0.0029	0.158*	0.664 (11)
C12M	1.1103 (9)	0.3553 (14)	0.0340 (10)	0.115 (3)*	0.664 (11)
C14M	0.7934 (9)	0.3911 (14)	−0.0596 (9)	0.115 (3)*	0.664 (11)
C8M	0.6308 (9)	0.3973 (14)	−0.1115 (11)	0.132 (4)*	0.664 (11)
H8M	0.5588	0.4271	−0.0353	0.158*	0.664 (11)
C7M	0.5666 (8)	0.3686 (15)	−0.2625 (12)	0.143 (4)*	0.664 (11)
H7M	0.4408	0.3765	−0.3005	0.172*	0.664 (11)
C6M	0.6606 (11)	0.3294 (14)	−0.3731 (11)	0.143 (4)*	0.664 (11)
H6M	0.6115	0.3085	−0.4806	0.172*	0.664 (11)
C5M	0.8147 (11)	0.3214 (15)	−0.3302 (10)	0.132 (4)*	0.664 (11)
H5M	0.8836	0.2947	−0.4052	0.158*	0.664 (11)
C13M	0.8878 (8)	0.3523 (17)	−0.1745 (10)	0.115 (3)*	0.664 (11)
C9M	0.8621 (12)	0.4154 (19)	0.0983 (13)	0.115 (3)*	0.664 (11)
C10M	1.0421 (12)	0.336 (2)	−0.1238 (11)	0.115 (3)*	0.664 (11)
H10M	1.1032	0.3111	−0.1986	0.138*	0.664 (11)
C15M	0.7505 (18)	0.447 (2)	0.2159 (19)	0.153 (8)*	0.664 (11)
H15A	0.8081	0.4622	0.3207	0.229*	0.664 (11)
H15B	0.6947	0.5020	0.1722	0.229*	0.664 (11)
H15C	0.6784	0.3971	0.2294	0.229*	0.664 (11)
C11D	1.0313 (15)	0.4189 (15)	0.2070 (18)	0.114 (5)*	0.336 (11)
C1D	1.064 (2)	0.397 (2)	0.3722 (18)	0.147 (6)*	0.336 (11)
H1D	0.9936	0.4112	0.4452	0.176*	0.336 (11)
C2D	1.204 (2)	0.355 (3)	0.4324 (18)	0.153 (6)*	0.336 (11)
H2D	1.2215	0.3353	0.5563	0.183*	0.336 (11)
C3D	1.3123 (19)	0.334 (3)	0.330 (2)	0.153 (6)*	0.336 (11)
H3D	1.4181	0.3045	0.3763	0.183*	0.336 (11)
C4D	1.2820 (17)	0.357 (2)	0.164 (2)	0.147 (6)*	0.336 (11)
H4D	1.3545	0.3423	0.0783	0.176*	0.336 (11)
C12D	1.1430 (17)	0.3995 (18)	0.1028 (17)	0.114 (5)*	0.336 (11)
C14D	0.8217 (17)	0.4137 (15)	−0.0223 (18)	0.114 (5)*	0.336 (11)
C8D	0.6681 (16)	0.391 (2)	−0.071 (2)	0.147 (6)*	0.336 (11)
H8D	0.5892	0.4113	0.0081	0.176*	0.336 (11)
C7D	0.6227 (18)	0.349 (3)	−0.223 (2)	0.153 (6)*	0.336 (11)
H7D	0.5058	0.3355	−0.2563	0.183*	0.336 (11)
C6D	0.731 (2)	0.330 (3)	−0.325 (2)	0.153 (6)*	0.336 (11)
H6D	0.6913	0.2994	−0.4255	0.183*	0.336 (11)
C5D	0.886 (2)	0.351 (3)	−0.278 (2)	0.147 (6)*	0.336 (11)
H5D	0.9803	0.3361	−0.3456	0.176*	0.336 (11)
C13D	0.9320 (16)	0.3930 (19)	−0.128 (2)	0.114 (5)*	0.336 (11)
C9D	0.885 (2)	0.4662 (13)	0.133 (2)	0.114 (5)*	0.336 (11)
C10D	1.099 (2)	0.4239 (14)	−0.074 (2)	0.114 (5)*	0.336 (11)
H10D	1.1657	0.3859	−0.1365	0.137*	0.336 (11)
C15D	0.779 (3)	0.466 (3)	0.265 (3)	0.109 (9)*	0.336 (11)
H15D	0.6825	0.4963	0.2244	0.164*	0.336 (11)
H15E	0.7597	0.4024	0.2966	0.164*	0.336 (11)
H15F	0.8276	0.5005	0.3596	0.164*	0.336 (11)

Geometric parameters (Å, º)

C11M—C9M	1.396 (10)	C11D—C12D	1.3982
C11M—C1M	1.4276	C11D—C9D	1.490 (15)
C11M—C12M	1.4381	C1D—C2D	1.3819
C1M—C2M	1.3469	C2D—C3D	1.3688
C2M—C3M	1.4079	C3D—C4D	1.3852
C3M—C4M	1.3384	C4D—C12D	1.3862
C4M—C12M	1.4191	C12D—C10D	1.489 (14)
C12M—C10M	1.378 (10)	C14D—C8D	1.3760
C14M—C9M	1.396 (11)	C14D—C13D	1.4011
C14M—C8M	1.4224	C14D—C9D	1.514 (15)
C14M—C13M	1.4345	C8D—C7D	1.3950
C8M—C7M	1.3527	C7D—C6D	1.3667
C7M—C6M	1.4087	C6D—C5D	1.3792
C6M—C5M	1.3417	C5D—C13D	1.3807
C5M—C13M	1.4193	C13D—C10D	1.526 (14)
C13M—C10M	1.369 (11)	C9D—C15D	1.514 (16)
C9M—C15M	1.519 (14)	C9D—C10D^i	1.64 (2)
C11D—C1D	1.3836	C10D—C9D^i	1.64 (2)
C9M—C11M—C1M	125.1 (7)	C2D—C1D—C11D	120.5
C9M—C11M—C12M	118.4 (7)	C3D—C2D—C1D	120.8
C1M—C11M—C12M	116.6	C2D—C3D—C4D	119.5
C2M—C1M—C11M	122.0	C3D—C4D—C12D	120.3
C1M—C2M—C3M	120.9	C4D—C12D—C11D	120.1
C4M—C3M—C2M	119.7	C4D—C12D—C10D	123.8 (11)
C3M—C4M—C12M	122.0	C11D—C12D—C10D	116.0 (11)
C10M—C12M—C4M	121.4 (7)	C8D—C14D—C13D	119.1
C10M—C12M—C11M	119.6 (7)	C8D—C14D—C9D	126.1 (10)
C4M—C12M—C11M	118.9	C13D—C14D—C9D	114.6 (10)
C9M—C14M—C8M	123.4 (6)	C14D—C8D—C7D	120.4
C9M—C14M—C13M	119.4 (7)	C6D—C7D—C8D	119.9
C8M—C14M—C13M	117.1	C7D—C6D—C5D	120.5
C7M—C8M—C14M	122.1	C6D—C5D—C13D	120.1
C8M—C7M—C6M	120.2	C5D—C13D—C14D	120.0
C5M—C6M—C7M	120.3	C5D—C13D—C10D	122.5 (11)
C6M—C5M—C13M	121.6	C14D—C13D—C10D	117.4 (11)
C10M—C13M—C5M	121.8 (8)	C11D—C9D—C15D	105.7 (14)
C10M—C13M—C14M	118.9 (7)	C11D—C9D—C14D	108.8 (13)
C5M—C13M—C14M	118.8	C15D—C9D—C14D	114.4 (16)
C14M—C9M—C11M	121.2 (10)	C11D—C9D—C10D^i	116.8 (15)
C14M—C9M—C15M	115.5 (9)	C15D—C9D—C10D^i	106.9 (19)
C11M—C9M—C15M	122.7 (9)	C14D—C9D—C10D^i	104.6 (14)
C13M—C10M—C12M	122.4 (10)	C12D—C10D—C13D	109.2 (12)
C1D—C11D—C12D	118.7	C12D—C10D—C9D^i	119.2 (16)
C1D—C11D—C9D	124.0 (10)	C13D—C10D—C9D^i	107.2 (16)
C12D—C11D—C9D	117.2 (10)

Symmetry code: (i) −x+2, −y+1, −z.

(0.1GPa_25hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.297 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.485 (2) Å	Cell parameters from 760 reflections
b = 13.72 (3) Å	θ = 5.7–23.6°
c = 8.568 (2) Å	µ = 0.07 mm^−1
β = 99.15 (2)°	T = 298 K
V = 985 (2) Å^3	Block, colourless
Z = 4	0.28 × 0.25 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	587 independent reflections
Radiation source: fine-focus sealed tube	336 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.086
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.6°, θmin = 5.7°
φ– and ω scans	h = −10→10
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −4→4
Tmin = 0.58, Tmax = 1.00	l = −10→9
4480 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.105	H-atom parameters constrained
wR(F^2) = 0.330	w = 1/[σ^2(Fo^2) + (0.189P)^2 + 0.5333P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
587 reflections	Δρmax = 0.16 e Å^−3
69 parameters	Δρmin = −0.16 e Å^−3
76 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11M	1.031 (3)	0.389 (4)	0.187 (3)	0.072 (4)*	0.119 (10)
C1M	1.108 (4)	0.412 (5)	0.343 (4)	0.083 (10)*	0.119 (10)
H1M	1.0374	0.4449	0.4267	0.100*	0.119 (10)
C2M	1.266 (4)	0.398 (6)	0.389 (4)	0.069 (10)*	0.119 (10)
H2M	1.3200	0.4128	0.4990	0.083*	0.119 (10)
C3M	1.362 (3)	0.360 (7)	0.284 (4)	0.077 (14)*	0.119 (10)
H3M	1.4813	0.3513	0.3205	0.092*	0.119 (10)
C4M	1.295 (3)	0.337 (7)	0.136 (4)	0.085 (10)*	0.119 (10)
H4M	1.3568	0.3083	0.0565	0.102*	0.119 (10)
C12M	1.130 (3)	0.349 (5)	0.082 (3)	0.072 (4)*	0.119 (10)
C14M	0.805 (4)	0.382 (5)	−0.021 (3)	0.072 (4)*	0.119 (10)
C8M	0.639 (4)	0.391 (7)	−0.079 (4)	0.086 (10)*	0.119 (10)
H8M	0.5640	0.4206	−0.0089	0.103*	0.119 (10)
C7M	0.576 (4)	0.365 (7)	−0.229 (4)	0.080 (6)*	0.119 (10)
H7M	0.4472	0.3752	−0.2712	0.095*	0.119 (10)
C6M	0.674 (5)	0.326 (7)	−0.331 (4)	0.075 (7)*	0.119 (10)
H6M	0.6250	0.3074	−0.4376	0.090*	0.119 (10)
C5M	0.831 (5)	0.316 (6)	−0.282 (3)	0.073 (14)*	0.119 (10)
H5M	0.9029	0.2892	−0.3517	0.088*	0.119 (10)
C13M	0.904 (3)	0.344 (5)	−0.128 (3)	0.072 (4)*	0.119 (10)
C9M	0.870 (4)	0.408 (6)	0.133 (4)	0.072 (4)*	0.119 (10)
C10M	1.065 (4)	0.330 (6)	−0.075 (4)	0.072 (4)*	0.119 (10)
H10M	1.1305	0.3086	−0.1446	0.087*	0.119 (10)
C15M	0.765 (7)	0.441 (8)	0.251 (6)	0.082 (13)*	0.119 (10)
H15A	0.6586	0.4516	0.1967	0.124*	0.119 (10)
H15B	0.7647	0.3922	0.3303	0.124*	0.119 (10)
H15C	0.8066	0.5011	0.2992	0.124*	0.119 (10)
C11D	1.0209 (6)	0.4171 (8)	0.1924 (6)	0.0677 (15)*	0.881 (10)
C1D	1.0518 (7)	0.3966 (9)	0.3525 (6)	0.077 (3)*	0.881 (10)
H1D	0.9761	0.4106	0.4173	0.093*	0.881 (10)
C2D	1.1970 (7)	0.3576 (10)	0.4198 (5)	0.079 (3)*	0.881 (10)
H2D	1.2126	0.3390	0.5395	0.095*	0.881 (10)
C3D	1.3124 (6)	0.3376 (9)	0.3295 (6)	0.070 (3)*	0.881 (10)
H3D	1.4220	0.3102	0.3811	0.084*	0.881 (10)
C4D	1.2843 (6)	0.3585 (10)	0.1693 (6)	0.077 (3)*	0.881 (10)
H4D	1.3622	0.3447	0.0921	0.092*	0.881 (10)
C12D	1.1400 (6)	0.3988 (9)	0.1007 (5)	0.0677 (15)*	0.881 (10)
C14D	0.8153 (6)	0.4115 (8)	−0.0479 (6)	0.0677 (15)*	0.881 (10)
C8D	0.6593 (5)	0.3891 (10)	−0.1077 (7)	0.080 (3)*	0.881 (10)
H8D	0.5733	0.4112	−0.0417	0.096*	0.881 (10)
C7D	0.6213 (6)	0.3441 (11)	−0.2550 (7)	0.084 (3)*	0.881 (10)
H7D	0.5023	0.3302	−0.2971	0.101*	0.881 (10)
C6D	0.7395 (8)	0.3220 (10)	−0.3403 (6)	0.084 (3)*	0.881 (10)
H6D	0.7039	0.2894	−0.4377	0.101*	0.881 (10)
C5D	0.8967 (6)	0.3430 (10)	−0.2815 (6)	0.077 (3)*	0.881 (10)
H5D	0.9981	0.3262	−0.3354	0.093*	0.881 (10)
C13D	0.9355 (5)	0.3880 (9)	−0.1362 (6)	0.0677 (15)*	0.881 (10)
C9D	0.8668 (9)	0.4644 (10)	0.1095 (8)	0.0677 (15)*	0.881 (10)
C10D	1.1036 (8)	0.4213 (11)	−0.0752 (8)	0.0677 (15)*	0.881 (10)
H10D	1.1766	0.3828	−0.1284	0.081*	0.881 (10)
C15D	0.7350 (11)	0.4622 (15)	0.2138 (10)	0.082 (7)	0.881 (10)
H15D	0.6402	0.4924	0.1585	0.123*	0.881 (10)
H15E	0.7121	0.3959	0.2379	0.123*	0.881 (10)
H15F	0.7704	0.4970	0.3102	0.123*	0.881 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15D	0.084 (5)	0.09 (2)	0.076 (5)	0.029 (7)	0.023 (4)	0.030 (8)

Geometric parameters (Å, º)

C11M—C9M	1.396 (17)	C11D—C12D	1.3981
C11M—C1M	1.4275	C11D—C9D	1.530 (9)
C11M—C12M	1.4381	C1D—C2D	1.3819
C1M—C2M	1.3469	C2D—C3D	1.3688
C2M—C3M	1.4079	C3D—C4D	1.3852
C3M—C4M	1.3384	C4D—C12D	1.3862
C4M—C12M	1.4190	C12D—C10D	1.521 (8)
C12M—C10M	1.391 (17)	C14D—C8D	1.3760
C14M—C9M	1.401 (16)	C14D—C13D	1.4011
C14M—C8M	1.4224	C14D—C9D	1.533 (9)
C14M—C13M	1.4345	C8D—C7D	1.3950
C8M—C7M	1.3527	C7D—C6D	1.3667
C7M—C6M	1.4088	C6D—C5D	1.3792
C6M—C5M	1.3417	C5D—C13D	1.3808
C5M—C13M	1.4193	C13D—C10D	1.509 (9)
C13M—C10M	1.382 (17)	C9D—C15D	1.539 (10)
C9M—C15M	1.510 (19)	C9D—C10D^i	1.623 (16)
C11D—C1D	1.3836	C10D—C9D^i	1.623 (16)
C9M—C11M—C1M	123.2 (16)	C2D—C1D—C11D	120.5
C9M—C11M—C12M	120.1 (16)	C3D—C2D—C1D	120.8
C1M—C11M—C12M	116.6	C2D—C3D—C4D	119.5
C2M—C1M—C11M	122.0	C3D—C4D—C12D	120.3
C1M—C2M—C3M	120.9	C4D—C12D—C11D	120.1
C4M—C3M—C2M	119.7	C4D—C12D—C10D	121.9 (4)
C3M—C4M—C12M	122.0	C11D—C12D—C10D	118.0 (4)
C10M—C12M—C4M	121.2 (17)	C8D—C14D—C13D	119.1
C10M—C12M—C11M	119.7 (17)	C8D—C14D—C9D	123.8 (4)
C4M—C12M—C11M	118.9	C13D—C14D—C9D	117.0 (4)
C9M—C14M—C8M	121.8 (16)	C14D—C8D—C7D	120.4
C9M—C14M—C13M	121.1 (16)	C6D—C7D—C8D	119.9
C8M—C14M—C13M	117.1	C7D—C6D—C5D	120.5
C7M—C8M—C14M	122.1	C6D—C5D—C13D	120.1
C8M—C7M—C6M	120.2	C5D—C13D—C14D	120.0
C5M—C6M—C7M	120.3	C5D—C13D—C10D	121.6 (4)
C6M—C5M—C13M	121.6	C14D—C13D—C10D	118.1 (5)
C10M—C13M—C5M	122.1 (17)	C11D—C9D—C14D	108.1 (8)
C10M—C13M—C14M	119.0 (17)	C11D—C9D—C15D	111.6 (7)
C5M—C13M—C14M	118.8	C14D—C9D—C15D	111.7 (8)
C11M—C9M—C14M	118.8 (19)	C11D—C9D—C10D^i	110.4 (7)
C11M—C9M—C15M	119 (2)	C14D—C9D—C10D^i	109.2 (7)
C14M—C9M—C15M	122 (2)	C15D—C9D—C10D^i	105.8 (11)
C13M—C10M—C12M	121 (2)	C13D—C10D—C12D	108.3 (6)
C1D—C11D—C12D	118.7	C13D—C10D—C9D^i	113.3 (8)
C1D—C11D—C9D	124.1 (4)	C12D—C10D—C9D^i	111.3 (8)
C12D—C11D—C9D	117.1 (4)

Symmetry code: (i) −x+2, −y+1, −z.

(0.1GPa_31hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4440 (4) Å	Cell parameters from 1378 reflections
b = 13.728 (9) Å	θ = 5.7–24.2°
c = 8.5839 (4) Å	µ = 0.07 mm^−1
β = 99.365 (4)°	T = 298 K
V = 981.8 (6) Å^3	Block, colourless
Z = 4	0.28 × 0.25 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	565 independent reflections
Radiation source: fine-focus sealed tube	417 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.7°, θmin = 5.8°
φ– and ω scans	h = −10→10
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −4→4
Tmin = 0.52, Tmax = 1.00	l = −10→9
4488 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.163	w = 1/[σ^2(Fo^2) + (0.0832P)^2 + 0.5071P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
565 reflections	Δρmax = 0.14 e Å^−3
86 parameters	Δρmin = −0.12 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11D	1.0218 (4)	0.4160 (8)	0.1919 (4)	0.0395 (11)*
C1D	1.0530 (4)	0.3964 (9)	0.3517 (4)	0.0483 (12)*
H1D	0.9755	0.4096	0.4143	0.058*
C2D	1.1983 (5)	0.3575 (9)	0.4189 (4)	0.055 (8)
H2D	1.2182	0.3442	0.5265	0.066*
C3D	1.3129 (5)	0.3384 (9)	0.3288 (5)	0.045 (9)
H3D	1.4112	0.3126	0.3753	0.054*
C4D	1.2843 (4)	0.3571 (9)	0.1694 (4)	0.0483 (12)*
H4D	1.3630	0.3438	0.1081	0.058*
C12D	1.1392 (4)	0.3955 (8)	0.1004 (4)	0.0405 (11)*
C14D	0.8154 (4)	0.4119 (8)	−0.0465 (4)	0.0420 (11)*
C8D	0.6575 (5)	0.3874 (9)	−0.1088 (5)	0.0504 (12)*
H8D	0.5764	0.3996	−0.0500	0.061*
C7D	0.6199 (6)	0.3456 (10)	−0.2548 (5)	0.074 (9)
H7D	0.5132	0.3326	−0.2960	0.089*
C6D	0.7369 (6)	0.3231 (10)	−0.3405 (5)	0.060 (10)
H6D	0.7106	0.2947	−0.4397	0.072*
C5D	0.8947 (5)	0.3426 (10)	−0.2792 (5)	0.0555 (13)*
H5D	0.9753	0.3249	−0.3357	0.067*
C13D	0.9341 (4)	0.3878 (8)	−0.1360 (4)	0.0422 (11)*
C9D	0.8656 (4)	0.4632 (9)	0.1095 (4)	0.0401 (12)*
C10D	1.1043 (4)	0.4204 (9)	−0.0742 (4)	0.0426 (12)*
H10D	1.1771	0.3820	−0.1279	0.051*
C15D	0.7344 (4)	0.4603 (9)	0.2148 (5)	0.067 (9)
H15D	0.7716	0.4936	0.3121	0.100*
H15E	0.6392	0.4916	0.1612	0.100*
H15F	0.7105	0.3938	0.2366	0.100*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2D	0.064 (3)	0.06 (3)	0.040 (2)	0.008 (5)	0.0008 (17)	−0.001 (5)
C3D	0.051 (2)	0.02 (3)	0.055 (2)	0.013 (4)	−0.0051 (17)	−0.001 (5)
C7D	0.060 (3)	0.09 (3)	0.063 (3)	−0.016 (5)	−0.012 (2)	0.011 (6)
C6D	0.078 (3)	0.04 (3)	0.053 (3)	−0.006 (5)	−0.009 (2)	0.000 (6)
C15D	0.047 (2)	0.10 (3)	0.054 (2)	0.008 (4)	0.0172 (17)	0.006 (5)

Geometric parameters (Å, º)

C11D—C1D	1.381 (6)	C14D—C9D	1.511 (9)
C11D—C12D	1.390 (6)	C8D—C7D	1.368 (9)
C11D—C9D	1.535 (8)	C7D—C6D	1.360 (8)
C1D—C2D	1.376 (8)	C6D—C5D	1.377 (7)
C2D—C3D	1.359 (7)	C5D—C13D	1.369 (9)
C3D—C4D	1.375 (6)	C13D—C10D	1.516 (7)
C4D—C12D	1.376 (8)	C9D—C15D	1.540 (6)
C12D—C10D	1.518 (6)	C9D—C10D^i	1.654 (16)
C14D—C8D	1.395 (6)	C10D—C9D^i	1.654 (16)
C14D—C13D	1.398 (6)
C1D—C11D—C12D	118.9 (4)	C7D—C6D—C5D	119.5 (6)
C1D—C11D—C9D	123.5 (4)	C13D—C5D—C6D	120.6 (5)
C12D—C11D—C9D	117.6 (4)	C5D—C13D—C14D	120.6 (4)
C2D—C1D—C11D	120.3 (4)	C5D—C13D—C10D	121.7 (4)
C3D—C2D—C1D	120.4 (4)	C14D—C13D—C10D	117.5 (6)
C2D—C3D—C4D	120.3 (5)	C14D—C9D—C11D	107.9 (7)
C3D—C4D—C12D	120.0 (4)	C14D—C9D—C15D	112.5 (5)
C4D—C12D—C11D	120.1 (4)	C11D—C9D—C15D	111.4 (5)
C4D—C12D—C10D	121.8 (3)	C14D—C9D—C10D^i	108.5 (5)
C11D—C12D—C10D	118.1 (4)	C11D—C9D—C10D^i	110.3 (5)
C8D—C14D—C13D	117.3 (5)	C15D—C9D—C10D^i	106.2 (8)
C8D—C14D—C9D	124.4 (4)	C13D—C10D—C12D	107.4 (5)
C13D—C14D—C9D	118.3 (4)	C13D—C10D—C9D^i	112.7 (7)
C7D—C8D—C14D	121.2 (4)	C12D—C10D—C9D^i	112.8 (7)
C6D—C7D—C8D	120.7 (5)

Symmetry code: (i) −x+2, −y+1, −z.

(0.4GPa_0hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.302 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.782 (6) Å	Cell parameters from 906 reflections
b = 14.1170 (9) Å	θ = 5.6–23.9°
c = 7.9575 (5) Å	µ = 0.07 mm^−1
β = 96.241 (18)°	T = 298 K
V = 980.7 (7) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	603 independent reflections
Radiation source: fine-focus sealed tube	331 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.5°, θmin = 5.6°
φ– and ω scans	h = −3→3
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −17→16
Tmin = 0.17, Tmax = 1.00	l = −9→9
4693 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.057P)^2 + 0.6265P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
603 reflections	Δρmax = 0.10 e Å^−3
66 parameters	Δρmin = −0.11 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.101 (2)	0.5795 (4)	0.3085 (7)	0.0479 (18)*
H1	0.0483	0.5511	0.3908	0.057*
C2	0.251 (2)	0.5987 (4)	0.3423 (8)	0.0548 (19)*
H2	0.3006	0.5828	0.4479	0.066*
C3	0.3377 (17)	0.6422 (3)	0.2228 (7)	0.0643 (19)*
H3	0.4415	0.6546	0.2500	0.077*
C4	0.268 (2)	0.6651 (4)	0.0701 (8)	0.0524 (18)*
H4	0.3235	0.6941	−0.0082	0.063*
C5	−0.1901 (18)	0.6794 (3)	−0.3382 (7)	0.0436 (18)*
H5	−0.1321	0.7025	−0.4202	0.052*
C6	−0.346 (2)	0.6694 (4)	−0.3707 (8)	0.050 (2)*
H6	−0.3935	0.6892	−0.4750	0.060*
C7	−0.4368 (16)	0.6308 (3)	−0.2531 (7)	0.0594 (18)*
H7	−0.5421	0.6247	−0.2797	0.071*
C8	−0.3687 (19)	0.6024 (3)	−0.0996 (8)	0.0497 (18)*
H8	−0.4288	0.5758	−0.0226	0.060*
C9	−0.1365 (18)	0.5865 (3)	0.1074 (7)	0.0402 (17)*
C10	0.0382 (19)	0.6690 (3)	−0.1346 (7)	0.0461 (18)*
H10	0.0952	0.6949	−0.2152	0.055*
C11	0.0196 (18)	0.6025 (3)	0.1467 (6)	0.0334 (14)*
C12	0.1104 (18)	0.6462 (3)	0.0257 (7)	0.0401 (16)*
C13	−0.1197 (18)	0.6531 (3)	−0.1750 (6)	0.0363 (16)*
C14	−0.2093 (18)	0.6121 (3)	−0.0537 (7)	0.0365 (15)*
C15	−0.2294 (16)	0.5438 (3)	0.2383 (6)	0.060 (10)
H15A	−0.3343	0.5375	0.1912	0.089*
H15B	−0.1890	0.4825	0.2710	0.089*
H15C	−0.2238	0.5843	0.3357	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15	0.06 (3)	0.065 (3)	0.053 (3)	−0.012 (6)	−0.002 (6)	0.006 (3)

Geometric parameters (Å, º)

C1—C2	1.35 (2)	C7—H7	0.9300
C1—C11	1.438 (10)	C8—C14	1.41 (2)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.418 (15)	C9—C11	1.39 (2)
C2—H2	0.9300	C9—C14	1.416 (9)
C3—C4	1.341 (9)	C9—C15	1.516 (14)
C3—H3	0.9300	C10—C12	1.399 (9)
C4—C12	1.41 (2)	C10—C13	1.41 (2)
C4—H4	0.9300	C10—H10	0.9300
C5—C6	1.37 (2)	C11—C12	1.453 (15)
C5—C13	1.425 (9)	C13—C14	1.432 (15)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.404 (15)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.361 (9)
C2—C1—C11	120.8 (11)	C11—C9—C14	119.9 (11)
C2—C1—H1	119.6	C11—C9—C15	120.1 (7)
C11—C1—H1	119.6	C14—C9—C15	120.0 (12)
C1—C2—C3	122.5 (8)	C12—C10—C13	120.6 (11)
C1—C2—H2	118.7	C12—C10—H10	119.7
C3—C2—H2	118.7	C13—C10—H10	119.7
C4—C3—C2	119.0 (13)	C9—C11—C1	122.9 (10)
C4—C3—H3	120.5	C9—C11—C12	121.2 (7)
C2—C3—H3	120.5	C1—C11—C12	115.8 (12)
C3—C4—C12	121.4 (11)	C10—C12—C4	121.2 (11)
C3—C4—H4	119.3	C10—C12—C11	118.4 (12)
C12—C4—H4	119.3	C4—C12—C11	120.4 (7)
C6—C5—C13	118.0 (11)	C10—C13—C5	119.1 (11)
C6—C5—H5	121.0	C10—C13—C14	120.7 (7)
C13—C5—H5	121.0	C5—C13—C14	120.3 (13)
C5—C6—C7	122.8 (8)	C8—C14—C9	123.1 (11)
C5—C6—H6	118.6	C8—C14—C13	117.7 (7)
C7—C6—H6	118.6	C9—C14—C13	119.1 (13)
C8—C7—C6	119.1 (12)	C9—C15—H15A	109.5
C8—C7—H7	120.4	C9—C15—H15B	109.5
C6—C7—H7	120.4	H15A—C15—H15B	109.5
C7—C8—C14	122.0 (11)	C9—C15—H15C	109.5
C7—C8—H8	119.0	H15A—C15—H15C	109.5
C14—C8—H8	119.0	H15B—C15—H15C	109.5

(0.4GPa_15minUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.303 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.785 (7) Å	Cell parameters from 882 reflections
b = 14.1121 (10) Å	θ = 5.6–23.9°
c = 7.9525 (6) Å	µ = 0.07 mm^−1
β = 96.26 (2)°	T = 298 K
V = 980.0 (8) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	605 independent reflections
Radiation source: fine-focus sealed tube	322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.082
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.5°, θmin = 5.6°
φ– and ω scans	h = −3→3
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −17→16
Tmin = 0.19, Tmax = 1.00	l = −9→9
4727 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.174	w = 1/[σ^2(Fo^2) + (0.0696P)^2 + 0.5459P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
605 reflections	Δρmax = 0.12 e Å^−3
66 parameters	Δρmin = −0.11 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.101 (2)	0.5798 (4)	0.3079 (8)	0.0463 (19)*
H1	0.0480	0.5514	0.3895	0.056*
C2	0.253 (2)	0.5987 (4)	0.3424 (8)	0.053 (2)*
H2	0.3026	0.5823	0.4477	0.064*
C3	0.3366 (18)	0.6421 (4)	0.2233 (7)	0.0614 (19)*
H3	0.4402	0.6549	0.2500	0.074*
C4	0.266 (2)	0.6651 (4)	0.0712 (8)	0.0513 (19)*
H4	0.3225	0.6945	−0.0065	0.062*
C5	−0.1906 (19)	0.6795 (3)	−0.3383 (7)	0.0434 (19)*
H5	−0.1326	0.7033	−0.4198	0.052*
C6	−0.346 (2)	0.6690 (4)	−0.3713 (8)	0.050 (2)*
H6	−0.3936	0.6880	−0.4762	0.059*
C7	−0.4369 (17)	0.6309 (3)	−0.2538 (7)	0.0557 (18)*
H7	−0.5422	0.6250	−0.2804	0.067*
C8	−0.369 (2)	0.6028 (4)	−0.1003 (8)	0.0484 (18)*
H8	−0.4295	0.5767	−0.0233	0.058*
C9	−0.1345 (19)	0.5861 (4)	0.1090 (7)	0.0384 (17)*
C10	0.037 (2)	0.6691 (4)	−0.1348 (7)	0.0455 (18)*
H10	0.0929	0.6955	−0.2158	0.055*
C11	0.0223 (19)	0.6035 (3)	0.1456 (7)	0.0342 (15)*
C12	0.1100 (18)	0.6462 (3)	0.0245 (7)	0.0384 (16)*
C13	−0.1200 (19)	0.6526 (3)	−0.1739 (7)	0.0351 (16)*
C14	−0.2089 (19)	0.6117 (3)	−0.0529 (7)	0.0365 (16)*
C15	−0.2282 (17)	0.5439 (4)	0.2387 (6)	0.059 (10)
H15A	−0.3327	0.5373	0.1904	0.089*
H15B	−0.1878	0.4827	0.2724	0.089*
H15C	−0.2236	0.5847	0.3356	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15	0.06 (3)	0.064 (3)	0.051 (3)	0.002 (6)	0.003 (6)	0.006 (3)

Geometric parameters (Å, º)

C1—C2	1.36 (2)	C7—H7	0.9300
C1—C11	1.436 (11)	C8—C14	1.42 (2)
C1—H1	0.9300	C8—H8	0.9300
C2—C3	1.402 (15)	C9—C11	1.40 (2)
C2—H2	0.9300	C9—C14	1.425 (10)
C3—C4	1.337 (9)	C9—C15	1.510 (15)
C3—H3	0.9300	C10—C12	1.394 (9)
C4—C12	1.41 (2)	C10—C13	1.40 (2)
C4—H4	0.9300	C10—H10	0.9300
C5—C6	1.37 (2)	C11—C12	1.430 (15)
C5—C13	1.436 (9)	C13—C14	1.426 (16)
C5—H5	0.9300	C15—H15A	0.9600
C6—C7	1.399 (16)	C15—H15B	0.9600
C6—H6	0.9300	C15—H15C	0.9600
C7—C8	1.359 (9)
C2—C1—C11	120.1 (12)	C11—C9—C14	119.2 (11)
C2—C1—H1	119.9	C11—C9—C15	121.7 (7)
C11—C1—H1	119.9	C14—C9—C15	119.1 (13)
C1—C2—C3	121.7 (8)	C12—C10—C13	120.6 (11)
C1—C2—H2	119.2	C12—C10—H10	119.7
C3—C2—H2	119.2	C13—C10—H10	119.7
C4—C3—C2	119.5 (13)	C9—C11—C12	121.6 (7)
C4—C3—H3	120.2	C9—C11—C1	120.8 (11)
C2—C3—H3	120.2	C12—C11—C1	117.5 (13)
C3—C4—C12	122.3 (12)	C10—C12—C4	122.3 (11)
C3—C4—H4	118.9	C10—C12—C11	118.8 (13)
C12—C4—H4	118.9	C4—C12—C11	118.9 (7)
C6—C5—C13	117.9 (12)	C10—C13—C14	121.1 (8)
C6—C5—H5	121.0	C10—C13—C5	118.4 (11)
C13—C5—H5	121.0	C14—C13—C5	120.5 (13)
C5—C6—C7	122.8 (8)	C8—C14—C9	124.1 (12)
C5—C6—H6	118.6	C8—C14—C13	117.1 (7)
C7—C6—H6	118.6	C9—C14—C13	118.8 (13)
C8—C7—C6	119.1 (13)	C9—C15—H15A	109.5
C8—C7—H7	120.5	C9—C15—H15B	109.5
C6—C7—H7	120.5	H15A—C15—H15B	109.5
C7—C8—C14	122.5 (11)	C9—C15—H15C	109.5
C7—C8—H8	118.7	H15A—C15—H15C	109.5
C14—C8—H8	118.7	H15B—C15—H15C	109.5

(0.4GPa_4hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.304 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.7518 (10) Å	Cell parameters from 813 reflections
b = 14.1290 (14) Å	θ = 5.6–23.5°
c = 7.9658 (9) Å	µ = 0.07 mm^−1
β = 96.24 (3)°	T = 298 K
V = 979.17 (19) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	591 independent reflections
Radiation source: fine-focus sealed tube	313 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.083
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.0°, θmin = 5.6°
φ– and ω scans	h = −3→3
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −16→16
Tmin = 0.10, Tmax = 1.00	l = −9→9
4662 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.064	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0853P)^2 + 0.1783P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
591 reflections	Δρmax = 0.11 e Å^−3
66 parameters	Δρmin = −0.09 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11M	1.0260 (19)	0.3971 (3)	0.1475 (7)	0.0376 (16)*
C1M	1.102 (2)	0.4202 (4)	0.3083 (8)	0.051 (2)*
H1M	1.0482	0.4493	0.3885	0.061*
C2M	1.250 (2)	0.4004 (4)	0.3447 (9)	0.059 (2)*
H2M	1.2978	0.4147	0.4516	0.071*
C3M	1.3370 (18)	0.3576 (3)	0.2240 (7)	0.067 (2)*
H3M	1.4411	0.3455	0.2515	0.081*
C4M	1.269 (2)	0.3352 (4)	0.0721 (8)	0.0552 (19)*
H4M	1.3258	0.3067	−0.0058	0.066*
C12M	1.1099 (19)	0.3539 (3)	0.0261 (7)	0.0440 (17)*
C14M	0.7932 (19)	0.3891 (3)	−0.0533 (7)	0.0390 (17)*
C8M	0.6332 (19)	0.3970 (3)	−0.1000 (8)	0.0494 (19)*
H8M	0.5721	0.4227	−0.0230	0.059*
C7M	0.5653 (17)	0.3685 (3)	−0.2530 (7)	0.0608 (19)*
H7M	0.4595	0.3738	−0.2797	0.073*
C6M	0.658 (2)	0.3307 (4)	−0.3707 (8)	0.051 (2)*
H6M	0.6112	0.3118	−0.4759	0.061*
C5M	0.8122 (19)	0.3209 (3)	−0.3365 (7)	0.046 (2)*
H5M	0.8716	0.2972	−0.4169	0.055*
C13M	0.8793 (19)	0.3479 (4)	−0.1746 (7)	0.0401 (17)*
C9M	0.8672 (19)	0.4132 (4)	0.1086 (7)	0.0425 (18)*
C10M	1.036 (2)	0.3310 (3)	−0.1330 (7)	0.0479 (18)*
H10M	1.0920	0.3039	−0.2130	0.057*
C15M	0.7709 (17)	0.4559 (3)	0.2381 (6)	0.071 (11)
H15A	0.6661	0.4615	0.1893	0.107*
H15B	0.7759	0.4157	0.3357	0.107*
H15C	0.8103	0.5175	0.2706	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15M	0.09 (3)	0.065 (3)	0.059 (4)	0.004 (6)	0.001 (7)	−0.008 (3)

Geometric parameters (Å, º)

C11M—C9M	1.41 (2)	C14M—C13M	1.414 (16)
C11M—C12M	1.415 (15)	C14M—C9M	1.420 (9)
C11M—C1M	1.416 (10)	C8M—C7M	1.358 (8)
C1M—C2M	1.32 (2)	C7M—C6M	1.409 (16)
C2M—C3M	1.424 (16)	C6M—C5M	1.36 (2)
C3M—C4M	1.329 (9)	C5M—C13M	1.410 (9)
C4M—C12M	1.42 (2)	C13M—C10M	1.39 (2)
C12M—C10M	1.397 (9)	C9M—C15M	1.526 (15)
C14M—C8M	1.41 (2)
C9M—C11M—C12M	119.5 (8)	C13M—C14M—C9M	119.7 (14)
C9M—C11M—C1M	121.2 (11)	C7M—C8M—C14M	122.5 (11)
C12M—C11M—C1M	119.3 (13)	C8M—C7M—C6M	118.9 (12)
C2M—C1M—C11M	120.1 (12)	C5M—C6M—C7M	122.5 (8)
C1M—C2M—C3M	121.6 (8)	C6M—C5M—C13M	117.6 (12)
C4M—C3M—C2M	119.6 (13)	C10M—C13M—C5M	118.2 (11)
C3M—C4M—C12M	121.4 (12)	C10M—C13M—C14M	119.4 (8)
C10M—C12M—C11M	119.6 (13)	C5M—C13M—C14M	122.4 (14)
C10M—C12M—C4M	122.4 (11)	C11M—C9M—C14M	120.2 (11)
C11M—C12M—C4M	118.0 (8)	C11M—C9M—C15M	121.3 (7)
C8M—C14M—C13M	116.0 (7)	C14M—C9M—C15M	118.5 (13)
C8M—C14M—C9M	124.2 (12)	C13M—C10M—C12M	121.6 (11)

(0.4GPa_10hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.310 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.70 (5) Å	Cell parameters from 422 reflections
b = 14.110 (8) Å	θ = 5.6–23.2°
c = 7.995 (5) Å	µ = 0.07 mm^−1
β = 96.57 (14)°	T = 298 K
V = 975 (6) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	586 independent reflections
Radiation source: fine-focus sealed tube	212 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.164
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.0°, θmin = 5.6°
φ– and ω scans	h = −3→3
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −16→16
Tmin = 0.09, Tmax = 1.00	l = −9→9
4596 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.084	H-atom parameters constrained
wR(F^2) = 0.308	w = 1/[σ^2(Fo^2) + (0.1722P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
586 reflections	Δρmax = 0.16 e Å^−3
52 parameters	Δρmin = −0.11 e Å^−3
65 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C11M	1.0225 (11)	0.3986 (4)	0.1476 (7)	0.0640 (16)*	0.900 (6)
C1M	1.1042 (12)	0.4200 (4)	0.3082 (6)	0.0748 (19)*	0.900 (6)
H1M	1.0422	0.4555	0.4027	0.090*	0.900 (6)
C2M	1.2558 (12)	0.4004 (4)	0.3454 (6)	0.078 (2)*	0.900 (6)
H2M	1.3128	0.4136	0.4585	0.094*	0.900 (6)
C3M	1.3408 (11)	0.3583 (4)	0.2254 (9)	0.078 (2)*	0.900 (6)
H3M	1.4559	0.3449	0.2553	0.094*	0.900 (6)
C4M	1.2699 (12)	0.3366 (4)	0.0728 (7)	0.0748 (19)*	0.900 (6)
H4M	1.3234	0.3050	−0.0171	0.090*	0.900 (6)
C12M	1.1101 (12)	0.3543 (4)	0.0271 (5)	0.0640 (16)*	0.900 (6)
C14M	0.7957 (12)	0.3871 (4)	−0.0531 (5)	0.0640 (16)*	0.900 (6)
C8M	0.6336 (11)	0.3963 (4)	−0.0991 (8)	0.0748 (19)*	0.900 (6)
H8M	0.5653	0.4260	−0.0163	0.090*	0.900 (6)
C7M	0.5652 (11)	0.3706 (4)	−0.2529 (9)	0.078 (2)*	0.900 (6)
H7M	0.4400	0.3808	−0.2861	0.094*	0.900 (6)
C6M	0.6541 (13)	0.3316 (4)	−0.3725 (6)	0.078 (2)*	0.900 (6)
H6M	0.6020	0.3129	−0.4818	0.094*	0.900 (6)
C5M	0.8075 (12)	0.3208 (4)	−0.3355 (6)	0.0748 (19)*	0.900 (6)
H5M	0.8729	0.2942	−0.4168	0.090*	0.900 (6)
C13M	0.8850 (11)	0.3486 (4)	−0.1772 (7)	0.0640 (16)*	0.900 (6)
C9M	0.8633 (16)	0.4130 (5)	0.1060 (9)	0.0640 (16)*	0.900 (6)
C10M	1.0361 (18)	0.3308 (5)	−0.1297 (9)	0.0640 (16)*	0.900 (6)
H10M	1.0933	0.3013	−0.2062	0.077*	0.900 (6)
C15M	0.766 (2)	0.4543 (7)	0.2335 (10)	0.082 (3)*	0.900 (6)
H15A	0.8313	0.4680	0.3360	0.122*	0.900 (6)
H15B	0.7179	0.5117	0.1896	0.122*	0.900 (6)
H15C	0.6882	0.4095	0.2560	0.122*	0.900 (6)
C11D	1.013 (5)	0.4176 (17)	0.209 (3)	0.069 (7)*	0.100 (6)
C1D	1.047 (6)	0.393 (2)	0.376 (3)	0.073 (9)*	0.100 (6)
H1D	0.9789	0.4082	0.4545	0.088*	0.100 (6)
C2D	1.184 (6)	0.347 (3)	0.432 (4)	0.089 (9)*	0.100 (6)
H2D	1.2017	0.3257	0.5575	0.107*	0.100 (6)
C3D	1.288 (5)	0.325 (3)	0.322 (5)	0.089 (9)*	0.100 (6)
H3D	1.3917	0.2922	0.3645	0.107*	0.100 (6)
C4D	1.257 (5)	0.350 (3)	0.154 (5)	0.073 (9)*	0.100 (6)
H4D	1.3262	0.3348	0.0621	0.088*	0.100 (6)
C12D	1.121 (4)	0.397 (2)	0.097 (4)	0.069 (7)*	0.100 (6)
C14D	0.806 (4)	0.4253 (18)	−0.028 (4)	0.069 (7)*	0.100 (6)
C8D	0.651 (4)	0.404 (3)	−0.063 (5)	0.073 (9)*	0.100 (6)
H8D	0.5766	0.4333	0.0155	0.088*	0.100 (6)
C7D	0.599 (5)	0.350 (3)	−0.205 (5)	0.089 (9)*	0.100 (6)
H7D	0.4811	0.3375	−0.2290	0.107*	0.100 (6)
C6D	0.701 (7)	0.319 (3)	−0.309 (4)	0.089 (9)*	0.100 (6)
H6D	0.6568	0.2807	−0.4007	0.107*	0.100 (6)
C5D	0.857 (6)	0.338 (3)	−0.275 (4)	0.073 (9)*	0.100 (6)
H5D	0.9472	0.3145	−0.3438	0.088*	0.100 (6)
C13D	0.910 (5)	0.392 (2)	−0.135 (4)	0.069 (7)*	0.100 (6)
C9D	0.873 (4)	0.4747 (18)	0.134 (3)	0.069 (7)*	0.100 (6)
C10D	1.077 (5)	0.4175 (16)	−0.089 (4)	0.069 (7)*	0.100 (6)
H10D	1.1383	0.3746	−0.1511	0.083*	0.100 (6)
C15D	0.755 (6)	0.487 (5)	0.260 (6)	0.107 (19)*	0.100 (6)
H15D	0.8025	0.5184	0.3589	0.161*	0.100 (6)
H15E	0.6692	0.5245	0.2098	0.161*	0.100 (6)
H15F	0.7175	0.4260	0.2900	0.161*	0.100 (6)

Geometric parameters (Å, º)

C11M—C9M	1.402 (15)	C11D—C12D	1.3982
C11M—C1M	1.4276	C11D—C9D	1.525 (17)
C11M—C12M	1.4381	C1D—C2D	1.3819
C1M—C2M	1.3469	C2D—C3D	1.3688
C2M—C3M	1.4080	C3D—C4D	1.3852
C3M—C4M	1.3384	C4D—C12D	1.3862
C4M—C12M	1.4191	C12D—C10D	1.519 (17)
C12M—C10M	1.382 (8)	C14D—C8D	1.3760
C14M—C9M	1.387 (8)	C14D—C13D	1.4011
C14M—C8M	1.4224	C14D—C9D	1.523 (16)
C14M—C13M	1.4345	C8D—C7D	1.3950
C8M—C7M	1.3527	C7D—C6D	1.3666
C7M—C6M	1.4087	C6D—C5D	1.3792
C6M—C5M	1.3417	C5D—C13D	1.3808
C5M—C13M	1.4193	C13D—C10D	1.504 (19)
C13M—C10M	1.350 (15)	C9D—C15D	1.534 (19)
C9M—C15M	1.513 (14)	C9D—C10D^i	1.633 (18)
C11D—C1D	1.3836	C10D—C9D^i	1.633 (18)
C9M—C11M—C1M	124.1 (6)	C2D—C1D—C11D	120.5
C9M—C11M—C12M	119.3 (6)	C3D—C2D—C1D	120.8
C1M—C11M—C12M	116.6	C2D—C3D—C4D	119.5
C2M—C1M—C11M	122.0	C3D—C4D—C12D	120.3
C1M—C2M—C3M	120.9	C4D—C12D—C11D	120.1
C4M—C3M—C2M	119.7	C4D—C12D—C10D	121.3 (17)
C3M—C4M—C12M	122.0	C11D—C12D—C10D	118.3 (17)
C10M—C12M—C4M	122.2 (8)	C8D—C14D—C13D	119.1
C10M—C12M—C11M	119.0 (8)	C8D—C14D—C9D	123.2 (16)
C4M—C12M—C11M	118.9	C13D—C14D—C9D	117.3 (17)
C9M—C14M—C8M	121.1 (8)	C14D—C8D—C7D	120.4
C9M—C14M—C13M	121.8 (8)	C6D—C7D—C8D	119.9
C8M—C14M—C13M	117.1	C7D—C6D—C5D	120.5
C7M—C8M—C14M	122.0	C6D—C5D—C13D	120.1
C8M—C7M—C6M	120.2	C5D—C13D—C14D	120.0
C5M—C6M—C7M	120.3	C5D—C13D—C10D	123.7 (17)
C6M—C5M—C13M	121.6	C14D—C13D—C10D	116.3 (17)
C10M—C13M—C5M	123.2 (6)	C14D—C9D—C11D	107.8 (17)
C10M—C13M—C14M	117.6 (6)	C14D—C9D—C15D	113 (2)
C5M—C13M—C14M	118.8	C11D—C9D—C15D	112 (2)
C14M—C9M—C11M	118.9 (9)	C14D—C9D—C10D^i	109.0 (18)
C14M—C9M—C15M	120.6 (11)	C11D—C9D—C10D^i	111 (2)
C11M—C9M—C15M	120.5 (8)	C15D—C9D—C10D^i	105 (2)
C13M—C10M—C12M	123.2 (10)	C13D—C10D—C12D	108.7 (18)
C1D—C11D—C12D	118.7	C13D—C10D—C9D^i	116 (2)
C1D—C11D—C9D	126.0 (16)	C12D—C10D—C9D^i	111 (2)
C12D—C11D—C9D	115.0 (16)

Symmetry code: (i) −x+2, −y+1, −z.

(0.4GPa_20hUV)

Crystal data

C15H12	F(000) = 408
Mr = 192.25	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.48 (5) Å	Cell parameters from 350 reflections
b = 13.582 (7) Å	θ = 5.7–15.4°
c = 8.538 (5) Å	µ = 0.07 mm^−1
β = 99.20 (17)°	T = 298 K
V = 971 (6) Å^3	Block, colourless
Z = 4	0.22 × 0.20 × 0.05 mm

Data collection

KM4 with Eos CCD diffractometer	541 independent reflections
Radiation source: fine-focus sealed tube	177 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.283
Detector resolution: 15.9718 pixels mm^-1	θmax = 25.4°, θmin = 5.7°
φ– and ω scans	h = −2→2
Absorption correction: multi-scan SCALE3 ABSPACK (Rigaku Oxford Diffraction, 2015).	k = −16→15
Tmin = 0.40, Tmax = 1.00	l = −10→10
4445 measured reflections

Refinement

Refinement on F^2	Primary atom site location: isomorphous structure methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.140	H-atom parameters constrained
wR(F^2) = 0.405	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
541 reflections	Δρmax = 0.23 e Å^−3
42 parameters	Δρmin = −0.16 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C11D	1.019 (2)	0.4161 (7)	0.1931 (13)	0.069 (5)*
C1D	1.050 (2)	0.3969 (7)	0.3542 (12)	0.085 (5)*
H1D	0.9746	0.4118	0.4190	0.102*
C2D	1.196 (2)	0.3579 (7)	0.4224 (8)	0.090 (5)*
H2D	1.2116	0.3403	0.5430	0.108*
C3D	1.311 (2)	0.3366 (7)	0.3320 (12)	0.077 (5)*
H3D	1.4205	0.3093	0.3843	0.093*
C4D	1.282 (2)	0.3562 (7)	0.1707 (11)	0.074 (5)*
H4D	1.3597	0.3414	0.0934	0.089*
C12D	1.138 (2)	0.3965 (7)	0.1012 (8)	0.075 (5)*
C14D	0.805 (2)	0.4096 (5)	−0.0457 (9)	0.061 (4)*
C8D	0.648 (2)	0.3881 (6)	−0.1051 (12)	0.070 (5)*
H8D	0.5626	0.4111	−0.0383	0.084*
C7D	0.608 (2)	0.3432 (6)	−0.2530 (13)	0.086 (5)*
H7D	0.4886	0.3299	−0.2949	0.103*
C6D	0.725 (3)	0.3200 (5)	−0.3394 (9)	0.080 (5)*
H6D	0.6886	0.2874	−0.4372	0.096*
C5D	0.883 (2)	0.3400 (6)	−0.2809 (11)	0.077 (5)*
H5D	0.9840	0.3222	−0.3356	0.092*
C13D	0.924 (2)	0.3850 (6)	−0.1350 (12)	0.060 (4)*
C9D	0.872 (5)	0.4616 (10)	0.1124 (18)	0.070 (5)*
C10D	1.097 (4)	0.4182 (9)	−0.0784 (13)	0.059 (4)*
H10D	1.1676	0.3790	−0.1338	0.070*
C15D	0.732 (5)	0.4595 (11)	0.2100 (17)	0.10 (3)
H15D	0.6398	0.4904	0.1503	0.153*
H15E	0.7074	0.3925	0.2322	0.153*
H15F	0.7631	0.4943	0.3080	0.153*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C15D	0.13 (11)	0.116 (13)	0.066 (10)	−0.04 (2)	0.038 (17)	−0.006 (8)

Geometric parameters (Å, º)

C11D—C1D	1.3836	C14D—C9D	1.548 (18)
C11D—C12D	1.3982	C8D—C7D	1.3950
C11D—C9D	1.46 (4)	C7D—C6D	1.3667
C1D—C2D	1.3819	C6D—C5D	1.3792
C2D—C3D	1.3688	C5D—C13D	1.3807
C3D—C4D	1.3852	C13D—C10D	1.54 (3)
C4D—C12D	1.3861	C9D—C15D	1.55 (5)
C12D—C10D	1.545 (12)	C9D—C10D^i	1.69 (2)
C14D—C8D	1.3760	C10D—C9D^i	1.69 (2)
C14D—C13D	1.4011
C1D—C11D—C12D	118.7	C7D—C6D—C5D	120.5
C1D—C11D—C9D	124.2 (14)	C6D—C5D—C13D	120.1
C12D—C11D—C9D	117.0 (15)	C5D—C13D—C14D	120.0
C2D—C1D—C11D	120.5	C5D—C13D—C10D	120.1 (10)
C3D—C2D—C1D	120.8	C14D—C13D—C10D	119.6 (11)
C2D—C3D—C4D	119.5	C11D—C9D—C14D	112.6 (18)
C3D—C4D—C12D	120.3	C11D—C9D—C15D	113.9 (15)
C4D—C12D—C11D	120.1	C14D—C9D—C15D	105 (3)
C4D—C12D—C10D	122.9 (15)	C11D—C9D—C10D^i	110 (2)
C11D—C12D—C10D	116.9 (16)	C14D—C9D—C10D^i	109.8 (9)
C8D—C14D—C13D	119.1	C15D—C9D—C10D^i	105.5 (18)
C8D—C14D—C9D	128.1 (18)	C13D—C10D—C12D	107.9 (17)
C13D—C14D—C9D	112.8 (19)	C13D—C10D—C9D^i	113.7 (19)
C14D—C8D—C7D	120.4	C12D—C10D—C9D^i	109.8 (10)
C6D—C7D—C8D	119.9

Symmetry code: (i) −x+2, −y+1, −z.