Structural transformations and stability of benzo[a]pyrene under high pressure

Benzo[a]pyrene (BaP), C₂₀H₁₂, is a representative of polycyclic aromatic hydro­carbons (PAHs), which are ubiquitous in nature and the universe, where they are subjected to extreme conditions. This paper reports the results of investigations of the high-pressure behavior of BaP up to 28 GPa using in situ synchrotron single-crystal X-ray diffraction. We identified two previously unknown polymorphs, BaP-II (P2₁/c) at 4.8 GPa and BaP-III (P1) at 7.1 GPa. The structural transformation from BaP-I (P2₁/c) to BaP-II (P2₁/c) manifests as an abrupt change in the intermolecular angle and the unit-cell parameters a and b, whereas the transformation from BaP-II (P2₁/c) to BaP-III (P1) is characterized by a decrease in symmetry. According to density functional theory calculations, BaP-III is the most stable phase above 3.5 GPa. These studies advance our understanding of the structural dynamics and stability of PAHs under high pressure.

1. Introduction

Polycyclic aromatic hydro­carbons (PAHs) are complex organic compounds consisting of two or more condensed benzene rings. Owing to their exceptional properties and widespread applications, these compounds have attracted significant attention from geoscientists, chemists and physicists (Silinsh & Cápek, 1997; Farchioni, 2001; Allamandola et al., 1987). PAHs are ubiquitous in interstellar space, comprising 20% of the carbon in the universe and potentially representing the most abundant free organic molecules in space (Allamandola et al., 1985; Ehrenfreund & Charnley, 2000; d'Hendecourt & Ehrenfreund, 1997). It is thought that research into the evolution of PAHs under pressure may help us to understand the origins of our universe (Mimura et al., 2005; Mimura & Toyama, 2005).

Benzo[a]pyrene (BaP) is one of the two isomeric species of benzopyrene (C₂₀H₁₂), a representative of PAHs, formed by a benzene ring fused to pyrene. The compound is abundant (Bukowska et al., 2022) and can be found, for example, in coal tar as a product of incomplete combustion of organic matter at high temperatures. It is a yellow solid under ambient conditions.

Crystals of BaP were first described by Iball (1936), who obtained them from BaP solutions in the form of needles and plates and determined their symmetry and unit-cell parameters using X-ray diffraction (XRD). The needle-shaped crystals were monoclinic (P2₁/c) whereas the plate-shaped crystals were orthorhombic (P2₁2₁2₁). The crystal structure of the monoclinic BaP was later solved (Iball & Young, 1956) and refined (Iball et al., 1976). Subsequently, one more ortho­rhombic BaP polymorph was reported (Contag, 1978). However, it was found to be unstable and gradually, within 6 months, transformed into the known monoclinic BaP. Low-temperature single-crystal XRD (SC-XRD) measurements at 120 K (Carrell et al., 1997) enabled a more precise structure analysis.

In this work, we have investigated the behavior of BaP in the pressure range from ambient to 35 GPa using synchrotron SC-XRD in a diamond anvil cell (DAC). We have observed two previously unknown high-pressure polymorphs, BaP-II and BaP-III, and report the results of the analysis of their structures under pressure.

2. Experimental

2.1. Sample preparation

A crystalline powder of BaP of 96% purity was purchased from Merck. Single crystals were selected under an optical microscope and preselected for high-pressure XRD studies in DAC No. 1 at ambient pressure (see Table S1 of the supporting information for a summary of all experiments). The two preselected crystals and a piece of ruby were loaded in the membrane-type DAC No. 2 equipped with Boehler–Almax type diamonds (Boehler, 2006) with culets 250 µm in size and a rhenium gasket with a hole ∼120 µm in diameter and a thickness of ∼30 µm. He was used as a pressure-transmitting medium. The DAC No. 2 was gradually pressurized from 2.2 to 35 GPa.

2.2. SC-XRD experiments

SC-XRD studies at room temperature were conducted in DAC No. 1 and DAC No. 2 on the ID15B beamline (λ = 0.4100 Å, ESRF) with a beam size of approximately 2 × 2 µm. In both experiments a micro-grain of tungsten was placed at the center of the pressure chamber along with the sample. The strong X-ray absorption signal of tungsten was used to adjust the rotation center. The pressure was determined by the ruby luminescence method (Mao et al., 1986). At each pressure step, the data were collected in step scans of 0.5° on rotating the DAC from −34 to +34° about the vertical axis (ω scan). For single-crystal data analysis (peak search, unit-cell finding and data integration), the CrysAlisPro software (Rigaku Oxford Diffraction, 2015) was employed, and the crystal structures were determined using SHELX (Sheldrick, 2008) and refined utilizing Olex2 (Dolomanov et al., 2009). Crystal structure visualization was performed using VESTA (Momma & Izumi, 2011). EoSFIT7 (Angel et al., 2014) was used to fit the pressure–volume data.

2.3. Theoretical calculations

Our density functional theory (DFT) calculations were performed using the Vienna Ab-initio Simulation Package (VASP) (Kresse & Furthmüller, 1996) with the projector-augmented-wave method (Blöchl, 1994) and the generalized gradient approximation functional was used for calculating the exchange-correlation energy, as proposed by Perdew, Burke & Ernzerhof (PBE) (Kresse & Joubert, 1999). Additionally, we employed the DFT-D3 method for dispersion correction (Grimme et al., 2011). The Brillouin zone was sampled with a 7 × 1 × 2 Monkhorst–Pack (Monkhorst & Pack, 1976) special k-point grid for BaP-I and BaP-II, and 7 × 2 × 1 for BaP-III. Furthermore, the valence states 2s²2p² for carbon and 1s¹ for hydrogen were used with the energy cutoff of 520 eV for the plane-wave basis set. The geometries were optimized until the remaining atomic forces were less than 5 × 10⁻³ eV Å⁻¹ and the energy convergence criterion was set at 10⁻⁵ eV.

3. Results

On compression of BaP-I (P2₁/c) to 4.8 GPa in an He pressure medium, we observed a phase transition to a previously unknown monoclinic polymorph BaP-II (P2₁/c). The next phase transition occurred at 7.1 GPa to BaP-III with a triclinic structure (P1), which was preserved up to about 28 GPa. At the next pressure step of 35 GPa, the XRD pattern disappeared. Below we describe in detail the structures of all BaP polymorphs observed in this work.

The structure of BaP-I determined at ambient and 2.2 GPa [Fig. 1(a)] is similar to the previously reported monoclinic structure (Carrell et al., 1997). For a detailed comparison with BaP-I at 120 K, see Table S2. The structure is monoclinic (space group No. 14, P2₁/c) with the following unit-cell parameters under ambient conditions: a = 4.5384(3) Å, b = 20.439(5) Å, c = 13.531(2) Å, β = 97.006(8)° and V = 1245.8(4) ų.

Figure 1 Crystal structures of BaP polymorphs. (a) BaP-I under ambient conditions, as viewed along the a (top) and c (bottom) axes; (b) BaP-II at 4.8 GPa, viewed along the a (top) and c (bottom) axes; (c) BaP-III at 7.1 GPa, as viewed along the a (top) and b (bottom) axes: carbon atoms – black, hydrogen atoms – white.

The structure of the previously unknown monoclinic polymorph, BaP-II (space group No. 14, P2₁/c), was solved and refined at 4.8 GPa [Table S3, Fig. 1(b)] with the unit-cell parameters a = 3.59710(10) Å, b = 21.658(9) Å, c = 12.7908(9) Å, β = 95.339(5)° and V = 992.2(4) ų. The arrangement of molecules in BaP-II is similar to that in BaP-I. In both structures, the molecules display a herringbone pattern projected along the a direction [Figs. 1(a) and 1(b), top], but the intermolecular angles in BaP-I and BaP-II are noticeably different [see the projections along the b axis in Figs. 1(a) and 1(b), bottom]. In our previous study of pyrene under pressure (Zhou et al., 2024), we also noticed that the phase transformation of pyrene-I to pyrene-II is accompanied by a change of the intermolecular angle, whereas the space-group symmetry remains the same.

Further compression of BaP-II led to the formation of a new triclinic polymorph, BaP-III (space group No. 2, P1), which we first observed at 7.1 GPa [Fig. 1(c)]. The unit-cell parameters at 7.1 GPa are as follows: a = 3.4912(1) Å, b = 12.687(3) Å, c = 21.531(6) Å, α = 91.51(2)°, β = 90.434(9)°, γ = 95.820(8)° and V = 911.5(2) ų. Table S4 provides detailed crystallographic data for BaP-III at six pressure points in the range 7.1–27.9 GPa. As the α and β angles are very close to 90°, the structure of BaP-III, if viewed along the a and b directions, looks very similar to those of BaP-I and BaP-II (Fig. 1). However, crystallographically, due to the lower symmetry, the molecular arrangement in BaP-III is missing the herringbone pattern. A detailed geometrical analysis of the structures in different polymorphs is given in the Discussion below.

4. Discussion

4.1. Compressional behavior of the polymorphs of BaP

The compressional behavior of the polymorphs of BaP up to 27.9 GPa is presented in Fig. 2. The values of the unit-cell volume per formula unit for BaP-I, BaP-II and BaP-III as a function of pressure were obtained from our experiments (Table S5). In Fig. 2 they are shown by solid symbols of different colors. These pressure–volume data were fitted using the third-order Birch–Murnaghan equation of state (EoS) with the volume V₀ = 311.45 ų, which is the volume of BaP-I under ambient conditions. The bulk modulus, K₀, and its first derivative, K′, were determined to be 7.7(7) GPa and 10.10(10), respectively.

Figure 2 Pressure dependence of the unit-cell volume per formula unit for polymorphs of BaP up to 27.9 GPa. The experimental data for BaP-I are shown by green solid triangles, for BaP-II by red inversed solid triangles and for BaP-III by blue solid circles. The solid black line shows the fit of all pressure–volume experimental points using the third-order Birch–Murnaghan EoS with the parameters V0 = 311.45 Å^3, K0 = 7.7(7) GPa and K′ = 10.10(10). The dashed black line shows the fit of the calculated pressure–volume data points with the parameters V0 = 295.92 Å^3, K0 = 11.53(14) GPa and K′ = 8.28(9).

The pressure–volume data points calculated using DFT for each polymorph (Table S6) are consistent with the pressure points at which the phases were observed experimentally. The calculated data have also been fitted using the third-order Birch–Murnaghan EoS. The EoS parameters appeared to be as follows: V₀ = 295.92 ų, K₀ = 11.53(14) GPa and K′ = 8.28(9). The volume values from the calculated data fitting are consistently lower than those from the experimental data fitting. This observation can be attributed to the fact that DFT calculations simulate the structures of polymorphs at 0 K, where their volumes are always smaller than those obtained from experiments at room temperature.

The dependences of the lattice parameters of BaP polymorphs on pressure is shown in Fig. 3 (see Table S7 for numerical values). On compression of BaP-I, the a and b parameters gradually shorten, but they change substantially during the transition from BaP-I to BaP-II: the value of the a parameter decreases from 4.2338(2) to 3.59710(10) Å, while the b parameter increases from 19.838(4) to 21.658(9) Å. The c parameter continuously shortens in all phases. The β angle decreases from 97.006(8) to 95.613(5)° on compression of BaP-I at pressures still below ∼3 GPa. After a phase transition at 4.8 GPa β slightly rises to 95.820(8)° in BaP-III and does not change considerably on compression to the maximum pressure of about 28 GPa.

Figure 3 Lattice parameters of BaP polymorphs as a function of pressure up to 27.9 GPa. Lattice parameters (a) a, (b) b, (c) c and (d) β are designated in the y axes for the structures of BaP-I and BaP-II. For the triclinic structure of BaP-III the corresponding lattice parameters are given in brackets in the legend. (As the α and β angles in the triclinic structure of BaP-III are very close to 90°, then b of BaP-I and BaP-II corresponds to c in BaP-III and vice versa, while β corresponds to γ in BaP-III). Green solid triangles – BaP-I, red inversed solid triangles – BaP-II and blue solid circles – BaP-III.

4.2. Theoretical calculations

DFT calculations were conducted at ten pressure points between 1 bar and 40 GPa. Relaxed structural parameters are detailed in Tables S8–S10, which include data for BaP-I at ambient pressure, BaP-II at 4.8 GPa and BaP-III at 7.1 GPa.

The enthalpy differences (ΔH) for the two polymorphs (BaP-I and BaP-III) relative to BaP-II were calculated as a function of pressure from ambient pressure up to 7.1 GPa at 0 K (Fig. 4) as described in the Methods. They revealed that, at ambient pressure, BaP-I is relatively more stable than BaP-II and BaP-III. We found that, at 2.2 GPa, BaP-I relaxed into an atomic configuration with an enthalpy much higher than that of BaP-II and BaP-III. At 3.5 GPa, starting from the atomic configuration of BaP-I, atomic positions relaxed to those of BaP-II. According to the calculations, BaP-III is the most stable phase above 3.5 GPa.

Figure 4 ΔH values for the two polymorphs BaP-I and BaP-III relative to BaP-II calculated up to 7.1 GPa. Designations for different polymorphs are as follows: BaP-I – green solid triangles, BaP-III – blue solid circles and BaP-II – red inversed solid triangles.

4.3. Geometrical analysis of the structures of BaP polymorphs

Fig. 5 illustrates the structures of BaP-I and BaP-II viewed along the [540] direction [Figs. 5(a) and 5(b)], and of BaP-III viewed along the [504] direction [Fig. 5(c)], chosen to optimally display the topology of the molecular structures of these different polymorphs. To accurately calculate the intermolecular distances in BaP polymorphs, the molecules were approximated by mean molecular planes considering 20 carbon atoms in a molecule, using the NumPy and SciPy libraries in Python (blue lines in Fig. 5). The intermolecular distances (d, d₁ and d₂) and interplanar angles (δ) were calculated using the same software. They are listed in Table S11 and presented graphically in Fig. 6 as a function of pressure. It is clear that the structure of BaP-I undergoes gradual compaction on compression, characterized by a gradual decrease in the intermolecular distances [Fig. 6(a)]. The intermolecular angle in BaP-I changes slightly from 72.9° at ambient pressure to 73.5° at 2.2 GPa, whereas in the BaP-I to BaP-II transformation, the applied stress leads to an abrupt change in the intermolecular angle from 73.5° at 2.2 GPa in BaP-I to 53.5° at 4.8 GPa in BaP-II. Further compression of BaP-II to 7.1 GPa results in a decrease of symmetry to P1, indicating the transformation to BaP-III. On further compression of BaP-III from 4.8 to 27.9 GPa, the angle slowly rises to 54.8°. Interestingly, compared with the behavior of pyrene molecules, which showed curvature with increasing pressure, as found in our previous study of pyrene (Zhou et al., 2024), in BaP polymorphs the molecules remain flat up to about 28 GPa, the highest pressure achieved in this study.

Figure 5 Visualization of intermolecular distances and interplanar angles in the structures of BaP polymorphs. (a) BaP-I and (b) BaP-II, as viewed along the [504] direction; (c) BaP-III, as viewed along the [540] direction (hydrogen atoms are not shown, carbon atoms are shown as black dots). The blue lines represent the planes of the flat molecules; in BaP-I and BaP-II all intermolecular distances are equal (designated d); d1 and d2 are the interplanar distances in BaP-III, which are almost equal; δ is the interplanar angle.

Figure 6 Variation of (a) intermolecular distances (see Fig. 5 for designations) and (b) interplanar angles in the BaP polymorphs with pressure (see Fig. 5 for δ).

4.4. Evolution of intermolecular interactions on compression

To visualize intermolecular interactions and explore their evolution on compression, we constructed Hirshfeld surfaces for the three BaP polymorphs using the CrystalExplorer program (Spackman et al., 2021). Those mapped with the shape index are shown in Fig. 7. Corresponding fingerprint plots are provided in Fig. S1 of the supporting information. The methodology of the Hirshfeld surface analysis is described in detail in a comprehensive review by McKinnon et al. (2004) and in the paper by Spackman & Jayatilaka (2009).

Figure 7 Hirshfeld surfaces of BaP polymorphs mapped with the shape index. The front and back views of Hirshfeld surfaces for (a) BaP-I at ambient pressure, (b) BaP-II at 4.8 GPa and (c) BaP-III at 21.1 GPa. Shape index is mapped from −1.0 (red) to 0.0 (green) to 1.0 (blue).

The analysis of the Hirshfeld surfaces of BaP polymorphs – even based purely on visual inspection – shows that the two sides of a molecule are involved in quite similar contacts with neighboring molecules, participating in a planar stacking arrangement of molecules (π⋯π stacking) showing up as the alternating red and blue triangles in both the front and the back sides of the Hirshfeld surfaces (Fig. 7) (McKinnon et al., 2004; Spackman & Jayatilaka, 2009), as well as a red region near the center of the fingerprint plot (Fig. S1 of the supporting information). These features are quite obvious for all polymorphs (Figs. 7 and S1). For BaP-I the red region in the fingerprint plot is in the vicinity of (d_i, d_e) ≃ 1.8–2.0 Å, a range typical of the interplanar spacing of PAHs (d_i and d_e are the distances from the internal or external atoms to the Hirshfeld surface). With increasing pressure this red feature moves to lower (d_i, d_e) values, indicating a decrease in the intermolecular distances [see also Fig. 6(a)]. Blue signifies convex surface curvatures of the Hirshfeld surface corresponding to the direct H⋯H contacts. The red regions of concave curvature reflect the C⋯H interactions between the molecules.

One can break down the Hirshfeld surface into patches associated with specific atom-type/atom-type pairs to highlight just those regions on the surface, and sum the areas of surface patches associated with various contacts (Spackman & Jayatilaka, 2009). We have made the calculations using the Crystal­Explorer program (Spackman et al., 2021) for all BaP polymorphs as a function of pressure (Table S12). As seen, for BaP-I the H⋯H interactions are associated with nearly 60% of the surface area, whereas the contribution of the C⋯C interactions is about 20%, and the sum of all C⋯H interactions is also about 20%. Fig. S2 presents percentage contributions to the Hirshfeld surface area for the various close intermolecular contacts (C⋯C, H⋯H, C_e⋯H_i and C_i⋯H_e) as a function of pressure for the molecules in the BaP polymorphs. The percentage contribution of C⋯C intermolecular contacts increases with pressure, while that of H⋯H contacts decreases, showing an abrupt change as a result of the BaP-I to BaP-II transition: while the C⋯C contribution still shows an increase (although non-monotonic), the H⋯H contribution also increases, likely as a result of a sharp decrease of the interplanar angle by about 20°. The C⋯H contribution decreases as there is a decrease in the offset of stacked molecules following the BaP-I to BaP-II transition. However, in the BaP-II to BaP-III transition, there are no abrupt changes in the percentage contribution of direct H⋯H contacts (which continues to decrease monotonically) while that of the C⋯C contacts increases consistently, and the total C⋯H contribution shows almost no change. The shortest H⋯H contacts considerably decrease in BaP-II compared with those in BaP-I, but do not noticeably decrease on further compression (see the positions of the sharp features in the left lower corners of the fingerprint plots for BaP-I and BaP-III in Fig. S1). To summarize, in all three polymorphs, the molecules are involved in similar contacts with neighboring molecules, participating in a planar stacking arrangement. A general trend is observed with an increase in the percentage contribution of C⋯C intermolecular contacts and a decrease in H⋯H contacts on compression.

5. Conclusions

We have presented the results of high-pressure studies of BaP up to about 28 GPa. These provide insights into the structural transformations in a representative of a broad class of organic materials: PAHs. These studies combined in situ synchrotron SC-XRD in a diamond anvil cell and ab initio calculations. At 4.8 GPa, BaP-I was found to transform to a previously unknown BaP-II phase with the same space group (P2₁/c). The transformation manifests as an abrupt change in the intermolecular angle and unit-cell parameters. The second previously unknown polymorph, BaP-III, was detected at 7.1 GPa and preserved under an He pressure medium up to 27.9 GPa. According to the DFT calculations, BaP-III is the most stable phase above 3.5 GPa.

6. Related literature

The following references are cited in the supporting information: Carrell et al. (1997).

Supporting information

Computing details

(benzoapyrene_0GPa)

Crystal data

C20H12	F(000) = 528
Mr = 252.30	Dx = 1.345 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.410 Å
a = 4.5384 (3) Å	Cell parameters from 302 reflections
b = 20.439 (5) Å	θ = 2.6–15.0°
c = 13.531 (2) Å	µ = 0.04 mm^−1
β = 97.006 (8)°	T = 293 K
V = 1245.8 (4) Å^3	Block, clear colourless
Z = 4	0.01 × 0.01 × 0.01 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1877 independent reflections
Radiation source: synchrotron	661 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.035
ω scans	θmax = 21.6°, θmin = 2.6°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −7→7
Tmin = 0.296, Tmax = 1.000	k = −22→18
3094 measured reflections	l = −19→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.0949P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
1877 reflections	Δρmax = 0.08 e Å^−3
181 parameters	Δρmin = −0.09 e Å^−3

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
C001	−0.3158 (6)	0.4606 (3)	0.6504 (3)	0.0774 (15)
H001	−0.404908	0.458074	0.584842	0.093*
C002	0.2356 (6)	0.6528 (2)	0.5597 (2)	0.0689 (13)
H002	0.141746	0.650225	0.494731	0.083*
C003	0.3064 (5)	0.6117 (2)	0.7322 (2)	0.0535 (11)
C004	0.5137 (5)	0.6624 (2)	0.7561 (2)	0.0581 (10)
C005	0.2387 (5)	0.5664 (2)	0.8047 (2)	0.0580 (11)
C006	0.5820 (5)	0.6230 (2)	0.9273 (2)	0.0638 (12)
H006	0.673508	0.626158	0.992436	0.077*
C007	0.5829 (6)	0.7088 (2)	0.6828 (3)	0.0652 (13)
C008	−0.1096 (5)	0.5105 (2)	0.6781 (3)	0.0652 (12)
C009	0.1626 (5)	0.6063 (2)	0.6309 (2)	0.0642 (13)
C00A	0.0292 (5)	0.5143 (2)	0.7772 (2)	0.0621 (12)
C00B	0.3820 (5)	0.5749 (2)	0.9036 (2)	0.0667 (12)
H00B	0.336293	0.546525	0.953202	0.080*
C00C	−0.0378 (6)	0.5575 (2)	0.6070 (2)	0.0663 (13)
H00C	−0.131142	0.554817	0.541977	0.080*
C00D	0.6565 (5)	0.6687 (2)	0.8557 (2)	0.0651 (12)
C00E	−0.0457 (6)	0.4672 (2)	0.8451 (3)	0.0701 (13)
H00E	0.043702	0.468862	0.910677	0.084*
C00F	0.8646 (6)	0.7196 (3)	0.8766 (3)	0.0763 (14)
H00F	0.960865	0.723826	0.941040	0.092*
C00G	0.4377 (6)	0.7009 (2)	0.5835 (2)	0.0733 (13)
H00G	0.483206	0.729483	0.534109	0.088*
C00H	−0.2470 (7)	0.4189 (3)	0.8173 (3)	0.0860 (14)
H00H	−0.292303	0.387977	0.863639	0.103*
C00I	0.7891 (6)	0.7572 (2)	0.7101 (3)	0.0762 (14)
H00I	0.834574	0.787124	0.662367	0.091*
C00J	0.9291 (6)	0.7626 (3)	0.8057 (3)	0.0801 (14)
H00J	1.067748	0.795550	0.821867	0.096*
C00K	−0.3866 (6)	0.4159 (3)	0.7179 (3)	0.0894 (16)
H00K	−0.526090	0.383543	0.698959	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C001	0.0637 (15)	0.072 (6)	0.095 (3)	−0.001 (2)	0.0019 (15)	−0.011 (2)
C002	0.0787 (15)	0.071 (5)	0.055 (2)	0.0065 (19)	0.0020 (13)	0.0060 (15)
C003	0.0548 (11)	0.042 (4)	0.062 (2)	0.0086 (15)	−0.0002 (10)	−0.0028 (13)
C004	0.0585 (11)	0.052 (4)	0.064 (2)	0.0109 (16)	0.0085 (11)	−0.0005 (15)
C005	0.0600 (12)	0.045 (4)	0.068 (2)	0.0054 (16)	0.0049 (12)	0.0014 (14)
C006	0.0718 (14)	0.063 (4)	0.054 (2)	0.0085 (19)	−0.0033 (12)	−0.0017 (14)
C007	0.0664 (15)	0.051 (5)	0.078 (2)	0.0079 (18)	0.0090 (13)	0.0002 (16)
C008	0.0603 (13)	0.053 (5)	0.081 (3)	0.0077 (18)	0.0020 (13)	−0.0057 (17)
C009	0.0633 (13)	0.067 (5)	0.060 (2)	0.0115 (18)	0.0008 (12)	−0.0007 (15)
C00A	0.0633 (13)	0.051 (5)	0.071 (3)	0.0090 (17)	0.0059 (13)	0.0001 (15)
C00B	0.0730 (14)	0.066 (4)	0.060 (2)	0.0097 (18)	0.0059 (12)	0.0062 (14)
C00C	0.0690 (14)	0.058 (5)	0.068 (2)	0.0086 (19)	−0.0062 (13)	−0.0045 (16)
C00D	0.0570 (12)	0.071 (5)	0.066 (2)	0.0099 (18)	0.0027 (12)	−0.0120 (15)
C00E	0.0800 (17)	0.051 (5)	0.081 (3)	0.004 (2)	0.0141 (15)	0.0002 (17)
C00F	0.0703 (16)	0.070 (6)	0.086 (3)	0.007 (2)	−0.0003 (15)	−0.0177 (18)
C00G	0.0860 (17)	0.066 (5)	0.070 (2)	0.018 (2)	0.0154 (15)	0.0160 (16)
C00H	0.0954 (19)	0.060 (6)	0.108 (3)	0.003 (3)	0.0317 (18)	0.006 (2)
C00I	0.0802 (17)	0.047 (6)	0.103 (3)	0.000 (2)	0.0169 (16)	0.0001 (18)
C00J	0.0837 (19)	0.047 (6)	0.110 (4)	−0.010 (2)	0.0164 (17)	−0.013 (2)
C00K	0.0728 (17)	0.076 (6)	0.121 (4)	−0.009 (2)	0.0167 (18)	−0.025 (3)

Geometric parameters (Å, º)

C001—H001	0.9300	C008—C00A	1.412 (5)
C001—C008	1.405 (6)	C008—C00C	1.426 (5)
C001—C00K	1.358 (6)	C009—C00C	1.361 (5)
C002—H002	0.9300	C00A—C00E	1.401 (5)
C002—C009	1.422 (5)	C00B—H00B	0.9300
C002—C00G	1.356 (5)	C00C—H00C	0.9300
C003—C004	1.410 (5)	C00D—C00F	1.410 (6)
C003—C005	1.409 (5)	C00E—H00E	0.9300
C003—C009	1.449 (4)	C00E—C00H	1.367 (6)
C004—C007	1.434 (5)	C00F—H00F	0.9300
C004—C00D	1.428 (4)	C00F—C00J	1.359 (6)
C005—C00A	1.446 (5)	C00G—H00G	0.9300
C005—C00B	1.425 (4)	C00H—H00H	0.9300
C006—H006	0.9300	C00H—C00K	1.417 (5)
C006—C00B	1.349 (5)	C00I—H00I	0.9300
C006—C00D	1.416 (5)	C00I—C00J	1.374 (5)
C007—C00G	1.431 (5)	C00J—H00J	0.9300
C007—C00I	1.382 (6)	C00K—H00K	0.9300
C008—C001—H001	119.6	C005—C00B—H00B	119.0
C00K—C001—H001	119.6	C006—C00B—C005	121.9 (4)
C00K—C001—C008	120.9 (4)	C006—C00B—H00B	119.0
C009—C002—H002	119.0	C008—C00C—H00C	118.9
C00G—C002—H002	119.0	C009—C00C—C008	122.2 (3)
C00G—C002—C009	122.0 (3)	C009—C00C—H00C	118.9
C004—C003—C009	118.9 (3)	C006—C00D—C004	117.8 (4)
C005—C003—C004	121.3 (3)	C00F—C00D—C004	118.1 (4)
C005—C003—C009	119.8 (3)	C00F—C00D—C006	124.0 (3)
C003—C004—C007	121.6 (3)	C00A—C00E—H00E	119.2
C003—C004—C00D	119.7 (3)	C00H—C00E—C00A	121.6 (4)
C00D—C004—C007	118.7 (4)	C00H—C00E—H00E	119.2
C003—C005—C00A	119.8 (3)	C00D—C00F—H00F	118.9
C003—C005—C00B	117.4 (4)	C00J—C00F—C00D	122.1 (4)
C00B—C005—C00A	122.8 (3)	C00J—C00F—H00F	118.9
C00B—C006—H006	119.1	C002—C00G—C007	121.7 (4)
C00B—C006—C00D	121.9 (3)	C002—C00G—H00G	119.1
C00D—C006—H006	119.1	C007—C00G—H00G	119.1
C00G—C007—C004	117.4 (4)	C00E—C00H—H00H	120.1
C00I—C007—C004	119.2 (3)	C00E—C00H—C00K	119.9 (4)
C00I—C007—C00G	123.4 (4)	C00K—C00H—H00H	120.1
C001—C008—C00A	120.0 (4)	C007—C00I—H00I	119.1
C001—C008—C00C	120.6 (3)	C00J—C00I—C007	121.9 (4)
C00A—C008—C00C	119.5 (4)	C00J—C00I—H00I	119.1
C002—C009—C003	118.3 (4)	C00F—C00J—C00I	119.9 (4)
C00C—C009—C002	122.2 (3)	C00F—C00J—H00J	120.0
C00C—C009—C003	119.5 (3)	C00I—C00J—H00J	120.0
C008—C00A—C005	119.2 (4)	C001—C00K—C00H	119.7 (5)
C00E—C00A—C005	122.8 (3)	C001—C00K—H00K	120.2
C00E—C00A—C008	118.0 (4)	C00H—C00K—H00K	120.2
C001—C008—C00A—C005	−179.4 (3)	C008—C001—C00K—C00H	−1.2 (7)
C001—C008—C00A—C00E	0.0 (6)	C008—C00A—C00E—C00H	−0.1 (6)
C001—C008—C00C—C009	−179.4 (3)	C009—C002—C00G—C007	−2.0 (6)
C002—C009—C00C—C008	179.6 (4)	C009—C003—C004—C007	0.6 (5)
C003—C004—C007—C00G	−1.3 (5)	C009—C003—C004—C00D	179.7 (3)
C003—C004—C007—C00I	−179.6 (3)	C009—C003—C005—C00A	0.8 (5)
C003—C004—C00D—C006	0.0 (5)	C009—C003—C005—C00B	−178.7 (3)
C003—C004—C00D—C00F	179.4 (3)	C00A—C005—C00B—C006	178.4 (3)
C003—C005—C00A—C008	−1.4 (5)	C00A—C008—C00C—C009	0.3 (6)
C003—C005—C00A—C00E	179.2 (3)	C00A—C00E—C00H—C00K	−0.4 (6)
C003—C005—C00B—C006	−2.0 (5)	C00B—C005—C00A—C008	178.1 (3)
C003—C009—C00C—C008	−1.0 (5)	C00B—C005—C00A—C00E	−1.2 (6)
C004—C003—C005—C00A	−178.8 (3)	C00B—C006—C00D—C004	−0.3 (5)
C004—C003—C005—C00B	1.6 (5)	C00B—C006—C00D—C00F	−179.8 (3)
C004—C003—C009—C002	−0.5 (5)	C00C—C008—C00A—C005	0.8 (5)
C004—C003—C009—C00C	180.0 (3)	C00C—C008—C00A—C00E	−179.8 (4)
C004—C007—C00G—C002	2.0 (5)	C00D—C004—C007—C00G	179.6 (3)
C004—C007—C00I—C00J	−0.4 (6)	C00D—C004—C007—C00I	1.3 (5)
C004—C00D—C00F—C00J	0.8 (6)	C00D—C006—C00B—C005	1.4 (6)
C005—C003—C004—C007	−179.8 (3)	C00D—C00F—C00J—C00I	0.1 (7)
C005—C003—C004—C00D	−0.6 (5)	C00E—C00H—C00K—C001	1.0 (6)
C005—C003—C009—C002	179.9 (3)	C00G—C002—C009—C003	1.2 (5)
C005—C003—C009—C00C	0.4 (5)	C00G—C002—C009—C00C	−179.3 (3)
C005—C00A—C00E—C00H	179.3 (3)	C00G—C007—C00I—C00J	−178.6 (4)
C006—C00D—C00F—C00J	−179.8 (4)	C00I—C007—C00G—C002	−179.8 (3)
C007—C004—C00D—C006	179.1 (3)	C00K—C001—C008—C00A	0.7 (6)
C007—C004—C00D—C00F	−1.5 (5)	C00K—C001—C008—C00C	−179.6 (4)
C007—C00I—C00J—C00F	−0.3 (6)

(benzoapyrene_2.2GPa)

Crystal data

C20H12	F(000) = 528
Mr = 252.30	Dx = 1.553 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.410 Å
a = 4.2338 (2) Å	Cell parameters from 558 reflections
b = 19.838 (4) Å	θ = 2.8–19.2°
c = 12.9059 (10) Å	µ = 0.04 mm^−1
β = 95.613 (5)°	T = 293 K
V = 1078.8 (2) Å^3	Block, clear yellowish colourless
Z = 4	0.02 × 0.01 × 0.01 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1646 independent reflections
Radiation source: synchrotron	831 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.013
ω scans	θmax = 21.4°, θmin = 2.8°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −6→6
Tmin = 0.081, Tmax = 1.000	k = −19→13
2644 measured reflections	l = −17→19

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.069	H-atom parameters constrained
wR(F^2) = 0.243	w = 1/[σ^2(Fo^2) + (0.1566P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
1646 reflections	Δρmax = 0.25 e Å^−3
181 parameters	Δρmin = −0.20 e Å^−3

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
C001	0.9753 (5)	0.4875 (2)	0.2231 (2)	0.0414 (11)
C002	0.4528 (5)	0.3356 (2)	0.2466 (2)	0.0405 (11)
C003	0.6750 (4)	0.3883 (2)	0.2705 (2)	0.0396 (11)
C004	1.0367 (5)	0.4436 (2)	0.4010 (2)	0.0469 (12)
H004	1.131373	0.446908	0.468973	0.056*
C005	0.7511 (5)	0.4336 (2)	0.1948 (2)	0.0410 (12)
C006	0.7400 (5)	0.3443 (2)	0.4513 (2)	0.0476 (12)
H006	0.837733	0.346842	0.518892	0.057*
C007	0.3903 (5)	0.3765 (2)	0.06792 (19)	0.0475 (12)
H007	0.296501	0.372946	−0.000083	0.057*
C008	0.3049 (5)	0.3299 (2)	0.1426 (2)	0.0432 (11)
C009	1.1185 (5)	0.4905 (2)	0.3268 (2)	0.0451 (12)
C00A	1.3416 (5)	0.5420 (2)	0.3545 (2)	0.0493 (13)
H00A	1.434150	0.544302	0.422771	0.059*
C00B	1.2776 (5)	0.5852 (2)	0.1806 (3)	0.0535 (12)
H00B	1.329021	0.616950	0.132001	0.064*
C00C	0.1534 (5)	0.2384 (2)	0.2959 (2)	0.0497 (12)
H00C	0.103228	0.207439	0.345890	0.060*
C00D	0.8212 (5)	0.3928 (2)	0.3766 (2)	0.0417 (11)
C00E	1.4246 (5)	0.5879 (3)	0.2845 (3)	0.0533 (13)
H00E	1.575352	0.620822	0.303965	0.064*
C00F	0.0826 (5)	0.2777 (2)	0.1196 (2)	0.0499 (13)
H00F	−0.013662	0.273043	0.052074	0.060*
C00G	0.0067 (6)	0.2341 (3)	0.1946 (2)	0.0518 (13)
H00G	−0.145344	0.200984	0.178127	0.062*
C00H	0.5267 (5)	0.2950 (2)	0.4272 (2)	0.0499 (11)
H00H	0.476925	0.264866	0.478326	0.060*
C00I	0.6033 (5)	0.4262 (2)	0.0914 (2)	0.0454 (10)
H00I	0.653866	0.455811	0.039642	0.054*
C00J	0.3742 (5)	0.2886 (2)	0.3221 (2)	0.0457 (12)
C00K	1.0618 (5)	0.5361 (2)	0.1524 (2)	0.0470 (12)
H00K	0.968829	0.534808	0.084131	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C001	0.0373 (10)	0.041 (4)	0.0455 (17)	0.0030 (12)	0.0048 (9)	0.0021 (14)
C002	0.0355 (10)	0.041 (4)	0.0448 (18)	0.0029 (11)	0.0050 (9)	0.0000 (13)
C003	0.0353 (9)	0.042 (4)	0.0408 (16)	0.0057 (11)	0.0016 (8)	−0.0006 (13)
C004	0.0399 (10)	0.063 (5)	0.0370 (16)	0.0061 (13)	−0.0026 (9)	−0.0060 (13)
C005	0.0370 (10)	0.045 (4)	0.0410 (18)	0.0026 (11)	0.0030 (9)	0.0021 (12)
C006	0.0466 (11)	0.060 (4)	0.0359 (16)	0.0082 (13)	0.0017 (9)	0.0044 (13)
C007	0.0426 (11)	0.063 (4)	0.0356 (16)	0.0055 (13)	−0.0026 (9)	−0.0014 (12)
C008	0.0363 (10)	0.048 (4)	0.0448 (17)	0.0041 (11)	0.0012 (9)	−0.0029 (13)
C009	0.0369 (10)	0.054 (4)	0.0448 (17)	0.0058 (12)	0.0027 (9)	−0.0027 (14)
C00A	0.0398 (11)	0.052 (5)	0.055 (2)	0.0032 (13)	−0.0012 (10)	−0.0040 (15)
C00B	0.0522 (13)	0.046 (5)	0.064 (2)	0.0028 (15)	0.0162 (11)	0.0055 (16)
C00C	0.0476 (12)	0.049 (4)	0.054 (2)	−0.0013 (13)	0.0127 (10)	0.0006 (14)
C00D	0.0388 (10)	0.043 (4)	0.0428 (18)	0.0062 (11)	0.0008 (9)	−0.0007 (13)
C00E	0.0435 (12)	0.043 (5)	0.073 (3)	−0.0036 (14)	0.0085 (12)	−0.0066 (18)
C00F	0.0423 (11)	0.060 (5)	0.0471 (19)	0.0018 (13)	0.0021 (10)	−0.0085 (15)
C00G	0.0494 (13)	0.049 (5)	0.058 (2)	−0.0029 (14)	0.0113 (11)	−0.0091 (16)
C00H	0.0451 (12)	0.063 (4)	0.0414 (17)	0.0049 (13)	0.0065 (9)	0.0084 (13)
C00I	0.0457 (11)	0.051 (4)	0.0393 (17)	0.0062 (13)	0.0040 (9)	0.0062 (12)
C00J	0.0382 (11)	0.043 (4)	0.056 (2)	0.0056 (12)	0.0070 (9)	0.0013 (15)
C00K	0.0452 (12)	0.044 (5)	0.052 (2)	0.0052 (13)	0.0068 (10)	−0.0016 (14)

Geometric parameters (Å, º)

C001—C005	1.453 (5)	C008—C00F	1.411 (6)
C001—C009	1.415 (4)	C009—C00A	1.412 (6)
C001—C00K	1.400 (5)	C00A—H00A	0.9300
C002—C003	1.420 (5)	C00A—C00E	1.355 (6)
C002—C008	1.429 (4)	C00B—H00B	0.9300
C002—C00J	1.411 (5)	C00B—C00E	1.422 (4)
C003—C005	1.389 (5)	C00B—C00K	1.360 (5)
C003—C00D	1.450 (3)	C00C—H00C	0.9300
C004—H004	0.9300	C00C—C00G	1.394 (4)
C004—C009	1.404 (5)	C00C—C00J	1.386 (5)
C004—C00D	1.374 (5)	C00E—H00E	0.9300
C005—C00I	1.425 (4)	C00F—H00F	0.9300
C006—H006	0.9300	C00F—C00G	1.360 (6)
C006—C00D	1.427 (5)	C00G—H00G	0.9300
C006—C00H	1.347 (5)	C00H—H00H	0.9300
C007—H007	0.9300	C00H—C00J	1.449 (4)
C007—C008	1.409 (5)	C00I—H00I	0.9300
C007—C00I	1.350 (5)	C00K—H00K	0.9300
C009—C001—C005	118.5 (3)	C00E—C00B—H00B	120.0
C00K—C001—C005	123.3 (3)	C00K—C00B—H00B	120.0
C00K—C001—C009	118.2 (3)	C00K—C00B—C00E	120.0 (3)
C003—C002—C008	118.9 (3)	C00G—C00C—H00C	120.0
C00J—C002—C003	122.1 (3)	C00J—C00C—H00C	120.0
C00J—C002—C008	119.0 (3)	C00J—C00C—C00G	120.1 (4)
C002—C003—C00D	117.6 (3)	C004—C00D—C003	118.3 (3)
C005—C003—C002	121.2 (2)	C004—C00D—C006	122.5 (3)
C005—C003—C00D	121.2 (3)	C006—C00D—C003	119.2 (3)
C009—C004—H004	118.9	C00A—C00E—C00B	119.0 (4)
C00D—C004—H004	118.9	C00A—C00E—H00E	120.5
C00D—C004—C009	122.1 (3)	C00B—C00E—H00E	120.5
C003—C005—C001	119.4 (2)	C008—C00F—H00F	119.5
C003—C005—C00I	118.7 (3)	C00G—C00F—C008	121.1 (3)
C00I—C005—C001	121.9 (3)	C00G—C00F—H00F	119.5
C00D—C006—H006	118.9	C00C—C00G—H00G	119.5
C00H—C006—H006	118.9	C00F—C00G—C00C	121.0 (4)
C00H—C006—C00D	122.3 (3)	C00F—C00G—H00G	119.5
C008—C007—H007	118.8	C006—C00H—H00H	119.8
C00I—C007—H007	118.8	C006—C00H—C00J	120.4 (3)
C00I—C007—C008	122.5 (2)	C00J—C00H—H00H	119.8
C007—C008—C002	118.2 (3)	C005—C00I—H00I	119.7
C007—C008—C00F	123.3 (3)	C007—C00I—C005	120.5 (3)
C00F—C008—C002	118.5 (3)	C007—C00I—H00I	119.7
C004—C009—C001	120.4 (3)	C002—C00J—C00H	118.4 (3)
C004—C009—C00A	120.6 (3)	C00C—C00J—C002	120.3 (3)
C00A—C009—C001	118.9 (3)	C00C—C00J—C00H	121.3 (3)
C009—C00A—H00A	119.1	C001—C00K—H00K	119.0
C00E—C00A—C009	121.9 (3)	C00B—C00K—C001	122.0 (3)
C00E—C00A—H00A	119.1	C00B—C00K—H00K	119.0
C001—C005—C00I—C007	−178.5 (3)	C009—C001—C005—C00I	−178.4 (3)
C001—C009—C00A—C00E	−0.7 (6)	C009—C001—C00K—C00B	0.2 (6)
C002—C003—C005—C001	178.9 (3)	C009—C004—C00D—C003	−0.1 (5)
C002—C003—C005—C00I	−0.4 (5)	C009—C004—C00D—C006	179.1 (3)
C002—C003—C00D—C004	−180.0 (3)	C009—C00A—C00E—C00B	1.4 (6)
C002—C003—C00D—C006	0.7 (5)	C00D—C003—C005—C001	−1.6 (5)
C002—C008—C00F—C00G	0.8 (5)	C00D—C003—C005—C00I	179.1 (3)
C003—C002—C008—C007	0.9 (5)	C00D—C004—C009—C001	1.0 (5)
C003—C002—C008—C00F	−179.5 (3)	C00D—C004—C009—C00A	−179.8 (3)
C003—C002—C00J—C00C	179.3 (3)	C00D—C006—C00H—C00J	1.2 (6)
C003—C002—C00J—C00H	0.0 (5)	C00E—C00B—C00K—C001	0.4 (6)
C003—C005—C00I—C007	0.8 (5)	C00G—C00C—C00J—C002	−0.3 (5)
C004—C009—C00A—C00E	−179.9 (4)	C00G—C00C—C00J—C00H	179.0 (3)
C005—C001—C009—C004	−2.0 (5)	C00H—C006—C00D—C003	−1.3 (5)
C005—C001—C009—C00A	178.7 (3)	C00H—C006—C00D—C004	179.4 (3)
C005—C001—C00K—C00B	−178.6 (3)	C00I—C007—C008—C002	−0.5 (6)
C005—C003—C00D—C004	0.5 (5)	C00I—C007—C008—C00F	179.9 (3)
C005—C003—C00D—C006	−178.8 (3)	C00J—C002—C003—C005	179.5 (3)
C006—C00H—C00J—C002	−0.6 (5)	C00J—C002—C003—C00D	−0.1 (5)
C006—C00H—C00J—C00C	−179.8 (3)	C00J—C002—C008—C007	−179.0 (3)
C007—C008—C00F—C00G	−179.6 (4)	C00J—C002—C008—C00F	0.6 (5)
C008—C002—C003—C005	−0.4 (5)	C00J—C00C—C00G—C00F	1.7 (6)
C008—C002—C003—C00D	−180.0 (3)	C00K—C001—C005—C003	−178.9 (3)
C008—C002—C00J—C00C	−0.8 (5)	C00K—C001—C005—C00I	0.4 (5)
C008—C002—C00J—C00H	179.9 (3)	C00K—C001—C009—C004	179.1 (3)
C008—C007—C00I—C005	−0.3 (6)	C00K—C001—C009—C00A	−0.1 (5)
C008—C00F—C00G—C00C	−2.0 (6)	C00K—C00B—C00E—C00A	−1.2 (6)
C009—C001—C005—C003	2.3 (5)

(benzoapyrene_4.8GPa)

Crystal data

C20H12	F(000) = 528
Mr = 252.30	Dx = 1.689 Mg m^−3
Monoclinic, P21/c	Synchrotron radiation, λ = 0.410 Å
a = 3.5971 (1) Å	Cell parameters from 347 reflections
b = 21.658 (9) Å	θ = 3.3–18.4°
c = 12.7908 (9) Å	µ = 0.04 mm^−1
β = 95.339 (5)°	T = 293 K
V = 992.2 (4) Å^3	Block, clear reddish colourless
Z = 4	0.02 × 0.01 × 0.01 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1313 independent reflections
Radiation source: synchrotron	796 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.020
ω scans	θmax = 21.5°, θmin = 3.3°
Absorption correction: multi-scan CrysAlisPro 1.171.43.70a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −6→5
Tmin = 0.190, Tmax = 1.000	k = −11→15
2486 measured reflections	l = −21→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.052	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.1059P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1313 reflections	Δρmax = 0.20 e Å^−3
181 parameters	Δρmin = −0.16 e Å^−3

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
C001	0.9560 (5)	0.4913 (2)	0.21894 (14)	0.0312 (18)
C002	0.4951 (5)	0.3365 (2)	0.23624 (14)	0.0338 (19)
C003	0.6983 (4)	0.3907 (2)	0.26420 (13)	0.0308 (19)
C004	1.0480 (5)	0.4511 (2)	0.39873 (15)	0.0334 (19)
H004	1.149032	0.455947	0.467838	0.040*
C005	0.7525 (5)	0.4365 (2)	0.18844 (14)	0.0319 (17)
C006	0.7899 (5)	0.3509 (2)	0.44576 (14)	0.0347 (18)
H006	0.895827	0.354644	0.514613	0.042*
C007	0.4104 (5)	0.3734 (2)	0.05571 (14)	0.0351 (18)
H007	0.315833	0.368099	−0.013881	0.042*
C008	0.3476 (5)	0.3270 (2)	0.13099 (15)	0.0317 (18)
C009	1.1032 (5)	0.4978 (2)	0.32472 (15)	0.034 (2)
C00A	1.3072 (5)	0.5519 (3)	0.35532 (16)	0.0357 (19)
H00A	1.405078	0.556249	0.424815	0.043*
C00B	1.2134 (5)	0.5905 (3)	0.18101 (17)	0.041 (2)
H00B	1.250341	0.621485	0.132671	0.049*
C00C	0.2349 (5)	0.2374 (3)	0.28234 (18)	0.040 (2)
H00C	0.198227	0.207070	0.331811	0.048*
C00D	0.8503 (5)	0.3991 (2)	0.37117 (14)	0.0302 (18)
C00E	1.3632 (5)	0.5976 (2)	0.28526 (18)	0.042 (2)
H00E	1.498163	0.632831	0.306317	0.050*
C00F	0.1436 (5)	0.2740 (3)	0.10398 (17)	0.037 (2)
H00F	0.042045	0.268375	0.035103	0.045*
C00G	0.0903 (5)	0.2296 (3)	0.17900 (18)	0.045 (2)
H00G	−0.044376	0.194083	0.159745	0.054*
C00H	0.5871 (5)	0.3015 (2)	0.41827 (16)	0.034 (2)
H00H	0.541196	0.272717	0.469496	0.040*
C00I	0.6035 (5)	0.4246 (2)	0.08364 (14)	0.0252 (17)
H00I	0.641718	0.453670	0.032172	0.030*
C00J	0.4366 (5)	0.2910 (2)	0.31259 (16)	0.032 (2)
C00K	1.0152 (5)	0.5394 (2)	0.14868 (15)	0.0312 (19)
H00K	0.917258	0.536282	0.078984	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C001	0.0269 (7)	0.036 (6)	0.0312 (9)	0.0044 (12)	0.0061 (6)	−0.0067 (13)
C002	0.0272 (7)	0.044 (6)	0.0315 (9)	0.0026 (12)	0.0091 (6)	−0.0012 (13)
C003	0.0286 (7)	0.038 (6)	0.0271 (9)	0.0043 (13)	0.0071 (6)	−0.0005 (12)
C004	0.0327 (8)	0.040 (6)	0.0267 (8)	0.0061 (13)	0.0013 (6)	−0.0012 (12)
C005	0.0290 (7)	0.042 (5)	0.0252 (8)	0.0058 (12)	0.0047 (6)	−0.0014 (12)
C006	0.0370 (8)	0.040 (6)	0.0281 (8)	0.0083 (14)	0.0070 (7)	0.0035 (13)
C007	0.0313 (7)	0.047 (6)	0.0273 (9)	0.0012 (13)	0.0047 (6)	−0.0052 (13)
C008	0.0301 (7)	0.031 (6)	0.0351 (9)	0.0024 (12)	0.0082 (6)	−0.0054 (13)
C009	0.0290 (8)	0.042 (7)	0.0307 (9)	0.0023 (12)	0.0062 (7)	−0.0014 (13)
C00A	0.0298 (8)	0.039 (6)	0.0385 (10)	0.0022 (12)	0.0042 (7)	−0.0101 (14)
C00B	0.0334 (8)	0.049 (7)	0.0428 (11)	0.0032 (13)	0.0116 (7)	0.0040 (16)
C00C	0.0377 (9)	0.035 (8)	0.0492 (12)	−0.0001 (15)	0.0155 (9)	0.0025 (16)
C00D	0.0318 (7)	0.030 (6)	0.0294 (9)	0.0063 (13)	0.0067 (6)	−0.0014 (12)
C00E	0.0294 (8)	0.044 (7)	0.0526 (12)	−0.0004 (13)	0.0097 (7)	−0.0127 (18)
C00F	0.0318 (8)	0.040 (7)	0.0403 (10)	−0.0002 (13)	0.0077 (7)	−0.0085 (15)
C00G	0.0358 (10)	0.047 (8)	0.0545 (13)	0.0020 (15)	0.0141 (9)	−0.0034 (19)
C00H	0.0379 (9)	0.027 (7)	0.0372 (10)	0.0074 (14)	0.0123 (8)	0.0097 (14)
C00I	0.0347 (8)	0.013 (6)	0.0288 (8)	0.0022 (12)	0.0078 (6)	0.0015 (12)
C00J	0.0320 (8)	0.028 (7)	0.0380 (10)	0.0021 (12)	0.0107 (7)	0.0018 (14)
C00K	0.0320 (8)	0.029 (6)	0.0337 (9)	0.0039 (13)	0.0072 (7)	0.0018 (14)

Geometric parameters (Å, º)

C001—C005	1.430 (6)	C008—C00F	1.387 (7)
C001—C009	1.414 (3)	C009—C00A	1.417 (6)
C001—C00K	1.406 (5)	C00A—H00A	0.9300
C002—C003	1.412 (6)	C00A—C00E	1.364 (6)
C002—C008	1.416 (3)	C00B—H00B	0.9300
C002—C00J	1.418 (5)	C00B—C00E	1.399 (3)
C003—C005	1.412 (5)	C00B—C00K	1.360 (6)
C003—C00D	1.437 (3)	C00C—H00C	0.9300
C004—H004	0.9300	C00C—C00G	1.385 (3)
C004—C009	1.413 (5)	C00C—C00J	1.403 (7)
C004—C00D	1.360 (6)	C00E—H00E	0.9300
C005—C00I	1.420 (3)	C00F—H00F	0.9300
C006—H006	0.9300	C00F—C00G	1.385 (6)
C006—C00D	1.444 (5)	C00G—H00G	0.9300
C006—C00H	1.324 (6)	C00H—H00H	0.9300
C007—H007	0.9300	C00H—C00J	1.427 (3)
C007—C008	1.425 (5)	C00I—H00I	0.9300
C007—C00I	1.339 (6)	C00K—H00K	0.9300
C009—C001—C005	118.8 (3)	C00E—C00B—H00B	119.2
C00K—C001—C005	123.1 (2)	C00K—C00B—H00B	119.2
C00K—C001—C009	118.1 (3)	C00K—C00B—C00E	121.6 (4)
C003—C002—C008	120.1 (3)	C00G—C00C—H00C	119.9
C003—C002—C00J	120.7 (2)	C00G—C00C—C00J	120.2 (4)
C008—C002—C00J	119.1 (3)	C00J—C00C—H00C	119.9
C002—C003—C005	120.7 (2)	C003—C00D—C006	118.1 (4)
C002—C003—C00D	119.2 (3)	C004—C00D—C003	119.6 (3)
C005—C003—C00D	120.0 (4)	C004—C00D—C006	122.3 (2)
C009—C004—H004	119.3	C00A—C00E—C00B	118.6 (4)
C00D—C004—H004	119.3	C00A—C00E—H00E	120.7
C00D—C004—C009	121.5 (2)	C00B—C00E—H00E	120.7
C003—C005—C001	119.7 (2)	C008—C00F—H00F	119.8
C003—C005—C00I	117.2 (4)	C00G—C00F—C008	120.4 (2)
C00I—C005—C001	123.1 (3)	C00G—C00F—H00F	119.8
C00D—C006—H006	119.3	C00C—C00G—H00G	119.6
C00H—C006—H006	119.3	C00F—C00G—C00C	120.8 (4)
C00H—C006—C00D	121.5 (2)	C00F—C00G—H00G	119.6
C008—C007—H007	119.5	C006—C00H—H00H	118.9
C00I—C007—H007	119.5	C006—C00H—C00J	122.1 (3)
C00I—C007—C008	121.0 (2)	C00J—C00H—H00H	118.9
C002—C008—C007	118.1 (4)	C005—C00I—H00I	118.6
C00F—C008—C002	120.0 (3)	C007—C00I—C005	122.8 (3)
C00F—C008—C007	121.9 (2)	C007—C00I—H00I	118.6
C001—C009—C00A	119.1 (3)	C002—C00J—C00H	118.3 (3)
C004—C009—C001	120.4 (3)	C00C—C00J—C002	119.4 (2)
C004—C009—C00A	120.6 (2)	C00C—C00J—C00H	122.3 (3)
C009—C00A—H00A	119.2	C001—C00K—H00K	119.5
C00E—C00A—C009	121.5 (2)	C00B—C00K—C001	121.0 (2)
C00E—C00A—H00A	119.2	C00B—C00K—H00K	119.5
C001—C005—C00I—C007	−179.4 (3)	C009—C001—C005—C00I	−178.0 (2)
C001—C009—C00A—C00E	0.2 (4)	C009—C001—C00K—C00B	1.0 (4)
C002—C003—C005—C001	179.3 (3)	C009—C004—C00D—C003	1.0 (4)
C002—C003—C005—C00I	−1.7 (4)	C009—C004—C00D—C006	−179.8 (2)
C002—C003—C00D—C004	179.7 (3)	C009—C00A—C00E—C00B	0.2 (4)
C002—C003—C00D—C006	0.5 (4)	C00D—C003—C005—C001	−0.6 (4)
C002—C008—C00F—C00G	−1.5 (4)	C00D—C003—C005—C00I	178.4 (2)
C003—C002—C008—C007	−0.1 (4)	C00D—C004—C009—C001	−0.7 (4)
C003—C002—C008—C00F	−179.1 (3)	C00D—C004—C009—C00A	179.4 (3)
C003—C002—C00J—C00C	−179.7 (3)	C00D—C006—C00H—C00J	4.1 (5)
C003—C002—C00J—C00H	0.2 (4)	C00E—C00B—C00K—C001	−0.6 (4)
C003—C005—C00I—C007	1.7 (4)	C00G—C00C—C00J—C002	−0.8 (5)
C004—C009—C00A—C00E	−179.9 (2)	C00G—C00C—C00J—C00H	179.2 (2)
C005—C001—C009—C004	−0.3 (4)	C00H—C006—C00D—C003	−2.9 (4)
C005—C001—C009—C00A	179.6 (3)	C00H—C006—C00D—C004	177.9 (3)
C005—C001—C00K—C00B	−179.4 (3)	C00I—C007—C008—C002	0.1 (4)
C005—C003—C00D—C004	−0.4 (4)	C00I—C007—C008—C00F	179.0 (3)
C005—C003—C00D—C006	−179.6 (2)	C00J—C002—C003—C005	−179.2 (2)
C006—C00H—C00J—C002	−2.7 (4)	C00J—C002—C003—C00D	0.7 (4)
C006—C00H—C00J—C00C	177.2 (3)	C00J—C002—C008—C007	−180.0 (2)
C007—C008—C00F—C00G	179.5 (3)	C00J—C002—C008—C00F	1.1 (4)
C008—C002—C003—C005	1.0 (4)	C00J—C00C—C00G—C00F	0.4 (4)
C008—C002—C003—C00D	−179.1 (2)	C00K—C001—C005—C003	−178.7 (2)
C008—C002—C00J—C00C	0.1 (4)	C00K—C001—C005—C00I	2.4 (4)
C008—C002—C00J—C00H	−179.9 (2)	C00K—C001—C009—C004	179.3 (2)
C008—C007—C00I—C005	−0.8 (5)	C00K—C001—C009—C00A	−0.8 (4)
C008—C00F—C00G—C00C	0.8 (4)	C00K—C00B—C00E—C00A	0.0 (4)
C009—C001—C005—C003	0.9 (4)

(benzoapyrene_7.1GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 1.767 Mg m^−3
a = 3.4912 (1) Å	Synchrotron radiation, λ = 0.410 Å
b = 12.687 (3) Å	Cell parameters from 373 reflections
c = 21.531 (6) Å	θ = 3.4–18.8°
α = 91.51 (2)°	µ = 0.05 mm^−1
β = 90.434 (9)°	T = 293 K
γ = 95.820 (8)°	Block, clear colourless
V = 948.4 (3) Å^3	0.02 × 0.02 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1531 independent reflections
Radiation source: synchrotron	867 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.031
ω scans	θmax = 21.0°, θmin = 3.4°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.164, Tmax = 1.000	k = −15→16
2260 measured reflections	l = −16→21

Refinement

Refinement on F^2	66 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0973P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
1531 reflections	Δρmax = 0.20 e Å^−3
361 parameters	Δρmin = −0.15 e Å^−3

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	0.5265 (8)	0.2857 (6)	0.5063 (5)	0.035 (7)
C3	0.4547 (14)	0.2227 (8)	0.0088 (7)	0.028 (5)
C5	0.9781 (8)	0.2543 (5)	0.6626 (5)	0.025 (4)
C7	−0.0231 (10)	0.2332 (7)	0.1652 (6)	0.029 (9)
C9	0.7716 (8)	0.2323 (5)	0.6073 (5)	0.023 (7)
C11	0.1838 (11)	0.2627 (7)	0.1110 (6)	0.026 (5)
C13	0.3994 (8)	0.1046 (5)	0.5417 (5)	0.028 (7)
H13	0.278145	0.036513	0.535066	0.034*
C15	0.5296 (14)	0.4017 (8)	0.0524 (8)	0.041 (10)
H15	0.620931	0.472477	0.047750	0.049*
C17	0.7319 (8)	0.3112 (6)	0.5640 (5)	0.029 (7)
C19	0.2484 (10)	0.1894 (7)	0.0646 (6)	0.027 (9)
C21	0.6564 (8)	0.0469 (6)	0.6394 (5)	0.046 (8)
H21	0.534270	−0.021180	0.633220	0.055*
C23	0.2617 (12)	0.4444 (8)	0.1534 (8)	0.057 (11)
H23	0.356628	0.515014	0.149299	0.068*
C25	1.0918 (9)	0.4385 (6)	0.6322 (5)	0.027 (6)
H25	1.201056	0.507516	0.640145	0.033*
C27	−0.0911 (11)	0.0510 (7)	0.1242 (6)	0.047 (9)
H27	−0.181045	−0.019783	0.128961	0.057*
C31	−0.1620 (11)	0.1255 (7)	0.1713 (6)	0.025 (4)
C33	0.3574 (8)	0.1806 (6)	0.4955 (5)	0.043 (8)
C35	0.5958 (13)	0.3324 (8)	0.0072 (7)	0.029 (10)
C37	0.1496 (9)	0.1561 (6)	0.4406 (5)	0.035 (8)
H37	0.031332	0.087712	0.433816	0.042*
C47	−0.3030 (9)	0.2743 (6)	0.2641 (5)	0.030 (4)
H47	−0.349456	0.322182	0.295890	0.036*
C51	0.3285 (12)	0.3735 (7)	0.1070 (7)	0.026 (5)
C55	0.8677 (16)	0.2965 (9)	−0.0935 (9)	0.042 (11)
H55	1.014674	0.320503	−0.127142	0.050*
C75	−0.0932 (12)	0.3064 (8)	0.2117 (7)	0.032 (5)
C79	0.5208 (13)	0.1543 (8)	−0.0397 (8)	0.058 (11)
H79	0.429405	0.083075	−0.037126	0.069*
C53	0.1152 (9)	0.2300 (6)	0.3965 (5)	0.038 (8)
H53	−0.017801	0.211739	0.359544	0.046*
C67	0.0592 (8)	0.4158 (6)	0.2062 (5)	0.032 (8)
H67	0.022013	0.465697	0.237401	0.038*
C63	−0.4422 (12)	0.1654 (8)	0.2668 (7)	0.026 (4)
H63	−0.593067	0.143169	0.300329	0.032*
C43	0.7194 (8)	0.1881 (6)	−0.0923 (5)	0.034 (4)
H43	0.754005	0.141632	−0.125452	0.041*
C57	1.3447 (8)	0.3800 (6)	0.7313 (6)	0.044 (8)
H57	1.458724	0.448322	0.739817	0.053*
C39	0.8023 (16)	0.3634 (9)	−0.0485 (9)	0.047 (10)
H39	0.892920	0.434319	−0.052503	0.056*
C29	1.1382 (8)	0.3591 (6)	0.6771 (5)	0.030 (7)
C41	0.2835 (9)	0.3337 (6)	0.4078 (5)	0.029 (8)
H41	0.254061	0.385189	0.378717	0.035*
C45	1.2317 (9)	0.2003 (6)	0.7614 (5)	0.033 (8)
H45	1.258897	0.148424	0.790375	0.039*
C49	0.6020 (8)	0.1255 (5)	0.5936 (5)	0.034 (8)
C59	−0.3689 (11)	0.0956 (8)	0.2247 (7)	0.039 (10)
H59	−0.454695	0.024635	0.229977	0.046*
C61	1.3870 (9)	0.3018 (6)	0.7734 (5)	0.031 (8)
H61	1.522575	0.318477	0.810264	0.037*
C65	0.8732 (8)	0.0680 (6)	0.6900 (5)	0.030 (4)
H65	0.923153	0.013120	0.715756	0.036*
C69	0.8978 (8)	0.4161 (6)	0.5799 (5)	0.043 (8)
H69	0.868282	0.470215	0.552472	0.051*
C71	0.1085 (8)	0.0800 (5)	0.0709 (5)	0.033 (9)
H71	0.150636	0.029907	0.040064	0.040*
C73	1.0307 (8)	0.1737 (6)	0.7054 (5)	0.037 (7)
C77	0.4822 (9)	0.3594 (6)	0.4590 (5)	0.032 (8)
H77	0.598257	0.428314	0.464344	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0219 (15)	0.041 (7)	0.046 (18)	0.0121 (17)	0.014 (3)	−0.003 (11)
C3	0.0281 (17)	0.028 (5)	0.028 (11)	0.008 (2)	−0.002 (3)	−0.004 (7)
C5	0.0259 (13)	0.035 (5)	0.015 (10)	0.0082 (16)	0.007 (2)	−0.007 (6)
C7	0.0232 (17)	0.036 (8)	0.03 (2)	0.006 (2)	0.002 (3)	0.004 (14)
C9	0.0263 (14)	0.029 (6)	0.017 (16)	0.0091 (16)	0.012 (2)	−0.004 (10)
C11	0.0225 (15)	0.034 (5)	0.023 (11)	0.009 (2)	0.003 (3)	−0.008 (7)
C13	0.0287 (16)	0.030 (7)	0.026 (18)	0.0064 (16)	0.013 (3)	−0.010 (11)
C15	0.0282 (19)	0.039 (9)	0.06 (2)	0.004 (2)	−0.004 (4)	0.014 (15)
C17	0.0264 (15)	0.035 (7)	0.028 (17)	0.0118 (16)	0.013 (2)	−0.002 (11)
C19	0.0230 (17)	0.039 (9)	0.02 (2)	0.010 (2)	0.008 (3)	−0.004 (14)
C21	0.0283 (16)	0.054 (7)	0.058 (18)	0.0108 (18)	0.012 (3)	0.022 (12)
C23	0.030 (2)	0.051 (10)	0.09 (3)	0.009 (3)	0.001 (4)	0.032 (16)
C25	0.0286 (15)	0.035 (6)	0.018 (15)	0.0057 (18)	0.007 (3)	−0.009 (10)
C27	0.0309 (18)	0.043 (9)	0.07 (2)	0.003 (2)	−0.002 (3)	0.028 (14)
C31	0.0277 (15)	0.021 (5)	0.025 (11)	0.0046 (19)	−0.003 (3)	−0.015 (7)
C33	0.0237 (15)	0.051 (8)	0.056 (18)	0.0064 (18)	0.008 (3)	0.016 (12)
C35	0.0247 (18)	0.031 (9)	0.03 (2)	0.006 (2)	0.000 (3)	−0.005 (15)
C37	0.0297 (16)	0.040 (8)	0.034 (19)	0.0044 (19)	0.014 (3)	−0.010 (12)
C47	0.0320 (14)	0.035 (5)	0.023 (10)	0.0096 (18)	0.001 (3)	−0.015 (7)
C51	0.0265 (16)	0.026 (5)	0.025 (11)	0.006 (2)	−0.004 (3)	−0.007 (7)
C55	0.026 (2)	0.058 (11)	0.04 (3)	0.011 (3)	0.004 (4)	0.010 (17)
C75	0.0289 (16)	0.046 (6)	0.023 (11)	0.014 (2)	0.004 (3)	−0.002 (7)
C79	0.0256 (19)	0.048 (10)	0.10 (3)	0.005 (2)	−0.008 (4)	0.027 (16)
C53	0.0281 (16)	0.055 (8)	0.033 (18)	0.0107 (18)	0.005 (3)	0.002 (12)
C67	0.0294 (16)	0.035 (8)	0.032 (19)	0.0088 (18)	−0.002 (3)	−0.011 (12)
C63	0.0303 (17)	0.039 (5)	0.011 (11)	0.010 (2)	0.001 (3)	−0.008 (7)
C43	0.0293 (14)	0.051 (6)	0.023 (10)	0.0092 (19)	−0.002 (3)	−0.010 (7)
C57	0.0240 (16)	0.055 (8)	0.06 (2)	0.0094 (18)	0.005 (3)	−0.002 (12)
C39	0.025 (2)	0.057 (10)	0.06 (2)	0.008 (2)	0.005 (4)	0.026 (16)
C29	0.0252 (14)	0.046 (7)	0.021 (17)	0.0075 (17)	0.008 (2)	0.002 (11)
C41	0.0347 (17)	0.038 (8)	0.02 (2)	0.0114 (19)	0.003 (3)	−0.010 (13)
C45	0.0335 (17)	0.053 (8)	0.014 (18)	0.015 (2)	0.012 (3)	0.000 (12)
C49	0.0253 (15)	0.044 (7)	0.035 (18)	0.0070 (17)	0.011 (3)	0.008 (12)
C59	0.0297 (19)	0.048 (9)	0.04 (2)	0.013 (2)	0.005 (3)	0.007 (15)
C61	0.0298 (16)	0.051 (8)	0.013 (18)	0.0129 (19)	0.006 (3)	−0.011 (12)
C65	0.0307 (14)	0.041 (5)	0.019 (10)	0.0104 (17)	0.012 (2)	0.000 (7)
C69	0.0282 (15)	0.039 (7)	0.062 (18)	0.0069 (18)	0.008 (3)	0.012 (12)
C71	0.0315 (15)	0.036 (8)	0.03 (2)	0.0074 (18)	0.002 (3)	−0.002 (14)
C73	0.0237 (15)	0.061 (7)	0.028 (17)	0.0112 (18)	0.010 (3)	0.009 (11)
C77	0.0274 (16)	0.035 (7)	0.032 (18)	0.0054 (17)	0.007 (3)	−0.006 (12)

Geometric parameters (Å, º)

C1—C17	1.442 (15)	C31—C59	1.402 (14)
C1—C33	1.414 (11)	C33—C37	1.394 (15)
C1—C77	1.419 (7)	C35—C39	1.447 (15)
C3—C19	1.455 (14)	C37—H37	0.9300
C3—C35	1.430 (13)	C37—C53	1.364 (7)
C3—C79	1.38 (3)	C47—H47	0.9300
C5—C9	1.393 (13)	C47—C75	1.397 (12)
C5—C29	1.415 (12)	C47—C63	1.420 (11)
C5—C73	1.420 (6)	C55—H55	0.9300
C7—C11	1.415 (13)	C55—C43	1.421 (13)
C7—C31	1.412 (10)	C55—C39	1.31 (3)
C7—C75	1.39 (2)	C75—C67	1.443 (10)
C9—C17	1.403 (6)	C79—H79	0.9300
C9—C49	1.445 (11)	C79—C43	1.388 (13)
C11—C19	1.38 (2)	C53—H53	0.9300
C11—C51	1.449 (11)	C53—C41	1.400 (12)
C13—H13	0.9300	C67—H67	0.9300
C13—C33	1.420 (7)	C63—H63	0.9300
C13—C49	1.325 (12)	C63—C59	1.30 (3)
C15—H15	0.9300	C43—H43	0.9300
C15—C35	1.33 (3)	C57—H57	0.9300
C15—C51	1.409 (15)	C57—C29	1.373 (14)
C17—C69	1.428 (12)	C57—C61	1.379 (7)
C19—C71	1.434 (9)	C39—H39	0.9300
C21—H21	0.9300	C41—H41	0.9300
C21—C49	1.446 (6)	C41—C77	1.312 (13)
C21—C65	1.328 (13)	C45—H45	0.9300
C23—H23	0.9300	C45—C61	1.362 (11)
C23—C51	1.36 (3)	C45—C73	1.406 (15)
C23—C67	1.380 (14)	C59—H59	0.9300
C25—H25	0.9300	C61—H61	0.9300
C25—C29	1.434 (6)	C65—H65	0.9300
C25—C69	1.320 (14)	C65—C73	1.427 (12)
C27—H27	0.9300	C69—H69	0.9300
C27—C31	1.41 (2)	C71—H71	0.9300
C27—C71	1.385 (12)	C77—H77	0.9300
C33—C1—C17	118.5 (5)	C43—C55—H55	119.2
C33—C1—C77	117.2 (9)	C39—C55—H55	119.2
C77—C1—C17	124.2 (7)	C39—C55—C43	121.5 (9)
C35—C3—C19	115.9 (14)	C7—C75—C47	120.3 (7)
C79—C3—C19	123.3 (8)	C7—C75—C67	119.6 (8)
C79—C3—C35	120.8 (10)	C47—C75—C67	120.1 (12)
C9—C5—C29	119.8 (4)	C3—C79—H79	119.0
C9—C5—C73	121.5 (7)	C3—C79—C43	122.1 (8)
C29—C5—C73	118.7 (9)	C43—C79—H79	119.0
C31—C7—C11	118.3 (13)	C37—C53—H53	120.6
C75—C7—C11	122.0 (7)	C37—C53—C41	118.8 (10)
C75—C7—C31	119.7 (9)	C41—C53—H53	120.6
C5—C9—C17	121.4 (7)	C23—C67—C75	118.2 (12)
C5—C9—C49	119.4 (4)	C23—C67—H67	120.9
C17—C9—C49	119.1 (8)	C75—C67—H67	120.9
C7—C11—C51	116.7 (12)	C47—C63—H63	118.5
C19—C11—C7	121.7 (7)	C59—C63—C47	123.0 (9)
C19—C11—C51	121.7 (9)	C59—C63—H63	118.5
C33—C13—H13	118.2	C55—C43—H43	121.3
C49—C13—H13	118.2	C79—C43—C55	117.4 (13)
C49—C13—C33	123.6 (7)	C79—C43—H43	121.3
C35—C15—H15	118.3	C29—C57—H57	119.3
C35—C15—C51	123.4 (8)	C29—C57—C61	121.5 (8)
C51—C15—H15	118.3	C61—C57—H57	119.3
C9—C17—C1	120.3 (7)	C35—C39—H39	118.4
C9—C17—C69	117.3 (9)	C55—C39—C35	123.3 (9)
C69—C17—C1	122.3 (5)	C55—C39—H39	118.4
C11—C19—C3	120.4 (8)	C5—C29—C25	117.6 (9)
C11—C19—C71	120.1 (8)	C57—C29—C5	119.5 (5)
C71—C19—C3	119.6 (12)	C57—C29—C25	122.8 (7)
C49—C21—H21	118.6	C53—C41—H41	119.5
C65—C21—H21	118.6	C77—C41—C53	121.0 (5)
C65—C21—C49	122.8 (6)	C77—C41—H41	119.5
C51—C23—H23	118.6	C61—C45—H45	119.9
C51—C23—C67	122.8 (8)	C61—C45—C73	120.3 (5)
C67—C23—H23	118.6	C73—C45—H45	119.9
C29—C25—H25	119.2	C9—C49—C21	116.9 (8)
C69—C25—H25	119.2	C13—C49—C9	119.6 (4)
C69—C25—C29	121.6 (7)	C13—C49—C21	123.5 (7)
C31—C27—H27	119.0	C31—C59—H59	119.5
C71—C27—H27	119.0	C63—C59—C31	121.0 (8)
C71—C27—C31	122.1 (6)	C63—C59—H59	119.5
C27—C31—C7	119.7 (9)	C57—C61—H61	119.7
C59—C31—C7	118.6 (13)	C45—C61—C57	120.6 (9)
C59—C31—C27	121.7 (8)	C45—C61—H61	119.7
C1—C33—C13	118.7 (9)	C21—C65—H65	119.6
C37—C33—C1	118.8 (5)	C21—C65—C73	120.8 (4)
C37—C33—C13	122.5 (7)	C73—C65—H65	119.6
C3—C35—C39	114.9 (14)	C17—C69—H69	119.0
C15—C35—C3	122.6 (10)	C25—C69—C17	122.0 (5)
C15—C35—C39	122.4 (9)	C25—C69—H69	119.0
C33—C37—H37	119.2	C19—C71—H71	120.9
C53—C37—C33	121.7 (7)	C27—C71—C19	118.2 (10)
C53—C37—H37	119.2	C27—C71—H71	120.9
C75—C47—H47	121.4	C5—C73—C65	118.3 (9)
C75—C47—C63	117.3 (11)	C45—C73—C5	119.4 (7)
C63—C47—H47	121.4	C45—C73—C65	122.3 (5)
C15—C51—C11	115.9 (13)	C1—C77—H77	118.8
C23—C51—C11	120.7 (9)	C41—C77—C1	122.4 (7)
C23—C51—C15	123.4 (8)	C41—C77—H77	118.8
C1—C17—C69—C25	−178.7 (6)	C35—C15—C51—C23	179.8 (9)
C1—C33—C37—C53	1.9 (11)	C37—C53—C41—C77	2.2 (11)
C3—C19—C71—C27	−179.2 (5)	C47—C75—C67—C23	−179.4 (5)
C3—C35—C39—C55	−2.1 (14)	C47—C63—C59—C31	−3.7 (14)
C3—C79—C43—C55	2.4 (10)	C51—C11—C19—C3	−2.1 (12)
C5—C9—C17—C1	178.1 (6)	C51—C11—C19—C71	178.5 (4)
C5—C9—C17—C69	−2.6 (10)	C51—C15—C35—C3	2.5 (15)
C5—C9—C49—C13	178.8 (6)	C51—C15—C35—C39	179.8 (6)
C5—C9—C49—C21	0.6 (10)	C51—C23—C67—C75	−1.1 (10)
C7—C11—C19—C3	178.6 (5)	C75—C7—C11—C19	−179.2 (8)
C7—C11—C19—C71	−0.8 (11)	C75—C7—C11—C51	1.5 (10)
C7—C11—C51—C15	−179.2 (6)	C75—C7—C31—C27	180.0 (8)
C7—C11—C51—C23	−0.6 (10)	C75—C7—C31—C59	0.1 (10)
C7—C31—C59—C63	2.1 (12)	C75—C47—C63—C59	3.1 (11)
C7—C75—C67—C23	1.9 (9)	C79—C3—C19—C11	−178.5 (8)
C9—C5—C29—C25	−2.4 (10)	C79—C3—C19—C71	0.9 (11)
C9—C5—C29—C57	−179.3 (6)	C79—C3—C35—C15	178.2 (10)
C9—C5—C73—C45	−178.2 (6)	C79—C3—C35—C39	0.7 (11)
C9—C5—C73—C65	1.4 (10)	C53—C41—C77—C1	−2.4 (11)
C9—C17—C69—C25	2.0 (11)	C67—C23—C51—C11	0.5 (12)
C11—C7—C31—C27	0.2 (10)	C67—C23—C51—C15	179.0 (5)
C11—C7—C31—C59	−179.7 (6)	C63—C47—C75—C7	−0.9 (9)
C11—C7—C75—C47	179.2 (4)	C63—C47—C75—C67	−179.5 (5)
C11—C7—C75—C67	−2.2 (12)	C43—C55—C39—C35	3.6 (18)
C11—C19—C71—C27	0.2 (9)	C39—C55—C43—C79	−3.7 (13)
C13—C33—C37—C53	−179.4 (7)	C29—C5—C9—C17	2.9 (11)
C15—C35—C39—C55	−179.5 (11)	C29—C5—C9—C49	−178.6 (6)
C17—C1—C33—C13	−0.5 (10)	C29—C5—C73—C45	1.3 (10)
C17—C1—C33—C37	178.3 (6)	C29—C5—C73—C65	−179.1 (6)
C17—C1—C77—C41	−178.0 (7)	C29—C25—C69—C17	−1.7 (12)
C17—C9—C49—C13	−2.7 (10)	C29—C57—C61—C45	1.7 (11)
C17—C9—C49—C21	179.1 (6)	C49—C9—C17—C1	−0.4 (10)
C19—C3—C35—C15	−2.9 (12)	C49—C9—C17—C69	178.9 (6)
C19—C3—C35—C39	179.6 (6)	C49—C13—C33—C1	−2.8 (11)
C19—C3—C79—C43	−179.8 (4)	C49—C13—C33—C37	178.6 (7)
C19—C11—C51—C15	1.5 (10)	C49—C21—C65—C73	7.2 (12)
C19—C11—C51—C23	−179.9 (8)	C61—C57—C29—C5	−2.7 (11)
C21—C65—C73—C5	−5.5 (11)	C61—C57—C29—C25	−179.5 (8)
C21—C65—C73—C45	174.1 (7)	C61—C45—C73—C5	−2.4 (11)
C27—C31—C59—C63	−177.9 (8)	C61—C45—C73—C65	178.1 (6)
C31—C7—C11—C19	0.6 (10)	C65—C21—C49—C9	−4.7 (11)
C31—C7—C11—C51	−178.8 (5)	C65—C21—C49—C13	177.1 (7)
C31—C7—C75—C47	−0.6 (11)	C69—C25—C29—C5	1.9 (11)
C31—C7—C75—C67	178.1 (4)	C69—C25—C29—C57	178.7 (7)
C31—C27—C71—C19	0.6 (9)	C71—C27—C31—C7	−0.8 (11)
C33—C1—C17—C9	1.9 (10)	C71—C27—C31—C59	179.1 (4)
C33—C1—C17—C69	−177.4 (6)	C73—C5—C9—C17	−177.6 (7)
C33—C1—C77—C41	2.2 (11)	C73—C5—C9—C49	0.9 (10)
C33—C13—C49—C9	4.3 (11)	C73—C5—C29—C25	178.1 (6)
C33—C13—C49—C21	−177.6 (7)	C73—C5—C29—C57	1.2 (11)
C33—C37—C53—C41	−2.0 (11)	C73—C45—C61—C57	0.9 (11)
C35—C3—C19—C11	2.7 (10)	C77—C1—C17—C9	−178.0 (7)
C35—C3—C19—C71	−177.9 (5)	C77—C1—C17—C69	2.8 (11)
C35—C3—C79—C43	−1.1 (13)	C77—C1—C33—C13	179.4 (7)
C35—C15—C51—C11	−1.7 (12)	C77—C1—C33—C37	−1.9 (10)

(benzoapyrene_9.1GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 1.838 Mg m^−3
a = 3.4134 (1) Å	Synchrotron radiation, λ = 0.410 Å
b = 12.5674 (19) Å	Cell parameters from 523 reflections
c = 21.367 (5) Å	θ = 3.5–19.1°
α = 91.675 (15)°	µ = 0.05 mm^−1
β = 90.433 (7)°	T = 293 K
γ = 95.755 (6)°	Block, clear colourless
V = 911.5 (2) Å^3	0.01 × 0.01 × 0.01 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1617 independent reflections
Radiation source: synchrotron	1036 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.017
ω scans	θmax = 21.3°, θmin = 3.5°
Absorption correction: multi-scan CrysAlisPro 1.171.43.70a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.360, Tmax = 1.000	k = −15→17
2374 measured reflections	l = −18→23

Refinement

Refinement on F^2	24 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.1029P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max < 0.001
1617 reflections	Δρmax = 0.18 e Å^−3
361 parameters	Δρmin = −0.19 e Å^−3

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	−0.0333 (9)	0.2330 (5)	0.1653 (4)	0.019 (4)
C3	0.9800 (6)	0.2525 (4)	0.6623 (3)	0.033 (5)
C5	0.5217 (6)	0.2865 (4)	0.5063 (3)	0.025 (5)
C7	0.4552 (10)	0.2230 (6)	0.0097 (5)	0.020 (7)
C9	0.5973 (10)	0.3333 (6)	0.0061 (5)	0.022 (6)
C11	0.3476 (6)	0.1808 (4)	0.4937 (4)	0.033 (5)
C13	−0.1756 (9)	0.1236 (6)	0.1714 (5)	0.025 (6)
C15	1.1440 (6)	0.3572 (4)	0.6778 (4)	0.032 (5)
C17	0.7707 (6)	0.2305 (4)	0.6073 (4)	0.048 (5)
C19	0.1778 (8)	0.2645 (5)	0.1115 (4)	0.017 (4)
C21	0.7300 (6)	0.3098 (4)	0.5621 (3)	0.028 (5)
C23	0.2445 (8)	0.1883 (5)	0.0634 (4)	0.026 (6)
C25	0.3890 (6)	0.1016 (4)	0.5388 (3)	0.031 (5)
H25	0.266824	0.032918	0.530969	0.037*
C27	0.5257 (10)	0.4041 (6)	0.0537 (5)	0.031 (7)
H27	0.619991	0.475624	0.049862	0.038*
C29	−0.0969 (9)	0.0504 (6)	0.1243 (5)	0.020 (6)
H29	−0.184330	−0.021441	0.128749	0.024*
C31	1.0957 (6)	0.4394 (4)	0.6343 (4)	0.023 (5)
H31	1.201958	0.509167	0.643526	0.028*
C33	0.8058 (10)	0.3653 (6)	−0.0483 (5)	0.039 (7)
H33	0.898464	0.437063	−0.051703	0.046*
C35	0.1347 (6)	0.1573 (4)	0.4392 (4)	0.031 (5)
H35	0.010060	0.088595	0.432431	0.038*
C37	0.6547 (6)	0.0423 (4)	0.6372 (3)	0.036 (5)
H37	0.530908	−0.026580	0.630778	0.043*
C39	0.2524 (10)	0.4473 (7)	0.1546 (6)	0.048 (7)
H39	0.347405	0.518782	0.151040	0.057*
C41	0.9000 (6)	0.4166 (4)	0.5808 (4)	0.038 (5)
H41	0.870265	0.472168	0.553896	0.046*
C43	0.1032 (6)	0.0801 (4)	0.0719 (3)	0.030 (6)
H43	0.147898	0.028735	0.041301	0.036*
C45	0.5959 (6)	0.1216 (4)	0.5919 (4)	0.034 (5)
C47	0.3233 (9)	0.3754 (6)	0.1067 (5)	0.021 (6)
C49	0.5236 (11)	0.1528 (6)	−0.0409 (5)	0.026 (7)
H49	0.428712	0.080993	−0.038824	0.032*
C51	0.4793 (6)	0.3626 (4)	0.4596 (3)	0.032 (5)
H51	0.594558	0.432350	0.465797	0.039*
C53	−0.1069 (8)	0.3066 (6)	0.2120 (5)	0.048 (7)
C55	1.0344 (6)	0.1697 (4)	0.7052 (4)	0.041 (5)
C57	1.3515 (7)	0.3777 (5)	0.7325 (4)	0.045 (5)
H57	1.467041	0.446790	0.741295	0.054*
C59	−0.3864 (9)	0.0935 (6)	0.2241 (5)	0.031 (6)
H59	−0.480097	0.022066	0.228645	0.037*
C61	0.7250 (6)	0.1869 (4)	−0.0931 (3)	0.028 (4)
H61	0.761999	0.139390	−0.126211	0.033*
C63	0.2765 (7)	0.3356 (5)	0.4067 (4)	0.034 (5)
H63	0.251267	0.387139	0.376969	0.040*
C65	0.8759 (11)	0.2960 (7)	−0.0955 (6)	0.047 (7)
H65	1.023564	0.319935	−0.129659	0.057*
C67	0.1019 (7)	0.2313 (5)	0.3953 (4)	0.031 (5)
H67	−0.034771	0.213142	0.358070	0.037*
C69	0.8797 (6)	0.0638 (4)	0.6878 (3)	0.033 (5)
H69	0.937709	0.007804	0.712635	0.040*
C71	0.0487 (6)	0.4171 (4)	0.2068 (4)	0.045 (5)
H71	0.010354	0.466966	0.238628	0.053*
C73	1.2362 (7)	0.1966 (5)	0.7617 (4)	0.038 (6)
H73	1.262479	0.143752	0.790565	0.046*
C75	−0.3199 (6)	0.2745 (5)	0.2643 (4)	0.028 (5)
H75	−0.369961	0.324052	0.295699	0.034*
C77	1.3955 (7)	0.2991 (5)	0.7753 (4)	0.043 (5)
H77	1.531287	0.315701	0.812778	0.051*
C79	−0.4582 (9)	0.1668 (6)	0.2693 (5)	0.024 (6)
H79	−0.602185	0.144969	0.304249	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0208 (11)	0.026 (5)	0.012 (9)	0.0077 (15)	0.001 (2)	−0.003 (6)
C3	0.0179 (10)	0.045 (5)	0.037 (11)	0.0074 (12)	0.0071 (16)	0.015 (8)
C5	0.0198 (11)	0.033 (5)	0.025 (11)	0.0077 (12)	0.0075 (16)	0.000 (8)
C7	0.0211 (13)	0.024 (7)	0.017 (15)	0.0068 (16)	0.004 (2)	−0.001 (10)
C9	0.0199 (13)	0.024 (7)	0.022 (14)	0.0043 (16)	0.003 (2)	0.000 (10)
C11	0.0195 (11)	0.041 (6)	0.042 (12)	0.0084 (13)	0.0086 (17)	0.013 (8)
C13	0.0211 (12)	0.027 (7)	0.028 (14)	0.0052 (16)	0.000 (2)	0.006 (10)
C15	0.0200 (11)	0.032 (5)	0.045 (12)	0.0067 (12)	0.0040 (17)	0.004 (8)
C17	0.0175 (10)	0.050 (5)	0.080 (12)	0.0088 (12)	0.0100 (17)	0.039 (8)
C19	0.0194 (10)	0.024 (5)	0.008 (9)	0.0053 (15)	−0.0008 (19)	−0.006 (6)
C21	0.0199 (11)	0.033 (5)	0.030 (11)	0.0063 (12)	0.0061 (16)	0.007 (8)
C23	0.0210 (12)	0.032 (6)	0.026 (14)	0.0073 (16)	0.004 (2)	0.012 (10)
C25	0.0226 (11)	0.029 (5)	0.042 (11)	0.0035 (12)	0.0079 (17)	0.010 (8)
C27	0.0221 (13)	0.040 (7)	0.034 (15)	0.0057 (18)	0.001 (2)	0.015 (10)
C29	0.0263 (14)	0.025 (7)	0.009 (14)	0.0062 (17)	0.004 (2)	−0.003 (10)
C31	0.0228 (11)	0.024 (5)	0.024 (12)	0.0071 (12)	0.0064 (17)	−0.004 (8)
C33	0.0205 (14)	0.043 (7)	0.054 (15)	0.0063 (17)	0.002 (2)	0.024 (10)
C35	0.0234 (11)	0.033 (6)	0.038 (12)	0.0062 (13)	0.0112 (18)	0.001 (8)
C37	0.0229 (11)	0.037 (6)	0.051 (12)	0.0096 (13)	0.0127 (17)	0.020 (8)
C39	0.0255 (14)	0.051 (8)	0.070 (16)	0.0095 (19)	0.006 (3)	0.038 (11)
C41	0.0215 (11)	0.035 (5)	0.060 (11)	0.0081 (12)	0.0091 (17)	0.020 (8)
C43	0.0241 (11)	0.037 (6)	0.031 (13)	0.0087 (13)	0.0042 (18)	0.010 (9)
C45	0.0194 (10)	0.031 (5)	0.053 (11)	0.0050 (12)	0.0063 (17)	0.012 (8)
C47	0.0210 (13)	0.027 (7)	0.014 (15)	0.0047 (16)	−0.002 (2)	−0.002 (10)
C49	0.0230 (14)	0.031 (7)	0.026 (15)	0.0065 (17)	0.002 (2)	0.004 (11)
C51	0.0224 (11)	0.032 (5)	0.044 (11)	0.0064 (13)	0.0044 (17)	0.011 (8)
C53	0.0209 (13)	0.060 (7)	0.066 (15)	0.0101 (18)	0.004 (2)	0.040 (10)
C55	0.0200 (11)	0.046 (5)	0.060 (12)	0.0084 (12)	0.0053 (17)	0.025 (8)
C57	0.0221 (11)	0.046 (6)	0.070 (13)	0.0097 (13)	0.0069 (19)	0.022 (9)
C59	0.0235 (13)	0.037 (7)	0.032 (14)	0.0078 (16)	0.003 (2)	0.014 (10)
C61	0.0262 (11)	0.045 (5)	0.014 (8)	0.0127 (15)	0.0013 (18)	−0.002 (6)
C63	0.0261 (12)	0.049 (6)	0.029 (12)	0.0117 (14)	0.0066 (19)	0.016 (9)
C65	0.0198 (14)	0.055 (8)	0.071 (16)	0.0119 (19)	0.009 (2)	0.034 (11)
C67	0.0234 (11)	0.042 (6)	0.028 (12)	0.0083 (13)	0.0023 (17)	−0.001 (8)
C69	0.0240 (11)	0.039 (5)	0.038 (11)	0.0089 (13)	0.0089 (17)	0.018 (8)
C71	0.0228 (11)	0.044 (6)	0.070 (12)	0.0086 (13)	0.0029 (18)	0.027 (9)
C73	0.0246 (12)	0.053 (6)	0.039 (13)	0.0132 (15)	0.0079 (19)	0.016 (9)
C75	0.0252 (12)	0.041 (6)	0.020 (12)	0.0097 (14)	0.0027 (18)	0.002 (9)
C77	0.0226 (12)	0.048 (6)	0.059 (12)	0.0107 (14)	0.0043 (19)	0.013 (9)
C79	0.0257 (13)	0.030 (7)	0.017 (13)	0.0099 (18)	0.006 (2)	−0.001 (9)

Geometric parameters (Å, º)

C1—C13	1.422 (8)	C35—H35	0.9300
C1—C19	1.407 (8)	C35—C67	1.353 (5)
C1—C53	1.383 (18)	C37—H37	0.9300
C3—C15	1.407 (9)	C37—C45	1.436 (4)
C3—C17	1.377 (10)	C37—C69	1.327 (9)
C3—C55	1.432 (4)	C39—H39	0.9300
C5—C11	1.417 (8)	C39—C47	1.38 (2)
C5—C21	1.391 (10)	C39—C71	1.361 (9)
C5—C51	1.419 (5)	C41—H41	0.9300
C7—C9	1.426 (9)	C43—H43	0.9300
C7—C23	1.415 (9)	C49—H49	0.9300
C7—C49	1.41 (2)	C49—C61	1.370 (8)
C9—C27	1.37 (2)	C51—H51	0.9300
C9—C33	1.414 (9)	C51—C63	1.338 (10)
C11—C25	1.422 (4)	C53—C71	1.444 (8)
C11—C35	1.376 (10)	C53—C75	1.386 (8)
C13—C29	1.390 (18)	C55—C69	1.419 (9)
C13—C59	1.383 (9)	C55—C73	1.402 (11)
C15—C31	1.430 (4)	C57—H57	0.9300
C15—C57	1.366 (10)	C57—C77	1.383 (5)
C17—C21	1.425 (4)	C59—H59	0.9300
C17—C45	1.464 (9)	C59—C79	1.356 (19)
C19—C23	1.419 (16)	C61—H61	0.9300
C19—C47	1.438 (8)	C61—C65	1.419 (9)
C21—C41	1.452 (9)	C63—H63	0.9300
C23—C43	1.414 (7)	C63—C67	1.398 (9)
C25—H25	0.9300	C65—H65	0.9300
C25—C45	1.337 (10)	C67—H67	0.9300
C27—H27	0.9300	C69—H69	0.9300
C27—C47	1.369 (9)	C71—H71	0.9300
C29—H29	0.9300	C73—H73	0.9300
C29—C43	1.357 (8)	C73—C77	1.369 (9)
C31—H31	0.9300	C75—H75	0.9300
C31—C41	1.329 (10)	C75—C79	1.395 (8)
C33—H33	0.9300	C77—H77	0.9300
C33—C65	1.35 (2)	C79—H79	0.9300
C19—C1—C13	119.3 (9)	C21—C41—H41	118.2
C53—C1—C13	119.6 (6)	C31—C41—C21	123.6 (3)
C53—C1—C19	121.2 (6)	C31—C41—H41	118.2
C15—C3—C55	118.4 (6)	C23—C43—H43	119.6
C17—C3—C15	120.8 (3)	C29—C43—C23	120.7 (8)
C17—C3—C55	120.9 (5)	C29—C43—H43	119.6
C11—C5—C51	117.0 (6)	C25—C45—C17	119.8 (3)
C21—C5—C11	119.3 (3)	C25—C45—C37	124.0 (5)
C21—C5—C51	123.7 (5)	C37—C45—C17	116.2 (6)
C23—C7—C9	118.8 (10)	C27—C47—C19	117.2 (10)
C49—C7—C9	118.8 (6)	C27—C47—C39	123.3 (7)
C49—C7—C23	122.4 (7)	C39—C47—C19	119.5 (6)
C27—C9—C7	120.1 (6)	C7—C49—H49	118.9
C27—C9—C33	122.5 (7)	C61—C49—C7	122.2 (6)
C33—C9—C7	117.4 (10)	C61—C49—H49	118.9
C5—C11—C25	118.9 (6)	C5—C51—H51	119.4
C35—C11—C5	119.8 (3)	C63—C51—C5	121.1 (5)
C35—C11—C25	121.3 (5)	C63—C51—H51	119.4
C29—C13—C1	118.9 (6)	C1—C53—C71	119.5 (6)
C59—C13—C1	118.9 (10)	C1—C53—C75	120.4 (6)
C59—C13—C29	122.2 (6)	C75—C53—C71	120.0 (9)
C3—C15—C31	118.2 (7)	C69—C55—C3	117.7 (6)
C57—C15—C3	120.0 (3)	C73—C55—C3	118.9 (6)
C57—C15—C31	121.8 (6)	C73—C55—C69	123.4 (3)
C3—C17—C21	122.2 (5)	C15—C57—H57	118.9
C3—C17—C45	120.4 (3)	C15—C57—C77	122.2 (6)
C21—C17—C45	117.3 (6)	C77—C57—H57	118.9
C1—C19—C23	120.5 (6)	C13—C59—H59	119.6
C1—C19—C47	118.3 (9)	C79—C59—C13	120.8 (6)
C23—C19—C47	121.2 (6)	C79—C59—H59	119.6
C5—C21—C17	121.8 (5)	C49—C61—H61	120.7
C5—C21—C41	123.4 (3)	C49—C61—C65	118.7 (9)
C17—C21—C41	114.7 (6)	C65—C61—H61	120.7
C7—C23—C19	119.0 (6)	C51—C63—H63	119.4
C43—C23—C7	122.7 (9)	C51—C63—C67	121.2 (3)
C43—C23—C19	118.3 (5)	C67—C63—H63	119.4
C11—C25—H25	118.6	C33—C65—C61	120.2 (6)
C45—C25—C11	122.8 (5)	C33—C65—H65	119.9
C45—C25—H25	118.6	C61—C65—H65	119.9
C9—C27—H27	118.2	C35—C67—C63	119.0 (7)
C47—C27—C9	123.7 (7)	C35—C67—H67	120.5
C47—C27—H27	118.2	C63—C67—H67	120.5
C13—C29—H29	118.9	C37—C69—C55	122.0 (3)
C43—C29—C13	122.3 (5)	C37—C69—H69	119.0
C43—C29—H29	118.9	C55—C69—H69	119.0
C15—C31—H31	119.8	C39—C71—C53	119.0 (9)
C41—C31—C15	120.5 (5)	C39—C71—H71	120.5
C41—C31—H31	119.8	C53—C71—H71	120.5
C9—C33—H33	118.6	C55—C73—H73	119.3
C65—C33—C9	122.7 (7)	C77—C73—C55	121.4 (3)
C65—C33—H33	118.6	C77—C73—H73	119.3
C11—C35—H35	119.1	C53—C75—H75	120.4
C67—C35—C11	121.8 (6)	C53—C75—C79	119.1 (8)
C67—C35—H35	119.1	C79—C75—H75	120.4
C45—C37—H37	118.9	C57—C77—H77	120.5
C69—C37—H37	118.9	C73—C77—C57	119.1 (7)
C69—C37—C45	122.3 (5)	C73—C77—H77	120.5
C47—C39—H39	118.8	C59—C79—C75	121.2 (6)
C71—C39—H39	118.8	C59—C79—H79	119.4
C71—C39—C47	122.4 (6)	C75—C79—H79	119.4
C1—C13—C29—C43	−1.6 (9)	C19—C1—C53—C71	−2.5 (8)
C1—C13—C59—C79	0.2 (8)	C19—C1—C53—C75	179.1 (3)
C1—C19—C23—C7	179.5 (3)	C19—C23—C43—C29	1.1 (6)
C1—C19—C23—C43	−1.8 (7)	C21—C5—C11—C25	0.4 (8)
C1—C19—C47—C27	−179.6 (4)	C21—C5—C11—C35	178.8 (5)
C1—C19—C47—C39	0.0 (8)	C21—C5—C51—C63	179.8 (5)
C1—C53—C71—C39	2.5 (7)	C21—C17—C45—C25	−3.7 (8)
C1—C53—C75—C79	0.2 (7)	C21—C17—C45—C37	177.6 (4)
C3—C15—C31—C41	0.1 (8)	C23—C7—C9—C27	−0.7 (9)
C3—C15—C57—C77	−2.6 (8)	C23—C7—C9—C33	−179.9 (4)
C3—C17—C21—C5	179.3 (4)	C23—C7—C49—C61	179.5 (3)
C3—C17—C21—C41	−4.5 (7)	C23—C19—C47—C27	0.4 (7)
C3—C17—C45—C25	179.1 (4)	C23—C19—C47—C39	−180.0 (6)
C3—C17—C45—C37	0.4 (7)	C25—C11—C35—C67	−178.3 (5)
C3—C55—C69—C37	−7.3 (8)	C27—C9—C33—C65	−179.8 (7)
C3—C55—C73—C77	−2.8 (8)	C29—C13—C59—C79	180.0 (6)
C5—C11—C25—C45	−2.1 (8)	C31—C15—C57—C77	179.1 (5)
C5—C11—C35—C67	3.4 (8)	C33—C9—C27—C47	179.7 (4)
C5—C21—C41—C31	179.3 (4)	C35—C11—C25—C45	179.5 (5)
C5—C51—C63—C67	−0.6 (8)	C45—C17—C21—C5	2.1 (7)
C7—C9—C27—C47	0.6 (10)	C45—C17—C21—C41	178.4 (4)
C7—C9—C33—C65	−0.6 (9)	C45—C37—C69—C55	8.7 (9)
C7—C23—C43—C29	179.9 (4)	C47—C19—C23—C7	−0.6 (8)
C7—C49—C61—C65	1.3 (8)	C47—C19—C23—C43	178.2 (3)
C9—C7—C23—C19	0.7 (8)	C47—C39—C71—C53	−1.3 (8)
C9—C7—C23—C43	−178.0 (4)	C49—C7—C9—C27	178.1 (7)
C9—C7—C49—C61	0.7 (10)	C49—C7—C9—C33	−1.0 (8)
C9—C27—C47—C19	−0.4 (9)	C49—C7—C23—C19	−178.1 (6)
C9—C27—C47—C39	180.0 (7)	C49—C7—C23—C43	3.2 (9)
C9—C33—C65—C61	2.6 (11)	C49—C61—C65—C33	−2.9 (8)
C11—C5—C21—C17	−0.6 (8)	C51—C5—C11—C25	178.9 (4)
C11—C5—C21—C41	−176.5 (4)	C51—C5—C11—C35	−2.7 (8)
C11—C5—C51—C63	1.4 (7)	C51—C5—C21—C17	−178.9 (5)
C11—C25—C45—C17	3.8 (8)	C51—C5—C21—C41	5.2 (8)
C11—C25—C45—C37	−177.6 (5)	C51—C63—C67—C35	1.1 (8)
C11—C35—C67—C63	−2.5 (8)	C53—C1—C13—C29	−179.5 (6)
C13—C1—C19—C23	0.7 (7)	C53—C1—C13—C59	0.2 (8)
C13—C1—C19—C47	−179.2 (4)	C53—C1—C19—C23	−178.8 (5)
C13—C1—C53—C71	178.0 (3)	C53—C1—C19—C47	1.2 (7)
C13—C1—C53—C75	−0.4 (8)	C53—C75—C79—C59	0.3 (8)
C13—C29—C43—C23	0.6 (7)	C55—C3—C15—C31	178.8 (4)
C13—C59—C79—C75	−0.5 (10)	C55—C3—C15—C57	0.4 (8)
C15—C3—C17—C21	3.9 (8)	C55—C3—C17—C21	−176.4 (5)
C15—C3—C17—C45	−179.1 (4)	C55—C3—C17—C45	0.6 (8)
C15—C3—C55—C69	−177.7 (4)	C55—C73—C77—C57	0.8 (8)
C15—C3—C55—C73	2.2 (7)	C57—C15—C31—C41	178.5 (5)
C15—C31—C41—C21	−1.1 (8)	C59—C13—C29—C43	178.7 (3)
C15—C57—C77—C73	2.0 (8)	C69—C37—C45—C17	−5.1 (8)
C17—C3—C15—C31	−1.5 (8)	C69—C37—C45—C25	176.3 (5)
C17—C3—C15—C57	−179.9 (4)	C69—C55—C73—C77	177.1 (4)
C17—C3—C55—C69	2.5 (7)	C71—C39—C47—C19	0.1 (10)
C17—C3—C55—C73	−177.5 (4)	C71—C39—C47—C27	179.7 (3)
C17—C21—C41—C31	3.1 (7)	C71—C53—C75—C79	−178.2 (4)
C19—C1—C13—C29	0.9 (8)	C73—C55—C69—C37	172.8 (5)
C19—C1—C13—C59	−179.3 (4)	C75—C53—C71—C39	−179.1 (4)

(benzoapyrene_11.8GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 1.901 Mg m^−3
a = 3.3501 (1) Å	Synchrotron radiation, λ = 0.410 Å
b = 12.453 (2) Å	Cell parameters from 526 reflections
c = 21.244 (5) Å	θ = 3.6–19.3°
α = 91.709 (18)°	µ = 0.05 mm^−1
β = 90.417 (8)°	T = 293 K
γ = 95.599 (7)°	Block, black
V = 881.6 (3) Å^3	0.02 × 0.02 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1482 independent reflections
Radiation source: synchrotron	979 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.023
ω scans	θmax = 21.3°, θmin = 3.5°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.042, Tmax = 1.000	k = −14→16
2203 measured reflections	l = −18→22

Refinement

Refinement on F^2	78 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.168	w = 1/[σ^2(Fo^2) + (0.1283P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
1482 reflections	Δρmax = 0.21 e Å^−3
361 parameters	Δρmin = −0.18 e Å^−3

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	−0.0407 (9)	0.2358 (6)	0.1674 (5)	0.020 (4)
C3	0.9838 (7)	0.2508 (5)	0.6630 (4)	0.034 (6)
C5	0.5186 (7)	0.2871 (5)	0.5065 (4)	0.036 (6)
C7	0.4554 (9)	0.2228 (7)	0.0093 (6)	0.022 (4)
C9	0.5981 (10)	0.3335 (7)	0.0056 (6)	0.021 (4)
C11	0.3407 (7)	0.1799 (5)	0.4931 (4)	0.024 (3)
C13	−0.1857 (9)	0.1228 (7)	0.1712 (5)	0.030 (8)
C15	1.1497 (7)	0.3577 (5)	0.6791 (4)	0.025 (3)
C17	0.7709 (7)	0.2284 (5)	0.6064 (4)	0.027 (6)
C19	0.1717 (9)	0.2647 (6)	0.1110 (5)	0.021 (3)
C21	0.7287 (7)	0.3107 (5)	0.5639 (4)	0.041 (6)
C23	0.2411 (9)	0.1891 (6)	0.0645 (5)	0.022 (4)
C25	0.3833 (7)	0.1006 (5)	0.5384 (4)	0.026 (6)
H25	0.259367	0.031328	0.530585	0.031*
C27	0.5240 (10)	0.4038 (7)	0.0516 (6)	0.036 (8)
H27	0.615926	0.476048	0.046986	0.044*
C29	−0.1056 (10)	0.0507 (7)	0.1259 (5)	0.022 (4)
H29	−0.191054	−0.021686	0.131269	0.026*
C31	1.1002 (7)	0.4399 (5)	0.6351 (4)	0.035 (6)
H31	1.204534	0.510616	0.644417	0.042*
C33	0.8126 (12)	0.3664 (8)	−0.0490 (6)	0.026 (8)
H33	0.908271	0.438689	−0.052313	0.032*
C35	0.1236 (7)	0.1580 (5)	0.4399 (4)	0.025 (6)
H35	−0.008580	0.089348	0.433426	0.030*
C37	0.6560 (7)	0.0398 (5)	0.6368 (4)	0.024 (6)
H37	0.531648	−0.029690	0.629897	0.029*
C39	0.2484 (12)	0.4491 (8)	0.1546 (6)	0.028 (8)
H39	0.347309	0.521046	0.151204	0.034*
C41	0.9033 (7)	0.4158 (5)	0.5801 (4)	0.048 (6)
H41	0.881680	0.470515	0.551729	0.058*
C43	0.0989 (7)	0.0793 (5)	0.0713 (4)	0.023 (4)
H43	0.141149	0.027804	0.040137	0.028*
C45	0.5953 (7)	0.1211 (5)	0.5923 (4)	0.027 (5)
C47	0.3173 (12)	0.3752 (8)	0.1059 (7)	0.038 (9)
C49	0.5265 (10)	0.1534 (7)	−0.0396 (6)	0.025 (4)
H49	0.432859	0.080959	−0.036761	0.029*
C51	0.4772 (7)	0.3632 (5)	0.4592 (4)	0.034 (6)
H51	0.596248	0.433358	0.465487	0.040*
C53	−0.1190 (10)	0.3077 (7)	0.2121 (5)	0.032 (7)
C55	1.0394 (7)	0.1667 (5)	0.7052 (4)	0.025 (6)
C57	1.3615 (7)	0.3774 (5)	0.7340 (4)	0.041 (7)
H57	1.480734	0.446826	0.742974	0.049*
C59	−0.4009 (10)	0.0932 (7)	0.2249 (6)	0.022 (4)
H59	−0.496168	0.021190	0.229574	0.026*
C61	0.7324 (7)	0.1863 (5)	−0.0935 (4)	0.026 (4)
H61	0.768882	0.137461	−0.126430	0.031*
C63	0.2695 (7)	0.3367 (5)	0.4053 (4)	0.025 (6)
H63	0.247611	0.388487	0.375105	0.030*
C65	0.8830 (12)	0.2948 (9)	−0.0969 (7)	0.036 (9)
H65	1.030700	0.318217	−0.131639	0.043*
C67	0.0907 (7)	0.2335 (5)	0.3949 (4)	0.028 (3)
H67	−0.051401	0.215088	0.357764	0.034*
C69	0.8855 (7)	0.0613 (5)	0.6878 (4)	0.025 (6)
H69	0.945926	0.004643	0.712580	0.030*
C71	0.0403 (7)	0.4181 (5)	0.2067 (4)	0.031 (7)
H71	0.001175	0.468300	0.238778	0.038*
C73	1.2428 (8)	0.1927 (6)	0.7618 (4)	0.043 (7)
H73	1.271395	0.138749	0.790339	0.052*
C75	−0.3346 (7)	0.2757 (5)	0.2655 (4)	0.029 (6)
H75	−0.384415	0.325649	0.297198	0.035*
C77	1.4045 (7)	0.2976 (5)	0.7765 (4)	0.045 (6)
H77	1.539632	0.313785	0.814538	0.054*
C79	−0.4739 (10)	0.1666 (8)	0.2703 (6)	0.031 (8)
H79	−0.619865	0.144313	0.305400	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0189 (11)	0.027 (5)	0.016 (8)	0.0061 (17)	−0.002 (2)	−0.002 (6)
C3	0.0183 (11)	0.044 (6)	0.040 (13)	0.0097 (13)	0.0083 (18)	0.012 (9)
C5	0.0177 (11)	0.047 (6)	0.044 (13)	0.0090 (14)	0.0064 (18)	0.015 (9)
C7	0.0210 (12)	0.030 (5)	0.017 (8)	0.0073 (19)	0.000 (2)	0.000 (6)
C9	0.0201 (12)	0.024 (5)	0.018 (8)	0.0050 (18)	0.000 (2)	−0.004 (6)
C11	0.0193 (10)	0.029 (4)	0.023 (8)	0.0076 (13)	0.0087 (17)	−0.005 (5)
C13	0.0206 (13)	0.032 (8)	0.038 (17)	0.0075 (19)	0.002 (2)	0.008 (12)
C15	0.0197 (10)	0.034 (4)	0.023 (8)	0.0084 (13)	0.0070 (17)	−0.005 (5)
C17	0.0185 (11)	0.039 (6)	0.025 (12)	0.0079 (13)	0.0060 (17)	0.003 (9)
C19	0.0202 (11)	0.026 (4)	0.018 (6)	0.0066 (16)	0.000 (2)	−0.004 (4)
C21	0.0188 (11)	0.047 (7)	0.058 (13)	0.0075 (14)	0.0076 (18)	0.024 (9)
C23	0.0234 (12)	0.026 (5)	0.017 (8)	0.0054 (17)	0.000 (2)	0.000 (6)
C25	0.0227 (12)	0.026 (6)	0.029 (13)	0.0080 (13)	0.0120 (18)	−0.001 (9)
C27	0.0231 (14)	0.042 (8)	0.046 (17)	0.007 (2)	0.004 (3)	0.022 (12)
C29	0.0256 (13)	0.025 (5)	0.016 (8)	0.0077 (18)	0.002 (2)	−0.004 (6)
C31	0.0219 (12)	0.036 (7)	0.049 (14)	0.0053 (14)	0.0045 (19)	0.011 (10)
C33	0.0221 (16)	0.035 (9)	0.023 (17)	0.005 (2)	0.003 (3)	0.004 (12)
C35	0.0235 (12)	0.030 (7)	0.023 (14)	0.0065 (14)	0.010 (2)	−0.012 (10)
C37	0.0230 (12)	0.024 (6)	0.026 (13)	0.0084 (13)	0.0096 (18)	−0.005 (9)
C39	0.0251 (15)	0.031 (9)	0.029 (18)	0.004 (2)	−0.002 (3)	0.005 (13)
C41	0.0209 (12)	0.051 (7)	0.075 (14)	0.0087 (14)	0.0072 (19)	0.032 (10)
C43	0.0261 (11)	0.025 (4)	0.019 (8)	0.0069 (14)	0.0026 (19)	−0.001 (6)
C45	0.0204 (11)	0.029 (6)	0.032 (12)	0.0054 (13)	0.0072 (18)	0.002 (9)
C47	0.0212 (15)	0.040 (9)	0.054 (19)	0.010 (2)	0.003 (3)	0.016 (14)
C49	0.0245 (12)	0.024 (5)	0.026 (8)	0.0069 (18)	0.000 (2)	−0.003 (6)
C51	0.0227 (12)	0.039 (7)	0.041 (14)	0.0072 (14)	0.0059 (18)	0.010 (10)
C53	0.0222 (14)	0.043 (8)	0.034 (16)	0.016 (2)	0.007 (2)	0.011 (12)
C55	0.0206 (11)	0.033 (6)	0.022 (13)	0.0092 (13)	0.0061 (18)	0.000 (9)
C57	0.0213 (12)	0.044 (7)	0.059 (15)	0.0096 (14)	0.006 (2)	0.010 (10)
C59	0.0218 (12)	0.023 (5)	0.021 (8)	0.0058 (17)	0.002 (2)	−0.005 (6)
C61	0.0260 (11)	0.036 (5)	0.018 (8)	0.0120 (15)	0.0032 (19)	−0.007 (6)
C63	0.0252 (13)	0.031 (7)	0.021 (14)	0.0125 (14)	0.008 (2)	−0.006 (10)
C65	0.0176 (15)	0.051 (10)	0.041 (19)	0.008 (2)	0.004 (3)	0.011 (13)
C67	0.0235 (11)	0.037 (5)	0.024 (8)	0.0053 (14)	0.0004 (18)	−0.008 (6)
C69	0.0248 (12)	0.032 (6)	0.019 (13)	0.0095 (14)	0.0099 (19)	0.002 (9)
C71	0.0237 (12)	0.041 (8)	0.031 (15)	0.0124 (16)	0.004 (2)	0.000 (11)
C73	0.0236 (13)	0.061 (7)	0.050 (15)	0.0164 (16)	0.010 (2)	0.021 (11)
C75	0.0255 (13)	0.043 (7)	0.020 (14)	0.0136 (16)	0.005 (2)	−0.001 (10)
C77	0.0230 (12)	0.060 (7)	0.055 (14)	0.0117 (15)	0.007 (2)	0.021 (10)
C79	0.0249 (14)	0.040 (9)	0.032 (17)	0.012 (2)	0.009 (3)	0.011 (12)

Geometric parameters (Å, º)

C1—C13	1.448 (10)	C35—H35	0.9300
C1—C19	1.435 (10)	C35—C67	1.372 (5)
C1—C53	1.331 (19)	C37—H37	0.9300
C3—C15	1.422 (10)	C37—C45	1.434 (5)
C3—C17	1.401 (11)	C37—C69	1.328 (10)
C3—C55	1.424 (5)	C39—H39	0.9300
C5—C11	1.427 (10)	C39—C47	1.40 (2)
C5—C21	1.412 (12)	C39—C71	1.358 (10)
C5—C51	1.416 (5)	C41—H41	0.9300
C7—C9	1.418 (11)	C43—H43	0.9300
C7—C23	1.432 (10)	C49—H49	0.9300
C7—C49	1.37 (2)	C49—C61	1.392 (9)
C9—C27	1.33 (2)	C51—H51	0.9300
C9—C33	1.418 (11)	C51—C63	1.351 (12)
C11—C25	1.416 (5)	C53—C71	1.434 (9)
C11—C35	1.345 (11)	C53—C75	1.397 (9)
C13—C29	1.34 (2)	C55—C69	1.401 (10)
C13—C59	1.393 (10)	C55—C73	1.390 (12)
C15—C31	1.428 (5)	C57—H57	0.9300
C15—C57	1.363 (12)	C57—C77	1.381 (5)
C17—C21	1.403 (5)	C59—H59	0.9300
C17—C45	1.429 (10)	C59—C79	1.35 (2)
C19—C23	1.380 (18)	C61—H61	0.9300
C19—C47	1.422 (11)	C61—C65	1.398 (11)
C21—C41	1.412 (11)	C63—H63	0.9300
C23—C43	1.414 (8)	C63—C67	1.375 (10)
C25—H25	0.9300	C65—H65	0.9300
C25—C45	1.347 (11)	C67—H67	0.9300
C27—H27	0.9300	C69—H69	0.9300
C27—C47	1.388 (12)	C71—H71	0.9300
C29—H29	0.9300	C73—H73	0.9300
C29—C43	1.388 (9)	C73—C77	1.390 (11)
C31—H31	0.9300	C75—H75	0.9300
C31—C41	1.350 (12)	C75—C79	1.399 (10)
C33—H33	0.9300	C77—H77	0.9300
C33—C65	1.37 (2)	C79—H79	0.9300
C19—C1—C13	115.4 (11)	C21—C41—H41	118.7
C53—C1—C13	121.5 (6)	C31—C41—C21	122.5 (4)
C53—C1—C19	123.1 (6)	C31—C41—H41	118.7
C15—C3—C55	118.9 (7)	C23—C43—H43	120.9
C17—C3—C15	120.6 (4)	C29—C43—C23	118.1 (9)
C17—C3—C55	120.5 (6)	C29—C43—H43	120.9
C21—C5—C11	119.6 (4)	C17—C45—C37	117.6 (7)
C21—C5—C51	124.1 (6)	C25—C45—C17	119.2 (4)
C51—C5—C11	116.3 (7)	C25—C45—C37	123.2 (6)
C9—C7—C23	118.0 (12)	C27—C47—C19	117.0 (13)
C49—C7—C9	119.0 (7)	C27—C47—C39	123.3 (8)
C49—C7—C23	123.0 (7)	C39—C47—C19	119.7 (7)
C27—C9—C7	120.5 (7)	C7—C49—H49	118.5
C27—C9—C33	121.6 (7)	C7—C49—C61	123.0 (7)
C33—C9—C7	117.9 (12)	C61—C49—H49	118.5
C25—C11—C5	118.2 (7)	C5—C51—H51	119.1
C35—C11—C5	119.8 (4)	C63—C51—C5	121.9 (6)
C35—C11—C25	121.9 (6)	C63—C51—H51	119.1
C29—C13—C1	121.1 (6)	C1—C53—C71	119.2 (6)
C29—C13—C59	122.3 (7)	C1—C53—C75	120.8 (6)
C59—C13—C1	116.5 (11)	C75—C53—C71	119.9 (10)
C3—C15—C31	117.8 (7)	C69—C55—C3	118.2 (7)
C57—C15—C3	119.7 (4)	C73—C55—C3	118.8 (6)
C57—C15—C31	122.5 (6)	C73—C55—C69	123.0 (4)
C3—C17—C21	120.3 (6)	C15—C57—H57	119.0
C3—C17—C45	119.6 (4)	C15—C57—C77	122.1 (7)
C21—C17—C45	120.2 (7)	C77—C57—H57	119.0
C23—C19—C1	122.0 (6)	C13—C59—H59	119.3
C23—C19—C47	121.3 (8)	C79—C59—C13	121.4 (7)
C47—C19—C1	116.6 (11)	C79—C59—H59	119.3
C17—C21—C5	119.9 (6)	C49—C61—H61	120.8
C17—C21—C41	118.3 (7)	C49—C61—C65	118.3 (10)
C41—C21—C5	121.9 (4)	C65—C61—H61	120.8
C19—C23—C7	119.4 (6)	C51—C63—H63	119.9
C19—C23—C43	120.2 (6)	C51—C63—C67	120.2 (4)
C43—C23—C7	120.4 (10)	C67—C63—H63	119.9
C11—C25—H25	118.5	C33—C65—C61	120.0 (7)
C45—C25—C11	122.9 (6)	C33—C65—H65	120.0
C45—C25—H25	118.5	C61—C65—H65	120.0
C9—C27—H27	118.2	C35—C67—C63	119.4 (8)
C9—C27—C47	123.6 (8)	C35—C67—H67	120.3
C47—C27—H27	118.2	C63—C67—H67	120.3
C13—C29—H29	118.5	C37—C69—C55	122.0 (3)
C13—C29—C43	123.1 (6)	C37—C69—H69	119.0
C43—C29—H29	118.5	C55—C69—H69	119.0
C15—C31—H31	119.8	C39—C71—C53	119.8 (10)
C41—C31—C15	120.5 (6)	C39—C71—H71	120.1
C41—C31—H31	119.8	C53—C71—H71	120.1
C9—C33—H33	119.1	C55—C73—H73	119.3
C65—C33—C9	121.8 (8)	C77—C73—C55	121.4 (4)
C65—C33—H33	119.1	C77—C73—H73	119.3
C11—C35—H35	118.9	C53—C75—H75	120.8
C11—C35—C67	122.3 (6)	C53—C75—C79	118.4 (10)
C67—C35—H35	118.9	C79—C75—H75	120.8
C45—C37—H37	119.2	C57—C77—C73	119.1 (8)
C69—C37—H37	119.2	C57—C77—H77	120.5
C69—C37—C45	121.6 (5)	C73—C77—H77	120.5
C47—C39—H39	119.2	C59—C79—C75	121.4 (7)
C71—C39—H39	119.2	C59—C79—H79	119.3
C71—C39—C47	121.5 (7)	C75—C79—H79	119.3
C1—C13—C29—C43	−3.6 (10)	C19—C1—C53—C71	−4.9 (9)
C1—C13—C59—C79	0.9 (9)	C19—C1—C53—C75	178.6 (3)
C1—C19—C23—C7	−179.9 (3)	C19—C23—C43—C29	−0.7 (7)
C1—C19—C23—C43	0.5 (8)	C21—C5—C11—C25	−0.1 (8)
C1—C19—C47—C27	179.8 (4)	C21—C5—C11—C35	176.8 (5)
C1—C19—C47—C39	−0.2 (9)	C21—C5—C51—C63	−179.4 (6)
C1—C53—C71—C39	3.7 (8)	C21—C17—C45—C25	−1.2 (9)
C1—C53—C75—C79	−1.4 (8)	C21—C17—C45—C37	178.6 (5)
C3—C15—C31—C41	−0.3 (8)	C23—C7—C9—C27	−1.8 (8)
C3—C15—C57—C77	−3.4 (10)	C23—C7—C9—C33	179.5 (4)
C3—C17—C21—C5	179.1 (5)	C23—C7—C49—C61	179.6 (3)
C3—C17—C21—C41	−0.4 (9)	C23—C19—C47—C27	1.4 (8)
C3—C17—C45—C25	178.5 (5)	C23—C19—C47—C39	−178.6 (6)
C3—C17—C45—C37	−1.7 (8)	C25—C11—C35—C67	−178.0 (6)
C3—C55—C69—C37	−7.2 (8)	C27—C9—C33—C65	−178.8 (8)
C3—C55—C73—C77	−2.5 (9)	C29—C13—C59—C79	179.2 (7)
C5—C11—C25—C45	−2.4 (9)	C31—C15—C57—C77	179.4 (6)
C5—C11—C35—C67	5.2 (10)	C33—C9—C27—C47	−179.6 (5)
C5—C21—C41—C31	179.1 (5)	C35—C11—C25—C45	−179.2 (6)
C5—C51—C63—C67	0.0 (9)	C45—C17—C21—C5	−1.2 (9)
C7—C9—C27—C47	1.7 (11)	C45—C17—C21—C41	179.3 (5)
C7—C9—C33—C65	−0.1 (10)	C45—C37—C69—C55	8.3 (9)
C7—C23—C43—C29	179.7 (4)	C47—C19—C23—C7	−1.6 (9)
C7—C49—C61—C65	1.8 (7)	C47—C19—C23—C43	178.9 (4)
C9—C7—C23—C19	1.7 (7)	C47—C39—C71—C53	−0.9 (9)
C9—C7—C23—C43	−178.8 (4)	C49—C7—C9—C27	178.0 (6)
C9—C7—C49—C61	−0.2 (9)	C49—C7—C9—C33	−0.7 (8)
C9—C27—C47—C19	−1.5 (10)	C49—C7—C23—C19	−178.1 (5)
C9—C27—C47—C39	178.5 (7)	C49—C7—C23—C43	1.4 (8)
C9—C33—C65—C61	1.7 (12)	C49—C61—C65—C33	−2.5 (9)
C11—C5—C21—C17	1.8 (9)	C51—C5—C11—C25	178.5 (5)
C11—C5—C21—C41	−178.7 (5)	C51—C5—C11—C35	−4.6 (8)
C11—C5—C51—C63	2.1 (8)	C51—C5—C21—C17	−176.7 (5)
C11—C25—C45—C17	3.0 (9)	C51—C5—C21—C41	2.8 (10)
C11—C25—C45—C37	−176.8 (5)	C51—C63—C67—C35	0.3 (9)
C11—C35—C67—C63	−3.0 (10)	C53—C1—C13—C29	180.0 (6)
C13—C1—C19—C23	−1.6 (7)	C53—C1—C13—C59	−1.7 (8)
C13—C1—C19—C47	179.9 (4)	C53—C1—C19—C23	−178.4 (6)
C13—C1—C53—C71	178.5 (3)	C53—C1—C19—C47	3.1 (8)
C13—C1—C53—C75	2.0 (9)	C53—C75—C79—C59	0.6 (8)
C13—C29—C43—C23	2.3 (8)	C55—C3—C15—C31	178.1 (5)
C13—C59—C79—C75	−0.4 (10)	C55—C3—C15—C57	0.8 (9)
C15—C3—C17—C21	1.9 (9)	C55—C3—C17—C21	−177.8 (5)
C15—C3—C17—C45	−177.8 (5)	C55—C3—C17—C45	2.5 (8)
C15—C3—C55—C69	−177.9 (5)	C55—C73—C77—C57	0.0 (9)
C15—C3—C55—C73	2.1 (8)	C57—C15—C31—C41	177.0 (6)
C15—C31—C41—C21	1.7 (9)	C59—C13—C29—C43	178.2 (3)
C15—C57—C77—C73	3.1 (9)	C69—C37—C45—C17	−3.7 (9)
C17—C3—C15—C31	−1.5 (8)	C69—C37—C45—C25	176.1 (6)
C17—C3—C15—C57	−178.9 (5)	C69—C55—C73—C77	177.6 (5)
C17—C3—C55—C69	1.7 (8)	C71—C39—C47—C19	−0.8 (11)
C17—C3—C55—C73	−178.3 (5)	C71—C39—C47—C27	179.2 (3)
C17—C21—C41—C31	−1.4 (9)	C71—C53—C75—C79	−177.8 (4)
C19—C1—C13—C29	3.1 (8)	C73—C55—C69—C37	172.7 (5)
C19—C1—C13—C59	−178.6 (4)	C75—C53—C71—C39	−179.7 (4)

(benzoapyrene_14.2GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 1.959 Mg m^−3
a = 3.2931 (2) Å	Synchrotron radiation, λ = 0.410 Å
b = 12.347 (4) Å	Cell parameters from 438 reflections
c = 21.133 (7) Å	θ = 3.6–18.5°
α = 91.42 (3)°	µ = 0.05 mm^−1
β = 90.439 (11)°	T = 293 K
γ = 95.290 (11)°	Block, black
V = 855.3 (4) Å^3	0.02 × 0.02 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1448 independent reflections
Radiation source: synchrotron	790 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.022
ω scans	θmax = 21.3°, θmin = 3.6°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.023, Tmax = 1.000	k = −15→16
2119 measured reflections	l = −14→20

Refinement

Refinement on F^2	90 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.076	H-atom parameters constrained
wR(F^2) = 0.231	w = 1/[σ^2(Fo^2) + (0.1529P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1448 reflections	Δρmax = 0.23 e Å^−3
361 parameters	Δρmin = −0.20 e Å^−3

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	1.0481 (17)	0.7663 (9)	0.8347 (8)	0.027 (5)
C3	0.9897 (13)	0.2515 (8)	0.6642 (8)	0.058 (12)
C5	0.5156 (13)	0.2841 (9)	0.5051 (7)	0.034 (11)
C7	0.5420 (16)	0.7759 (9)	0.9902 (8)	0.024 (5)
C9	0.4019 (17)	0.6670 (10)	0.9952 (8)	0.028 (5)
C11	0.3385 (15)	0.1813 (9)	0.4938 (7)	0.025 (5)
C13	1.1939 (16)	0.8757 (9)	0.8274 (8)	0.026 (5)
C15	1.1532 (15)	0.3562 (9)	0.6792 (8)	0.045 (12)
C17	0.7727 (13)	0.2261 (8)	0.6055 (8)	0.048 (11)
C19	0.8284 (16)	0.7338 (10)	0.8876 (8)	0.027 (11)
C21	0.7329 (15)	0.3100 (9)	0.5624 (8)	0.061 (12)
C23	0.7599 (16)	0.8124 (9)	0.9365 (8)	0.034 (12)
C25	0.3828 (15)	0.0987 (9)	0.5383 (8)	0.044 (12)
H25	0.257957	0.029166	0.529827	0.052*
C27	0.4755 (17)	0.5939 (10)	0.9485 (8)	0.029 (12)
H27	0.380872	0.521208	0.953022	0.035*
C29	1.1127 (17)	0.9522 (10)	0.8756 (8)	0.026 (11)
H29	1.201492	1.025266	0.870972	0.031*
C31	1.1020 (16)	0.4381 (9)	0.6337 (8)	0.036 (12)
H31	1.210580	0.509114	0.642522	0.044*
C33	0.1820 (18)	0.6365 (10)	1.0506 (9)	0.048 (11)
H33	0.084484	0.563775	1.054113	0.058*
C35	0.1152 (16)	0.1562 (10)	0.4378 (9)	0.058 (13)
H35	−0.011340	0.086327	0.430850	0.069*
C37	0.6577 (14)	0.0365 (9)	0.6361 (8)	0.069 (12)
H37	0.532187	−0.033532	0.629555	0.083*
C39	0.7507 (17)	0.5476 (10)	0.8445 (9)	0.028 (8)
H39	0.645462	0.475371	0.847576	0.034*
C41	0.9050 (15)	0.4158 (9)	0.5795 (8)	0.055 (12)
H41	0.878872	0.471799	0.551588	0.066*
C43	0.9068 (14)	0.9204 (8)	0.9284 (7)	0.038 (10)
H43	0.863060	0.971986	0.959859	0.045*
C45	0.5952 (14)	0.1176 (8)	0.5912 (8)	0.042 (11)
C47	0.6846 (17)	0.6240 (10)	0.8951 (8)	0.027 (5)
C49	0.4708 (18)	0.8483 (11)	1.0412 (9)	0.038 (12)
H49	0.568318	0.921062	1.038289	0.045*
C51	0.4714 (16)	0.3645 (10)	0.4584 (8)	0.064 (11)
H51	0.584848	0.435613	0.465288	0.077*
C53	1.1185 (17)	0.6882 (10)	0.7857 (8)	0.032 (5)
C55	1.0481 (16)	0.1652 (9)	0.7051 (8)	0.050 (12)
C57	1.3698 (16)	0.3775 (10)	0.7350 (9)	0.070 (13)
H57	1.487213	0.447439	0.744577	0.084*
C59	1.4161 (16)	0.9065 (9)	0.7753 (8)	0.027 (8)
H59	1.524492	0.978363	0.771768	0.033*
C61	0.2639 (15)	0.8156 (9)	1.0948 (7)	0.032 (11)
H61	0.227860	0.864360	1.128071	0.039*
C63	0.2632 (16)	0.3360 (10)	0.4041 (8)	0.032 (5)
H63	0.243130	0.387817	0.373354	0.038*
C65	0.107 (2)	0.7045 (11)	1.0973 (9)	0.046 (11)
H65	−0.047040	0.679962	1.131635	0.056*
C67	0.0817 (16)	0.2329 (10)	0.3933 (8)	0.061 (11)
H67	−0.063402	0.215489	0.355944	0.073*
C69	0.8928 (14)	0.0586 (9)	0.6876 (7)	0.044 (12)
H69	0.955490	0.001572	0.712769	0.052*
C71	0.9631 (14)	0.5791 (8)	0.7928 (7)	0.030 (5)
H71	1.007824	0.527801	0.761197	0.037*
C73	1.2518 (16)	0.1916 (10)	0.7636 (8)	0.035 (12)
H73	1.276356	0.138111	0.793270	0.042*
C75	1.3443 (15)	0.7225 (9)	0.7340 (8)	0.049 (11)
H75	1.404967	0.671665	0.703085	0.058*
C77	1.4111 (16)	0.2956 (10)	0.7760 (8)	0.063 (12)
H77	1.553058	0.311487	0.813808	0.076*
C79	1.4807 (19)	0.8293 (11)	0.7270 (9)	0.041 (13)
H79	1.616429	0.851095	0.690372	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.024 (2)	0.033 (6)	0.025 (11)	0.003 (3)	−0.005 (4)	−0.006 (7)
C3	0.0161 (19)	0.052 (11)	0.11 (3)	0.008 (3)	0.006 (5)	0.031 (17)
C5	0.0163 (19)	0.043 (10)	0.04 (3)	0.008 (3)	0.001 (5)	−0.009 (16)
C7	0.018 (2)	0.025 (6)	0.026 (11)	−0.005 (3)	−0.012 (4)	−0.008 (7)
C9	0.021 (2)	0.041 (7)	0.024 (11)	0.005 (3)	−0.006 (4)	−0.005 (8)
C11	0.023 (2)	0.033 (6)	0.019 (11)	0.007 (3)	0.004 (4)	−0.012 (7)
C13	0.023 (2)	0.026 (6)	0.028 (11)	0.004 (3)	−0.006 (4)	−0.007 (7)
C15	0.018 (2)	0.051 (11)	0.07 (3)	0.005 (3)	−0.002 (5)	0.006 (17)
C17	0.0163 (19)	0.045 (10)	0.08 (3)	0.006 (3)	0.007 (5)	0.016 (17)
C19	0.023 (2)	0.048 (11)	0.01 (2)	0.012 (4)	−0.002 (6)	0.001 (16)
C21	0.023 (2)	0.068 (12)	0.10 (3)	0.013 (4)	0.013 (5)	0.044 (18)
C23	0.024 (2)	0.041 (11)	0.04 (3)	0.008 (4)	0.003 (6)	0.004 (17)
C25	0.022 (2)	0.039 (10)	0.07 (3)	0.002 (3)	0.000 (5)	0.011 (17)
C27	0.027 (2)	0.024 (11)	0.03 (3)	0.003 (4)	−0.006 (6)	−0.009 (18)
C29	0.031 (2)	0.036 (11)	0.01 (3)	0.010 (4)	−0.001 (6)	−0.004 (17)
C31	0.026 (2)	0.029 (11)	0.05 (3)	0.000 (4)	−0.002 (6)	−0.003 (18)
C33	0.019 (2)	0.062 (11)	0.06 (3)	0.001 (4)	−0.007 (5)	0.025 (17)
C35	0.027 (2)	0.062 (12)	0.09 (3)	0.006 (4)	0.006 (6)	0.03 (2)
C37	0.021 (2)	0.065 (11)	0.12 (3)	0.011 (3)	0.010 (5)	0.046 (18)
C39	0.029 (2)	0.025 (8)	0.031 (19)	0.003 (3)	−0.006 (5)	−0.003 (12)
C41	0.021 (2)	0.050 (11)	0.10 (3)	0.009 (3)	0.008 (5)	0.030 (17)
C43	0.027 (2)	0.047 (10)	0.04 (2)	0.009 (3)	−0.002 (5)	0.008 (15)
C45	0.019 (2)	0.031 (10)	0.08 (3)	0.003 (3)	0.004 (5)	0.003 (16)
C47	0.025 (2)	0.036 (6)	0.022 (11)	0.007 (3)	−0.007 (4)	−0.006 (8)
C49	0.027 (2)	0.039 (11)	0.05 (3)	0.006 (4)	−0.003 (6)	0.009 (18)
C51	0.025 (2)	0.066 (10)	0.10 (2)	0.012 (4)	0.010 (5)	0.042 (16)
C53	0.025 (2)	0.046 (7)	0.026 (11)	0.010 (3)	−0.007 (4)	−0.005 (8)
C55	0.025 (2)	0.038 (11)	0.09 (3)	0.012 (4)	0.012 (6)	0.013 (18)
C57	0.020 (2)	0.065 (12)	0.13 (3)	0.012 (4)	0.009 (6)	0.029 (19)
C59	0.023 (2)	0.019 (8)	0.038 (19)	−0.006 (3)	−0.008 (5)	−0.011 (12)
C61	0.029 (2)	0.053 (11)	0.02 (3)	0.013 (4)	−0.002 (5)	−0.005 (17)
C63	0.029 (2)	0.038 (6)	0.030 (11)	0.010 (3)	0.001 (4)	−0.007 (8)
C65	0.024 (3)	0.051 (11)	0.07 (3)	0.010 (4)	0.010 (6)	0.015 (16)
C67	0.026 (2)	0.081 (12)	0.08 (2)	0.021 (4)	0.012 (5)	0.028 (16)
C69	0.024 (2)	0.059 (12)	0.05 (3)	0.012 (4)	0.006 (5)	0.016 (18)
C71	0.027 (2)	0.035 (6)	0.030 (11)	0.008 (3)	−0.007 (4)	−0.009 (7)
C73	0.024 (2)	0.043 (11)	0.04 (3)	0.009 (4)	−0.002 (5)	−0.006 (18)
C75	0.027 (2)	0.054 (11)	0.07 (3)	0.014 (4)	0.008 (6)	0.014 (17)
C77	0.028 (2)	0.077 (12)	0.09 (3)	0.022 (4)	0.012 (6)	0.031 (18)
C79	0.031 (3)	0.059 (13)	0.04 (3)	0.017 (5)	0.011 (7)	0.01 (2)

Geometric parameters (Å, º)

C1—C13	1.404 (13)	C35—H35	0.9300
C1—C19	1.385 (15)	C35—C67	1.362 (11)
C1—C53	1.43 (3)	C37—H37	0.9300
C3—C15	1.383 (18)	C37—C45	1.425 (10)
C3—C17	1.44 (2)	C37—C69	1.34 (2)
C3—C55	1.414 (9)	C39—H39	0.9300
C5—C11	1.362 (17)	C39—C47	1.44 (3)
C5—C21	1.42 (2)	C39—C71	1.349 (15)
C5—C51	1.432 (10)	C41—H41	0.9300
C7—C9	1.388 (14)	C43—H43	0.9300
C7—C23	1.408 (14)	C49—H49	0.9300
C7—C49	1.42 (3)	C49—C61	1.375 (15)
C9—C27	1.36 (3)	C51—H51	0.9300
C9—C33	1.422 (17)	C51—C63	1.35 (3)
C11—C25	1.419 (10)	C53—C71	1.409 (14)
C11—C35	1.40 (2)	C53—C75	1.380 (14)
C13—C29	1.42 (3)	C55—C69	1.406 (18)
C13—C59	1.369 (15)	C55—C73	1.42 (3)
C15—C31	1.432 (10)	C57—H57	0.9300
C15—C57	1.38 (3)	C57—C77	1.363 (11)
C17—C21	1.411 (10)	C59—H59	0.9300
C17—C45	1.435 (17)	C59—C79	1.41 (3)
C19—C23	1.43 (3)	C61—H61	0.9300
C19—C47	1.407 (14)	C61—C65	1.423 (17)
C21—C41	1.41 (2)	C63—H63	0.9300
C23—C43	1.392 (13)	C63—C67	1.37 (2)
C25—H25	0.9300	C65—H65	0.9300
C25—C45	1.32 (2)	C67—H67	0.9300
C27—H27	0.9300	C69—H69	0.9300
C27—C47	1.369 (16)	C71—H71	0.9300
C29—H29	0.9300	C73—H73	0.9300
C29—C43	1.358 (14)	C73—C77	1.361 (19)
C31—H31	0.9300	C75—H75	0.9300
C31—C41	1.32 (3)	C75—C79	1.364 (15)
C33—H33	0.9300	C77—H77	0.9300
C33—C65	1.32 (3)	C79—H79	0.9300
C13—C1—C53	119.3 (9)	C21—C41—H41	118.8
C19—C1—C13	120.9 (16)	C31—C41—C21	122.5 (8)
C19—C1—C53	119.8 (11)	C31—C41—H41	118.8
C15—C3—C17	121.3 (7)	C23—C43—H43	119.3
C15—C3—C55	120.6 (14)	C29—C43—C23	121.4 (15)
C55—C3—C17	118.1 (12)	C29—C43—H43	119.3
C11—C5—C21	119.9 (8)	C25—C45—C17	119.0 (7)
C11—C5—C51	118.6 (14)	C25—C45—C37	123.9 (11)
C21—C5—C51	121.5 (12)	C37—C45—C17	117.1 (13)
C9—C7—C23	120.5 (16)	C19—C47—C39	118.2 (10)
C9—C7—C49	118.3 (10)	C27—C47—C19	119.6 (16)
C23—C7—C49	121.2 (11)	C27—C47—C39	122.2 (11)
C7—C9—C33	117.3 (16)	C7—C49—H49	118.5
C27—C9—C7	120.5 (10)	C61—C49—C7	123.0 (11)
C27—C9—C33	122.3 (11)	C61—C49—H49	118.5
C5—C11—C25	120.3 (14)	C5—C51—H51	120.3
C5—C11—C35	120.0 (8)	C63—C51—C5	119.4 (12)
C35—C11—C25	119.7 (12)	C63—C51—H51	120.3
C1—C13—C29	118.5 (9)	C71—C53—C1	118.8 (9)
C59—C13—C1	120.3 (15)	C75—C53—C1	118.6 (11)
C59—C13—C29	121.2 (10)	C75—C53—C71	122.6 (16)
C3—C15—C31	117.3 (14)	C3—C55—C73	117.6 (12)
C57—C15—C3	119.9 (8)	C69—C55—C3	119.6 (14)
C57—C15—C31	122.7 (12)	C69—C55—C73	122.8 (7)
C21—C17—C3	118.9 (12)	C15—C57—H57	120.1
C21—C17—C45	120.3 (14)	C77—C57—C15	119.8 (13)
C45—C17—C3	120.8 (7)	C77—C57—H57	120.1
C1—C19—C23	119.5 (11)	C13—C59—H59	120.0
C1—C19—C47	120.9 (16)	C13—C59—C79	120.0 (10)
C47—C19—C23	119.6 (10)	C79—C59—H59	120.0
C17—C21—C5	118.4 (12)	C49—C61—H61	121.3
C17—C21—C41	118.0 (15)	C49—C61—C65	117.5 (16)
C41—C21—C5	123.6 (7)	C65—C61—H61	121.3
C7—C23—C19	117.9 (10)	C51—C63—H63	119.1
C43—C23—C7	123.4 (16)	C51—C63—C67	121.8 (8)
C43—C23—C19	118.7 (9)	C67—C63—H63	119.1
C11—C25—H25	119.0	C33—C65—C61	119.6 (10)
C45—C25—C11	122.1 (12)	C33—C65—H65	120.2
C45—C25—H25	119.0	C61—C65—H65	120.2
C9—C27—H27	119.0	C35—C67—C63	119.4 (16)
C9—C27—C47	122.0 (11)	C35—C67—H67	120.3
C47—C27—H27	119.0	C63—C67—H67	120.3
C13—C29—H29	119.5	C37—C69—C55	122.3 (7)
C43—C29—C13	120.9 (10)	C37—C69—H69	118.9
C43—C29—H29	119.5	C55—C69—H69	118.9
C15—C31—H31	119.0	C39—C71—C53	121.2 (15)
C41—C31—C15	122.0 (12)	C39—C71—H71	119.4
C41—C31—H31	119.0	C53—C71—H71	119.4
C9—C33—H33	117.9	C55—C73—H73	120.2
C65—C33—C9	124.3 (12)	C77—C73—C55	119.5 (8)
C65—C33—H33	117.9	C77—C73—H73	120.2
C11—C35—H35	119.6	C53—C75—H75	119.2
C67—C35—C11	120.7 (13)	C79—C75—C53	121.6 (16)
C67—C35—H35	119.6	C79—C75—H75	119.2
C45—C37—H37	119.2	C57—C77—H77	118.8
C69—C37—H37	119.2	C73—C77—C57	122.3 (16)
C69—C37—C45	121.6 (11)	C73—C77—H77	118.8
C47—C39—H39	119.5	C59—C79—H79	120.0
C71—C39—H39	119.5	C75—C79—C59	120.1 (11)
C71—C39—C47	121.0 (11)	C75—C79—H79	120.0
C1—C13—C29—C43	1.5 (15)	C19—C1—C53—C71	−0.4 (15)
C1—C13—C59—C79	3.4 (15)	C19—C1—C53—C75	−178.9 (7)
C1—C19—C23—C7	−178.8 (7)	C19—C23—C43—C29	−0.2 (13)
C1—C19—C23—C43	1.9 (14)	C21—C5—C11—C25	−2.3 (13)
C1—C19—C47—C27	178.7 (9)	C21—C5—C11—C35	178.5 (9)
C1—C19—C47—C39	−3.6 (13)	C21—C5—C51—C63	179.6 (9)
C1—C53—C71—C39	0.1 (13)	C21—C17—C45—C25	−2.4 (13)
C1—C53—C75—C79	−3.7 (15)	C21—C17—C45—C37	178.3 (8)
C3—C15—C31—C41	0.4 (14)	C23—C7—C9—C27	0.5 (14)
C3—C15—C57—C77	−2.0 (15)	C23—C7—C9—C33	−179.6 (8)
C3—C17—C21—C5	−179.5 (8)	C23—C7—C49—C61	−179.2 (7)
C3—C17—C21—C41	−0.8 (12)	C23—C19—C47—C27	1.0 (13)
C3—C17—C45—C25	176.9 (8)	C23—C19—C47—C39	178.7 (9)
C3—C17—C45—C37	−2.4 (12)	C25—C11—C35—C67	−177.5 (8)
C3—C55—C69—C37	−6.2 (13)	C27—C9—C33—C65	179.3 (12)
C3—C55—C73—C77	−5.3 (13)	C29—C13—C59—C79	−177.8 (10)
C5—C11—C25—C45	−0.4 (14)	C31—C15—C57—C77	−179.3 (9)
C5—C11—C35—C67	1.8 (15)	C33—C9—C27—C47	179.5 (8)
C5—C21—C41—C31	179.1 (9)	C35—C11—C25—C45	178.8 (9)
C5—C51—C63—C67	2.1 (15)	C45—C17—C21—C5	−0.2 (13)
C7—C9—C27—C47	−0.6 (16)	C45—C17—C21—C41	178.5 (7)
C7—C9—C33—C65	−0.6 (16)	C45—C37—C69—C55	8.5 (15)
C7—C23—C43—C29	−179.4 (8)	C47—C19—C23—C7	−1.1 (13)
C7—C49—C61—C65	−1.8 (14)	C47—C19—C23—C43	179.6 (7)
C9—C7—C23—C19	0.4 (13)	C47—C39—C71—C53	−1.6 (14)
C9—C7—C23—C43	179.6 (8)	C49—C7—C9—C27	−177.7 (10)
C9—C7—C49—C61	−1.0 (15)	C49—C7—C9—C33	2.3 (13)
C9—C27—C47—C19	−0.2 (15)	C49—C7—C23—C19	178.5 (10)
C9—C27—C47—C39	−177.7 (10)	C49—C7—C23—C43	−2.3 (14)
C9—C33—C65—C61	−2.3 (18)	C49—C61—C65—C33	3.4 (15)
C11—C5—C21—C17	2.5 (13)	C51—C5—C11—C25	178.6 (9)
C11—C5—C21—C41	−176.2 (8)	C51—C5—C11—C35	−0.6 (13)
C11—C5—C51—C63	−1.3 (14)	C51—C5—C21—C17	−178.4 (8)
C11—C25—C45—C17	2.7 (14)	C51—C5—C21—C41	2.9 (14)
C11—C25—C45—C37	−178.0 (8)	C51—C63—C67—C35	−1.0 (15)
C11—C35—C67—C63	−1.0 (15)	C53—C1—C13—C29	178.4 (9)
C13—C1—C19—C23	−1.9 (14)	C53—C1—C13—C59	−2.8 (14)
C13—C1—C19—C47	−179.6 (8)	C53—C1—C19—C23	179.9 (9)
C13—C1—C53—C71	−178.6 (6)	C53—C1—C19—C47	2.2 (14)
C13—C1—C53—C75	2.9 (14)	C53—C75—C79—C59	4.3 (16)
C13—C29—C43—C23	−1.6 (14)	C55—C3—C15—C31	176.4 (8)
C13—C59—C79—C75	−4.2 (16)	C55—C3—C15—C57	−1.1 (14)
C15—C3—C17—C21	0.9 (13)	C55—C3—C17—C21	−176.2 (7)
C15—C3—C17—C45	−178.4 (7)	C55—C3—C17—C45	4.5 (13)
C15—C3—C55—C69	−177.5 (8)	C55—C73—C77—C57	2.4 (14)
C15—C3—C55—C73	4.7 (12)	C57—C15—C31—C41	177.8 (10)
C15—C31—C41—C21	−0.3 (15)	C59—C13—C29—C43	−177.2 (8)
C15—C57—C77—C73	1.3 (15)	C69—C37—C45—C17	−4.1 (13)
C17—C3—C15—C31	−0.7 (13)	C69—C37—C45—C25	176.6 (10)
C17—C3—C15—C57	−178.2 (8)	C69—C55—C73—C77	176.9 (7)
C17—C3—C55—C69	−0.3 (12)	C71—C39—C47—C19	3.4 (14)
C17—C3—C55—C73	−178.2 (8)	C71—C39—C47—C27	−179.0 (7)
C17—C21—C41—C31	0.5 (14)	C71—C53—C75—C79	177.8 (9)
C19—C1—C13—C29	0.2 (14)	C73—C55—C69—C37	171.5 (9)
C19—C1—C13—C59	179.0 (9)	C75—C53—C71—C39	178.6 (9)

(benzoapyrene_21.1GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 2.085 Mg m^−3
a = 3.1883 (4) Å	Synchrotron radiation, λ = 0.410 Å
b = 12.1605 (18) Å	Cell parameters from 581 reflections
c = 20.825 (6) Å	θ = 3.7–20.0°
α = 91.99 (2)°	µ = 0.05 mm^−1
β = 90.297 (18)°	T = 293 K
γ = 95.206 (11)°	Block, black
V = 803.6 (3) Å^3	0.02 × 0.02 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	1242 independent reflections
Radiation source: synchrotron	801 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.023
ω scans	θmax = 21.2°, θmin = 3.7°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −5→5
Tmin = 0.062, Tmax = 1.000	k = −19→19
1711 measured reflections	l = −12→11

Refinement

Refinement on F^2	72 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.063	H-atom parameters constrained
wR(F^2) = 0.211	w = 1/[σ^2(Fo^2) + (0.1784P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
1242 reflections	Δρmax = 0.18 e Å^−3
361 parameters	Δρmin = −0.16 e Å^−3

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	−0.0678 (10)	0.2352 (3)	0.1655 (6)	0.036 (8)
C3	1.0023 (10)	0.7529 (3)	0.3359 (6)	0.028 (4)
C5	1.4903 (11)	0.7122 (3)	0.4942 (6)	0.028 (4)
C7	0.4592 (10)	0.2214 (3)	0.0094 (6)	0.032 (8)
C9	0.6015 (10)	0.3342 (3)	0.0028 (6)	0.050 (8)
C11	1.6701 (11)	0.8196 (3)	0.5072 (7)	0.028 (9)
C13	−0.2154 (10)	0.1235 (3)	0.1734 (6)	0.043 (8)
C15	0.8356 (11)	0.6447 (3)	0.3212 (7)	0.026 (4)
C17	1.2243 (11)	0.7744 (3)	0.3922 (6)	0.025 (4)
C19	0.1567 (10)	0.2663 (3)	0.1109 (6)	0.038 (8)
C21	1.2652 (11)	0.6899 (3)	0.4358 (6)	0.035 (9)
C23	0.2310 (10)	0.1889 (3)	0.0622 (6)	0.027 (4)
C25	1.6290 (10)	0.9029 (3)	0.4641 (6)	0.028 (8)
H25	1.757427	0.973392	0.473685	0.034*
C27	0.5205 (11)	0.4088 (3)	0.0514 (7)	0.040 (9)
H27	0.617773	0.482565	0.047032	0.047*
C29	−0.1347 (10)	0.0469 (3)	0.1243 (6)	0.040 (8)
H29	−0.233901	−0.026805	0.128235	0.048*
C31	0.8797 (12)	0.5605 (3)	0.3629 (6)	0.030 (8)
H31	0.768162	0.488734	0.352357	0.035*
C33	0.8227 (11)	0.3657 (4)	−0.0521 (6)	0.028 (9)
H33	0.908485	0.440189	−0.056603	0.033*
C35	1.9035 (12)	0.8423 (4)	0.5628 (7)	0.033 (9)
H35	2.038345	0.912732	0.570144	0.040*
C37	1.3365 (11)	0.9676 (3)	0.3649 (6)	0.031 (4)
H37	1.470672	1.037943	0.372596	0.037*
C39	0.2361 (11)	0.4561 (3)	0.1560 (6)	0.049 (9)
H39	0.345033	0.529435	0.153573	0.058*
C41	1.0887 (12)	0.5839 (3)	0.4196 (6)	0.033 (8)
H41	1.113756	0.527583	0.448102	0.039*
C43	0.0817 (11)	0.0771 (3)	0.0719 (6)	0.031 (4)
H43	0.135805	0.023349	0.040942	0.037*
C45	1.4008 (11)	0.8837 (3)	0.4071 (6)	0.029 (8)
C47	0.3072 (11)	0.3804 (3)	0.1049 (6)	0.046 (9)
C49	0.5385 (11)	0.1495 (3)	−0.0434 (6)	0.048 (9)
H49	0.434481	0.075625	−0.042379	0.058*
C51	1.5357 (12)	0.6330 (3)	0.5413 (7)	0.029 (4)
H51	1.411736	0.561394	0.534088	0.035*
C53	−0.1481 (11)	0.3120 (3)	0.2140 (6)	0.041 (8)
C55	0.9413 (12)	0.8392 (3)	0.2937 (6)	0.027 (4)
C57	0.6123 (11)	0.6255 (4)	0.2633 (7)	0.033 (4)
H57	0.489746	0.554740	0.252861	0.040*
C59	−0.4429 (11)	0.0945 (3)	0.2246 (6)	0.036 (9)
H59	−0.554798	0.021497	0.227440	0.043*
C61	0.7591 (11)	0.1847 (4)	−0.0947 (7)	0.053 (10)
H61	0.808218	0.135490	−0.128449	0.063*
C63	1.7551 (12)	0.6584 (4)	0.5969 (7)	0.031 (9)
H63	1.779082	0.605202	0.627350	0.037*
C65	0.9141 (11)	0.2957 (4)	−0.0971 (7)	0.045 (9)
H65	1.083478	0.319400	−0.131028	0.054*
C67	1.9414 (11)	0.7645 (4)	0.6072 (7)	0.050 (10)
H67	2.094063	0.782819	0.644822	0.060*
C69	1.0855 (11)	0.9478 (3)	0.3137 (6)	0.035 (8)
H69	1.004182	1.006792	0.290837	0.042*
C71	0.0182 (11)	0.4249 (3)	0.2071 (6)	0.032 (4)
H71	−0.028670	0.477143	0.239312	0.038*
C73	0.7277 (12)	0.8150 (4)	0.2370 (7)	0.044 (9)
H73	0.689520	0.871039	0.208854	0.053*
C75	−0.3745 (12)	0.2802 (3)	0.2652 (7)	0.031 (9)
H75	−0.438191	0.333133	0.296061	0.038*
C77	0.5704 (10)	0.7091 (3)	0.2215 (6)	0.035 (4)
H77	0.433356	0.693281	0.182317	0.042*
C79	−0.5177 (10)	0.1696 (3)	0.2736 (6)	0.031 (9)
H79	−0.657833	0.147409	0.310662	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0262 (14)	0.034 (2)	0.05 (2)	0.0045 (13)	0.004 (4)	−0.011 (4)
C3	0.0268 (15)	0.0334 (19)	0.023 (12)	0.0044 (13)	0.009 (3)	−0.003 (4)
C5	0.0269 (14)	0.0329 (18)	0.025 (13)	0.0049 (13)	0.003 (3)	−0.002 (4)
C7	0.0284 (15)	0.033 (2)	0.03 (3)	0.0033 (13)	0.006 (4)	−0.006 (5)
C9	0.0285 (15)	0.0293 (19)	0.09 (3)	0.0032 (13)	0.011 (4)	−0.004 (4)
C11	0.0289 (16)	0.034 (2)	0.02 (3)	0.0049 (14)	0.007 (5)	−0.002 (5)
C13	0.0266 (15)	0.038 (2)	0.07 (3)	0.0073 (13)	0.001 (4)	−0.012 (5)
C15	0.0296 (15)	0.0314 (18)	0.016 (12)	0.0044 (13)	0.004 (3)	−0.003 (4)
C17	0.0268 (14)	0.0332 (18)	0.016 (12)	0.0059 (13)	0.009 (3)	0.003 (4)
C19	0.0258 (15)	0.0300 (19)	0.06 (2)	0.0039 (12)	0.005 (4)	−0.007 (4)
C21	0.0276 (15)	0.034 (2)	0.04 (3)	0.0051 (13)	0.008 (4)	−0.006 (5)
C23	0.0267 (14)	0.0282 (17)	0.025 (12)	0.0062 (11)	−0.001 (3)	0.000 (3)
C25	0.0280 (15)	0.0308 (18)	0.02 (3)	0.0005 (13)	0.003 (4)	−0.012 (4)
C27	0.0312 (15)	0.0277 (18)	0.06 (3)	0.0016 (12)	0.003 (4)	−0.006 (4)
C29	0.0319 (15)	0.0233 (17)	0.07 (2)	0.0013 (12)	0.011 (4)	0.000 (4)
C31	0.0331 (16)	0.029 (2)	0.03 (2)	0.0029 (14)	0.009 (4)	−0.003 (4)
C33	0.0318 (16)	0.036 (2)	0.02 (3)	0.0034 (13)	0.003 (4)	0.004 (4)
C35	0.0325 (16)	0.035 (2)	0.03 (3)	0.0031 (14)	0.010 (4)	−0.003 (4)
C37	0.0308 (15)	0.0339 (18)	0.027 (12)	0.0043 (12)	0.002 (3)	−0.008 (4)
C39	0.0334 (16)	0.0300 (18)	0.08 (3)	0.0035 (13)	0.011 (4)	−0.008 (4)
C41	0.0317 (16)	0.0298 (19)	0.04 (3)	0.0042 (14)	0.010 (4)	−0.007 (4)
C43	0.0326 (15)	0.0313 (18)	0.028 (12)	0.0033 (12)	0.007 (3)	−0.007 (3)
C45	0.0277 (15)	0.036 (2)	0.02 (3)	0.0051 (14)	0.006 (4)	−0.009 (4)
C47	0.0297 (17)	0.035 (2)	0.07 (3)	0.0061 (14)	0.007 (5)	−0.007 (5)
C49	0.0353 (17)	0.0278 (18)	0.08 (3)	0.0060 (13)	0.021 (5)	0.009 (4)
C51	0.0327 (16)	0.0332 (18)	0.021 (12)	0.0054 (14)	0.013 (3)	0.004 (4)
C53	0.0301 (15)	0.0287 (19)	0.06 (3)	0.0048 (13)	0.007 (4)	−0.008 (4)
C55	0.0269 (14)	0.0357 (18)	0.019 (12)	0.0049 (13)	0.005 (3)	0.000 (4)
C57	0.0332 (16)	0.0361 (19)	0.030 (13)	0.0050 (14)	0.006 (4)	−0.005 (4)
C59	0.0316 (15)	0.0318 (19)	0.05 (3)	0.0047 (13)	0.006 (4)	0.003 (4)
C61	0.0328 (17)	0.050 (2)	0.08 (3)	0.0118 (15)	0.012 (5)	−0.010 (5)
C63	0.0351 (18)	0.036 (2)	0.02 (3)	0.0087 (14)	0.004 (5)	0.004 (5)
C65	0.0258 (15)	0.053 (2)	0.06 (3)	0.0080 (14)	0.006 (4)	0.003 (5)
C67	0.0333 (16)	0.041 (2)	0.07 (3)	0.0065 (15)	0.014 (5)	−0.010 (5)
C69	0.0313 (15)	0.037 (2)	0.04 (2)	0.0065 (13)	0.001 (4)	−0.008 (5)
C71	0.0320 (15)	0.0332 (19)	0.029 (12)	0.0061 (13)	−0.003 (3)	−0.008 (4)
C73	0.0316 (17)	0.041 (2)	0.06 (3)	0.0102 (15)	0.015 (5)	0.005 (5)
C75	0.0334 (16)	0.039 (2)	0.02 (3)	0.0075 (14)	0.008 (4)	−0.003 (5)
C77	0.0310 (16)	0.040 (2)	0.033 (13)	0.0039 (13)	0.008 (3)	−0.006 (4)
C79	0.0305 (16)	0.039 (2)	0.02 (3)	0.0076 (13)	0.001 (4)	−0.006 (4)

Geometric parameters (Å, º)

C1—C13	1.412 (7)	C35—H35	0.9300
C1—C19	1.391 (15)	C35—C67	1.358 (15)
C1—C53	1.393 (12)	C37—H37	0.9300
C3—C15	1.397 (6)	C37—C45	1.399 (13)
C3—C17	1.371 (17)	C37—C69	1.331 (16)
C3—C55	1.418 (14)	C39—H39	0.9300
C5—C11	1.395 (6)	C39—C47	1.415 (13)
C5—C21	1.413 (18)	C39—C71	1.321 (15)
C5—C51	1.415 (15)	C41—H41	0.9300
C7—C9	1.416 (6)	C43—H43	0.9300
C7—C23	1.371 (14)	C49—H49	0.9300
C7—C49	1.419 (13)	C49—C61	1.344 (15)
C9—C27	1.376 (12)	C51—H51	0.9300
C9—C33	1.393 (15)	C51—C63	1.361 (17)
C11—C25	1.391 (14)	C53—C71	1.439 (6)
C11—C35	1.380 (19)	C53—C75	1.339 (15)
C13—C29	1.399 (12)	C55—C69	1.407 (7)
C13—C59	1.332 (14)	C55—C73	1.370 (17)
C15—C31	1.383 (15)	C57—H57	0.9300
C15—C57	1.398 (19)	C57—C77	1.376 (14)
C17—C21	1.409 (15)	C59—H59	0.9300
C17—C45	1.419 (6)	C59—C79	1.381 (13)
C19—C23	1.396 (12)	C61—H61	0.9300
C19—C47	1.437 (6)	C61—C65	1.397 (6)
C21—C41	1.389 (6)	C63—H63	0.9300
C23—C43	1.420 (7)	C63—C67	1.379 (6)
C25—H25	0.9300	C65—H65	0.9300
C25—C45	1.390 (17)	C67—H67	0.9300
C27—H27	0.9300	C69—H69	0.9300
C27—C47	1.348 (16)	C71—H71	0.9300
C29—H29	0.9300	C73—H73	0.9300
C29—C43	1.339 (15)	C73—C77	1.366 (7)
C31—H31	0.9300	C75—H75	0.9300
C31—C41	1.361 (16)	C75—C79	1.398 (7)
C33—H33	0.9300	C77—H77	0.9300
C33—C65	1.297 (13)	C79—H79	0.9300
C19—C1—C13	120.4 (7)	C21—C41—H41	119.2
C19—C1—C53	121.5 (5)	C31—C41—C21	121.5 (9)
C53—C1—C13	118.2 (9)	C31—C41—H41	119.2
C15—C3—C55	120.7 (10)	C23—C43—H43	119.1
C17—C3—C15	118.8 (9)	C29—C43—C23	121.9 (7)
C17—C3—C55	120.6 (5)	C29—C43—H43	119.1
C11—C5—C21	118.3 (9)	C25—C45—C17	118.0 (9)
C11—C5—C51	117.6 (10)	C25—C45—C37	122.6 (5)
C21—C5—C51	124.1 (5)	C37—C45—C17	119.4 (10)
C9—C7—C49	116.0 (9)	C27—C47—C19	117.8 (7)
C23—C7—C9	120.1 (7)	C27—C47—C39	123.5 (5)
C23—C7—C49	123.8 (5)	C39—C47—C19	118.7 (9)
C27—C9—C7	118.7 (9)	C7—C49—H49	118.9
C27—C9—C33	122.2 (5)	C61—C49—C7	122.1 (5)
C33—C9—C7	119.1 (7)	C61—C49—H49	118.9
C25—C11—C5	121.1 (11)	C5—C51—H51	119.0
C35—C11—C5	119.2 (9)	C63—C51—C5	122.0 (5)
C35—C11—C25	119.7 (5)	C63—C51—H51	119.0
C29—C13—C1	117.8 (9)	C1—C53—C71	118.0 (9)
C59—C13—C1	120.3 (7)	C75—C53—C1	120.1 (5)
C59—C13—C29	121.9 (5)	C75—C53—C71	121.8 (7)
C3—C15—C57	117.4 (9)	C69—C55—C3	118.0 (10)
C31—C15—C3	121.4 (11)	C73—C55—C3	119.4 (5)
C31—C15—C57	121.2 (5)	C73—C55—C69	122.5 (8)
C3—C17—C21	120.5 (6)	C15—C57—H57	119.3
C3—C17—C45	119.2 (9)	C77—C57—C15	121.3 (5)
C21—C17—C45	120.3 (11)	C77—C57—H57	119.3
C1—C19—C23	121.0 (5)	C13—C59—H59	119.0
C1—C19—C47	118.8 (7)	C13—C59—C79	122.0 (5)
C23—C19—C47	120.1 (9)	C79—C59—H59	119.0
C17—C21—C5	120.5 (5)	C49—C61—H61	120.2
C41—C21—C5	120.8 (9)	C49—C61—C65	119.5 (8)
C41—C21—C17	118.6 (11)	C65—C61—H61	120.2
C7—C23—C19	119.8 (5)	C51—C63—H63	120.6
C7—C23—C43	122.9 (7)	C51—C63—C67	118.9 (10)
C19—C23—C43	117.2 (9)	C67—C63—H63	120.6
C11—C25—H25	119.2	C33—C65—C61	120.2 (9)
C45—C25—C11	121.7 (5)	C33—C65—H65	119.9
C45—C25—H25	119.2	C61—C65—H65	119.9
C9—C27—H27	118.3	C35—C67—C63	120.5 (11)
C47—C27—C9	123.4 (5)	C35—C67—H67	119.8
C47—C27—H27	118.3	C63—C67—H67	119.8
C13—C29—H29	119.1	C37—C69—C55	121.1 (8)
C43—C29—C13	121.7 (5)	C37—C69—H69	119.5
C43—C29—H29	119.1	C55—C69—H69	119.5
C15—C31—H31	120.4	C39—C71—C53	121.6 (7)
C41—C31—C15	119.1 (5)	C39—C71—H71	119.2
C41—C31—H31	120.4	C53—C71—H71	119.2
C9—C33—H33	118.6	C55—C73—H73	119.8
C65—C33—C9	122.8 (6)	C77—C73—C55	120.4 (10)
C65—C33—H33	118.6	C77—C73—H73	119.8
C11—C35—H35	119.1	C53—C75—H75	119.1
C67—C35—C11	121.7 (5)	C53—C75—C79	121.8 (7)
C67—C35—H35	119.1	C79—C75—H75	119.1
C45—C37—H37	119.6	C57—C77—H77	119.6
C69—C37—H37	119.6	C73—C77—C57	120.8 (11)
C69—C37—C45	120.8 (5)	C73—C77—H77	119.6
C47—C39—H39	119.3	C59—C79—C75	117.4 (9)
C71—C39—H39	119.3	C59—C79—H79	121.3
C71—C39—C47	121.4 (5)	C75—C79—H79	121.3
C1—C13—C29—C43	1.2 (12)	C19—C1—C53—C71	−1.7 (12)
C1—C13—C59—C79	−4.7 (13)	C19—C1—C53—C75	178.2 (7)
C1—C19—C23—C7	−178.9 (6)	C19—C23—C43—C29	2.3 (11)
C1—C19—C23—C43	−2.3 (12)	C21—C5—C11—C25	0.2 (8)
C1—C19—C47—C27	−179.4 (7)	C21—C5—C11—C35	−177.8 (5)
C1—C19—C47—C39	2.5 (11)	C21—C5—C51—C63	−179.9 (6)
C1—C53—C71—C39	0.9 (12)	C21—C17—C45—C25	2.9 (8)
C1—C53—C75—C79	3.4 (14)	C21—C17—C45—C37	−176.5 (5)
C3—C15—C31—C41	0.3 (8)	C23—C7—C9—C27	2.5 (12)
C3—C15—C57—C77	2.1 (9)	C23—C7—C9—C33	−178.2 (7)
C3—C17—C21—C5	−179.4 (5)	C23—C7—C49—C61	179.1 (7)
C3—C17—C21—C41	2.2 (8)	C23—C19—C47—C27	−0.3 (12)
C3—C17—C45—C25	−179.2 (5)	C23—C19—C47—C39	−178.3 (7)
C3—C17—C45—C37	1.5 (8)	C25—C11—C35—C67	177.9 (5)
C3—C55—C69—C37	11.8 (9)	C27—C9—C33—C65	177.5 (8)
C3—C55—C73—C77	0.8 (8)	C29—C13—C59—C79	179.0 (7)
C5—C11—C25—C45	1.4 (9)	C31—C15—C57—C77	−179.6 (5)
C5—C11—C35—C67	−4.1 (9)	C33—C9—C27—C47	180.0 (7)
C5—C21—C41—C31	−178.4 (5)	C35—C11—C25—C45	179.3 (5)
C5—C51—C63—C67	−0.5 (8)	C45—C17—C21—C5	−1.4 (8)
C7—C9—C27—C47	−0.8 (13)	C45—C17—C21—C41	−179.9 (4)
C7—C9—C33—C65	−1.8 (13)	C45—C37—C69—C55	−12.1 (11)
C7—C23—C43—C29	178.9 (7)	C47—C19—C23—C7	2.0 (12)
C7—C49—C61—C65	−0.5 (13)	C47—C19—C23—C43	178.6 (6)
C9—C7—C23—C19	−3.1 (12)	C47—C39—C71—C53	1.6 (13)
C9—C7—C23—C43	−179.5 (7)	C49—C7—C9—C27	177.7 (7)
C9—C7—C49—C61	4.1 (12)	C49—C7—C9—C33	−3.1 (11)
C9—C27—C47—C19	−0.3 (13)	C49—C7—C23—C19	−177.8 (7)
C9—C27—C47—C39	177.7 (7)	C49—C7—C23—C43	5.7 (13)
C9—C33—C65—C61	5.7 (13)	C49—C61—C65—C33	−4.5 (13)
C11—C5—C21—C17	−0.1 (8)	C51—C5—C11—C25	−178.1 (5)
C11—C5—C21—C41	178.4 (5)	C51—C5—C11—C35	3.9 (8)
C11—C5—C51—C63	−1.7 (7)	C51—C5—C21—C17	178.1 (5)
C11—C25—C45—C17	−2.9 (8)	C51—C5—C21—C41	−3.5 (8)
C11—C25—C45—C37	176.5 (5)	C51—C63—C67—C35	0.5 (8)
C11—C35—C67—C63	1.9 (8)	C53—C1—C13—C29	179.8 (7)
C13—C1—C19—C23	1.8 (13)	C53—C1—C13—C59	3.3 (12)
C13—C1—C19—C47	−179.1 (7)	C53—C1—C19—C23	−179.2 (6)
C13—C1—C53—C71	177.4 (7)	C53—C1—C19—C47	−0.1 (12)
C13—C1—C53—C75	−2.7 (13)	C53—C75—C79—C59	−4.5 (12)
C13—C29—C43—C23	−1.9 (13)	C55—C3—C15—C31	−177.7 (5)
C13—C59—C79—C75	5.2 (12)	C55—C3—C15—C57	0.6 (8)
C15—C3—C17—C21	−3.1 (8)	C55—C3—C17—C21	176.5 (5)
C15—C3—C17—C45	178.9 (5)	C55—C3—C17—C45	−1.4 (8)
C15—C3—C55—C69	174.7 (5)	C55—C73—C77—C57	1.9 (8)
C15—C3—C55—C73	−2.0 (8)	C57—C15—C31—C41	−178.0 (5)
C15—C31—C41—C21	−1.3 (8)	C59—C13—C29—C43	177.6 (7)
C15—C57—C77—C73	−3.5 (8)	C69—C37—C45—C17	5.3 (9)
C17—C3—C15—C31	1.9 (8)	C69—C37—C45—C25	−174.0 (6)
C17—C3—C15—C57	−179.8 (5)	C69—C55—C73—C77	−175.8 (5)
C17—C3—C55—C69	−4.9 (8)	C71—C39—C47—C19	−3.3 (12)
C17—C3—C55—C73	178.3 (5)	C71—C39—C47—C27	178.7 (7)
C17—C21—C41—C31	0.1 (8)	C71—C53—C75—C79	−176.6 (8)
C19—C1—C13—C29	−1.2 (12)	C73—C55—C69—C37	−171.5 (6)
C19—C1—C13—C59	−177.6 (7)	C75—C53—C71—C39	−179.0 (8)

(benzoapyrene_27.9GPa)

Crystal data

C20H12	Z = 4
Mr = 252.30	F(000) = 528
Triclinic, P1	Dx = 2.195 Mg m^−3
a = 3.1077 (4) Å	Synchrotron radiation, λ = 0.410 Å
b = 11.995 (2) Å	Cell parameters from 482 reflections
c = 20.571 (8) Å	θ = 3.9–16.1°
α = 91.56 (3)°	µ = 0.06 mm^−1
β = 89.92 (3)°	T = 293 K
γ = 95.171 (13)°	Block, black
V = 763.4 (3) Å^3	0.02 × 0.02 × 0.02 mm

Data collection

Esperanto-CrysAlisPro-abstract goniometer imported esperanto images diffractometer	764 independent reflections
Radiation source: synchrotron	431 reflections with I > 2σ(I)
Detector resolution: 13.3333 pixels mm^-1	Rint = 0.059
ω scans	θmax = 15.9°, θmin = 3.8°
Absorption correction: multi-scan CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	h = −4→4
Tmin = 0.044, Tmax = 1.000	k = −15→15
988 measured reflections	l = −11→6

Refinement

Refinement on F^2	186 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.143	H-atom parameters constrained
wR(F^2) = 0.364	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.68	(Δ/σ)max < 0.001
764 reflections	Δρmax = 0.31 e Å^−3
361 parameters	Δρmin = −0.34 e Å^−3

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	1.078 (3)	0.7640 (10)	0.8305 (17)	0.04 (2)
C3	1.011 (3)	0.2464 (10)	0.667 (2)	0.07 (3)
C5	0.508 (3)	0.2907 (10)	0.5031 (18)	0.029 (4)
C7	0.533 (3)	0.7775 (10)	0.9907 (17)	0.037 (4)
C9	0.399 (4)	0.6661 (12)	1.001 (2)	0.04 (3)
C11	0.328 (3)	0.1789 (11)	0.495 (2)	0.07 (3)
C13	1.236 (3)	0.8772 (11)	0.8247 (17)	0.039 (10)
C15	1.174 (3)	0.3561 (11)	0.675 (2)	0.035 (4)
C17	0.778 (3)	0.2231 (9)	0.6040 (17)	0.026 (4)
C19	0.847 (4)	0.7313 (12)	0.8895 (19)	0.042 (4)
C21	0.739 (3)	0.3106 (10)	0.5602 (19)	0.032 (6)
C23	0.775 (3)	0.8119 (11)	0.9365 (19)	0.038 (4)
C25	0.364 (3)	0.0946 (9)	0.5355 (17)	0.04 (2)
H25	0.228532	0.023780	0.525916	0.045*
C27	0.476 (4)	0.5892 (12)	0.951 (2)	0.041 (4)
H27	0.371244	0.514668	0.954692	0.049*
C29	1.154 (4)	0.9542 (10)	0.8763 (19)	0.037 (10)
H29	1.260391	1.028818	0.872974	0.044*
C31	1.131 (3)	0.4391 (10)	0.640 (2)	0.034 (4)
H31	1.235948	0.511356	0.653260	0.041*
C33	0.167 (4)	0.6325 (13)	1.052 (2)	0.043 (4)
H33	0.059663	0.557645	1.053098	0.052*
C35	0.082 (4)	0.1567 (12)	0.431 (2)	0.045 (10)
H35	−0.044849	0.085014	0.421123	0.055*
C37	0.674 (3)	0.0307 (9)	0.6383 (18)	0.032 (10)
H37	0.520063	−0.039081	0.633034	0.038*
C39	0.764 (3)	0.5399 (11)	0.843 (2)	0.042 (4)
H39	0.639047	0.466517	0.844041	0.051*
C41	0.913 (3)	0.4162 (9)	0.5797 (17)	0.04 (2)
H41	0.885758	0.475298	0.552087	0.044*
C43	0.929 (3)	0.9229 (12)	0.930 (2)	0.043 (10)
H43	0.876674	0.975860	0.961771	0.051*
C45	0.607 (3)	0.1142 (11)	0.592 (2)	0.034 (4)
C47	0.697 (4)	0.6191 (10)	0.896 (2)	0.041 (10)
C49	0.456 (3)	0.8541 (11)	1.0406 (19)	0.039 (4)
H49	0.562211	0.928882	1.038057	0.046*
C51	0.463 (3)	0.3704 (11)	0.459 (2)	0.07 (3)
H51	0.588668	0.442656	0.466872	0.088*
C53	1.164 (4)	0.6843 (11)	0.788 (2)	0.044 (4)
C55	1.075 (3)	0.1552 (11)	0.706 (2)	0.040 (4)
C57	1.406 (3)	0.3754 (11)	0.739 (2)	0.06 (3)
H57	1.524844	0.447204	0.750283	0.067*
C59	1.469 (3)	0.9044 (10)	0.7736 (18)	0.035 (4)
H59	1.590142	0.977878	0.770969	0.042*
C61	0.219 (3)	0.8168 (13)	1.094 (2)	0.054 (10)
H61	0.152426	0.869896	1.125585	0.065*
C63	0.233 (3)	0.3473 (11)	0.4010 (19)	0.034 (4)
H63	0.204708	0.403076	0.371149	0.041*
C65	0.074 (3)	0.7052 (13)	1.105 (2)	0.07 (3)
H65	−0.069562	0.681027	1.141988	0.080*
C67	0.044 (3)	0.2377 (12)	0.389 (2)	0.045 (10)
H67	−0.111754	0.221502	0.350769	0.055*
C69	0.931 (3)	0.0463 (11)	0.6854 (19)	0.036 (4)
H69	1.025369	−0.014429	0.706699	0.044*
C71	0.994 (3)	0.5720 (10)	0.7948 (18)	0.035 (6)
H71	1.053476	0.519363	0.762845	0.042*
C73	1.293 (3)	0.1828 (12)	0.770 (2)	0.041 (4)
H73	1.317971	0.128887	0.801579	0.049*
C75	1.397 (3)	0.7175 (13)	0.731 (2)	0.048 (10)
H75	1.450118	0.664322	0.698984	0.058*
C77	1.449 (3)	0.2895 (11)	0.7803 (19)	0.040 (4)
H77	1.599713	0.307137	0.818815	0.048*
C79	1.546 (4)	0.8298 (12)	0.723 (2)	0.042 (4)
H79	1.689609	0.853401	0.685459	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.027 (4)	0.038 (6)	0.06 (7)	0.001 (4)	0.005 (12)	−0.002 (12)
C3	0.031 (5)	0.028 (6)	0.16 (9)	0.001 (4)	−0.003 (14)	0.005 (14)
C5	0.027 (3)	0.031 (4)	0.031 (9)	0.002 (3)	−0.007 (5)	0.006 (6)
C7	0.036 (4)	0.039 (5)	0.037 (9)	0.009 (3)	−0.002 (5)	−0.003 (6)
C9	0.033 (5)	0.045 (7)	0.05 (8)	0.008 (4)	−0.011 (13)	0.010 (13)
C11	0.024 (4)	0.035 (7)	0.16 (9)	0.004 (4)	−0.012 (14)	−0.010 (14)
C13	0.031 (4)	0.037 (6)	0.05 (3)	0.005 (4)	−0.019 (9)	−0.013 (10)
C15	0.032 (4)	0.038 (5)	0.036 (9)	0.003 (4)	−0.006 (6)	0.000 (6)
C17	0.024 (3)	0.027 (4)	0.027 (8)	0.000 (3)	−0.010 (5)	0.003 (5)
C19	0.040 (4)	0.044 (5)	0.042 (9)	0.012 (4)	0.001 (6)	0.002 (6)
C21	0.027 (4)	0.030 (5)	0.038 (16)	0.002 (4)	−0.021 (8)	0.010 (9)
C23	0.036 (4)	0.041 (5)	0.039 (9)	0.008 (3)	−0.002 (5)	−0.001 (6)
C25	0.029 (4)	0.022 (5)	0.06 (7)	−0.002 (4)	−0.024 (11)	−0.005 (11)
C27	0.040 (4)	0.041 (5)	0.042 (9)	0.001 (4)	−0.006 (6)	0.007 (6)
C29	0.042 (5)	0.026 (5)	0.04 (3)	0.003 (4)	−0.011 (10)	0.012 (9)
C31	0.034 (4)	0.032 (5)	0.035 (8)	−0.002 (4)	−0.004 (6)	0.005 (6)
C33	0.043 (4)	0.044 (5)	0.044 (9)	0.008 (4)	−0.009 (6)	−0.002 (6)
C35	0.035 (4)	0.041 (6)	0.06 (3)	0.001 (5)	−0.011 (10)	−0.010 (11)
C37	0.028 (4)	0.028 (5)	0.04 (3)	−0.005 (3)	−0.017 (9)	0.012 (10)
C39	0.043 (4)	0.042 (5)	0.042 (9)	0.004 (4)	−0.004 (6)	0.000 (6)
C41	0.027 (4)	0.029 (6)	0.05 (7)	0.001 (4)	−0.008 (12)	0.004 (11)
C43	0.036 (5)	0.048 (7)	0.05 (3)	0.015 (4)	−0.008 (10)	0.017 (11)
C45	0.031 (4)	0.037 (5)	0.034 (9)	−0.002 (4)	−0.005 (6)	0.004 (6)
C47	0.037 (5)	0.033 (6)	0.05 (3)	0.004 (4)	−0.009 (10)	0.020 (11)
C49	0.035 (4)	0.041 (5)	0.041 (9)	0.004 (3)	−0.010 (5)	0.005 (6)
C51	0.033 (5)	0.033 (7)	0.16 (8)	0.014 (4)	0.000 (14)	0.010 (14)
C53	0.044 (4)	0.045 (5)	0.045 (9)	0.009 (4)	−0.002 (6)	0.003 (6)
C55	0.034 (4)	0.045 (5)	0.040 (9)	0.003 (4)	−0.006 (6)	0.001 (6)
C57	0.031 (5)	0.037 (7)	0.10 (8)	0.004 (4)	−0.030 (13)	−0.011 (14)
C59	0.037 (4)	0.032 (5)	0.036 (9)	0.002 (3)	−0.005 (6)	0.005 (6)
C61	0.032 (5)	0.064 (8)	0.07 (3)	0.010 (5)	−0.017 (10)	−0.004 (13)
C63	0.030 (4)	0.037 (5)	0.037 (9)	0.004 (3)	−0.011 (6)	0.005 (6)
C65	0.023 (4)	0.078 (10)	0.10 (8)	0.009 (5)	−0.006 (12)	0.003 (18)
C67	0.029 (4)	0.054 (8)	0.05 (3)	0.009 (4)	−0.005 (9)	−0.002 (12)
C69	0.033 (4)	0.038 (5)	0.038 (9)	0.001 (3)	−0.007 (6)	0.008 (6)
C71	0.039 (4)	0.029 (5)	0.037 (16)	0.007 (4)	−0.019 (8)	0.013 (8)
C73	0.037 (4)	0.045 (5)	0.042 (9)	0.008 (4)	−0.003 (6)	0.001 (6)
C75	0.033 (4)	0.050 (7)	0.06 (3)	0.005 (4)	−0.007 (10)	−0.006 (12)
C77	0.030 (4)	0.050 (5)	0.041 (9)	0.003 (4)	−0.009 (6)	−0.003 (6)
C79	0.037 (4)	0.048 (5)	0.042 (9)	0.008 (4)	−0.002 (5)	0.006 (6)

Geometric parameters (Å, º)

C1—C13	1.41 (2)	C35—H35	0.9300
C1—C19	1.45 (5)	C35—C67	1.33 (4)
C1—C53	1.33 (3)	C37—H37	0.9300
C3—C15	1.373 (17)	C37—C45	1.42 (4)
C3—C17	1.49 (5)	C37—C69	1.26 (4)
C3—C55	1.40 (4)	C39—H39	0.9300
C5—C11	1.413 (16)	C39—C47	1.46 (4)
C5—C21	1.38 (5)	C39—C71	1.27 (4)
C5—C51	1.36 (4)	C41—H41	0.9300
C7—C9	1.39 (2)	C43—H43	0.9300
C7—C23	1.40 (4)	C49—H49	0.9300
C7—C49	1.39 (3)	C49—C61	1.39 (5)
C9—C27	1.41 (4)	C51—H51	0.9300
C9—C33	1.32 (5)	C51—C63	1.39 (5)
C11—C25	1.34 (4)	C53—C71	1.41 (2)
C11—C35	1.52 (6)	C53—C75	1.42 (5)
C13—C29	1.43 (3)	C55—C69	1.39 (2)
C13—C59	1.31 (4)	C55—C73	1.51 (6)
C15—C31	1.26 (4)	C57—H57	0.9300
C15—C57	1.49 (6)	C57—C77	1.37 (4)
C17—C21	1.42 (4)	C59—H59	0.9300
C17—C45	1.380 (16)	C59—C79	1.39 (4)
C19—C23	1.38 (4)	C61—H61	0.9300
C19—C47	1.39 (2)	C61—C65	1.39 (3)
C21—C41	1.381 (19)	C63—H63	0.9300
C23—C43	1.39 (2)	C63—C67	1.406 (18)
C25—H25	0.9300	C65—H65	0.9300
C25—C45	1.40 (5)	C67—H67	0.9300
C27—H27	0.9300	C69—H69	0.9300
C27—C47	1.35 (5)	C71—H71	0.9300
C29—H29	0.9300	C73—H73	0.9300
C29—C43	1.34 (5)	C73—C77	1.337 (18)
C31—H31	0.9300	C75—H75	0.9300
C31—C41	1.43 (5)	C75—C79	1.40 (2)
C33—H33	0.9300	C77—H77	0.9300
C33—C65	1.42 (4)	C79—H79	0.9300
C13—C1—C19	118 (2)	C21—C41—C31	123 (2)
C53—C1—C13	123 (3)	C21—C41—H41	118.4
C53—C1—C19	118.4 (19)	C31—C41—H41	118.4
C15—C3—C17	113 (3)	C23—C43—H43	120.0
C15—C3—C55	129 (3)	C29—C43—C23	120 (2)
C55—C3—C17	117.6 (17)	C29—C43—H43	120.0
C21—C5—C11	114 (3)	C17—C45—C25	116 (3)
C51—C5—C11	123 (3)	C17—C45—C37	120 (3)
C51—C5—C21	123.5 (14)	C25—C45—C37	124.2 (14)
C9—C7—C23	123 (2)	C19—C47—C39	119 (3)
C9—C7—C49	117 (3)	C27—C47—C19	118 (2)
C49—C7—C23	120.3 (15)	C27—C47—C39	122.5 (15)
C7—C9—C27	117 (3)	C7—C49—H49	120.6
C33—C9—C7	123 (2)	C61—C49—C7	118.8 (15)
C33—C9—C27	119.8 (18)	C61—C49—H49	120.6
C5—C11—C35	114 (3)	C5—C51—H51	119.0
C25—C11—C5	127 (3)	C5—C51—C63	122.1 (15)
C25—C11—C35	119.8 (15)	C63—C51—H51	119.0
C1—C13—C29	118 (2)	C1—C53—C71	121 (3)
C59—C13—C1	117.8 (18)	C1—C53—C75	117.6 (18)
C59—C13—C29	123.7 (15)	C71—C53—C75	121 (2)
C3—C15—C57	112 (3)	C3—C55—C73	116.0 (17)
C31—C15—C3	130 (3)	C69—C55—C3	121 (3)
C31—C15—C57	118.5 (17)	C69—C55—C73	123 (3)
C21—C17—C3	120.1 (14)	C15—C57—H57	119.3
C45—C17—C3	116 (3)	C77—C57—C15	121.4 (15)
C45—C17—C21	124 (3)	C77—C57—H57	119.3
C23—C19—C1	119.4 (18)	C13—C59—H59	118.1
C23—C19—C47	122 (3)	C13—C59—C79	123.8 (15)
C47—C19—C1	118 (2)	C79—C59—H59	118.1
C5—C21—C17	120.4 (14)	C49—C61—H61	117.7
C41—C21—C5	122 (2)	C49—C61—C65	125 (2)
C41—C21—C17	117 (3)	C65—C61—H61	117.7
C19—C23—C7	117.3 (17)	C51—C63—H63	120.8
C19—C23—C43	121 (3)	C51—C63—C67	118 (3)
C43—C23—C7	121 (2)	C67—C63—H63	120.8
C11—C25—H25	120.2	C33—C65—H65	123.5
C11—C25—C45	119.5 (15)	C61—C65—C33	113 (3)
C45—C25—H25	120.2	C61—C65—H65	123.5
C9—C27—H27	118.6	C35—C67—C63	122 (3)
C47—C27—C9	122.7 (18)	C35—C67—H67	119.2
C47—C27—H27	118.6	C63—C67—H67	119.2
C13—C29—H29	118.8	C37—C69—C55	120 (2)
C43—C29—C13	122.4 (15)	C37—C69—H69	120.2
C43—C29—H29	118.8	C55—C69—H69	120.2
C15—C31—H31	121.8	C39—C71—C53	123 (2)
C15—C31—C41	116.5 (17)	C39—C71—H71	118.5
C41—C31—H31	121.8	C53—C71—H71	118.5
C9—C33—H33	118.5	C55—C73—H73	122.1
C9—C33—C65	123.0 (17)	C77—C73—C55	116 (3)
C65—C33—H33	118.5	C77—C73—H73	122.1
C11—C35—H35	119.3	C53—C75—H75	119.8
C67—C35—C11	121.4 (16)	C79—C75—C53	120 (2)
C67—C35—H35	119.3	C79—C75—H75	119.8
C45—C37—H37	118.3	C57—C77—H77	117.1
C69—C37—H37	118.3	C73—C77—C57	126 (3)
C69—C37—C45	123.4 (13)	C73—C77—H77	117.1
C47—C39—H39	120.4	C59—C79—C75	117 (3)
C71—C39—H39	120.4	C59—C79—H79	121.5
C71—C39—C47	119.2 (15)	C75—C79—H79	121.5
C1—C13—C29—C43	−1 (3)	C19—C1—C53—C71	8 (4)
C1—C13—C59—C79	4 (4)	C19—C1—C53—C75	−178.8 (19)
C1—C19—C23—C7	176.7 (18)	C19—C23—C43—C29	0 (4)
C1—C19—C23—C43	−2 (4)	C21—C5—C11—C25	−1 (3)
C1—C19—C47—C27	−179 (2)	C21—C5—C11—C35	−178.7 (17)
C1—C19—C47—C39	−2 (3)	C21—C5—C51—C63	179.0 (18)
C1—C53—C71—C39	−2 (4)	C21—C17—C45—C25	−4 (3)
C1—C53—C75—C79	3 (4)	C21—C17—C45—C37	177.8 (15)
C3—C15—C31—C41	−6 (3)	C23—C7—C9—C27	−7 (4)
C3—C15—C57—C77	1 (3)	C23—C7—C9—C33	−179 (3)
C3—C17—C21—C5	−177.3 (16)	C23—C7—C49—C61	−179 (2)
C3—C17—C21—C41	−2 (2)	C23—C19—C47—C27	0 (4)
C3—C17—C45—C25	175.9 (16)	C23—C19—C47—C39	176 (2)
C3—C17—C45—C37	−3 (2)	C25—C11—C35—C67	−179.2 (17)
C3—C55—C69—C37	−13 (3)	C27—C9—C33—C65	−180 (2)
C3—C55—C73—C77	−8 (2)	C29—C13—C59—C79	−179 (2)
C5—C11—C25—C45	−1 (3)	C31—C15—C57—C77	177.4 (16)
C5—C11—C35—C67	−1 (3)	C33—C9—C27—C47	177 (2)
C5—C21—C41—C31	176.3 (17)	C35—C11—C25—C45	177.1 (18)
C5—C51—C63—C67	0 (2)	C45—C17—C21—C5	2 (3)
C7—C9—C27—C47	5 (4)	C45—C17—C21—C41	177.4 (15)
C7—C9—C33—C65	−8 (4)	C45—C37—C69—C55	18 (3)
C7—C23—C43—C29	−179 (2)	C47—C19—C23—C7	−2 (4)
C7—C49—C61—C65	5 (4)	C47—C19—C23—C43	179 (2)
C9—C7—C23—C19	6 (4)	C47—C39—C71—C53	−5 (4)
C9—C7—C23—C43	−176 (2)	C49—C7—C9—C27	179.9 (19)
C9—C7—C49—C61	−6 (3)	C49—C7—C9—C33	8 (4)
C9—C27—C47—C19	−1 (4)	C49—C7—C23—C19	179 (2)
C9—C27—C47—C39	−178 (2)	C49—C7—C23—C43	−3 (4)
C9—C33—C65—C61	5 (4)	C49—C61—C65—C33	−4 (4)
C11—C5—C21—C17	0 (2)	C51—C5—C11—C25	178.7 (17)
C11—C5—C21—C41	−174.9 (16)	C51—C5—C11—C35	0 (2)
C11—C5—C51—C63	0 (2)	C51—C5—C21—C17	−179.3 (16)
C11—C25—C45—C17	3 (3)	C51—C5—C21—C41	6 (3)
C11—C25—C45—C37	−178.6 (16)	C51—C63—C67—C35	0 (3)
C11—C35—C67—C63	1 (3)	C53—C1—C13—C29	−175 (3)
C13—C1—C19—C23	3 (4)	C53—C1—C13—C59	2 (4)
C13—C1—C19—C47	−179 (2)	C53—C1—C19—C23	176 (2)
C13—C1—C53—C71	−179 (2)	C53—C1—C19—C47	−5 (4)
C13—C1—C53—C75	−5 (4)	C53—C75—C79—C59	2 (3)
C13—C29—C43—C23	1 (4)	C55—C3—C15—C31	178 (2)
C13—C59—C79—C75	−6 (4)	C55—C3—C15—C57	−7 (3)
C15—C3—C17—C21	0 (2)	C55—C3—C17—C21	−174.2 (16)
C15—C3—C17—C45	180.0 (14)	C55—C3—C17—C45	6 (2)
C15—C3—C55—C69	−172 (2)	C55—C73—C77—C57	4 (2)
C15—C3—C55—C73	10 (3)	C57—C15—C31—C41	179.0 (18)
C15—C31—C41—C21	2 (2)	C59—C13—C29—C43	−177 (2)
C15—C57—C77—C73	−1 (3)	C69—C37—C45—C17	−10 (3)
C17—C3—C15—C31	5 (3)	C69—C37—C45—C25	172 (2)
C17—C3—C15—C57	−179.7 (15)	C69—C55—C73—C77	173.9 (13)
C17—C3—C55—C69	1 (3)	C71—C39—C47—C19	7 (4)
C17—C3—C55—C73	−177.1 (15)	C71—C39—C47—C27	−176 (2)
C17—C21—C41—C31	1 (2)	C71—C53—C75—C79	177 (2)
C19—C1—C13—C29	−1 (3)	C73—C55—C69—C37	165 (2)
C19—C1—C13—C59	175 (2)	C75—C53—C71—C39	−176 (3)