The crystal structure of hexaphenylbenzene under high hydrostatic pressure
Turner, Gemma F.; Stapleton, Nicholas; Brookes, James; Spagnoli, Dino; Sussardi, Alif N.; Jones, Anita C.; McGonigal, Paul R.; Moggach, Stephen A.; CrystEngComm 26 (2024) 459–467; doi:10.1039/D3CE01122D

data_7247914
_publ_section_title
;
 The crystal structure of hexaphenylbenzene under high hydrostatic
 pressure
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              459
_journal_page_last               467
_journal_paper_doi               10.1039/D3CE01122D
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C42 H30'
_chemical_formula_sum            'C42 H30'
_chemical_formula_weight         534.66
_chemical_name_common            C6Ph6
_chemical_name_systematic        Hexaphenylbenzene
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1790(17)
_cell_length_b                   11.8019(17)
_cell_length_c                   20.61(3)
_cell_measurement_pressure       220000
_cell_measurement_reflns_used    1869
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      19.7740
_cell_measurement_theta_min      3.4400
_cell_volume                     2962(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_pressure         220000
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'Hybrid photon'
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.470
_diffrn_measured_fraction_theta_max 0.471
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -22.00   3.00   0.50   60.00    --   17.95  15.00   0.00   50
  2  \w    -14.00  12.00   0.50   60.00    --  -18.26  15.00   0.00   52
  3  \w    -36.00 -16.00   0.50   60.00    --   17.95  38.00  30.00   40
  4  \w    -15.00  10.00   0.50   60.00    --   17.95  82.00 -29.00   50
  5  \w    -32.00  -5.00   0.50   60.00    --   17.95 114.00 -45.00   54
  6  \w    -36.00 -10.00   0.50   60.00    --  -18.26  77.00 -30.00   52
  7  \w    -32.00  -7.00   0.50   60.00    --   17.95 -15.00-169.00   50
  8  \w    -32.00  -7.00   0.50   60.00    --  -18.26 -15.00-169.00   50
  9  \w     -3.00  25.00   0.50   60.00    --  -18.26 -19.00-180.00   56
 10  \w      8.00  42.00   0.50   60.00    --  -18.26 -38.00-180.00   68
 11  \w     25.00  51.00   0.50   60.00    --   17.95-112.00  42.00   52
 12  \w     -4.00  18.00   0.50   60.00    --  -18.26 -57.00  30.00   44
 13  \w    -53.00 -28.00   0.50   60.00    --   17.95 112.00 135.00   50
 14  \w    -99.00 -71.00   0.50   60.00    --  -18.26-178.00 -90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Synergy-S'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0011338000
_diffrn_orient_matrix_UB_12      -0.0011758000
_diffrn_orient_matrix_UB_13      -0.0342078000
_diffrn_orient_matrix_UB_21      -0.0572963000
_diffrn_orient_matrix_UB_22      0.0117146000
_diffrn_orient_matrix_UB_23      0.0005520000
_diffrn_orient_matrix_UB_31      0.0113494000
_diffrn_orient_matrix_UB_32      0.0590860000
_diffrn_orient_matrix_UB_33      -0.0008716000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1187
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_Laue_measured_fraction_full 0.470
_diffrn_reflns_Laue_measured_fraction_max 0.471
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6996
_diffrn_reflns_point_group_measured_fraction_full 0.442
_diffrn_reflns_point_group_measured_fraction_max 0.442
_diffrn_reflns_theta_full        19.761
_diffrn_reflns_theta_max         19.761
_diffrn_reflns_theta_min         3.346
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 258 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -10.0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.358
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         1183
_refine_ls_number_restraints     53
_refine_ls_restrained_S_all      1.343
_refine_ls_R_factor_all          0.1709
_refine_ls_R_factor_gt           0.1160
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3033
_refine_ls_wR_factor_ref         0.3662
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.411
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                789
_reflns_number_total             1183
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01122d2.cif
_cod_data_source_block           C6Ph6_022GPa
_cod_depositor_comments
'Adding full bibliography for 7247910--7247915.cif.'
_cod_original_cell_volume        2963(4)
_cod_database_code               7247914
_chemical_oxdiff_formula         'C42 H30'
_chemical_oxdiff_usercomment
'Hexphenylbenzene at 0.22 GPa in MiTeGen LVCO-5 Cryo Oil.'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.983
_reflns_odcompleteness_completeness 29.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C37-C5
 2.508 with sigma of 0.01
 C1-C12
 2.512 with sigma of 0.02
 C3-C20
 2.488 with sigma of 0.02
 C6-C7
 2.478 with sigma of 0.02
 C7-C2
 2.513 with sigma of 0.02
 C4-C30
 2.499 with sigma of 0.02
 C1-C13
 2.52 with sigma of 0.02
 C2-C14
 2.478 with sigma of 0.02
 C13-C3
 2.476 with sigma of 0.02
 C2-C19
 2.519 with sigma of 0.02
 C19-C4
 2.504 with sigma of 0.02
 C5-C36
 2.474 with sigma of 0.02
 C3-C25
 2.478 with sigma of 0.02
 C26-C4
 2.485 with sigma of 0.02
 C25-C5
 2.515 with sigma of 0.02
 C24-C3
 2.51 with sigma of 0.02
 C31-C4
 2.494 with sigma of 0.02
 C18-C2
 2.484 with sigma of 0.02
 C31-C6
 2.479 with sigma of 0.02
 C8-C1
 2.474 with sigma of 0.02
 C5-C37
 2.508 with sigma of 0.02
 C37-C1
 2.5 with sigma of 0.02
 C38-C6
 2.497 with sigma of 0.02
 C6-C42
 2.515 with sigma of 0.02
 C32-C5
 2.478 with sigma of 0.02
3. Restrained planarity
 C6, C1, C2, C5, C3, C4, C37, C7, C19, C13, C25, C31
 with sigma of 0.1
 C31, C34, C32, C33, C36, C35
 with sigma of 0.1
 C7, C8, C10, C9, C12, C11
 with sigma of 0.1
 C19, C20, C21, C23, C24, C22
 with sigma of 0.1
 C37, C42, C40, C39, C38, C41
 with sigma of 0.1
 C25, C30, C26, C29, C28, C27
 with sigma of 0.1
 C13, C14, C18, C15, C16, C17
 with sigma of 0.1
4.a Aromatic/amide H refined with riding coordinates:
 C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C30(H30), C29(H29),
 C28(H28), C27(H27), C26(H26), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C18(H18), C17(H17), C16(H16), C15(H15), C14(H14), C36(H36), C35(H35),
 C34(H34), C33(H33), C32(H32), C12(H12), C11(H11), C10(H10), C9(H9), C8(H8)
4.b Fitted hexagon refined as free rotating group:
 C37(C38,C39,C40,C41,C42), C25(C30,C29,C28,C27,C26), C6(C5,C4,C3,C2,C1),
 C19(C20,C21,C22,C23,C24), C13(C18,C17,C16,C15,C14), C31(C36,C35,C34,C33,C32),
 C7(C12,C11,C10,C9,C8)
;
_olex2_exptl_crystal_mounting_method
'Loaded in a Merrill-Bassett diamond anvil cell in a PTM of MiTeGen LVCO-5 Cryo Oil.'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.976
_oxdiff_exptl_absorpt_empirical_full_min 0.570