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_7247913
_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         '2(C21 H15)'
_chemical_formula_sum            'C42 H30'
_chemical_formula_weight         534.66
_chemical_name_common            C6Ph6
_chemical_name_systematic        Hexaphenylbenzene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-12-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.276(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4453(14)
_cell_length_b                   18.97(2)
_cell_length_c                   11.5585(17)
_cell_measurement_pressure       2320000
_cell_measurement_reflns_used    1016
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.7470
_cell_measurement_theta_min      3.5040
_cell_volume                     2509(3)
_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  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_pressure         2320000
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid photon'
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.436
_diffrn_measured_fraction_theta_max 0.436
_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    -47.00  32.00   0.50  190.00    --    9.15  26.00  -8.00  158
  2  \w      6.00  40.00   0.50  190.00    --    9.15 -57.00-150.00   68
  3  \w     44.00  70.00   0.50  190.00    --    9.15 -99.00-150.00   52
  4  \w     38.00  63.00   0.50  190.00    --   -9.42-114.00-135.00   50
  5  \w     15.00  42.00   0.50  190.00    --   -9.42 -77.00-150.00   54
  6  \w    -34.00  -8.00   0.50  190.00    --    9.15  57.00-180.00   52
  7  \w    -49.00  -5.00   0.50  190.00    --   -9.42  67.00 157.00   88
;
_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      -0.0006585000
_diffrn_orient_matrix_UB_12      0.0374598000
_diffrn_orient_matrix_UB_13      0.0012012000
_diffrn_orient_matrix_UB_21      0.0130374000
_diffrn_orient_matrix_UB_22      -0.0003436000
_diffrn_orient_matrix_UB_23      0.0602655000
_diffrn_orient_matrix_UB_31      0.0604840000
_diffrn_orient_matrix_UB_32      0.0007786000
_diffrn_orient_matrix_UB_33      -0.0115649000
_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  0.1165
_diffrn_reflns_av_unetI/netI     0.1032
_diffrn_reflns_Laue_measured_fraction_full 0.436
_diffrn_reflns_Laue_measured_fraction_max 0.436
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4489
_diffrn_reflns_point_group_measured_fraction_full 0.436
_diffrn_reflns_point_group_measured_fraction_max 0.436
_diffrn_reflns_theta_full        18.907
_diffrn_reflns_theta_max         18.907
_diffrn_reflns_theta_min         3.526
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.07406
_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    1.415
_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         0.304
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         868
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.1739
_refine_ls_R_factor_gt           0.1211
_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          0.3115
_refine_ls_wR_factor_ref         0.3489
_reflns_Friedel_coverage         0.000
_reflns_number_gt                526
_reflns_number_total             868
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01122d2.cif
_cod_data_source_block           C6Ph6_232GPa
_cod_depositor_comments
'Adding full bibliography for 7247910--7247915.cif.'
_cod_original_cell_volume        2510(3)
_cod_database_code               7247913
_chemical_oxdiff_formula         'C42 H30'
_chemical_oxdiff_usercomment
'Hexaphenylbenzene at 2.32 GPa in MiTeGen LVCO-5 Cryo Oil.'
_reflns_odcompleteness_completeness 46.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     18.81
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1A-C2A
 1.39 with sigma of 0.02
 C1A-C3A_$1
 1.39 with sigma of 0.02
 C3A_$1-C2A_$1
 1.39 with sigma of 0.02
 C2A_$1-C1A_$1
 1.39 with sigma of 0.02
 C3A-C1A_$1
 1.39 with sigma of 0.02
 C2A-C3A
 1.39 with sigma of 0.02
 C2-C1
 1.39 with sigma of 0.02
 C1-C3_$2
 1.39 with sigma of 0.02
 C3_$2-C2_$2
 1.39 with sigma of 0.02
 C1_$2-C2_$2
 1.39 with sigma of 0.02
 C3-C1_$2
 1.39 with sigma of 0.02
 C2-C3
 1.39 with sigma of 0.02
 C2_$2-C3
 2.42 with sigma of 0.02
 C3_$2-C1_$2
 2.42 with sigma of 0.02
 C1-C3
 2.42 with sigma of 0.02
 C2-C1_$2
 2.42 with sigma of 0.02
 C2-C3_$2
 2.42 with sigma of 0.02
 C1-C2_$2
 2.42 with sigma of 0.02
 C3A_$1-C2A
 2.42 with sigma of 0.02
 C1A_$1-C2A
 2.42 with sigma of 0.02
 C2A_$1-C3A
 2.42 with sigma of 0.02
 C1A-C2A_$1
 2.42 with sigma of 0.02
 C1A-C3A
 2.42 with sigma of 0.02
 C3A_$1-C1A_$1
 2.42 with sigma of 0.02
3. Restrained planarity
 C1_$2, C1, C3_$2, C3, C2_$2, C2
 with sigma of 0.1
 C3A, C1A_$1, C1A, C2A_$1, C2A, C3A_$1
 with sigma of 0.1
 C20A_$1, C21A_$1, C19A_$1, C18A_$1, C17A_$1, C16A_$1
 with sigma of 0.1
 C13A_$1, C14A_$1, C15A_$1, C10A_$1, C11A_$1, C12A_$1
 with sigma of 0.1
 C4A_$1, C5A_$1, C6A_$1, C7A_$1, C8A_$1, C9A_$1
 with sigma of 0.1
 C16A, C21A, C20A, C19A, C18A, C17A
 with sigma of 0.1
 C13A, C12A, C11A, C10A, C15A, C14A
 with sigma of 0.1
 C4A, C5A, C6A, C7A, C8A, C9A
 with sigma of 0.1
 C5, C6, C7, C8, C9, C4
 with sigma of 0.1
 C10, C14, C15, C13, C12, C11
 with sigma of 0.1
 C17, C21, C16, C18, C19, C20
 with sigma of 0.1
 C16, C21, C20, C19, C18, C17, C3
 with sigma of 0.01
 C10, C11, C15, C14, C13, C12, C2
 with sigma of 0.01
 C4, C9, C8, C7, C6, C5, C1
 with sigma of 0.01
 C3A, C17A, C18A, C19A, C20A, C21A, C16A
 with sigma of 0.01
 C10A, C15A, C14A, C12A, C11A, C2A, C13A
 with sigma of 0.01
 C9A, C8A, C7A, C6A, C5A, C4A, C1A
 with sigma of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C7(H7), C6(H6), C5(H5), C11(H11), C15(H15), C14(H14),
 C13(H13), C12(H12), C21(H21), C20(H20), C19(H19), C18(H18), C17(H17),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C15A(H15A),
 C14A(H14A), C13A(H13A), C12A(H12A), C11A(H11A), C9A(H9A), C8A(H8A), C7A(H7A),
 C6A(H6A), C5A(H5A)
4.b Fitted hexagon refined as free rotating group:
 C4(C9,C8,C7,C6,C5), C11(C10,C15,C14,C13,C12), C16(C21,C20,C19,C18,C17),
 C17A(C18A,C19A,C20A,C21A,C16A), C10A(C15A,C14A,C13A,C12A,C11A), C9A(C8A,C7A,
 C6A,C5A,C4A)
;
_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 12.848
_oxdiff_exptl_absorpt_empirical_full_min 0.455