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_7247912
_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             2023-08-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-11-08 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.196(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4968(17)
_cell_length_b                   19.231(3)
_cell_length_c                   11.6579(12)
_cell_measurement_pressure       1740000
_cell_measurement_reflns_used    1097
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      18.7880
_cell_measurement_theta_min      3.4770
_cell_volume                     2576.9(6)
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_pressure         1740000
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'Hybrid Photon'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.441
_diffrn_measured_fraction_theta_max 0.441
_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     -4.00  18.00   0.50  230.00    --  -13.47 -57.00  30.00   44
  2  \w    -34.00  16.00   0.50  230.00    --   13.15  67.00 -23.00  100
  3  \w    -38.00  -9.00   0.50  230.00    --  -13.47  77.00 -30.00   58
  4  \w    -43.00  16.00   0.50  230.00    --   13.15  38.00-180.00  118
  5  \w    -28.00  37.00   0.50  230.00    --  -13.47 -57.00-150.00  130
  6  \w     -7.00  18.00   0.50  230.00    --  -13.47 -38.00-150.00   50
  7  \w    -64.00   4.00   0.50  230.00    --  -13.47  57.00-180.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008562000
_diffrn_orient_matrix_UB_12      0.0368741000
_diffrn_orient_matrix_UB_13      0.0016483000
_diffrn_orient_matrix_UB_21      0.0125842000
_diffrn_orient_matrix_UB_22      -0.0005099000
_diffrn_orient_matrix_UB_23      0.0598089000
_diffrn_orient_matrix_UB_31      0.0604067000
_diffrn_orient_matrix_UB_32      0.0007648000
_diffrn_orient_matrix_UB_33      -0.0111361000
_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  0.0995
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.441
_diffrn_reflns_Laue_measured_fraction_max 0.441
_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            5319
_diffrn_reflns_point_group_measured_fraction_full 0.441
_diffrn_reflns_point_group_measured_fraction_max 0.441
_diffrn_reflns_theta_full        18.931
_diffrn_reflns_theta_max         18.931
_diffrn_reflns_theta_min         3.496
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64274
_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    1.378
_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          0.013
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.374
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         909
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.318
_refine_ls_R_factor_all          0.1600
_refine_ls_R_factor_gt           0.1136
_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          0.3225
_refine_ls_wR_factor_ref         0.3667
_reflns_Friedel_coverage         0.000
_reflns_number_gt                597
_reflns_number_total             909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01122d2.cif
_cod_data_source_block           C6Ph6_174GPa
_cod_depositor_comments
'Adding full bibliography for 7247910--7247915.cif.'
_cod_database_code               7247912
_chemical_oxdiff_formula         'C42 H30'
_chemical_oxdiff_usercomment
'Hexphenylbenzene at 1.74 GPa in MiTeGen LVCO-5 Cryo Oil.'
_reflns_odcompleteness_completeness 35.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     20.77
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.991(4)
 0.009(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. 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
4. 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
5.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)
5.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)
;
_shelx_res_checksum              5911
_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 3.183
_oxdiff_exptl_absorpt_empirical_full_min 0.429