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_7247910
_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                   11.9478(13)
_cell_length_b                   11.6849(13)
_cell_length_c                   19.94(2)
_cell_measurement_pressure       570000
_cell_measurement_reflns_used    2281
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      20.7690
_cell_measurement_theta_min      3.4020
_cell_volume                     2784(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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_pressure         570000
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'Hybrid photon'
_diffrn_detector_type            HyPix-6000HE
_diffrn_measured_fraction_theta_full 0.473
_diffrn_measured_fraction_theta_max 0.473
_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  100.00    --   17.95  15.00   0.00   50
  2  \w     -1.00  26.00   0.50  100.00    --   17.95  40.00 -12.00   54
  3  \w    -18.00  10.00   0.50  100.00    --   17.95  82.00 -29.00   56
  4  \w    -34.00  -9.00   0.50  100.00    --  -18.26  77.00 -30.00   50
  5  \w    -21.00  11.00   0.50  100.00    --  -18.26  40.00 -12.00   64
  6  \w    -22.00   3.00   0.50  100.00    --  -18.26  15.00   0.00   50
  7  \w    -53.00 -28.00   0.50  100.00    --   17.95 112.00 135.00   50
  8  \w    -68.00 -43.00   0.50  100.00    --  -18.26 112.00 135.00   50
  9  \w     68.00  93.00   0.50  100.00    --   17.95 178.00  90.00   50
 10  \w    -32.00  -7.00   0.50  100.00    --   17.95 -15.00-169.00   50
 11  \w    -32.00  -7.00   0.50  100.00    --  -18.26 -15.00-169.00   50
 12  \w     14.00  43.00   0.50  100.00    --  -18.26 -38.00-180.00   58
 13  \w      6.00  32.00   0.50  100.00    --  -18.26 -53.00-162.00   52
 14  \w     23.00  48.00   0.50  100.00    --   17.95-112.00  42.00   50
 15  \w     71.00  96.00   0.50  100.00    --   17.95-178.00  90.00   50
;
_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      -0.0009727000
_diffrn_orient_matrix_UB_12      -0.0011796000
_diffrn_orient_matrix_UB_13      -0.0352674000
_diffrn_orient_matrix_UB_21      -0.0584546000
_diffrn_orient_matrix_UB_22      0.0119452000
_diffrn_orient_matrix_UB_23      0.0004630000
_diffrn_orient_matrix_UB_31      0.0116707000
_diffrn_orient_matrix_UB_32      0.0597622000
_diffrn_orient_matrix_UB_33      -0.0008814000
_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  0.0877
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.473
_diffrn_reflns_Laue_measured_fraction_max 0.473
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6454
_diffrn_reflns_point_group_measured_fraction_full 0.438
_diffrn_reflns_point_group_measured_fraction_max 0.438
_diffrn_reflns_theta_full        18.836
_diffrn_reflns_theta_max         18.836
_diffrn_reflns_theta_min         3.410
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51797
_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    1.276
_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         0.335
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 262 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   1.547
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     85
_refine_ls_number_reflns         958
_refine_ls_number_restraints     95
_refine_ls_restrained_S_all      1.573
_refine_ls_R_factor_all          0.1403
_refine_ls_R_factor_gt           0.1108
_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          0.3120
_refine_ls_wR_factor_ref         0.3642
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.399
_reflns_Friedel_fraction_max     0.399
_reflns_number_gt                753
_reflns_number_total             958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01122d2.cif
_cod_data_source_block           C6Ph6_057GPa
_cod_depositor_comments
'Adding full bibliography for 7247910--7247915.cif.'
_cod_original_cell_volume        2783(3)
_cod_database_code               7247910
_chemical_oxdiff_formula         'C42 H36'
_chemical_oxdiff_usercomment
'Hexphenylbenzene at 0.57 GPa in MiTeGen LVCO-5 Cryo Oil.'
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.981
_reflns_odcompleteness_completeness 32.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     23.21
_olex2_refinement_description
;
1. Fixed Uiso
 At 1 times of:
  H14 of C14, H16 of C16, H15 of C15, H17 of C17, H21 of C21, H23 of C23, H20
  of C20, H22 of C22, H18 of C18, H40 of C40, H9 of C9, H42 of C42, H39 of C39,
  H41 of C41, H10 of C10, H38 of C38, H8 of C8, H30 of C30, H26 of C26, H28 of
  C28, H29 of C29, H27 of C27, H33 of C33, H34 of C34, H32 of C32, H35 of C35,
  H36 of C36, H12 of C12, H11 of C11
 At 1.2 times of:
  H24 of C24
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
 C19, C25, C31, C37, C7, C1, C2, C3, C5, C4, C6, C13
 with sigma of 0.1
 C13, C18, C17, C16, C15, C14
 with sigma of 0.1
 C19, C20, C21, C22, C23, C24
 with sigma of 0.1
 C25, C30, C29, C28, C27, C26
 with sigma of 0.1
 C31, C36, C35, C34, C33, C32
 with sigma of 0.1
 C42, C37, C38, C39, C40, C41
 with sigma of 0.1
 C7, C12, C11, C10, C9, C8
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C16 \\sim C17 \\sim C18 \\sim C13 \\sim C14 \\sim C15: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C21 \\sim C20 \\sim C19 \\sim C24 \\sim C23 \\sim C22: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C37 \\sim C38 \\sim C39 \\sim C40 \\sim C41 \\sim C42: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C1: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 C25, C30, C29, 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, C42, C37, C38, C39, C40, C41, C28, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Aromatic/amide H refined with riding coordinates:
 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), C42(H42), C38(H38), C39(H39), C40(H40), C41(H41)
6.b Fitted hexagon refined as free rotating group:
 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),
 C42(C37,C38,C39,C40,C41)
;
_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 3.237
_oxdiff_exptl_absorpt_empirical_full_min 0.553