Effect of geometry factors on the priority of σ-hole⋯π and π-hole⋯π bond in phosphorescent cocrystals formed by pyrene or phenanthrene and trihaloperfluorobenzenes
Li, Lili; Wu, Wen Xin; Liu, Zheng Fei; Jin, Wei Jun; New Journal of Chemistry 42 (2018) 10633–; doi:10.1039/C7NJ04536K

data_7056867
_publ_section_title
;
 Effect of geometry factors on the priority of \s-hole&#x22EF;\p and
 \p-hole&#x22EF;\p bond in phosphorescent cocrystals formed by pyrene or
 phenanthrene and trihaloperfluorobenzenes
;
_journal_issue                   13
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10633
_journal_paper_doi               10.1039/C7NJ04536K
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'Br3 C6 F3, C16 H10'
_chemical_formula_sum            'C22 H10 Br3 F3'
_chemical_formula_weight         571.03
_chemical_name_systematic        Pyr-TBrPB
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-01-02 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.132(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8395(3)
_cell_length_b                   14.7083(4)
_cell_length_c                   17.2969(5)
_cell_measurement_reflns_used    4306
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7270
_cell_measurement_theta_min      5.7490
_cell_volume                     1949.89(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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     30.00  70.00   1.00    1.00    --   41.49-125.00-120.00   40
  2  \w     25.00  56.00   1.00    1.00    --   41.49-125.00 -60.00   31
  3  \w     83.00 109.00   1.00    1.70    --  107.52 -94.00 -60.00   26
  4  \w     40.00 108.00   1.00    1.70    --  107.52 -94.00-120.00   68
  5  \w     35.00 124.00   1.00    1.70    --  107.52 -45.00-150.00   89
  6  \w     82.00 172.00   1.00    1.70    --  107.52  30.00  30.00   90
  7  \w    102.00 131.00   1.00    1.70    --  107.52 125.00 -60.00   29
  8  \w    106.00 146.00   1.00    1.70    --  107.52 125.00 -30.00   40
  9  \w     25.00  99.00   1.00    1.70    --  107.52 -94.00-180.00   74
 10  \w   -122.00  47.00   1.00    1.00    --  -41.49   0.00 120.00  169
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1729247000
_diffrn_orient_matrix_UB_12      -0.0519385000
_diffrn_orient_matrix_UB_13      -0.0059009000
_diffrn_orient_matrix_UB_21      -0.0111449000
_diffrn_orient_matrix_UB_22      0.0338150000
_diffrn_orient_matrix_UB_23      0.0831096000
_diffrn_orient_matrix_UB_31      -0.1017440000
_diffrn_orient_matrix_UB_32      0.0844569000
_diffrn_orient_matrix_UB_33      -0.0368619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7388
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.003
_diffrn_reflns_theta_min         3.983
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.945
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.560
_refine_diff_density_min         -1.133
_refine_diff_density_rms         0.146
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0824
_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^)+(0.1268P)^2^+9.2215P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3277
_reflns_number_total             3820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj04536k2.cif
_cod_data_source_block           20170607b
_cod_depositor_comments
'Adding full bibliography for 7056866--7056869.cif.'
_cod_database_code               7056867
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1f1Br1
_chemical_oxdiff_usercomment     LB-41
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8)
\\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11) \\sim Ueq,
Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C20) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C20(H20), C21(H21), C22(H22),
 C18(H18), C19(H19)
3.b Fitted hexagon refined as free rotating group:
 C7(C8,C9,C10,C11,C12), C15(C16,C17,C20,C21,C22)
;
_shelx_res_checksum              24722
_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 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.689