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_7056869
_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         'C6 F3 I3, 0.5(C14 H10)'
_chemical_formula_sum            'C13 H5 F3 I3'
_chemical_formula_weight         598.87
_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
_audit_creation_date             2017-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-11-16 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.930(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7866(4)
_cell_length_b                   24.3582(14)
_cell_length_c                   9.1687(5)
_cell_measurement_reflns_used    5899
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      29.6280
_cell_measurement_theta_min      3.8360
_cell_volume                     1492.97(15)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_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    -20.00  34.00   1.00    2.55    --   12.76 -37.00  90.00   54
  2  \w    -20.00  72.00   1.00    2.55    --   12.76  77.00  30.00   92
  3  \w     37.00 101.00   1.00    2.55    --   12.76 178.00 -60.00   64
  4  \w     48.00  74.00   1.00    2.55    --   12.76 178.00  90.00   26
  5  \w    -60.00  34.00   1.00    2.55    --   12.76 -77.00 -90.00   94
  6  \w    -19.00   6.00   1.00    2.55    --  -11.04 -99.00-120.00   25
;
_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      -0.0279915000
_diffrn_orient_matrix_UB_12      -0.0269645000
_diffrn_orient_matrix_UB_13      0.0174356000
_diffrn_orient_matrix_UB_21      -0.0759321000
_diffrn_orient_matrix_UB_22      -0.0000142000
_diffrn_orient_matrix_UB_23      -0.0637042000
_diffrn_orient_matrix_UB_31      0.0684529000
_diffrn_orient_matrix_UB_32      -0.0110243000
_diffrn_orient_matrix_UB_33      -0.0425822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.345
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70307
_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            colourless
_exptl_crystal_density_diffrn    2.664
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.375
_refine_diff_density_min         -1.435
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     120
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0123P)^2^+2.0149P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0477
_refine_ls_wR_factor_ref         0.0508
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3351
_reflns_number_total             3851
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj04536k2.cif
_cod_data_source_block           20170718c
_cod_depositor_comments
'Adding full bibliography for 7056866--7056869.cif.'
_cod_database_code               7056869
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c1h1f1i1
_chemical_oxdiff_usercomment     1
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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(C18) \\sim Ueq,
Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: C7(0.5) C8(0.5) H8(0.5) C9(0.5) H9(0.5) C10(0.5) H10(0.5) C11(0.5)
 H11(0.5) C12(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_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 1.476
_oxdiff_exptl_absorpt_empirical_full_min 0.798