D–π–A-type fluorinated tolanes with a diphenylamino group: crystal polymorphism formation and photophysical behavior
Yamada, Shigeyuki; Kobayashi, Kazuki; Morita, Masato; Konno, Tsutomu; CrystEngComm  (2022) –; doi:10.1039/D1CE01671G

data_7244255
_publ_section_title
;
 D--\p--A-type fluorinated tolanes with a diphenylamino group: crystal
 polymorphism formation and photophysical behavior
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01671G
_journal_year                    2022
_chemical_formula_moiety         'C27 H14 F4 N2'
_chemical_formula_sum            'C27 H14 F4 N2'
_chemical_formula_weight         442.40
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                95.086(2)
_cell_angle_beta                 100.768(2)
_cell_angle_gamma                95.042(2)
_cell_formula_units_Z            4
_cell_length_a                   9.8311(3)
_cell_length_b                   10.2683(3)
_cell_length_c                   22.2426(5)
_cell_measurement_reflns_used    14614
_cell_measurement_temperature    297
_cell_measurement_theta_max      28.3310
_cell_measurement_theta_min      2.0700
_cell_volume                     2184.59(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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      5.00  31.00   0.25    3.09    --    5.00  76.00 -90.00  104
  2  \w     38.00  64.00   0.25    3.09    --    5.00  57.00 -90.00  104
  3  \w    -10.00  25.00   0.25    3.09    --    5.00  57.00-150.00  140
  4  \w    -39.00   9.00   0.25    3.09    --  -11.60  57.00 120.00  192
  5  \w    -53.00  -9.00   0.25    3.09    --  -11.60  76.00-150.00  176
  6  \w     53.00  78.00   0.25    3.09    --  -11.60  57.00 120.00  100
  7  \w    -47.00  68.00   0.25    3.09    --  -11.60  57.00  60.00  460
  8  \w    -53.00  37.00   0.25    3.09    --  -11.60  76.00 -30.00  360
  9  \w   -101.00  72.00   0.25    3.09    --  -11.60  19.00-120.00  692
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0139849000
_diffrn_orient_matrix_UB_12      0.0167823000
_diffrn_orient_matrix_UB_13      -0.0306425000
_diffrn_orient_matrix_UB_21      -0.0060254000
_diffrn_orient_matrix_UB_22      -0.0674971000
_diffrn_orient_matrix_UB_23      -0.0112661000
_diffrn_orient_matrix_UB_31      -0.0722767000
_diffrn_orient_matrix_UB_32      -0.0052289000
_diffrn_orient_matrix_UB_33      0.0003237000
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            35595
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.118
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70412
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.647
_exptl_crystal_size_mid          0.513
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         9988
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.2049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1363
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6486
_reflns_number_total             9988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01671g2.cif
_cod_data_source_block           nph2-4f-cf_kb-2(y)
_cod_database_code               7244255
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H14F4N2
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00H(H00H), C00I(H00I), C00M(H00M), C00T(H00T), C011(H011),
 C013(H013), C016(H016), C018(H018), C01A(H01A), C01C(H01C), C01D(H01D),
 C01E(H01E), C01F(H01F), C01G(H01G), C01I(H01I), C01J(H01J), C01K(H01K),
 C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O), C01P(H01P), C01Q(H01Q),
 C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U)
;
_shelx_res_checksum              34175
_shelx_hkl_checksum              69996
_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.364