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_7244254
_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      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
_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                90
_cell_angle_beta                 97.476(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1660(3)
_cell_length_b                   21.8984(7)
_cell_length_c                   13.6849(4)
_cell_measurement_reflns_used    11420
_cell_measurement_temperature    297
_cell_measurement_theta_max      29.2970
_cell_measurement_theta_min      2.3420
_cell_volume                     2129.23(13)
_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      7.00  32.00   0.25    2.58    --    5.00  51.00-158.00  100
  2  \w     11.00  61.00   0.25    2.58    --  -11.60  51.00-158.00  200
  3  \w     -6.00  20.00   0.25    2.58    --    5.00  57.00-150.00  104
  4  \w     29.00  87.00   0.25    2.58    --    5.00  38.00  60.00  232
  5  \w    -35.00  -9.00   0.25    2.58    --    5.00  38.00  60.00  104
  6  \w    -41.00  78.00   0.25    2.58    --  -11.60  57.00 120.00  476
  7  \w     53.00  78.00   0.25    2.58    --  -11.60  57.00 -90.00  100
  8  \w    -47.00  19.00   0.25    2.58    --  -11.60  57.00 -90.00  264
;
_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      0.0174082000
_diffrn_orient_matrix_UB_12      -0.0124123000
_diffrn_orient_matrix_UB_13      -0.0458389000
_diffrn_orient_matrix_UB_21      0.0871338000
_diffrn_orient_matrix_UB_22      0.0157897000
_diffrn_orient_matrix_UB_23      0.0039790000
_diffrn_orient_matrix_UB_31      0.0455536000
_diffrn_orient_matrix_UB_32      -0.0253937000
_diffrn_orient_matrix_UB_33      0.0248391000
_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  0.0213
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23064
_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         2.390
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44656
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.629
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.151
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.117
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0076(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0376
_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^)+(0.0476P)^2^+0.1953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3638
_reflns_number_total             4858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01671g2.cif
_cod_data_source_block           nph2-4f-cn_kb-3(o)_2
_cod_database_code               7244254
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H14F4N2
_reflns_odcompleteness_completeness 99.58
_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:
 C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K),
 C00N(H00N), C00O(H00O), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X)
;
_shelx_res_checksum              12979
_shelx_hkl_checksum              44806
_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 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.442