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_7244256
_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 H18 N2'
_chemical_formula_sum            'C27 H18 N2'
_chemical_formula_weight         370.43
_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                76.568(3)
_cell_angle_beta                 78.786(4)
_cell_angle_gamma                73.558(4)
_cell_formula_units_Z            2
_cell_length_a                   7.6818(4)
_cell_length_b                   9.1974(3)
_cell_length_c                   15.4502(5)
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    297
_cell_measurement_theta_max      26.7250
_cell_measurement_theta_min      2.4370
_cell_volume                     1008.58(7)
_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      8.00  33.00   0.25    0.80    --    5.00  57.00 -60.00  100
  2  \w     10.00  67.00   0.25    0.80    --    5.00  19.00 150.00  228
  3  \w    -60.00 -33.00   0.25    0.80    --    5.00  19.00 150.00  108
  4  \w    -53.00  49.00   0.25    0.80    --  -11.60  76.00-120.00  408
  5  \w    -52.00  47.00   0.25    0.80    --  -11.60  76.00   0.00  396
  6  \w    -53.00  16.00   0.25    0.80    --  -11.60  76.00 120.00  276
  7  \w     48.00  75.00   0.25    0.80    --  -11.60  57.00-180.00  108
  8  \w    -44.00 -18.00   0.25    0.80    --  -11.60  76.00 -90.00  104
  9  \w    -15.00  12.00   0.25    0.80    --  -11.60  76.00 -90.00  108
 10  \w    -44.00   7.00   0.25    0.80    --  -11.60  57.00-180.00  204
;
_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      0.0156967000
_diffrn_orient_matrix_UB_12      0.0534758000
_diffrn_orient_matrix_UB_13      -0.0400910000
_diffrn_orient_matrix_UB_21      -0.0331315000
_diffrn_orient_matrix_UB_22      0.0613724000
_diffrn_orient_matrix_UB_23      0.0242140000
_diffrn_orient_matrix_UB_31      0.0900225000
_diffrn_orient_matrix_UB_32      -0.0087778000
_diffrn_orient_matrix_UB_33      0.0088015000
_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  0.0192
_diffrn_reflns_av_unetI/netI     0.0203
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14254
_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         27.478
_diffrn_reflns_theta_min         2.351
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89228
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.681
_exptl_crystal_size_mid          0.404
_exptl_crystal_size_min          0.283
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.061(5)
_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   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0547P)^2^+0.0543P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1201
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3275
_reflns_number_total             4588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01671g2.cif
_cod_data_source_block           nph2-4h-cn_kb5
_cod_original_cell_volume        1008.58(8)
_cod_database_code               7244256
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C27H18N2
_reflns_odcompleteness_completeness 99.59
_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:
 C007(H007), C008(H008), C00A(H00A), C00C(H00C), C00D(H00D), C00G(H00G),
 C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
;
_shelx_res_checksum              38182
_shelx_hkl_checksum              20120
_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 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.669