Syntheses of heterotriptycenes and their Pt complexes that emit circularly polarised fluorescence and phosphorescence.
Inoue, Ryo; Furumoto, Kyosuke; Morisaki, Yasuhiro; Chemical communications (Cambridge, England) 59 (2023) 5571–5574; doi:10.1039/d3cc01190a

data_7131543
_publ_section_title
;
 Syntheses of heterotriptycenes and their Pt complexes that emit
 circularly polarised fluorescence and phosphorescence.
;
_journal_issue                   37
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5571
_journal_page_last               5574
_journal_paper_doi               10.1039/d3cc01190a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Br, C29 H21 F N O4'
_chemical_formula_sum            'C29 H21 Br F N O4'
_chemical_formula_weight         546.38
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-21
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-04 deposited with the CCDC.	2023-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   12.0615(7)
_cell_length_b                   14.3870(9)
_cell_length_c                   61.506(3)
_cell_measurement_reflns_used    7019
_cell_measurement_temperature    150
_cell_measurement_theta_max      29.8200
_cell_measurement_theta_min      2.2050
_cell_volume                     10673.1(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.940
_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   -110.00  70.00   0.50   40.00    --  -20.00  45.00   0.00  360
  2  \w   -110.00  -9.00   0.50   40.00    --  -20.00  45.00  90.00  202
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0074390000
_diffrn_orient_matrix_UB_12      -0.0023097000
_diffrn_orient_matrix_UB_13      0.0114249000
_diffrn_orient_matrix_UB_21      0.0499765000
_diffrn_orient_matrix_UB_22      -0.0251577000
_diffrn_orient_matrix_UB_23      -0.0015460000
_diffrn_orient_matrix_UB_31      0.0301256000
_diffrn_orient_matrix_UB_32      0.0423054000
_diffrn_orient_matrix_UB_33      -0.0002721000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1571
_diffrn_reflns_av_unetI/netI     0.2802
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       84
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_number            39313
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.150
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             4448
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.685
_refine_diff_density_min         -1.091
_refine_diff_density_rms         0.158
_refine_ls_abs_structure_details
;
 Flack x determined using 1703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(11)
_refine_ls_extinction_coef       0.00056(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         15536
_refine_ls_number_restraints     864
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.2175
_refine_ls_R_factor_gt           0.1201
_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^)+(0.1023P)^2^+7.6460P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2296
_refine_ls_wR_factor_ref         0.2761
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                7382
_reflns_number_total             15536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01190a2.cif
_cod_data_source_block           20230209-pydmadff2-hbr
_cod_depositor_comments
'Adding full bibliography for 7131542--7131543.cif.'
_cod_original_cell_volume        10673.1(11)
_cod_database_code               7131543
_shelx_shelxl_version_number     2019/2
_chemical_oxdiff_formula         C29H21NO4BrF
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.925
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C01M \\sim C01P \\sim C016 \\sim C01K \\sim C01Z \\sim C01A: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C00I \\sim C011 \\sim C01J \\sim C01S \\sim C01T \\sim C01U: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
O005 \\sim O00C \\sim C018 \\sim C01H: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
N00F \\sim C00K \\sim C00Q \\sim C00T \\sim C014 \\sim C00L: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
N00A \\sim C00D \\sim C00M \\sim C7 \\sim C01L \\sim C11: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C12 \\sim C00M: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
N00F \\sim C00K \\sim C00L \\sim C00Q \\sim C00T \\sim C014: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
C01D \\sim O006 \\sim C01E: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 1.7A
C01J \\sim C8 \\sim C7: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 1.7A
C12 \\sim C2 \\sim C1 \\sim C15 \\sim C00O \\sim C00R: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(C01U) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.05
Uanis(O007) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C01H) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C00K) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C01D) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C017) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C00H, C00J, C00X, C013, C01I, C01N
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00F, C00Q, C00T, C014, C00L, C00K
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01A, C01P, C01Z, C01K, C01M, C016
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C016, C01A, C01K, C01M, C01P, C01Z
 with sigma for 1-2 distances of 0.008 and sigma for 1-3 distances of 0.008
 C00T, C00X, C013, C014, C019, C01M, C01P, C01V
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C017, C01U
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00S, C9, C10, C00P, C00N, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01K, C01M, C01P, C01Z, C01A, C016
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C00I, C011, C01J, C01S, C01T, C01U
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O007, O008, C017
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C010, C020, C01C, C00G, C01Q, C01R
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C01H, O005
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O00C, C018, C01H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00K, C00L, C00G, N00F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00A, C00D, C00M, C7, C11, C01L
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00M, N00A, C00D, C7, C01L, C11
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C00M
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N00F, C00K, C00Q, C014, C00L, C00T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00K, C00L, C00Q, N00F, C00T, C014
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N00A, C00D, C00M, C7, C01L, C11
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C01D, O006, C01E
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C00K, C00L, N00F, C00Q, C014, C00T
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C00K, C00G
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C00G, C00K, N00F, C00L
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8, C01J, C7
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C8, C01J, C9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C2, C12, C00R, C15, C00O, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Br01, Br02, F003, F004, O005, O006, O007, O008, O009, N00A, H00A, O00B, O00C,
 C00D, H00D, O00E, N00F, H00F, C00G, C00H, H00H, C00I, H00I, C00J, C00K, C00L,
 H00L, C00M, C00N, H00N, C00O, C00P, H00P, C00Q, H00Q, C00R, H00R, C00S, C00T,
 C5, H5, C6, H6, C7, C00X, C8, H8, C00Z, C010, H010, C011, H011, C9, C013, C014,
  C1, H1, C016, H016, C017, C018, C019, H019, C01A, H01G, C2, H2, C01C, C01D,
 H01H, H01I, H01J, C01E, C12, C10, H10, C01H, H01K, H01M, H01N, C01I, H01O,
 C01J, C01K, H01P, C01L, H01L, C01M, C01N, C11, C01P, C01Q, H01Q, C01R, H01R,
 C01S, C01T, C01U, C01V, H01V, C01W, H01A, H01B, H01C, C15, H15, C01Y, H01D,
 H01E, H01F, C01Z, H01Z, C020, H020
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C017, O008, C01U, O007
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C019(H019), C01V(H01V)
4.b Aromatic/amide H refined with riding coordinates:
 N00A(H00A), C00D(H00D), N00F(H00F), C00H(H00H), C00I(H00I), C00L(H00L),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C6(H6), C010(H010), C011(H011),
  C1(H1), C016(H016), C01A(H01G), C2(H2), C10(H10), C01I(H01O), C01K(H01P),
 C01L(H01L), C01Q(H01Q), C01R(H01R), C15(H15), C01Z(H01Z), C020(H020)
4.c Idealised Me refined as rotating group:
 C01D(H01H,H01I,H01J), C01H(H01K,H01M,H01N), C01W(H01A,H01B,H01C), C01Y(H01D,
 H01E,H01F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              73281
_shelx_hkl_checksum              16206
_shelx_fab_checksum              59746
_olex2_exptl_crystal_mounting_method fiber
_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 3.566
_oxdiff_exptl_absorpt_empirical_full_min 0.637