Asymmetric 1,2-diaxial synthesis of bi-(hetero)aryl benzofulvene atropisomers <i>via</i> transient directing group-assisted dehydrogenative coupling.
Hore, Soumyadip; Singh, Abhijeet; Singh, Ravi P.; Chemical communications (Cambridge, England) 60 (2024) 2524–2527; doi:10.1039/d3cc06011j

data_7132691
_publ_section_title
;
 Asymmetric 1,2-diaxial synthesis of bi-(hetero)aryl benzofulvene
 atropisomers <i>via</i> transient directing group-assisted
 dehydrogenative coupling.
;
_journal_issue                   18
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2524
_journal_page_last               2527
_journal_paper_doi               10.1039/d3cc06011j
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C33 H21 F O'
_chemical_formula_sum            'C33 H21 F O'
_chemical_formula_weight         452.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-03
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-08 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.733(3)
_cell_length_b                   16.125(7)
_cell_length_c                   16.631(7)
_cell_measurement_reflns_used    8987
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      28.332
_cell_measurement_theta_min      1.759
_cell_volume                     2342.0(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      299.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            71032
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         1.759
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0719 after correction.
The Ratio of minimum to maximum transmission is 0.9422.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.094
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details
;
 Flack x determined using 1180 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         5768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0517P)^2^+0.0938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3448
_reflns_number_total             5768
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06011j2.cif
_cod_data_source_block           sxbsahvxhv_0m_a
_cod_depositor_comments          'Adding full bibliography for 7132691.cif.'
_cod_original_cell_volume        2342.0(18)
_cod_database_code               7132691
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C13(H13), C17(H17), C18(H18),
 C19(H19), C20(H20), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31), C32(H32), C33(H33)
;
_shelx_res_checksum              92698
_shelx_hkl_checksum              71374
_olex2_submission_special_instructions 'No special instructions were received'