Reductive coupling of azonaphthalenes for the synthesis of BINAMs <i>via</i> a diboron-enabled [5,5]-sigmatropic rearrangement.
Qi, Liang-Wen; Twumasi, Emmanuella Bema; Li, Xiao-Wei; Li, Rui; Lu, Yixin; Chemical science 16 (2025) 1441–1446; doi:10.1039/d4sc06273f

data_1573455
_publ_section_title
;
 Reductive coupling of azonaphthalenes for the synthesis of BINAMs
 <i>via</i> a diboron-enabled [5,5]-sigmatropic rearrangement.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1441
_journal_page_last               1446
_journal_paper_doi               10.1039/d4sc06273f
_journal_volume                  16
_journal_year                    2025
_chemical_formula_sum            'C34 H22 Br2 F2 N4 O2'
_chemical_formula_weight         716.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     'Dual Space'
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2023-09-14 deposited with the CCDC.	2024-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 127.298(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8725(9)
_cell_length_b                   29.1188(18)
_cell_length_c                   9.3620(6)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.48
_cell_measurement_theta_min      3.03
_cell_volume                     3008.4(3)
_computing_cell_refinement       'APEX4 v2021.10-1 (Bruker AXS)'
_computing_data_collection       'APEX4 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL--2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXT--(Sheldrick 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            52265
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         2.293
_diffrn_source                   'Microfocus Sealed Tube'
_exptl_absorpt_coefficient_mu    2.746
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0893 before and 0.0551 after correction. 
The Ratio of minimum to maximum transmission is 0.8234. 
The \l/2 correction factor is not present. 
;
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.299
_exptl_crystal_size_mid          0.294
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.902
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     250
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0266
_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^)+(0.0280P)^2^+4.8264P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0665
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3810
_reflns_number_total             4220
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc06273f2.cif
_cod_data_source_block           N265
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'Not Measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1573455.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1573455
_shelx_shelxl_version_number     2019/1
_computing_bruker_data_scaling   'SADABS V2016/2 (Bruker AXS Inc.)'
_shelx_res_checksum              9626
_shelx_hkl_checksum              18852