Cu-catalyzed borylative cyclization of N-(o-alkynylaryl)imines
Zhang, Tingting; Gui, Jinhai; Mo, Yu; Pu, Yuchuan; Zhao, Hongping; Liu, Yong; He, Chengyu; Chemical Communications 61 (2025) 6799–6802; doi:10.1039/D5CC00679A

data_7134374
_publ_section_title
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 Cu-catalyzed borylative cyclization of N-(o-alkynylaryl)imines
;
_journal_issue                   37
_journal_name_full               'Chemical Communications'
_journal_page_first              6799
_journal_page_last               6802
_journal_paper_doi               10.1039/D5CC00679A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C29 H27 B F3 N O3'
_chemical_formula_sum            'C29 H27 B F3 N O3'
_chemical_formula_weight         505.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-01-09 deposited with the CCDC.	2025-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.046(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9881(4)
_cell_length_b                   13.1835(4)
_cell_length_c                   14.3886(4)
_cell_measurement_reflns_used    4714
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      68.275
_cell_measurement_theta_min      0.985
_cell_volume                     2574.10(13)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      291.0
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34191
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.279
_diffrn_reflns_theta_min         3.954
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1750 before and 0.1042 after correction.
The Ratio of minimum to maximum transmission is 0.6707.
The \l/2 correction factor is Not present.
;
_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    1.304
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1012P)^2^+1.3046P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1777
_refine_ls_wR_factor_ref         0.1881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3861
_reflns_number_total             4642
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc00679a2.cif
_cod_data_source_block           a1_gjh_0m
_cod_depositor_comments          'Adding full bibliography for 7134374.cif.'
_cod_database_code               7134374
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.792
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L),
 C00O(H00O), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X)
2.c Idealised Me refined as rotating group:
 C00Y(H00B,H00C,H00D), C00Z(H00E,H00K,H00M), C010(H01A,H01B,H01C), C011(H01D,
 H01E,H01F)
;
_shelx_res_checksum              19996
_shelx_hkl_checksum              82112
_olex2_submission_special_instructions 'No special instructions were received'