Unexpected formation of α-formylated BOPHY in the reaction with copper salts
Prasannan, Dijo; Nemykin, Victor N.; New Journal of Chemistry 49 (2025) 19649–19655; doi:10.1039/D5NJ02748A

data_7064071
_publ_section_title
;
 Unexpected formation of \a-formylated BOPHY in the reaction with copper
 salts
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19649
_journal_page_last               19655
_journal_paper_doi               10.1039/D5NJ02748A
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C21 H21 B2 F4 N5 O'
_chemical_formula_sum            'C21 H21 B2 F4 N5 O'
_chemical_formula_weight         457.05
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-11
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.807(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2694(7)
_cell_length_b                   32.322(2)
_cell_length_c                   7.3866(4)
_cell_measurement_reflns_used    3396
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.47
_cell_volume                     2040.0(2)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1523
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            40713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         2.384
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1451 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.8747.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.226
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.226
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.1121
_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^)+(0.0336P)^2^+7.0229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.1970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3335
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02748a2.cif
_cod_data_source_block           tmbophy_cpd9_a
_cod_depositor_comments
'Adding full bibliography for 7064069--7064073.cif.'
_cod_database_code               7064071
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.980
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C12(H12), C14(H14), C16(H16), C19(H19), N1(H1)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              3899
_olex2_submission_special_instructions 'No special instructions were received'