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_7064070
_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         'C14 H15 B F2 N4 O'
_chemical_formula_sum            'C14 H15 B F2 N4 O'
_chemical_formula_weight         304.11
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-11
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-16 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.939(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5311(4)
_cell_length_b                   20.6790(12)
_cell_length_c                   9.2357(4)
_cell_measurement_reflns_used    4797
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.77
_cell_measurement_theta_min      2.45
_cell_volume                     1416.74(13)
_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 D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21068
_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         26.729
_diffrn_reflns_theta_min         2.446
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1441 before and 0.0750 after correction.
The Ratio of minimum to maximum transmission is 0.9218.
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    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.096
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0418P)^2^+0.9107P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1171
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2279
_reflns_number_total             3005
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02748a2.cif
_cod_data_source_block           mo_dijo_tmbophy_alkyne_frn_2_r_a
_cod_depositor_comments
'Adding full bibliography for 7064069--7064073.cif.'
_cod_database_code               7064070
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.983
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              54384
_olex2_submission_special_instructions 'No special instructions were received'