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_7064069
_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         '1.333(C14 H14 B2 F4 N4 O)'
_chemical_formula_sum            'C18.67 H18.67 B2.67 F5.33 N5.33 O1.33'
_chemical_formula_weight         469.21
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-14
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-06-10 deposited with the CCDC.	2025-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   11.5405(7)
_cell_length_b                   9.9104(6)
_cell_length_c                   25.9429(16)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.82
_cell_volume                     2967.1(3)
_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 0.996
_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  0.0595
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            30444
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.362
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1495 before and 0.0729 after correction.
The Ratio of minimum to maximum transmission is 0.8129.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.036
_refine_diff_density_max         1.454
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0559
_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^)+(0.0629P)^2^+3.7206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3166
_reflns_number_total             3695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02748a2.cif
_cod_data_source_block           bophy_aldehyde_a
_cod_depositor_comments
'Adding full bibliography for 7064069--7064073.cif.'
_cod_database_code               7064069
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.945
_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), C6(H6), C9(H9), C14(H14)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              33482
_olex2_submission_special_instructions 'No special instructions were received'