Copper-catalyzed propargylic substitution for the highly selective construction of multi-substituted 1,4-enynes
Li, Yuntao; Wang, Xu; Li, Anqi; Zhao, Jixing; Li, Shi-Wu; Yang, Shengwen; Zhao, Zhifei; New Journal of Chemistry 50 (2026) 4543–4549; doi:10.1039/D6NJ00029K

data_7064241
_publ_section_title
;
 Copper-catalyzed propargylic substitution for the highly selective
 construction of multi-substituted 1,4-enynes
;
_journal_issue                   10
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              4543
_journal_page_last               4549
_journal_paper_doi               10.1039/D6NJ00029K
_journal_volume                  50
_journal_year                    2026
_chemical_formula_moiety         'C18 H16 Br N'
_chemical_formula_sum            'C18 H16 Br N'
_chemical_formula_weight         326.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-10-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2025-12-01 deposited with the CCDC.	2026-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.831(3)
_cell_angle_beta                 95.528(3)
_cell_angle_gamma                95.559(3)
_cell_formula_units_Z            2
_cell_length_a                   5.8713(5)
_cell_length_b                   9.6203(9)
_cell_length_c                   13.4415(12)
_cell_measurement_reflns_used    7745
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.20
_cell_measurement_theta_min      4.62
_cell_volume                     751.92(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8691
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.228
_diffrn_reflns_theta_min         4.619
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.618
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.4430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0538 after correction.
The Ratio of minimum to maximum transmission is 0.5878.
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    1.441
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.117
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0410P)^2^+0.3598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2811
_reflns_number_total             2884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6nj00029k2.cif
_cod_data_source_block           11
_cod_depositor_comments          'Adding full bibliography for 7064241.cif.'
_cod_database_code               7064241
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.517
_shelx_estimated_absorpt_t_min   0.465
_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 Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
2.d :
 C12(H12)
;
_shelx_res_checksum              68060
_olex2_submission_special_instructions 'No special instructions were received'