Mechanochemical one-pot Barbier/Simmons-Smith reaction <i>via</i> sequential zinc activation.
Alharthi, Asma A.; Kariuki, Benson M.; Morrill, Louis C.; Browne, Duncan L.; Chemical communications (Cambridge, England) 62 (2026) 1864–1868; doi:10.1039/d5cc05732a

data_7135521
_publ_section_title
;
 Mechanochemical one-pot Barbier/Simmons-Smith reaction <i>via</i>
 sequential zinc activation.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1864
_journal_page_last               1868
_journal_paper_doi               10.1039/d5cc05732a
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C21 H23 N O5'
_chemical_formula_sum            'C21 H23 N O5'
_chemical_formula_weight         369.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-10 deposited with the CCDC.	2025-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.294(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   37.342(3)
_cell_length_b                   6.4577(6)
_cell_length_c                   15.8102(9)
_cell_measurement_reflns_used    807
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      67.6110
_cell_measurement_theta_min      5.6270
_cell_volume                     3796.3(5)
_computing_cell_refinement       'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_data_collection
'CrysAlisPro system (CCD 43.120a (release 16-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.120a (Rigaku OD, 2024)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 10.5082
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5495
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.836
_diffrn_reflns_theta_min         4.757
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.120a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     723
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1524
_refine_ls_R_factor_gt           0.0817
_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^)+(0.0981P)^2^+0.7241P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2358
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2568
_reflns_number_total             5495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc05732a2.cif
_cod_data_source_block           lm2503
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7135521
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.694
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              4269