Nickel-Catalyzed Direct Acylation of Aryl and Alkyl Bromides with Acylimidazoles
Zhuo, Junming; Zhang, Yong; Li, Zijian; Li, Chao; ACS Catalysis 10 (2020) 3895–3903; doi:10.1021/acscatal.0c00246

data_4517496
_publ_section_title
;
 Nickel-Catalyzed Direct Acylation of Aryl and Alkyl Bromides with
 Acylimidazoles
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3895
_journal_page_last               3903
_journal_paper_doi               10.1021/acscatal.0c00246
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_sum            'C39 H54 O5'
_chemical_formula_weight         602.82
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.803(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2802(6)
_cell_length_b                   7.2838(4)
_cell_length_c                   37.4807(17)
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      21.3660
_cell_measurement_theta_min      2.1750
_cell_volume                     3352.2(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            12868
_diffrn_reflns_point_group_measured_fraction_full 0.712
_diffrn_reflns_point_group_measured_fraction_max 0.620
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.377
_diffrn_reflns_theta_min         2.717
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 748 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1091
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0459P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.258
_reflns_Friedel_fraction_full    0.372
_reflns_Friedel_fraction_max     0.275
_reflns_number_gt                3656
_reflns_number_total             5715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00246_si_003.cif
_cod_data_source_block           3
_cod_depositor_comments
;Adding full bibliography for 4517495--4517497.cif.

 Adding full bibliography for 4517495--4517497.cif.
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4517496
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              88511
_shelx_hkl_checksum              84498