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_4517497
_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 rm
_chemical_formula_moiety         'C22 H32 O4'
_chemical_formula_sum            'C22 H32 O4'
_chemical_formula_weight         360.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 100.70(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9236(12)
_cell_length_b                   13.586(3)
_cell_length_c                   12.496(3)
_cell_measurement_reflns_used    3016
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      27.8784
_cell_measurement_theta_min      1.6585
_cell_volume                     988.2(4)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      113.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0901
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11979
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.853
_diffrn_reflns_theta_min         2.236
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       prism
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1098 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0447
_refine_ls_shift/su_max          0.130
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3102
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00246_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;Adding full bibliography for 4517495--4517497.cif.

 Adding full bibliography for 4517495--4517497.cif.
;
_cod_original_cell_volume        988.1(4)
_cod_database_code               4517497
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              41009
_shelx_hkl_checksum              3508
_olex2_submission_special_instructions 'No special instructions were received'