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_4517495
_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_moiety         'C27 H34 O3'
_chemical_formula_sum            'C27 H34 O3'
_chemical_formula_weight         406.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4470(2)
_cell_length_b                   14.6245(4)
_cell_length_c                   19.8929(5)
_cell_measurement_reflns_used    7318
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      29.2080
_cell_measurement_theta_min      2.4690
_cell_volume                     2166.51(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0233
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15686
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58878
_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    1.246
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4910
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0554P)^2^+0.2269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0945
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                4491
_reflns_number_total             4910
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs0c00246_si_002.cif
_cod_data_source_block           3
_cod_depositor_comments
;Adding full bibliography for 4517495--4517497.cif.

 Adding full bibliography for 4517495--4517497.cif.
;
_cod_database_code               4517495
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.065) H1B(0.065) H1C(0.065) H3(0.033) H4(0.032) H6(0.031)
 H7(0.031) H9(0.03) H10A(0.039) H10B(0.039) H11A(0.038) H11B(0.038) H12(0.026)
 H14A(0.042) H14B(0.042) H14C(0.042) H15A(0.03) H15B(0.03) H16A(0.03)
 H16B(0.03) H17(0.024) H18(0.026) H19A(0.032) H19B(0.032) H20A(0.033)
 H20B(0.033) H23A(0.041) H23B(0.041) H23C(0.041) H24A(0.032) H24B(0.032)
 H25A(0.037) H25B(0.037) H27(0.032)
 Fixed X: H1A(1.0431) H1B(1.1644) H1C(1.1445) H3(0.6606) H4(0.4275) H6(0.6616)
 H7(0.9001) H9(0.3799) H10A(0.0808) H10B(0.0511) H11A(0.0154) H11B(0.0101)
 H12(0.314) H14A(0.204) H14B(0.3363) H14C(0.4037) H15A(0.6143) H15B(0.6521)
 H16A(0.7283) H16B(0.5846) H17(0.5158) H18(0.2365) H19A(0.0451) H19B(0.211)
 H20A(0.1254) H20B(0.1253) H23A(0.3401) H23B(0.4632) H23C(0.544) H24A(0.7779)
 H24B(0.7367) H25A(0.7035) H25B(0.8491) H27(0.3468)
 Fixed Y: H1A(0.0841) H1B(0.11) H1C(0.1781) H3(0.2573) H4(0.3193) H6(0.2399)
 H7(0.1795) H9(0.2459) H10A(0.231) H10B(0.3317) H11A(0.2794) H11B(0.382)
 H12(0.2814) H14A(0.4722) H14B(0.5145) H14C(0.4923) H15A(0.3128) H15B(0.3986)
 H16A(0.4282) H16B(0.4978) H17(0.347) H18(0.4623) H19A(0.3581) H19B(0.3001)
 H20A(0.3902) H20B(0.4785) H23A(0.5758) H23B(0.6077) H23C(0.5961) H24A(0.4974)
 H24B(0.4015) H25A(0.5705) H25B(0.4959) H27(0.4057)
 Fixed Z: H1A(0.8753) H1B(0.9369) H1C(0.8765) H3(0.9754) H4(0.915) H6(0.7432)
 H7(0.8032) H9(0.7024) H10A(0.7072) H10B(0.7331) H11A(0.6039) H11B(0.6286)
 H12(0.5871) H14A(0.6976) H14B(0.6448) H14C(0.7177) H15A(0.6279) H15B(0.6732)
 H16A(0.5589) H16B(0.5852) H17(0.5005) H18(0.5469) H19A(0.4923) H19B(0.4687)
 H20A(0.3787) H20B(0.4234) H23A(0.4863) H23B(0.4268) H23C(0.499) H24A(0.4572)
 H24B(0.4256) H25A(0.3571) H25B(0.3416) H27(0.3015)
;
_olex2_submission_special_instructions 'No special instructions were received'