Copper-catalyzed regioselective [3+2] annulation of malonate-tethered acyl oximes with isatins.
Duan, Jindian; Mao, Yiyang; Xian, Anmei; Rong, Binsen; Xu, Gaochen; Li, Zhenjiang; Zhao, Lili; Zhu, Ning; Guo, Kai; Chemical communications (Cambridge, England) 57 (2021) 3379–3382; doi:10.1039/d0cc07995b

data_7127988
_publ_section_title
;
 Copper-catalyzed regioselective [3+2] annulation of malonate-tethered
 acyl oximes with isatins.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3379
_journal_page_last               3382
_journal_paper_doi               10.1039/d0cc07995b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C21 H17 Cl N2 O6'
_chemical_formula_weight         428.82
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-02-24 deposited with the CCDC.	2021-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   32.8416(15)
_cell_length_b                   32.8416(15)
_cell_length_c                   9.7790(5)
_cell_measurement_reflns_used    5772
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.827
_cell_measurement_theta_min      4.405
_cell_volume                     9134.3(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.528
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             3996
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4662
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0727P)^2^+7.2360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1552
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3398
_reflns_number_total             4662
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc07995b2.cif
_cod_data_source_block           mo_dd19225_0m
_cod_depositor_comments          'Adding full bibliography for 7127988.cif.'
_cod_original_cell_volume        9134.3(10)
_cod_database_code               7127988
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.973
_shelxl_version_number           2013-4
_shelx_res_checksum              62729