Zn(OAc)2-Catalyzed tandem cyclization of isocyanides, α-diazoketones, and anhydrides: a general route to polysubstituted maleimides
Liang, Yong-Xin; Meng, Xiang-He Meng; Yang, Ming; Mehfooz, Haroon; Zhao, Yu-long; Chemical Communications  (2019) –; doi:10.1039/C9CC05802H

data_7124235
_publ_section_title
;
 Zn(OAc)2-Catalyzed tandem cyclization of isocyanides, \a-diazoketones,
 and anhydrides: a general route to polysubstituted maleimides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05802H
_journal_year                    2019
_chemical_formula_sum            'C20 H17 N O6'
_chemical_formula_weight         367.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2019-07-13 deposited with the CCDC.    2019-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.52(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.524(7)
_cell_length_b                   14.474(13)
_cell_length_c                   16.108(15)
_cell_measurement_reflns_used    3350
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      3.05
_cell_volume                     1754(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10742
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.052
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1147 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(5)
_refine_ls_extinction_coef       0.0163(17)
_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   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3052
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0335
_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^)+(0.0389P)^2^+0.3945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.974
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2623
_reflns_number_total             3052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05802h2.cif
_cod_data_source_block           zhaoyl190304_1_0m
_cod_database_code               7124235
_shelxl_version_number           2014-3
_shelx_res_checksum              86141