Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles.
Xie, Jialin; Huang, Yuanqiong; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin; Organic letters 19 (2017) 6056–6059; doi:10.1021/acs.orglett.7b02767

data_1547841
_publ_section_title
;
 Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization
 Cascade Reaction: Atom-Economical Access to Tetrasubstituted
 4,5-Biscarbonyl Imidazoles.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              6056
_journal_page_last               6059
_journal_paper_doi               10.1021/acs.orglett.7b02767
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C23 H24 N2 O5'
_chemical_formula_sum            'C23 H24 N2 O5'
_chemical_formula_weight         408.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-16
_audit_creation_method
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Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
????
;
_cell_angle_alpha                61.574(8)
_cell_angle_beta                 78.040(13)
_cell_angle_gamma                87.766(14)
_cell_formula_units_Z            2
_cell_length_a                   10.0991(16)
_cell_length_b                   10.6816(13)
_cell_length_c                   11.0208(11)
_cell_measurement_reflns_used    3044
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     1020.4(2)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_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      133.15
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13101
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.584
_diffrn_reflns_theta_min         3.102
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4628
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0943P)^2^+0.3602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1608
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             4628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02767_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 1547841.cif.'
_cod_database_code               1547841
_shelx_shelxl_version_number     2014/8
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.963
_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 Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              79650
_shelx_hkl_checksum              49426
_olex2_submission_special_instructions 'No special instructions were received'