Copper-catalyzed domino reaction to construct functionalized indolizinones
Wang, Li-Xia; hu, benquan; shen, gang; Tang, Yalin; Yang, Luo; RSC Adv.  (2015) –; doi:10.1039/C5RA20119E

data_7223220
_publ_section_title
;
 Copper-catalyzed domino reaction to construct functionalized
 indolizinones
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA20119E
_journal_year                    2015
_chemical_formula_moiety
'C22 H20 Cu N4 O4, 2(C4 H8 O2), 2(C2 H3 O2), 2(H2 O)'
_chemical_formula_sum            'C34 H46 Cu N4 O14'
_chemical_formula_weight         798.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-09-29 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.46(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.129(4)
_cell_length_b                   7.8255(16)
_cell_length_c                   24.473(5)
_cell_measurement_reflns_used    5525
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4677
_cell_measurement_theta_min      1.9281
_cell_volume                     3683.3(15)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
scan:
    Number of images: 300
               Slice: -110.0000 - 40.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9633
              2theta: -20.0739
scan:
    Number of images: 330
               Slice: -110.0000 - 55.0000
         Image width: 0.5000
            Exp time: 5.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9633
              2theta: -20.0739
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0428
_diffrn_orient_matrix_UB_12      -0.0176
_diffrn_orient_matrix_UB_13      -0.0237
_diffrn_orient_matrix_UB_21      0.0666
_diffrn_orient_matrix_UB_22      -0.0171
_diffrn_orient_matrix_UB_23      -0.1077
_diffrn_orient_matrix_UB_31      -0.0062
_diffrn_orient_matrix_UB_32      -0.0443
_diffrn_orient_matrix_UB_33      0.0032
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12728
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_min         2.150
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5678
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       block
_exptl_crystal_F_000             1676
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0945
_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^)+(0.0451P)^2^+38.4406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2122
_refine_ls_wR_factor_ref         0.2145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3987
_reflns_number_total             4204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra20119e2.cif
_cod_data_source_block           mx3864
_cod_database_code               7223220
_diffrn_number_total             4515
_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, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O2-H2
 0.85 with sigma of 0.01
 C6-H2
 1.878816 with sigma of 0.02
 Cu1-H2
 3.226193 with sigma of 0.02
3.a Free rotating group:
 O5(H5A,H5B)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C14(H14A,H14B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              28661
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'