Copper-catalyzed condensation of imines and α-diazo-β-dicarbonyl compounds: modular and regiocontrolled synthesis of multisubstituted pyrroles
Tan, Wei Wen; Yoshikai, Naohiko; Chem. Sci. 6 (2015) 6448–; doi:10.1039/C5SC02322J

data_1529323
_publ_section_title
;
 Copper-catalyzed condensation of imines and \a-diazo-\b-dicarbonyl
 compounds: modular and regiocontrolled synthesis of multisubstituted
 pyrroles
;
_journal_issue                   11
_journal_name_full               'Chem. Sci.'
_journal_page_first              6448
_journal_paper_doi               10.1039/C5SC02322J
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C27 H23 N O3'
_chemical_formula_weight         409.46
_chemical_name_systematic
'Ethyl 1-oxo-2,10b-diphenyl-1,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinoline-3-carboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-05-05 deposited with the CCDC.
2015-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.912(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9721(5)
_cell_length_b                   14.3477(7)
_cell_length_c                   15.3171(10)
_cell_measurement_reflns_used    3355
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      28.3793
_cell_measurement_theta_min      2.5637
_cell_volume                     2096.7(2)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22285
_diffrn_reflns_theta_full        29.32
_diffrn_reflns_theta_max         29.32
_diffrn_reflns_theta_min         1.99
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate and hexane'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.340
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.524
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         5696
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0857P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1661
_reflns_number_gt                3906
_reflns_number_total             5696
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02322j2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1529322--1529323.cif.'
_cod_database_code               1529323
_shelx_res_checksum              93646
_shelx_hkl_checksum              33000