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_1529322
_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            'C24 H27 N O3'
_chemical_formula_weight         377.46
_chemical_melting_point          98.5(5)
_chemical_name_systematic
'Ethyl 3-isopropyl-1-(4-methoxyphenyl)-5-(o-tolyl)-1H-pyrrole-2-carboxylate'
_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
_audit_update_record
;
2014-12-23 deposited with the CCDC.
2015-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                93.847(3)
_cell_angle_beta                 101.554(3)
_cell_angle_gamma                114.578(3)
_cell_formula_units_Z            4
_cell_length_a                   11.3191(5)
_cell_length_b                   11.4640(5)
_cell_length_c                   18.1291(7)
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      25.2899
_cell_measurement_theta_min      2.6835
_cell_volume                     2065.90(17)
_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 (Sheldrick, 2014)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0615
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38462
_diffrn_reflns_theta_full        28.47
_diffrn_reflns_theta_max         28.47
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and EtOAc'
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.436
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         10388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0941P)^2^+0.0529P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1329
_refine_ls_wR_factor_ref         0.1745
_reflns_number_gt                6874
_reflns_number_total             10388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5sc02322j2.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '98-99' was changed to '98.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1529322--1529323.cif.
;
_cod_original_cell_volume        2065.90(16)
_cod_database_code               1529322
_shelx_res_checksum              29247
_shelx_hkl_checksum              75443