Multicomponent and multicatalytic asymmetric synthesis of furo[2,3-b]pyrrole derivatives: further insights into the mode of action of chiral phosphoric acid catalysts
Cala, Lara; Villar, Pedro; de Lera, Ángel R.; Fañanás, Francisco J.; Álvarez, Rosana; Rodríguez, Félix; Chemical Science  (2020) –; doi:10.1039/D0SC03342A

data_1558872
_publ_section_title
;
 Multicomponent and multicatalytic asymmetric synthesis of
 furo[2,3-b]pyrrole derivatives: further insights into the mode of action
 of chiral phosphoric acid catalysts
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03342A
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H24 Cl1 N3 O6'
_chemical_formula_sum            'C23 H24 Cl N3 O6'
_chemical_formula_weight         473.9
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1p160y
_audit_creation_date             2017-02-20T13:36:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2017-05-16 deposited with the CCDC.	2020-08-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.46480(10)
_cell_length_b                   15.9282(2)
_cell_length_c                   16.6678(2)
_cell_measurement_reflns_used    11023
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      69.639
_cell_measurement_theta_min      5.239
_cell_measurement_wavelength     1.5418
_cell_volume                     2247.30(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.264
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0704075
_diffrn_orient_matrix_UB_12      0.014925
_diffrn_orient_matrix_UB_13      0.0840178
_diffrn_orient_matrix_UB_21      -0.1643725
_diffrn_orient_matrix_UB_22      0.0129091
_diffrn_orient_matrix_UB_23      -0.0376597
_diffrn_orient_matrix_UB_31      -0.0337639
_diffrn_orient_matrix_UB_32      -0.0947008
_diffrn_orient_matrix_UB_33      0.0080565
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13091
_diffrn_reflns_theta_full        69.67
_diffrn_reflns_theta_max         69.67
_diffrn_reflns_theta_min         5.31
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.899
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.84612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.002(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0374P)^2^+0.2981P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                4006
_reflns_number_total             4087
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            d0sc03342a2.cif
_cod_data_source_block           17013_lc1940ef1
_cod_database_code               1558872