Catalytic Asymmetric 1,3-Dipolar Cycloaddition/Hydroamination Sequence: Expeditious Access to Enantioenriched Pyrroloisoquinoline Derivatives.
Molina, Alba; Pascual-Escudero, Ana; Adrio, Javier; Carretero, Juan C.; The Journal of organic chemistry 82 (2017) 11238–11246; doi:10.1021/acs.joc.7b01927

data_4032918
_publ_section_title
;
 Catalytic Asymmetric 1,3-Dipolar Cycloaddition/Hydroamination Sequence:
 Expeditious Access to Enantioenriched Pyrroloisoquinoline Derivatives.
;
_journal_issue                   20
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11238
_journal_page_last               11246
_journal_paper_doi               10.1021/acs.joc.7b01927
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_sum            'C27 H30 N2 O4'
_chemical_formula_weight         446.53
_chemical_name_common            amcterbutilo
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.66(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.136(10)
_cell_length_b                   6.549(7)
_cell_length_c                   17.967(18)
_cell_measurement_reflns_used    1029
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      16.0933
_cell_measurement_theta_min      2.3550
_cell_volume                     1191(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.1435
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14139
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         1.14
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.298
_refine_ls_abs_structure_details
;

Flack x determined using 683 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         4326
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0697
_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^)+(0.0862P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1957
_reflns_number_gt                2158
_reflns_number_total             4326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01927_si_002.cif
_cod_data_source_block           02152AlbaMolina
_cod_depositor_comments          'Adding full bibliography for 4032918.cif.'
_cod_original_cell_volume        1191.(2)
_cod_database_code               4032918
_shelx_res_checksum              41215
_shelx_hkl_checksum              96325