Highly Atroposelective Synthesis of Arylpyrroles by Catalytic Asymmetric Paal-Knorr Reaction.
Zhang, Lei; Zhang, Jian; Ma, Ji; Cheng, Dao-Juan; Tan, Bin; Journal of the American Chemical Society 139 (2017) 1714–1717; doi:10.1021/jacs.6b09634

data_4125717
_publ_section_title
;
 Highly Atroposelective Synthesis of Arylpyrroles by Catalytic Asymmetric
 Paal-Knorr Reaction.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1714
_journal_page_last               1717
_journal_paper_doi               10.1021/jacs.6b09634
_journal_volume                  139
_journal_year                    2017
_chemical_formula_moiety         'C31 H30 Br N O2'
_chemical_formula_sum            'C31 H30 Br N O2'
_chemical_formula_weight         528.47
_space_group_crystal_system      orthorhombic
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_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
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_cell_length_b                   11.813(2)
_cell_length_c                   24.565(6)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    566(2)
_cell_measurement_theta_max      67.8
_cell_measurement_theta_min      22.9
_cell_volume                     3384.0(11)
_computing_cell_refinement
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_collection
;
CrysAlis Pro (Agilent, 2013)
;
_computing_data_reduction
;
CrysAlis Pro (Agilent, 2013)
;
_computing_molecular_graphics    '(K. Brandenburg, Diamond 3.1, 2009)'
_computing_publication_material  '(K. Brandenburg, Diamond 3.1, 2009)'
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_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      566(2)
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.710
_diffrn_reflns_av_R_equivalents  0.055
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            5721
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.656
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.236
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.357
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5721
_refine_ls_number_restraints     144
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0814
_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^)+(0.1295P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2243
_refine_ls_wR_factor_ref         0.2436
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3425
_reflns_number_total             5721
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09634_si_002.cif
_cod_data_source_block           3fa
_cod_original_cell_volume        3383.9(11)
_cod_database_code               4125717
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.781
_shelx_estimated_absorpt_t_max   0.817
_exptl_absorpt_special_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_shelx_res_checksum              51934
_shelx_hkl_checksum              78523