Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones.
Wang, Yichen; Chen, Yuzhen; Li, Xiaoping; Mao, Yukang; Chen, Weiwen; Zhan, Ruoting; Huang, Huicai; Organic & biomolecular chemistry 17 (2019) 3945–3950; doi:10.1039/c9ob00419j

data_7156748
_publ_section_title
;
 Enantioselective synthesis of pyrano[2,3-c]pyrrole via an organocatalytic
 [4 + 2] cyclization reaction of dioxopyrrolidines and azlactones.
;
_journal_issue                   16
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3945
_journal_page_last               3950
_journal_paper_doi               10.1039/c9ob00419j
_journal_volume                  17
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C35 H29 Br N2 O5'
_chemical_formula_sum            'C35 H29 Br N2 O5'
_chemical_formula_weight         637.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.3581(2)
_cell_length_b                   25.0827(3)
_cell_length_c                   6.72000(10)
_cell_measurement_reflns_used    8611
_cell_measurement_temperature    118.4(8)
_cell_measurement_theta_max      76.0520
_cell_measurement_theta_min      2.8800
_cell_volume                     3262.92(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      118.4(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -119.00 -43.00   0.50    0.05    --  -46.37 -45.00-116.00  152
  2  \w   -119.00 -41.00   0.50    0.20    -- -102.00 168.00  43.00  156
  3  \w   -174.00-135.00   0.50    0.20    -- -102.00 -77.00  54.00   78
  4  \w    139.00 177.00   0.50    0.20    --  107.00  45.00  33.00   76
  5  \w   -107.00 -81.00   0.50    0.05    --  -46.37-125.00  30.00   52
  6  \w   -118.00 -93.00   0.50    0.05    --  -46.37-125.00   0.00   50
  7  \w     18.00  80.00   0.50    0.05    --   46.37-125.00 -90.00  124
  8  \w   -175.00 -82.00   0.50    0.20    -- -102.00 -77.00-180.00  186
  9  \w   -123.00 -78.00   0.50    0.20    -- -102.00 -77.00  54.00   90
 10  \w     44.00  69.00   0.50    0.20    --  107.00 -94.00-120.00   50
 11  \w     63.00  88.00   0.50    0.20    --  107.00 -94.00 -30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1881919000
_diffrn_orient_matrix_UB_12      0.0333961000
_diffrn_orient_matrix_UB_13      -0.0238058000
_diffrn_orient_matrix_UB_21      0.1248653000
_diffrn_orient_matrix_UB_22      -0.0297024000
_diffrn_orient_matrix_UB_23      0.0460767000
_diffrn_orient_matrix_UB_31      0.0390233000
_diffrn_orient_matrix_UB_32      -0.0658577000
_diffrn_orient_matrix_UB_33      -0.0329167000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12229
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.555
_diffrn_reflns_theta_min         2.883
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.063
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_description       needle
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.871
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0304
_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^)+(0.0250P)^2^+3.5719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.860
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                5598
_reflns_number_total             5985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob00419j2.cif
_cod_data_source_block           180913_yc01_sqd
_cod_depositor_comments          'Adding full bibliography for 7156748.cif.'
_cod_database_code               7156748
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O N Br'
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.820
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C34(H34), C27(H27), C31(H31), C20(H20), C33(H33), C16(H16), C17(H17),
 C1(H1), C19(H19), C30(H30), C26(H26), C23(H23), C25(H25), C5(H5), C24(H24),
 C2(H2A), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C35(H35A,H35B,H35C)
;
_shelx_res_checksum              42920
_shelx_hkl_checksum              10694
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.549
_oxdiff_exptl_absorpt_empirical_full_min 0.715