Asymmetric Barton–Zard Reaction To Access 3-Pyrrole-Containing Axially Chiral Skeletons
He, Xiao-Long; Zhao, Hui-Ru; Song, Xue; Jiang, Bo; Du, Wei; Chen, Ying-Chun; ACS Catalysis 9 (2019) 4374–; doi:10.1021/acscatal.9b00767

data_4514690
_publ_section_title
;
 Asymmetric Barton--Zard Reaction To Access 3-Pyrrole-Containing Axially
 Chiral Skeletons
;
_journal_issue                   5
_journal_name_full               'ACS Catalysis'
_journal_page_first              4374
_journal_paper_doi               10.1021/acscatal.9b00767
_journal_volume                  9
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 N3 O4'
_chemical_formula_sum            'C24 H25 N3 O4'
_chemical_formula_weight         419.47
_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_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
_audit_creation_date             2018-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2464(3)
_cell_length_b                   10.0773(4)
_cell_length_c                   23.4808(9)
_cell_measurement_reflns_used    3316
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.9420
_cell_measurement_theta_min      6.0890
_cell_volume                     2187.91(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
  1 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  -90.0000 94

  2 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

  3 omega   23.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000    0.0000 67

  4 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

  5 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -30.0000 84

  6 omega   27.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 77

  7 omega   39.00   70.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 31

  8 omega   66.00  104.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 38

  9 omega   45.00   90.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 45

 10 omega   50.00   88.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 38

 11 omega   63.00  122.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 59

 12 omega  109.00  173.00   1.0000    3.9000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0280147000
_diffrn_orient_matrix_UB_12      -0.1046656000
_diffrn_orient_matrix_UB_13      -0.0465514000
_diffrn_orient_matrix_UB_21      0.0489860000
_diffrn_orient_matrix_UB_22      -0.0997394000
_diffrn_orient_matrix_UB_23      0.0458593000
_diffrn_orient_matrix_UB_31      -0.1566565000
_diffrn_orient_matrix_UB_32      -0.0499105000
_diffrn_orient_matrix_UB_33      0.0059655000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7009
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.505
_diffrn_reflns_theta_min         5.141
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       needle
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0499
_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^)+(0.0966P)^2^+0.1838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.487
_reflns_Friedel_fraction_full    0.689
_reflns_Friedel_fraction_max     0.638
_reflns_number_gt                3451
_reflns_number_total             3616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b00767_si_003.cif
_cod_data_source_block           5aa
_cod_database_code               4514690
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.78
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B), C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), C00A(H00A), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00O(H00O), C00P(H00P), C00R(H00R), C00S(H00S), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00M(H00C,H00D,H00E), C00Q(H00G,H00L,H00M), C00T(H00N,H00Q,H00T), C00V(H00V,
 H00W,H00X)
;
_shelx_res_checksum              32911
_shelx_hkl_checksum              42857
_olex2_submission_special_instructions 'No special instructions were received'