Chemo-, Regio-, and Stereoselective Construction of Core Skeleton of Furo[2,3-b]pyrrole via Multicomponent Bicyclization Reaction.
Man, Ning-Ning; Wang, Jia-Qi; Zhang, Li-Ming; Wen, Li-Rong; Li, Ming; The Journal of organic chemistry 82 (2017) 5566–5573; doi:10.1021/acs.joc.7b00371

data_4032550
_publ_section_title
;
 Chemo-, Regio-, and Stereoselective Construction of Core Skeleton of
 Furo[2,3-b]pyrrole via Multicomponent Bicyclization Reaction.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5566
_journal_page_last               5573
_journal_paper_doi               10.1021/acs.joc.7b00371
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H24 N2 O4 S'
_chemical_formula_sum            'C28 H24 N2 O4 S'
_chemical_formula_weight         484.55
_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   mixed
_audit_creation_date             2014-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.859(3)
_cell_length_b                   12.130(3)
_cell_length_c                   18.229(5)
_cell_measurement_reflns_used    6486
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4764
_cell_measurement_theta_min      1.6789
_cell_volume                     2401.1(11)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution
;
'SHELXS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device
;
Saturn724 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0073
_diffrn_orient_matrix_UB_12      0.0174
_diffrn_orient_matrix_UB_13      -0.0901
_diffrn_orient_matrix_UB_21      -0.0070
_diffrn_orient_matrix_UB_22      0.0808
_diffrn_orient_matrix_UB_23      0.0150
_diffrn_orient_matrix_UB_31      0.0545
_diffrn_orient_matrix_UB_32      0.0037
_diffrn_orient_matrix_UB_33      0.0052
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16183
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_min         3.367
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.13(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0243P)^2^+0.7894P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5198
_reflns_number_total             5467
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00371_si_001.cif
_cod_data_source_block           sa3369
_cod_original_cell_volume        2401.2(10)
_cod_database_code               4032550
_shelxl_version_number           2013-4
_diffrn_number_total             3124
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              57512
_shelx_hkl_checksum              77766