Catalytic Asymmetric [4 + 1] Cyclization of Benzofuran-Derived Azadienes with 3-Chlorooxindoles.
Wang, Cong-Shuai; Li, Tian-Zhen; Cheng, Yu-Chun; Zhou, Ji; Mei, Guang-Jian; Shi, Feng; The Journal of organic chemistry 84 (2019) 3214–3222; doi:10.1021/acs.joc.8b03004

data_4033918
_publ_section_title
;
 Catalytic Asymmetric [4 + 1] Cyclization of Benzofuran-Derived Azadienes
 with 3-Chlorooxindoles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3214
_journal_page_last               3222
_journal_paper_doi               10.1021/acs.joc.8b03004
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C31 H24 N2 O5 S'
_chemical_formula_sum            'C31 H24 N2 O5 S'
_chemical_formula_weight         536.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                83.441(5)
_cell_angle_beta                 74.668(4)
_cell_angle_gamma                84.081(5)
_cell_formula_units_Z            2
_cell_length_a                   9.8432(8)
_cell_length_b                   10.4209(9)
_cell_length_c                   14.3197(12)
_cell_measurement_reflns_used    9323
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.31
_cell_measurement_theta_min      5.30
_cell_volume                     1403.2(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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_temperature      170
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14431
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.284
_diffrn_reflns_theta_min         5.494
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1233 before and 0.0735 after correction. The Ratio of minimum to maximum transmission is 0.7183. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.044
_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     354
_refine_ls_number_reflns         5288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0367P)^2^+0.6528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1122
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4513
_reflns_number_total             5288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03004_si_002.cif
_cod_data_source_block           sf20181025-wcs
_cod_database_code               4033918
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.901
_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:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C16(H16), C17(H17),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29),
  C30(H30)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              27821
_shelx_hkl_checksum              15507
_shelx_fab_checksum              81577
_olex2_submission_special_instructions 'No special instructions were received'