Enantioselective N-Heterocyclic Carbene-Catalyzed Synthesis of Spirocyclic Oxindole-benzofuroazepinones.
Gao, Zhong-Hua; Chen, Kun-Quan; Zhang, Yan; Kong, Ling-Mei; Li, Yan; Ye, Song; The Journal of organic chemistry 83 (2018) 15225–15235; doi:10.1021/acs.joc.8b02497

data_4034766
_publ_section_title
;
 Enantioselective N-Heterocyclic Carbene-Catalyzed Synthesis of
 Spirocyclic Oxindole-benzofuroazepinones.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15225
_journal_page_last               15235
_journal_paper_doi               10.1021/acs.joc.8b02497
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C39 H29 Br N2 O5 S'
_chemical_formula_sum            'C39 H29 Br N2 O5 S'
_chemical_formula_weight         717.61
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-06
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.4667(3)
_cell_length_b                   15.7431(3)
_cell_length_c                   33.5575(7)
_cell_measurement_reflns_used    21048
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.9898
_cell_measurement_theta_min      2.2290
_cell_volume                     6586.1(2)
_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  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_av_unetI/netI     0.1368
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            88605
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.853
_diffrn_reflns_theta_min         2.233
_diffrn_source                   'Sealed Tube'
_exptl_absorpt_coefficient_mu    1.360
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.156
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     867
_refine_ls_number_reflns         18847
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0723
_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^)+(0.0316P)^2^+0.6417P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                10754
_reflns_number_total             18847
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02497_si_002.cif
_cod_data_source_block           sa5242
_cod_database_code               4034766
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.758
_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:
 C2(H2), C2A(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C14(H14A,H14B), C6A(H6AA,H6AB), C14A(H14C,H14D)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30),
  C31(H31), C34(H34), C35(H35), C37(H37), C38(H38), C8A(H8A), C9A(H9A),
 C10A(H10A), C11A(H11A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A),
 C20A(H20A), C22A(H22A), C23A(H23A), C25A(H25A), C26A(H26A), C28A(H28A),
 C29A(H29A), C30A(H30A), C31A(H31A), C34A(H34A), C35A(H35A), C37A(H37A),
 C38A(H38A)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C39A(H39D,H39E,H39F)
;
_shelx_res_checksum              71218
_shelx_hkl_checksum              38326
_olex2_submission_special_instructions 'No special instructions were received'