Synthesis of Chiral Trispirocyclic Oxindoles via Organic-Base/Au(I)-Catalyzed Sequential Reactions
Guo, Wengang; Li, Lu; Ding, Qian; Lin, Xiangfeng; Liu, Xianghui; Wang, Kai; Liu, Yan; Fan, Hongjun; Li, Can; ACS Catalysis 8 (2018) 10180–; doi:10.1021/acscatal.8b02157

data_4515763
_publ_section_title
;
 Synthesis of Chiral Trispirocyclic Oxindoles via
 Organic-Base/Au(I)-Catalyzed Sequential Reactions
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              10180
_journal_paper_doi               10.1021/acscatal.8b02157
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C27 H26 Cl F N4 O7, H2 O'
_chemical_formula_sum            'C27 H28 Cl F N4 O8'
_chemical_formula_weight         590.98
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2999(13)
_cell_length_b                   14.3668(16)
_cell_length_c                   15.8349(18)
_cell_measurement_reflns_used    3346
_cell_measurement_temperature    130
_cell_measurement_theta_max      20.38
_cell_measurement_theta_min      2.53
_cell_volume                     2798.2(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28503
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.677
_diffrn_reflns_theta_min         1.914
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0877 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.8689.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.345
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 1977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         8639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0670
_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^)+(0.1011P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1906
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                5898
_reflns_number_total             8639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b02157_si_004.cif
_cod_data_source_block           mo_dm15030_0m
_cod_database_code               4515763
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.965
_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, All O(H,H) groups
2.a Free rotating group:
 O8(H8A,H8B)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C7(H7), C17(H17), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              98587
_shelx_hkl_checksum              35780
_olex2_submission_special_instructions 'No special instructions were received'