The asymmetric synthesis of polycyclic 3-spirooxindole alkaloids via the cascade reaction of 2-isocyanoethylindoles
Zhao, Xiaohu; Liu, Xiaohua; Xiong, Qian; Mei, Hongjiang; Ma, Baiwei; Lin, Lili; Feng, Xiaoming; Chemical Communications (Cambridge, United Kingdom) 51 (2015) 16076–16079; doi:10.1039/c5cc06353a

data_7118052
_publ_section_title
;
 The asymmetric synthesis of polycyclic 3-spirooxindole alkaloids via the
 cascade reaction of 2-isocyanoethylindoles
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   89
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              16076
_journal_page_last               16079
_journal_paper_doi               10.1039/c5cc06353a
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         '3(C29 H32 Cl N3 O3), C29 H26 Cl N3 O3'
_chemical_formula_sum            'C116 H128 Cl4 N12 O12'
_chemical_formula_weight         2024.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-29
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-27 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.701(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2218(2)
_cell_length_b                   27.5508(6)
_cell_length_c                   24.8963(5)
_cell_measurement_temperature    120
_cell_volume                     6318.3(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            76898
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.487
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62602
_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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.064
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 8479 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1348
_refine_ls_number_reflns         25799
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0565
_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^)+(0.1048P)^2^+0.7091P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1615
_refine_ls_wR_factor_ref         0.1706
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                21248
_reflns_number_total             25799
_reflns_threshold_expression     'I > 2\s(I)'
_cod_duplicate_entry             7118020
_cod_data_source_file            c5cc06353a2.cif
_cod_data_source_block           1-sr
_cod_database_code               7118052
_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
2. Others
 Sof(C86')=1-FVAR(1)
 Sof(C86)=FVAR(1)
 Sof(C87')=1-FVAR(2)
 Sof(C87)=FVAR(2)
 Fixed Sof: Cl4(0.5) Cl4'(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C10(H10L), C37(H37), C39(H39), C66(H66), C68(H68), C95(H95), C97(H97)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C41(H41A,H41B), C42(H42A,H42B), C70(H70A,
 H70B), C71(H71A,H71B), C99(H99A,H99B), C100(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), N7(H7), N10(H10), C2(H2), C3(H3), C5(H5), C20(H20), C21(H21),
 C22(H22), C23(H23), C31(H31), C32(H32), C34(H34), C49(H49), C50(H50), C51(H51),
  C52(H52), C60(H60), C61(H61), C63(H63), C78(H78), C79(H79), C80(H80),
 C81(H81), C89(H89), C90(H90), C92(H92), C107(H107), C108(H108), C109(H109),
 C110(H110)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C44(H44A,H44B,H44C), C45(H45A,
 H45B,H45C), C46(H46A,H46B,H46C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C75(H75A,H75B,
 H75C), C85(H85A,H85B,H85C), C102(H10C,H10D,H10E), C103(H10F,H10G,H10H),
 C104(H10I,H10J,H10K), C114(H11A,H11B,H11C), C115(H11D,H11E,H11F), C116(H11G,
 H11H,H11I)
;
_shelx_res_checksum              18877
_shelx_hkl_checksum              82017
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'