Total syntheses of (±)-spiroindimicins B and C enabled by a late-stage Schöllkopf‒Magnus‒Barton‒Zard (SMBZ) reaction
Blair, Lachlan M.; Sperry, Jonathan; Chemical Communications (Cambridge, United Kingdom) 52 (2016) 800–802; doi:10.1039/c5cc09060a

data_7118483
_publ_section_title
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 Total syntheses of (+-)-spiroindimicins B and C enabled by a late-stage
 Sch\"ollkopf--Magnus--Barton--Zard (SMBZ) reaction
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_journal_coden_ASTM              CHCOFS
_journal_issue                   4
_journal_name_full
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 Chemical Communications (Cambridge, United Kingdom)
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_journal_page_first              800
_journal_page_last               802
_journal_paper_doi               10.1039/c5cc09060a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C34 H29 Cl2 N3 O6 S'
_chemical_formula_weight         678.56
_chemical_melting_point          199.0(10)
_chemical_name_systematic
'5'-(tert-butyl) 3'-methyl 5,8'-dichloro-1-tosylspiro[indoline-3,4'-pyrrolo[3',4':3,4]cyclopenta[1,2-b]indole]-3',5'(2'H)-dicarboxylate'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-11-04 deposited with the CCDC.
2015-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                73.289(5)
_cell_angle_beta                 72.517(5)
_cell_angle_gamma                76.408(5)
_cell_formula_units_Z            2
_cell_length_a                   9.468(5)
_cell_length_b                   12.672(5)
_cell_length_c                   14.441(5)
_cell_measurement_temperature    372(2)
_cell_volume                     1561.7(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      372(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33016
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.9681
_exptl_absorpt_correction_T_min  0.8970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method
'liquid-liquid diffusion with CDCl3-Et2O'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         7370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0681P)^2^+0.2425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                5021
_reflns_number_total             7370
_reflns_threshold_expression     >2\s(I)
_cod_duplicate_entry             7118180
_cod_data_source_file            c5cc09060a2.cif
_cod_data_source_block           lbs305a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '198-200' was changed to '199.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4093 2015-10-18 17:28:56Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7118483