An organocatalytic domino Michael addition strategy: construction of bispiro[oxindole-thiazolidinone-hexahydroxanthone]s with five contiguous stereocenters.
Song, Yong-Xing; Lin, Ye; Yan, Li; Du, Da-Ming; Organic & biomolecular chemistry 18 (2020) 7373–7378; doi:10.1039/d0ob01613f

data_7157701
_publ_section_title
;
 An organocatalytic domino Michael addition strategy: construction of
 bispiro[oxindole-thiazolidinone-hexahydroxanthone]s with five contiguous
 stereocenters.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7373
_journal_page_last               7378
_journal_paper_doi               10.1039/d0ob01613f
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C37 H34 N2 O8 S2'
_chemical_formula_sum            'C37 H34 N2 O8 S2'
_chemical_formula_weight         698.78
_chemical_melting_point          434.5(5)
_chemical_name_systematic
'(3R,3'S,4'R,4a'S,9a'R)-1-(tert-Butyl) 3'-ethyl 3''-benzyl-2,4'',9'-trioxo-2''-thioxo-4a',9a'- dihydro-1'H,3'H,9'H-dispiro[indoline-3,2'-xanthene-4',5''-thiazolidine]-1,3'-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2020-06-18 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.061(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.292(5)
_cell_length_b                   8.1908(13)
_cell_length_c                   16.147(3)
_cell_measurement_reflns_used    8342
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.42
_cell_volume                     4232.4(12)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20566
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.189
_diffrn_reflns_theta_max         25.189
_diffrn_reflns_theta_min         2.164
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.097
_exptl_crystal_description       cube
_exptl_crystal_F_000             1464
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Petroleum ether-ethyl acetate 3:1'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.983
_exptl_transmission_factor_min   0.950
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 2740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         7557
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0533P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                6620
_reflns_number_total             7557
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01613f2.cif
_cod_data_source_block           1_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '434-435' was changed to
'434.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157701.cif.
;
_cod_original_cell_volume        4232.3(12)
_cod_database_code               7157701
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.950
_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. Restrained distances
 C27-C28
 1.51 with sigma of 0.01
 S1-C30
 1.82 with sigma of 0.001
 C28-C27 = C28A-C27A
 1.53 with sigma of 0.02
 O4-C27A = O4-C27
 1.43 with sigma of 0.02
 C23A-C22 = C23-C22 = C24A-C22 = C24-C22 = C25-C22 = C25A-C22
 1.53 with sigma of 0.02
3. Rigid bond restraints
 S1, C30, C22, C25, O8, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
S1 \\sim C30 \\sim C22 \\sim C25 \\sim O8 \\sim C22: within 3.8A with sigma of
0.01 and sigma for terminal atoms of 0.02
C27A \\sim C27 \\sim C28 \\sim C28A: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.01
C25 \\sim C25A \\sim C24 \\sim C24A \\sim C23A \\sim C23 \\sim O6 \\sim C29:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.01
Uanis(S1) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
Uanis(C27A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C28A)
\\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C29) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
Uanis(C25) \\sim Ueq, Uanis(C25A) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C24A)
\\sim Ueq, Uanis(C23A) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
5. Others
 Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=
 Sof(H23F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(2)
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C13(H13), C8(H8), C9(H9)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C31(H31A,H31B), C27(H27A,H27B), C27A(H27C,H27D)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1), C3(H3), C2(H2), C15(H15), C18(H18), C16(H16), C17(H17),
 C37(H37), C33(H33), C36(H36), C35(H35), C34(H34)
6.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C28(H28A,H28B,
 H28C), C28A(H28D,H28E,H28F), C24A(H24D,H24E,H24F), C23A(H23D,H23E,H23F),
 C25A(H25D,H25E,H25F)
;
_shelx_res_checksum              80426
_shelx_hkl_checksum              87272
_shelx_fab_checksum              77974
_olex2_submission_special_instructions 'No special instructions were received'