Diastereoselective ABB' Three-Component Synthesis of Highly Functionalized Spirooxindoles Bearing Five Consecutive Asymmetric Carbons.
Vivekanand, Thavaraj; Vachan, B. S.; Karuppasamy, Muthu; Muthukrishnan, Isravel; Maheswari, C. Uma; Nagarajan, Subbiah; Bhuvanesh, Nattamai; Sridharan, Vellaisamy; The Journal of organic chemistry 84 (2019) 4009–4016; doi:10.1021/acs.joc.8b03270

data_4034282
_publ_section_title
;
 Diastereoselective ABB' Three-Component Synthesis of Highly
 Functionalized Spirooxindoles Bearing Five Consecutive Asymmetric
 Carbons.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4009
_journal_page_last               4016
_journal_paper_doi               10.1021/acs.joc.8b03270
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C29 H31 N O7'
_chemical_formula_sum            'C29 H31 N O7'
_chemical_formula_weight         505.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                105.636(2)
_cell_angle_beta                 104.250(2)
_cell_angle_gamma                96.415(2)
_cell_formula_units_Z            4
_cell_length_a                   10.5687(17)
_cell_length_b                   13.919(2)
_cell_length_c                   18.485(3)
_cell_measurement_reflns_used    8156
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.360
_cell_measurement_theta_min      2.303
_cell_volume                     2491.4(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29301
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.456
_diffrn_reflns_theta_min         1.638
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.9262.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.473
_exptl_crystal_size_min          0.468
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     706
_refine_ls_number_reflns         11215
_refine_ls_number_restraints     128
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0422
_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^)+(0.0528P)^2^+0.3448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1114
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8633
_reflns_number_total             11215
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03270_si_002.cif
_cod_data_source_block           vs01
_cod_database_code               4034282
_shelx_estimated_absorpt_t_max   0.956
_shelx_estimated_absorpt_t_min   0.954
_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, All O(H) groups
2. Restrained distances
 O5C-C22C \\sim O5B-C22B
 with sigma of 0.02
 O5C-C21B \\sim O5B-C21B
 with sigma of 0.02
 C23B-C22B \\sim C23B-C22C
 with sigma of 0.02
 C23B-C22B \\sim C23C-C22C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O5B \\sim O5C \\sim C22B \\sim C22C \\sim C23B \\sim C23C \\sim C21B \\sim O4B:
within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 O5B, O5C, C22B, C22C, C23B, C23C, C21B, O4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O5C)=Sof(C22C)=Sof(H22C)=Sof(H22D)=Sof(C23C)=Sof(H23D)=Sof(H23E)=
 Sof(H23F)=1-FVAR(1)
 Sof(O5B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(C23B)=Sof(H23A)=Sof(H23B)=
 Sof(H23C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C16B(H16B), C17B(H17B), C18B(H18B)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C22(H22E,H22F), C28(H28C,H28D), C9B(H9BA,H9BB), C22B(H22A,H22B),
 C28B(H28A,H28B), C22C(H22C,H22D)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C5B(H5B), C6B(H6B), C7B(H7B), C8B(H8B), C11B(H11B), C12B(H12B),
 C13B(H13B), C14B(H14B), C15B(H15B)
6.d Idealised Me refined as rotating group:
 C20(H20D,H20E,H20F), C23(H23G,H23H,H23I), C26(H26D,H26E,H26F), C29(H29D,H29E,
 H29F), C20B(H20A,H20B,H20C), C23B(H23A,H23B,H23C), C26B(H26A,H26B,H26C),
 C29B(H29A,H29B,H29C), C23C(H23D,H23E,H23F)
6.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2B(H2B)
;
_shelx_res_checksum              64838
_shelx_hkl_checksum              29019
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'