Studies on the asymmetric synthesis of pandamarilactonines: an unexpected syn-selective vinylogous Mannich reaction of N-tert-butanesulfinimines
Ye, Jian-Liang; Zhang, Yu-Feng; Liu, Yang; Zhang, Jin-Yuan; Ruan, Yuan-Ping; Huang, Pei-Qiang; Organic Chemistry Frontiers 2 (2015) 697–; doi:10.1039/C5QO00098J

data_1553132
_publ_section_title
;
 Studies on the asymmetric synthesis of pandamarilactonines: an unexpected
 syn-selective vinylogous Mannich reaction of N-tert-butanesulfinimines
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              697
_journal_paper_doi               10.1039/C5QO00098J
_journal_volume                  2
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H23 N O3 S'
_chemical_formula_sum            'C13 H23 N O3 S'
_chemical_formula_weight         273.39
_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_Int_Tables_number      4
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-03-25 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.531(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.291(2)
_cell_length_b                   5.9808(12)
_cell_length_c                   12.068(2)
_cell_measurement_reflns_used    4213
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.35
_cell_volume                     722.1(2)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.9880
_diffrn_measured_fraction_theta_max 0.9880
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4174
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_min  0.845984
_exptl_absorpt_process_details
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0532 before and 0.0281 after correction.
The Ratio of minimum to maximum transmission is 0.8460.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.2573
_exptl_crystal_description       pillar
_exptl_crystal_F_000             296.3836
_refine_diff_density_max         0.3993
_refine_diff_density_min         -0.3000
_refine_diff_density_rms         0.0707
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_d_res_high            0.8107
_refine_ls_d_res_low             11.7328
_refine_ls_goodness_of_fit_ref   1.0660
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0660
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.0874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0880
_reflns_Friedel_coverage         0.784
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2517
_reflns_number_total             2522
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5qo00098j2.cif
_cod_data_source_block           y0121m
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C2.889 H5.111 N0.222 O0.667 S0.222'
_cod_original_formula_weight         60.76
_cod_original_formula_moiety         '0.22(C13 H23 N O3 S)'
_cod_original_formula_units_Z            9
_cod_original_cell_volume        722.1(3)
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               1553132
_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.a Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10)
2.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C8(H8a,H8b,H8c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c),
 C17(H17a,H17b,H17c)
;
_olex2_submission_special_instructions 'No special instructions were received'