Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar Cycloaddition of Azomethine Imines.
Tong, Thu Minh Thi; Soeta, Takahiro; Suga, Takuya; Kawamoto, Keisuke; Hayashi, Yoshihito; Ukaji, Yutaka; The Journal of organic chemistry 82 (2017) 1969–1976; doi:10.1021/acs.joc.6b02816

data_4032158
_publ_section_title
;
 Formal Total Synthesis of Manzacidin C Based on Asymmetric 1,3-Dipolar
 Cycloaddition of Azomethine Imines.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1969
_journal_page_last               1976
_journal_paper_doi               10.1021/acs.joc.6b02816
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C23 H27 N3 O3'
_chemical_formula_weight         393.47
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-10-29 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 95.5090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5902(2)
_cell_length_b                   9.9373(3)
_cell_length_c                   10.7178(3)
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      4.14
_cell_volume                     1016.70(5)
_computing_cell_refinement       'SAINT (Bruker AXS)'
_computing_data_collection       'APEX3 (Bruker AXS)'
_computing_data_reduction        'SAINT (Bruker AXS)'
_computing_molecular_graphics    'ShelXle (H?bschle et al., 2011)'
_computing_publication_material  'APEX3 (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8263
_diffrn_reflns_point_group_measured_fraction_full 0.918
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.450
_diffrn_reflns_theta_min         4.144
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6463
_exptl_absorpt_correction_type   'Multi-scan (SADABS; Bruker, 2015)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       Block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.054
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3643
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0401P)^2^+0.1609P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0670
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.849
_reflns_Friedel_fraction_max     0.824
_reflns_number_gt                3636
_reflns_number_total             3643
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02816_si_002.cif
_cod_data_source_block           ukaji001_0m_a
_cod_depositor_comments          'Adding full bibliography for 4032158.cif.'
_cod_database_code               4032158
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              79628
_shelx_hkl_checksum              45168