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_4032263
_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            'C21 H31 N3 O3'
_chemical_formula_weight         373.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5338(2)
_cell_length_b                   15.4969(4)
_cell_length_c                   17.6570(5)
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      72.51
_cell_measurement_theta_min      2.85
_cell_volume                     2061.46(10)
_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      90(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.955
_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  0.0168
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15100
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.502
_diffrn_reflns_theta_min         5.768
_diffrn_source                   'rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6865
_exptl_absorpt_correction_type   'Multi-scan (SADABS; Bruker, 2015)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       Block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.055
_exptl_crystal_size_mid          0.004
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3901
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0424P)^2^+0.3881P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.948
_reflns_number_gt                3898
_reflns_number_total             3901
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02816_si_003.cif
_cod_data_source_block           ukaji003_0m_a
_cod_database_code               4032263
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              20560
_shelx_hkl_checksum              27876