Total Synthesis of Sieboldine A.
Shao, Hui; Wang, Yun-Peng; Fang, Kun; Zhao, Yu-Ming; Tu, Yong-Qiang; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01660

data_4038727
_publ_section_title
;
 Total Synthesis of Sieboldine A.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01660
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         ' C15 H19.44 O3'
_chemical_formula_sum            'C15 H19.44 O3'
_chemical_formula_weight         247.75
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9886(2)
_cell_length_b                   9.9248(2)
_cell_length_c                   16.3400(4)
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      66.62
_cell_measurement_theta_min      5.21
_cell_volume                     1295.52(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5694
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.611
_diffrn_reflns_theta_max         66.611
_diffrn_reflns_theta_min         5.214
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.35(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.241
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     175
_refine_ls_restrained_S_all      1.225
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0408
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1372
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                2146
_reflns_number_total             2237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01660_si_002.cif
_cod_data_source_block           a
_cod_original_formula_sum        ' C15 H19.44 O3'
_cod_database_code               4038727
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              4156
_shelx_hkl_checksum              64781