Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H and (-)-Isodaphlongamine H.
Hugelshofer, Cedric L.; Palani, Vignesh; Sarpong, Richmond; Journal of the American Chemical Society 141 (2019) 8431–8435; doi:10.1021/jacs.9b03576

data_4128757
_publ_section_title
;
 Calyciphylline B-Type Alkaloids: Total Syntheses of (-)-Daphlongamine H
 and (-)-Isodaphlongamine H.
;
_journal_issue                   21
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8431
_journal_page_last               8435
_journal_paper_doi               10.1021/jacs.9b03576
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C27 H43 N O3 Si'
_chemical_formula_sum            'C27 H43 N O3 Si'
_chemical_formula_weight         457.71
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 99.2147(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.19798(5)
_cell_length_b                   7.89375(4)
_cell_length_c                   20.23662(10)
_cell_measurement_reflns_used    50418
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.8030
_cell_measurement_theta_min      4.3880
_cell_volume                     1292.669(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            55132
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        74.000
_diffrn_reflns_theta_max         74.487
_diffrn_reflns_theta_min         4.427
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.070
_refine_diff_density_max         1.152
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 2405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         5275
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0937P)^2^+1.2089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5247
_reflns_number_total             5275
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b03576_si_003.cif
_cod_data_source_block           CH8_097p
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128757
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.666
_shelx_estimated_absorpt_t_max   0.933
_shelx_res_checksum              8640
_shelx_hkl_checksum              13