Total Synthesis and Anti-Cancer Activity of All Known Communesin Alkaloids and Related Derivatives.
Pompeo, Matthew M.; Cheah, Jaime H.; Movassaghi, Mohammad; Journal of the American Chemical Society 141 (2019) 14411–14420; doi:10.1021/jacs.9b07397

data_4128792
_publ_section_title
;
 Total Synthesis and Anti-Cancer Activity of All Known Communesin
 Alkaloids and Related Derivatives.
;
_journal_issue                   36
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14411
_journal_page_last               14420
_journal_paper_doi               10.1021/jacs.9b07397
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C33 H44 N4 O4 S Si, C H4 O'
_chemical_formula_sum            'C34 H48 N4 O5 S Si'
_chemical_formula_weight         652.91
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.123(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9317(5)
_cell_length_b                   15.4939(11)
_cell_length_c                   13.8939(11)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.18
_cell_measurement_theta_min      3.18
_cell_volume                     1706.3(2)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.4
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Photon2 CPAD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22916
_diffrn_reflns_point_group_measured_fraction_full 0.869
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.183
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.552
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5696
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.391
_exptl_crystal_size_mid          0.033
_exptl_crystal_size_min          0.022
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.688
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
; 
 Flack x determined using 1415 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.061(16)
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5423
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0665
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1146P)^2^+0.5462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.1861
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.731
_reflns_Friedel_fraction_max     0.729
_reflns_number_gt                4396
_reflns_number_total             5423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07397_si_003.cif
_cod_data_source_block           IV-68-12
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4128792
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.582
_shelx_estimated_absorpt_t_max   0.967
_shelx_res_checksum              11226
_shelx_hkl_checksum              72218