Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy.
Kim, Daria E.; Zweig, Joshua E.; Newhouse, Timothy R.; Journal of the American Chemical Society 141 (2019) 1479–1483; doi:10.1021/jacs.8b13127

data_4128097
_publ_section_title
;
 Total Synthesis of Paspaline A and Emindole PB Enabled by Computational
 Augmentation of a Transform-Guided Retrosynthetic Strategy.
;
_journal_issue                   4
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1479
_journal_page_last               1483
_journal_paper_doi               10.1021/jacs.8b13127
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H38 N O2, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C28.5 H39 Cl N O2'
_chemical_formula_weight         463.05
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     SHELXT
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                75.681(2)
_cell_angle_beta                 81.697(2)
_cell_angle_gamma                89.964(2)
_cell_formula_units_Z            4
_cell_length_a                   11.4162(3)
_cell_length_b                   13.3892(4)
_cell_length_c                   18.7283(5)
_cell_measurement_reflns_used    60824
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      66.5340
_cell_measurement_theta_min      2.4390
_cell_volume                     2742.85(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB-2014/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 22.2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            96656
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         2.462
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    1.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.39.16b (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.121
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
; 
 Flack x determined using 7830 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.053(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1205
_refine_ls_number_reflns         18194
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1177P)^2^+0.8876P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1574
_refine_ls_wR_factor_ref         0.1592
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.894
_reflns_Friedel_fraction_max     0.894
_reflns_number_gt                17485
_reflns_number_total             18194
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b13127_si_004.cif
_cod_data_source_block           007a-18048
_cod_original_formula_sum        'C28.50 H39 Cl N O2'
_cod_database_code               4128097
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.767
_shelx_estimated_absorpt_t_max   0.946
_shelx_res_checksum              74775
_shelx_hkl_checksum              57490
_shelx_fab_checksum              96347