Anomalous Chromophore Disruption Enables an Eight-Step Synthesis and Stereochemical Reassignment of (+)-Marineosin A.
Feng, Zhengao; Allred, Tyler K.; Hurlow, Evan E.; Harran, Patrick G.; Journal of the American Chemical Society 141 (2019) 2274–2278; doi:10.1021/jacs.9b00396

data_4128155
_publ_section_title
;
 Anomalous Chromophore Disruption Enables an Eight-Step Synthesis and
 Stereochemical Reassignment of (+)-Marineosin A.
;
_journal_issue                   6
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2274
_journal_page_last               2278
_journal_paper_doi               10.1021/jacs.9b00396
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C26.50 H37.50 Cl N3 O2'
_chemical_formula_sum            'C26.5 H37.5 Cl N3 O2'
_chemical_formula_weight         465.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 129.718(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.1593(15)
_cell_length_b                   8.7821(4)
_cell_length_c                   23.3882(10)
_cell_measurement_reflns_used    9065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.27
_cell_measurement_theta_min      2.68
_cell_volume                     5238.9(4)
_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-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0624
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38002
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.424
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'I\mS micro--focus source'
_exptl_absorpt_coefficient_mu    1.493
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       needle
_exptl_crystal_F_000             2004
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 3207 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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     609
_refine_ls_number_reflns         9489
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0700P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1199
_reflns_Friedel_coverage         0.837
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                7892
_reflns_number_total             9489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b00396_si_004.cif
_cod_data_source_block           cu_har1802lts
_cod_original_formula_sum        'C26.50 H37.50 Cl N3 O2'
_cod_database_code               4128155
_shelxl_version_number           2014/6
_shelx_res_checksum              71792
_shelx_hkl_checksum              74836