Total Synthesis and Stereochemical Assignment of Streptide.
Isley, Nicholas A.; Endo, Yusuke; Wu, Zhi-Chen; Covington, Brett C.; Bushin, Leah B.; Seyedsayamdost, Mohammad R.; Boger, Dale L.; Journal of the American Chemical Society 141 (2019) 17361–17369; doi:10.1021/jacs.9b09067

data_4127900
_publ_section_title
;
 Total Synthesis and Stereochemical Assignment of Streptide.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17361
_journal_page_last               17369
_journal_paper_doi               10.1021/jacs.9b09067
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C38 H34 Br N5 O6 S'
_chemical_formula_sum            'C38 H34 Br N5 O6 S'
_chemical_formula_weight         768.67
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.535(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.5382(5)
_cell_length_b                   8.2269(2)
_cell_length_c                   14.7591(4)
_cell_measurement_reflns_used    9465
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.82
_cell_measurement_theta_min      3.05
_cell_volume                     1735.50(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31472
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        68.000
_diffrn_reflns_theta_max         70.039
_diffrn_reflns_theta_min         3.045
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  0.5225
_exptl_absorpt_correction_T_min  0.3744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0908 before and 0.0691 after correction. The Ratio of minimum to maximum transmission is 0.7166. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.015
_refine_diff_density_max         1.095
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 2782 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         6529
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0567P)^2^+0.5079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6292
_reflns_number_total             6529
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09067_si_003.cif
_cod_data_source_block           boger89b
_cod_database_code               4127900
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.558
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3
 0.88 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28), C29(H29), C33(H33),
  C34(H34), C36(H36), C37(H37)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              52298
_shelx_hkl_checksum              96144
_olex2_submission_special_instructions 'No special instructions were received'