11-Step Total Synthesis of Araiosamines.
Tian, Maoqun; Yan, Ming; Baran, Phil S.; Journal of the American Chemical Society 138 (2016) 14234–14237; doi:10.1021/jacs.6b09701

data_4131130
_publ_section_title
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 11-Step Total Synthesis of Araiosamines.
;
_journal_issue                   43
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14234
_journal_page_last               14237
_journal_paper_doi               10.1021/jacs.6b09701
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C30 H23 Br3 N4 O2, C H4 O, C3 H6 O'
_chemical_formula_sum            'C34 H33 Br3 N4 O4'
_chemical_formula_weight         801.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-02-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                89.3780(10)
_cell_angle_beta                 70.0490(10)
_cell_angle_gamma                72.2580(10)
_cell_formula_units_Z            2
_cell_length_a                   10.2153(2)
_cell_length_b                   11.9013(2)
_cell_length_c                   14.8471(3)
_cell_measurement_reflns_used    9834
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.034
_cell_measurement_theta_min      3.184
_cell_volume                     1607.25(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.976
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36110
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.330
_diffrn_reflns_theta_min         3.184
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.026
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1028 before and 0.0555 after correction.
The Ratio of minimum to maximum transmission is 0.6545.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_description       plate
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         5751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0338P)^2^+2.1465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4754
_reflns_number_total             5751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09701_si_008.cif
_cod_data_source_block           baran568_a
_cod_database_code               4131130
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C2(H2A), C1(H1B), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N3(H3), N2(H2), N4(H4), C30(H30), C26(H26), C28(H28), C14(H14),
 C22(H22), C25(H25), C10(H10), C12(H12), C9(H9), C17(H17), C20(H20), C18(H18)
2.d Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4B)
;
_shelx_res_checksum              81884
_shelx_hkl_checksum              54265
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id MT3-117
_olex2_submission_special_instructions 'No special instructions were received'