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_4131133
_publ_section_title
;
 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_absolute_configuration ad
_chemical_formula_moiety         'C30 H32 Br2 N4 O4, C2 H3 N'
_chemical_formula_sum            'C32 H35 Br2 N5 O4'
_chemical_formula_weight         713.47
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-07-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_cell_angle_alpha                102.075(6)
_cell_angle_beta                 93.922(4)
_cell_angle_gamma                101.361(4)
_cell_formula_units_Z            2
_cell_length_a                   6.1564(10)
_cell_length_b                   15.590(3)
_cell_length_c                   17.998(3)
_cell_measurement_reflns_used    3991
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      19.460
_cell_measurement_theta_min      2.329
_cell_volume                     1645.2(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48397
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        23.332
_diffrn_reflns_theta_max         23.332
_diffrn_reflns_theta_min         1.368
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.506
_exptl_absorpt_correction_T_max  0.0243
_exptl_absorpt_correction_T_min  0.0099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0715 after correction.
The Ratio of minimum to maximum transmission is 0.4074.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       Needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.053
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.038
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 2443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.040(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     789
_refine_ls_number_reflns         9304
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0699
_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^)+(0.0722P)^2^+2.4796P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                6948
_reflns_number_total             9304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b09701_si_003.cif
_cod_data_source_block           Baran603
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1645.3(5)
_cod_database_code               4131133
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.879
_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.a Ternary CH refined with riding coordinates:
 C2(H2A), C3(H3A), C2'(H2'A), C3'(H3'A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), C8(H8), C9(H9), C10(H10), C12(H12), C16(H16), C17(H17),
 C18(H18), C20(H20), N2'(H2'), N3'(H3'), C8'(H8'), C9'(H9'), C10'(H10'),
 C12'(H12'), C16'(H16'), C17'(H17'), C18'(H18'), C20'(H20')
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C23'(H23D,H23E,H23F),
 C24'(H24D,H24E,H24F), C25'(H25D,H25E,H25F), C28'(H28D,H28E,H28F), C29'(H29D,
 H29E,H29F), C30'(H30D,H30E,H30F), C2S(H2SA,H2SB,H2SC), C4S(H4SA,H4SB,H4SC)
;
_shelx_res_checksum              41958
_shelx_hkl_checksum              3427
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'