Asymmetric Synthesis of the Aromatic Fragment of Sespendole.
Ono, Yoshiki; Nakazaki, Atsuo; Ueki, Kaori; Higuchi, Keiko; Sriphana, Uraiwan; Adachi, Masaatsu; Nishikawa, Toshio; The Journal of organic chemistry 84 (2019) 9750–9757; doi:10.1021/acs.joc.9b01597

data_4034385
_publ_section_title
;
 Asymmetric Synthesis of the Aromatic Fragment of Sespendole.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9750
_journal_page_last               9757
_journal_paper_doi               10.1021/acs.joc.9b01597
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C18 H15 Br N2 O6'
_chemical_formula_sum            'C18 H15 Br N2 O6'
_chemical_formula_weight         435.23
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                94.618(3)
_cell_angle_beta                 95.332(4)
_cell_angle_gamma                94.579(4)
_cell_formula_units_Z            2
_cell_length_a                   8.3957(5)
_cell_length_b                   10.1273(6)
_cell_length_c                   10.8640(6)
_cell_measurement_reflns_used    4841
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      4.11
_cell_volume                     913.18(9)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10464
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.212
_diffrn_reflns_theta_min         4.103
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.420
_exptl_absorpt_correction_T_max  0.708
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440.00
_exptl_crystal_size_max          0.187
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.101
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.58
_refine_ls_extinction_coef       0.0091(10)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0567
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0833P)^2^+0.0679P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2550
_reflns_number_total             3256
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo9b01597_si_001.cif
_cod_data_source_block           180412-ono-01-
_cod_database_code               4034385
_shelx_res_checksum              23251
_shelx_hkl_checksum              14195