Rapid and Systematic Exploration of Chemical Space Relevant to Artemisinins: Anti-malarial Activities of Skeletally Diversified Tetracyclic Peroxides and 6-Aza-artemisinins.
Bonepally, Karunakar Reddy; Takahashi, Norihito; Matsuoka, Naoya; Koi, Hikari; Mizoguchi, Haruki; Hiruma, Takahisa; Ochiai, Kyohei; Suzuki, Shun; Yamagishi, Yutaka; Oikawa, Hideaki; Ishiyama, Aki; Hokari, Rei; Iwatsuki, Masato; Otoguro, Kazuhiko; Omura, Satoshi; Kato, Nobutaka; Oguri, Hiroki; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01017

data_4038569
_publ_section_title
;
 Rapid and Systematic Exploration of Chemical Space Relevant to
 Artemisinins: Anti-malarial Activities of Skeletally Diversified
 Tetracyclic Peroxides and 6-Aza-artemisinins.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01017
_journal_year                    2020
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C19 H20 Br N O6'
_chemical_formula_sum            'C19 H20 Br N O6'
_chemical_formula_weight         438.27
_chemical_name_systematic
'9-desmethyl-6-aza(pBrbenzoylated)-artemisinin '
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1mqbj6
_audit_update_record
;
2016-10-21 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.873(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            2
_cell_length_a                   8.7395(6)
_cell_length_b                   8.7830(6)
_cell_length_c                   11.9719(9)
_cell_measurement_reflns_used    9457
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.04
_cell_volume                     914.13(11)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r15'
_computing_data_collection       'CrystalClear-SM Auto 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r15'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9682
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.292
_exptl_absorpt_correction_T_max  0.201
_exptl_absorpt_correction_T_min  0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             448.00
_exptl_crystal_size_max          1.200
_exptl_crystal_size_mid          0.900
_exptl_crystal_size_min          0.700
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.230
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4155
_refine_ls_R_factor_gt           0.0316
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[0.0002Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0695
_reflns_number_gt                3864
_reflns_number_total             4155
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo0c01017_si_003.cif
_cod_data_source_block           User-defined
_cod_database_code               4038569