Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen Stitching Strategy.
Hu, Xirui; Maimone, Thomas J.; Journal of the American Chemical Society 136 (2014) 5287–5290; doi:10.1021/ja502208z

data_4121567
_publ_section_title
;
 Four-Step Synthesis of the Antimalarial Cardamom Peroxide via an Oxygen
 Stitching Strategy.
;
_journal_issue                   14
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5287
_journal_page_last               5290
_journal_paper_doi               10.1021/ja502208z
_journal_volume                  136
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_chemical_name_common            XH-211-3
_chemical_name_systematic
; 
 maimone24 
;
_space_group.centring_type       P
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8100(3)
_cell_length_b                   9.9666(4)
_cell_length_c                   27.5837(12)
_cell_measurement_reflns_used    9263
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      3.20
_cell_volume                     1872.18(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28889
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.390
_diffrn_reflns_theta_min         3.204
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 1354 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0364
_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^)+(0.0591P)^2^+0.5174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3308
_reflns_number_total             3424
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja502208z_si_004.cif
_cod_data_source_block           maimone24
_cod_depositor_comments
;Adding full bibliography for 4121564--4121567.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4121567
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.986
_shelxl_version_number           2014-1
_shelx_res_checksum              74148
_shelx_hkl_checksum              80054