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_4121564
_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-194-2
_chemical_name_systematic
; 
 maimone23 
;
_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
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7606(4)
_cell_length_b                   10.0156(5)
_cell_length_c                   54.297(3)
_cell_measurement_reflns_used    9580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.26
_cell_volume                     3676.5(3)
_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-2013
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.975
_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  0.0490
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         1.0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_number            47377
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.283
_diffrn_reflns_theta_min         3.256
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
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_refine_diff_density_max         0.336
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
; 
 Flack x determined using 2472 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         6367
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0284P)^2^+3.8933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1281
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.918
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                6284
_reflns_number_total             6367
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja502208z_si_003.cif
_cod_data_source_block           maimone23
_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               4121564
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.979
_shelxl_version_number           2013-4
_shelx_res_checksum              2776
_shelx_hkl_checksum              15021