Varying degrees of homostructurality in a series of cocrystals of antimalarial drug 11-azaartemisinin with salicylic acids
Roy, Monalisa; Li, Keyao; Nisar, Madiha; Wong, Lawrence W.-Y.; Sung, Herman H.-Y.; Haynes, Richard K.; Williams, Ian D.; Acta Crystallographica Section C 77 (2021) 262–270; doi:10.1107/S2053229621004460

data_2022373
_publ_section_title
;
 Varying degrees of homostructurality in a series of cocrystals of
 antimalarial drug 11-azaartemisinin with salicylic acids
;
_journal_coeditor_code           DV3004
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              262
_journal_page_last               270
_journal_paper_doi               10.1107/S2053229621004460
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration rmad
_chemical_formula_iupac          'C15 H23 N O4, C7 H5 Br O3'
_chemical_formula_moiety         'C15 H23 N O4, C7 H5 Br O3'
_chemical_formula_sum            'C22 H28 Br N O7'
_chemical_formula_weight         498.36
_chemical_name_common
;
11-Azaartemisinin--5-bromosalicylic acid (1/1)
;
_chemical_name_systematic
'1,5,9-Trimethyl-14,15,16-trioxa-11-azatetracyclo[10.3.1.0^4,13^.0^8,13^]hexadecan-10-one; 5-bromosalicylic acid'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.844(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9325(4)
_cell_length_b                   9.0196(3)
_cell_length_c                   12.3942(4)
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      71.7170
_cell_measurement_theta_min      3.5470
_cell_volume                     1107.86(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type
'Rigaku OD SuperNova Dual source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6416
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         72.510
_diffrn_reflns_theta_min         3.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    2.906
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96066
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       needle
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.392
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0101P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0611
_reflns_number_gt                2929
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dv3004sup1.cif
_cod_data_source_block           mona16cult
_cod_depositor_comments
'Adding full bibliography for 2022370--2022375.cif.'
_cod_original_cell_volume        1107.88(6)
_cod_database_code               2022373
_cod_database_fobs_code          2022373
_shelx_estimated_absorpt_t_min   0.760
_shelx_estimated_absorpt_t_max   0.944
_shelx_hkl_checksum              52793
_shelx_res_checksum              80759