Cocrystals of the antimalarial drug 11-azaartemisinin with three alkenoic acids of 1:1 or 2:1 stoichiometry
Nisar, Madiha; Wong, Lawrence W.-Y.; Sung, Herman H.-Y.; Haynes, Richard K.; Williams, Ian D.; Acta Crystallographica Section C 74 (2018) –; doi:10.1107/S2053229618006320

data_2021136
_publ_section_title
;
 Cocrystals of the antimalarial drug 11-azaartemisinin with three alkenoic
 acids of 1:1 or 2:1 stoichiometry
;
_journal_coeditor_code           LF3073
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229618006320
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          '2C15 H23 N O4, C4 H4 O4'
_chemical_formula_moiety         '2(C15 H23 N O4), C4 H4 O4'
_chemical_formula_sum            'C34 H50 N2 O12'
_chemical_formula_weight         678.76
_chemical_name_common
;
11-Azaartemisinin--fumaric 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--(2<i>E</i>)-but-2-enedioic acid (1/1)'
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5470)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4731(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.57929(11)
_cell_length_b                   10.05214(16)
_cell_length_c                   17.7765(2)
_cell_measurement_reflns_used    10873
_cell_measurement_temperature    99.96(13)
_cell_measurement_theta_max      75.5340
_cell_measurement_theta_min      4.6330
_cell_volume                     1700.83(4)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_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
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      99.96(13)
_diffrn_detector_area_resol_mean 10.3577
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku SuperNova Dual Source diffractometer with an Atlas detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15361
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.497
_diffrn_reflns_theta_min         4.646
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.162
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2330 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.11(6)
_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     455
_refine_ls_number_reflns         5657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0254
_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^)+(0.0392P)^2^+0.2051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                5564
_reflns_number_total             5657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lf3073sup1.cif
_cod_data_source_block           madiha46cult
_cod_original_cell_volume        1700.82(4)
_cod_database_code               2021136
_shelx_estimated_absorpt_t_min   0.732
_shelx_estimated_absorpt_t_max   0.907
_shelx_hkl_checksum              11464
_shelx_res_checksum              55277
_shelxl_version_number           2.014
_cod_database_fobs_code 2021136