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_2021133
_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          'C15 H23 N O4, C9 H8 O2'
_chemical_formula_moiety         'C15 H23 N O4, C9 H8 O2'
_chemical_formula_sum            'C24 H31 N O6'
_chemical_formula_weight         429.50
_chemical_name_common
;
11-Azaartemisinin--<i>trans</i>-cinnamic 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>)-3-Phenylprop-2-enoic acid (1/1)'
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 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                91.085(4)
_cell_angle_beta                 110.515(4)
_cell_angle_gamma                93.998(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5552(4)
_cell_length_b                   10.3175(5)
_cell_length_c                   11.9645(6)
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      75.3200
_cell_measurement_theta_min      3.9390
_cell_volume                     1100.85(9)
_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      99.97(11)
_diffrn_detector_area_resol_mean 10.3577
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'kappa 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  0.0319
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16397
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.486
_diffrn_reflns_theta_min         3.949
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.176
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.05(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     581
_refine_ls_number_reflns         7242
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0420P)^2^+0.0075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0769
_reflns_number_gt                6766
_reflns_number_total             7242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            lf3073sup1.cif
_cod_data_source_block           madiha47cult
_cod_original_cell_volume        1100.84(9)
_cod_database_code               2021133
_cod_database_fobs_code          2021133
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.978
_shelx_hkl_checksum              8877
_shelx_res_checksum              50722
_shelxl_version_number           2.014