Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals of oxyresveratrol and zwitterionic proline
Ouiyangkul, Passaporn; Saithong, Saowanit; Tantishaiyakul, Vimon; Acta Crystallographica Section E 76 (2020) 1528–1534; doi:10.1107/S2056989020011536

data_2243567
_publ_section_title
;
 Syntheses and crystal structures of hydrated and anhydrous 1:2 cocrystals
 of oxyresveratrol and zwitterionic proline
;
_journal_coeditor_code           HB7935
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1528
_journal_page_last               1534
_journal_paper_doi               10.1107/S2056989020011536
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C14 H12 O4, 2C5 H9 N O2, H2 O'
_chemical_formula_moiety         'C14 H12 O4, 2(C5 H9 N O2), H2 O'
_chemical_formula_sum            'C24 H32 N2 O9'
_chemical_formula_weight         492.51
_chemical_name_systematic
;
4-[(<i>E</i>)-2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,3-diol
bis[(<i>S</i>)-pyrrolidin-1-ium-2-carboxylate] monohydrate
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.9759(2)
_cell_length_b                   10.6052(2)
_cell_length_c                   22.8535(4)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      3.29
_cell_volume                     2417.82(8)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al</i>., 2020)
;
_computing_publication_material
;
WinGX  (Farrugia, 2012) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      297(2)
_diffrn_detector
'PHOTON II Charge-Integrating Pixel Array area detector'
_diffrn_detector_area_resol_mean 7.39
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'graphiteDouble Bounce Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0154
_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       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            27568
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.942
_diffrn_source                   'Sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.312
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4237
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0439
_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^)+(0.0603P)^2^+1.0192P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1167
_reflns_number_gt                4046
_reflns_number_total             4237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7935sup1.cif
_cod_data_source_block           I
_cod_database_code               2243567
_cod_database_fobs_code          2243567
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.988
_shelx_hkl_checksum              88912
_shelx_res_checksum              3740