Recurrent motifs in pharmaceutical cocrystals involving Glycolic acid: X-ray characterization, Hirshfeld surface analysis and DFT calculations
Alvarez-Lorenzo, Carmen; Castineiras, Alfonso; Frontera, Antonio; Garcia-Santos, Isabel; González-Pérez, Josefa Maria; Niclos-Gutierrez, Juan; Rodríguez-González, Iria; Vilchez, Esther; Zaręba, Jan Kazimierz; CrystEngComm  (2020) –; doi:10.1039/D0CE01064B

data_7241102
_publ_section_title
;
 Recurrent motifs in pharmaceutical cocrystals involving Glycolic acid:
 X-ray characterization, Hirshfeld surface analysis and DFT calculations
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01064B
_journal_year                    2020
_chemical_formula_moiety         'C2 H4 O3, C2 H3 O3, H4 N'
_chemical_formula_sum            'C4 H11 N O6'
_chemical_formula_weight         169.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-04 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.012(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.81770(10)
_cell_length_b                   18.7165(7)
_cell_length_c                   10.7428(4)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.46
_cell_measurement_theta_min      4.725
_cell_volume                     725.74(4)
_computing_cell_refinement       'APEX3 Software (Bruker, 2018)'
_computing_data_collection       'APEX3 Software (Bruker, 2018)'
_computing_data_reduction        'APEX3 Software (Bruker, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.522
_diffrn_reflns_theta_min         4.725
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0314P)^2^+0.3407P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1391
_reflns_number_total             1487
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01064b2.cif
_cod_data_source_block           19ac01
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241102
_shelx_estimated_absorpt_t_min   0.829
_shelx_estimated_absorpt_t_max   0.903
_shelxl_version_number           2013-3
_shelx_res_checksum              94122