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_7241101
_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         'C8 H10 N4 O2, 2(C2 H4 O3)'
_chemical_formula_sum            'C12 H18 N4 O8'
_chemical_formula_weight         346.30
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-07-01 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8076(15)
_cell_length_b                   6.3120(6)
_cell_length_c                   13.8556(13)
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.01
_cell_measurement_theta_min      2.42
_cell_volume                     1469.9(2)
_computing_cell_refinement       'APEX2 Software (Bruker, 2013)'
_computing_data_collection       'APEX2 Software (Bruker, 2013)'
_computing_data_reduction        'APEX2 Software (Bruker, 2013)'
_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 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16112
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.532
_diffrn_reflns_theta_min         1.905
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.133
_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    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0397P)^2^+0.5828P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1774
_reflns_number_total             2428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01064b2.cif
_cod_data_source_block           14evi02
_cod_database_code               7241101
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.986