An experimental and theoretical charge density study of theophylline and malonic acid cocrystallization
Hawkins, Bryson A.; Du, Jonathan J.; Lai, Felcia; Stanton, Stephen A.; Williams, Peter A.; Groundwater, Paul W.; Platts, James A.; Overgaard, Jacob; Hibbs, David E.; RSC Advances 12 (2022) 15670–15684; doi:10.1039/D1RA08389A

data_7244972
_publ_section_title
;
 An experimental and theoretical charge density study of theophylline and
 malonic acid cocrystallization
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              15670
_journal_page_last               15684
_journal_paper_doi               10.1039/D1RA08389A
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C7 H8 N4 O2'
_chemical_formula_sum            'C7 H8 N4 O2'
_chemical_formula_weight         180.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-03 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.3625(2)
_cell_length_b                   3.77810(10)
_cell_length_c                   8.47980(10)
_cell_measurement_reflns_used    54614
_cell_measurement_temperature    150(0)
_cell_measurement_theta_max      63.806
_cell_measurement_theta_min      4.064
_cell_volume                     780.51(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(0)
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_number            8913
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         52.123
_diffrn_reflns_theta_min         4.119
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 3642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         8913
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.303
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.0885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                8396
_reflns_number_total             8913
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra08389a2.cif
_cod_data_source_block           shelx_CCDC1
_cod_database_code               7244972
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.910
_olex2_refinement_description
;
1. Restrained distances
 C6-H6A
 1.059 with sigma of 0.02
 C6-H6B
 1.059 with sigma of 0.02
 C6-H6C
 1.059 with sigma of 0.02
 C7-H7A
 1.059 with sigma of 0.02
 C7-H7B
 1.059 with sigma of 0.02
 C7-H7C
 1.059 with sigma of 0.02
 C1-H1
 1.083 with sigma of 0.02
 N1-H1A
 1.009 with sigma of 0.02
;
_shelx_res_checksum              6346
_olex2_submission_original_sample_id 'THEO AN FOrm II'
_olex2_submission_special_instructions 'No special instructions were received'