Theobromine cocrystals with monohydroxybenzoic acids – synthesis, X-ray structural analysis, solubility and thermal properties
Gołdyn, Mateusz; Larowska, Daria; Nowak, Weronika; Bartoszak-Adamska, Elżbieta; CrystEngComm 21 (2019) 5721–; doi:10.1039/C9CE01020C

data_7233367
_publ_section_title
;
 Theobromine cocrystals with monohydroxybenzoic acids -- synthesis, X-ray
 structural analysis, solubility and thermal properties
;
_journal_issue                   38
_journal_name_full               CrystEngComm
_journal_page_first              5721
_journal_paper_doi               10.1039/C9CE01020C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O3'
_chemical_formula_sum            'C14 H14 N4 O5'
_chemical_formula_weight         318.29
_chemical_name_systematic        'theobromine 3-hydroxybenzoic acid'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-18 deposited with the CCDC.    2019-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.841(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4812(2)
_cell_length_b                   23.7503(7)
_cell_length_c                   9.3288(3)
_cell_measurement_reflns_used    4115
_cell_measurement_temperature    149.95(10)
_cell_measurement_theta_max      74.1890
_cell_measurement_theta_min      3.7050
_cell_volume                     1405.43(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      2.00  97.00   1.00    1.53    --   41.24-125.00 -90.00   95
  2  \w     13.00 113.00   1.00    1.53    --   41.24  57.00  30.00  100
  3  \w     17.00 116.00   1.00    1.53    --   41.24  37.00 -30.00   99
  4  \w     36.00  69.00   1.00    6.10    --  112.00 -30.00  30.00   33
  5  \w     79.00 158.00   1.00    6.10    --  112.00  77.00 -90.00   79
  6  \w     79.00 158.00   1.00    6.10    --  112.00 111.00 -60.00   79
  7  \w     36.00 113.00   1.00    6.10    --  112.00-111.00   0.00   77
  8  \w     36.00  69.00   1.00    6.10    --  112.00 -30.00-150.00   33
  9  \w     36.00 145.00   1.00    6.10    --  112.00 -77.00-150.00  109
 10  \w     36.00 107.00   1.00    6.10    --  112.00-111.00 -90.00   71
 11  \w     39.00  77.00   1.00    6.10    --  112.00 -45.00-120.00   38
 12  \w    105.00 157.00   1.00    6.10    --  112.00  61.00 -60.00   52
 13  \w     36.00 110.00   1.00    6.10    --  112.00-111.00-180.00   74
 14  \w     84.00 138.00   1.00    6.10    --  112.00  61.00  60.00   54
 15  \w     52.00 111.00   1.00    6.10    --  112.00-111.00 -60.00   59
 16  \w     77.00 128.00   1.00    6.10    --  112.00 179.00 -90.00   51
 17  \w     36.00  61.00   1.00    6.10    --  112.00 -30.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2423096000
_diffrn_orient_matrix_UB_12      0.0048978000
_diffrn_orient_matrix_UB_13      -0.0334964000
_diffrn_orient_matrix_UB_21      0.0180212000
_diffrn_orient_matrix_UB_22      0.0643034000
_diffrn_orient_matrix_UB_23      0.0206061000
_diffrn_orient_matrix_UB_31      -0.0000618000
_diffrn_orient_matrix_UB_32      0.0071033000
_diffrn_orient_matrix_UB_33      -0.1640421000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.006
_diffrn_reflns_theta_min         3.722
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_preparation
'theobromine and 3-hydroxybenzoic acid in stoichometric ratio (1:1) was dissolved in ethanol-water solution'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol-water'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0377
_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^)+(0.0459P)^2^+0.5392P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1016
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2625
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01020c2.cif
_cod_data_source_block           tb-k3hb-1-1-etoh-h20-5-5(3)-150k
_cod_depositor_comments
'Adding full bibliography for 7233366--7233368.cif.'
_cod_original_cell_volume        1405.44(8)
_cod_database_code               7233367
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_usercomment     RT
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              84119
_olex2_date_sample_data_collection 2018-11-28
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TB-3HBA
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.206
_oxdiff_exptl_absorpt_empirical_full_min 0.637