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_7233368
_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, 2(C7 H6 O3), H2 O'
_chemical_formula_sum            'C21 H22 N4 O9'
_chemical_formula_weight         474.42
_chemical_name_systematic
'theobromine di(4-hydroxybenzoic acid) monohydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-12
_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                99.639(3)
_cell_angle_beta                 91.740(3)
_cell_angle_gamma                99.464(3)
_cell_formula_units_Z            4
_cell_length_a                   7.0166(2)
_cell_length_b                   12.4761(4)
_cell_length_c                   24.6450(8)
_cell_measurement_reflns_used    8972
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      75.9360
_cell_measurement_theta_min      3.6340
_cell_volume                     2094.29(12)
_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      130.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.970
_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    -65.00 -39.00   1.00    2.00    --  -41.36  57.00-150.00   26
  2  \w   -104.00 -32.00   1.00    2.00    --  -41.36 -37.00  60.00   72
  3  \w     26.00 118.00   1.00    2.00    --   41.36  77.00 -60.00   92
  4  \w      3.00  97.00   1.00    2.00    --   41.36-125.00  60.00   94
  5  \w    -27.00  64.00   1.00    2.00    --   41.36 -57.00-180.00   91
  6  \w    122.00 154.00   1.00   11.00    --  112.00  30.00  90.00   32
  7  \w     37.00  82.00   1.00   11.00    --  112.00 -94.00 -30.00   45
  8  \w     46.00  77.00   1.00   11.00    --  112.00 -45.00 -60.00   31
  9  \w     36.00  66.00   1.00   11.00    --  112.00 -30.00 -30.00   30
 10  \w     40.00 112.00   1.00   11.00    --  112.00 -77.00  30.00   72
 11  \w     40.00 112.00   1.00   11.00    --  112.00-111.00 -60.00   72
 12  \w     84.00 112.00   1.00   11.00    --  112.00  30.00  90.00   28
 13  \w     64.00  90.00   1.00   11.00    --  112.00-111.00 -90.00   26
 14  \w     44.00  69.00   1.00   11.00    --  112.00 -45.00  30.00   25
 15  \w     36.00  98.00   1.00   11.00    --  112.00-111.00-120.00   62
 16  \w     44.00  77.00   1.00   11.00    --  112.00 -45.00-180.00   33
 17  \w     96.00 146.00   1.00   11.00    --  112.00  30.00   0.00   50
 18  \w     60.00 113.00   1.00   11.00    --  112.00-111.00  30.00   53
 19  \w     70.00 112.00   1.00   11.00    --  112.00-111.00 120.00   42
 20  \w     77.00 156.00   1.00   11.00    --  112.00  15.00-120.00   79
 21  \w     43.00  75.00   1.00   11.00    --  112.00 -45.00-120.00   32
 22  \w     38.00  88.00   1.00   11.00    --  112.00 -77.00 120.00   50
 23  \w     88.00 126.00   1.00   11.00    --  112.00  30.00-180.00   38
 24  \w     51.00  76.00   1.00   11.00    --  112.00 -45.00 120.00   25
 25  \w     63.00  88.00   1.00   11.00    --  112.00  15.00 -30.00   25
 26  \w    101.00 156.00   1.00   11.00    --  112.00  15.00 -30.00   55
 27  \w     56.00 113.00   1.00   11.00    --  112.00-111.00-150.00   57
 28  \w     87.00 135.00   1.00   11.00    --  112.00  45.00 120.00   48
;
_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      0.0029119000
_diffrn_orient_matrix_UB_12      -0.0500266000
_diffrn_orient_matrix_UB_13      0.0530243000
_diffrn_orient_matrix_UB_21      -0.1919126000
_diffrn_orient_matrix_UB_22      0.0389996000
_diffrn_orient_matrix_UB_23      0.0150736000
_diffrn_orient_matrix_UB_31      -0.1135037000
_diffrn_orient_matrix_UB_32      -0.1101913000
_diffrn_orient_matrix_UB_33      -0.0315554000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16429
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.607
_diffrn_reflns_theta_min         3.645
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90097
_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_primary    colourless
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_preparation
'theobromine and 4-hydroxybenzoic acid in stoichometric ratio (1:2) was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol-water'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         8559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0664P)^2^+0.8557P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1388
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7299
_reflns_number_total             8559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01020c2.cif
_cod_data_source_block           tb-k4hb-wat130k
_cod_depositor_comments
'Adding full bibliography for 7233366--7233368.cif.'
_cod_database_code               7233368
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C42 H44 N8 O18'
_chemical_oxdiff_usercomment     '130 K, 0.05 x 0.11 x 0.21 mm'
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.815
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Others
 Fixed Sof: H1C(0.5) H2C(0.5) H1D(0.25) H2D(0.75)
;
_shelx_res_checksum              2164
_olex2_date_sample_data_collection 2019-02-01
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-4HB-WAT
_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.784