Synthon hierarchy in theobromine cocrystals with hydroxybenzoic acids as coformers
Gołdyn, Mateusz; Larowska, Daria; Nowak, Weronika; Bartoszak-Adamska, Elżbieta; CrystEngComm  (2019) –; doi:10.1039/C9CE01195A

data_7235245
_publ_section_title
;
 Synthon hierarchy in theobromine cocrystals with hydroxybenzoic acids as
 coformers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C9CE01195A
_journal_year                    2019
_chemical_formula_moiety         'C7 H8 N4 O2, C7 H6 O4'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_name_systematic        'theobromine-2,5-dihydroxybenzoic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-03 deposited with the CCDC.	2019-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                79.391(4)
_cell_angle_beta                 78.550(4)
_cell_angle_gamma                77.232(4)
_cell_formula_units_Z            2
_cell_length_a                   6.8492(3)
_cell_length_b                   7.9605(4)
_cell_length_c                   14.0276(8)
_cell_measurement_reflns_used    5805
_cell_measurement_temperature    130.3(4)
_cell_measurement_theta_max      75.8000
_cell_measurement_theta_min      3.2210
_cell_volume                     723.16(7)
_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      130.3(4)
_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 0.979
_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    -97.00  -2.00   1.00    1.25    --  -41.24 125.00 -60.00   95
  2  \w      2.00  97.00   1.00    1.25    --   41.24-125.00-180.00   95
  3  \w    -33.00  66.00   1.00    1.25    --   41.24 -37.00  30.00   99
  4  \w     17.00 116.00   1.00    1.25    --   41.24  37.00 -60.00   99
  5  \w     13.00 113.00   1.00    1.25    --   41.24  57.00-180.00  100
  6  \w     36.00  69.00   1.00   11.25    --  112.00 -30.00-150.00   33
  7  \w     39.00  77.00   1.00   11.25    --  112.00 -45.00 120.00   38
  8  \w     29.00 110.00   1.00   11.25    --  112.00 -94.00  60.00   81
  9  \w     29.00 110.00   1.00   11.25    --  112.00 -94.00 150.00   81
 10  \w     36.00  69.00   1.00   11.25    --  112.00 -30.00 -90.00   33
 11  \w     36.00 113.00   1.00   11.25    --  112.00-111.00-180.00   77
 12  \w     36.00 113.00   1.00   11.25    --  112.00-111.00-120.00   77
 13  \w     36.00  69.00   1.00   11.25    --  112.00 -30.00  60.00   33
 14  \w     36.00  69.00   1.00   11.25    --  112.00 -30.00 -60.00   33
 15  \w     39.00  77.00   1.00   11.25    --  112.00 -45.00  30.00   38
 16  \w     36.00 113.00   1.00   11.25    --  112.00-111.00 -30.00   77
 17  \w     36.00 145.00   1.00   11.25    --  112.00 -77.00-120.00  109
 18  \w     84.00 158.00   1.00   11.25    --  112.00  30.00-120.00   74
 19  \w     36.00 145.00   1.00   11.25    --  112.00 -77.00   0.00  109
 20  \w     24.00 158.00   1.00   11.25    --  112.00   0.00-150.00  134
 21  \w     36.00 113.00   1.00   11.25    --  112.00-111.00  30.00   77
 22  \w     84.00 158.00   1.00   11.25    --  112.00  30.00  60.00   74
 23  \w     39.00  77.00   1.00   11.25    --  112.00 -45.00-180.00   38
 24  \w     86.00 158.00   1.00   11.25    --  112.00  45.00 -60.00   72
 25  \w   -121.00   0.00   1.00    1.25    --  -41.24 -19.00  60.00  121
 26  \w   -116.00 -17.00   1.00    1.25    --  -41.24 -37.00   0.00   99
 27  \w    -39.00  82.00   1.00    1.25    --   41.24 -19.00-180.00  121
 28  \w      9.00 117.00   1.00    1.25    --   41.24  77.00-120.00  108
 29  \w      9.00 117.00   1.00    1.25    --   41.24  77.00 -30.00  108
 30  \w      9.00 117.00   1.00    1.25    --   41.24  77.00 120.00  108
 31  \w      9.00 117.00   1.00    1.25    --   41.24  77.00  30.00  108
 32  \w     86.00 137.00   1.00   11.25    --  112.00  45.00 -30.00   51
 33  \w     83.00 158.00   1.00   11.25    --  112.00  61.00  90.00   75
 34  \w     83.00 158.00   1.00   11.25    --  112.00  61.00-180.00   75
 35  \w     79.00 158.00   1.00   11.25    --  112.00  77.00-120.00   79
 36  \w     86.00 158.00   1.00   11.25    --  112.00  45.00   0.00   72
;
_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      0.0522100000
_diffrn_orient_matrix_UB_12      -0.0935246000
_diffrn_orient_matrix_UB_13      -0.0912828000
_diffrn_orient_matrix_UB_21      -0.2279168000
_diffrn_orient_matrix_UB_22      0.0174137000
_diffrn_orient_matrix_UB_23      -0.0015604000
_diffrn_orient_matrix_UB_31      -0.0007338000
_diffrn_orient_matrix_UB_32      0.1766108000
_diffrn_orient_matrix_UB_33      -0.0670619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11318
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.366
_diffrn_reflns_theta_min         3.250
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82536
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_preparation
'theobromine and 2,5-dihydroxybenzoic acid was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method
'cocrystallization by slow evaporation from methanol-water solution'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0519
_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^)+(0.1061P)^2^+0.2879P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1553
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2678
_reflns_number_total             2963
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01195a2.cif
_cod_data_source_block           tb-k25dhb-1-1bnext
_cod_database_code               7235245
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 H14 N4 O6'
_chemical_oxdiff_usercomment     '130.5 K (poczatek) 0.04 x 0.10 x 0.28'
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.758
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
;
_shelx_res_checksum              79102
_olex2_date_sample_data_collection 2019-03-09
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-25DHBA
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.725