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_7235242
_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-3,4-dihydroxybenzoic acid'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.7527(5)
_cell_length_b                   14.2120(2)
_cell_length_c                   7.2608(2)
_cell_measurement_reflns_used    3752
_cell_measurement_temperature    130.9(8)
_cell_measurement_theta_max      74.5510
_cell_measurement_theta_min      3.2740
_cell_volume                     2760.62(10)
_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      130.9(8)
_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 0.977
_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    -98.00 -15.00   1.00   16.50    --  -41.36 -57.00  90.00   83
  2  \w    -94.00 -56.00   1.00   16.50    --  -41.36 125.00 -90.00   38
  3  \w    -10.00  63.00   1.00   16.50    --   41.36 -37.00 -90.00   73
  4  \w     38.00  64.00   1.00   64.00    --  112.00 -30.00  30.00   26
  5  \w     85.00 111.00   1.00   64.00    --  112.00  61.00 150.00   26
  6  \w     49.00 104.00   1.00   64.00    --  112.00-111.00 150.00   55
  7  \w     40.00  66.00   1.00   64.00    --  112.00 -45.00 -60.00   26
  8  \w     38.00  63.00   1.00   64.00    --  112.00 -30.00 -90.00   25
  9  \w     87.00 113.00   1.00   64.00    --  112.00-111.00  60.00   26
 10  \w     39.00  73.00   1.00   64.00    --  112.00 -45.00 120.00   34
 11  \w     45.00  75.00   1.00   64.00    --  112.00 -45.00  60.00   30
 12  \w    127.00 155.00   1.00   64.00    --  112.00  61.00 150.00   28
 13  \w     97.00 158.00   1.00   64.00    --  112.00  30.00-120.00   61
;
_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      0.0133710000
_diffrn_orient_matrix_UB_12      0.1054173000
_diffrn_orient_matrix_UB_13      -0.0054047000
_diffrn_orient_matrix_UB_21      -0.0068155000
_diffrn_orient_matrix_UB_22      0.0003170000
_diffrn_orient_matrix_UB_23      -0.2107003000
_diffrn_orient_matrix_UB_31      -0.0555728000
_diffrn_orient_matrix_UB_32      0.0253244000
_diffrn_orient_matrix_UB_33      0.0247605000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.438
_diffrn_reflns_theta_min         3.304
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51299
_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    1.609
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_preparation
'theobromine and 3,4-dihydroxybenzoic acid in stoichometric ratio (1:1) was dissolved in methanol-water solution'
_exptl_crystal_recrystallization_method
'cocrystallization by slow evaporation from methanol-water solution'
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         2827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0533
_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^)+(0.0664P)^2^+2.9797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1441
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2530
_reflns_number_total             2827
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01195a2.cif
_cod_data_source_block           tb-k34dhb-1-1-meoh-h20
_cod_database_code               7235242
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 H14 N4 O6'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.714
_olex2_refinement_description
;
;
_shelx_res_checksum              14279
_olex2_date_sample_data_collection 2019-02-23
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-34DHBA
_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 2.093
_oxdiff_exptl_absorpt_empirical_full_min 0.179