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_7235243
_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 H6 O4, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O6'
_chemical_formula_weight         334.29
_chemical_name_systematic        'theobromine-3,5-dihydroxybenzoic 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'
_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                 92.3554(17)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4617(3)
_cell_length_b                   12.7978(3)
_cell_length_c                   15.7666(3)
_cell_measurement_reflns_used    6232
_cell_measurement_temperature    130.8(6)
_cell_measurement_theta_max      75.2160
_cell_measurement_theta_min      4.4450
_cell_volume                     2915.58(11)
_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      130.8(6)
_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 0.994
_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    -69.00 -15.00   1.00    5.00    --  -41.24  57.00 150.00   54
  2  \w   -119.00  -1.00   1.00    5.00    --  -41.24 -19.00 -60.00  118
  3  \w     20.00  76.00   1.00    5.00    --   41.24-125.00-150.00   56
  4  \w     64.00  95.00   1.00   20.00    --  112.00  15.00  60.00   31
  5  \w     36.00  68.00   1.00   20.00    --  112.00 -30.00-120.00   32
  6  \w     43.00  69.00   1.00   20.00    --  112.00 -30.00  30.00   26
  7  \w     36.00  69.00   1.00   20.00    --  112.00 -30.00-150.00   33
  8  \w     40.00  67.00   1.00   20.00    --  112.00 -45.00 120.00   27
  9  \w     39.00  65.00   1.00   20.00    --  112.00 -45.00 -60.00   26
 10  \w     48.00  73.00   1.00   20.00    --  112.00 -45.00 150.00   25
 11  \w     45.00 106.00   1.00   20.00    --  112.00-111.00 -30.00   61
 12  \w     47.00  73.00   1.00   20.00    --  112.00 -61.00  90.00   26
 13  \w     86.00 131.00   1.00   20.00    --  112.00 -61.00  90.00   45
 14  \w     68.00  97.00   1.00   20.00    --  112.00  15.00 -60.00   29
 15  \w     39.00  65.00   1.00   20.00    --  112.00 -45.00  30.00   26
 16  \w     36.00  62.00   1.00   20.00    --  112.00 -30.00 -90.00   26
 17  \w    128.00 154.00   1.00   20.00    --  112.00  15.00 -60.00   26
 18  \w     36.00 109.00   1.00   20.00    --  112.00 -77.00   0.00   73
 19  \w    113.00 138.00   1.00   20.00    --  112.00 -77.00   0.00   25
 20  \w    112.00 157.00   1.00   20.00    --  112.00  15.00  60.00   45
 21  \w     93.00 145.00   1.00   20.00    --  112.00  30.00-150.00   52
 22  \w     38.00  67.00   1.00   20.00    --  112.00 -30.00 -30.00   29
 23  \w    106.00 132.00   1.00   20.00    --  112.00  45.00 120.00   26
 24  \w     53.00  78.00   1.00   20.00    --  112.00-111.00-120.00   25
 25  \w     46.00  71.00   1.00   20.00    --  112.00-111.00  90.00   25
 26  \w     39.00  72.00   1.00   20.00    --  112.00 -45.00-180.00   33
;
_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      0.0789307000
_diffrn_orient_matrix_UB_12      0.0721211000
_diffrn_orient_matrix_UB_13      0.0327199000
_diffrn_orient_matrix_UB_21      -0.0609086000
_diffrn_orient_matrix_UB_22      0.0386862000
_diffrn_orient_matrix_UB_23      0.0715493000
_diffrn_orient_matrix_UB_31      0.0377641000
_diffrn_orient_matrix_UB_32      -0.0882954000
_diffrn_orient_matrix_UB_33      0.0580644000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.087
_diffrn_reflns_theta_min         3.058
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85748
_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    1.523
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1392
_exptl_crystal_preparation
'theobromine and 3,5-dihydroxybenzoic acid in stoichometri ratio was dissolved in water and next this mixture was heated and mixed for 30 minutes.'
_exptl_crystal_recrystallization_method
'cocrystallization by slow evaporation from water solution'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     545
_refine_ls_number_reflns         6048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0470
_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^)+(0.0732P)^2^+0.9562P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1354
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5330
_reflns_number_total             6048
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01195a2.cif
_cod_data_source_block           tb-k35dhb-1-1-odp
_cod_original_cell_volume        2915.58(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7235243
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C28 H28 N8 O12'
_chemical_oxdiff_usercomment     '130 K, 0.12 x 0.12 x 0.14 [mm]'
_shelx_estimated_absorpt_t_max   0.886
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              78642
_olex2_date_sample_data_collection 2019-01-26
_olex2_exptl_crystal_mounting_method 'crystal was mounted on loop by glue'
_olex2_submission_original_sample_id TBR-35DHBA
_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 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.798