Structure of the caffeine-pyrogallol complex: revisiting a pioneering structural analysis of a model pharmaceutical cocrystal.
Al Rahal, Okba; Ferguson, Michael; Lennox, Cameron B.; Male, Louise; Friščić, Tomislav; Chemical communications (Cambridge, England) 60 (2024) 7431–7434; doi:10.1039/d4cc02289k

data_7133127
_publ_section_title
;
 Structure of the caffeine-pyrogallol complex: revisiting a pioneering
 structural analysis of a model pharmaceutical cocrystal.
;
_journal_issue                   58
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7431
_journal_page_last               7434
_journal_paper_doi               10.1039/d4cc02289k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C8 H10 N4 O2, C6 H6 O3'
_chemical_formula_sum            'C14 H16 N4 O5'
_chemical_formula_weight         320.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-26 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.937(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8775(12)
_cell_length_b                   7.5913(4)
_cell_length_c                   15.0147(12)
_cell_measurement_reflns_used    6121
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      72.6390
_cell_measurement_theta_min      5.8470
_cell_volume                     1410.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_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    -83.00   8.00   1.00    2.50    --  -41.27 108.00 -90.00   91
  2  \w    -34.00  67.00   1.00    2.50    --   41.27 -33.00  21.00  101
  3  \w     77.00 178.00   1.00   10.00    --  102.80  33.00 179.00  101
  4  \w     27.00 109.00   1.00   10.00    --  102.80-108.00 171.00   82
  5  \w    104.00 178.00   1.00   10.00    --  102.80  95.00  10.00   74
  6  \w   -116.00 -17.00   1.00    2.50    --  -41.27 -38.00-180.00   99
  7  \w      6.00  81.00   1.00    2.50    --   41.27 -99.00 120.00   75
  8  \w     61.00 146.00   1.00   10.00    --  102.80 178.00   0.00   85
  9  \w    103.00 178.00   1.00   10.00    --  102.80  77.00-120.00   75
 10  \w     77.00 176.00   1.00   10.00    --  102.80  45.00   0.00   99
 11  \w    104.00 176.00   1.00   10.00    --  102.80 111.00 -90.00   72
 12  \w     20.00 107.00   1.00   10.00    --  102.80 -94.00   0.00   87
 13  \w   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00  60.00  100
 14  \w   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00 150.00  100
 15  \w   -113.00 -13.00   1.00    2.50    --  -41.27 -57.00 -60.00  100
 16  \w     74.00 156.00   1.00   10.00    --  102.80  61.00-150.00   82
 17  \w     74.00 175.00   1.00   10.00    --  102.80  61.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0303110000
_diffrn_orient_matrix_UB_12      0.1492415000
_diffrn_orient_matrix_UB_13      -0.0771908000
_diffrn_orient_matrix_UB_21      -0.0093640000
_diffrn_orient_matrix_UB_22      0.1289331000
_diffrn_orient_matrix_UB_23      0.0752098000
_diffrn_orient_matrix_UB_31      0.1203752000
_diffrn_orient_matrix_UB_32      0.0482284000
_diffrn_orient_matrix_UB_33      0.0402754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12680
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.051
_diffrn_reflns_theta_min         3.603
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.105
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0469
_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^)+(0.0634P)^2^+0.5286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2275
_reflns_number_total             2730
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc02289k2.cif
_cod_data_source_block           caf-pyg
_cod_depositor_comments
'Adding full bibliography for 7133127--7133128.cif.'
_cod_database_code               7133127
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C14 H16 N4 O5'
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.829
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              37729
_shelx_hkl_checksum              37363
_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 1.227
_oxdiff_exptl_absorpt_empirical_full_min 0.870