Six novel multicomponent systems of theobromine with carboxylic acids: crystallographic structures, solubility determination and DFT calculations
Yuan, Xin-Yue; Cheng, Yan; Liu, Jun; Sun, Qi-Lei; Xue, Fu-Min; CrystEngComm 25 (2023) 5682–5696; doi:10.1039/D3CE00762F

data_7247413
_publ_section_title
;
 Six novel multicomponent systems of theobromine with carboxylic acids:
 crystallographic structures, solubility determination and DFT
 calculations
;
_journal_issue                   40
_journal_name_full               CrystEngComm
_journal_page_first              5682
_journal_page_last               5696
_journal_paper_doi               10.1039/D3CE00762F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C7 H8 N4 O2, C9 H8 O3'
_chemical_formula_sum            'C16 H16 N4 O5'
_chemical_formula_weight         344.33
_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   geom
_audit_creation_date             2022-11-08
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-09-05 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                80.367(4)
_cell_angle_beta                 69.633(4)
_cell_angle_gamma                67.650(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8706(5)
_cell_length_b                   9.1259(5)
_cell_length_c                   11.3422(4)
_cell_measurement_reflns_used    4254
_cell_measurement_temperature    213.00(10)
_cell_measurement_theta_max      75.3810
_cell_measurement_theta_min      4.1610
_cell_volume                     795.46(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      213.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     32.00  59.00   1.00    0.10    --   48.42 -57.00 120.00   27
  2  \w    -21.00  21.00   1.00    0.10    --   48.42 -57.00 120.00   42
  3  \w    -28.00  26.00   1.00    0.10    --  -48.42  22.00 -11.00   54
  4  \w    -75.00 -22.00   1.00    0.20    --  -91.75 125.00-150.00   53
  5  \w    -78.00 -23.00   1.00    0.20    --  -91.75 125.00  30.00   55
  6  \w    -20.00  29.00   1.00    0.10    --   48.42 -22.00-177.00   49
  7  \w     37.00  95.00   1.00    0.10    --   48.42-125.00-120.00   58
  8  \w     80.00 110.00   1.00    0.20    --  106.65-125.00  90.00   30
  9  \w     70.00 104.00   1.00    0.20    --  106.65-125.00  60.00   34
 10  \w     38.00  66.00   1.00    0.20    --  106.65-125.00  60.00   28
 11  \w     39.00  68.00   1.00    0.20    --  106.65-125.00  90.00   29
 12  \w     77.00 103.00   1.00    0.20    --  106.65 -99.00 120.00   26
 13  \w     36.00 106.00   1.00    0.20    --  106.65 -99.00 150.00   70
 14  \w     41.00  71.00   1.00    0.20    --  106.65 -99.00 120.00   30
 15  \w     34.00  97.00   1.00    0.20    --  106.65 -99.00 -90.00   63
 16  \w     36.00 105.00   1.00    0.20    --  106.65 -99.00 -60.00   69
 17  \w     37.00  63.00   1.00    0.20    --  106.65 -57.00   0.00   26
 18  \w     36.00  65.00   1.00    0.20    --  106.65 -57.00 -30.00   29
 19  \w     45.00 105.00   1.00    0.20    --  106.65 -77.00 150.00   60
 20  \w    101.00 177.00   1.00    0.20    --  106.65  22.00 -11.00   76
 21  \w    123.00 177.00   1.00    0.20    --  106.65  38.00-150.00   54
 22  \w     94.00 120.00   1.00    0.20    --  106.65  38.00-150.00   26
 23  \w     63.00 105.00   1.00    0.10    --   48.42  22.00 -11.00   42
 24  \w   -117.00 -78.00   1.00    0.20    --  -91.75 -57.00 -30.00   39
 25  \w   -149.00-123.00   1.00    0.20    --  -91.75 -57.00 -30.00   26
 26  \w   -163.00-125.00   1.00    0.20    --  -91.75 -22.00-177.00   38
 27  \w   -110.00 -81.00   1.00    0.20    --  -91.75 -22.00-177.00   29
 28  \w   -122.00 -36.00   1.00    0.10    --  -48.42 -22.00-177.00   86
 29  \w   -154.00 -84.00   1.00    0.20    --  -91.75 -19.00 120.00   70
 30  \w   -102.00 -74.00   1.00    0.10    --  -48.42-125.00 120.00   28
 31  \w   -163.00 -88.00   1.00    0.20    --  -91.75 -99.00 -30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0991366000
_diffrn_orient_matrix_UB_12      0.1054434000
_diffrn_orient_matrix_UB_13      0.0027786000
_diffrn_orient_matrix_UB_21      -0.1701969000
_diffrn_orient_matrix_UB_22      0.1401986000
_diffrn_orient_matrix_UB_23      0.0408309000
_diffrn_orient_matrix_UB_31      -0.0162782000
_diffrn_orient_matrix_UB_32      -0.0509422000
_diffrn_orient_matrix_UB_33      0.1391063000
_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  0.0338
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7567
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.161
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.438
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0697P)^2^+0.0854P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2411
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00762f2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7247410--7247413.cif.'
_cod_original_cell_volume        795.47(8)
_cod_database_code               7247413
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_shelx_res_checksum              42369
_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 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.848