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_7247411
_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 H6 O5, C7 H8 N4 O2'
_chemical_formula_sum            'C14 H14 N4 O7'
_chemical_formula_weight         350.29
_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   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
;
2022-12-07 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.122(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9228(2)
_cell_length_b                   6.33067(19)
_cell_length_c                   29.1969(6)
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    212.99(10)
_cell_measurement_theta_max      72.0430
_cell_measurement_theta_min      3.0080
_cell_volume                     1458.57(6)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      212.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     41.00  66.00   1.00    0.70    --   48.67-124.00 116.00   25
  2  \w     70.00 106.00   1.00    0.70    --   48.67-147.00 -48.00   36
  3  \w     36.00  63.00   1.00    4.50    --  106.65 -57.00-120.00   27
  4  \w     80.00 152.00   1.00    4.50    --  106.65 147.00   1.00   72
  5  \w     80.00 106.00   1.00    4.50    --  106.65 -99.00 120.00   26
  6  \w     36.00 111.00   1.00    4.50    --  106.65-124.00 116.00   75
  7  \w     34.00  74.00   1.00    4.50    --  106.65 -99.00 120.00   40
  8  \w     35.00 103.00   1.00    4.50    --  106.65-125.00  30.00   68
  9  \w    101.00 127.00   1.00    4.50    --  106.65-147.00 -48.00   26
 10  \w    -85.00 -19.00   1.00    4.50    --  -91.75 125.00 150.00   66
 11  \w    -76.00 -51.00   1.00    4.50    --  -91.75 124.00-164.00   25
 12  \w    -82.00 -56.00   1.00    0.70    --  -48.67 124.00-164.00   26
 13  \w    -27.00  25.00   1.00    0.70    --  -48.67  19.00-120.00   52
 14  \w    -26.00  25.00   1.00    0.70    --  -48.67  19.00 -60.00   51
 15  \w    -65.00 -20.00   1.00    4.50    --  -91.75  57.00  30.00   45
 16  \w   -165.00 -79.00   1.00    4.50    --  -91.75 -19.00 120.00   86
 17  \w   -143.00-118.00   1.00    4.50    --  -91.75-124.00 116.00   25
 18  \w   -118.00 -74.00   1.00    0.70    --  -48.67-125.00 150.00   44
 19  \w   -114.00 -88.00   1.00    0.70    --  -48.67-124.00 116.00   26
 20  \w   -119.00 -61.00   1.00    0.70    --  -48.67-147.00 -48.00   58
 21  \w    -99.00 -70.00   1.00    4.50    --  -91.75-147.00 -48.00   29
 22  \w   -158.00-125.00   1.00    4.50    --  -91.75 -57.00-120.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0360579000
_diffrn_orient_matrix_UB_12      -0.2218115000
_diffrn_orient_matrix_UB_13      -0.0185580000
_diffrn_orient_matrix_UB_21      0.1121261000
_diffrn_orient_matrix_UB_22      0.0981877000
_diffrn_orient_matrix_UB_23      -0.0348593000
_diffrn_orient_matrix_UB_31      0.1556242000
_diffrn_orient_matrix_UB_32      -0.0196481000
_diffrn_orient_matrix_UB_33      0.0353269000
_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  0.0388
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         3.039
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96589
_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    1.595
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.5167P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2130
_reflns_number_total             2591
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00762f2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7247410--7247413.cif.'
_cod_original_cell_volume        1458.57(7)
_cod_database_code               7247411
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.936
_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), C2(H2A), C5(H5), C3(H3)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4), O7(H7), O3(H3A)
;
_shelx_res_checksum              62875
_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 1.276
_oxdiff_exptl_absorpt_empirical_full_min 0.829