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_7247410
_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, C7 H6 O5, 4(H2 O)'
_chemical_formula_sum            'C14 H22 N4 O11'
_chemical_formula_weight         422.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2022-08-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-12-07 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.662(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.5643(12)
_cell_length_b                   15.1720(14)
_cell_length_c                   13.1988(9)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      72.362
_cell_measurement_theta_min      3.813
_cell_volume                     3596.5(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8VENTURE'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15585
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         3.814
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1019 before and 0.0410 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
The \l/2 correction factor is Not present.
;
_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    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0827P)^2^+3.5363P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3049
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00762f2.cif
_cod_data_source_block           cu_220811_10_0m
_cod_depositor_comments
'Adding full bibliography for 7247410--7247413.cif.'
_cod_database_code               7247410
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.798
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
O9 \\sim O5: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
O11 \\sim O3: within 2A with sigma of 0.004 and sigma for terminal atoms of
0.008 within 2A
3. Others
 Sof(O5)=Sof(H5A)=Sof(H5B)=1-FVAR(1)
 Sof(O9)=Sof(H9D)=Sof(H9E)=FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(H3B)=1-FVAR(2)
 Sof(O11)=Sof(H11A)=Sof(H11B)=FVAR(2)
4.a Riding coordinates:
 O13(H13D,H13E), O2(H2A,H2B), O9(H9D,H9E), O5(H5A,H5B), O11(H11A,H11B), O3(H3A,
 H3B)
4.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C6(H6), C11(H11)
4.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
4.d Idealised tetrahedral OH refined as rotating group:
 O8(H8), O10(H10), O12(H12), O7(H7)
;
_shelx_res_checksum              34217
_olex2_submission_special_instructions 'No special instructions were received'