Synthesis and Characterization of a (−)-Epicatechin and Barbituric Acid Cocrystal: Single-Crystal X-ray Diffraction and Vibrational Spectroscopic Studies
Budziak-Wieczorek, Iwona; Maciołek, Urszula; ACS Omega 6 (2021) 8199–8209; doi:10.1021/acsomega.0c06239

data_4518551
_publ_section_title
;
 Synthesis and Characterization of a (&#x2212;)-Epicatechin and Barbituric
 Acid Cocrystal: Single-Crystal X-ray Diffraction and Vibrational
 Spectroscopic Studies
;
_journal_issue                   12
_journal_name_full               'ACS Omega'
_journal_page_first              8199
_journal_page_last               8209
_journal_paper_doi               10.1021/acsomega.0c06239
_journal_volume                  6
_journal_year                    2021
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C15 H14 O6, C4 H4 N2 O3, 1.5(H2 O)'
_chemical_formula_sum            'C19 H21 N2 O10.5'
_chemical_formula_weight         445.385
_chemical_name_common            -Epicatechin
_chemical_name_systematic
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc26qc3f
_audit_creation_date             2021-01-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-22 deposited with the CCDC.	2021-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                67.444(6)
_cell_angle_beta                 87.953(5)
_cell_angle_gamma                88.503(5)
_cell_formula_units_Z            2
_cell_length_a                   7.3043(5)
_cell_length_b                   11.8154(8)
_cell_length_c                   12.0064(6)
_cell_measurement_reflns_used    4168
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      3.9580
_cell_volume                     956.23(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 5.2763
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9609
_diffrn_measurement_details
;
  1 omega  -26.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9396  -37.0000  -30.0000 91
  2 omega   35.00   77.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -45.0000 -150.0000 42
  3 omega   96.00  134.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -77.0000 -150.0000 38
  4 omega   66.00  148.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969   15.0000  -90.0000 82
  5 omega   95.00  130.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969   45.0000  -60.0000 35
  6 omega   83.00  157.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969   30.0000    0.0000 74
  7 omega   79.00  109.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -94.0000    0.0000 30
  8 omega   59.00  105.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -94.0000 -120.0000 46
  9 omega   44.00   71.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -45.0000    0.0000 27
 10 omega   32.00   69.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -30.0000   60.0000 37
 11 omega   40.00   77.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -45.0000  120.0000 37
 12 omega   46.00   93.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -94.0000   90.0000 47
 13 omega   45.00  108.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -94.0000  150.0000 63
 14 omega   33.00   61.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -30.0000   90.0000 28
 15 omega   32.00   67.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -30.0000   30.0000 35
 16 omega   31.00   64.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -30.0000  -30.0000 33
 17 omega   31.00   64.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969  -77.0000 -150.0000 33
 18 omega   31.00  104.00   1.0000    3.1400
omega____ theta____ kappa____ phi______ frames
    -      106.9969 -111.0000   30.0000 73
 19 omega   18.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.9396   37.0000  150.0000 97
 20 omega  -49.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9396  -57.0000  120.0000 33
 21 omega  -64.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9396   57.0000  -90.0000 91
 22 omega  -94.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9396  125.0000  -30.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.9986
_diffrn_reflns_Laue_measured_fraction_max 0.9609
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6303
_diffrn_reflns_point_group_measured_fraction_full 0.5940
_diffrn_reflns_point_group_measured_fraction_max 0.5675
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.83
_diffrn_reflns_theta_min         3.99
_exptl_absorpt_coefficient_mu    1.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       plate
_exptl_crystal_F_000             467.895
_exptl_crystal_preparation       'Crystallisation from 97% ethanol'
_exptl_crystal_recrystallization_method 'Crystallisation by solvent evaporation'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.1716
_refine_diff_density_min         -0.2661
_refine_diff_density_rms         0.0472
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_d_res_high            0.8027
_refine_ls_d_res_low             11.0837
_refine_ls_goodness_of_fit_ref   1.0800
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     596
_refine_ls_number_reflns         4387
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0800
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0593
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0942P)^2^+0.6138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1779
_reflns_Friedel_coverage         0.174
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              11
_reflns_limit_k_min              -14
_reflns_limit_l_max              10
_reflns_limit_l_min              -14
_reflns_number_gt                4013
_reflns_number_total             4387
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao0c06239_si_002.cif
_cod_data_source_block           epikat_barb2
_cod_depositor_comments
;
          Adding full bibliography for 4518551.cif.

2025-07-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_Hall     ' P 1'
_cod_original_formula_moiety     '2(C15 H14 O6), 2(C4 H4 N2 O3), 3(H2 O)'
_cod_original_formula_sum        'C38 H42 N4 O21'
_cod_original_formula_units_Z    1
_cod_original_formula_weight     890.771
_cod_database_code               4518551
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3E(H6E,H5E), O1E(H2,H1), O2E(H3E,H4E)
2.b Ternary CH refined with riding coordinates:
 C1B(H1B), C2B(H2B), C1A(H1A), C2A(H2A)
2.c Secondary CH2 refined with riding coordinates:
 C3B(H4B,H5B), C3A(H5A,H4A), C3C(H4C,H3C), C3D(H3D,H4D)
2.d Aromatic/amide H refined with riding coordinates:
 C8B(H9B), C6B(H7B), C14B(H13B), C15B(H14B), C15A(H14A), C14A(H13A),
 C11A(H10A), C8A(H9A), C6A(H7A), N1C(H1C), N2C(H2C), N1D(H1D), N2D(H2D)
2.e Idealised tetrahedral OH refined as rotating group:
 O4B(H8B), O5B(H11B), O6B(H12B), O2B(H3B), O6A(H12A), O5A(H11A), O3A(H6A),
 O2A(H3A)
;
_olex2_exptl_crystal_mounting_method 'oil mounted'
_olex2_submission_special_instructions 'No special instructions were received'