#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:35:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020861.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020861
loop_
_publ_author_name
'Sridhar, Balasubramanian'
'Nanubolu, Jagadeesh Babu'
'Ravikumar, Krishnan'
_publ_section_title
;
 Four cocrystals of thymine with phenolic coformers: influence of the
 coformer on hydrogen bonding
;
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_page_first              602
_journal_paper_doi               10.1107/S2053229615011614
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C5 H6 N2 O2 , 2C6 H6 O3'
_chemical_formula_moiety         'C5 H6 N2 O2, 2(C6 H6 O3)'
_chemical_formula_sum            'C17 H18 N2 O8'
_chemical_formula_weight         378.33
_chemical_name_common            'Thymine--pyrogallol (1/2)'
_chemical_name_systematic
;
5-Methylpyrimidine-2,4(1H,3H)-dione--benzene-1,2,3-triol (1/2)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                97.218(3)
_cell_angle_beta                 99.189(3)
_cell_angle_gamma                108.549(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9652(13)
_cell_length_b                   10.2125(19)
_cell_length_c                   12.951(2)
_cell_measurement_reflns_used    5658
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.02
_cell_measurement_theta_min      2.92
_cell_volume                     846.7(3)
_computing_cell_refinement
;
SAINT (Bruker, 2001)
;
_computing_data_collection
;
SMART (Bruker, 2001)
;
_computing_data_reduction
;
SAINT (Bruker, 2001)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 2005)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9492
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.058
_diffrn_reflns_theta_min         1.622
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_description       plate
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.214
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0427
_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/[σ²(Fo²)+(0.0811P)²+0.1267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1311
_reflns_number_gt                3295
_reflns_number_total             3876
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3185sup1_IV.cif
_cod_data_source_block           IV
_cod_database_code               2020861
_cod_database_fobs_code          2020861
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C2 0.3691(2) 0.78633(13) 0.46045(10) 0.0347(3) Uani d 1 . .
C C4 0.33483(19) 0.79165(13) 0.26989(10) 0.0318(3) Uani d 1 . .
C C5 0.24976(19) 0.63993(13) 0.24749(10) 0.0344(3) Uani d 1 . .
C C6 0.2361(2) 0.57387(14) 0.33104(11) 0.0389(3) Uani d 1 . .
H H6 0.1848 0.4761 0.3179 0.047 Uiso calc 1 . .
C C9 0.1803(2) 0.56287(15) 0.13386(11) 0.0437(3) Uani d 1 . .
H H9A 0.1270 0.4635 0.1323 0.065 Uiso calc 1 . .
H H9B 0.2959 0.5844 0.0994 0.065 Uiso calc 1 . .
H H9C 0.0738 0.5916 0.0973 0.065 Uiso calc 1 . .
N N1 0.2946(2) 0.64448(12) 0.43483(9) 0.0400(3) Uani d 1 . .
H H1N 0.297(3) 0.602(2) 0.4876(16) 0.056(5) Uiso d 1 . .
N N3 0.38754(18) 0.85454(11) 0.37635(8) 0.0349(3) Uani d 1 . .
H H2N 0.443(3) 0.951(2) 0.3935(14) 0.051(5) Uiso d 1 . .
O O7 0.41733(18) 0.85216(10) 0.55386(7) 0.0448(3) Uani d 1 . .
O O8 0.36205(16) 0.86785(10) 0.20225(7) 0.0415(2) Uani d 1 . .
C C10A 0.0768(2) 0.84928(13) 0.75311(10) 0.0338(3) Uani d 1 . .
C C11A 0.24804(18) 0.84800(12) 0.82449(9) 0.0304(3) Uani d 1 . .
C C12A 0.2351(2) 0.83645(13) 0.92954(10) 0.0335(3) Uani d 1 . .
C C13A 0.0518(2) 0.83135(14) 0.96268(11) 0.0397(3) Uani d 1 . .
H H13A 0.0425 0.8258 1.0329 0.048 Uiso calc 1 . .
C C14A -0.1163(2) 0.83453(16) 0.89047(12) 0.0437(3) Uani d 1 . .
H H14A -0.2376 0.8315 0.9131 0.052 Uiso calc 1 . .
C C15A -0.1064(2) 0.84208(15) 0.78540(12) 0.0415(3) Uani d 1 . .
H H15A -0.2206 0.8423 0.7372 0.050 Uiso calc 1 . .
O O16A 0.08891(17) 0.86224(11) 0.64914(7) 0.0415(2) Uani d 1 . .
H H1O 0.205(4) 0.852(2) 0.6359(17) 0.069(6) Uiso d 1 . .
O O17A 0.42668(14) 0.85211(10) 0.78862(7) 0.0353(2) Uani d 1 . .
H H2O 0.504(3) 0.942(2) 0.7919(14) 0.049(5) Uiso d 1 . .
O O18A 0.40493(16) 0.83019(12) 0.99403(8) 0.0452(3) Uani d 1 . .
H H3O 0.389(3) 0.833(2) 1.0608(16) 0.055(5) Uiso d 1 . .
C C10B 0.2995(2) 0.48722(14) 0.69600(11) 0.0370(3) Uani d 1 . .
C C11B 0.2169(2) 0.36068(14) 0.62317(10) 0.0357(3) Uani d 1 . .
C C12B 0.1639(2) 0.23452(14) 0.66014(11) 0.0385(3) Uani d 1 . .
C C13B 0.1944(2) 0.23437(15) 0.76864(12) 0.0433(3) Uani d 1 . .
H H13B 0.1599 0.1499 0.7932 0.052 Uiso calc 1 . .
C C14B 0.2767(2) 0.36140(16) 0.84004(11) 0.0434(3) Uani d 1 . .
H H14B 0.2970 0.3615 0.9128 0.052 Uiso calc 1 . .
C C15B 0.3291(2) 0.48821(15) 0.80470(11) 0.0407(3) Uani d 1 . .
H H15B 0.3835 0.5729 0.8532 0.049 Uiso calc 1 . .
O O16B 0.3469(2) 0.60497(11) 0.65181(9) 0.0547(3) Uani d 1 . .
H H4O 0.390(3) 0.674(2) 0.6982(17) 0.060(6) Uiso d 1 . .
O O17B 0.19057(19) 0.36604(12) 0.51664(8) 0.0487(3) Uani d 1 . .
H H5O 0.127(4) 0.287(3) 0.4805(19) 0.076(7) Uiso d 1 . .
O O18B 0.0806(2) 0.11680(11) 0.58150(9) 0.0582(3) Uani d 1 . .
H H6O 0.070(3) 0.047(3) 0.6076(17) 0.070(6) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O7 C2 N1 . . 123.07(12)
O7 C2 N3 . . 121.49(12)
N1 C2 N3 . . 115.45(11)
O8 C4 N3 . . 118.63(11)
O8 C4 C5 . . 125.50(12)
N3 C4 C5 . . 115.87(11)
C6 C5 C4 . . 117.53(11)
C6 C5 C9 . . 122.94(12)
C4 C5 C9 . . 119.53(12)
C5 C6 N1 . . 122.91(12)
C5 C6 H6 . . 118.5
N1 C6 H6 . . 118.5
C5 C9 H9A . . 109.5
C5 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C5 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C2 N1 C6 . . 122.16(12)
C2 N1 H1N . . 115.2(14)
C6 N1 H1N . . 122.4(14)
C2 N3 C4 . . 126.04(11)
C2 N3 H2N . . 115.8(11)
C4 N3 H2N . . 118.2(11)
O16A C10A C15A . . 118.78(12)
O16A C10A C11A . . 120.24(12)
C15A C10A C11A . . 120.95(12)
O17A C11A C10A . . 119.23(11)
O17A C11A C12A . . 120.88(11)
C10A C11A C12A . . 119.83(11)
O18A C12A C11A . . 116.90(11)
O18A C12A C13A . . 123.79(12)
C11A C12A C13A . . 119.31(12)
C14A C13A C12A . . 119.87(12)
C14A C13A H13A . . 120.1
C12A C13A H13A . . 120.1
C15A C14A C13A . . 121.10(13)
C15A C14A H14A . . 119.4
C13A C14A H14A . . 119.4
C14A C15A C10A . . 118.89(13)
C14A C15A H15A . . 120.6
C10A C15A H15A . . 120.6
C10A O16A H1O . . 109.7(14)
C11A O17A H2O . . 108.6(11)
C12A O18A H3O . . 110.7(12)
O16B C10B C15B . . 124.48(13)
O16B C10B C11B . . 114.95(12)
C15B C10B C11B . . 120.57(12)
O17B C11B C12B . . 122.51(12)
O17B C11B C10B . . 118.05(12)
C12B C11B C10B . . 119.44(12)
O18B C12B C13B . . 125.14(13)
O18B C12B C11B . . 114.43(13)
C13B C12B C11B . . 120.43(13)
C14B C13B C12B . . 119.35(13)
C14B C13B H13B . . 120.3
C12B C13B H13B . . 120.3
C15B C14B C13B . . 121.05(13)
C15B C14B H14B . . 119.5
C13B C14B H14B . . 119.5
C14B C15B C10B . . 119.16(13)
C14B C15B H15B . . 120.4
C10B C15B H15B . . 120.4
C10B O16B H4O . . 109.6(14)
C11B O17B H5O . . 110.4(16)
C12B O18B H6O . . 109.7(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 O7 . 1.2452(16)
C2 N1 . 1.3505(17)
C2 N3 . 1.3663(16)
C4 O8 . 1.2407(15)
C4 N3 . 1.3836(16)
C4 C5 . 1.4436(18)
C5 C6 . 1.3456(19)
C5 C9 . 1.5028(18)
C6 N1 . 1.3739(17)
C6 H6 . 0.9300
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
N1 H1N . 0.85(2)
N3 H2N . 0.92(2)
C10A O16A . 1.3827(16)
C10A C15A . 1.388(2)
C10A C11A . 1.3921(18)
C11A O17A . 1.3864(15)
C11A C12A . 1.3951(17)
C12A O18A . 1.3592(16)
C12A C13A . 1.3982(19)
C13A C14A . 1.389(2)
C13A H13A . 0.9300
C14A C15A . 1.384(2)
C14A H14A . 0.9300
C15A H15A . 0.9300
O16A H1O . 0.89(2)
O17A H2O . 0.90(2)
O18A H3O . 0.89(2)
C10B O16B . 1.3650(17)
C10B C15B . 1.3881(19)
C10B C11B . 1.3922(19)
C11B O17B . 1.3729(16)
C11B C12B . 1.3908(19)
C12B O18B . 1.3708(17)
C12B C13B . 1.388(2)
C13B C14B . 1.387(2)
C13B H13B . 0.9300
C14B C15B . 1.386(2)
C14B H14B . 0.9300
C15B H15B . 0.9300
O16B H4O . 0.81(2)
O17B H5O . 0.83(3)
O18B H6O . 0.82(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1N O16B . 0.85(2) 2.09(2) 2.8713(17) 151(2)
N1 H1N O17B . 0.85(2) 2.38(2) 3.0701(16) 138(2)
N3 H2N O7 2_676 0.92(2) 1.91(2) 2.8237(16) 172(2)
O16A H1O O7 . 0.89(2) 1.95(2) 2.7903(16) 156(2)
O16A H1O O17A . 0.89(2) 2.31(2) 2.7665(14) 112(2)
O17A H2O O8 2_676 0.90(2) 1.85(2) 2.7460(15) 174(2)
O18A H3O O8 1_556 0.89(2) 1.87(2) 2.7530(14) 172(2)
O16B H4O O17A . 0.81(2) 1.96(2) 2.7364(15) 163(2)
O17B H5O O16A 2_566 0.83(3) 2.12(3) 2.8904(15) 155(2)
O17B H5O O18B . 0.83(3) 2.27(2) 2.6970(16) 112(2)
O18B H6O O16A 1_545 0.82(2) 2.06(2) 2.8602(16) 166(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
O8 C4 C5 C6 . . . . 178.31(13)
N3 C4 C5 C6 . . . . -2.22(18)
O8 C4 C5 C9 . . . . -1.9(2)
N3 C4 C5 C9 . . . . 177.60(12)
C4 C5 C6 N1 . . . . 1.6(2)
C9 C5 C6 N1 . . . . -178.25(13)
O7 C2 N1 C6 . . . . 177.90(13)
N3 C2 N1 C6 . . . . -1.7(2)
C5 C6 N1 C2 . . . . 0.5(2)
O7 C2 N3 C4 . . . . -178.71(13)
N1 C2 N3 C4 . . . . 0.9(2)
O8 C4 N3 C2 . . . . -179.45(12)
C5 C4 N3 C2 . . . . 1.05(19)
O16A C10A C11A O17A . . . . -3.50(18)
C15A C10A C11A O17A . . . . 178.53(12)
O16A C10A C11A C12A . . . . 179.29(11)
C15A C10A C11A C12A . . . . 1.32(19)
O17A C11A C12A O18A . . . . 0.30(18)
C10A C11A C12A O18A . . . . 177.46(11)
O17A C11A C12A C13A . . . . -179.43(11)
C10A C11A C12A C13A . . . . -2.27(18)
O18A C12A C13A C14A . . . . -178.23(13)
C11A C12A C13A C14A . . . . 1.5(2)
C12A C13A C14A C15A . . . . 0.3(2)
C13A C14A C15A C10A . . . . -1.3(2)
O16A C10A C15A C14A . . . . -177.56(13)
C11A C10A C15A C14A . . . . 0.4(2)
O16B C10B C11B O17B . . . . -0.37(19)
C15B C10B C11B O17B . . . . 179.85(13)
O16B C10B C11B C12B . . . . 179.83(13)
C15B C10B C11B C12B . . . . 0.0(2)
O17B C11B C12B O18B . . . . -1.0(2)
C10B C11B C12B O18B . . . . 178.84(13)
O17B C11B C12B C13B . . . . 179.69(13)
C10B C11B C12B C13B . . . . -0.5(2)
O18B C12B C13B C14B . . . . -178.74(15)
C11B C12B C13B C14B . . . . 0.5(2)
C12B C13B C14B C15B . . . . -0.1(2)
C13B C14B C15B C10B . . . . -0.4(2)
O16B C10B C15B C14B . . . . -179.37(14)
C11B C10B C15B C14B . . . . 0.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139062542
