#------------------------------------------------------------------------------
#$Date: 2017-08-25 10:02:23 +0300 (Fri, 25 Aug 2017) $
#$Revision: 199946 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020860.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_2020860
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          '2C5 H6 N2 O2 , C6 H6 O2'
_chemical_formula_moiety         '2(C5 H6 N2 O2), C6 H6 O2'
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34
_chemical_name_common            'Thymine--hydroquinone (2/1)'
_chemical_name_systematic
;
5-Methylpyrimidine-2,4(1H,3H)-dione--benzene-1,4-diol (2/1)
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 97.639(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.204(3)
_cell_length_b                   6.9634(13)
_cell_length_c                   8.4505(15)
_cell_measurement_reflns_used    5536
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      2.89
_cell_volume                     828.4(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 0.997
_diffrn_measured_fraction_theta_max 0.967
_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  0.0158
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9216
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.327
_diffrn_reflns_theta_min         2.894
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.163
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0423
_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)+(0.0761P)²+0.1217P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                1795
_reflns_number_total             1993
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3185sup1_III.cif
_cod_data_source_block           III
_cod_database_code               2020860
_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   0.979
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.05890(8) 0.07119(14) 0.68305(13) 0.0326(2) Uani d 1 . .
C C4 0.16775(7) -0.11392(15) 0.54085(13) 0.0333(2) Uani d 1 . .
C C5 0.20629(8) 0.06465(15) 0.48908(14) 0.0357(3) Uani d 1 . .
C C6 0.16838(8) 0.22928(16) 0.53445(13) 0.0368(3) Uani d 1 . .
H H6 0.1917 0.3451 0.5011 0.044 Uiso calc 1 . .
C C9 0.28532(10) 0.05661(18) 0.38818(19) 0.0506(3) Uani d 1 . .
H H9A 0.3000 0.1842 0.3561 0.076 Uiso calc 1 . .
H H9B 0.2661 -0.0202 0.2951 0.076 Uiso calc 1 . .
H H9C 0.3405 0.0006 0.4486 0.076 Uiso calc 1 . .
N N1 0.09611(7) 0.23300(13) 0.62866(11) 0.0368(2) Uani d 1 . .
H H1N 0.0699(10) -0.201(2) 0.6705(18) 0.050(4) Uiso d 1 . .
N N3 0.09643(6) -0.09626(12) 0.63644(11) 0.0339(2) Uani d 1 . .
H H2N 0.0694(10) 0.340(2) 0.6545(18) 0.047(4) Uiso d 1 . .
O O7 -0.00587(6) 0.07241(10) 0.76821(11) 0.0417(2) Uani d 1 . .
O O8 0.19223(6) -0.27636(11) 0.50584(11) 0.0452(2) Uani d 1 . .
C C10 0.40986(8) -0.46666(16) 0.41857(14) 0.0394(3) Uani d 1 . .
C C11 0.43502(8) -0.39291(17) 0.57083(14) 0.0432(3) Uani d 1 . .
H H11 0.3914 -0.3210 0.6187 0.052 Uiso calc 1 . .
C C12 0.52483(9) -0.42616(17) 0.65162(16) 0.0455(3) Uani d 1 . .
H H12 0.5414 -0.3762 0.7536 0.055 Uiso calc 1 . .
O O13 0.32155(7) -0.43836(14) 0.33328(12) 0.0513(3) Uani d 1 . .
H H3O 0.2831(14) -0.376(3) 0.393(2) 0.074(5) 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 . . 123.04(9)
O7 C2 N3 . . 121.50(9)
N1 C2 N3 . . 115.46(10)
O8 C4 N3 . . 118.33(9)
O8 C4 C5 . . 125.85(10)
N3 C4 C5 . . 115.82(9)
C6 C5 C4 . . 117.64(10)
C6 C5 C9 . . 123.59(10)
C4 C5 C9 . . 118.78(10)
C5 C6 N1 . . 122.51(9)
C5 C6 H6 . . 118.7
N1 C6 H6 . . 118.7
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 . . 122.36(9)
C2 N1 H2N . . 115.1(10)
C6 N1 H2N . . 122.5(10)
C2 N3 C4 . . 126.19(9)
C2 N3 H1N . . 114.3(9)
C4 N3 H1N . . 119.5(9)
O13 C10 C12 . 3_646 117.99(11)
O13 C10 C11 . . 122.52(10)
C12 C10 C11 3_646 . 119.49(11)
C12 C11 C10 . . 120.17(11)
C12 C11 H11 . . 119.9
C10 C11 H11 . . 119.9
C11 C12 C10 . 3_646 120.34(12)
C11 C12 H12 . . 119.8
C10 C12 H12 3_646 . 119.8
C10 O13 H3O . . 110.5(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 O7 . 1.2412(13)
C2 N1 . 1.3509(13)
C2 N3 . 1.3619(13)
C4 O8 . 1.2310(13)
C4 N3 . 1.3825(14)
C4 C5 . 1.4495(14)
C5 C6 . 1.3439(15)
C5 C9 . 1.4983(16)
C6 N1 . 1.3805(14)
C6 H6 . 0.9300
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
N1 H2N . 0.879(16)
N3 H1N . 0.886(17)
C10 O13 . 1.3753(15)
C10 C12 3_646 1.3841(16)
C10 C11 . 1.3873(18)
C11 C12 . 1.3839(17)
C11 H11 . 0.9300
C12 C10 3_646 1.3841(16)
C12 H12 . 0.9300
O13 H3O . 0.91(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 H2N O7 2_556 0.879(16) 2.002(17) 2.8784(12) 174.6(14)
N3 H1N O7 2_546 0.886(17) 1.926(17) 2.8111(12) 176.1(14)
O13 H3O O8 . 0.91(2) 1.84(2) 2.7359(13) 171.6(18)
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 . . . . 177.60(11)
N3 C4 C5 C6 . . . . -1.58(16)
O8 C4 C5 C9 . . . . -2.16(19)
N3 C4 C5 C9 . . . . 178.65(10)
C4 C5 C6 N1 . . . . 0.82(17)
C9 C5 C6 N1 . . . . -179.42(11)
O7 C2 N1 C6 . . . . 179.78(10)
N3 C2 N1 C6 . . . . -1.05(16)
C5 C6 N1 C2 . . . . 0.56(18)
O7 C2 N3 C4 . . . . 179.34(10)
N1 C2 N3 C4 . . . . 0.15(17)
O8 C4 N3 C2 . . . . -178.10(10)
C5 C4 N3 C2 . . . . 1.15(17)
O13 C10 C11 C12 . . . . 179.81(11)
C12 C10 C11 C12 3_646 . . . 0.1(2)
C10 C11 C12 C10 . . . 3_646 -0.1(2)

_cod_database_fobs_code 2020860
