#------------------------------------------------------------------------------
#$Date: 2017-08-25 10:02:13 +0300 (Fri, 25 Aug 2017) $
#$Revision: 199945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/08/2020859.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_2020859
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--catechol (2/1)'
_chemical_name_systematic
;
5-Methylpyrimidine-2,4(1H,3H)-dione--benzene-1,3-diol (2/1)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9499(7)
_cell_length_b                   9.0237(10)
_cell_length_c                   26.828(3)
_cell_measurement_reflns_used    5292
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      3.04
_cell_volume                     1682.5(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 1.000
_diffrn_measured_fraction_theta_max 0.984
_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  0.0269
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18036
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.286
_diffrn_reflns_theta_min         1.518
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.98
_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    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.242
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0604P)²+0.6359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1804
_reflns_number_total             2053
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3185sup1_II.cif
_cod_data_source_block           II
_cod_database_code               2020859
_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   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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 -0.07636(19) 0.32869(16) 0.47064(5) 0.0316(3) Uani d 1 . .
C C4 0.1030(2) 0.49840(16) 0.41648(5) 0.0325(3) Uani d 1 . .
C C5 -0.0782(2) 0.54865(18) 0.39597(6) 0.0375(4) Uani d 1 . .
C C6 -0.2403(2) 0.49198(18) 0.41510(6) 0.0390(4) Uani d 1 . .
H H6 -0.3578 0.5258 0.4030 0.047 Uiso calc 1 . .
C C9 -0.0753(3) 0.6606(2) 0.35470(8) 0.0594(5) Uani d 1 . .
H H9A -0.2047 0.6891 0.3467 0.089 Uiso calc 1 . .
H H9B -0.0152 0.6181 0.3258 0.089 Uiso calc 1 . .
H H9C -0.0040 0.7462 0.3652 0.089 Uiso calc 1 . .
N N1 -0.24038(19) 0.38586(15) 0.45190(5) 0.0377(3) Uani d 1 . .
H H1N -0.346(3) 0.354(2) 0.4646(7) 0.048(5) Uiso d 1 . .
N N3 0.08942(17) 0.38759(14) 0.45211(5) 0.0331(3) Uani d 1 . .
H H2N 0.195(3) 0.355(2) 0.4653(7) 0.041(5) Uiso d 1 . .
O O7 -0.07500(14) 0.23058(13) 0.50296(4) 0.0413(3) Uani d 1 . .
O O8 0.26309(15) 0.54574(14) 0.40549(4) 0.0425(3) Uani d 1 . .
C C10 0.5000 0.7480(2) 0.2500 0.0400(5) Uani d 1 . .
H H10 0.5000 0.8510 0.2500 0.048 Uiso calc 1 . .
C C11 0.4423(2) 0.67069(18) 0.29187(6) 0.0372(4) Uani d 1 . .
C C12 0.4383(3) 0.51775(19) 0.29181(7) 0.0509(5) Uani d 1 . .
H H12 0.3946 0.4659 0.3195 0.061 Uiso calc 1 . .
C C13 0.5000 0.4434(3) 0.2500 0.0655(8) Uani d 1 . .
H H13 0.5000 0.3403 0.2500 0.079 Uiso calc 1 . .
O O14 0.3922(2) 0.74992(15) 0.33346(5) 0.0522(4) Uani d 1 . .
H H1O 0.346(4) 0.687(3) 0.3553(9) 0.075(7) 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 . . 122.73(13)
O7 C2 N3 . . 121.83(13)
N1 C2 N3 . . 115.44(13)
O8 C4 N3 . . 118.57(13)
O8 C4 C5 . . 126.03(13)
N3 C4 C5 . . 115.39(12)
C6 C5 C4 . . 117.83(14)
C6 C5 C9 . . 123.46(14)
C4 C5 C9 . . 118.71(13)
C5 C6 N1 . . 122.74(13)
C5 C6 H6 . . 118.6
N1 C6 H6 . . 118.6
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 . . 122.26(13)
C2 N1 H1N . . 116.5(13)
C6 N1 H1N . . 121.2(13)
C2 N3 C4 . . 126.18(12)
C2 N3 H2N . . 116.0(12)
C4 N3 H2N . . 117.7(12)
C11 C10 C11 3_655 . 119.4(2)
C11 C10 H10 3_655 . 120.3
C11 C10 H10 . . 120.3
O14 C11 C12 . . 121.17(15)
O14 C11 C10 . . 118.19(15)
C12 C11 C10 . . 120.63(15)
C13 C12 C11 . . 118.84(17)
C13 C12 H12 . . 120.6
C11 C12 H12 . . 120.6
C12 C13 C12 3_655 . 121.6(2)
C12 C13 H13 3_655 . 119.2
C12 C13 H13 . . 119.2
C11 O14 H1O . . 107.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C2 O7 . 1.2393(18)
C2 N1 . 1.3485(18)
C2 N3 . 1.3627(18)
C4 O8 . 1.2276(17)
C4 N3 . 1.3867(19)
C4 C5 . 1.447(2)
C5 C6 . 1.340(2)
C5 C9 . 1.499(2)
C6 N1 . 1.375(2)
C6 H6 . 0.9300
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
N1 H1N . 0.86(2)
N3 H2N . 0.86(2)
C10 C11 3_655 1.3817(19)
C10 C11 . 1.3818(19)
C10 H10 . 0.9300
C11 O14 . 1.3701(19)
C11 C12 . 1.380(2)
C12 C13 . 1.376(2)
C12 H12 . 0.9300
C13 C12 3_655 1.376(2)
C13 H13 . 0.9300
O14 H1O . 0.88(3)
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 O7 4_456 0.86(2) 1.97(2) 2.8247(17) 175(2)
N3 H2N O7 4_556 0.86(2) 1.97(2) 2.8336(16) 176(2)
O14 H1O O8 . 0.88(3) 1.94(3) 2.8167(17) 175(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 . . . . -175.07(16)
N3 C4 C5 C6 . . . . 4.2(2)
O8 C4 C5 C9 . . . . 4.9(3)
N3 C4 C5 C9 . . . . -175.78(16)
C4 C5 C6 N1 . . . . -2.1(2)
C9 C5 C6 N1 . . . . 177.90(18)
O7 C2 N1 C6 . . . . -178.27(15)
N3 C2 N1 C6 . . . . 2.6(2)
C5 C6 N1 C2 . . . . -1.5(3)
O7 C2 N3 C4 . . . . -179.22(14)
N1 C2 N3 C4 . . . . -0.1(2)
O8 C4 N3 C2 . . . . 176.05(14)
C5 C4 N3 C2 . . . . -3.3(2)
C11 C10 C11 O14 3_655 . . . 177.76(16)
C11 C10 C11 C12 3_655 . . . -1.30(12)
O14 C11 C12 C13 . . . . -176.48(14)
C10 C11 C12 C13 . . . . 2.6(2)
C11 C12 C13 C12 . . . 3_655 -1.26(12)

_cod_database_fobs_code 2020859
