#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/25/4502584.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4502584
loop_
_publ_author_name
'Lee, Tu'
'Wang, Pu Yun'
_publ_section_title
;
 Screening, Manufacturing, Photoluminescence, and Molecular Recognition of
 Co-Crystals: Cytosine with Dicarboxylic Acids
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1419
_journal_paper_doi               10.1021/cg901412d
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C9 H13 N6 O5'
_chemical_formula_weight         285.25
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.689(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.5157(2)
_cell_length_b                   15.1368(6)
_cell_length_c                   12.6989(5)
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.5
_cell_volume                     1226.48(8)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Bruker APEX2'
_computing_publication_material  'Bruker APEX2'
_computing_structure_refinement  'Shelxtl-97 (Sheldrick, 2008)'
_computing_structure_solution    'Shelxtl-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10466
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6885
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0940
_refine_ls_R_factor_gt           0.0779
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1534P)²+1.1441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2414
_refine_ls_wR_factor_ref         0.2588
_reflns_number_gt                1914
_reflns_number_total             2494
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901412d_si_003.cif
_cod_data_source_block           090412_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4502584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4650(5) 0.3450(2) 0.4831(3) 0.0438(7) Uani 1 1 d .
C2 C 0.4932(5) 0.4101(2) 0.6564(2) 0.0439(7) Uani 1 1 d .
C3 C 0.4748(6) 0.3242(2) 0.7023(3) 0.0547(9) Uani 1 1 d .
H3 H 0.4775 0.3169 0.7753 0.066 Uiso 1 1 calc R
C4 C 0.4539(6) 0.2556(2) 0.6349(3) 0.0539(9) Uani 1 1 d .
H4 H 0.4416 0.1993 0.6622 0.065 Uiso 1 1 calc R
C5 C 0.0438(5) 0.6506(3) 0.5566(3) 0.0543(9) Uani 1 1 d .
C6 C 0.0491(6) 0.6832(3) 0.7397(3) 0.0623(10) Uani 1 1 d .
H6 H 0.0581 0.7271 0.7917 0.075 Uiso 1 1 calc R
C7 C 0.0332(6) 0.6007(3) 0.7711(3) 0.0602(9) Uani 1 1 d .
H7 H 0.0295 0.5855 0.8416 0.072 Uiso 1 1 calc R
C8 C 0.0219(5) 0.5353(3) 0.6855(3) 0.0540(9) Uani 1 1 d .
C9 C 0.5627(5) 0.5433(2) 0.0046(3) 0.0472(8) Uani 1 1 d .
N1 N 0.4848(4) 0.41817(17) 0.5507(2) 0.0413(6) Uani 1 1 d .
N2 N 0.4498(5) 0.26475(18) 0.5291(2) 0.0510(7) Uani 1 1 d .
H2 H 0.4371 0.2183 0.4893 0.061 Uiso 1 1 calc R
N3 N 0.5168(4) 0.48150(19) 0.7150(2) 0.0504(7) Uani 1 1 d .
H3A H 0.5266 0.5321 0.6856 0.060 Uiso 1 1 calc R
H3B H 0.5227 0.4780 0.7831 0.060 Uiso 1 1 calc R
N4 N 0.0266(4) 0.5585(2) 0.5867(2) 0.0491(7) Uani 1 1 d .
N5 N 0.0535(5) 0.7091(2) 0.6383(3) 0.0636(9) Uani 1 1 d .
H5 H 0.0627 0.7645 0.6252 0.076 Uiso 1 1 calc R
N6 N 0.0040(5) 0.4513(2) 0.7027(3) 0.0623(9) Uani 1 1 d .
H6A H -0.0041 0.4144 0.6506 0.075 Uiso 1 1 calc R
H6B H 0.0001 0.4326 0.7662 0.075 Uiso 1 1 calc R
O1 O 0.4608(4) 0.35245(16) 0.38600(19) 0.0543(6) Uani 1 1 d .
O2 O 0.0471(4) 0.67121(18) 0.4662(2) 0.0650(8) Uani 1 1 d .
O3 O 0.7035(4) 0.54919(19) -0.0485(2) 0.0702(8) Uani 1 1 d .
O4 O 0.5134(6) 0.60175(17) 0.0632(3) 0.0749(9) Uani 1 1 d .
H4A H 0.3855 0.6071 0.0509 0.112 Uiso 1 1 calc R
O5 O 0.0598(4) 0.88596(18) 0.5853(2) 0.0612(7) Uani 1 1 d .
H1W H -0.0424 0.9025 0.5389 0.080 Uiso 1 1 d .
H2W H 0.1841 0.9119 0.5711 0.080 Uiso 1 1 d .
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'
O O 0.0106 0.0060 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
O1 C1 N2 121.5(3) .
O1 C1 N1 121.7(3) .
N2 C1 N1 116.9(3) .
N3 C2 N1 118.3(3) .
N3 C2 C3 121.8(3) .
N1 C2 C3 119.9(3) .
C4 C3 C2 116.7(3) .
C4 C3 H3 121.7 .
C2 C3 H3 121.7 .
C3 C4 N2 122.6(3) .
C3 C4 H4 118.7 .
N2 C4 H4 118.7 .
O2 C5 N5 123.9(4) .
O2 C5 N4 121.3(3) .
N5 C5 N4 114.7(3) .
C7 C6 N5 125.4(4) .
C7 C6 H6 117.3 .
N5 C6 H6 117.3 .
C6 C7 C8 114.3(4) .
C6 C7 H7 122.9 .
C8 C7 H7 122.9 .
N6 C8 N4 116.4(3) .
N6 C8 C7 122.0(4) .
N4 C8 C7 121.6(4) .
O4 C9 O3 125.5(3) .
O4 C9 C9 117.1(3) 3_665
O3 C9 C9 117.3(3) 3_665
C2 N1 C1 121.8(3) .
C4 N2 C1 122.1(3) .
C4 N2 H2 118.9 .
C1 N2 H2 118.9 .
C2 N3 H3A 120.0 .
C2 N3 H3B 120.0 .
H3A N3 H3B 120.0 .
C8 N4 C5 121.8(3) .
C6 N5 C5 122.2(4) .
C6 N5 H5 118.9 .
C5 N5 H5 118.9 .
C8 N6 H6A 120.0 .
C8 N6 H6B 120.0 .
H6A N6 H6B 120.0 .
C9 O4 H4A 109.5 .
H1W O5 H2W 109.4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.233(4) .
C1 N2 1.360(4) .
C1 N1 1.391(4) .
C2 N3 1.304(4) .
C2 N1 1.337(4) .
C2 C3 1.440(5) .
C3 C4 1.335(5) .
C3 H3 0.9300 .
C4 N2 1.345(5) .
C4 H4 0.9300 .
C5 O2 1.194(5) .
C5 N5 1.355(5) .
C5 N4 1.456(5) .
C6 C7 1.321(6) .
C6 N5 1.352(5) .
C6 H6 0.9300 .
C7 C8 1.461(5) .
C7 H7 0.9300 .
C8 N6 1.300(5) .
C8 N4 1.309(5) .
C9 O4 1.240(4) .
C9 O3 1.246(4) .
C9 C9 1.536(6) 3_665
N2 H2 0.8600 .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N5 H5 0.8600 .
N6 H6A 0.8600 .
N6 H6B 0.8600 .
O4 H4A 0.8200 .
O5 H1W 0.8334 .
O5 H2W 0.9493 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144973
