#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105170.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_2105170
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Egert, Ernst'
_publ_section_title
;
 Cocrystals of 5-fluorocytosine. II. Coformers with variable
 hydrogen-bonding sites
;
_journal_coeditor_code           GP5053
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              444
_journal_page_last               452
_journal_paper_doi               10.1107/S0108768112029977
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C4 H4 F N3 O, C5 H7 N3 O, H2 O'
_chemical_formula_sum            'C9 H13 F N6 O3'
_chemical_formula_weight         272.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.103(12)
_cell_angle_beta                 93.662(13)
_cell_angle_gamma                95.766(13)
_cell_formula_units_Z            2
_cell_length_a                   5.1193(8)
_cell_length_b                   9.3392(15)
_cell_length_c                   12.4862(19)
_cell_measurement_reflns_used    2601
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      4.02
_cell_volume                     587.63(16)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics
'Mercury (Macrae et al., 2008) and XP (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       ω
_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  0.1813
_diffrn_reflns_av_sigmaI/netI    0.1350
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8436
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.783
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         2070
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.784
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                1124
_reflns_number_total             2070
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gp5053.cif
_cod_data_source_block           IVb
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               2105170
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 -0.0530(5) -0.0477(3) 0.7209(2) 0.0227(6) Uani d . 1 1
C C2 0.1476(6) 0.0437(3) 0.6993(2) 0.0209(7) Uani d . 1 1
N N3 0.2458(5) 0.1631(3) 0.76886(19) 0.0210(6) Uani d . 1 1
H H3 0.376(7) 0.221(3) 0.753(3) 0.025 Uiso d . 1 1
C C4 0.1448(6) 0.2007(3) 0.8679(2) 0.0214(7) Uani d . 1 1
C C5 -0.0698(6) 0.1053(3) 0.8911(2) 0.0246(7) Uani d . 1 1
H H5 -0.1526 0.1242 0.9566 0.030 Uiso calc R 1 1
C C6 -0.1578(6) -0.0146(3) 0.8186(2) 0.0234(7) Uani d . 1 1
N N21 0.2636(6) 0.0212(3) 0.6061(2) 0.0303(7) Uani d D 1 1
H H21A 0.198(7) -0.059(3) 0.565(2) 0.036 Uiso d D 1 1
H H21B 0.402(5) 0.080(3) 0.588(3) 0.036 Uiso d D 1 1
O O41 0.2478(4) 0.3120(2) 0.92671(16) 0.0271(6) Uani d . 1 1
C C61 -0.3800(7) -0.1210(3) 0.8406(3) 0.0306(8) Uani d . 1 1
H H61A -0.3126 -0.2130 0.8522 0.046 Uiso calc R 1 1
H H61B -0.5117 -0.1376 0.7786 0.046 Uiso calc R 1 1
H H61C -0.4612 -0.0823 0.9055 0.046 Uiso calc R 1 1
N N1' 1.0402(5) 0.3988(3) 0.6031(2) 0.0229(6) Uani d . 1 1
H H1' 1.102(7) 0.368(3) 0.541(3) 0.027 Uiso d . 1 1
C C2' 0.8096(6) 0.3209(3) 0.6229(2) 0.0205(7) Uani d . 1 1
N N3' 0.6997(5) 0.3510(2) 0.71785(19) 0.0206(6) Uani d . 1 1
C C4' 0.8169(6) 0.4591(3) 0.7921(2) 0.0190(7) Uani d . 1 1
C C5' 1.0530(6) 0.5391(3) 0.7704(2) 0.0224(7) Uani d . 1 1
C C6' 1.1624(6) 0.5089(3) 0.6769(2) 0.0237(7) Uani d . 1 1
H H6' 1.3208 0.5626 0.6623 0.028 Uiso calc R 1 1
O O21' 0.7045(4) 0.2209(2) 0.55116(16) 0.0272(5) Uani d . 1 1
N N41' 0.7071(6) 0.4875(3) 0.8843(2) 0.0280(7) Uani d D 1 1
H H41A 0.558(5) 0.429(3) 0.897(3) 0.034 Uiso d D 1 1
H H41B 0.786(6) 0.557(3) 0.935(2) 0.034 Uiso d D 1 1
F F51' 1.1630(4) 0.64720(19) 0.84809(15) 0.0347(5) Uani d . 1 1
O O1W -0.2989(5) -0.3032(2) 0.58184(18) 0.0283(5) Uani d D 1 1
H H1W -0.439(5) -0.276(3) 0.545(2) 0.034 Uiso d D 1 1
H H2W -0.207(6) -0.228(3) 0.623(2) 0.034 Uiso d D 1 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'
F F 0.0171 0.0103 '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
C2 N1 C6 116.2(2)
N1 C2 N21 120.9(3)
N1 C2 N3 122.5(3)
N21 C2 N3 116.6(3)
C2 N3 C4 123.0(3)
C2 N3 H3 120(2)
C4 N3 H3 117(2)
O41 C4 N3 118.6(3)
O41 C4 C5 126.5(3)
N3 C4 C5 114.9(3)
C6 C5 C4 119.5(3)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 N1 123.8(3)
C5 C6 C61 121.6(3)
N1 C6 C61 114.6(3)
C2 N21 H21A 113(2)
C2 N21 H21B 124(2)
H21A N21 H21B 123(3)
C6 C61 H61A 109.5
C6 C61 H61B 109.5
H61A C61 H61B 109.5
C6 C61 H61C 109.5
H61A C61 H61C 109.5
H61B C61 H61C 109.5
C6' N1' C2' 121.5(3)
C6' N1' H1' 125(2)
C2' N1' H1' 114(2)
O21' C2' N3' 121.1(3)
O21' C2' N1' 118.6(3)
N3' C2' N1' 120.3(3)
C4' N3' C2' 119.3(3)
N41' C4' N3' 118.6(3)
N41' C4' C5' 121.5(3)
N3' C4' C5' 119.8(3)
C6' C5' F51' 121.7(3)
C6' C5' C4' 120.9(3)
F51' C5' C4' 117.4(3)
C5' C6' N1' 118.1(3)
C5' C6' H6' 120.9
N1' C6' H6' 120.9
C4' N41' H41A 119(2)
C4' N41' H41B 119(2)
H41A N41' H41B 122(3)
H1W O1W H2W 112(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.331(4)
N1 C6 1.377(4)
C2 N21 1.343(4)
C2 N3 1.358(4)
N3 C4 1.390(4)
N3 H3 0.87(3)
C4 O41 1.244(3)
C4 C5 1.411(4)
C5 C6 1.368(4)
C5 H5 0.9500
C6 C61 1.496(4)
N21 H21A 0.871(18)
N21 H21B 0.910(18)
C61 H61A 0.9800
C61 H61B 0.9800
C61 H61C 0.9800
N1' C6' 1.363(4)
N1' C2' 1.376(4)
N1' H1' 0.88(3)
C2' O21' 1.262(3)
C2' N3' 1.355(4)
N3' C4' 1.347(4)
C4' N41' 1.323(4)
C4' C5' 1.415(4)
C5' C6' 1.338(4)
C5' F51' 1.361(3)
C6' H6' 0.9500
N41' H41A 0.924(18)
N41' H41B 0.893(18)
O1W H1W 0.898(18)
O1W H2W 0.891(18)
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
N3 H3 N3' . 0.87(3) 2.06(3) 2.921(3) 177(3)
N21 H21A O21' 2_656 0.871(18) 2.09(3) 2.831(3) 143(3)
N21 H21B O21' . 0.910(18) 2.043(19) 2.952(4) 177(3)
N1' H1' O1W 2_656 0.88(3) 1.96(3) 2.829(3) 170(3)
N41' H41A O41 . 0.924(18) 1.922(19) 2.845(4) 178(3)
N41' H41B O41 2_667 0.893(18) 2.02(2) 2.807(3) 146(3)
O1W H1W O21' 2_556 0.898(18) 1.913(19) 2.803(3) 171(3)
O1W H2W N1 . 0.891(18) 2.013(19) 2.896(3) 171(3)
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
C6 N1 C2 N21 -179.9(3)
C6 N1 C2 N3 0.1(4)
N1 C2 N3 C4 -0.4(5)
N21 C2 N3 C4 179.6(3)
C2 N3 C4 O41 179.8(3)
C2 N3 C4 C5 -0.3(4)
O41 C4 C5 C6 -178.8(3)
N3 C4 C5 C6 1.2(4)
C4 C5 C6 N1 -1.7(5)
C4 C5 C6 C61 178.4(3)
C2 N1 C6 C5 1.0(5)
C2 N1 C6 C61 -179.1(3)
C6' N1' C2' O21' 179.5(3)
C6' N1' C2' N3' -0.9(5)
O21' C2' N3' C4' -179.6(3)
N1' C2' N3' C4' 0.8(4)
C2' N3' C4' N41' 179.8(3)
C2' N3' C4' C5' -0.3(4)
N41' C4' C5' C6' 179.8(3)
N3' C4' C5' C6' -0.1(5)
N41' C4' C5' F51' -0.2(4)
N3' C4' C5' F51' 179.9(3)
F51' C5' C6' N1' 180.0(3)
C4' C5' C6' N1' 0.0(5)
C2' N1' C6' C5' 0.5(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654571
2 PubChem 139064081
