#------------------------------------------------------------------------------
#$Date: 2025-08-19 12:01:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/51/2105165.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_2105165
loop_
_publ_author_name
'Tutughamiarso, Maya'
'Wagner, Guido'
'Egert, Ernst'
_publ_section_title
;
 Cocrystals of 5-fluorocytosine. I. Coformers with fixed hydrogen-bonding
 sites
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              431
_journal_page_last               443
_journal_paper_doi               10.1107/S010876811202561X
_journal_volume                  68
_journal_year                    2012
_chemical_formula_moiety         'C4 H4 F N3 O, C8 H11 N5 O3'
_chemical_formula_sum            'C12 H15 F N8 O4'
_chemical_formula_weight         354.32
_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                 98.155(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.0859(5)
_cell_length_b                   9.0414(5)
_cell_length_c                   22.8754(16)
_cell_measurement_reflns_used    9824
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      3.6
_cell_volume                     1450.73(17)
_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 0.998
_diffrn_measured_fraction_theta_max 0.989
_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  0.0733
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11519
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.52
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.330
_refine_ls_extinction_coef       0.020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.950
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0391
_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)+(0.0688P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0983
_reflns_number_gt                2202
_reflns_number_total             2718
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gp5052.cif
_cod_data_source_block           VII
_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 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1450.73(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2105165
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_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 0.31615(16) 0.63847(13) 0.46492(6) 0.0191(3) Uani d D 1 1
H H1 0.282(2) 0.5820(19) 0.4938(8) 0.028(5) Uiso d D 1 1
C C2 0.38770(19) 0.77873(16) 0.47575(6) 0.0193(3) Uani d . 1 1
N N21 0.4025(2) 0.82458(17) 0.53167(6) 0.0271(3) Uani d . 1 1
H H21A 0.375(3) 0.764(2) 0.5596(9) 0.033(5) Uiso d . 1 1
H H21B 0.447(3) 0.913(2) 0.5402(10) 0.039(5) Uiso d . 1 1
N N3 0.43674(16) 0.86735(13) 0.43384(5) 0.0192(3) Uani d . 1 1
C C4 0.40557(18) 0.80386(16) 0.37951(6) 0.0178(3) Uani d . 1 1
C C5 0.33311(19) 0.66518(16) 0.36467(6) 0.0186(3) Uani d . 1 1
C C6 0.28091(19) 0.57301(15) 0.40952(7) 0.0189(3) Uani d . 1 1
O O61 0.20669(15) 0.44856(11) 0.40312(5) 0.0262(3) Uani d . 1 1
N N7 0.31657(17) 0.64076(14) 0.30431(5) 0.0223(3) Uani d . 1 1
C C8 0.3794(2) 0.76291(16) 0.28366(7) 0.0216(3) Uani d . 1 1
H H8 0.3851 0.7790 0.2429 0.026 Uiso calc R 1 1
N N9 0.43674(16) 0.86634(13) 0.32676(5) 0.0185(3) Uani d . 1 1
C C91 0.49976(19) 1.01439(16) 0.31408(7) 0.0204(3) Uani d . 1 1
H H91A 0.5635 1.0605 0.3509 0.025 Uiso calc R 1 1
H H91B 0.5934 1.0085 0.2859 0.025 Uiso calc R 1 1
O O92 0.34457(14) 1.10231(11) 0.28994(4) 0.0217(3) Uani d . 1 1
C C93 0.2348(2) 1.15385(18) 0.33420(7) 0.0275(4) Uani d . 1 1
H H93A 0.3109 1.2250 0.3607 0.033 Uiso calc R 1 1
H H93B 0.2010 1.0695 0.3583 0.033 Uiso calc R 1 1
C C94 0.0568(2) 1.22747(19) 0.30455(8) 0.0319(4) Uani d . 1 1
H H94A -0.0162 1.1556 0.2776 0.038 Uiso calc R 1 1
H H94B -0.0232 1.2551 0.3350 0.038 Uiso calc R 1 1
O O95 0.09130(19) 1.35572(13) 0.27195(6) 0.0375(3) Uani d . 1 1
H H95 0.1521 1.4178 0.2946 0.045 Uiso calc R 1 1
N N1' 0.20902(18) 0.40773(16) 0.65852(6) 0.0267(3) Uani d . 1 1
H H1' 0.232(3) 0.437(2) 0.6954(11) 0.044(6) Uiso d . 1 1
C C2' 0.2483(2) 0.49881(18) 0.61312(7) 0.0237(3) Uani d . 1 1
O O21' 0.31230(16) 0.62467(13) 0.62475(5) 0.0300(3) Uani d . 1 1
N N3' 0.21615(17) 0.44579(14) 0.55692(6) 0.0231(3) Uani d . 1 1
C C4' 0.14772(19) 0.30924(18) 0.54615(7) 0.0235(3) Uani d . 1 1
N N41' 0.1136(2) 0.25984(17) 0.49089(6) 0.0293(3) Uani d D 1 1
H H41A 0.138(3) 0.319(2) 0.4610(9) 0.050(6) Uiso d D 1 1
H H41B 0.068(3) 0.169(3) 0.4817(10) 0.049(6) Uiso d . 1 1
C C5' 0.1111(2) 0.21774(18) 0.59389(8) 0.0258(4) Uani d . 1 1
F F51' 0.04437(15) 0.07822(11) 0.58108(5) 0.0387(3) Uani d . 1 1
C C6' 0.1412(2) 0.26770(18) 0.64919(7) 0.0268(4) Uani d . 1 1
H H6' 0.1161 0.2073 0.6812 0.032 Uiso calc R 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 124.85(13)
C2 N1 H1 121.7(12)
C6 N1 H1 113.4(12)
N3 C2 N21 120.64(14)
N3 C2 N1 123.50(13)
N21 C2 N1 115.85(14)
C2 N21 H21A 120.5(13)
C2 N21 H21B 118.4(14)
H21A N21 H21B 121.0(19)
C2 N3 C4 112.26(12)
N3 C4 N9 127.04(13)
N3 C4 C5 128.03(14)
N9 C4 C5 104.91(13)
C4 C5 N7 111.46(13)
C4 C5 C6 118.99(13)
N7 C5 C6 129.50(13)
O61 C6 N1 120.80(14)
O61 C6 C5 126.83(14)
N1 C6 C5 112.33(12)
C8 N7 C5 103.93(12)
N7 C8 N9 113.38(13)
N7 C8 H8 123.3
N9 C8 H8 123.3
C8 N9 C4 106.31(12)
C8 N9 C91 123.38(12)
C4 N9 C91 130.10(12)
O92 C91 N9 110.74(11)
O92 C91 H91A 109.5
N9 C91 H91A 109.5
O92 C91 H91B 109.5
N9 C91 H91B 109.5
H91A C91 H91B 108.1
C91 O92 C93 112.19(11)
O92 C93 C94 109.22(13)
O92 C93 H93A 109.8
C94 C93 H93A 109.8
O92 C93 H93B 109.8
C94 C93 H93B 109.8
H93A C93 H93B 108.3
O95 C94 C93 113.83(14)
O95 C94 H94A 108.8
C93 C94 H94A 108.8
O95 C94 H94B 108.8
C93 C94 H94B 108.8
H94A C94 H94B 107.7
C94 O95 H95 109.5
C6' N1' C2' 122.69(15)
C6' N1' H1' 116.3(14)
C2' N1' H1' 121.0(14)
O21' C2' N3' 122.22(14)
O21' C2' N1' 119.44(15)
N3' C2' N1' 118.34(14)
C4' N3' C2' 120.48(14)
N41' C4' N3' 119.83(15)
N41' C4' C5' 120.39(15)
N3' C4' C5' 119.78(15)
C4' N41' H41A 119.3(15)
C4' N41' H41B 122.7(15)
H41A N41' H41B 118(2)
C6' C5' F51' 121.44(15)
C6' C5' C4' 120.64(15)
F51' C5' C4' 117.92(15)
C5' C6' N1' 118.05(15)
C5' C6' H6' 121.0
N1' C6' H6' 121.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3751(19)
N1 C6 1.3888(19)
N1 H1 0.895(15)
C2 N3 1.3328(19)
C2 N21 1.335(2)
N21 H21A 0.88(2)
N21 H21B 0.87(2)
N3 C4 1.3583(19)
C4 N9 1.3783(19)
C4 C5 1.379(2)
C5 N7 1.3866(19)
C5 C6 1.411(2)
C6 O61 1.2418(18)
N7 C8 1.304(2)
C8 N9 1.3775(19)
C8 H8 0.9500
N9 C91 1.4533(19)
C91 O92 1.4049(17)
C91 H91A 0.9900
C91 H91B 0.9900
O92 C93 1.4393(18)
C93 C94 1.500(2)
C93 H93A 0.9900
C93 H93B 0.9900
C94 O95 1.419(2)
C94 H94A 0.9900
C94 H94B 0.9900
O95 H95 0.8400
N1' C6' 1.360(2)
N1' C2' 1.384(2)
N1' H1' 0.88(2)
C2' O21' 1.240(2)
C2' N3' 1.361(2)
N3' C4' 1.336(2)
C4' N41' 1.330(2)
C4' C5' 1.423(2)
N41' H41A 0.908(16)
N41' H41B 0.90(2)
C5' C6' 1.332(2)
C5' F51' 1.3643(19)
C6' H6' 0.9500
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 H1 N3' . 0.895(15) 2.002(15) 2.8964(18) 176.3(17)
N21 H21B N3 3_676 0.87(2) 2.20(2) 3.0698(19) 177(2)
N21 H21A O21' . 0.88(2) 2.05(2) 2.9317(19) 179.7(19)
O95 H95 N7 1_565 0.84 2.32 3.0663(18) 147.7
O95 H95 O61 1_565 0.84 2.47 3.1112(16) 133.5
N1' H1' O92 4_576 0.88(2) 2.22(2) 3.0246(18) 151.6(19)
N41' H41A O61 . 0.908(16) 1.878(16) 2.7844(18) 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
C6 N1 C2 N3 -1.9(2)
C6 N1 C2 N21 176.72(13)
N21 C2 N3 C4 -177.76(13)
N1 C2 N3 C4 0.79(19)
C2 N3 C4 N9 178.48(13)
C2 N3 C4 C5 -0.2(2)
N3 C4 C5 N7 178.21(12)
N9 C4 C5 N7 -0.67(15)
N3 C4 C5 C6 0.5(2)
N9 C4 C5 C6 -178.37(12)
C2 N1 C6 O61 -176.19(13)
C2 N1 C6 C5 2.03(19)
C4 C5 C6 O61 176.76(13)
N7 C5 C6 O61 -0.5(2)
C4 C5 C6 N1 -1.33(18)
N7 C5 C6 N1 -178.55(13)
C4 C5 N7 C8 0.36(15)
C6 C5 N7 C8 177.75(14)
C5 N7 C8 N9 0.11(15)
N7 C8 N9 C4 -0.53(16)
N7 C8 N9 C91 -175.70(12)
N3 C4 N9 C8 -178.21(13)
C5 C4 N9 C8 0.70(14)
N3 C4 N9 C91 -3.5(2)
C5 C4 N9 C91 175.42(13)
C8 N9 C91 O92 73.11(16)
C4 N9 C91 O92 -100.82(16)
N9 C91 O92 C93 77.46(15)
C91 O92 C93 C94 -171.75(13)
O92 C93 C94 O95 -63.25(18)
C6' N1' C2' O21' -179.03(13)
C6' N1' C2' N3' 0.5(2)
O21' C2' N3' C4' 179.74(13)
N1' C2' N3' C4' 0.2(2)
C2' N3' C4' N41' 178.75(13)
C2' N3' C4' C5' -1.0(2)
N41' C4' C5' C6' -178.61(14)
N3' C4' C5' C6' 1.2(2)
N41' C4' C5' F51' 1.3(2)
N3' C4' C5' F51' -178.90(12)
F51' C5' C6' N1' 179.60(12)
C4' C5' C6' N1' -0.5(2)
C2' N1' C6' C5' -0.4(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654568
2 PubChem 139064077
