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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/81/4508164.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_4508164
loop_
_publ_author_name
'da Silva, Cecília C. P.'
'de Oliveira, Rebeka'
'Tenorio, Juan C.'
'Honorato, Sara B.'
'Ayala, Alejandro P.'
'Ellena, Javier'
_publ_section_title
;
 The Continuum in 5-Fluorocytosine. Toward Salt Formation
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4315
_journal_paper_doi               10.1021/cg400662n
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C8 H8 F N3 O5'
_chemical_formula_sum            'C8 H8 F N3 O5'
_chemical_formula_weight         245.17
_chemical_name_common            'Maleate of 5-FC'
_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
_cell_angle_beta                 113.573(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3450(5)
_cell_length_b                   11.8620(6)
_cell_length_c                   18.9540(8)
_cell_measurement_reflns_used    4083
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      2.91
_cell_volume                     1925.73(17)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.057
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7612
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0545
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0723P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                2130
_reflns_number_total             3907
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            cg400662n_si_002.cif
_cod_data_source_block           MALEATE
_cod_original_cell_volume        1925.73(16)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4508164
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_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_type_symbol
F51 0.58734(17) -0.05659(11) 0.10147(9) 0.0314(4) Uani d . 1 F
N1 0.9602(2) 0.04723(17) 0.23121(12) 0.0244(5) Uani d . 1 N
H1 1.0567 0.0179 0.2682 0.037 Uiso d R 1 H
N3 0.7973(2) 0.19862(17) 0.17241(12) 0.0235(5) Uani d . 1 N
H3 0.7941 0.2785 0.1717 0.035 Uiso d R 1 H
N4 0.5411(2) 0.17182(17) 0.08709(13) 0.0263(6) Uani d . 1 N
H41A 0.529 0.2505 0.0867 0.039 Uiso d R 1 H
H41B 0.4555 0.1231 0.0599 0.039 Uiso d R 1 H
O21 1.0452(2) 0.22846(14) 0.26025(11) 0.0298(5) Uani d . 1 O
C2 0.9418(3) 0.1627(2) 0.22408(15) 0.0231(6) Uani d . 1 C
C4 0.6762(3) 0.1304(2) 0.13146(15) 0.0229(6) Uani d . 1 C
C5 0.7058(3) 0.0132(2) 0.14217(15) 0.0243(6) Uani d . 1 C
C6 0.8441(3) -0.0260(2) 0.19038(15) 0.0254(7) Uani d . 1 C
H6 0.8614 -0.1033 0.1962 0.03 Uiso calc R 1 H
F51' 0.08051(16) 0.17751(11) 0.10871(8) 0.0289(4) Uani d . 1 F
N1' 0.4578(2) 0.27944(17) 0.23623(12) 0.0247(5) Uani d . 1 N
H1' 0.5538 0.2532 0.2645 0.037 Uiso d R 1 H
N3' 0.2940(2) 0.43135(17) 0.18101(12) 0.0231(5) Uani d . 1 N
H3' 0.2789 0.5065 0.1771 0.035 Uiso d R 1 H
N41' 0.0377(2) 0.40685(17) 0.09431(12) 0.0263(6) Uani d . 1 N
H41C 0.0282 0.4831 0.0918 0.04 Uiso d R 1 H
H41D -0.0441 0.3598 0.0683 0.04 Uiso d R 1 H
O21' 0.5434(2) 0.45950(15) 0.26724(11) 0.0291(5) Uani d . 1 O
C3' 0.4393(3) 0.3942(2) 0.23075(15) 0.0237(6) Uani d . 1 C
C4' 0.1710(3) 0.3641(2) 0.13896(15) 0.0216(6) Uani d . 1 C
C5' 0.2013(3) 0.2462(2) 0.14857(15) 0.0236(6) Uani d . 1 C
C6' 0.3397(3) 0.2061(2) 0.19544(15) 0.0243(7) Uani d . 1 C
H6' 0.3566 0.1287 0.2006 0.029 Uiso calc R 1 H
O6 0.7561(2) 0.20294(14) 0.50730(10) 0.0261(5) Uani d . 1 O
O5 0.7089(2) 0.02200(14) 0.48085(10) 0.0266(5) Uani d . 1 O
H5 0.619 -0.0286 0.4495 0.032 Uiso d R 1 H
O4 0.4747(2) -0.09168(14) 0.40618(10) 0.0265(5) Uani d . 1 O
O3 0.2266(2) -0.06588(14) 0.32921(10) 0.0281(5) Uani d . 1 O
C10 0.6636(3) 0.1282(2) 0.47226(15) 0.0240(6) Uani d . 1 C
C9 0.5010(3) 0.1591(2) 0.42092(15) 0.0247(7) Uani d . 1 C
H9 0.4824 0.2363 0.4173 0.03 Uiso calc R 1 H
C8 0.3764(3) 0.0975(2) 0.37905(15) 0.0256(6) Uani d . 1 C
H8 0.2872 0.1386 0.3505 0.031 Uiso calc R 1 H
C7 0.3589(3) -0.0280(2) 0.37110(15) 0.0227(6) Uani d . 1 C
O6' -0.2537(2) 0.93726(15) -0.01070(11) 0.0311(5) Uani d . 1 O
O5' -0.2086(2) 0.75606(15) 0.01531(10) 0.0302(5) Uani d . 1 O
H5' -0.1099 0.7019 0.0457 0.036 Uiso d R 1 H
O4' 0.0202(2) 0.64123(15) 0.09165(10) 0.0289(5) Uani d . 1 O
O3' 0.2666(2) 0.66599(14) 0.17405(10) 0.0269(5) Uani d . 1 O
C10' -0.1619(3) 0.8619(2) 0.02240(16) 0.0260(7) Uani d . 1 C
C9' 0.0027(3) 0.8917(2) 0.07130(15) 0.0262(7) Uani d . 1 C
H9' 0.0241 0.9684 0.0723 0.031 Uiso calc R 1 H
C8' 0.1261(3) 0.8291(2) 0.11421(16) 0.0268(7) Uani d . 1 C
H8' 0.2183 0.8687 0.14 0.032 Uiso calc R 1 H
C7' 0.1362(3) 0.7041(2) 0.12651(16) 0.0230(6) Uani d . 1 C
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 0 '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 0.006 '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
C6 N1 C2 122.4(2)
C6 N1 H1 119.1
C2 N1 H1 118.4
C4 N3 C2 125.3(2)
C4 N3 H3 125.1
C2 N3 H3 109.6
C4 N4 H41A 117.5
C4 N4 H41B 120.6
H41A N4 H41B 121.7
O21 C2 N1 122.8(2)
O21 C2 N3 122.1(2)
N1 C2 N3 115.1(2)
N4 C4 N3 121.2(2)
N4 C4 C5 123.1(2)
N3 C4 C5 115.7(2)
C6 C5 F51 121.8(2)
C6 C5 C4 121.4(2)
F51 C5 C4 116.9(2)
C5 C6 N1 120.0(2)
C5 C6 H6 120
N1 C6 H6 120
C3' N1' C6' 122.5(2)
C3' N1' H1' 117.1
C6' N1' H1' 120.2
C4' N3' C3' 125.6(2)
C4' N3' H3' 117.5
C3' N3' H3' 116.9
C4' N41' H41C 118.2
C4' N41' H41D 119.4
H41C N41' H41D 122.4
O21' C3' N1' 122.7(2)
O21' C3' N3' 121.9(2)
N1' C3' N3' 115.4(2)
N41' C4' N3' 121.2(2)
N41' C4' C5' 123.9(2)
N3' C4' C5' 114.9(2)
C6' C5' F51' 122.0(2)
C6' C5' C4' 121.8(2)
F51' C5' C4' 116.2(2)
C5' C6' N1' 119.8(2)
C5' C6' H6' 120.1
N1' C6' H6' 120.1
C10 O5 H5 110.2
C7 O4 H5 112.9
O6 C10 O5 120.0(2)
O6 C10 C9 119.3(2)
O5 C10 C9 120.7(2)
C8 C9 C10 132.5(2)
C8 C9 H9 113.8
C10 C9 H9 113.8
C9 C8 C7 129.6(2)
C9 C8 H8 115.2
C7 C8 H8 115.2
O3 C7 O4 122.5(2)
O3 C7 C8 117.4(2)
O4 C7 C8 120.2(2)
C10' O5' H5' 109.6
C7' O4' H5' 112.2
O6' C10' O5' 120.5(2)
O6' C10' C9' 119.0(2)
O5' C10' C9' 120.5(2)
C8' C9' C10' 132.2(3)
C8' C9' H9' 113.9
C10' C9' H9' 113.9
C9' C8' C7' 129.0(3)
C9' C8' H8' 115.5
C7' C8' H8' 115.5
O4' C7' O3' 122.6(2)
O4' C7' C8' 121.0(2)
O3' C7' C8' 116.4(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F51 C5 1.351(3)
N1 C6 1.363(3)
N1 C2 1.380(3)
N1 H1 0.9593
N3 C4 1.354(3)
N3 C2 1.381(3)
N3 H3 0.9477
N4 C4 1.301(3)
N4 H41A 0.9403
N4 H41B 0.9537
O21 C2 1.218(3)
C4 C5 1.416(4)
C5 C6 1.333(4)
C6 H6 0.93
F51' C5' 1.352(3)
N1' C3' 1.370(3)
N1' C6' 1.375(3)
N1' H1' 0.897
N3' C4' 1.364(3)
N3' C3' 1.379(3)
N3' H3' 0.9011
N41' C4' 1.296(3)
N41' H41C 0.9084
N41' H41D 0.9157
O21' C3' 1.220(3)
C4' C5' 1.424(4)
C5' C6' 1.330(4)
C6' H6' 0.93
O6 C10 1.232(3)
O5 C10 1.318(3)
O5 H5 1.0099
O4 C7 1.268(3)
O4 H5 1.4717
O3 C7 1.255(3)
C10 C9 1.486(4)
C9 C8 1.334(3)
C9 H9 0.93
C8 C7 1.499(3)
C8 H8 0.93
O6' C10' 1.224(3)
O5' C10' 1.319(3)
O5' H5' 1.0821
O4' C7' 1.263(3)
O4' H5' 1.3807
O3' C7' 1.274(3)
C10' C9' 1.487(4)
C9' C8' 1.339(3)
C9' H9' 0.93
C8' C7' 1.498(3)
C8' H8' 0.93
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 O21 -179.8(3)
C6 N1 C2 N3 -0.2(4)
C4 N3 C2 O21 -178.6(3)
C4 N3 C2 N1 1.7(4)
C2 N3 C4 N4 176.2(2)
C2 N3 C4 C5 -2.0(4)
N4 C4 C5 C6 -177.4(3)
N3 C4 C5 C6 0.7(4)
N4 C4 C5 F51 2.4(4)
N3 C4 C5 F51 -179.5(2)
F51 C5 C6 N1 -179.2(2)
C4 C5 C6 N1 0.6(4)
C2 N1 C6 C5 -0.9(4)
C6' N1' C3' O21' 179.5(3)
C6' N1' C3' N3' -0.4(4)
C4' N3' C3' O21' -179.1(3)
C4' N3' C3' N1' 0.8(4)
C3' N3' C4' N41' 179.1(3)
C3' N3' C4' C5' -0.7(4)
N41' C4' C5' C6' -179.6(3)
N3' C4' C5' C6' 0.2(4)
N41' C4' C5' F51' -1.0(4)
N3' C4' C5' F51' 178.8(2)
F51' C5' C6' N1' -178.4(2)
C4' C5' C6' N1' 0.1(4)
C3' N1' C6' C5' 0.0(4)
O6 C10 C9 C8 -177.0(3)
O5 C10 C9 C8 2.6(5)
C10 C9 C8 C7 1.3(5)
C9 C8 C7 O3 178.0(3)
C9 C8 C7 O4 -1.6(5)
O6' C10' C9' C8' 179.0(3)
O5' C10' C9' C8' -0.4(5)
C10' C9' C8' C7' 0.1(5)
C9' C8' C7' O4' 3.3(5)
C9' C8' C7' O3' -176.1(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146609
