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#$Date: 2023-09-05 22:32:21 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/70/7247003.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_7247003
loop_
_publ_author_name
'Kanagavel, Manimurugan'
'Nechipadappu, Sunil Kumar'
_publ_section_title
;
 Trimorphic forms of 5-fluorocytosine--gentisic acid with enhanced
 hydration stability
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              4199
_journal_page_last               4212
_journal_paper_doi               10.1039/D3CE00450C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C7 H6 O4, C4 H4 F N3 O'
_chemical_formula_sum            'C11 H10 F N3 O5'
_chemical_formula_weight         283.22
_chemical_name_common            'FLUCYTOSINE-GENTISIC ACID form II'
_chemical_name_systematic        'FLUCYTOSINE-GENTISIC ACID form II'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2023-04-13 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.71(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.715(2)
_cell_length_b                   14.634(8)
_cell_length_c                   22.239(15)
_cell_measurement_reflns_used    3208
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      25.2
_cell_measurement_theta_min      2.42
_cell_volume                     1207.7(12)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14777
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.553
_diffrn_reflns_theta_min         2.302
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: WATER'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3691
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0375P)²+0.2689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2048
_reflns_number_total             3691
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00450c2.cif
_cod_data_source_block           5FC-GEA_FII
_cod_depositor_comments
'Adding full bibliography for 7247002--7247004.cif.'
_cod_original_cell_volume        1207.8(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247003
_shelx_shelxl_version_number     2018/3
_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   0.974
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6807(4) 0.80561(11) 0.45971(8) 0.0301(4) Uani 1 1 d . . . . .
C2 C 0.4613(5) 0.74377(11) 0.55035(8) 0.0336(4) Uani 1 1 d . . . . .
H2 H 0.355976 0.696043 0.570809 0.040 Uiso 1 1 calc R U . . .
C3 C 0.5526(4) 0.82098(11) 0.57855(8) 0.0314(4) Uani 1 1 d . . . . .
C4 C 0.7233(4) 0.89290(11) 0.54724(8) 0.0284(4) Uani 1 1 d . . . . .
F1 F 0.4949(3) 0.83340(7) 0.63779(5) 0.0503(3) Uani 1 1 d . . . . .
N1 N 0.5255(4) 0.73618(10) 0.49085(7) 0.0336(4) Uani 1 1 d . . . . .
H1N H 0.464(5) 0.6824(15) 0.4675(9) 0.058(6) Uiso 1 1 d . . . . .
N2 N 0.7856(4) 0.88273(9) 0.48848(6) 0.0293(3) Uani 1 1 d . . . . .
N3 N 0.8246(4) 0.96836(10) 0.57533(8) 0.0374(4) Uani 1 1 d . . . . .
H2N H 0.933(5) 1.0130(15) 0.5535(10) 0.058(6) Uiso 1 1 d . . . . .
H3N H 0.758(5) 0.9765(13) 0.6114(9) 0.048(6) Uiso 1 1 d . . . . .
O1 O 0.7250(3) 0.79486(8) 0.40417(6) 0.0419(3) Uani 1 1 d . . . . .
C5 C 0.3697(5) 0.58915(12) 0.36234(8) 0.0363(4) Uani 1 1 d . . . . .
C6 C 0.2857(4) 0.51089(11) 0.32292(8) 0.0304(4) Uani 1 1 d . . . . .
C7 C 0.1366(4) 0.43162(11) 0.34672(8) 0.0318(4) Uani 1 1 d . . . . .
C8 C 0.0691(5) 0.35698(12) 0.30928(8) 0.0355(4) Uani 1 1 d . . . . .
H8 H -0.030374 0.304141 0.324758 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1480(5) 0.36053(12) 0.24948(8) 0.0366(4) Uani 1 1 d . . . . .
H9 H 0.102249 0.310002 0.224935 0.044 Uiso 1 1 calc R U . . .
C10 C 0.2960(5) 0.43916(11) 0.22542(8) 0.0330(4) Uani 1 1 d . . . . .
C11 C 0.3622(4) 0.51381(12) 0.26192(8) 0.0334(4) Uani 1 1 d . . . . .
H11 H 0.458519 0.566656 0.245912 0.040 Uiso 1 1 calc R U . . .
O2 O 0.3069(4) 0.58891(9) 0.41670(6) 0.0480(4) Uani 1 1 d . . . . .
O3 O 0.5171(4) 0.65930(9) 0.33669(6) 0.0516(4) Uani 1 1 d D . . . .
H3O H 0.574(6) 0.7047(15) 0.3643(9) 0.085(8) Uiso 1 1 d D . . . .
O4 O 0.0527(4) 0.42416(9) 0.40591(6) 0.0447(4) Uani 1 1 d . . . . .
H4O H 0.121(6) 0.4830(18) 0.4237(11) 0.079(8) Uiso 1 1 d . . . . .
O5 O 0.3836(4) 0.44538(9) 0.16634(6) 0.0479(4) Uani 1 1 d . . . . .
H5O H 0.333(6) 0.3910(17) 0.1426(11) 0.077(8) 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'
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'
F F 0.0171 0.0103 '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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N2 121.40(14) . . ?
O1 C1 N1 118.59(15) . . ?
N2 C1 N1 120.01(16) . . ?
C3 C2 N1 118.44(15) . . ?
C3 C2 H2 120.8 . . ?
N1 C2 H2 120.8 . . ?
C2 C3 F1 121.58(14) . . ?
C2 C3 C4 120.42(16) . . ?
F1 C3 C4 117.99(15) . . ?
N3 C4 N2 119.70(15) . . ?
N3 C4 C3 120.75(16) . . ?
N2 C4 C3 119.54(15) . . ?
C2 N1 C1 121.86(15) . . ?
C2 N1 H1N 122.9(12) . . ?
C1 N1 H1N 115.2(12) . . ?
C1 N2 C4 119.67(13) . . ?
C4 N3 H2N 118.0(13) . . ?
C4 N3 H3N 118.2(13) . . ?
H2N N3 H3N 123.2(19) . . ?
O2 C5 O3 121.93(17) . . ?
O2 C5 C6 122.36(15) . . ?
O3 C5 C6 115.71(16) . . ?
C11 C6 C7 119.59(15) . . ?
C11 C6 C5 120.55(15) . . ?
C7 C6 C5 119.84(16) . . ?
O4 C7 C8 118.04(15) . . ?
O4 C7 C6 122.73(15) . . ?
C8 C7 C6 119.23(16) . . ?
C9 C8 C7 120.58(16) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.55(16) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
O5 C10 C11 117.93(15) . . ?
O5 C10 C9 122.59(16) . . ?
C11 C10 C9 119.48(16) . . ?
C10 C11 C6 120.56(15) . . ?
C10 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C5 O3 H3O 111.3(15) . . ?
C7 O4 H4O 104.6(14) . . ?
C10 O5 H5O 114.8(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.264(2) . ?
C1 N2 1.346(2) . ?
C1 N1 1.372(2) . ?
C2 C3 1.329(2) . ?
C2 N1 1.360(2) . ?
C2 H2 0.9300 . ?
C3 F1 1.357(2) . ?
C3 C4 1.427(2) . ?
C4 N3 1.315(2) . ?
C4 N2 1.346(2) . ?
N1 H1N 0.96(2) . ?
N3 H2N 0.92(2) . ?
N3 H3N 0.86(2) . ?
C5 O2 1.242(2) . ?
C5 O3 1.307(2) . ?
C5 C6 1.467(2) . ?
C6 C11 1.400(2) . ?
C6 C7 1.400(2) . ?
C7 O4 1.371(2) . ?
C7 C8 1.389(2) . ?
C8 C9 1.376(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9300 . ?
C10 O5 1.372(2) . ?
C10 C11 1.376(2) . ?
C11 H11 0.9300 . ?
O3 H3O 0.922(16) . ?
O4 H4O 0.98(3) . ?
O5 H5O 0.97(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H2N N2 0.92(2) 2.10(2) 3.009(2) 174.2(19) 3_776 yes
N3 H3N O5 0.86(2) 2.21(2) 2.948(2) 143.5(18) 4_576 yes
O5 H5O O1 0.97(3) 1.76(3) 2.723(2) 175(2) 2_645 yes
N1 H1N O2 0.96(2) 1.85(2) 2.810(2) 172.6(19) . yes
O3 H3O O1 0.922(16) 1.672(17) 2.583(2) 169(2) . yes
O4 H4O O2 0.98(3) 1.71(3) 2.596(2) 150(2) . yes
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 F1 179.69(15) . . . . ?
N1 C2 C3 C4 -1.8(3) . . . . ?
C2 C3 C4 N3 -177.87(17) . . . . ?
F1 C3 C4 N3 0.7(2) . . . . ?
C2 C3 C4 N2 1.2(3) . . . . ?
F1 C3 C4 N2 179.80(15) . . . . ?
C3 C2 N1 C1 0.0(3) . . . . ?
O1 C1 N1 C2 -178.35(16) . . . . ?
N2 C1 N1 C2 2.3(3) . . . . ?
O1 C1 N2 C4 177.83(16) . . . . ?
N1 C1 N2 C4 -2.9(2) . . . . ?
N3 C4 N2 C1 -179.76(16) . . . . ?
C3 C4 N2 C1 1.2(2) . . . . ?
O2 C5 C6 C11 -179.75(17) . . . . ?
O3 C5 C6 C11 -0.1(2) . . . . ?
O2 C5 C6 C7 -1.4(3) . . . . ?
O3 C5 C6 C7 178.22(16) . . . . ?
C11 C6 C7 O4 -179.57(16) . . . . ?
C5 C6 C7 O4 2.1(3) . . . . ?
C11 C6 C7 C8 0.4(3) . . . . ?
C5 C6 C7 C8 -177.96(16) . . . . ?
O4 C7 C8 C9 -179.94(16) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 O5 179.08(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
O5 C10 C11 C6 -178.62(15) . . . . ?
C9 C10 C11 C6 0.7(3) . . . . ?
C7 C6 C11 C10 -0.8(3) . . . . ?
C5 C6 C11 C10 177.55(16) . . . . ?
