#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:02:42 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312703.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_2312703
loop_
_publ_author_name
'Kanagavel, Manimurugan'
'Balasubramanian, Sridhar'
'Nechipadappu, Sunil Kumar'
_publ_section_title
;
 Variable stoichiometry and a salt-cocrystal intermediate in
 multicomponent systems of flucytosine: structural elucidation and their
 impact on stability.
;
_journal_coeditor_code           YH5039
_journal_issue                   6
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              793
_journal_page_last               806
_journal_paper_doi               10.1107/S2052520624010278
_journal_volume                  80
_journal_year                    2024
_chemical_formula_moiety         'C6 H6 O2, 4(C4 H4 F N3 O)'
_chemical_formula_sum            'C22 H22 F4 N12 O6'
_chemical_formula_weight         626.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                111.5170(10)
_cell_angle_beta                 99.093(2)
_cell_angle_gamma                110.410(5)
_cell_formula_units_Z            1
_cell_length_a                   7.2415(2)
_cell_length_b                   10.1036(3)
_cell_length_c                   10.6423(3)
_cell_measurement_reflns_used    8338
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.22
_cell_measurement_theta_min      2.23
_cell_volume                     641.36(5)
_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 0.993
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15403
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_min         2.405
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6090
_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    1.622
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3904
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0721P)²+0.0697P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1266
_refine_ls_wR_factor_ref         0.1472
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2567
_reflns_number_total             3904
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yh5039sup1.cif
_cod_data_source_block           new_FCY-RES
_cod_depositor_comments
'Adding full bibliography for 2312700--2312704.cif.'
_cod_original_cell_volume        641.36(4)
_cod_database_code               2312703
_cod_database_fobs_code          2312703
_shelx_shelxl_version_number     2019/3
_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   0.978
_shelx_estimated_absorpt_t_max   0.983
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
C1A C 1.03106(18) 0.76527(15) 0.96125(12) 0.0351(3) Uani 1 1 d . . . . .
C2A C 0.82363(18) 0.49564(15) 0.81065(12) 0.0349(3) Uani 1 1 d . . . . .
C3A C 0.8833(2) 0.51685(16) 0.69469(12) 0.0390(3) Uani 1 1 d . . . . .
C4A C 1.0111(2) 0.66094(17) 0.71554(13) 0.0397(3) Uani 1 1 d . . . . .
H4A H 1.049374 0.676082 0.640679 0.048 Uiso 1 1 calc R U . . .
F1A F 0.80579(15) 0.38841(11) 0.56574(8) 0.0604(3) Uani 1 1 d . . . . .
N1A N 1.08397(17) 0.78488(14) 0.84795(11) 0.0374(2) Uani 1 1 d . . . . .
H1N H 1.180(3) 0.881(2) 0.8682(16) 0.056(5) Uiso 1 1 d . . . . .
N2A N 0.89698(15) 0.61965(13) 0.93882(10) 0.0355(2) Uani 1 1 d . . . . .
N3A N 0.69302(19) 0.35398(15) 0.79022(13) 0.0458(3) Uani 1 1 d . . . . .
H2N H 0.656(3) 0.271(2) 0.7063(19) 0.066(5) Uiso 1 1 d . . . . .
H3N H 0.658(3) 0.3487(19) 0.8670(17) 0.058(5) Uiso 1 1 d . . . . .
O1A O 1.10615(15) 0.88258(11) 1.08096(9) 0.0475(3) Uani 1 1 d . . . . .
C1B C 0.45381(18) 0.19513(15) 1.02562(12) 0.0333(3) Uani 1 1 d . . . . .
C2B C 0.65056(18) 0.46665(15) 1.17226(12) 0.0345(3) Uani 1 1 d . . . . .
C3B C 0.5882(2) 0.44728(16) 1.28781(12) 0.0388(3) Uani 1 1 d . . . . .
C4B C 0.4620(2) 0.30308(16) 1.26844(13) 0.0396(3) Uani 1 1 d . . . . .
H4B H 0.421831 0.289053 1.343199 0.048 Uiso 1 1 calc R U . . .
F1B F 0.66157(15) 0.57727(10) 1.41535(8) 0.0605(3) Uani 1 1 d . . . . .
N1B N 0.39421(17) 0.17823(14) 1.13795(11) 0.0381(3) Uani 1 1 d . . . . .
H4N H 0.309(3) 0.083(2) 1.1185(17) 0.065(5) Uiso 1 1 d . . . . .
N2B N 0.58295(15) 0.34051(12) 1.04559(10) 0.0342(2) Uani 1 1 d . . . . .
N3B N 0.77789(19) 0.60758(14) 1.19043(13) 0.0457(3) Uani 1 1 d . . . . .
H5N H 0.811(3) 0.687(2) 1.2716(18) 0.060(5) Uiso 1 1 d . . . . .
H6N H 0.814(2) 0.6084(19) 1.1144(16) 0.051(4) Uiso 1 1 d . . . . .
O1B O 0.38751(14) 0.07519(11) 0.90832(9) 0.0430(2) Uani 1 1 d . . . . .
C1 C -0.1470(2) 0.01130(17) 0.56730(13) 0.0466(3) Uani 1 1 d . . . . .
H1 H -0.244743 0.019425 0.613034 0.070 Uiso 0.5 1 calc R U P A 1
C3 C 0.1810(2) 0.00081(16) 0.56996(13) 0.0455(3) Uani 1 1 d . . . . .
H3 H 0.301771 0.001884 0.616842 0.068 Uiso 0.5 1 calc R U P B 1
C2 C 0.0322(2) 0.01122(17) 0.63549(13) 0.0453(3) Uani 1 1 d . . . . .
H2 H 0.053171 0.018256 0.726662 0.054 Uiso 1 1 calc R U . . .
O1 O -0.2784(3) 0.0335(3) 0.6341(2) 0.0541(5) Uani 0.5 1 d D . P C 2
H1O H -0.232(7) 0.063(6) 0.723(2) 0.121(18) Uiso 0.5 1 d D . P D 2
O2 O 0.3760(3) 0.0133(3) 0.63906(19) 0.0512(5) Uani 0.5 1 d D . P E 2
H2O H 0.389(6) 0.045(5) 0.730(2) 0.093(14) Uiso 0.5 1 d D . P F 2
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
O1A C1A N2A 121.80(10) . . ?
O1A C1A N1A 118.91(11) . . ?
N2A C1A N1A 119.28(11) . . ?
N3A C2A N2A 119.86(10) . . ?
N3A C2A C3A 120.43(11) . . ?
N2A C2A C3A 119.70(11) . . ?
C4A C3A F1A 121.81(11) . . ?
C4A C3A C2A 119.97(11) . . ?
F1A C3A C2A 118.22(11) . . ?
C3A C4A N1A 118.81(11) . . ?
C3A C4A H4A 120.6 . . ?
N1A C4A H4A 120.6 . . ?
C4A N1A C1A 121.72(11) . . ?
C4A N1A H1N 121.3(10) . . ?
C1A N1A H1N 116.6(10) . . ?
C2A N2A C1A 120.46(9) . . ?
C2A N3A H2N 118.5(12) . . ?
C2A N3A H3N 116.3(11) . . ?
H2N N3A H3N 125.0(16) . . ?
O1B C1B N2B 121.72(10) . . ?
O1B C1B N1B 118.87(11) . . ?
N2B C1B N1B 119.41(11) . . ?
N3B C2B N2B 119.57(11) . . ?
N3B C2B C3B 120.72(12) . . ?
N2B C2B C3B 119.69(11) . . ?
C4B C3B F1B 121.76(11) . . ?
C4B C3B C2B 120.02(11) . . ?
F1B C3B C2B 118.21(11) . . ?
C3B C4B N1B 118.64(11) . . ?
C3B C4B H4B 120.7 . . ?
N1B C4B H4B 120.7 . . ?
C4B N1B C1B 121.95(11) . . ?
C4B N1B H4N 122.7(11) . . ?
C1B N1B H4N 115.4(11) . . ?
C2B N2B C1B 120.28(9) . . ?
C2B N3B H5N 117.0(12) . . ?
C2B N3B H6N 115.0(11) . . ?
H5N N3B H6N 128.0(16) . . ?
O1 C1 C2 120.48(14) . . ?
O1 C1 C3 119.35(16) . 2_556 ?
C2 C1 C3 120.01(13) . 2_556 ?
C2 C1 H1 120.0 . . ?
C3 C1 H1 120.0 2_556 . ?
C2 C3 C1 118.99(13) . 2_556 ?
C2 C3 O2 123.52(13) . . ?
C1 C3 O2 117.32(14) 2_556 . ?
C2 C3 H3 120.5 . . ?
C1 C3 H3 120.5 2_556 . ?
C1 C2 C3 121.00(12) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C1 O1 H1O 113(3) . . ?
C3 O2 H2O 107(3) . . ?
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
C1A O1A 1.2439(14) . ?
C1A N2A 1.3554(16) . ?
C1A N1A 1.3814(14) . ?
C2A N3A 1.3240(16) . ?
C2A N2A 1.3288(15) . ?
C2A C3A 1.4331(16) . ?
C3A C4A 1.3354(18) . ?
C3A F1A 1.3507(14) . ?
C4A N1A 1.3571(16) . ?
C4A H4A 0.9300 . ?
N1A H1N 0.891(18) . ?
N3A H2N 0.890(18) . ?
N3A H3N 0.908(17) . ?
C1B O1B 1.2460(14) . ?
C1B N2B 1.3518(15) . ?
C1B N1B 1.3806(14) . ?
C2B N3B 1.3194(17) . ?
C2B N2B 1.3331(15) . ?
C2B C3B 1.4301(16) . ?
C3B C4B 1.3385(19) . ?
C3B F1B 1.3517(14) . ?
C4B N1B 1.3522(16) . ?
C4B H4B 0.9300 . ?
N1B H4N 0.86(2) . ?
N3B H5N 0.859(17) . ?
N3B H6N 0.892(16) . ?
C1 O1 1.307(2) . ?
C1 C2 1.384(2) . ?
C1 C3 1.3941(17) 2_556 ?
C1 H1 0.9300 . ?
C3 C2 1.3862(19) . ?
C3 O2 1.425(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
O1 H1O 0.851(19) . ?
O2 H2O 0.883(18) . ?
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
N1A H1N O1B 0.891(18) 1.852(18) 2.7427(14) 177.2(16) 1_665 yes
N3A H2N O1^b 0.890(18) 2.476(19) 3.149(3) 132.8(14) 1_655 yes
N1B H4N O1A 0.86(2) 1.89(2) 2.7508(15) 174.8(17) 1_445 yes
O1^b H1O^b O1A 0.851(19) 1.92(2) 2.766(2) 173(5) 2_667 yes
N3A H2N O2^b 0.890(18) 2.426(19) 2.994(3) 122.0(14) . yes
N3A H3N N2B 0.908(17) 2.079(17) 2.9867(15) 178.8(16) . yes
N3B H6N N2A 0.892(16) 2.080(16) 2.9707(15) 177.3(15) . yes
O2^b H2O^b O1B 0.883(18) 1.81(2) 2.6801(19) 170(4) . yes
O2^b H2O^b O1B 0.883(18) 1.81(2) 2.6801(19) 170(4) . yes
