#------------------------------------------------------------------------------
#$Date: 2024-12-07 19:02:42 +0200 (Sat, 07 Dec 2024) $
#$Revision: 296755 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312702.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_2312702
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         '2(C4 H4 F N3 O), 0.5(C6 H6 O2)'
_chemical_formula_sum            'C11 H11 F2 N6 O3'
_chemical_formula_weight         313.26
_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
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                110.7561(6)
_cell_angle_beta                 99.6967(7)
_cell_angle_gamma                95.2484(8)
_cell_formula_units_Z            2
_cell_length_a                   7.29120(10)
_cell_length_b                   9.3029(2)
_cell_length_c                   10.7855(2)
_cell_measurement_reflns_used    6014
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      36.225
_cell_measurement_theta_min      2.375
_cell_volume                     665.19(2)
_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 0.948
_diffrn_measured_fraction_theta_max 0.977
_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  0.0325
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15769
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.351
_diffrn_reflns_theta_min         2.873
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6502
_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    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             322
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         6304
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0561
_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)+(0.0879P)²+0.1003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1528
_refine_ls_wR_factor_ref         0.1787
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4315
_reflns_number_total             6304
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yh5039sup1.cif
_cod_data_source_block           FCY-HQN
_cod_depositor_comments
'Adding full bibliography for 2312700--2312704.cif.'
_cod_database_code               2312702
_cod_database_fobs_code          2312702
_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   0.973
_shelx_estimated_absorpt_t_max   0.980
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 0.15646(14) -0.33335(11) -0.09718(10) 0.03173(19) Uani 1 1 d . . . . .
C2A C -0.01620(14) -0.30089(11) -0.28644(10) 0.03041(18) Uani 1 1 d . . . . .
C3A C -0.08517(15) -0.46389(12) -0.34630(11) 0.0345(2) Uani 1 1 d . . . . .
C4A C -0.03008(16) -0.55602(12) -0.28008(11) 0.0360(2) Uani 1 1 d . . . . .
H4A H -0.073858 -0.662724 -0.318108 0.043 Uiso 1 1 calc R U . . .
F1A F -0.20470(13) -0.52101(10) -0.46880(8) 0.0534(2) Uani 1 1 d . . . . .
O1A O 0.26741(14) -0.27838(10) 0.01515(9) 0.0444(2) Uani 1 1 d . . . . .
N1A N 0.08984(14) -0.49135(10) -0.15745(10) 0.03550(19) Uani 1 1 d D . . . .
H4N H 0.144(2) -0.5493(19) -0.1083(16) 0.053(4) Uiso 1 1 d D . . . .
N2A N 0.09860(13) -0.24061(9) -0.16448(9) 0.03238(17) Uani 1 1 d . . . . .
N3A N -0.06649(16) -0.20745(12) -0.35072(11) 0.0409(2) Uani 1 1 d . . . . .
H5N H -0.023(3) -0.106(2) -0.3061(18) 0.060(5) Uiso 1 1 d . . . . .
H6N H -0.133(3) -0.242(2) -0.424(2) 0.064(5) Uiso 1 1 d . . . . .
C1B C 0.19852(14) 0.17131(10) -0.08719(9) 0.02891(17) Uani 1 1 d . . . . .
C2B C 0.36519(14) 0.38544(11) 0.10086(9) 0.02922(17) Uani 1 1 d . . . . .
C3B C 0.41716(16) 0.28404(13) 0.16871(10) 0.0346(2) Uani 1 1 d . . . . .
C4B C 0.35357(17) 0.13004(13) 0.10744(11) 0.0368(2) Uani 1 1 d . . . . .
H4B H 0.383414 0.062943 0.151629 0.044 Uiso 1 1 calc R U . . .
F1B F 0.52774(14) 0.34727(10) 0.29394(8) 0.0556(2) Uani 1 1 d . . . . .
O1B O 0.10562(13) 0.11386(9) -0.20793(7) 0.03792(18) Uani 1 1 d . . . . .
N1B N 0.24509(14) 0.07452(10) -0.02005(9) 0.03480(19) Uani 1 1 d D . . . .
H1N H 0.196(2) -0.0311(17) -0.0717(16) 0.056(5) Uiso 1 1 d D . . . .
N2B N 0.25423(12) 0.32654(9) -0.02311(8) 0.02958(16) Uani 1 1 d . . . . .
N3B N 0.42315(16) 0.53810(11) 0.15929(10) 0.0390(2) Uani 1 1 d . . . . .
H2N H 0.496(2) 0.570(2) 0.2304(17) 0.047(4) Uiso 1 1 d . . . . .
H3N H 0.379(2) 0.595(2) 0.1127(17) 0.052(4) Uiso 1 1 d . . . . .
C1 C 0.37709(17) -0.04524(13) -0.43033(12) 0.0376(2) Uani 1 1 d . . . . .
H1 H 0.294734 -0.075795 -0.383777 0.045 Uiso 1 1 calc R U . . .
C2 C 0.38637(14) 0.10201(11) -0.43630(9) 0.03087(18) Uani 1 1 d . . . . .
C3 C 0.50904(16) 0.14654(12) -0.50603(11) 0.0374(2) Uani 1 1 d . . . . .
H3 H 0.515155 0.244957 -0.510234 0.045 Uiso 1 1 calc R U . . .
O1 O 0.27579(13) 0.20798(9) -0.37715(8) 0.03882(19) Uani 1 1 d . . . . .
H1O H 0.216(3) 0.174(2) -0.3235(18) 0.061(5) 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
O1A C1A N2A 121.28(9) . . ?
O1A C1A N1A 120.31(9) . . ?
N2A C1A N1A 118.41(9) . . ?
N2A C2A N3A 119.38(9) . . ?
N2A C2A C3A 119.83(9) . . ?
N3A C2A C3A 120.78(10) . . ?
C4A C3A F1A 121.98(9) . . ?
C4A C3A C2A 119.59(9) . . ?
F1A C3A C2A 118.43(9) . . ?
C3A C4A N1A 119.04(9) . . ?
C3A C4A H4A 120.5 . . ?
N1A C4A H4A 120.5 . . ?
C4A N1A C1A 122.16(9) . . ?
C4A N1A H4N 124.0(10) . . ?
C1A N1A H4N 113.7(10) . . ?
C2A N2A C1A 120.93(8) . . ?
C2A N3A H5N 116.5(12) . . ?
C2A N3A H6N 120.5(15) . . ?
H5N N3A H6N 123.0(19) . . ?
O1B C1B N2B 120.93(8) . . ?
O1B C1B N1B 119.55(8) . . ?
N2B C1B N1B 119.52(9) . . ?
N3B C2B N2B 119.10(9) . . ?
N3B C2B C3B 121.28(9) . . ?
N2B C2B C3B 119.62(9) . . ?
F1B C3B C4B 122.10(9) . . ?
F1B C3B C2B 118.11(9) . . ?
C4B C3B C2B 119.78(9) . . ?
C3B C4B N1B 118.69(9) . . ?
C3B C4B H4B 120.7 . . ?
N1B C4B H4B 120.7 . . ?
C4B N1B C1B 121.73(9) . . ?
C4B N1B H1N 125.0(11) . . ?
C1B N1B H1N 113.3(11) . . ?
C2B N2B C1B 120.50(8) . . ?
C2B N3B H2N 117.6(12) . . ?
C2B N3B H3N 116.2(11) . . ?
H2N N3B H3N 126.1(17) . . ?
C3 C1 C2 119.86(9) 2_654 . ?
C3 C1 H1 120.1 2_654 . ?
C2 C1 H1 120.1 . . ?
O1 C2 C3 117.17(9) . . ?
O1 C2 C1 123.09(9) . . ?
C3 C2 C1 119.74(9) . . ?
C2 C3 C1 120.40(9) . 2_654 ?
C2 C3 H3 119.8 . . ?
C1 C3 H3 119.8 2_654 . ?
C2 O1 H1O 109.7(12) . . ?
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 1.2405(13) . ?
C1A N2A 1.3625(12) . ?
C1A N1A 1.3801(13) . ?
C2A N2A 1.3288(13) . ?
C2A N3A 1.3307(13) . ?
C2A C3A 1.4234(14) . ?
C3A C4A 1.3439(15) . ?
C3A F1A 1.3481(12) . ?
C4A N1A 1.3514(14) . ?
C4A H4A 0.9300 . ?
N1A H4N 0.947(14) . ?
N3A H5N 0.89(2) . ?
N3A H6N 0.793(19) . ?
C1B O1B 1.2584(12) . ?
C1B N2B 1.3486(12) . ?
C1B N1B 1.3732(12) . ?
C2B N3B 1.3262(13) . ?
C2B N2B 1.3333(12) . ?
C2B C3B 1.4249(14) . ?
C3B F1B 1.3429(12) . ?
C3B C4B 1.3447(16) . ?
C4B N1B 1.3560(14) . ?
C4B H4B 0.9300 . ?
N1B H1N 0.940(14) . ?
N3B H2N 0.793(17) . ?
N3B H3N 0.897(18) . ?
C1 C3 1.3875(16) 2_654 ?
C1 C2 1.3901(14) . ?
C1 H1 0.9300 . ?
C2 O1 1.3791(13) . ?
C2 C3 1.3845(14) . ?
C3 H3 0.9300 . ?
O1 H1O 0.90(2) . ?
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
N3A H6N O1 0.793(19) 2.36(2) 3.0697(13) 149.7(19) 2_554 yes
N3B H2N O1 0.793(17) 2.389(17) 3.0494(13) 141.5(16) 2_665 yes
N3B H3N O1A 0.897(18) 1.979(19) 2.8745(14) 176.6(16) 1_565 yes
C3 H3 F1B 0.93 2.62 3.3269(13) 133.5 1_554 yes
N1A H4N N2B 0.947(14) 1.871(14) 2.8165(12) 175.7(15) 1_545 yes
O1 H1O O1B 0.90(2) 1.81(2) 2.7081(11) 176.9(18) . yes
N3A H5N O1B 0.89(2) 1.99(2) 2.8777(13) 172.9(17) . yes
N1B H1N N2A 0.940(14) 1.852(15) 2.7913(12) 176.8(16) . 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
N2A C2A C3A C4A -1.47(16) . . . . ?
N3A C2A C3A C4A 179.06(11) . . . . ?
N2A C2A C3A F1A 178.55(9) . . . . ?
N3A C2A C3A F1A -0.91(16) . . . . ?
F1A C3A C4A N1A -179.90(10) . . . . ?
C2A C3A C4A N1A 0.13(17) . . . . ?
C3A C4A N1A C1A 0.61(17) . . . . ?
O1A C1A N1A C4A -179.52(10) . . . . ?
N2A C1A N1A C4A -0.05(15) . . . . ?
N3A C2A N2A C1A -178.45(10) . . . . ?
C3A C2A N2A C1A 2.08(15) . . . . ?
O1A C1A N2A C2A 178.14(10) . . . . ?
N1A C1A N2A C2A -1.33(15) . . . . ?
N3B C2B C3B F1B -0.28(15) . . . . ?
N2B C2B C3B F1B -179.44(9) . . . . ?
N3B C2B C3B C4B 178.97(10) . . . . ?
N2B C2B C3B C4B -0.19(16) . . . . ?
F1B C3B C4B N1B -178.90(10) . . . . ?
C2B C3B C4B N1B 1.88(16) . . . . ?
C3B C4B N1B C1B -0.26(16) . . . . ?
O1B C1B N1B C4B 176.38(9) . . . . ?
N2B C1B N1B C4B -3.13(15) . . . . ?
N3B C2B N2B C1B 177.60(9) . . . . ?
C3B C2B N2B C1B -3.23(14) . . . . ?
O1B C1B N2B C2B -174.65(9) . . . . ?
N1B C1B N2B C2B 4.85(14) . . . . ?
C3 C1 C2 O1 179.09(10) 2_654 . . . ?
C3 C1 C2 C3 0.13(19) 2_654 . . . ?
O1 C2 C3 C1 -179.15(10) . . . 2_654 ?
C1 C2 C3 C1 -0.13(19) . . . 2_654 ?
