#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:38:17 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298855 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/00/7250032.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_7250032
loop_
_publ_author_name
'Song, Lixing'
'Wei, Lijie'
'Liu, Chunling'
'Liu, Yiwei'
'Lian, Xiang'
_publ_section_title
;
 Halogen-bonded cocrystallization of racetam pharmaceuticals and
 perfluorinated iodobenzenes
;
_journal_issue                   14
_journal_name_full               CrystEngComm
_journal_page_first              2233
_journal_page_last               2240
_journal_paper_doi               10.1039/D5CE00090D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C8 H14 N2 O2, C6 F3 I3'
_chemical_formula_sum            'C14 H14 F3 I3 N2 O2'
_chemical_formula_weight         679.97
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-12-26 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                93.461(5)
_cell_angle_beta                 95.913(4)
_cell_angle_gamma                111.472(5)
_cell_formula_units_Z            2
_cell_length_a                   8.5467(4)
_cell_length_b                   9.5605(5)
_cell_length_c                   13.0160(7)
_cell_measurement_reflns_used    4298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3870
_cell_measurement_theta_min      2.7440
_cell_volume                     978.93(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.16b (Rigaku OD, 2018)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8685
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.301
_diffrn_reflns_theta_min         2.302
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.307
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.731
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     23
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0400
_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)+(0.0305P)²+1.5120P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3431
_reflns_number_total             4580
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00090d2.cif
_cod_data_source_block           ETI_TFTI_meoh
_cod_depositor_comments
'Adding full bibliography for 7250032--7250035.cif.'
_cod_database_code               7250032
_shelx_shelxl_version_number     2014/7
_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.
;
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
O3 O -0.0484(4) -0.0219(3) 0.1117(3) 0.0435(8) Uani 1 1 d . . . . .
C2 C -0.083(2) 0.0771(16) 0.0736(16) 0.029(4) Uani 0.60(5) 1 d D U P A 1
C4 C -0.257(2) 0.0410(19) 0.014(2) 0.042(5) Uani 0.60(5) 1 d D . P A 1
H4A H -0.2623 -0.0014 -0.0569 0.050 Uiso 0.60(5) 1 calc R U P A 1
H4B H -0.3439 -0.0306 0.0469 0.050 Uiso 0.60(5) 1 calc R U P A 1
C5 C -0.280(3) 0.189(3) 0.014(3) 0.094(9) Uani 0.60(5) 1 d D . P A 1
H5A H -0.3336 0.1984 -0.0532 0.113 Uiso 0.60(5) 1 calc R U P A 1
H5B H -0.3486 0.1986 0.0666 0.113 Uiso 0.60(5) 1 calc R U P A 1
C6 C -0.104(3) 0.3074(16) 0.038(4) 0.057(6) Uani 0.60(5) 1 d D . P A 1
H6A H -0.0618 0.3458 -0.0254 0.068 Uiso 0.60(5) 1 calc R U P A 1
H6B H -0.1026 0.3910 0.0844 0.068 Uiso 0.60(5) 1 calc R U P A 1
N1 N -0.0028(14) 0.2291(16) 0.0869(12) 0.035(5) Uani 0.60(5) 1 d D . P A 1
C2B C -0.117(3) 0.070(2) 0.086(2) 0.027(6) Uani 0.40(5) 1 d D U P A 2
C4B C -0.283(3) 0.063(3) 0.029(3) 0.047(9) Uani 0.40(5) 1 d D . P A 2
H4C H -0.3216 -0.0149 -0.0292 0.057 Uiso 0.40(5) 1 calc R U P A 2
H4D H -0.3692 0.0416 0.0751 0.057 Uiso 0.40(5) 1 calc R U P A 2
C5B C -0.248(5) 0.216(4) -0.008(5) 0.091(16) Uani 0.40(5) 1 d D . P A 2
H5C H -0.2431 0.2108 -0.0823 0.109 Uiso 0.40(5) 1 calc R U P A 2
H5D H -0.3356 0.2527 0.0065 0.109 Uiso 0.40(5) 1 calc R U P A 2
C6B C -0.080(5) 0.317(3) 0.050(5) 0.072(13) Uani 0.40(5) 1 d D . P A 2
H6C H -0.0094 0.3803 0.0040 0.087 Uiso 0.40(5) 1 calc R U P A 2
H6D H -0.0945 0.3806 0.1059 0.087 Uiso 0.40(5) 1 calc R U P A 2
N1B N -0.0039(15) 0.214(3) 0.091(2) 0.046(9) Uani 0.40(5) 1 d D . P A 2
C7 C 0.1659(6) 0.2944(5) 0.1480(4) 0.0386(11) Uani 1 1 d D . . . .
H7 H 0.1976 0.2110 0.1699 0.046 Uiso 1 1 calc R U . A 1
C8 C 0.2977(6) 0.3858(5) 0.0819(4) 0.0446(12) Uani 1 1 d . . . . .
O9 O 0.4136(5) 0.5036(4) 0.1203(3) 0.0631(12) Uani 1 1 d . . . . .
N10 N 0.2827(6) 0.3303(5) -0.0162(3) 0.0592(14) Uani 1 1 d . . . . .
H10A H 0.3556 0.3771 -0.0555 0.071 Uiso 1 1 calc R U . . .
H10B H 0.2000 0.2475 -0.0404 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1632(7) 0.3902(6) 0.2454(4) 0.0499(14) Uani 1 1 d . . . . .
H11A H 0.2768 0.4337 0.2835 0.060 Uiso 1 1 calc R U . . .
H11B H 0.1308 0.4727 0.2250 0.060 Uiso 1 1 calc R U . . .
C12 C 0.0428(9) 0.3019(7) 0.3163(5) 0.072(2) Uani 1 1 d . . . . .
H12A H -0.0720 0.2735 0.2837 0.108 Uiso 1 1 calc R U . . .
H12B H 0.0591 0.3633 0.3806 0.108 Uiso 1 1 calc R U . . .
H12C H 0.0647 0.2126 0.3298 0.108 Uiso 1 1 calc R U . . .
C16 C 0.7845(6) 0.1067(5) 0.5412(4) 0.0400(11) Uani 1 1 d . . . . .
C15 C 0.7596(7) 0.2338(6) 0.5110(4) 0.0474(13) Uani 1 1 d . . . . .
C14 C 0.6724(7) 0.2372(6) 0.4171(4) 0.0481(13) Uani 1 1 d . . . . .
C13 C 0.6120(6) 0.1049(5) 0.3496(4) 0.0422(12) Uani 1 1 d . . . . .
C18 C 0.6327(6) -0.0252(5) 0.3743(4) 0.0398(11) Uani 1 1 d . . . . .
C17 C 0.7175(6) -0.0222(5) 0.4706(4) 0.0392(11) Uani 1 1 d . . . . .
I2 I 0.91179(5) 0.10434(5) 0.68595(3) 0.06069(14) Uani 1 1 d . . . . .
I1 I 0.64707(7) 0.43457(5) 0.37504(5) 0.08597(19) Uani 1 1 d . . . . .
I3 I 0.53742(4) -0.22298(4) 0.27162(3) 0.04954(12) Uani 1 1 d . . . . .
F2 F 0.8252(5) 0.3608(3) 0.5769(3) 0.0721(10) Uani 1 1 d . . . . .
F1 F 0.5306(4) 0.1052(4) 0.2552(3) 0.0675(10) Uani 1 1 d . . . . .
F3 F 0.7389(4) -0.1469(3) 0.4975(2) 0.0581(9) Uani 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'
I I -0.4742 1.8119 '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
O3 C2 C4 120.0(14) . . ?
O3 C2 N1 131.2(13) . . ?
N1 C2 C4 107.9(7) . . ?
C2 C4 H4A 110.7 . . ?
C2 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C5 C4 C2 105.2(8) . . ?
C5 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 C4 105.3(14) . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C5 C6 H6A 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 108.9 . . ?
N1 C6 C5 104.4(9) . . ?
N1 C6 H6A 110.9 . . ?
N1 C6 H6B 110.9 . . ?
C2 N1 C6 112.6(7) . . ?
C2 N1 C7 118.8(13) . . ?
C6 N1 C7 128.5(13) . . ?
O3 C2B C4B 137(2) . . ?
O3 C2B N1B 113(2) . . ?
N1B C2B C4B 108.1(9) . . ?
C2B C4B H4C 110.6 . . ?
C2B C4B H4D 110.6 . . ?
H4C C4B H4D 108.7 . . ?
C5B C4B C2B 105.7(9) . . ?
C5B C4B H4C 110.6 . . ?
C5B C4B H4D 110.6 . . ?
C4B C5B H5C 110.6 . . ?
C4B C5B H5D 110.6 . . ?
H5C C5B H5D 108.7 . . ?
C6B C5B C4B 105.9(16) . . ?
C6B C5B H5C 110.6 . . ?
C6B C5B H5D 110.6 . . ?
C5B C6B H6C 110.8 . . ?
C5B C6B H6D 110.8 . . ?
H6C C6B H6D 108.9 . . ?
N1B C6B C5B 104.7(11) . . ?
N1B C6B H6C 110.8 . . ?
N1B C6B H6D 110.8 . . ?
C2B N1B C6B 112.8(9) . . ?
C2B N1B C7 133(2) . . ?
C6B N1B C7 112(2) . . ?
N1 C7 H7 107.9 . . ?
N1 C7 C8 110.8(8) . . ?
N1 C7 C11 110.7(8) . . ?
N1B C7 C8 114.6(13) . . ?
N1B C7 C11 112.3(12) . . ?
C8 C7 H7 107.9 . . ?
C11 C7 H7 107.9 . . ?
C11 C7 C8 111.5(4) . . ?
O9 C8 C7 120.4(4) . . ?
O9 C8 N10 122.5(5) . . ?
N10 C8 C7 117.1(4) . . ?
C8 N10 H10A 120.0 . . ?
C8 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C7 C11 H11A 108.9 . . ?
C7 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C7 113.3(4) . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 C17 116.7(4) . . ?
C15 C16 I2 122.3(4) . . ?
C17 C16 I2 121.0(4) . . ?
C14 C15 C16 123.5(5) . . ?
F2 C15 C16 118.1(5) . . ?
F2 C15 C14 118.5(5) . . ?
C15 C14 C13 116.6(5) . . ?
C15 C14 I1 121.3(4) . . ?
C13 C14 I1 122.0(4) . . ?
C18 C13 C14 123.0(4) . . ?
F1 C13 C14 118.4(4) . . ?
F1 C13 C18 118.7(4) . . ?
C13 C18 C17 117.6(4) . . ?
C13 C18 I3 121.9(3) . . ?
C17 C18 I3 120.5(4) . . ?
C18 C17 C16 122.7(4) . . ?
F3 C17 C16 118.1(4) . . ?
F3 C17 C18 119.2(4) . . ?
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
O3 C2 1.210(14) . ?
O3 C2B 1.27(2) . ?
C2 C4 1.510(10) . ?
C2 N1 1.352(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.499(19) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.497(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.463(10) . ?
N1 C7 1.465(7) . ?
C2B C4B 1.508(11) . ?
C2B N1B 1.349(10) . ?
C4B H4C 0.9700 . ?
C4B H4D 0.9700 . ?
C4B C5B 1.497(19) . ?
C5B H5C 0.9700 . ?
C5B H5D 0.9700 . ?
C5B C6B 1.495(17) . ?
C6B H6C 0.9700 . ?
C6B H6D 0.9700 . ?
C6B N1B 1.462(11) . ?
N1B C7 1.463(9) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(7) . ?
C7 C11 1.526(7) . ?
C8 O9 1.230(5) . ?
C8 N10 1.328(6) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.509(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 C15 1.381(7) . ?
C16 C17 1.389(6) . ?
C16 I2 2.082(5) . ?
C15 C14 1.373(8) . ?
C15 F2 1.342(6) . ?
C14 C13 1.390(7) . ?
C14 I1 2.075(5) . ?
C13 C18 1.371(7) . ?
C13 F1 1.349(6) . ?
C18 C17 1.374(6) . ?
C18 I3 2.091(4) . ?
C17 F3 1.332(5) . ?
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
O3 C2 C4 C5 159(3) . . . . ?
O3 C2 N1 C6 -171(3) . . . . ?
O3 C2 N1 C7 8(4) . . . . ?
O3 C2B C4B C5B -158(5) . . . . ?
O3 C2B N1B C6B 173(4) . . . . ?
O3 C2B N1B C7 -23(5) . . . . ?
C2 C4 C5 C6 20(4) . . . . ?
C2 N1 C7 C8 119.3(17) . . . . ?
C2 N1 C7 C11 -116.4(17) . . . . ?
C4 C2 N1 C6 -2(3) . . . . ?
C4 C2 N1 C7 176.9(16) . . . . ?
C4 C5 C6 N1 -21(5) . . . . ?
C5 C6 N1 C2 14(4) . . . . ?
C5 C6 N1 C7 -164(3) . . . . ?
C6 N1 C7 C8 -62(3) . . . . ?
C6 N1 C7 C11 62(3) . . . . ?
N1 C2 C4 C5 -12(3) . . . . ?
N1 C7 C8 O9 142.7(8) . . . . ?
N1 C7 C8 N10 -38.7(9) . . . . ?
N1 C7 C11 C12 59.9(10) . . . . ?
C2B C4B C5B C6B -14(6) . . . . ?
C2B N1B C7 C8 132(3) . . . . ?
C2B N1B C7 C11 -100(3) . . . . ?
C4B C2B N1B C6B 5(5) . . . . ?
C4B C2B N1B C7 170(3) . . . . ?
C4B C5B C6B N1B 17(7) . . . . ?
C5B C6B N1B C2B -14(7) . . . . ?
C5B C6B N1B C7 178(4) . . . . ?
C6B N1B C7 C8 -64(4) . . . . ?
C6B N1B C7 C11 65(4) . . . . ?
N1B C2B C4B C5B 6(5) . . . . ?
N1B C7 C8 O9 147.9(13) . . . . ?
N1B C7 C8 N10 -33.5(13) . . . . ?
N1B C7 C11 C12 53.5(14) . . . . ?
C8 C7 C11 C12 -176.3(5) . . . . ?
C11 C7 C8 O9 18.9(7) . . . . ?
C11 C7 C8 N10 -162.5(5) . . . . ?
C16 C15 C14 C13 -1.8(8) . . . . ?
C16 C15 C14 I1 -177.9(4) . . . . ?
C15 C16 C17 C18 1.1(8) . . . . ?
C15 C16 C17 F3 -179.7(5) . . . . ?
C15 C14 C13 C18 1.6(8) . . . . ?
C15 C14 C13 F1 -177.9(5) . . . . ?
C14 C13 C18 C17 -0.1(8) . . . . ?
C14 C13 C18 I3 179.2(4) . . . . ?
C13 C18 C17 C16 -1.3(8) . . . . ?
C13 C18 C17 F3 179.5(4) . . . . ?
C17 C16 C15 C14 0.6(8) . . . . ?
C17 C16 C15 F2 -179.0(5) . . . . ?
I2 C16 C15 C14 -178.3(4) . . . . ?
I2 C16 C15 F2 2.2(7) . . . . ?
I2 C16 C17 C18 180.0(4) . . . . ?
I2 C16 C17 F3 -0.9(7) . . . . ?
I1 C14 C13 C18 177.6(4) . . . . ?
I1 C14 C13 F1 -1.8(7) . . . . ?
I3 C18 C17 C16 179.4(4) . . . . ?
I3 C18 C17 F3 0.2(7) . . . . ?
F2 C15 C14 C13 177.7(5) . . . . ?
F2 C15 C14 I1 1.6(7) . . . . ?
F1 C13 C18 C17 179.4(5) . . . . ?
F1 C13 C18 I3 -1.4(7) . . . . ?
