Halogen-bonded cocrystallization of racetam pharmaceuticals and perfluorinated iodobenzenes
Song, Lixing; Wei, Lijie; Liu, Chunling; Liu, Yiwei; Lian, Xiang; CrystEngComm 27 (2025) 2233–2240; doi:10.1039/D5CE00090D

data_7250033
_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         'C12 H13 N O3, C6 F3 I3'
_chemical_formula_sum            'C18 H13 F3 I3 N O3'
_chemical_formula_weight         728.99
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-01-06 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.0048(13)
_cell_length_b                   4.8659(3)
_cell_length_c                   15.7552(9)
_cell_measurement_reflns_used    3470
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.2490
_cell_measurement_theta_min      3.1420
_cell_volume                     2146.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       MAR
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '125 images, \D\F 1.2\% '
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9956
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_min         2.967
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_exptl_absorpt_coefficient_mu    4.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_description       plate
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details
;
 Flack x determined using 1453 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0361
_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/[\s^2^(Fo^2^)+(0.0752P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1013
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                3440
_reflns_number_total             3675
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00090d2.cif
_cod_data_source_block           ANI_TFTI_meoh
_cod_depositor_comments
'Adding full bibliography for 7250032--7250035.cif.'
_cod_database_code               7250033
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H4A(0.121) H4B(0.121) H5A(0.129) H5B(0.129) H6A(0.086) H6B(0.086)
 H14(0.07) H13(0.078) H11(0.071) H10(0.067) H16A(0.141) H16B(0.141) H16C(0.141)
 Fixed X: H4A(0.3699) H4B(0.3555) H5A(0.4067) H5B(0.4246) H6A(0.4884)
 H6B(0.4704) H14(0.5329) H13(0.5198) H11(0.4022) H10(0.4154) H16A(0.4153)
 H16B(0.4158) H16C(0.3858)
 Fixed Y: H4A(0.4263) H4B(0.6722) H5A(0.9201) H5B(0.6661) H6A(0.6457)
 H6B(0.9005) H14(0.0604) H13(-0.185) H11(0.2624) H10(0.5054) H16A(0.0947) H16B(-
 0.2124) H16C(-0.1268)
 Fixed Z: H4A(0.2148) H4B(0.2746) H5A(0.2111) H5B(0.1581) H6A(0.2354)
 H6B(0.2885) H14(0.4638) H13(0.586) H11(0.6328) H10(0.509) H16A(0.7641)
 H16B(0.7942) H16C(0.7145)
;
_shelx_res_checksum              13683
_olex2_submission_special_instructions 'No special instructions were received'