N-Iodophthalimide as a halogen bond donor, a comparison with N-iodosuccinimide and N-iodosaccharin
Jeon, Ie-Rang; Jeannin, Olivier; Robert, Antoine; Barrière, Frédéric; Fourmigué, Marc; CrystEngComm 26 (2024) 6075–6081; doi:10.1039/D4CE00654B

data_7249380
_publ_section_title
;
 N-Iodophthalimide as a halogen bond donor, a comparison with
 N-iodosuccinimide and N-iodosaccharin
;
_journal_issue                   42
_journal_name_full               CrystEngComm
_journal_page_first              6075
_journal_page_last               6081
_journal_paper_doi               10.1039/D4CE00654B
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C28 H32 I K N2 O10'
_chemical_formula_sum            'C28 H32 I K N2 O10'
_chemical_formula_weight         722.55
_chemical_name_systematic
'[Potassium(18-crown-6)][iodonium bis(phtamlimidate)]'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2018-03-15T15:30:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                102.724(8)
_cell_angle_beta                 99.561(7)
_cell_angle_gamma                114.396(7)
_cell_formula_units_Z            2
_cell_length_a                   9.9210(19)
_cell_length_b                   11.407(3)
_cell_length_c                   16.152(3)
_cell_measurement_reflns_used    3975
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.69
_cell_measurement_theta_min      2.3
_cell_measurement_wavelength     0.71073
_cell_volume                     1554.3(6)
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.075282
_diffrn_orient_matrix_UB_12      -0.083722
_diffrn_orient_matrix_UB_13      -0.05047
_diffrn_orient_matrix_UB_21      -0.025224
_diffrn_orient_matrix_UB_22      -0.05188
_diffrn_orient_matrix_UB_23      0.042581
_diffrn_orient_matrix_UB_31      -0.084058
_diffrn_orient_matrix_UB_32      0.025182
_diffrn_orient_matrix_UB_33      0.006029
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10644
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.664
_diffrn_reflns_theta_min         2.351
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_T_max  0.907
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             732
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/hexane'
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     542
_refine_ls_number_reflns         6707
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.0688P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0954
_reflns_Friedel_coverage         0
_reflns_number_gt                5270
_reflns_number_total             6707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00654b1.cif
_cod_data_source_block           shelx_CCDC3
_cod_depositor_comments
'Adding full bibliography for 7249377--7249386.cif.'
_cod_database_code               7249380
_shelx_res_checksum              97486
_shelx_hkl_checksum              36493