#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:29:44 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296459 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249386.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_7249386
loop_
_publ_author_name
'Jeon, Ie-Rang'
'Jeannin, Olivier'
'Robert, Antoine'
'Barrière, Frédéric'
'Fourmigué, Marc'
_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         'C24 H16 I2 N4 O6 S2'
_chemical_formula_sum            'C24 H16 I2 N4 O6 S2'
_chemical_formula_weight         774.33
_chemical_name_common            (NISacc)2(p-bipy)
_chemical_name_systematic        bis(N-iodosaccharin)(4,4'-bipyridine)
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_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             2018-02-27T16:47:54-00:00
_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                90
_cell_angle_beta                 105.954(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6873(9)
_cell_length_b                   9.2187(10)
_cell_length_c                   16.9914(16)
_cell_measurement_reflns_used    7516
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.44
_cell_measurement_wavelength     0.71073
_cell_volume                     1308.4(2)
_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 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28084
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_min         2.438
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_T_max  0.731
_exptl_absorpt_correction_T_min  0.575
_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    1.966
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             748
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/hexane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     173
_refine_ls_number_reflns         28084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0324
_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/[σ²(Fo²)+(0.0258P)²+2.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0
_reflns_number_gt                22562
_reflns_number_total             28084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00654b1.cif
_cod_data_source_block           shelx_CCDC9
_cod_depositor_comments
'Adding full bibliography for 7249377--7249386.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249386
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
I1 I 0.18453(4) 0.07721(4) 1.19560(2) 0.03743(13) Uani 1 1 d . . . . .
S002 S 0.39556(16) 0.26187(15) 1.09357(8) 0.0356(3) Uani 1 1 d . . . . .
O1 O 0.3181(5) 0.3972(4) 1.0973(3) 0.0477(10) Uani 1 1 d . . . . .
O3 O 0.1677(5) -0.0710(4) 1.0107(2) 0.0483(10) Uani 1 1 d . . . . .
O2 O 0.5417(4) 0.2383(4) 1.1553(2) 0.0470(10) Uani 1 1 d . . . . .
N2 N 0.0980(5) 0.0389(5) 1.3132(3) 0.0387(11) Uani 1 1 d . . . . .
N1 N 0.2715(5) 0.1255(5) 1.0902(3) 0.0384(11) Uani 1 1 d . . . . .
C2 C 0.3261(7) 0.1061(6) 0.9632(3) 0.0355(13) Uani 1 1 d . . . . .
C7 C 0.2443(7) 0.0396(6) 1.0210(3) 0.0367(13) Uani 1 1 d . . . . .
C10 C 0.0197(6) 0.0081(6) 1.4606(3) 0.0290(11) Uani 1 1 d . . . . .
C3 C 0.3214(7) 0.0565(6) 0.8861(3) 0.0471(15) Uani 1 1 d . . . . .
H3 H 0.2618 -0.025 0.8642 0.056 Uiso 1 1 calc R U . . .
C1 C 0.4150(6) 0.2273(6) 0.9945(3) 0.0351(13) Uani 1 1 d . . . . .
C12 C 0.0271(7) 0.1463(6) 1.3428(3) 0.0498(16) Uani 1 1 d . . . . .
H12 H 0.004 0.2322 1.3132 0.06 Uiso 1 1 calc R U . . .
C9 C 0.0924(6) -0.1021(6) 1.4285(3) 0.0379(13) Uani 1 1 d . . . . .
H9 H 0.1157 -0.1899 1.4561 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1301(6) -0.0822(6) 1.3562(3) 0.0418(13) Uani 1 1 d . . . . .
H8 H 0.1806 -0.1573 1.3365 0.05 Uiso 1 1 calc R U . . .
C6 C 0.5007(7) 0.3038(7) 0.9512(4) 0.0467(15) Uani 1 1 d . . . . .
H6 H 0.5594 0.3859 0.9729 0.056 Uiso 1 1 calc R U . . .
C5 C 0.4956(7) 0.2536(8) 0.8744(4) 0.0565(18) Uani 1 1 d . . . . .
H5 H 0.5524 0.3029 0.8436 0.068 Uiso 1 1 calc R U . . .
C4 C 0.4092(8) 0.1330(8) 0.8418(4) 0.0568(19) Uani 1 1 d . . . . .
H4 H 0.4089 0.1016 0.7897 0.068 Uiso 1 1 calc R U . . .
C11 C -0.0130(7) 0.1346(6) 1.4153(3) 0.0467(16) Uani 1 1 d . . . . .
H11 H -0.0621 0.2119 1.4339 0.056 Uiso 1 1 calc R U . . .
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
N1 I1 N2 176.36(16) . . ?
O2 S002 O1 115.9(3) . . ?
O2 S002 N1 110.6(2) . . ?
O1 S002 N1 110.9(2) . . ?
O2 S002 C1 112.0(2) . . ?
O1 S002 C1 111.7(3) . . ?
N1 S002 C1 93.6(2) . . ?
C8 N2 C12 117.8(5) . . ?
C8 N2 I1 122.0(4) . . ?
C12 N2 I1 119.9(4) . . ?
C7 N1 S002 115.0(4) . . ?
C7 N1 I1 124.5(3) . . ?
S002 N1 I1 120.0(2) . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 C7 126.5(5) . . ?
C1 C2 C7 113.3(5) . . ?
O3 C7 N1 124.6(5) . . ?
O3 C7 C2 126.5(5) . . ?
N1 C7 C2 108.9(5) . . ?
C11 C10 C9 116.4(5) . . ?
C11 C10 C10 121.7(6) . 3_558 ?
C9 C10 C10 121.8(6) . 3_558 ?
C2 C3 C4 117.8(6) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C6 C1 C2 122.5(5) . . ?
C6 C1 S002 128.6(5) . . ?
C2 C1 S002 108.9(4) . . ?
N2 C12 C11 122.5(5) . . ?
N2 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C8 C9 C10 120.2(5) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
N2 C8 C9 123.0(5) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
C5 C6 C1 117.0(6) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
C4 C5 C6 122.0(6) . . ?
C4 C5 H5 119 . . ?
C6 C5 H5 119 . . ?
C5 C4 C3 120.6(6) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
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
I1 N1 2.172(4) . ?
I1 N2 2.346(4) . ?
S002 O2 1.424(4) . ?
S002 O1 1.427(4) . ?
S002 N1 1.647(4) . ?
S002 C1 1.766(5) . ?
O3 C7 1.205(6) . ?
N2 C8 1.322(6) . ?
N2 C12 1.335(7) . ?
N1 C7 1.383(7) . ?
C2 C3 1.378(8) . ?
C2 C1 1.379(7) . ?
C2 C7 1.493(7) . ?
C10 C11 1.383(7) . ?
C10 C9 1.385(7) . ?
C10 C10 1.479(9) 3_558 ?
C3 C4 1.401(8) . ?
C3 H3 0.93 . ?
C1 C6 1.377(7) . ?
C12 C11 1.373(7) . ?
C12 H12 0.93 . ?
C9 C8 1.367(7) . ?
C9 H9 0.93 . ?
C8 H8 0.93 . ?
C6 C5 1.374(9) . ?
C6 H6 0.93 . ?
C5 C4 1.370(9) . ?
C5 H5 0.93 . ?
C4 H4 0.93 . ?
C11 H11 0.93 . ?
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
O2 S002 N1 C7 -110.6(4) . . . . ?
O1 S002 N1 C7 119.3(4) . . . . ?
C1 S002 N1 C7 4.5(4) . . . . ?
O2 S002 N1 I1 62.6(3) . . . . ?
O1 S002 N1 I1 -67.4(3) . . . . ?
C1 S002 N1 I1 177.7(3) . . . . ?
S002 N1 C7 O3 173.9(5) . . . . ?
I1 N1 C7 O3 1.0(8) . . . . ?
S002 N1 C7 C2 -5.7(6) . . . . ?
I1 N1 C7 C2 -178.6(3) . . . . ?
C3 C2 C7 O3 3.6(9) . . . . ?
C1 C2 C7 O3 -175.3(5) . . . . ?
C3 C2 C7 N1 -176.9(5) . . . . ?
C1 C2 C7 N1 4.2(6) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C7 C2 C3 C4 -178.8(5) . . . . ?
C3 C2 C1 C6 0.5(8) . . . . ?
C7 C2 C1 C6 179.4(5) . . . . ?
C3 C2 C1 S002 179.9(4) . . . . ?
C7 C2 C1 S002 -1.1(6) . . . . ?
O2 S002 C1 C6 -68.5(5) . . . . ?
O1 S002 C1 C6 63.4(5) . . . . ?
N1 S002 C1 C6 177.6(5) . . . . ?
O2 S002 C1 C2 112.1(4) . . . . ?
O1 S002 C1 C2 -116.0(4) . . . . ?
N1 S002 C1 C2 -1.8(4) . . . . ?
C8 N2 C12 C11 -0.1(9) . . . . ?
I1 N2 C12 C11 -174.0(5) . . . . ?
C11 C10 C9 C8 0.8(8) . . . . ?
C10 C10 C9 C8 -178.6(6) 3_558 . . . ?
C12 N2 C8 C9 0.7(8) . . . . ?
I1 N2 C8 C9 174.5(4) . . . . ?
C10 C9 C8 N2 -1.1(9) . . . . ?
C2 C1 C6 C5 -0.5(8) . . . . ?
S002 C1 C6 C5 -179.9(5) . . . . ?
C1 C6 C5 C4 0.1(9) . . . . ?
C6 C5 C4 C3 0.4(10) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
N2 C12 C11 C10 -0.1(10) . . . . ?
C9 C10 C11 C12 -0.3(8) . . . . ?
C10 C10 C11 C12 179.2(6) 3_558 . . . ?
