#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:29:44 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296459 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/93/7249383.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_7249383
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_absolute_configuration ;
_chemical_formula_moiety         'C12 H12 N2, 2(C8 H4 I N O2), C H2 Cl2'
_chemical_formula_sum            'C29 H22 Cl2 I2 N4 O4'
_chemical_formula_weight         815.21
_chemical_name_common            (NIPht)2(o-Me2bipy),(CH2Cl2)
_chemical_name_systematic
'Bis(N-iodophalimide)(5,5?-dimethyl-2,2?-bipyridine), (dichloromethane)'
_space_group_IT_number           32
_space_group_name_Hall           'P 2 -2ab'
_space_group_name_H-M_alt        'P b a 2'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      32
_symmetry_space_group_name_Hall  'P 2 -2ab'
_symmetry_space_group_name_H-M   'P b a 2'
_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             2018-03-30T16:48:19-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   25.6531(16)
_cell_length_b                   14.2270(8)
_cell_length_c                   4.1646(3)
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.8
_cell_measurement_theta_min      2.78
_cell_measurement_wavelength     0.71073
_cell_volume                     1519.94(17)
_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 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_UB_11      -0.034281
_diffrn_orient_matrix_UB_12      -0.021791
_diffrn_orient_matrix_UB_13      -0.08675
_diffrn_orient_matrix_UB_21      0.015317
_diffrn_orient_matrix_UB_22      -0.003109
_diffrn_orient_matrix_UB_23      -0.220547
_diffrn_orient_matrix_UB_31      0.010477
_diffrn_orient_matrix_UB_32      -0.066753
_diffrn_orient_matrix_UB_33      0.038592
_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  0.0542
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13219
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.779
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_correction_T_min  0.817
_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    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/pentane'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
;
 Flack x determined using 915 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3449
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.04
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0326P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0759
_refine_ls_wR_factor_ref         0.0818
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2655
_reflns_number_total             3449
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00654b1.cif
_cod_data_source_block           shelx_CCDC6
_cod_depositor_comments
'Adding full bibliography for 7249377--7249386.cif.'
_cod_database_code               7249383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, 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
C1 C 0.1702(3) 0.3878(5) 0.4174(16) 0.031(2) Uani 1 1 d . . . . .
C2 C 0.1662(3) 0.4715(5) 0.578(2) 0.046(3) Uani 1 1 d . . . . .
H2 H 0.1346 0.4912 0.6644 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2111(4) 0.5260(6) 0.607(3) 0.058(3) Uani 1 1 d . . . . .
H3 H 0.2097 0.5833 0.7137 0.069 Uiso 1 1 calc R U . . .
C4 C 0.2574(3) 0.4953(5) 0.477(4) 0.054(2) Uani 1 1 d . . . . .
H4 H 0.2868 0.5331 0.4981 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2620(3) 0.4098(6) 0.317(3) 0.047(2) Uani 1 1 d . . . . .
H5 H 0.2936 0.3894 0.2325 0.056 Uiso 1 1 calc R U . . .
C6 C 0.2164(3) 0.3564(5) 0.289(2) 0.0351(18) Uani 1 1 d . . . . .
C7 C 0.2078(3) 0.2637(5) 0.131(2) 0.0354(18) Uani 1 1 d . . . . .
C8 C 0.1292(3) 0.3158(5) 0.337(2) 0.0357(18) Uani 1 1 d . . . . .
C9 C 0.4808(3) 0.4600(5) 0.6632(18) 0.0295(16) Uani 1 1 d . . . . .
C10 C 0.3960(3) 0.4060(6) 0.740(2) 0.042(2) Uani 1 1 d . . . . .
H10 H 0.3619 0.4182 0.8019 0.05 Uiso 1 1 calc R U . . .
C11 C 0.4082(3) 0.3164(5) 0.640(2) 0.0382(19) Uani 1 1 d . . . . .
C12 C 0.4594(3) 0.3000(5) 0.548(2) 0.044(3) Uani 1 1 d . . . . .
H12 H 0.4693 0.2407 0.4765 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4954(3) 0.3714(5) 0.561(2) 0.042(3) Uani 1 1 d . . . . .
H13 H 0.5297 0.36 0.5008 0.051 Uiso 1 1 calc R U . . .
C14 C 0.3663(4) 0.2403(6) 0.633(3) 0.060(3) Uani 1 1 d . . . . .
H14A H 0.3342 0.2652 0.7159 0.09 Uiso 1 1 calc R U . . .
H14B H 0.3772 0.1881 0.7633 0.09 Uiso 1 1 calc R U . . .
H14C H 0.3612 0.2195 0.4163 0.09 Uiso 1 1 calc R U . . .
N1 N 0.1552(3) 0.2434(4) 0.1708(17) 0.0371(16) Uani 1 1 d . . . . .
N2 N 0.4311(2) 0.4779(4) 0.7542(16) 0.0313(14) Uani 1 1 d . . . . .
O1 O 0.2391(2) 0.2148(4) -0.007(3) 0.0616(17) Uani 1 1 d . . . . .
O2 O 0.0830(2) 0.3166(4) 0.4049(18) 0.058(2) Uani 1 1 d . . . . .
I1 I 0.11623(2) 0.12669(3) -0.0140(3) 0.03654(14) Uani 1 1 d . . . . .
Cl1 Cl 0.45417(14) 0.0606(3) 1.0758(8) 0.0993(12) Uani 1 1 d . . . . .
C15 C 0.5117(11) 0.0400(16) 0.911(7) 0.095(9) Uani 0.5 1 d . . P . .
H15A H 0.5333 0.0953 0.9384 0.114 Uiso 0.5 1 calc R U P . .
H15B H 0.5069 0.0303 0.6826 0.114 Uiso 0.5 1 calc R U P . .
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 122.5(7) . . ?
C2 C1 C8 130.4(7) . . ?
C6 C1 C8 107.1(6) . . ?
C1 C2 C3 117.7(8) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 120.2(8) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.5(8) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 116.4(8) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C1 C6 C5 120.7(7) . . ?
C1 C6 C7 109.3(6) . . ?
C5 C6 C7 130.0(8) . . ?
O1 C7 N1 125.6(7) . . ?
O1 C7 C6 128.3(7) . . ?
N1 C7 C6 106.1(6) . . ?
O2 C8 N1 125.4(7) . . ?
O2 C8 C1 128.5(7) . . ?
N1 C8 C1 106.0(6) . . ?
N2 C9 C13 120.8(7) . . ?
N2 C9 C9 118.3(7) . 2_665 ?
C13 C9 C9 120.8(8) . 2_665 ?
N2 C10 C11 124.0(7) . . ?
N2 C10 H10 118 . . ?
C11 C10 H10 118 . . ?
C10 C11 C12 117.0(7) . . ?
C10 C11 C14 120.3(7) . . ?
C12 C11 C14 122.8(7) . . ?
C13 C12 C11 120.0(7) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C12 C13 C9 120.3(7) . . ?
C12 C13 H13 119.9 . . ?
C9 C13 H13 119.9 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C8 111.4(6) . . ?
C7 N1 I1 125.9(5) . . ?
C8 N1 I1 122.5(5) . . ?
C9 N2 C10 117.9(6) . . ?
Cl1 C15 Cl1 114.5(14) . 2_655 ?
Cl1 C15 H15A 108.6 . . ?
Cl1 C15 H15A 108.6 2_655 . ?
Cl1 C15 H15B 108.6 . . ?
Cl1 C15 H15B 108.6 2_655 . ?
H15A C15 H15B 107.6 . . ?
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
C1 C2 1.368(10) . ?
C1 C6 1.377(11) . ?
C1 C8 1.505(10) . ?
C2 C3 1.393(12) . ?
C2 H2 0.93 . ?
C3 C4 1.376(14) . ?
C3 H3 0.93 . ?
C4 C5 1.394(13) . ?
C4 H4 0.93 . ?
C5 C6 1.399(12) . ?
C5 H5 0.93 . ?
C6 C7 1.489(10) . ?
C7 O1 1.210(10) . ?
C7 N1 1.390(10) . ?
C8 O2 1.217(9) . ?
C8 N1 1.410(10) . ?
C9 N2 1.355(9) . ?
C9 C13 1.383(10) . ?
C9 C9 1.505(14) 2_665 ?
C10 N2 1.363(10) . ?
C10 C11 1.376(12) . ?
C10 H10 0.93 . ?
C11 C12 1.390(11) . ?
C11 C14 1.525(11) . ?
C12 C13 1.374(11) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
N1 I1 2.085(6) . ?
Cl1 C15 1.65(3) . ?
C15 Cl1 1.81(2) 2_655 ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
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
C6 C1 C2 C3 0.5(12) . . . . ?
C8 C1 C2 C3 -177.7(8) . . . . ?
C1 C2 C3 C4 -0.2(15) . . . . ?
C2 C3 C4 C5 -0.5(19) . . . . ?
C3 C4 C5 C6 0.8(17) . . . . ?
C2 C1 C6 C5 -0.2(12) . . . . ?
C8 C1 C6 C5 178.4(8) . . . . ?
C2 C1 C6 C7 179.9(7) . . . . ?
C8 C1 C6 C7 -1.5(8) . . . . ?
C4 C5 C6 C1 -0.5(13) . . . . ?
C4 C5 C6 C7 179.4(10) . . . . ?
C1 C6 C7 O1 179.8(9) . . . . ?
C5 C6 C7 O1 0.0(16) . . . . ?
C1 C6 C7 N1 0.6(9) . . . . ?
C5 C6 C7 N1 -179.3(9) . . . . ?
C2 C1 C8 O2 -1.2(14) . . . . ?
C6 C1 C8 O2 -179.7(9) . . . . ?
C2 C1 C8 N1 -179.7(8) . . . . ?
C6 C1 C8 N1 1.8(9) . . . . ?
N2 C10 C11 C12 -0.3(14) . . . . ?
N2 C10 C11 C14 179.9(9) . . . . ?
C10 C11 C12 C13 0.6(14) . . . . ?
C14 C11 C12 C13 -179.7(9) . . . . ?
C11 C12 C13 C9 -0.7(14) . . . . ?
N2 C9 C13 C12 0.5(12) . . . . ?
C9 C9 C13 C12 -176.9(7) 2_665 . . . ?
O1 C7 N1 C8 -178.7(9) . . . . ?
C6 C7 N1 C8 0.6(9) . . . . ?
O1 C7 N1 I1 -2.6(14) . . . . ?
C6 C7 N1 I1 176.7(5) . . . . ?
O2 C8 N1 C7 180.0(9) . . . . ?
C1 C8 N1 C7 -1.4(9) . . . . ?
O2 C8 N1 I1 3.8(12) . . . . ?
C1 C8 N1 I1 -177.7(5) . . . . ?
C13 C9 N2 C10 -0.2(11) . . . . ?
C9 C9 N2 C10 177.2(6) 2_665 . . . ?
C11 C10 N2 C9 0.2(13) . . . . ?
