# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2366101'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-02-19T15:55:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H4 I N O2'
_chemical_formula_moiety         'C8 H4 I N O2'
_chemical_formula_weight         273.02
_chemical_absolute_configuration ;

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.9049(2)
_cell_length_b                   7.0364(2)
_cell_length_c                   24.1144(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     832.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2804
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      25.95
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    2.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.761
_exptl_absorpt_correction_T_max  0.859

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6060  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.115137
_diffrn_orient_matrix_ub_12      -0.05801
_diffrn_orient_matrix_ub_13      -0.029744
_diffrn_orient_matrix_ub_21      -0.164224
_diffrn_orient_matrix_ub_22      0.065617
_diffrn_orient_matrix_ub_23      0.015405
_diffrn_orient_matrix_ub_31      0.036602
_diffrn_orient_matrix_ub_32      0.111924
_diffrn_orient_matrix_ub_33      -0.024448
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_number            5953
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.016
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_coverage         0.65
_reflns_number_total             1914
_reflns_number_gt                1807
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1914
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0572
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 680 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_diff_density_max         0.543
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'

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 1.1088(10) -0.0829(7) 0.6273(2) 0.0295(11) Uani 1 1 d . . . . .
C2 C 1.1058(12) 0.0674(7) 0.5908(2) 0.0329(12) Uani 1 1 d . . . . .
C3 C 1.2709(12) 0.0684(8) 0.5443(2) 0.0405(14) Uani 1 1 d . . . . .
H3 H 1.2683 0.1691 0.5193 0.049 Uiso 1 1 calc R U . . .
C4 C 1.4379(13) -0.0851(9) 0.5366(2) 0.0464(15) Uani 1 1 d . . . . .
H4 H 1.5513 -0.088 0.5057 0.056 Uiso 1 1 calc R U . . .
C5 C 1.4438(11) -0.2362(8) 0.5733(2) 0.0470(13) Uani 1 1 d . . . . .
H5 H 1.5619 -0.3373 0.567 0.056 Uiso 1 1 calc R U . . .
C6 C 1.2741(10) -0.2382(8) 0.6197(2) 0.0407(12) Uani 1 1 d . . . . .
H6 H 1.273 -0.3399 0.6443 0.049 Uiso 1 1 calc R U . . .
C7 C 0.9099(11) -0.0406(7) 0.6724(2) 0.0314(12) Uani 1 1 d . . . . .
C8 C 0.9100(11) 0.2108(7) 0.61099(19) 0.0337(11) Uani 1 1 d . . . . .
N1 N 0.7992(9) 0.1362(6) 0.65985(16) 0.0323(10) Uani 1 1 d . . . . .
O1 O 0.8556(8) -0.1364(5) 0.71234(15) 0.0480(10) Uani 1 1 d . . . . .
O2 O 0.8501(10) 0.3627(6) 0.59147(16) 0.0518(12) Uani 1 1 d . . . . .
I1 I 0.52836(7) 0.26855(4) 0.71075(2) 0.03523(12) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C6 1.373(7) . ?
C1 C2 1.376(7) . ?
C1 C7 1.491(8) . ?
C2 C3 1.384(7) . ?
C2 C8 1.475(7) . ?
C3 C4 1.368(8) . ?
C3 H3 0.93 . ?
C4 C5 1.383(8) . ?
C4 H4 0.93 . ?
C5 C6 1.394(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 O1 1.205(6) . ?
C7 N1 1.391(6) . ?
C8 O2 1.205(6) . ?
C8 N1 1.399(6) . ?
N1 I1 2.034(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
C6 C1 C2 122.1(5) . . ?
C6 C1 C7 130.0(5) . . ?
C2 C1 C7 107.8(4) . . ?
C1 C2 C3 121.1(5) . . ?
C1 C2 C8 108.7(4) . . ?
C3 C2 C8 130.1(5) . . ?
C4 C3 C2 117.0(6) . . ?
C4 C3 H3 121.5 . . ?
C2 C3 H3 121.5 . . ?
C3 C4 C5 122.2(6) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 120.5(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 116.9(5) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 C7 N1 126.1(5) . . ?
O1 C7 C1 128.0(5) . . ?
N1 C7 C1 106.0(4) . . ?
O2 C8 N1 124.5(5) . . ?
O2 C8 C2 129.6(5) . . ?
N1 C8 C2 105.9(4) . . ?
C7 N1 C8 111.6(4) . . ?
C7 N1 I1 122.2(3) . . ?
C8 N1 I1 126.2(3) . . ?

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 0.1(8) . . . . ?
C7 C1 C2 C3 -179.9(5) . . . . ?
C6 C1 C2 C8 -179.5(5) . . . . ?
C7 C1 C2 C8 0.6(6) . . . . ?
C1 C2 C3 C4 -0.6(8) . . . . ?
C8 C2 C3 C4 178.8(5) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
C7 C1 C6 C5 -179.1(5) . . . . ?
C4 C5 C6 C1 -1.4(8) . . . . ?
C6 C1 C7 O1 0.8(10) . . . . ?
C2 C1 C7 O1 -179.3(6) . . . . ?
C6 C1 C7 N1 179.8(5) . . . . ?
C2 C1 C7 N1 -0.3(6) . . . . ?
C1 C2 C8 O2 179.1(6) . . . . ?
C3 C2 C8 O2 -0.4(10) . . . . ?
C1 C2 C8 N1 -0.7(6) . . . . ?
C3 C2 C8 N1 179.8(6) . . . . ?
O1 C7 N1 C8 178.9(5) . . . . ?
C1 C7 N1 C8 -0.2(6) . . . . ?
O1 C7 N1 I1 2.4(8) . . . . ?
C1 C7 N1 I1 -176.7(3) . . . . ?
O2 C8 N1 C7 -179.3(5) . . . . ?
C2 C8 N1 C7 0.5(6) . . . . ?
O2 C8 N1 I1 -3.0(8) . . . . ?
C2 C8 N1 I1 176.8(3) . . . . ?



# END of CIF
_chemical_name_systematic        N-iodophtalimide
_chemical_name_common            NIPht
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2366103'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-02-20T11:11:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H16 I2 N4 O4'
_chemical_formula_moiety         'C26 H16 I2 N4 O4'
_chemical_formula_weight         702.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.8622(3)
_cell_length_b                   33.380(3)
_cell_length_c                   8.0329(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.989(3)
_cell_angle_gamma                90
_cell_volume                     1259.38(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2593
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      26.6
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.975

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5826  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.01101
_diffrn_orient_matrix_ub_12      0.0283
_diffrn_orient_matrix_ub_13      0.03861
_diffrn_orient_matrix_ub_21      -0.1416
_diffrn_orient_matrix_ub_22      -0.008226
_diffrn_orient_matrix_ub_23      0.064286
_diffrn_orient_matrix_ub_31      0.158618
_diffrn_orient_matrix_ub_32      -0.005379
_diffrn_orient_matrix_ub_33      0.104809
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_number            6306
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.695
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             2870
_reflns_number_gt                2178
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0195P)²+2.2220P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2870
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.92
_refine_diff_density_rms         0.116

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'

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 -0.0480(9) 0.16222(14) 0.7465(6) 0.0348(11) Uani 1 1 d . . . . .
C2 C -0.1389(10) 0.18432(15) 0.5971(6) 0.0359(11) Uani 1 1 d . . . . .
C3 C -0.3171(11) 0.21664(17) 0.5871(7) 0.0526(14) Uani 1 1 d . . . . .
H3 H -0.3772 0.2317 0.4869 0.063 Uiso 1 1 calc R U . . .
C4 C -0.4026(12) 0.22551(17) 0.7355(8) 0.0552(15) Uani 1 1 d . . . . .
H4 H -0.5248 0.247 0.7337 0.066 Uiso 1 1 calc R U . . .
C5 C -0.3141(13) 0.2039(2) 0.8831(8) 0.0623(18) Uani 1 1 d . . . . .
H5 H -0.3772 0.2108 0.9792 0.075 Uiso 1 1 calc R U . . .
C6 C -0.1316(12) 0.17174(18) 0.8922(7) 0.0533(15) Uani 1 1 d . . . . .
H6 H -0.0677 0.1571 0.9934 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1369(10) 0.12964(16) 0.7118(6) 0.0389(11) Uani 1 1 d . . . . .
C8 C -0.0105(10) 0.16613(15) 0.4643(6) 0.0384(11) Uani 1 1 d . . . . .
C9 C 0.7206(12) 0.01550(17) 0.2945(7) 0.0548(15) Uani 1 1 d . . . . .
H9 H 0.6851 0.0034 0.391 0.066 Uiso 1 1 calc R U . . .
C10 C 0.8660(13) -0.00567(17) 0.1991(7) 0.0564(16) Uani 1 1 d . . . . .
H10 H 0.9285 -0.0315 0.2323 0.068 Uiso 1 1 calc R U . . .
C11 C 0.9207(9) 0.01104(15) 0.0538(6) 0.0348(11) Uani 1 1 d . . . . .
C12 C 0.8245(12) 0.04937(18) 0.0153(7) 0.0529(15) Uani 1 1 d . . . . .
H12 H 0.8562 0.0623 -0.0806 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6803(11) 0.06885(19) 0.1192(6) 0.0540(15) Uani 1 1 d . . . . .
H13 H 0.6173 0.0949 0.0907 0.065 Uiso 1 1 calc R U . . .
N1 N 0.1532(8) 0.13392(12) 0.5436(5) 0.0356(9) Uani 1 1 d . . . . .
N2 N 0.6281(8) 0.05234(14) 0.2561(5) 0.0447(11) Uani 1 1 d . . . . .
O1 O 0.2514(9) 0.10306(12) 0.8081(5) 0.0611(11) Uani 1 1 d . . . . .
O2 O -0.0430(9) 0.17628(12) 0.3159(5) 0.0600(11) Uani 1 1 d . . . . .
I1 I 0.37672(6) 0.09506(2) 0.41909(4) 0.04059(12) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C6 1.372(6) . ?
C1 C2 1.380(6) . ?
C1 C7 1.483(7) . ?
C2 C3 1.373(7) . ?
C2 C8 1.497(6) . ?
C3 C4 1.392(7) . ?
C3 H3 0.93 . ?
C4 C5 1.360(8) . ?
C4 H4 0.93 . ?
C5 C6 1.382(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 O1 1.214(6) . ?
C7 N1 1.381(6) . ?
C8 O2 1.210(5) . ?
C8 N1 1.390(6) . ?
C9 N2 1.318(7) . ?
C9 C10 1.366(7) . ?
C9 H9 0.93 . ?
C10 C11 1.380(7) . ?
C10 H10 0.93 . ?
C11 C12 1.370(7) . ?
C11 C11 1.494(8) 3_755 ?
C12 C13 1.383(7) . ?
C12 H12 0.93 . ?
C13 N2 1.312(6) . ?
C13 H13 0.93 . ?
N1 I1 2.104(4) . ?
N2 I1 2.464(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
C6 C1 C2 121.3(5) . . ?
C6 C1 C7 131.1(5) . . ?
C2 C1 C7 107.6(4) . . ?
C3 C2 C1 121.8(4) . . ?
C3 C2 C8 130.5(5) . . ?
C1 C2 C8 107.7(4) . . ?
C2 C3 C4 116.1(5) . . ?
C2 C3 H3 121.9 . . ?
C4 C3 H3 121.9 . . ?
C5 C4 C3 122.5(5) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.5(5) . . ?
C1 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
O1 C7 N1 124.5(5) . . ?
O1 C7 C1 128.1(4) . . ?
N1 C7 C1 107.4(4) . . ?
O2 C8 N1 125.5(4) . . ?
O2 C8 C2 128.1(5) . . ?
N1 C8 C2 106.4(4) . . ?
N2 C9 C10 123.1(5) . . ?
N2 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
C9 C10 C11 120.4(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 116.1(4) . . ?
C12 C11 C11 121.8(6) . 3_755 ?
C10 C11 C11 122.1(6) . 3_755 ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120 . . ?
C13 C12 H12 120 . . ?
N2 C13 C12 123.1(5) . . ?
N2 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
C7 N1 C8 110.9(4) . . ?
C7 N1 I1 124.7(3) . . ?
C8 N1 I1 124.3(3) . . ?
C13 N2 C9 117.4(4) . . ?
C13 N2 I1 115.6(4) . . ?
C9 N2 I1 127.0(3) . . ?
N1 I1 N2 176.20(15) . . ?

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 -0.2(8) . . . . ?
C7 C1 C2 C3 179.3(5) . . . . ?
C6 C1 C2 C8 -179.9(5) . . . . ?
C7 C1 C2 C8 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.6(8) . . . . ?
C8 C2 C3 C4 179.0(5) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 C6 0.3(9) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
C7 C1 C6 C5 -178.4(5) . . . . ?
C4 C5 C6 C1 -1.1(9) . . . . ?
C6 C1 C7 O1 2.0(9) . . . . ?
C2 C1 C7 O1 -177.5(5) . . . . ?
C6 C1 C7 N1 -179.5(5) . . . . ?
C2 C1 C7 N1 1.0(5) . . . . ?
C3 C2 C8 O2 -1.3(9) . . . . ?
C1 C2 C8 O2 178.4(5) . . . . ?
C3 C2 C8 N1 180.0(5) . . . . ?
C1 C2 C8 N1 -0.4(5) . . . . ?
N2 C9 C10 C11 -0.7(9) . . . . ?
C9 C10 C11 C12 0.8(8) . . . . ?
C9 C10 C11 C11 179.9(6) . . . 3_755 ?
C10 C11 C12 C13 -0.4(8) . . . . ?
C11 C11 C12 C13 -179.6(5) 3_755 . . . ?
C11 C12 C13 N2 -0.1(9) . . . . ?
O1 C7 N1 C8 177.3(5) . . . . ?
C1 C7 N1 C8 -1.2(5) . . . . ?
O1 C7 N1 I1 0.5(7) . . . . ?
C1 C7 N1 I1 -178.0(3) . . . . ?
O2 C8 N1 C7 -177.8(5) . . . . ?
C2 C8 N1 C7 1.0(5) . . . . ?
O2 C8 N1 I1 -1.0(7) . . . . ?
C2 C8 N1 I1 177.8(3) . . . . ?
C12 C13 N2 C9 0.3(8) . . . . ?
C12 C13 N2 I1 178.6(4) . . . . ?
C10 C9 N2 C13 0.1(9) . . . . ?
C10 C9 N2 I1 -178.0(4) . . . . ?



# END of CIF
_chemical_name_systematic        
"Bis(N(iodophtalimide)(4,4'-bipyridine), alpha phase"
_chemical_name_common            alpha-(NIPht)2(p-bipy)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2366102'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2024-03-29T15:54:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C15 H14 I N3 O2'
_chemical_formula_sum            'C15 H14 I N3 O2'
_chemical_formula_weight         395.19

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2802(9)
_cell_length_b                   11.8980(11)
_cell_length_c                   13.5467(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.135(3)
_cell_angle_gamma                90
_cell_volume                     1472.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9853
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_T_max  0.916

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6601  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.8853                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      -0.044896
_diffrn_orient_matrix_ub_12      -0.066363
_diffrn_orient_matrix_ub_13      0.028282
_diffrn_orient_matrix_ub_21      -0.099773
_diffrn_orient_matrix_ub_22      0.031293
_diffrn_orient_matrix_ub_23      -0.024941
_diffrn_orient_matrix_ub_31      -0.003483
_diffrn_orient_matrix_ub_32      -0.040997
_diffrn_orient_matrix_ub_33      -0.064818
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_number            20445
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.811
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_Friedel_coverage         0
_reflns_number_total             3308
_reflns_number_gt                3086
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0117P)²+0.8853P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3308
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.016
_refine_ls_wR_factor_ref         0.0399
_refine_ls_wR_factor_gt          0.0381
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
I I -0.4742 1.8119 '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'

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 0.08737(18) 0.30390(13) 0.45313(12) 0.0259(3) Uani 1 1 d . . . . .
H1 H 0.078429 0.2574 0.395366 0.031 Uiso 1 1 calc R U . . .
C2 C -0.02108(17) 0.29992(13) 0.50967(11) 0.0243(3) Uani 1 1 d . . . . .
H2 H -0.103498 0.252496 0.490028 0.029 Uiso 1 1 calc R U . . .
C3 C -0.01071(16) 0.36647(12) 0.59756(11) 0.0212(3) Uani 1 1 d . . . . .
C4 C 0.11609(16) 0.43479(14) 0.61984(11) 0.0239(3) Uani 1 1 d . . . . .
H4 H 0.130794 0.480802 0.678067 0.029 Uiso 1 1 calc R U . . .
C5 C 0.21702(17) 0.43449(14) 0.55771(12) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.299704 0.482413 0.573758 0.031 Uiso 1 1 calc R U . . .
C6 C -0.09251(18) 0.42857(16) 0.75006(12) 0.0296(3) Uani 1 1 d . . . . .
H6A H -0.004911 0.40073 0.79447 0.044 Uiso 1 1 calc R U . . .
H6B H -0.178035 0.418582 0.782532 0.044 Uiso 1 1 calc R U . . .
H6C H -0.080253 0.508536 0.736306 0.044 Uiso 1 1 calc R U . . .
C7 C -0.24603(18) 0.29839(16) 0.62845(14) 0.0332(4) Uani 1 1 d . . . . .
H7A H -0.292135 0.315897 0.559412 0.05 Uiso 1 1 calc R U . . .
H7B H -0.314349 0.315568 0.673914 0.05 Uiso 1 1 calc R U . . .
H7C H -0.220474 0.21843 0.633565 0.05 Uiso 1 1 calc R U . . .
C8 C 0.54086(17) 0.46908(14) 0.20183(12) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.66493(16) 0.31655(13) 0.27861(12) 0.0241(3) Uani 1 1 d . . . . .
C10 C 0.73895(17) 0.35109(13) 0.19373(12) 0.0239(3) Uani 1 1 d . . . . .
C11 C 0.66268(17) 0.44261(13) 0.14638(12) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.70221(18) 0.49231(15) 0.06321(13) 0.0286(3) Uani 1 1 d . . . . .
H12 H 0.649699 0.554626 0.031015 0.034 Uiso 1 1 calc R U . . .
C13 C 0.82255(19) 0.44725(16) 0.02832(13) 0.0326(4) Uani 1 1 d . . . . .
H13 H 0.851764 0.47876 -0.02951 0.039 Uiso 1 1 calc R U . . .
C14 C 0.90083(19) 0.35698(16) 0.07650(15) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.983643 0.329092 0.051853 0.04 Uiso 1 1 calc R U . . .
C15 C 0.85949(17) 0.30682(14) 0.16044(13) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.912027 0.24488 0.19329 0.035 Uiso 1 1 calc R U . . .
I1 I 0.38572(2) 0.37811(2) 0.37552(2) 0.02353(4) Uani 1 1 d . . . . .
N1 N 0.20608(15) 0.37035(11) 0.47522(10) 0.0243(3) Uani 1 1 d . . . . .
N2 N -0.11389(15) 0.36572(12) 0.65592(11) 0.0261(3) Uani 1 1 d . . . . .
N3 N 0.54817(15) 0.38980(11) 0.27799(10) 0.0248(3) Uani 1 1 d . . . . .
O1 O 0.45205(14) 0.54506(11) 0.18515(10) 0.0354(3) Uani 1 1 d . . . . .
O2 O 0.69845(13) 0.24030(10) 0.33769(9) 0.0312(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 1.346(2) . ?
C1 C2 1.369(2) . ?
C1 H1 0.95 . ?
C2 C3 1.419(2) . ?
C2 H2 0.95 . ?
C3 N2 1.345(2) . ?
C3 C4 1.418(2) . ?
C4 C5 1.365(2) . ?
C4 H4 0.95 . ?
C5 N1 1.342(2) . ?
C5 H5 0.95 . ?
C6 N2 1.461(2) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 N2 1.457(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 O1 1.217(2) . ?
C8 N3 1.391(2) . ?
C8 C11 1.497(2) . ?
C9 O2 1.214(2) . ?
C9 N3 1.389(2) . ?
C9 C10 1.497(2) . ?
C10 C15 1.382(2) . ?
C10 C11 1.392(2) . ?
C11 C12 1.378(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.95 . ?
C13 C14 1.393(3) . ?
C13 H13 0.95 . ?
C14 C15 1.396(3) . ?
C14 H14 0.95 . ?
C15 H15 0.95 . ?
I1 N3 2.1769(14) . ?
I1 N1 2.3247(14) . ?

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 C1 C2 123.34(15) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 120.15(14) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
N2 C3 C4 121.91(14) . . ?
N2 C3 C2 122.64(14) . . ?
C4 C3 C2 115.45(14) . . ?
C5 C4 C3 120.06(14) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
N1 C5 C4 123.73(14) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N3 125.76(15) . . ?
O1 C8 C11 127.55(15) . . ?
N3 C8 C11 106.68(13) . . ?
O2 C9 N3 125.59(15) . . ?
O2 C9 C10 127.79(15) . . ?
N3 C9 C10 106.62(13) . . ?
C15 C10 C11 121.53(16) . . ?
C15 C10 C9 130.79(16) . . ?
C11 C10 C9 107.68(14) . . ?
C12 C11 C10 121.69(15) . . ?
C12 C11 C8 130.79(15) . . ?
C10 C11 C8 107.52(14) . . ?
C11 C12 C13 117.16(16) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 H12 121.4 . . ?
C14 C13 C12 121.37(17) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 121.04(16) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 117.20(16) . . ?
C10 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
N3 I1 N1 177.68(5) . . ?
C5 N1 C1 117.26(14) . . ?
C5 N1 I1 120.28(10) . . ?
C1 N1 I1 122.45(11) . . ?
C3 N2 C7 120.52(14) . . ?
C3 N2 C6 120.54(13) . . ?
C7 N2 C6 118.88(14) . . ?
C9 N3 C8 111.47(13) . . ?
C9 N3 I1 125.37(11) . . ?
C8 N3 I1 123.03(10) . . ?

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
N1 C1 C2 C3 -1.1(2) . . . . ?
C1 C2 C3 N2 -179.90(15) . . . . ?
C1 C2 C3 C4 0.4(2) . . . . ?
N2 C3 C4 C5 -178.89(15) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 N1 -1.4(3) . . . . ?
O2 C9 C10 C15 0.7(3) . . . . ?
N3 C9 C10 C15 -179.66(16) . . . . ?
O2 C9 C10 C11 -179.97(15) . . . . ?
N3 C9 C10 C11 -0.29(17) . . . . ?
C15 C10 C11 C12 1.0(2) . . . . ?
C9 C10 C11 C12 -178.40(14) . . . . ?
C15 C10 C11 C8 -179.41(14) . . . . ?
C9 C10 C11 C8 1.15(16) . . . . ?
O1 C8 C11 C12 -2.5(3) . . . . ?
N3 C8 C11 C12 177.87(16) . . . . ?
O1 C8 C11 C10 178.00(17) . . . . ?
N3 C8 C11 C10 -1.62(17) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C8 C11 C12 C13 -179.61(16) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 1.4(3) . . . . ?
C11 C10 C15 C14 -0.7(2) . . . . ?
C9 C10 C15 C14 178.61(15) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C4 C5 N1 C1 0.7(2) . . . . ?
C4 C5 N1 I1 179.89(12) . . . . ?
C2 C1 N1 C5 0.6(2) . . . . ?
C2 C1 N1 I1 -178.56(12) . . . . ?
C4 C3 N2 C7 177.22(15) . . . . ?
C2 C3 N2 C7 -2.5(2) . . . . ?
C4 C3 N2 C6 -5.4(2) . . . . ?
C2 C3 N2 C6 174.90(15) . . . . ?
O2 C9 N3 C8 178.91(15) . . . . ?
C10 C9 N3 C8 -0.78(17) . . . . ?
O2 C9 N3 I1 -5.1(2) . . . . ?
C10 C9 N3 I1 175.20(10) . . . . ?
O1 C8 N3 C9 -178.16(16) . . . . ?
C11 C8 N3 C9 1.48(17) . . . . ?
O1 C8 N3 I1 5.7(2) . . . . ?
C11 C8 N3 I1 -174.62(10) . . . . ?



# END of CIF
_chemical_name_systematic        (N-iodophtalimide)(4-dimethylaminopyridine)
_chemical_name_common            (NIPht)(DMAP)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2366110'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-03-15T15:30:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C28 H32 I K N2 O10'
_chemical_formula_moiety         'C28 H32 I K N2 O10'
_chemical_formula_weight         722.55

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9210(19)
_cell_length_b                   11.407(3)
_cell_length_c                   16.152(3)
_cell_angle_alpha                102.724(8)
_cell_angle_beta                 99.561(7)
_cell_angle_gamma                114.396(7)
_cell_volume                     1554.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3975
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      26.69
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_T_max  0.907

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5977  0.7455                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.0485
_diffrn_reflns_number            10644
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         27.664
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.926
_reflns_Friedel_coverage         0
_reflns_number_total             6707
_reflns_number_gt                5270
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+0.0688P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6707
_refine_ls_number_parameters     542
_refine_ls_number_restraints     34
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.05
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
K K 0.2009 0.2494 '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_
_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 0.8103(3) 0.0072(3) 0.3494(2) 0.0457(8) Uani 1 1 d . . . . .
C2 C 0.9824(3) 0.0718(3) 0.3652(2) 0.0424(7) Uani 1 1 d . . . . .
C3 C 1.0909(4) 0.0413(4) 0.4051(2) 0.0559(9) Uani 1 1 d . . . . .
H3 H 1.0641 -0.028 0.4303 0.067 Uiso 1 1 calc R U . . .
C4 C 1.2427(4) 0.1184(4) 0.4065(3) 0.0654(11) Uani 1 1 d . . . . .
H4 H 1.3193 0.1001 0.4328 0.078 Uiso 1 1 calc R U . . .
C5 C 1.2815(4) 0.2208(4) 0.3697(3) 0.0637(11) Uani 1 1 d . . . . .
H5 H 1.3842 0.271 0.3718 0.076 Uiso 1 1 calc R U . . .
C6 C 1.1717(4) 0.2510(4) 0.3298(2) 0.0539(9) Uani 1 1 d . . . . .
H6 H 1.1984 0.3204 0.3047 0.065 Uiso 1 1 calc R U . . .
C7 C 1.0213(3) 0.1750(3) 0.32842(19) 0.0385(7) Uani 1 1 d . . . . .
C8 C 0.8762(3) 0.1791(3) 0.2909(2) 0.0418(7) Uani 1 1 d . . . . .
C9 C 0.2017(3) 0.0290(3) 0.1519(2) 0.0454(8) Uani 1 1 d . . . . .
C10 C 0.0304(3) -0.0341(3) 0.1362(2) 0.0407(7) Uani 1 1 d . . . . .
C11 C -0.0779(4) -0.0026(4) 0.0970(2) 0.0568(9) Uani 1 1 d . . . . .
H11 H -0.0505 0.0681 0.0732 0.068 Uiso 1 1 calc R U . . .
C12 C -0.2306(4) -0.0808(4) 0.0945(3) 0.0650(11) Uani 1 1 d . . . . .
H12 H -0.3071 -0.0621 0.0684 0.078 Uiso 1 1 calc R U . . .
C13 C -0.2696(4) -0.1843(4) 0.1297(3) 0.0615(10) Uani 1 1 d . . . . .
H13 H -0.3724 -0.2345 0.1276 0.074 Uiso 1 1 calc R U . . .
C14 C -0.1602(4) -0.2166(3) 0.1686(2) 0.0531(9) Uani 1 1 d . . . . .
H14 H -0.1875 -0.2878 0.1921 0.064 Uiso 1 1 calc R U . . .
C15 C -0.0092(3) -0.1390(3) 0.1711(2) 0.0402(7) Uani 1 1 d . . . . .
C16 C 0.1342(3) -0.1463(3) 0.2068(2) 0.0451(8) Uani 1 1 d . . . . .
C17 C 1.2875(18) 0.5180(16) 0.1342(11) 0.070(4) Uani 0.540(7) 1 d D . P A 1
H17A H 1.3829 0.5239 0.1232 0.084 Uiso 0.540(7) 1 calc R U P A 1
H17B H 1.278 0.5961 0.1256 0.084 Uiso 0.540(7) 1 calc R U P A 1
C18 C 1.1530(12) 0.3899(10) 0.0707(7) 0.078(3) Uani 0.540(7) 1 d D . P A 1
H18A H 1.1518 0.3875 0.0102 0.094 Uiso 0.540(7) 1 calc R U P A 1
H18B H 1.1617 0.3115 0.0795 0.094 Uiso 0.540(7) 1 calc R U P A 1
C19 C 0.888(2) 0.3061(18) 0.0126(11) 0.081(5) Uani 0.540(7) 1 d D . P A 1
H19A H 0.8872 0.2206 -0.0139 0.097 Uiso 0.540(7) 1 calc R U P A 1
H19B H 0.8908 0.3521 -0.0314 0.097 Uiso 0.540(7) 1 calc R U P A 1
C20 C 0.7471(13) 0.2809(13) 0.0435(8) 0.084(3) Uani 0.540(7) 1 d D . P A 1
H20A H 0.6562 0.2242 -0.0072 0.1 Uiso 0.540(7) 1 calc R U P A 1
H20B H 0.7444 0.2304 0.0848 0.1 Uiso 0.540(7) 1 calc R U P A 1
C21 C 0.6009(13) 0.3856(18) 0.1072(7) 0.112(9) Uani 0.540(7) 1 d D . P A 1
H21A H 0.5863 0.4631 0.1023 0.134 Uiso 0.540(7) 1 calc R U P A 1
H21B H 0.513 0.3044 0.0649 0.134 Uiso 0.540(7) 1 calc R U P A 1
C22 C 0.6040(10) 0.3784(9) 0.1938(8) 0.086(4) Uani 0.540(7) 1 d D . P A 1
H22A H 0.6221 0.3031 0.2003 0.103 Uiso 0.540(7) 1 calc R U P A 1
H22B H 0.5052 0.3629 0.2039 0.103 Uiso 0.540(7) 1 calc R U P A 1
C23 C 0.7192(14) 0.5044(17) 0.3435(10) 0.071(5) Uani 0.540(7) 1 d D . P A 1
H23A H 0.7163 0.4219 0.3521 0.085 Uiso 0.540(7) 1 calc R U P A 1
H23B H 0.626 0.5071 0.3521 0.085 Uiso 0.540(7) 1 calc R U P A 1
C24 C 0.8583(14) 0.6260(12) 0.4106(8) 0.090(3) Uani 0.540(7) 1 d D . P A 1
H24A H 0.8734 0.7078 0.3961 0.108 Uiso 0.540(7) 1 calc R U P A 1
H24B H 0.8443 0.6368 0.4693 0.108 Uiso 0.540(7) 1 calc R U P A 1
C25 C 1.1111(17) 0.6541(18) 0.4807(9) 0.120(6) Uani 0.540(7) 1 d D . P A 1
H25A H 1.0904 0.5893 0.513 0.144 Uiso 0.540(7) 1 calc R U P A 1
H25B H 1.1193 0.7368 0.5189 0.144 Uiso 0.540(7) 1 calc R U P A 1
C26 C 1.2590(19) 0.6846(19) 0.4644(8) 0.158(8) Uani 0.540(7) 1 d D . P A 1
H26A H 1.3224 0.7824 0.4895 0.189 Uiso 0.540(7) 1 calc R U P A 1
H26B H 1.3061 0.6449 0.4993 0.189 Uiso 0.540(7) 1 calc R U P A 1
C27 C 1.4105(12) 0.6471(13) 0.3747(7) 0.061(3) Uani 0.540(7) 1 d D . P A 1
H27A H 1.4139 0.5683 0.3864 0.073 Uiso 0.540(7) 1 calc R U P A 1
H27B H 1.5 0.7281 0.416 0.073 Uiso 0.540(7) 1 calc R U P A 1
C28 C 1.4129(10) 0.6409(9) 0.2831(7) 0.073(3) Uani 0.540(7) 1 d D . P A 1
H28A H 1.4036 0.7171 0.2709 0.087 Uiso 0.540(7) 1 calc R U P A 1
H28B H 1.5109 0.6477 0.2761 0.087 Uiso 0.540(7) 1 calc R U P A 1
O5 O 1.2915(7) 0.5188(6) 0.2225(6) 0.0581(18) Uani 0.540(7) 1 d D . P A 1
O6 O 1.0160(9) 0.3861(9) 0.0859(5) 0.080(2) Uani 0.540(7) 1 d D . P A 1
O7 O 0.7385(12) 0.3981(11) 0.0844(8) 0.097(3) Uani 0.540(7) 1 d D . P A 1
O8 O 0.7237(8) 0.5022(6) 0.2567(5) 0.0557(18) Uani 0.540(7) 1 d D . P A 1
O9 O 0.9878(9) 0.6032(9) 0.4082(5) 0.089(2) Uani 0.540(7) 1 d D . P A 1
O10 O 1.2734(9) 0.6498(7) 0.3858(4) 0.076(2) Uani 0.540(7) 1 d D . P A 1
C17B C 1.3582(16) 0.5838(16) 0.2073(10) 0.082(4) Uani 0.460(7) 1 d D . P A 2
H17C H 1.4656 0.6042 0.2156 0.098 Uiso 0.460(7) 1 calc R U P A 2
H17D H 1.3481 0.662 0.1997 0.098 Uiso 0.460(7) 1 calc R U P A 2
C18B C 1.260(2) 0.4642(19) 0.1279(14) 0.090(7) Uani 0.460(7) 1 d D . P A 2
H18C H 1.2964 0.4787 0.0772 0.108 Uiso 0.460(7) 1 calc R U P A 2
H18D H 1.264 0.3845 0.1371 0.108 Uiso 0.460(7) 1 calc R U P A 2
C19B C 1.0112(17) 0.3493(14) 0.0322(11) 0.084(4) Uani 0.460(7) 1 d D . P A 2
H19C H 1.0456 0.2815 0.0161 0.101 Uiso 0.460(7) 1 calc R U P A 2
H19D H 1.0157 0.3932 -0.0131 0.101 Uiso 0.460(7) 1 calc R U P A 2
C20B C 0.847(2) 0.2806(19) 0.0356(12) 0.071(5) Uani 0.460(7) 1 d D . P A 2
H20C H 0.7808 0.2199 -0.0233 0.085 Uiso 0.460(7) 1 calc R U P A 2
H20D H 0.8403 0.226 0.0745 0.085 Uiso 0.460(7) 1 calc R U P A 2
C21B C 0.6451(15) 0.2953(13) 0.0805(12) 0.154(9) Uani 0.460(7) 1 d D . P A 2
H21C H 0.5699 0.2282 0.0255 0.184 Uiso 0.460(7) 1 calc R U P A 2
H21D H 0.6581 0.2497 0.123 0.184 Uiso 0.460(7) 1 calc R U P A 2
C22B C 0.601(2) 0.3950(15) 0.1142(14) 0.152(15) Uani 0.460(7) 1 d D . P A 2
H22C H 0.4915 0.3504 0.1083 0.183 Uiso 0.460(7) 1 calc R U P A 2
H22D H 0.6183 0.455 0.0785 0.183 Uiso 0.460(7) 1 calc R U P A 2
C23B C 0.6330(16) 0.4335(14) 0.2748(9) 0.082(4) Uani 0.460(7) 1 d D . P A 2
H23C H 0.6455 0.3544 0.2777 0.098 Uiso 0.460(7) 1 calc R U P A 2
H23D H 0.5245 0.4095 0.2653 0.098 Uiso 0.460(7) 1 calc R U P A 2
C24B C 0.728(2) 0.548(2) 0.3598(13) 0.084(7) Uani 0.460(7) 1 d D . P A 2
H24C H 0.7384 0.6337 0.3525 0.101 Uiso 0.460(7) 1 calc R U P A 2
H24D H 0.6799 0.533 0.4067 0.101 Uiso 0.460(7) 1 calc R U P A 2
C25B C 0.9754(17) 0.6542(15) 0.4559(9) 0.117(6) Uani 0.460(7) 1 d D . P A 2
H25C H 0.964 0.618 0.5048 0.14 Uiso 0.460(7) 1 calc R U P A 2
H25D H 0.9424 0.724 0.465 0.14 Uiso 0.460(7) 1 calc R U P A 2
C26B C 1.1388(15) 0.7207(14) 0.4635(9) 0.086(4) Uani 0.460(7) 1 d D . P A 2
H26C H 1.1618 0.8009 0.4454 0.103 Uiso 0.460(7) 1 calc R U P A 2
H26D H 1.1962 0.7513 0.5255 0.103 Uiso 0.460(7) 1 calc R U P A 2
C27B C 1.3313(18) 0.6422(14) 0.4288(10) 0.138(11) Uani 0.460(7) 1 d D . P A 2
H27C H 1.3178 0.5531 0.4291 0.166 Uiso 0.460(7) 1 calc R U P A 2
H27D H 1.4014 0.7084 0.4854 0.166 Uiso 0.460(7) 1 calc R U P A 2
C28B C 1.3941(19) 0.6767(19) 0.3559(12) 0.165(14) Uani 0.460(7) 1 d D . P A 2
H28C H 1.3776 0.7498 0.3432 0.198 Uiso 0.460(7) 1 calc R U P A 2
H28D H 1.5042 0.7052 0.3714 0.198 Uiso 0.460(7) 1 calc R U P A 2
O5B O 1.3138(9) 0.5572(9) 0.2820(7) 0.075(2) Uani 0.460(7) 1 d D . P A 2
O6B O 1.1072(12) 0.4435(10) 0.1116(6) 0.079(3) Uani 0.460(7) 1 d D . P A 2
O7B O 0.7898(13) 0.3751(12) 0.0665(7) 0.084(3) Uani 0.460(7) 1 d D . P A 2
O8B O 0.6828(12) 0.4744(12) 0.2043(8) 0.083(3) Uani 0.460(7) 1 d D . P A 2
O9B O 0.8730(13) 0.5514(9) 0.3798(5) 0.085(3) Uani 0.460(7) 1 d D . P A 2
O10B O 1.1916(11) 0.6430(10) 0.4150(7) 0.104(3) Uani 0.460(7) 1 d D . P A 2
N1 N 0.7568(3) 0.0782(3) 0.30578(18) 0.0434(6) Uani 1 1 d . . . . .
N2 N 0.2550(3) -0.0429(3) 0.19386(18) 0.0438(6) Uani 1 1 d . . . . .
O1 O 0.7337(3) -0.0870(3) 0.37187(19) 0.0749(9) Uani 1 1 d . . . . .
O2 O 0.8645(3) 0.2581(2) 0.25372(18) 0.0611(7) Uani 1 1 d . . . . .
O3 O 0.2802(3) 0.1260(3) 0.13148(19) 0.0712(8) Uani 1 1 d . . . . .
O4 O 0.1455(3) -0.2276(3) 0.2416(2) 0.0692(8) Uani 1 1 d . . . . .
K1 K 1.00320(7) 0.51393(7) 0.24337(4) 0.04460(17) Uani 1 1 d . . . . .
I1 I 0.50574(2) 0.01721(2) 0.24960(2) 0.04387(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 1.206(4) . ?
C1 N1 1.384(4) . ?
C1 C2 1.503(4) . ?
C2 C3 1.369(5) . ?
C2 C7 1.377(4) . ?
C3 C4 1.388(5) . ?
C3 H3 0.93 . ?
C4 C5 1.370(6) . ?
C4 H4 0.93 . ?
C5 C6 1.376(5) . ?
C5 H5 0.93 . ?
C6 C7 1.375(4) . ?
C6 H6 0.93 . ?
C7 C8 1.490(4) . ?
C8 O2 1.220(4) . ?
C8 N1 1.369(4) . ?
C9 O3 1.213(4) . ?
C9 N2 1.377(4) . ?
C9 C10 1.495(4) . ?
C10 C11 1.370(4) . ?
C10 C15 1.373(4) . ?
C11 C12 1.392(5) . ?
C11 H11 0.93 . ?
C12 C13 1.365(6) . ?
C12 H12 0.93 . ?
C13 C14 1.383(5) . ?
C13 H13 0.93 . ?
C14 C15 1.378(4) . ?
C14 H14 0.93 . ?
C15 C16 1.486(4) . ?
C16 O4 1.218(4) . ?
C16 N2 1.376(4) . ?
C17 O5 1.417(15) . ?
C17 C18 1.498(14) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 O6 1.406(11) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 O6 1.383(19) . ?
C19 C20 1.501(13) . ?
C19 H19A 0.97 . ?
C19 H19B 0.97 . ?
C20 O7 1.398(13) . ?
C20 K1 3.444(12) . ?
C20 H20A 0.97 . ?
C20 H20B 0.97 . ?
C21 C22 1.415(14) . ?
C21 O7 1.432(13) . ?
C21 H21A 0.97 . ?
C21 H21B 0.97 . ?
C22 O8 1.421(10) . ?
C22 K1 3.473(9) . ?
C22 H22A 0.97 . ?
C22 H22B 0.97 . ?
C23 O8 1.404(15) . ?
C23 C24 1.504(14) . ?
C23 K1 3.450(13) . ?
C23 H23A 0.97 . ?
C23 H23B 0.97 . ?
C24 O9 1.417(12) . ?
C24 K1 3.504(11) . ?
C24 H24A 0.97 . ?
C24 H24B 0.97 . ?
C25 O9 1.358(13) . ?
C25 C26 1.445(15) . ?
C25 H25A 0.97 . ?
C25 H25B 0.97 . ?
C26 O10 1.294(12) . ?
C26 H26A 0.97 . ?
C26 H26B 0.97 . ?
C27 O10 1.413(11) . ?
C27 C28 1.470(13) . ?
C27 H27A 0.97 . ?
C27 H27B 0.97 . ?
C28 O5 1.404(10) . ?
C28 H28A 0.97 . ?
C28 H28B 0.97 . ?
O5 K1 2.915(7) . ?
O6 K1 2.690(8) . ?
O7 K1 2.938(12) . ?
O8 K1 2.767(7) . ?
O9 K1 2.686(7) . ?
O10 K1 2.798(7) . ?
C17B O5B 1.402(13) . ?
C17B C18B 1.474(16) . ?
C17B K1 3.456(12) . ?
C17B H17C 0.97 . ?
C17B H17D 0.97 . ?
C18B O6B 1.398(17) . ?
C18B H18C 0.97 . ?
C18B H18D 0.97 . ?
C19B O6B 1.360(17) . ?
C19B C20B 1.506(16) . ?
C19B H19C 0.97 . ?
C19B H19D 0.97 . ?
C20B O7B 1.445(16) . ?
C20B K1 3.417(19) . ?
C20B H20C 0.97 . ?
C20B H20D 0.97 . ?
C21B C22B 1.412(16) . ?
C21B O7B 1.436(16) . ?
C21B K1 3.528(13) . ?
C21B H21C 0.97 . ?
C21B H21D 0.97 . ?
C22B O8B 1.420(16) . ?
C22B H22C 0.97 . ?
C22B H22D 0.97 . ?
C23B O8B 1.409(13) . ?
C23B C24B 1.499(16) . ?
C23B H23C 0.97 . ?
C23B H23D 0.97 . ?
C24B O9B 1.408(16) . ?
C24B H24C 0.97 . ?
C24B H24D 0.97 . ?
C25B O9B 1.372(13) . ?
C25B C26B 1.448(16) . ?
C25B H25C 0.97 . ?
C25B H25D 0.97 . ?
C26B O10B 1.375(14) . ?
C26B K1 3.481(13) . ?
C26B H26C 0.97 . ?
C26B H26D 0.97 . ?
C27B O10B 1.370(15) . ?
C27B C28B 1.476(16) . ?
C27B H27C 0.97 . ?
C27B H27D 0.97 . ?
C28B O5B 1.410(16) . ?
C28B K1 3.466(16) . ?
C28B H28C 0.97 . ?
C28B H28D 0.97 . ?
O5B K1 2.845(8) . ?
O6B K1 2.627(8) . ?
O7B K1 2.895(11) . ?
O8B K1 2.955(10) . ?
O9B K1 2.774(9) . ?
O10B K1 2.748(9) . ?
N1 I1 2.247(2) . ?
N2 I1 2.246(2) . ?
O2 K1 2.722(2) . ?
O4 K1 2.701(3) 1_445 ?
K1 O4 2.701(3) 1_665 ?

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
O1 C1 N1 126.6(3) . . ?
O1 C1 C2 126.4(3) . . ?
N1 C1 C2 107.0(3) . . ?
C3 C2 C7 121.8(3) . . ?
C3 C2 C1 131.1(3) . . ?
C7 C2 C1 107.1(3) . . ?
C2 C3 C4 117.1(4) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.7(3) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 120.9(3) . . ?
C6 C7 C8 131.7(3) . . ?
C2 C7 C8 107.4(3) . . ?
O2 C8 N1 125.6(3) . . ?
O2 C8 C7 126.6(3) . . ?
N1 C8 C7 107.9(3) . . ?
O3 C9 N2 125.9(3) . . ?
O3 C9 C10 126.5(3) . . ?
N2 C9 C10 107.6(3) . . ?
C11 C10 C15 121.7(3) . . ?
C11 C10 C9 131.5(3) . . ?
C15 C10 C9 106.8(3) . . ?
C10 C11 C12 117.4(3) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 117.3(3) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 C16 107.7(3) . . ?
C14 C15 C16 131.2(3) . . ?
O4 C16 N2 125.4(3) . . ?
O4 C16 C15 127.2(3) . . ?
N2 C16 C15 107.5(3) . . ?
O5 C17 C18 109.7(11) . . ?
O5 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
O5 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
O6 C18 C17 108.6(11) . . ?
O6 C18 H18A 110 . . ?
C17 C18 H18A 110 . . ?
O6 C18 H18B 110 . . ?
C17 C18 H18B 110 . . ?
H18A C18 H18B 108.3 . . ?
O6 C19 C20 107.5(12) . . ?
O6 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O6 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
O7 C20 C19 114.9(13) . . ?
O7 C20 K1 57.4(6) . . ?
C19 C20 K1 85.3(8) . . ?
O7 C20 H20A 108.5 . . ?
C19 C20 H20A 108.5 . . ?
K1 C20 H20A 164.3 . . ?
O7 C20 H20B 108.5 . . ?
C19 C20 H20B 108.5 . . ?
K1 C20 H20B 73.6 . . ?
H20A C20 H20B 107.5 . . ?
C22 C21 O7 113.4(12) . . ?
C22 C21 H21A 108.9 . . ?
O7 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
O7 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 O8 109.3(10) . . ?
C21 C22 K1 88.2(7) . . ?
O8 C22 K1 49.4(5) . . ?
C21 C22 H22A 109.8 . . ?
O8 C22 H22A 109.8 . . ?
K1 C22 H22A 76.6 . . ?
C21 C22 H22B 109.8 . . ?
O8 C22 H22B 109.8 . . ?
K1 C22 H22B 157.4 . . ?
H22A C22 H22B 108.3 . . ?
O8 C23 C24 111.0(11) . . ?
O8 C23 K1 50.1(5) . . ?
C24 C23 K1 79.5(6) . . ?
O8 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
K1 C23 H23A 85.3 . . ?
O8 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
K1 C23 H23B 159.2 . . ?
H23A C23 H23B 108 . . ?
O9 C24 C23 107.3(11) . . ?
O9 C24 K1 44.6(5) . . ?
C23 C24 K1 75.5(7) . . ?
O9 C24 H24A 110.3 . . ?
C23 C24 H24A 110.3 . . ?
K1 C24 H24A 93.6 . . ?
O9 C24 H24B 110.3 . . ?
C23 C24 H24B 110.3 . . ?
K1 C24 H24B 152.5 . . ?
H24A C24 H24B 108.5 . . ?
O9 C25 C26 116.4(12) . . ?
O9 C25 H25A 108.2 . . ?
C26 C25 H25A 108.2 . . ?
O9 C25 H25B 108.2 . . ?
C26 C25 H25B 108.2 . . ?
H25A C25 H25B 107.3 . . ?
O10 C26 C25 122.9(15) . . ?
O10 C26 H26A 106.6 . . ?
C25 C26 H26A 106.6 . . ?
O10 C26 H26B 106.6 . . ?
C25 C26 H26B 106.6 . . ?
H26A C26 H26B 106.6 . . ?
O10 C27 C28 108.6(9) . . ?
O10 C27 H27A 110 . . ?
C28 C27 H27A 110 . . ?
O10 C27 H27B 110 . . ?
C28 C27 H27B 110 . . ?
H27A C27 H27B 108.4 . . ?
O5 C28 C27 110.9(9) . . ?
O5 C28 H28A 109.5 . . ?
C27 C28 H28A 109.5 . . ?
O5 C28 H28B 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 108 . . ?
C28 O5 C17 110.6(10) . . ?
C28 O5 K1 107.3(6) . . ?
C17 O5 K1 105.0(7) . . ?
C19 O6 C18 113.0(10) . . ?
C19 O6 K1 123.7(8) . . ?
C18 O6 K1 123.3(7) . . ?
C20 O7 C21 119.5(12) . . ?
C20 O7 K1 98.9(7) . . ?
C21 O7 K1 111.4(7) . . ?
C23 O8 C22 110.8(9) . . ?
C23 O8 K1 107.0(6) . . ?
C22 O8 K1 107.7(6) . . ?
C25 O9 C24 122.3(12) . . ?
C25 O9 K1 122.0(8) . . ?
C24 O9 K1 113.7(7) . . ?
C26 O10 C27 120.4(12) . . ?
C26 O10 K1 117.3(10) . . ?
C27 O10 K1 120.1(6) . . ?
O5B C17B C18B 109.6(15) . . ?
O5B C17B K1 53.1(6) . . ?
C18B C17B K1 81.3(10) . . ?
O5B C17B H17C 109.7 . . ?
C18B C17B H17C 109.7 . . ?
K1 C17B H17C 162.7 . . ?
O5B C17B H17D 109.7 . . ?
C18B C17B H17D 109.7 . . ?
K1 C17B H17D 79.1 . . ?
H17C C17B H17D 108.2 . . ?
O6B C18B C17B 109.3(15) . . ?
O6B C18B H18C 109.8 . . ?
C17B C18B H18C 109.8 . . ?
O6B C18B H18D 109.8 . . ?
C17B C18B H18D 109.8 . . ?
H18C C18B H18D 108.3 . . ?
O6B C19B C20B 111.4(14) . . ?
O6B C19B H19C 109.4 . . ?
C20B C19B H19C 109.4 . . ?
O6B C19B H19D 109.4 . . ?
C20B C19B H19D 109.4 . . ?
H19C C19B H19D 108 . . ?
O7B C20B C19B 113.3(14) . . ?
O7B C20B K1 56.9(8) . . ?
C19B C20B K1 82.2(10) . . ?
O7B C20B H20C 108.9 . . ?
C19B C20B H20C 108.9 . . ?
K1 C20B H20C 165.4 . . ?
O7B C20B H20D 108.9 . . ?
C19B C20B H20D 108.9 . . ?
K1 C20B H20D 76.3 . . ?
H20C C20B H20D 107.7 . . ?
C22B C21B O7B 102.0(14) . . ?
C22B C21B K1 85.2(9) . . ?
O7B C21B K1 52.8(6) . . ?
C22B C21B H21C 111.4 . . ?
O7B C21B H21C 111.4 . . ?
K1 C21B H21C 160.4 . . ?
C22B C21B H21D 111.4 . . ?
O7B C21B H21D 111.4 . . ?
K1 C21B H21D 72 . . ?
H21C C21B H21D 109.2 . . ?
C21B C22B O8B 113.9(12) . . ?
C21B C22B H22C 108.8 . . ?
O8B C22B H22C 108.8 . . ?
C21B C22B H22D 108.8 . . ?
O8B C22B H22D 108.8 . . ?
H22C C22B H22D 107.7 . . ?
O8B C23B C24B 108.8(15) . . ?
O8B C23B H23C 109.9 . . ?
C24B C23B H23C 109.9 . . ?
O8B C23B H23D 109.9 . . ?
C24B C23B H23D 109.9 . . ?
H23C C23B H23D 108.3 . . ?
O9B C24B C23B 105.6(13) . . ?
O9B C24B H24C 110.6 . . ?
C23B C24B H24C 110.6 . . ?
O9B C24B H24D 110.6 . . ?
C23B C24B H24D 110.6 . . ?
H24C C24B H24D 108.8 . . ?
O9B C25B C26B 120.1(14) . . ?
O9B C25B H25C 107.3 . . ?
C26B C25B H25C 107.3 . . ?
O9B C25B H25D 107.3 . . ?
C26B C25B H25D 107.3 . . ?
H25C C25B H25D 106.9 . . ?
O10B C26B C25B 115.8(12) . . ?
O10B C26B K1 47.6(6) . . ?
C25B C26B K1 81.3(8) . . ?
O10B C26B H26C 108.3 . . ?
C25B C26B H26C 108.3 . . ?
K1 C26B H26C 91 . . ?
O10B C26B H26D 108.3 . . ?
C25B C26B H26D 108.3 . . ?
K1 C26B H26D 154.5 . . ?
H26C C26B H26D 107.4 . . ?
O10B C27B C28B 107.3(14) . . ?
O10B C27B H27C 110.3 . . ?
C28B C27B H27C 110.3 . . ?
O10B C27B H27D 110.3 . . ?
C28B C27B H27D 110.3 . . ?
H27C C27B H27D 108.5 . . ?
O5B C28B C27B 105.9(13) . . ?
O5B C28B K1 52.8(7) . . ?
C27B C28B K1 81.1(9) . . ?
O5B C28B H28C 110.6 . . ?
C27B C28B H28C 110.6 . . ?
K1 C28B H28C 77.3 . . ?
O5B C28B H28D 110.6 . . ?
C27B C28B H28D 110.6 . . ?
K1 C28B H28D 162.8 . . ?
H28C C28B H28D 108.7 . . ?
C17B O5B C28B 109.8(11) . . ?
C17B O5B K1 103.6(7) . . ?
C28B O5B K1 103.9(9) . . ?
C19B O6B C18B 114.1(12) . . ?
C19B O6B K1 122.2(9) . . ?
C18B O6B K1 120.4(10) . . ?
C21B O7B C20B 105.6(12) . . ?
C21B O7B K1 103.9(8) . . ?
C20B O7B K1 98.3(10) . . ?
C23B O8B C22B 122.1(14) . . ?
C23B O8B K1 103.3(8) . . ?
C22B O8B K1 109.9(9) . . ?
C25B O9B C24B 112.7(14) . . ?
C25B O9B K1 114.0(10) . . ?
C24B O9B K1 118.7(9) . . ?
C27B O10B C26B 132.4(12) . . ?
C27B O10B K1 114.9(10) . . ?
C26B O10B K1 110.7(8) . . ?
C8 N1 C1 110.6(2) . . ?
C8 N1 I1 124.3(2) . . ?
C1 N1 I1 124.5(2) . . ?
C16 N2 C9 110.3(3) . . ?
C16 N2 I1 124.6(2) . . ?
C9 N2 I1 124.64(19) . . ?
C8 O2 K1 146.0(2) . . ?
C16 O4 K1 144.9(2) . 1_445 ?
O9 K1 O6 169.9(3) . . ?
O6B K1 O4 88.1(2) . 1_665 ?
O9 K1 O4 90.35(19) . 1_665 ?
O6 K1 O4 98.8(2) . 1_665 ?
O6B K1 O2 94.0(2) . . ?
O9 K1 O2 87.13(19) . . ?
O6 K1 O2 83.6(2) . . ?
O4 K1 O2 177.28(8) 1_665 . ?
O6B K1 O10B 121.7(3) . . ?
O4 K1 O10B 79.6(2) 1_665 . ?
O2 K1 O10B 97.7(2) . . ?
O9 K1 O8 63.8(2) . . ?
O6 K1 O8 118.5(2) . . ?
O4 K1 O8 98.19(15) 1_665 . ?
O2 K1 O8 81.63(15) . . ?
O6B K1 O9B 172.3(3) . . ?
O4 K1 O9B 99.6(2) 1_665 . ?
O2 K1 O9B 78.3(2) . . ?
O10B K1 O9B 60.8(3) . . ?
O9 K1 O10 60.4(2) . . ?
O6 K1 O10 118.1(2) . . ?
O4 K1 O10 73.80(16) 1_665 . ?
O2 K1 O10 104.00(16) . . ?
O8 K1 O10 123.4(2) . . ?
O6B K1 O5B 61.3(3) . . ?
O4 K1 O5B 80.92(17) 1_665 . ?
O2 K1 O5B 98.50(17) . . ?
O10B K1 O5B 60.5(3) . . ?
O9B K1 O5B 120.2(3) . . ?
O6B K1 O7B 61.5(3) . . ?
O4 K1 O7B 101.6(3) 1_665 . ?
O2 K1 O7B 81.0(3) . . ?
O10B K1 O7B 176.8(3) . . ?
O9B K1 O7B 115.9(3) . . ?
O5B K1 O7B 122.5(3) . . ?
O9 K1 O5 118.3(2) . . ?
O6 K1 O5 59.3(2) . . ?
O4 K1 O5 82.65(14) 1_665 . ?
O2 K1 O5 97.63(14) . . ?
O8 K1 O5 177.79(19) . . ?
O10 K1 O5 58.8(2) . . ?
N2 I1 N1 179.74(10) . . ?

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
O1 C1 C2 C3 1.5(6) . . . . ?
N1 C1 C2 C3 -179.8(3) . . . . ?
O1 C1 C2 C7 179.8(4) . . . . ?
N1 C1 C2 C7 -1.5(4) . . . . ?
C7 C2 C3 C4 -0.5(5) . . . . ?
C1 C2 C3 C4 177.6(3) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C7 0.3(6) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C5 C6 C7 C8 -179.3(3) . . . . ?
C3 C2 C7 C6 0.6(5) . . . . ?
C1 C2 C7 C6 -177.9(3) . . . . ?
C3 C2 C7 C8 179.7(3) . . . . ?
C1 C2 C7 C8 1.2(3) . . . . ?
C6 C7 C8 O2 -1.9(6) . . . . ?
C2 C7 C8 O2 179.1(3) . . . . ?
C6 C7 C8 N1 178.5(3) . . . . ?
C2 C7 C8 N1 -0.5(3) . . . . ?
O3 C9 C10 C11 0.2(6) . . . . ?
N2 C9 C10 C11 -179.8(3) . . . . ?
O3 C9 C10 C15 -179.0(4) . . . . ?
N2 C9 C10 C15 1.1(4) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C9 C10 C11 C12 -178.6(3) . . . . ?
C10 C11 C12 C13 0.0(6) . . . . ?
C11 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
C9 C10 C15 C14 178.8(3) . . . . ?
C11 C10 C15 C16 179.3(3) . . . . ?
C9 C10 C15 C16 -1.5(3) . . . . ?
C13 C14 C15 C10 -0.1(5) . . . . ?
C13 C14 C15 C16 -179.7(3) . . . . ?
C10 C15 C16 O4 -178.6(4) . . . . ?
C14 C15 C16 O4 1.0(6) . . . . ?
C10 C15 C16 N2 1.5(4) . . . . ?
C14 C15 C16 N2 -178.9(3) . . . . ?
O5 C17 C18 O6 61.5(14) . . . . ?
O6 C19 C20 O7 58.7(16) . . . . ?
O6 C19 C20 K1 8.0(11) . . . . ?
O7 C21 C22 O8 63.9(17) . . . . ?
O7 C21 C22 K1 18.4(12) . . . . ?
O8 C23 C24 O9 -71.4(14) . . . . ?
K1 C23 C24 O9 -31.7(8) . . . . ?
O8 C23 C24 K1 -39.7(9) . . . . ?
O9 C25 C26 O10 -9(3) . . . . ?
O10 C27 C28 O5 -64.5(11) . . . . ?
C27 C28 O5 C17 175.6(10) . . . . ?
C27 C28 O5 K1 61.6(8) . . . . ?
C18 C17 O5 C28 -177.5(10) . . . . ?
C18 C17 O5 K1 -62.1(12) . . . . ?
C20 C19 O6 C18 165.4(11) . . . . ?
C20 C19 O6 K1 -12.3(16) . . . . ?
C17 C18 O6 C19 155.8(12) . . . . ?
C17 C18 O6 K1 -26.4(12) . . . . ?
C19 C20 O7 C21 172.9(13) . . . . ?
K1 C20 O7 C21 -120.9(13) . . . . ?
C19 C20 O7 K1 -66.2(11) . . . . ?
C22 C21 O7 C20 90.7(15) . . . . ?
C22 C21 O7 K1 -23.6(16) . . . . ?
C24 C23 O8 C22 172.1(10) . . . . ?
K1 C23 O8 C22 117.1(8) . . . . ?
C24 C23 O8 K1 55.0(13) . . . . ?
C21 C22 O8 C23 173.5(12) . . . . ?
K1 C22 O8 C23 -116.7(9) . . . . ?
C21 C22 O8 K1 -69.8(10) . . . . ?
C26 C25 O9 C24 -150.1(15) . . . . ?
C26 C25 O9 K1 13(2) . . . . ?
C23 C24 O9 C25 -149.6(13) . . . . ?
K1 C24 O9 C25 164.0(13) . . . . ?
C23 C24 O9 K1 46.4(11) . . . . ?
C25 C26 O10 C27 -162.3(16) . . . . ?
C25 C26 O10 K1 1(3) . . . . ?
C28 C27 O10 C26 -165.0(13) . . . . ?
C28 C27 O10 K1 32.1(12) . . . . ?
O5B C17B C18B O6B 65.1(17) . . . . ?
K1 C17B C18B O6B 19.5(12) . . . . ?
O6B C19B C20B O7B 54.0(17) . . . . ?
O6B C19B C20B K1 5.1(10) . . . . ?
O7B C21B C22B O8B -76.6(18) . . . . ?
K1 C21B C22B O8B -26.3(15) . . . . ?
O8B C23B C24B O9B -75.1(16) . . . . ?
O9B C25B C26B O10B -28(2) . . . . ?
O9B C25B C26B K1 5.6(14) . . . . ?
O10B C27B C28B O5B -78.0(17) . . . . ?
O10B C27B C28B K1 -30.9(10) . . . . ?
C18B C17B O5B C28B -172.6(14) . . . . ?
K1 C17B O5B C28B -110.5(11) . . . . ?
C18B C17B O5B K1 -62.0(12) . . . . ?
C27B C28B O5B C17B 175.5(13) . . . . ?
K1 C28B O5B C17B 110.3(9) . . . . ?
C27B C28B O5B K1 65.2(15) . . . . ?
C20B C19B O6B C18B 151.5(14) . . . . ?
C20B C19B O6B K1 -7.9(16) . . . . ?
C17B C18B O6B C19B 170.1(13) . . . . ?
C17B C18B O6B K1 -30.1(19) . . . . ?
C22B C21B O7B C20B 177.4(14) . . . . ?
K1 C21B O7B C20B 102.9(12) . . . . ?
C22B C21B O7B K1 74.5(12) . . . . ?
C19B C20B O7B C21B -170.0(14) . . . . ?
K1 C20B O7B C21B -107.1(10) . . . . ?
C19B C20B O7B K1 -62.9(14) . . . . ?
C24B C23B O8B C22B -171.0(12) . . . . ?
C24B C23B O8B K1 64.9(11) . . . . ?
C21B C22B O8B C23B -87.0(19) . . . . ?
C21B C22B O8B K1 34.1(19) . . . . ?
C26B C25B O9B C24B -146.8(18) . . . . ?
C26B C25B O9B K1 -8(2) . . . . ?
C23B C24B O9B C25B 178.8(13) . . . . ?
C23B C24B O9B K1 41.7(18) . . . . ?
C28B C27B O10B C26B -117.5(19) . . . . ?
C28B C27B O10B K1 44.9(14) . . . . ?
C25B C26B O10B C27B -149.1(16) . . . . ?
K1 C26B O10B C27B 163(2) . . . . ?
C25B C26B O10B K1 48.0(18) . . . . ?
O2 C8 N1 C1 179.9(3) . . . . ?
C7 C8 N1 C1 -0.4(4) . . . . ?
O2 C8 N1 I1 8.3(5) . . . . ?
C7 C8 N1 I1 -172.07(19) . . . . ?
O1 C1 N1 C8 179.9(4) . . . . ?
C2 C1 N1 C8 1.2(4) . . . . ?
O1 C1 N1 I1 -8.5(5) . . . . ?
C2 C1 N1 I1 172.79(19) . . . . ?
O4 C16 N2 C9 179.3(3) . . . . ?
C15 C16 N2 C9 -0.8(4) . . . . ?
O4 C16 N2 I1 -8.4(5) . . . . ?
C15 C16 N2 I1 171.50(19) . . . . ?
O3 C9 N2 C16 179.9(3) . . . . ?
C10 C9 N2 C16 -0.1(4) . . . . ?
O3 C9 N2 I1 7.6(5) . . . . ?
C10 C9 N2 I1 -172.42(19) . . . . ?
N1 C8 O2 K1 147.7(3) . . . . ?
C7 C8 O2 K1 -31.9(6) . . . . ?
N2 C16 O4 K1 -147.1(3) . . . 1_445 ?
C15 C16 O4 K1 33.1(7) . . . 1_445 ?



# END of CIF
_chemical_name_systematic        
'[Potassium(18-crown-6)][iodonium bis(phtamlimidate)]'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2366109'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-03-20T11:56:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C24 H16 I2 N4 O6 S2'
_chemical_formula_moiety         'C24 H16 I2 N4 O6 S2'
_chemical_formula_weight         774.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0405(6)
_cell_length_b                   12.0158(8)
_cell_length_c                   17.3956(12)
_cell_angle_alpha                94.170(2)
_cell_angle_beta                 102.710(2)
_cell_angle_gamma                105.874(2)
_cell_volume                     1561.04(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9599
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.08
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.810
_exptl_absorpt_correction_T_max  0.957

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5601  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_ub_11      -0.04268
_diffrn_orient_matrix_ub_12      0.018529
_diffrn_orient_matrix_ub_13      -0.054646
_diffrn_orient_matrix_ub_21      -0.027423
_diffrn_orient_matrix_ub_22      0.069321
_diffrn_orient_matrix_ub_23      0.02349
_diffrn_orient_matrix_ub_31      0.123534
_diffrn_orient_matrix_ub_32      0.049907
_diffrn_orient_matrix_ub_33      0.002429
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_number            19283
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         27.464
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             7101
_reflns_number_gt                4889
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0471P)²+0.1928P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7101
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.57
_refine_diff_density_rms         0.114

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 0.9448(6) 0.0144(4) 0.1372(3) 0.0360(10) Uani 1 1 d . . . . .
C2 C 0.8672(6) 0.0537(4) 0.1936(3) 0.0383(11) Uani 1 1 d . . . . .
C3 C 0.6826(7) 0.0233(4) 0.1786(3) 0.0513(13) Uani 1 1 d . . . . .
H3 H 0.6277 0.047 0.216 0.062 Uiso 1 1 calc R U . . .
C4 C 0.5822(7) -0.0433(5) 0.1066(3) 0.0556(14) Uani 1 1 d . . . . .
H4 H 0.4583 -0.063 0.0948 0.067 Uiso 1 1 calc R U . . .
C5 C 0.6628(7) -0.0807(4) 0.0525(3) 0.0516(14) Uani 1 1 d . . . . .
H5 H 0.5922 -0.1262 0.0049 0.062 Uiso 1 1 calc R U . . .
C6 C 0.8461(7) -0.0525(4) 0.0667(3) 0.0469(12) Uani 1 1 d . . . . .
H6 H 0.9002 -0.0782 0.0297 0.056 Uiso 1 1 calc R U . . .
C7 C 1.0006(7) 0.1264(4) 0.2643(3) 0.0461(12) Uani 1 1 d . . . . .
C8 C 1.1615(6) 0.2963(4) 0.8225(3) 0.0430(12) Uani 1 1 d . . . . .
C9 C 1.3309(6) 0.3298(4) 0.8737(3) 0.0441(12) Uani 1 1 d . . . . .
C10 C 1.3530(8) 0.3659(5) 0.9539(4) 0.0650(16) Uani 1 1 d . . . . .
H10 H 1.4653 0.3885 0.9893 0.078 Uiso 1 1 calc R U . . .
C11 C 1.2035(9) 0.3673(6) 0.9794(4) 0.0737(18) Uani 1 1 d . . . . .
H11 H 1.2163 0.3912 1.033 0.088 Uiso 1 1 calc R U . . .
C12 C 1.0361(9) 0.3348(6) 0.9289(4) 0.0784(19) Uani 1 1 d . . . . .
H12 H 0.9383 0.337 0.9485 0.094 Uiso 1 1 calc R U . . .
C13 C 1.0116(7) 0.2984(5) 0.8484(4) 0.0626(16) Uani 1 1 d . . . . .
H13 H 0.8988 0.2764 0.8134 0.075 Uiso 1 1 calc R U . . .
C14 C 1.4718(7) 0.3227(4) 0.8329(3) 0.0495(13) Uani 1 1 d . . . . .
C15 C 1.7359(5) 0.3546(3) 0.5109(3) 0.0314(10) Uani 1 1 d . . . . .
C16 C 1.8321(6) 0.4408(4) 0.5747(3) 0.0369(11) Uani 1 1 d . . . . .
H16 H 1.8872 0.4213 0.6225 0.044 Uiso 1 1 calc R U . . .
C17 C 1.8452(6) 0.5563(4) 0.5665(3) 0.0444(12) Uani 1 1 d . . . . .
H17 H 1.9097 0.6152 0.6087 0.053 Uiso 1 1 calc R U . . .
C18 C 1.7619(7) 0.5834(4) 0.4955(3) 0.0478(13) Uani 1 1 d . . . . .
H18 H 1.7709 0.6606 0.4883 0.057 Uiso 1 1 calc R U . . .
C19 C 1.6651(7) 0.4930(4) 0.4355(3) 0.0464(13) Uani 1 1 d . . . . .
H19 H 1.6058 0.5106 0.3879 0.056 Uiso 1 1 calc R U . . .
C20 C 1.7335(5) 0.2300(3) 0.5152(3) 0.0311(10) Uani 1 1 d . . . . .
C21 C 1.7819(6) 0.1715(4) 0.4560(3) 0.0387(11) Uani 1 1 d . . . . .
H21 H 1.8047 0.2064 0.4119 0.046 Uiso 1 1 calc R U . . .
C22 C 1.7954(6) 0.0606(4) 0.4636(3) 0.0454(13) Uani 1 1 d . . . . .
H22 H 1.83 0.02 0.4255 0.055 Uiso 1 1 calc R U . . .
C23 C 1.7568(7) 0.0118(4) 0.5288(3) 0.0448(12) Uani 1 1 d . . . . .
H23 H 1.7645 -0.0629 0.5352 0.054 Uiso 1 1 calc R U . . .
C24 C 1.7065(7) 0.0734(4) 0.5844(3) 0.0429(12) Uani 1 1 d . . . . .
H24 H 1.6811 0.0393 0.6285 0.051 Uiso 1 1 calc R U . . .
N1 N 1.1703(5) 0.1350(3) 0.2573(2) 0.0446(10) Uani 1 1 d . . . . .
N2 N 1.3942(5) 0.2845(4) 0.7526(2) 0.0466(10) Uani 1 1 d . . . . .
N3 N 1.6518(5) 0.3818(3) 0.4421(2) 0.0367(9) Uani 1 1 d . . . . .
N4 N 1.6930(5) 0.1806(3) 0.5775(2) 0.0321(8) Uani 1 1 d . . . . .
O1 O 1.2537(5) -0.0288(4) 0.1918(3) 0.0722(12) Uani 1 1 d . . . . .
O2 O 1.2592(5) 0.1447(4) 0.1271(2) 0.0744(13) Uani 1 1 d . . . . .
O3 O 0.9690(5) 0.1728(3) 0.3218(2) 0.0680(12) Uani 1 1 d . . . . .
O4 O 1.0910(5) 0.1342(3) 0.6977(2) 0.0624(10) Uani 1 1 d . . . . .
O5 O 1.1285(5) 0.3352(4) 0.6740(2) 0.0740(12) Uani 1 1 d . . . . .
O6 O 1.6273(5) 0.3436(4) 0.8635(2) 0.0695(12) Uani 1 1 d . . . . .
S1 S 1.17876(16) 0.06455(12) 0.17411(8) 0.0465(3) Uani 1 1 d . . . . .
S2 S 1.17475(16) 0.25628(12) 0.72589(8) 0.0458(3) Uani 1 1 d . . . . .
I1 I 1.40319(4) 0.24453(3) 0.34133(2) 0.03988(11) Uani 1 1 d . . . . .
I2 I 1.53815(4) 0.24361(3) 0.67021(2) 0.04007(11) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C6 1.364(6) . ?
C1 C2 1.392(6) . ?
C1 S1 1.762(5) . ?
C2 C3 1.388(6) . ?
C2 C7 1.475(6) . ?
C3 C4 1.385(7) . ?
C3 H3 0.93 . ?
C4 C5 1.369(7) . ?
C4 H4 0.93 . ?
C5 C6 1.379(7) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 O3 1.218(5) . ?
C7 N1 1.373(6) . ?
C8 C13 1.382(7) . ?
C8 C9 1.388(6) . ?
C8 S2 1.748(5) . ?
C9 C10 1.389(7) . ?
C9 C14 1.481(7) . ?
C10 C11 1.373(8) . ?
C10 H10 0.93 . ?
C11 C12 1.371(8) . ?
C11 H11 0.93 . ?
C12 C13 1.390(8) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C14 O6 1.194(6) . ?
C14 N2 1.385(6) . ?
C15 N3 1.348(5) . ?
C15 C16 1.385(6) . ?
C15 C20 1.500(6) . ?
C16 C17 1.383(6) . ?
C16 H16 0.93 . ?
C17 C18 1.377(7) . ?
C17 H17 0.93 . ?
C18 C19 1.375(7) . ?
C18 H18 0.93 . ?
C19 N3 1.326(5) . ?
C19 H19 0.93 . ?
C20 N4 1.333(5) . ?
C20 C21 1.388(6) . ?
C21 C22 1.379(6) . ?
C21 H21 0.93 . ?
C22 C23 1.370(7) . ?
C22 H22 0.93 . ?
C23 C24 1.371(7) . ?
C23 H23 0.93 . ?
C24 N4 1.334(5) . ?
C24 H24 0.93 . ?
N1 S1 1.647(4) . ?
N1 I1 2.131(4) . ?
N2 S2 1.654(4) . ?
N2 I2 2.138(4) . ?
N3 I1 2.455(4) . ?
N4 I2 2.439(4) . ?
O1 S1 1.433(4) . ?
O2 S1 1.422(4) . ?
O4 S2 1.433(4) . ?
O5 S2 1.422(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
C6 C1 C2 122.5(4) . . ?
C6 C1 S1 128.9(4) . . ?
C2 C1 S1 108.6(3) . . ?
C3 C2 C1 119.4(4) . . ?
C3 C2 C7 127.9(5) . . ?
C1 C2 C7 112.7(4) . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 120.9(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.7(5) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 117.2(5) . . ?
C1 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
O3 C7 N1 123.4(5) . . ?
O3 C7 C2 126.2(5) . . ?
N1 C7 C2 110.4(4) . . ?
C13 C8 C9 122.2(5) . . ?
C13 C8 S2 128.2(4) . . ?
C9 C8 S2 109.6(4) . . ?
C8 C9 C10 119.8(5) . . ?
C8 C9 C14 112.9(5) . . ?
C10 C9 C14 127.3(5) . . ?
C11 C10 C9 117.8(5) . . ?
C11 C10 H10 121.1 . . ?
C9 C10 H10 121.1 . . ?
C12 C11 C10 122.5(6) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 120.4(6) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 117.3(5) . . ?
C8 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
O6 C14 N2 124.6(5) . . ?
O6 C14 C9 126.3(5) . . ?
N2 C14 C9 109.1(4) . . ?
N3 C15 C16 120.8(4) . . ?
N3 C15 C20 118.6(4) . . ?
C16 C15 C20 120.5(4) . . ?
C17 C16 C15 119.2(4) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 118.0(4) . . ?
C19 C18 H18 121 . . ?
C17 C18 H18 121 . . ?
N3 C19 C18 123.3(5) . . ?
N3 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
N4 C20 C21 122.0(4) . . ?
N4 C20 C15 119.1(4) . . ?
C21 C20 C15 118.9(4) . . ?
C22 C21 C20 118.9(5) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 C21 118.4(5) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N4 C24 C23 122.1(4) . . ?
N4 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C7 N1 S1 114.4(3) . . ?
C7 N1 I1 122.7(3) . . ?
S1 N1 I1 122.6(2) . . ?
C14 N2 S2 115.0(3) . . ?
C14 N2 I2 123.4(3) . . ?
S2 N2 I2 121.2(2) . . ?
C19 N3 C15 119.1(4) . . ?
C19 N3 I1 113.3(3) . . ?
C15 N3 I1 125.0(3) . . ?
C20 N4 C24 118.7(4) . . ?
C20 N4 I2 127.8(3) . . ?
C24 N4 I2 112.4(3) . . ?
O2 S1 O1 117.0(3) . . ?
O2 S1 N1 110.4(2) . . ?
O1 S1 N1 109.6(2) . . ?
O2 S1 C1 111.2(2) . . ?
O1 S1 C1 112.3(2) . . ?
N1 S1 C1 93.9(2) . . ?
O5 S2 O4 116.5(3) . . ?
O5 S2 N2 109.8(2) . . ?
O4 S2 N2 110.3(2) . . ?
O5 S2 C8 111.5(3) . . ?
O4 S2 C8 113.0(2) . . ?
N2 S2 C8 93.3(2) . . ?
N1 I1 N3 174.18(14) . . ?
N2 I2 N4 175.42(14) . . ?

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 0.7(7) . . . . ?
S1 C1 C2 C3 -178.7(4) . . . . ?
C6 C1 C2 C7 -178.9(4) . . . . ?
S1 C1 C2 C7 1.7(5) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C7 C2 C3 C4 178.0(5) . . . . ?
C2 C3 C4 C5 1.6(8) . . . . ?
C3 C4 C5 C6 -0.9(8) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
S1 C1 C6 C5 179.4(4) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C3 C2 C7 O3 -0.5(9) . . . . ?
C1 C2 C7 O3 179.1(5) . . . . ?
C3 C2 C7 N1 179.1(5) . . . . ?
C1 C2 C7 N1 -1.4(6) . . . . ?
C13 C8 C9 C10 0.5(8) . . . . ?
S2 C8 C9 C10 179.7(4) . . . . ?
C13 C8 C9 C14 -178.9(5) . . . . ?
S2 C8 C9 C14 0.2(5) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C14 C9 C10 C11 179.2(5) . . . . ?
C9 C10 C11 C12 -0.1(10) . . . . ?
C10 C11 C12 C13 0.0(11) . . . . ?
C9 C8 C13 C12 -0.5(8) . . . . ?
S2 C8 C13 C12 -179.5(5) . . . . ?
C11 C12 C13 C8 0.3(10) . . . . ?
C8 C9 C14 O6 -177.9(5) . . . . ?
C10 C9 C14 O6 2.7(9) . . . . ?
C8 C9 C14 N2 0.5(6) . . . . ?
C10 C9 C14 N2 -178.9(5) . . . . ?
N3 C15 C16 C17 -1.7(7) . . . . ?
C20 C15 C16 C17 174.2(4) . . . . ?
C15 C16 C17 C18 0.3(7) . . . . ?
C16 C17 C18 C19 1.3(8) . . . . ?
C17 C18 C19 N3 -1.8(8) . . . . ?
N3 C15 C20 N4 -132.7(4) . . . . ?
C16 C15 C20 N4 51.3(6) . . . . ?
N3 C15 C20 C21 50.3(6) . . . . ?
C16 C15 C20 C21 -125.7(5) . . . . ?
N4 C20 C21 C22 -2.7(7) . . . . ?
C15 C20 C21 C22 174.2(4) . . . . ?
C20 C21 C22 C23 1.4(7) . . . . ?
C21 C22 C23 C24 -0.2(7) . . . . ?
C22 C23 C24 N4 0.2(8) . . . . ?
O3 C7 N1 S1 179.9(4) . . . . ?
C2 C7 N1 S1 0.4(6) . . . . ?
O3 C7 N1 I1 -6.2(7) . . . . ?
C2 C7 N1 I1 174.3(3) . . . . ?
O6 C14 N2 S2 177.4(5) . . . . ?
C9 C14 N2 S2 -1.0(5) . . . . ?
O6 C14 N2 I2 4.9(8) . . . . ?
C9 C14 N2 I2 -173.6(3) . . . . ?
C18 C19 N3 C15 0.5(8) . . . . ?
C18 C19 N3 I1 163.0(4) . . . . ?
C16 C15 N3 C19 1.3(7) . . . . ?
C20 C15 N3 C19 -174.7(4) . . . . ?
C16 C15 N3 I1 -159.0(3) . . . . ?
C20 C15 N3 I1 25.0(5) . . . . ?
C21 C20 N4 C24 2.7(6) . . . . ?
C15 C20 N4 C24 -174.1(4) . . . . ?
C21 C20 N4 I2 -163.9(3) . . . . ?
C15 C20 N4 I2 19.2(5) . . . . ?
C23 C24 N4 C20 -1.5(7) . . . . ?
C23 C24 N4 I2 167.1(4) . . . . ?
C7 N1 S1 O2 114.8(4) . . . . ?
I1 N1 S1 O2 -59.1(3) . . . . ?
C7 N1 S1 O1 -114.9(4) . . . . ?
I1 N1 S1 O1 71.2(3) . . . . ?
C7 N1 S1 C1 0.5(4) . . . . ?
I1 N1 S1 C1 -173.4(3) . . . . ?
C6 C1 S1 O2 65.8(5) . . . . ?
C2 C1 S1 O2 -114.8(4) . . . . ?
C6 C1 S1 O1 -67.5(5) . . . . ?
C2 C1 S1 O1 111.8(4) . . . . ?
C6 C1 S1 N1 179.4(5) . . . . ?
C2 C1 S1 N1 -1.3(4) . . . . ?
C14 N2 S2 O5 115.3(4) . . . . ?
I2 N2 S2 O5 -71.9(3) . . . . ?
C14 N2 S2 O4 -114.9(4) . . . . ?
I2 N2 S2 O4 57.8(3) . . . . ?
C14 N2 S2 C8 1.0(4) . . . . ?
I2 N2 S2 C8 173.8(3) . . . . ?
C13 C8 S2 O5 65.5(6) . . . . ?
C9 C8 S2 O5 -113.5(4) . . . . ?
C13 C8 S2 O4 -67.9(5) . . . . ?
C9 C8 S2 O4 113.0(4) . . . . ?
C13 C8 S2 N2 178.4(5) . . . . ?
C9 C8 S2 N2 -0.7(4) . . . . ?





_chemical_name_systematic        Bis(N-iodosaccharin)(2,2'-bipyridine)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2366104'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-24T09:52:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C26 H16 I2 N4 O4'
_chemical_formula_moiety         'C26 H16 I2 N4 O4'
_chemical_formula_weight         702.23

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   7.5392(8)
_cell_length_b                   9.4310(10)
_cell_length_c                   17.2253(18)
_cell_angle_alpha                90
_cell_angle_beta                 97.896(3)
_cell_angle_gamma                90
_cell_volume                     1213.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4213
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.46
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             676

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.924

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      2
_diffrn_orient_matrix_ub_12      -0.132804
_diffrn_orient_matrix_ub_13      -0.012704
_diffrn_orient_matrix_ub_21      2
_diffrn_orient_matrix_ub_22      0.008357
_diffrn_orient_matrix_ub_23      -0.014615
_diffrn_orient_matrix_ub_31      2
_diffrn_orient_matrix_ub_32      -0.014997
_diffrn_orient_matrix_ub_33      0.104249
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_number            2727
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.387
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_reflns_Friedel_coverage         0
_reflns_number_total             2727
_reflns_number_gt                2216
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_secondary   'dual - dual-space method e.g. SHELXD'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0229P)²+1.7040P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2727
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0726
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_restrained_S_all      1.188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.134

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
I I -0.4742 1.8119 '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'

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 0.1743(7) 0.3998(5) 0.5601(3) 0.0338(12) Uani 1 1 d . . . . .
C2 C 0.1068(6) 0.2710(5) 0.5316(3) 0.0318(11) Uani 1 1 d . . . . .
C3 C 0.0255(7) 0.1783(6) 0.5775(3) 0.0415(13) Uani 1 1 d . . . . .
H3 H -0.0197 0.0914 0.5583 0.05 Uiso 1 1 calc R U . . .
C4 C 0.0146(8) 0.2206(7) 0.6534(3) 0.0521(16) Uani 1 1 d . . . . .
H4 H -0.0414 0.1612 0.6857 0.062 Uiso 1 1 calc R U . . .
C5 C 0.0833(8) 0.3469(7) 0.6828(3) 0.0508(16) Uani 1 1 d . . . . .
H5 H 0.0754 0.3702 0.7347 0.061 Uiso 1 1 calc R U . . .
C6 C 0.1644(7) 0.4409(6) 0.6368(3) 0.0422(13) Uani 1 1 d . . . . .
H6 H 0.2101 0.5273 0.6563 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2543(7) 0.4723(5) 0.4963(3) 0.0328(11) Uani 1 1 d . . . . .
C8 C 0.1439(7) 0.2587(6) 0.4495(3) 0.0364(11) Uani 1 1 d . . . . .
C9 C 0.3593(8) 0.5769(6) 0.1529(3) 0.0459(13) Uani 1 1 d . . . . .
H9 H 0.2974 0.6473 0.1758 0.055 Uiso 1 1 calc R U . . .
C10 C 0.3904(8) 0.5957(5) 0.0772(3) 0.0443(15) Uani 1 1 d . . . . .
H10 H 0.3502 0.6774 0.05 0.053 Uiso 1 1 calc R U . . .
C11 C 0.4821(6) 0.4927(5) 0.0408(3) 0.0288(11) Uani 1 1 d . . . . .
C12 C 0.5353(8) 0.3727(6) 0.0850(3) 0.0422(14) Uani 1 1 d . . . . .
H12 H 0.5946 0.2993 0.0634 0.051 Uiso 1 1 calc R U . . .
C13 C 0.4994(8) 0.3635(6) 0.1610(3) 0.0439(13) Uani 1 1 d . . . . .
H13 H 0.5376 0.2833 0.19 0.053 Uiso 1 1 calc R U . . .
I1 I 0.32337(5) 0.42310(3) 0.32536(2) 0.03448(11) Uani 1 1 d . . . . .
N1 N 0.2367(6) 0.3800(4) 0.4335(3) 0.0349(10) Uani 1 1 d . . . . .
N2 N 0.4125(6) 0.4640(5) 0.1952(2) 0.0374(11) Uani 1 1 d . . . . .
O1 O 0.3209(6) 0.5885(4) 0.4983(2) 0.0455(9) Uani 1 1 d . . . . .
O2 O 0.1031(6) 0.1638(4) 0.4033(2) 0.0578(12) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.381(7) . ?
C1 C6 1.388(8) . ?
C1 C7 1.490(7) . ?
C2 C3 1.379(7) . ?
C2 C8 1.484(7) . ?
C3 C4 1.380(8) . ?
C3 H3 0.93 . ?
C4 C5 1.368(9) . ?
C4 H4 0.93 . ?
C5 C6 1.386(8) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 O1 1.204(6) . ?
C7 N1 1.381(7) . ?
C8 O2 1.208(6) . ?
C8 N1 1.388(6) . ?
C9 N2 1.321(7) . ?
C9 C10 1.369(8) . ?
C9 H9 0.93 . ?
C10 C11 1.390(7) . ?
C10 H10 0.93 . ?
C11 C12 1.393(7) . ?
C11 C11 1.474(10) 3_665 ?
C12 C13 1.375(8) . ?
C12 H12 0.93 . ?
C13 N2 1.334(7) . ?
C13 H13 0.93 . ?
I1 N1 2.096(4) . ?
I1 N2 2.457(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 121.2(5) . . ?
C2 C1 C7 107.9(4) . . ?
C6 C1 C7 130.8(5) . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 C8 130.9(5) . . ?
C1 C2 C8 107.4(4) . . ?
C4 C3 C2 116.7(5) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C5 C4 C3 122.2(6) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 121.3(6) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 116.8(5) . . ?
C1 C6 H6 121.6 . . ?
C5 C6 H6 121.6 . . ?
O1 C7 N1 126.2(5) . . ?
O1 C7 C1 127.3(5) . . ?
N1 C7 C1 106.5(4) . . ?
O2 C8 N1 124.7(5) . . ?
O2 C8 C2 128.4(5) . . ?
N1 C8 C2 106.9(4) . . ?
N2 C9 C10 123.5(5) . . ?
N2 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C9 C10 C11 120.0(5) . . ?
C9 C10 H10 120 . . ?
C11 C10 H10 120 . . ?
C10 C11 C12 116.4(5) . . ?
C10 C11 C11 122.2(5) . 3_665 ?
C12 C11 C11 121.4(6) . 3_665 ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
N2 C13 C12 123.3(5) . . ?
N2 C13 H13 118.4 . . ?
C12 C13 H13 118.4 . . ?
N1 I1 N2 176.79(15) . . ?
C7 N1 C8 111.1(4) . . ?
C7 N1 I1 124.5(3) . . ?
C8 N1 I1 124.3(3) . . ?
C9 N2 C13 117.3(5) . . ?
C9 N2 I1 121.9(4) . . ?
C13 N2 I1 120.2(4) . . ?



# END of CIF
_chemical_name_systematic        
"Bis(N(iodophtalimide)(4,4'-bipyridine), beta phase"
_chemical_name_common            beta-(NIPht)2(p-bipy)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC6
_database_code_depnum_ccdc_archive 'CCDC 2366105'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-03-30T16:48:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C29 H22 Cl2 I2 N4 O4'
_chemical_formula_moiety         'C12 H12 N2, 2(C8 H4 I N O2), C H2 Cl2'
_chemical_formula_weight         815.21
_chemical_absolute_configuration ;

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b a 2'
_symmetry_space_group_name_Hall  'P 2 -2ab'
_symmetry_Int_Tables_number      32
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'

_cell_length_a                   25.6531(16)
_cell_length_b                   14.2270(8)
_cell_length_c                   4.1646(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1519.94(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2945
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      23.8
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.919

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.6361  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_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_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_number            13219
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.779
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_coverage         0.747
_reflns_number_total             3449
_reflns_number_gt                2655
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     'direct - structure invariant direct methods'
_atom_sites_solution_secondary   'direct - structure invariant direct methods'
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     191
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.0818
_refine_ls_wR_factor_gt          0.0759
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_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_diff_density_max         0.593
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.092

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?



# END of CIF
_chemical_name_systematic        
'Bis(N-iodophalimide)(5,5?-dimethyl-2,2?-bipyridine), (dichloromethane)'
_chemical_name_common            (NIPht)2(o-Me2bipy),(CH2Cl2)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC7
_database_code_depnum_ccdc_archive 'CCDC 2366107'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2024-04-12T11:27:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C18 H16 I2 N4 O4'
_chemical_formula_sum            'C18 H16 I2 N4 O4'
_chemical_formula_weight         606.15

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   21.488(2)
_cell_length_b                   10.0888(8)
_cell_length_c                   9.4428(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.324(3)
_cell_angle_gamma                90
_cell_volume                     2047.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1160

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.883

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# Estimated minimum and maximum transmission:  0.6568  0.7456                #
# The ratio of these values is more reliable than their absolute values!     #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.060001
_diffrn_orient_matrix_ub_12      -0.005338
_diffrn_orient_matrix_ub_13      -0.038116
_diffrn_orient_matrix_ub_21      0.06871
_diffrn_orient_matrix_ub_22      0.063865
_diffrn_orient_matrix_ub_23      0.019012
_diffrn_orient_matrix_ub_31      0.053797
_diffrn_orient_matrix_ub_32      -0.075615
_diffrn_orient_matrix_ub_33      0.018748
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_number            26687
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_reflns_Friedel_coverage         0
_reflns_number_total             4638
_reflns_number_gt                4525
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+2.8728P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4638
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0447
_refine_ls_wR_factor_gt          0.0444
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
I I -0.4742 1.8119 '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'

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 0.76417(10) 0.4006(2) 0.7929(2) 0.0203(4) Uani 1 1 d . . . . .
C2 C 0.82161(11) 0.3783(3) 0.8561(3) 0.0281(5) Uani 1 1 d . . . . .
H2 H 0.84151 0.445985 0.909617 0.034 Uiso 1 1 calc R U . . .
C3 C 0.84949(11) 0.2552(3) 0.8399(3) 0.0328(6) Uani 1 1 d . . . . .
H3 H 0.888691 0.237358 0.882857 0.039 Uiso 1 1 calc R U . . .
C4 C 0.81980(12) 0.1594(3) 0.7611(3) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.837914 0.074191 0.74947 0.038 Uiso 1 1 calc R U . . .
C5 C 0.76323(11) 0.1893(2) 0.6993(3) 0.0297(5) Uani 1 1 d . . . . .
H5 H 0.742954 0.123371 0.643981 0.036 Uiso 1 1 calc R U . . .
C6 C 0.72983(10) 0.5264(2) 0.8203(2) 0.0196(4) Uani 1 1 d . . . . .
C7 C 0.67666(11) 0.5247(2) 0.9030(3) 0.0254(5) Uani 1 1 d . . . . .
H7 H 0.660094 0.442843 0.935283 0.031 Uiso 1 1 calc R U . . .
C8 C 0.64795(12) 0.6426(3) 0.9381(3) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.611962 0.64313 0.996018 0.034 Uiso 1 1 calc R U . . .
C9 C 0.67242(12) 0.7594(2) 0.8875(3) 0.0306(5) Uani 1 1 d . . . . .
H9 H 0.653766 0.842018 0.910225 0.037 Uiso 1 1 calc R U . . .
C10 C 0.72455(13) 0.7539(2) 0.8034(3) 0.0329(6) Uani 1 1 d . . . . .
H10 H 0.740659 0.834492 0.766584 0.04 Uiso 1 1 calc R U . . .
C11 C 0.58407(12) 0.4436(2) 0.2724(2) 0.0272(5) Uani 1 1 d . . . . .
C12 C 0.52154(14) 0.4587(3) 0.2004(3) 0.0358(6) Uani 1 1 d . . . . .
H12A H 0.521729 0.416212 0.105853 0.043 Uiso 1 1 calc R U . . .
H12B H 0.510651 0.55343 0.189105 0.043 Uiso 1 1 calc R U . . .
C13 C 0.47586(12) 0.3897(3) 0.2979(3) 0.0334(6) Uani 1 1 d . . . . .
H13A H 0.440608 0.448909 0.320995 0.04 Uiso 1 1 calc R U . . .
H13B H 0.459365 0.307983 0.253386 0.04 Uiso 1 1 calc R U . . .
C14 C 0.51330(11) 0.3572(2) 0.4289(3) 0.0256(5) Uani 1 1 d . . . . .
C15 C 0.94431(12) 0.8268(3) 0.4485(3) 0.0346(6) Uani 1 1 d . . . . .
C16 C 0.99938(13) 0.8117(4) 0.3510(3) 0.0465(8) Uani 1 1 d . . . . .
H16A H 0.992585 0.861889 0.262193 0.056 Uiso 1 1 calc R U . . .
H16B H 1.037848 0.844562 0.397327 0.056 Uiso 1 1 calc R U . . .
C17 C 1.00419(14) 0.6650(4) 0.3212(3) 0.0475(8) Uani 1 1 d . . . . .
H17A H 1.044896 0.630025 0.353505 0.057 Uiso 1 1 calc R U . . .
H17B H 0.999504 0.647301 0.218541 0.057 Uiso 1 1 calc R U . . .
C18 C 0.95169(12) 0.6023(3) 0.4031(3) 0.0380(7) Uani 1 1 d . . . . .
I1 I 0.64794(2) 0.35208(2) 0.55151(2) 0.02045(5) Uani 1 1 d . . . . .
I2 I 0.84472(2) 0.66693(2) 0.60855(2) 0.02603(5) Uani 1 1 d . . . . .
N1 N 0.73570(9) 0.30774(19) 0.7143(2) 0.0228(4) Uani 1 1 d . . . . .
N2 N 0.75368(9) 0.6401(2) 0.7710(2) 0.0260(4) Uani 1 1 d . . . . .
N3 N 0.57488(9) 0.38547(19) 0.4038(2) 0.0228(4) Uani 1 1 d . . . . .
N4 N 0.92061(9) 0.7018(2) 0.4747(2) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.63414(9) 0.47776(19) 0.22679(19) 0.0365(4) Uani 1 1 d . . . . .
O2 O 0.49340(9) 0.3127(2) 0.5393(2) 0.0356(4) Uani 1 1 d . . . . .
O3 O 0.92395(9) 0.9277(2) 0.4983(2) 0.0454(5) Uani 1 1 d . . . . .
O4 O 0.93786(10) 0.4870(2) 0.4080(2) 0.0498(6) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 1.340(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.491(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.95 . ?
C3 C4 1.375(4) . ?
C3 H3 0.95 . ?
C4 C5 1.379(4) . ?
C4 H4 0.95 . ?
C5 N1 1.342(3) . ?
C5 H5 0.95 . ?
C6 N2 1.341(3) . ?
C6 C7 1.388(3) . ?
C7 C8 1.381(3) . ?
C7 H7 0.95 . ?
C8 C9 1.376(4) . ?
C8 H8 0.95 . ?
C9 C10 1.378(4) . ?
C9 H9 0.95 . ?
C10 N2 1.344(3) . ?
C10 H10 0.95 . ?
C11 O1 1.211(3) . ?
C11 N3 1.388(3) . ?
C11 C12 1.510(4) . ?
C12 C13 1.518(4) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 C14 1.508(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 O2 1.215(3) . ?
C14 N3 1.375(3) . ?
C15 O3 1.205(4) . ?
C15 N4 1.382(3) . ?
C15 C16 1.511(4) . ?
C16 C17 1.510(5) . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 C18 1.511(4) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 O4 1.201(4) . ?
C18 N4 1.384(4) . ?
I1 N3 2.1212(19) . ?
I1 N1 2.4673(19) . ?
I2 N4 2.099(2) . ?
I2 N2 2.507(2) . ?

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 C1 C2 121.8(2) . . ?
N1 C1 C6 117.79(19) . . ?
C2 C1 C6 120.2(2) . . ?
C1 C2 C3 118.8(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 118.7(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.6(2) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N2 C6 C7 121.6(2) . . ?
N2 C6 C1 118.52(19) . . ?
C7 C6 C1 119.77(19) . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 118.6(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 123.1(2) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
O1 C11 N3 124.7(2) . . ?
O1 C11 C12 127.0(2) . . ?
N3 C11 C12 108.3(2) . . ?
C11 C12 C13 104.9(2) . . ?
C11 C12 H12A 110.8 . . ?
C13 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C13 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
C14 C13 C12 104.7(2) . . ?
C14 C13 H13A 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.9 . . ?
O2 C14 N3 124.6(2) . . ?
O2 C14 C13 126.5(2) . . ?
N3 C14 C13 108.8(2) . . ?
O3 C15 N4 124.5(3) . . ?
O3 C15 C16 127.6(3) . . ?
N4 C15 C16 107.9(3) . . ?
C17 C16 C15 105.5(2) . . ?
C17 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
C16 C17 C18 105.2(3) . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17A 110.7 . . ?
C16 C17 H17B 110.7 . . ?
C18 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
O4 C18 N4 124.3(2) . . ?
O4 C18 C17 127.7(3) . . ?
N4 C18 C17 108.0(3) . . ?
N3 I1 N1 177.27(7) . . ?
N4 I2 N2 176.52(8) . . ?
C1 N1 C5 118.8(2) . . ?
C1 N1 I1 124.25(14) . . ?
C5 N1 I1 115.58(16) . . ?
C6 N2 C10 118.2(2) . . ?
C6 N2 I2 127.26(15) . . ?
C10 N2 I2 114.42(16) . . ?
C14 N3 C11 112.6(2) . . ?
C14 N3 I1 124.26(16) . . ?
C11 N3 I1 123.13(16) . . ?
C15 N4 C18 113.3(2) . . ?
C15 N4 I2 123.29(19) . . ?
C18 N4 I2 123.44(18) . . ?

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
N1 C1 C2 C3 -1.4(4) . . . . ?
C6 C1 C2 C3 173.6(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
N1 C1 C6 N2 -117.4(2) . . . . ?
C2 C1 C6 N2 67.3(3) . . . . ?
N1 C1 C6 C7 66.7(3) . . . . ?
C2 C1 C6 C7 -108.6(3) . . . . ?
N2 C6 C7 C8 -1.2(4) . . . . ?
C1 C6 C7 C8 174.6(2) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 N2 -1.7(4) . . . . ?
O1 C11 C12 C13 175.5(2) . . . . ?
N3 C11 C12 C13 -5.8(3) . . . . ?
C11 C12 C13 C14 8.0(3) . . . . ?
C12 C13 C14 O2 172.6(2) . . . . ?
C12 C13 C14 N3 -7.8(3) . . . . ?
O3 C15 C16 C17 -179.9(3) . . . . ?
N4 C15 C16 C17 1.2(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 O4 179.0(3) . . . . ?
C16 C17 C18 N4 -1.0(3) . . . . ?
C2 C1 N1 C5 1.3(3) . . . . ?
C6 C1 N1 C5 -173.9(2) . . . . ?
C2 C1 N1 I1 -164.43(17) . . . . ?
C6 C1 N1 I1 20.4(3) . . . . ?
C4 C5 N1 C1 -0.2(4) . . . . ?
C4 C5 N1 I1 166.7(2) . . . . ?
C7 C6 N2 C10 -0.2(3) . . . . ?
C1 C6 N2 C10 -176.0(2) . . . . ?
C7 C6 N2 I2 -175.94(17) . . . . ?
C1 C6 N2 I2 8.2(3) . . . . ?
C9 C10 N2 C6 1.7(4) . . . . ?
C9 C10 N2 I2 178.0(2) . . . . ?
O2 C14 N3 C11 -175.9(2) . . . . ?
C13 C14 N3 C11 4.5(3) . . . . ?
O2 C14 N3 I1 1.7(3) . . . . ?
C13 C14 N3 I1 -177.95(15) . . . . ?
O1 C11 N3 C14 179.7(2) . . . . ?
C12 C11 N3 C14 0.9(3) . . . . ?
O1 C11 N3 I1 2.1(3) . . . . ?
C12 C11 N3 I1 -176.70(15) . . . . ?
O3 C15 N4 C18 179.1(3) . . . . ?
C16 C15 N4 C18 -1.9(3) . . . . ?
O3 C15 N4 I2 -0.5(4) . . . . ?
C16 C15 N4 I2 178.48(16) . . . . ?
O4 C18 N4 C15 -178.1(3) . . . . ?
C17 C18 N4 C15 1.8(3) . . . . ?
O4 C18 N4 I2 1.5(4) . . . . ?
C17 C18 N4 I2 -178.55(17) . . . . ?



# END of CIF
_chemical_name_systematic        Bis(N-iodosuccinimide)(2,2'-bipyridine)
_chemical_name_common            (NISucc)2(o-bipy)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/pentane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC8
_database_code_depnum_ccdc_archive 'CCDC 2366108'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2024-03-22T13:54:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H20 I2 N4 O4'
_chemical_formula_weight         634.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   8.4092(8)
_cell_length_b                   16.8459(18)
_cell_length_c                   15.5232(16)
_cell_angle_alpha                90
_cell_angle_beta                 94.164(4)
_cell_angle_gamma                90
_cell_volume                     2193.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.5
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_T_max  0.944

#-------------------------------- Remark --------------------------------------#
# SADABS output:                                                               #
# Estimated minimum and maximum transmission:  0.5134  0.7456                  #
# The ratio of these values is more reliable than their absolute values!       #
# Ratio of Min/Max transmission:               0.6886                          #
#------------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_orient_matrix_ub_11      0.00003
_diffrn_orient_matrix_ub_12      0.059337
_diffrn_orient_matrix_ub_13      0.001847
_diffrn_orient_matrix_ub_21      0.047621
_diffrn_orient_matrix_ub_22      0.001553
_diffrn_orient_matrix_ub_23      -0.057161
_diffrn_orient_matrix_ub_31      -0.109309
_diffrn_orient_matrix_ub_32      0.000693
_diffrn_orient_matrix_ub_33      -0.030018
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_number            37649
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.428
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_reflns_Friedel_coverage         0
_reflns_number_total             5000
_reflns_number_gt                4791
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+5.4031P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5000
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0439
_refine_ls_wR_factor_gt          0.0428
_refine_ls_goodness_of_fit_ref   0.72
_refine_ls_restrained_S_all      0.72
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.664
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
I I -0.4742 1.8119 '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'

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 0.6141(2) 0.74230(11) 0.61259(12) 0.0156(3) Uani 1 1 d . . . . .
C2 C 0.4771(2) 0.86089(12) 0.59822(13) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.41521 0.896734 0.562434 0.024 Uiso 1 1 calc R U . . .
C3 C 0.5118(2) 0.88139(12) 0.68445(13) 0.0215(4) Uani 1 1 d . . . . .
C4 C 0.6011(2) 0.82754(13) 0.73528(12) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.627091 0.838848 0.794589 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6526(2) 0.75722(12) 0.70000(13) 0.0215(4) Uani 1 1 d . . . . .
H5 H 0.713024 0.719959 0.734714 0.026 Uiso 1 1 calc R U . . .
C6 C 0.6665(2) 0.66796(11) 0.57175(11) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.7980(2) 0.60777(12) 0.46360(12) 0.0188(4) Uani 1 1 d . . . . .
H7 H 0.85874 0.612781 0.414619 0.023 Uiso 1 1 calc R U . . .
C8 C 0.7632(2) 0.53201(11) 0.49179(12) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.6777(3) 0.52647(12) 0.56491(13) 0.0229(4) Uani 1 1 d . . . . .
H9 H 0.65225 0.47584 0.587076 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6296(2) 0.59479(12) 0.60552(13) 0.0216(4) Uani 1 1 d . . . . .
H10 H 0.572144 0.591402 0.655863 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4507(3) 0.95812(14) 0.71939(16) 0.0322(5) Uani 1 1 d . . . . .
H11A H 0.368832 0.946675 0.759448 0.048 Uiso 1 1 calc R U . . .
H11B H 0.40461 0.990645 0.671537 0.048 Uiso 1 1 calc R U . . .
H11C H 0.539 0.986963 0.7499 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8170(3) 0.45958(12) 0.44581(14) 0.0259(4) Uani 1 1 d . . . . .
H12A H 0.731107 0.441279 0.40453 0.039 Uiso 1 1 calc R U . . .
H12B H 0.843989 0.417523 0.487988 0.039 Uiso 1 1 calc R U . . .
H12C H 0.911146 0.472602 0.414874 0.039 Uiso 1 1 calc R U . . .
C13 C 0.2580(2) 0.80058(11) 0.23207(12) 0.0178(4) Uani 1 1 d . . . . .
C14 C 0.1495(2) 0.68453(11) 0.28071(12) 0.0178(3) Uani 1 1 d . . . . .
C15 C 0.0792(2) 0.69415(12) 0.18832(13) 0.0216(4) Uani 1 1 d . . . . .
H15A H -0.038645 0.69686 0.186377 0.026 Uiso 1 1 calc R U . . .
H15B H 0.110194 0.649156 0.152101 0.026 Uiso 1 1 calc R U . . .
C16 C 0.1481(2) 0.77181(12) 0.15697(12) 0.0217(4) Uani 1 1 d . . . . .
H16A H 0.208071 0.762819 0.105265 0.026 Uiso 1 1 calc R U . . .
H16B H 0.062381 0.810894 0.142521 0.026 Uiso 1 1 calc R U . . .
C17 C 0.9919(2) 0.91783(11) 0.31389(12) 0.0200(4) Uani 1 1 d . . . . .
C18 C 1.1088(2) 0.94154(11) 0.45045(12) 0.0180(3) Uani 1 1 d . . . . .
C19 C 1.1820(2) 1.00171(12) 0.39297(13) 0.0230(4) Uani 1 1 d . . . . .
H19A H 1.297957 0.992293 0.391152 0.028 Uiso 1 1 calc R U . . .
H19B H 1.165281 1.056312 0.414092 0.028 Uiso 1 1 calc R U . . .
C20 C 1.0966(3) 0.98977(12) 0.30402(13) 0.0233(4) Uani 1 1 d . . . . .
H20A H 1.031442 1.036866 0.286736 0.028 Uiso 1 1 calc R U . . .
H20B H 1.174031 0.980131 0.260099 0.028 Uiso 1 1 calc R U . . .
I1 I 0.38366(2) 0.76443(2) 0.41861(2) 0.01607(4) Uani 1 1 d . . . . .
I2 I 0.88041(2) 0.79766(2) 0.44702(2) 0.01604(4) Uani 1 1 d . . . . .
N1 N 0.52612(19) 0.79361(9) 0.56299(10) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.75075(19) 0.67424(9) 0.50158(10) 0.0171(3) Uani 1 1 d . . . . .
N3 N 0.25049(19) 0.74771(9) 0.30004(10) 0.0169(3) Uani 1 1 d . . . . .
N4 N 1.00429(18) 0.89478(9) 0.39981(10) 0.0171(3) Uani 1 1 d . . . . .
O1 O 0.33935(18) 0.86004(9) 0.23483(10) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.12482(19) 0.63067(9) 0.32978(9) 0.0269(3) Uani 1 1 d . . . . .
O3 O 0.91077(19) 0.88426(10) 0.25735(10) 0.0299(3) Uani 1 1 d . . . . .
O4 O 1.13672(17) 0.93400(9) 0.52767(9) 0.0224(3) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 N1 1.343(2) . ?
C1 C5 1.395(3) . ?
C1 C6 1.485(2) . ?
C2 N1 1.336(2) . ?
C2 C3 1.393(3) . ?
C2 H2 0.95 . ?
C3 C4 1.387(3) . ?
C3 C11 1.506(3) . ?
C4 C5 1.388(3) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C6 N2 1.346(2) . ?
C6 C10 1.383(3) . ?
C7 N2 1.339(2) . ?
C7 C8 1.387(3) . ?
C7 H7 0.95 . ?
C8 C9 1.390(3) . ?
C8 C12 1.500(3) . ?
C9 C10 1.387(3) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 O1 1.212(2) . ?
C13 N3 1.386(2) . ?
C13 C16 1.514(3) . ?
C14 O2 1.212(2) . ?
C14 N3 1.381(2) . ?
C14 C15 1.520(3) . ?
C15 C16 1.525(3) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
C16 H16A 0.99 . ?
C16 H16B 0.99 . ?
C17 O3 1.212(3) . ?
C17 N4 1.386(2) . ?
C17 C20 1.512(3) . ?
C18 O4 1.211(2) . ?
C18 N4 1.382(2) . ?
C18 C19 1.511(3) . ?
C19 C20 1.523(3) . ?
C19 H19A 0.99 . ?
C19 H19B 0.99 . ?
C20 H20A 0.99 . ?
C20 H20B 0.99 . ?
I1 N3 2.1028(16) . ?
I1 N1 2.5120(16) . ?
I2 N4 2.0999(15) . ?
I2 N2 2.5225(16) . ?

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 C1 C5 121.40(17) . . ?
N1 C1 C6 117.78(16) . . ?
C5 C1 C6 120.81(17) . . ?
N1 C2 C3 123.68(19) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C4 C3 C2 116.84(18) . . ?
C4 C3 C11 122.76(19) . . ?
C2 C3 C11 120.4(2) . . ?
C3 C4 C5 120.37(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C1 118.72(19) . . ?
C4 C5 H5 120.6 . . ?
C1 C5 H5 120.6 . . ?
N2 C6 C10 121.48(17) . . ?
N2 C6 C1 117.98(16) . . ?
C10 C6 C1 120.54(16) . . ?
N2 C7 C8 123.66(17) . . ?
N2 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
C7 C8 C9 116.92(17) . . ?
C7 C8 C12 121.36(17) . . ?
C9 C8 C12 121.71(18) . . ?
C10 C9 C8 120.05(18) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C6 C10 C9 119.11(17) . . ?
C6 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 N3 124.12(18) . . ?
O1 C13 C16 127.11(18) . . ?
N3 C13 C16 108.77(16) . . ?
O2 C14 N3 124.82(18) . . ?
O2 C14 C15 126.88(18) . . ?
N3 C14 C15 108.29(16) . . ?
C14 C15 C16 105.17(15) . . ?
C14 C15 H15A 110.7 . . ?
C16 C15 H15A 110.7 . . ?
C14 C15 H15B 110.7 . . ?
C16 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
C13 C16 C15 104.71(15) . . ?
C13 C16 H16A 110.8 . . ?
C15 C16 H16A 110.8 . . ?
C13 C16 H16B 110.8 . . ?
C15 C16 H16B 110.8 . . ?
H16A C16 H16B 108.9 . . ?
O3 C17 N4 124.43(18) . . ?
O3 C17 C20 127.00(18) . . ?
N4 C17 C20 108.57(17) . . ?
O4 C18 N4 124.93(17) . . ?
O4 C18 C19 126.64(18) . . ?
N4 C18 C19 108.43(16) . . ?
C18 C19 C20 105.13(16) . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19B 110.7 . . ?
C20 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
C17 C20 C19 104.71(16) . . ?
C17 C20 H20A 110.8 . . ?
C19 C20 H20A 110.8 . . ?
C17 C20 H20B 110.8 . . ?
C19 C20 H20B 110.8 . . ?
H20A C20 H20B 108.9 . . ?
N3 I1 N1 175.09(6) . . ?
N4 I2 N2 175.41(6) . . ?
C2 N1 C1 118.98(17) . . ?
C2 N1 I1 112.95(12) . . ?
C1 N1 I1 126.34(12) . . ?
C7 N2 C6 118.76(16) . . ?
C7 N2 I2 113.08(12) . . ?
C6 N2 I2 127.03(12) . . ?
C14 N3 C13 113.03(16) . . ?
C14 N3 I1 124.99(12) . . ?
C13 N3 I1 121.98(13) . . ?
C18 N4 C17 112.82(16) . . ?
C18 N4 I2 123.82(12) . . ?
C17 N4 I2 123.34(13) . . ?

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
N1 C2 C3 C4 -0.6(3) . . . . ?
N1 C2 C3 C11 -179.44(18) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C11 C3 C4 C5 179.17(19) . . . . ?
C3 C4 C5 C1 0.6(3) . . . . ?
N1 C1 C5 C4 -1.3(3) . . . . ?
C6 C1 C5 C4 179.98(18) . . . . ?
N1 C1 C6 N2 56.4(2) . . . . ?
C5 C1 C6 N2 -124.89(19) . . . . ?
N1 C1 C6 C10 -123.9(2) . . . . ?
C5 C1 C6 C10 54.9(3) . . . . ?
N2 C7 C8 C9 -1.6(3) . . . . ?
N2 C7 C8 C12 178.99(18) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C12 C8 C9 C10 -179.82(19) . . . . ?
N2 C6 C10 C9 -1.5(3) . . . . ?
C1 C6 C10 C9 178.80(19) . . . . ?
C8 C9 C10 C6 0.7(3) . . . . ?
O2 C14 C15 C16 179.52(19) . . . . ?
N3 C14 C15 C16 -1.5(2) . . . . ?
O1 C13 C16 C15 178.99(19) . . . . ?
N3 C13 C16 C15 -1.7(2) . . . . ?
C14 C15 C16 C13 1.8(2) . . . . ?
O4 C18 C19 C20 -175.64(18) . . . . ?
N4 C18 C19 C20 5.2(2) . . . . ?
O3 C17 C20 C19 -174.8(2) . . . . ?
N4 C17 C20 C19 4.6(2) . . . . ?
C18 C19 C20 C17 -5.7(2) . . . . ?
C3 C2 N1 C1 -0.1(3) . . . . ?
C3 C2 N1 I1 165.80(15) . . . . ?
C5 C1 N1 C2 1.1(3) . . . . ?
C6 C1 N1 C2 179.85(16) . . . . ?
C5 C1 N1 I1 -162.74(14) . . . . ?
C6 C1 N1 I1 16.0(2) . . . . ?
C8 C7 N2 C6 0.9(3) . . . . ?
C8 C7 N2 I2 169.59(15) . . . . ?
C10 C6 N2 C7 0.7(3) . . . . ?
C1 C6 N2 C7 -179.55(16) . . . . ?
C10 C6 N2 I2 -166.25(14) . . . . ?
C1 C6 N2 I2 13.5(2) . . . . ?
O2 C14 N3 C13 179.47(18) . . . . ?
C15 C14 N3 C13 0.4(2) . . . . ?
O2 C14 N3 I1 0.0(3) . . . . ?
C15 C14 N3 I1 -179.02(12) . . . . ?
O1 C13 N3 C14 -179.82(18) . . . . ?
C16 C13 N3 C14 0.8(2) . . . . ?
O1 C13 N3 I1 -0.4(3) . . . . ?
C16 C13 N3 I1 -179.71(12) . . . . ?
O4 C18 N4 C17 178.35(18) . . . . ?
C19 C18 N4 C17 -2.4(2) . . . . ?
O4 C18 N4 I2 -2.8(3) . . . . ?
C19 C18 N4 I2 176.43(12) . . . . ?
O3 C17 N4 C18 177.97(19) . . . . ?
C20 C17 N4 C18 -1.4(2) . . . . ?
O3 C17 N4 I2 -0.9(3) . . . . ?
C20 C17 N4 I2 179.70(12) . . . . ?



# END of CIF
_chemical_name_systematic        
Bis(N-iodosuccinimide)(5,5?-dimethyl-2,2?-bipyridine)
_chemical_name_common            (NISucc)2(o-Me2bipy)
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC9
_database_code_depnum_ccdc_archive 'CCDC 2366106'
loop_
_audit_author_name
_audit_author_address
'Olivier Jeannin'
;University Rennes
France
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_date             2018-02-27T16:47:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H16 I2 N4 O6 S2'
_chemical_formula_sum            'C24 H16 I2 N4 O6 S2'
_chemical_formula_weight         774.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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'

_cell_length_a                   8.6873(9)
_cell_length_b                   9.2187(10)
_cell_length_c                   16.9914(16)
_cell_angle_alpha                90
_cell_angle_beta                 105.954(3)
_cell_angle_gamma                90
_cell_volume                     1308.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7516
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.20
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.966
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  0.731

#------------------------------- Remark -------------------------------------#
# SADABS output:                                                             #
# HKLF 5 dataset constructed from all observations involving domain 1        #
#   40403 Corrected reflections written to file twin5.hkl                    #
# Reflections not merged                                                     #
# Single reflections that also occur in composites omitted                   #
# Racemic twinning not included for all components                           #
# Second component not inverted relative to first                            #
# Minimum and maximum apparent transmission:  0.542474  0.745553             #
#                                                                            #
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_number            28084
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             28084
_reflns_number_gt                22562
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2014)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2014)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0258P)²+2.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         28084
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0732
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.086

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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 . . . ?



# END of CIF
_chemical_name_systematic        bis(N-iodosaccharin)(4,4'-bipyridine)
_chemical_name_common            (NISacc)2(p-bipy)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
