# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_nk699_a
_database_code_depnum_ccdc_archive 'CCDC 2257393'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C7 H10 N'
_chemical_formula_sum            'C7 H10 Cl4 I N'
_chemical_formula_weight         376.86
_chemical_melting_point          ?
_chemical_oxdiff_formula         IClCHN
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3175(7)
_cell_length_b                   9.8500(5)
_cell_length_c                   7.6668(5)
_cell_angle_alpha                90.0
_cell_angle_beta                 101.728(7)
_cell_angle_gamma                90.0
_cell_volume                     615.01(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1023
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      28.1360
_cell_measurement_theta_min      3.3930
_cell_oxdiff_angle_alpha         89.991(4)
_cell_oxdiff_angle_beta          101.721(5)
_cell_oxdiff_angle_gamma         90.025(5)
_cell_oxdiff_length_a            8.3148(5)
_cell_oxdiff_length_b            9.8542(6)
_cell_oxdiff_length_c            7.6659(4)
_cell_oxdiff_measurement_reflns_used 1023
_cell_oxdiff_volume              615.01(6)
_shelx_estimated_absorpt_T_max   0.748
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    3.430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.035
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2679
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         29.027
_diffrn_reflns_theta_min         2.501
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  93.00   0.50    6.22    --   11.26  19.00  60.00  226
  2  ω     28.00  85.00   0.50    6.22    --   11.26  57.00  90.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0772525000
_diffrn_orient_matrix_UB_12      -0.0329845000
_diffrn_orient_matrix_UB_13      -0.0110967000
_diffrn_orient_matrix_UB_21      -0.0146664000
_diffrn_orient_matrix_UB_22      0.0137366000
_diffrn_orient_matrix_UB_23      -0.0927137000
_diffrn_orient_matrix_UB_31      0.0375139000
_diffrn_orient_matrix_UB_32      -0.0624852000
_diffrn_orient_matrix_UB_33      -0.0145172000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1043
_reflns_number_total             1360
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.251
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1360
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C6, N1, C7, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Fixed Sof: N1(0.5) C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C7(0.5) H7A(0.5) H7B(0.5)
 H7C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 1.000000 0.500000 1.000000 0.01778(18) Uani 1 2 d S . P . .
Cl2 Cl 0.6952(2) 0.48599(15) 0.9397(4) 0.0566(6) Uani 1 1 d . . . . .
Cl1 Cl 1.0071(2) 0.30148(17) 0.8012(2) 0.0561(5) Uani 1 1 d . . . . .
N1 N 1.5497(18) 0.0583(12) 0.9668(15) 0.030(2) Uani 0.5 1 d . U P A -1
C1 C 1.4943(15) -0.0726(14) 0.9534(18) 0.025(3) Uani 0.5 1 d . U P A -1
C2 C 1.346(2) -0.0918(14) 1.0131(19) 0.031(3) Uani 0.5 1 d . U P A -1
H2 H 1.303458 -0.181241 1.012894 0.037 Uiso 0.5 1 calc R U P A -1
C3 C 1.2642(15) 0.0076(13) 1.0688(17) 0.030(3) Uani 0.5 1 d . U P A -1
H3 H 1.165720 -0.011565 1.108801 0.036 Uiso 0.5 1 calc R U P A -1
C4 C 1.3212(16) 0.1429(13) 1.0699(17) 0.032(3) Uani 0.5 1 d . U P A -1
H4 H 1.261004 0.216357 1.105108 0.039 Uiso 0.5 1 calc R U P A -1
C5 C 1.4650(17) 0.1625(14) 1.0187(18) 0.032(3) Uani 0.5 1 d . U P A -1
H5 H 1.507848 0.251866 1.019031 0.038 Uiso 0.5 1 calc R U P A -1
C6 C 1.7038(18) 0.0838(19) 0.901(2) 0.042(3) Uani 0.5 1 d . U P A -1
H6A H 1.686911 0.060117 0.774789 0.063 Uiso 0.5 1 calc R U P A -1
H6B H 1.792540 0.028139 0.969236 0.063 Uiso 0.5 1 calc R U P A -1
H6C H 1.733354 0.180026 0.916954 0.063 Uiso 0.5 1 calc R U P A -1
C7 C 1.583(2) -0.1826(14) 0.893(2) 0.042(4) Uani 0.5 1 d . U P A -1
H7A H 1.593480 -0.165626 0.769810 0.063 Uiso 0.5 1 calc R U P A -1
H7B H 1.523419 -0.267817 0.898564 0.063 Uiso 0.5 1 calc R U P A -1
H7C H 1.692534 -0.189289 0.969348 0.063 Uiso 0.5 1 calc R U P A -1


_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 Cl2 2.4862(17) 3_767 ?
I1 Cl2 2.4863(17) . ?
I1 Cl1 2.4873(16) . ?
I1 Cl1 2.4872(16) 3_767 ?
N1 C1 1.367(16) . ?
N1 C5 1.349(19) . ?
N1 C6 1.490(19) . ?
C1 C2 1.41(2) . ?
C1 C7 1.440(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.313(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.414(17) . ?
C4 H4 0.9500 . ?
C4 C5 1.35(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
Cl2 I1 Cl2 180.0 3_767 . ?
Cl2 I1 Cl1 89.58(7) . . ?
Cl2 I1 Cl1 90.42(7) . 3_767 ?
Cl2 I1 Cl1 90.42(7) 3_767 . ?
Cl2 I1 Cl1 89.59(7) 3_767 3_767 ?
Cl1 I1 Cl1 180.00(8) 3_767 . ?
C1 N1 C6 115.7(13) . . ?
C5 N1 C1 123.4(16) . . ?
C5 N1 C6 120.5(13) . . ?
N1 C1 C2 113.9(15) . . ?
N1 C1 C7 123.2(14) . . ?
C2 C1 C7 122.8(13) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 C1 123.4(15) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.8(12) . . ?
C5 C4 H4 121.6 . . ?
N1 C5 H5 119.2 . . ?
C4 C5 N1 121.7(13) . . ?
C4 C5 H5 119.2 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 3.0(19) . . . . ?
C1 N1 C5 C4 3.4(19) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C5 -3(2) . . . . ?
C3 C4 C5 N1 0.7(19) . . . . ?
C5 N1 C1 C2 -5.1(17) . . . . ?
C5 N1 C1 C7 178.1(14) . . . . ?
C6 N1 C1 C2 -178.6(13) . . . . ?
C6 N1 C1 C7 4.5(16) . . . . ?
C6 N1 C5 C4 176.6(12) . . . . ?
C7 C1 C2 C3 179.9(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.821
####################################################################### 
# 
# 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_nk698_a
_database_code_depnum_ccdc_archive 'CCDC 2257394'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C7 H10 N'
_chemical_formula_sum            'C7 H10 Cl4 I N'
_chemical_formula_weight         376.86
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.3707(3)
_cell_length_b                   11.8303(9)
_cell_length_c                   11.8442(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.985(3)
_cell_angle_gamma                90
_cell_volume                     611.59(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      29.54
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    3.449
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0877 before and 0.0505 after correction.
The Ratio of minimum to maximum transmission is 0.8413.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.034
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6479
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.580
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1479
_reflns_number_total             1712
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         1712
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0415
_refine_ls_wR_factor_ref         0.0432
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N1, C2}
3. Uiso/Uaniso restraints and constraints
Uanis(N1) = Uanis(C2)
4. Others
 Fixed Sof: N1(0.5) C2(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4)
5.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 1.000000 0.01963(6) Uani 1 2 d S . P . .
Cl1 Cl 0.66867(12) 0.42553(4) 0.81611(4) 0.02866(11) Uani 1 1 d . . . . .
Cl2 Cl 0.26548(12) 0.66845(4) 0.90035(5) 0.02994(12) Uani 1 1 d . . . . .
C3 C 1.1974(4) 0.42392(16) 0.55049(18) 0.0255(4) Uani 1 1 d . . . . .
H3 H 1.334794 0.371161 0.586203 0.031 Uiso 1 1 calc R U . A 1
C4 C 1.0950(5) 0.51379(16) 0.61106(19) 0.0248(4) Uani 1 1 d . . . . .
H4 H 1.162248 0.522799 0.688097 0.030 Uiso 1 1 calc R U . . .
C1 C 1.2167(5) 0.31212(16) 0.3733(2) 0.0307(5) Uani 1 1 d . . . . .
H1A H 1.064277 0.251325 0.371837 0.046 Uiso 1 1 calc R U . B 1
H1B H 1.409957 0.284564 0.408912 0.046 Uiso 1 1 calc R U . B 1
H1C H 1.250199 0.336435 0.295816 0.046 Uiso 1 1 calc R U . B 1
N1 N 1.1043(4) 0.40905(14) 0.43889(16) 0.0217(4) Uani 0.5 1 d . . P C 1
C2 C 1.1043(4) 0.40905(14) 0.43889(16) 0.0217(4) Uani 0.5 1 d . . P C 2


_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 Cl1 2.4962(5) . ?
I1 Cl1 2.4962(5) 3_667 ?
I1 Cl2 2.5078(5) . ?
I1 Cl2 2.5078(5) 3_667 ?
C3 H3 0.9500 . ?
C3 C4 1.371(3) . ?
C3 N1 1.374(3) . ?
C3 C2 1.374(3) . ?
C4 H4 0.9500 . ?
C4 N1 1.374(3) 3_766 ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 N1 1.483(3) . ?
C1 C2 1.483(3) . ?

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
Cl1 I1 Cl1 180.0 . 3_667 ?
Cl1 I1 Cl2 89.894(17) 3_667 . ?
Cl1 I1 Cl2 90.106(17) . . ?
Cl1 I1 Cl2 89.893(17) . 3_667 ?
Cl1 I1 Cl2 90.107(17) 3_667 3_667 ?
Cl2 I1 Cl2 180.0 3_667 . ?
C4 C3 H3 119.5 . . ?
C4 C3 N1 120.96(18) . . ?
C4 C3 C2 120.96(18) . . ?
N1 C3 H3 119.5 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 N1 120.5(2) . 3_766 ?
N1 C4 H4 119.8 3_766 . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
C3 N1 C4 118.58(18) . 3_766 ?
C3 N1 C1 120.89(17) . . ?
C4 N1 C1 120.53(19) 3_766 . ?
C3 C2 C4 118.58(18) . 3_766 ?
C3 C2 C1 120.89(17) . . ?
C4 C2 C1 120.53(19) 3_766 . ?

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
C4 C3 N1 C4 -0.2(3) . . . 3_766 ?
C4 C3 N1 C1 179.66(18) . . . . ?
C4 C3 C2 C4 -0.2(3) . . . 3_766 ?
C4 C3 C2 C1 179.66(18) . . . . ?
N1 C3 C4 N1 0.2(3) . . . 3_766 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nk770_a
_database_code_depnum_ccdc_archive 'CCDC 2257399'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C12 H14 N2, Cl'
_chemical_formula_sum            'C12 H14 Cl5 I N2'
_chemical_formula_weight         490.40
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4887(5)
_cell_length_b                   7.6756(5)
_cell_length_c                   8.0494(5)
_cell_angle_alpha                93.199(2)
_cell_angle_beta                 110.363(2)
_cell_angle_gamma                95.058(3)
_cell_volume                     430.22(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5068
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.56
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.798
_exptl_absorpt_coefficient_mu    2.628
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0483 after correction.
The Ratio of minimum to maximum transmission is 0.8619.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5544
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.579
_diffrn_reflns_theta_min         2.676
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2207
_reflns_number_total             2276
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.403
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.113
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0161P)²+0.7968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), N1(H1A), C2(H2), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.500000 0.000000 1.000000 0.01924(8) Uani 1 2 d S . P . .
C1 C 0.7161(5) 0.6703(4) 0.5316(4) 0.0280(6) Uani 1 1 d . . . . .
H1 H 0.670893 0.781269 0.506809 0.034 Uiso 1 1 calc R U . . .
N1 N 0.6904(4) 0.5490(3) 0.3986(3) 0.0262(5) Uani 1 1 d . . . . .
H1A H 0.630282 0.572652 0.288564 0.031 Uiso 1 1 calc R U . . .
Cl1 Cl 0.83965(12) -0.00987(12) 1.19737(12) 0.0397(2) Uani 1 1 d . . . . .
Cl2 Cl 0.59871(13) 0.03611(11) 0.73759(10) 0.03378(18) Uani 1 1 d . . . . .
C2 C 0.8073(4) 0.6367(4) 0.7045(4) 0.0257(6) Uani 1 1 d . . . . .
H2 H 0.824548 0.724032 0.798846 0.031 Uiso 1 1 calc R U . . .
Cl3 Cl 0.500000 0.500000 0.000000 0.0302(2) Uani 1 2 d S . P . .
C3 C 0.8748(4) 0.4745(4) 0.7420(4) 0.0213(5) Uani 1 1 d . . . . .
C5 C 0.7539(4) 0.3909(4) 0.4277(4) 0.0250(6) Uani 1 1 d . . . . .
H5 H 0.734632 0.306906 0.330083 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8461(4) 0.3507(4) 0.5979(4) 0.0238(6) Uani 1 1 d . . . . .
H4 H 0.890629 0.238940 0.618187 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9743(5) 0.4247(4) 0.9278(4) 0.0255(6) Uani 1 1 d . . . . .
H6A H 1.093165 0.374853 0.932111 0.031 Uiso 1 1 calc R U . . .
H6B H 0.890092 0.331557 0.953515 0.031 Uiso 1 1 calc R U . . .


_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 Cl1 2.4969(8) 2_657 ?
I1 Cl1 2.4969(8) . ?
I1 Cl2 2.4902(8) 2_657 ?
I1 Cl2 2.4901(8) . ?
C1 H1 0.9500 . ?
C1 N1 1.329(4) . ?
C1 C2 1.371(4) . ?
N1 H1A 0.8800 . ?
N1 C5 1.345(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(4) . ?
C3 C4 1.401(4) . ?
C3 C6 1.508(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.369(4) . ?
C4 H4 0.9500 . ?
C6 C6 1.515(5) 2_767 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
Cl1 I1 Cl1 180.0 . 2_657 ?
Cl2 I1 Cl1 88.84(3) 2_657 . ?
Cl2 I1 Cl1 88.84(3) . 2_657 ?
Cl2 I1 Cl1 91.16(3) 2_657 2_657 ?
Cl2 I1 Cl1 91.16(3) . . ?
Cl2 I1 Cl2 180.0 . 2_657 ?
N1 C1 H1 119.7 . . ?
N1 C1 C2 120.5(3) . . ?
C2 C1 H1 119.7 . . ?
C1 N1 H1A 119.2 . . ?
C1 N1 C5 121.6(3) . . ?
C5 N1 H1A 119.2 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 117.6(3) . . ?
C2 C3 C6 123.9(3) . . ?
C4 C3 C6 118.5(3) . . ?
N1 C5 H5 119.9 . . ?
N1 C5 C4 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C6 C6 114.5(3) . 2_767 ?
C3 C6 H6A 108.6 . . ?
C3 C6 H6B 108.6 . . ?
C6 C6 H6A 108.6 2_767 . ?
C6 C6 H6B 108.6 2_767 . ?
H6A C6 H6B 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
C1 N1 C5 C4 0.6(5) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C1 C2 C3 C6 -179.1(3) . . . . ?
N1 C1 C2 C3 0.3(5) . . . . ?
N1 C5 C4 C3 -0.1(4) . . . . ?
C2 C1 N1 C5 -0.7(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C3 C6 C6 -9.6(5) . . . 2_767 ?
C4 C3 C6 C6 171.1(3) . . . 2_767 ?
C6 C3 C4 C5 179.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nk704_a
_database_code_depnum_ccdc_archive 'CCDC 2257396'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C8 H12 N'
_chemical_formula_sum            'C8 H12 Cl4 I N'
_chemical_formula_weight         390.89
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.4476(6)
_cell_length_b                   9.9715(4)
_cell_length_c                   7.8504(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.6000(10)
_cell_angle_gamma                90
_cell_volume                     1332.91(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9025
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.00
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.648
_exptl_absorpt_coefficient_mu    3.169
_exptl_absorpt_correction_T_max  0.7466
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0525 before and 0.0448 after correction.
The Ratio of minimum to maximum transmission is 0.9091.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.948
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13777
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.372
_diffrn_reflns_theta_min         2.367
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2021
_reflns_number_total             2315
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         2315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0166
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+0.7387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0365
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.39466(2) 0.79149(4) 0.55384(5) 0.03039(8) Uani 1 1 d . . . . .
I1 I 0.250000 0.750000 0.500000 0.01887(4) Uani 1 2 d S . P . .
Cl2 Cl 0.23727(2) 0.94528(4) 0.69174(5) 0.02965(8) Uani 1 1 d . . . . .
N1 N 0.500000 0.77299(16) 0.250000 0.0235(3) Uani 1 2 d S T P . .
C1 C 0.500000 0.9204(2) 0.250000 0.0381(5) Uani 1 2 d S T P . .
H1A H 0.462378 0.953206 0.316573 0.057 Uiso 0.5 1 calc R U P . .
H1B H 0.484947 0.953206 0.129626 0.057 Uiso 0.5 1 calc R U P . .
H1C H 0.552675 0.953206 0.303800 0.057 Uiso 0.5 1 calc R U P . .
C2 C 0.37208(11) 0.7838(2) 0.0387(3) 0.0394(4) Uani 1 1 d . . . . .
H2A H 0.3315(15) 0.725(2) -0.019(3) 0.059 Uiso 1 1 d . U . . .
H2B H 0.3513(13) 0.839(2) 0.108(3) 0.059 Uiso 1 1 d . U . . .
H2C H 0.3880(13) 0.836(2) -0.050(3) 0.059 Uiso 1 1 d . U . . .
C3 C 0.43861(8) 0.70595(15) 0.14747(18) 0.0246(3) Uani 1 1 d . . . . .
C4 C 0.43890(8) 0.56842(15) 0.14691(19) 0.0272(3) Uani 1 1 d . . . . .
H4 H 0.396721 0.521003 0.075006 0.033 Uiso 1 1 calc R U . . .
C5 C 0.500000 0.4985(2) 0.250000 0.0285(4) Uani 1 2 d S T P . .
H5 H 0.500001 0.403266 0.249999 0.034 Uiso 1 2 calc R U P . .


_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
Cl1 I1 2.5010(4) . ?
I1 Cl2 2.5005(3) . ?
I1 Cl2 2.5006(3) 7_566 ?
N1 C1 1.470(3) . ?
N1 C3 1.3659(16) 2_655 ?
N1 C3 1.3659(16) . ?
C1 H1A 0.9800 . ?
C1 H1A 0.9800 2_655 ?
C1 H1B 0.9800 . ?
C1 H1B 0.9800 2_655 ?
C1 H1C 0.9800 2_655 ?
C1 H1C 0.9800 . ?
C2 H2A 0.96(2) . ?
C2 H2B 0.91(2) . ?
C2 H2C 0.96(2) . ?
C2 C3 1.499(2) . ?
C3 C4 1.371(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3787(17) . ?
C5 H5 0.9500 . ?

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
Cl1 I1 Cl1 180.0 . 7_566 ?
Cl2 I1 Cl1 90.669(12) . 7_566 ?
Cl2 I1 Cl1 90.668(12) 7_566 . ?
Cl2 I1 Cl1 89.331(12) . . ?
Cl2 I1 Cl1 89.333(12) 7_566 7_566 ?
Cl2 I1 Cl2 180.0 . 7_566 ?
C3 N1 C1 119.30(8) 2_655 . ?
C3 N1 C1 119.30(8) . . ?
C3 N1 C3 121.39(17) 2_655 . ?
N1 C1 H1A 109.470(7) . 2_655 ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.471(2) . 2_655 ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.470(17) . 2_655 ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1A 141.1 . 2_655 ?
H1A C1 H1B 56.3 . 2_655 ?
H1A C1 H1B 109.5 2_655 2_655 ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 56.3 . 2_655 ?
H1A C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 2_655 2_655 ?
H1B C1 H1A 56.3 . 2_655 ?
H1B C1 H1B 141.1 . 2_655 ?
H1B C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 2_655 2_655 ?
H1B C1 H1C 56.3 . 2_655 ?
H1C C1 H1A 56.3 . 2_655 ?
H1C C1 H1B 56.2 . 2_655 ?
H1C C1 H1C 141.1 . 2_655 ?
H2A C2 H2B 108(2) . . ?
H2A C2 H2C 107(2) . . ?
H2B C2 H2C 109.2(19) . . ?
C3 C2 H2A 110.6(14) . . ?
C3 C2 H2B 109.5(14) . . ?
C3 C2 H2C 112.6(13) . . ?
N1 C3 C2 119.50(15) . . ?
N1 C3 C4 119.23(13) . . ?
C4 C3 C2 121.26(14) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.43(14) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C4 119.28(19) 2_655 . ?
C4 C5 H5 120.4 . . ?
C4 C5 H5 120.4 2_655 . ?

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 C3 C4 C5 0.69(19) . . . . ?
C1 N1 C3 C2 -0.70(15) . . . . ?
C1 N1 C3 C4 179.65(9) . . . . ?
C2 C3 C4 C5 -178.95(13) . . . . ?
C3 N1 C3 C2 179.30(15) 2_655 . . . ?
C3 N1 C3 C4 -0.35(9) 2_655 . . . ?
C3 C4 C5 C4 -0.35(10) . . . 2_655 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nk695_a
_database_code_depnum_ccdc_archive 'CCDC 2257401'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C4 H12 N'
_chemical_formula_sum            'C4 H12 Cl4 I N'
_chemical_formula_weight         342.85
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   16.4343(5)
_cell_length_b                   16.4343(5)
_cell_length_c                   11.4451(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2677.02(19)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    4432
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      27.3860
_cell_measurement_theta_min      2.2810
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    3.535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8458
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.901
_diffrn_reflns_theta_min         1.779
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector_area_resol_mean 10.6168
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.795
_reflns_number_gt                5777
_reflns_number_total             6216
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1970 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(19)
_refine_ls_extinction_coef       0.00027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         6216
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0164P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0614
_refine_ls_wR_factor_ref         0.0643
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9239(7)
 0.0761(7)
2. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N3-C9 \\sim N3-C9A
 with sigma of 0.02
 N3-C10 \\sim N3-C10A
 with sigma of 0.02
 N3-C11 \\sim N3-C11A
 with sigma of 0.02
 N3-C12 \\sim N3-C12A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2) = Uanis(C3) = Uanis(C4) = Uanis(C5) = Uanis(C6) =
Uanis(C7) = Uanis(C8) = Uanis(C9) = Uanis(C10) = Uanis(C11) = Uanis(C12)
Uanis(C1A) = Uanis(C3A) = Uanis(C4A) = Uanis(C6A) = Uanis(C7A) = Uanis(C8A) =
Uanis(C9A) = Uanis(C10A) = Uanis(C11A) = Uanis(C12A)
5. Others
 Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=1-FVAR(2)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=Sof(C8)=
 Sof(H8A)=Sof(H8B)=Sof(H8C)=FVAR(2)
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10D)=Sof(H10E)=
 Sof(H10F)=Sof(C11A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=1-FVAR(3)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 FVAR(3)
6.a Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,
 H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C),
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C1A(H1AA,H1AB,
 H1AC), C3A(H3AA,H3AB,H3AC), C4A(H4AA,H4AB,H4AC), C6A(H6AA,H6AB,H6AC), C7A(H7AA,
 H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C10A(H10D,H10E,H10F),
 C11A(H11D,H11E,H11F), C12A(H12D,H12E,H12F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.25779(4) 0.46934(4) 0.25578(4) 0.02993(14) Uani 1 1 d . . . . .
I2 I 0.53251(4) 0.38857(4) 0.53512(5) 0.03127(15) Uani 1 1 d . . . . .
I3 I 0.87656(4) 0.80724(4) 0.12713(5) 0.03508(16) Uani 1 1 d . . . . .
Cl1 Cl 0.3769(2) 0.4659(2) 0.3897(2) 0.0653(9) Uani 1 1 d . . . . .
Cl2 Cl 0.1417(2) 0.4685(2) 0.1210(2) 0.0607(8) Uani 1 1 d . . . . .
Cl3 Cl 0.2657(2) 0.3551(2) 0.1220(3) 0.0621(9) Uani 1 1 d . . . . .
Cl4 Cl 0.2419(3) 0.5851(2) 0.3811(3) 0.0678(9) Uani 1 1 d . . . . .
Cl5 Cl 0.5439(2) 0.2706(2) 0.4060(3) 0.0752(10) Uani 1 1 d . . . . .
Cl6 Cl 0.5259(2) 0.5050(2) 0.6615(2) 0.0588(8) Uani 1 1 d . . . . .
Cl7 Cl 0.6691(2) 0.5179(2) 0.4340(2) 0.0577(8) Uani 1 1 d . . . . .
Cl8 Cl 0.3927(2) 0.2623(2) 0.6406(3) 0.0615(8) Uani 1 1 d . . . . .
Cl9 Cl 0.7661(2) 0.8203(3) -0.0096(3) 0.0706(9) Uani 1 1 d . . . . .
Cl10 Cl 0.7427(3) 0.6908(3) 0.2445(3) 0.1025(14) Uani 1 1 d . . . . .
Cl11 Cl 0.9832(3) 0.7926(3) 0.2671(3) 0.0836(12) Uani 1 1 d . . . . .
Cl12 Cl 1.0148(2) 0.9231(3) 0.0126(3) 0.0698(9) Uani 1 1 d . . . . .
N1 N 0.5504(7) 0.4453(7) 0.0462(7) 0.050(3) Uani 1 1 d . . . . .
N3 N 0.5660(7) 0.7882(7) 0.4073(8) 0.051(2) Uani 1 1 d D . . . .
N2 N 0.8654(6) 0.7654(6) 0.6564(6) 0.038(2) Uani 1 1 d . . . . .
C1 C 0.527(2) 0.518(2) 0.025(3) 0.079(2) Uani 0.465(18) 1 d . . P A 1
H1A H 0.567526 0.573593 0.071965 0.118 Uiso 0.465(18) 1 calc R U P A 1
H1B H 0.460962 0.494813 0.046465 0.118 Uiso 0.465(18) 1 calc R U P A 1
H1C H 0.535528 0.535034 -0.058108 0.118 Uiso 0.465(18) 1 calc R U P A 1
C2 C 0.4779(9) 0.3699(10) -0.0315(11) 0.079(2) Uani 1 1 d . . . B 1
H2A H 0.505513 0.372741 -0.108358 0.118 Uiso 1 1 calc R U . B 1
H2B H 0.424098 0.379620 -0.040299 0.118 Uiso 1 1 calc R U . B 1
H2C H 0.456984 0.308124 0.003679 0.118 Uiso 1 1 calc R U . B 1
C3 C 0.520(2) 0.404(2) 0.164(3) 0.079(2) Uani 0.465(18) 1 d . . P A 1
H3A H 0.536529 0.355628 0.176788 0.118 Uiso 0.465(18) 1 calc R U P A 1
H3B H 0.451512 0.376722 0.170993 0.118 Uiso 0.465(18) 1 calc R U P A 1
H3C H 0.550927 0.453853 0.223121 0.118 Uiso 0.465(18) 1 calc R U P A 1
C4 C 0.638(2) 0.459(2) 0.019(3) 0.079(2) Uani 0.465(18) 1 d . . P A 1
H4A H 0.678472 0.482426 0.088054 0.118 Uiso 0.465(18) 1 calc R U P A 1
H4B H 0.665260 0.504893 -0.044381 0.118 Uiso 0.465(18) 1 calc R U P A 1
H4C H 0.632176 0.399248 -0.005792 0.118 Uiso 0.465(18) 1 calc R U P A 1
C5 C 0.7669(9) 0.7135(10) 0.6945(12) 0.079(2) Uani 1 1 d . . . C 2
H5A H 0.761933 0.678497 0.766046 0.118 Uiso 1 1 calc R U . C 2
H5B H 0.728366 0.669461 0.633060 0.118 Uiso 1 1 calc R U . C 2
H5C H 0.744672 0.757767 0.709833 0.118 Uiso 1 1 calc R U . C 2
C6 C 0.8947(17) 0.6957(18) 0.630(2) 0.079(2) Uani 0.606(15) 1 d . . P C 2
H6A H 0.963195 0.727722 0.622559 0.118 Uiso 0.606(15) 1 calc R U P C 2
H6B H 0.865520 0.663353 0.556977 0.118 Uiso 0.606(15) 1 calc R U P C 2
H6C H 0.874657 0.649739 0.693874 0.118 Uiso 0.606(15) 1 calc R U P C 2
C7 C 0.8817(17) 0.8239(19) 0.554(2) 0.079(2) Uani 0.606(15) 1 d . . P C 2
H7A H 0.872690 0.876754 0.573877 0.118 Uiso 0.606(15) 1 calc R U P C 2
H7B H 0.837342 0.786393 0.491868 0.118 Uiso 0.606(15) 1 calc R U P C 2
H7C H 0.946149 0.847853 0.525651 0.118 Uiso 0.606(15) 1 calc R U P C 2
C8 C 0.9189(16) 0.8207(17) 0.756(2) 0.079(2) Uani 0.606(15) 1 d . . P C 2
H8A H 0.893104 0.859803 0.783007 0.118 Uiso 0.606(15) 1 calc R U P C 2
H8B H 0.984740 0.861008 0.733383 0.118 Uiso 0.606(15) 1 calc R U P C 2
H8C H 0.914983 0.778621 0.819249 0.118 Uiso 0.606(15) 1 calc R U P C 2
C9 C 0.572(3) 0.710(2) 0.463(3) 0.079(2) Uani 0.427(14) 1 d D . P D 3
H9A H 0.612376 0.734037 0.532711 0.118 Uiso 0.427(14) 1 calc R U P D 3
H9B H 0.599708 0.685163 0.407923 0.118 Uiso 0.427(14) 1 calc R U P D 3
H9C H 0.509472 0.660763 0.485865 0.118 Uiso 0.427(14) 1 calc R U P D 3
C10 C 0.4741(18) 0.744(3) 0.348(3) 0.079(2) Uani 0.427(14) 1 d D . P D 3
H10A H 0.423793 0.713919 0.405900 0.118 Uiso 0.427(14) 1 calc R U P D 3
H10B H 0.470160 0.696836 0.292393 0.118 Uiso 0.427(14) 1 calc R U P D 3
H10C H 0.467210 0.792258 0.305779 0.118 Uiso 0.427(14) 1 calc R U P D 3
C11 C 0.626(2) 0.833(2) 0.299(2) 0.079(2) Uani 0.427(14) 1 d D . P D 3
H11A H 0.622150 0.889435 0.277555 0.118 Uiso 0.427(14) 1 calc R U P D 3
H11B H 0.601989 0.788534 0.233782 0.118 Uiso 0.427(14) 1 calc R U P D 3
H11C H 0.691104 0.851511 0.314845 0.118 Uiso 0.427(14) 1 calc R U P D 3
C12 C 0.569(2) 0.865(2) 0.476(3) 0.079(2) Uani 0.427(14) 1 d D . P D 3
H12A H 0.536043 0.840273 0.550627 0.118 Uiso 0.427(14) 1 calc R U P D 3
H12B H 0.538634 0.893906 0.432757 0.118 Uiso 0.427(14) 1 calc R U P D 3
H12C H 0.634647 0.912573 0.492099 0.118 Uiso 0.427(14) 1 calc R U P D 3
C1A C 0.603(2) 0.544(2) -0.011(2) 0.096(4) Uani 0.535(18) 1 d . . P A 4
H1AA H 0.562117 0.571670 -0.009751 0.143 Uiso 0.535(18) 1 calc R U P A 4
H1AB H 0.617947 0.537625 -0.092310 0.143 Uiso 0.535(18) 1 calc R U P A 4
H1AC H 0.660492 0.583777 0.032093 0.143 Uiso 0.535(18) 1 calc R U P A 4
C3A C 0.515(2) 0.461(2) 0.160(2) 0.096(4) Uani 0.535(18) 1 d . . P A 4
H3AA H 0.559991 0.470844 0.222063 0.143 Uiso 0.535(18) 1 calc R U P A 4
H3AB H 0.454123 0.405558 0.178417 0.143 Uiso 0.535(18) 1 calc R U P A 4
H3AC H 0.507427 0.516171 0.153462 0.143 Uiso 0.535(18) 1 calc R U P A 4
C4A C 0.626(2) 0.422(2) 0.083(3) 0.096(4) Uani 0.535(18) 1 d . . P A 4
H4AA H 0.667999 0.467700 0.139972 0.143 Uiso 0.535(18) 1 calc R U P A 4
H4AB H 0.662147 0.423089 0.013814 0.143 Uiso 0.535(18) 1 calc R U P A 4
H4AC H 0.595809 0.358622 0.117383 0.143 Uiso 0.535(18) 1 calc R U P A 4
C6A C 0.929(3) 0.730(3) 0.715(3) 0.096(4) Uani 0.394(15) 1 d . . P C 5
H6AA H 0.991785 0.783932 0.727734 0.143 Uiso 0.394(15) 1 calc R U P C 5
H6AB H 0.932517 0.684764 0.663310 0.143 Uiso 0.394(15) 1 calc R U P C 5
H6AC H 0.901127 0.700497 0.789767 0.143 Uiso 0.394(15) 1 calc R U P C 5
C7A C 0.865(3) 0.758(3) 0.526(3) 0.096(4) Uani 0.394(15) 1 d . . P C 5
H7AA H 0.816573 0.769949 0.494147 0.143 Uiso 0.394(15) 1 calc R U P C 5
H7AB H 0.851765 0.695318 0.504054 0.143 Uiso 0.394(15) 1 calc R U P C 5
H7AC H 0.926654 0.805173 0.495828 0.143 Uiso 0.394(15) 1 calc R U P C 5
C8A C 0.910(3) 0.867(3) 0.686(4) 0.096(4) Uani 0.394(15) 1 d . . P C 5
H8AA H 0.959567 0.903922 0.628534 0.143 Uiso 0.394(15) 1 calc R U P C 5
H8AB H 0.937794 0.877986 0.764001 0.143 Uiso 0.394(15) 1 calc R U P C 5
H8AC H 0.862693 0.886565 0.683739 0.143 Uiso 0.394(15) 1 calc R U P C 5
C9A C 0.623(2) 0.759(2) 0.476(2) 0.096(4) Uani 0.573(14) 1 d D . P D 6
H9AA H 0.605116 0.753247 0.558801 0.143 Uiso 0.573(14) 1 calc R U P D 6
H9AB H 0.690064 0.806823 0.468589 0.143 Uiso 0.573(14) 1 calc R U P D 6
H9AC H 0.613345 0.698796 0.447559 0.143 Uiso 0.573(14) 1 calc R U P D 6
C10A C 0.527(2) 0.736(2) 0.299(2) 0.096(4) Uani 0.573(14) 1 d D . P D 6
H10D H 0.469674 0.676397 0.316004 0.143 Uiso 0.573(14) 1 calc R U P D 6
H10E H 0.573300 0.722384 0.262379 0.143 Uiso 0.573(14) 1 calc R U P D 6
H10F H 0.512564 0.773069 0.245022 0.143 Uiso 0.573(14) 1 calc R U P D 6
C11A C 0.6421(18) 0.8844(17) 0.372(2) 0.096(4) Uani 0.573(14) 1 d D . P D 6
H11D H 0.614213 0.923374 0.352686 0.143 Uiso 0.573(14) 1 calc R U P D 6
H11E H 0.674984 0.879470 0.303075 0.143 Uiso 0.573(14) 1 calc R U P D 6
H11F H 0.686756 0.913273 0.436230 0.143 Uiso 0.573(14) 1 calc R U P D 6
C12A C 0.4960(18) 0.789(2) 0.485(2) 0.096(4) Uani 0.573(14) 1 d D . P D 6
H12D H 0.443097 0.725002 0.493773 0.143 Uiso 0.573(14) 1 calc R U P D 6
H12E H 0.473614 0.829228 0.451450 0.143 Uiso 0.573(14) 1 calc R U P D 6
H12F H 0.524420 0.813644 0.561432 0.143 Uiso 0.573(14) 1 calc R U P D 6


_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 Cl1 2.508(3) . ?
I1 Cl2 2.447(3) . ?
I1 Cl3 2.477(3) . ?
I1 Cl4 2.499(3) . ?
I2 Cl5 2.518(3) . ?
I2 Cl6 2.444(3) . ?
I2 Cl7 2.475(3) . ?
I2 Cl8 2.505(3) . ?
I3 Cl9 2.485(3) . ?
I3 Cl10 2.469(3) . ?
I3 Cl11 2.474(3) . ?
I3 Cl12 2.486(3) . ?
N1 C1 1.45(3) . ?
N1 C2 1.506(15) . ?
N1 C3 1.48(3) . ?
N1 C4 1.37(3) . ?
N1 C1A 1.55(3) . ?
N1 C3A 1.50(3) . ?
N1 C4A 1.53(3) . ?
N3 C9 1.48(2) . ?
N3 C10 1.47(2) . ?
N3 C11 1.53(2) . ?
N3 C12 1.47(2) . ?
N3 C9A 1.48(2) . ?
N3 C10A 1.47(2) . ?
N3 C11A 1.50(2) . ?
N3 C12A 1.46(2) . ?
N2 C5 1.470(14) . ?
N2 C6 1.48(2) . ?
N2 C7 1.46(2) . ?
N2 C8 1.45(2) . ?
N2 C6A 1.57(4) . ?
N2 C7A 1.49(4) . ?
N2 C8A 1.49(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

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
Cl2 I1 Cl1 178.03(11) . . ?
Cl2 I1 Cl3 86.70(10) . . ?
Cl2 I1 Cl4 89.35(10) . . ?
Cl3 I1 Cl1 91.33(10) . . ?
Cl3 I1 Cl4 176.04(11) . . ?
Cl4 I1 Cl1 92.62(11) . . ?
Cl6 I2 Cl5 178.48(12) . . ?
Cl6 I2 Cl7 88.89(11) . . ?
Cl6 I2 Cl8 88.98(10) . . ?
Cl7 I2 Cl5 90.11(11) . . ?
Cl7 I2 Cl8 177.77(11) . . ?
Cl8 I2 Cl5 92.03(10) . . ?
Cl9 I3 Cl12 91.69(11) . . ?
Cl10 I3 Cl9 90.18(14) . . ?
Cl10 I3 Cl11 88.42(14) . . ?
Cl10 I3 Cl12 178.10(15) . . ?
Cl11 I3 Cl9 178.50(13) . . ?
Cl11 I3 Cl12 89.73(13) . . ?
C1 N1 C2 98.7(15) . . ?
C1 N1 C3 110.8(19) . . ?
C3 N1 C2 102.5(15) . . ?
C4 N1 C1 121(2) . . ?
C4 N1 C2 109.5(16) . . ?
C4 N1 C3 111.8(19) . . ?
C3A N1 C1A 104.5(18) . . ?
C3A N1 C4A 103.9(16) . . ?
C4A N1 C1A 106.6(18) . . ?
C9 N3 C11 118(2) . . ?
C10 N3 C9 106(2) . . ?
C10 N3 C11 97(2) . . ?
C12 N3 C9 122(2) . . ?
C12 N3 C10 105(2) . . ?
C12 N3 C11 106(2) . . ?
C9A N3 C11A 98.8(18) . . ?
C10A N3 C9A 115.1(17) . . ?
C10A N3 C11A 106.2(15) . . ?
C12A N3 C9A 108.1(17) . . ?
C12A N3 C10A 114.1(17) . . ?
C12A N3 C11A 113.6(17) . . ?
C5 N2 C6 107.5(12) . . ?
C7 N2 C5 114.1(13) . . ?
C7 N2 C6 108.9(14) . . ?
C8 N2 C5 106.1(12) . . ?
C8 N2 C6 108.4(15) . . ?
C8 N2 C7 111.6(16) . . ?
C7A N2 C6A 112(2) . . ?
C8A N2 C6A 106(2) . . ?
C8A N2 C7A 107(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
N2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C1A H1AA 109.5 . . ?
N1 C1A H1AB 109.5 . . ?
N1 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
N1 C3A H3AA 109.5 . . ?
N1 C3A H3AB 109.5 . . ?
N1 C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
N1 C4A H4AA 109.5 . . ?
N1 C4A H4AB 109.5 . . ?
N1 C4A H4AC 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
N2 C6A H6AA 109.5 . . ?
N2 C6A H6AB 109.5 . . ?
N2 C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
N2 C7A H7AA 109.5 . . ?
N2 C7A H7AB 109.5 . . ?
N2 C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
N2 C8A H8AA 109.5 . . ?
N2 C8A H8AB 109.5 . . ?
N2 C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
N3 C9A H9AA 109.5 . . ?
N3 C9A H9AB 109.5 . . ?
N3 C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
N3 C10A H10D 109.5 . . ?
N3 C10A H10E 109.5 . . ?
N3 C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
N3 C11A H11D 109.5 . . ?
N3 C11A H11E 109.5 . . ?
N3 C11A H11F 109.5 . . ?
H11D C11A H11E 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
N3 C12A H12D 109.5 . . ?
N3 C12A H12E 109.5 . . ?
N3 C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9239(7)
2 0.0761(7)

####################################################################### 
# 
# 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_nk697_a
_database_code_depnum_ccdc_archive 'CCDC 2257400'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C9 H14 N'
_chemical_formula_sum            'C9 H14 Cl4 I N'
_chemical_formula_weight         404.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         IClCHN
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 0.0000 0.0000 '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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   8.4156(4)
_cell_length_b                   16.0769(6)
_cell_length_c                   10.9381(4)
_cell_angle_alpha                90.0
_cell_angle_beta                 103.705(4)
_cell_angle_gamma                90.0
_cell_volume                     1437.75(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3633
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      28.6640
_cell_measurement_theta_min      2.7620
_cell_oxdiff_angle_alpha         90.034(2)
_cell_oxdiff_angle_beta          103.738(2)
_cell_oxdiff_angle_gamma         89.963(2)
_cell_oxdiff_length_a            8.4129(2)
_cell_oxdiff_length_b            16.0754(4)
_cell_oxdiff_length_c            10.9442(3)
_cell_oxdiff_measurement_reflns_used 3633
_cell_oxdiff_volume              1437.75(7)
_shelx_estimated_absorpt_T_max   0.667
_shelx_estimated_absorpt_T_min   0.527
_exptl_absorpt_coefficient_mu    2.942
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.784
_diffrn_reflns_theta_min         2.297
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  31.00   0.50    4.44    --  -10.63 -19.00  30.00  192
  2  ω    -33.00  49.00   0.50    4.44    --  -10.63  57.00-120.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0672349000
_diffrn_orient_matrix_UB_12      -0.0270119000
_diffrn_orient_matrix_UB_13      0.0018721000
_diffrn_orient_matrix_UB_21      0.0506404000
_diffrn_orient_matrix_UB_22      0.0261835000
_diffrn_orient_matrix_UB_23      0.0451827000
_diffrn_orient_matrix_UB_31      -0.0211734000
_diffrn_orient_matrix_UB_32      -0.0230577000
_diffrn_orient_matrix_UB_33      0.0490560000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2744
_reflns_number_total             3177
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.00111(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0115P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0430
_refine_ls_wR_factor_ref         0.0468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.16814(2) 0.44999(2) 0.67470(2) 0.02065(8) Uani 1 1 d . . . . .
Cl1 Cl 0.28782(12) 0.59201(4) 0.70081(9) 0.0446(2) Uani 1 1 d . . . . .
N1 N 0.4352(3) 0.76150(13) 0.3918(2) 0.0188(5) Uani 1 1 d . . . . .
C1 C 0.4318(3) 0.69647(16) 0.2930(2) 0.0184(6) Uani 1 1 d . . . . .
Cl2 Cl 0.24730(11) 0.43169(5) 0.46877(7) 0.0372(2) Uani 1 1 d . . . . .
C2 C 0.3687(3) 0.61815(16) 0.3041(3) 0.0268(7) Uani 1 1 d . . . . .
H2 H 0.330268 0.603828 0.376302 0.032 Uiso 1 1 calc R U . . .
Cl3 Cl 0.05252(10) 0.30542(5) 0.66204(8) 0.0364(2) Uani 1 1 d . . . . .
C3 C 0.3624(4) 0.56123(19) 0.2089(3) 0.0369(8) Uani 1 1 d . . . . .
H3 H 0.319643 0.507235 0.216055 0.044 Uiso 1 1 calc R U . . .
C4 C 0.4169(4) 0.5813(2) 0.1042(3) 0.0370(8) Uani 1 1 d . . . . .
H4 H 0.410053 0.541872 0.038466 0.044 Uiso 1 1 calc R U . . .
Cl4 Cl 0.08694(10) 0.46916(4) 0.87734(7) 0.02864(18) Uani 1 1 d . . . . .
C5 C 0.4816(4) 0.65910(19) 0.0949(3) 0.0311(8) Uani 1 1 d . . . . .
H5 H 0.521896 0.672719 0.023214 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4887(3) 0.71779(17) 0.1891(3) 0.0237(7) Uani 1 1 d . . . . .
H6 H 0.531931 0.771682 0.182056 0.028 Uiso 1 1 calc R U . . .
C8 C 0.3840(4) 0.72842(18) 0.5050(3) 0.0291(7) Uani 1 1 d . . . . .
H8A H 0.270608 0.708889 0.479968 0.044 Uiso 1 1 calc R U . . .
H8B H 0.392496 0.772687 0.567855 0.044 Uiso 1 1 calc R U . . .
H8C H 0.455478 0.682081 0.541198 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6057(3) 0.79593(17) 0.4388(3) 0.0267(7) Uani 1 1 d . . . . .
H7A H 0.681145 0.750507 0.472277 0.040 Uiso 1 1 calc R U . . .
H7B H 0.605994 0.836703 0.505479 0.040 Uiso 1 1 calc R U . . .
H7C H 0.640569 0.822933 0.369203 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3199(4) 0.83094(17) 0.3374(3) 0.0281(7) Uani 1 1 d . . . . .
H9A H 0.355074 0.856308 0.266696 0.042 Uiso 1 1 calc R U . . .
H9B H 0.320431 0.873044 0.402263 0.042 Uiso 1 1 calc R U . . .
H9C H 0.209023 0.808634 0.307732 0.042 Uiso 1 1 calc R U . . .


_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 Cl1 2.4844(8) . ?
I1 Cl2 2.5130(7) . ?
I1 Cl3 2.5109(8) . ?
I1 Cl4 2.4886(7) . ?
N1 C1 1.500(3) . ?
N1 C8 1.502(3) . ?
N1 C7 1.510(3) . ?
N1 C9 1.506(3) . ?
C1 C2 1.383(4) . ?
C1 C6 1.376(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.378(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
Cl1 I1 Cl2 91.39(3) . . ?
Cl1 I1 Cl3 176.64(3) . . ?
Cl1 I1 Cl4 88.46(2) . . ?
Cl3 I1 Cl2 91.36(3) . . ?
Cl4 I1 Cl2 179.32(3) . . ?
Cl4 I1 Cl3 88.80(2) . . ?
C1 N1 C8 112.8(2) . . ?
C1 N1 C7 110.8(2) . . ?
C1 N1 C9 109.3(2) . . ?
C8 N1 C7 106.5(2) . . ?
C8 N1 C9 107.7(2) . . ?
C9 N1 C7 109.5(2) . . ?
C2 C1 N1 120.9(2) . . ?
C6 C1 N1 118.1(2) . . ?
C6 C1 C2 121.0(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(3) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 118.8(3) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 177.6(3) . . . . ?
N1 C1 C6 C5 -178.0(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C1 C6 C5 0.0(4) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -1.5(5) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C8 N1 C1 C2 7.0(4) . . . . ?
C8 N1 C1 C6 -175.0(2) . . . . ?
C7 N1 C1 C2 126.3(3) . . . . ?
C7 N1 C1 C6 -55.6(3) . . . . ?
C9 N1 C1 C2 -112.8(3) . . . . ?
C9 N1 C1 C6 65.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.059
_oxdiff_exptl_absorpt_empirical_full_min 0.948
####################################################################### 
# 
# 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_nk772_b
_database_code_depnum_ccdc_archive 'CCDC 2257398'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(Cl4 I), C12 H14 N2'
_chemical_formula_sum            'C12 H14 Cl8 I2 N2'
_chemical_formula_weight         723.65
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           106
_space_group_name_H-M_alt        'P 42 b c'
_space_group_name_Hall           'P 4c -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z+1/2'
'y, -x, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   11.5876(8)
_cell_length_b                   11.5876(8)
_cell_length_c                   16.4371(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2207.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    3.819
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0783 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.8251.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.178
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.543
_diffrn_reflns_theta_min         2.478
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                3154
_reflns_number_total             3676
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.099
_refine_ls_abs_structure_details 
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.048(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         3676
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0300
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0127P)²+1.4993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0570
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.36068(2) 0.90049(3) 0.41507(3) 0.02460(8) Uani 1 1 d . . . . .
Cl1 Cl 0.34936(15) 0.92280(14) 0.56614(9) 0.0373(4) Uani 1 1 d . . . . .
Cl2 Cl 0.37793(14) 0.87493(17) 0.26545(10) 0.0385(4) Uani 1 1 d . . . . .
Cl3 Cl 0.52907(12) 0.76703(12) 0.43610(8) 0.0340(3) Uani 1 1 d . . . . .
Cl4 Cl 0.19607(12) 1.03649(14) 0.39287(8) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.2436(5) 0.6575(4) 0.6632(3) 0.0269(12) Uani 1 1 d . . . . .
C1 C 0.1326(6) 0.7213(7) 0.6604(5) 0.0341(15) Uani 1 1 d . . . . .
H1A H 0.140802 0.788942 0.625127 0.051 Uiso 1 1 calc R U . . .
H1B H 0.111692 0.746314 0.715432 0.051 Uiso 1 1 calc R U . . .
H1C H 0.072139 0.670710 0.638875 0.051 Uiso 1 1 calc R U . . .
C2 C 0.2790(5) 0.6094(5) 0.7334(3) 0.0268(12) Uani 1 1 d . . . . .
H2 H 0.234020 0.618470 0.781243 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3797(5) 0.5474(5) 0.7362(3) 0.0267(12) Uani 1 1 d . . . . .
H3 H 0.404112 0.513494 0.785897 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4462(4) 0.5339(4) 0.6663(3) 0.0225(10) Uani 1 1 d . . . . .
C5 C 0.4071(4) 0.5859(4) 0.5952(3) 0.0255(10) Uani 1 1 d . . . . .
H5 H 0.450970 0.579422 0.546551 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3054(5) 0.6467(4) 0.5950(3) 0.0269(11) Uani 1 1 d . . . . .
H6 H 0.278722 0.681183 0.546082 0.032 Uiso 1 1 calc R U . . .


_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 Cl1 2.5000(17) . ?
I1 Cl2 2.4852(18) . ?
I1 Cl3 2.5138(14) . ?
I1 Cl4 2.5010(15) . ?
N1 C1 1.484(7) . ?
N1 C2 1.344(7) . ?
N1 C6 1.336(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.371(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(7) . ?
C4 C4 1.474(10) 2_665 ?
C4 C5 1.392(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(8) . ?
C6 H6 0.9500 . ?

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
Cl1 I1 Cl3 88.15(5) . . ?
Cl1 I1 Cl4 92.28(5) . . ?
Cl2 I1 Cl1 178.14(7) . . ?
Cl2 I1 Cl3 90.02(5) . . ?
Cl2 I1 Cl4 89.55(5) . . ?
Cl4 I1 Cl3 178.75(5) . . ?
C2 N1 C1 119.8(5) . . ?
C6 N1 C1 119.0(5) . . ?
C6 N1 C2 121.1(6) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2 119.8 . . ?
N1 C2 C3 120.4(5) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(5) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C4 121.9(3) . 2_665 ?
C3 C4 C5 117.7(5) . . ?
C5 C4 C4 120.4(3) . 2_665 ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
N1 C6 C5 120.4(5) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?

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 0.1(8) . . . . ?
C1 N1 C2 C3 178.1(5) . . . . ?
C1 N1 C6 C5 -178.5(5) . . . . ?
C2 N1 C6 C5 -0.1(8) . . . . ?
C2 C3 C4 C4 -178.8(6) . . . 2_665 ?
C2 C3 C4 C5 0.5(8) . . . . ?
C3 C4 C5 C6 -0.9(7) . . . . ?
C4 C4 C5 C6 178.4(6) 2_665 . . . ?
C4 C5 C6 N1 0.7(8) . . . . ?
C6 N1 C2 C3 -0.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nk705_a
_database_code_depnum_ccdc_archive 'CCDC 2257397'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C8 H12 N'
_chemical_formula_sum            'C8 H12 Cl4 I N'
_chemical_formula_weight         390.89
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3598(15)
_cell_length_b                   8.5116(11)
_cell_length_c                   15.140(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.486(4)
_cell_angle_gamma                90
_cell_volume                     1371.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4152
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.837
_shelx_estimated_absorpt_T_min   0.709
_exptl_absorpt_coefficient_mu    3.081
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0910 before and 0.0663 after correction.
The Ratio of minimum to maximum transmission is 0.7703.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13909
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         1.914
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2334
_reflns_number_total             2811
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.390
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2811
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+1.6046P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.69387(19) 1.30945(17) 0.66741(12) 0.0756(6) Uani 1 1 d . . . . .
Cl2 Cl 0.48730(14) 0.99678(17) 0.66516(10) 0.0489(3) Uani 1 1 d . . . . .
I1 I 0.66906(3) 1.03180(3) 0.61145(2) 0.03402(15) Uani 1 1 d . . . . .
Cl3 Cl 0.64835(11) 0.75159(13) 0.56231(9) 0.0391(3) Uani 1 1 d . . . . .
Cl4 Cl 0.85140(13) 1.06528(18) 0.55677(13) 0.0589(4) Uani 1 1 d . . . . .
N1 N 0.2882(4) 0.5088(5) 0.6117(3) 0.0336(9) Uani 1 1 d . . . . .
C1 C 0.1921(5) 0.6049(6) 0.6075(3) 0.0392(12) Uani 1 1 d . . . . .
H1 H 0.196152 0.712551 0.592163 0.047 Uiso 1 1 calc R U . . .
C2 C 0.0881(5) 0.5504(6) 0.6249(4) 0.0402(12) Uani 1 1 d . . . . .
C3 C 0.0869(4) 0.3911(6) 0.6474(3) 0.0341(10) Uani 1 1 d . . . . .
H3 H 0.015941 0.349225 0.658649 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1864(4) 0.2933(6) 0.6536(3) 0.0325(10) Uani 1 1 d . . . . .
C5 C 0.2881(4) 0.3573(6) 0.6343(3) 0.0332(10) Uani 1 1 d . . . . .
H5 H 0.357539 0.292555 0.637359 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3982(5) 0.5749(7) 0.5925(4) 0.0452(13) Uani 1 1 d . . . . .
H6A H 0.467571 0.499158 0.612041 0.068 Uiso 1 1 calc R U . . .
H6B H 0.424823 0.672836 0.627956 0.068 Uiso 1 1 calc R U . . .
H6C H 0.374754 0.596245 0.524913 0.068 Uiso 1 1 calc R U . . .
C7 C -0.0170(6) 0.6586(8) 0.6214(5) 0.0581(16) Uani 1 1 d . . . . .
H7A H -0.000032 0.706016 0.683610 0.087 Uiso 1 1 calc R U . . .
H7B H -0.095871 0.599249 0.603373 0.087 Uiso 1 1 calc R U . . .
H7C H -0.024165 0.741453 0.574858 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1900(5) 0.1241(6) 0.6804(4) 0.0432(12) Uani 1 1 d . . . . .
H8A H 0.232876 0.113320 0.748655 0.065 Uiso 1 1 calc R U . . .
H8B H 0.235395 0.064025 0.647324 0.065 Uiso 1 1 calc R U . . .
H8C H 0.103957 0.083939 0.662939 0.065 Uiso 1 1 calc R U . . .


_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
Cl1 I1 2.4930(15) . ?
Cl2 I1 2.4877(15) . ?
I1 Cl3 2.4849(12) . ?
I1 Cl4 2.5015(16) . ?
N1 C1 1.348(6) . ?
N1 C5 1.335(6) . ?
N1 C6 1.489(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(8) . ?
C2 C3 1.399(8) . ?
C2 C7 1.494(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(7) . ?
C4 C5 1.398(7) . ?
C4 C8 1.493(7) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Cl1 I1 Cl4 89.79(7) . . ?
Cl2 I1 Cl1 90.60(6) . . ?
Cl2 I1 Cl4 179.60(5) . . ?
Cl3 I1 Cl1 177.71(5) . . ?
Cl3 I1 Cl2 88.88(5) . . ?
Cl3 I1 Cl4 90.74(5) . . ?
C1 N1 C6 118.9(4) . . ?
C5 N1 C1 121.7(4) . . ?
C5 N1 C6 119.4(4) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.4(5) . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 117.0(5) . . ?
C1 C2 C7 120.9(5) . . ?
C3 C2 C7 122.1(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(5) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 C8 123.0(4) . . ?
C5 C4 C8 119.1(4) . . ?
N1 C5 C4 120.4(4) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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 0.2(7) . . . . ?
N1 C1 C2 C7 179.1(5) . . . . ?
C1 N1 C5 C4 0.6(7) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C2 C3 C4 C8 178.0(5) . . . . ?
C3 C4 C5 N1 0.7(7) . . . . ?
C5 N1 C1 C2 -1.1(7) . . . . ?
C6 N1 C1 C2 -179.8(5) . . . . ?
C6 N1 C5 C4 179.3(5) . . . . ?
C7 C2 C3 C4 -177.8(5) . . . . ?
C8 C4 C5 N1 -178.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_nk774_b
_database_code_depnum_ccdc_archive 'CCDC 2257395'
loop_
_audit_author_name
_audit_author_address
'Nikita Korobeynikov'
;Nikolaev Institute of Inorganic Chemistry of SB RAS (NIIC SB RAS)
Russia
;
_audit_update_record             
;
2023-04-19 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 I, C6 H7 Cl N'
_chemical_formula_sum            'C6 H7 Cl5 I N'
_chemical_formula_weight         397.28
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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 0.0000 0.0000 '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'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.2044(2)
_cell_length_b                   9.6553(3)
_cell_length_c                   8.2874(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.8870(10)
_cell_angle_gamma                90
_cell_volume                     631.42(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9321
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    3.552
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0596 before and 0.0502 after correction.
The Ratio of minimum to maximum transmission is 0.9148.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.052
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            28732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.521
_diffrn_reflns_theta_min         2.555
_diffrn_ambient_temperature      150.00
_diffrn_detector                 PIXEL
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Incoatec HELIOS multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IuS3.0 microfocus X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3782
_reflns_number_total             3847
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.328(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3847
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0150
_refine_ls_R_factor_gt           0.0145
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+0.1620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0336
_refine_ls_wR_factor_ref         0.0338
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.672(16)
 0.328(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.44672(2) 0.75317(3) 0.26629(2) 0.02061(4) Uani 1 1 d . . . . .
Cl1 Cl 0.76890(11) 0.40084(10) 0.38508(10) 0.03977(19) Uani 1 1 d . . . . .
N1 N 1.1337(3) 0.2637(4) 0.2049(3) 0.0274(5) Uani 1 1 d . . . . .
C1 C 1.0303(4) 0.3490(3) 0.2594(4) 0.0276(6) Uani 1 1 d . . . . .
H1 H 1.047411 0.446431 0.262193 0.033 Uiso 1 1 calc R U . . .
Cl2 Cl 0.75714(9) 0.77858(9) 0.34120(10) 0.0358(2) Uani 1 1 d . . . . .
C2 C 0.8989(4) 0.2918(3) 0.3111(4) 0.0256(6) Uani 1 1 d . . . . .
C3 C 0.8725(4) 0.1524(4) 0.3063(4) 0.0307(7) Uani 1 1 d . . . . .
H3 H 0.780922 0.114164 0.341103 0.037 Uiso 1 1 calc R U . . .
Cl3 Cl 0.12871(9) 0.72073(7) 0.18803(10) 0.03385(19) Uani 1 1 d . . . . .
Cl4 Cl 0.47634(10) 0.58014(8) 0.49693(11) 0.03418(17) Uani 1 1 d . . . . .
C4 C 0.9814(4) 0.0674(3) 0.2499(4) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.965420 -0.030150 0.245221 0.040 Uiso 1 1 calc R U . . .
C5 C 1.1131(4) 0.1259(4) 0.2007(4) 0.0313(7) Uani 1 1 d . . . . .
H5 H 1.189660 0.068506 0.163516 0.038 Uiso 1 1 calc R U . . .
Cl5 Cl 0.42147(11) 0.93259(9) 0.04357(10) 0.03794(18) Uani 1 1 d . . . . .
C6 C 1.2783(5) 0.3252(4) 0.1456(4) 0.0391(8) Uani 1 1 d . . . . .
H6A H 1.386053 0.308299 0.230298 0.059 Uiso 1 1 calc R U . . .
H6B H 1.260914 0.425180 0.128943 0.059 Uiso 1 1 calc R U . . .
H6C H 1.281058 0.281745 0.039556 0.059 Uiso 1 1 calc R U . . .


_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 Cl2 2.4629(7) . ?
I1 Cl3 2.5298(7) . ?
I1 Cl4 2.4999(8) . ?
I1 Cl5 2.4983(8) . ?
Cl1 C2 1.726(3) . ?
N1 C1 1.346(4) . ?
N1 C5 1.340(5) . ?
N1 C6 1.524(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(5) . ?
C2 C3 1.362(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(5) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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
Cl2 I1 Cl3 178.57(3) . . ?
Cl2 I1 Cl4 89.80(3) . . ?
Cl2 I1 Cl5 89.32(3) . . ?
Cl4 I1 Cl3 89.48(3) . . ?
Cl5 I1 Cl3 91.45(3) . . ?
Cl5 I1 Cl4 177.93(3) . . ?
C1 N1 C6 119.2(3) . . ?
C5 N1 C1 122.0(3) . . ?
C5 N1 C6 118.8(3) . . ?
N1 C1 H1 120.8 . . ?
N1 C1 C2 118.4(3) . . ?
C2 C1 H1 120.8 . . ?
C1 C2 Cl1 118.5(2) . . ?
C3 C2 Cl1 120.3(3) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.9(3) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 120.2(3) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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
Cl1 C2 C3 C4 -178.5(3) . . . . ?
N1 C1 C2 Cl1 178.7(2) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 N1 C5 C4 1.2(5) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C5 N1 C1 C2 -0.4(4) . . . . ?
C6 N1 C1 C2 179.4(3) . . . . ?
C6 N1 C5 C4 -178.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.672(16)
2 0.328(16)

