# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1_PF6
_database_code_depnum_ccdc_archive 'CCDC 2079430'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2021-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 I1 N2, F6 P1'
_chemical_formula_sum            'C14 H26 F6 I N2 P'
_chemical_formula_weight         494.23
_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'
F F 0.0171 0.0103 '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'
P P 0.1023 0.0942 '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      cubic
_space_group_IT_number           205
_space_group_name_H-M_alt        'P a -3'
_space_group_name_Hall           '-P 2ac 2ab 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
'-z, -x, -y'
'-z-1/2, x-1/2, y'
'z-1/2, x, -y-1/2'
'z, -x-1/2, y-1/2'
'-y, -z, -x'
'y, -z-1/2, x-1/2'
'-y-1/2, z-1/2, x'
'y-1/2, z, -x-1/2'

_cell_length_a                   12.3792(3)
_cell_length_b                   12.3792(3)
_cell_length_c                   12.3792(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1897.05(14)
_cell_formula_units_Z            4.00008
_cell_measurement_reflns_used    867
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.559
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0822 before and 0.0740 after correction. The Ratio of minimum to maximum transmission is 0.7995. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13625
_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         27.052
_diffrn_reflns_theta_min         2.850
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                552
_reflns_number_total             705
_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_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.808
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     50
_refine_ls_number_reflns         705
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.164
_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)+(0.0278P)²+1.4547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Fixed Sof: F103(0.33333) F104(0.33333)
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.5000 0.5000 0.5000 0.03072(16) Uani 1 6 d S T P . .
P101 P 0.5000 0.5000 0.0000 0.0347(4) Uani 1 6 d S T P . .
F102 F 0.42579(14) 0.57421(14) 0.07421(14) 0.0602(8) Uani 1 3 d S T P A .
F103 F 0.589(3) 0.506(4) 0.091(3) 0.065(5) Uani 0.3333 1 d . . . A -1
F104 F 0.547(4) 0.462(5) 0.1135(8) 0.061(4) Uani 0.3333 1 d . . . A -2
N1 N 0.39268(15) 0.39268(15) 0.39268(15) 0.0291(7) Uani 1 3 d S T P . .
C2 C 0.3391(2) 0.4604(2) 0.3088(2) 0.0407(6) Uani 1 1 d . . . . .
H2A H 0.3947 0.4948 0.2627 0.049 Uiso 1 1 calc R . . . .
H2B H 0.2969 0.5184 0.3442 0.049 Uiso 1 1 calc R . . . .
C3 C 0.2637(2) 0.3912(2) 0.2386(2) 0.0424(7) Uani 1 1 d . . . . .
H3A H 0.1882 0.4159 0.2473 0.051 Uiso 1 1 calc R . . . .
H3B H 0.2839 0.3985 0.1616 0.051 Uiso 1 1 calc R . . . .
C8 C 0.2735(2) 0.2735(2) 0.2735(2) 0.0421(11) Uani 1 3 d S T P . .
H8 H 0.2268 0.2268 0.2268 0.050 Uiso 1 3 calc RS T 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
I1 N1 2.301(3) . ?
I1 N1 2.301(3) 13_666 ?
P101 F102 1.591(3) 13_665 ?
P101 F102 1.591(3) . ?
P101 F103 1.580(9) . ?
P101 F104 1.593(8) . ?
N1 C2 1.490(3) 9 ?
N1 C2 1.490(3) 5 ?
N1 C2 1.490(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.537(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C8 1.524(3) . ?
C8 C3 1.524(3) 9 ?
C8 C3 1.524(3) 5 ?
C8 H8 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 I1 N1 180.00(7) . 13_666 ?
F102 P101 F102 180.0 . 13_665 ?
F102 P101 F104 82.7(5) . . ?
F102 P101 F104 97.3(5) 13_665 . ?
F103 P101 F102 92.0(8) . 13_665 ?
F103 P101 F102 88.0(8) . . ?
C2 N1 I1 109.51(16) 9 . ?
C2 N1 I1 109.51(16) 5 . ?
C2 N1 I1 109.51(16) . . ?
C2 N1 C2 109.43(16) 9 5 ?
C2 N1 C2 109.43(16) 5 . ?
C2 N1 C2 109.43(16) 9 . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
N1 C2 C3 110.5(2) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C8 C3 C2 109.0(3) . . ?
C8 C3 H3A 109.9 . . ?
C8 C3 H3B 109.9 . . ?
C3 C8 C3 108.9(2) 9 5 ?
C3 C8 C3 108.9(2) 5 . ?
C3 C8 C3 108.9(2) 9 . ?
C3 C8 H8 110.1 9 . ?
C3 C8 H8 110.1 5 . ?
C3 C8 H8 110.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN/DIPE'
####################################################################### 
# 
# 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_1_NO3
_database_code_depnum_ccdc_archive 'CCDC 2079431'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2021-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT111_1_NO3               
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Numerous other potential 
symmetries were extensively tested 
for this dataset, including those 
suggested by ADDSYM. However, the 
space group selected (Pca2~1~) 
was the only one ultimately able 
to be solved and refined to a 
chemically sensible structure.
;
_vrf_PLAT113_1_NO3               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pbcn Check 
RESPONSE: Numerous other potential 
symmetries were extensively tested 
for this dataset, including those 
suggested by ADDSYM. However, the 
space group selected (Pca2~1~) 
was the only one ultimately able 
to be solved and refined to a 
chemically sensible structure.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 I N2, N O3'
_chemical_formula_sum            'C14 H26 I N3 O3'
_chemical_formula_weight         411.28
_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 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.8822(3)
_cell_length_b                   10.4099(3)
_cell_length_c                   11.3834(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1645.04(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.2410
_cell_measurement_theta_min      3.8420
_shelx_estimated_absorpt_T_max   0.458
_shelx_estimated_absorpt_T_min   0.140
_exptl_absorpt_coefficient_mu    15.418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33186
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5515
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.128
_diffrn_reflns_theta_min         4.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  20.00   1.00    1.00    --  -41.90  19.00 120.00   92
  2  ω     29.00  75.00   1.00    1.00    --   41.90-125.00-120.00   46
  3  ω     68.00 107.00   1.00    1.00    --  112.00 -94.00 150.00   39
  4  ω     42.00 140.00   1.00    1.00    --  112.00 -61.00-120.00   98
  5  ω     42.00 138.00   1.00    1.00    --  112.00 -45.00 -30.00   96
  6  ω    131.00 175.00   1.00    1.00    --  112.00 111.00 -60.00   44
  7  ω     27.00  92.00   1.00    1.00    --   42.15-125.00  60.00   65
  8  ω     63.00 109.00   1.00    1.00    --  112.00-111.00  90.00   46
  9  ω    113.00 177.00   1.00    1.00    --  112.00  61.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0233711000
_diffrn_orient_matrix_UB_12      -0.0191861000
_diffrn_orient_matrix_UB_13      0.1310941000
_diffrn_orient_matrix_UB_21      0.0686174000
_diffrn_orient_matrix_UB_22      0.1162095000
_diffrn_orient_matrix_UB_23      -0.0041380000
_diffrn_orient_matrix_UB_31      -0.0839706000
_diffrn_orient_matrix_UB_32      0.0897569000
_diffrn_orient_matrix_UB_33      0.0332189000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.895
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2180
_reflns_number_total             2510
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.033
_refine_diff_density_min         -1.366
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(2)
_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     191
_refine_ls_number_reflns         2510
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.045
_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)+(0.0722P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.85(2)
 0.15(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b), C6(H6a,H6b), C7(H7a,H7b),
 C12(H12a,H12b), C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,H16b),
  C17(H17a,H17b)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.26022(3) 0.25084(3) 0.5064(4) 0.01390(18) Uani 1 1 d . . . . .
O102 O 0.6368(5) 0.1265(6) 0.2540(5) 0.0404(16) Uani 1 1 d . . . . .
O103 O 0.6629(4) 0.3288(6) 0.2817(6) 0.0417(15) Uani 1 1 d . . . . .
O104 O 0.5220(5) 0.2624(5) 0.2286(8) 0.0397(18) Uani 1 1 d . . . . .
N1 N 0.3460(3) 0.4297(4) 0.4495(5) 0.0147(10) Uani 1 1 d . . . . .
N11 N 0.1736(3) 0.0732(4) 0.5627(5) 0.0144(11) Uani 1 1 d . . . . .
N101 N 0.6078(5) 0.2390(5) 0.2552(6) 0.0191(15) Uani 1 1 d . . . . .
C2 C 0.3089(4) 0.5489(5) 0.5071(7) 0.0217(12) Uani 1 1 d . . . . .
H2A H 0.3208 0.5449 0.5909 0.026 Uiso 1 1 calc R . . . .
H2B H 0.2399 0.5556 0.4949 0.026 Uiso 1 1 calc R . . . .
C3 C 0.3597(5) 0.6678(6) 0.4545(7) 0.0218(13) Uani 1 1 d . . . . .
H3A H 0.3149 0.7156 0.4059 0.026 Uiso 1 1 calc R . . . .
H3B H 0.3816 0.7237 0.5172 0.026 Uiso 1 1 calc R . . . .
C4 C 0.4503(4) 0.4109(6) 0.4814(6) 0.0218(15) Uani 1 1 d . . . . .
H4A H 0.4768 0.3398 0.4369 0.026 Uiso 1 1 calc R . . . .
H4B H 0.4556 0.3905 0.5643 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5079(5) 0.5350(6) 0.4544(8) 0.0250(14) Uani 1 1 d . . . . .
H5A H 0.5262 0.5770 0.5271 0.030 Uiso 1 1 calc R . . . .
H5B H 0.5661 0.5139 0.4113 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3378(5) 0.4437(6) 0.3201(6) 0.0203(13) Uani 1 1 d . . . . .
H6A H 0.2720 0.4657 0.2996 0.024 Uiso 1 1 calc R . . . .
H6B H 0.3535 0.3627 0.2825 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4063(6) 0.5489(6) 0.2753(7) 0.0222(14) Uani 1 1 d . . . . .
H7A H 0.4594 0.5104 0.2326 0.027 Uiso 1 1 calc R . . . .
H7B H 0.3722 0.6062 0.2226 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4448(5) 0.6245(6) 0.3813(6) 0.0195(13) Uani 1 1 d . . . . .
H8 H 0.4821 0.6989 0.3547 0.023 Uiso 1 1 calc R . . . .
C12 C 0.1659(5) 0.0686(5) 0.6935(6) 0.0208(13) Uani 1 1 d . . . . .
H12A H 0.1414 0.1501 0.7222 0.025 Uiso 1 1 calc R . . . .
H12B H 0.2293 0.0554 0.7271 0.025 Uiso 1 1 calc R . . . .
C13 C 0.0991(6) -0.0390(6) 0.7330(7) 0.0222(14) Uani 1 1 d . . . . .
H13A H 0.0413 -0.0033 0.7680 0.027 Uiso 1 1 calc R . . . .
H13B H 0.1310 -0.0921 0.7912 0.027 Uiso 1 1 calc R . . . .
C14 C 0.0746(4) 0.0820(5) 0.5100(7) 0.0198(12) Uani 1 1 d . . . . .
H14A H 0.0797 0.0917 0.4255 0.024 Uiso 1 1 calc R . . . .
H14B H 0.0417 0.1570 0.5409 0.024 Uiso 1 1 calc R . . . .
C15 C 0.0163(4) -0.0391(6) 0.5388(7) 0.0239(15) Uani 1 1 d . . . . .
H15A H -0.0453 -0.0153 0.5727 0.029 Uiso 1 1 calc R . . . .
H15B H 0.0043 -0.0876 0.4675 0.029 Uiso 1 1 calc R . . . .
C16 C 0.2214(4) -0.0472(5) 0.5197(8) 0.0187(13) Uani 1 1 d . . . . .
H16A H 0.2875 -0.0500 0.5471 0.022 Uiso 1 1 calc R . . . .
H16B H 0.2219 -0.0483 0.4345 0.022 Uiso 1 1 calc R . . . .
C17 C 0.1659(4) -0.1647(6) 0.5663(6) 0.0201(13) Uani 1 1 d . . . . .
H17A H 0.1512 -0.2225 0.5019 0.024 Uiso 1 1 calc R . . . .
H17B H 0.2053 -0.2107 0.6227 0.024 Uiso 1 1 calc R . . . .
C18 C 0.0726(4) -0.1203(5) 0.6249(6) 0.0184(13) Uani 1 1 d . . . . .
H18 H 0.0342 -0.1949 0.6489 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 N1 2.303(5) . ?
I1 N11 2.297(5) . ?
O102 N101 1.238(8) . ?
O103 N101 1.245(9) . ?
O104 N101 1.253(11) . ?
N1 C2 1.495(7) . ?
N1 C4 1.505(7) . ?
N1 C6 1.485(9) . ?
N11 C12 1.494(9) . ?
N11 C14 1.503(7) . ?
N11 C16 1.500(7) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.545(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C8 1.514(9) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.550(8) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C8 1.526(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.538(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.535(10) . ?
C8 H8 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.522(9) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C18 1.537(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.533(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C18 1.512(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.539(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.529(8) . ?
C18 H18 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
N11 I1 N1 179.6(2) . . ?
C2 N1 I1 111.7(4) . . ?
C2 N1 C4 109.5(5) . . ?
C4 N1 I1 108.9(3) . . ?
C6 N1 I1 108.6(4) . . ?
C6 N1 C2 109.1(5) . . ?
C6 N1 C4 109.1(5) . . ?
C12 N11 I1 109.9(4) . . ?
C12 N11 C14 109.5(5) . . ?
C12 N11 C16 109.3(5) . . ?
C14 N11 I1 108.6(3) . . ?
C16 N11 I1 110.5(4) . . ?
C16 N11 C14 109.0(5) . . ?
O102 N101 O103 120.9(7) . . ?
O102 N101 O104 119.3(7) . . ?
O103 N101 O104 119.8(6) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
N1 C2 C3 109.7(5) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C8 C3 C2 109.3(5) . . ?
C8 C3 H3A 109.8 . . ?
C8 C3 H3B 109.8 . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
N1 C4 C5 109.9(5) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C8 C5 C4 108.7(5) . . ?
C8 C5 H5A 109.9 . . ?
C8 C5 H5B 109.9 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 C7 110.5(5) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 C6 108.7(6) . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
C3 C8 C5 109.2(6) . . ?
C3 C8 C7 108.3(6) . . ?
C3 C8 H8 110.3 . . ?
C5 C8 C7 108.4(5) . . ?
C5 C8 H8 110.3 . . ?
C7 C8 H8 110.3 . . ?
N11 C12 H12A 109.4 . . ?
N11 C12 H12B 109.4 . . ?
N11 C12 C13 111.2(5) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 110.0 . . ?
C12 C13 H13B 110.0 . . ?
C12 C13 C18 108.3(6) . . ?
H13A C13 H13B 108.4 . . ?
C18 C13 H13A 110.0 . . ?
C18 C13 H13B 110.0 . . ?
N11 C14 H14A 109.6 . . ?
N11 C14 H14B 109.6 . . ?
N11 C14 C15 110.3(5) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C18 C15 C14 109.0(5) . . ?
C18 C15 H15A 109.9 . . ?
C18 C15 H15B 109.9 . . ?
N11 C16 H16A 109.8 . . ?
N11 C16 H16B 109.8 . . ?
N11 C16 C17 109.3(5) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 C16 109.5(5) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C13 C18 H18 110.0 . . ?
C15 C18 C13 109.5(5) . . ?
C15 C18 C17 108.9(5) . . ?
C15 C18 H18 110.0 . . ?
C17 C18 C13 108.2(5) . . ?
C17 C18 H18 110.0 . . ?

_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 2.158
_oxdiff_exptl_absorpt_empirical_full_min 0.652
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.85(2)
2 0.15(2)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN/DIPE'
####################################################################### 
# 
# 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_I2_quin
_database_code_depnum_ccdc_archive 'CCDC 2079433'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2021-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H13 I2 N'
_chemical_formula_sum            'C7 H13 I2 N'
_chemical_formula_weight         364.98
_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 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   10.0222(7)
_cell_length_b                   7.9210(5)
_cell_length_c                   13.7704(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.604(8)
_cell_angle_gamma                90
_cell_volume                     1023.25(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.8470
_cell_measurement_theta_min      6.5420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    47.774
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41643
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 5 0.0105
0 -4 -5 0.0065
0 3 -7 0.0270
0 -3 7 0.0270
6 1 -5 0.0235
-6 -1 5 0.0245

_exptl_crystal_size_max          0.064
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.017
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.4027 4.3480 4.6298 -0.0785 0.9969 -0.0090
0.4027 -4.3480 -4.6298 0.0785 -0.9969 0.0090
-0.4414 2.7151 -6.8676 0.9693 0.0761 -0.2338
0.4414 -2.7151 6.8676 -0.9693 -0.0761 0.2338
6.2863 0.9195 -4.6008 0.4096 0.0330 0.9117
-6.2863 -0.9195 4.6008 -0.4096 -0.0330 -0.9117

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1055
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 0.859
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8880
_diffrn_reflns_point_group_measured_fraction_full 0.859
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.096
_diffrn_reflns_theta_min         6.559
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.859
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  34.00   1.00    3.00    --  -41.65  77.00 120.00  108
  2  ω    -70.00  31.00   1.00    3.00    --  -41.65  57.00 -90.00  101
  3  ω    -70.00  31.00   1.00    3.00    --  -41.65  57.00  30.00  101
  4  ω     36.00 145.00   1.00   12.00    --  112.00 -77.00 -90.00  109
  5  ω     36.00 109.00   1.00   12.00    --  112.00-111.00 -60.00   73
  6  ω    103.00 178.00   1.00   12.00    --  112.00  77.00 -90.00   75
  7  ω    104.00 178.00   1.00   12.00    --  112.00 111.00   0.00   74
  8  ω     61.00 146.00   1.00   12.00    --  112.00 178.00-180.00   85
  9  ω     29.00 107.00   1.00   12.00    --  112.00 -94.00-180.00   78
 10  ω     36.00 140.00   1.00   12.00    --  112.00 -30.00-120.00  104
 11  ω     36.00 109.00   1.00   12.00    --  112.00-111.00 150.00   73
 12  ω     36.00 109.00   1.00   12.00    --  112.00-111.00  30.00   73
 13  ω    104.00 178.00   1.00   12.00    --  112.00 111.00 -30.00   74
 14  ω    103.00 178.00   1.00   12.00    --  112.00  77.00 -60.00   75
 15  ω     86.00 178.00   1.00   12.00    --  112.00  45.00  60.00   92
 16  ω      7.00  33.00   1.00    3.00    --   41.65  84.00 167.01   26
 17  ω      9.00  42.00   1.00    3.00    --   41.65  80.00-108.15   33
 18  ω      8.00  42.00   1.00    3.00    --   41.65  81.00  38.60   34
 19  ω     59.00 178.00   1.00   12.00    --  112.00  15.00 -30.00  119
 20  ω     85.00 178.00   1.00   12.00    --  112.00  51.00 129.71   93
 21  ω     83.00 178.00   1.00   12.00    --  112.00  61.00   0.00   95
 22  ω     86.00 139.00   1.00   12.00    --  112.00  45.00-120.00   53
 23  ω     86.00 178.00   1.00   12.00    --  112.00  45.00  90.00   92
 24  ω     84.00 178.00   1.00   12.00    --  112.00  30.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0240850000
_diffrn_orient_matrix_UB_12      0.0903377000
_diffrn_orient_matrix_UB_13      -0.1038776000
_diffrn_orient_matrix_UB_21      0.0207721000
_diffrn_orient_matrix_UB_22      0.1720064000
_diffrn_orient_matrix_UB_23      0.0555885000
_diffrn_orient_matrix_UB_31      0.1611207000
_diffrn_orient_matrix_UB_32      -0.0087081000
_diffrn_orient_matrix_UB_33      0.0202497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1411
_reflns_number_total             1742
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.524
_refine_diff_density_min         -2.721
_refine_diff_density_rms         0.346
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.021
_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)+(0.1292P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1757
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C6 \\sim C7 \\sim C8: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.77286(7) 1.05382(9) 0.57669(5) 0.0279(3) Uani 1 1 d . . . . .
I2 I 0.84358(9) 1.33215(11) 0.71908(6) 0.0385(3) Uani 1 1 d . . . . .
N1 N 0.7260(11) 0.8196(14) 0.4648(7) 0.028(2) Uani 1 1 d . U . . .
C2 C 0.6462(16) 0.6876(15) 0.4988(9) 0.033(3) Uani 1 1 d . . . . .
H2A H 0.5631 0.7378 0.5078 0.039 Uiso 1 1 calc R . . . .
H2B H 0.7064 0.6421 0.5652 0.039 Uiso 1 1 calc R . . . .
C3 C 0.5984(16) 0.5422(17) 0.4180(10) 0.035(3) Uani 1 1 d . . . . .
H3A H 0.6220 0.4336 0.4523 0.042 Uiso 1 1 calc R . . . .
H3B H 0.4962 0.5468 0.3815 0.042 Uiso 1 1 calc R . . . .
C4 C 0.6331(17) 0.8749(19) 0.3575(10) 0.039(3) Uani 1 1 d . . . . .
H4A H 0.6737 0.9740 0.3372 0.046 Uiso 1 1 calc R . . . .
H4B H 0.5387 0.9037 0.3569 0.046 Uiso 1 1 calc R . . . .
C5 C 0.6229(19) 0.728(2) 0.2803(9) 0.042(3) Uani 1 1 d . . . . .
H5A H 0.5249 0.7137 0.2342 0.051 Uiso 1 1 calc R . . . .
H5B H 0.6807 0.7534 0.2385 0.051 Uiso 1 1 calc R . . . .
C6 C 0.8615(17) 0.7517(19) 0.4622(13) 0.045(4) Uani 1 1 d . U . . .
H6A H 0.9276 0.7354 0.5325 0.054 Uiso 1 1 calc R . . . .
H6B H 0.9036 0.8315 0.4279 0.054 Uiso 1 1 calc R . . . .
C7 C 0.8348(16) 0.580(2) 0.4031(14) 0.048(3) Uani 1 1 d . U . . .
H7A H 0.8876 0.5761 0.3561 0.058 Uiso 1 1 calc R . . . .
H7B H 0.8662 0.4875 0.4518 0.058 Uiso 1 1 calc R . . . .
C8 C 0.6764(15) 0.5657(17) 0.3428(10) 0.033(3) Uani 1 1 d . U . . .
H8 H 0.6583 0.4688 0.2956 0.040 Uiso 1 1 calc R . . . .


_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 I2 2.8688(11) . ?
I1 N1 2.351(10) . ?
N1 C2 1.489(15) . ?
N1 C4 1.507(15) . ?
N1 C6 1.473(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.555(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C8 1.513(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.56(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C8 1.54(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.56(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.51(2) . ?
C8 H8 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
N1 I1 I2 177.1(3) . . ?
C2 N1 I1 110.7(6) . . ?
C2 N1 C4 107.3(10) . . ?
C4 N1 I1 109.0(8) . . ?
C6 N1 I1 109.3(8) . . ?
C6 N1 C2 110.7(11) . . ?
C6 N1 C4 109.9(10) . . ?
N1 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
N1 C2 C3 111.0(9) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
C2 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
H3A C3 H3B 108.5 . . ?
C8 C3 C2 107.2(11) . . ?
C8 C3 H3A 110.3 . . ?
C8 C3 H3B 110.3 . . ?
N1 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
N1 C4 C5 108.8(11) . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C4 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C8 C5 C4 108.5(10) . . ?
C8 C5 H5A 110.0 . . ?
C8 C5 H5B 110.0 . . ?
N1 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
N1 C6 C7 109.9(11) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 C6 107.9(12) . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
C3 C8 C5 108.9(12) . . ?
C3 C8 C7 109.2(12) . . ?
C3 C8 H8 109.7 . . ?
C5 C8 H8 109.7 . . ?
C7 C8 C5 109.6(13) . . ?
C7 C8 H8 109.7 . . ?

_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 2.815
_oxdiff_exptl_absorpt_empirical_full_min 0.423
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6864 5800 6177 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3136 5733 6177 nmt -0.9997 0.0023 -0.5113 -0.0022 -1.0006 -0.0003 -0.0015
-0.0001 1.0000

_twin_special_details            
;
Component 2 rotated by -179.8508° 
around [-0.25 -0.00 0.97] (reciprocal) or [-0.00 -0.00 1.00] (direct)
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN/DIPE'
####################################################################### 
# 
# 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_ClCH2quin_AgCl2
_database_code_depnum_ccdc_archive 'CCDC 2084411'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_STRVA01_ClCH2quin_AgCl2     
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: The structure was refined 
as an inversion twin, therefore this 
checkcif alert is no longer relevant.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Ag Cl2, C8 H15 Cl N'
_chemical_formula_sum            'C8 H15 Ag Cl3 N'
_chemical_formula_weight         339.43
_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'
Ag Ag -0.8971 1.1015 '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'
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           110
_space_group_name_H-M_alt        'I 41 c d'
_space_group_name_Hall           'I 4bw -2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-y, x+1/2, z+1/4'
'y+1/2, -x, z+3/4'
'x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'-y, -x+1/2, z+3/4'
'y+1/2, x, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1, z+1'
'-y+1/2, x+1, z+3/4'
'y+1, -x+1/2, z+5/4'
'x+1/2, -y+1/2, z+1'
'-x+1, y+1, z+1/2'
'-y+1/2, -x+1, z+5/4'
'y+1, x+1/2, z+3/4'

_cell_length_a                   18.1238(3)
_cell_length_b                   18.1238(3)
_cell_length_c                   13.8565(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4551.47(18)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.5400
_cell_measurement_theta_min      2.8890
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.385
_exptl_absorpt_coefficient_mu    2.431
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2688
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 25 -1 0.0478
-25 -2 1 0.0766
25 2 -1 0.0836
-12 1 17 0.1695
9 -1 -18 0.2166
-25 -3 -4 0.1161
18 0 -14 0.1677
6 3 19 0.2278
3 -25 2 0.0574
1 -25 1 0.0625
8 12 -16 0.1868
-13 -12 14 0.1495

_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0005 24.9998 -0.9999 0.9757 0.0626 -0.0702
-25.0003 -2.0001 1.0001 0.0498 -0.4465 0.8746
25.0003 2.0001 -1.0001 -0.0498 0.4465 -0.8746
-12.0002 0.9999 17.0001 0.0798 -0.9842 0.0663
9.0002 -0.9999 -18.0000 -0.0631 0.9833 0.0607
-25.0003 -3.0001 -3.9999 0.0171 -0.2140 0.9837
18.0003 0.0001 -14.0001 -0.0755 0.9405 -0.3463
6.0000 3.0000 19.0000 0.0623 -0.7892 -0.6228
3.0005 -24.9998 1.9999 -0.9872 -0.0776 -0.0214
1.0005 -24.9998 0.9999 -0.9757 -0.0626 0.0702
7.9999 12.0000 -16.0000 0.4436 0.8904 -0.0112
-13.0000 -12.0000 14.0000 -0.4155 -0.8763 0.2299

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.338
_diffrn_reflns_theta_min         2.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  -5.00   1.00    3.00    --   19.23 -19.00-120.00   49
  2  ω     33.00  60.00   1.00    3.00    --   19.23 -19.00-120.00   27
  3  ω    -17.00  24.00   1.00    3.00    --   19.23 -57.00 150.00   41
  4  ω    -50.00 -18.00   1.00    3.00    --   19.07 -57.00 150.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0051440000
_diffrn_orient_matrix_UB_12      0.0387738000
_diffrn_orient_matrix_UB_13      -0.0012179000
_diffrn_orient_matrix_UB_21      0.0158865000
_diffrn_orient_matrix_UB_22      0.0012702000
_diffrn_orient_matrix_UB_23      -0.0467543000
_diffrn_orient_matrix_UB_31      -0.0354123000
_diffrn_orient_matrix_UB_32      -0.0050589000
_diffrn_orient_matrix_UB_33      -0.0207978000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2216
_reflns_number_total             2292
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.34(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2292
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.061
_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)+(0.0182P)²+0.0439P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0432
_refine_ls_wR_factor_ref         0.0440
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.66(4)
 0.34(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C11(H11A,H11B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Ag51 Ag 0.74561(2) 0.73405(2) 0.57078(5) 0.01749(9) Uani 1 1 d . . . . .
Cl12 Cl 0.48440(6) 0.87975(6) 0.68288(9) 0.0282(3) Uani 1 1 d . . . . .
Cl52 Cl 0.70266(5) 0.84344(5) 0.67746(6) 0.0164(2) Uani 1 1 d . . . . .
Cl53 Cl 0.72585(6) 0.63915(6) 0.71143(7) 0.0185(2) Uani 1 1 d . . . . .
N1 N 0.49877(19) 0.73264(17) 0.7142(3) 0.0142(7) Uani 1 1 d . . . . .
C2 C 0.5395(2) 0.7177(2) 0.6213(3) 0.0189(9) Uani 1 1 d . . . . .
H2A H 0.5921 0.7149 0.6337 0.023 Uiso 1 1 calc R . . . .
H2B H 0.5307 0.7574 0.5758 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5121(2) 0.6445(2) 0.5790(3) 0.0251(10) Uani 1 1 d . . . . .
H3A H 0.4803 0.6540 0.5241 0.030 Uiso 1 1 calc R . . . .
H3B H 0.5538 0.6154 0.5571 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5224(2) 0.6765(2) 0.7892(3) 0.0213(9) Uani 1 1 d . . . . .
H4A H 0.4913 0.6808 0.8459 0.026 Uiso 1 1 calc R . . . .
H4B H 0.5730 0.6859 0.8084 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5161(2) 0.5988(2) 0.7475(3) 0.0261(10) Uani 1 1 d . . . . .
H5A H 0.4929 0.5663 0.7942 0.031 Uiso 1 1 calc R . . . .
H5B H 0.5648 0.5796 0.7330 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4164(2) 0.7245(2) 0.6969(3) 0.0169(9) Uani 1 1 d . . . . .
H6A H 0.4017 0.7541 0.6419 0.020 Uiso 1 1 calc R . . . .
H6B H 0.3893 0.7416 0.7530 0.020 Uiso 1 1 calc R . . . .
C7 C 0.3986(2) 0.6433(2) 0.6780(3) 0.0237(10) Uani 1 1 d . . . . .
H7A H 0.3751 0.6218 0.7343 0.028 Uiso 1 1 calc R . . . .
H7B H 0.3649 0.6391 0.6239 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4698(2) 0.6021(2) 0.6557(3) 0.0193(9) Uani 1 1 d . . . . .
H8 H 0.4587 0.5521 0.6329 0.023 Uiso 1 1 calc R . . . .
C11 C 0.5181(2) 0.8063(2) 0.7546(3) 0.0215(10) Uani 1 1 d . . . . .
H11A H 0.5713 0.8103 0.7596 0.026 Uiso 1 1 calc R . . . .
H11B H 0.4977 0.8105 0.8191 0.026 Uiso 1 1 calc R . . . .


_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
Ag51 Cl52 2.5927(11) . ?
Ag51 Cl52 2.6216(11) 11_644 ?
Ag51 Cl53 2.5845(11) 11_644 ?
Ag51 Cl53 2.6237(12) . ?
Cl12 C11 1.769(4) . ?
Cl52 Ag51 2.6215(11) 12_464 ?
Cl53 Ag51 2.5845(11) 12_464 ?
N1 C2 1.508(5) . ?
N1 C4 1.517(5) . ?
N1 C6 1.520(5) . ?
N1 C11 1.490(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.533(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C8 1.519(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.525(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C8 1.525(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.529(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.522(5) . ?
C8 H8 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
Cl52 Ag51 Cl52 114.39(2) . 11_644 ?
Cl52 Ag51 Cl53 109.66(3) 11_644 . ?
Cl52 Ag51 Cl53 92.11(4) . . ?
Cl53 Ag51 Cl52 92.35(4) 11_644 11_644 ?
Cl53 Ag51 Cl52 128.38(3) 11_644 . ?
Cl53 Ag51 Cl53 120.54(2) 11_644 . ?
Ag51 Cl52 Ag51 84.03(3) . 12_464 ?
Ag51 Cl53 Ag51 84.14(3) 12_464 . ?
C2 N1 C4 109.0(3) . . ?
C2 N1 C6 109.3(3) . . ?
C4 N1 C6 108.7(3) . . ?
C11 N1 C2 111.5(3) . . ?
C11 N1 C4 106.1(3) . . ?
C11 N1 C6 112.2(3) . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
N1 C2 C3 108.8(3) . . ?
H2A C2 H2B 108.3 . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C8 C3 C2 109.5(3) . . ?
C8 C3 H3A 109.8 . . ?
C8 C3 H3B 109.8 . . ?
N1 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
N1 C4 C5 109.8(3) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C4 C5 C8 108.7(3) . . ?
H5A C5 H5B 108.3 . . ?
C8 C5 H5A 109.9 . . ?
C8 C5 H5B 109.9 . . ?
N1 C6 H6A 109.9 . . ?
N1 C6 H6B 109.9 . . ?
N1 C6 C7 109.1(3) . . ?
H6A C6 H6B 108.3 . . ?
C7 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 C6 109.1(3) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C3 C8 C5 109.0(3) . . ?
C3 C8 C7 108.8(3) . . ?
C3 C8 H8 110.2 . . ?
C5 C8 H8 110.2 . . ?
C7 C8 C5 108.4(3) . . ?
C7 C8 H8 110.2 . . ?
Cl12 C11 H11A 109.1 . . ?
Cl12 C11 H11B 109.1 . . ?
N1 C11 Cl12 112.5(3) . . ?
N1 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?


_ins_header                      
;
TITL OHD052-1_scale in I4(1)cd 
REM I4(1)cd (#110 in standard setting)
CELL 0.71073  18.123751  18.123751  13.856526  90.0000  90.0000  90.0000
ZERR   16.00   0.000251   0.000251   0.000306   0.0000   0.0000   0.0000
LATT -2
SYMM -x+1/2,-y+1/2, z+1/2 
SYMM -y, x+1/2, z+1/4 
SYMM  y+1/2,-x, z+3/4 
SYMM  x,-y, z+1/2 
SYMM -x+1/2, y+1/2, z 
SYMM -y,-x+1/2, z+3/4 
SYMM  y+1/2, x, z+1/4 
SFAC C H B N F Ag
UNIT 224.00 416.00 16.00 32.00 64.00 16.00
TREF
HKLF 4
END
;
_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 1.175
_oxdiff_exptl_absorpt_empirical_full_min 0.826
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.66(4)
2 0.34(4)

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

data_I2_quin_2
_database_code_depnum_ccdc_archive 'CCDC 2079434'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2021-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H13 I2 N'
_chemical_formula_sum            'C7 H13 I2 N'
_chemical_formula_weight         364.98
_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 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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                   6.7067(7)
_cell_length_b                   8.4046(8)
_cell_length_c                   9.5027(7)
_cell_angle_alpha                91.599(7)
_cell_angle_beta                 104.779(8)
_cell_angle_gamma                97.372(8)
_cell_volume                     512.61(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.5230
_cell_measurement_theta_min      6.9090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    47.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 5 0 0.0092
0 -5 0 0.0032
0 0 6 0.0262
0 0 -6 0.0262
4 -1 1 0.0315
-4 1 -1 0.0315
2 0 -6 0.0287
-2 0 6 0.0287

_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.012
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.4177 5.3176 -0.4331 -0.0785 0.9969 -0.0090
-0.4177 -5.3176 0.4331 0.0785 -0.9969 0.0090
0.2290 -0.1099 5.8658 0.0089 -0.0011 -1.0000
-0.2290 0.1099 -5.8658 -0.0089 0.0011 1.0000
3.9492 -0.6230 1.0766 -0.8793 0.0226 -0.4758
-3.9492 0.6230 -1.0766 0.8793 -0.0226 0.4758
2.0402 -0.2384 -6.0009 -0.5220 0.0144 0.8528
-2.0402 0.2384 6.0009 0.5220 -0.0144 -0.8528

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0981
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5477
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.084
_diffrn_reflns_theta_min         6.896
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    4.00    --  -41.65 -37.00  30.00   99
  2  ω   -114.00 -14.00   1.00    4.00    --  -41.65 -57.00 150.00  100
  3  ω    -21.00  74.00   1.00    4.00    --   41.65 -77.00 -90.00   95
  4  ω      9.00  42.00   1.00    4.00    --   41.65  79.00  45.74   33
  5  ω     36.00 109.00   1.00   16.00    --  112.00-111.00  60.00   73
  6  ω     36.00 140.00   1.00   16.00    --  112.00 -30.00-180.00  104
  7  ω     86.00 178.00   1.00   16.00    --  112.00  45.00   0.00   92
  8  ω     36.00 109.00   1.00   16.00    --  112.00-111.00 120.00   73
  9  ω     36.00 109.00   1.00   16.00    --  112.00-111.00-120.00   73
 10  ω    104.00 178.00   1.00   16.00    --  112.00 111.00 -90.00   74
 11  ω     84.00 178.00   1.00   16.00    --  112.00  30.00  90.00   94
 12  ω     36.00 109.00   1.00   16.00    --  112.00-111.00 -30.00   73
 13  ω     40.00 141.00   1.00   16.00    --  112.00 -61.00 -60.00  101
 14  ω     39.00 142.00   1.00   16.00    --  112.00 -66.00-155.00  103
 15  ω    104.00 178.00   1.00   16.00    --  112.00 111.00 -60.00   74
 16  ω     61.00 146.00   1.00   16.00    --  112.00 178.00-150.00   85
 17  ω    -87.00  -6.00   1.00    4.00    --  -41.65 125.00  60.00   81
 18  ω   -114.00 -14.00   1.00    4.00    --  -41.65 -57.00 -90.00  100
 19  ω      9.00  42.00   1.00    4.00    --   41.65  80.00 -94.83   33
 20  ω     86.00 178.00   1.00   16.00    --  112.00  44.00 146.35   92
 21  ω     86.00 178.00   1.00   16.00    --  112.00  45.00 -60.00   92
 22  ω     84.00 178.00   1.00   16.00    --  112.00  54.00  29.10   94
 23  ω     59.00 178.00   1.00   16.00    --  112.00  15.00-120.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2248826000
_diffrn_orient_matrix_UB_12      0.0037544000
_diffrn_orient_matrix_UB_13      0.0103758000
_diffrn_orient_matrix_UB_21      0.0343750000
_diffrn_orient_matrix_UB_22      0.1849244000
_diffrn_orient_matrix_UB_23      0.0019423000
_diffrn_orient_matrix_UB_31      -0.0762476000
_diffrn_orient_matrix_UB_32      -0.0093589000
_diffrn_orient_matrix_UB_33      -0.1676697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1572
_reflns_number_total             1843
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.759
_refine_diff_density_min         -1.305
_refine_diff_density_rms         0.235
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.008
_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)+(0.0816P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.60860(7) 0.54786(5) 0.77683(5) 0.0251(2) Uani 1 1 d . . . . .
I2 I 0.36981(8) 0.79232(6) 0.83117(5) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.7969(9) 0.3422(8) 0.7284(7) 0.0227(12) Uani 1 1 d . . . . .
C2 C 0.8945(12) 0.3891(9) 0.6112(8) 0.0264(15) Uani 1 1 d . . . . .
H2A H 0.9746 0.4953 0.6356 0.032 Uiso 1 1 calc R . . . .
H2B H 0.7878 0.3929 0.5211 0.032 Uiso 1 1 calc R . . . .
C3 C 1.0404(12) 0.2650(10) 0.5902(9) 0.0285(15) Uani 1 1 d . . . . .
H3A H 1.0129 0.2324 0.4876 0.034 Uiso 1 1 calc R . . . .
H3B H 1.1847 0.3137 0.6246 0.034 Uiso 1 1 calc R . . . .
C4 C 0.9639(14) 0.3229(11) 0.8632(8) 0.0341(18) Uani 1 1 d . . . . .
H4A H 0.9043 0.3088 0.9456 0.041 Uiso 1 1 calc R . . . .
H4B H 1.0678 0.4180 0.8846 0.041 Uiso 1 1 calc R . . . .
C5 C 1.0658(18) 0.1731(15) 0.8361(11) 0.051(3) Uani 1 1 d . . . . .
H5A H 1.2162 0.1991 0.8683 0.061 Uiso 1 1 calc R . . . .
H5B H 1.0233 0.0864 0.8920 0.061 Uiso 1 1 calc R . . . .
C6 C 0.6521(13) 0.1907(9) 0.6832(11) 0.0373(19) Uani 1 1 d . . . . .
H6A H 0.5344 0.2093 0.6047 0.045 Uiso 1 1 calc R . . . .
H6B H 0.5998 0.1539 0.7645 0.045 Uiso 1 1 calc R . . . .
C7 C 0.7662(15) 0.0606(9) 0.6311(12) 0.040(2) Uani 1 1 d . . . . .
H7A H 0.7371 -0.0395 0.6753 0.048 Uiso 1 1 calc R . . . .
H7B H 0.7179 0.0415 0.5260 0.048 Uiso 1 1 calc R . . . .
C8 C 1.0012(14) 0.1196(10) 0.6756(9) 0.0322(17) Uani 1 1 d . . . . .
H8 H 1.0793 0.0346 0.6556 0.039 Uiso 1 1 calc R . . . .


_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 I2 2.8741(7) . ?
I1 N1 2.368(7) . ?
N1 C2 1.468(10) . ?
N1 C4 1.499(9) . ?
N1 C6 1.479(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.560(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C8 1.518(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.553(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C8 1.513(13) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.551(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.535(12) . ?
C8 H8 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
N1 I1 I2 178.46(14) . . ?
C2 N1 I1 108.9(4) . . ?
C2 N1 C4 109.0(6) . . ?
C2 N1 C6 109.9(6) . . ?
C4 N1 I1 109.1(5) . . ?
C6 N1 I1 109.2(5) . . ?
C6 N1 C4 110.8(7) . . ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
N1 C2 C3 109.7(6) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C8 C3 C2 109.1(6) . . ?
C8 C3 H3A 109.9 . . ?
C8 C3 H3B 109.9 . . ?
N1 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
N1 C4 C5 108.3(7) . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C8 C5 C4 110.2(7) . . ?
C8 C5 H5A 109.6 . . ?
C8 C5 H5B 109.6 . . ?
N1 C6 H6A 109.7 . . ?
N1 C6 H6B 109.7 . . ?
N1 C6 C7 109.9(6) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 C6 108.7(7) . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C3 C8 C7 107.7(7) . . ?
C3 C8 H8 110.8 . . ?
C5 C8 C3 108.0(8) . . ?
C5 C8 C7 108.7(8) . . ?
C5 C8 H8 110.8 . . ?
C7 C8 H8 110.8 . . ?

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
I1 N1 C2 C3 173.4(4) . . . . ?
I1 N1 C4 C5 172.5(7) . . . . ?
I1 N1 C6 C7 172.4(6) . . . . ?
N1 C2 C3 C8 11.3(8) . . . . ?
N1 C4 C5 C8 13.0(12) . . . . ?
N1 C6 C7 C8 12.5(11) . . . . ?
C2 N1 C4 C5 -68.7(9) . . . . ?
C2 N1 C6 C7 53.0(9) . . . . ?
C2 C3 C8 C5 -64.9(8) . . . . ?
C2 C3 C8 C7 52.3(8) . . . . ?
C4 N1 C2 C3 54.5(8) . . . . ?
C4 N1 C6 C7 -67.5(9) . . . . ?
C4 C5 C8 C3 50.8(11) . . . . ?
C4 C5 C8 C7 -65.8(11) . . . . ?
C6 N1 C2 C3 -67.1(8) . . . . ?
C6 N1 C4 C5 52.3(10) . . . . ?
C6 C7 C8 C3 -66.0(10) . . . . ?
C6 C7 C8 C5 50.8(10) . . . . ?

_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 2.276
_oxdiff_exptl_absorpt_empirical_full_min 0.432
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.6941 5282 944 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.3059 5260 944 nmt 0.9982 -0.0031 -0.0017 -0.3248 -0.9985 0.0041 -0.7266
-0.0033 -1.0008

_twin_special_details            
;
Component 2 rotated by -179.7854° 
 around [0.93 -0.15 -0.34] (reciprocal) or [1.00 -0.00 -0.00] (direct)
;

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN/DIPE'
####################################################################### 
# 
# 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_1_ClO4
_database_code_depnum_ccdc_archive 'CCDC 2079432'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2021-04-22 deposited with the CCDC.	2021-05-20 downloaded from the CCDC.
;
_audit_creation_date             2021-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_STRVA01_1_ClO4              
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: This checkcif alert 
is irrelevant, as the final 
structure was refined as an 
inversion twin.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H26 I1 N2, Cl1 O4'
_chemical_formula_sum            'C14 H26 Cl I N2 O4'
_chemical_formula_weight         448.72
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      cubic
_space_group_IT_number           198
_space_group_name_H-M_alt        'P 21 3'
_space_group_name_Hall           'P 2ac 2ab 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'z, x, y'
'z+1/2, -x+1/2, -y'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y, z, x'
'-y, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x'
'-y+1/2, -z, x+1/2'

_cell_length_a                   11.9987(2)
_cell_length_b                   11.9987(2)
_cell_length_c                   11.9987(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1727.44(9)
_cell_formula_units_Z            3.99996
_cell_measurement_reflns_used    1461
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      75.8200
_cell_measurement_theta_min      5.1810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85504
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.725
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 0 0 0.0526
-7 0 4 0.0584
-7 4 1 0.0588
-7 -1 -3 0.0672
3 -5 -5 0.0656
-8 1 -1 0.0559
-6 -3 3 0.0545
0 -8 -1 0.0487
0 8 1 0.0487
1 0 8 0.0532
-1 0 -8 0.0532
-8 0 0 0.0526
0 6 -5 0.0722

_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.097
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.7775 -0.1677 -0.2695 0.1814 -0.9781 0.1023
-6.5982 -0.1496 4.1246 -0.5118 0.7453 -0.4274
-6.5812 4.0204 1.0831 -0.5511 0.8016 0.2316
-7.1720 -1.0480 -2.8473 0.2333 0.9718 0.0334
2.8272 -4.9937 -5.2681 0.9715 -0.2333 -0.0410
-7.6328 1.3716 -0.6979 -0.1814 0.9786 0.0969
-6.3465 -3.3563 2.9988 -0.1374 0.7441 -0.6538
-0.2078 -7.7663 -0.5345 0.6772 0.0527 -0.7339
0.2078 7.7663 0.5345 -0.6772 -0.0527 0.7339
1.1701 0.3882 7.6968 -0.7639 -0.3169 -0.5621
-1.1701 -0.3882 -7.6968 0.7639 0.3169 0.5621
-7.7775 0.1677 0.2695 -0.1814 0.9781 -0.1023
0.1657 6.1583 -4.7669 -0.0287 0.0715 0.9970

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2149
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.956
_diffrn_reflns_theta_min         5.213
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -56.00   1.00    1.00    --  -41.90-160.00-152.00   58
  2  ω    102.00 178.00   1.00    2.00    --  112.00  30.00  60.00   76
  3  ω   -118.00 -93.00   1.00    1.00    --  -42.15   0.00  30.00   25
  4  ω     52.00 105.00   1.00    2.00    --  112.00-111.00   0.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0181788000
_diffrn_orient_matrix_UB_12      -0.0809486000
_diffrn_orient_matrix_UB_13      -0.0979314000
_diffrn_orient_matrix_UB_21      -0.1265562000
_diffrn_orient_matrix_UB_22      -0.0018949000
_diffrn_orient_matrix_UB_23      -0.0218384000
_diffrn_orient_matrix_UB_31      0.0125307000
_diffrn_orient_matrix_UB_32      0.0996634000
_diffrn_orient_matrix_UB_33      -0.0799680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1078
_reflns_number_total             1130
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.488(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1130
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.039
_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)+(0.0305P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0580
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.512(16)
 0.488(16)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.74645(2) 0.24645(2) 0.25355(2) 0.00965(14) Uani 1 3 d S T P . .
Cl51 Cl 0.73582(8) 0.76418(8) 0.23582(8) 0.0134(3) Uani 1 3 d S T P . .
O52 O 0.8050(2) 0.6950(2) 0.3050(2) 0.0181(11) Uani 1 3 d S T P . .
O53 O 0.7303(3) 0.7172(3) 0.1251(2) 0.0261(7) Uani 1 1 d . . . . .
N1 N 0.8572(3) 0.3572(3) 0.1428(3) 0.0098(10) Uani 1 3 d S T P . .
N11 N 0.6361(3) 0.1361(3) 0.3639(3) 0.0104(10) Uani 1 3 d S T P . .
C2 C 0.8768(3) 0.4664(3) 0.1989(3) 0.0132(8) Uani 1 1 d . . . . .
H2A H 0.8996 0.4540 0.2755 0.016 Uiso 1 1 calc R . . . .
H2B H 0.8083 0.5093 0.1996 0.016 Uiso 1 1 calc R . . . .
C3 C 0.9684(3) 0.5316(3) 0.1362(4) 0.0175(9) Uani 1 1 d . . . . .
H3A H 0.9479 0.6096 0.1304 0.021 Uiso 1 1 calc R . . . .
H3B H 1.0384 0.5265 0.1762 0.021 Uiso 1 1 calc R . . . .
C8 C 0.9806(5) 0.4806(5) 0.0194(5) 0.0180(15) Uani 1 3 d S T P . .
H8 H 1.0277 0.5277 -0.0277 0.022 Uiso 1 3 calc RS T P . .
C12 C 0.5647(3) 0.0640(3) 0.2919(3) 0.0135(8) Uani 1 1 d . . . . .
H12A H 0.6108 0.0102 0.2530 0.016 Uiso 1 1 calc R . . . .
H12B H 0.5269 0.1094 0.2367 0.016 Uiso 1 1 calc R . . . .
C13 C 0.4783(3) 0.0027(3) 0.3640(4) 0.0158(8) Uani 1 1 d . . . . .
H13A H 0.4051 0.0353 0.3532 0.019 Uiso 1 1 calc R . . . .
H13B H 0.4749 -0.0753 0.3429 0.019 Uiso 1 1 calc R . . . .
C18 C 0.5136(5) 0.0136(5) 0.4864(5) 0.019(2) Uani 1 3 d S T P . .
H18 H 0.4664 -0.0336 0.5336 0.023 Uiso 1 3 calc RS T 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
I1 N1 2.302(5) . ?
I1 N11 2.293(5) . ?
Cl51 O52 1.437(5) . ?
Cl51 O53 1.445(3) . ?
Cl51 O53 1.445(3) 12_664 ?
Cl51 O53 1.445(3) 6_566 ?
N1 C2 1.491(4) . ?
N1 C2 1.491(4) 8_645 ?
N1 C2 1.491(4) 11_556 ?
N11 C12 1.493(4) . ?
N11 C12 1.493(4) 8_645 ?
N11 C12 1.493(4) 11_556 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.545(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C8 1.536(5) . ?
C8 C3 1.536(5) 11_556 ?
C8 C3 1.536(5) 8_645 ?
C8 H8 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.537(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C18 1.535(5) . ?
C18 C13 1.535(5) 8_645 ?
C18 C13 1.535(5) 11_556 ?
C18 H18 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
N11 I1 N1 180.00(10) . . ?
O52 Cl51 O53 109.39(14) . . ?
O52 Cl51 O53 109.39(14) . 6_566 ?
O52 Cl51 O53 109.39(14) . 12_664 ?
O53 Cl51 O53 109.55(14) 12_664 6_566 ?
O53 Cl51 O53 109.55(14) 6_566 . ?
O53 Cl51 O53 109.55(14) 12_664 . ?
C2 N1 I1 109.7(2) 11_556 . ?
C2 N1 I1 109.7(2) . . ?
C2 N1 I1 109.7(2) 8_645 . ?
C2 N1 C2 109.2(2) 8_645 11_556 ?
C2 N1 C2 109.2(2) 11_556 . ?
C2 N1 C2 109.2(2) 8_645 . ?
C12 N11 I1 109.4(3) . . ?
C12 N11 I1 109.4(3) 11_556 . ?
C12 N11 I1 109.4(3) 8_645 . ?
C12 N11 C12 109.5(3) . 11_556 ?
C12 N11 C12 109.5(3) 11_556 8_645 ?
C12 N11 C12 109.5(3) . 8_645 ?
N1 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
N1 C2 C3 109.7(3) . . ?
H2A C2 H2B 108.2 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C8 C3 C2 108.1(5) . . ?
C8 C3 H3A 110.1 . . ?
C8 C3 H3B 110.1 . . ?
C3 C8 C3 108.3(4) 8_645 11_556 ?
C3 C8 C3 108.3(4) 8_645 . ?
C3 C8 C3 108.3(4) 11_556 . ?
C3 C8 H8 110.6 8_645 . ?
C3 C8 H8 110.6 . . ?
C3 C8 H8 110.6 11_556 . ?
N11 C12 H12A 109.7 . . ?
N11 C12 H12B 109.7 . . ?
N11 C12 C13 109.8(4) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C12 C13 H13A 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C18 C13 C12 108.2(5) . . ?
C18 C13 H13A 110.1 . . ?
C18 C13 H13B 110.1 . . ?
C13 C18 C13 108.8(4) . 11_556 ?
C13 C18 C13 108.8(4) . 8_645 ?
C13 C18 C13 108.8(4) 11_556 8_645 ?
C13 C18 H18 110.2 . . ?
C13 C18 H18 110.2 11_556 . ?
C13 C18 H18 110.2 8_645 . ?


_ins_header                      
;
TITL OHD196_2_numabs in P2(1)3 
REM P2(1)3 (#198 in standard setting)
CELL 1.54184  11.998674  11.998674  11.998674  90.0000  90.0000  90.0000
ZERR    4.00   0.000164   0.000164   0.000164   0.0000   0.0000   0.0000
LATT -1
SYMM -x+1/2,-y, z+1/2 
SYMM -x, y+1/2,-z+1/2 
SYMM  x+1/2,-y+1/2,-z 
SYMM  z, x, y 
SYMM  z+1/2,-x+1/2,-y 
SYMM -z+1/2,-x, y+1/2 
SYMM -z, x+1/2,-y+1/2 
SYMM  y, z, x 
SYMM -y, z+1/2,-x+1/2 
SYMM  y+1/2,-z+1/2,-x 
SYMM -y+1/2,-z, x+1/2 
SFAC C H N O Cl I
UNIT 56.00 104.00 8.00 16.00 4.00 4.00
TREF
HKLF 4
END
;
_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 1.171
_oxdiff_exptl_absorpt_empirical_full_min 0.846
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.512(16)
2 0.488(16)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN/TBME'
