# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 1973198'
loop_
_audit_author_name
_audit_author_address
'Ena Luis'
;UNSW Sydney
Australia
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            167-C.HI
_chemical_melting_point          ?
_chemical_formula_moiety         'C7.50 H8.50 I0.50 N'
_chemical_formula_sum            'C7.50 H8.50 I0.50 N'
_chemical_formula_weight         176.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.3978(4)
_cell_length_b                   11.4140(4)
_cell_length_c                   17.0191(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1437.07(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    151(2)
_cell_measurement_reflns_used    2114
_cell_measurement_theta_min      2.986
_cell_measurement_theta_max      30.524

_exptl_crystal_description       'truncated block'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.213
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5902
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker Quazar Multilayer Optics'
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7072
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.986
_diffrn_reflns_theta_max         30.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2114
_reflns_number_gt                1726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex II software'
_computing_cell_refinement       'Bruker Apex II software'
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0213P)²+0.5006P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2114
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0454
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.2500 0.2500 0.03288(2) 0.02212(6) Uani 1 2 d S T P . .
C3 C 0.85372(19) 0.36187(12) 0.21019(8) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.8260(2) 0.46744(15) 0.33091(10) 0.0263(3) Uani 1 1 d . . . . .
C5 C 1.0025(2) 0.29145(15) 0.32540(9) 0.0224(3) Uani 1 1 d . . . . .
N1 N 0.80617(17) 0.34800(11) 0.12881(7) 0.0184(2) Uani 1 1 d . . . . .
C8 C 0.7859(2) 0.45686(14) 0.25159(10) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.9670(2) 0.28094(13) 0.24561(9) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.9311(2) 0.38377(15) 0.36773(9) 0.0260(3) Uani 1 1 d . . . . .
C2 C 0.8393(2) 0.44893(14) 0.07692(10) 0.0283(4) Uani 1 1 d . . . . .
H2A H 0.8270 0.4244 0.0220 0.042 Uiso 1 1 calc R U . . .
H2B H 0.9617 0.4789 0.0859 0.042 Uiso 1 1 calc R U . . .
H2C H 0.7511 0.5107 0.0884 0.042 Uiso 1 1 calc R U . . .
C1 C 0.7500 0.2500 0.09630(13) 0.0198(4) Uani 1 2 d S T P . .
H7 H 0.785(3) 0.5323(19) 0.3589(12) 0.032(6) Uiso 1 1 d . . . . .
H8 H 0.707(3) 0.5131(19) 0.2272(10) 0.023(5) Uiso 1 1 d . . . . .
H4 H 1.021(3) 0.2208(17) 0.2147(9) 0.020(5) Uiso 1 1 d . . . . .
H6 H 0.959(3) 0.3921(16) 0.4218(11) 0.038(5) Uiso 1 1 d . . . . .
H1 H 0.7500 0.2500 0.0408(17) 0.033(10) Uiso 1 2 d S . P . .
H5 H 1.077(3) 0.2334(14) 0.3523(12) 0.027(5) Uiso 1 1 d . . . . .


_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
C3 C4 1.385(2) . ?
C3 C8 1.387(2) . ?
C3 N1 1.4377(18) . ?
C7 C6 1.382(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.93(2) . ?
C5 C6 1.381(2) . ?
C5 C4 1.388(2) . ?
C5 H5 0.974(19) . ?
N1 C1 1.3153(16) . ?
N1 C2 1.4721(19) . ?
C8 H8 0.96(2) . ?
C4 H4 0.954(18) . ?
C6 H6 0.948(19) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C1 N1 1.3153(16) 2_655 ?
C1 H1 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 C3 C8 121.27(14) . . ?
C4 C3 N1 119.59(13) . . ?
C8 C3 N1 119.15(13) . . ?
C6 C7 C8 120.09(15) . . ?
C6 C7 H7 120.0(13) . . ?
C8 C7 H7 119.8(13) . . ?
C6 C5 C4 120.25(15) . . ?
C6 C5 H5 119.3(11) . . ?
C4 C5 H5 120.4(12) . . ?
C1 N1 C3 125.19(14) . . ?
C1 N1 C2 117.75(14) . . ?
C3 N1 C2 116.81(13) . . ?
C3 C8 C7 119.02(15) . . ?
C3 C8 H8 121.4(11) . . ?
C7 C8 H8 119.5(11) . . ?
C3 C4 C5 118.85(14) . . ?
C3 C4 H4 119.7(10) . . ?
C5 C4 H4 121.4(10) . . ?
C5 C6 C7 120.38(15) . . ?
C5 C6 H6 119.9(12) . . ?
C7 C6 H6 119.6(12) . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C1 N1 130.2(2) . 2_655 ?
N1 C1 H1 114.88(10) . . ?
N1 C1 H1 114.88(10) 2_655 . ?

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.065

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_21
_database_code_depnum_ccdc_archive 'CCDC 1973199'
loop_
_audit_author_name
_audit_author_address
'Ena Luis'
;UNSW Sydney
Australia
;
_audit_update_record             
;
2019-12-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            '166-B.HI half dichloromethane solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19.50 H26 Cl I N2'
_chemical_formula_sum            'C19.50 H26 Cl I N2'
_chemical_formula_weight         450.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.6780(5)
_cell_length_b                   26.8240(8)
_cell_length_c                   11.0601(3)
_cell_angle_alpha                90
_cell_angle_beta                 124.7010(10)
_cell_angle_gamma                90
_cell_volume                     4067.9(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5670
_cell_measurement_theta_min      1.668
_cell_measurement_theta_max      30.533

_exptl_crystal_description       'trapezoid plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_F_000             1816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.709
_shelx_estimated_absorpt_T_min   0.784
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6578
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Bruker Quazar Multilayer Optics'
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18215
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         30.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5670
_reflns_number_gt                4646
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker Apex II software'
_computing_cell_refinement       'Bruker Apex II software'
_computing_data_reduction        X-Seed
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'X-Seed / POV-Ray'
_computing_publication_material  'Microsoft Office 2010'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+5.9758P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5670
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0689
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.38659(2) 0.7500 0.03700(7) Uani 1 2 d S T P . .
I2 I 0.0000 0.30143(2) 0.7500 0.02799(6) Uani 1 2 d S T P . .
Cl1S Cl 0.02724(10) 0.52899(4) 0.14657(13) 0.0874(3) Uani 1 1 d . . . . .
N1 N 0.22028(13) 0.35825(6) 0.2907(2) 0.0223(4) Uani 1 1 d . . . . .
N2 N 0.36937(13) 0.35873(6) 0.30745(19) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.31267(16) 0.34781(8) 0.3508(2) 0.0209(4) Uani 1 1 d . . . . .
C1S C 0.0392(6) 0.5586(2) 0.2880(10) 0.070(2) Uani 0.5 1 d . . P . .
H1S1 H 0.0156 0.5932 0.2584 0.084 Uiso 0.5 1 calc R U P . .
H1S2 H 0.1092 0.5600 0.3697 0.084 Uiso 0.5 1 calc R U P . .
H1 H 0.3420(16) 0.3312(8) 0.436(3) 0.014(5) Uiso 1 1 d . . . . .
H5 H 0.090(2) 0.2344(11) 0.384(3) 0.048(9) Uiso 1 1 d . . . . .
H15 H 0.357(2) 0.4977(11) 0.086(3) 0.045(8) Uiso 1 1 d . . . . .
H18A H 0.422(2) 0.4968(12) 0.343(4) 0.054(9) Uiso 1 1 d . . . . .
H19A H 0.130(2) 0.3658(10) 0.066(3) 0.042(8) Uiso 1 1 d . . . . .
H9A H 0.129(2) 0.2695(10) 0.136(3) 0.037(7) Uiso 1 1 d . . . . .
H19B H 0.180(2) 0.4145(11) 0.148(4) 0.048(9) Uiso 1 1 d . . . . .
H10A H 0.174(2) 0.4359(12) 0.537(4) 0.063(10) Uiso 1 1 d . . . . .
H18B H 0.370(2) 0.4596(11) 0.380(4) 0.058(9) Uiso 1 1 d . . . . .
H19C H 0.095(3) 0.3949(11) 0.147(4) 0.054(9) Uiso 1 1 d . . . . .
H2A H 0.473(2) 0.3102(11) 0.342(4) 0.053(9) Uiso 1 1 d . . . . .
H7 H 0.104(2) 0.3656(10) 0.566(3) 0.041(7) Uiso 1 1 d . . . . .
H9B H 0.228(2) 0.2523(10) 0.269(3) 0.038(7) Uiso 1 1 d . . . . .
H2B H 0.512(2) 0.3646(10) 0.401(3) 0.041(8) Uiso 1 1 d . . . . .
H2C H 0.488(2) 0.3305(10) 0.487(3) 0.043(8) Uiso 1 1 d . . . . .
H14 H 0.281(2) 0.4590(12) -0.143(4) 0.058(9) Uiso 1 1 d . . . . .
H9C H 0.140(2) 0.2224(12) 0.226(4) 0.054(9) Uiso 1 1 d . . . . .
H13 H 0.248(2) 0.3736(11) -0.172(4) 0.047(8) Uiso 1 1 d . . . . .
H10B H 0.167(3) 0.4379(13) 0.385(4) 0.070(11) Uiso 1 1 d . . . . .
H6 H 0.062(2) 0.2820(11) 0.533(3) 0.050(8) Uiso 1 1 d . . . . .
H10C H 0.254(3) 0.4229(13) 0.522(4) 0.058(11) Uiso 1 1 d . . . . .
H18C H 0.473(3) 0.4470(12) 0.414(4) 0.058(10) Uiso 1 1 d . . . . .
H17A H 0.237(3) 0.2986(11) 0.047(4) 0.062(10) Uiso 1 1 d . . . . .
H17B H 0.335(3) 0.2900(14) 0.088(5) 0.079(13) Uiso 1 1 d . . . . .
H17C H 0.252(3) 0.2973(13) -0.069(5) 0.079(12) Uiso 1 1 d . . . . .
C2 C 0.47035(17) 0.33951(10) 0.3951(3) 0.0295(5) Uani 1 1 d . . . . .
C3 C 0.17673(16) 0.33630(8) 0.3611(2) 0.0241(4) Uani 1 1 d . . . . .
C4 C 0.14923(16) 0.28634(9) 0.3330(2) 0.0265(5) Uani 1 1 d . . . . .
C5 C 0.10673(18) 0.26626(11) 0.4001(3) 0.0341(5) Uani 1 1 d . . . . .
C6 C 0.09190(18) 0.29499(11) 0.4888(3) 0.0401(7) Uani 1 1 d . . . . .
C7 C 0.11904(18) 0.34419(12) 0.5132(3) 0.0384(6) Uani 1 1 d . . . . .
C8 C 0.16286(17) 0.36636(10) 0.4506(3) 0.0314(5) Uani 1 1 d . . . . .
C9 C 0.1618(2) 0.25489(10) 0.2326(3) 0.0320(5) Uani 1 1 d . . . . .
C10 C 0.1961(3) 0.41934(12) 0.4818(4) 0.0446(7) Uani 1 1 d . . . . .
C11 C 0.34265(15) 0.38720(7) 0.1787(2) 0.0201(4) Uani 1 1 d . . . . .
C12 C 0.30237(15) 0.36255(8) 0.0458(2) 0.0232(4) Uani 1 1 d . . . . .
C13 C 0.2805(2) 0.39088(10) -0.0748(3) 0.0360(6) Uani 1 1 d . . . . .
C14 C 0.3002(2) 0.44122(11) -0.0599(3) 0.0460(7) Uani 1 1 d . . . . .
C15 C 0.3423(2) 0.46462(10) 0.0736(3) 0.0417(6) Uani 1 1 d . . . . .
C16 C 0.36498(17) 0.43801(8) 0.1973(3) 0.0269(5) Uani 1 1 d . . . . .
C17 C 0.2839(2) 0.30771(9) 0.0310(3) 0.0309(5) Uani 1 1 d . . . . .
C18 C 0.4104(2) 0.46288(10) 0.3437(4) 0.0422(7) Uani 1 1 d . . . . .
C19 C 0.15381(18) 0.38568(10) 0.1532(3) 0.0291(5) Uani 1 1 d . . . . .


_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
Cl1S C1S 1.662(8) . ?
Cl1S C1S 1.815(8) 2 ?
N1 C1 1.315(3) . ?
N1 C3 1.458(2) . ?
N1 C19 1.471(3) . ?
N2 C1 1.314(2) . ?
N2 C11 1.445(3) . ?
N2 C2 1.477(3) . ?
C1 H1 0.90(2) . ?
C1S Cl1S 1.815(8) 2 ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
C2 H2A 1.00(3) . ?
C2 H2B 0.94(3) . ?
C2 H2C 0.92(3) . ?
C3 C4 1.393(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.502(3) . ?
C5 C6 1.376(4) . ?
C5 H5 0.89(3) . ?
C6 C7 1.371(4) . ?
C6 H6 0.94(3) . ?
C7 C8 1.394(3) . ?
C7 H7 0.94(3) . ?
C8 C10 1.493(4) . ?
C9 H9A 0.96(3) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.93(3) . ?
C10 H10A 0.99(3) . ?
C10 H10B 1.02(4) . ?
C10 H10C 0.80(4) . ?
C11 C12 1.388(3) . ?
C11 C16 1.397(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.493(3) . ?
C13 C14 1.378(4) . ?
C13 H13 1.00(3) . ?
C14 C15 1.373(4) . ?
C14 H14 0.92(3) . ?
C15 C16 1.392(4) . ?
C15 H15 0.91(3) . ?
C16 C18 1.498(4) . ?
C17 H17A 0.93(3) . ?
C17 H17B 0.86(4) . ?
C17 H17C 0.96(4) . ?
C18 H18A 0.93(3) . ?
C18 H18B 0.97(3) . ?
C18 H18C 0.98(3) . ?
C19 H19A 0.96(3) . ?
C19 H19B 0.90(3) . ?
C19 H19C 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1S Cl1S C1S 35.8(5) . 2 ?
C1 N1 C3 116.16(18) . . ?
C1 N1 C19 127.28(17) . . ?
C3 N1 C19 116.30(17) . . ?
C1 N2 C11 126.53(18) . . ?
C1 N2 C2 118.12(19) . . ?
C11 N2 C2 115.33(16) . . ?
N2 C1 N1 130.4(2) . . ?
N2 C1 H1 114.9(14) . . ?
N1 C1 H1 114.7(14) . . ?
Cl1S C1S Cl1S 113.2(4) . 2 ?
Cl1S C1S H1S1 108.9 . . ?
Cl1S C1S H1S1 108.9 2 . ?
Cl1S C1S H1S2 108.9 . . ?
Cl1S C1S H1S2 108.9 2 . ?
H1S1 C1S H1S2 107.8 . . ?
N2 C2 H2A 107.8(19) . . ?
N2 C2 H2B 108.3(18) . . ?
H2A C2 H2B 109(2) . . ?
N2 C2 H2C 110.6(18) . . ?
H2A C2 H2C 110(2) . . ?
H2B C2 H2C 110(3) . . ?
C4 C3 C8 123.25(19) . . ?
C4 C3 N1 118.05(18) . . ?
C8 C3 N1 118.69(19) . . ?
C5 C4 C3 117.1(2) . . ?
C5 C4 C9 120.3(2) . . ?
C3 C4 C9 122.59(19) . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 121.0(19) . . ?
C4 C5 H5 117.9(19) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 117.7(18) . . ?
C5 C6 H6 121.9(18) . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 122.4(17) . . ?
C8 C7 H7 116.1(17) . . ?
C3 C8 C7 116.8(2) . . ?
C3 C8 C10 121.7(2) . . ?
C7 C8 C10 121.5(2) . . ?
C4 C9 H9A 110.9(16) . . ?
C4 C9 H9B 110.5(17) . . ?
H9A C9 H9B 107(2) . . ?
C4 C9 H9C 112.1(19) . . ?
H9A C9 H9C 110(3) . . ?
H9B C9 H9C 106(2) . . ?
C8 C10 H10A 110.5(19) . . ?
C8 C10 H10B 109(2) . . ?
H10A C10 H10B 109(3) . . ?
C8 C10 H10C 114(3) . . ?
H10A C10 H10C 111(3) . . ?
H10B C10 H10C 103(3) . . ?
C12 C11 C16 123.3(2) . . ?
C12 C11 N2 118.95(18) . . ?
C16 C11 N2 117.63(19) . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 C17 122.1(2) . . ?
C13 C12 C17 120.6(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 122.0(17) . . ?
C12 C13 H13 117.6(17) . . ?
C15 C14 C13 121.2(2) . . ?
C15 C14 H14 121(2) . . ?
C13 C14 H14 118(2) . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 122.2(19) . . ?
C16 C15 H15 117.2(19) . . ?
C15 C16 C11 117.1(2) . . ?
C15 C16 C18 121.4(2) . . ?
C11 C16 C18 121.5(2) . . ?
C12 C17 H17A 112.4(19) . . ?
C12 C17 H17B 114(3) . . ?
H17A C17 H17B 108(3) . . ?
C12 C17 H17C 111(2) . . ?
H17A C17 H17C 100(3) . . ?
H17B C17 H17C 111(3) . . ?
C16 C18 H18A 114(2) . . ?
C16 C18 H18B 112(2) . . ?
H18A C18 H18B 107(3) . . ?
C16 C18 H18C 108.6(19) . . ?
H18A C18 H18C 107(3) . . ?
H18B C18 H18C 108(3) . . ?
N1 C19 H19A 113.3(17) . . ?
N1 C19 H19B 113(2) . . ?
H19A C19 H19B 111(3) . . ?
N1 C19 H19C 109.7(19) . . ?
H19A C19 H19C 104(3) . . ?
H19B C19 H19C 106(3) . . ?

_refine_diff_density_max         0.873
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.080

_shelxl_version_number           2014-3

