# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_CH_B1_0025
_database_code_depnum_ccdc_archive 'CCDC 1851428'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Petr Motloch'
_cambridge_user_crsid            pm567
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             PM-219
_cambridge_data_id               CH_B1_0025

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 N5 +, I -'
_chemical_formula_sum            'C12 H24 I N5'
_chemical_formula_weight         365.26

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3581(5)
_cell_length_b                   8.7357(5)
_cell_length_c                   12.2791(8)
_cell_angle_alpha                104.472(4)
_cell_angle_beta                 102.631(5)
_cell_angle_gamma                104.192(4)
_cell_volume                     803.31(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2572
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      65.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    15.600
_shelx_estimated_absorpt_T_min   0.219
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4400
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8605
_diffrn_reflns_av_unetI/netI     0.1099
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.895
_diffrn_reflns_theta_max         67.347
_diffrn_reflns_theta_full        67.347
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2822
_reflns_number_gt                1951
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0533P)²+4.3234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2822
_refine_ls_number_parameters     182
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0655
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.103
_refine_diff_density_min         -1.046
_refine_diff_density_rms         0.165

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 0.11663(10) 0.91994(8) 0.34712(7) 0.0427(3) Uani 1 1 d . . . . .
N1 N 0.3454(11) 0.3410(9) 0.5373(8) 0.041(2) Uani 1 1 d . . . . .
H1A H 0.441213 0.356508 0.516800 0.050 Uiso 1 1 calc R U . . .
H1B H 0.281949 0.239517 0.528275 0.050 Uiso 1 1 calc R U . . .
N2 N 0.3900(9) 0.6231(9) 0.5958(7) 0.0281(18) Uani 1 1 d . . . . .
N3 N 0.1463(10) 0.4366(9) 0.6110(7) 0.0328(19) Uani 1 1 d . . . . .
H3 H 0.089326 0.333019 0.602318 0.039 Uiso 1 1 calc R U . . .
N4 N 0.4345(10) 0.9026(9) 0.6572(7) 0.0301(18) Uani 1 1 d . . . . .
H4 H 0.533311 0.908090 0.641674 0.036 Uiso 1 1 calc R U . A 1
N5 N -0.0672(10) 0.5116(10) 0.6771(7) 0.035(2) Uani 1 1 d . . . . .
H5 H -0.118653 0.403624 0.656982 0.042 Uiso 1 1 calc R U . B 1
C1 C 0.2969(12) 0.4701(11) 0.5815(8) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.3318(12) 0.7501(11) 0.6407(8) 0.027(2) Uani 1 1 d . . . . .
C3 C 0.1734(12) 0.7240(11) 0.6685(9) 0.033(2) Uani 1 1 d . . . . .
H3A H 0.131778 0.813851 0.695794 0.039 Uiso 1 1 calc R U . . .
C4 C 0.0830(11) 0.5621(11) 0.6539(8) 0.024(2) Uani 1 1 d . . . . .
C5 C 0.4036(10) 1.0600(10) 0.6977(7) 0.030(2) Uani 0.5 1 d D . P C 1
H5A H 0.277703 1.039424 0.667767 0.036 Uiso 0.5 1 calc R U P C 1
H5B H 0.460472 1.135043 0.659160 0.036 Uiso 0.5 1 calc R U P C 1
C6 C 0.4585(14) 1.1510(11) 0.8239(7) 0.067(4) Uani 0.5 1 d D U P C 1
H6 H 0.381601 1.078438 0.855634 0.080 Uiso 0.5 1 calc R U P C 1
C7 C 0.4162(19) 1.3074(12) 0.8513(10) 0.074(4) Uani 0.5 1 d D U P C 1
H7A H 0.298291 1.288305 0.803576 0.111 Uiso 0.5 1 calc R U P C 1
H7B H 0.424297 1.345688 0.935093 0.111 Uiso 0.5 1 calc R U P C 1
H7C H 0.497706 1.392376 0.833617 0.111 Uiso 0.5 1 calc R U P C 1
C8 C 0.630(2) 1.167(2) 0.8904(13) 0.056(6) Uani 0.5 1 d D U P C 1
H8A H 0.652222 1.230260 0.973281 0.084 Uiso 0.5 1 calc R U P C 1
H8B H 0.640592 1.056365 0.884383 0.084 Uiso 0.5 1 calc R U P C 1
H8C H 0.715091 1.226542 0.858821 0.084 Uiso 0.5 1 calc R U P C 1
C5A C 0.4036(10) 1.0600(10) 0.6977(7) 0.030(2) Uani 0.5 1 d D . P C 2
H5C H 0.277703 1.039424 0.667767 0.036 Uiso 0.5 1 calc R U P C 2
H5D H 0.460472 1.135043 0.659160 0.036 Uiso 0.5 1 calc R U P C 2
C6A C 0.4585(14) 1.1510(11) 0.8239(7) 0.067(4) Uani 0.5 1 d D U P C 2
H6A H 0.586945 1.193411 0.841262 0.080 Uiso 0.5 1 calc R U P C 2
C7A C 0.4162(19) 1.3074(12) 0.8513(10) 0.074(4) Uani 0.5 1 d D U P C 2
H7D H 0.433027 1.361019 0.791674 0.111 Uiso 0.5 1 calc R U P C 2
H7E H 0.295375 1.283183 0.851490 0.111 Uiso 0.5 1 calc R U P C 2
H7F H 0.491892 1.382167 0.929122 0.111 Uiso 0.5 1 calc R U P C 2
C8A C 0.441(3) 1.055(2) 0.9022(13) 0.071(8) Uani 0.5 1 d D U P C 2
H8D H 0.482278 1.129395 0.983764 0.106 Uiso 0.5 1 calc R U P C 2
H8E H 0.319735 0.989240 0.883426 0.106 Uiso 0.5 1 calc R U P C 2
H8F H 0.510653 0.979068 0.892933 0.106 Uiso 0.5 1 calc R U P C 2
C9 C -0.1505(12) 0.6220(11) 0.7329(7) 0.038(3) Uani 0.5 1 d D . P D 1
H9A H -0.276768 0.564574 0.702126 0.045 Uiso 0.5 1 calc R U P D 1
H9B H -0.127133 0.721423 0.706660 0.045 Uiso 0.5 1 calc R U P D 1
C10 C -0.1036(14) 0.6806(12) 0.8623(8) 0.061(3) Uani 0.5 1 d D U P D 1
H10 H -0.130813 0.577745 0.885792 0.074 Uiso 0.5 1 calc R U P D 1
C11 C -0.2139(19) 0.7757(17) 0.9052(11) 0.099(5) Uani 0.5 1 d D U P D 1
H11A H -0.335735 0.712565 0.862900 0.148 Uiso 0.5 1 calc R U P D 1
H11B H -0.194087 0.794048 0.989768 0.148 Uiso 0.5 1 calc R U P D 1
H11C H -0.185107 0.883425 0.891268 0.148 Uiso 0.5 1 calc R U P D 1
C12 C 0.0792(17) 0.768(3) 0.9218(14) 0.067(7) Uani 0.5 1 d D U P D 1
H12A H 0.099146 0.802388 1.007212 0.100 Uiso 0.5 1 calc R U P D 1
H12B H 0.146071 0.693365 0.900533 0.100 Uiso 0.5 1 calc R U P D 1
H12C H 0.115561 0.866315 0.897601 0.100 Uiso 0.5 1 calc R U P D 1
C9A C -0.1505(12) 0.6220(11) 0.7329(7) 0.038(3) Uani 0.5 1 d D . P D 2
H9C H -0.276768 0.564574 0.702126 0.045 Uiso 0.5 1 calc R U P D 2
H9D H -0.127133 0.721423 0.706660 0.045 Uiso 0.5 1 calc R U P D 2
C10A C -0.1036(14) 0.6806(12) 0.8623(8) 0.061(3) Uani 0.5 1 d D U P D 2
H10A H 0.012546 0.766713 0.886938 0.074 Uiso 0.5 1 calc R U P D 2
C11A C -0.2139(19) 0.7757(17) 0.9052(11) 0.099(5) Uani 0.5 1 d D U P D 2
H11D H -0.226987 0.853486 0.861155 0.148 Uiso 0.5 1 calc R U P D 2
H11E H -0.327892 0.698396 0.893560 0.148 Uiso 0.5 1 calc R U P D 2
H11F H -0.160049 0.838156 0.989222 0.148 Uiso 0.5 1 calc R U P D 2
C12A C -0.073(3) 0.560(2) 0.9197(14) 0.072(8) Uani 0.5 1 d D U P D 2
H12D H -0.042554 0.610639 1.005226 0.108 Uiso 0.5 1 calc R U P D 2
H12E H -0.177243 0.462944 0.892526 0.108 Uiso 0.5 1 calc R U P D 2
H12F H 0.022862 0.524196 0.900044 0.108 Uiso 0.5 1 calc R U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.321(11) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C1 1.318(11) . ?
N2 C2 1.359(11) . ?
N3 C1 1.369(11) . ?
N3 C4 1.370(11) . ?
N3 H3 0.8800 . ?
N4 C2 1.334(11) . ?
N4 C5A 1.447(10) . ?
N4 C5 1.447(10) . ?
N4 H4 0.8800 . ?
N5 C4 1.341(11) . ?
N5 C9A 1.446(11) . ?
N5 C9 1.446(11) . ?
N5 H5 0.8800 . ?
C2 C3 1.418(12) . ?
C3 C4 1.376(12) . ?
C3 H3A 0.9500 . ?
C5 C6 1.463(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.441(10) . ?
C6 C7 1.471(8) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5A C6A 1.463(8) . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A C8A 1.436(10) . ?
C6A C7A 1.471(8) . ?
C6A H6A 1.0000 . ?
C7A H7D 0.9800 . ?
C7A H7E 0.9800 . ?
C7A H7F 0.9800 . ?
C8A H8D 0.9800 . ?
C8A H8E 0.9800 . ?
C8A H8F 0.9800 . ?
C9 C10 1.472(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C12 1.453(10) . ?
C10 C11 1.478(8) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C9A C10A 1.472(8) . ?
C9A H9C 0.9900 . ?
C9A H9D 0.9900 . ?
C10A C12A 1.450(10) . ?
C10A C11A 1.478(8) . ?
C10A H10A 1.0000 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 118.0(8) . . ?
C1 N3 C4 120.9(7) . . ?
C1 N3 H3 119.6 . . ?
C4 N3 H3 119.6 . . ?
C2 N4 C5A 128.0(7) . . ?
C2 N4 C5 128.0(7) . . ?
C2 N4 H4 116.0 . . ?
C5 N4 H4 116.0 . . ?
C4 N5 C9A 124.7(8) . . ?
C4 N5 C9 124.7(8) . . ?
C4 N5 H5 117.7 . . ?
C9 N5 H5 117.7 . . ?
N2 C1 N1 121.0(8) . . ?
N2 C1 N3 122.2(8) . . ?
N1 C1 N3 116.8(8) . . ?
N4 C2 N2 115.3(8) . . ?
N4 C2 C3 121.8(8) . . ?
N2 C2 C3 122.9(8) . . ?
C4 C3 C2 116.6(8) . . ?
C4 C3 H3A 121.7 . . ?
C2 C3 H3A 121.7 . . ?
N5 C4 N3 114.7(8) . . ?
N5 C4 C3 125.9(8) . . ?
N3 C4 C3 119.4(8) . . ?
N4 C5 C6 119.6(7) . . ?
N4 C5 H5A 107.4 . . ?
C6 C5 H5A 107.4 . . ?
N4 C5 H5B 107.4 . . ?
C6 C5 H5B 107.4 . . ?
H5A C5 H5B 106.9 . . ?
C8 C6 C5 116.9(8) . . ?
C8 C6 C7 113.4(8) . . ?
C5 C6 C7 113.3(6) . . ?
C8 C6 H6 103.7 . . ?
C5 C6 H6 103.7 . . ?
C7 C6 H6 103.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C5A C6A 119.6(7) . . ?
N4 C5A H5C 107.4 . . ?
C6A C5A H5C 107.4 . . ?
N4 C5A H5D 107.4 . . ?
C6A C5A H5D 107.4 . . ?
H5C C5A H5D 106.9 . . ?
C8A C6A C5A 117.3(8) . . ?
C8A C6A C7A 117.5(8) . . ?
C5A C6A C7A 113.3(6) . . ?
C8A C6A H6A 101.6 . . ?
C5A C6A H6A 101.6 . . ?
C7A C6A H6A 101.6 . . ?
C6A C7A H7D 109.5 . . ?
C6A C7A H7E 109.5 . . ?
H7D C7A H7E 109.5 . . ?
C6A C7A H7F 109.5 . . ?
H7D C7A H7F 109.5 . . ?
H7E C7A H7F 109.5 . . ?
C6A C8A H8D 109.5 . . ?
C6A C8A H8E 109.5 . . ?
H8D C8A H8E 109.5 . . ?
C6A C8A H8F 109.5 . . ?
H8D C8A H8F 109.5 . . ?
H8E C8A H8F 109.5 . . ?
N5 C9 C10 118.6(7) . . ?
N5 C9 H9A 107.7 . . ?
C10 C9 H9A 107.7 . . ?
N5 C9 H9B 107.7 . . ?
C10 C9 H9B 107.7 . . ?
H9A C9 H9B 107.1 . . ?
C12 C10 C9 114.7(8) . . ?
C12 C10 C11 112.2(8) . . ?
C9 C10 C11 112.0(6) . . ?
C12 C10 H10 105.7 . . ?
C9 C10 H10 105.7 . . ?
C11 C10 H10 105.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N5 C9A C10A 118.6(7) . . ?
N5 C9A H9C 107.7 . . ?
C10A C9A H9C 107.7 . . ?
N5 C9A H9D 107.7 . . ?
C10A C9A H9D 107.7 . . ?
H9C C9A H9D 107.1 . . ?
C12A C10A C9A 115.8(8) . . ?
C12A C10A C11A 115.8(8) . . ?
C9A C10A C11A 112.0(6) . . ?
C12A C10A H10A 103.8 . . ?
C9A C10A H10A 103.8 . . ?
C11A C10A H10A 103.8 . . ?
C10A C11A H11D 109.5 . . ?
C10A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C10A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
C10A C12A H12D 109.5 . . ?
C10A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C10A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 179.3(9) . . . . ?
C2 N2 C1 N3 -0.4(14) . . . . ?
C4 N3 C1 N2 1.9(15) . . . . ?
C4 N3 C1 N1 -177.8(9) . . . . ?
C5A N4 C2 N2 176.6(8) . . . . ?
C5 N4 C2 N2 176.6(8) . . . . ?
C5A N4 C2 C3 -3.5(15) . . . . ?
C5 N4 C2 C3 -3.5(15) . . . . ?
C1 N2 C2 N4 177.6(8) . . . . ?
C1 N2 C2 C3 -2.3(14) . . . . ?
N4 C2 C3 C4 -176.5(9) . . . . ?
N2 C2 C3 C4 3.4(15) . . . . ?
C9A N5 C4 N3 174.0(8) . . . . ?
C9 N5 C4 N3 174.0(8) . . . . ?
C9A N5 C4 C3 -6.6(16) . . . . ?
C9 N5 C4 C3 -6.6(16) . . . . ?
C1 N3 C4 N5 178.8(8) . . . . ?
C1 N3 C4 C3 -0.7(14) . . . . ?
C2 C3 C4 N5 178.7(9) . . . . ?
C2 C3 C4 N3 -1.9(14) . . . . ?
C2 N4 C5 C6 89.6(12) . . . . ?
N4 C5 C6 C8 46.1(14) . . . . ?
N4 C5 C6 C7 -179.2(9) . . . . ?
C2 N4 C5A C6A 89.6(12) . . . . ?
N4 C5A C6A C8A -37.2(15) . . . . ?
N4 C5A C6A C7A -179.2(9) . . . . ?
C4 N5 C9 C10 -88.0(11) . . . . ?
N5 C9 C10 C12 57.3(14) . . . . ?
N5 C9 C10 C11 -173.3(9) . . . . ?
C4 N5 C9A C10A -88.0(11) . . . . ?
N5 C9A C10A C12A -37.6(15) . . . . ?
N5 C9A C10A C11A -173.3(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N2 0.88 2.19 3.025(11) 159.0 2_666 yes
N1 H1B I1 0.88 2.88 3.598(8) 139.5 1_545 yes
N3 H3 I1 0.88 2.74 3.568(7) 156.8 2_566 yes
N4 H4^a I1 0.88 2.90 3.709(7) 153.9 2_676 yes
N5 H5^a I1 0.88 2.82 3.619(8) 151.9 2_566 yes

####################################################################### 
# 
# 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_CH_B1_0026
_database_code_depnum_ccdc_archive 'CCDC 1851429'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2018-06-25 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2018/1

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.0  (Andrew D. Bond, July 2015)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Petr Motloch'
_cambridge_user_crsid            pm567
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             PM-218
_cambridge_data_id               CH_B1_0026

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H25 N5 2+, 2(Cl -)'
_chemical_formula_sum            'C12 H25 Cl2 N5'
_chemical_formula_weight         310.27

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'

_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, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   17.7220(6)
_cell_length_b                   17.7220(6)
_cell_length_c                   28.3433(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8901.8(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    4255
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      53.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.926
_exptl_crystal_F_000             2656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.595
_shelx_estimated_absorpt_T_min   0.713
_shelx_estimated_absorpt_T_max   0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'

_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27017
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.1446
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         54.398
_diffrn_reflns_theta_full        54.398
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2729
_reflns_number_gt                1728
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.1116P)²+10.2674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2729
_refine_ls_number_parameters     192
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1176
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2281
_refine_ls_wR_factor_gt          0.1971
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.053

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.40621(15) 0.81501(9) 0.45040(8) 0.1251(8) Uani 1 1 d . . . . .
Cl2 Cl 0.35503(8) 0.69383(8) 0.65555(6) 0.0827(5) Uani 1 1 d . . . . .
N1 N 0.3927(3) 0.7358(3) 0.5488(2) 0.0885(15) Uani 1 1 d . . . . .
H1A H 0.399706 0.772907 0.529183 0.106 Uiso 1 1 calc R U . . .
H1B H 0.386170 0.744887 0.578660 0.106 Uiso 1 1 calc R U . . .
N2 N 0.4017(3) 0.6517(2) 0.48759(19) 0.0783(13) Uani 1 1 d . . . . .
H2A H 0.405314 0.689412 0.468103 0.094 Uiso 1 1 calc R U . . .
N3 N 0.3808(2) 0.6090(2) 0.56334(18) 0.0710(12) Uani 1 1 d . . . . .
H3B H 0.369738 0.618715 0.592622 0.085 Uiso 1 1 calc R U . . .
N4 N 0.4174(4) 0.5694(3) 0.4249(2) 0.0951(16) Uani 1 1 d . . . . .
H4A H 0.417994 0.522915 0.415056 0.114 Uiso 1 1 calc R U . A 1
N5 N 0.3778(3) 0.4827(3) 0.5821(2) 0.0871(15) Uani 1 1 d . . . . .
H5A H 0.375223 0.436198 0.572336 0.105 Uiso 1 1 calc R U . . .
C1 C 0.3918(3) 0.6661(3) 0.5333(3) 0.0747(16) Uani 1 1 d . . . . .
C2 C 0.4065(3) 0.5789(3) 0.4698(2) 0.0770(16) Uani 1 1 d . . . . .
C3 C 0.3980(3) 0.5208(3) 0.5024(2) 0.0752(16) Uani 1 1 d . . . . .
H3A H 0.400270 0.470409 0.492108 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3864(3) 0.5353(3) 0.5488(2) 0.0717(15) Uani 1 1 d . . . . .
C5 C 0.4289(5) 0.6271(4) 0.3889(3) 0.117(3) Uani 0.725(19) 1 d D . P B 1
H5B H 0.471403 0.611948 0.368939 0.141 Uiso 0.725(19) 1 calc R U P B 1
H5C H 0.442846 0.674412 0.404531 0.141 Uiso 0.725(19) 1 calc R U P B 1
C6 C 0.3629(7) 0.6416(6) 0.3583(4) 0.144(6) Uani 0.725(19) 1 d D U P B 1
H6 H 0.319025 0.656319 0.377821 0.173 Uiso 0.725(19) 1 calc R U P B 1
C7 C 0.3443(9) 0.5731(8) 0.3304(5) 0.246(8) Uani 0.725(19) 1 d D U P B 1
H7A H 0.301016 0.583344 0.310461 0.369 Uiso 0.725(19) 1 calc R U P B 1
H7B H 0.387174 0.559565 0.310826 0.369 Uiso 0.725(19) 1 calc R U P B 1
H7C H 0.332710 0.531808 0.351598 0.369 Uiso 0.725(19) 1 calc R U P B 1
C8 C 0.3816(13) 0.7040(8) 0.3239(6) 0.216(9) Uani 0.725(19) 1 d D U P B 1
H8A H 0.338403 0.713591 0.303830 0.323 Uiso 0.725(19) 1 calc R U P B 1
H8B H 0.394181 0.749541 0.341269 0.323 Uiso 0.725(19) 1 calc R U P B 1
H8C H 0.424342 0.689066 0.304693 0.323 Uiso 0.725(19) 1 calc R U P B 1
C5A C 0.4289(5) 0.6271(4) 0.3889(3) 0.117(3) Uani 0.275(19) 1 d D . P B 2
H5A1 H 0.479369 0.648551 0.393176 0.141 Uiso 0.275(19) 1 calc R U P B 2
H5A2 H 0.392401 0.667758 0.394422 0.141 Uiso 0.275(19) 1 calc R U P B 2
C6A C 0.4216(11) 0.6025(13) 0.3390(4) 0.151(16) Uani 0.275(19) 1 d D U P B 2
H6A H 0.458560 0.561827 0.332798 0.182 Uiso 0.275(19) 1 calc R U P B 2
C7A C 0.3443(9) 0.5731(8) 0.3304(5) 0.246(8) Uani 0.275(19) 1 d D U P B 2
H7A1 H 0.339950 0.557157 0.297757 0.369 Uiso 0.275(19) 1 calc R U P B 2
H7A2 H 0.334874 0.530512 0.351008 0.369 Uiso 0.275(19) 1 calc R U P B 2
H7A3 H 0.307753 0.612556 0.336721 0.369 Uiso 0.275(19) 1 calc R U P B 2
C8A C 0.437(2) 0.667(2) 0.3067(6) 0.155(15) Uani 0.275(19) 1 d D U P B 2
H8A1 H 0.487860 0.685908 0.312546 0.233 Uiso 0.275(19) 1 calc R U P B 2
H8A2 H 0.433443 0.650183 0.274249 0.233 Uiso 0.275(19) 1 calc R U P B 2
H8A3 H 0.400982 0.706909 0.312371 0.233 Uiso 0.275(19) 1 calc R U P B 2
C9 C 0.3724(5) 0.4943(4) 0.6322(3) 0.108(2) Uani 1 1 d D . . . .
H9A H 0.338630 0.537187 0.637864 0.130 Uiso 1 1 calc R U . . .
H9B H 0.422380 0.508380 0.644042 0.130 Uiso 1 1 calc R U . . .
C10 C 0.3449(6) 0.4298(6) 0.6601(3) 0.154(4) Uani 1 1 d D U . . .
H10 H 0.379945 0.386913 0.655626 0.184 Uiso 1 1 calc R U . . .
C11 C 0.2680(6) 0.4060(7) 0.6452(4) 0.190(5) Uani 1 1 d D U . . .
H11A H 0.251806 0.363566 0.664281 0.285 Uiso 1 1 calc R U . . .
H11B H 0.233154 0.447670 0.649383 0.285 Uiso 1 1 calc R U . . .
H11C H 0.269025 0.391309 0.612257 0.285 Uiso 1 1 calc R U . . .
C12 C 0.3437(8) 0.4502(8) 0.7113(3) 0.220(7) Uani 1 1 d D U . . .
H12A H 0.325539 0.407548 0.729516 0.331 Uiso 1 1 calc R U . . .
H12B H 0.394228 0.463285 0.721505 0.331 Uiso 1 1 calc R U . . .
H12C H 0.310368 0.492969 0.716077 0.331 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.311(7) . ?
N1 H1A 0.8700 . ?
N1 H1B 0.8700 . ?
N2 C1 1.331(8) . ?
N2 C2 1.388(7) . ?
N2 H2A 0.8700 . ?
N3 C1 1.338(8) . ?
N3 C4 1.372(7) . ?
N3 H3B 0.8700 . ?
N4 C2 1.298(8) . ?
N4 C5A 1.459(9) . ?
N4 C5 1.459(9) . ?
N4 H4A 0.8700 . ?
N5 C4 1.335(8) . ?
N5 C9 1.440(9) . ?
N5 H5A 0.8700 . ?
C2 C3 1.393(9) . ?
C3 C4 1.355(9) . ?
C3 H3A 0.9400 . ?
C5 C6 1.477(9) . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.485(10) . ?
C6 C8 1.511(10) . ?
C6 H6 0.9900 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C5A C6A 1.485(11) . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C6A C7A 1.485(11) . ?
C6A C8A 1.490(11) . ?
C6A H6A 0.9900 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C7A H7A3 0.9700 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C8A H8A3 0.9700 . ?
C9 C10 1.472(8) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.488(9) . ?
C10 C12 1.495(9) . ?
C10 H10 0.9900 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 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
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 C2 122.7(5) . . ?
C1 N2 H2A 118.7 . . ?
C2 N2 H2A 118.7 . . ?
C1 N3 C4 121.2(6) . . ?
C1 N3 H3B 119.4 . . ?
C4 N3 H3B 119.4 . . ?
C2 N4 C5A 128.0(5) . . ?
C2 N4 C5 128.0(5) . . ?
C2 N4 H4A 116.0 . . ?
C5 N4 H4A 116.0 . . ?
C4 N5 C9 127.2(5) . . ?
C4 N5 H5A 116.4 . . ?
C9 N5 H5A 116.4 . . ?
N1 C1 N2 120.4(6) . . ?
N1 C1 N3 120.0(6) . . ?
N2 C1 N3 119.6(5) . . ?
N4 C2 N2 119.0(5) . . ?
N4 C2 C3 124.9(5) . . ?
N2 C2 C3 116.0(6) . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3A 119.3 . . ?
C2 C3 H3A 119.3 . . ?
N5 C4 C3 124.7(5) . . ?
N5 C4 N3 116.4(6) . . ?
C3 C4 N3 118.9(5) . . ?
N4 C5 C6 115.0(7) . . ?
N4 C5 H5B 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N4 C5 H5C 108.5 . . ?
C6 C5 H5C 108.5 . . ?
H5B C5 H5C 107.5 . . ?
C5 C6 C7 110.3(7) . . ?
C5 C6 C8 109.4(8) . . ?
C7 C6 C8 107.7(8) . . ?
C5 C6 H6 109.8 . . ?
C7 C6 H6 109.8 . . ?
C8 C6 H6 109.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C5A C6A 116.6(10) . . ?
N4 C5A H5A1 108.1 . . ?
C6A C5A H5A1 108.1 . . ?
N4 C5A H5A2 108.1 . . ?
C6A C5A H5A2 108.1 . . ?
H5A1 C5A H5A2 107.3 . . ?
C7A C6A C5A 109.9(9) . . ?
C7A C6A C8A 109.9(10) . . ?
C5A C6A C8A 110.0(10) . . ?
C7A C6A H6A 109.0 . . ?
C5A C6A H6A 109.0 . . ?
C8A C6A H6A 109.0 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C6A C8A H8A1 109.5 . . ?
C6A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C6A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
N5 C9 C10 116.2(6) . . ?
N5 C9 H9A 108.2 . . ?
C10 C9 H9A 108.2 . . ?
N5 C9 H9B 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C9 C10 C11 111.7(7) . . ?
C9 C10 C12 109.8(7) . . ?
C11 C10 C12 109.3(7) . . ?
C9 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C12 C10 H10 108.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 175.5(5) . . . . ?
C2 N2 C1 N3 -4.8(8) . . . . ?
C4 N3 C1 N1 -174.0(5) . . . . ?
C4 N3 C1 N2 6.2(8) . . . . ?
C5A N4 C2 N2 2.7(11) . . . . ?
C5 N4 C2 N2 2.7(11) . . . . ?
C5A N4 C2 C3 -178.2(7) . . . . ?
C5 N4 C2 C3 -178.2(7) . . . . ?
C1 N2 C2 N4 -178.9(6) . . . . ?
C1 N2 C2 C3 2.0(8) . . . . ?
N4 C2 C3 C4 -179.7(6) . . . . ?
N2 C2 C3 C4 -0.6(8) . . . . ?
C9 N5 C4 C3 173.8(7) . . . . ?
C9 N5 C4 N3 -8.2(9) . . . . ?
C2 C3 C4 N5 -180.0(5) . . . . ?
C2 C3 C4 N3 2.1(8) . . . . ?
C1 N3 C4 N5 177.0(5) . . . . ?
C1 N3 C4 C3 -4.9(8) . . . . ?
C2 N4 C5 C6 -104.2(9) . . . . ?
N4 C5 C6 C7 -63.7(12) . . . . ?
N4 C5 C6 C8 178.1(11) . . . . ?
C2 N4 C5A C6A -165.7(11) . . . . ?
N4 C5A C6A C7A 60.8(18) . . . . ?
N4 C5A C6A C8A -178.1(17) . . . . ?
C4 N5 C9 C10 165.7(7) . . . . ?
N5 C9 C10 C11 -59.5(11) . . . . ?
N5 C9 C10 C12 179.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A Cl1 0.87 2.36 3.131(6) 148.3 . yes
N1 H1B Cl2 0.87 2.42 3.187(6) 146.8 . yes
N2 H2A Cl1 0.87 2.28 3.082(5) 152.9 . yes
N3 H3B Cl2 0.87 2.24 3.050(5) 154.6 . yes
N4 H4A^a Cl2 0.87 2.33 3.174(5) 164.1 4_454 yes
N5 H5A Cl1 0.87 2.31 3.151(5) 163.1 14_546 yes

