# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1917395'
loop_
_audit_author_name
_audit_author_address
'Timothy Prior'
;University of Hull
United Kingdom
;
_audit_update_record             
;
2019-05-20 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C15 H36 N5, 2(F6 P), C2 H3 N, Br
;

_chemical_formula_sum            'C17 H39 Br F12 N6 P2'
_chemical_formula_weight         697.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 '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 0.0080 0.0040 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0211 0.0125 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1183 0.1134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.7405 2.7887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9823(8)
_cell_length_b                   13.9805(14)
_cell_length_c                   24.662(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2752.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      2.401
_cell_measurement_theta_max      29.691

_exptl_crystal_description       blade
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_F_000             1424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    2.114
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7831
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'ALS beamline 11.3.1.'
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'omega-phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48044
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.401
_diffrn_reflns_theta_max         29.832
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6085
_reflns_number_gt                5430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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 APEX3 v2016.1.0'
_computing_cell_refinement       'Bruker SAINT v8.37A'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0557P)²+1.9739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2096 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.039(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6085
_refine_ls_number_parameters     350
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.068
_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
Br1 Br 0.68635(7) 0.33324(4) 0.54925(2) 0.03075(15) Uani 1 1 d . . . . .
C1 C 0.4919(7) 0.3523(4) 0.7246(2) 0.0316(12) Uani 1 1 d . . . . .
H1A H 0.381927 0.383574 0.730105 0.038 Uiso 1 1 calc R U . . .
H1B H 0.549229 0.348321 0.760087 0.038 Uiso 1 1 calc R U . . .
C2 C 0.4661(8) 0.2520(4) 0.7017(2) 0.0351(13) Uani 1 1 d . . . . .
H2A H 0.572751 0.215981 0.703756 0.042 Uiso 1 1 calc R U . . .
H2B H 0.381954 0.217669 0.723891 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2253(6) 0.2839(4) 0.6404(2) 0.0258(11) Uani 1 1 d . . . . .
H3A H 0.156347 0.225808 0.645763 0.031 Uiso 1 1 calc R U . . .
H3B H 0.199956 0.328252 0.670599 0.031 Uiso 1 1 calc R U . . .
C4 C 0.1733(6) 0.3300(3) 0.58880(19) 0.0240(9) Uani 1 1 d . . . . .
H4A H 0.205138 0.287215 0.558538 0.029 Uiso 1 1 calc R U . . .
H4B H 0.049569 0.335055 0.588721 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1692(6) 0.4609(3) 0.52626(18) 0.0204(9) Uani 1 1 d . . . . .
H5A H 0.153746 0.531066 0.528728 0.024 Uiso 1 1 calc R U . . .
H5B H 0.057278 0.431620 0.521371 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2752(6) 0.4386(4) 0.4777(2) 0.0227(10) Uani 1 1 d . . . . .
H6A H 0.223529 0.468381 0.445299 0.027 Uiso 1 1 calc R U . . .
H6B H 0.275615 0.368505 0.471953 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4742(6) 0.5759(3) 0.4982(2) 0.0224(10) Uani 1 1 d . . . . .
H7A H 0.362134 0.604343 0.504092 0.027 Uiso 1 1 calc R U . . .
H7B H 0.527648 0.610730 0.467769 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5798(6) 0.5903(3) 0.5493(2) 0.0235(10) Uani 1 1 d . . . . .
H8A H 0.690904 0.560701 0.543285 0.028 Uiso 1 1 calc R U . . .
H8B H 0.597699 0.659728 0.554503 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6254(6) 0.5685(4) 0.6471(2) 0.0261(11) Uani 1 1 d . . . . .
H9A H 0.623633 0.637569 0.656017 0.031 Uiso 1 1 calc R U . . .
H9B H 0.740771 0.551706 0.635857 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5793(6) 0.5115(4) 0.6971(2) 0.0247(11) Uani 1 1 d . . . . .
H10A H 0.654592 0.529397 0.727307 0.030 Uiso 1 1 calc R U . . .
H10B H 0.463037 0.527026 0.707927 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7708(7) 0.3789(4) 0.6886(3) 0.0316(12) Uani 1 1 d . . . . .
H11A H 0.813092 0.385544 0.725747 0.047 Uiso 1 1 calc R U . . .
H11B H 0.836901 0.419352 0.664231 0.047 Uiso 1 1 calc R U . . .
H11C H 0.780007 0.311996 0.677190 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4374(7) 0.1622(4) 0.6160(3) 0.0378(13) Uani 1 1 d . . . . .
H12A H 0.556515 0.145675 0.617994 0.057 Uiso 1 1 calc R U . . .
H12B H 0.403546 0.167500 0.577914 0.057 Uiso 1 1 calc R U . . .
H12C H 0.371099 0.112127 0.633728 0.057 Uiso 1 1 calc R U . . .
C13 C 0.5417(8) 0.4507(5) 0.4303(2) 0.0372(13) Uani 1 1 d . . . . .
H13A H 0.495271 0.490346 0.401202 0.056 Uiso 1 1 calc R U . . .
H13B H 0.526380 0.383000 0.421359 0.056 Uiso 1 1 calc R U . . .
H13C H 0.661487 0.464399 0.434370 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2176(6) 0.4964(3) 0.62057(19) 0.0219(10) Uani 1 1 d . . . . .
H14A H 0.241666 0.466737 0.656183 0.026 Uiso 1 1 calc R U . . .
H14B H 0.099210 0.517528 0.620587 0.026 Uiso 1 1 calc R U . . .
C15 C 0.3310(6) 0.5822(3) 0.61239(19) 0.0207(9) Uani 1 1 d . . . . .
H15A H 0.289074 0.621182 0.581735 0.025 Uiso 1 1 calc R U . . .
H15B H 0.329745 0.622546 0.645389 0.025 Uiso 1 1 calc R U . . .
C16 C -0.0434(7) 0.7428(4) 0.6161(3) 0.0343(13) Uani 1 1 d . . . . .
C17 C -0.0600(9) 0.8141(4) 0.6576(3) 0.0478(16) Uani 1 1 d . . . . .
H17A H 0.040041 0.854766 0.657908 0.072 Uiso 1 1 calc R U . . .
H17B H -0.072336 0.782874 0.692936 0.072 Uiso 1 1 calc R U . . .
H17C H -0.159038 0.853498 0.650269 0.072 Uiso 1 1 calc R U . . .
N1 N 0.5932(5) 0.4089(3) 0.68673(17) 0.0231(9) Uani 1 1 d . . . . .
N2 N 0.4081(5) 0.2558(3) 0.64406(19) 0.0251(9) Uani 1 1 d D . . . .
H2 H 0.463(3) 0.297(2) 0.6283(8) 0.030 Uiso 1 1 calc DR U . . .
N3 N 0.2429(5) 0.4258(3) 0.57760(16) 0.0178(8) Uani 1 1 d . . . . .
N4 N 0.4533(5) 0.4727(3) 0.48231(17) 0.0224(9) Uani 1 1 d D . . . .
H4 H 0.498(2) 0.4404(16) 0.5061(12) 0.027 Uiso 1 1 calc DR U . . .
N5 N 0.5076(5) 0.5500(3) 0.60079(16) 0.0176(8) Uani 1 1 d D . . . .
H5 H 0.5039(5) 0.492(3) 0.5968(3) 0.021 Uiso 1 1 calc DR U . . .
N6 N -0.0312(7) 0.6850(4) 0.5834(3) 0.0478(14) Uani 1 1 d . . . . .
P1 P 0.46024(18) 0.87356(10) 0.59560(7) 0.0322(3) Uani 1 1 d . . . . .
F1 F 0.5034(5) 0.7886(2) 0.63688(16) 0.0454(9) Uani 1 1 d . . . . .
F2 F 0.3389(5) 0.8038(3) 0.56313(19) 0.0642(12) Uani 1 1 d . . . . .
F3 F 0.6129(4) 0.8415(3) 0.55804(16) 0.0458(9) Uani 1 1 d . . . . .
F4 F 0.4185(4) 0.9584(2) 0.55360(16) 0.0448(9) Uani 1 1 d . . . . .
F5 F 0.5811(6) 0.9430(3) 0.62823(18) 0.0570(11) Uani 1 1 d . . . . .
F6 F 0.3095(6) 0.9060(3) 0.6331(2) 0.0750(15) Uani 1 1 d . . . . .
P2 P 0.06634(17) 0.59577(10) 0.76754(5) 0.0257(3) Uani 1 1 d . . . . .
F7 F 0.1622(6) 0.6114(4) 0.82333(15) 0.0713(14) Uani 1 1 d . . . . .
F8 F -0.0898(4) 0.5544(3) 0.79976(13) 0.0453(9) Uani 1 1 d . . . . .
F9 F 0.1400(6) 0.4925(3) 0.76029(19) 0.0651(12) Uani 1 1 d . . . . .
F10 F -0.0305(5) 0.5851(3) 0.71156(13) 0.0447(9) Uani 1 1 d . . . . .
F11 F 0.2222(4) 0.6397(3) 0.73530(14) 0.0447(9) Uani 1 1 d . . . . .
F12 F -0.0076(6) 0.7025(3) 0.77286(18) 0.0609(12) 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
C1 N1 1.467(7) . ?
C1 C2 1.525(8) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.496(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.486(7) . ?
C3 N2 1.514(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N3 1.475(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N3 1.480(6) . ?
C5 C6 1.500(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N4 1.504(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N4 1.504(6) . ?
C7 C8 1.531(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N5 1.503(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N5 1.501(6) . ?
C9 C10 1.513(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N1 1.462(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N1 1.479(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N2 1.499(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 N4 1.495(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 N3 1.462(6) . ?
C14 C15 1.516(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N5 1.508(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N6 1.146(8) . ?
C16 C17 1.435(10) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N2 H2 0.82(4) . ?
N4 H4 0.82(4) . ?
N5 H5 0.82(4) . ?
P1 F6 1.585(4) . ?
P1 F5 1.587(4) . ?
P1 F2 1.591(4) . ?
P1 F3 1.595(4) . ?
P1 F1 1.602(4) . ?
P1 F4 1.609(4) . ?
P2 F9 1.570(4) . ?
P2 F8 1.588(3) . ?
P2 F7 1.589(4) . ?
P2 F10 1.590(4) . ?
P2 F11 1.599(3) . ?
P2 F12 1.609(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.6(4) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 111.1(4) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 N2 115.7(4) . . ?
C4 C3 H3A 108.4 . . ?
N2 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
N2 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
N3 C4 C3 116.7(4) . . ?
N3 C4 H4A 108.1 . . ?
C3 C4 H4A 108.1 . . ?
N3 C4 H4B 108.1 . . ?
C3 C4 H4B 108.1 . . ?
H4A C4 H4B 107.3 . . ?
N3 C5 C6 113.0(4) . . ?
N3 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N3 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 N4 114.0(4) . . ?
C5 C6 H6A 108.8 . . ?
N4 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
N4 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N4 C7 C8 113.6(4) . . ?
N4 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N4 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N5 C8 C7 115.9(4) . . ?
N5 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
N5 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N5 C9 C10 112.1(4) . . ?
N5 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N5 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
N1 C10 C9 110.9(4) . . ?
N1 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 110.8(4) . . ?
N3 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N5 C15 C14 110.3(4) . . ?
N5 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N5 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N6 C16 C17 179.2(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 N1 C1 112.1(4) . . ?
C10 N1 C11 110.2(4) . . ?
C1 N1 C11 110.8(4) . . ?
C2 N2 C12 111.1(4) . . ?
C2 N2 C3 111.3(5) . . ?
C12 N2 C3 110.4(4) . . ?
C2 N2 H2 107.9 . . ?
C12 N2 H2 107.9 . . ?
C3 N2 H2 107.9 . . ?
C14 N3 C4 115.1(4) . . ?
C14 N3 C5 109.9(4) . . ?
C4 N3 C5 108.1(4) . . ?
C13 N4 C6 108.4(4) . . ?
C13 N4 C7 111.6(4) . . ?
C6 N4 C7 115.4(4) . . ?
C13 N4 H4 107.0 . . ?
C6 N4 H4 107.0 . . ?
C7 N4 H4 107.0 . . ?
C9 N5 C8 109.7(4) . . ?
C9 N5 C15 112.9(4) . . ?
C8 N5 C15 114.0(4) . . ?
C9 N5 H5 106.6 . . ?
C8 N5 H5 106.6 . . ?
C15 N5 H5 106.6 . . ?
F6 P1 F5 89.4(3) . . ?
F6 P1 F2 90.4(3) . . ?
F5 P1 F2 179.8(3) . . ?
F6 P1 F3 179.6(3) . . ?
F5 P1 F3 90.1(2) . . ?
F2 P1 F3 90.0(2) . . ?
F6 P1 F1 90.3(2) . . ?
F5 P1 F1 90.0(2) . . ?
F2 P1 F1 89.8(2) . . ?
F3 P1 F1 89.8(2) . . ?
F6 P1 F4 90.4(2) . . ?
F5 P1 F4 90.1(2) . . ?
F2 P1 F4 90.1(2) . . ?
F3 P1 F4 89.53(19) . . ?
F1 P1 F4 179.3(2) . . ?
F9 P2 F8 90.9(2) . . ?
F9 P2 F7 92.6(3) . . ?
F8 P2 F7 89.7(2) . . ?
F9 P2 F10 89.8(2) . . ?
F8 P2 F10 91.05(19) . . ?
F7 P2 F10 177.5(3) . . ?
F9 P2 F11 90.3(2) . . ?
F8 P2 F11 178.8(2) . . ?
F7 P2 F11 90.2(2) . . ?
F10 P2 F11 89.0(2) . . ?
F9 P2 F12 178.0(2) . . ?
F8 P2 F12 90.5(2) . . ?
F7 P2 F12 88.8(3) . . ?
F10 P2 F12 88.8(2) . . ?
F11 P2 F12 88.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 N2 -49.2(6) . . . . ?
N2 C3 C4 N3 -67.3(6) . . . . ?
N3 C5 C6 N4 -54.0(5) . . . . ?
N4 C7 C8 N5 -64.3(5) . . . . ?
N5 C9 C10 N1 63.3(5) . . . . ?
N3 C14 C15 N5 -47.6(5) . . . . ?
C9 C10 N1 C1 -158.0(4) . . . . ?
C9 C10 N1 C11 78.1(5) . . . . ?
C2 C1 N1 C10 162.1(4) . . . . ?
C2 C1 N1 C11 -74.3(6) . . . . ?
C1 C2 N2 C12 161.0(5) . . . . ?
C1 C2 N2 C3 -75.5(6) . . . . ?
C4 C3 N2 C2 154.6(4) . . . . ?
C4 C3 N2 C12 -81.5(5) . . . . ?
C15 C14 N3 C4 164.8(4) . . . . ?
C15 C14 N3 C5 -72.8(5) . . . . ?
C3 C4 N3 C14 -53.6(6) . . . . ?
C3 C4 N3 C5 -177.0(4) . . . . ?
C6 C5 N3 C14 140.1(4) . . . . ?
C6 C5 N3 C4 -93.4(4) . . . . ?
C5 C6 N4 C13 -177.0(4) . . . . ?
C5 C6 N4 C7 -51.0(6) . . . . ?
C8 C7 N4 C13 -112.5(5) . . . . ?
C8 C7 N4 C6 123.1(4) . . . . ?
C10 C9 N5 C8 -167.4(4) . . . . ?
C10 C9 N5 C15 64.2(5) . . . . ?
C7 C8 N5 C9 179.4(4) . . . . ?
C7 C8 N5 C15 -52.8(5) . . . . ?
C14 C15 N5 C9 -108.5(4) . . . . ?
C14 C15 N5 C8 125.4(4) . . . . ?

_refine_diff_density_max         1.414
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.083


####################################################################### 
# 
# 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_gb08a
_database_code_depnum_ccdc_archive 'CCDC 1917396'
loop_
_audit_author_name
_audit_author_address
'Jeannette Krause'
;University of Cincinnati
United States of America
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H33 Cu N5, 0.45(Cl O4), 1.55(Cl)'
_chemical_formula_sum            'C15 H33 Cl2 Cu N5 O1.79'
_chemical_formula_weight         446.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0076 0.0040 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
O O 0.0132 0.0074 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
Cl Cl 0.1697 0.1896 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'
Cu Cu 0.2913 1.4803 'L. Kissel & R.H. Pratt, Acta Cryst A (1990), A46, 170-175'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8067(14)
_cell_length_b                   15.792(2)
_cell_length_c                   14.030(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.357(4)
_cell_angle_gamma                90
_cell_volume                     1951.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2803
_cell_measurement_theta_min      2.8125
_cell_measurement_theta_max      25.1205

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             941
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    1.783
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7057
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

_exptl_special_details           
; 
loop mount with paratone
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'ALS beamline 11.3.1.'
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'omega-phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            20954
_diffrn_reflns_av_unetI/netI     0.1545
_diffrn_reflns_av_R_equivalents  0.1643
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.117
_diffrn_reflns_theta_max         29.076
_diffrn_reflns_theta_full        27.706
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4026
_reflns_number_gt                2053
_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 APEX3 v2016.1.0'
_computing_cell_refinement       'Bruker SAINT v8.37A'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis,2007)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'


_refine_special_details          
;
One chlorine anion was found to be disordered over three sites 
and was modeled with refined site occupancies of 0.81, 0.17, 0.12. 
The second anion was found to be a site disordered chloride/perchlorate 
and was modeled with refined site occupancies of 0.55, 0.45.
Restraints were applied to the disordered species. 
Cl1A and Cl1B were refined isotropically since they are very minor
components (11 and 8%, respectively).
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0939P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4026
_refine_ls_number_parameters     268
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1734
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2109
_refine_ls_wR_factor_gt          0.1748
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_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
Cu1 Cu 0.74078(10) 0.25258(6) 0.91504(6) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.5986(7) 0.3290(4) 0.8421(4) 0.0295(15) Uani 1 1 d . . . . .
N2 N 0.5750(7) 0.1633(4) 0.9045(4) 0.0282(15) Uani 1 1 d . . . . .
N3 N 0.8942(7) 0.1565(4) 0.9229(4) 0.0306(15) Uani 1 1 d . . . . .
N4 N 0.9118(7) 0.3263(4) 0.8630(4) 0.0321(16) Uani 1 1 d . . . . .
N5 N 0.7259(7) 0.3478(4) 1.0254(4) 0.0285(15) Uani 1 1 d . . . . .
C1 C 0.5043(10) 0.2698(5) 0.7846(6) 0.041(2) Uani 1 1 d . . . . .
H1A H 0.564871 0.247310 0.731034 0.050 Uiso 1 1 calc R U . . .
H1B H 0.415957 0.300509 0.757535 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4503(9) 0.1985(5) 0.8448(5) 0.039(2) Uani 1 1 d . . . . .
H2A H 0.367604 0.218740 0.886491 0.047 Uiso 1 1 calc R U . . .
H2B H 0.408601 0.153322 0.803303 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5123(10) 0.1305(5) 0.9945(6) 0.044(2) Uani 1 1 d . . . . .
H3A H 0.437872 0.085982 0.980480 0.065 Uiso 1 1 calc R U . . .
H3B H 0.462706 0.176645 1.029095 0.065 Uiso 1 1 calc R U . . .
H3C H 0.594624 0.107043 1.033705 0.065 Uiso 1 1 calc R U . . .
C4 C 0.6604(10) 0.0967(5) 0.8518(6) 0.038(2) Uani 1 1 d . . . . .
H4A H 0.681742 0.116599 0.786323 0.046 Uiso 1 1 calc R U . . .
H4B H 0.598138 0.044677 0.847264 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8076(10) 0.0773(5) 0.9027(6) 0.045(2) Uani 1 1 d . . . . .
H5A H 0.785973 0.047757 0.963315 0.053 Uiso 1 1 calc R U . . .
H5B H 0.869837 0.039224 0.862745 0.053 Uiso 1 1 calc R U . . .
C6 C 0.9853(9) 0.1453(5) 1.0117(5) 0.040(2) Uani 1 1 d . . . . .
H6A H 1.056167 0.098064 1.003612 0.060 Uiso 1 1 calc R U . . .
H6B H 0.917307 0.133292 1.065050 0.060 Uiso 1 1 calc R U . . .
H6C H 1.042487 0.197307 1.024978 0.060 Uiso 1 1 calc R U . . .
C7 C 0.9956(9) 0.1801(5) 0.8430(5) 0.035(2) Uani 1 1 d . . . . .
H7A H 0.941135 0.172357 0.781635 0.042 Uiso 1 1 calc R U . . .
H7B H 1.085701 0.142582 0.843024 0.042 Uiso 1 1 calc R U . . .
C8 C 1.0452(9) 0.2703(5) 0.8527(6) 0.040(2) Uani 1 1 d . . . . .
H8A H 1.112303 0.276237 0.909140 0.048 Uiso 1 1 calc R U . . .
H8B H 1.103587 0.287140 0.795630 0.048 Uiso 1 1 calc R U . . .
C9 C 0.8501(9) 0.3528(5) 0.7681(5) 0.038(2) Uani 1 1 d . . . . .
H9A H 0.848203 0.303574 0.724375 0.046 Uiso 1 1 calc R U . . .
H9B H 0.916247 0.396778 0.740144 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6902(9) 0.3874(5) 0.7798(6) 0.042(2) Uani 1 1 d . . . . .
H10A H 0.694741 0.444431 0.809110 0.050 Uiso 1 1 calc R U . . .
H10B H 0.640602 0.392717 0.716581 0.050 Uiso 1 1 calc R U . . .
C11 C 0.9399(10) 0.3987(5) 0.9279(6) 0.042(2) Uani 1 1 d . . . . .
H11A H 0.888382 0.449651 0.902336 0.050 Uiso 1 1 calc R U . . .
H11B H 1.050203 0.410511 0.930716 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8828(9) 0.3809(5) 1.0271(6) 0.041(2) Uani 1 1 d . . . . .
H12A H 0.950387 0.339147 1.058476 0.049 Uiso 1 1 calc R U . . .
H12B H 0.885941 0.433785 1.065038 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5128(10) 0.3754(5) 0.9146(5) 0.039(2) Uani 1 1 d . . . . .
H13A H 0.438745 0.336673 0.944561 0.047 Uiso 1 1 calc R U . . .
H13B H 0.455189 0.421761 0.883478 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6146(9) 0.4122(5) 0.9906(6) 0.037(2) Uani 1 1 d . . . . .
H14A H 0.669903 0.461489 0.964430 0.044 Uiso 1 1 calc R U . . .
H14B H 0.552182 0.432129 1.044547 0.044 Uiso 1 1 calc R U . . .
C15 C 0.6830(10) 0.3166(6) 1.1205(5) 0.042(2) Uani 1 1 d . . . . .
H15A H 0.691094 0.362917 1.166801 0.063 Uiso 1 1 calc R U . . .
H15B H 0.751154 0.270471 1.139430 0.063 Uiso 1 1 calc R U . . .
H15C H 0.578182 0.295828 1.118553 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.7435(3) 0.6584(3) 0.8987(2) 0.0833(15) Uani 0.807(3) 1 d . . P A 1
Cl1A Cl 0.743(2) 0.7195(11) 0.9263(12) 0.024(4) Uiso 0.110(3) 1 d . . P B 2
Cl1B Cl 0.700(3) 0.5911(18) 0.855(2) 0.048(8) Uiso 0.082(3) 1 d . . P C 3
Cl2 Cl 0.2590(10) 0.9722(4) 0.7923(4) 0.021(2) Uani 0.552(10) 1 d . . P D 1
Cl2A Cl 0.2478(14) 0.9741(8) 0.7980(9) 0.070(6) Uani 0.448(10) 1 d D . P D 2
O1 O 0.2503(16) 1.0144(7) 0.8742(8) 0.056(5) Uani 0.448(10) 1 d D U P D 2
O2 O 0.2699(14) 0.8967(7) 0.8049(8) 0.042(4) Uani 0.448(10) 1 d D . P D 2
O3 O 0.1116(17) 0.9842(10) 0.7671(11) 0.114(6) Uani 0.448(10) 1 d D U P D 2
O4 O 0.333(2) 1.0047(9) 0.7365(10) 0.100(8) Uani 0.448(10) 1 d D . 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
Cu1 N1 2.013(6) . ?
Cu1 N3 2.034(6) . ?
Cu1 N2 2.035(6) . ?
Cu1 N4 2.042(6) . ?
Cu1 N5 2.162(6) . ?
N1 C13 1.467(9) . ?
N1 C1 1.486(9) . ?
N1 C10 1.508(9) . ?
N2 C3 1.475(9) . ?
N2 C2 1.486(9) . ?
N2 C4 1.491(9) . ?
N3 C7 1.485(9) . ?
N3 C6 1.488(9) . ?
N3 C5 1.491(10) . ?
N4 C8 1.479(9) . ?
N4 C11 1.481(9) . ?
N4 C9 1.494(9) . ?
N5 C15 1.474(9) . ?
N5 C12 1.477(9) . ?
N5 C14 1.493(9) . ?
C1 C2 1.487(11) . ?
C4 C5 1.507(11) . ?
C7 C8 1.497(11) . ?
C9 C10 1.521(11) . ?
C11 C12 1.509(11) . ?
C13 C14 1.505(11) . ?
Cl2A O2 1.242(12) . ?
Cl2A O1 1.243(11) . ?
Cl2A O4 1.246(13) . ?
Cl2A O3 1.283(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N3 152.3(2) . . ?
N1 Cu1 N2 86.3(2) . . ?
N3 Cu1 N2 87.9(2) . . ?
N1 Cu1 N4 86.2(3) . . ?
N3 Cu1 N4 87.3(3) . . ?
N2 Cu1 N4 154.1(2) . . ?
N1 Cu1 N5 84.7(2) . . ?
N3 Cu1 N5 121.5(2) . . ?
N2 Cu1 N5 119.2(2) . . ?
N4 Cu1 N5 84.7(2) . . ?
C13 N1 C1 113.7(6) . . ?
C13 N1 C10 112.0(6) . . ?
C1 N1 C10 111.7(6) . . ?
C13 N1 Cu1 105.6(4) . . ?
C1 N1 Cu1 104.1(4) . . ?
C10 N1 Cu1 109.2(5) . . ?
C3 N2 C2 109.6(6) . . ?
C3 N2 C4 111.7(6) . . ?
C2 N2 C4 111.0(6) . . ?
C3 N2 Cu1 117.0(5) . . ?
C2 N2 Cu1 108.0(5) . . ?
C4 N2 Cu1 99.2(4) . . ?
C7 N3 C6 109.8(6) . . ?
C7 N3 C5 112.1(6) . . ?
C6 N3 C5 109.4(6) . . ?
C7 N3 Cu1 100.0(5) . . ?
C6 N3 Cu1 119.2(5) . . ?
C5 N3 Cu1 106.0(5) . . ?
C8 N4 C11 113.1(6) . . ?
C8 N4 C9 111.4(6) . . ?
C11 N4 C9 113.0(6) . . ?
C8 N4 Cu1 106.4(5) . . ?
C11 N4 Cu1 109.9(5) . . ?
C9 N4 Cu1 102.3(5) . . ?
C15 N5 C12 110.4(6) . . ?
C15 N5 C14 110.6(6) . . ?
C12 N5 C14 112.1(6) . . ?
C15 N5 Cu1 115.7(5) . . ?
C12 N5 Cu1 101.4(4) . . ?
C14 N5 Cu1 106.4(4) . . ?
N1 C1 C2 110.3(6) . . ?
N2 C2 C1 111.5(7) . . ?
N2 C4 C5 110.1(6) . . ?
N3 C5 C4 110.9(6) . . ?
N3 C7 C8 110.3(6) . . ?
N4 C8 C7 110.3(7) . . ?
N4 C9 C10 109.7(6) . . ?
N1 C10 C9 109.9(6) . . ?
N4 C11 C12 111.6(6) . . ?
N5 C12 C11 111.5(6) . . ?
N1 C13 C14 112.1(7) . . ?
N5 C14 C13 110.9(6) . . ?
O2 Cl2A O1 115.7(11) . . ?
O2 Cl2A O4 109.9(11) . . ?
O1 Cl2A O4 112.9(11) . . ?
O2 Cl2A O3 107.1(11) . . ?
O1 Cl2A O3 103.8(11) . . ?
O4 Cl2A O3 106.6(12) . . ?

_refine_diff_density_max         1.111
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.142



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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1981500'
loop_
_audit_author_name
_audit_author_address
'Timothy Prior'
;University of Hull
United Kingdom
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
8(C15 H31 N5), 5(C H4 O), 16(I), 8(H2 O)
;
_chemical_formula_sum            'C15.62 H35.50 I2 N5 O1.62'
_chemical_formula_weight         573.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 -0.3993 1.9038 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0115 0.0064 '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                   16.5537(9)
_cell_length_b                   18.0400(9)
_cell_length_c                   15.0137(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.514(2)
_cell_angle_gamma                90
_cell_volume                     4445.0(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9732
_cell_measurement_theta_min      2.3155
_cell_measurement_theta_max      29.066

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             2266
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    3.006
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6624
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS v2016.2 (Sheldrick)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   
'Beamline 12.2.1 at the Advanced Light Source (ALS)'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'omega-phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50133
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         29.100
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5526
_reflns_number_gt                4913
_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 APEX3 v2016.9.0'
_computing_cell_refinement       'Bruker SAINT v8.38A'
_computing_data_reduction        'Bruker SAINT v8.38A'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0142P)²+10.0003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5526
_refine_ls_number_parameters     242
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0532
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.002
_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
I2 I 0.500000 0.56649(2) 0.250000 0.02481(6) Uani 1 2 d S T P . .
I3 I 0.000000 0.30004(2) 0.750000 0.02750(6) Uani 1 2 d S T P . .
I1 I 0.18827(2) 0.36902(2) 0.32590(2) 0.03216(6) Uani 1 1 d . . . . .
N5 N 0.36945(12) 0.70646(10) 0.45900(13) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.42825(12) 0.59622(11) 0.53832(13) 0.0203(4) Uani 1 1 d . . . . .
N4 N 0.59089(13) 0.70393(11) 0.50154(14) 0.0243(4) Uani 1 1 d . . . . .
N1 N 0.23661(12) 0.61269(11) 0.37647(14) 0.0241(4) Uani 1 1 d . . . . .
N2 N 0.25970(12) 0.59692(11) 0.52889(13) 0.0227(4) Uani 1 1 d . . . . .
C12 C 0.38269(14) 0.62588(12) 0.45860(15) 0.0189(5) Uani 1 1 d . . . . .
H12 H 0.410579 0.612478 0.405635 0.023 Uiso 1 1 calc R U . . .
C11 C 0.30064(14) 0.58628(13) 0.45106(15) 0.0203(5) Uani 1 1 d . . . . .
H11 H 0.309706 0.532002 0.443132 0.024 Uiso 1 1 calc R U . . .
C8 C 0.44350(15) 0.75059(13) 0.48162(16) 0.0223(5) Uani 1 1 d . . . . .
H8A H 0.459313 0.748285 0.547473 0.027 Uiso 1 1 calc R U . . .
H8B H 0.430417 0.802920 0.465948 0.027 Uiso 1 1 calc R U . . .
C5 C 0.51627(14) 0.58604(13) 0.54340(17) 0.0236(5) Uani 1 1 d . . . . .
H5A H 0.528376 0.571476 0.482960 0.028 Uiso 1 1 calc R U . . .
H5B H 0.531793 0.543793 0.584142 0.028 Uiso 1 1 calc R U . . .
C9 C 0.31955(15) 0.72898(14) 0.37601(16) 0.0253(5) Uani 1 1 d . . . . .
H9A H 0.344330 0.710845 0.323556 0.030 Uiso 1 1 calc R U . . .
H9B H 0.316478 0.783737 0.372717 0.030 Uiso 1 1 calc R U . . .
C7 C 0.51757(15) 0.72764(14) 0.43584(16) 0.0237(5) Uani 1 1 d . . . . .
H7A H 0.501541 0.686148 0.394089 0.028 Uiso 1 1 calc R U . . .
H7B H 0.533565 0.769842 0.399786 0.028 Uiso 1 1 calc R U . . .
C6 C 0.57115(16) 0.65108(14) 0.57490(16) 0.0253(5) Uani 1 1 d . . . . .
H6A H 0.622998 0.631271 0.606247 0.030 Uiso 1 1 calc R U . . .
H6B H 0.544779 0.679777 0.619343 0.030 Uiso 1 1 calc R U . . .
C3 C 0.30887(16) 0.57036(14) 0.61063(16) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.315699 0.515950 0.607408 0.032 Uiso 1 1 calc R U . . .
H3B H 0.281029 0.581749 0.663492 0.032 Uiso 1 1 calc R U . . .
C2 C 0.18121(16) 0.56004(15) 0.50444(19) 0.0308(6) Uani 1 1 d . . . . .
H2A H 0.140379 0.577678 0.542223 0.037 Uiso 1 1 calc R U . . .
H2B H 0.186684 0.505571 0.510559 0.037 Uiso 1 1 calc R U . . .
C14 C 0.65085(16) 0.66882(16) 0.44755(18) 0.0310(6) Uani 1 1 d . . . . .
H14A H 0.626404 0.624600 0.417114 0.046 Uiso 1 1 calc R U . . .
H14B H 0.700013 0.654690 0.487563 0.046 Uiso 1 1 calc R U . . .
H14C H 0.665266 0.704239 0.402713 0.046 Uiso 1 1 calc R U . . .
O1W O 0.0702(2) 0.44460(16) 0.6173(2) 0.0785(9) Uani 1 1 d D . . . .
H1D H 0.040403 0.489122 0.618129 0.118 Uiso 1 1 d DG U . . .
H1C H 0.046537 0.415318 0.658367 0.118 Uiso 1 1 d DG U . . .
C15 C 0.63013(17) 0.77095(15) 0.54834(18) 0.0314(6) Uani 1 1 d . . . . .
H15A H 0.649146 0.804288 0.503929 0.047 Uiso 1 1 calc R U . . .
H15B H 0.676529 0.755401 0.591634 0.047 Uiso 1 1 calc R U . . .
H15C H 0.590320 0.796853 0.579988 0.047 Uiso 1 1 calc R U . . .
C10 C 0.23485(16) 0.69682(14) 0.37445(17) 0.0271(5) Uani 1 1 d . . . . .
H10A H 0.200125 0.713641 0.319456 0.032 Uiso 1 1 calc R U . . .
H10B H 0.210491 0.715366 0.426995 0.032 Uiso 1 1 calc R U . . .
C4 C 0.39189(16) 0.60790(14) 0.62052(16) 0.0246(5) Uani 1 1 d . . . . .
H4A H 0.385753 0.661643 0.631194 0.030 Uiso 1 1 calc R U . . .
H4B H 0.427459 0.586669 0.672390 0.030 Uiso 1 1 calc R U . . .
C13 C 0.25015(18) 0.58196(16) 0.28716(17) 0.0334(6) Uani 1 1 d . . . . .
H13A H 0.302755 0.599281 0.271917 0.050 Uiso 1 1 calc R U . . .
H13B H 0.206466 0.598771 0.241213 0.050 Uiso 1 1 calc R U . . .
H13C H 0.250113 0.527681 0.289802 0.050 Uiso 1 1 calc R U . . .
C1 C 0.15771(16) 0.58239(16) 0.40645(19) 0.0328(6) Uani 1 1 d . . . . .
H1A H 0.114784 0.620942 0.401034 0.039 Uiso 1 1 calc R U . . .
H1B H 0.137559 0.539053 0.369623 0.039 Uiso 1 1 calc R U . . .
C17 C -0.0234(4) 0.4091(3) 0.3452(4) 0.0598(16) Uani 0.625 1 d D . P A 1
H17A H -0.026717 0.453972 0.308169 0.090 Uiso 0.625 1 calc DR U P A 1
H17B H -0.078351 0.390112 0.348561 0.090 Uiso 0.625 1 calc DR U P A 1
H17C H 0.008565 0.371380 0.318331 0.090 Uiso 0.625 1 calc DR U P A 1
O16 O 0.0143(2) 0.4258(2) 0.4315(3) 0.0516(9) Uani 0.625 1 d D . P A 1
H16 H 0.0669(12) 0.419(4) 0.431(3) 0.077 Uiso 0.625 1 d D U P B 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N5 C9 1.460(3) . ?
N5 C8 1.464(3) . ?
N5 C12 1.470(3) . ?
N3 C12 1.432(3) . ?
N3 C4 1.457(3) . ?
N3 C5 1.461(3) . ?
N4 C14 1.501(3) . ?
N4 C15 1.503(3) . ?
N4 C7 1.522(3) . ?
N4 C6 1.524(3) . ?
N1 C13 1.495(3) . ?
N1 C11 1.515(3) . ?
N1 C10 1.518(3) . ?
N1 C1 1.537(3) . ?
N2 C11 1.438(3) . ?
N2 C3 1.462(3) . ?
N2 C2 1.463(3) . ?
C12 C11 1.526(3) . ?
C12 H12 1.0000 . ?
C11 H11 1.0000 . ?
C8 C7 1.539(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C9 C10 1.515(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 C4 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C2 C1 1.526(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O1W H1D 0.944 . ?
O1W H1C 0.9362 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C17 O16 1.396(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O16 H16 0.881(19) . ?

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
C9 N5 C8 114.20(18) . . ?
C9 N5 C12 109.86(18) . . ?
C8 N5 C12 114.70(18) . . ?
C12 N3 C4 115.02(19) . . ?
C12 N3 C5 120.22(19) . . ?
C4 N3 C5 119.57(19) . . ?
C14 N4 C15 108.42(19) . . ?
C14 N4 C7 107.22(19) . . ?
C15 N4 C7 109.66(19) . . ?
C14 N4 C6 110.21(19) . . ?
C15 N4 C6 106.61(19) . . ?
C7 N4 C6 114.59(19) . . ?
C13 N1 C11 111.96(19) . . ?
C13 N1 C10 111.0(2) . . ?
C11 N1 C10 109.82(18) . . ?
C13 N1 C1 111.3(2) . . ?
C11 N1 C1 102.18(18) . . ?
C10 N1 C1 110.3(2) . . ?
C11 N2 C3 111.62(19) . . ?
C11 N2 C2 103.46(19) . . ?
C3 N2 C2 116.1(2) . . ?
N3 C12 N5 115.37(19) . . ?
N3 C12 C11 104.68(18) . . ?
N5 C12 C11 109.36(18) . . ?
N3 C12 H12 109.1 . . ?
N5 C12 H12 109.1 . . ?
C11 C12 H12 109.1 . . ?
N2 C11 N1 101.54(18) . . ?
N2 C11 C12 112.75(19) . . ?
N1 C11 C12 115.96(18) . . ?
N2 C11 H11 108.7 . . ?
N1 C11 H11 108.7 . . ?
C12 C11 H11 108.7 . . ?
N5 C8 C7 116.24(19) . . ?
N5 C8 H8A 108.2 . . ?
C7 C8 H8A 108.2 . . ?
N5 C8 H8B 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
N3 C5 C6 118.1(2) . . ?
N3 C5 H5A 107.8 . . ?
C6 C5 H5A 107.8 . . ?
N3 C5 H5B 107.8 . . ?
C6 C5 H5B 107.8 . . ?
H5A C5 H5B 107.1 . . ?
N5 C9 C10 109.02(19) . . ?
N5 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 . . ?
N5 C9 H9B 109.9 . . ?
C10 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N4 C7 C8 113.61(19) . . ?
N4 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
N4 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C5 C6 N4 115.7(2) . . ?
C5 C6 H6A 108.4 . . ?
N4 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
N4 C6 H6B 108.4 . . ?
H6A C6 H6B 107.4 . . ?
N2 C3 C4 109.43(19) . . ?
N2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
N2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
N2 C2 C1 103.2(2) . . ?
N2 C2 H2A 111.1 . . ?
C1 C2 H2A 111.1 . . ?
N2 C2 H2B 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H1D O1W H1C 101.9 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C10 N1 111.5(2) . . ?
C9 C10 H10A 109.3 . . ?
N1 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
N1 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
N3 C4 C3 108.7(2) . . ?
N3 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
N3 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C1 N1 104.9(2) . . ?
C2 C1 H1A 110.8 . . ?
N1 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
N1 C1 H1B 110.8 . . ?
H1A C1 H1B 108.8 . . ?
O16 C17 H17A 109.5 . . ?
O16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C17 O16 H16 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N3 C12 N5 60.3(3) . . . . ?
C5 N3 C12 N5 -94.2(2) . . . . ?
C4 N3 C12 C11 -60.0(2) . . . . ?
C5 N3 C12 C11 145.6(2) . . . . ?
C9 N5 C12 N3 -177.57(19) . . . . ?
C8 N5 C12 N3 52.2(3) . . . . ?
C9 N5 C12 C11 -59.9(2) . . . . ?
C8 N5 C12 C11 169.84(18) . . . . ?
C3 N2 C11 N1 176.43(18) . . . . ?
C2 N2 C11 N1 50.8(2) . . . . ?
C3 N2 C11 C12 -58.8(3) . . . . ?
C2 N2 C11 C12 175.60(19) . . . . ?
C13 N1 C11 N2 -158.5(2) . . . . ?
C10 N1 C11 N2 77.8(2) . . . . ?
C1 N1 C11 N2 -39.3(2) . . . . ?
C13 N1 C11 C12 78.9(3) . . . . ?
C10 N1 C11 C12 -44.8(3) . . . . ?
C1 N1 C11 C12 -161.8(2) . . . . ?
N3 C12 C11 N2 57.9(2) . . . . ?
N5 C12 C11 N2 -66.3(2) . . . . ?
N3 C12 C11 N1 174.32(18) . . . . ?
N5 C12 C11 N1 50.2(3) . . . . ?
C9 N5 C8 C7 -83.5(3) . . . . ?
C12 N5 C8 C7 44.6(3) . . . . ?
C12 N3 C5 C6 87.2(3) . . . . ?
C4 N3 C5 C6 -66.1(3) . . . . ?
C8 N5 C9 C10 -162.8(2) . . . . ?
C12 N5 C9 C10 66.7(2) . . . . ?
C14 N4 C7 C8 168.6(2) . . . . ?
C15 N4 C7 C8 -73.9(2) . . . . ?
C6 N4 C7 C8 45.9(3) . . . . ?
N5 C8 C7 N4 -118.6(2) . . . . ?
N3 C5 C6 N4 -89.0(3) . . . . ?
C14 N4 C6 C5 -74.0(3) . . . . ?
C15 N4 C6 C5 168.5(2) . . . . ?
C7 N4 C6 C5 47.0(3) . . . . ?
C11 N2 C3 C4 55.3(3) . . . . ?
C2 N2 C3 C4 173.5(2) . . . . ?
C11 N2 C2 C1 -41.1(2) . . . . ?
C3 N2 C2 C1 -163.8(2) . . . . ?
N5 C9 C10 N1 -61.3(3) . . . . ?
C13 N1 C10 C9 -75.2(3) . . . . ?
C11 N1 C10 C9 49.2(3) . . . . ?
C1 N1 C10 C9 161.0(2) . . . . ?
C12 N3 C4 C3 60.6(3) . . . . ?
C5 N3 C4 C3 -144.8(2) . . . . ?
N2 C3 C4 N3 -54.1(3) . . . . ?
N2 C2 C1 N1 15.3(3) . . . . ?
C13 N1 C1 C2 133.9(2) . . . . ?
C11 N1 C1 C2 14.2(2) . . . . ?
C10 N1 C1 C2 -102.5(2) . . . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.090



