# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

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

data_dan9579_1e
_database_code_depnum_ccdc_archive 'CCDC 2267508'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H38 I2 N6'
_chemical_formula_iupac          ?
_chemical_formula_weight         616.36

_chemical_melting_point          ?

_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
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                   28.4678(8)
_cell_length_b                   28.4678(8)
_cell_length_c                   6.3147(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5117.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9787
_cell_measurement_theta_min      4.3929
_cell_measurement_theta_max      69.9883
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.424
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2448

_exptl_absorpt_coefficient_mu    19.425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.24
_exptl_absorpt_correction_T_max  0.43

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            36089
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         70.07
_diffrn_reflns_theta_full        70.07
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_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.

The hydrogens at N1, N2 and N3 atoms were refined freely.
;

_reflns_number_total             2425
_reflns_number_gt                2256
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0518
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         2425
_refine_ls_number_parameters     143
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0253P)²+10.2939P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.551
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.41458(2) 0.40978(2) 0.63258(2) 0.01349(7) Uani d . . . 1 . .
N N1 0.43661(6) 0.51820(6) 0.3329(3) 0.0114(3) Uani d . . . 1 . .
H H1 0.4288(9) 0.4944(9) 0.400(4) 0.011(6) Uiso d . . . 1 . .
N N2 0.39138(6) 0.56510(6) 0.5519(3) 0.0113(3) Uani d . . . 1 . .
H H2 0.3877(9) 0.5899(10) 0.609(4) 0.013(7) Uiso d . . . 1 . .
N N3 0.45615(6) 0.59663(6) 0.3822(3) 0.0105(3) Uani d . . . 1 . .
H H3 0.4818(10) 0.5900(9) 0.340(4) 0.016(7) Uiso d . . . 1 . .
C C1 0.42794(7) 0.56073(7) 0.4224(3) 0.0097(4) Uani d . . . 1 . .
C C2 0.46897(7) 0.50999(7) 0.1644(3) 0.0099(4) Uani d . . . 1 . .
C C3 0.47064(7) 0.53900(7) -0.0125(3) 0.0116(4) Uani d . . . 1 . .
H H3A 0.4504 0.5655 -0.022 0.014 Uiso calc U . R 1 . .
C C4 0.50192(7) 0.52919(7) -0.1752(3) 0.0114(4) Uani d . . . 1 . .
H H4A 0.5035 0.5494 -0.2948 0.014 Uiso calc U . R 1 . .
C C11 0.34933(7) 0.53487(7) 0.5523(3) 0.0124(4) Uani d . . . 1 . .
H H11 0.3577 0.504 0.4868 0.015 Uiso calc U . R 1 . .
C C12 0.31145(8) 0.55815(8) 0.4181(3) 0.0179(4) Uani d . . . 1 . .
H H12A 0.3037 0.589 0.4779 0.027 Uiso calc U . R 1 . .
H H12B 0.2833 0.5384 0.4169 0.027 Uiso calc U . R 1 . .
H H12C 0.323 0.5621 0.2729 0.027 Uiso calc U . R 1 . .
C C13 0.33410(8) 0.52643(7) 0.7801(3) 0.0157(4) Uani d . . . 1 . .
H H13A 0.3591 0.5098 0.8562 0.024 Uiso calc U . R 1 . .
H H13B 0.3054 0.5074 0.7815 0.024 Uiso calc U . R 1 . .
H H13C 0.328 0.5566 0.8493 0.024 Uiso calc U . R 1 . .
C C21 0.44848(7) 0.64576(7) 0.4473(3) 0.0111(4) Uani d . . . 1 . .
H H21 0.4139 0.6516 0.4574 0.013 Uiso calc U . R 1 . .
C C22 0.47069(8) 0.65503(8) 0.6624(3) 0.0147(4) Uani d . . . 1 . .
H H22A 0.4549 0.6359 0.7701 0.022 Uiso calc U . R 1 . .
H H22B 0.4674 0.6884 0.6981 0.022 Uiso calc U . R 1 . .
H H22C 0.5041 0.6468 0.6575 0.022 Uiso calc U . R 1 . .
C C23 0.46882(8) 0.67718(7) 0.2758(3) 0.0167(4) Uani d . . . 1 . .
H H23A 0.502 0.6693 0.2539 0.025 Uiso calc U . R 1 . .
H H23B 0.4661 0.7101 0.3194 0.025 Uiso calc U . R 1 . .
H H23C 0.4515 0.6724 0.1435 0.025 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.359(3) ?
N1 C2 . 1.427(3) ?
N1 H1 . 0.83(3) ?
N2 C1 . 1.330(3) ?
N2 C11 . 1.474(3) ?
N2 H2 . 0.80(3) ?
N3 C1 . 1.324(3) ?
N3 C21 . 1.474(3) ?
N3 H3 . 0.80(3) ?
C2 C3 . 1.390(3) ?
C2 C4 9_665 1.391(3) ?
C3 C4 . 1.388(3) ?
C3 H3A . 0.95 ?
C4 C2 9_665 1.391(3) ?
C4 H4A . 0.95 ?
C11 C13 . 1.521(3) ?
C11 C12 . 1.524(3) ?
C11 H11 . 1.0 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C21 C23 . 1.519(3) ?
C21 C22 . 1.521(3) ?
C21 H21 . 1.0 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C2 . . 125.01(18) ?
C1 N1 H1 . . 117.6(17) ?
C2 N1 H1 . . 115.0(17) ?
C1 N2 C11 . . 125.60(18) ?
C1 N2 H2 . . 117.5(19) ?
C11 N2 H2 . . 114.2(19) ?
C1 N3 C21 . . 126.08(18) ?
C1 N3 H3 . . 115.7(19) ?
C21 N3 H3 . . 117.0(19) ?
N3 C1 N2 . . 121.35(18) ?
N3 C1 N1 . . 119.85(18) ?
N2 C1 N1 . . 118.79(18) ?
C3 C2 C4 . 9_665 119.70(19) ?
C3 C2 N1 . . 121.60(18) ?
C4 C2 N1 9_665 . 118.65(18) ?
C4 C3 C2 . . 119.82(19) ?
C4 C3 H3A . . 120.1 ?
C2 C3 H3A . . 120.1 ?
C3 C4 C2 . 9_665 120.47(19) ?
C3 C4 H4A . . 119.8 ?
C2 C4 H4A 9_665 . 119.8 ?
N2 C11 C13 . . 108.98(17) ?
N2 C11 C12 . . 108.64(17) ?
C13 C11 C12 . . 113.16(17) ?
N2 C11 H11 . . 108.7 ?
C13 C11 H11 . . 108.7 ?
C12 C11 H11 . . 108.7 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N3 C21 C23 . . 107.67(16) ?
N3 C21 C22 . . 110.59(16) ?
C23 C21 C22 . . 112.07(17) ?
N3 C21 H21 . . 108.8 ?
C23 C21 H21 . . 108.8 ?
C22 C21 H21 . . 108.8 ?
C21 C22 H22A . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C21 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C21 C23 H23A . . 109.5 ?
C21 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C21 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 N3 C1 N2 . . . . -8.4(3) ?
C21 N3 C1 N1 . . . . 172.67(18) ?
C11 N2 C1 N3 . . . . 157.26(19) ?
C11 N2 C1 N1 . . . . -23.8(3) ?
C2 N1 C1 N3 . . . . -12.6(3) ?
C2 N1 C1 N2 . . . . 168.46(19) ?
C1 N1 C2 C3 . . . . -45.4(3) ?
C1 N1 C2 C4 . . . 9_665 137.2(2) ?
C4 C2 C3 C4 9_665 . . . -1.2(3) ?
N1 C2 C3 C4 . . . . -178.56(18) ?
C2 C3 C4 C2 . . . 9_665 1.2(3) ?
C1 N2 C11 C13 . . . . 141.4(2) ?
C1 N2 C11 C12 . . . . -94.9(2) ?
C1 N3 C21 C23 . . . . -146.7(2) ?
C1 N3 C21 C22 . . . . 90.6(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 I1 . 0.83(3) 2.85(3) 3.6744(18) 172.(2) ?
N2 H2 I1 3 0.80(3) 3.06(3) 3.8081(18) 158.(2) ?
N3 H3 I1 9_666 0.80(3) 2.96(3) 3.6856(18) 153.(2) ?
C11 H11 I1 . 1.0 3.27 4.048(2) 136.3 ?
C13 H13C I1 3 0.98 3.1 3.990(2) 151.7 ?

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

data_dan9751_1j
_database_code_depnum_ccdc_archive 'CCDC 2267509'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-06-05 deposited with the CCDC.	2023-11-16 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H60 I2 N6 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         862.70

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.8424(2)
_cell_length_b                   14.7304(3)
_cell_length_c                   12.1460(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.8630(10)
_cell_angle_gamma                90
_cell_volume                     1937.66(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      4.0820
_cell_measurement_theta_max      66.6212
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    13.039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.25
_exptl_absorpt_correction_T_max  0.42

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            25772
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_theta_min         4.08
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_full        66.63
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_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.

The hydrogen atoms at N1, N2, N3 and O1 were refined freely.
;

_reflns_number_total             3425
_reflns_number_gt                3279
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0224
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0547
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         3425
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0259P)²+1.7290P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.544
_refine_diff_density_min         -0.608
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.38725(2) 0.47006(2) 0.14152(2) 0.01946(7) Uani d . . . 1 . .
N N1 0.76015(17) 0.58821(13) 0.31969(16) 0.0111(4) Uani d . . . 1 . .
H H1 0.735(3) 0.550(2) 0.269(3) 0.014(7) Uiso d . . . 1 . .
N N2 0.75183(17) 0.74133(13) 0.36871(16) 0.0106(4) Uani d . . . 1 . .
H H2 0.708(2) 0.7838(19) 0.362(2) 0.008(6) Uiso d . . . 1 . .
N N3 0.58923(17) 0.67333(13) 0.21229(16) 0.0114(4) Uani d . . . 1 . .
H H3 0.555(3) 0.624(2) 0.185(2) 0.016(7) Uiso d . . . 1 . .
O O1 0.68868(19) 0.44650(13) 0.15310(17) 0.0246(4) Uani d . . . 1 . .
H H1A 0.624(4) 0.436(3) 0.149(3) 0.039(11) Uiso d . . . 1 . .
H H2A 0.677(4) 0.463(3) 0.081(5) 0.064(14) Uiso d . . . 1 . .
C C1 0.7013(2) 0.66885(14) 0.30147(18) 0.0092(4) Uani d . . . 1 . .
C C11 0.8439(2) 0.55407(14) 0.43410(18) 0.0095(4) Uani d . . . 1 . .
C C12 0.8119(2) 0.55335(14) 0.53052(19) 0.0117(4) Uani d . . . 1 . .
H H12 0.7343 0.577 0.5223 0.014 Uiso calc U . R 1 . .
C C13 0.8939(2) 0.51760(15) 0.64193(18) 0.0126(5) Uani d . . . 1 . .
H H13 0.871 0.5174 0.7084 0.015 Uiso calc U . R 1 . .
C C14 1.0057(2) 0.48325(14) 0.65532(18) 0.0111(4) Uani d . . . 1 . .
H H14 1.0602 0.4599 0.7311 0.013 Uiso calc U . R 1 . .
C C15 1.0413(2) 0.48219(13) 0.55673(18) 0.0090(4) Uani d . . . 1 . .
C C21 0.88430(19) 0.75808(14) 0.44109(18) 0.0099(4) Uani d . . . 1 . .
H H21 0.9317 0.7022 0.4398 0.012 Uiso calc U . R 1 . .
C C22 0.9288(2) 0.83658(15) 0.38630(18) 0.0121(4) Uani d . . . 1 . .
H H22A 0.9175 0.8205 0.3033 0.014 Uiso calc U . R 1 . .
H H22B 0.8788 0.8913 0.3821 0.014 Uiso calc U . R 1 . .
C C23 1.0650(2) 0.85715(16) 0.4618(2) 0.0176(5) Uani d . . . 1 . .
H H23A 1.1158 0.8047 0.4584 0.021 Uiso calc U . R 1 . .
H H23B 1.0904 0.9105 0.4277 0.021 Uiso calc U . R 1 . .
C C24 1.0882(2) 0.87639(16) 0.5926(2) 0.0182(5) Uani d . . . 1 . .
H H24A 1.045 0.9329 0.5969 0.022 Uiso calc U . R 1 . .
H H24B 1.1778 0.8855 0.6401 0.022 Uiso calc U . R 1 . .
C C25 1.0428(2) 0.79814(16) 0.64672(19) 0.0175(5) Uani d . . . 1 . .
H H25A 1.0917 0.7429 0.6499 0.021 Uiso calc U . R 1 . .
H H25B 1.0549 0.8138 0.73 0.021 Uiso calc U . R 1 . .
C C26 0.9063(2) 0.77913(15) 0.57151(18) 0.0132(4) Uani d . . . 1 . .
H H26A 0.8567 0.8327 0.5736 0.016 Uiso calc U . R 1 . .
H H26B 0.8793 0.7269 0.6062 0.016 Uiso calc U . R 1 . .
C C31 0.5272(2) 0.75590(14) 0.14706(18) 0.0109(4) Uani d . . . 1 . .
H H31 0.5633 0.8094 0.2005 0.013 Uiso calc U . R 1 . .
C C32 0.5512(2) 0.76745(18) 0.0342(2) 0.0220(5) Uani d . . . 1 . .
H H32A 0.5212 0.7133 -0.0177 0.026 Uiso calc U . R 1 . .
H H32B 0.6411 0.7731 0.0565 0.026 Uiso calc U . R 1 . .
C C33 0.4849(3) 0.85240(19) -0.0352(2) 0.0276(6) Uani d . . . 1 . .
H H33A 0.5202 0.9071 0.0143 0.033 Uiso calc U . R 1 . .
H H33B 0.4982 0.8577 -0.1103 0.033 Uiso calc U . R 1 . .
C C34 0.3480(2) 0.84755(18) -0.0656(2) 0.0228(5) Uani d . . . 1 . .
H H34A 0.3116 0.7955 -0.1199 0.027 Uiso calc U . R 1 . .
H H34B 0.3074 0.9036 -0.1082 0.027 Uiso calc U . R 1 . .
C C35 0.3247(2) 0.83677(17) 0.0476(2) 0.0208(5) Uani d . . . 1 . .
H H35A 0.2349 0.8315 0.0256 0.025 Uiso calc U . R 1 . .
H H35B 0.355 0.8913 0.0988 0.025 Uiso calc U . R 1 . .
C C36 0.3902(2) 0.75245(18) 0.1186(2) 0.0239(6) Uani d . . . 1 . .
H H36A 0.3781 0.749 0.1945 0.029 Uiso calc U . R 1 . .
H H36B 0.3537 0.6973 0.0708 0.029 Uiso calc U . R 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.349(3) ?
N1 C11 . 1.433(3) ?
N1 H1 . 0.80(3) ?
N2 C1 . 1.330(3) ?
N2 C21 . 1.476(3) ?
N2 H2 . 0.80(3) ?
N3 C1 . 1.333(3) ?
N3 C31 . 1.475(3) ?
N3 H3 . 0.83(3) ?
O1 H1A . 0.77(4) ?
O1 H2A . 0.86(5) ?
C11 C12 . 1.369(3) ?
C11 C15 3_766 1.422(3) ?
C12 C13 . 1.410(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.365(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.422(3) ?
C14 H14 . 0.95 ?
C15 C11 3_766 1.422(3) ?
C15 C15 3_766 1.429(4) ?
C21 C26 . 1.530(3) ?
C21 C22 . 1.530(3) ?
C21 H21 . 1.0 ?
C22 C23 . 1.528(3) ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.524(3) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 C25 . 1.529(3) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 C26 . 1.527(3) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 H26A . 0.99 ?
C26 H26B . 0.99 ?
C31 C36 . 1.517(3) ?
C31 C32 . 1.518(3) ?
C31 H31 . 1.0 ?
C32 C33 . 1.535(3) ?
C32 H32A . 0.99 ?
C32 H32B . 0.99 ?
C33 C34 . 1.512(4) ?
C33 H33A . 0.99 ?
C33 H33B . 0.99 ?
C34 C35 . 1.516(3) ?
C34 H34A . 0.99 ?
C34 H34B . 0.99 ?
C35 C36 . 1.531(3) ?
C35 H35A . 0.99 ?
C35 H35B . 0.99 ?
C36 H36A . 0.99 ?
C36 H36B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C11 . . 125.24(18) ?
C1 N1 H1 . . 119.(2) ?
C11 N1 H1 . . 113.(2) ?
C1 N2 C21 . . 127.25(19) ?
C1 N2 H2 . . 117.0(18) ?
C21 N2 H2 . . 115.1(18) ?
C1 N3 C31 . . 126.37(18) ?
C1 N3 H3 . . 116.5(19) ?
C31 N3 H3 . . 116.7(19) ?
H1A O1 H2A . . 104.(4) ?
N2 C1 N3 . . 120.78(19) ?
N2 C1 N1 . . 122.1(2) ?
N3 C1 N1 . . 117.08(19) ?
C12 C11 C15 . 3_766 121.10(19) ?
C12 C11 N1 . . 120.7(2) ?
C15 C11 N1 3_766 . 118.18(18) ?
C11 C12 C13 . . 120.2(2) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C14 C13 C12 . . 120.72(19) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 120.54(19) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C14 C15 C11 . 3_766 122.55(19) ?
C14 C15 C15 . 3_766 119.2(2) ?
C11 C15 C15 3_766 3_766 118.3(2) ?
N2 C21 C26 . . 110.20(17) ?
N2 C21 C22 . . 109.73(17) ?
C26 C21 C22 . . 110.67(17) ?
N2 C21 H21 . . 108.7 ?
C26 C21 H21 . . 108.7 ?
C22 C21 H21 . . 108.7 ?
C23 C22 C21 . . 110.75(17) ?
C23 C22 H22A . . 109.5 ?
C21 C22 H22A . . 109.5 ?
C23 C22 H22B . . 109.5 ?
C21 C22 H22B . . 109.5 ?
H22A C22 H22B . . 108.1 ?
C24 C23 C22 . . 111.36(18) ?
C24 C23 H23A . . 109.4 ?
C22 C23 H23A . . 109.4 ?
C24 C23 H23B . . 109.4 ?
C22 C23 H23B . . 109.4 ?
H23A C23 H23B . . 108.0 ?
C23 C24 C25 . . 111.18(19) ?
C23 C24 H24A . . 109.4 ?
C25 C24 H24A . . 109.4 ?
C23 C24 H24B . . 109.4 ?
C25 C24 H24B . . 109.4 ?
H24A C24 H24B . . 108.0 ?
C26 C25 C24 . . 110.65(18) ?
C26 C25 H25A . . 109.5 ?
C24 C25 H25A . . 109.5 ?
C26 C25 H25B . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 108.1 ?
C25 C26 C21 . . 110.61(18) ?
C25 C26 H26A . . 109.5 ?
C21 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
C21 C26 H26B . . 109.5 ?
H26A C26 H26B . . 108.1 ?
N3 C31 C36 . . 110.42(18) ?
N3 C31 C32 . . 110.08(17) ?
C36 C31 C32 . . 111.80(19) ?
N3 C31 H31 . . 108.1 ?
C36 C31 H31 . . 108.1 ?
C32 C31 H31 . . 108.1 ?
C31 C32 C33 . . 110.27(19) ?
C31 C32 H32A . . 109.6 ?
C33 C32 H32A . . 109.6 ?
C31 C32 H32B . . 109.6 ?
C33 C32 H32B . . 109.6 ?
H32A C32 H32B . . 108.1 ?
C34 C33 C32 . . 110.8(2) ?
C34 C33 H33A . . 109.5 ?
C32 C33 H33A . . 109.5 ?
C34 C33 H33B . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 108.1 ?
C33 C34 C35 . . 110.7(2) ?
C33 C34 H34A . . 109.5 ?
C35 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
C35 C34 H34B . . 109.5 ?
H34A C34 H34B . . 108.1 ?
C34 C35 C36 . . 111.0(2) ?
C34 C35 H35A . . 109.4 ?
C36 C35 H35A . . 109.4 ?
C34 C35 H35B . . 109.4 ?
C36 C35 H35B . . 109.4 ?
H35A C35 H35B . . 108.0 ?
C31 C36 C35 . . 110.63(19) ?
C31 C36 H36A . . 109.5 ?
C35 C36 H36A . . 109.5 ?
C31 C36 H36B . . 109.5 ?
C35 C36 H36B . . 109.5 ?
H36A C36 H36B . . 108.1 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 N2 C1 N3 . . . . -158.24(19) ?
C21 N2 C1 N1 . . . . 21.7(3) ?
C31 N3 C1 N2 . . . . 23.8(3) ?
C31 N3 C1 N1 . . . . -156.19(19) ?
C11 N1 C1 N2 . . . . 32.5(3) ?
C11 N1 C1 N3 . . . . -147.6(2) ?
C1 N1 C11 C12 . . . . 50.1(3) ?
C1 N1 C11 C15 . . . 3_766 -132.3(2) ?
C15 C11 C12 C13 3_766 . . . 1.0(3) ?
N1 C11 C12 C13 . . . . 178.48(19) ?
C11 C12 C13 C14 . . . . -0.1(3) ?
C12 C13 C14 C15 . . . . -0.5(3) ?
C13 C14 C15 C11 . . . 3_766 -179.1(2) ?
C13 C14 C15 C15 . . . 3_766 0.2(4) ?
C1 N2 C21 C26 . . . . -125.7(2) ?
C1 N2 C21 C22 . . . . 112.2(2) ?
N2 C21 C22 C23 . . . . 178.32(17) ?
C26 C21 C22 C23 . . . . 56.5(2) ?
C21 C22 C23 C24 . . . . -55.5(2) ?
C22 C23 C24 C25 . . . . 55.5(3) ?
C23 C24 C25 C26 . . . . -56.1(3) ?
C24 C25 C26 C21 . . . . 57.2(2) ?
N2 C21 C26 C25 . . . . -179.05(18) ?
C22 C21 C26 C25 . . . . -57.5(2) ?
C1 N3 C31 C36 . . . . -142.5(2) ?
C1 N3 C31 C32 . . . . 93.6(2) ?
N3 C31 C32 C33 . . . . 179.0(2) ?
C36 C31 C32 C33 . . . . 55.9(3) ?
C31 C32 C33 C34 . . . . -56.7(3) ?
C32 C33 C34 C35 . . . . 57.6(3) ?
C33 C34 C35 C36 . . . . -57.1(3) ?
N3 C31 C36 C35 . . . . -178.36(19) ?
C32 C31 C36 C35 . . . . -55.4(3) ?
C34 C35 C36 C31 . . . . 55.6(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . 0.80(3) 2.00(3) 2.790(3) 174.(3) ?
N2 H2 I1 2_655 0.80(3) 2.96(3) 3.7302(19) 163.(2) ?
N3 H3 I1 . 0.83(3) 2.92(3) 3.7097(19) 160.(2) ?
O1 H1A I1 . 0.77(4) 2.81(4) 3.532(2) 158.(4) ?
O1 H2A I1 3_665 0.86(5) 2.69(5) 3.538(2) 172.(4) ?

