# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1497631'
_audit_update_record             
;
2016-08-04 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C40 H35 Cl4 N4 O3'
_chemical_formula_moiety         'C38 H31 N4 O3, 2(C H2 Cl2)'
_chemical_formula_weight         761.55
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        I2/a
_space_group_name_Hall           '-I 2ya'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'
#------------------------------------------------------------------------------
_cell_length_a                   16.901(3)
_cell_length_b                   9.2057(13)
_cell_length_c                   47.963(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.149(6)
_cell_angle_gamma                90.0000
_cell_volume                     7461(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7018
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3160.00
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.569
_exptl_absorpt_correction_T_max  0.951

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 11.628
_diffrn_reflns_number            58867
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       57
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             6853
_reflns_number_gt                4270
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.1008
_refine_ls_wR_factor_ref         0.3125
_refine_ls_wR_factor_gt          0.2810
_refine_ls_number_restraints     6
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6853
_refine_ls_number_parameters     481
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.21
_refine_diff_density_min         -0.88
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl51 Cl 0.88316(16) 0.3690(2) 0.37651(4) 0.1364(9) Uani 1 1 d . . . . .
Cl52 Cl 0.82698(8) 0.07519(16) 0.37217(3) 0.0816(5) Uani 1 1 d . . . . .
Cl61 Cl 0.5942(2) -0.3549(7) 0.39283(11) 0.1182(14) Uani 0.5 1 d D . P A 1
Cl62 Cl 0.7559(6) -0.3673(17) 0.3790(2) 0.299(8) Uani 0.5 1 d D . P A 1
Cl6A Cl 0.6107(3) -0.2620(6) 0.40246(8) 0.1079(12) Uani 0.5 1 d D . P B 2
Cl6B Cl 0.7599(2) -0.2880(6) 0.38645(13) 0.1136(17) Uani 0.5 1 d D . P B 2
O1 O 1.18514(15) 0.2598(3) 0.53481(6) 0.0552(8) Uani 1 1 d . . . . .
O6 O 0.95892(15) 0.2461(3) 0.45424(5) 0.0502(7) Uani 1 1 d . . . . .
O7 O 0.86429(14) 0.2506(3) 0.48673(5) 0.0496(7) Uani 1 1 d . . . . .
N1 N 1.11216(18) 0.2561(4) 0.52764(6) 0.0465(8) Uani 1 1 d . . . . .
N25 N 0.21581(18) 0.0725(4) 0.26221(6) 0.0550(9) Uani 1 1 d . . . . .
N29 N 0.1251(2) 0.3102(5) 0.31192(9) 0.0791(12) Uani 1 1 d . . . . .
N35 N 0.3564(2) -0.1608(6) 0.22901(7) 0.0758(12) Uani 1 1 d . . . . .
C2 C 1.0855(2) 0.2543(4) 0.49806(7) 0.0409(9) Uani 1 1 d . . . . .
C3 C 0.9968(2) 0.2507(4) 0.50215(7) 0.0420(9) Uani 1 1 d . . . . .
C4 C 0.9784(2) 0.2497(4) 0.52884(8) 0.0467(9) Uani 1 1 d . . . . .
H4 H 0.9254 0.2474 0.5350 0.056 Uiso 1 1 calc R U . . .
C5 C 1.0478(2) 0.2526(4) 0.54828(7) 0.0445(9) Uani 1 1 d . . . . .
C6 C 0.9408(2) 0.2491(4) 0.47844(8) 0.0424(9) Uani 1 1 d . . . . .
C8 C 0.8062(2) 0.2421(4) 0.46533(7) 0.0438(9) Uani 1 1 d . . . . .
C9 C 0.7747(2) 0.3676(5) 0.45431(8) 0.0504(10) Uani 1 1 d . . . . .
H9 H 0.7910 0.4599 0.4612 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7186(2) 0.3565(5) 0.43285(9) 0.0532(10) Uani 1 1 d . . . . .
H10 H 0.6959 0.4421 0.4250 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6950(2) 0.2203(5) 0.42264(8) 0.0479(10) Uani 1 1 d . . . . .
C12 C 0.7253(2) 0.0973(5) 0.43531(8) 0.0482(9) Uani 1 1 d . . . . .
H12 H 0.7075 0.0044 0.4292 0.058 Uiso 1 1 calc R U . . .
C13 C 0.7810(2) 0.1068(5) 0.45675(8) 0.0493(10) Uani 1 1 d . . . . .
H13 H 0.8016 0.0215 0.4654 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6393(2) 0.2062(5) 0.39989(8) 0.0516(10) Uani 1 1 d . . . . .
C15 C 0.5924(2) 0.1893(5) 0.38088(8) 0.0520(10) Uani 1 1 d . . . . .
C16 C 0.5335(2) 0.1719(5) 0.35923(7) 0.0503(10) Uani 1 1 d . . . . .
C17 C 0.4794(2) 0.2817(5) 0.35374(8) 0.0534(10) Uani 1 1 d . . . . .
H17 H 0.4830 0.3706 0.3638 0.064 Uiso 1 1 calc R U . . .
C18 C 0.4206(2) 0.2628(5) 0.33389(8) 0.0504(10) Uani 1 1 d . . . . .
H18 H 0.3846 0.3401 0.3303 0.060 Uiso 1 1 calc R U . . .
C19 C 0.4121(2) 0.1340(5) 0.31893(7) 0.0507(10) Uani 1 1 d . . . . .
C20 C 0.4677(2) 0.0246(5) 0.32414(8) 0.0529(10) Uani 1 1 d . . . . .
H20 H 0.4647 -0.0639 0.3140 0.064 Uiso 1 1 calc R U . . .
C21 C 0.5273(2) 0.0446(5) 0.34405(8) 0.0538(10) Uani 1 1 d . . . . .
H21 H 0.5647 -0.0308 0.3473 0.065 Uiso 1 1 calc R U . . .
C22 C 0.3443(2) 0.1118(5) 0.29927(8) 0.0502(10) Uani 1 1 d . . . . .
C23 C 0.2722(2) 0.1791(5) 0.30351(8) 0.0540(10) Uani 1 1 d . . . . .
H23 H 0.2655 0.2397 0.3193 0.065 Uiso 1 1 calc R U . . .
C24 C 0.2096(2) 0.1581(5) 0.28459(8) 0.0543(10) Uani 1 1 d . . . . .
C26 C 0.2851(2) 0.0053(5) 0.25809(7) 0.0539(10) Uani 1 1 d . . . . .
C27 C 0.3501(2) 0.0225(5) 0.27600(7) 0.0518(10) Uani 1 1 d . . . . .
H27 H 0.3982 -0.0264 0.2724 0.062 Uiso 1 1 calc R U . . .
C28 C 0.1325(2) 0.2327(5) 0.28825(9) 0.0554(11) Uani 1 1 d . . . . .
C30 C 0.0574(3) 0.3805(7) 0.31537(13) 0.0959(19) Uani 1 1 d . . . . .
H30 H 0.0508 0.4325 0.3323 0.115 Uiso 1 1 calc R U . . .
C31 C -0.0028(3) 0.3827(7) 0.29631(13) 0.0859(17) Uani 1 1 d . . . . .
H31 H -0.0488 0.4393 0.2994 0.103 Uiso 1 1 calc R U . . .
C32 C 0.0037(3) 0.3022(7) 0.27260(11) 0.0732(14) Uani 1 1 d . . . . .
H32 H -0.0382 0.2999 0.2591 0.088 Uiso 1 1 calc R U . . .
C33 C 0.0723(2) 0.2241(6) 0.26856(9) 0.0605(12) Uani 1 1 d . . . . .
H33 H 0.0778 0.1653 0.2524 0.073 Uiso 1 1 calc R U . . .
C34 C 0.2895(2) -0.0880(5) 0.23271(8) 0.0564(11) Uani 1 1 d . . . . .
C36 C 0.3618(3) -0.2449(7) 0.20660(11) 0.0865(18) Uani 1 1 d . . . . .
H36 H 0.4095 -0.2970 0.2039 0.104 Uiso 1 1 calc R U . . .
C37 C 0.3011(3) -0.2604(7) 0.18701(10) 0.0802(16) Uani 1 1 d . . . . .
H37 H 0.3070 -0.3202 0.1710 0.096 Uiso 1 1 calc R U . . .
C38 C 0.2320(3) -0.1862(8) 0.19151(10) 0.0854(17) Uani 1 1 d . . . . .
H38 H 0.1884 -0.1958 0.1788 0.102 Uiso 1 1 calc R U . . .
C39 C 0.2264(3) -0.0983(6) 0.21432(9) 0.0740(15) Uani 1 1 d . . . . .
H39 H 0.1793 -0.0449 0.2175 0.089 Uiso 1 1 calc R U . . .
C40 C 1.1150(2) 0.3904(5) 0.48354(8) 0.0516(10) Uani 1 1 d . . . . .
H40A H 1.0961 0.4767 0.4934 0.077 Uiso 1 1 calc R U . . .
H40B H 1.0950 0.3919 0.4642 0.077 Uiso 1 1 calc R U . . .
H40C H 1.1730 0.3904 0.4837 0.077 Uiso 1 1 calc R U . . .
C41 C 1.1174(2) 0.1185(5) 0.48366(8) 0.0511(10) Uani 1 1 d . . . . .
H41A H 1.1754 0.1207 0.4842 0.077 Uiso 1 1 calc R U . . .
H41B H 1.0983 0.1163 0.4642 0.077 Uiso 1 1 calc R U . . .
H41C H 1.0989 0.0316 0.4934 0.077 Uiso 1 1 calc R U . . .
C42 C 1.0504(2) 0.3882(5) 0.56632(8) 0.0554(10) Uani 1 1 d . . . . .
H42A H 1.0442 0.4743 0.5545 0.083 Uiso 1 1 calc R U . . .
H42B H 1.1013 0.3929 0.5764 0.083 Uiso 1 1 calc R U . . .
H42C H 1.0074 0.3848 0.5797 0.083 Uiso 1 1 calc R U . . .
C43 C 1.0552(2) 0.1160(5) 0.56616(9) 0.0555(10) Uani 1 1 d . . . . .
H43A H 1.0125 0.1141 0.5797 0.083 Uiso 1 1 calc R U . . .
H43B H 1.1065 0.1163 0.5761 0.083 Uiso 1 1 calc R U . . .
H43C H 1.0514 0.0300 0.5542 0.083 Uiso 1 1 calc R U . . .
C51 C 0.8919(4) 0.1913(8) 0.38863(12) 0.0926(18) Uani 1 1 d . . . . .
H51A H 0.9466 0.1569 0.3857 0.111 Uiso 1 1 calc R U . . .
H51B H 0.8822 0.1898 0.4089 0.111 Uiso 1 1 calc R U . . .
C61 C 0.6800(8) -0.2463(15) 0.3804(4) 0.126(5) Uiso 0.5 1 d D . P A 1
H61A H 0.6684 -0.2044 0.3618 0.152 Uiso 0.5 1 calc R U P A 1
H61B H 0.6929 -0.1665 0.3936 0.152 Uiso 0.5 1 calc R U P A 1
C61A C 0.6754(6) -0.3780(13) 0.3763(2) 0.086(3) Uiso 0.5 1 d D . P B 2
H61C H 0.6767 -0.4830 0.3807 0.103 Uiso 0.5 1 calc R U P B 2
H61D H 0.6606 -0.3623 0.3564 0.103 Uiso 0.5 1 calc R U P B 2


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl51 C51 1.741(7) . ?
Cl52 C51 1.713(7) . ?
Cl61 C61 1.868(14) . ?
Cl62 C61 1.701(14) . ?
Cl6A C61A 1.992(11) . ?
Cl6B C61A 1.714(11) . ?
O1 N1 1.274(4) . ?
O6 C6 1.207(5) . ?
O7 C6 1.360(4) . ?
O7 C8 1.408(4) . ?
N1 C2 1.480(5) . ?
N1 C5 1.486(5) . ?
N25 C24 1.337(5) . ?
N25 C26 1.343(5) . ?
N29 C30 1.326(6) . ?
N29 C28 1.349(6) . ?
N35 C36 1.329(6) . ?
N35 C34 1.329(6) . ?
C2 C3 1.516(5) . ?
C2 C40 1.523(5) . ?
C2 C41 1.532(5) . ?
C3 C4 1.324(5) . ?
C3 C6 1.466(5) . ?
C4 C5 1.483(5) . ?
C4 H4 0.9500 . ?
C5 C42 1.519(6) . ?
C5 C43 1.525(6) . ?
C8 C9 1.373(6) . ?
C8 C13 1.377(6) . ?
C9 C10 1.389(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(6) . ?
C11 C14 1.433(5) . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.206(5) . ?
C15 C16 1.433(5) . ?
C16 C21 1.382(6) . ?
C16 C17 1.384(6) . ?
C17 C18 1.373(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(6) . ?
C19 C22 1.484(5) . ?
C20 C21 1.386(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.386(6) . ?
C22 C27 1.391(6) . ?
C23 C24 1.394(5) . ?
C23 H23 0.9500 . ?
C24 C28 1.487(6) . ?
C26 C27 1.389(5) . ?
C26 C34 1.493(6) . ?
C27 H27 0.9500 . ?
C28 C33 1.377(6) . ?
C30 C31 1.355(7) . ?
C30 H30 0.9500 . ?
C31 C32 1.364(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(7) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C39 1.374(6) . ?
C36 C37 1.384(7) . ?
C36 H36 0.9500 . ?
C37 C38 1.373(8) . ?
C37 H37 0.9500 . ?
C38 C39 1.365(7) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61A H61C 0.9900 . ?
C61A H61D 0.9900 . ?

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
C6 O7 C8 116.0(3) . . ?
O1 N1 C2 122.2(3) . . ?
O1 N1 C5 122.6(3) . . ?
C2 N1 C5 115.2(3) . . ?
C24 N25 C26 118.2(3) . . ?
C30 N29 C28 117.3(4) . . ?
C36 N35 C34 118.3(4) . . ?
N1 C2 C3 99.2(3) . . ?
N1 C2 C40 109.4(3) . . ?
C3 C2 C40 114.3(3) . . ?
N1 C2 C41 109.8(3) . . ?
C3 C2 C41 113.5(3) . . ?
C40 C2 C41 110.1(3) . . ?
C4 C3 C6 126.2(4) . . ?
C4 C3 C2 112.2(3) . . ?
C6 C3 C2 121.7(3) . . ?
C3 C4 C5 114.2(3) . . ?
C3 C4 H4 122.9 . . ?
C5 C4 H4 122.9 . . ?
C4 C5 N1 99.3(3) . . ?
C4 C5 C42 112.7(3) . . ?
N1 C5 C42 110.4(3) . . ?
C4 C5 C43 113.2(3) . . ?
N1 C5 C43 109.8(3) . . ?
C42 C5 C43 110.8(3) . . ?
O6 C6 O7 122.9(3) . . ?
O6 C6 C3 125.0(3) . . ?
O7 C6 C3 112.1(3) . . ?
C9 C8 C13 122.1(3) . . ?
C9 C8 O7 119.5(3) . . ?
C13 C8 O7 118.4(3) . . ?
C8 C9 C10 118.4(4) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 118.7(3) . . ?
C12 C11 C14 119.6(4) . . ?
C10 C11 C14 121.7(4) . . ?
C11 C12 C13 121.1(4) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 118.8(4) . . ?
C8 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C15 C14 C11 177.8(5) . . ?
C14 C15 C16 177.0(4) . . ?
C21 C16 C17 118.4(3) . . ?
C21 C16 C15 121.4(4) . . ?
C17 C16 C15 120.2(4) . . ?
C18 C17 C16 120.3(4) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 122.1(4) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C18 C19 C20 117.4(3) . . ?
C18 C19 C22 121.0(4) . . ?
C20 C19 C22 121.5(4) . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C16 C21 C20 121.5(4) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C27 117.2(3) . . ?
C23 C22 C19 121.0(4) . . ?
C27 C22 C19 121.8(4) . . ?
C22 C23 C24 120.0(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
N25 C24 C23 122.3(4) . . ?
N25 C24 C28 116.7(3) . . ?
C23 C24 C28 121.0(4) . . ?
N25 C26 C27 122.5(4) . . ?
N25 C26 C34 116.3(3) . . ?
C27 C26 C34 121.2(4) . . ?
C26 C27 C22 119.8(4) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
N29 C28 C33 121.8(4) . . ?
N29 C28 C24 116.2(3) . . ?
C33 C28 C24 122.0(4) . . ?
N29 C30 C31 124.1(5) . . ?
N29 C30 H30 117.9 . . ?
C31 C30 H30 117.9 . . ?
C30 C31 C32 118.8(5) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C31 C32 C33 118.8(4) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 H32 120.6 . . ?
C28 C33 C32 119.0(5) . . ?
C28 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
N35 C34 C39 122.1(4) . . ?
N35 C34 C26 117.1(3) . . ?
C39 C34 C26 120.8(4) . . ?
N35 C36 C37 123.2(5) . . ?
N35 C36 H36 118.4 . . ?
C37 C36 H36 118.4 . . ?
C38 C37 C36 117.6(5) . . ?
C38 C37 H37 121.2 . . ?
C36 C37 H37 121.2 . . ?
C39 C38 C37 119.6(4) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C34 119.4(5) . . ?
C38 C39 H39 120.3 . . ?
C34 C39 H39 120.3 . . ?
C2 C40 H40A 109.5 . . ?
C2 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C2 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C2 C41 H41A 109.5 . . ?
C2 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C2 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C5 C42 H42A 109.5 . . ?
C5 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C5 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C5 C43 H43A 109.5 . . ?
C5 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C5 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
Cl52 C51 Cl51 112.5(3) . . ?
Cl52 C51 H51A 109.1 . . ?
Cl51 C51 H51A 109.1 . . ?
Cl52 C51 H51B 109.1 . . ?
Cl51 C51 H51B 109.1 . . ?
H51A C51 H51B 107.8 . . ?
Cl62 C61 Cl61 104.7(8) . . ?
Cl62 C61 H61A 110.8 . . ?
Cl61 C61 H61A 110.8 . . ?
Cl62 C61 H61B 110.8 . . ?
Cl61 C61 H61B 110.8 . . ?
H61A C61 H61B 108.9 . . ?
Cl6B C61A Cl6A 91.5(5) . . ?
Cl6B C61A H61C 113.4 . . ?
Cl6A C61A H61C 113.4 . . ?
Cl6B C61A H61D 113.4 . . ?
Cl6A C61A H61D 113.4 . . ?
H61C C61A H61D 110.7 . . ?

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
O1 N1 C2 C3 -179.8(3) . . . . ?
C5 N1 C2 C3 0.5(4) . . . . ?
O1 N1 C2 C40 -59.9(4) . . . . ?
C5 N1 C2 C40 120.4(3) . . . . ?
O1 N1 C2 C41 61.1(4) . . . . ?
C5 N1 C2 C41 -118.6(3) . . . . ?
N1 C2 C3 C4 -0.4(4) . . . . ?
C40 C2 C3 C4 -116.6(4) . . . . ?
C41 C2 C3 C4 116.0(4) . . . . ?
N1 C2 C3 C6 179.5(3) . . . . ?
C40 C2 C3 C6 63.2(5) . . . . ?
C41 C2 C3 C6 -64.2(5) . . . . ?
C6 C3 C4 C5 -179.7(4) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 N1 0.2(4) . . . . ?
C3 C4 C5 C42 117.0(4) . . . . ?
C3 C4 C5 C43 -116.1(4) . . . . ?
O1 N1 C5 C4 179.8(3) . . . . ?
C2 N1 C5 C4 -0.5(4) . . . . ?
O1 N1 C5 C42 61.2(5) . . . . ?
C2 N1 C5 C42 -119.1(3) . . . . ?
O1 N1 C5 C43 -61.3(4) . . . . ?
C2 N1 C5 C43 118.4(3) . . . . ?
C8 O7 C6 O6 2.6(5) . . . . ?
C8 O7 C6 C3 -177.0(3) . . . . ?
C4 C3 C6 O6 -177.9(4) . . . . ?
C2 C3 C6 O6 2.3(6) . . . . ?
C4 C3 C6 O7 1.8(5) . . . . ?
C2 C3 C6 O7 -178.0(3) . . . . ?
C6 O7 C8 C9 -93.1(4) . . . . ?
C6 O7 C8 C13 88.9(4) . . . . ?
C13 C8 C9 C10 -3.2(6) . . . . ?
O7 C8 C9 C10 178.8(3) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C9 C10 C11 C12 3.6(6) . . . . ?
C9 C10 C11 C14 -177.8(4) . . . . ?
C10 C11 C12 C13 -3.4(6) . . . . ?
C14 C11 C12 C13 177.9(3) . . . . ?
C9 C8 C13 C12 3.5(6) . . . . ?
O7 C8 C13 C12 -178.6(3) . . . . ?
C11 C12 C13 C8 0.0(6) . . . . ?
C21 C16 C17 C18 0.9(6) . . . . ?
C15 C16 C17 C18 -177.0(4) . . . . ?
C16 C17 C18 C19 0.9(6) . . . . ?
C17 C18 C19 C20 -2.2(6) . . . . ?
C17 C18 C19 C22 175.0(4) . . . . ?
C18 C19 C20 C21 1.6(6) . . . . ?
C22 C19 C20 C21 -175.5(4) . . . . ?
C17 C16 C21 C20 -1.4(6) . . . . ?
C15 C16 C21 C20 176.5(4) . . . . ?
C19 C20 C21 C16 0.1(6) . . . . ?
C18 C19 C22 C23 -29.3(6) . . . . ?
C20 C19 C22 C23 147.7(4) . . . . ?
C18 C19 C22 C27 151.0(4) . . . . ?
C20 C19 C22 C27 -32.0(6) . . . . ?
C27 C22 C23 C24 -1.1(6) . . . . ?
C19 C22 C23 C24 179.2(4) . . . . ?
C26 N25 C24 C23 0.0(6) . . . . ?
C26 N25 C24 C28 179.0(4) . . . . ?
C22 C23 C24 N25 0.9(7) . . . . ?
C22 C23 C24 C28 -178.1(4) . . . . ?
C24 N25 C26 C27 -0.6(6) . . . . ?
C24 N25 C26 C34 -179.4(4) . . . . ?
N25 C26 C27 C22 0.3(6) . . . . ?
C34 C26 C27 C22 179.1(4) . . . . ?
C23 C22 C27 C26 0.5(6) . . . . ?
C19 C22 C27 C26 -179.8(4) . . . . ?
C30 N29 C28 C33 -1.1(8) . . . . ?
C30 N29 C28 C24 178.5(5) . . . . ?
N25 C24 C28 N29 175.3(4) . . . . ?
C23 C24 C28 N29 -5.6(6) . . . . ?
N25 C24 C28 C33 -5.0(6) . . . . ?
C23 C24 C28 C33 174.0(4) . . . . ?
C28 N29 C30 C31 -2.2(10) . . . . ?
N29 C30 C31 C32 3.6(11) . . . . ?
C30 C31 C32 C33 -1.5(9) . . . . ?
N29 C28 C33 C32 3.0(7) . . . . ?
C24 C28 C33 C32 -176.7(4) . . . . ?
C31 C32 C33 C28 -1.6(8) . . . . ?
C36 N35 C34 C39 0.5(8) . . . . ?
C36 N35 C34 C26 179.8(5) . . . . ?
N25 C26 C34 N35 -176.9(4) . . . . ?
C27 C26 C34 N35 4.2(6) . . . . ?
N25 C26 C34 C39 2.4(6) . . . . ?
C27 C26 C34 C39 -176.5(5) . . . . ?
C34 N35 C36 C37 -0.1(9) . . . . ?
N35 C36 C37 C38 -1.0(10) . . . . ?
C36 C37 C38 C39 1.7(9) . . . . ?
C37 C38 C39 C34 -1.3(9) . . . . ?
N35 C34 C39 C38 0.1(8) . . . . ?
C26 C34 C39 C38 -179.1(5) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1497632'
_audit_update_record             
;
2016-08-04 deposited with the CCDC.
2018-03-29 downloaded from the CCDC.
;
_audit_creation_date             2015-04-13
_audit_creation_method           'by CrystalStructure 4.1'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H17 I N O3'
_chemical_formula_moiety         'C15 H17 I N O3'
_chemical_formula_weight         386.21
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.0407(16)
_cell_length_b                   9.359(2)
_cell_length_c                   10.1910(19)
_cell_angle_alpha                105.821(3)
_cell_angle_beta                 94.648(3)
_cell_angle_gamma                105.915(4)
_cell_volume                     786.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2685
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.40
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             382.00
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_T_max  0.903

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 11.628
_diffrn_reflns_number            9770
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         2.107
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2873
_reflns_number_gt                2630
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0234
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0551
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2873
_refine_ls_number_parameters     185
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0249P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.29
_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 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
I14 I 1.05319(2) 0.40893(2) 0.25035(2) 0.03378(8) Uani 1 1 d . . . . .
O1 O 0.2979(2) 1.2622(2) 0.3169(2) 0.0388(5) Uani 1 1 d . . . . .
O6 O 0.7227(2) 0.9594(2) 0.2384(2) 0.0479(5) Uani 1 1 d . . . . .
O7 O 0.5383(2) 0.72996(19) 0.2033(2) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.3296(2) 1.1350(2) 0.2909(2) 0.0280(5) Uani 1 1 d . . . . .
C2 C 0.4907(3) 1.1293(3) 0.2759(3) 0.0266(5) Uani 1 1 d . . . . .
C3 C 0.4601(3) 0.9548(3) 0.2438(2) 0.0248(5) Uani 1 1 d . . . . .
C4 C 0.3110(3) 0.8774(3) 0.2345(3) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.2728 0.7674 0.2159 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2093(3) 0.9807(3) 0.2563(3) 0.0279(5) Uani 1 1 d . . . . .
C6 C 0.5892(3) 0.8873(3) 0.2286(3) 0.0295(6) Uani 1 1 d . . . . .
C8 C 0.6555(3) 0.6582(3) 0.2109(3) 0.0305(6) Uani 1 1 d . . . . .
C9 C 0.7095(3) 0.6493(3) 0.3379(3) 0.0321(6) Uani 1 1 d . . . . .
H9 H 0.6680 0.6907 0.4172 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8243(3) 0.5801(3) 0.3489(3) 0.0296(6) Uani 1 1 d . . . . .
H10 H 0.8639 0.5750 0.4363 0.036 Uiso 1 1 calc R U . . .
C11 C 0.8817(3) 0.5176(3) 0.2313(3) 0.0266(5) Uani 1 1 d . . . . .
C12 C 0.8238(3) 0.5242(3) 0.1041(3) 0.0293(5) Uani 1 1 d . . . . .
H12 H 0.8617 0.4791 0.0237 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7102(3) 0.5968(3) 0.0936(3) 0.0315(6) Uani 1 1 d . . . . .
H13 H 0.6712 0.6038 0.0069 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5999(3) 1.2258(3) 0.4123(3) 0.0346(6) Uani 1 1 d . . . . .
H15A H 0.5677 1.1799 0.4852 0.041 Uiso 1 1 calc R U . . .
H15B H 0.5954 1.3331 0.4372 0.041 Uiso 1 1 calc R U . . .
H15C H 0.7069 1.2263 0.4022 0.041 Uiso 1 1 calc R U . . .
C16 C 0.5408(3) 1.1899(3) 0.1576(3) 0.0356(6) Uani 1 1 d . . . . .
H16A H 0.5418 1.2988 0.1782 0.043 Uiso 1 1 calc R U . . .
H16B H 0.4673 1.1264 0.0721 0.043 Uiso 1 1 calc R U . . .
H16C H 0.6456 1.1836 0.1459 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1215(3) 0.9734(3) 0.3761(3) 0.0409(7) Uani 1 1 d . . . . .
H17A H 0.0707 1.0552 0.3938 0.049 Uiso 1 1 calc R U . . .
H17B H 0.1948 0.9894 0.4590 0.049 Uiso 1 1 calc R U . . .
H17C H 0.0424 0.8710 0.3531 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0989(3) 0.9537(3) 0.1245(3) 0.0411(7) Uani 1 1 d . . . . .
H18A H 0.1588 0.9615 0.0494 0.049 Uiso 1 1 calc R U . . .
H18B H 0.0447 1.0328 0.1402 0.049 Uiso 1 1 calc R U . . .
H18C H 0.0222 0.8496 0.0992 0.049 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
I14 C11 2.097(2) . ?
O1 N1 1.264(3) . ?
O6 C6 1.191(3) . ?
O7 C6 1.360(3) . ?
O7 C8 1.409(3) . ?
N1 C5 1.481(3) . ?
N1 C2 1.490(3) . ?
C2 C3 1.515(3) . ?
C2 C16 1.517(4) . ?
C2 C15 1.526(4) . ?
C3 C4 1.325(3) . ?
C3 C6 1.472(3) . ?
C4 C5 1.495(3) . ?
C4 H4 0.9500 . ?
C5 C17 1.516(4) . ?
C5 C18 1.525(4) . ?
C8 C13 1.371(4) . ?
C8 C9 1.378(4) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C6 O7 C8 115.78(19) . . ?
O1 N1 C5 123.24(19) . . ?
O1 N1 C2 121.46(19) . . ?
C5 N1 C2 114.89(18) . . ?
N1 C2 C3 98.80(18) . . ?
N1 C2 C16 109.3(2) . . ?
C3 C2 C16 113.4(2) . . ?
N1 C2 C15 108.9(2) . . ?
C3 C2 C15 113.9(2) . . ?
C16 C2 C15 111.7(2) . . ?
C4 C3 C6 126.4(2) . . ?
C4 C3 C2 113.0(2) . . ?
C6 C3 C2 120.6(2) . . ?
C3 C4 C5 113.1(2) . . ?
C3 C4 H4 123.4 . . ?
C5 C4 H4 123.4 . . ?
N1 C5 C4 99.79(19) . . ?
N1 C5 C17 109.7(2) . . ?
C4 C5 C17 113.9(2) . . ?
N1 C5 C18 109.5(2) . . ?
C4 C5 C18 112.3(2) . . ?
C17 C5 C18 111.1(2) . . ?
O6 C6 O7 123.1(2) . . ?
O6 C6 C3 125.3(2) . . ?
O7 C6 C3 111.6(2) . . ?
C13 C8 C9 121.9(2) . . ?
C13 C8 O7 120.1(2) . . ?
C9 C8 O7 118.0(2) . . ?
C8 C9 C10 119.5(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 I14 120.96(18) . . ?
C10 C11 I14 118.70(18) . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 118.7(2) . . ?
C8 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C2 C15 H15A 109.5 . . ?
C2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16A 109.5 . . ?
C2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C18 H18A 109.5 . . ?
C5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O1 N1 C2 C3 -178.9(2) . . . . ?
C5 N1 C2 C3 -6.1(3) . . . . ?
O1 N1 C2 C16 -60.2(3) . . . . ?
C5 N1 C2 C16 112.6(2) . . . . ?
O1 N1 C2 C15 62.0(3) . . . . ?
C5 N1 C2 C15 -125.1(2) . . . . ?
N1 C2 C3 C4 3.1(3) . . . . ?
C16 C2 C3 C4 -112.4(2) . . . . ?
C15 C2 C3 C4 118.4(2) . . . . ?
N1 C2 C3 C6 -175.8(2) . . . . ?
C16 C2 C3 C6 68.7(3) . . . . ?
C15 C2 C3 C6 -60.5(3) . . . . ?
C6 C3 C4 C5 179.5(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
O1 N1 C5 C4 179.1(2) . . . . ?
C2 N1 C5 C4 6.4(3) . . . . ?
O1 N1 C5 C17 -61.0(3) . . . . ?
C2 N1 C5 C17 126.3(2) . . . . ?
O1 N1 C5 C18 61.2(3) . . . . ?
C2 N1 C5 C18 -111.5(2) . . . . ?
C3 C4 C5 N1 -4.2(3) . . . . ?
C3 C4 C5 C17 -120.9(2) . . . . ?
C3 C4 C5 C18 111.7(3) . . . . ?
C8 O7 C6 O6 9.7(4) . . . . ?
C8 O7 C6 C3 -169.4(2) . . . . ?
C4 C3 C6 O6 -179.3(3) . . . . ?
C2 C3 C6 O6 -0.6(4) . . . . ?
C4 C3 C6 O7 -0.2(4) . . . . ?
C2 C3 C6 O7 178.5(2) . . . . ?
C6 O7 C8 C13 -93.7(3) . . . . ?
C6 O7 C8 C9 87.7(3) . . . . ?
C13 C8 C9 C10 1.5(4) . . . . ?
O7 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 -1.2(4) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C9 C10 C11 I14 -178.82(18) . . . . ?
C10 C11 C12 C13 1.5(4) . . . . ?
I14 C11 C12 C13 -179.98(18) . . . . ?
C9 C8 C13 C12 -0.2(4) . . . . ?
O7 C8 C13 C12 -178.8(2) . . . . ?
C11 C12 C13 C8 -1.3(4) . . . . ?

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
