# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry B.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1523227'
_audit_update_record             
;
2016-12-17 deposited with the CCDC.
2017-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 I N2'
_chemical_formula_weight         390.25

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   7.2991(12)
_cell_length_b                   18.472(3)
_cell_length_c                   12.541(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1690.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.6010
_exptl_absorpt_correction_T_max  0.7037
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5902
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1509
_reflns_number_gt                1422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0165P)²+0.6418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_number_reflns         1509
_refine_ls_number_parameters     126
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0430
_refine_ls_wR_factor_gt          0.0418
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.060
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.0000 0.317152(13) 0.05301(6) 0.05497(10) Uani 1 2 d S . .
C16 C 0.0000 0.1939(4) 0.4406(8) 0.055(3) Uani 1 2 d S . .
H16A H 0.1220 0.1748 0.4357 0.082 Uiso 0.50 1 calc PR . .
H16B H -0.0417 0.2076 0.3708 0.082 Uiso 0.50 1 calc PR . .
H16C H -0.0803 0.1577 0.4694 0.082 Uiso 0.50 1 calc PR . .
C8 C 0.0000 0.2569(5) 0.6137(6) 0.0400(16) Uani 1 2 d S . .
C7 C 0.0000 0.1901(3) 0.6723(8) 0.043(2) Uani 1 2 d S . .
H7 H 0.0000 0.1473 0.6332 0.052 Uiso 1 2 calc SR . .
N2 N 0.0000 0.2570(3) 0.5098(4) 0.0386(15) Uani 1 2 d S . .
C9 C 0.0000 0.3353(4) 0.6551(6) 0.0411(17) Uani 1 2 d S . .
C6 C 0.0000 0.1846(2) 0.7784(4) 0.0481(10) Uani 1 2 d S . .
H6 H 0.0000 0.2271 0.8182 0.058 Uiso 1 2 calc SR . .
C10 C 0.0000 0.37654(17) 0.5524(10) 0.0431(7) Uani 1 2 d S . .
C3 C 0.0000 0.1156(2) 0.9458(4) 0.0582(12) Uani 1 2 d S . .
H3 H 0.0000 0.1591 0.9830 0.070 Uiso 1 2 calc SR . .
C5 C 0.0000 0.1150(2) 0.8366(3) 0.0465(10) Uani 1 2 d S . .
C13 C 0.0000 0.3508(3) 0.3627(4) 0.0537(11) Uani 1 2 d S . .
H13 H 0.0000 0.3178 0.3068 0.064 Uiso 1 2 calc SR . .
C17 C 0.1735(4) 0.35076(17) 0.7207(2) 0.0553(8) Uani 1 1 d . . .
H17A H 0.1847 0.4020 0.7320 0.083 Uiso 1 1 calc R . .
H17B H 0.2789 0.3334 0.6827 0.083 Uiso 1 1 calc R . .
H17C H 0.1651 0.3265 0.7882 0.083 Uiso 1 1 calc R . .
C12 C 0.0000 0.4498(2) 0.5331(5) 0.0575(18) Uani 1 2 d S . .
H12 H 0.0000 0.4828 0.5891 0.069 Uiso 1 2 calc SR . .
C4 C 0.0000 0.0477(3) 0.7870(5) 0.0639(15) Uani 1 2 d S . .
H4 H 0.0000 0.0440 0.7131 0.077 Uiso 1 2 calc SR . .
N1 N 0.0000 -0.0137(2) 0.9566(4) 0.0695(11) Uani 1 2 d S . .
C2 C 0.0000 -0.0143(3) 0.8508(6) 0.0720(17) Uani 1 2 d S . .
H2 H 0.0000 -0.0591 0.8168 0.086 Uiso 1 2 calc SR . .
C1 C 0.0000 0.0506(3) 0.9997(5) 0.0716(15) Uani 1 2 d S . .
H1 H 0.0000 0.0527 1.0738 0.086 Uiso 1 2 calc SR . .
C15 C 0.0000 0.4238(3) 0.3447(4) 0.0682(14) Uani 1 2 d S . .
H15 H 0.0000 0.4407 0.2749 0.082 Uiso 1 2 calc SR . .
C14 C 0.0000 0.4733(3) 0.4279(5) 0.0719(15) Uani 1 2 d S . .
H14 H 0.0000 0.5226 0.4131 0.086 Uiso 1 2 calc SR . .
C11 C 0.0000 0.3286(4) 0.4669(7) 0.0413(19) Uani 1 2 d S . .


_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
C16 N2 1.454(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C8 N2 1.303(5) . ?
C8 C7 1.437(11) . ?
C8 C9 1.537(10) . ?
C7 C6 1.335(12) . ?
C7 H7 0.9300 . ?
N2 C11 1.427(8) . ?
C9 C10 1.497(13) . ?
C9 C17 1.537(5) . ?
C9 C17 1.537(5) 4 ?
C6 C5 1.478(6) . ?
C6 H6 0.9300 . ?
C10 C12 1.374(5) . ?
C10 C11 1.391(13) . ?
C3 C5 1.370(7) . ?
C3 C1 1.377(6) . ?
C3 H3 0.9300 . ?
C5 C4 1.390(6) . ?
C13 C15 1.367(7) . ?
C13 C11 1.369(9) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C12 C14 1.389(9) . ?
C12 H12 0.9300 . ?
C4 C2 1.397(7) . ?
C4 H4 0.9300 . ?
N1 C1 1.305(6) . ?
N1 C2 1.327(8) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C15 C14 1.388(8) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?

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
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C8 C7 120.8(9) . . ?
N2 C8 C9 109.7(8) . . ?
C7 C8 C9 129.5(8) . . ?
C6 C7 C8 125.1(7) . . ?
C6 C7 H7 117.5 . . ?
C8 C7 H7 117.5 . . ?
C8 N2 C11 112.3(8) . . ?
C8 N2 C16 126.6(9) . . ?
C11 N2 C16 121.1(8) . . ?
C10 C9 C17 111.4(4) . . ?
C10 C9 C17 111.4(4) . 4 ?
C17 C9 C17 111.0(5) . 4 ?
C10 C9 C8 100.9(6) . . ?
C17 C9 C8 110.9(4) . . ?
C17 C9 C8 110.9(4) 4 . ?
C7 C6 C5 123.9(4) . . ?
C7 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
C12 C10 C11 119.4(10) . . ?
C12 C10 C9 130.8(9) . . ?
C11 C10 C9 109.8(3) . . ?
C5 C3 C1 118.9(4) . . ?
C5 C3 H3 120.5 . . ?
C1 C3 H3 120.5 . . ?
C3 C5 C4 117.0(4) . . ?
C3 C5 C6 119.1(4) . . ?
C4 C5 C6 123.9(4) . . ?
C15 C13 C11 117.0(5) . . ?
C15 C13 H13 121.5 . . ?
C11 C13 H13 121.5 . . ?
C9 C17 H17A 109.5 . . ?
C9 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C9 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C12 C14 118.4(7) . . ?
C10 C12 H12 120.8 . . ?
C14 C12 H12 120.8 . . ?
C5 C4 C2 118.6(6) . . ?
C5 C4 H4 120.7 . . ?
C2 C4 H4 120.7 . . ?
C1 N1 C2 115.0(4) . . ?
N1 C2 C4 124.4(6) . . ?
N1 C2 H2 117.8 . . ?
C4 C2 H2 117.8 . . ?
N1 C1 C3 126.2(5) . . ?
N1 C1 H1 116.9 . . ?
C3 C1 H1 116.9 . . ?
C13 C15 C14 121.7(5) . . ?
C13 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C14 C12 120.5(5) . . ?
C15 C14 H14 119.7 . . ?
C12 C14 H14 119.7 . . ?
C13 C11 C10 123.0(7) . . ?
C13 C11 N2 129.6(7) . . ?
C10 C11 N2 107.4(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
N2 C8 C7 C6 180.000(2) . . . . ?
C9 C8 C7 C6 0.000(2) . . . . ?
C7 C8 N2 C11 180.000(2) . . . . ?
C9 C8 N2 C11 0.000(2) . . . . ?
C7 C8 N2 C16 0.000(3) . . . . ?
C9 C8 N2 C16 180.000(2) . . . . ?
N2 C8 C9 C10 0.000(3) . . . . ?
C7 C8 C9 C10 180.000(3) . . . . ?
N2 C8 C9 C17 -118.2(4) . . . . ?
C7 C8 C9 C17 61.8(4) . . . . ?
N2 C8 C9 C17 118.2(4) . . . 4 ?
C7 C8 C9 C17 -61.8(4) . . . 4 ?
C8 C7 C6 C5 180.000(2) . . . . ?
C17 C9 C10 C12 -62.3(4) . . . . ?
C17 C9 C10 C12 62.3(4) 4 . . . ?
C8 C9 C10 C12 180.000(2) . . . . ?
C17 C9 C10 C11 117.7(4) . . . . ?
C17 C9 C10 C11 -117.7(4) 4 . . . ?
C8 C9 C10 C11 0.000(2) . . . . ?
C1 C3 C5 C4 0.000(2) . . . . ?
C1 C3 C5 C6 180.000(1) . . . . ?
C7 C6 C5 C3 180.000(1) . . . . ?
C7 C6 C5 C4 0.000(2) . . . . ?
C11 C10 C12 C14 0.000(3) . . . . ?
C9 C10 C12 C14 180.000(3) . . . . ?
C3 C5 C4 C2 0.000(2) . . . . ?
C6 C5 C4 C2 180.000(1) . . . . ?
C1 N1 C2 C4 0.000(2) . . . . ?
C5 C4 C2 N1 0.000(2) . . . . ?
C2 N1 C1 C3 0.000(2) . . . . ?
C5 C3 C1 N1 0.000(2) . . . . ?
C11 C13 C15 C14 0.000(2) . . . . ?
C13 C15 C14 C12 0.000(2) . . . . ?
C10 C12 C14 C15 0.000(2) . . . . ?
C15 C13 C11 C10 0.000(3) . . . . ?
C15 C13 C11 N2 180.000(2) . . . . ?
C12 C10 C11 C13 0.000(3) . . . . ?
C9 C10 C11 C13 180.000(2) . . . . ?
C12 C10 C11 N2 180.000(3) . . . . ?
C9 C10 C11 N2 0.000(2) . . . . ?
C8 N2 C11 C13 180.000(2) . . . . ?
C16 N2 C11 C13 0.000(3) . . . . ?
C8 N2 C11 C10 0.000(2) . . . . ?
C16 N2 C11 C10 180.000(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1523228'
_audit_update_record             
;
2016-12-17 deposited with the CCDC.
2017-04-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 I2 N2 O'
_chemical_formula_weight         585.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.632(5)
_cell_length_b                   6.968(5)
_cell_length_c                   24.753(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.016(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2166.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             1132
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.917
_shelx_estimated_absorpt_T_min   0.475
_shelx_estimated_absorpt_T_max   0.593
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14676
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3919
_reflns_number_gt                3697
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0459P)²+3.9074P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.012
_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
C1 C 0.6947(2) 0.1783(5) 0.10432(13) 0.0294(7) Uani 1 1 d . . . . .
H1 H 0.7555 0.1594 0.1283 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5954(2) 0.1861(5) 0.12446(13) 0.0244(6) Uani 1 1 d . . . . .
H2 H 0.5908 0.1724 0.1615 0.029 Uiso 1 1 calc R U . . .
C3 C 0.5039(2) 0.2143(4) 0.08933(13) 0.0168(6) Uani 1 1 d . . . . .
C4 C 0.5136(3) 0.2334(4) 0.03278(14) 0.0183(7) Uani 1 1 d . . . . .
C5 C 0.6174(3) 0.2265(4) 0.01482(15) 0.0196(7) Uani 1 1 d . . . . .
C6 C 0.6327(3) 0.2478(4) -0.04070(17) 0.0266(8) Uani 1 1 d . . . . .
H6 H 0.7008 0.2427 -0.0516 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5463(3) 0.2759(4) -0.07827(14) 0.0287(8) Uani 1 1 d . . . . .
H7 H 0.5556 0.2904 -0.1148 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4432(3) 0.2826(5) -0.06117(15) 0.0270(8) Uani 1 1 d . . . . .
H8 H 0.3850 0.3011 -0.0869 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4268(3) 0.2627(4) -0.00781(14) 0.0199(7) Uani 1 1 d . . . . .
H9 H 0.3579 0.2683 0.0021 0.024 Uiso 1 1 calc R U . . .
C10 C 0.3992(2) 0.2241(4) 0.10945(12) 0.0178(7) Uani 1 1 d . . . . .
H10 H 0.3403 0.2278 0.0836 0.021 Uiso 1 1 calc R U . . .
C11 C 0.3805(3) 0.2283(4) 0.16186(14) 0.0174(6) Uani 1 1 d . . . . .
H11 H 0.4380 0.2256 0.1886 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2746(3) 0.2369(3) 0.17805(13) 0.0143(6) Uani 1 1 d . . . . .
C13 C 0.1690(3) 0.2456(4) 0.14186(13) 0.0153(6) Uani 1 1 d . . . . .
C14 C 0.0910(3) 0.2517(4) 0.18346(15) 0.0193(7) Uani 1 1 d . . . . .
C15 C 0.1437(3) 0.2467(4) 0.23469(15) 0.0200(7) Uani 1 1 d . . . . .
C16 C 0.0950(3) 0.2490(4) 0.28185(16) 0.0238(8) Uani 1 1 d . . . . .
H16 H 0.1335 0.2460 0.3160 0.029 Uiso 1 1 calc R U . . .
C17 C -0.0156(3) 0.2561(4) 0.27507(18) 0.0309(9) Uani 1 1 d . . . . .
H17 H -0.0531 0.2568 0.3055 0.037 Uiso 1 1 calc R U . . .
C18 C -0.0707(3) 0.2620(4) 0.22358(18) 0.0315(9) Uani 1 1 d . . . . .
H18 H -0.1446 0.2674 0.2203 0.038 Uiso 1 1 calc R U . . .
C19 C -0.0193(3) 0.2602(4) 0.17683(18) 0.0283(8) Uani 1 1 d . . . . .
H19 H -0.0570 0.2645 0.1425 0.034 Uiso 1 1 calc R U . . .
C20 C 0.3350(3) 0.2317(4) 0.27712(14) 0.0224(7) Uani 1 1 d . . . . .
H20A H 0.3679 0.1073 0.2795 0.034 Uiso 1 1 calc R U . . .
H20B H 0.3011 0.2557 0.3094 0.034 Uiso 1 1 calc R U . . .
H20C H 0.3883 0.3279 0.2735 0.034 Uiso 1 1 calc R U . . .
C21 C 0.1600(2) 0.4310(4) 0.10675(12) 0.0199(6) Uani 1 1 d . . . . .
H21A H 0.0875 0.4484 0.0917 0.030 Uiso 1 1 calc R U . . .
H21B H 0.2047 0.4196 0.0779 0.030 Uiso 1 1 calc R U . . .
H21C H 0.1822 0.5395 0.1290 0.030 Uiso 1 1 calc R U . . .
C22 C 0.1514(2) 0.0626(4) 0.10619(12) 0.0210(6) Uani 1 1 d . . . . .
H22A H 0.1708 -0.0488 0.1278 0.032 Uiso 1 1 calc R U . . .
H22B H 0.1948 0.0695 0.0766 0.032 Uiso 1 1 calc R U . . .
H22C H 0.0778 0.0540 0.0921 0.032 Uiso 1 1 calc R U . . .
I1 I 0.35340(2) 0.73454(3) 0.21984(2) 0.01872(10) Uani 1 1 d . . . . .
I2 I 0.12819(2) 0.25209(3) 0.44290(2) 0.02727(10) Uani 1 1 d . . . . .
N1 N 0.7038(2) 0.1972(4) 0.05198(12) 0.0254(6) Uani 1 1 d . . . . .
N2 N 0.2553(2) 0.2383(3) 0.22963(11) 0.0159(5) Uani 1 1 d . . . . .
O1 O 0.8929(2) 0.2786(4) 0.01706(15) 0.0466(8) Uani 1 1 d . . . . .
H1A H 0.8287 0.2710 0.0030 0.056 Uiso 1 1 d R U . . .
H1B H 0.9336 0.2946 -0.0078 0.070 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.319(4) . ?
C1 C2 1.398(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.424(5) . ?
C3 C10 1.462(4) . ?
C4 C9 1.422(5) . ?
C4 C5 1.429(5) . ?
C5 N1 1.367(5) . ?
C5 C6 1.416(5) . ?
C6 C7 1.371(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.365(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.343(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.438(5) . ?
C11 H11 0.9300 . ?
C12 N2 1.325(4) . ?
C12 C13 1.527(4) . ?
C13 C14 1.499(5) . ?
C13 C22 1.554(4) . ?
C13 C21 1.554(4) . ?
C14 C15 1.369(5) . ?
C14 C19 1.387(5) . ?
C15 C16 1.375(5) . ?
C15 N2 1.430(5) . ?
C16 C17 1.390(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(6) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N2 1.466(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O1 H1A 0.8499 . ?
O1 H1B 0.8499 . ?

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 121.4(3) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 C10 121.2(3) . . ?
C4 C3 C10 120.3(3) . . ?
C9 C4 C3 124.6(3) . . ?
C9 C4 C5 116.7(3) . . ?
C3 C4 C5 118.6(3) . . ?
N1 C5 C6 119.2(3) . . ?
N1 C5 C4 119.3(3) . . ?
C6 C5 C4 121.4(3) . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 121.6(4) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C4 C9 H9 119.5 . . ?
C11 C10 C3 126.0(3) . . ?
C11 C10 H10 117.0 . . ?
C3 C10 H10 117.0 . . ?
C10 C11 C12 122.2(3) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
N2 C12 C11 122.6(3) . . ?
N2 C12 C13 109.1(3) . . ?
C11 C12 C13 128.2(3) . . ?
C14 C13 C12 101.2(3) . . ?
C14 C13 C22 110.4(2) . . ?
C12 C13 C22 111.4(2) . . ?
C14 C13 C21 110.2(2) . . ?
C12 C13 C21 111.7(2) . . ?
C22 C13 C21 111.5(3) . . ?
C15 C14 C19 119.7(3) . . ?
C15 C14 C13 110.2(3) . . ?
C19 C14 C13 130.1(4) . . ?
C14 C15 C16 124.6(4) . . ?
C14 C15 N2 107.9(3) . . ?
C16 C15 N2 127.4(3) . . ?
C15 C16 C17 115.5(4) . . ?
C15 C16 H16 122.2 . . ?
C17 C16 H16 122.2 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 122.2(4) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C14 117.0(4) . . ?
C18 C19 H19 121.5 . . ?
C14 C19 H19 121.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C22 H22A 109.5 . . ?
C13 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C13 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 N1 C5 122.0(3) . . ?
C12 N2 C15 111.5(3) . . ?
C12 N2 C20 126.3(3) . . ?
C15 N2 C20 122.1(3) . . ?
H1A O1 H1B 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
N1 C1 C2 C3 0.0(6) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C1 C2 C3 C10 -179.7(3) . . . . ?
C2 C3 C4 C9 179.9(3) . . . . ?
C10 C3 C4 C9 0.0(4) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C10 C3 C4 C5 178.9(3) . . . . ?
C9 C4 C5 N1 -179.5(3) . . . . ?
C3 C4 C5 N1 1.6(4) . . . . ?
C9 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C5 C6 -178.9(3) . . . . ?
N1 C5 C6 C7 179.5(3) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 0.3(5) . . . . ?
C7 C8 C9 C4 -0.2(5) . . . . ?
C3 C4 C9 C8 179.0(3) . . . . ?
C5 C4 C9 C8 0.1(4) . . . . ?
C2 C3 C10 C11 7.5(5) . . . . ?
C4 C3 C10 C11 -172.6(3) . . . . ?
C3 C10 C11 C12 -179.6(3) . . . . ?
C10 C11 C12 N2 179.0(3) . . . . ?
C10 C11 C12 C13 -1.0(4) . . . . ?
N2 C12 C13 C14 0.0(3) . . . . ?
C11 C12 C13 C14 180.0(2) . . . . ?
N2 C12 C13 C22 -117.4(3) . . . . ?
C11 C12 C13 C22 62.7(3) . . . . ?
N2 C12 C13 C21 117.2(3) . . . . ?
C11 C12 C13 C21 -62.8(3) . . . . ?
C12 C13 C14 C15 -0.2(3) . . . . ?
C22 C13 C14 C15 117.9(3) . . . . ?
C21 C13 C14 C15 -118.5(3) . . . . ?
C12 C13 C14 C19 -179.8(3) . . . . ?
C22 C13 C14 C19 -61.7(4) . . . . ?
C21 C13 C14 C19 61.9(4) . . . . ?
C19 C14 C15 C16 0.1(4) . . . . ?
C13 C14 C15 C16 -179.5(2) . . . . ?
C19 C14 C15 N2 180.0(2) . . . . ?
C13 C14 C15 N2 0.3(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
N2 C15 C16 C17 -179.5(2) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C14 0.1(4) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C13 C14 C19 C18 179.3(3) . . . . ?
C2 C1 N1 C5 0.4(5) . . . . ?
C6 C5 N1 C1 179.3(3) . . . . ?
C4 C5 N1 C1 -1.2(5) . . . . ?
C11 C12 N2 C15 -179.8(2) . . . . ?
C13 C12 N2 C15 0.2(3) . . . . ?
C11 C12 N2 C20 0.0(4) . . . . ?
C13 C12 N2 C20 -179.9(2) . . . . ?
C14 C15 N2 C12 -0.3(3) . . . . ?
C16 C15 N2 C12 179.5(3) . . . . ?
C14 C15 N2 C20 179.8(2) . . . . ?
C16 C15 N2 C20 -0.3(4) . . . . ?

_refine_diff_density_max         0.698
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.172

_shelxl_version_number           2013-2



