# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_114s
_database_code_depnum_ccdc_archive 'CCDC 2248096'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 I N2 O2'
_chemical_formula_weight         383.20

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'
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                   8.4502(4)
_cell_length_b                   21.4984(12)
_cell_length_c                   8.7348(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.103(3)
_cell_angle_gamma                90
_cell_volume                     1532.00(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1946
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      20.08

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2786
_exptl_absorpt_correction_T_max  0.3595
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14741
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.784
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4058
_reflns_number_gt                2160
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0164P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0570
_refine_ls_goodness_of_fit_ref   0.770
_refine_ls_restrained_S_all      0.770
_refine_ls_shift/su_max          0.001
_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
O1 O 0.8671(3) 0.86494(11) 0.2532(4) 0.0677(9) Uani 1 1 d . . . . .
N2 N 0.9973(3) 0.84098(12) 0.2326(4) 0.0400(7) Uani 1 1 d . . . . .
C3 C 1.1337(4) 0.88111(15) 0.2102(5) 0.0437(10) Uani 1 1 d . . . . .
C4 C 1.1766(9) 0.9278(4) 0.3443(12) 0.093(2) Uani 1 1 d . . . . .
H4A H 1.285(8) 0.943(3) 0.375(7) 0.14(2) Uiso 1 1 d . . . . .
H4B H 1.084(8) 0.947(3) 0.337(7) 0.13(2) Uiso 1 1 d . . . . .
H4C H 1.192(6) 0.904(2) 0.427(6) 0.07(2) Uiso 1 1 d . . . . .
C5 C 1.0677(6) 0.9155(2) 0.0557(7) 0.0972(19) Uani 1 1 d . . . . .
H5A H 1.151458 0.942096 0.035957 0.146 Uiso 1 1 calc R U . . .
H5B H 1.034592 0.886072 -0.029333 0.146 Uiso 1 1 calc R U . . .
H5C H 0.974979 0.940174 0.062319 0.146 Uiso 1 1 calc R U . . .
C6 C 1.2673(4) 0.83268(16) 0.2055(5) 0.0403(9) Uani 1 1 d . . . . .
C7 C 1.3422(9) 0.8375(3) 0.0660(8) 0.0689(15) Uani 1 1 d . . . . .
H7A H 1.396(5) 0.876(2) 0.070(5) 0.080(15) Uiso 1 1 d . . . . .
H7B H 1.426(5) 0.812(2) 0.092(5) 0.071(17) Uiso 1 1 d . . . . .
H7C H 1.257(6) 0.836(2) -0.032(7) 0.10(2) Uiso 1 1 d . . . . .
C8 C 1.4024(6) 0.8280(3) 0.3603(7) 0.0610(13) Uani 1 1 d . . . . .
H8A H 1.468(6) 0.864(2) 0.384(6) 0.096(17) Uiso 1 1 d . . . . .
H8B H 1.365(5) 0.8211(17) 0.450(5) 0.061(14) Uiso 1 1 d . . . . .
H8C H 1.478(5) 0.794(2) 0.362(5) 0.076(14) Uiso 1 1 d . . . . .
N9 N 1.1740(4) 0.77306(13) 0.1915(4) 0.0440(8) Uani 1 1 d . . . . .
O10 O 1.2422(3) 0.72176(12) 0.1721(4) 0.0712(9) Uani 1 1 d . . . . .
C11 C 1.0231(4) 0.77974(14) 0.2147(4) 0.0346(8) Uani 1 1 d . . . . .
C12 C 0.9098(4) 0.72939(14) 0.2214(4) 0.0359(8) Uani 1 1 d . . . . .
C13 C 0.7866(5) 0.73733(18) 0.2978(5) 0.0520(11) Uani 1 1 d . . . . .
H13A H 0.769(4) 0.7745(16) 0.340(4) 0.047(10) Uiso 1 1 d . . . . .
C14 C 0.6810(5) 0.68921(18) 0.3069(6) 0.0567(12) Uani 1 1 d . . . . .
H14A H 0.596(4) 0.6950(14) 0.358(4) 0.046(10) Uiso 1 1 d . . . . .
C15 C 0.6916(4) 0.63258(16) 0.2350(5) 0.0437(9) Uani 1 1 d . . . . .
C16 C 0.5777(5) 0.58398(16) 0.2419(5) 0.0479(10) Uani 1 1 d . . . . .
C17 C 0.4800(5) 0.54500(16) 0.2476(5) 0.0510(10) Uani 1 1 d . . . . .
I18 I 0.31966(3) 0.47758(2) 0.25834(4) 0.05439(11) Uani 1 1 d . . . . .
C19 C 0.8123(5) 0.62493(19) 0.1586(5) 0.0528(12) Uani 1 1 d . . . . .
H19A H 0.818(4) 0.5928(16) 0.109(4) 0.044(11) Uiso 1 1 d . . . . .
C20 C 0.9214(6) 0.67198(19) 0.1522(5) 0.0497(11) Uani 1 1 d . . . . .
H20A H 0.984(4) 0.6656(16) 0.105(4) 0.042(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.269(3) . ?
N2 C11 1.350(4) . ?
N2 C3 1.493(4) . ?
C3 C4 1.513(7) . ?
C3 C5 1.512(5) . ?
C3 C6 1.544(5) . ?
C4 H4A 0.95(6) . ?
C4 H4B 0.88(6) . ?
C4 H4C 0.86(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N9 1.493(4) . ?
C6 C7 1.516(6) . ?
C6 C8 1.528(6) . ?
C7 H7A 0.94(5) . ?
C7 H7B 0.88(4) . ?
C7 H7C 0.96(5) . ?
C8 H8A 0.94(5) . ?
C8 H8B 0.93(4) . ?
C8 H8C 0.97(4) . ?
N9 O10 1.276(3) . ?
N9 C11 1.349(4) . ?
C11 C12 1.456(4) . ?
C12 C13 1.386(5) . ?
C12 C20 1.389(5) . ?
C13 C14 1.382(5) . ?
C13 H13A 0.91(3) . ?
C14 C15 1.383(5) . ?
C14 H14A 0.95(4) . ?
C15 C19 1.366(5) . ?
C15 C16 1.433(5) . ?
C16 C17 1.187(4) . ?
C17 I18 2.003(4) . ?
C19 C20 1.380(5) . ?
C19 H19A 0.82(3) . ?
C20 H20A 0.77(3) . ?

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
O1 N2 C11 125.7(3) . . ?
O1 N2 C3 120.8(3) . . ?
C11 N2 C3 113.3(3) . . ?
N2 C3 C4 108.6(4) . . ?
N2 C3 C5 106.4(3) . . ?
C4 C3 C5 109.0(5) . . ?
N2 C3 C6 102.0(3) . . ?
C4 C3 C6 116.0(4) . . ?
C5 C3 C6 114.1(3) . . ?
C3 C4 H4A 118(4) . . ?
C3 C4 H4B 104(4) . . ?
H4A C4 H4B 130(5) . . ?
C3 C4 H4C 102(3) . . ?
H4A C4 H4C 92(5) . . ?
H4B C4 H4C 106(6) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N9 C6 C7 108.4(3) . . ?
N9 C6 C8 105.9(3) . . ?
C7 C6 C8 110.1(4) . . ?
N9 C6 C3 101.9(3) . . ?
C7 C6 C3 115.8(4) . . ?
C8 C6 C3 113.8(4) . . ?
C6 C7 H7A 109(3) . . ?
C6 C7 H7B 103(3) . . ?
H7A C7 H7B 101(4) . . ?
C6 C7 H7C 110(3) . . ?
H7A C7 H7C 108(4) . . ?
H7B C7 H7C 125(4) . . ?
C6 C8 H8A 113(3) . . ?
C6 C8 H8B 114(3) . . ?
H8A C8 H8B 105(4) . . ?
C6 C8 H8C 114(3) . . ?
H8A C8 H8C 106(4) . . ?
H8B C8 H8C 103(4) . . ?
O10 N9 C11 126.1(3) . . ?
O10 N9 C6 120.4(3) . . ?
C11 N9 C6 113.3(3) . . ?
N9 C11 N2 108.0(3) . . ?
N9 C11 C12 125.7(3) . . ?
N2 C11 C12 126.3(3) . . ?
C13 C12 C20 117.8(3) . . ?
C13 C12 C11 120.8(3) . . ?
C20 C12 C11 121.4(3) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13A 117(2) . . ?
C12 C13 H13A 122(2) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14A 119(2) . . ?
C13 C14 H14A 121(2) . . ?
C19 C15 C14 118.2(4) . . ?
C19 C15 C16 121.9(3) . . ?
C14 C15 C16 119.9(4) . . ?
C17 C16 C15 178.1(4) . . ?
C16 C17 I18 178.5(3) . . ?
C15 C19 C20 121.6(4) . . ?
C15 C19 H19A 121(2) . . ?
C20 C19 H19A 117(3) . . ?
C19 C20 C12 120.7(4) . . ?
C19 C20 H20A 117(3) . . ?
C12 C20 H20A 122(3) . . ?

_refine_diff_density_max         0.456
_refine_diff_density_min         -0.722
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_mk162s
_database_code_depnum_ccdc_archive 'CCDC 2248097'
loop_
_audit_author_name
_audit_author_address
'Galina Romanenko'
;International Tomography Center
Russia
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 I N2 O2'
_chemical_formula_weight         383.20

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'
O O 0.0106 0.0060 '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'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7329(16)
_cell_length_b                   12.393(2)
_cell_length_c                   14.382(2)
_cell_angle_alpha                78.384(9)
_cell_angle_beta                 72.269(9)
_cell_angle_gamma                72.195(9)
_cell_volume                     1562.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7787
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.17

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    2.053
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3631
_exptl_absorpt_correction_T_max  0.4946
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28791
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.738
_diffrn_reflns_theta_max         28.733
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7807
_reflns_number_gt                4562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7807
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_refine_ls_shift/su_max          0.001
_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
I1 I 0.27426(3) 0.36797(2) 1.00889(2) 0.06944(11) Uani 1 1 d . . . . .
O1 O 0.4271(3) 0.8687(2) 0.76471(19) 0.0720(8) Uani 1 1 d . . . . .
N2 N 0.4333(3) 0.9525(2) 0.79998(19) 0.0440(7) Uani 1 1 d . . . . .
C3 C 0.5426(4) 1.0215(3) 0.7466(2) 0.0425(8) Uani 1 1 d . . . . .
C4 C 0.5553(4) 1.0384(4) 0.6373(2) 0.0620(11) Uani 1 1 d . . . . .
H4A H 0.610819 1.093613 0.605168 0.093 Uiso 1 1 calc R U . . .
H4B H 0.457104 1.065049 0.626612 0.093 Uiso 1 1 calc R U . . .
H4C H 0.605914 0.967135 0.610877 0.093 Uiso 1 1 calc R U . . .
C5 C 0.6918(4) 0.9522(3) 0.7676(3) 0.0561(10) Uani 1 1 d . . . . .
H5A H 0.716818 0.876936 0.749078 0.084 Uiso 1 1 calc R U . . .
H5B H 0.683784 0.946876 0.836493 0.084 Uiso 1 1 calc R U . . .
H5C H 0.768531 0.989216 0.730462 0.084 Uiso 1 1 calc R U . . .
C6 C 0.4720(4) 1.1295(3) 0.7993(2) 0.0408(8) Uani 1 1 d . . . . .
C7 C 0.3526(4) 1.2174(3) 0.7556(3) 0.0540(9) Uani 1 1 d . . . . .
H7A H 0.399713 1.257186 0.695757 0.081 Uiso 1 1 calc R U . . .
H7B H 0.293133 1.270919 0.801619 0.081 Uiso 1 1 calc R U . . .
H7C H 0.289685 1.179398 0.741930 0.081 Uiso 1 1 calc R U . . .
C8 C 0.5831(4) 1.1863(3) 0.8100(3) 0.0504(9) Uani 1 1 d . . . . .
H8A H 0.642568 1.207599 0.746076 0.076 Uiso 1 1 calc R U . . .
H8B H 0.646873 1.133990 0.847978 0.076 Uiso 1 1 calc R U . . .
H8C H 0.530214 1.253140 0.842677 0.076 Uiso 1 1 calc R U . . .
N9 N 0.3909(3) 1.0801(2) 0.89689(18) 0.0407(6) Uani 1 1 d . . . . .
O10 O 0.3493(3) 1.1320(2) 0.97375(17) 0.0607(7) Uani 1 1 d . . . . .
C11 C 0.3588(4) 0.9842(3) 0.8905(2) 0.0390(8) Uani 1 1 d . . . . .
C12 C 0.2617(4) 0.9238(3) 0.9671(2) 0.0381(7) Uani 1 1 d . . . . .
C13 C 0.1515(4) 0.9800(3) 1.0424(2) 0.0412(8) Uani 1 1 d . . . . .
H13 H 0.139783 1.056828 1.044828 0.049 Uiso 1 1 calc R U . . .
C14 C 0.0599(4) 0.9214(3) 1.1132(2) 0.0463(8) Uani 1 1 d . . . . .
H14 H -0.013969 0.959412 1.162840 0.056 Uiso 1 1 calc R U . . .
C15 C 0.0766(4) 0.8071(3) 1.1112(3) 0.0493(9) Uani 1 1 d . . . . .
H15 H 0.015216 0.768275 1.159977 0.059 Uiso 1 1 calc R U . . .
C16 C 0.1842(4) 0.7505(3) 1.0369(3) 0.0467(8) Uani 1 1 d . . . . .
C17 C 0.2764(4) 0.8095(3) 0.9648(2) 0.0470(9) Uani 1 1 d . . . . .
H17 H 0.348776 0.771595 0.914494 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2033(4) 0.6319(3) 1.0319(3) 0.0559(10) Uani 1 1 d . . . . .
C19 C 0.2258(5) 0.5339(3) 1.0250(3) 0.0624(11) Uani 1 1 d . . . . .
I1B I 0.91002(3) -0.13475(2) 0.40064(2) 0.05348(9) Uani 1 1 d . . . . .
O1B O 0.8828(2) 0.62999(19) 0.44507(17) 0.0496(6) Uani 1 1 d . . . . .
N2B N 0.7878(3) 0.5802(2) 0.50632(18) 0.0349(6) Uani 1 1 d . . . . .
C3B C 0.6880(3) 0.6299(3) 0.5985(2) 0.0336(7) Uani 1 1 d . . . . .
C4B C 0.5590(4) 0.7223(3) 0.5670(2) 0.0454(8) Uani 1 1 d . . . . .
H4BA H 0.598143 0.778025 0.518002 0.068 Uiso 1 1 calc R U . . .
H4BB H 0.492453 0.758612 0.623067 0.068 Uiso 1 1 calc R U . . .
H4BC H 0.505484 0.687944 0.540367 0.068 Uiso 1 1 calc R U . . .
C5B C 0.7700(4) 0.6804(3) 0.6448(2) 0.0445(8) Uani 1 1 d . . . . .
H5BA H 0.861895 0.625693 0.651237 0.067 Uiso 1 1 calc R U . . .
H5BB H 0.709020 0.699610 0.708648 0.067 Uiso 1 1 calc R U . . .
H5BC H 0.791434 0.747902 0.604147 0.067 Uiso 1 1 calc R U . . .
C6B C 0.6411(3) 0.5225(3) 0.6599(2) 0.0364(7) Uani 1 1 d . . . . .
C7B C 0.7539(4) 0.4473(3) 0.7146(2) 0.0493(9) Uani 1 1 d . . . . .
H7BA H 0.852637 0.436748 0.671139 0.074 Uiso 1 1 calc R U . . .
H7BB H 0.732251 0.374565 0.737890 0.074 Uiso 1 1 calc R U . . .
H7BC H 0.748285 0.483090 0.769488 0.074 Uiso 1 1 calc R U . . .
C8B C 0.4836(4) 0.5450(3) 0.7264(2) 0.0513(9) Uani 1 1 d . . . . .
H8BA H 0.413402 0.578779 0.687304 0.077 Uiso 1 1 calc R U . . .
H8BB H 0.472282 0.596217 0.771798 0.077 Uiso 1 1 calc R U . . .
H8BC H 0.465197 0.474388 0.762152 0.077 Uiso 1 1 calc R U . . .
N9B N 0.6545(3) 0.4581(2) 0.57731(18) 0.0370(6) Uani 1 1 d . . . . .
O10B O 0.5885(3) 0.3796(2) 0.59150(17) 0.0534(6) Uani 1 1 d . . . . .
C11B C 0.7532(3) 0.4882(2) 0.4944(2) 0.0328(7) Uani 1 1 d . . . . .
C12B C 0.8133(3) 0.4272(3) 0.4078(2) 0.0328(7) Uani 1 1 d . . . . .
C13B C 0.8568(3) 0.4839(3) 0.3140(2) 0.0387(8) Uani 1 1 d . . . . .
H13B H 0.849850 0.561541 0.305836 0.046 Uiso 1 1 calc R U . . .
C14B C 0.9101(4) 0.4245(3) 0.2334(2) 0.0439(8) Uani 1 1 d . . . . .
H14B H 0.937509 0.462884 0.170842 0.053 Uiso 1 1 calc R U . . .
C15B C 0.9233(4) 0.3102(3) 0.2442(3) 0.0473(9) Uani 1 1 d . . . . .
H15B H 0.958629 0.271493 0.188968 0.057 Uiso 1 1 calc R U . . .
C16B C 0.8845(3) 0.2513(3) 0.3364(2) 0.0385(7) Uani 1 1 d . . . . .
C17B C 0.8270(3) 0.3111(3) 0.4182(2) 0.0359(7) Uani 1 1 d . . . . .
H17B H 0.797661 0.272657 0.480441 0.043 Uiso 1 1 calc R U . . .
C18B C 0.8977(4) 0.1300(3) 0.3510(3) 0.0467(8) Uani 1 1 d . . . . .
C19B C 0.9047(4) 0.0308(3) 0.3683(3) 0.0496(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C19 2.009(4) . ?
I1 O10 2.899(2) 1_545 ?
I1 C18 3.194(4) . ?
O1 N2 1.268(3) . ?
N2 C11 1.354(4) . ?
N2 C3 1.499(4) . ?
C3 C4 1.515(4) . ?
C3 C5 1.529(4) . ?
C3 C6 1.539(4) . ?
C6 N9 1.497(4) . ?
C6 C8 1.516(4) . ?
C6 C7 1.526(4) . ?
N9 O10 1.286(3) . ?
N9 C11 1.344(4) . ?
C11 C12 1.461(4) . ?
C12 C17 1.386(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.380(4) . ?
C14 C15 1.381(5) . ?
C15 C16 1.379(5) . ?
C16 C17 1.394(5) . ?
C16 C18 1.439(5) . ?
C18 C19 1.186(5) . ?
I1B C19B 1.999(4) . ?
I1B O1B 2.932(2) 1_545 ?
I1B C18B 3.187(4) . ?
O1B N2B 1.283(3) . ?
N2B C11B 1.338(4) . ?
N2B C3B 1.503(4) . ?
C3B C5B 1.507(4) . ?
C3B C4B 1.533(4) . ?
C3B C6B 1.554(4) . ?
C6B N9B 1.513(4) . ?
C6B C8B 1.515(4) . ?
C6B C7B 1.516(4) . ?
N9B O10B 1.275(3) . ?
N9B C11B 1.351(4) . ?
C11B C12B 1.459(4) . ?
C12B C17B 1.385(4) . ?
C12B C13B 1.395(4) . ?
C13B C14B 1.377(4) . ?
C14B C15B 1.365(4) . ?
C15B C16B 1.381(4) . ?
C16B C17B 1.395(4) . ?
C16B C18B 1.446(5) . ?
C18B C19B 1.189(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 I1 O10 176.77(12) . 1_545 ?
C19 I1 C18 1.07(14) . . ?
O10 I1 C18 176.00(8) 1_545 . ?
O1 N2 C11 126.7(3) . . ?
O1 N2 C3 121.5(3) . . ?
C11 N2 C3 111.4(3) . . ?
N2 C3 C4 110.0(3) . . ?
N2 C3 C5 105.8(3) . . ?
C4 C3 C5 110.6(3) . . ?
N2 C3 C6 100.4(2) . . ?
C4 C3 C6 116.0(3) . . ?
C5 C3 C6 113.1(3) . . ?
N9 C6 C8 111.6(3) . . ?
N9 C6 C7 106.2(3) . . ?
C8 C6 C7 110.1(3) . . ?
N9 C6 C3 100.0(2) . . ?
C8 C6 C3 114.7(3) . . ?
C7 C6 C3 113.5(3) . . ?
O10 N9 C11 126.3(3) . . ?
O10 N9 C6 121.5(3) . . ?
C11 N9 C6 112.0(2) . . ?
N9 O10 I1 135.03(19) . 1_565 ?
N9 C11 N2 107.8(3) . . ?
N9 C11 C12 126.6(3) . . ?
N2 C11 C12 125.6(3) . . ?
C17 C12 C13 119.0(3) . . ?
C17 C12 C11 120.0(3) . . ?
C13 C12 C11 121.0(3) . . ?
C14 C13 C12 119.9(3) . . ?
C13 C14 C15 120.9(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 C18 121.4(3) . . ?
C17 C16 C18 119.2(3) . . ?
C12 C17 C16 120.9(3) . . ?
C19 C18 C16 176.8(4) . . ?
C19 C18 I1 1.8(2) . . ?
C16 C18 I1 175.0(3) . . ?
C18 C19 I1 177.1(4) . . ?
C19B I1B O1B 173.39(11) . 1_545 ?
C19B I1B C18B 0.71(13) . . ?
O1B I1B C18B 172.92(7) 1_545 . ?
N2B O1B I1B 134.46(17) . 1_565 ?
O1B N2B C11B 126.7(3) . . ?
O1B N2B C3B 121.4(2) . . ?
C11B N2B C3B 111.6(2) . . ?
N2B C3B C5B 111.6(2) . . ?
N2B C3B C4B 105.8(2) . . ?
C5B C3B C4B 110.7(3) . . ?
N2B C3B C6B 100.2(2) . . ?
C5B C3B C6B 114.3(2) . . ?
C4B C3B C6B 113.5(2) . . ?
N9B C6B C8B 110.4(2) . . ?
N9B C6B C7B 105.7(2) . . ?
C8B C6B C7B 111.6(3) . . ?
N9B C6B C3B 99.5(2) . . ?
C8B C6B C3B 115.3(3) . . ?
C7B C6B C3B 113.2(2) . . ?
O10B N9B C11B 127.2(2) . . ?
O10B N9B C6B 121.5(2) . . ?
C11B N9B C6B 111.0(2) . . ?
N2B C11B N9B 108.8(3) . . ?
N2B C11B C12B 126.5(3) . . ?
N9B C11B C12B 124.7(3) . . ?
C17B C12B C13B 119.0(3) . . ?
C17B C12B C11B 119.8(3) . . ?
C13B C12B C11B 121.2(3) . . ?
C14B C13B C12B 119.9(3) . . ?
C15B C14B C13B 120.8(3) . . ?
C14B C15B C16B 120.6(3) . . ?
C15B C16B C17B 119.0(3) . . ?
C15B C16B C18B 122.3(3) . . ?
C17B C16B C18B 118.7(3) . . ?
C12B C17B C16B 120.6(3) . . ?
C19B C18B C16B 176.4(4) . . ?
C19B C18B I1B 1.2(2) . . ?
C16B C18B I1B 175.4(2) . . ?
C18B C19B I1B 178.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H7A O10B 0.96 2.65 3.535(4) 153.0 1_565 yes
C8 H8C I1 0.96 3.09 3.938(4) 148.8 1_565 yes
C4B H4BB O1 0.96 2.49 3.384(4) 154.4 . yes
C5B H5BC I1B 0.96 3.04 3.898(3) 148.9 1_565 yes
C7B H7BA O1B 0.96 2.60 3.544(4) 169.5 2_766 yes

_refine_diff_density_max         0.536
_refine_diff_density_min         -1.364
_refine_diff_density_rms         0.116

