# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_tpa_i2_la
_database_code_depnum_ccdc_archive 'CCDC 2165898'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H30 I4 N4 O, 2(C H4 O)'
_chemical_formula_sum            'C41 H30 I4 N4 O3'
_chemical_formula_weight         1134.29
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4847(12)
_cell_length_b                   9.8569(13)
_cell_length_c                   23.787(3)
_cell_angle_alpha                91.327(3)
_cell_angle_beta                 100.187(3)
_cell_angle_gamma                114.405(3)
_cell_volume                     1981.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.663
_cell_measurement_theta_min      2.282
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.278
_exptl_absorpt_coefficient_mu    3.188
_exptl_absorpt_correction_T_max  0.6939
_exptl_absorpt_correction_T_min  0.5634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.8119.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.901
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            39928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.702
_diffrn_reflns_theta_min         2.282
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6396
_reflns_number_total             8311
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.013
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.00062(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     517
_refine_ls_number_reflns         8311
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+9.4389P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0818
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 O2-C21 = O1-C1
 1.2 with sigma of 0.01
 O2S-C2S = O1S-C1S = O3S-C3S = C4S-O4S = O5S-C5S = O6S-C6S = O7S-C7S
 1.45 with sigma of 0.01
 N4-C21 \\sim N5-C21 \\sim N1-C1 \\sim N2-C1
 with sigma of 0.01
 N4_$1-C22 \\sim N5-C22 \\sim N1_$2-C2 \\sim N2-C2
 with sigma of 0.01
 N5-C21 \\sim N4-C21 \\sim N2-C1 \\sim N1-C1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 1*[Sof(O1S)+Sof(C1S)]+1*[Sof(O2S)+Sof(C2S)]+1*[Sof(O3S)+Sof(C3S)]=1 with esd
 of 0.001
 1*[Sof(O4S)+Sof(C4S)]+1*[Sof(O5S)+Sof(C5S)]+1*[Sof(O6S)+Sof(C6S)]+1*[Sof(O7S)+
 Sof(C7S)]=1 with esd of 0.001
 Sof(O1S)=Sof(C1S)=FVAR(1)
 Sof(O2S)=Sof(C2S)=FVAR(2)
 Sof(O3S)=Sof(C3S)=FVAR(3)
 Sof(O4S)=Sof(C4S)=FVAR(4)
 Sof(O5S)=Sof(C5S)=FVAR(5)
 Sof(O6S)=Sof(C6S)=FVAR(6)
 Sof(O7S)=Sof(C7S)=FVAR(7)
 Uiso(O1S)=Uiso(C1S)=Uiso(O4S)=Uiso(C4S)=Uiso(O3S)=Uiso(C3S)=Uiso(O6S)=
 Uiso(C6S)=Uiso(O2S)=Uiso(C2S)=Uiso(O5S)=Uiso(C5S)=Uiso(O7S)=Uiso(C7S)=FVAR(8)
 Fixed Sof: O1(0.5) N1(0.5) H1(0.5) N2(0.5) H2(0.5) C1(0.5) H2AA(0.5)
 H2AB(0.5) H2BC(0.5) H2BD(0.5) O2(0.5) N4(0.5) H4A(0.5) N5(0.5) H5A(0.5)
 H22A(0.5) H22B(0.5) H22C(0.5) H22D(0.5)
5.a Riding coordinates:
 N1(H1), N2(H2), C2(H2AA,H2AB), C2(H2BC,H2BD), N4(H4A), N5(H5A), C22(H22A,
 H22B), C22(H22C,H22D)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48322(4) 0.69566(4) 0.03579(2) 0.02720(10) Uani 1 1 d . . . . .
I2 I -0.63289(4) 0.07003(4) 0.08508(2) 0.02663(10) Uani 1 1 d . . . . .
O1 O 0.6349(9) 0.4926(11) 0.5008(4) 0.045(2) Uani 0.5 1 d D . . . .
N1 N 0.5146(11) 0.6187(12) 0.5365(4) 0.058(4) Uani 0.5 1 d D . . . .
H1 H 0.422720 0.622613 0.538327 0.070 Uiso 0.5 1 d R . . . .
N2 N 0.3706(11) 0.4128(12) 0.4773(4) 0.050(3) Uani 0.5 1 d D . . . .
H2 H 0.289011 0.420644 0.488789 0.060 Uiso 0.5 1 d R . . . .
N3 N 0.0776(5) 0.3553(5) 0.20959(17) 0.0228(9) Uani 1 1 d . . . . .
C1 C 0.5203(11) 0.5166(16) 0.4994(8) 0.030(3) Uani 0.5 1 d D U . . .
C2 C 0.3264(10) 0.2765(9) 0.4359(3) 0.063(2) Uani 1 1 d D . . . .
H2AA H 0.252004 0.186338 0.445980 0.075 Uiso 0.5 1 d R . . A 1
H2AB H 0.421874 0.266488 0.434770 0.075 Uiso 0.5 1 d R . . A 1
H2BC H 0.340114 0.187668 0.430770 0.075 Uiso 0.5 1 d R . . B 2
H2BD H 0.248874 0.257818 0.458970 0.075 Uiso 0.5 1 d R . . B 2
C3 C 0.2619(7) 0.3028(7) 0.3763(2) 0.0364(14) Uani 1 1 d . . . . .
C4 C 0.3369(6) 0.4290(7) 0.3515(2) 0.0296(12) Uani 1 1 d . . . . .
H4 H 0.433292 0.505616 0.372291 0.036 Uiso 1 1 calc R . . . .
C5 C 0.2752(6) 0.4474(6) 0.2969(2) 0.0224(11) Uani 1 1 d . . . . .
H5 H 0.329297 0.536356 0.280377 0.027 Uiso 1 1 calc R . . . .
C6 C 0.1356(6) 0.3379(6) 0.2661(2) 0.0205(10) Uani 1 1 d . . . . .
C7 C 0.0570(6) 0.2115(6) 0.2912(2) 0.0262(11) Uani 1 1 d . . . . .
H7 H -0.040451 0.135499 0.270875 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1205(7) 0.1956(7) 0.3462(2) 0.0345(13) Uani 1 1 d . . . . .
H8 H 0.065019 0.108666 0.363566 0.041 Uiso 1 1 calc R . . . .
C9 C 0.1825(5) 0.4383(6) 0.1744(2) 0.0203(10) Uani 1 1 d . . . . .
C10 C 0.2962(5) 0.3982(5) 0.1616(2) 0.0209(10) Uani 1 1 d . . . . .
H10 H 0.313071 0.319219 0.179190 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3858(5) 0.4728(5) 0.1230(2) 0.0217(11) Uani 1 1 d . . . . .
H11 H 0.466238 0.446960 0.114360 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3576(5) 0.5857(5) 0.0970(2) 0.0210(10) Uani 1 1 d . . . . .
C13 C 0.2465(6) 0.6278(6) 0.1111(2) 0.0279(12) Uani 1 1 d . . . . .
H13 H 0.229488 0.707125 0.093763 0.033 Uiso 1 1 calc R . . . .
C14 C 0.1604(6) 0.5548(6) 0.1500(2) 0.0262(12) Uani 1 1 d . . . . .
H14 H 0.084493 0.584768 0.160441 0.031 Uiso 1 1 calc R . . . .
C15 C -0.0850(5) 0.2862(5) 0.1838(2) 0.0190(10) Uani 1 1 d . . . . .
C16 C -0.1290(6) 0.2252(6) 0.1271(2) 0.0239(11) Uani 1 1 d . . . . .
H16 H -0.050320 0.225645 0.107220 0.029 Uiso 1 1 calc R . . . .
C17 C -0.2848(6) 0.1638(6) 0.0990(2) 0.0233(11) Uani 1 1 d . . . . .
H17 H -0.314085 0.122451 0.059976 0.028 Uiso 1 1 calc R . . . .
C18 C -0.3963(5) 0.1634(5) 0.1279(2) 0.0192(10) Uani 1 1 d . . . . .
C19 C -0.3558(6) 0.2216(5) 0.1845(2) 0.0204(10) Uani 1 1 d . . . . .
H19 H -0.435270 0.219253 0.204383 0.024 Uiso 1 1 calc R . . . .
C20 C -0.1989(5) 0.2835(5) 0.2124(2) 0.0202(10) Uani 1 1 d . . . . .
H20 H -0.170107 0.324291 0.251498 0.024 Uiso 1 1 calc R . . . .
I3 I 0.35990(5) 1.04699(4) 0.29900(2) 0.03742(11) Uani 1 1 d . . . . .
I4 I 0.95206(4) 0.74881(4) 0.00359(2) 0.03320(11) Uani 1 1 d . . . . .
O2 O 1.1339(8) 0.5201(9) 0.4995(4) 0.0385(19) Uani 0.5 1 d D . . . .
N4 N 0.9719(10) 0.5653(10) 0.5457(3) 0.033(2) Uani 0.5 1 d D . . . .
H4A H 0.872598 0.555648 0.543065 0.040 Uiso 0.5 1 d R . . . .
N5 N 0.8690(9) 0.4157(10) 0.4612(3) 0.032(2) Uani 0.5 1 d D . . . .
H5A H 0.771711 0.392926 0.467522 0.039 Uiso 0.5 1 d R . . . .
N6 N 0.8070(5) 0.7594(5) 0.24874(19) 0.0287(10) Uani 1 1 d . . . . .
C21 C 1.000000 0.500000 0.500000 0.0313(18) Uani 1 2 d DS TU P . .
C22 C 0.8922(8) 0.3590(7) 0.4056(2) 0.0401(15) Uani 1 1 d D . . . .
H22A H 0.813357 0.259868 0.392906 0.048 Uiso 0.5 1 d R . . C 1
H22B H 0.994417 0.360058 0.408046 0.048 Uiso 0.5 1 d R . . C 1
H22C H 0.919677 0.289728 0.386966 0.048 Uiso 0.5 1 d R . . D 2
H22D H 0.794087 0.304278 0.416926 0.048 Uiso 0.5 1 d R . . D 2
C23 C 0.8696(6) 0.4608(6) 0.3616(2) 0.0257(11) Uani 1 1 d . . . . .
C24 C 0.7223(6) 0.4549(6) 0.3424(2) 0.0297(12) Uani 1 1 d . . . . .
H24 H 0.634306 0.383968 0.355535 0.036 Uiso 1 1 calc R . . . .
C25 C 0.7006(6) 0.5502(6) 0.3046(2) 0.0321(13) Uani 1 1 d . . . . .
H25 H 0.597578 0.544597 0.291497 0.039 Uiso 1 1 calc R . . . .
C26 C 0.8266(6) 0.6541(5) 0.2853(2) 0.0228(11) Uani 1 1 d . . . . .
C27 C 0.9750(6) 0.6569(6) 0.3034(2) 0.0246(11) Uani 1 1 d . . . . .
H27 H 1.062907 0.725742 0.289596 0.029 Uiso 1 1 calc R . . . .
C28 C 0.9947(6) 0.5610(6) 0.3409(2) 0.0264(12) Uani 1 1 d . . . . .
H28 H 1.096766 0.563485 0.352995 0.032 Uiso 1 1 calc R . . . .
C29 C 0.7058(6) 0.8239(6) 0.2593(2) 0.0250(11) Uani 1 1 d . . . . .
C30 C 0.7150(7) 0.8774(7) 0.3146(2) 0.0340(13) Uani 1 1 d . . . . .
H30 H 0.790660 0.870781 0.345085 0.041 Uiso 1 1 calc R . . . .
C31 C 0.6174(6) 0.9398(6) 0.3263(2) 0.0329(13) Uani 1 1 d . . . . .
H31 H 0.625529 0.976292 0.364568 0.039 Uiso 1 1 calc R . . . .
C32 C 0.5078(6) 0.9494(6) 0.2825(2) 0.0288(12) Uani 1 1 d . . . . .
C33 C 0.4971(7) 0.8969(6) 0.2274(2) 0.0306(13) Uani 1 1 d . . . . .
H33 H 0.420773 0.903207 0.197030 0.037 Uiso 1 1 calc R . . . .
C34 C 0.5969(7) 0.8346(6) 0.2156(2) 0.0297(12) Uani 1 1 d . . . . .
H34 H 0.589866 0.799406 0.177258 0.036 Uiso 1 1 calc R . . . .
C35 C 0.8406(6) 0.7556(6) 0.1932(2) 0.0246(11) Uani 1 1 d . . . . .
C36 C 0.9124(7) 0.8879(6) 0.1701(3) 0.0379(15) Uani 1 1 d . . . . .
H36 H 0.939956 0.980865 0.191617 0.045 Uiso 1 1 calc R . . . .
C37 C 0.9439(7) 0.8853(6) 0.1163(2) 0.0375(14) Uani 1 1 d . . . . .
H37 H 0.991717 0.976466 0.100060 0.045 Uiso 1 1 calc R . . . .
C38 C 0.9066(6) 0.7522(6) 0.0860(2) 0.0235(11) Uani 1 1 d . . . . .
C39 C 0.8362(5) 0.6213(6) 0.1081(2) 0.0221(11) Uani 1 1 d . . . . .
H39 H 0.809279 0.528677 0.086484 0.027 Uiso 1 1 calc R . . . .
C40 C 0.8041(6) 0.6234(6) 0.1619(2) 0.0226(11) Uani 1 1 d . . . . .
H40 H 0.755822 0.531682 0.177731 0.027 Uiso 1 1 calc R . . . .
O1S O 0.3496(16) 0.8064(15) 0.4958(5) 0.0793(19) Uiso 0.460(9) 1 d D . . E 1
C1S C 0.394(3) 0.823(3) 0.4401(7) 0.0793(19) Uiso 0.460(9) 1 d D . . E 1
O4S O 0.927(3) 0.947(3) 0.4424(11) 0.0793(19) Uiso 0.260(11) 1 d D . . F 1
C4S C 0.897(5) 0.791(3) 0.4472(17) 0.0793(19) Uiso 0.260(11) 1 d D . . F 1
O3S O 0.563(3) 0.951(3) 0.4625(9) 0.0793(19) Uiso 0.270(7) 1 d D . . G 3
C3S C 0.728(3) 1.038(4) 0.4887(14) 0.0793(19) Uiso 0.270(7) 1 d D . . G 3
O6S O 0.987(3) 0.832(2) 0.4504(8) 0.0793(19) Uiso 0.378(15) 1 d D . . H 3
C6S C 1.104(3) 0.929(3) 0.5002(10) 0.0793(19) Uiso 0.378(15) 1 d D . . H 3
O2S O 0.471(3) 0.812(3) 0.4437(10) 0.0793(19) Uiso 0.271(9) 1 d D . . I 2
C2S C 0.338(4) 0.846(4) 0.4475(16) 0.0793(19) Uiso 0.271(9) 1 d D . . I 2
O5S O 1.073(5) 0.853(4) 0.4465(14) 0.0793(19) Uiso 0.198(12) 1 d D . . J 2
C5S C 0.965(6) 0.902(7) 0.468(2) 0.0793(19) Uiso 0.198(12) 1 d D . . J 2
O7S O 1.142(5) 0.949(5) 0.4903(18) 0.0793(19) Uiso 0.164(13) 1 d D . . K 4
C7S C 1.019(7) 0.943(8) 0.443(2) 0.0793(19) Uiso 0.164(13) 1 d D . . K 4


_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 C12 2.082(5) . ?
I2 C18 2.089(5) . ?
O1 N1 1.493(12) 2_666 ?
O1 N2 1.082(11) 2_666 ?
O1 H2 0.854(14) 2_666 ?
O1 C1 1.200(9) . ?
O1 C1 1.436(15) 2_666 ?
N1 H1 0.8964 . ?
N1 N2 1.339(13) 2_666 ?
N1 C1 1.450(17) 2_666 ?
N1 C1 1.348(9) . ?
N1 C2 1.450(9) 2_666 ?
N2 H2 0.8957 . ?
N2 C1 1.360(9) . ?
N2 C1 1.023(16) 2_666 ?
N2 C2 1.510(9) . ?
N3 C6 1.402(6) . ?
N3 C9 1.419(6) . ?
N3 C15 1.413(6) . ?
C1 C1 0.39(3) 2_666 ?
C2 H2AA 0.9472 . ?
C2 H2AB 0.9556 . ?
C2 H2BC 0.9454 . ?
C2 H2BD 0.9547 . ?
C2 C3 1.513(8) . ?
C3 C4 1.360(8) . ?
C3 C8 1.372(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(7) . ?
C6 C7 1.375(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.369(7) . ?
C9 C14 1.372(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(7) . ?
C12 C13 1.369(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.363(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(7) . ?
C15 C20 1.368(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.375(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.358(7) . ?
C18 C19 1.375(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(7) . ?
C20 H20 0.9500 . ?
I3 C32 2.083(5) . ?
I4 C38 2.082(5) . ?
O2 C21 1.204(6) . ?
N4 H4A 0.8974 . ?
N4 C21 1.371(7) . ?
N4 C22 1.481(8) 2_766 ?
N5 H5A 0.8970 . ?
N5 C21 1.339(7) . ?
N5 C22 1.509(8) . ?
N6 C26 1.418(6) . ?
N6 C29 1.404(7) . ?
N6 C35 1.416(7) . ?
C22 H22A 0.9530 . ?
C22 H22B 0.9564 . ?
C22 H22C 0.9511 . ?
C22 H22D 0.9540 . ?
C22 C23 1.516(8) . ?
C23 C24 1.367(7) . ?
C23 C28 1.373(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.367(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.376(7) . ?
C26 C27 1.386(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.360(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(8) . ?
C29 C34 1.369(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.365(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.370(8) . ?
C32 C33 1.370(8) . ?
C33 H33 0.9500 . ?
C33 C34 1.384(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.377(7) . ?
C35 C40 1.364(7) . ?
C36 H36 0.9500 . ?
C36 C37 1.368(8) . ?
C37 H37 0.9500 . ?
C37 C38 1.360(8) . ?
C38 C39 1.354(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.369(7) . ?
C40 H40 0.9500 . ?
O1S C1S 1.451(10) . ?
O4S C4S 1.448(10) . ?
O3S C3S 1.449(10) . ?
O6S C6S 1.464(10) . ?
O2S C2S 1.447(10) . ?
O5S C5S 1.454(10) . ?
O7S C7S 1.455(10) . ?

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
C1 N1 H1 120.9 . . ?
C1 N2 H2 119.4 . . ?
C1 N2 C2 125.7(9) . . ?
C2 N2 H2 114.9 . . ?
C6 N3 C9 120.8(4) . . ?
C6 N3 C15 122.5(4) . . ?
C15 N3 C9 116.6(4) . . ?
O1 C1 N1 123.4(11) . . ?
O1 C1 N2 123.1(10) . . ?
N1 C1 N2 109.1(10) . . ?
N1 C2 H2BC 101.1 2_666 . ?
N1 C2 H2BD 114.8 2_666 . ?
N1 C2 C3 117.3(7) 2_666 . ?
N2 C2 H2AA 114.4 . . ?
N2 C2 H2AB 106.8 . . ?
N2 C2 H2BC 143.8 . . ?
N2 C2 H2BD 69.7 . . ?
N2 C2 C3 109.4(6) . . ?
H2AA C2 H2AB 109.0 . . ?
H2BC C2 H2BD 107.7 . . ?
C3 C2 H2AA 109.1 . . ?
C3 C2 H2AB 107.8 . . ?
C3 C2 H2BC 105.3 . . ?
C3 C2 H2BD 109.4 . . ?
C4 C3 C2 122.9(6) . . ?
C4 C3 C8 118.5(5) . . ?
C8 C3 C2 118.6(6) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(5) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N3 119.8(4) . . ?
C7 C6 N3 121.2(4) . . ?
C7 C6 C5 119.0(5) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(5) . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 121.4(6) . . ?
C3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 N3 121.4(4) . . ?
C10 C9 C14 120.3(5) . . ?
C14 C9 N3 118.2(4) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.3(5) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 I1 120.8(4) . . ?
C13 C12 I1 118.5(4) . . ?
C13 C12 C11 120.7(5) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.4(5) . . ?
C14 C13 H13 120.3 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.5(5) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 N3 118.7(4) . . ?
C20 C15 N3 122.0(4) . . ?
C20 C15 C16 119.2(4) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.1(5) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 118.9(5) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 I2 118.8(4) . . ?
C17 C18 C19 121.2(4) . . ?
C19 C18 I2 120.0(4) . . ?
C18 C19 H19 120.2 . . ?
C18 C19 C20 119.6(5) . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 120.0(5) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 N4 C22 116.5(6) . 2_766 ?
C22 N4 H4A 127.3 2_766 . ?
H5A N5 H22D 85.1 . . ?
C21 N5 H5A 122.3 . . ?
C21 N5 C22 116.7(6) . . ?
C21 N5 H22D 149.3 . . ?
C22 N5 H5A 121.0 . . ?
C22 N5 H22D 38.4 . . ?
C29 N6 C26 118.4(4) . . ?
C29 N6 C35 119.6(4) . . ?
C35 N6 C26 118.1(4) . . ?
O2 C21 N4 118.6(5) . . ?
O2 C21 N5 127.6(5) . . ?
N5 C21 N4 113.8(5) . . ?
N4 C22 H22A 137.4 2_766 . ?
N4 C22 H22B 55.3 2_766 . ?
N4 C22 H22C 103.6 2_766 . ?
N4 C22 H22D 114.1 2_766 . ?
N4 C22 C23 114.6(6) 2_766 . ?
N5 C22 H22A 110.4 . . ?
N5 C22 H22B 113.7 . . ?
N5 C22 H22C 146.7 . . ?
N5 C22 H22D 62.5 . . ?
N5 C22 C23 106.3(5) . . ?
H22A C22 H22B 109.0 . . ?
H22C C22 H22D 108.3 . . ?
C23 C22 H22A 108.0 . . ?
C23 C22 H22B 109.3 . . ?
C23 C22 H22C 106.9 . . ?
C23 C22 H22D 108.8 . . ?
C24 C23 C22 119.7(5) . . ?
C24 C23 C28 118.9(5) . . ?
C28 C23 C22 121.4(5) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.5(5) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 N6 121.1(5) . . ?
C25 C26 C27 118.7(5) . . ?
C27 C26 N6 120.2(5) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 119.9(5) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 119.4 . . ?
C27 C28 C23 121.2(5) . . ?
C27 C28 H28 119.4 . . ?
C30 C29 N6 119.9(5) . . ?
C34 C29 N6 121.1(5) . . ?
C34 C29 C30 119.0(5) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.3(5) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.7(5) . . ?
C32 C31 H31 120.2 . . ?
C31 C32 I3 120.5(4) . . ?
C31 C32 C33 119.8(5) . . ?
C33 C32 I3 119.7(4) . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.3(5) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 120.0(5) . . ?
C29 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C36 C35 N6 119.5(5) . . ?
C40 C35 N6 121.5(5) . . ?
C40 C35 C36 119.0(5) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 120.0(5) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.9(5) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 I4 119.7(4) . . ?
C39 C38 I4 119.4(4) . . ?
C39 C38 C37 120.8(5) . . ?
C38 C39 H39 120.3 . . ?
C38 C39 C40 119.5(5) . . ?
C40 C39 H39 120.3 . . ?
C35 C40 C39 120.8(5) . . ?
C35 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?

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
N1 H1 O2 0.90 2.48 3.271(12) 147.2 1_455 yes
N2 H2 O2 0.90 2.12 2.965(11) 156.5 1_455 yes
N4 H4A O1 0.90 2.12 2.956(11) 154.8 . yes
N5 H5A O1 0.90 2.16 2.914(12) 141.5 . yes

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
I1 C12 C13 C14 178.4(4) . . . . ?
I2 C18 C19 C20 -179.8(3) . . . . ?
O1 N1 C1 O1 -167(2) 2_666 . . . ?
O1 N1 C1 N1 -35(5) 2_666 . . 2_666 ?
O1 N1 C1 N2 -10.1(11) 2_666 . . . ?
O1 N1 C1 N2 179.9(18) 2_666 . . 2_666 ?
O1 N1 C1 C1 -35(5) 2_666 . . 2_666 ?
O1 N2 C1 O1 170(2) 2_666 . . . ?
O1 N2 C1 N1 -174.9(13) 2_666 . . 2_666 ?
O1 N2 C1 N1 12.9(14) 2_666 . . . ?
O1 N2 C1 N2 79(6) 2_666 . . 2_666 ?
O1 N2 C1 C1 79(6) 2_666 . . 2_666 ?
O1 N2 C2 N1 154(4) 2_666 . . 2_666 ?
O1 N2 C2 C3 44(4) 2_666 . . . ?
N1 O1 C1 O1 45(6) 2_666 . . 2_666 ?
N1 O1 C1 N1 168(2) 2_666 . . . ?
N1 O1 C1 N2 -178.2(17) 2_666 . . 2_666 ?
N1 O1 C1 N2 13.6(15) 2_666 . . . ?
N1 O1 C1 C1 45(6) 2_666 . . 2_666 ?
N1 N2 C1 O1 -15.1(17) 2_666 . . . ?
N1 N2 C1 O1 174.9(13) 2_666 . . 2_666 ?
N1 N2 C1 N1 -172.3(18) 2_666 . . . ?
N1 N2 C1 N2 -106(7) 2_666 . . 2_666 ?
N1 N2 C1 C1 -106(7) 2_666 . . 2_666 ?
N1 N2 C2 C3 -110.1(8) 2_666 . . . ?
N1 C2 C3 C4 -9.1(10) 2_666 . . . ?
N1 C2 C3 C8 171.8(7) 2_666 . . . ?
N2 O1 C1 O1 -137(7) 2_666 . . 2_666 ?
N2 O1 C1 N1 -14.2(15) 2_666 . . . ?
N2 O1 C1 N1 178.2(17) 2_666 . . 2_666 ?
N2 O1 C1 N2 -168(3) 2_666 . . . ?
N2 O1 C1 C1 -137(7) 2_666 . . 2_666 ?
N2 N1 C1 O1 -179.9(18) 2_666 . . 2_666 ?
N2 N1 C1 O1 13.0(13) 2_666 . . . ?
N2 N1 C1 N1 145(7) 2_666 . . 2_666 ?
N2 N1 C1 N2 170(2) 2_666 . . . ?
N2 N1 C1 C1 145(7) 2_666 . . 2_666 ?
N2 C2 C3 C4 49.3(9) . . . . ?
N2 C2 C3 C8 -129.7(7) . . . . ?
N3 C6 C7 C8 177.6(5) . . . . ?
N3 C9 C10 C11 173.9(4) . . . . ?
N3 C9 C14 C13 -172.9(5) . . . . ?
N3 C15 C16 C17 -176.5(5) . . . . ?
N3 C15 C20 C19 176.6(4) . . . . ?
C1 O1 C1 O1 -0.01(2) 2_666 . . 2_666 ?
C1 O1 C1 N1 123(8) 2_666 . . . ?
C1 O1 C1 N1 -45(6) 2_666 . . 2_666 ?
C1 O1 C1 N2 137(7) 2_666 . . 2_666 ?
C1 O1 C1 N2 -31(5) 2_666 . . . ?
C1 N1 C1 O1 -132(8) 2_666 . . . ?
C1 N1 C1 O1 35(5) 2_666 . . 2_666 ?
C1 N1 C1 N1 0.00(3) 2_666 . . 2_666 ?
C1 N1 C1 N2 25(5) 2_666 . . . ?
C1 N1 C1 N2 -145(7) 2_666 . . 2_666 ?
C1 N2 C1 O1 -79(6) 2_666 . . 2_666 ?
C1 N2 C1 O1 91(7) 2_666 . . . ?
C1 N2 C1 N1 -67(6) 2_666 . . . ?
C1 N2 C1 N1 106(7) 2_666 . . 2_666 ?
C1 N2 C1 N2 0.02(7) 2_666 . . 2_666 ?
C1 N2 C2 N1 5.5(14) . . . 2_666 ?
C1 N2 C2 N1 -7(2) 2_666 . . 2_666 ?
C1 N2 C2 C3 -117(2) 2_666 . . . ?
C1 N2 C2 C3 -104.6(15) . . . . ?
C2 N1 C1 O1 18(3) 2_666 . . . ?
C2 N1 C1 O1 -174.5(10) 2_666 . . 2_666 ?
C2 N1 C1 N1 151(6) 2_666 . . 2_666 ?
C2 N1 C1 N2 5.3(16) 2_666 . . 2_666 ?
C2 N1 C1 N2 175.4(12) 2_666 . . . ?
C2 N1 C1 C1 151(6) 2_666 . . 2_666 ?
C2 N2 C1 O1 169.6(14) . . . 2_666 ?
C2 N2 C1 O1 -20(3) . . . . ?
C2 N2 C1 N1 -5.3(14) . . . 2_666 ?
C2 N2 C1 N1 -177.5(11) . . . . ?
C2 N2 C1 N2 -111(6) . . . 2_666 ?
C2 N2 C1 C1 -111(6) . . . 2_666 ?
C2 C3 C4 C5 179.1(5) . . . . ?
C2 C3 C8 C7 -178.6(5) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C4 C3 C8 C7 2.3(9) . . . . ?
C4 C5 C6 N3 -177.3(5) . . . . ?
C4 C5 C6 C7 1.5(7) . . . . ?
C5 C6 C7 C8 -1.1(8) . . . . ?
C6 N3 C9 C10 59.5(7) . . . . ?
C6 N3 C9 C14 -124.9(5) . . . . ?
C6 N3 C15 C16 -139.4(5) . . . . ?
C6 N3 C15 C20 43.4(7) . . . . ?
C6 C7 C8 C3 -0.8(8) . . . . ?
C8 C3 C4 C5 -1.9(8) . . . . ?
C9 N3 C6 C5 29.5(7) . . . . ?
C9 N3 C6 C7 -149.2(5) . . . . ?
C9 N3 C15 C16 37.5(6) . . . . ?
C9 N3 C15 C20 -139.8(5) . . . . ?
C9 C10 C11 C12 -1.1(7) . . . . ?
C10 C9 C14 C13 2.8(8) . . . . ?
C10 C11 C12 I1 -177.3(3) . . . . ?
C10 C11 C12 C13 2.7(7) . . . . ?
C11 C12 C13 C14 -1.6(8) . . . . ?
C12 C13 C14 C9 -1.2(8) . . . . ?
C14 C9 C10 C11 -1.6(7) . . . . ?
C15 N3 C6 C5 -153.7(5) . . . . ?
C15 N3 C6 C7 27.6(7) . . . . ?
C15 N3 C9 C10 -117.4(5) . . . . ?
C15 N3 C9 C14 58.2(6) . . . . ?
C15 C16 C17 C18 -0.2(8) . . . . ?
C16 C15 C20 C19 -0.6(7) . . . . ?
C16 C17 C18 I2 -180.0(4) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.9(7) . . . . ?
C18 C19 C20 C15 -0.2(7) . . . . ?
C20 C15 C16 C17 0.8(7) . . . . ?
I3 C32 C33 C34 178.6(4) . . . . ?
I4 C38 C39 C40 -179.0(3) . . . . ?
O2 N4 C21 O2 180.002(7) 2_766 . . . ?
O2 N4 C21 N5 178.2(8) 2_766 . . 2_766 ?
O2 N4 C21 N5 -1.8(8) 2_766 . . . ?
O2 N5 C21 O2 179.998(7) 2_766 . . . ?
O2 N5 C21 N4 -178.0(8) 2_766 . . 2_766 ?
O2 N5 C21 N4 2.0(8) 2_766 . . . ?
O2 N5 C22 N4 65(4) 2_766 . . 2_766 ?
O2 N5 C22 C23 -44(5) 2_766 . . . ?
N4 O2 C21 N4 180.000(5) 2_766 . . . ?
N4 O2 C21 N5 -177.9(9) 2_766 . . 2_766 ?
N4 O2 C21 N5 2.1(9) 2_766 . . . ?
N4 N5 C21 O2 178.0(8) 2_766 . . 2_766 ?
N4 N5 C21 O2 -2.0(8) 2_766 . . . ?
N4 N5 C21 N4 180.000(5) 2_766 . . . ?
N4 N5 C22 C23 -109.3(6) 2_766 . . . ?
N4 C22 C23 C24 -133.0(6) 2_766 . . . ?
N4 C22 C23 C28 46.0(7) 2_766 . . . ?
N5 O2 C21 N4 177.9(9) 2_766 . . 2_766 ?
N5 O2 C21 N4 -2.1(9) 2_766 . . . ?
N5 O2 C21 N5 180.001(4) 2_766 . . . ?
N5 N4 C21 O2 -178.2(8) 2_766 . . 2_766 ?
N5 N4 C21 O2 1.8(8) 2_766 . . . ?
N5 N4 C21 N5 180.000(6) 2_766 . . . ?
N5 C22 C23 C24 -69.8(7) . . . . ?
N5 C22 C23 C28 109.2(6) . . . . ?
N6 C26 C27 C28 176.5(5) . . . . ?
N6 C29 C30 C31 -179.6(5) . . . . ?
N6 C29 C34 C33 179.1(5) . . . . ?
N6 C35 C36 C37 -179.3(5) . . . . ?
N6 C35 C40 C39 179.5(4) . . . . ?
C21 N5 C22 N4 8.6(6) . . . 2_766 ?
C21 N5 C22 C23 -100.7(7) . . . . ?
C22 N4 C21 O2 172.9(10) 2_766 . . 2_766 ?
C22 N4 C21 O2 -7.1(10) 2_766 . . . ?
C22 N4 C21 N5 171.1(7) 2_766 . . . ?
C22 N4 C21 N5 -8.9(7) 2_766 . . 2_766 ?
C22 N5 C21 O2 169.2(11) . . . 2_766 ?
C22 N5 C21 O2 -10.8(11) . . . . ?
C22 N5 C21 N4 171.2(7) . . . . ?
C22 N5 C21 N4 -8.8(7) . . . 2_766 ?
C22 C23 C24 C25 177.2(5) . . . . ?
C22 C23 C28 C27 -176.9(5) . . . . ?
C23 C24 C25 C26 -0.3(9) . . . . ?
C24 C23 C28 C27 2.1(8) . . . . ?
C24 C25 C26 N6 -176.2(5) . . . . ?
C24 C25 C26 C27 2.2(8) . . . . ?
C25 C26 C27 C28 -2.0(8) . . . . ?
C26 N6 C29 C30 46.0(7) . . . . ?
C26 N6 C29 C34 -133.9(5) . . . . ?
C26 N6 C35 C36 -142.2(5) . . . . ?
C26 N6 C35 C40 37.5(7) . . . . ?
C26 C27 C28 C23 -0.2(8) . . . . ?
C28 C23 C24 C25 -1.9(8) . . . . ?
C29 N6 C26 C25 39.5(7) . . . . ?
C29 N6 C26 C27 -138.9(5) . . . . ?
C29 N6 C35 C36 60.4(7) . . . . ?
C29 N6 C35 C40 -119.9(5) . . . . ?
C29 C30 C31 C32 0.1(9) . . . . ?
C30 C29 C34 C33 -0.8(8) . . . . ?
C30 C31 C32 I3 -179.1(4) . . . . ?
C30 C31 C32 C33 -0.2(8) . . . . ?
C31 C32 C33 C34 -0.3(8) . . . . ?
C32 C33 C34 C29 0.7(8) . . . . ?
C34 C29 C30 C31 0.3(9) . . . . ?
C35 N6 C26 C25 -118.2(6) . . . . ?
C35 N6 C26 C27 63.4(6) . . . . ?
C35 N6 C29 C30 -156.7(5) . . . . ?
C35 N6 C29 C34 23.4(7) . . . . ?
C35 C36 C37 C38 -1.1(10) . . . . ?
C36 C35 C40 C39 -0.8(8) . . . . ?
C36 C37 C38 I4 179.2(5) . . . . ?
C36 C37 C38 C39 1.0(9) . . . . ?
C37 C38 C39 C40 -0.9(7) . . . . ?
C38 C39 C40 C35 0.7(7) . . . . ?
C40 C35 C36 C37 1.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT315_tpa_i2_la           
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).        C1S Check 
RESPONSE: No hydrogen atoms were added or calculated for the disordered 
interstitial methanol molecules.
;
# start Validation Reply Form
_vrf_PLAT430_tpa_i2_la           
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.25 Ang.  
RESPONSE: Erroneously identified contact because of disorder. This distance is
between two half-occupied carbonyl oxygen atoms and does not exist in any 
asymmetric unit.
;
####################################################################### 
# 
# 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_mh_i2cho
_database_code_depnum_ccdc_archive 'CCDC 2165900'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2020-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 I2 N O1'
_chemical_formula_sum            'C19 H13 I2 N O'
_chemical_formula_weight         525.10
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   9.7182(3)
_cell_length_b                   8.0639(2)
_cell_length_c                   11.5611(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.3914(9)
_cell_angle_gamma                90
_cell_volume                     864.59(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9954
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.249
_cell_measurement_theta_min      2.196
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.669
_exptl_absorpt_coefficient_mu    3.641
_exptl_absorpt_correction_T_max  0.4920
_exptl_absorpt_correction_T_min  0.4318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0533 before and 0.0466 after correction. 
The Ratio of minimum to maximum transmission is 0.8776.
 The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.017
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24434
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.288
_diffrn_reflns_theta_min         2.196
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                4035
_reflns_number_total             4193
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.946
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Flack x determined using 1867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.166
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0165P)²+1.9317P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0662
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C10-C19 = C16-C20A = C16-C20B
 1.47 with sigma of 0.02
 O1-C19 = O2A-C20A = O2B-C20B
 1.25 with sigma of 0.02
 C9-C19 \\sim C11-C19
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(O1) = Uiso(C19)
Uiso(C20A) = Uiso(C20B)
4. Others
 1*[Sof(I3)]+1*[Sof(O2A)+Sof(C20A)+Sof(H20A)]+1*[Sof(O2B)+Sof(C20B)+Sof(H20B)]=
 1 with esd of 0.00001
 1*[Sof(I2)+Sof(O1)+Sof(C19)+Sof(H19)]+1*[Sof(O2A)+Sof(C20A)+Sof(H20A)]+1*
 [Sof(O2B)+Sof(C20B)+Sof(H20B)]=1 with esd of 0.00001
 Sof(I2)=1-FVAR(1)
 Sof(O1)=Sof(C19)=Sof(H19)=FVAR(1)
 Sof(O2A)=Sof(C20A)=Sof(H20A)=FVAR(3)
 Sof(O2B)=Sof(C20B)=Sof(H20B)=FVAR(4)
5.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C20A(H20A), C20B(H20B), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8),
 C9(H9), C11(H11), C12(H12), C14(H14), C15(H15), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.04169(3) -0.01448(7) 0.03148(3) 0.03507(15) Uani 1 1 d . . . . .
I2 I 1.04199(5) 0.51680(9) 0.30915(5) 0.0333(2) Uani 0.7446(19) 1 d . . P A 1
O1 O 1.105(3) 0.572(3) 0.356(2) 0.051(5) Uiso 0.2554(19) 1 d D . P A 2
C19 C 1.006(3) 0.467(4) 0.317(3) 0.051(5) Uiso 0.2554(19) 1 d D . P A 2
H19 H 1.019627 0.400360 0.253762 0.061 Uiso 0.2554(19) 1 calc R . P A 2
I3 I 0.4937(3) 0.2524(3) 0.9716(2) 0.0434(8) Uani 0.2555(19) 1 d . . P B 1
O2A O 0.4043(18) 0.328(2) 0.9608(14) 0.039(3) Uiso 0.342(3) 1 d D . P B 2
C20A C 0.502(6) 0.252(10) 0.931(3) 0.059(7) Uiso 0.342(3) 1 d D . P B 2
H20A H 0.576911 0.194303 0.988810 0.070 Uiso 0.342(3) 1 calc R . P B 2
O2B O 0.571(2) 0.191(2) 1.0088(16) 0.056(4) Uiso 0.402(3) 1 d D . P B 3
C20B C 0.485(6) 0.261(8) 0.925(2) 0.059(7) Uiso 0.402(3) 1 d D . P B 3
H20B H 0.409229 0.321958 0.941482 0.070 Uiso 0.402(3) 1 calc R . P B 3
N1 N 0.5034(7) 0.2496(8) 0.4367(6) 0.0297(14) Uani 1 1 d . . . . .
C1 C 0.3765(8) 0.1972(8) 0.3428(6) 0.0290(13) Uani 1 1 d . . . . .
C2 C 0.2865(9) 0.0760(8) 0.3702(6) 0.0360(15) Uani 1 1 d . . . . .
H2 H 0.309370 0.033232 0.450260 0.043 Uiso 1 1 calc R . . . .
C3 C 0.1655(8) 0.0182(8) 0.2827(6) 0.0350(15) Uani 1 1 d . . . . .
H3 H 0.104650 -0.062215 0.302297 0.042 Uiso 1 1 calc R . . . .
C4 C 0.1348(7) 0.0799(8) 0.1656(6) 0.0298(13) Uani 1 1 d . . . . .
C5 C 0.2225(7) 0.2012(8) 0.1367(6) 0.0275(12) Uani 1 1 d . . . . .
H5 H 0.200287 0.243065 0.056455 0.033 Uiso 1 1 calc R . . . .
C6 C 0.3420(7) 0.2595(8) 0.2261(6) 0.0266(12) Uani 1 1 d . . . . .
H6 H 0.400760 0.342982 0.207123 0.032 Uiso 1 1 calc R . . . .
C7 C 0.6249(7) 0.3050(8) 0.4080(6) 0.0294(13) Uani 1 1 d . . . . .
C8 C 0.6650(7) 0.2375(8) 0.3116(6) 0.0276(12) Uani 1 1 d . . . . .
H8 H 0.609817 0.149490 0.265739 0.033 Uiso 1 1 calc R . . . .
C9 C 0.7853(7) 0.2972(8) 0.2812(6) 0.0283(12) Uani 1 1 d D . . . .
H9 H 0.809513 0.252074 0.213845 0.034 Uiso 1 1 calc R . . . .
C10 C 0.8688(7) 0.4224(8) 0.3500(6) 0.0327(14) Uani 1 1 d D . . . .
C11 C 0.8336(8) 0.4877(8) 0.4491(6) 0.0357(15) Uani 1 1 d D . . . .
H11 H 0.891647 0.572109 0.497116 0.043 Uiso 1 1 calc R . . . .
C12 C 0.7136(9) 0.4292(8) 0.4773(6) 0.0370(15) Uani 1 1 d . . . . .
H12 H 0.690594 0.474106 0.545265 0.044 Uiso 1 1 calc R . . . .
C13 C 0.4984(9) 0.2533(11) 0.5582(6) 0.0306(17) Uani 1 1 d . . . . .
C14 C 0.6192(9) 0.2000(11) 0.6508(8) 0.0352(19) Uani 1 1 d . . . . .
H14 H 0.702987 0.161899 0.632723 0.042 Uiso 1 1 calc R . . . .
C15 C 0.6146(10) 0.2038(11) 0.7702(7) 0.0354(19) Uani 1 1 d . . . . .
H15 H 0.696598 0.169689 0.833874 0.042 Uiso 1 1 calc R . . . .
C16 C 0.4931(9) 0.2560(11) 0.7970(6) 0.0319(18) Uani 1 1 d D . . . .
C17 C 0.3769(11) 0.3087(10) 0.7040(7) 0.0348(19) Uani 1 1 d . . . . .
H17 H 0.293662 0.345855 0.723357 0.042 Uiso 1 1 calc R . . . .
C18 C 0.3744(9) 0.3108(11) 0.5862(8) 0.0325(18) Uani 1 1 d . . . . .
H18 H 0.292343 0.349588 0.524475 0.039 Uiso 1 1 calc R . . . .


_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 C4 2.082(6) . ?
I2 C10 2.027(7) . ?
O1 C19 1.26(2) . ?
C19 H19 0.9500 . ?
C19 C10 1.53(2) . ?
I3 C16 2.018(7) . ?
O2A C20A 1.26(3) . ?
C20A H20A 0.9500 . ?
C20A C16 1.53(3) . ?
O2B C20B 1.21(3) . ?
C20B H20B 0.9500 . ?
C20B C16 1.51(2) . ?
N1 C1 1.441(9) . ?
N1 C7 1.392(10) . ?
N1 C13 1.421(9) . ?
C1 C2 1.409(9) . ?
C1 C6 1.383(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(10) . ?
C3 H3 0.9500 . ?
C3 C4 1.388(9) . ?
C4 C5 1.402(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(9) . ?
C7 C12 1.406(9) . ?
C8 H8 0.9500 . ?
C8 C9 1.403(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(9) . ?
C10 C11 1.394(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.400(11) . ?
C13 C18 1.415(11) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(11) . ?
C15 H15 0.9500 . ?
C15 C16 1.373(12) . ?
C16 C17 1.373(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.355(11) . ?
C18 H18 0.9500 . ?

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 C19 H19 112.9 . . ?
O1 C19 C10 134(2) . . ?
C10 C19 H19 112.9 . . ?
O2A C20A H20A 121.7 . . ?
O2A C20A C16 117(3) . . ?
C16 C20A H20A 121.7 . . ?
O2B C20B H20B 118.5 . . ?
O2B C20B C16 123(3) . . ?
C16 C20B H20B 118.5 . . ?
C7 N1 C1 120.7(5) . . ?
C7 N1 C13 120.8(6) . . ?
C13 N1 C1 118.4(6) . . ?
C2 C1 N1 118.9(6) . . ?
C6 C1 N1 122.1(6) . . ?
C6 C1 C2 119.0(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(6) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(6) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 I1 119.0(5) . . ?
C3 C4 C5 120.9(6) . . ?
C5 C4 I1 120.2(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.6(6) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
N1 C7 C8 121.6(6) . . ?
N1 C7 C12 120.8(6) . . ?
C8 C7 C12 117.6(6) . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(6) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(6) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 I2 121.6(5) . . ?
C9 C10 C19 115.6(11) . . ?
C9 C10 C11 120.1(6) . . ?
C11 C10 I2 118.3(5) . . ?
C11 C10 C19 124.0(11) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(6) . . ?
C12 C11 H11 120.1 . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.6(7) . . ?
C11 C12 H12 119.2 . . ?
C14 C13 N1 118.7(7) . . ?
C14 C13 C18 120.2(7) . . ?
C18 C13 N1 121.1(7) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.8(8) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(8) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 I3 118.4(6) . . ?
C15 C16 C20A 115.5(16) . . ?
C15 C16 C20B 122.0(16) . . ?
C15 C16 C17 118.7(7) . . ?
C17 C16 I3 122.9(6) . . ?
C17 C16 C20A 125.8(17) . . ?
C17 C16 C20B 119.3(16) . . ?
C16 C17 H17 118.2 . . ?
C18 C17 C16 123.6(9) . . ?
C18 C17 H17 118.2 . . ?
C13 C18 H18 121.2 . . ?
C17 C18 C13 117.7(8) . . ?
C17 C18 H18 121.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C4 C5 C6 -178.2(5) . . . . ?
I2 C10 C11 C12 178.2(5) . . . . ?
O1 C19 C10 C9 178(4) . . . . ?
O1 C19 C10 C11 -8(6) . . . . ?
C19 C10 C11 C12 -174(2) . . . . ?
I3 C16 C17 C18 -179.5(7) . . . . ?
O2A C20A C16 C15 167(5) . . . . ?
O2A C20A C16 C17 -12(9) . . . . ?
C20A C16 C17 C18 180(4) . . . . ?
O2B C20B C16 C15 -15(8) . . . . ?
O2B C20B C16 C17 167(5) . . . . ?
C20B C16 C17 C18 179(3) . . . . ?
N1 C1 C2 C3 -178.3(7) . . . . ?
N1 C1 C6 C5 177.2(6) . . . . ?
N1 C7 C8 C9 178.2(6) . . . . ?
N1 C7 C12 C11 -179.0(7) . . . . ?
N1 C13 C14 C15 179.9(8) . . . . ?
N1 C13 C18 C17 179.2(8) . . . . ?
C1 N1 C7 C8 -34.7(10) . . . . ?
C1 N1 C7 C12 146.7(7) . . . . ?
C1 N1 C13 C14 140.0(8) . . . . ?
C1 N1 C13 C18 -40.5(12) . . . . ?
C1 C2 C3 C4 1.0(11) . . . . ?
C2 C1 C6 C5 -1.4(10) . . . . ?
C2 C3 C4 I1 177.2(5) . . . . ?
C2 C3 C4 C5 -1.4(10) . . . . ?
C3 C4 C5 C6 0.3(10) . . . . ?
C4 C5 C6 C1 1.0(10) . . . . ?
C6 C1 C2 C3 0.3(11) . . . . ?
C7 N1 C1 C2 150.8(7) . . . . ?
C7 N1 C1 C6 -27.8(10) . . . . ?
C7 N1 C13 C14 -43.9(12) . . . . ?
C7 N1 C13 C18 135.5(8) . . . . ?
C7 C8 C9 C10 1.9(9) . . . . ?
C8 C7 C12 C11 2.4(10) . . . . ?
C8 C9 C10 I2 -178.9(5) . . . . ?
C8 C9 C10 C19 174.2(18) . . . . ?
C8 C9 C10 C11 0.3(10) . . . . ?
C9 C10 C11 C12 -1.1(10) . . . . ?
C10 C11 C12 C7 -0.3(11) . . . . ?
C12 C7 C8 C9 -3.1(9) . . . . ?
C13 N1 C1 C2 -33.2(10) . . . . ?
C13 N1 C1 C6 148.3(7) . . . . ?
C13 N1 C7 C8 149.4(7) . . . . ?
C13 N1 C7 C12 -29.2(10) . . . . ?
C13 C14 C15 C16 1.1(13) . . . . ?
C14 C13 C18 C17 -1.3(12) . . . . ?
C14 C15 C16 I3 178.6(7) . . . . ?
C14 C15 C16 C20A 179(4) . . . . ?
C14 C15 C16 C20B 180(3) . . . . ?
C14 C15 C16 C17 -1.6(13) . . . . ?
C15 C16 C17 C18 0.7(13) . . . . ?
C16 C17 C18 C13 0.8(13) . . . . ?
C18 C13 C14 C15 0.4(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_tpa_a
_database_code_depnum_ccdc_archive 'CCDC 2165901'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2019-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H30 I4 N4 O, 0.72(C4 H8 O2)'
_chemical_formula_sum            'C41.89 H35.78 I4 N4 O2.45'
_chemical_formula_weight         1141.92
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5202(4)
_cell_length_b                   10.0356(4)
_cell_length_c                   23.9703(9)
_cell_angle_alpha                92.092(2)
_cell_angle_beta                 100.214(2)
_cell_angle_gamma                114.586(2)
_cell_volume                     2033.89(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9980
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.360
_cell_measurement_theta_min      2.309
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.418
_exptl_absorpt_coefficient_mu    3.106
_exptl_absorpt_correction_T_max  0.6465
_exptl_absorpt_correction_T_min  0.5171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1241 before and 0.0559 after correction.
The Ratio of minimum to maximum transmission is 0.7998.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1093
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.399
_diffrn_reflns_theta_max         26.399
_diffrn_reflns_theta_min         2.249
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7239
_reflns_number_total             8313
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.121
_refine_ls_extinction_coef       0.00083(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.242
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         8313
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.242
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+9.7083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-C21 = O1-C1
 1.2 with sigma of 0.01
 O71-C72 = O51-C52 = O61-C62
 1.21 with sigma of 0.015
 C72-C71 = C52-C51 = C62-C61
 1.478 with sigma of 0.015
 O72-C72 = O62-C62 = O52-C52
 1.324 with sigma of 0.015
 O62-C63 = O52-C53 = O72-C73
 1.456 with sigma of 0.015
 C54-C53 = C74-C73 = C64-C63
 1.456 with sigma of 0.015
 O71-C71 = C51-O51 = C61-O61
 2.39 with sigma of 0.02
 O72-C71 = C51-O52 = C61-O62
 2.33 with sigma of 0.02
 O72-C74 = O52-C54 = O62-C64
 2.37 with sigma of 0.02
 N4-C21 \\sim N5-C21 \\sim N1-C1 \\sim N2-C1
 with sigma of 0.01
 N4_$1-C22 \\sim N5-C22 \\sim N1_$2-C2 \\sim N2-C2
 with sigma of 0.01
 N5-C21 \\sim N4-C21 \\sim N2-C1 \\sim N1-C1
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
4. Others
 Sof(O51)=Sof(O52)=Sof(C51)=Sof(H51A)=Sof(H51B)=Sof(H51C)=Sof(C52)=Sof(C53)=
 Sof(H53A)=Sof(H53B)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(H54C)=FVAR(1)
 Sof(O61)=Sof(O62)=Sof(C61)=Sof(H61A)=Sof(H61B)=Sof(H61C)=Sof(C62)=Sof(C63)=
 Sof(H63A)=Sof(H63B)=Sof(C64)=Sof(H64A)=Sof(H64B)=Sof(H64C)=FVAR(2)
 Sof(O71)=Sof(O72)=Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=Sof(C72)=Sof(C73)=
 Sof(H73A)=Sof(H73B)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(3)
 Uiso(O51)=Uiso(O52)=Uiso(C51)=Uiso(C52)=Uiso(C53)=Uiso(C54)=Uiso(O61)=
 Uiso(O62)=Uiso(C61)=Uiso(C62)=Uiso(C63)=Uiso(C64)=Uiso(O71)=Uiso(O72)=
 Uiso(C71)=Uiso(C72)=Uiso(C73)=Uiso(C74)=FVAR(4)
 Fixed Sof: O1(0.5) N1(0.5) H1(0.5) N2(0.5) H2(0.5) C1(0.5) H2AA(0.5)
 H2AB(0.5) H2BC(0.5) H2BD(0.5) O2(0.5) N4(0.5) H4A(0.5) N5(0.5) H5A(0.5)
 C21(0.5) H22A(0.5) H22B(0.5) H22C(0.5) H22D(0.5)
5.a Riding coordinates:
 N1(H1), N2(H2), C2(H2AA,H2AB), C2(H2BC,H2BD), N4(H4A), N5(H5A), C22(H22A,
 H22B), C22(H22C,H22D)
5.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C63(H63A,H63B), C73(H73A,H73B)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40)
5.d Idealised Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C54(H54A,H54B,H54C), C61(H61A,H61B,H61C), C64(H64A,H64B,
 H64C), C71(H71A,H71B,H71C), C74(H74A,H74B,H74C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48432(4) 0.69737(4) 0.03630(2) 0.02601(9) Uani 1 1 d . . . . .
I2 I -0.63387(4) 0.07123(4) 0.08449(2) 0.02508(9) Uani 1 1 d . . . . .
O1 O 0.6366(8) 0.4874(8) 0.4959(3) 0.0242(15) Uani 0.5 1 d D . P . .
N1 N 0.5177(9) 0.6124(9) 0.5335(3) 0.030(2) Uani 0.5 1 d D . P . .
H1 H 0.425771 0.616329 0.535228 0.036 Uiso 0.5 1 d R . P . .
N2 N 0.3688(10) 0.3961(9) 0.4767(3) 0.0256(19) Uani 0.5 1 d D . P . .
H2 H 0.287220 0.403924 0.488188 0.031 Uiso 0.5 1 d R . P . .
N3 N 0.0814(5) 0.3620(5) 0.21065(17) 0.0228(9) Uani 1 1 d . . . . .
C1 C 0.5177(11) 0.499(2) 0.5004(12) 0.019(2) Uani 0.5 1 d D U P . .
C2 C 0.3347(6) 0.2739(6) 0.4340(2) 0.0266(11) Uani 1 1 d D . . . .
H2AA H 0.260316 0.183699 0.444116 0.032 Uiso 0.5 1 d R . P A 1
H2AB H 0.430186 0.263839 0.432916 0.032 Uiso 0.5 1 d R . P A 1
H2BC H 0.348426 0.185029 0.428906 0.032 Uiso 0.5 1 d R . P B 2
H2BD H 0.257186 0.255169 0.457096 0.032 Uiso 0.5 1 d R . P B 2
C3 C 0.2667(6) 0.3011(6) 0.3760(2) 0.0205(10) Uani 1 1 d . . . . .
C4 C 0.3444(6) 0.4283(6) 0.3523(2) 0.0227(11) Uani 1 1 d . . . . .
H4 H 0.442148 0.502201 0.373363 0.027 Uiso 1 1 calc R . . . .
C5 C 0.2822(6) 0.4499(5) 0.2983(2) 0.0207(10) Uani 1 1 d . . . . .
H5 H 0.336684 0.538857 0.283192 0.025 Uiso 1 1 calc R . . . .
C6 C 0.1409(5) 0.3425(5) 0.26638(19) 0.0178(10) Uani 1 1 d . . . . .
C7 C 0.0594(6) 0.2159(5) 0.2907(2) 0.0192(10) Uani 1 1 d . . . . .
H7 H -0.039701 0.142866 0.270150 0.023 Uiso 1 1 calc R . . . .
C8 C 0.1233(6) 0.1967(5) 0.3449(2) 0.0209(10) Uani 1 1 d . . . . .
H8 H 0.067164 0.109950 0.360941 0.025 Uiso 1 1 calc R . . . .
C9 C 0.1877(5) 0.4444(5) 0.17587(19) 0.0188(10) Uani 1 1 d . . . . .
C10 C 0.3019(6) 0.4049(6) 0.1624(2) 0.0212(10) Uani 1 1 d . . . . .
H10 H 0.320093 0.328362 0.179801 0.025 Uiso 1 1 calc R . . . .
C11 C 0.3901(6) 0.4779(5) 0.1231(2) 0.0209(10) Uani 1 1 d . . . . .
H11 H 0.469004 0.451935 0.113711 0.025 Uiso 1 1 calc R . . . .
C12 C 0.3608(6) 0.5898(5) 0.0979(2) 0.0213(10) Uani 1 1 d . . . . .
C13 C 0.2511(6) 0.6331(6) 0.1126(2) 0.0268(11) Uani 1 1 d . . . . .
H13 H 0.234569 0.711343 0.096048 0.032 Uiso 1 1 calc R . . . .
C14 C 0.1652(6) 0.5600(6) 0.1521(2) 0.0267(11) Uani 1 1 d . . . . .
H14 H 0.090238 0.589562 0.163060 0.032 Uiso 1 1 calc R . . . .
C15 C -0.0815(5) 0.2918(5) 0.1841(2) 0.0173(9) Uani 1 1 d . . . . .
C16 C -0.1262(6) 0.2281(6) 0.1281(2) 0.0234(11) Uani 1 1 d . . . . .
H16 H -0.047700 0.226792 0.108820 0.028 Uiso 1 1 calc R . . . .
C17 C -0.2831(6) 0.1658(6) 0.0992(2) 0.0228(11) Uani 1 1 d . . . . .
H17 H -0.312027 0.123030 0.060528 0.027 Uiso 1 1 calc R . . . .
C18 C -0.3959(5) 0.1672(5) 0.1278(2) 0.0182(10) Uani 1 1 d . . . . .
C19 C -0.3545(5) 0.2288(5) 0.1843(2) 0.0178(10) Uani 1 1 d . . . . .
H19 H -0.433730 0.228596 0.203493 0.021 Uiso 1 1 calc R . . . .
C20 C -0.1975(5) 0.2906(5) 0.21296(19) 0.0172(9) Uani 1 1 d . . . . .
H20 H -0.168978 0.331892 0.251843 0.021 Uiso 1 1 calc R . . . .
I3 I 0.37151(4) 1.05535(4) 0.30249(2) 0.03196(10) Uani 1 1 d . . . . .
I4 I 0.95314(4) 0.74772(4) 0.00267(2) 0.03148(10) Uani 1 1 d . . . . .
O2 O 1.1490(7) 0.5089(8) 0.5041(3) 0.0232(15) Uani 0.5 1 d D . P . .
N4 N 0.9767(9) 0.5549(9) 0.5466(3) 0.0237(18) Uani 0.5 1 d D . P . .
H4A H 0.877365 0.545221 0.543933 0.028 Uiso 0.5 1 d R . P . .
N5 N 0.8901(10) 0.4187(9) 0.4596(3) 0.0222(18) Uani 0.5 1 d D . P . .
H5A H 0.792771 0.395925 0.466005 0.027 Uiso 0.5 1 d R . P . .
N6 N 0.8145(5) 0.7658(5) 0.24905(18) 0.0247(9) Uani 1 1 d . . . . .
C21 C 1.0169(12) 0.497(2) 0.5030(6) 0.015(3) Uani 0.5 1 d D U P . .
C22 C 0.9035(6) 0.3688(6) 0.40311(19) 0.0241(11) Uani 1 1 d D . . . .
H22A H 0.824589 0.269665 0.390410 0.029 Uiso 0.5 1 d R . P C 1
H22B H 1.005659 0.369845 0.405520 0.029 Uiso 0.5 1 d R . P C 1
H22C H 0.930919 0.299515 0.384470 0.029 Uiso 0.5 1 d R . P D 2
H22D H 0.805319 0.314055 0.414400 0.029 Uiso 0.5 1 d R . P D 2
C23 C 0.8808(6) 0.4716(5) 0.36064(19) 0.0197(10) Uani 1 1 d . . . . .
C24 C 0.7310(6) 0.4658(6) 0.3411(2) 0.0230(11) Uani 1 1 d . . . . .
H24 H 0.643147 0.396284 0.353982 0.028 Uiso 1 1 calc R . . . .
C25 C 0.7084(6) 0.5587(6) 0.3038(2) 0.0242(11) Uani 1 1 d . . . . .
H25 H 0.605031 0.551570 0.290500 0.029 Uiso 1 1 calc R . . . .
C26 C 0.8359(6) 0.6639(5) 0.2850(2) 0.0208(10) Uani 1 1 d . . . . .
C27 C 0.9853(6) 0.6672(5) 0.3032(2) 0.0224(11) Uani 1 1 d . . . . .
H27 H 1.073122 0.735443 0.289951 0.027 Uiso 1 1 calc R . . . .
C28 C 1.0058(6) 0.5723(6) 0.3401(2) 0.0232(11) Uani 1 1 d . . . . .
H28 H 1.107990 0.575656 0.351848 0.028 Uiso 1 1 calc R . . . .
C29 C 0.7146(6) 0.8315(5) 0.2602(2) 0.0211(10) Uani 1 1 d . . . . .
C30 C 0.7224(6) 0.8807(6) 0.3166(2) 0.0266(11) Uani 1 1 d . . . . .
H30 H 0.795722 0.870820 0.346768 0.032 Uiso 1 1 calc R . . . .
C31 C 0.6256(6) 0.9434(6) 0.3292(2) 0.0293(12) Uani 1 1 d . . . . .
H31 H 0.632653 0.977012 0.367596 0.035 Uiso 1 1 calc R . . . .
C32 C 0.5180(6) 0.9567(5) 0.2852(2) 0.0232(11) Uani 1 1 d . . . . .
C33 C 0.5076(6) 0.9070(5) 0.2294(2) 0.0255(11) Uani 1 1 d . . . . .
H33 H 0.433042 0.915559 0.199419 0.031 Uiso 1 1 calc R . . . .
C34 C 0.6062(6) 0.8445(5) 0.2171(2) 0.0247(11) Uani 1 1 d . . . . .
H34 H 0.598606 0.810578 0.178687 0.030 Uiso 1 1 calc R . . . .
C35 C 0.8466(6) 0.7613(6) 0.1931(2) 0.0213(10) Uani 1 1 d . . . . .
C36 C 0.9159(7) 0.8908(6) 0.1699(2) 0.0342(14) Uani 1 1 d . . . . .
H36 H 0.942681 0.982785 0.191259 0.041 Uiso 1 1 calc R . . . .
C37 C 0.9465(7) 0.8873(6) 0.1155(2) 0.0291(12) Uani 1 1 d . . . . .
H37 H 0.992986 0.976519 0.099435 0.035 Uiso 1 1 calc R . . . .
C38 C 0.9092(5) 0.7538(6) 0.0850(2) 0.0215(10) Uani 1 1 d . . . . .
C39 C 0.8408(6) 0.6250(5) 0.1077(2) 0.0198(10) Uani 1 1 d . . . . .
H39 H 0.814190 0.533118 0.086329 0.024 Uiso 1 1 calc R . . . .
C40 C 0.8103(5) 0.6288(5) 0.1620(2) 0.0198(10) Uani 1 1 d . . . . .
H40 H 0.764019 0.539311 0.177956 0.024 Uiso 1 1 calc R . . . .
O51 O 0.155(2) 0.944(2) 0.5365(8) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
O52 O 0.215(3) 0.860(6) 0.4601(17) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
C51 C -0.044(2) 0.836(4) 0.4519(11) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
H51A H -0.121383 0.761190 0.469310 0.068 Uiso 0.202(6) 1 calc R . P E -1
H51B H -0.046791 0.795263 0.413756 0.068 Uiso 0.202(6) 1 calc R . P E -1
H51C H -0.068570 0.921698 0.448789 0.068 Uiso 0.202(6) 1 calc R . P E -1
C52 C 0.117(3) 0.884(4) 0.4880(9) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
C53 C 0.374(3) 0.883(4) 0.4872(11) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
H53A H 0.372334 0.836165 0.522943 0.054 Uiso 0.202(6) 1 calc R . P E -1
H53B H 0.444191 0.989759 0.496868 0.054 Uiso 0.202(6) 1 calc R . P E -1
C54 C 0.434(3) 0.815(4) 0.4467(14) 0.0451(16) Uiso 0.202(6) 1 d D . P E -1
H54A H 0.386572 0.819476 0.407474 0.068 Uiso 0.202(6) 1 calc R . P E -1
H54B H 0.406379 0.712198 0.452883 0.068 Uiso 0.202(6) 1 calc R . P E -1
H54C H 0.549444 0.869785 0.453072 0.068 Uiso 0.202(6) 1 calc R . P E -1
O61 O 0.067(2) 0.9590(17) 0.5528(6) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
O62 O 0.0003(19) 0.9538(17) 0.4592(6) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
C61 C -0.017(3) 1.138(2) 0.5160(9) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
H61A H -0.107492 1.111453 0.534576 0.068 Uiso 0.269(5) 1 calc R . P F -2
H61B H -0.045894 1.161111 0.477417 0.068 Uiso 0.269(5) 1 calc R . P F -2
H61C H 0.072798 1.224747 0.538299 0.068 Uiso 0.269(5) 1 calc R . P F -2
C62 C 0.026(3) 1.012(2) 0.5124(6) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
C63 C 0.024(3) 0.821(2) 0.4513(12) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
H63A H -0.033073 0.767886 0.412743 0.054 Uiso 0.269(5) 1 calc R . P F -2
H63B H -0.019679 0.754986 0.479781 0.054 Uiso 0.269(5) 1 calc R . P F -2
C64 C 0.192(3) 0.859(5) 0.4581(17) 0.0451(16) Uiso 0.269(5) 1 d D . P F -2
H64A H 0.218027 0.858141 0.420434 0.068 Uiso 0.269(5) 1 calc R . P F -2
H64B H 0.217136 0.787701 0.479274 0.068 Uiso 0.269(5) 1 calc R . P F -2
H64C H 0.253666 0.958444 0.479290 0.068 Uiso 0.269(5) 1 calc R . P F -2
O71 O 0.603(2) 1.160(2) 0.5522(7) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
O72 O 0.3552(15) 0.9909(19) 0.5074(7) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
C71 C 0.568(3) 0.994(3) 0.4727(10) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
H71A H 0.629316 1.072134 0.451457 0.068 Uiso 0.251(5) 1 calc R . P G -3
H71B H 0.478657 0.916884 0.446025 0.068 Uiso 0.251(5) 1 calc R . P G -3
H71C H 0.636175 0.952202 0.492729 0.068 Uiso 0.251(5) 1 calc R . P G -3
C72 C 0.5102(18) 1.057(2) 0.5141(9) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
C73 C 0.249(2) 0.872(4) 0.4633(15) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
H73A H 0.261310 0.780475 0.470932 0.054 Uiso 0.251(5) 1 calc R . P G -3
H73B H 0.274969 0.896910 0.425726 0.054 Uiso 0.251(5) 1 calc R . P G -3
C74 C 0.085(2) 0.847(3) 0.4621(12) 0.0451(16) Uiso 0.251(5) 1 d D . P G -3
H74A H 0.027422 0.829561 0.422395 0.068 Uiso 0.251(5) 1 calc R . P G -3
H74B H 0.084280 0.933820 0.481785 0.068 Uiso 0.251(5) 1 calc R . P G -3
H74C H 0.033664 0.760381 0.481384 0.068 Uiso 0.251(5) 1 calc R . P G -3


_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 C12 2.098(5) . ?
I2 C18 2.101(5) . ?
O1 C1 1.209(9) . ?
N1 H1 0.9002 . ?
N1 C1 1.361(8) . ?
N1 C2 1.448(7) 2_666 ?
N2 H2 0.9000 . ?
N2 C1 1.362(8) . ?
N2 C2 1.455(7) . ?
N3 C6 1.409(6) . ?
N3 C9 1.434(6) . ?
N3 C15 1.419(6) . ?
C2 H2AA 0.9603 . ?
C2 H2AB 0.9601 . ?
C2 H2BC 0.9600 . ?
C2 H2BD 0.9605 . ?
C2 C3 1.512(7) . ?
C3 C4 1.383(7) . ?
C3 C8 1.381(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(7) . ?
C6 C7 1.396(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(7) . ?
C9 C14 1.388(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.394(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(7) . ?
C12 C13 1.379(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(7) . ?
C15 C20 1.400(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.377(7) . ?
C18 C19 1.386(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(6) . ?
C20 H20 0.9500 . ?
I3 C32 2.103(5) . ?
I4 C38 2.093(5) . ?
O2 C21 1.207(9) . ?
N4 H4A 0.9001 . ?
N4 C21 1.363(8) . ?
N4 C22 1.435(7) 2_766 ?
N5 H5A 0.9001 . ?
N5 C21 1.365(8) . ?
N5 C22 1.473(7) . ?
N6 C26 1.416(6) . ?
N6 C29 1.417(6) . ?
N6 C35 1.431(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 H22D 0.9599 . ?
C22 C23 1.527(7) . ?
C23 C24 1.396(7) . ?
C23 C28 1.387(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.370(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.398(7) . ?
C26 C27 1.398(7) . ?
C27 H27 0.9500 . ?
C27 C28 1.371(7) . ?
C28 H28 0.9500 . ?
C29 C30 1.401(7) . ?
C29 C34 1.377(7) . ?
C30 H30 0.9500 . ?
C30 C31 1.379(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(8) . ?
C32 C33 1.382(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.379(7) . ?
C35 C40 1.376(7) . ?
C36 H36 0.9500 . ?
C36 C37 1.388(7) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(7) . ?
C38 C39 1.367(7) . ?
C39 H39 0.9500 . ?
C39 C40 1.385(7) . ?
C40 H40 0.9500 . ?
O51 C52 1.209(14) . ?
O52 C52 1.332(14) . ?
O52 C53 1.458(15) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C51 C52 1.485(14) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C53 C54 1.482(15) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
O61 C62 1.206(13) . ?
O62 C62 1.322(13) . ?
O62 C63 1.451(14) . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C61 C62 1.488(13) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C63 C64 1.459(14) . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
O71 C72 1.253(13) . ?
O72 C72 1.318(13) . ?
O72 C73 1.446(15) . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C71 C72 1.459(13) . ?
C73 H73A 0.9900 . ?
C73 H73B 0.9900 . ?
C73 C74 1.470(14) . ?
C74 H74A 0.9800 . ?
C74 H74B 0.9800 . ?
C74 H74C 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
C1 N1 H1 120.0 . . ?
C1 N1 C2 120.0(7) . 2_666 ?
C2 N1 H1 120.0 2_666 . ?
C1 N2 H2 118.2 . . ?
C1 N2 C2 123.5(8) . . ?
C2 N2 H2 118.3 . . ?
C6 N3 C9 120.2(4) . . ?
C6 N3 C15 123.0(4) . . ?
C15 N3 C9 116.5(4) . . ?
O1 C1 N1 123.5(9) . . ?
O1 C1 N2 124.1(9) . . ?
N1 C1 N2 112.3(8) . . ?
N2 C2 H2AA 109.7 . . ?
N2 C2 H2AB 109.4 . . ?
N2 C2 C3 110.1(5) . . ?
H2AA C2 H2AB 108.3 . . ?
H2BC C2 H2BD 107.2 . . ?
C3 C2 H2AA 109.5 . . ?
C3 C2 H2AB 109.8 . . ?
C3 C2 H2BC 107.6 . . ?
C3 C2 H2BD 107.8 . . ?
C4 C3 C2 122.0(5) . . ?
C8 C3 C2 119.8(4) . . ?
C8 C3 C4 118.2(4) . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(5) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 N3 120.3(4) . . ?
C5 C6 C7 118.7(4) . . ?
C7 C6 N3 121.0(4) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C3 C8 C7 121.5(5) . . ?
C3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 N3 122.0(4) . . ?
C10 C9 C14 120.2(4) . . ?
C14 C9 N3 117.7(4) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.1(5) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 I1 120.6(4) . . ?
C13 C12 I1 118.1(4) . . ?
C13 C12 C11 121.3(4) . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.7(5) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C13 120.8(5) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 N3 119.4(4) . . ?
C16 C15 C20 119.2(4) . . ?
C20 C15 N3 121.3(4) . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.6(5) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.7(4) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 I2 118.8(3) . . ?
C17 C18 C19 120.9(4) . . ?
C19 C18 I2 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.1(4) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 120.3 . . ?
C19 C20 C15 119.5(4) . . ?
C19 C20 H20 120.3 . . ?
C21 N4 H4A 120.8 . . ?
C21 N4 C22 118.4(7) . 2_766 ?
C21 N5 H5A 118.2 . . ?
C21 N5 C22 123.7(8) . . ?
C21 N5 H22D 155.7 . . ?
C22 N5 H5A 118.2 . . ?
C22 N5 H22D 39.4 . . ?
C26 N6 C29 119.0(4) . . ?
C26 N6 C35 118.2(4) . . ?
C29 N6 C35 119.2(4) . . ?
O2 C21 N4 123.4(8) . . ?
O2 C21 N5 124.2(9) . . ?
N4 C21 N5 112.3(8) . . ?
N5 C22 H22A 110.0 . . ?
N5 C22 H22B 109.7 . . ?
N5 C22 H22C 141.7 . . ?
N5 C22 H22D 63.6 . . ?
N5 C22 C23 109.2(5) . . ?
H22A C22 H22B 108.3 . . ?
H22C C22 H22D 107.8 . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.9 . . ?
C23 C22 H22C 108.8 . . ?
C23 C22 H22D 109.0 . . ?
C24 C23 C22 120.2(4) . . ?
C28 C23 C22 121.9(4) . . ?
C28 C23 C24 117.9(5) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(5) . . ?
C25 C24 H24 119.4 . . ?
C24 C25 H25 119.7 . . ?
C24 C25 C26 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 N6 120.7(5) . . ?
C25 C26 C27 118.3(5) . . ?
C27 C26 N6 120.9(4) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.3(4) . . ?
C28 C27 H27 119.8 . . ?
C23 C28 H28 119.2 . . ?
C27 C28 C23 121.6(5) . . ?
C27 C28 H28 119.2 . . ?
C30 C29 N6 119.6(5) . . ?
C34 C29 N6 121.6(4) . . ?
C34 C29 C30 118.7(5) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.2(5) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 120.3 . . ?
C30 C31 C32 119.3(5) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 I3 120.4(4) . . ?
C33 C32 I3 119.4(4) . . ?
C33 C32 C31 120.2(5) . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.1(5) . . ?
C34 C33 H33 119.9 . . ?
C29 C34 C33 120.5(5) . . ?
C29 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 N6 119.9(5) . . ?
C40 C35 N6 120.8(4) . . ?
C40 C35 C36 119.3(5) . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.3(5) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 120.2 . . ?
C38 C37 C36 119.7(5) . . ?
C38 C37 H37 120.2 . . ?
C37 C38 I4 119.8(4) . . ?
C39 C38 I4 119.8(4) . . ?
C39 C38 C37 120.4(4) . . ?
C38 C39 H39 120.1 . . ?
C38 C39 C40 119.8(5) . . ?
C40 C39 H39 120.1 . . ?
C35 C40 C39 120.5(4) . . ?
C35 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C52 O52 C53 124(3) . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
O51 C52 O52 124(2) . . ?
O51 C52 C51 123.2(18) . . ?
O52 C52 C51 112.6(16) . . ?
O52 C53 H53A 110.1 . . ?
O52 C53 H53B 110.1 . . ?
O52 C53 C54 108.2(15) . . ?
H53A C53 H53B 108.4 . . ?
C54 C53 H53A 110.1 . . ?
C54 C53 H53B 110.1 . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C62 O62 C63 116.7(17) . . ?
H61A C61 H61B 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C62 C61 H61A 109.5 . . ?
C62 C61 H61B 109.5 . . ?
C62 C61 H61C 109.5 . . ?
O61 C62 O62 122.3(16) . . ?
O61 C62 C61 125.0(14) . . ?
O62 C62 C61 112.4(13) . . ?
O62 C63 H63A 109.7 . . ?
O62 C63 H63B 109.7 . . ?
O62 C63 C64 110.0(16) . . ?
H63A C63 H63B 108.2 . . ?
C64 C63 H63A 109.7 . . ?
C64 C63 H63B 109.7 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64B 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C72 O72 C73 125.5(16) . . ?
H71A C71 H71B 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C72 C71 H71A 109.5 . . ?
C72 C71 H71B 109.5 . . ?
C72 C71 H71C 109.5 . . ?
O71 C72 O72 126.0(16) . . ?
O71 C72 C71 121.2(15) . . ?
O72 C72 C71 112.7(13) . . ?
O72 C73 H73A 109.7 . . ?
O72 C73 H73B 109.7 . . ?
O72 C73 C74 109.7(15) . . ?
H73A C73 H73B 108.2 . . ?
C74 C73 H73A 109.7 . . ?
C74 C73 H73B 109.7 . . ?
C73 C74 H74A 109.5 . . ?
C73 C74 H74B 109.5 . . ?
C73 C74 H74C 109.5 . . ?
H74A C74 H74B 109.5 . . ?
H74A C74 H74C 109.5 . . ?
H74B C74 H74C 109.5 . . ?

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
N1 H1 O2 0.90 2.35 3.151(10) 147.6 1_455 yes
N2 H2 O2 0.90 2.07 2.915(10) 155.7 1_455 yes
N4 H4A O1 0.90 2.20 3.023(10) 152.4 . yes
N5 H5A O1 0.90 2.24 3.023(10) 144.7 . yes

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
I1 C12 C13 C14 178.2(4) . . . . ?
I2 C18 C19 C20 179.3(3) . . . . ?
N2 C2 C3 C4 55.1(7) . . . . ?
N2 C2 C3 C8 -125.3(6) . . . . ?
N3 C6 C7 C8 177.6(4) . . . . ?
N3 C9 C10 C11 172.6(4) . . . . ?
N3 C9 C14 C13 -172.2(5) . . . . ?
N3 C15 C16 C17 -176.2(5) . . . . ?
N3 C15 C20 C19 176.0(4) . . . . ?
C2 N2 C1 N1 172.0(14) . . . . ?
C2 C3 C4 C5 178.4(4) . . . . ?
C2 C3 C8 C7 -178.1(4) . . . . ?
C3 C4 C5 C6 -1.0(7) . . . . ?
C4 C3 C8 C7 1.6(7) . . . . ?
C4 C5 C6 N3 -177.3(4) . . . . ?
C4 C5 C6 C7 3.0(7) . . . . ?
C5 C6 C7 C8 -2.6(7) . . . . ?
C6 N3 C9 C10 58.1(7) . . . . ?
C6 N3 C9 C14 -126.7(5) . . . . ?
C6 N3 C15 C16 -135.7(5) . . . . ?
C6 N3 C15 C20 46.7(7) . . . . ?
C6 C7 C8 C3 0.3(7) . . . . ?
C8 C3 C4 C5 -1.2(7) . . . . ?
C9 N3 C6 C5 30.9(7) . . . . ?
C9 N3 C6 C7 -149.3(5) . . . . ?
C9 N3 C15 C16 38.4(6) . . . . ?
C9 N3 C15 C20 -139.2(5) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C9 C14 C13 3.1(8) . . . . ?
C10 C11 C12 I1 -177.7(3) . . . . ?
C10 C11 C12 C13 2.6(7) . . . . ?
C11 C12 C13 C14 -2.0(8) . . . . ?
C12 C13 C14 C9 -0.8(8) . . . . ?
C14 C9 C10 C11 -2.5(7) . . . . ?
C15 N3 C6 C5 -155.2(5) . . . . ?
C15 N3 C6 C7 24.6(7) . . . . ?
C15 N3 C9 C10 -116.1(5) . . . . ?
C15 N3 C9 C14 59.1(6) . . . . ?
C15 C16 C17 C18 -0.5(8) . . . . ?
C16 C15 C20 C19 -1.5(7) . . . . ?
C16 C17 C18 I2 -179.4(4) . . . . ?
C16 C17 C18 C19 -0.3(7) . . . . ?
C17 C18 C19 C20 0.2(7) . . . . ?
C18 C19 C20 C15 0.7(7) . . . . ?
C20 C15 C16 C17 1.5(8) . . . . ?
I3 C32 C33 C34 178.5(4) . . . . ?
I4 C38 C39 C40 -179.4(3) . . . . ?
N5 C22 C23 C24 -72.8(6) . . . . ?
N5 C22 C23 C28 107.4(6) . . . . ?
N6 C26 C27 C28 177.0(4) . . . . ?
N6 C29 C30 C31 -179.1(5) . . . . ?
N6 C29 C34 C33 178.8(5) . . . . ?
N6 C35 C36 C37 -179.6(5) . . . . ?
N6 C35 C40 C39 179.6(4) . . . . ?
C22 N5 C21 N4 167.8(11) . . . . ?
C22 C23 C24 C25 178.9(4) . . . . ?
C22 C23 C28 C27 -178.1(4) . . . . ?
C23 C24 C25 C26 -1.2(8) . . . . ?
C24 C23 C28 C27 2.1(7) . . . . ?
C24 C25 C26 N6 -176.2(5) . . . . ?
C24 C25 C26 C27 2.9(7) . . . . ?
C25 C26 C27 C28 -2.1(7) . . . . ?
C26 N6 C29 C30 42.5(7) . . . . ?
C26 N6 C29 C34 -135.6(5) . . . . ?
C26 N6 C35 C36 -142.6(5) . . . . ?
C26 N6 C35 C40 36.9(7) . . . . ?
C26 C27 C28 C23 -0.4(7) . . . . ?
C28 C23 C24 C25 -1.3(7) . . . . ?
C29 N6 C26 C25 41.3(7) . . . . ?
C29 N6 C26 C27 -137.8(5) . . . . ?
C29 N6 C35 C36 58.8(7) . . . . ?
C29 N6 C35 C40 -121.7(5) . . . . ?
C29 C30 C31 C32 0.5(8) . . . . ?
C30 C29 C34 C33 0.7(7) . . . . ?
C30 C31 C32 I3 -178.8(4) . . . . ?
C30 C31 C32 C33 0.3(8) . . . . ?
C31 C32 C33 C34 -0.6(8) . . . . ?
C32 C33 C34 C29 0.0(8) . . . . ?
C34 C29 C30 C31 -1.0(8) . . . . ?
C35 N6 C26 C25 -117.4(5) . . . . ?
C35 N6 C26 C27 63.5(6) . . . . ?
C35 N6 C29 C30 -159.0(5) . . . . ?
C35 N6 C29 C34 22.9(7) . . . . ?
C35 C36 C37 C38 -0.8(9) . . . . ?
C36 C35 C40 C39 -0.9(8) . . . . ?
C36 C37 C38 I4 179.4(4) . . . . ?
C36 C37 C38 C39 0.7(8) . . . . ?
C37 C38 C39 C40 -0.7(7) . . . . ?
C38 C39 C40 C35 0.8(7) . . . . ?
C40 C35 C36 C37 0.9(9) . . . . ?
C52 O52 C53 C54 168(5) . . . . ?
C53 O52 C52 O51 10(8) . . . . ?
C53 O52 C52 C51 -173(4) . . . . ?
C62 O62 C63 C64 -79(3) . . . . ?
C63 O62 C62 O61 0(4) . . . . ?
C63 O62 C62 C61 -174(2) . . . . ?
C72 O72 C73 C74 -169(3) . . . . ?
C73 O72 C72 O71 -180(3) . . . . ?
C73 O72 C72 C71 -2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT430_tpa_a               
;
PROBLEM: Short Inter D...A Contact  O1       ..O2       .       2.03 Ang.  
RESPONSE: Erroneously identified contact because of disorder. This distance is
between two half-occupied carbonyl oxygen atoms and does not exist in any 
asymmetric unit.
;
_exptl_crystal_recrystallization_method 'Slow Evaporation'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       'Conductive, Persistent radical'
####################################################################### 
# 
# 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_mh_i2_u_etoac
_database_code_depnum_ccdc_archive 'CCDC 2165899'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_audit_creation_date             2021-02-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 I2 N3 O'
_chemical_formula_sum            'C20 H17 I2 N3 O'
_chemical_formula_weight         569.17
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4579(4)
_cell_length_b                   9.9193(4)
_cell_length_c                   23.4761(9)
_cell_angle_alpha                90.9100(10)
_cell_angle_beta                 99.539(2)
_cell_angle_gamma                114.9540(10)
_cell_volume                     1960.13(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9682
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.13
_cell_measurement_theta_min      2.36
_exptl_absorpt_coefficient_mu    3.223
_exptl_absorpt_correction_T_max  0.4954
_exptl_absorpt_correction_T_min  0.3647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0887 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.7362.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.929
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            76938
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.188
_diffrn_reflns_theta_min         2.275
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 PHOTON-II
_diffrn_detector_area_resol_mean 7.39
_diffrn_detector_type            'area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11902
_reflns_number_total             14982
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ Ver. 8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker APEX3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT+ Ver. 8.40B (Bruker, 2019)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.949
_refine_diff_density_min         -1.079
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       0.00151(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         14982
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0158P)²+1.5166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0553
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N2-H2 = N4-H4A = N4-H4B = N5-H5A
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C24(H24), C25(H25), C27(H27), C28(H28),
  C30(H30), C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 1.23049(2) 0.97638(2) 0.09239(2) 0.02330(4) Uani 1 1 d . . . . .
I2 I 0.05075(2) 0.31735(2) 0.03327(2) 0.02176(3) Uani 1 1 d . . . . .
O1 O 0.66132(18) 0.70535(18) 0.50276(7) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.4198(2) 0.6235(2) 0.52914(9) 0.0265(4) Uani 1 1 d D . . . .
H1A H 0.427(3) 0.542(2) 0.5380(12) 0.039(8) Uiso 1 1 d D . . . .
H1B H 0.333(3) 0.632(4) 0.5237(14) 0.056(10) Uiso 1 1 d D . . . .
N2 N 0.5079(2) 0.8265(2) 0.47702(7) 0.0204(3) Uani 1 1 d D . . . .
H2 H 0.417(2) 0.821(3) 0.4733(11) 0.026(7) Uiso 1 1 d D . . . .
N3 N 0.6416(2) 0.7533(2) 0.21673(7) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.5352(2) 0.7171(2) 0.50267(9) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.6234(3) 0.9344(2) 0.44764(9) 0.0217(4) Uani 1 1 d . . . . .
H2A H 0.729913 0.968136 0.472422 0.026 Uiso 1 1 calc R U . . .
H2B H 0.599925 1.022466 0.443918 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6299(2) 0.8793(2) 0.38778(8) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.7400(2) 0.9771(2) 0.35768(9) 0.0186(4) Uani 1 1 d . . . . .
H4 H 0.811912 1.073601 0.375894 0.022 Uiso 1 1 calc R U . . .
C5 C 0.7469(2) 0.9370(2) 0.30172(8) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.822732 1.005832 0.281953 0.022 Uiso 1 1 calc R U . . .
C6 C 0.6423(2) 0.7950(2) 0.27435(8) 0.0174(4) Uani 1 1 d . . . . .
C7 C 0.5354(2) 0.6948(2) 0.30497(8) 0.0178(4) Uani 1 1 d . . . . .
H7 H 0.466182 0.596865 0.287469 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5292(2) 0.7371(2) 0.36100(8) 0.0173(4) Uani 1 1 d . . . . .
H8 H 0.455145 0.667770 0.381215 0.021 Uiso 1 1 calc R U . . .
C9 C 0.7787(2) 0.8103(2) 0.19125(8) 0.0172(4) Uani 1 1 d . . . . .
C10 C 0.9271(2) 0.8314(2) 0.22143(8) 0.0173(4) Uani 1 1 d . . . . .
H10 H 0.940360 0.813664 0.261179 0.021 Uiso 1 1 calc R U . . .
C11 C 1.0563(2) 0.8785(2) 0.19348(9) 0.0184(4) Uani 1 1 d . . . . .
H11 H 1.157283 0.891704 0.214020 0.022 Uiso 1 1 calc R U . . .
C12 C 1.0376(2) 0.9063(2) 0.13557(9) 0.0181(4) Uani 1 1 d . . . . .
C13 C 0.8910(2) 0.8884(2) 0.10517(9) 0.0210(4) Uani 1 1 d . . . . .
H13 H 0.878379 0.907928 0.065617 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7631(2) 0.8415(2) 0.13349(9) 0.0214(4) Uani 1 1 d . . . . .
H14 H 0.662718 0.830327 0.113071 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4985(2) 0.6492(2) 0.17990(8) 0.0181(4) Uani 1 1 d . . . . .
C16 C 0.4967(2) 0.5203(2) 0.15527(9) 0.0218(4) Uani 1 1 d . . . . .
H16 H 0.583733 0.496351 0.167076 0.026 Uiso 1 1 calc R U . . .
C17 C 0.3688(2) 0.4262(2) 0.11361(9) 0.0212(4) Uani 1 1 d . . . . .
H17 H 0.369333 0.339661 0.095917 0.025 Uiso 1 1 calc R U . . .
C18 C 0.2401(2) 0.4593(2) 0.09795(8) 0.0174(4) Uani 1 1 d . . . . .
C19 C 0.2373(2) 0.5849(2) 0.12429(9) 0.0186(4) Uani 1 1 d . . . . .
H19 H 0.147172 0.605284 0.114317 0.022 Uiso 1 1 calc R U . . .
C20 C 0.3678(2) 0.6802(2) 0.16537(9) 0.0191(4) Uani 1 1 d . . . . .
H20 H 0.367321 0.766398 0.183412 0.023 Uiso 1 1 calc R U . . .
I3 I 0.46640(2) 0.11480(2) 0.31133(2) 0.03106(4) Uani 1 1 d . . . . .
I4 I -0.45037(2) 0.25264(2) 0.00237(2) 0.02612(4) Uani 1 1 d . . . . .
O2 O 0.15664(17) 0.70431(17) 0.49457(7) 0.0224(3) Uani 1 1 d . . . . .
N4 N -0.0506(2) 0.6474(2) 0.54177(9) 0.0251(4) Uani 1 1 d D . . . .
H4A H -0.030(3) 0.576(2) 0.5548(11) 0.025(7) Uiso 1 1 d D . . . .
H4B H -0.146(2) 0.636(3) 0.5393(12) 0.033(8) Uiso 1 1 d D . . . .
N5 N -0.0223(2) 0.7981(2) 0.46710(7) 0.0211(3) Uani 1 1 d D . . . .
H5A H -0.112(2) 0.789(3) 0.4713(12) 0.036(8) Uiso 1 1 d D . . . .
N6 N -0.0414(2) 0.3726(2) 0.25382(7) 0.0227(4) Uani 1 1 d . . . . .
C21 C 0.0335(2) 0.7146(2) 0.50014(8) 0.0181(4) Uani 1 1 d . . . . .
C22 C 0.0438(3) 0.8537(2) 0.41575(9) 0.0219(4) Uani 1 1 d . . . . .
H22A H 0.159104 0.917831 0.427766 0.026 Uiso 1 1 calc R U . . .
H22B H -0.006247 0.916266 0.397643 0.026 Uiso 1 1 calc R U . . .
C23 C 0.0191(2) 0.7297(2) 0.37112(8) 0.0188(4) Uani 1 1 d . . . . .
C24 C 0.1465(2) 0.7293(2) 0.34915(9) 0.0214(4) Uani 1 1 d . . . . .
H24 H 0.249295 0.808531 0.361706 0.026 Uiso 1 1 calc R U . . .
C25 C 0.1261(2) 0.6150(3) 0.30912(9) 0.0240(4) Uani 1 1 d . . . . .
H25 H 0.214250 0.618036 0.293828 0.029 Uiso 1 1 calc R U . . .
C26 C -0.0220(2) 0.4966(2) 0.29137(9) 0.0204(4) Uani 1 1 d . . . . .
C27 C -0.1516(2) 0.4978(2) 0.31170(9) 0.0222(4) Uani 1 1 d . . . . .
H27 H -0.254658 0.419640 0.298437 0.027 Uiso 1 1 calc R U . . .
C28 C -0.1304(2) 0.6131(2) 0.35132(9) 0.0220(4) Uani 1 1 d . . . . .
H28 H -0.219489 0.612488 0.365190 0.026 Uiso 1 1 calc R U . . .
C29 C 0.0730(2) 0.3148(2) 0.26581(9) 0.0198(4) Uani 1 1 d . . . . .
C30 C 0.1203(3) 0.2907(3) 0.32276(9) 0.0271(5) Uani 1 1 d . . . . .
H30 H 0.073838 0.311650 0.352621 0.032 Uiso 1 1 calc R U . . .
C31 C 0.2340(3) 0.2366(3) 0.33655(10) 0.0279(5) Uani 1 1 d . . . . .
H31 H 0.265936 0.221574 0.375547 0.033 Uiso 1 1 calc R U . . .
C32 C 0.3003(3) 0.2048(2) 0.29276(10) 0.0232(4) Uani 1 1 d . . . . .
C33 C 0.2547(3) 0.2276(2) 0.23616(9) 0.0227(4) Uani 1 1 d . . . . .
H33 H 0.300974 0.205654 0.206441 0.027 Uiso 1 1 calc R U . . .
C34 C 0.1413(3) 0.2825(2) 0.22242(9) 0.0210(4) Uani 1 1 d . . . . .
H34 H 0.110293 0.297909 0.183387 0.025 Uiso 1 1 calc R U . . .
C35 C -0.1341(2) 0.3465(2) 0.19714(9) 0.0197(4) Uani 1 1 d . . . . .
C36 C -0.2264(3) 0.2006(2) 0.17182(9) 0.0274(5) Uani 1 1 d . . . . .
H36 H -0.227555 0.119093 0.192745 0.033 Uiso 1 1 calc R U . . .
C37 C -0.3162(3) 0.1737(2) 0.11656(9) 0.0250(4) Uani 1 1 d . . . . .
H37 H -0.377881 0.074040 0.099389 0.030 Uiso 1 1 calc R U . . .
C38 C -0.3160(2) 0.2924(2) 0.08627(8) 0.0187(4) Uani 1 1 d . . . . .
C39 C -0.2244(2) 0.4378(2) 0.11060(9) 0.0203(4) Uani 1 1 d . . . . .
H39 H -0.223435 0.519056 0.089522 0.024 Uiso 1 1 calc R U . . .
C40 C -0.1341(2) 0.4641(2) 0.16601(9) 0.0194(4) Uani 1 1 d . . . . .
H40 H -0.071346 0.563895 0.182832 0.023 Uiso 1 1 calc 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
I1 C12 2.0985(19) . ?
I2 C18 2.0970(19) . ?
O1 C1 1.246(2) . ?
N1 H1A 0.862(17) . ?
N1 H1B 0.847(18) . ?
N1 C1 1.352(3) . ?
N2 H2 0.833(16) . ?
N2 C1 1.347(3) . ?
N2 C2 1.449(3) . ?
N3 C6 1.406(2) . ?
N3 C9 1.417(2) . ?
N3 C15 1.432(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.520(3) . ?
C3 C4 1.392(3) . ?
C3 C8 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(3) . ?
C6 C7 1.394(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 C13 1.387(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 C20 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(3) . ?
C18 C19 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(3) . ?
C20 H20 0.9500 . ?
I3 C32 2.103(2) . ?
I4 C38 2.0912(19) . ?
O2 C21 1.239(2) . ?
N4 H4A 0.859(16) . ?
N4 H4B 0.851(17) . ?
N4 C21 1.365(3) . ?
N5 H5A 0.838(17) . ?
N5 C21 1.348(3) . ?
N5 C22 1.459(3) . ?
N6 C26 1.430(3) . ?
N6 C29 1.416(3) . ?
N6 C35 1.420(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.516(3) . ?
C23 C24 1.389(3) . ?
C23 C28 1.392(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.385(3) . ?
C26 C27 1.392(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.395(3) . ?
C29 C34 1.392(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.386(3) . ?
C32 C33 1.380(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(3) . ?
C35 C40 1.386(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.381(3) . ?
C37 H37 0.9500 . ?
C37 C38 1.385(3) . ?
C38 C39 1.383(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.387(3) . ?
C40 H40 0.9500 . ?

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
H1A N1 H1B 123(3) . . ?
C1 N1 H1A 116(2) . . ?
C1 N1 H1B 117(2) . . ?
C1 N2 H2 117.6(18) . . ?
C1 N2 C2 121.26(18) . . ?
C2 N2 H2 120.2(18) . . ?
C6 N3 C9 123.26(16) . . ?
C6 N3 C15 120.89(16) . . ?
C9 N3 C15 115.84(15) . . ?
O1 C1 N1 122.3(2) . . ?
O1 C1 N2 121.49(19) . . ?
N2 C1 N1 116.16(19) . . ?
N2 C2 H2A 108.4 . . ?
N2 C2 H2B 108.4 . . ?
N2 C2 C3 115.69(17) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C4 C3 C2 118.42(18) . . ?
C8 C3 C2 123.31(18) . . ?
C8 C3 C4 118.26(18) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.50(19) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.98(18) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 N3 121.33(18) . . ?
C7 C6 N3 119.88(18) . . ?
C7 C6 C5 118.78(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.52(18) . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 120.90(18) . . ?
C3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C10 C9 N3 122.13(18) . . ?
C10 C9 C14 118.97(18) . . ?
C14 C9 N3 118.87(18) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.07(18) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.06(18) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 I1 120.72(15) . . ?
C13 C12 I1 118.71(15) . . ?
C13 C12 C11 120.57(18) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.87(19) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.44(19) . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N3 118.48(18) . . ?
C20 C15 N3 121.31(18) . . ?
C20 C15 C16 120.04(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.45(19) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.3 . . ?
C16 C17 C18 119.45(19) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 I2 118.48(14) . . ?
C17 C18 C19 120.65(18) . . ?
C19 C18 I2 120.86(14) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.38(18) . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 119.92(18) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
H4A N4 H4B 117(3) . . ?
C21 N4 H4A 113.0(17) . . ?
C21 N4 H4B 120.0(19) . . ?
C21 N5 H5A 115(2) . . ?
C21 N5 C22 119.31(17) . . ?
C22 N5 H5A 122.7(19) . . ?
C29 N6 C26 117.65(16) . . ?
C29 N6 C35 119.82(17) . . ?
C35 N6 C26 118.80(17) . . ?
O2 C21 N4 122.08(19) . . ?
O2 C21 N5 122.14(19) . . ?
N5 C21 N4 115.72(18) . . ?
N5 C22 H22A 109.0 . . ?
N5 C22 H22B 109.0 . . ?
N5 C22 C23 113.01(18) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.0 . . ?
C23 C22 H22B 109.0 . . ?
C24 C23 C22 120.46(18) . . ?
C24 C23 C28 118.12(19) . . ?
C28 C23 C22 121.42(18) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.08(19) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.34(19) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 N6 120.64(18) . . ?
C25 C26 C27 119.14(19) . . ?
C27 C26 N6 120.19(18) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 C26 120.06(19) . . ?
C28 C27 H27 120.0 . . ?
C23 C28 H28 119.4 . . ?
C27 C28 C23 121.17(19) . . ?
C27 C28 H28 119.4 . . ?
C30 C29 N6 119.30(19) . . ?
C34 C29 N6 121.90(18) . . ?
C34 C29 C30 118.8(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 C29 121.2(2) . . ?
C31 C30 H30 119.4 . . ?
C30 C31 H31 120.4 . . ?
C32 C31 C30 119.2(2) . . ?
C32 C31 H31 120.4 . . ?
C31 C32 I3 120.38(16) . . ?
C33 C32 I3 119.15(17) . . ?
C33 C32 C31 120.4(2) . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.3(2) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 120.08(19) . . ?
C33 C34 H34 120.0 . . ?
C36 C35 N6 119.95(19) . . ?
C40 C35 N6 121.11(18) . . ?
C40 C35 C36 118.93(19) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 C35 120.6(2) . . ?
C37 C36 H36 119.7 . . ?
C36 C37 H37 120.1 . . ?
C36 C37 C38 119.77(19) . . ?
C38 C37 H37 120.1 . . ?
C37 C38 I4 120.02(15) . . ?
C39 C38 I4 119.53(15) . . ?
C39 C38 C37 120.43(18) . . ?
C38 C39 H39 120.3 . . ?
C38 C39 C40 119.49(19) . . ?
C40 C39 H39 120.3 . . ?
C35 C40 C39 120.81(19) . . ?
C35 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?

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
N1 H1A O1 0.862(17) 2.36(2) 3.068(3) 139(3) 2_666 yes
N1 H1B O2 0.847(18) 2.10(2) 2.921(2) 162(3) . yes
N2 H2 O2 0.833(16) 2.378(19) 3.122(2) 149(2) . yes
N4 H4A O2 0.859(16) 2.67(2) 3.252(3) 126(2) 2_566 yes
N4 H4B O1 0.851(17) 2.26(2) 3.017(2) 149(2) 1_455 yes
N5 H5A O1 0.838(17) 2.207(19) 3.005(2) 159(3) 1_455 yes

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
I1 C12 C13 C14 179.73(15) . . . . ?
I2 C18 C19 C20 -177.35(15) . . . . ?
N2 C2 C3 C4 -179.14(18) . . . . ?
N2 C2 C3 C8 2.2(3) . . . . ?
N3 C6 C7 C8 -176.74(18) . . . . ?
N3 C9 C10 C11 175.84(18) . . . . ?
N3 C9 C14 C13 -175.84(19) . . . . ?
N3 C15 C16 C17 -171.54(19) . . . . ?
N3 C15 C20 C19 172.62(18) . . . . ?
C1 N2 C2 C3 77.3(2) . . . . ?
C2 N2 C1 O1 0.9(3) . . . . ?
C2 N2 C1 N1 179.52(19) . . . . ?
C2 C3 C4 C5 -176.65(19) . . . . ?
C2 C3 C8 C7 176.98(19) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C3 C8 C7 -1.6(3) . . . . ?
C4 C5 C6 N3 177.12(19) . . . . ?
C4 C5 C6 C7 -1.8(3) . . . . ?
C5 C6 C7 C8 2.2(3) . . . . ?
C6 N3 C9 C10 40.4(3) . . . . ?
C6 N3 C9 C14 -141.8(2) . . . . ?
C6 N3 C15 C16 -122.5(2) . . . . ?
C6 N3 C15 C20 62.2(3) . . . . ?
C6 C7 C8 C3 -0.5(3) . . . . ?
C8 C3 C4 C5 2.0(3) . . . . ?
C9 N3 C6 C5 30.4(3) . . . . ?
C9 N3 C6 C7 -150.7(2) . . . . ?
C9 N3 C15 C16 57.8(3) . . . . ?
C9 N3 C15 C20 -117.4(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C10 C9 C14 C13 2.0(3) . . . . ?
C10 C11 C12 I1 -179.69(14) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C9 -0.9(3) . . . . ?
C14 C9 C10 C11 -1.9(3) . . . . ?
C15 N3 C6 C5 -149.3(2) . . . . ?
C15 N3 C6 C7 29.6(3) . . . . ?
C15 N3 C9 C10 -139.9(2) . . . . ?
C15 N3 C9 C14 37.9(3) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C16 C15 C20 C19 -2.6(3) . . . . ?
C16 C17 C18 I2 178.55(16) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C20 2.1(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C20 C15 C16 C17 3.8(3) . . . . ?
I3 C32 C33 C34 177.93(16) . . . . ?
I4 C38 C39 C40 -179.33(15) . . . . ?
N5 C22 C23 C24 -128.1(2) . . . . ?
N5 C22 C23 C28 51.4(3) . . . . ?
N6 C26 C27 C28 175.4(2) . . . . ?
N6 C29 C30 C31 -178.9(2) . . . . ?
N6 C29 C34 C33 179.2(2) . . . . ?
N6 C35 C36 C37 -179.5(2) . . . . ?
N6 C35 C40 C39 179.76(19) . . . . ?
C21 N5 C22 C23 61.3(2) . . . . ?
C22 N5 C21 O2 12.6(3) . . . . ?
C22 N5 C21 N4 -170.02(19) . . . . ?
C22 C23 C24 C25 178.7(2) . . . . ?
C22 C23 C28 C27 -178.2(2) . . . . ?
C23 C24 C25 C26 -1.6(3) . . . . ?
C24 C23 C28 C27 1.4(3) . . . . ?
C24 C25 C26 N6 -174.9(2) . . . . ?
C24 C25 C26 C27 3.5(3) . . . . ?
C25 C26 C27 C28 -3.0(3) . . . . ?
C26 N6 C29 C30 45.7(3) . . . . ?
C26 N6 C29 C34 -133.7(2) . . . . ?
C26 N6 C35 C36 -145.1(2) . . . . ?
C26 N6 C35 C40 35.3(3) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C28 C23 C24 C25 -0.8(3) . . . . ?
C29 N6 C26 C25 43.5(3) . . . . ?
C29 N6 C26 C27 -134.9(2) . . . . ?
C29 N6 C35 C36 57.1(3) . . . . ?
C29 N6 C35 C40 -122.5(2) . . . . ?
C29 C30 C31 C32 -0.6(4) . . . . ?
C30 C29 C34 C33 -0.2(3) . . . . ?
C30 C31 C32 I3 -177.61(17) . . . . ?
C30 C31 C32 C33 0.4(3) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C29 0.0(3) . . . . ?
C34 C29 C30 C31 0.5(3) . . . . ?
C35 N6 C26 C25 -114.7(2) . . . . ?
C35 N6 C26 C27 66.9(3) . . . . ?
C35 N6 C29 C30 -156.3(2) . . . . ?
C35 N6 C29 C34 24.3(3) . . . . ?
C35 C36 C37 C38 -0.7(4) . . . . ?
C36 C35 C40 C39 0.2(3) . . . . ?
C36 C37 C38 I4 179.58(18) . . . . ?
C36 C37 C38 C39 1.1(3) . . . . ?
C37 C38 C39 C40 -0.8(3) . . . . ?
C38 C39 C40 C35 0.2(3) . . . . ?
C40 C35 C36 C37 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
