# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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 
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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_brnph3dmc_thiole
_database_code_depnum_ccdc_archive 'CCDC 2091812'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2019-04-03
_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            
'supramolecular host-guest complex with assembled bromotriphenylamine bis-urea macrocycle and 2,1,3-benzothiadiazole'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.5(C6 H4 N2 S)'
_chemical_formula_sum            'C45 H38 Br2 N7 O2 S0.50'
_chemical_formula_weight         884.67
_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'
Br Br -0.2901 2.4595 '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'
S S 0.1246 0.1234 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.8195(17)
_cell_length_b                   4.6302(5)
_cell_length_c                   26.812(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.182(2)
_cell_angle_gamma                90
_cell_volume                     1933.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6292
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.172
_cell_measurement_theta_min      2.616
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.409
_exptl_absorpt_coefficient_mu    2.174
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1304 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8925.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             902
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20014
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.210
_diffrn_reflns_theta_max         25.211
_diffrn_reflns_theta_min         1.308
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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                2726
_reflns_number_total             3477
_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         0.499
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+4.7414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0899
_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-H1 = N2-H2
 0.85 with sigma of 0.02
 S1S-N1S = S1S-N2S
 1.615 with sigma of 0.005
 N1S-C1S = N2S-C2S
 1.35 with sigma of 0.01
 S1S-C1S = S1S-C1S
 2.38 with sigma of 0.01
 N2S-C1S \\sim N1S-C2S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H1)
Uiso(C1S) = Uiso(C2S) = Uiso(C3S) = Uiso(C4S) = Uiso(C5S) = Uiso(C6S)
Uiso(N2S) = Uiso(N1S)
4. Others
 Fixed Sof: S1S(0.25) N1S(0.25) N2S(0.25) C1S(0.25) C2S(0.25) C3S(0.25)
 H3S(0.25) C4S(0.25) H4S(0.25) C5S(0.25) H5S(0.25) C6S(0.25) H6S(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
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), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S)
5.c Fitted hexagon refined as free rotating group:
 C1S(C2S,C3S,C4S,C5S,C6S)
;
_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
Br1 Br 1.17713(2) 0.86120(10) 0.72101(2) 0.03499(14) Uani 1 1 d . . . . .
O1 O 0.60127(15) 0.8863(6) 0.33827(10) 0.0342(6) Uani 1 1 d . . . . .
N1 N 0.53387(17) 0.4560(7) 0.31945(11) 0.0214(7) Uani 1 1 d D . . . .
H1 H 0.541(2) 0.278(4) 0.3220(13) 0.017(7) Uiso 1 1 d D . . . .
N2 N 0.67314(18) 0.4678(7) 0.35911(11) 0.0202(6) Uani 1 1 d D . . . .
H2 H 0.667(2) 0.289(4) 0.3581(13) 0.017(7) Uiso 1 1 d D . . . .
N3 N 0.82268(17) 0.6614(7) 0.59584(10) 0.0272(7) Uani 1 1 d . . . . .
C1 C 0.60233(19) 0.6193(8) 0.33891(12) 0.0189(7) Uani 1 1 d . . . . .
C2 C 0.7548(2) 0.6041(9) 0.37884(12) 0.0243(8) Uani 1 1 d . . . . .
H2A H 0.754719 0.801537 0.364649 0.029 Uiso 1 1 calc R . . . .
H2B H 0.801138 0.494022 0.367034 0.029 Uiso 1 1 calc R . . . .
C3 C 0.77470(19) 0.6234(8) 0.43597(12) 0.0219(7) Uani 1 1 d . . . . .
C4 C 0.8484(2) 0.5110(10) 0.46358(14) 0.0334(10) Uani 1 1 d . . . . .
H4 H 0.888869 0.420305 0.446390 0.040 Uiso 1 1 calc R . . . .
C5 C 0.8655(2) 0.5264(10) 0.51626(14) 0.0359(10) Uani 1 1 d . . . . .
H5 H 0.917545 0.448861 0.534427 0.043 Uiso 1 1 calc R . . . .
C6 C 0.8077(2) 0.6528(8) 0.54219(12) 0.0230(8) Uani 1 1 d . . . . .
C7 C 0.7343(2) 0.7721(10) 0.51480(15) 0.0403(11) Uani 1 1 d . . . . .
H7 H 0.694445 0.866935 0.531901 0.048 Uiso 1 1 calc R . . . .
C8 C 0.7183(3) 0.7546(10) 0.46274(15) 0.0454(12) Uani 1 1 d . . . . .
H8 H 0.666699 0.835549 0.444611 0.054 Uiso 1 1 calc R . . . .
C9 C 0.9067(2) 0.6994(8) 0.62361(12) 0.0215(8) Uani 1 1 d . . . . .
C10 C 0.9636(2) 0.8903(9) 0.60723(14) 0.0305(9) Uani 1 1 d . . . . .
H10 H 0.946630 0.992847 0.576397 0.037 Uiso 1 1 calc R . . . .
C11 C 1.0445(2) 0.9328(9) 0.63521(14) 0.0309(9) Uani 1 1 d . . . . .
H11 H 1.083292 1.062032 0.623472 0.037 Uiso 1 1 calc R . . . .
C12 C 1.0687(2) 0.7880(8) 0.68001(13) 0.0244(8) Uani 1 1 d . . . . .
C13 C 1.0140(2) 0.5917(8) 0.69670(13) 0.0257(8) Uani 1 1 d . . . . .
H13 H 1.031739 0.488019 0.727343 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9337(2) 0.5486(8) 0.66835(13) 0.0257(8) Uani 1 1 d . . . . .
H14 H 0.896004 0.413157 0.679580 0.031 Uiso 1 1 calc R . . . .
C15 C 0.7535(2) 0.6087(8) 0.62225(13) 0.0236(8) Uani 1 1 d . . . . .
C16 C 0.7470(2) 0.7586(9) 0.66587(13) 0.0285(9) Uani 1 1 d . . . . .
H16 H 0.788087 0.903510 0.677969 0.034 Uiso 1 1 calc R . . . .
C17 C 0.6810(2) 0.6997(9) 0.69221(13) 0.0273(9) Uani 1 1 d . . . . .
H17 H 0.677991 0.803394 0.722407 0.033 Uiso 1 1 calc R . . . .
C18 C 0.6200(2) 0.4940(8) 0.67544(13) 0.0231(8) Uani 1 1 d . . . . .
C19 C 0.6256(3) 0.3511(10) 0.63113(17) 0.0488(12) Uani 1 1 d . . . . .
H19 H 0.582979 0.212947 0.618110 0.059 Uiso 1 1 calc R . . . .
C20 C 0.6924(3) 0.4049(10) 0.60514(18) 0.0499(13) Uani 1 1 d . . . . .
H20 H 0.695776 0.299537 0.575162 0.060 Uiso 1 1 calc R . . . .
C21 C 0.5482(2) 0.4265(8) 0.70408(12) 0.0244(8) Uani 1 1 d . . . . .
H21A H 0.542917 0.214265 0.706773 0.029 Uiso 1 1 calc R . . . .
H21B H 0.563467 0.504766 0.738874 0.029 Uiso 1 1 calc R . . . .
S1S S 0.5241(5) 0.2499(17) 0.4563(2) 0.085(2) Uani 0.25 1 d D . P A -1
N1S N 0.4955(16) 0.344(2) 0.5090(5) 0.086(4) Uiso 0.25 1 d D . P A -1
N2S N 0.5340(13) 0.561(2) 0.4310(5) 0.086(4) Uiso 0.25 1 d D . P A -1
C1S C 0.4959(11) 0.6371(16) 0.5090(4) 0.052(2) Uiso 0.25 1 d D . P A -1
C2S C 0.5172(10) 0.753(2) 0.4650(4) 0.052(2) Uiso 0.25 1 d DG . P A -1
C3S C 0.5205(10) 1.051(2) 0.4590(5) 0.052(2) Uiso 0.25 1 d G . P A -1
H3S H 0.535066 1.129588 0.428941 0.063 Uiso 0.25 1 calc R . P A -1
C4S C 0.5026(10) 1.2326(17) 0.4970(6) 0.052(2) Uiso 0.25 1 d G . P A -1
H4S H 0.504945 1.436051 0.492956 0.063 Uiso 0.25 1 calc R . P A -1
C5S C 0.4814(10) 1.1169(18) 0.5410(5) 0.052(2) Uiso 0.25 1 d G . P A -1
H5S H 0.469161 1.241278 0.567029 0.063 Uiso 0.25 1 calc R . P A -1
C6S C 0.4780(11) 0.8191(19) 0.5470(4) 0.052(2) Uiso 0.25 1 d G . P A -1
H6S H 0.463497 0.740039 0.577087 0.063 Uiso 0.25 1 calc R . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.897(3) . ?
O1 C1 1.236(4) . ?
N1 H1 0.832(18) . ?
N1 C1 1.348(4) . ?
N1 C21 1.446(4) 3_666 ?
N2 H2 0.832(18) . ?
N2 C1 1.351(4) . ?
N2 C2 1.451(4) . ?
N3 C6 1.416(4) . ?
N3 C9 1.414(4) . ?
N3 C15 1.425(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.511(4) . ?
C3 C4 1.369(5) . ?
C3 C8 1.381(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.373(5) . ?
C6 C7 1.376(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(5) . ?
C9 C14 1.389(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.370(5) . ?
C12 C13 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.376(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(5) . ?
C15 C20 1.371(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(5) . ?
C18 C19 1.377(5) . ?
C18 C21 1.511(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(5) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
S1S N1S 1.617(5) . ?
S1S N2S 1.613(5) . ?
N1S C1S 1.357(9) . ?
N2S C2S 1.333(9) . ?
C1S C2S 1.3900 . ?
C1S C6S 1.3900 . ?
C2S C3S 1.3900 . ?
C3S H3S 0.9500 . ?
C3S C4S 1.3900 . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3900 . ?
C5S H5S 0.9500 . ?
C5S C6S 1.3900 . ?
C6S H6S 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
C1 N1 H1 116(2) . . ?
C1 N1 C21 123.8(3) . 3_666 ?
C21 N1 H1 121(2) 3_666 . ?
C1 N2 H2 115(2) . . ?
C1 N2 C2 122.8(3) . . ?
C2 N2 H2 122(2) . . ?
C6 N3 C15 119.7(3) . . ?
C9 N3 C6 120.7(3) . . ?
C9 N3 C15 119.4(3) . . ?
O1 C1 N1 123.2(3) . . ?
O1 C1 N2 122.2(3) . . ?
N1 C1 N2 114.6(3) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
N2 C2 C3 114.1(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 122.1(3) . . ?
C4 C3 C8 116.9(3) . . ?
C8 C3 C2 121.0(3) . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 N3 121.3(3) . . ?
C5 C6 C7 118.4(3) . . ?
C7 C6 N3 120.3(3) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.3(4) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 118.9 . . ?
C7 C8 C3 122.2(3) . . ?
C7 C8 H8 118.9 . . ?
C10 C9 N3 121.0(3) . . ?
C10 C9 C14 118.4(3) . . ?
C14 C9 N3 120.6(3) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 Br1 120.3(3) . . ?
C11 C12 C13 120.8(3) . . ?
C13 C12 Br1 118.9(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C16 C15 N3 120.9(3) . . ?
C20 C15 N3 120.6(3) . . ?
C20 C15 C16 118.4(3) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.5(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 C21 121.7(3) . . ?
C19 C18 C21 120.5(3) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(4) . . ?
C20 C19 H19 119.4 . . ?
C15 C20 C19 120.7(4) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N1 C21 C18 113.4(3) 3_666 . ?
N1 C21 H21A 108.9 3_666 . ?
N1 C21 H21B 108.9 3_666 . ?
C18 C21 H21A 108.9 . . ?
C18 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
N2S S1S N1S 101.0(6) . . ?
C1S N1S S1S 105.5(6) . . ?
C2S N2S S1S 105.1(6) . . ?
N1S C1S C2S 112.8(5) . . ?
N1S C1S C6S 127.2(5) . . ?
C2S C1S C6S 120.0 . . ?
N2S C2S C1S 115.6(6) . . ?
N2S C2S C3S 124.4(6) . . ?
C3S C2S C1S 120.0 . . ?
C2S C3S H3S 120.0 . . ?
C2S C3S C4S 120.0 . . ?
C4S C3S H3S 120.0 . . ?
C3S C4S H4S 120.0 . . ?
C5S C4S C3S 120.0 . . ?
C5S C4S H4S 120.0 . . ?
C4S C5S H5S 120.0 . . ?
C4S C5S C6S 120.0 . . ?
C6S C5S H5S 120.0 . . ?
C1S C6S H6S 120.0 . . ?
C5S C6S C1S 120.0 . . ?
C5S C6S H6S 120.0 . . ?

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 O1 0.832(18) 2.06(2) 2.857(4) 160(3) 1_545 yes
N2 H2 O1 0.832(18) 2.16(2) 2.938(4) 156(3) 1_545 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
Br1 C12 C13 C14 176.8(3) . . . . ?
N2 C2 C3 C4 124.1(4) . . . . ?
N2 C2 C3 C8 -55.4(5) . . . . ?
N3 C6 C7 C8 -177.7(4) . . . . ?
N3 C9 C10 C11 178.1(3) . . . . ?
N3 C9 C14 C13 -177.5(3) . . . . ?
N3 C15 C16 C17 -178.0(3) . . . . ?
N3 C15 C20 C19 179.3(4) . . . . ?
C1 N2 C2 C3 102.4(4) . . . . ?
C2 N2 C1 O1 -3.8(5) . . . . ?
C2 N2 C1 N1 175.8(3) . . . . ?
C2 C3 C4 C5 -179.1(4) . . . . ?
C2 C3 C8 C7 179.2(4) . . . . ?
C3 C4 C5 C6 0.9(7) . . . . ?
C4 C3 C8 C7 -0.3(7) . . . . ?
C4 C5 C6 N3 177.8(4) . . . . ?
C4 C5 C6 C7 -2.2(6) . . . . ?
C5 C6 C7 C8 2.3(7) . . . . ?
C6 N3 C9 C10 39.9(5) . . . . ?
C6 N3 C9 C14 -140.8(4) . . . . ?
C6 N3 C15 C16 -143.2(4) . . . . ?
C6 N3 C15 C20 37.6(5) . . . . ?
C6 C7 C8 C3 -1.1(7) . . . . ?
C8 C3 C4 C5 0.4(6) . . . . ?
C9 N3 C6 C5 36.2(6) . . . . ?
C9 N3 C6 C7 -143.8(4) . . . . ?
C9 N3 C15 C16 41.7(5) . . . . ?
C9 N3 C15 C20 -137.6(4) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C9 C14 C13 1.7(5) . . . . ?
C10 C11 C12 Br1 -176.2(3) . . . . ?
C10 C11 C12 C13 2.3(6) . . . . ?
C11 C12 C13 C14 -1.7(5) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C14 C9 C10 C11 -1.1(6) . . . . ?
C15 N3 C6 C5 -138.9(4) . . . . ?
C15 N3 C6 C7 41.1(5) . . . . ?
C15 N3 C9 C10 -145.0(4) . . . . ?
C15 N3 C9 C14 34.2(5) . . . . ?
C15 C16 C17 C18 -0.8(6) . . . . ?
C16 C15 C20 C19 0.0(7) . . . . ?
C16 C17 C18 C19 -1.0(6) . . . . ?
C16 C17 C18 C21 179.5(3) . . . . ?
C17 C18 C19 C20 2.3(7) . . . . ?
C17 C18 C21 N1 104.7(4) . . . 3_666 ?
C18 C19 C20 C15 -1.8(8) . . . . ?
C19 C18 C21 N1 -74.8(5) . . . 3_666 ?
C20 C15 C16 C17 1.3(6) . . . . ?
C21 N1 C1 O1 -0.2(5) 3_666 . . . ?
C21 N1 C1 N2 -179.8(3) 3_666 . . . ?
C21 C18 C19 C20 -178.2(4) . . . . ?
S1S N1S C1S C2S 1.9(16) . . . . ?
S1S N1S C1S C6S -178.1(9) . . . . ?
S1S N2S C2S C1S -1.0(16) . . . . ?
S1S N2S C2S C3S 178.3(8) . . . . ?
N1S S1S N2S C2S 1.9(16) . . . . ?
N1S C1S C2S N2S -0.6(17) . . . . ?
N1S C1S C2S C3S -180.0(12) . . . . ?
N1S C1S C6S C5S 180.0(14) . . . . ?
N2S S1S N1S C1S -2.3(16) . . . . ?
N2S C2S C3S C4S -179.3(16) . . . . ?
C1S C2S C3S C4S 0.0 . . . . ?
C2S C1S C6S C5S 0.0 . . . . ?
C2S C3S C4S C5S 0.0 . . . . ?
C3S C4S C5S C6S 0.0 . . . . ?
C4S C5S C6S C1S 0.0 . . . . ?
C6S C1S C2S N2S 179.4(14) . . . . ?
C6S C1S C2S C3S 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_brtpamc_clbq
_database_code_depnum_ccdc_archive 'CCDC 2091813'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_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            
'supramolecular host-guest complex with assembled bromotriphenylamine bis-urea macrocycle and 2,5-dichlorobenzoquinone'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, 0.31(C6 H2 Cl2 O2)'
_chemical_formula_sum            'C43.88 H36.62 Br2 Cl0.62 N6 O2.62'
_chemical_formula_weight         871.89
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.782(5)
_cell_length_b                   4.6143(15)
_cell_length_c                   26.780(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.354(5)
_cell_angle_gamma                90
_cell_volume                     1918.5(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2779
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.032
_cell_measurement_theta_min      2.200
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.488
_exptl_absorpt_coefficient_mu    2.205
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6584
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1360 before and 0.0535 after correction. 
The Ratio of minimum to maximum transmission is 0.8835. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             887
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1100
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            14472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.080
_diffrn_reflns_theta_max         25.080
_diffrn_reflns_theta_min         2.200
_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                2292
_reflns_number_total             3409
_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         0.785
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+2.1342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1137
_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
 O1S-C2S
 1.22 with sigma of 0.015
 C2S-C1S
 1.496 with sigma of 0.015
 C3S_$2-C1S
 1.476 with sigma of 0.01
 C3S-C2S
 1.34 with sigma of 0.015
 Cl1S-C1S
 1.71 with sigma of 0.015
 N1-H1 = N2-H2
 0.87 with sigma of 0.02
3. Others
 Sof(Cl1S)=Sof(O1S)=Sof(C1S)=Sof(C2S)=Sof(C3S)=Sof(H3S)=FVAR(1)
4.a Riding coordinates:
 C3S(H3S)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
4.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)
;
_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
Br1 Br 1.17601(3) 0.86151(13) 0.72153(2) 0.03144(18) Uani 1 1 d . . . . .
O1 O 0.60263(19) 0.8874(8) 0.33635(12) 0.0258(8) Uani 1 1 d . . . . .
N1 N 0.5339(2) 0.4585(9) 0.31863(15) 0.0221(10) Uani 1 1 d D . . . .
H1 H 0.537(3) 0.276(5) 0.3238(16) 0.009(12) Uiso 1 1 d D . . . .
N2 N 0.6741(2) 0.4688(9) 0.35794(14) 0.0172(9) Uani 1 1 d D . . . .
H2 H 0.669(3) 0.284(5) 0.3568(18) 0.021(15) Uiso 1 1 d D . . . .
N3 N 0.8211(2) 0.6720(10) 0.59514(13) 0.0254(10) Uani 1 1 d . . . . .
C1 C 0.6030(3) 0.6206(12) 0.33760(15) 0.0164(10) Uani 1 1 d . . . . .
C2 C 0.7558(3) 0.6067(12) 0.37802(15) 0.0198(11) Uani 1 1 d . . . . .
H2A H 0.755854 0.804233 0.363615 0.024 Uiso 1 1 calc R . . . .
H2B H 0.802600 0.495782 0.366679 0.024 Uiso 1 1 calc R . . . .
C3 C 0.7747(2) 0.6277(11) 0.43502(15) 0.0160(10) Uani 1 1 d . . . . .
C4 C 0.8488(3) 0.5166(12) 0.46294(17) 0.0247(12) Uani 1 1 d . . . . .
H4 H 0.889818 0.427546 0.445926 0.030 Uiso 1 1 calc R . . . .
C5 C 0.8653(3) 0.5315(12) 0.51601(16) 0.0246(12) Uani 1 1 d . . . . .
H5 H 0.916988 0.451916 0.534631 0.030 Uiso 1 1 calc R . . . .
C6 C 0.8069(3) 0.6611(11) 0.54112(16) 0.0232(11) Uani 1 1 d . . . . .
C7 C 0.7335(3) 0.7795(12) 0.51326(17) 0.0325(14) Uani 1 1 d . . . . .
H7 H 0.693484 0.875373 0.530178 0.039 Uiso 1 1 calc R . . . .
C8 C 0.7172(3) 0.7609(12) 0.46111(17) 0.0305(13) Uani 1 1 d . . . . .
H8 H 0.665453 0.840953 0.442651 0.037 Uiso 1 1 calc R . . . .
C9 C 0.9052(3) 0.7077(11) 0.62307(16) 0.0225(12) Uani 1 1 d . . . . .
C10 C 0.9626(3) 0.8942(13) 0.60719(18) 0.0358(14) Uani 1 1 d . . . . .
H10 H 0.946223 0.994988 0.576019 0.043 Uiso 1 1 calc R . . . .
C11 C 1.0431(3) 0.9385(12) 0.63526(18) 0.0339(14) Uani 1 1 d . . . . .
H11 H 1.081897 1.070070 0.623941 0.041 Uiso 1 1 calc R . . . .
C12 C 1.0668(3) 0.7895(11) 0.68014(16) 0.0214(12) Uani 1 1 d . . . . .
C13 C 1.0124(3) 0.5974(12) 0.69646(16) 0.0272(13) Uani 1 1 d . . . . .
H13 H 1.029869 0.495217 0.727389 0.033 Uiso 1 1 calc R . . . .
C14 C 0.9319(3) 0.5519(12) 0.66790(17) 0.0275(13) Uani 1 1 d . . . . .
H14 H 0.894273 0.414013 0.678715 0.033 Uiso 1 1 calc R . . . .
C15 C 0.7519(3) 0.6149(12) 0.62116(16) 0.0229(11) Uani 1 1 d . . . . .
C16 C 0.7462(3) 0.7619(12) 0.66528(18) 0.0289(13) Uani 1 1 d . . . . .
H16 H 0.787548 0.906211 0.677652 0.035 Uiso 1 1 calc R . . . .
C17 C 0.6806(3) 0.7005(12) 0.69161(18) 0.0266(13) Uani 1 1 d . . . . .
H17 H 0.678193 0.802333 0.722158 0.032 Uiso 1 1 calc R . . . .
C18 C 0.6194(3) 0.4977(11) 0.67484(16) 0.0219(11) Uani 1 1 d . . . . .
C19 C 0.6242(4) 0.3554(13) 0.62992(18) 0.0403(14) Uani 1 1 d . . . . .
H19 H 0.581461 0.216713 0.616879 0.048 Uiso 1 1 calc R . . . .
C20 C 0.6904(3) 0.4121(12) 0.60373(18) 0.0362(14) Uani 1 1 d . . . . .
H20 H 0.693242 0.309128 0.573355 0.043 Uiso 1 1 calc R . . . .
C21 C 0.5486(3) 0.4241(12) 0.70373(17) 0.0258(12) Uani 1 1 d . . . . .
H21A H 0.543717 0.210677 0.705663 0.031 Uiso 1 1 calc R . . . .
H21B H 0.564649 0.498421 0.738843 0.031 Uiso 1 1 calc R . . . .
Cl1S Cl 0.5204(3) 1.1564(12) 0.47528(18) 0.0420(14) Uiso 0.312(3) 1 d D . P . .
O1S O 0.4720(7) 0.901(3) 0.5649(4) 0.037(3) Uiso 0.312(3) 1 d D . P . .
C1S C 0.5103(9) 0.801(2) 0.4890(5) 0.025(4) Uiso 0.312(3) 1 d D . P . .
C2S C 0.4823(10) 0.704(3) 0.5369(5) 0.029(4) Uiso 0.312(3) 1 d D . P . .
C3S C 0.4757(9) 0.420(3) 0.5468(5) 0.026(4) Uiso 0.312(3) 1 d D . P . .
H3S H 0.460475 0.362603 0.578400 0.031 Uiso 0.312(3) 1 d R . P . .


_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
Br1 C12 1.903(4) . ?
O1 C1 1.232(6) . ?
N1 H1 0.854(19) . ?
N1 C1 1.344(6) . ?
N1 C21 1.438(6) 3_666 ?
N2 H2 0.857(19) . ?
N2 C1 1.351(6) . ?
N2 C2 1.452(6) . ?
N3 C6 1.425(5) . ?
N3 C9 1.411(6) . ?
N3 C15 1.422(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.505(6) . ?
C3 C4 1.369(6) . ?
C3 C8 1.385(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(6) . ?
C6 C7 1.374(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(7) . ?
C9 C14 1.398(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(7) . ?
C12 C13 1.360(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(6) . ?
C15 C20 1.368(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(6) . ?
C17 H17 0.9500 . ?
C17 C18 1.362(7) . ?
C18 C19 1.385(7) . ?
C18 C21 1.507(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(7) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
Cl1S C1S 1.693(11) . ?
O1S C2S 1.207(12) . ?
C1S C2S 1.499(12) . ?
C1S C3S 1.442(9) 3_666 ?
C2S C3S 1.345(13) . ?
C3S H3S 0.9582 . ?

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 118(3) . . ?
C1 N1 C21 124.1(4) . 3_666 ?
C21 N1 H1 117(3) 3_666 . ?
C1 N2 H2 116(3) . . ?
C1 N2 C2 122.7(4) . . ?
C2 N2 H2 121(3) . . ?
C9 N3 C6 120.2(3) . . ?
C9 N3 C15 119.6(3) . . ?
C15 N3 C6 119.8(4) . . ?
O1 C1 N1 123.1(4) . . ?
O1 C1 N2 121.9(4) . . ?
N1 C1 N2 115.0(5) . . ?
N2 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
N2 C2 C3 113.9(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 121.6(4) . . ?
C4 C3 C8 117.6(4) . . ?
C8 C3 C2 120.8(4) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(4) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 N3 121.1(4) . . ?
C5 C6 C7 118.8(4) . . ?
C7 C6 N3 120.1(4) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.8(4) . . ?
C8 C7 H7 119.6 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.3(4) . . ?
C7 C8 H8 119.3 . . ?
C10 C9 N3 121.3(4) . . ?
C10 C9 C14 118.3(4) . . ?
C14 C9 N3 120.3(4) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.5(5) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.0(5) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 Br1 119.8(4) . . ?
C13 C12 Br1 119.0(3) . . ?
C13 C12 C11 121.2(4) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C16 C15 N3 120.2(4) . . ?
C20 C15 N3 121.3(4) . . ?
C20 C15 C16 118.5(4) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(4) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 C19 117.7(4) . . ?
C17 C18 C21 122.2(4) . . ?
C19 C18 C21 120.1(5) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 121.0(5) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 C19 120.7(5) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N1 C21 C18 113.6(4) 3_666 . ?
N1 C21 H21A 108.8 3_666 . ?
N1 C21 H21B 108.8 3_666 . ?
C18 C21 H21A 108.8 . . ?
C18 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C2S C1S Cl1S 122.0(10) . . ?
C3S C1S Cl1S 120.6(10) 3_666 . ?
C3S C1S C2S 117.4(10) 3_666 . ?
O1S C2S C1S 113.4(12) . . ?
O1S C2S C3S 126.0(13) . . ?
C3S C2S C1S 120.4(11) . . ?
Cl1S C3S H3S 122.8 3_676 . ?
C1S C3S Cl1S 117.9(9) 3_666 3_676 ?
C1S C3S H3S 119.1 3_666 . ?
C2S C3S C1S 122.1(12) . 3_666 ?
C2S C3S H3S 118.8 . . ?

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 O1 0.854(19) 2.07(3) 2.857(6) 153(4) 1_545 yes
N2 H2 O1 0.857(19) 2.13(3) 2.927(5) 154(4) 1_545 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
Br1 C12 C13 C14 177.4(4) . . . . ?
N2 C2 C3 C4 124.5(5) . . . . ?
N2 C2 C3 C8 -55.5(7) . . . . ?
N3 C6 C7 C8 -177.4(5) . . . . ?
N3 C9 C10 C11 177.3(5) . . . . ?
N3 C9 C14 C13 -176.8(4) . . . . ?
N3 C15 C16 C17 -177.9(4) . . . . ?
N3 C15 C20 C19 178.9(5) . . . . ?
C1 N2 C2 C3 101.6(5) . . . . ?
C2 N2 C1 O1 -2.4(6) . . . . ?
C2 N2 C1 N1 177.0(4) . . . . ?
C2 C3 C4 C5 -178.7(5) . . . . ?
C2 C3 C8 C7 179.5(5) . . . . ?
C3 C4 C5 C6 -0.4(8) . . . . ?
C4 C3 C8 C7 -0.4(8) . . . . ?
C4 C5 C6 N3 178.2(5) . . . . ?
C4 C5 C6 C7 -1.3(8) . . . . ?
C5 C6 C7 C8 2.1(8) . . . . ?
C6 N3 C9 C10 40.3(7) . . . . ?
C6 N3 C9 C14 -139.6(5) . . . . ?
C6 N3 C15 C16 -145.1(5) . . . . ?
C6 N3 C15 C20 35.9(7) . . . . ?
C6 C7 C8 C3 -1.2(9) . . . . ?
C8 C3 C4 C5 1.2(8) . . . . ?
C9 N3 C6 C5 35.8(7) . . . . ?
C9 N3 C6 C7 -144.7(5) . . . . ?
C9 N3 C15 C16 41.8(7) . . . . ?
C9 N3 C15 C20 -137.3(5) . . . . ?
C9 C10 C11 C12 0.7(8) . . . . ?
C10 C9 C14 C13 3.3(7) . . . . ?
C10 C11 C12 Br1 -176.8(4) . . . . ?
C10 C11 C12 C13 1.0(8) . . . . ?
C11 C12 C13 C14 -0.4(8) . . . . ?
C12 C13 C14 C9 -1.7(7) . . . . ?
C14 C9 C10 C11 -2.8(8) . . . . ?
C15 N3 C6 C5 -137.3(5) . . . . ?
C15 N3 C6 C7 42.2(7) . . . . ?
C15 N3 C9 C10 -146.6(5) . . . . ?
C15 N3 C9 C14 33.5(7) . . . . ?
C15 C16 C17 C18 -0.8(8) . . . . ?
C16 C15 C20 C19 -0.2(8) . . . . ?
C16 C17 C18 C19 -0.7(8) . . . . ?
C16 C17 C18 C21 178.7(5) . . . . ?
C17 C18 C19 C20 1.7(8) . . . . ?
C17 C18 C21 N1 105.0(5) . . . 3_666 ?
C18 C19 C20 C15 -1.3(9) . . . . ?
C19 C18 C21 N1 -75.7(6) . . . 3_666 ?
C20 C15 C16 C17 1.2(8) . . . . ?
C21 N1 C1 O1 -2.0(7) 3_666 . . . ?
C21 N1 C1 N2 178.6(4) 3_666 . . . ?
C21 C18 C19 C20 -177.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
####################################################################### 
# 
# 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_i_tpa_me
_database_code_depnum_ccdc_archive 'CCDC 2091814'
loop_
_audit_author_name
_audit_author_address
'Mark D. Smith'
;University of South Carolina
United States of America
;
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_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            
'supramolecular host-guest complex with assembled bromotriphenylamine bis-urea macrocycle and iodine'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H36 Br2 N6 O2, I0.68'
_chemical_formula_sum            'C42 H36 Br2 I0.69 N6 O2'
_chemical_formula_weight         903.51
_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'
Br Br -0.2901 2.4595 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.871(3)
_cell_length_b                   4.6048(10)
_cell_length_c                   26.839(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.177(4)
_cell_angle_gamma                90
_cell_volume                     1930.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9903
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.366
_cell_measurement_theta_min      2.188
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.371
_exptl_absorpt_coefficient_mu    2.692
_exptl_absorpt_correction_T_max  0.6198
_exptl_absorpt_correction_T_min  0.5033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1559 before and 0.0598 after correction. 
The Ratio of minimum to maximum transmission is 0.8120. 
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             905
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            32724
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         1.304
_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 0.994
_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                3106
_reflns_number_total             3965
_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         0.784
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0016(3)
_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   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3965
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.123
_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)+(0.0260P)²+7.5619P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          SQUEEZE
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
2.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)
;
_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
Br1 Br 1.17525(3) 0.86665(12) 0.72120(2) 0.03190(16) Uani 1 1 d . . . . .
O1 O 0.60172(18) 0.8860(7) 0.33709(11) 0.0286(7) Uani 1 1 d . . . . .
N1 N 0.5332(2) 0.4538(9) 0.31916(14) 0.0246(8) Uani 1 1 d . . . . .
H1 H 0.538(3) 0.274(10) 0.3224(15) 0.013(11) Uiso 1 1 d . . . . .
N2 N 0.6732(2) 0.4644(9) 0.35814(12) 0.0209(7) Uani 1 1 d . . . . .
H2 H 0.670(3) 0.288(11) 0.3582(16) 0.019(12) Uiso 1 1 d . . . . .
N3 N 0.8218(2) 0.6645(9) 0.59522(12) 0.0295(9) Uani 1 1 d . . . . .
C1 C 0.6024(2) 0.6190(10) 0.33821(12) 0.0194(8) Uani 1 1 d . . . . .
C2 C 0.7546(2) 0.6028(10) 0.37797(13) 0.0229(9) Uani 1 1 d . . . . .
H2A H 0.754467 0.801065 0.363701 0.027 Uiso 1 1 calc R . . . .
H2B H 0.801017 0.492269 0.366322 0.027 Uiso 1 1 calc R . . . .
C3 C 0.7740(2) 0.6229(10) 0.43487(13) 0.0214(8) Uani 1 1 d . . . . .
C4 C 0.8495(2) 0.5180(10) 0.46273(14) 0.0233(9) Uani 1 1 d . . . . .
H4 H 0.890782 0.433154 0.445486 0.028 Uiso 1 1 calc R . . . .
C5 C 0.8667(3) 0.5333(10) 0.51521(15) 0.0262(9) Uani 1 1 d . . . . .
H5 H 0.919152 0.459357 0.533355 0.031 Uiso 1 1 calc R . . . .
C6 C 0.8072(2) 0.6570(10) 0.54130(13) 0.0253(9) Uani 1 1 d . . . . .
C7 C 0.7317(3) 0.7695(11) 0.51371(15) 0.0293(10) Uani 1 1 d . . . . .
H7 H 0.691122 0.859256 0.530873 0.035 Uiso 1 1 calc R . . . .
C8 C 0.7154(3) 0.7512(10) 0.46152(15) 0.0261(9) Uani 1 1 d . . . . .
H8 H 0.663355 0.827454 0.443300 0.031 Uiso 1 1 calc R . . . .
C9 C 0.9057(2) 0.7025(10) 0.62297(13) 0.0229(9) Uani 1 1 d . . . . .
C10 C 0.9627(3) 0.8950(10) 0.60665(15) 0.0294(10) Uani 1 1 d . . . . .
H10 H 0.945940 0.998348 0.575869 0.035 Uiso 1 1 calc R . . . .
C11 C 1.0436(3) 0.9374(10) 0.63479(15) 0.0296(10) Uani 1 1 d . . . . .
H11 H 1.082649 1.066320 0.623132 0.036 Uiso 1 1 calc R . . . .
C12 C 1.0670(2) 0.7916(10) 0.67964(14) 0.0240(9) Uani 1 1 d . . . . .
C13 C 1.0130(2) 0.5946(10) 0.69653(14) 0.0259(9) Uani 1 1 d . . . . .
H13 H 1.030782 0.491860 0.727289 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9324(2) 0.5486(10) 0.66793(14) 0.0252(10) Uani 1 1 d . . . . .
H14 H 0.894953 0.411434 0.678983 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7530(2) 0.6115(10) 0.62156(14) 0.0235(9) Uani 1 1 d . . . . .
C16 C 0.7476(2) 0.7603(10) 0.66561(14) 0.0258(9) Uani 1 1 d . . . . .
H16 H 0.789147 0.903842 0.677864 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6815(2) 0.7008(10) 0.69223(14) 0.0240(9) Uani 1 1 d . . . . .
H17 H 0.678909 0.802532 0.722713 0.029 Uiso 1 1 calc R . . . .
C18 C 0.6200(2) 0.4966(10) 0.67482(14) 0.0231(9) Uani 1 1 d . . . . .
C19 C 0.6235(3) 0.3549(11) 0.62968(15) 0.0312(10) Uani 1 1 d . . . . .
H19 H 0.579954 0.219851 0.616482 0.037 Uiso 1 1 calc R . . . .
C20 C 0.6901(3) 0.4087(11) 0.60352(15) 0.0318(10) Uani 1 1 d . . . . .
H20 H 0.692596 0.306164 0.573108 0.038 Uiso 1 1 calc R . . . .
C21 C 0.5487(2) 0.4268(10) 0.70408(15) 0.0269(10) Uani 1 1 d . . . . .
H21A H 0.543400 0.213352 0.706603 0.032 Uiso 1 1 calc R . . . .
H21B H 0.564362 0.504683 0.738875 0.032 Uiso 1 1 calc R . . . .
I1 I 0.5070(2) 0.2172(11) 0.46959(15) 0.0531(13) Uiso 0.153(3) 1 d . . . . .
I2 I 0.4986(3) 0.9322(8) 0.50068(19) 0.0345(14) Uiso 0.0804(12) 1 d . . . . .
I3 I 0.4871(6) 0.573(5) 0.5147(4) 0.040(4) Uiso 0.045(4) 1 d . . . . .
I4 I 0.4920(6) 0.700(3) 0.5056(5) 0.019(4) Uiso 0.038(3) 1 d . . . . .
I5 I 0.5231(10) 0.331(5) 0.4778(7) 0.014(7) Uiso 0.026(4) 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.908(4) . ?
O1 C1 1.230(5) . ?
N1 H1 0.83(4) . ?
N1 C1 1.360(5) . ?
N1 C21 1.447(5) 3_666 ?
N2 H2 0.82(5) . ?
N2 C1 1.358(5) . ?
N2 C2 1.454(5) . ?
N3 C6 1.425(5) . ?
N3 C9 1.417(5) . ?
N3 C15 1.423(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.507(5) . ?
C3 C4 1.382(5) . ?
C3 C8 1.400(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(6) . ?
C6 C7 1.392(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(6) . ?
C9 C14 1.399(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.371(6) . ?
C12 C13 1.378(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(6) . ?
C15 C20 1.391(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.398(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.376(6) . ?
C18 C19 1.386(6) . ?
C18 C21 1.521(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(6) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
I1 I1 2.616(8) 3_656 ?
I1 I1 3.102(11) 3_666 ?
I1 I2 1.069(5) 3_666 ?
I1 I2 1.573(6) 1_545 ?
I1 I3 1.05(2) 3_666 ?
I1 I3 2.09(2) . ?
I1 I4 0.766(12) 3_666 ?
I1 I4 2.596(16) 1_545 ?
I1 I4 2.452(13) . ?
I1 I5 0.61(2) . ?
I1 I5 2.97(2) 3_656 ?
I1 I5 2.61(3) 3_666 ?
I2 I2 0.628(7) 3_676 ?
I2 I3 2.38(2) 3_666 ?
I2 I3 2.33(2) 3_676 ?
I2 I3 1.71(2) . ?
I2 I4 2.921(13) 3_666 ?
I2 I4 1.711(14) 3_676 ?
I2 I4 1.084(14) . ?
I2 I5 1.99(2) 1_565 ?
I2 I5 1.41(2) 3_666 ?
I2 I5 2.88(3) . ?
I3 I3 1.16(4) 3_666 ?
I3 I4 1.43(3) 3_666 ?
I3 I4 0.646(16) . ?
I3 I5 1.66(4) . ?
I3 I5 0.526(18) 3_666 ?
I4 I4 2.79(3) 3_676 ?
I4 I4 1.89(2) 3_666 ?
I4 I5 1.96(3) . ?
I4 I5 0.562(14) 3_666 ?
I5 I5 2.17(5) 3_666 ?

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 118(3) . . ?
C1 N1 C21 123.7(4) . 3_666 ?
C21 N1 H1 119(3) 3_666 . ?
C1 N2 H2 119(3) . . ?
C1 N2 C2 122.3(4) . . ?
C2 N2 H2 119(3) . . ?
C9 N3 C6 120.4(3) . . ?
C9 N3 C15 119.5(3) . . ?
C15 N3 C6 119.9(3) . . ?
O1 C1 N1 123.1(4) . . ?
O1 C1 N2 122.5(4) . . ?
N2 C1 N1 114.4(4) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 H2B 108.7 . . ?
N2 C2 C3 114.0(3) . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 C8 117.5(3) . . ?
C8 C3 C2 120.5(3) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(4) . . ?
C6 C5 H5 119.9 . . ?
C5 C6 N3 121.1(4) . . ?
C7 C6 N3 120.1(4) . . ?
C7 C6 C5 118.7(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 H7 119.8 . . ?
C3 C8 H8 119.3 . . ?
C7 C8 C3 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C10 C9 N3 121.1(4) . . ?
C10 C9 C14 118.6(4) . . ?
C14 C9 N3 120.3(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 Br1 120.0(3) . . ?
C11 C12 C13 121.6(4) . . ?
C13 C12 Br1 118.3(3) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 119.0(4) . . ?
C14 C13 H13 120.5 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 N3 120.6(4) . . ?
C16 C15 C20 118.8(4) . . ?
C20 C15 N3 120.6(4) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 C21 121.1(4) . . ?
C19 C18 C21 120.0(4) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.5(4) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 120.5(4) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N1 C21 C18 113.0(3) 3_666 . ?
N1 C21 H21A 109.0 3_666 . ?
N1 C21 H21B 109.0 3_666 . ?
C18 C21 H21A 109.0 . . ?
C18 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?

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 O1 0.83(4) 2.06(5) 2.840(5) 156(4) 1_545 yes
N2 H2 O1 0.82(5) 2.17(5) 2.911(5) 151(4) 1_545 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
Br1 C12 C13 C14 176.8(3) . . . . ?
N2 C2 C3 C4 126.2(4) . . . . ?
N2 C2 C3 C8 -54.0(6) . . . . ?
N3 C6 C7 C8 -177.1(4) . . . . ?
N3 C9 C10 C11 178.0(4) . . . . ?
N3 C9 C14 C13 -177.0(4) . . . . ?
N3 C15 C16 C17 -177.9(4) . . . . ?
N3 C15 C20 C19 179.2(4) . . . . ?
C1 N2 C2 C3 101.7(4) . . . . ?
C2 N2 C1 O1 -2.4(6) . . . . ?
C2 N2 C1 N1 176.9(3) . . . . ?
C2 C3 C4 C5 -179.1(4) . . . . ?
C2 C3 C8 C7 179.4(4) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C3 C8 C7 -0.8(7) . . . . ?
C4 C5 C6 N3 177.4(4) . . . . ?
C4 C5 C6 C7 -1.4(7) . . . . ?
C5 C6 C7 C8 1.7(7) . . . . ?
C6 N3 C9 C10 39.8(6) . . . . ?
C6 N3 C9 C14 -141.0(4) . . . . ?
C6 N3 C15 C16 -143.9(4) . . . . ?
C6 N3 C15 C20 36.2(6) . . . . ?
C6 C7 C8 C3 -0.6(7) . . . . ?
C8 C3 C4 C5 1.1(7) . . . . ?
C9 N3 C6 C5 35.0(7) . . . . ?
C9 N3 C6 C7 -146.2(4) . . . . ?
C9 N3 C15 C16 40.8(6) . . . . ?
C9 N3 C15 C20 -139.1(4) . . . . ?
C9 C10 C11 C12 -1.2(7) . . . . ?
C10 C9 C14 C13 2.2(6) . . . . ?
C10 C11 C12 Br1 -175.8(3) . . . . ?
C10 C11 C12 C13 2.6(7) . . . . ?
C11 C12 C13 C14 -1.6(6) . . . . ?
C12 C13 C14 C9 -0.8(6) . . . . ?
C14 C9 C10 C11 -1.2(6) . . . . ?
C15 N3 C6 C5 -140.2(5) . . . . ?
C15 N3 C6 C7 38.6(7) . . . . ?
C15 N3 C9 C10 -144.9(4) . . . . ?
C15 N3 C9 C14 34.2(6) . . . . ?
C15 C16 C17 C18 -0.9(6) . . . . ?
C16 C15 C20 C19 -0.6(7) . . . . ?
C16 C17 C18 C19 -1.5(6) . . . . ?
C16 C17 C18 C21 178.9(4) . . . . ?
C17 C18 C19 C20 2.8(7) . . . . ?
C17 C18 C21 N1 105.8(4) . . . 3_666 ?
C18 C19 C20 C15 -1.8(7) . . . . ?
C19 C18 C21 N1 -73.8(5) . . . 3_666 ?
C20 C15 C16 C17 2.0(6) . . . . ?
C21 N1 C1 O1 -0.4(6) 3_666 . . . ?
C21 N1 C1 N2 -179.7(3) 3_666 . . . ?
C21 C18 C19 C20 -177.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
