# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_mcg13116
_database_code_depnum_ccdc_archive 'CCDC 2010995'
loop_
_audit_author_name
_audit_author_address
'Michael Sinnwell'
;Pacific Northwest National Lab
United States of America
;
_audit_update_record             
;
2020-06-20 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-06-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            TPCB
_chemical_name_systematic        rctt-tetrakis-(5-pyrimidyl)-cyclobutane
_chemical_formula_moiety         'C20 H16 N8'
_chemical_formula_sum            'C20 H16 N8'
_chemical_formula_weight         368.41
_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'
N N 0.0061 0.0033 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.6660(16)
_cell_length_b                   7.1513(7)
_cell_length_c                   17.0738(17)
_cell_angle_alpha                90
_cell_angle_beta                 111.938(5)
_cell_angle_gamma                90
_cell_volume                     1774.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3010
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9868
_exptl_absorpt_correction_T_min  0.8276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_preparation       'solvent evaporation'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         3.015
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1375
_reflns_number_total             1618
_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       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+1.9570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1400
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid body (RIGU) restrains
 C9A, C9B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C10A, C10B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Same fragment restrains
{C9A, C10A} sigma for 1-2: 0.02, 1-3: 0.04
{C9A, C10A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{C9B, C10B}
4. Others
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(H10B)=1-FVAR(1)
 Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9A(H9A), C10A(H10A), C9B(H9B), C10B(H10B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C8(H8)
;
_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
N1 N 0.16075(15) 0.5780(3) 0.24065(12) 0.0662(6) Uani 1 1 d . . . . .
N2 N 0.11660(17) 0.7293(3) 0.34278(15) 0.0763(7) Uani 1 1 d . . . . .
N3 N 0.55944(16) 0.3423(3) 0.65873(15) 0.0757(7) Uani 1 1 d . . . . .
N4 N 0.55005(15) 0.2264(4) 0.52660(14) 0.0771(7) Uani 1 1 d . . . . .
C1 C 0.12197(18) 0.7134(4) 0.26703(17) 0.0686(7) Uani 1 1 d . . . . .
H1 H 0.095270 0.808899 0.228706 0.082 Uiso 1 1 calc R U . . .
C2 C 0.15477(19) 0.5887(4) 0.39604(16) 0.0658(7) Uani 1 1 d . . . . .
H2 H 0.151526 0.591733 0.449315 0.079 Uiso 1 1 calc R U . . .
C3 C 0.19832(14) 0.4408(3) 0.37627(14) 0.0507(5) Uani 1 1 d . . . . .
C4 C 0.19799(16) 0.4434(4) 0.29611(15) 0.0588(6) Uani 1 1 d . . . . .
H4 H 0.225716 0.344129 0.279479 0.071 Uiso 1 1 calc R U . . .
C5 C 0.59460(17) 0.2784(4) 0.60472(17) 0.0675(7) Uani 1 1 d . . . . .
H5 H 0.658394 0.269286 0.624509 0.081 Uiso 1 1 calc R U . . .
C6 C 0.46932(18) 0.3551(4) 0.62960(17) 0.0706(7) Uani 1 1 d . . . . .
H6 H 0.442044 0.399223 0.665929 0.085 Uiso 1 1 calc R U . . .
C7 C 0.41294(15) 0.3077(3) 0.54916(14) 0.0547(6) Uani 1 1 d . . . . .
C8 C 0.45823(18) 0.2418(4) 0.49939(16) 0.0715(8) Uani 1 1 d . . . . .
H8 H 0.423424 0.206249 0.444236 0.086 Uiso 1 1 calc R U . . .
C9A C 0.24479(17) 0.2806(3) 0.43444(15) 0.0449(7) Uani 0.887(6) 1 d D . P A 1
H9A H 0.276830 0.199599 0.407986 0.054 Uiso 0.887(6) 1 calc R U P A 1
C10A C 0.31092(17) 0.3406(3) 0.52393(15) 0.0455(7) Uani 0.887(6) 1 d D . P A 1
H10A H 0.300691 0.473183 0.531978 0.055 Uiso 0.887(6) 1 calc R U P A 1
C9B C 0.3084(10) 0.226(2) 0.4804(10) 0.039(5) Uani 0.113(6) 1 d D . P A 2
H9B H 0.306829 0.183761 0.425270 0.047 Uiso 0.113(6) 1 calc R U P A 2
C10B C 0.2477(11) 0.396(2) 0.4790(10) 0.037(5) Uani 0.113(6) 1 d D . P A 2
H10B H 0.280582 0.501461 0.513565 0.045 Uiso 0.113(6) 1 calc R U P A 2


_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
N1 C1 1.309(3) . ?
N1 C4 1.323(3) . ?
N2 C1 1.332(3) . ?
N2 C2 1.338(3) . ?
N3 C5 1.320(3) . ?
N3 C6 1.313(3) . ?
N4 C5 1.307(3) . ?
N4 C8 1.341(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 C4 1.367(3) . ?
C3 C9A 1.513(3) . ?
C3 C10B 1.663(16) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.369(3) . ?
C7 C8 1.378(4) . ?
C7 C10A 1.510(3) . ?
C7 C9B 1.722(15) . ?
C8 H8 0.9300 . ?
C9A H9A 0.9800 . ?
C9A C10A 1.575(3) 7_556 ?
C9A C10A 1.552(3) . ?
C10A H10A 0.9800 . ?
C9B H9B 0.9800 . ?
C9B C10B 1.535(16) . ?
C9B C10B 1.57(2) 7_556 ?
C10B H10B 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 C4 115.4(2) . . ?
C1 N2 C2 114.9(2) . . ?
C6 N3 C5 115.4(2) . . ?
C5 N4 C8 115.1(2) . . ?
N1 C1 N2 127.1(2) . . ?
N1 C1 H1 116.5 . . ?
N2 C1 H1 116.5 . . ?
N2 C2 H2 118.3 . . ?
N2 C2 C3 123.4(2) . . ?
C3 C2 H2 118.3 . . ?
C2 C3 C9A 125.9(2) . . ?
C2 C3 C10B 88.2(5) . . ?
C4 C3 C2 114.9(2) . . ?
C4 C3 C9A 119.2(2) . . ?
C4 C3 C10B 152.2(6) . . ?
N1 C4 C3 124.2(2) . . ?
N1 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
N3 C5 H5 116.3 . . ?
N4 C5 N3 127.5(2) . . ?
N4 C5 H5 116.3 . . ?
N3 C6 H6 117.9 . . ?
N3 C6 C7 124.2(2) . . ?
C7 C6 H6 117.9 . . ?
C6 C7 C8 114.5(2) . . ?
C6 C7 C10A 117.7(2) . . ?
C6 C7 C9B 149.4(6) . . ?
C8 C7 C10A 127.7(2) . . ?
C8 C7 C9B 92.4(5) . . ?
N4 C8 C7 123.2(2) . . ?
N4 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
C3 C9A H9A 110.4 . . ?
C3 C9A C10A 120.1(2) . 7_556 ?
C3 C9A C10A 114.7(2) . . ?
C10A C9A H9A 110.4 7_556 . ?
C10A C9A H9A 110.4 . . ?
C10A C9A C10A 89.22(18) . 7_556 ?
C7 C10A C9A 119.43(19) . 7_556 ?
C7 C10A C9A 118.9(2) . . ?
C7 C10A H10A 108.8 . . ?
C9A C10A C9A 90.78(18) . 7_556 ?
C9A C10A H10A 108.8 . . ?
C9A C10A H10A 108.8 7_556 . ?
C7 C9B H9B 115.8 . . ?
C10B C9B C7 115.7(11) 7_556 . ?
C10B C9B C7 99.7(10) . . ?
C10B C9B H9B 115.8 . . ?
C10B C9B H9B 115.8 7_556 . ?
C10B C9B C10B 89.9(12) . 7_556 ?
C3 C10B H10B 114.7 . . ?
C9B C10B C3 102.2(11) . . ?
C9B C10B C3 117.2(11) 7_556 . ?
C9B C10B H10B 114.7 7_556 . ?
C9B C10B H10B 114.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C2 C3 C4 -1.8(4) . . . . ?
N2 C2 C3 C9A 178.3(3) . . . . ?
N2 C2 C3 C10B 162.3(7) . . . . ?
N3 C6 C7 C8 0.6(4) . . . . ?
N3 C6 C7 C10A -176.7(3) . . . . ?
N3 C6 C7 C9B 150.1(11) . . . . ?
C1 N1 C4 C3 -0.6(4) . . . . ?
C1 N2 C2 C3 1.5(4) . . . . ?
C2 N2 C1 N1 -0.7(4) . . . . ?
C2 C3 C4 N1 1.3(4) . . . . ?
C2 C3 C9A C10A -48.3(3) . . . . ?
C2 C3 C9A C10A 56.1(3) . . . 7_556 ?
C2 C3 C10B C9B -178.6(10) . . . . ?
C2 C3 C10B C9B 84.9(12) . . . 7_556 ?
C3 C9A C10A C7 -112.3(2) . . . . ?
C3 C9A C10A C9A 123.0(2) . . . 7_556 ?
C4 N1 C1 N2 0.2(4) . . . . ?
C4 C3 C9A C10A 131.9(2) . . . . ?
C4 C3 C9A C10A -123.7(2) . . . 7_556 ?
C4 C3 C10B C9B -127.4(13) . . . 7_556 ?
C4 C3 C10B C9B -31(2) . . . . ?
C5 N3 C6 C7 -0.2(4) . . . . ?
C5 N4 C8 C7 0.1(4) . . . . ?
C6 N3 C5 N4 -0.3(5) . . . . ?
C6 C7 C8 N4 -0.6(4) . . . . ?
C6 C7 C10A C9A -68.2(3) . . . 7_556 ?
C6 C7 C10A C9A -177.5(2) . . . . ?
C6 C7 C9B C10B -23(2) . . . 7_556 ?
C6 C7 C9B C10B 71.2(17) . . . . ?
C7 C9B C10B C3 126.0(9) . . . . ?
C7 C9B C10B C9B -116.1(12) . . . 7_556 ?
C8 N4 C5 N3 0.4(5) . . . . ?
C8 C7 C10A C9A 114.9(3) . . . 7_556 ?
C8 C7 C10A C9A 5.6(4) . . . . ?
C8 C7 C9B C10B 129.0(12) . . . 7_556 ?
C8 C7 C9B C10B -136.3(10) . . . . ?
C9A C3 C4 N1 -178.8(2) . . . . ?
C10A C7 C8 N4 176.4(3) . . . . ?
C10A C9A C10A C7 124.7(2) 7_556 . . . ?
C10A C9A C10A C9A 0.000(2) 7_556 . . 7_556 ?
C9B C7 C8 N4 -165.6(6) . . . . ?
C10B C3 C4 N1 -142.6(13) . . . . ?
C10B C9B C10B C3 -117.9(12) 7_556 . . . ?
C10B C9B C10B C9B 0.001(2) 7_556 . . 7_556 ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_r23219
_database_code_depnum_ccdc_archive 'CCDC 2010996'
loop_
_audit_author_name
_audit_author_address
'Michael Sinnwell'
;Pacific Northwest National Lab
United States of America
;
_audit_update_record             
;
2020-06-26 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-06-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'rctt-1,2,3,4-tetrakis-(5-pyrimdyl)cyclobutane tetrachloro-1,4-diiodobenzne'
_chemical_formula_moiety         '2(C6 Cl4 I2), C20 H16 N8, C7 H8'
_chemical_formula_sum            'C39 H24 Cl8 I4 N8'
_chemical_formula_weight         1395.86
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   8.9258(5)
_cell_length_b                   9.1762(6)
_cell_length_c                   14.6465(8)
_cell_angle_alpha                82.686(2)
_cell_angle_beta                 74.068(2)
_cell_angle_gamma                72.653(2)
_cell_volume                     1099.72(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6944
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.361
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0999 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.8710.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13882
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      102(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4331
_reflns_number_total             4990
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.036
_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)+(0.0181P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0480
_refine_ls_wR_factor_ref         0.0499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17-C18
 1.51 with sigma of 0.02
 C18-C19 = C18-C23 = C20-C21
 1.39 with sigma of 0.02
 C19-C20 = C21-C22 = C22-C23
 1.38 with sigma of 0.02
 C18-C20
 2.42 with sigma of 0.04
 C19-C21
 2.39 with sigma of 0.04
 C18-C22
 2.41 with sigma of 0.04
 C20-C22 = C21-C23
 2.4 with sigma of 0.04
 C17-C19 = C17-C23
 2.52 with sigma of 0.04
 C18-C19 \\sim C19-C20 \\sim C20-C21 \\sim C21-C22 \\sim C22-C23 \\sim C23-C18
 with sigma of 0.02
 C18-C22 \\sim C18-C20 \\sim C23-C21 \\sim C19-C23 \\sim C20-C22 \\sim C19-C21
 with sigma of 0.04
 C17-C23 \\sim C17-C19
 with sigma of 0.04
3. Restrained planarity
 C17, C18, C19, C20, C21, C22, C23
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 C17, C18, C19, C20, C21, C22, C23
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: C17(0.5) H17A(0.5) H17B(0.5) H17C(0.5) C18(0.5) C19(0.5) H19(0.5)
 C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C23(0.5) H23(0.5)
7.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
7.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23)
7.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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 0.45232(2) 1.35600(2) 0.34619(2) 0.01760(5) Uani 1 1 d . . . . .
I2 I 0.06770(2) 0.83033(2) 0.63047(2) 0.01561(5) Uani 1 1 d . . . . .
Cl1 Cl 0.53646(8) 0.98333(7) 0.30680(4) 0.01932(13) Uani 1 1 d . . . . .
Cl2 Cl 0.36311(8) 0.75414(7) 0.42954(4) 0.01931(13) Uani 1 1 d . . . . .
Cl3 Cl 0.00055(9) 1.19521(8) 0.67529(5) 0.02654(16) Uani 1 1 d . . . . .
Cl4 Cl 0.17638(9) 1.42329(7) 0.55451(5) 0.02342(14) Uani 1 1 d . . . . .
C11 C 0.3439(3) 1.1957(3) 0.43403(18) 0.0156(5) Uani 1 1 d . . . . .
C12 C 0.3863(3) 1.0439(3) 0.40876(17) 0.0153(5) Uani 1 1 d . . . . .
C13 C 0.3095(3) 0.9387(3) 0.46436(18) 0.0148(5) Uani 1 1 d . . . . .
C14 C 0.1890(3) 0.9843(3) 0.54706(18) 0.0153(5) Uani 1 1 d . . . . .
C15 C 0.1487(3) 1.1349(3) 0.57375(18) 0.0164(5) Uani 1 1 d . . . . .
C16 C 0.2264(3) 1.2395(3) 0.51835(18) 0.0157(5) Uani 1 1 d . . . . .
N1 N 0.5879(3) 0.5779(2) 0.22275(16) 0.0208(5) Uani 1 1 d . . . . .
N2 N 0.8270(3) 0.6471(3) 0.13572(18) 0.0251(6) Uani 1 1 d . . . . .
N3 N 0.1417(3) 1.3239(2) 0.21750(16) 0.0187(5) Uani 1 1 d . . . . .
N4 N 0.2960(3) 1.4833(2) 0.11781(16) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.7461(4) 0.5622(3) 0.1996(2) 0.0259(7) Uani 1 1 d . . . . .
H1 H 0.807687 0.482958 0.231464 0.031 Uiso 1 1 calc R U . . .
C2 C 0.7341(3) 0.7612(3) 0.09154(19) 0.0192(6) Uani 1 1 d . . . . .
H2 H 0.784661 0.822805 0.045621 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5680(3) 0.7918(3) 0.11054(17) 0.0135(5) Uani 1 1 d . . . . .
C4 C 0.4991(3) 0.6936(3) 0.17787(18) 0.0160(5) Uani 1 1 d . . . . .
H4 H 0.387501 0.708792 0.192240 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1708(3) 1.4583(3) 0.18642(19) 0.0184(5) Uani 1 1 d . . . . .
H5 H 0.095772 1.544050 0.215646 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2511(3) 1.2008(3) 0.17309(18) 0.0153(5) Uani 1 1 d . . . . .
H6 H 0.235728 1.104686 0.192528 0.018 Uiso 1 1 calc R U . . .
C7 C 0.3842(3) 1.2112(3) 0.10038(17) 0.0125(5) Uani 1 1 d . . . . .
C8 C 0.4013(3) 1.3591(3) 0.07671(18) 0.0160(5) Uani 1 1 d . . . . .
H8 H 0.491349 1.371155 0.029532 0.019 Uiso 1 1 calc R U . . .
C9 C 0.5063(3) 1.0775(3) 0.04945(17) 0.0127(5) Uani 1 1 d . . . . .
H9 H 0.610167 1.062169 0.064976 0.015 Uiso 1 1 calc R U . . .
C10 C 0.4648(3) 0.9217(3) 0.06175(17) 0.0126(5) Uani 1 1 d . . . . .
H10 H 0.349678 0.935321 0.093025 0.015 Uiso 1 1 calc R U . . .
C17 C 1.1602(7) 0.7424(7) -0.0787(5) 0.0298(14) Uani 0.5 1 d D U P A -1
H17A H 1.089334 0.704733 -0.102428 0.045 Uiso 0.5 1 calc R U P A -1
H17B H 1.201727 0.669632 -0.032200 0.045 Uiso 0.5 1 calc R U P A -1
H17C H 1.248587 0.757136 -0.130213 0.045 Uiso 0.5 1 calc R U P A -1
C18 C 1.0678(7) 0.8917(7) -0.0337(4) 0.0160(13) Uani 0.5 1 d D U P A -1
C19 C 0.9950(9) 1.0152(8) -0.0869(5) 0.0170(16) Uani 0.5 1 d D U P A -1
H19 H 1.007856 1.005836 -0.151286 0.020 Uiso 0.5 1 calc R U P A -1
C20 C 0.9031(9) 1.1528(8) -0.0456(5) 0.0236(16) Uani 0.5 1 d D U P A -1
H20 H 0.854029 1.234154 -0.081947 0.028 Uiso 0.5 1 calc R U P A -1
C21 C 0.8854(9) 1.1676(8) 0.0497(5) 0.0269(16) Uani 0.5 1 d D U P A -1
H21 H 0.824139 1.259165 0.077779 0.032 Uiso 0.5 1 calc R U P A -1
C22 C 0.9588(10) 1.0463(9) 0.1033(6) 0.0270(17) Uani 0.5 1 d D U P A -1
H22 H 0.948324 1.056730 0.167275 0.032 Uiso 0.5 1 calc R U P A -1
C23 C 1.0481(9) 0.9090(8) 0.0618(4) 0.0187(16) Uani 0.5 1 d D U P A -1
H23 H 1.095527 0.827333 0.098644 0.022 Uiso 0.5 1 calc R U 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
I1 C11 2.107(2) . ?
I2 C14 2.100(3) . ?
Cl1 C12 1.733(3) . ?
Cl2 C13 1.721(3) . ?
Cl3 C15 1.720(3) . ?
Cl4 C16 1.724(3) . ?
C11 C12 1.401(4) . ?
C11 C16 1.397(4) . ?
C12 C13 1.397(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.398(4) . ?
C15 C16 1.397(4) . ?
N1 C1 1.325(4) . ?
N1 C4 1.340(3) . ?
N2 C1 1.335(4) . ?
N2 C2 1.344(3) . ?
N3 C5 1.333(3) . ?
N3 C6 1.354(3) . ?
N4 C5 1.338(3) . ?
N4 C8 1.331(3) . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 C4 1.391(3) . ?
C3 C10 1.506(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.379(4) . ?
C7 C8 1.399(3) . ?
C7 C9 1.497(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9800 . ?
C9 C10 1.577(3) 2_675 ?
C9 C10 1.558(3) . ?
C10 H10 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C18 1.500(8) . ?
C18 C19 1.389(7) . ?
C18 C23 1.384(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(8) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(7) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 I1 120.93(19) . . ?
C16 C11 I1 120.48(18) . . ?
C16 C11 C12 118.6(2) . . ?
C11 C12 Cl1 120.0(2) . . ?
C13 C12 Cl1 118.7(2) . . ?
C13 C12 C11 121.3(2) . . ?
C12 C13 Cl2 119.7(2) . . ?
C14 C13 Cl2 120.49(19) . . ?
C14 C13 C12 119.8(2) . . ?
C13 C14 I2 120.76(18) . . ?
C13 C14 C15 119.2(2) . . ?
C15 C14 I2 120.09(19) . . ?
C14 C15 Cl3 120.4(2) . . ?
C16 C15 Cl3 118.7(2) . . ?
C16 C15 C14 120.9(2) . . ?
C11 C16 Cl4 120.10(19) . . ?
C11 C16 C15 120.3(2) . . ?
C15 C16 Cl4 119.6(2) . . ?
C1 N1 C4 116.2(2) . . ?
C1 N2 C2 114.7(2) . . ?
C5 N3 C6 115.5(2) . . ?
C8 N4 C5 115.3(2) . . ?
N1 C1 N2 127.4(2) . . ?
N1 C1 H1 116.3 . . ?
N2 C1 H1 116.3 . . ?
N2 C2 H2 118.2 . . ?
N2 C2 C3 123.6(2) . . ?
C3 C2 H2 118.2 . . ?
C2 C3 C4 115.8(2) . . ?
C2 C3 C10 123.2(2) . . ?
C4 C3 C10 121.0(2) . . ?
N1 C4 C3 122.2(2) . . ?
N1 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N3 C5 N4 127.1(2) . . ?
N3 C5 H5 116.4 . . ?
N4 C5 H5 116.4 . . ?
N3 C6 H6 118.4 . . ?
N3 C6 C7 123.1(2) . . ?
C7 C6 H6 118.4 . . ?
C6 C7 C8 115.1(2) . . ?
C6 C7 C9 124.3(2) . . ?
C8 C7 C9 120.6(2) . . ?
N4 C8 C7 123.8(2) . . ?
N4 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C7 C9 H9 109.3 . . ?
C7 C9 C10 118.00(19) . 2_675 ?
C7 C9 C10 118.9(2) . . ?
C10 C9 H9 109.3 . . ?
C10 C9 H9 109.3 2_675 . ?
C10 C9 C10 90.84(18) . 2_675 ?
C3 C10 C9 118.7(2) . 2_675 ?
C3 C10 C9 116.4(2) . . ?
C3 C10 H10 110.3 . . ?
C9 C10 C9 89.16(18) . 2_675 ?
C9 C10 H10 110.3 2_675 . ?
C9 C10 H10 110.3 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C19 C18 C17 120.2(6) . . ?
C23 C18 C17 121.4(6) . . ?
C23 C18 C19 118.3(5) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.1(6) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.6(6) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(6) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.0(7) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 121.0(6) . . ?
C18 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C11 C12 Cl1 3.0(3) . . . . ?
I1 C11 C12 C13 -176.96(18) . . . . ?
I1 C11 C16 Cl4 -3.4(3) . . . . ?
I1 C11 C16 C15 176.55(19) . . . . ?
I2 C14 C15 Cl3 0.4(3) . . . . ?
I2 C14 C15 C16 -179.04(19) . . . . ?
Cl1 C12 C13 Cl2 -1.1(3) . . . . ?
Cl1 C12 C13 C14 179.58(19) . . . . ?
Cl2 C13 C14 I2 -0.8(3) . . . . ?
Cl2 C13 C14 C15 179.70(19) . . . . ?
Cl3 C15 C16 Cl4 1.8(3) . . . . ?
Cl3 C15 C16 C11 -178.16(19) . . . . ?
C11 C12 C13 Cl2 178.94(19) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C12 C11 C16 Cl4 177.46(19) . . . . ?
C12 C11 C16 C15 -2.6(4) . . . . ?
C12 C13 C14 I2 178.60(18) . . . . ?
C12 C13 C14 C15 -0.9(4) . . . . ?
C13 C14 C15 Cl3 179.96(19) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 Cl4 -178.78(19) . . . . ?
C14 C15 C16 C11 1.3(4) . . . . ?
C16 C11 C12 Cl1 -177.80(19) . . . . ?
C16 C11 C12 C13 2.2(4) . . . . ?
N2 C2 C3 C4 -1.7(4) . . . . ?
N2 C2 C3 C10 178.9(3) . . . . ?
N3 C6 C7 C8 1.5(4) . . . . ?
N3 C6 C7 C9 -179.5(2) . . . . ?
C1 N1 C4 C3 0.2(4) . . . . ?
C1 N2 C2 C3 1.0(4) . . . . ?
C2 N2 C1 N1 0.5(5) . . . . ?
C2 C3 C4 N1 1.1(4) . . . . ?
C2 C3 C10 C9 -43.1(4) . . . . ?
C2 C3 C10 C9 61.5(4) . . . 2_675 ?
C4 N1 C1 N2 -1.1(5) . . . . ?
C4 C3 C10 C9 137.6(2) . . . . ?
C4 C3 C10 C9 -117.8(3) . . . 2_675 ?
C5 N3 C6 C7 -0.1(4) . . . . ?
C5 N4 C8 C7 1.3(4) . . . . ?
C6 N3 C5 N4 -0.9(4) . . . . ?
C6 C7 C8 N4 -2.1(4) . . . . ?
C6 C7 C9 C10 122.4(3) . . . 2_675 ?
C6 C7 C9 C10 14.2(4) . . . . ?
C7 C9 C10 C3 -115.2(2) . . . . ?
C7 C9 C10 C9 123.0(2) . . . 2_675 ?
C8 N4 C5 N3 0.3(4) . . . . ?
C8 C7 C9 C10 -58.7(3) . . . 2_675 ?
C8 C7 C9 C10 -166.8(2) . . . . ?
C9 C7 C8 N4 178.8(2) . . . . ?
C10 C3 C4 N1 -179.6(2) . . . . ?
C10 C9 C10 C3 121.9(2) 2_675 . . . ?
C10 C9 C10 C9 -0.001(2) 2_675 . . 2_675 ?
C17 C18 C19 C20 177.3(7) . . . . ?
C17 C18 C23 C22 -178.2(7) . . . . ?
C18 C19 C20 C21 0.8(12) . . . . ?
C19 C18 C23 C22 -0.4(10) . . . . ?
C19 C20 C21 C22 0.1(12) . . . . ?
C20 C21 C22 C23 -1.0(13) . . . . ?
C21 C22 C23 C18 1.2(12) . . . . ?
C23 C18 C19 C20 -0.6(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
