# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2fwws0
_database_code_depnum_ccdc_archive 'CCDC 2261133'
loop_
_audit_author_name
_audit_author_address
'Chuanzhi Liu'
;School of Chemistry and Chemical Engineering, Shangqiu Normal University
China
;
_audit_update_record             
;
2023-05-06 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;
_audit_creation_date             2023-04-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 F4 I2, 2(C H Cl3), C53 H48 N4'
_chemical_formula_sum            'C61 H50 Cl6 F4 I2 N4'
_chemical_formula_weight         1381.55
_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'
F F 0.0171 0.0103 '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      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                   29.043(3)
_cell_length_b                   14.0514(12)
_cell_length_c                   20.8239(17)
_cell_angle_alpha                90
_cell_angle_beta                 133.661(2)
_cell_angle_gamma                90
_cell_volume                     6147.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.71
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.776
_shelx_estimated_absorpt_T_min   0.776
_exptl_absorpt_coefficient_mu    1.337
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4580
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.2153 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.6143.
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    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1871
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            75711
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.584
_diffrn_ambient_temperature      297.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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_source_current           35.0
_diffrn_source_power             1.225
_diffrn_source_voltage           35.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3854
_reflns_number_total             5405
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.088
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.133
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         5405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1424
_refine_ls_R_factor_gt           0.1065
_refine_ls_restrained_S_all      1.110
_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)+(0.0923P)²+121.6085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2425
_refine_ls_wR_factor_ref         0.2587
_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.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C6(H6), C7(H7), C4(H4), C3(H3), C10(H10), C20(H20), C19(H19),
 C24(H24), C23(H23), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C27(H27A,H27B,H27C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.31816(4) 0.63542(6) 0.19738(5) 0.0651(3) Uani 1 1 d . . . . .
Cl1 Cl 0.3506(3) 0.8669(4) 0.3332(3) 0.1258(19) Uani 1 1 d . . . . .
Cl2 Cl 0.3995(4) 1.0295(4) 0.4472(4) 0.151(3) Uani 1 1 d . . . . .
Cl3 Cl 0.4397(3) 0.8442(4) 0.5200(4) 0.138(2) Uani 1 1 d . . . . .
C2 C 0.5527(4) 0.0520(5) 0.7798(5) 0.0263(18) Uani 1 1 d . . . . .
C1 C 0.500000 0.1222(8) 0.750000 0.026(2) Uani 1 2 d S T P . .
C15 C 0.5216(4) 0.1893(5) 0.8242(5) 0.0233(17) Uani 1 1 d . . . . .
C18 C 0.5574(5) 0.3279(7) 0.9483(6) 0.037(2) Uani 1 1 d . . . . .
F2 F 0.2744(5) 0.8467(6) 0.1306(5) 0.102(3) Uani 1 1 d . . . . .
F1 F 0.2762(4) 0.5631(5) 0.0181(5) 0.085(2) Uani 1 1 d . . . . .
N2 N 0.7604(6) -0.3245(9) 0.9020(7) 0.076(3) Uani 1 1 d . . . . .
C11 C 0.7706(6) -0.2385(11) 0.8904(9) 0.077(4) Uani 1 1 d . . . . .
H11 H 0.806472 -0.227940 0.899860 0.092 Uiso 1 1 calc R U . . .
C12 C 0.7308(6) -0.1620(8) 0.8648(8) 0.058(3) Uani 1 1 d . . . . .
C8 C 0.6804(5) -0.1754(7) 0.8542(6) 0.044(2) Uani 1 1 d . . . . .
C5 C 0.6372(4) -0.0951(6) 0.8296(6) 0.038(2) Uani 1 1 d . . . . .
C6 C 0.5889(5) -0.0681(8) 0.7425(6) 0.050(3) Uani 1 1 d . . . . .
H6 H 0.584573 -0.098819 0.698994 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5472(5) 0.0023(7) 0.7180(6) 0.043(2) Uani 1 1 d . . . . .
H7 H 0.514322 0.017115 0.658207 0.052 Uiso 1 1 calc R U . . .
C14 C 0.7467(8) -0.0643(11) 0.8500(13) 0.099(5) Uani 1 1 d . . . . .
H14A H 0.775770 -0.073037 0.842820 0.148 Uiso 1 1 calc R U . . .
H14B H 0.765953 -0.024032 0.900270 0.148 Uiso 1 1 calc R U . . .
H14C H 0.708351 -0.035131 0.797545 0.148 Uiso 1 1 calc R U . . .
C4 C 0.6422(5) -0.0461(7) 0.8912(6) 0.048(3) Uani 1 1 d . . . . .
H4 H 0.673936 -0.062819 0.950788 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6016(5) 0.0270(7) 0.8671(6) 0.042(2) Uani 1 1 d . . . . .
H3 H 0.607330 0.060272 0.910819 0.050 Uiso 1 1 calc R U . . .
C10 C 0.7111(7) -0.3377(9) 0.8905(8) 0.069(4) Uani 1 1 d . . . . .
H10 H 0.703098 -0.398884 0.897863 0.082 Uiso 1 1 calc R U . . .
C9 C 0.6692(6) -0.2655(8) 0.8677(8) 0.054(3) Uani 1 1 d . . . . .
C13 C 0.6133(8) -0.2897(10) 0.8528(12) 0.097(5) Uani 1 1 d . . . . .
H13A H 0.611555 -0.248745 0.888031 0.145 Uiso 1 1 calc R U . . .
H13B H 0.616230 -0.354700 0.869433 0.145 Uiso 1 1 calc R U . . .
H13C H 0.575397 -0.281329 0.791142 0.145 Uiso 1 1 calc R U . . .
C20 C 0.4844(5) 0.2115(7) 0.8404(7) 0.048(3) Uani 1 1 d . . . . .
H20 H 0.446076 0.179551 0.809046 0.057 Uiso 1 1 calc R U . . .
C19 C 0.5016(5) 0.2786(8) 0.9006(8) 0.055(3) Uani 1 1 d . . . . .
H19 H 0.474895 0.291145 0.909560 0.066 Uiso 1 1 calc R U . . .
C21 C 0.5785(5) 0.4016(7) 1.0156(6) 0.041(2) Uani 1 1 d . . . . .
C25 C 0.6156(7) 0.3744(9) 1.1031(8) 0.072(4) Uani 1 1 d . . . . .
C24 C 0.6363(8) 0.4454(11) 1.1638(9) 0.084(5) Uani 1 1 d . . . . .
H24 H 0.662352 0.428058 1.223000 0.101 Uiso 1 1 calc R U . . .
N1 N 0.6218(6) 0.5348(8) 1.1439(8) 0.071(3) Uani 1 1 d . . . . .
C23 C 0.5867(6) 0.5584(8) 1.0622(9) 0.060(3) Uani 1 1 d . . . . .
H23 H 0.576253 0.622417 1.047698 0.072 Uiso 1 1 calc R U . . .
C22 C 0.5627(5) 0.4940(8) 0.9924(7) 0.047(3) Uani 1 1 d . . . . .
C27 C 0.5234(7) 0.5295(10) 0.9014(9) 0.080(4) Uani 1 1 d . . . . .
H27A H 0.543695 0.515089 0.880880 0.119 Uiso 1 1 calc R U . . .
H27B H 0.518255 0.597099 0.900500 0.119 Uiso 1 1 calc R U . . .
H27C H 0.482359 0.499368 0.863352 0.119 Uiso 1 1 calc R U . . .
C26 C 0.6346(11) 0.2747(12) 1.1338(10) 0.137(9) Uani 1 1 d . . . . .
H26A H 0.615957 0.233950 1.083968 0.206 Uiso 1 1 calc R U . . .
H26B H 0.620099 0.255897 1.161649 0.206 Uiso 1 1 calc R U . . .
H26C H 0.680148 0.269486 1.175738 0.206 Uiso 1 1 calc R U . . .
C17 C 0.5936(5) 0.3093(8) 0.9298(7) 0.053(3) Uani 1 1 d . . . . .
H17 H 0.630862 0.343627 0.958585 0.063 Uiso 1 1 calc R U . . .
C16 C 0.5756(5) 0.2414(8) 0.8697(7) 0.046(3) Uani 1 1 d . . . . .
H16 H 0.601546 0.229938 0.859334 0.056 Uiso 1 1 calc R U . . .
C30 C 0.2632(6) 0.7991(8) 0.0679(7) 0.054(3) Uani 1 1 d . . . . .
C29 C 0.2760(5) 0.7036(8) 0.0782(7) 0.050(3) Uani 1 1 d . . . . .
C28 C 0.2625(5) 0.6573(8) 0.0104(8) 0.055(3) Uani 1 1 d . . . . .
C31 C 0.3774(8) 0.9110(10) 0.4322(10) 0.087(5) Uani 1 1 d . . . . .
H31 H 0.342506 0.906404 0.429679 0.105 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 C29 2.092(9) . ?
Cl1 C31 1.740(14) . ?
Cl2 C31 1.735(14) . ?
Cl3 C31 1.710(18) . ?
C2 C1 1.546(11) . ?
C2 C7 1.373(12) . ?
C2 C3 1.371(12) . ?
C1 C15 1.527(10) . ?
C1 C15 1.527(10) 2_656 ?
C15 C20 1.370(12) . ?
C15 C16 1.358(12) . ?
C18 C19 1.367(14) . ?
C18 C21 1.492(13) . ?
C18 C17 1.375(14) . ?
F2 C30 1.293(13) . ?
F1 C28 1.360(13) . ?
N2 C11 1.306(19) . ?
N2 C10 1.292(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(17) . ?
C12 C8 1.335(16) . ?
C12 C14 1.547(19) . ?
C8 C5 1.491(13) . ?
C8 C9 1.383(15) . ?
C5 C6 1.375(13) . ?
C5 C4 1.372(14) . ?
C6 H6 0.9300 . ?
C6 C7 1.361(14) . ?
C7 H7 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.371(13) . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.391(17) . ?
C9 C13 1.47(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C19 1.358(14) . ?
C19 H19 0.9300 . ?
C21 C25 1.384(16) . ?
C21 C22 1.351(15) . ?
C25 C24 1.381(16) . ?
C25 C26 1.48(2) . ?
C24 H24 0.9300 . ?
C24 N1 1.298(18) . ?
N1 C23 1.284(17) . ?
C23 H23 0.9300 . ?
C23 C22 1.421(15) . ?
C22 C27 1.468(17) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.359(14) . ?
C16 H16 0.9300 . ?
C30 C29 1.370(15) . ?
C30 C28 1.382(15) 7_565 ?
C29 C28 1.344(16) . ?
C31 H31 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
C7 C2 C1 120.4(7) . . ?
C3 C2 C1 121.9(7) . . ?
C3 C2 C7 117.1(8) . . ?
C2 C1 C2 100.6(9) 2_656 . ?
C15 C1 C2 112.8(4) 2_656 2_656 ?
C15 C1 C2 112.8(4) . . ?
C15 C1 C2 113.7(4) 2_656 . ?
C15 C1 C2 113.7(4) . 2_656 ?
C15 C1 C15 103.8(9) . 2_656 ?
C20 C15 C1 123.2(7) . . ?
C16 C15 C1 120.5(7) . . ?
C16 C15 C20 115.6(8) . . ?
C19 C18 C21 123.1(9) . . ?
C19 C18 C17 117.0(9) . . ?
C17 C18 C21 119.8(9) . . ?
C10 N2 C11 117.5(11) . . ?
N2 C11 H11 118.2 . . ?
N2 C11 C12 123.6(14) . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C14 118.7(12) . . ?
C8 C12 C11 118.8(12) . . ?
C8 C12 C14 122.5(10) . . ?
C12 C8 C5 121.1(10) . . ?
C12 C8 C9 118.6(10) . . ?
C9 C8 C5 120.2(10) . . ?
C6 C5 C8 120.8(9) . . ?
C4 C5 C8 122.6(8) . . ?
C4 C5 C6 116.7(9) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.8(9) . . ?
C7 C6 H6 119.1 . . ?
C2 C7 H7 119.3 . . ?
C6 C7 C2 121.4(8) . . ?
C6 C7 H7 119.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 C5 121.6(9) . . ?
C3 C4 H4 119.2 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(8) . . ?
C4 C3 H3 119.4 . . ?
N2 C10 H10 118.2 . . ?
N2 C10 C9 123.6(13) . . ?
C9 C10 H10 118.2 . . ?
C8 C9 C10 117.7(12) . . ?
C8 C9 C13 123.3(10) . . ?
C10 C9 C13 118.8(12) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C20 H20 118.8 . . ?
C19 C20 C15 122.4(9) . . ?
C19 C20 H20 118.8 . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.1(9) . . ?
C20 C19 H19 119.4 . . ?
C25 C21 C18 119.1(9) . . ?
C22 C21 C18 120.9(9) . . ?
C22 C21 C25 120.0(9) . . ?
C21 C25 C26 123.3(11) . . ?
C24 C25 C21 117.1(12) . . ?
C24 C25 C26 119.5(12) . . ?
C25 C24 H24 117.7 . . ?
N1 C24 C25 124.6(13) . . ?
N1 C24 H24 117.7 . . ?
C23 N1 C24 117.3(10) . . ?
N1 C23 H23 117.6 . . ?
N1 C23 C22 124.8(12) . . ?
C22 C23 H23 117.6 . . ?
C21 C22 C23 116.2(11) . . ?
C21 C22 C27 123.9(10) . . ?
C23 C22 C27 120.0(11) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.6(9) . . ?
C16 C17 H17 119.7 . . ?
C15 C16 C17 123.1(9) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 H16 118.4 . . ?
F2 C30 C29 119.8(10) . . ?
F2 C30 C28 121.1(10) . 7_565 ?
C29 C30 C28 119.1(11) . 7_565 ?
C30 C29 I1 120.6(9) . . ?
C28 C29 I1 122.1(8) . . ?
C28 C29 C30 117.3(9) . . ?
F1 C28 C30 116.5(11) . 7_565 ?
C29 C28 F1 119.8(10) . . ?
C29 C28 C30 123.6(10) . 7_565 ?
Cl1 C31 H31 108.2 . . ?
Cl2 C31 Cl1 111.2(8) . . ?
Cl2 C31 H31 108.2 . . ?
Cl3 C31 Cl1 110.4(10) . . ?
Cl3 C31 Cl2 110.4(9) . . ?
Cl3 C31 H31 108.2 . . ?

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 C29 C28 F1 0.3(15) . . . . ?
I1 C29 C28 C30 -177.6(9) . . . 7_565 ?
C2 C1 C15 C20 -136.9(8) . . . . ?
C2 C1 C15 C20 -23.3(11) 2_656 . . . ?
C2 C1 C15 C16 52.9(11) . . . . ?
C2 C1 C15 C16 166.5(8) 2_656 . . . ?
C1 C2 C7 C6 -172.0(10) . . . . ?
C1 C2 C3 C4 169.7(9) . . . . ?
C1 C15 C20 C19 -173.1(10) . . . . ?
C1 C15 C16 C17 172.9(10) . . . . ?
C15 C1 C15 C20 99.6(9) 2_656 . . . ?
C15 C1 C15 C16 -70.6(8) 2_656 . . . ?
C15 C20 C19 C18 0.2(19) . . . . ?
C18 C21 C25 C24 177.5(12) . . . . ?
C18 C21 C25 C26 -2(2) . . . . ?
C18 C21 C22 C23 -178.5(9) . . . . ?
C18 C21 C22 C27 1.4(17) . . . . ?
C18 C17 C16 C15 0.9(18) . . . . ?
F2 C30 C29 I1 -3.5(16) . . . . ?
F2 C30 C29 C28 179.0(11) . . . . ?
N2 C11 C12 C8 2(2) . . . . ?
N2 C11 C12 C14 -177.8(14) . . . . ?
N2 C10 C9 C8 2.0(19) . . . . ?
N2 C10 C9 C13 177.5(13) . . . . ?
C11 N2 C10 C9 -1(2) . . . . ?
C11 C12 C8 C5 178.0(11) . . . . ?
C11 C12 C8 C9 -1.1(17) . . . . ?
C12 C8 C5 C6 83.6(14) . . . . ?
C12 C8 C5 C4 -98.0(13) . . . . ?
C12 C8 C9 C10 -0.9(17) . . . . ?
C12 C8 C9 C13 -176.2(13) . . . . ?
C8 C5 C6 C7 177.2(11) . . . . ?
C8 C5 C4 C3 -179.3(10) . . . . ?
C5 C8 C9 C10 -180.0(10) . . . . ?
C5 C8 C9 C13 4.7(18) . . . . ?
C5 C6 C7 C2 2.1(18) . . . . ?
C5 C4 C3 C2 2.4(17) . . . . ?
C6 C5 C4 C3 -0.9(16) . . . . ?
C7 C2 C1 C2 73.8(8) . . . 2_656 ?
C7 C2 C1 C15 -46.9(11) . . . 2_656 ?
C7 C2 C1 C15 -164.7(8) . . . . ?
C7 C2 C3 C4 -1.6(15) . . . . ?
C14 C12 C8 C5 -1.8(18) . . . . ?
C14 C12 C8 C9 179.1(13) . . . . ?
C4 C5 C6 C7 -1.3(17) . . . . ?
C3 C2 C1 C2 -97.2(9) . . . 2_656 ?
C3 C2 C1 C15 24.2(11) . . . . ?
C3 C2 C1 C15 142.0(8) . . . 2_656 ?
C3 C2 C7 C6 -0.5(15) . . . . ?
C10 N2 C11 C12 -1(2) . . . . ?
C9 C8 C5 C6 -97.3(13) . . . . ?
C9 C8 C5 C4 81.1(14) . . . . ?
C20 C15 C16 C17 2.0(16) . . . . ?
C19 C18 C21 C25 90.5(14) . . . . ?
C19 C18 C21 C22 -90.6(13) . . . . ?
C19 C18 C17 C16 -3.2(17) . . . . ?
C21 C18 C19 C20 -179.5(11) . . . . ?
C21 C18 C17 C16 178.9(10) . . . . ?
C21 C25 C24 N1 2(2) . . . . ?
C25 C21 C22 C23 0.4(16) . . . . ?
C25 C21 C22 C27 -179.7(13) . . . . ?
C25 C24 N1 C23 -1(2) . . . . ?
C24 N1 C23 C22 0(2) . . . . ?
N1 C23 C22 C21 0.3(17) . . . . ?
N1 C23 C22 C27 -179.6(12) . . . . ?
C22 C21 C25 C24 -1(2) . . . . ?
C22 C21 C25 C26 179.6(16) . . . . ?
C26 C25 C24 N1 -179.0(18) . . . . ?
C17 C18 C19 C20 2.7(17) . . . . ?
C17 C18 C21 C25 -91.7(14) . . . . ?
C17 C18 C21 C22 87.1(13) . . . . ?
C16 C15 C20 C19 -2.5(16) . . . . ?
C30 C29 C28 F1 177.7(10) . . . . ?
C30 C29 C28 C30 0(2) . . . 7_565 ?
C28 C30 C29 I1 177.6(8) 7_565 . . . ?
C28 C30 C29 C28 0.1(19) 7_565 . . . ?

_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_a
_audit_block_doi                 10.5517/ccdc.csd.cc2fwwz6
_database_code_depnum_ccdc_archive 'CCDC 2261139'
loop_
_audit_author_name
_audit_author_address
'Chuanzhi Liu'
;School of Chemistry and Chemical Engineering, Shangqiu Normal University
China
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C57 H52 Cl12 N4'
_chemical_formula_weight         1218.43

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I4(1)/a  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   21.037(5)
_cell_length_b                   21.037(5)
_cell_length_c                   14.026(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6208(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2482
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      19.43

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2504
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8333
_exptl_absorpt_correction_T_max  0.9088
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14383
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2658
_reflns_number_gt                1707
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+72.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00046(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     170
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1792
_refine_ls_R_factor_gt           0.1350
_refine_ls_wR_factor_ref         0.2750
_refine_ls_wR_factor_gt          0.2597
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2739(4) 0.3646(4) 0.7015(6) 0.084(2) Uani 1 1 d . . .
Cl1 Cl 0.8617(3) 0.51686(16) 0.8468(3) 0.1617(19) Uani 1 1 d . . .
Cl2 Cl 0.9499(2) 0.4123(2) 0.8388(3) 0.1611(18) Uani 1 1 d . . .
Cl3 Cl 0.90725(18) 0.45623(14) 1.0188(2) 0.1199(12) Uani 1 1 d . . .
C1 C 0.2816(4) 0.3786(5) 0.7898(8) 0.093(3) Uani 1 1 d . . .
H1A H 0.3178 0.4018 0.8052 0.112 Uiso 1 1 calc R . .
C2 C 0.2406(4) 0.3625(5) 0.8659(6) 0.080(3) Uani 1 1 d . . .
C3 C 0.1863(3) 0.3278(3) 0.8402(5) 0.0543(17) Uani 1 1 d . . .
C4 C 0.1773(4) 0.3113(4) 0.7452(5) 0.0600(19) Uani 1 1 d . . .
C5 C 0.2248(5) 0.3316(4) 0.6798(6) 0.075(2) Uani 1 1 d . . .
H5A H 0.2198 0.3200 0.6163 0.091 Uiso 1 1 calc R . .
C6 C 0.1213(5) 0.2752(5) 0.7111(7) 0.089(3) Uani 1 1 d . . .
H6A H 0.0946 0.2647 0.7643 0.134 Uiso 1 1 calc R . .
H6B H 0.1352 0.2368 0.6805 0.134 Uiso 1 1 calc R . .
H6C H 0.0978 0.3006 0.6665 0.134 Uiso 1 1 calc R . .
C7 C 0.2550(6) 0.3802(8) 0.9636(8) 0.153(6) Uani 1 1 d . . .
H7A H 0.2220 0.3651 1.0050 0.229 Uiso 1 1 calc R . .
H7B H 0.2577 0.4257 0.9683 0.229 Uiso 1 1 calc R . .
H7C H 0.2948 0.3617 0.9822 0.229 Uiso 1 1 calc R . .
C8 C 0.1404(3) 0.3083(3) 0.9138(5) 0.0464(15) Uani 1 1 d . . .
C9 C 0.0972(4) 0.3508(4) 0.9495(5) 0.065(2) Uani 1 1 d . . .
H9A H 0.0972 0.3926 0.9276 0.078 Uiso 1 1 calc R . .
C10 C 0.0530(3) 0.3319(3) 1.0187(5) 0.0581(19) Uani 1 1 d . . .
H10A H 0.0228 0.3610 1.0400 0.070 Uiso 1 1 calc R . .
C11 C 0.0531(3) 0.2720(3) 1.0555(4) 0.0373(13) Uani 1 1 d . . .
C12 C 0.0968(4) 0.2305(3) 1.0213(5) 0.061(2) Uani 1 1 d . . .
H12A H 0.0988 0.1896 1.0462 0.073 Uiso 1 1 calc R . .
C13 C 0.1388(4) 0.2480(3) 0.9495(6) 0.068(2) Uani 1 1 d . . .
H13A H 0.1666 0.2178 0.9251 0.082 Uiso 1 1 calc R . .
C14 C 0.0000 0.2500 1.1250 0.036(2) Uani 1 4 d S . .
C15 C 0.8708(4) 0.4307(4) 0.8800(5) 0.009(2) Uani 0.60 1 d PU . .
H15A H 0.8357 0.4005 0.8727 0.010 Uiso 1 1 calc R . .
C15' C 0.8821(7) 0.4437(7) 0.8941(10) 0.011(4) Uiso 0.40 1 d 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
N1 C1 1.283(13) . ?
N1 C5 1.281(11) . ?
Cl1 C15' 1.730(14) . ?
Cl1 C15 1.880(9) . ?
Cl2 C15' 1.753(14) . ?
Cl2 C15 1.802(9) . ?
Cl3 C15' 1.847(15) . ?
Cl3 C15 2.160(8) . ?
C1 C2 1.414(12) . ?
C1 H1A 0.9300 . ?
C2 C3 1.403(11) . ?
C2 C7 1.453(14) . ?
C3 C4 1.390(10) . ?
C3 C8 1.472(9) . ?
C4 C5 1.422(11) . ?
C4 C6 1.480(11) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.363(9) . ?
C8 C9 1.371(9) . ?
C9 C10 1.403(9) . ?
C9 H9A 0.9300 . ?
C10 C11 1.362(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.356(8) . ?
C11 C14 1.553(6) . ?
C12 C13 1.388(9) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C11 1.553(6) 6_454 ?
C14 C11 1.553(6) 15_557 ?
C14 C11 1.553(6) 12_668 ?
C15 H15A 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 C5 117.0(8) . . ?
C15' Cl1 C15 12.2(5) . . ?
C15' Cl2 C15 13.2(5) . . ?
C15' Cl3 C15 7.7(5) . . ?
N1 C1 C2 126.7(9) . . ?
N1 C1 H1A 116.7 . . ?
C2 C1 H1A 116.7 . . ?
C3 C2 C1 115.3(8) . . ?
C3 C2 C7 123.1(8) . . ?
C1 C2 C7 121.6(9) . . ?
C4 C3 C2 119.2(7) . . ?
C4 C3 C8 120.9(7) . . ?
C2 C3 C8 119.9(7) . . ?
C3 C4 C5 116.5(7) . . ?
C3 C4 C6 123.1(7) . . ?
C5 C4 C6 120.4(8) . . ?
N1 C5 C4 125.2(8) . . ?
N1 C5 H5A 117.4 . . ?
C4 C5 H5A 117.4 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.2(6) . . ?
C13 C8 C3 122.3(6) . . ?
C9 C8 C3 120.6(6) . . ?
C8 C9 C10 120.5(6) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 121.6(6) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
C12 C11 C10 117.6(6) . . ?
C12 C11 C14 121.2(5) . . ?
C10 C11 C14 120.8(5) . . ?
C11 C12 C13 121.1(6) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C8 C13 C12 122.0(6) . . ?
C8 C13 H13A 119.0 . . ?
C12 C13 H13A 119.0 . . ?
C11 C14 C11 113.2(2) 6_454 15_557 ?
C11 C14 C11 113.2(2) 6_454 12_668 ?
C11 C14 C11 102.3(4) 15_557 12_668 ?
C11 C14 C11 102.3(4) 6_454 . ?
C11 C14 C11 113.2(2) 15_557 . ?
C11 C14 C11 113.2(2) 12_668 . ?
Cl2 C15 Cl1 102.8(4) . . ?
Cl2 C15 Cl3 90.9(3) . . ?
Cl1 C15 Cl3 91.1(4) . . ?
Cl2 C15 H15A 121.5 . . ?
Cl1 C15 H15A 121.5 . . ?
Cl3 C15 H15A 121.5 . . ?
Cl1 C15' Cl2 111.5(8) . . ?
Cl1 C15' Cl3 107.9(8) . . ?
Cl2 C15' Cl3 103.9(8) . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.773
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2fwx08
_database_code_depnum_ccdc_archive 'CCDC 2261140'
loop_
_audit_author_name
_audit_author_address
'Chuanzhi Liu'
;School of Chemistry and Chemical Engineering, Shangqiu Normal University
China
;
_audit_update_record             
;
2023-08-10 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H48 Cl3 F8 I4 N4'
_chemical_formula_weight         1663.03

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

loop_
_symmetry_equiv_pos_as_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                   13.123(4)
_cell_length_b                   43.843(14)
_cell_length_c                   13.393(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.914(5)
_cell_angle_gamma                90.00
_cell_volume                     6989(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6733
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.81

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3228
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6004
_exptl_absorpt_correction_T_max  0.6837
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16395
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6077
_reflns_number_gt                4773
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0800P)²+15.9000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6077
_refine_ls_number_parameters     393
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.00901(4) 0.100896(8) 0.48167(4) 0.06525(17) Uani 1 1 d . . .
I2 I 0.79044(3) 0.217082(9) 0.69796(4) 0.06630(17) Uani 1 1 d . . .
F1 F 0.7865(6) 0.14467(11) 0.7103(6) 0.147(3) Uani 1 1 d . . .
F2 F 0.8738(7) 0.10051(9) 0.6344(7) 0.174(3) Uani 1 1 d . . .
F3 F 1.0197(3) 0.17470(8) 0.4736(3) 0.0670(9) Uani 1 1 d . . .
F4 F 0.9299(3) 0.21853(7) 0.5476(3) 0.0751(10) Uani 1 1 d . . .
N1 N 0.0995(5) 1.05442(11) 0.3940(4) 0.0659(14) Uani 1 1 d . . .
N2 N 0.7600(5) 0.76444(12) 0.6831(5) 0.0697(14) Uani 1 1 d . . .
C1 C 0.1741(7) 1.06158(14) 0.3563(6) 0.082(2) Uani 1 1 d . . .
H1A H 0.1852 1.0822 0.3476 0.098 Uiso 1 1 calc R . .
C2 C 0.2377(6) 1.04077(13) 0.3285(6) 0.0629(15) Uani 1 1 d . . .
C3 C 0.2197(4) 1.00981(11) 0.3417(4) 0.0454(12) Uani 1 1 d . . .
C4 C 0.1421(5) 1.00212(12) 0.3829(5) 0.0547(14) Uani 1 1 d . . .
C5 C 0.0838(5) 1.02547(14) 0.4043(5) 0.0608(15) Uani 1 1 d . . .
H5A H 0.0290 1.0201 0.4280 0.073 Uiso 1 1 calc R . .
C6 C 0.1208(7) 0.96907(16) 0.4030(9) 0.100(3) Uani 1 1 d . . .
H6A H 0.1688 0.9560 0.3843 0.151 Uiso 1 1 calc R . .
H6B H 0.0437 0.9640 0.3582 0.151 Uiso 1 1 calc R . .
H6C H 0.1365 0.9663 0.4792 0.151 Uiso 1 1 calc R . .
C7 C 0.3200(9) 1.05143(17) 0.2853(9) 0.112(3) Uani 1 1 d . . .
H7A H 0.3560 1.0341 0.2701 0.168 Uiso 1 1 calc R . .
H7B H 0.3756 1.0642 0.3392 0.168 Uiso 1 1 calc R . .
H7C H 0.2811 1.0629 0.2188 0.168 Uiso 1 1 calc R . .
C8 C 0.2884(4) 0.98563(10) 0.3175(4) 0.0407(11) Uani 1 1 d . . .
C9 C 0.2555(5) 0.97292(15) 0.2152(5) 0.0633(17) Uani 1 1 d . . .
H9A H 0.1879 0.9791 0.1589 0.076 Uiso 1 1 calc R . .
C10 C 0.3198(4) 0.95106(13) 0.1926(4) 0.0546(14) Uani 1 1 d . . .
H10A H 0.2948 0.9431 0.1219 0.065 Uiso 1 1 calc R . .
C11 C 0.4206(3) 0.94105(9) 0.2744(4) 0.0325(9) Uani 1 1 d . . .
C12 C 0.4547(4) 0.95436(13) 0.3773(4) 0.0529(13) Uani 1 1 d . . .
H12A H 0.5234 0.9488 0.4334 0.063 Uiso 1 1 calc R . .
C13 C 0.3879(4) 0.97583(12) 0.3981(4) 0.0530(13) Uani 1 1 d . . .
H13A H 0.4116 0.9837 0.4688 0.064 Uiso 1 1 calc R . .
C14 C 0.5000 0.91899(13) 0.2500 0.0320(13) Uani 1 2 d S . .
C15 C 0.5624(4) 0.89632(9) 0.3452(4) 0.0352(10) Uani 1 1 d . . .
C16 C 0.5146(5) 0.88596(14) 0.4133(5) 0.0644(17) Uani 1 1 d . . .
H16A H 0.4506 0.8955 0.4115 0.077 Uiso 1 1 calc R . .
C17 C 0.5610(6) 0.86145(15) 0.4846(6) 0.073(2) Uani 1 1 d . . .
H17A H 0.5303 0.8558 0.5330 0.088 Uiso 1 1 calc R . .
C18 C 0.6518(4) 0.84545(11) 0.4843(4) 0.0473(12) Uani 1 1 d . . .
C19 C 0.6998(5) 0.85600(13) 0.4183(5) 0.0624(17) Uani 1 1 d . . .
H19A H 0.7626 0.8461 0.4187 0.075 Uiso 1 1 calc R . .
C20 C 0.6572(4) 0.88113(13) 0.3508(5) 0.0572(15) Uani 1 1 d . . .
H20A H 0.6931 0.8880 0.3081 0.069 Uiso 1 1 calc R . .
C21 C 0.6935(4) 0.81715(11) 0.5534(4) 0.0456(12) Uani 1 1 d . . .
C22 C 0.7759(5) 0.81876(13) 0.6601(5) 0.0602(15) Uani 1 1 d . . .
C23 C 0.8069(6) 0.79157(16) 0.7227(6) 0.0731(19) Uani 1 1 d . . .
H23A H 0.8622 0.7925 0.7944 0.088 Uiso 1 1 calc R . .
C24 C 0.6846(5) 0.76341(12) 0.5807(5) 0.0623(15) Uani 1 1 d . . .
H24A H 0.6544 0.7445 0.5522 0.075 Uiso 1 1 calc R . .
C25 C 0.6463(5) 0.78885(13) 0.5109(5) 0.0560(13) Uani 1 1 d . . .
C26 C 0.5600(7) 0.78418(16) 0.3941(6) 0.085(2) Uani 1 1 d . . .
H26A H 0.5389 0.7631 0.3830 0.128 Uiso 1 1 calc R . .
H26B H 0.5912 0.7901 0.3439 0.128 Uiso 1 1 calc R . .
H26C H 0.4948 0.7964 0.3813 0.128 Uiso 1 1 calc R . .
C27 C 0.8300(8) 0.84874(17) 0.7130(6) 0.102(3) Uani 1 1 d . . .
H27A H 0.8011 0.8649 0.6601 0.153 Uiso 1 1 calc R . .
H27B H 0.9099 0.8474 0.7375 0.153 Uiso 1 1 calc R . .
H27C H 0.8130 0.8529 0.7748 0.153 Uiso 1 1 calc R . .
C28 C 0.8428(7) 0.15260(16) 0.6505(7) 0.089(2) Uani 1 1 d . . .
C29 C 0.8886(8) 0.12951(14) 0.6127(8) 0.096(3) Uani 1 1 d . . .
C30 C 0.9463(6) 0.13593(13) 0.5470(6) 0.0646(16) Uani 1 1 d . . .
C31 C 0.9603(5) 0.16660(12) 0.5305(5) 0.0519(13) Uani 1 1 d . . .
C32 C 0.9148(5) 0.18923(12) 0.5702(5) 0.0514(13) Uani 1 1 d . . .
C33 C 0.8545(5) 0.18290(13) 0.6315(5) 0.0595(15) Uani 1 1 d . . .
C34 C 0.5468(11) 0.8111(3) 0.7404(10) 0.067(3) Uani 0.50 1 d PU . .
Cl1 Cl 0.5710(14) 0.8469(4) 0.7775(17) 0.350(9) Uani 0.50 1 d PU . .
Cl2 Cl 0.4337(11) 0.7974(3) 0.6517(10) 0.468(7) Uani 1 1 d 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 C30 2.099(5) . ?
I2 C33 2.092(5) . ?
F1 C28 1.343(8) . ?
F2 C29 1.337(8) . ?
F3 C31 1.347(6) . ?
F4 C32 1.353(6) . ?
N1 C5 1.303(8) . ?
N1 C1 1.314(9) . ?
N2 C24 1.311(8) . ?
N2 C23 1.341(9) . ?
C1 C2 1.388(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.402(8) . ?
C2 C7 1.500(9) . ?
C3 C4 1.389(8) . ?
C3 C8 1.513(6) . ?
C4 C5 1.378(7) . ?
C4 C6 1.521(9) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.366(7) . ?
C8 C9 1.369(7) . ?
C9 C10 1.391(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.386(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(7) . ?
C11 C14 1.555(5) . ?
C12 C13 1.392(7) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.551(6) 2_655 ?
C14 C15 1.551(6) . ?
C14 C11 1.555(5) 2_655 ?
C15 C16 1.383(7) . ?
C15 C20 1.385(7) . ?
C16 C17 1.395(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.385(8) . ?
C17 H17A 0.9300 . ?
C18 C19 1.363(7) . ?
C18 C21 1.506(6) . ?
C19 C20 1.385(7) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C22 1.384(8) . ?
C21 C25 1.396(8) . ?
C22 C23 1.415(8) . ?
C22 C27 1.520(9) . ?
C23 H23A 0.9300 . ?
C24 C25 1.406(8) . ?
C24 H24A 0.9300 . ?
C25 C26 1.509(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C33 1.373(9) . ?
C28 C29 1.379(9) . ?
C29 C30 1.410(9) . ?
C30 C31 1.387(8) . ?
C31 C32 1.376(7) . ?
C32 C33 1.387(8) . ?
C34 C34 1.36(2) 2_656 ?
C34 Cl2 1.484(16) 2_656 ?
C34 Cl2 1.578(16) . ?
C34 Cl1 1.64(2) . ?
C34 Cl1 2.14(2) 2_656 ?
Cl1 Cl1 1.69(3) 2_656 ?
Cl1 C34 2.14(2) 2_656 ?
Cl1 Cl2 2.380(19) 2_656 ?
Cl2 C34 1.484(16) 2_656 ?
Cl2 Cl1 2.380(19) 2_656 ?
Cl2 Cl2 2.47(2) 2_656 ?

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
C5 N1 C1 116.8(5) . . ?
C24 N2 C23 117.5(5) . . ?
N1 C1 C2 125.1(6) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?
C1 C2 C3 116.8(6) . . ?
C1 C2 C7 120.7(6) . . ?
C3 C2 C7 122.5(5) . . ?
C4 C3 C2 118.4(5) . . ?
C4 C3 C8 121.2(5) . . ?
C2 C3 C8 120.3(5) . . ?
C5 C4 C3 117.8(5) . . ?
C5 C4 C6 120.7(6) . . ?
C3 C4 C6 121.4(5) . . ?
N1 C5 C4 125.1(6) . . ?
N1 C5 H5A 117.5 . . ?
C4 C5 H5A 117.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 117.2(4) . . ?
C13 C8 C3 120.6(4) . . ?
C9 C8 C3 122.3(5) . . ?
C8 C9 C10 122.2(5) . . ?
C8 C9 H9A 118.9 . . ?
C10 C9 H9A 118.9 . . ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 117.0(4) . . ?
C12 C11 C14 120.5(4) . . ?
C10 C11 C14 122.1(4) . . ?
C11 C12 C13 121.1(5) . . ?
C11 C12 H12A 119.5 . . ?
C13 C12 H12A 119.5 . . ?
C8 C13 C12 121.8(5) . . ?
C8 C13 H13A 119.1 . . ?
C12 C13 H13A 119.1 . . ?
C15 C14 C15 100.3(5) 2_655 . ?
C15 C14 C11 113.2(2) 2_655 2_655 ?
C15 C14 C11 113.8(2) . 2_655 ?
C15 C14 C11 113.8(2) 2_655 . ?
C15 C14 C11 113.2(2) . . ?
C11 C14 C11 103.1(4) 2_655 . ?
C16 C15 C20 116.9(4) . . ?
C16 C15 C14 121.6(4) . . ?
C20 C15 C14 120.2(4) . . ?
C15 C16 C17 121.1(5) . . ?
C15 C16 H16A 119.5 . . ?
C17 C16 H16A 119.5 . . ?
C18 C17 C16 121.1(5) . . ?
C18 C17 H17A 119.5 . . ?
C16 C17 H17A 119.5 . . ?
C19 C18 C17 117.6(5) . . ?
C19 C18 C21 122.0(5) . . ?
C17 C18 C21 120.4(4) . . ?
C18 C19 C20 121.6(5) . . ?
C18 C19 H19A 119.2 . . ?
C20 C19 H19A 119.2 . . ?
C15 C20 C19 121.6(5) . . ?
C15 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C22 C21 C25 119.1(5) . . ?
C22 C21 C18 121.1(5) . . ?
C25 C21 C18 119.9(5) . . ?
C21 C22 C23 118.3(5) . . ?
C21 C22 C27 122.3(5) . . ?
C23 C22 C27 119.4(6) . . ?
N2 C23 C22 122.9(6) . . ?
N2 C23 H23A 118.5 . . ?
C22 C23 H23A 118.5 . . ?
N2 C24 C25 124.7(6) . . ?
N2 C24 H24A 117.6 . . ?
C25 C24 H24A 117.6 . . ?
C21 C25 C24 117.5(5) . . ?
C21 C25 C26 123.6(5) . . ?
C24 C25 C26 118.9(6) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F1 C28 C33 119.6(6) . . ?
F1 C28 C29 117.6(6) . . ?
C33 C28 C29 122.8(6) . . ?
F2 C29 C28 119.5(6) . . ?
F2 C29 C30 119.5(6) . . ?
C28 C29 C30 121.0(6) . . ?
C31 C30 C29 115.8(5) . . ?
C31 C30 I1 122.8(4) . . ?
C29 C30 I1 121.4(4) . . ?
F3 C31 C32 118.5(5) . . ?
F3 C31 C30 119.5(5) . . ?
C32 C31 C30 122.0(5) . . ?
F4 C32 C31 118.0(5) . . ?
F4 C32 C33 119.7(5) . . ?
C31 C32 C33 122.2(5) . . ?
C28 C33 C32 116.1(5) . . ?
C28 C33 I2 121.2(5) . . ?
C32 C33 I2 122.7(4) . . ?
C34 C34 Cl2 67.3(9) 2_656 2_656 ?
C34 C34 Cl2 60.2(10) 2_656 . ?
Cl2 C34 Cl2 107.4(10) 2_656 . ?
C34 C34 Cl1 91.0(8) 2_656 . ?
Cl2 C34 Cl1 99.3(11) 2_656 . ?
Cl2 C34 Cl1 126.5(13) . . ?
C34 C34 Cl1 49.7(6) 2_656 2_656 ?
Cl2 C34 Cl1 103.1(10) 2_656 2_656 ?
Cl2 C34 Cl1 77.9(8) . 2_656 ?
Cl1 C34 Cl1 51.0(11) . 2_656 ?
C34 Cl1 Cl1 80.2(8) . 2_656 ?
C34 Cl1 C34 39.3(7) . 2_656 ?
Cl1 Cl1 C34 48.8(6) 2_656 2_656 ?
C34 Cl1 Cl2 38.0(6) . 2_656 ?
Cl1 Cl1 Cl2 88.0(7) 2_656 2_656 ?
C34 Cl1 Cl2 40.4(5) 2_656 2_656 ?
C34 Cl2 C34 52.5(10) 2_656 . ?
C34 Cl2 Cl1 42.7(8) 2_656 2_656 ?
C34 Cl2 Cl1 61.7(8) . 2_656 ?
C34 Cl2 Cl2 37.6(6) 2_656 2_656 ?
C34 Cl2 Cl2 35.0(5) . 2_656 ?
Cl1 Cl2 Cl2 72.6(6) 2_656 2_656 ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.104
