# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_y
_database_code_depnum_ccdc_archive 'CCDC 2270636'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2023-06-18 deposited with the CCDC.	2023-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-05-09
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 I N2 O2'
_chemical_formula_sum            'C21 H13 I N2 O2'
_chemical_formula_weight         452.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   17.518(3)
_cell_length_b                   5.2658(9)
_cell_length_c                   20.162(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.568(2)
_cell_angle_gamma                90
_cell_volume                     1773.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7560
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    1.824
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.5205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17816
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.969
_diffrn_reflns_theta_min         1.219
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                4474
_reflns_number_total             5732
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.633
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5732
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.034
_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)+(0.0381P)²+1.4632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), 
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.80519(2) 1.56624(4) 0.43582(2) 0.05389(8) Uani 1 1 d . . . . .
O1 O 0.87130(12) 0.8427(5) 0.62460(12) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.80196(14) 0.3555(4) 0.68240(11) 0.0540(5) Uani 1 1 d . . . . .
N1 N 0.71557(12) 1.0168(4) 0.55020(10) 0.0348(4) Uani 1 1 d . . . . .
N2 N 0.59738(13) 0.8673(5) 0.55567(12) 0.0435(5) Uani 1 1 d . . . . .
C1 C 0.76491(15) 1.1696(5) 0.52601(13) 0.0389(5) Uani 1 1 d . . . . .
H1 H 0.8202 1.1630 0.5456 0.047 Uiso 1 1 calc R . . . .
C2 C 0.73061(16) 1.3309(5) 0.47257(12) 0.0403(5) Uani 1 1 d . . . . .
C3 C 0.64705(18) 1.3432(6) 0.44280(13) 0.0477(6) Uani 1 1 d . . . . .
H3 H 0.6248 1.4577 0.4071 0.057 Uiso 1 1 calc R . . . .
C4 C 0.59861(17) 1.1876(6) 0.46622(13) 0.0471(6) Uani 1 1 d . . . . .
H4 H 0.5434 1.1920 0.4459 0.057 Uiso 1 1 calc R . . . .
C5 C 0.63303(16) 1.0206(6) 0.52148(13) 0.0398(5) Uani 1 1 d . . . . .
C6 C 0.65681(15) 0.7654(5) 0.60844(12) 0.0363(5) Uani 1 1 d . . . . .
C7 C 0.73229(15) 0.8448(5) 0.60591(12) 0.0354(5) Uani 1 1 d . . . . .
C8 C 0.63478(16) 0.6023(5) 0.65890(13) 0.0389(5) Uani 1 1 d . . . . .
C9 C 0.66699(19) 0.6413(6) 0.73045(14) 0.0487(6) Uani 1 1 d . . . . .
H9 H 0.7052 0.7671 0.7472 0.058 Uiso 1 1 calc R . . . .
C10 C 0.6417(2) 0.4912(8) 0.77655(17) 0.0612(8) Uani 1 1 d . . . . .
H10 H 0.6643 0.5146 0.8242 0.073 Uiso 1 1 calc R . . . .
C11 C 0.5839(2) 0.3092(7) 0.75293(18) 0.0633(9) Uani 1 1 d . . . . .
H11 H 0.5666 0.2118 0.7841 0.076 Uiso 1 1 calc R . . . .
C12 C 0.5517(2) 0.2729(7) 0.68160(18) 0.0587(8) Uani 1 1 d . . . . .
H12 H 0.5133 0.1474 0.6651 0.070 Uiso 1 1 calc R . . . .
C13 C 0.57568(18) 0.4192(5) 0.63514(15) 0.0461(6) Uani 1 1 d . . . . .
H13 H 0.5523 0.3958 0.5876 0.055 Uiso 1 1 calc R . . . .
C14 C 0.81289(15) 0.7677(5) 0.64088(13) 0.0381(5) Uani 1 1 d . . . . .
C15 C 0.82975(15) 0.5642(5) 0.69782(13) 0.0373(5) Uani 1 1 d . . . . .
C16 C 0.88370(15) 0.6277(5) 0.76831(13) 0.0366(5) Uani 1 1 d . . . . .
C17 C 0.93304(17) 0.8405(6) 0.78146(16) 0.0482(6) Uani 1 1 d . . . . .
H17 H 0.9319 0.9541 0.7458 0.058 Uiso 1 1 calc R . . . .
C18 C 0.98377(18) 0.8821(7) 0.84777(18) 0.0556(7) Uani 1 1 d . . . . .
H18 H 1.0173 1.0232 0.8565 0.067 Uiso 1 1 calc R . . . .
C19 C 0.9852(2) 0.7179(8) 0.90072(17) 0.0614(8) Uani 1 1 d . . . . .
H19 H 1.0202 0.7458 0.9450 0.074 Uiso 1 1 calc R . . . .
C20 C 0.9348(2) 0.5113(7) 0.88829(17) 0.0613(8) Uani 1 1 d . . . . .
H20 H 0.9347 0.4022 0.9246 0.074 Uiso 1 1 calc R . . . .
C21 C 0.8845(2) 0.4655(6) 0.82253(15) 0.0487(6) Uani 1 1 d . . . . .
H21 H 0.8508 0.3249 0.8144 0.058 Uiso 1 1 calc R . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.092(3) . ?
O1 C14 1.230(3) . ?
O2 C15 1.204(3) . ?
N1 C1 1.374(3) . ?
N1 C5 1.386(3) . ?
N1 C7 1.403(3) . ?
N2 C5 1.333(4) . ?
N2 C6 1.355(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.361(4) . ?
C2 C3 1.406(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(4) . ?
C6 C7 1.402(4) . ?
C6 C8 1.469(3) . ?
C7 C14 1.434(3) . ?
C8 C9 1.396(4) . ?
C8 C13 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.391(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.533(3) . ?
C15 C16 1.488(4) . ?
C16 C17 1.391(4) . ?
C16 C21 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(5) . ?
C21 H21 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
C1 N1 C5 122.2(2) . . ?
C1 N1 C7 131.3(2) . . ?
C5 N1 C7 106.4(2) . . ?
C5 N2 C6 106.1(2) . . ?
N1 C1 H1 120.9 . . ?
C2 C1 N1 118.1(2) . . ?
C2 C1 H1 120.9 . . ?
C1 C2 I1 118.5(2) . . ?
C1 C2 C3 121.4(3) . . ?
C3 C2 I1 120.16(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(3) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 119.0(2) . . ?
N2 C5 N1 111.6(2) . . ?
N2 C5 C4 129.3(2) . . ?
N2 C6 C7 111.3(2) . . ?
N2 C6 C8 118.4(2) . . ?
C7 C6 C8 130.3(2) . . ?
N1 C7 C14 120.9(2) . . ?
C6 C7 N1 104.5(2) . . ?
C6 C7 C14 134.2(2) . . ?
C9 C8 C6 121.4(3) . . ?
C13 C8 C6 119.4(2) . . ?
C13 C8 C9 119.0(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
O1 C14 C7 123.6(2) . . ?
O1 C14 C15 115.9(2) . . ?
C7 C14 C15 120.3(2) . . ?
O2 C15 C14 118.2(2) . . ?
O2 C15 C16 122.9(2) . . ?
C16 C15 C14 118.8(2) . . ?
C17 C16 C15 122.8(2) . . ?
C21 C16 C15 117.9(2) . . ?
C21 C16 C17 119.3(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.8 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.8 . . ?

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 C2 C3 C4 179.2(2) . . . . ?
O1 C14 C15 O2 -113.9(3) . . . . ?
O1 C14 C15 C16 62.2(3) . . . . ?
O2 C15 C16 C17 161.6(3) . . . . ?
O2 C15 C16 C21 -18.0(4) . . . . ?
N1 C1 C2 I1 179.58(18) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
N1 C7 C14 O1 -0.7(4) . . . . ?
N1 C7 C14 C15 -175.2(2) . . . . ?
N2 C6 C7 N1 3.6(3) . . . . ?
N2 C6 C7 C14 -168.7(3) . . . . ?
N2 C6 C8 C9 -129.8(3) . . . . ?
N2 C6 C8 C13 44.7(4) . . . . ?
C1 N1 C5 N2 -176.6(2) . . . . ?
C1 N1 C5 C4 -0.6(4) . . . . ?
C1 N1 C7 C6 174.5(3) . . . . ?
C1 N1 C7 C14 -12.0(4) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C2 C3 C4 C5 1.7(4) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C4 C5 N2 174.5(3) . . . . ?
C5 N1 C1 C2 0.7(4) . . . . ?
C5 N1 C7 C6 -2.6(3) . . . . ?
C5 N1 C7 C14 170.9(2) . . . . ?
C5 N2 C6 C7 -3.1(3) . . . . ?
C5 N2 C6 C8 175.2(2) . . . . ?
C6 N2 C5 N1 1.3(3) . . . . ?
C6 N2 C5 C4 -174.2(3) . . . . ?
C6 C7 C14 O1 170.6(3) . . . . ?
C6 C7 C14 C15 -3.9(4) . . . . ?
C6 C8 C9 C10 176.8(3) . . . . ?
C6 C8 C13 C12 -177.0(3) . . . . ?
C7 N1 C1 C2 -176.0(2) . . . . ?
C7 N1 C5 N2 0.9(3) . . . . ?
C7 N1 C5 C4 176.9(3) . . . . ?
C7 C6 C8 C9 48.1(4) . . . . ?
C7 C6 C8 C13 -137.4(3) . . . . ?
C7 C14 C15 O2 61.0(3) . . . . ?
C7 C14 C15 C16 -122.8(3) . . . . ?
C8 C6 C7 N1 -174.4(2) . . . . ?
C8 C6 C7 C14 13.3(5) . . . . ?
C8 C9 C10 C11 -1.7(6) . . . . ?
C9 C8 C13 C12 -2.4(4) . . . . ?
C9 C10 C11 C12 1.2(6) . . . . ?
C10 C11 C12 C13 -1.4(6) . . . . ?
C11 C12 C13 C8 2.0(5) . . . . ?
C13 C8 C9 C10 2.3(5) . . . . ?
C14 C15 C16 C17 -14.4(4) . . . . ?
C14 C15 C16 C21 166.0(2) . . . . ?
C15 C16 C17 C18 -177.6(3) . . . . ?
C15 C16 C21 C20 178.2(3) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C16 C21 C20 -1.4(5) . . . . ?
C17 C18 C19 C20 -1.1(5) . . . . ?
C18 C19 C20 C21 1.8(6) . . . . ?
C19 C20 C21 C16 -0.5(6) . . . . ?
C21 C16 C17 C18 2.0(4) . . . . ?

_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_t
_database_code_depnum_ccdc_archive 'CCDC 2270637'
loop_
_audit_author_name
_audit_author_address
'Xianggao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2023-06-18 deposited with the CCDC.	2023-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H17 Br2 I N2 O2 S, C H Cl3'
_chemical_formula_sum            'C27 H18 Br2 Cl3 I N2 O2 S'
_chemical_formula_weight         827.56
_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'
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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.396(7)
_cell_length_b                   12.162(10)
_cell_length_c                   14.231(10)
_cell_angle_alpha                110.606(11)
_cell_angle_beta                 105.796(10)
_cell_angle_gamma                91.123(10)
_cell_volume                     1452.5(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3650
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    4.230
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.2294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.1561
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9212
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.602
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                2566
_reflns_number_total             4967
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.964
_refine_diff_density_min         -1.545
_refine_diff_density_rms         0.250
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4967
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1759
_refine_ls_R_factor_gt           0.0959
_refine_ls_restrained_S_all      0.971
_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)+(0.1681P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2376
_refine_ls_wR_factor_ref         0.2855
_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 
 Cl1S-Cl3S \\sim Cl1T-Cl3T 
 with sigma of 0.04 
 Cl1S-Cl2S \\sim Cl1T-Cl2T 
 with sigma of 0.04 
 Cl3S-Cl2S \\sim Cl3T-Cl2T 
 with sigma of 0.04 
 Cl1S-C1S \\sim Cl1T-C1T 
 with sigma of 0.02 
 Cl3S-C1S \\sim Cl3T-C1T 
 with sigma of 0.02 
 Cl2S-C1S \\sim Cl2T-C1T 
 with sigma of 0.02 
3. Uiso/Uaniso restraints and constraints 
Uanis(C5) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C22) \\sim Ueq: with sigma of 
0.01 and sigma for terminal atoms of 0.02 
Uanis(Cl2S) \\sim Ueq, Uanis(Cl2T) \\sim Ueq: with sigma of 0.01 and sigma for 
terminal atoms of 0.02 
Uanis(C1S) = Uanis(C1T) 
Uanis(Cl3S) = Uanis(Cl3T) 
Uanis(Cl1T) = Uanis(Cl1S) 
4. Others 
 Sof(C1T)=Sof(H1T)=Sof(Cl1T)=Sof(Cl2T)=Sof(Cl3T)=1-FVAR(1) 
 Sof(C1S)=Sof(H1S)=Sof(Cl1S)=Sof(Cl2S)=Sof(Cl3S)=FVAR(1) 
5.a Ternary CH refined with riding coordinates: 
 C8(H8), C1S(H1S), C1T(H1T) 
5.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C4(H4), C5(H5), C6(H6), C11(H11), C16(H16), C17(H17), C18(H18), 
 C19(H19), C21(H21), C22(H22), C23(H23), C25(H25) 
5.c Idealised Me refined as rotating group: 
 C26(H26A,H26B,H26C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.8093(2) 0.87898(15) 0.92256(12) 0.0660(6) Uani 1 1 d . . . . .
Br2 Br 0.13574(19) 0.89129(15) 0.18840(12) 0.0591(5) Uani 1 1 d . . . . .
C1 C 0.8307(14) 0.6755(11) 0.6251(10) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.7932(15) 0.7554(11) 0.7076(10) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.7172 0.8006 0.6940 0.048 Uiso 1 1 calc R . . . .
C3 C 0.8655(16) 0.7698(13) 0.8099(10) 0.044(4) Uani 1 1 d . . . . .
C4 C 0.974(2) 0.7002(17) 0.8316(12) 0.071(5) Uani 1 1 d . . . . .
H4 H 1.0200 0.7069 0.9005 0.085 Uiso 1 1 calc R . . . .
C5 C 1.013(2) 0.6242(18) 0.7531(15) 0.080(5) Uani 1 1 d . U . . .
H5 H 1.0876 0.5781 0.7676 0.096 Uiso 1 1 calc R . . . .
C6 C 0.9432(18) 0.6108(15) 0.6467(11) 0.059(4) Uani 1 1 d . . . . .
H6 H 0.9741 0.5585 0.5926 0.071 Uiso 1 1 calc R . . . .
C7 C 0.7561(14) 0.6552(12) 0.5124(10) 0.037(3) Uani 1 1 d . U . . .
C8 C 0.6197(13) 0.7127(10) 0.4819(9) 0.028(3) Uani 1 1 d . . . . .
H8 H 0.5547 0.7015 0.5221 0.033 Uiso 1 1 calc R . . . .
C9 C 0.5280(13) 0.6556(11) 0.3655(9) 0.030(3) Uani 1 1 d . . . . .
C10 C 0.5089(14) 0.5162(11) 0.3293(9) 0.030(3) Uani 1 1 d . . . . .
C11 C 0.5385(13) 0.3631(10) 0.1725(9) 0.032(3) Uani 1 1 d . . . . .
H11 H 0.4974 0.3022 0.1861 0.039 Uiso 1 1 calc R . . . .
C12 C 0.6040(12) 0.5768(10) 0.2246(8) 0.023(3) Uani 1 1 d . . . . .
C13 C 0.5962(15) 0.3391(11) 0.0893(10) 0.036(3) Uani 1 1 d . . . . .
C14 C 0.6590(13) 0.4328(11) 0.0688(9) 0.031(3) Uani 1 1 d . . . . .
C15 C 0.6638(12) 0.5488(11) 0.1330(8) 0.027(3) Uani 1 1 d . . . . .
C16 C 0.7222(15) 0.6438(13) 0.1157(11) 0.042(3) Uani 1 1 d . . . . .
H16 H 0.7219 0.7214 0.1593 0.050 Uiso 1 1 calc R . . . .
C17 C 0.7806(17) 0.6201(14) 0.0320(11) 0.052(4) Uani 1 1 d . . . . .
H17 H 0.8171 0.6817 0.0172 0.062 Uiso 1 1 calc R . . . .
C18 C 0.7839(17) 0.5044(16) -0.0287(11) 0.060(5) Uani 1 1 d . . . . .
H18 H 0.8299 0.4892 -0.0814 0.072 Uiso 1 1 calc R . . . .
C19 C 0.7225(15) 0.4107(12) -0.0149(10) 0.039(3) Uani 1 1 d . . . . .
H19 H 0.7223 0.3335 -0.0596 0.047 Uiso 1 1 calc R . . . .
C20 C 0.3720(13) 0.6947(10) 0.3471(8) 0.026(3) Uani 1 1 d . . . . .
C21 C 0.2678(15) 0.6592(15) 0.3878(11) 0.051(4) Uani 1 1 d . . . . .
H21 H 0.2928 0.6099 0.4255 0.062 Uiso 1 1 calc R . . . .
C22 C 0.1288(17) 0.6959(15) 0.3731(13) 0.058(4) Uani 1 1 d . U . . .
H22 H 0.0618 0.6733 0.4025 0.069 Uiso 1 1 calc R . . . .
C23 C 0.0878(17) 0.7674(14) 0.3136(12) 0.056(4) Uani 1 1 d . . . . .
H23 H -0.0059 0.7929 0.3029 0.067 Uiso 1 1 calc R . . . .
C24 C 0.1914(13) 0.7985(11) 0.2717(9) 0.032(3) Uani 1 1 d . . . . .
C25 C 0.3315(13) 0.7648(11) 0.2891(9) 0.032(3) Uani 1 1 d . . . . .
H25 H 0.3995 0.7894 0.2614 0.038 Uiso 1 1 calc R . . . .
C26 C 0.830(2) 0.8815(15) 0.4867(14) 0.077(6) Uani 1 1 d . . . . .
H26A H 0.8111 0.8348 0.4134 0.116 Uiso 1 1 calc GR . . . .
H26B H 0.9070 0.8521 0.5277 0.116 Uiso 1 1 calc GR . . . .
H26C H 0.8608 0.9626 0.4997 0.116 Uiso 1 1 calc GR . . . .
I1 I 0.58287(15) 0.16073(9) -0.00493(9) 0.0717(5) Uani 1 1 d . . . . .
N1 N 0.6009(10) 0.6772(8) 0.2935(7) 0.026(2) Uani 1 1 d . . . . .
N2 N 0.5432(11) 0.4800(8) 0.2353(7) 0.027(2) Uani 1 1 d . . . . .
O1 O 0.8051(11) 0.5902(10) 0.4447(7) 0.058(3) Uani 1 1 d . . . . .
O2 O 0.4646(11) 0.4560(8) 0.3698(7) 0.042(2) Uani 1 1 d . . . . .
S1 S 0.6638(4) 0.8725(3) 0.5225(3) 0.0431(9) Uani 1 1 d . . . . .
C1S C 0.681(3) 0.094(3) 0.267(2) 0.085(8) Uani 0.70(2) 1 d D . P A 1
H1S H 0.6290 0.0932 0.1971 0.102 Uiso 0.70(2) 1 calc R . P A 1
Cl1S Cl 0.8279(17) 0.0197(16) 0.2539(14) 0.105(4) Uani 0.70(2) 1 d D . P A 1
Cl2S Cl 0.5599(15) 0.0547(14) 0.3078(15) 0.156(7) Uani 0.70(2) 1 d D U P A 1
Cl3S Cl 0.756(2) 0.2505(10) 0.3497(11) 0.125(5) Uani 0.70(2) 1 d D . P A 1
C1T C 0.734(5) 0.088(4) 0.327(4) 0.085(8) Uani 0.30(2) 1 d D . P A 2
H1T H 0.8129 0.0998 0.3918 0.102 Uiso 0.30(2) 1 calc R . P A 2
Cl1T Cl 0.811(5) 0.043(4) 0.227(3) 0.105(4) Uani 0.30(2) 1 d D . P A 2
Cl2T Cl 0.603(4) 0.005(3) 0.322(2) 0.111(10) Uani 0.30(2) 1 d D U P A 2
Cl3T Cl 0.674(4) 0.233(3) 0.336(3) 0.125(5) Uani 0.30(2) 1 d D . 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
Br1 C3 1.898(15) . ?
Br2 C24 1.892(13) . ?
C1 C2 1.372(18) . ?
C1 C6 1.36(2) . ?
C1 C7 1.492(18) . ?
C2 C3 1.374(18) . ?
C3 C4 1.38(2) . ?
C4 C5 1.32(2) . ?
C5 C6 1.43(2) . ?
C7 C8 1.505(17) . ?
C7 O1 1.218(14) . ?
C8 C9 1.536(17) . ?
C8 S1 1.824(12) . ?
C9 C10 1.580(17) . ?
C9 C20 1.532(16) . ?
C9 N1 1.467(14) . ?
C10 N2 1.383(14) . ?
C10 O2 1.207(13) . ?
C11 C13 1.376(17) . ?
C11 N2 1.379(15) . ?
C12 C15 1.491(14) . ?
C12 N1 1.276(14) . ?
C12 N2 1.371(14) . ?
C13 C14 1.426(17) . ?
C13 I1 2.090(13) . ?
C14 C15 1.377(16) . ?
C14 C19 1.418(15) . ?
C15 C16 1.395(18) . ?
C16 C17 1.386(18) . ?
C17 C18 1.37(2) . ?
C18 C19 1.37(2) . ?
C20 C21 1.397(17) . ?
C20 C25 1.374(17) . ?
C21 C22 1.37(2) . ?
C22 C23 1.41(2) . ?
C23 C24 1.381(19) . ?
C24 C25 1.370(17) . ?
C26 S1 1.781(18) . ?
C1S Cl1S 1.68(2) . ?
C1S Cl2S 1.55(3) . ?
C1S Cl3S 1.85(3) . ?
C1T Cl1T 1.69(3) . ?
C1T Cl2T 1.54(3) . ?
C1T Cl3T 1.84(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 124.0(12) . . ?
C6 C1 C2 118.4(13) . . ?
C6 C1 C7 117.6(12) . . ?
C1 C2 C3 121.4(14) . . ?
C2 C3 Br1 120.6(12) . . ?
C2 C3 C4 120.3(15) . . ?
C4 C3 Br1 119.1(11) . . ?
C5 C4 C3 119.0(15) . . ?
C4 C5 C6 121.6(18) . . ?
C1 C6 C5 119.2(16) . . ?
C1 C7 C8 120.5(11) . . ?
O1 C7 C1 119.5(12) . . ?
O1 C7 C8 120.0(12) . . ?
C7 C8 C9 114.4(10) . . ?
C7 C8 S1 111.9(9) . . ?
C9 C8 S1 111.5(8) . . ?
C8 C9 C10 110.2(10) . . ?
C20 C9 C8 111.1(9) . . ?
C20 C9 C10 107.9(9) . . ?
N1 C9 C8 113.8(9) . . ?
N1 C9 C10 103.3(8) . . ?
N1 C9 C20 110.1(9) . . ?
N2 C10 C9 102.9(9) . . ?
O2 C10 C9 128.3(10) . . ?
O2 C10 N2 128.6(11) . . ?
C13 C11 N2 118.2(11) . . ?
N1 C12 C15 129.3(10) . . ?
N1 C12 N2 115.9(9) . . ?
N2 C12 C15 114.8(10) . . ?
C11 C13 C14 120.7(12) . . ?
C11 C13 I1 116.7(9) . . ?
C14 C13 I1 122.6(9) . . ?
C15 C14 C13 120.1(10) . . ?
C15 C14 C19 117.9(11) . . ?
C19 C14 C13 122.0(12) . . ?
C14 C15 C12 120.1(10) . . ?
C14 C15 C16 122.4(10) . . ?
C16 C15 C12 117.5(11) . . ?
C17 C16 C15 118.6(14) . . ?
C18 C17 C16 119.2(13) . . ?
C19 C18 C17 122.7(11) . . ?
C18 C19 C14 119.0(12) . . ?
C21 C20 C9 120.9(11) . . ?
C25 C20 C9 120.5(10) . . ?
C25 C20 C21 118.7(11) . . ?
C22 C21 C20 121.0(14) . . ?
C21 C22 C23 120.1(14) . . ?
C24 C23 C22 117.7(13) . . ?
C23 C24 Br2 118.1(10) . . ?
C25 C24 Br2 119.8(10) . . ?
C25 C24 C23 122.1(12) . . ?
C24 C25 C20 120.3(11) . . ?
C12 N1 C9 107.5(9) . . ?
C11 N2 C10 124.1(10) . . ?
C12 N2 C10 109.1(9) . . ?
C12 N2 C11 126.1(9) . . ?
C26 S1 C8 101.5(7) . . ?
Cl1S C1S Cl3S 107.2(16) . . ?
Cl2S C1S Cl1S 122.0(18) . . ?
Cl2S C1S Cl3S 108.7(16) . . ?
Cl1T C1T Cl3T 108(2) . . ?
Cl2T C1T Cl1T 118(3) . . ?
Cl2T C1T Cl3T 109(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
