# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_lijiul0506
_database_code_depnum_ccdc_archive 'CCDC 1534568'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;
_audit_creation_date             2015-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            BrPzIIG
_chemical_name_systematic        
(3E,3'E)-3,3'-(pyrazine-2,5-diylbis(methanylylidene))bis(6-bromo-1-octylindolin-2-one)
_chemical_formula_moiety         'C19 H22 Br N2 O, C H Cl3'
_chemical_formula_sum            'C20 H23 Br Cl3 N2 O'
_chemical_formula_weight         493.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   4.9228(7)
_cell_length_b                   11.6856(18)
_cell_length_c                   19.2004(19)
_cell_angle_alpha                97.479(11)
_cell_angle_beta                 93.857(10)
_cell_angle_gamma                93.049(12)
_cell_volume                     1090.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1265
_cell_measurement_temperature    295.35(10)
_cell_measurement_theta_max      23.0610
_cell_measurement_theta_min      3.5170
_exptl_absorpt_coefficient_mu    2.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             502
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.1327
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7268
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.46
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.35(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   21.00   48.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000  -60.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   50.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000 -180.0000 18

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   48.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000   60.0000 17

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   82.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000   60.0000 60

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   80.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega  -10.00   80.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.4291   77.0000 -180.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega  -43.00  -16.00   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.9916   77.0000   60.0000 18
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0623876000
_diffrn_orient_matrix_UB_12      0.0257213000
_diffrn_orient_matrix_UB_13      0.0299116000
_diffrn_orient_matrix_UB_21      -0.0250604000
_diffrn_orient_matrix_UB_22      -0.0553573000
_diffrn_orient_matrix_UB_23      0.0104972000
_diffrn_orient_matrix_UB_31      0.1281257000
_diffrn_orient_matrix_UB_32      0.0060363000
_diffrn_orient_matrix_UB_33      0.0197795000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2585
_reflns_number_total             4277
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0217P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1165
_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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H20(0.75) H20A(0.25) Cl1(0.75) Cl3(0.75) Cl1'(0.25) Cl2'(0.25)
3.a Ternary CH refined with riding coordinates:
 C20(H20), C20(H20A)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C6(H6), C7(H7), C9(H9)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.50548(13) 0.33911(5) 0.35216(3) 0.0424(2) Uani 1 d . . .
O1 O 0.3873(7) 0.8049(3) 0.11704(16) 0.0301(8) Uani 1 d . . .
N1 N -0.3653(8) 0.4632(3) 0.05921(18) 0.0229(9) Uani 1 d . . .
N2 N 0.4969(8) 0.6898(3) 0.20202(19) 0.0235(9) Uani 1 d . . .
C1 C -0.4190(9) 0.5951(4) -0.0246(2) 0.0232(11) Uani 1 d . . .
H1 H -0.3557 0.6625 -0.0408 0.028 Uiso 1 calc . . R
C2 C -0.2793(9) 0.5622(4) 0.0349(2) 0.0206(11) Uani 1 d . . .
C3 C -0.0473(9) 0.6344(4) 0.0688(2) 0.0205(11) Uani 1 d . . .
H3 H -0.0100 0.7009 0.0485 0.025 Uiso 1 calc . . R
C4 C 0.1235(9) 0.6224(4) 0.1245(2) 0.0199(11) Uani 1 d . . .
C5 C 0.1679(9) 0.5397(4) 0.1743(2) 0.0196(11) Uani 1 d . . .
C6 C 0.0411(10) 0.4337(4) 0.1828(2) 0.0258(12) Uani 1 d . . .
H6 H -0.1101 0.4029 0.1534 0.031 Uiso 1 calc . . R
C7 C 0.1459(10) 0.3744(4) 0.2366(2) 0.0322(13) Uani 1 d . . .
H7 H 0.0658 0.3028 0.2427 0.039 Uiso 1 calc . . R
C8 C 0.3673(10) 0.4220(4) 0.2802(2) 0.0271(12) Uani 1 d . . .
C9 C 0.4984(10) 0.5276(4) 0.2741(2) 0.0251(12) Uani 1 d . . .
H9 H 0.6472 0.5583 0.3044 0.030 Uiso 1 calc . . R
C10 C 0.3958(9) 0.5849(4) 0.2203(2) 0.0213(11) Uani 1 d . . .
C11 C 0.3468(10) 0.7182(4) 0.1447(2) 0.0229(11) Uani 1 d . . .
C12 C 0.7150(10) 0.7667(4) 0.2400(2) 0.0246(12) Uani 1 d . . .
H12A H 0.7981 0.8127 0.2076 0.029 Uiso 1 calc . . R
H12B H 0.8540 0.7209 0.2588 0.029 Uiso 1 calc . . R
C13 C 0.6108(10) 0.8473(4) 0.3005(2) 0.0280(12) Uani 1 d . . .
H13A H 0.4632 0.8890 0.2820 0.034 Uiso 1 calc . . R
H13B H 0.5377 0.8010 0.3342 0.034 Uiso 1 calc . . R
C14 C 0.8308(10) 0.9340(4) 0.3385(2) 0.0291(12) Uani 1 d . . .
H14A H 0.9748 0.8924 0.3589 0.035 Uiso 1 calc . . R
H14B H 0.9095 0.9781 0.3045 0.035 Uiso 1 calc . . R
C15 C 0.7239(10) 1.0172(4) 0.3965(2) 0.0310(13) Uani 1 d . . .
H15A H 0.5675 1.0526 0.3769 0.037 Uiso 1 calc . . R
H15B H 0.6614 0.9734 0.4326 0.037 Uiso 1 calc . . R
C16 C 0.9308(10) 1.1122(4) 0.4307(2) 0.0287(12) Uani 1 d . . .
H16A H 0.9905 1.1573 0.3949 0.034 Uiso 1 calc . . R
H16B H 1.0888 1.0771 0.4497 0.034 Uiso 1 calc . . R
C17 C 0.8213(10) 1.1928(4) 0.4894(2) 0.0280(12) Uani 1 d . . .
H17A H 0.7819 1.1491 0.5276 0.034 Uiso 1 calc . . R
H17B H 0.6508 1.2203 0.4718 0.034 Uiso 1 calc . . R
C18 C 1.0142(11) 1.2972(4) 0.5188(3) 0.0371(14) Uani 1 d . . .
H18A H 1.1797 1.2704 0.5398 0.045 Uiso 1 calc . . R
H18B H 1.0639 1.3385 0.4804 0.045 Uiso 1 calc . . R
C19 C 0.8876(13) 1.3797(4) 0.5737(3) 0.0535(17) Uani 1 d . . .
H19A H 0.7267 1.4084 0.5528 0.080 Uiso 1 calc . . GR
H19B H 1.0165 1.4433 0.5909 0.080 Uiso 1 calc . . GR
H19C H 0.8398 1.3395 0.6121 0.080 Uiso 1 calc . . GR
Cl2 Cl 0.6866(4) 1.13698(14) 0.04404(10) 0.0784(6) Uani 1 d B . .
C20 C 0.6662(11) 1.0525(5) 0.1117(3) 0.0406(14) Uani 1 d . . .
H20 H 0.5077 0.9975 0.0992 0.049 Uiso 0.75 calc A 1 R
H20A H 0.5438 0.9826 0.1005 0.049 Uiso 0.25 calc A 2 R
Cl1 Cl 0.9605(6) 0.9703(2) 0.11426(16) 0.0567(8) Uani 0.75 d B 1 .
Cl3 Cl 0.6262(7) 1.1249(3) 0.19573(16) 0.0668(9) Uani 0.75 d B 1 .
Cl1' Cl 0.979(2) 1.0306(8) 0.1466(5) 0.066(3) Uani 0.25 d B 2 .
Cl2' Cl 0.528(2) 1.1718(7) 0.1691(5) 0.070(3) Uani 0.25 d B 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 C8 1.897(5) . ?
O1 C11 1.217(5) . ?
N1 C1 1.321(5) 2_465 ?
N1 C2 1.360(5) . ?
N2 C10 1.395(5) . ?
N2 C11 1.371(6) . ?
N2 C12 1.453(5) . ?
C1 N1 1.321(5) 2_465 ?
C1 H1 0.9300 . ?
C1 C2 1.402(6) . ?
C2 C3 1.447(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.341(6) . ?
C4 C5 1.459(6) . ?
C4 C11 1.521(6) . ?
C5 C6 1.391(6) . ?
C5 C10 1.414(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.375(6) . ?
C8 C9 1.384(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.532(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.522(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.520(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.517(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.519(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.527(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.523(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
Cl2 C20 1.736(5) . ?
C20 H20 0.9800 . ?
C20 H20A 0.9800 . ?
C20 Cl1 1.782(6) . ?
C20 Cl3 1.751(6) . ?
C20 Cl1' 1.686(11) . ?
C20 Cl2' 1.850(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.6(4) 2_465 . ?
C10 N2 C12 126.7(4) . . ?
C11 N2 C10 110.7(4) . . ?
C11 N2 C12 122.5(4) . . ?
N1 C1 H1 117.9 2_465 . ?
N1 C1 C2 124.3(4) 2_465 . ?
C2 C1 H1 117.9 . . ?
N1 C2 C1 119.1(4) . . ?
N1 C2 C3 121.8(4) . . ?
C1 C2 C3 119.1(4) . . ?
C2 C3 H3 114.3 . . ?
C4 C3 C2 131.4(4) . . ?
C4 C3 H3 114.3 . . ?
C3 C4 C5 138.6(4) . . ?
C3 C4 C11 115.9(4) . . ?
C5 C4 C11 105.5(4) . . ?
C6 C5 C4 134.0(4) . . ?
C6 C5 C10 119.3(4) . . ?
C10 C5 C4 106.7(4) . . ?
C5 C6 H6 120.7 . . ?
C5 C6 C7 118.7(5) . . ?
C7 C6 H6 120.7 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 Br1 118.9(4) . . ?
C7 C8 C9 123.4(5) . . ?
C9 C8 Br1 117.7(4) . . ?
C8 C9 H9 121.8 . . ?
C10 C9 C8 116.3(5) . . ?
C10 C9 H9 121.8 . . ?
N2 C10 C5 110.4(4) . . ?
C9 C10 N2 127.1(4) . . ?
C9 C10 C5 122.4(4) . . ?
O1 C11 N2 125.4(4) . . ?
O1 C11 C4 127.9(4) . . ?
N2 C11 C4 106.7(4) . . ?
N2 C12 H12A 109.2 . . ?
N2 C12 H12B 109.2 . . ?
N2 C12 C13 111.9(4) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 C12 113.2(4) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 113.0(4) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.5(4) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C15 C16 C17 113.6(4) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.6 . . ?
C16 C17 C18 114.4(4) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C17 112.5(4) . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Cl2 C20 H20 107.2 . . ?
Cl2 C20 H20A 114.8 . . ?
Cl2 C20 Cl1 108.5(3) . . ?
Cl2 C20 Cl3 116.7(3) . . ?
Cl2 C20 Cl2' 91.2(4) . . ?
H20 C20 H20A 15.1 . . ?
Cl1 C20 H20 107.2 . . ?
Cl1 C20 H20A 92.2 . . ?
Cl1 C20 Cl2' 136.4(5) . . ?
Cl3 C20 H20 107.2 . . ?
Cl3 C20 H20A 112.0 . . ?
Cl3 C20 Cl1 109.7(3) . . ?
Cl3 C20 Cl2' 29.8(3) . . ?
Cl1' C20 Cl2 111.0(4) . . ?
Cl1' C20 H20 129.4 . . ?
Cl1' C20 H20A 114.8 . . ?
Cl1' C20 Cl1 29.0(3) . . ?
Cl1' C20 Cl3 83.9(4) . . ?
Cl1' C20 Cl2' 107.9(5) . . ?
Cl2' C20 H20 103.2 . . ?
Cl2' C20 H20A 114.8 . . ?

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
Br1 C8 C9 C10 178.8(3) . . . . ?
N1 C1 C2 N1 0.9(7) 2_465 . . . ?
N1 C1 C2 C3 -179.2(4) 2_465 . . . ?
N1 C2 C3 C4 1.6(8) . . . . ?
N2 C12 C13 C14 -176.4(4) . . . . ?
C1 N1 C2 C1 -0.8(7) 2_465 . . . ?
C1 N1 C2 C3 179.2(4) 2_465 . . . ?
C1 C2 C3 C4 -178.3(5) . . . . ?
C2 C3 C4 C5 1.4(9) . . . . ?
C2 C3 C4 C11 180.0(4) . . . . ?
C3 C4 C5 C6 0.9(10) . . . . ?
C3 C4 C5 C10 179.5(5) . . . . ?
C3 C4 C11 O1 0.9(7) . . . . ?
C3 C4 C11 N2 180.0(4) . . . . ?
C4 C5 C6 C7 177.9(4) . . . . ?
C4 C5 C10 N2 -0.3(5) . . . . ?
C4 C5 C10 C9 -179.1(4) . . . . ?
C5 C4 C11 O1 179.9(4) . . . . ?
C5 C4 C11 N2 -1.0(5) . . . . ?
C5 C6 C7 C8 0.9(7) . . . . ?
C6 C5 C10 N2 178.5(4) . . . . ?
C6 C5 C10 C9 -0.2(7) . . . . ?
C6 C7 C8 Br1 -179.7(3) . . . . ?
C6 C7 C8 C9 -0.4(7) . . . . ?
C7 C8 C9 C10 -0.4(7) . . . . ?
C8 C9 C10 N2 -177.8(4) . . . . ?
C8 C9 C10 C5 0.7(7) . . . . ?
C10 N2 C11 O1 179.9(4) . . . . ?
C10 N2 C11 C4 0.8(5) . . . . ?
C10 N2 C12 C13 -84.0(5) . . . . ?
C10 C5 C6 C7 -0.6(7) . . . . ?
C11 N2 C10 C5 -0.3(5) . . . . ?
C11 N2 C10 C9 178.4(4) . . . . ?
C11 N2 C12 C13 90.6(5) . . . . ?
C11 C4 C5 C6 -177.8(5) . . . . ?
C11 C4 C5 C10 0.8(5) . . . . ?
C12 N2 C10 C5 174.8(4) . . . . ?
C12 N2 C10 C9 -6.5(7) . . . . ?
C12 N2 C11 O1 4.6(7) . . . . ?
C12 N2 C11 C4 -174.5(4) . . . . ?
C12 C13 C14 C15 177.5(4) . . . . ?
C13 C14 C15 C16 -174.3(4) . . . . ?
C14 C15 C16 C17 -178.8(4) . . . . ?
C15 C16 C17 C18 -173.2(4) . . . . ?
C16 C17 C18 C19 175.9(4) . . . . ?

_olex2_date_sample_data_collection 2015-05-06
_olex2_submission_special_instructions 'No special instructions were received'
