# Electronic Supplementary Material (ESI) for ChemComm.
# 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_151014ch
_database_code_depnum_ccdc_archive 'CCDC 1526997'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C33 H21 Br6 N3), C2.50 Cl5, 0.5(C Cl2)'
_chemical_formula_sum            'C69 H42 Br12 Cl6 N6'
_chemical_formula_weight         2126.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.811(4)
_cell_length_b                   15.977(4)
_cell_length_c                   17.680(6)
_cell_angle_alpha                115.619(7)
_cell_angle_beta                 108.577(8)
_cell_angle_gamma                91.4359(8)
_cell_volume                     3510.4(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3221
_cell_measurement_theta_min      30.9
_cell_measurement_theta_max      68.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.012
_exptl_crystal_F_000             2004
_exptl_transmission_factor_min   0.365
_exptl_transmission_factor_max   0.654
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    10.614
_shelx_estimated_absorpt_T_min   0.299
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            42365
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.588
_diffrn_reflns_theta_max         62.999
_diffrn_reflns_theta_full        62.999
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             10888
_reflns_number_gt                10240
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+17.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10888
_refine_ls_number_parameters     914
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1447
_refine_ls_wR_factor_gt          0.1429
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.007
_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_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
C1 C 0.0509(4) 0.2984(4) 0.6968(4) 0.0197(12) Uani 1 1 d . . . . .
C2 C -0.0308(4) 0.2390(4) 0.6212(4) 0.0237(13) Uani 1 1 d . . . . .
C3 C -0.0217(4) 0.2385(4) 0.5457(4) 0.0251(13) Uani 1 1 d . . . . .
C4 C 0.0657(4) 0.2984(4) 0.5729(4) 0.0221(12) Uani 1 1 d . . . . .
C5 C 0.0990(4) 0.3240(4) 0.5146(4) 0.0249(13) Uani 1 1 d . . . . .
C6 C 0.0384(5) 0.3699(4) 0.4733(4) 0.0292(14) Uani 1 1 d . . . . .
H1 H -0.0178 0.3851 0.4872 0.035 Uiso 1 1 calc R U . . .
C7 C 0.0577(5) 0.3938(5) 0.4130(5) 0.0344(15) Uani 1 1 d . . . . .
H2 H 0.0159 0.4259 0.3865 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1389(5) 0.3704(5) 0.3917(5) 0.0353(15) Uani 1 1 d . . . . .
H3 H 0.1527 0.3857 0.3498 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1993(5) 0.3251(4) 0.4312(4) 0.0292(14) Uani 1 1 d . . . . .
H4 H 0.2543 0.3089 0.4153 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1828(5) 0.3019(4) 0.4944(4) 0.0260(13) Uani 1 1 d . . . . .
C11 C 0.2573(4) 0.2592(4) 0.5363(4) 0.0232(12) Uani 1 1 d . . . . .
C12 C 0.3566(4) 0.2860(4) 0.5676(4) 0.0227(12) Uani 1 1 d . . . . .
C13 C 0.3997(4) 0.2198(4) 0.5925(4) 0.0214(12) Uani 1 1 d . . . . .
C14 C 0.3265(4) 0.1533(4) 0.5780(4) 0.0213(12) Uani 1 1 d . . . . .
C15 C 0.3338(4) 0.0719(4) 0.5993(4) 0.0197(12) Uani 1 1 d . . . . .
C16 C 0.3541(4) -0.0118(4) 0.5413(4) 0.0251(13) Uani 1 1 d . . . . .
H5 H 0.3596 -0.0175 0.4872 0.030 Uiso 1 1 calc R U . . .
C17 C 0.3664(4) -0.0859(4) 0.5617(4) 0.0263(13) Uani 1 1 d . . . . .
H6 H 0.3792 -0.1427 0.5214 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3599(4) -0.0771(4) 0.6415(5) 0.0255(13) Uani 1 1 d . . . . .
H7 H 0.3694 -0.1275 0.6563 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3397(4) 0.0049(4) 0.6991(4) 0.0230(12) Uani 1 1 d . . . . .
H8 H 0.3354 0.0105 0.7535 0.028 Uiso 1 1 calc R U . . .
C20 C 0.3256(4) 0.0804(4) 0.6783(4) 0.0199(12) Uani 1 1 d . . . . .
C21 C 0.3095(4) 0.1690(4) 0.7441(4) 0.0181(11) Uani 1 1 d . . . . .
C22 C 0.3762(4) 0.2470(4) 0.8121(4) 0.0181(11) Uani 1 1 d . . . . .
C23 C 0.3273(4) 0.3118(4) 0.8605(4) 0.0193(12) Uani 1 1 d . . . . .
C24 C 0.2300(4) 0.2719(4) 0.8206(4) 0.0176(11) Uani 1 1 d . . . . .
C25 C 0.1505(4) 0.3126(4) 0.8489(4) 0.0191(12) Uani 1 1 d . . . . .
C26 C 0.1598(4) 0.3406(4) 0.9382(4) 0.0226(12) Uani 1 1 d . . . . .
H9 H 0.2161 0.3336 0.9780 0.027 Uiso 1 1 calc R U . . .
C27 C 0.0878(5) 0.3786(4) 0.9693(4) 0.0267(13) Uani 1 1 d . . . . .
H10 H 0.0948 0.3966 1.0299 0.032 Uiso 1 1 calc R U . . .
C28 C 0.0061(4) 0.3901(4) 0.9125(4) 0.0263(13) Uani 1 1 d . . . . .
H11 H -0.0436 0.4152 0.9336 0.032 Uiso 1 1 calc R U . . .
C29 C -0.0030(4) 0.3649(4) 0.8242(4) 0.0229(13) Uani 1 1 d . . . . .
H12 H -0.0587 0.3740 0.7855 0.027 Uiso 1 1 calc R U . . .
C30 C 0.0685(4) 0.3263(4) 0.7915(4) 0.0194(12) Uani 1 1 d . . . . .
C31 C 0.1981(4) 0.4048(4) 0.7205(4) 0.0231(12) Uani 1 1 d . . . . .
H80 H 0.204(5) 0.455(5) 0.699(5) 0.032(18) Uiso 1 1 d . . . . .
H31 H 0.259(6) 0.376(5) 0.723(5) 0.04(2) Uiso 1 1 d . . . . .
C32 C 0.1468(4) 0.1137(5) 0.5040(5) 0.0276(14) Uani 1 1 d . . . . .
C33 C 0.1349(4) 0.1083(4) 0.7068(5) 0.0222(13) Uani 1 1 d . . . . .
H77 H 0.138(5) 0.076(5) 0.743(5) 0.025(17) Uiso 1 1 d . . . . .
H33 H 0.135(4) 0.069(5) 0.657(5) 0.010(15) Uiso 1 1 d . . . . .
N1 N 0.1078(3) 0.3330(3) 0.6641(3) 0.0189(10) Uani 1 1 d . . . . .
N2 N 0.2409(4) 0.1775(3) 0.5433(3) 0.0235(11) Uani 1 1 d . . . . .
N3 N 0.2190(3) 0.1846(3) 0.7489(3) 0.0181(10) Uani 1 1 d . . . . .
Br1 Br -0.13145(4) 0.16743(4) 0.62300(5) 0.03000(17) Uani 1 1 d . . . . .
Br2 Br -0.10610(5) 0.16458(5) 0.42690(5) 0.03648(18) Uani 1 1 d . . . . .
Br3 Br 0.42693(5) 0.39381(4) 0.58089(5) 0.03165(18) Uani 1 1 d . . . . .
Br4 Br 0.53330(4) 0.21870(4) 0.63106(4) 0.02718(16) Uani 1 1 d . . . . .
Br5 Br 0.51010(4) 0.26355(4) 0.84040(4) 0.02501(16) Uani 1 1 d . . . . .
Br6 Br 0.38593(4) 0.43075(4) 0.95764(4) 0.02657(16) Uani 1 1 d . . . . .
C34 C 0.2961(4) 1.0538(4) 0.1092(4) 0.0188(11) Uani 1 1 d . . . . .
C35 C 0.3474(4) 1.1057(4) 0.0853(4) 0.0218(12) Uani 1 1 d . . . . .
C36 C 0.2869(4) 1.1002(4) 0.0038(4) 0.0221(12) Uani 1 1 d . . . . .
C37 C 0.1964(4) 1.0456(4) -0.0226(4) 0.0210(12) Uani 1 1 d . . . . .
C38 C 0.1068(4) 1.0332(4) -0.0960(4) 0.0203(12) Uani 1 1 d . . . . .
C39 C 0.0754(4) 1.1153(4) -0.0955(4) 0.0217(12) Uani 1 1 d . . . . .
H13 H 0.1116 1.1753 -0.0481 0.026 Uiso 1 1 calc R U . . .
C40 C -0.0073(4) 1.1109(4) -0.1627(4) 0.0244(13) Uani 1 1 d . . . . .
H14 H -0.0267 1.1677 -0.1613 0.029 Uiso 1 1 calc R U . . .
C41 C -0.0614(4) 1.0254(4) -0.2312(4) 0.0252(13) Uani 1 1 d . . . . .
H15 H -0.1187 1.0228 -0.2766 0.030 Uiso 1 1 calc R U . . .
C42 C -0.0324(4) 0.9418(4) -0.2345(4) 0.0243(13) Uani 1 1 d . . . . .
H16 H -0.0698 0.8826 -0.2826 0.029 Uiso 1 1 calc R U . . .
C43 C 0.0514(4) 0.9445(4) -0.1677(4) 0.0209(12) Uani 1 1 d . . . . .
C44 C 0.0759(4) 0.8548(4) -0.1714(4) 0.0207(12) Uani 1 1 d . . . . .
C45 C 0.0201(4) 0.7833(4) -0.1723(4) 0.0233(12) Uani 1 1 d . . . . .
C46 C 0.0746(4) 0.7132(4) -0.1734(4) 0.0240(13) Uani 1 1 d . . . . .
C47 C 0.1640(4) 0.7402(4) -0.1731(4) 0.0218(12) Uani 1 1 d . . . . .
C48 C 0.2480(4) 0.6927(4) -0.1744(4) 0.0214(12) Uani 1 1 d . . . . .
C49 C 0.2654(5) 0.6468(4) -0.2539(5) 0.0274(13) Uani 1 1 d . . . . .
H17 H 0.2242 0.6478 -0.3069 0.033 Uiso 1 1 calc R U . . .
C50 C 0.3428(5) 0.5991(4) -0.2567(5) 0.0314(15) Uani 1 1 d . . . . .
H18 H 0.3549 0.5688 -0.3111 0.038 Uiso 1 1 calc R U . . .
C51 C 0.4011(5) 0.5964(4) -0.1806(5) 0.0306(15) Uani 1 1 d . . . . .
H19 H 0.4530 0.5627 -0.1827 0.037 Uiso 1 1 calc R U . . .
C52 C 0.3853(4) 0.6424(4) -0.1000(5) 0.0274(13) Uani 1 1 d . . . . .
H20 H 0.4263 0.6395 -0.0478 0.033 Uiso 1 1 calc R U . . .
C53 C 0.3104(4) 0.6922(4) -0.0953(4) 0.0217(12) Uani 1 1 d . . . . .
C54 C 0.2971(4) 0.7441(4) -0.0078(4) 0.0194(12) Uani 1 1 d . . . . .
C55 C 0.2573(4) 0.7107(4) 0.0369(4) 0.0208(12) Uani 1 1 d . . . . .
C56 C 0.2677(4) 0.7869(4) 0.1195(4) 0.0182(11) Uani 1 1 d . . . . .
C57 C 0.3139(4) 0.8672(4) 0.1260(4) 0.0185(11) Uani 1 1 d . . . . .
C58 C 0.3413(4) 0.9643(4) 0.2026(4) 0.0190(12) Uani 1 1 d . . . . .
C59 C 0.3802(4) 0.9728(4) 0.2891(4) 0.0222(12) Uani 1 1 d . . . . .
H21 H 0.3931 0.9180 0.2958 0.027 Uiso 1 1 calc R U . . .
C60 C 0.4007(4) 1.0592(4) 0.3656(4) 0.0251(13) Uani 1 1 d . . . . .
H22 H 0.4259 1.0628 0.4238 0.030 Uiso 1 1 calc R U . . .
C61 C 0.3841(4) 1.1400(4) 0.3568(4) 0.0256(13) Uani 1 1 d . . . . .
H23 H 0.3965 1.1992 0.4085 0.031 Uiso 1 1 calc R U . . .
C62 C 0.3495(4) 1.1331(4) 0.2720(4) 0.0243(13) Uani 1 1 d . . . . .
H24 H 0.3404 1.1891 0.2664 0.029 Uiso 1 1 calc R U . . .
C63 C 0.3270(4) 1.0476(4) 0.1942(4) 0.0189(11) Uani 1 1 d . . . . .
C64 C 0.1285(4) 0.9589(4) 0.0443(4) 0.0209(12) Uani 1 1 d . . . . .
H93 H 0.1536 0.9491 0.0976 0.031 Uiso 1 1 calc R U . . .
H94 H 0.0732 0.9911 0.0466 0.031 Uiso 1 1 calc R U . . .
H95 H 0.1075 0.8976 -0.0101 0.031 Uiso 1 1 calc R U . . .
N4 N 0.2050(3) 1.0172(3) 0.0424(3) 0.0174(10) Uani 1 1 d . . . . .
C65 C 0.2361(4) 0.8723(4) -0.1899(4) 0.0249(13) Uani 1 1 d . . . . .
H90 H 0.2918 0.8404 -0.1861 0.037 Uiso 1 1 calc R U . . .
H91 H 0.2077 0.8668 -0.2504 0.037 Uiso 1 1 calc R U . . .
H92 H 0.2574 0.9392 -0.1453 0.037 Uiso 1 1 calc R U . . .
N5 N 0.1635(3) 0.8280(3) -0.1717(3) 0.0208(10) Uani 1 1 d . . . . .
C66 C 0.4035(4) 0.8935(4) 0.0357(4) 0.0233(13) Uani 1 1 d . . . . .
H96 H 0.4183 0.9599 0.0814 0.035 Uiso 1 1 calc R U . . .
H97 H 0.4629 0.8671 0.0424 0.035 Uiso 1 1 calc R U . . .
H98 H 0.3772 0.8892 -0.0245 0.035 Uiso 1 1 calc R U . . .
N6 N 0.3317(3) 0.8398(3) 0.0473(3) 0.0182(10) Uani 1 1 d . . . . .
Br7 Br 0.47742(4) 1.16721(5) 0.14872(4) 0.02855(17) Uani 1 1 d . . . . .
Br8 Br 0.32201(4) 1.15465(4) -0.06003(4) 0.02486(16) Uani 1 1 d . . . . .
Br9 Br -0.10047(4) 0.78841(4) -0.15894(5) 0.02786(17) Uani 1 1 d . . . . .
Br10 Br 0.03051(5) 0.59678(5) -0.18270(5) 0.03311(18) Uani 1 1 d . . . . .
Br11 Br 0.20982(4) 0.58423(4) 0.00039(5) 0.02664(17) Uani 1 1 d . . . . .
Br12 Br 0.22155(4) 0.77793(4) 0.20376(4) 0.02260(16) Uani 1 1 d . . . . .
C67 C 0.2767(13) 0.4203(9) 0.2309(11) 0.052(4) Uani 0.5 1 d D U P A 5
Cl1 Cl 0.3044(4) 0.3277(4) 0.1500(3) 0.0613(13) Uani 0.5 1 d D U P A 5
Cl2 Cl 0.2974(5) 0.5245(4) 0.2219(4) 0.0828(18) Uani 0.5 1 d D U P A 5
C72 C 0.3485(4) 0.4364(3) 0.3391(4) 0.0144(10) Uiso 1 1 d D U . B 4
Cl4 Cl 0.3700(5) 0.5048(5) 0.4344(5) 0.188(2) Uiso 1 1 d D U . B 4
Cl3 Cl 0.2890(10) 0.5189(11) 0.3057(11) 0.385(7) Uiso 1 1 d D U . B 4
C74 C 0.3590(12) 0.640(2) 0.4757(12) 0.104(6) Uani 0.5 1 d D U P C 1
Cl7 Cl 0.4253(5) 0.6729(5) 0.5946(5) 0.0917(17) Uani 0.5 1 d D U P C 1
Cl8 Cl 0.2371(5) 0.6379(5) 0.4652(6) 0.104(2) Uani 0.5 1 d D U P C 1
C73 C 0.2680(19) 0.666(2) 0.4528(16) 0.104(7) Uani 0.5 1 d D U P D 2
Cl5 Cl 0.1566(4) 0.5836(3) 0.3796(4) 0.0697(13) Uani 0.5 1 d D U P D 2
Cl6 Cl 0.3150(9) 0.6513(6) 0.5510(6) 0.135(3) Uani 0.5 1 d D U P D 2
Cl9 Cl 0.3379(9) 0.3794(8) 0.1772(10) 0.149(4) Uani 0.5 1 d D U P E 3
Cl10 Cl 0.2173(7) 0.5105(10) 0.2233(7) 0.157(4) Uani 0.5 1 d D U P E 3
C75 C 0.320(3) 0.492(2) 0.184(3) 0.158(8) Uani 0.5 1 d D U P E 3
H76 H 0.078(5) 0.128(4) 0.695(4) 0.018(15) Uiso 1 1 d . . . . .
H81 H 0.194(6) 0.433(6) 0.777(6) 0.04(2) Uiso 1 1 d . . . . .
H85 H 0.116(6) 0.119(5) 0.459(6) 0.03(2) Uiso 1 1 d . . . . .
H86 H 0.107(5) 0.131(5) 0.551(5) 0.025(17) Uiso 1 1 d . . . . .
H87 H 0.166(6) 0.048(6) 0.486(6) 0.05(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.382(7) . ?
C1 C2 1.403(8) . ?
C1 C30 1.464(9) . ?
C2 C3 1.380(9) . ?
C2 Br1 1.873(6) . ?
C3 C4 1.402(8) . ?
C3 Br2 1.865(6) . ?
C4 N1 1.366(8) . ?
C4 C5 1.469(9) . ?
C5 C6 1.397(9) . ?
C5 C10 1.409(9) . ?
C6 C7 1.381(10) . ?
C6 H1 0.9500 . ?
C7 C8 1.384(10) . ?
C7 H2 0.9500 . ?
C8 C9 1.373(10) . ?
C8 H3 0.9500 . ?
C9 C10 1.404(9) . ?
C9 H4 0.9500 . ?
C10 C11 1.479(9) . ?
C11 C12 1.378(9) . ?
C11 N2 1.386(8) . ?
C12 C13 1.406(8) . ?
C12 Br3 1.873(6) . ?
C13 C14 1.378(8) . ?
C13 Br4 1.880(6) . ?
C14 N2 1.367(8) . ?
C14 C15 1.500(8) . ?
C15 C20 1.389(9) . ?
C15 C16 1.400(8) . ?
C16 C17 1.380(9) . ?
C16 H5 0.9500 . ?
C17 C18 1.392(9) . ?
C17 H6 0.9500 . ?
C18 C19 1.379(9) . ?
C18 H7 0.9500 . ?
C19 C20 1.408(8) . ?
C19 H8 0.9500 . ?
C20 C21 1.478(8) . ?
C21 C22 1.364(8) . ?
C21 N3 1.391(7) . ?
C22 C23 1.413(8) . ?
C22 Br5 1.865(5) . ?
C23 C24 1.378(8) . ?
C23 Br6 1.860(6) . ?
C24 N3 1.381(7) . ?
C24 C25 1.481(8) . ?
C25 C26 1.400(9) . ?
C25 C30 1.404(8) . ?
C26 C27 1.386(8) . ?
C26 H9 0.9500 . ?
C27 C28 1.380(10) . ?
C27 H10 0.9500 . ?
C28 C29 1.392(9) . ?
C28 H11 0.9500 . ?
C29 C30 1.397(8) . ?
C29 H12 0.9500 . ?
C31 N1 1.478(7) . ?
C31 H80 1.05(8) . ?
C31 H31 1.02(8) . ?
C31 H81 0.93(9) . ?
C32 N2 1.471(8) . ?
C32 H85 0.82(9) . ?
C32 H86 1.11(7) . ?
C32 H87 1.03(9) . ?
C33 N3 1.463(7) . ?
C33 H77 0.97(8) . ?
C33 H33 0.83(7) . ?
C33 H76 0.91(7) . ?
C34 N4 1.381(7) . ?
C34 C35 1.385(8) . ?
C34 C63 1.473(8) . ?
C35 C36 1.398(9) . ?
C35 Br7 1.873(6) . ?
C36 C37 1.402(8) . ?
C36 Br8 1.871(6) . ?
C37 N4 1.379(8) . ?
C37 C38 1.466(8) . ?
C38 C39 1.400(8) . ?
C38 C43 1.420(8) . ?
C39 C40 1.383(9) . ?
C39 H13 0.9500 . ?
C40 C41 1.369(9) . ?
C40 H14 0.9500 . ?
C41 C42 1.396(9) . ?
C41 H15 0.9500 . ?
C42 C43 1.400(9) . ?
C42 H16 0.9500 . ?
C43 C44 1.466(8) . ?
C44 N5 1.377(8) . ?
C44 C45 1.384(8) . ?
C45 C46 1.395(8) . ?
C45 Br9 1.873(6) . ?
C46 C47 1.379(8) . ?
C46 Br10 1.876(6) . ?
C47 N5 1.393(8) . ?
C47 C48 1.475(8) . ?
C48 C49 1.389(9) . ?
C48 C53 1.413(9) . ?
C49 C50 1.394(9) . ?
C49 H17 0.9500 . ?
C50 C51 1.368(10) . ?
C50 H18 0.9500 . ?
C51 C52 1.393(9) . ?
C51 H19 0.9500 . ?
C52 C53 1.385(8) . ?
C52 H20 0.9500 . ?
C53 C54 1.487(8) . ?
C54 C55 1.379(8) . ?
C54 N6 1.381(7) . ?
C55 C56 1.395(8) . ?
C55 Br11 1.872(6) . ?
C56 C57 1.381(8) . ?
C56 Br12 1.880(6) . ?
C57 N6 1.382(8) . ?
C57 C58 1.485(8) . ?
C58 C59 1.394(9) . ?
C58 C63 1.414(8) . ?
C59 C60 1.390(9) . ?
C59 H21 0.9500 . ?
C60 C61 1.384(9) . ?
C60 H22 0.9500 . ?
C61 C62 1.373(9) . ?
C61 H23 0.9500 . ?
C62 C63 1.390(8) . ?
C62 H24 0.9500 . ?
C64 N4 1.467(7) . ?
C64 H93 0.9800 . ?
C64 H94 0.9800 . ?
C64 H95 0.9800 . ?
C65 N5 1.462(7) . ?
C65 H90 0.9800 . ?
C65 H91 0.9800 . ?
C65 H92 0.9800 . ?
C66 N6 1.467(7) . ?
C66 H96 0.9800 . ?
C66 H97 0.9800 . ?
C66 H98 0.9800 . ?
C67 Cl1 1.725(14) . ?
C67 Cl2 1.768(13) . ?
C72 Cl4 1.477(8) . ?
C72 Cl3 1.806(13) . ?
C74 Cl8 1.754(16) . ?
C74 Cl7 1.833(18) . ?
C73 Cl6 1.773(18) . ?
C73 Cl5 1.786(18) . ?
Cl9 C75 1.790(19) . ?
Cl10 C75 1.846(19) . ?

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
N1 C1 C2 105.5(5) . . ?
N1 C1 C30 126.6(5) . . ?
C2 C1 C30 127.7(5) . . ?
C3 C2 C1 108.7(5) . . ?
C3 C2 Br1 126.2(5) . . ?
C1 C2 Br1 125.0(5) . . ?
C2 C3 C4 108.2(5) . . ?
C2 C3 Br2 126.2(4) . . ?
C4 C3 Br2 125.5(5) . . ?
N1 C4 C3 106.3(5) . . ?
N1 C4 C5 127.8(5) . . ?
C3 C4 C5 125.7(6) . . ?
C6 C5 C10 119.0(6) . . ?
C6 C5 C4 115.5(5) . . ?
C10 C5 C4 125.4(6) . . ?
C7 C6 C5 122.1(6) . . ?
C7 C6 H1 119.0 . . ?
C5 C6 H1 119.0 . . ?
C6 C7 C8 119.0(6) . . ?
C6 C7 H2 120.5 . . ?
C8 C7 H2 120.5 . . ?
C9 C8 C7 120.0(6) . . ?
C9 C8 H3 120.0 . . ?
C7 C8 H3 120.0 . . ?
C8 C9 C10 122.3(6) . . ?
C8 C9 H4 118.9 . . ?
C10 C9 H4 118.9 . . ?
C9 C10 C5 117.7(6) . . ?
C9 C10 C11 116.6(5) . . ?
C5 C10 C11 125.7(6) . . ?
C12 C11 N2 105.9(5) . . ?
C12 C11 C10 127.4(5) . . ?
N2 C11 C10 126.4(5) . . ?
C11 C12 C13 108.5(5) . . ?
C11 C12 Br3 127.6(5) . . ?
C13 C12 Br3 123.8(4) . . ?
C14 C13 C12 108.0(5) . . ?
C14 C13 Br4 126.4(5) . . ?
C12 C13 Br4 125.5(4) . . ?
N2 C14 C13 106.8(5) . . ?
N2 C14 C15 124.0(5) . . ?
C13 C14 C15 129.1(5) . . ?
C20 C15 C16 119.6(5) . . ?
C20 C15 C14 120.7(5) . . ?
C16 C15 C14 119.6(5) . . ?
C17 C16 C15 120.9(6) . . ?
C17 C16 H5 119.5 . . ?
C15 C16 H5 119.5 . . ?
C16 C17 C18 119.6(5) . . ?
C16 C17 H6 120.2 . . ?
C18 C17 H6 120.2 . . ?
C19 C18 C17 120.0(6) . . ?
C19 C18 H7 120.0 . . ?
C17 C18 H7 120.0 . . ?
C18 C19 C20 120.8(6) . . ?
C18 C19 H8 119.6 . . ?
C20 C19 H8 119.6 . . ?
C15 C20 C19 119.0(5) . . ?
C15 C20 C21 121.7(5) . . ?
C19 C20 C21 119.2(5) . . ?
C22 C21 N3 107.3(5) . . ?
C22 C21 C20 128.8(5) . . ?
N3 C21 C20 123.8(5) . . ?
C21 C22 C23 108.4(5) . . ?
C21 C22 Br5 126.1(4) . . ?
C23 C22 Br5 125.4(4) . . ?
C24 C23 C22 107.6(5) . . ?
C24 C23 Br6 127.4(4) . . ?
C22 C23 Br6 125.0(4) . . ?
C23 C24 N3 107.5(5) . . ?
C23 C24 C25 127.3(5) . . ?
N3 C24 C25 125.2(5) . . ?
C26 C25 C30 119.1(5) . . ?
C26 C25 C24 117.6(5) . . ?
C30 C25 C24 123.3(5) . . ?
C27 C26 C25 120.9(6) . . ?
C27 C26 H9 119.6 . . ?
C25 C26 H9 119.6 . . ?
C28 C27 C26 120.2(6) . . ?
C28 C27 H10 119.9 . . ?
C26 C27 H10 119.9 . . ?
C27 C28 C29 119.6(5) . . ?
C27 C28 H11 120.2 . . ?
C29 C28 H11 120.2 . . ?
C28 C29 C30 121.0(6) . . ?
C28 C29 H12 119.5 . . ?
C30 C29 H12 119.5 . . ?
C29 C30 C25 119.2(6) . . ?
C29 C30 C1 117.2(5) . . ?
C25 C30 C1 123.6(5) . . ?
N1 C31 H80 113(4) . . ?
N1 C31 H31 113(4) . . ?
H80 C31 H31 107(6) . . ?
N1 C31 H81 103(5) . . ?
H80 C31 H81 110(6) . . ?
H31 C31 H81 110(7) . . ?
N2 C32 H85 105(5) . . ?
N2 C32 H86 113(4) . . ?
H85 C32 H86 111(6) . . ?
N2 C32 H87 103(5) . . ?
H85 C32 H87 110(7) . . ?
H86 C32 H87 114(6) . . ?
N3 C33 H77 111(4) . . ?
N3 C33 H33 109(4) . . ?
H77 C33 H33 108(6) . . ?
N3 C33 H76 113(4) . . ?
H77 C33 H76 110(6) . . ?
H33 C33 H76 106(6) . . ?
C4 N1 C1 111.3(5) . . ?
C4 N1 C31 123.6(5) . . ?
C1 N1 C31 124.9(5) . . ?
C14 N2 C11 110.9(5) . . ?
C14 N2 C32 122.3(5) . . ?
C11 N2 C32 125.9(5) . . ?
C24 N3 C21 109.2(4) . . ?
C24 N3 C33 124.4(5) . . ?
C21 N3 C33 123.0(5) . . ?
N4 C34 C35 106.8(5) . . ?
N4 C34 C63 125.6(5) . . ?
C35 C34 C63 127.2(5) . . ?
C34 C35 C36 108.1(5) . . ?
C34 C35 Br7 125.7(5) . . ?
C36 C35 Br7 126.1(4) . . ?
C35 C36 C37 108.4(5) . . ?
C35 C36 Br8 125.5(4) . . ?
C37 C36 Br8 126.0(5) . . ?
N4 C37 C36 105.8(5) . . ?
N4 C37 C38 126.5(5) . . ?
C36 C37 C38 127.1(5) . . ?
C39 C38 C43 118.2(6) . . ?
C39 C38 C37 117.1(5) . . ?
C43 C38 C37 124.6(5) . . ?
C40 C39 C38 121.4(6) . . ?
C40 C39 H13 119.3 . . ?
C38 C39 H13 119.3 . . ?
C41 C40 C39 120.3(6) . . ?
C41 C40 H14 119.8 . . ?
C39 C40 H14 119.8 . . ?
C40 C41 C42 120.1(6) . . ?
C40 C41 H15 120.0 . . ?
C42 C41 H15 120.0 . . ?
C41 C42 C43 120.6(6) . . ?
C41 C42 H16 119.7 . . ?
C43 C42 H16 119.7 . . ?
C42 C43 C38 119.3(5) . . ?
C42 C43 C44 118.5(5) . . ?
C38 C43 C44 122.1(5) . . ?
N5 C44 C45 107.0(5) . . ?
N5 C44 C43 124.5(5) . . ?
C45 C44 C43 128.4(5) . . ?
C44 C45 C46 107.9(5) . . ?
C44 C45 Br9 125.4(4) . . ?
C46 C45 Br9 126.3(5) . . ?
C47 C46 C45 109.0(5) . . ?
C47 C46 Br10 125.3(4) . . ?
C45 C46 Br10 125.5(4) . . ?
C46 C47 N5 106.1(5) . . ?
C46 C47 C48 131.4(5) . . ?
N5 C47 C48 122.6(5) . . ?
C49 C48 C53 119.5(5) . . ?
C49 C48 C47 120.2(6) . . ?
C53 C48 C47 120.3(5) . . ?
C48 C49 C50 120.7(6) . . ?
C48 C49 H17 119.6 . . ?
C50 C49 H17 119.6 . . ?
C51 C50 C49 119.5(6) . . ?
C51 C50 H18 120.3 . . ?
C49 C50 H18 120.3 . . ?
C50 C51 C52 120.8(6) . . ?
C50 C51 H19 119.6 . . ?
C52 C51 H19 119.6 . . ?
C53 C52 C51 120.6(6) . . ?
C53 C52 H20 119.7 . . ?
C51 C52 H20 119.7 . . ?
C52 C53 C48 118.9(6) . . ?
C52 C53 C54 119.8(6) . . ?
C48 C53 C54 121.3(5) . . ?
C55 C54 N6 107.2(5) . . ?
C55 C54 C53 130.0(5) . . ?
N6 C54 C53 122.7(5) . . ?
C54 C55 C56 107.9(5) . . ?
C54 C55 Br11 126.6(5) . . ?
C56 C55 Br11 125.2(4) . . ?
C57 C56 C55 108.7(5) . . ?
C57 C56 Br12 127.3(5) . . ?
C55 C56 Br12 124.0(4) . . ?
C56 C57 N6 106.6(5) . . ?
C56 C57 C58 127.5(5) . . ?
N6 C57 C58 125.9(5) . . ?
C59 C58 C63 118.1(5) . . ?
C59 C58 C57 116.9(5) . . ?
C63 C58 C57 124.9(5) . . ?
C60 C59 C58 121.8(6) . . ?
C60 C59 H21 119.1 . . ?
C58 C59 H21 119.1 . . ?
C61 C60 C59 119.7(6) . . ?
C61 C60 H22 120.1 . . ?
C59 C60 H22 120.1 . . ?
C62 C61 C60 119.0(6) . . ?
C62 C61 H23 120.5 . . ?
C60 C61 H23 120.5 . . ?
C61 C62 C63 122.7(6) . . ?
C61 C62 H24 118.7 . . ?
C63 C62 H24 118.7 . . ?
C62 C63 C58 118.6(5) . . ?
C62 C63 C34 115.5(5) . . ?
C58 C63 C34 125.7(5) . . ?
N4 C64 H93 109.5 . . ?
N4 C64 H94 109.5 . . ?
H93 C64 H94 109.5 . . ?
N4 C64 H95 109.5 . . ?
H93 C64 H95 109.5 . . ?
H94 C64 H95 109.5 . . ?
C37 N4 C34 110.8(4) . . ?
C37 N4 C64 126.0(5) . . ?
C34 N4 C64 123.1(5) . . ?
N5 C65 H90 109.5 . . ?
N5 C65 H91 109.5 . . ?
H90 C65 H91 109.5 . . ?
N5 C65 H92 109.5 . . ?
H90 C65 H92 109.5 . . ?
H91 C65 H92 109.5 . . ?
C44 N5 C47 110.0(5) . . ?
C44 N5 C65 125.2(5) . . ?
C47 N5 C65 123.2(5) . . ?
N6 C66 H96 109.5 . . ?
N6 C66 H97 109.5 . . ?
H96 C66 H97 109.5 . . ?
N6 C66 H98 109.5 . . ?
H96 C66 H98 109.5 . . ?
H97 C66 H98 109.5 . . ?
C54 N6 C57 109.8(4) . . ?
C54 N6 C66 122.3(5) . . ?
C57 N6 C66 125.0(5) . . ?
Cl1 C67 Cl2 109.7(9) . . ?
Cl4 C72 Cl3 89.4(6) . . ?
Cl8 C74 Cl7 104.7(10) . . ?
Cl6 C73 Cl5 108.7(12) . . ?
Cl9 C75 Cl10 101.0(12) . . ?

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
N1 C1 C2 C3 0.3(6) . . . . ?
C30 C1 C2 C3 174.5(5) . . . . ?
N1 C1 C2 Br1 177.1(4) . . . . ?
C30 C1 C2 Br1 -8.7(9) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
Br1 C2 C3 C4 -177.3(4) . . . . ?
C1 C2 C3 Br2 175.5(4) . . . . ?
Br1 C2 C3 Br2 -1.3(8) . . . . ?
C2 C3 C4 N1 0.6(7) . . . . ?
Br2 C3 C4 N1 -175.4(4) . . . . ?
C2 C3 C4 C5 -174.5(6) . . . . ?
Br2 C3 C4 C5 9.4(9) . . . . ?
N1 C4 C5 C6 -114.1(7) . . . . ?
C3 C4 C5 C6 60.0(8) . . . . ?
N1 C4 C5 C10 69.2(9) . . . . ?
C3 C4 C5 C10 -116.7(7) . . . . ?
C10 C5 C6 C7 0.4(10) . . . . ?
C4 C5 C6 C7 -176.6(6) . . . . ?
C5 C6 C7 C8 1.0(10) . . . . ?
C6 C7 C8 C9 -0.8(10) . . . . ?
C7 C8 C9 C10 -0.8(10) . . . . ?
C8 C9 C10 C5 2.0(10) . . . . ?
C8 C9 C10 C11 -175.9(6) . . . . ?
C6 C5 C10 C9 -1.8(9) . . . . ?
C4 C5 C10 C9 174.8(6) . . . . ?
C6 C5 C10 C11 175.9(6) . . . . ?
C4 C5 C10 C11 -7.5(10) . . . . ?
C9 C10 C11 C12 42.7(9) . . . . ?
C5 C10 C11 C12 -135.1(7) . . . . ?
C9 C10 C11 N2 -130.0(6) . . . . ?
C5 C10 C11 N2 52.3(9) . . . . ?
N2 C11 C12 C13 0.5(7) . . . . ?
C10 C11 C12 C13 -173.3(6) . . . . ?
N2 C11 C12 Br3 -177.1(4) . . . . ?
C10 C11 C12 Br3 9.1(10) . . . . ?
C11 C12 C13 C14 -1.1(7) . . . . ?
Br3 C12 C13 C14 176.6(4) . . . . ?
C11 C12 C13 Br4 175.1(4) . . . . ?
Br3 C12 C13 Br4 -7.2(8) . . . . ?
C12 C13 C14 N2 1.2(7) . . . . ?
Br4 C13 C14 N2 -174.9(4) . . . . ?
C12 C13 C14 C15 -175.5(6) . . . . ?
Br4 C13 C14 C15 8.4(9) . . . . ?
N2 C14 C15 C20 -79.8(7) . . . . ?
C13 C14 C15 C20 96.4(7) . . . . ?
N2 C14 C15 C16 103.6(7) . . . . ?
C13 C14 C15 C16 -80.2(8) . . . . ?
C20 C15 C16 C17 -0.2(9) . . . . ?
C14 C15 C16 C17 176.5(5) . . . . ?
C15 C16 C17 C18 -1.0(9) . . . . ?
C16 C17 C18 C19 1.1(9) . . . . ?
C17 C18 C19 C20 0.0(9) . . . . ?
C16 C15 C20 C19 1.2(8) . . . . ?
C14 C15 C20 C19 -175.4(5) . . . . ?
C16 C15 C20 C21 176.6(5) . . . . ?
C14 C15 C20 C21 0.0(8) . . . . ?
C18 C19 C20 C15 -1.1(8) . . . . ?
C18 C19 C20 C21 -176.6(5) . . . . ?
C15 C20 C21 C22 -85.0(8) . . . . ?
C19 C20 C21 C22 90.4(7) . . . . ?
C15 C20 C21 N3 98.4(7) . . . . ?
C19 C20 C21 N3 -86.1(7) . . . . ?
N3 C21 C22 C23 0.4(6) . . . . ?
C20 C21 C22 C23 -176.6(6) . . . . ?
N3 C21 C22 Br5 177.8(4) . . . . ?
C20 C21 C22 Br5 0.7(9) . . . . ?
C21 C22 C23 C24 -0.1(7) . . . . ?
Br5 C22 C23 C24 -177.5(4) . . . . ?
C21 C22 C23 Br6 -178.1(4) . . . . ?
Br5 C22 C23 Br6 4.6(8) . . . . ?
C22 C23 C24 N3 -0.3(6) . . . . ?
Br6 C23 C24 N3 177.6(4) . . . . ?
C22 C23 C24 C25 178.6(5) . . . . ?
Br6 C23 C24 C25 -3.5(9) . . . . ?
C23 C24 C25 C26 -54.3(8) . . . . ?
N3 C24 C25 C26 124.3(6) . . . . ?
C23 C24 C25 C30 124.0(7) . . . . ?
N3 C24 C25 C30 -57.3(8) . . . . ?
C30 C25 C26 C27 2.1(8) . . . . ?
C24 C25 C26 C27 -179.4(5) . . . . ?
C25 C26 C27 C28 -0.7(8) . . . . ?
C26 C27 C28 C29 -1.0(8) . . . . ?
C27 C28 C29 C30 1.2(8) . . . . ?
C28 C29 C30 C25 0.3(8) . . . . ?
C28 C29 C30 C1 177.6(5) . . . . ?
C26 C25 C30 C29 -1.9(8) . . . . ?
C24 C25 C30 C29 179.8(5) . . . . ?
C26 C25 C30 C1 -179.1(5) . . . . ?
C24 C25 C30 C1 2.6(8) . . . . ?
N1 C1 C30 C29 120.1(6) . . . . ?
C2 C1 C30 C29 -53.0(8) . . . . ?
N1 C1 C30 C25 -62.6(8) . . . . ?
C2 C1 C30 C25 124.3(6) . . . . ?
C3 C4 N1 C1 -0.4(6) . . . . ?
C5 C4 N1 C1 174.6(6) . . . . ?
C3 C4 N1 C31 -175.3(5) . . . . ?
C5 C4 N1 C31 -0.3(9) . . . . ?
C2 C1 N1 C4 0.1(6) . . . . ?
C30 C1 N1 C4 -174.2(5) . . . . ?
C2 C1 N1 C31 174.9(5) . . . . ?
C30 C1 N1 C31 0.6(9) . . . . ?
C13 C14 N2 C11 -0.9(7) . . . . ?
C15 C14 N2 C11 176.0(5) . . . . ?
C13 C14 N2 C32 168.7(6) . . . . ?
C15 C14 N2 C32 -14.4(9) . . . . ?
C12 C11 N2 C14 0.2(7) . . . . ?
C10 C11 N2 C14 174.1(6) . . . . ?
C12 C11 N2 C32 -168.9(6) . . . . ?
C10 C11 N2 C32 5.0(10) . . . . ?
C23 C24 N3 C21 0.5(6) . . . . ?
C25 C24 N3 C21 -178.4(5) . . . . ?
C23 C24 N3 C33 160.1(5) . . . . ?
C25 C24 N3 C33 -18.8(9) . . . . ?
C22 C21 N3 C24 -0.6(6) . . . . ?
C20 C21 N3 C24 176.6(5) . . . . ?
C22 C21 N3 C33 -160.5(5) . . . . ?
C20 C21 N3 C33 16.7(9) . . . . ?
N4 C34 C35 C36 0.0(6) . . . . ?
C63 C34 C35 C36 -173.2(5) . . . . ?
N4 C34 C35 Br7 -177.2(4) . . . . ?
C63 C34 C35 Br7 9.7(9) . . . . ?
C34 C35 C36 C37 1.0(7) . . . . ?
Br7 C35 C36 C37 178.1(4) . . . . ?
C34 C35 C36 Br8 -177.9(4) . . . . ?
Br7 C35 C36 Br8 -0.8(8) . . . . ?
C35 C36 C37 N4 -1.5(6) . . . . ?
Br8 C36 C37 N4 177.3(4) . . . . ?
C35 C36 C37 C38 169.9(5) . . . . ?
Br8 C36 C37 C38 -11.2(9) . . . . ?
N4 C37 C38 C39 116.3(6) . . . . ?
C36 C37 C38 C39 -53.5(8) . . . . ?
N4 C37 C38 C43 -65.1(8) . . . . ?
C36 C37 C38 C43 125.1(7) . . . . ?
C43 C38 C39 C40 0.1(8) . . . . ?
C37 C38 C39 C40 178.8(5) . . . . ?
C38 C39 C40 C41 0.7(9) . . . . ?
C39 C40 C41 C42 -1.1(9) . . . . ?
C40 C41 C42 C43 0.6(9) . . . . ?
C41 C42 C43 C38 0.2(8) . . . . ?
C41 C42 C43 C44 176.6(5) . . . . ?
C39 C38 C43 C42 -0.6(8) . . . . ?
C37 C38 C43 C42 -179.2(5) . . . . ?
C39 C38 C43 C44 -176.9(5) . . . . ?
C37 C38 C43 C44 4.5(9) . . . . ?
C42 C43 C44 N5 125.4(6) . . . . ?
C38 C43 C44 N5 -58.3(8) . . . . ?
C42 C43 C44 C45 -56.8(9) . . . . ?
C38 C43 C44 C45 119.5(7) . . . . ?
N5 C44 C45 C46 -0.1(7) . . . . ?
C43 C44 C45 C46 -178.2(6) . . . . ?
N5 C44 C45 Br9 172.5(4) . . . . ?
C43 C44 C45 Br9 -5.5(10) . . . . ?
C44 C45 C46 C47 0.1(7) . . . . ?
Br9 C45 C46 C47 -172.5(5) . . . . ?
C44 C45 C46 Br10 -175.7(5) . . . . ?
Br9 C45 C46 Br10 11.7(9) . . . . ?
C45 C46 C47 N5 0.0(7) . . . . ?
Br10 C46 C47 N5 175.8(4) . . . . ?
C45 C46 C47 C48 -179.6(6) . . . . ?
Br10 C46 C47 C48 -3.8(10) . . . . ?
C46 C47 C48 C49 102.0(8) . . . . ?
N5 C47 C48 C49 -77.6(7) . . . . ?
C46 C47 C48 C53 -76.9(8) . . . . ?
N5 C47 C48 C53 103.5(7) . . . . ?
C53 C48 C49 C50 0.9(9) . . . . ?
C47 C48 C49 C50 -178.0(5) . . . . ?
C48 C49 C50 C51 1.1(9) . . . . ?
C49 C50 C51 C52 -1.4(9) . . . . ?
C50 C51 C52 C53 -0.3(9) . . . . ?
C51 C52 C53 C48 2.3(8) . . . . ?
C51 C52 C53 C54 -177.5(5) . . . . ?
C49 C48 C53 C52 -2.6(8) . . . . ?
C47 C48 C53 C52 176.3(5) . . . . ?
C49 C48 C53 C54 177.2(5) . . . . ?
C47 C48 C53 C54 -3.9(8) . . . . ?
C52 C53 C54 C55 -77.4(8) . . . . ?
C48 C53 C54 C55 102.8(7) . . . . ?
C52 C53 C54 N6 97.8(7) . . . . ?
C48 C53 C54 N6 -82.0(7) . . . . ?
N6 C54 C55 C56 0.1(6) . . . . ?
C53 C54 C55 C56 175.9(6) . . . . ?
N6 C54 C55 Br11 -173.7(4) . . . . ?
C53 C54 C55 Br11 2.2(9) . . . . ?
C54 C55 C56 C57 0.0(6) . . . . ?
Br11 C55 C56 C57 173.9(4) . . . . ?
C54 C55 C56 Br12 178.3(4) . . . . ?
Br11 C55 C56 Br12 -7.8(7) . . . . ?
C55 C56 C57 N6 -0.1(6) . . . . ?
Br12 C56 C57 N6 -178.3(4) . . . . ?
C55 C56 C57 C58 -179.1(5) . . . . ?
Br12 C56 C57 C58 2.6(9) . . . . ?
C56 C57 C58 C59 41.8(8) . . . . ?
N6 C57 C58 C59 -137.1(5) . . . . ?
C56 C57 C58 C63 -135.4(6) . . . . ?
N6 C57 C58 C63 45.7(8) . . . . ?
C63 C58 C59 C60 3.0(8) . . . . ?
C57 C58 C59 C60 -174.4(5) . . . . ?
C58 C59 C60 C61 -1.3(8) . . . . ?
C59 C60 C61 C62 -1.3(9) . . . . ?
C60 C61 C62 C63 2.2(9) . . . . ?
C61 C62 C63 C58 -0.5(8) . . . . ?
C61 C62 C63 C34 -176.6(5) . . . . ?
C59 C58 C63 C62 -2.0(8) . . . . ?
C57 C58 C63 C62 175.1(5) . . . . ?
C59 C58 C63 C34 173.6(5) . . . . ?
C57 C58 C63 C34 -9.2(8) . . . . ?
N4 C34 C63 C62 -114.3(6) . . . . ?
C35 C34 C63 C62 57.7(8) . . . . ?
N4 C34 C63 C58 70.0(8) . . . . ?
C35 C34 C63 C58 -118.1(7) . . . . ?
C36 C37 N4 C34 1.6(6) . . . . ?
C38 C37 N4 C34 -170.0(5) . . . . ?
C36 C37 N4 C64 179.5(5) . . . . ?
C38 C37 N4 C64 8.0(9) . . . . ?
C35 C34 N4 C37 -1.0(6) . . . . ?
C63 C34 N4 C37 172.3(5) . . . . ?
C35 C34 N4 C64 -179.0(5) . . . . ?
C63 C34 N4 C64 -5.7(8) . . . . ?
C45 C44 N5 C47 0.1(7) . . . . ?
C43 C44 N5 C47 178.3(6) . . . . ?
C45 C44 N5 C65 166.5(5) . . . . ?
C43 C44 N5 C65 -15.3(9) . . . . ?
C46 C47 N5 C44 -0.1(7) . . . . ?
C48 C47 N5 C44 179.6(5) . . . . ?
C46 C47 N5 C65 -166.7(5) . . . . ?
C48 C47 N5 C65 12.9(9) . . . . ?
C55 C54 N6 C57 -0.2(6) . . . . ?
C53 C54 N6 C57 -176.4(5) . . . . ?
C55 C54 N6 C66 161.1(5) . . . . ?
C53 C54 N6 C66 -15.1(8) . . . . ?
C56 C57 N6 C54 0.1(6) . . . . ?
C58 C57 N6 C54 179.2(5) . . . . ?
C56 C57 N6 C66 -160.5(5) . . . . ?
C58 C57 N6 C66 18.6(8) . . . . ?

_refine_diff_density_max         3.313
_refine_diff_density_min         -2.550
_refine_diff_density_rms         0.171



_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_160411ch
_database_code_depnum_ccdc_archive 'CCDC 1526998'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H25 N3, C3 H6 O'
_chemical_formula_sum            'C36 H31 N3 O'
_chemical_formula_weight         521.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.811(5)
_cell_length_b                   11.964(5)
_cell_length_c                   18.267(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.187(8)
_cell_angle_gamma                90
_cell_volume                     2736.7(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1284
_cell_measurement_theta_min      25.3
_cell_measurement_theta_max      68.1

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.596
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            32583
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_av_R_equivalents  0.1466
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         6.586
_diffrn_reflns_theta_max         62.996
_diffrn_reflns_theta_full        62.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4413
_reflns_number_gt                2967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1036P)²+1.5992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4413
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1860
_refine_ls_wR_factor_gt          0.1489
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38944(18) 0.08138(19) 0.22063(16) 0.0248(6) Uani 1 1 d . . . . .
N2 N 0.66428(18) 0.39691(19) 0.24527(15) 0.0238(6) Uani 1 1 d . . . . .
C3 C 0.4754(2) 0.1289(2) 0.19600(19) 0.0226(7) Uani 1 1 d . . . . .
N3 N 0.50745(18) 0.2842(2) 0.43169(15) 0.0255(6) Uani 1 1 d . . . . .
C5 C 0.4246(2) 0.0509(2) 0.2946(2) 0.0254(7) Uani 1 1 d . . . . .
C6 C 0.4749(2) 0.1944(2) 0.12960(19) 0.0242(7) Uani 1 1 d . . . . .
C7 C 0.4159(2) 0.2394(2) 0.38757(19) 0.0252(7) Uani 1 1 d . . . . .
C8 C 0.6968(2) 0.2589(2) 0.33027(19) 0.0235(7) Uani 1 1 d . . . . .
H16 H 0.7246 0.2185 0.3749 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7050(2) 0.3721(2) 0.31985(19) 0.0244(7) Uani 1 1 d . . . . .
C10 C 0.5505(2) 0.2855(2) 0.13697(19) 0.0235(7) Uani 1 1 d . . . . .
C11 C 0.6392(2) 0.2140(2) 0.26209(18) 0.0218(7) Uani 1 1 d . . . . .
C12 C 0.6208(2) 0.2994(2) 0.20901(19) 0.0229(7) Uani 1 1 d . . . . .
C13 C 0.7341(2) 0.5849(2) 0.5094(2) 0.0301(8) Uani 1 1 d . . . . .
H17 H 0.7415 0.6282 0.5538 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4598(2) 0.3963(2) 0.3329(2) 0.0277(8) Uani 1 1 d . . . . .
H18 H 0.4578 0.4564 0.2987 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5632(2) 0.1247(2) 0.25556(19) 0.0220(7) Uani 1 1 d . . . . .
C16 C 0.8090(2) 0.5936(2) 0.4659(2) 0.0316(8) Uani 1 1 d . . . . .
H19 H 0.8665 0.6449 0.4790 0.038 Uiso 1 1 calc R U . . .
C17 C 0.4152(2) 0.2399(2) -0.0021(2) 0.0290(7) Uani 1 1 d . . . . .
H20 H 0.3712 0.2235 -0.0496 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6348(2) 0.4478(2) 0.42507(18) 0.0235(7) Uani 1 1 d . . . . .
C19 C 0.4859(2) 0.3303(2) 0.0058(2) 0.0291(8) Uani 1 1 d . . . . .
H21 H 0.4883 0.3769 -0.0359 0.035 Uiso 1 1 calc R U . . .
C20 C 0.5522(2) 0.3514(2) 0.07437(19) 0.0269(7) Uani 1 1 d . . . . .
H22 H 0.6003 0.4127 0.0790 0.032 Uiso 1 1 calc R U . . .
C21 C 0.5327(2) 0.0700(2) 0.3159(2) 0.0253(7) Uani 1 1 d . . . . .
H23 H 0.5778 0.0502 0.3624 0.030 Uiso 1 1 calc R U . . .
C22 C 0.4094(2) 0.1748(2) 0.0589(2) 0.0266(8) Uani 1 1 d . . . . .
H24 H 0.3596 0.1149 0.0530 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3558(2) 0.0427(2) 0.34991(19) 0.0265(7) Uani 1 1 d . . . . .
C24 C 0.5358(2) 0.3797(2) 0.39694(19) 0.0244(7) Uani 1 1 d . . . . .
C25 C 0.8001(2) 0.5270(2) 0.40249(19) 0.0287(8) Uani 1 1 d . . . . .
H25 H 0.8527 0.5320 0.3730 0.034 Uiso 1 1 calc R U . . .
C26 C 0.7150(2) 0.4532(2) 0.38183(19) 0.0248(7) Uani 1 1 d . . . . .
C27 C 0.6473(2) 0.5129(2) 0.4888(2) 0.0289(8) Uani 1 1 d . . . . .
H26 H 0.5957 0.5086 0.5192 0.035 Uiso 1 1 calc R U . . .
C28 C 0.2342(2) -0.0555(3) 0.4113(2) 0.0351(9) Uani 1 1 d . . . . .
H27 H 0.1874 -0.1164 0.4133 0.042 Uiso 1 1 calc R U . . .
C29 C 0.3846(2) 0.3082(2) 0.3267(2) 0.0259(7) Uani 1 1 d . . . . .
H28 H 0.3235 0.2985 0.2875 0.031 Uiso 1 1 calc R U . . .
C30 C 0.2780(2) 0.0848(3) 0.1818(2) 0.0326(8) Uani 1 1 d . . . . .
H1 H 0.2624 0.0201 0.1483 0.049 Uiso 1 1 calc R U . . .
H2 H 0.2645 0.1537 0.1523 0.049 Uiso 1 1 calc R U . . .
H3 H 0.2322 0.0827 0.2184 0.049 Uiso 1 1 calc R U . . .
C31 C 0.3095(3) 0.1205(3) 0.4600(2) 0.0352(8) Uani 1 1 d . . . . .
H29 H 0.3163 0.1771 0.4971 0.042 Uiso 1 1 calc R U . . .
C32 C 0.2902(2) -0.0493(2) 0.3550(2) 0.0316(8) Uani 1 1 d . . . . .
H30 H 0.2843 -0.1079 0.3193 0.038 Uiso 1 1 calc R U . . .
C33 C 0.3625(2) 0.1319(2) 0.4018(2) 0.0275(7) Uani 1 1 d . . . . .
C34 C 0.2466(3) 0.0272(3) 0.4649(2) 0.0390(9) Uani 1 1 d . . . . .
H31 H 0.2117 0.0205 0.5057 0.047 Uiso 1 1 calc R U . . .
C35 C 0.5681(3) 0.2367(3) 0.5012(2) 0.0362(8) Uani 1 1 d . . . . .
H4 H 0.6446 0.2485 0.5041 0.054 Uiso 1 1 calc R U . . .
H5 H 0.5535 0.1564 0.5025 0.054 Uiso 1 1 calc R U . . .
H6 H 0.5471 0.2734 0.5439 0.054 Uiso 1 1 calc R U . . .
C36 C 0.6539(3) 0.5093(2) 0.2142(2) 0.0341(8) Uani 1 1 d . . . . .
H7 H 0.6733 0.5639 0.2548 0.051 Uiso 1 1 calc R U . . .
H8 H 0.5799 0.5220 0.1879 0.051 Uiso 1 1 calc R U . . .
H9 H 0.7015 0.5178 0.1791 0.051 Uiso 1 1 calc R U . . .
C37 C 0.8968(3) 0.2720(3) 0.1788(3) 0.0570(12) Uani 1 1 d . . . . .
H10 H 0.8908 0.3472 0.1571 0.086 Uiso 1 1 calc R U . . .
H11 H 0.8389 0.2599 0.2054 0.086 Uiso 1 1 calc R U . . .
H12 H 0.8918 0.2165 0.1387 0.086 Uiso 1 1 calc R U . . .
C38 C 1.0011(3) 0.2604(3) 0.2318(3) 0.0483(10) Uani 1 1 d . . . . .
O1 O 1.0741(3) 0.2164(3) 0.2110(2) 0.0945(13) Uani 1 1 d . . . . .
C40 C 1.0120(4) 0.3065(4) 0.3081(3) 0.0655(13) Uani 1 1 d . . . . .
H13 H 1.0787 0.2798 0.3398 0.098 Uiso 1 1 calc R U . . .
H14 H 0.9515 0.2820 0.3291 0.098 Uiso 1 1 calc R U . . .
H15 H 1.0130 0.3883 0.3058 0.098 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
N1 C5 1.379(4) . ?
N1 C3 1.396(4) . ?
N1 C30 1.454(4) . ?
N2 C9 1.384(4) . ?
N2 C12 1.398(4) . ?
N2 C36 1.455(4) . ?
C3 C15 1.391(4) . ?
C3 C6 1.443(5) . ?
N3 C7 1.383(4) . ?
N3 C24 1.392(4) . ?
N3 C35 1.457(4) . ?
C5 C21 1.376(4) . ?
C5 C23 1.478(4) . ?
C6 C22 1.403(5) . ?
C6 C10 1.446(4) . ?
C7 C29 1.374(5) . ?
C7 C33 1.504(4) . ?
C8 C9 1.374(4) . ?
C8 C11 1.413(4) . ?
C8 H16 0.9500 . ?
C9 C26 1.476(4) . ?
C10 C20 1.393(5) . ?
C10 C12 1.439(5) . ?
C11 C12 1.394(4) . ?
C11 C15 1.433(4) . ?
C13 C16 1.372(5) . ?
C13 C27 1.394(4) . ?
C13 H17 0.9500 . ?
C14 C24 1.369(5) . ?
C14 C29 1.416(4) . ?
C14 H18 0.9500 . ?
C15 C21 1.407(4) . ?
C16 C25 1.390(5) . ?
C16 H19 0.9500 . ?
C17 C22 1.374(5) . ?
C17 C19 1.398(4) . ?
C17 H20 0.9500 . ?
C18 C27 1.382(5) . ?
C18 C26 1.423(4) . ?
C18 C24 1.504(4) . ?
C19 C20 1.381(5) . ?
C19 H21 0.9500 . ?
C20 H22 0.9500 . ?
C21 H23 0.9500 . ?
C22 H24 0.9500 . ?
C23 C32 1.400(4) . ?
C23 C33 1.418(5) . ?
C25 C26 1.392(4) . ?
C25 H25 0.9500 . ?
C27 H26 0.9500 . ?
C28 C32 1.374(5) . ?
C28 C34 1.377(5) . ?
C28 H27 0.9500 . ?
C29 H28 0.9500 . ?
C30 H1 0.9800 . ?
C30 H2 0.9800 . ?
C30 H3 0.9800 . ?
C31 C33 1.384(5) . ?
C31 C34 1.390(4) . ?
C31 H29 0.9500 . ?
C32 H30 0.9500 . ?
C34 H31 0.9500 . ?
C35 H4 0.9800 . ?
C35 H5 0.9800 . ?
C35 H6 0.9800 . ?
C36 H7 0.9800 . ?
C36 H8 0.9800 . ?
C36 H9 0.9800 . ?
C37 C38 1.482(6) . ?
C37 H10 0.9800 . ?
C37 H11 0.9800 . ?
C37 H12 0.9800 . ?
C38 O1 1.203(5) . ?
C38 C40 1.477(6) . ?
C40 H13 0.9800 . ?
C40 H14 0.9800 . ?
C40 H15 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
C5 N1 C3 107.9(2) . . ?
C5 N1 C30 124.7(2) . . ?
C3 N1 C30 126.3(3) . . ?
C9 N2 C12 108.5(2) . . ?
C9 N2 C36 124.5(3) . . ?
C12 N2 C36 126.3(3) . . ?
C15 C3 N1 107.2(3) . . ?
C15 C3 C6 122.5(2) . . ?
N1 C3 C6 128.9(3) . . ?
C7 N3 C24 108.9(3) . . ?
C7 N3 C35 126.0(3) . . ?
C24 N3 C35 125.1(2) . . ?
C21 C5 N1 109.5(3) . . ?
C21 C5 C23 121.7(3) . . ?
N1 C5 C23 124.7(2) . . ?
C22 C6 C3 125.4(3) . . ?
C22 C6 C10 118.1(3) . . ?
C3 C6 C10 116.5(3) . . ?
C29 C7 N3 107.8(2) . . ?
C29 C7 C33 125.9(3) . . ?
N3 C7 C33 126.3(3) . . ?
C9 C8 C11 107.1(3) . . ?
C9 C8 H16 126.5 . . ?
C11 C8 H16 126.5 . . ?
C8 C9 N2 108.9(3) . . ?
C8 C9 C26 122.6(3) . . ?
N2 C9 C26 124.6(3) . . ?
C20 C10 C12 124.8(3) . . ?
C20 C10 C6 118.5(3) . . ?
C12 C10 C6 116.8(3) . . ?
C12 C11 C8 108.3(2) . . ?
C12 C11 C15 118.5(3) . . ?
C8 C11 C15 125.2(3) . . ?
C11 C12 N2 106.9(3) . . ?
C11 C12 C10 122.2(3) . . ?
N2 C12 C10 129.8(3) . . ?
C16 C13 C27 120.4(3) . . ?
C16 C13 H17 119.8 . . ?
C27 C13 H17 119.8 . . ?
C24 C14 C29 108.0(3) . . ?
C24 C14 H18 126.0 . . ?
C29 C14 H18 126.0 . . ?
C3 C15 C21 108.5(2) . . ?
C3 C15 C11 117.5(3) . . ?
C21 C15 C11 125.3(3) . . ?
C13 C16 C25 119.7(3) . . ?
C13 C16 H19 120.2 . . ?
C25 C16 H19 120.2 . . ?
C22 C17 C19 120.0(3) . . ?
C22 C17 H20 120.0 . . ?
C19 C17 H20 120.0 . . ?
C27 C18 C26 118.3(3) . . ?
C27 C18 C24 122.1(3) . . ?
C26 C18 C24 119.4(3) . . ?
C20 C19 C17 119.7(3) . . ?
C20 C19 H21 120.1 . . ?
C17 C19 H21 120.1 . . ?
C19 C20 C10 121.9(3) . . ?
C19 C20 H22 119.1 . . ?
C10 C20 H22 119.1 . . ?
C5 C21 C15 106.5(3) . . ?
C5 C21 H23 126.7 . . ?
C15 C21 H23 126.7 . . ?
C17 C22 C6 121.8(3) . . ?
C17 C22 H24 119.1 . . ?
C6 C22 H24 119.1 . . ?
C32 C23 C33 120.0(3) . . ?
C32 C23 C5 123.4(3) . . ?
C33 C23 C5 116.6(2) . . ?
C14 C24 N3 107.5(2) . . ?
C14 C24 C18 127.6(3) . . ?
N3 C24 C18 124.8(3) . . ?
C16 C25 C26 120.7(3) . . ?
C16 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C18 119.6(3) . . ?
C25 C26 C9 124.1(3) . . ?
C18 C26 C9 116.1(2) . . ?
C18 C27 C13 121.2(3) . . ?
C18 C27 H26 119.4 . . ?
C13 C27 H26 119.4 . . ?
C32 C28 C34 119.6(3) . . ?
C32 C28 H27 120.2 . . ?
C34 C28 H27 120.2 . . ?
C7 C29 C14 107.7(3) . . ?
C7 C29 H28 126.2 . . ?
C14 C29 H28 126.2 . . ?
N1 C30 H1 109.5 . . ?
N1 C30 H2 109.5 . . ?
H1 C30 H2 109.5 . . ?
N1 C30 H3 109.5 . . ?
H1 C30 H3 109.5 . . ?
H2 C30 H3 109.5 . . ?
C33 C31 C34 120.9(3) . . ?
C33 C31 H29 119.5 . . ?
C34 C31 H29 119.5 . . ?
C28 C32 C23 120.5(3) . . ?
C28 C32 H30 119.7 . . ?
C23 C32 H30 119.7 . . ?
C31 C33 C23 118.0(3) . . ?
C31 C33 C7 122.1(3) . . ?
C23 C33 C7 119.5(3) . . ?
C28 C34 C31 120.8(3) . . ?
C28 C34 H31 119.6 . . ?
C31 C34 H31 119.6 . . ?
N3 C35 H4 109.5 . . ?
N3 C35 H5 109.5 . . ?
H4 C35 H5 109.5 . . ?
N3 C35 H6 109.5 . . ?
H4 C35 H6 109.5 . . ?
H5 C35 H6 109.5 . . ?
N2 C36 H7 109.5 . . ?
N2 C36 H8 109.5 . . ?
H7 C36 H8 109.5 . . ?
N2 C36 H9 109.5 . . ?
H7 C36 H9 109.5 . . ?
H8 C36 H9 109.5 . . ?
C38 C37 H10 109.5 . . ?
C38 C37 H11 109.5 . . ?
H10 C37 H11 109.5 . . ?
C38 C37 H12 109.5 . . ?
H10 C37 H12 109.5 . . ?
H11 C37 H12 109.5 . . ?
O1 C38 C40 122.4(4) . . ?
O1 C38 C37 119.2(5) . . ?
C40 C38 C37 118.3(4) . . ?
C38 C40 H13 109.5 . . ?
C38 C40 H14 109.5 . . ?
H13 C40 H14 109.5 . . ?
C38 C40 H15 109.5 . . ?
H13 C40 H15 109.5 . . ?
H14 C40 H15 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C3 C15 1.1(3) . . . . ?
C30 N1 C3 C15 168.9(3) . . . . ?
C5 N1 C3 C6 -165.4(3) . . . . ?
C30 N1 C3 C6 2.5(5) . . . . ?
C3 N1 C5 C21 -4.5(3) . . . . ?
C30 N1 C5 C21 -172.6(3) . . . . ?
C3 N1 C5 C23 153.1(3) . . . . ?
C30 N1 C5 C23 -15.0(4) . . . . ?
C15 C3 C6 C22 156.5(3) . . . . ?
N1 C3 C6 C22 -38.9(5) . . . . ?
C15 C3 C6 C10 -21.7(4) . . . . ?
N1 C3 C6 C10 142.9(3) . . . . ?
C24 N3 C7 C29 -2.1(3) . . . . ?
C35 N3 C7 C29 -179.1(3) . . . . ?
C24 N3 C7 C33 175.6(3) . . . . ?
C35 N3 C7 C33 -1.4(5) . . . . ?
C11 C8 C9 N2 -6.2(3) . . . . ?
C11 C8 C9 C26 152.2(3) . . . . ?
C12 N2 C9 C8 5.2(3) . . . . ?
C36 N2 C9 C8 176.2(2) . . . . ?
C12 N2 C9 C26 -152.6(2) . . . . ?
C36 N2 C9 C26 18.3(4) . . . . ?
C22 C6 C10 C20 2.1(4) . . . . ?
C3 C6 C10 C20 -179.6(2) . . . . ?
C22 C6 C10 C12 -176.4(2) . . . . ?
C3 C6 C10 C12 1.9(4) . . . . ?
C9 C8 C11 C12 4.9(3) . . . . ?
C9 C8 C11 C15 -143.0(3) . . . . ?
C8 C11 C12 N2 -1.8(3) . . . . ?
C15 C11 C12 N2 148.7(2) . . . . ?
C8 C11 C12 C10 -170.5(2) . . . . ?
C15 C11 C12 C10 -20.0(4) . . . . ?
C9 N2 C12 C11 -2.1(3) . . . . ?
C36 N2 C12 C11 -172.8(3) . . . . ?
C9 N2 C12 C10 165.5(3) . . . . ?
C36 N2 C12 C10 -5.3(4) . . . . ?
C20 C10 C12 C11 -159.9(3) . . . . ?
C6 C10 C12 C11 18.6(4) . . . . ?
C20 C10 C12 N2 34.3(4) . . . . ?
C6 C10 C12 N2 -147.3(3) . . . . ?
N1 C3 C15 C21 2.7(3) . . . . ?
C6 C3 C15 C21 170.2(3) . . . . ?
N1 C3 C15 C11 -146.7(2) . . . . ?
C6 C3 C15 C11 20.8(4) . . . . ?
C12 C11 C15 C3 0.2(4) . . . . ?
C8 C11 C15 C3 145.3(3) . . . . ?
C12 C11 C15 C21 -143.5(3) . . . . ?
C8 C11 C15 C21 1.6(4) . . . . ?
C27 C13 C16 C25 -2.5(5) . . . . ?
C22 C17 C19 C20 2.1(4) . . . . ?
C17 C19 C20 C10 -0.5(4) . . . . ?
C12 C10 C20 C19 176.8(3) . . . . ?
C6 C10 C20 C19 -1.7(4) . . . . ?
N1 C5 C21 C15 6.1(3) . . . . ?
C23 C5 C21 C15 -152.3(3) . . . . ?
C3 C15 C21 C5 -5.3(3) . . . . ?
C11 C15 C21 C5 141.0(3) . . . . ?
C19 C17 C22 C6 -1.7(4) . . . . ?
C3 C6 C22 C17 -178.7(3) . . . . ?
C10 C6 C22 C17 -0.5(4) . . . . ?
C21 C5 C23 C32 -124.7(3) . . . . ?
N1 C5 C23 C32 80.3(4) . . . . ?
C21 C5 C23 C33 52.3(4) . . . . ?
N1 C5 C23 C33 -102.7(3) . . . . ?
C29 C14 C24 N3 -1.5(3) . . . . ?
C29 C14 C24 C18 176.4(3) . . . . ?
C7 N3 C24 C14 2.2(3) . . . . ?
C35 N3 C24 C14 179.3(3) . . . . ?
C7 N3 C24 C18 -175.8(3) . . . . ?
C35 N3 C24 C18 1.2(4) . . . . ?
C27 C18 C24 C14 111.7(4) . . . . ?
C26 C18 C24 C14 -63.0(4) . . . . ?
C27 C18 C24 N3 -70.6(4) . . . . ?
C26 C18 C24 N3 114.7(3) . . . . ?
C13 C16 C25 C26 1.3(5) . . . . ?
C16 C25 C26 C18 1.5(5) . . . . ?
C16 C25 C26 C9 -173.9(3) . . . . ?
C27 C18 C26 C25 -3.1(4) . . . . ?
C24 C18 C26 C25 171.8(3) . . . . ?
C27 C18 C26 C9 172.6(3) . . . . ?
C24 C18 C26 C9 -12.4(4) . . . . ?
C8 C9 C26 C25 121.5(3) . . . . ?
N2 C9 C26 C25 -83.6(4) . . . . ?
C8 C9 C26 C18 -54.1(4) . . . . ?
N2 C9 C26 C18 100.9(3) . . . . ?
C26 C18 C27 C13 2.0(4) . . . . ?
C24 C18 C27 C13 -172.8(3) . . . . ?
C16 C13 C27 C18 0.8(5) . . . . ?
N3 C7 C29 C14 1.1(3) . . . . ?
C33 C7 C29 C14 -176.6(3) . . . . ?
C24 C14 C29 C7 0.3(3) . . . . ?
C34 C28 C32 C23 -2.8(5) . . . . ?
C33 C23 C32 C28 -1.8(5) . . . . ?
C5 C23 C32 C28 175.1(3) . . . . ?
C34 C31 C33 C23 -3.7(5) . . . . ?
C34 C31 C33 C7 169.6(3) . . . . ?
C32 C23 C33 C31 5.0(5) . . . . ?
C5 C23 C33 C31 -172.1(3) . . . . ?
C32 C23 C33 C7 -168.5(3) . . . . ?
C5 C23 C33 C7 14.4(4) . . . . ?
C29 C7 C33 C31 -112.5(4) . . . . ?
N3 C7 C33 C31 70.2(4) . . . . ?
C29 C7 C33 C23 60.7(4) . . . . ?
N3 C7 C33 C23 -116.6(3) . . . . ?
C32 C28 C34 C31 4.2(5) . . . . ?
C33 C31 C34 C28 -0.9(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C30 H3 O1 0.98 2.56 3.191(4) 122.0 1_455
C40 H15 N1 0.98 2.72 3.601(5) 150.1 2_655
C30 H3 O1 0.98 2.56 3.191(4) 122.0 1_455

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.069



_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_160409ch
_database_code_depnum_ccdc_archive 'CCDC 1526996'
_audit_update_record             
;
2017-01-12 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C30 H19 N3), 0.667(C3 Cl7), 2(C0.50 Cl)'
_chemical_formula_sum            'C31.50 H19 Cl3.33 N3'
_chemical_formula_weight         557.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   10.647(3)
_cell_length_b                   9.151(2)
_cell_length_c                   25.792(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.319(8)
_cell_angle_gamma                90
_cell_volume                     2512.9(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1345
_cell_measurement_theta_min      25.3
_cell_measurement_theta_max      68.1

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1143
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.846
_shelx_estimated_absorpt_T_min   0.655
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            31006
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         6.600
_diffrn_reflns_theta_max         66.989
_diffrn_reflns_theta_full        66.989
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4463
_reflns_number_gt                2845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1776P)²+2.6745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4463
_refine_ls_number_parameters     419
_refine_ls_number_restraints     151
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2804
_refine_ls_wR_factor_gt          0.2440
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.010
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4437(3) 0.0245(3) 0.32947(12) 0.0300(7) Uani 1 1 d . . . . .
H1 H 0.509(4) 0.088(4) 0.3183(14) 0.024(9) Uiso 1 1 d . . . . .
N2 N 0.7099(3) -0.0369(3) 0.22482(12) 0.0332(8) Uani 1 1 d . . . . .
C3 C 0.2726(4) -0.0319(4) 0.22997(16) 0.0359(9) Uani 1 1 d . . . . .
H2 H 0.2100 -0.0200 0.2557 0.043 Uiso 1 1 calc R U . . .
C4 C 0.8499(4) 0.0894(4) 0.28682(15) 0.0327(9) Uani 1 1 d . . . . .
C5 C 0.4180(4) 0.1005(4) 0.41982(14) 0.0347(9) Uani 1 1 d . . . . .
C6 C 0.7493(3) -0.0126(4) 0.27180(14) 0.0305(8) Uani 1 1 d . . . . .
C7 C 0.9352(4) 0.1429(4) 0.25026(17) 0.0372(9) Uani 1 1 d . . . . .
H3 H 0.9265 0.1167 0.2148 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6791(4) -0.0882(4) 0.31188(15) 0.0330(9) Uani 1 1 d . . . . .
N3 N 0.7408(3) 0.1352(4) 0.42064(12) 0.0393(9) Uani 1 1 d . . . . .
C10 C 0.6081(4) -0.1479(4) 0.22788(15) 0.0336(9) Uani 1 1 d . . . . .
H4 H 0.6349 -0.2406 0.2106 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3737(4) -0.1605(5) 0.38081(16) 0.0400(10) Uani 1 1 d . . . . .
H5 H 0.3332 -0.2051 0.4095 0.048 Uiso 1 1 calc R U . . .
C12 C 1.0309(4) 0.2328(4) 0.26565(17) 0.0411(10) Uani 1 1 d . . . . .
H6 H 1.0887 0.2683 0.2407 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9592(4) 0.2241(4) 0.35394(17) 0.0392(10) Uani 1 1 d . . . . .
H7 H 0.9671 0.2536 0.3891 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6859(4) -0.0434(4) 0.36128(16) 0.0350(9) Uani 1 1 d . . . . .
C15 C 0.2462(4) -0.0040(5) 0.17882(17) 0.0417(10) Uani 1 1 d . . . . .
H8 H 0.1644 0.0282 0.1693 0.050 Uiso 1 1 calc R U . . .
C16 C 0.3935(4) -0.0781(4) 0.24338(14) 0.0310(9) Uani 1 1 d . . . . .
C17 C 0.8614(3) 0.1313(4) 0.33902(15) 0.0335(9) Uani 1 1 d . . . . .
C18 C 0.7662(4) 0.0779(4) 0.37603(15) 0.0336(9) Uani 1 1 d . . . . .
C19 C 0.4531(4) -0.0242(4) 0.38388(14) 0.0356(9) Uani 1 1 d . . . . .
C20 C 0.4853(4) -0.0962(4) 0.20552(15) 0.0337(9) Uani 1 1 d . . . . .
C21 C 0.4569(4) -0.0671(4) 0.15383(16) 0.0399(10) Uani 1 1 d . . . . .
H9 H 0.5192 -0.0779 0.1279 0.048 Uiso 1 1 calc R U . . .
C22 C 0.5182(4) 0.1459(5) 0.45047(14) 0.0391(10) Uani 1 1 d . . . . .
C23 C 0.6339(4) 0.0518(5) 0.44336(15) 0.0404(10) Uani 1 1 d . . . . .
H10 H 0.6593 0.0051 0.4769 0.048 Uiso 1 1 calc R U . . .
C24 C 0.5932(4) -0.0648(5) 0.40344(16) 0.0403(10) Uani 1 1 d . . . . .
H11 H 0.5975 -0.1657 0.4182 0.048 Uiso 1 1 calc R U . . .
C25 C 0.5800(4) -0.1759(4) 0.28555(15) 0.0364(9) Uani 1 1 d . . . . .
H12 H 0.5856 -0.2819 0.2946 0.044 Uiso 1 1 calc R U . . .
C26 C 1.0447(4) 0.2734(5) 0.31782(18) 0.0421(10) Uani 1 1 d . . . . .
H13 H 1.1125 0.3344 0.3282 0.051 Uiso 1 1 calc R U . . .
C27 C 0.3684(4) -0.2092(4) 0.33277(16) 0.0388(10) Uani 1 1 d . . . . .
H14 H 0.3243 -0.2941 0.3219 0.047 Uiso 1 1 calc R U . . .
C28 C 0.4432(4) -0.1095(4) 0.29733(15) 0.0365(9) Uani 1 1 d . . . . .
C29 C 0.3367(4) -0.0219(5) 0.14066(16) 0.0447(11) Uani 1 1 d . . . . .
H15 H 0.3160 -0.0031 0.1054 0.054 Uiso 1 1 calc R U . . .
C30 C 0.3040(4) 0.1725(5) 0.42115(17) 0.0450(11) Uani 1 1 d . . . . .
H16 H 0.2365 0.1408 0.3997 0.054 Uiso 1 1 calc R U . . .
C31 C 0.5031(5) 0.2663(5) 0.48300(16) 0.0490(12) Uani 1 1 d . . . . .
H17 H 0.5709 0.2990 0.5041 0.059 Uiso 1 1 calc R U . . .
C32 C 0.2887(5) 0.2889(6) 0.45337(18) 0.0549(12) Uani 1 1 d . . . . .
H18 H 0.2099 0.3374 0.4549 0.066 Uiso 1 1 calc R U . . .
C33 C 0.3894(5) 0.3375(5) 0.48424(17) 0.0542(13) Uani 1 1 d . . . . .
H19 H 0.3788 0.4200 0.5061 0.065 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1841(6) 0.8957(6) 0.0347(2) 0.1403(18) Uani 0.5 1 d D U P A 1
Cl5 Cl 0.0568(15) 0.8520(13) -0.0549(6) 0.310(6) Uani 0.5 1 d D U P A 1
C34 C 0.1059(9) 0.7760(9) -0.0033(3) 0.041(2) Uani 0.5 1 d D U P A 1
Cl2 Cl 0.0848(8) 0.8859(10) -0.1012(2) 0.159(4) Uani 0.3333 1 d D U P B 2
C35 C 0.0220(19) 0.855(3) -0.0345(8) 0.185(7) Uani 0.3333 1 d D U P B 2
Cl3 Cl 0.1797(7) 0.8608(10) -0.0205(3) 0.130(2) Uani 0.3333 1 d D U P B 2
Cl4 Cl 0.031(2) 0.665(2) -0.0484(8) 0.283(8) Uani 0.3333 1 d D U P B 2
C36 C 0.144(4) 0.585(6) -0.0947(13) 0.284(10) Uani 0.3333 1 d D U P C 3
Cl6 Cl 0.155(2) 0.607(4) -0.0259(9) 0.398(11) Uani 0.3333 1 d D U P C 3
Cl7 Cl 0.0126(10) 0.6956(13) -0.1105(3) 0.155(3) Uani 0.3333 1 d D U P C 3
C37 C 0.0393(17) -0.0978(18) 0.4396(7) 0.076(5) Uani 0.3333 1 d D U P D 4
Cl8 Cl 0.0096(11) -0.2277(12) 0.4862(3) 0.154(3) Uani 0.3333 1 d D U P D 4
Cl9 Cl -0.0771(12) -0.2168(15) 0.4196(6) 0.197(4) Uani 0.3333 1 d D U P D 4


_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 C19 1.475(5) . ?
N1 C28 1.480(5) . ?
N1 H1 0.95(4) . ?
N2 C6 1.299(5) . ?
N2 C10 1.488(5) . ?
C3 C15 1.371(6) . ?
C3 C16 1.397(6) . ?
C3 H2 0.9500 . ?
C4 C7 1.401(5) . ?
C4 C17 1.404(6) . ?
C4 C6 1.471(5) . ?
C5 C30 1.382(6) . ?
C5 C22 1.388(6) . ?
C5 C19 1.518(6) . ?
C6 C8 1.454(5) . ?
C7 C12 1.367(6) . ?
C7 H3 0.9500 . ?
C8 C14 1.340(6) . ?
C8 C25 1.487(6) . ?
N3 C18 1.294(5) . ?
N3 C23 1.493(5) . ?
C10 C20 1.503(6) . ?
C10 C25 1.540(5) . ?
C10 H4 1.0000 . ?
C11 C27 1.317(6) . ?
C11 C19 1.509(6) . ?
C11 H5 0.9500 . ?
C12 C26 1.403(6) . ?
C12 H6 0.9500 . ?
C13 C26 1.382(6) . ?
C13 C17 1.397(6) . ?
C13 H7 0.9500 . ?
C14 C18 1.451(5) . ?
C14 C24 1.486(6) . ?
C15 C29 1.391(6) . ?
C15 H8 0.9500 . ?
C16 C20 1.395(5) . ?
C16 C28 1.513(5) . ?
C17 C18 1.479(5) . ?
C19 C24 1.615(6) . ?
C20 C21 1.391(6) . ?
C21 C29 1.386(6) . ?
C21 H9 0.9500 . ?
C22 C31 1.395(6) . ?
C22 C23 1.515(6) . ?
C23 C24 1.543(6) . ?
C23 H10 1.0000 . ?
C24 H11 1.0000 . ?
C25 C28 1.609(6) . ?
C25 H12 1.0000 . ?
C26 H13 0.9500 . ?
C27 C28 1.519(5) . ?
C27 H14 0.9500 . ?
C29 H15 0.9500 . ?
C30 C32 1.362(7) . ?
C30 H16 0.9500 . ?
C31 C33 1.375(7) . ?
C31 H17 0.9500 . ?
C32 C33 1.403(7) . ?
C32 H18 0.9500 . ?
C33 H19 0.9500 . ?
Cl1 C34 1.686(10) . ?
Cl5 C34 1.589(14) . ?
Cl2 C35 1.87(2) . ?
C35 Cl3 1.72(2) . ?
C35 Cl4 1.78(2) . ?
C36 Cl7 1.77(2) . ?
C36 Cl6 1.79(2) . ?
C37 Cl8 1.722(16) . ?
C37 Cl9 1.727(17) . ?

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
C19 N1 C28 106.4(3) . . ?
C19 N1 H1 115(2) . . ?
C28 N1 H1 110(2) . . ?
C6 N2 C10 107.4(3) . . ?
C15 C3 C16 118.6(4) . . ?
C15 C3 H2 120.7 . . ?
C16 C3 H2 120.7 . . ?
C7 C4 C17 119.8(4) . . ?
C7 C4 C6 121.2(4) . . ?
C17 C4 C6 119.0(3) . . ?
C30 C5 C22 121.1(4) . . ?
C30 C5 C19 126.3(4) . . ?
C22 C5 C19 112.4(4) . . ?
N2 C6 C8 114.6(3) . . ?
N2 C6 C4 125.8(3) . . ?
C8 C6 C4 119.4(3) . . ?
C12 C7 C4 120.0(4) . . ?
C12 C7 H3 120.0 . . ?
C4 C7 H3 120.0 . . ?
C14 C8 C6 120.3(4) . . ?
C14 C8 C25 129.3(4) . . ?
C6 C8 C25 107.4(3) . . ?
C18 N3 C23 107.8(3) . . ?
N2 C10 C20 113.4(3) . . ?
N2 C10 C25 108.1(3) . . ?
C20 C10 C25 104.4(3) . . ?
N2 C10 H4 110.3 . . ?
C20 C10 H4 110.3 . . ?
C25 C10 H4 110.3 . . ?
C27 C11 C19 110.5(3) . . ?
C27 C11 H5 124.8 . . ?
C19 C11 H5 124.8 . . ?
C7 C12 C26 120.8(4) . . ?
C7 C12 H6 119.6 . . ?
C26 C12 H6 119.6 . . ?
C26 C13 C17 120.4(4) . . ?
C26 C13 H7 119.8 . . ?
C17 C13 H7 119.8 . . ?
C8 C14 C18 120.8(4) . . ?
C8 C14 C24 128.5(4) . . ?
C18 C14 C24 107.6(3) . . ?
C3 C15 C29 121.3(4) . . ?
C3 C15 H8 119.3 . . ?
C29 C15 H8 119.3 . . ?
C20 C16 C3 120.7(4) . . ?
C20 C16 C28 112.2(3) . . ?
C3 C16 C28 127.0(4) . . ?
C13 C17 C4 119.4(4) . . ?
C13 C17 C18 122.4(4) . . ?
C4 C17 C18 118.2(3) . . ?
N3 C18 C14 114.7(4) . . ?
N3 C18 C17 126.0(4) . . ?
C14 C18 C17 119.2(4) . . ?
N1 C19 C11 99.5(3) . . ?
N1 C19 C5 109.8(3) . . ?
C11 C19 C5 120.9(3) . . ?
N1 C19 C24 115.1(3) . . ?
C11 C19 C24 110.0(3) . . ?
C5 C19 C24 102.3(3) . . ?
C21 C20 C16 119.9(4) . . ?
C21 C20 C10 127.7(4) . . ?
C16 C20 C10 112.4(3) . . ?
C29 C21 C20 119.2(4) . . ?
C29 C21 H9 120.4 . . ?
C20 C21 H9 120.4 . . ?
C5 C22 C31 119.2(4) . . ?
C5 C22 C23 112.6(4) . . ?
C31 C22 C23 128.2(4) . . ?
N3 C23 C22 112.3(3) . . ?
N3 C23 C24 107.7(3) . . ?
C22 C23 C24 104.4(3) . . ?
N3 C23 H10 110.8 . . ?
C22 C23 H10 110.8 . . ?
C24 C23 H10 110.8 . . ?
C14 C24 C23 102.2(3) . . ?
C14 C24 C19 110.9(3) . . ?
C23 C24 C19 107.7(3) . . ?
C14 C24 H11 111.8 . . ?
C23 C24 H11 111.8 . . ?
C19 C24 H11 111.8 . . ?
C8 C25 C10 102.1(3) . . ?
C8 C25 C28 110.6(3) . . ?
C10 C25 C28 107.5(3) . . ?
C8 C25 H12 112.0 . . ?
C10 C25 H12 112.0 . . ?
C28 C25 H12 112.0 . . ?
C13 C26 C12 119.6(4) . . ?
C13 C26 H13 120.2 . . ?
C12 C26 H13 120.2 . . ?
C11 C27 C28 110.1(4) . . ?
C11 C27 H14 125.0 . . ?
C28 C27 H14 125.0 . . ?
N1 C28 C16 111.0(3) . . ?
N1 C28 C27 99.2(3) . . ?
C16 C28 C27 119.0(3) . . ?
N1 C28 C25 114.7(3) . . ?
C16 C28 C25 102.1(3) . . ?
C27 C28 C25 111.4(3) . . ?
C21 C29 C15 120.3(4) . . ?
C21 C29 H15 119.8 . . ?
C15 C29 H15 119.8 . . ?
C32 C30 C5 119.7(4) . . ?
C32 C30 H16 120.1 . . ?
C5 C30 H16 120.1 . . ?
C33 C31 C22 119.5(4) . . ?
C33 C31 H17 120.3 . . ?
C22 C31 H17 120.3 . . ?
C30 C32 C33 120.0(5) . . ?
C30 C32 H18 120.0 . . ?
C33 C32 H18 120.0 . . ?
C31 C33 C32 120.4(4) . . ?
C31 C33 H19 119.8 . . ?
C32 C33 H19 119.8 . . ?
Cl5 C34 Cl1 111.2(7) . . ?
Cl3 C35 Cl4 91.1(13) . . ?
Cl3 C35 Cl2 80.4(9) . . ?
Cl4 C35 Cl2 86.6(11) . . ?
Cl7 C36 Cl6 102.0(14) . . ?
Cl8 C37 Cl9 68.8(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
C10 N2 C6 C8 -4.6(4) . . . . ?
C10 N2 C6 C4 179.8(3) . . . . ?
C7 C4 C6 N2 -16.9(6) . . . . ?
C17 C4 C6 N2 164.3(3) . . . . ?
C7 C4 C6 C8 167.7(3) . . . . ?
C17 C4 C6 C8 -11.1(5) . . . . ?
C17 C4 C7 C12 1.5(6) . . . . ?
C6 C4 C7 C12 -177.3(4) . . . . ?
N2 C6 C8 C14 -161.5(3) . . . . ?
C4 C6 C8 C14 14.4(5) . . . . ?
N2 C6 C8 C25 0.7(4) . . . . ?
C4 C6 C8 C25 176.7(3) . . . . ?
C6 N2 C10 C20 121.8(3) . . . . ?
C6 N2 C10 C25 6.5(4) . . . . ?
C4 C7 C12 C26 -0.4(6) . . . . ?
C6 C8 C14 C18 -2.0(6) . . . . ?
C25 C8 C14 C18 -159.9(4) . . . . ?
C6 C8 C14 C24 155.5(4) . . . . ?
C25 C8 C14 C24 -2.4(7) . . . . ?
C16 C3 C15 C29 0.4(6) . . . . ?
C15 C3 C16 C20 -0.3(5) . . . . ?
C15 C3 C16 C28 177.7(3) . . . . ?
C26 C13 C17 C4 -0.6(6) . . . . ?
C26 C13 C17 C18 -178.8(4) . . . . ?
C7 C4 C17 C13 -1.0(5) . . . . ?
C6 C4 C17 C13 177.8(3) . . . . ?
C7 C4 C17 C18 177.3(3) . . . . ?
C6 C4 C17 C18 -3.9(5) . . . . ?
C23 N3 C18 C14 1.0(4) . . . . ?
C23 N3 C18 C17 176.7(3) . . . . ?
C8 C14 C18 N3 162.6(4) . . . . ?
C24 C14 C18 N3 0.9(5) . . . . ?
C8 C14 C18 C17 -13.4(5) . . . . ?
C24 C14 C18 C17 -175.1(3) . . . . ?
C13 C17 C18 N3 18.9(6) . . . . ?
C4 C17 C18 N3 -159.4(4) . . . . ?
C13 C17 C18 C14 -165.6(4) . . . . ?
C4 C17 C18 C14 16.2(5) . . . . ?
C28 N1 C19 C11 -36.5(4) . . . . ?
C28 N1 C19 C5 -164.3(3) . . . . ?
C28 N1 C19 C24 81.0(4) . . . . ?
C27 C11 C19 N1 22.7(4) . . . . ?
C27 C11 C19 C5 142.7(4) . . . . ?
C27 C11 C19 C24 -98.6(4) . . . . ?
C30 C5 C19 N1 60.2(5) . . . . ?
C22 C5 C19 N1 -115.2(4) . . . . ?
C30 C5 C19 C11 -54.5(6) . . . . ?
C22 C5 C19 C11 130.0(4) . . . . ?
C30 C5 C19 C24 -177.1(4) . . . . ?
C22 C5 C19 C24 7.5(4) . . . . ?
C3 C16 C20 C21 0.5(5) . . . . ?
C28 C16 C20 C21 -177.8(3) . . . . ?
C3 C16 C20 C10 -179.4(3) . . . . ?
C28 C16 C20 C10 2.3(4) . . . . ?
N2 C10 C20 C21 68.1(5) . . . . ?
C25 C10 C20 C21 -174.5(4) . . . . ?
N2 C10 C20 C16 -112.0(4) . . . . ?
C25 C10 C20 C16 5.4(4) . . . . ?
C16 C20 C21 C29 -0.8(6) . . . . ?
C10 C20 C21 C29 179.1(4) . . . . ?
C30 C5 C22 C31 -0.1(6) . . . . ?
C19 C5 C22 C31 175.6(3) . . . . ?
C30 C5 C22 C23 179.7(3) . . . . ?
C19 C5 C22 C23 -4.6(5) . . . . ?
C18 N3 C23 C22 -116.7(4) . . . . ?
C18 N3 C23 C24 -2.4(4) . . . . ?
C5 C22 C23 N3 115.6(4) . . . . ?
C31 C22 C23 N3 -64.6(5) . . . . ?
C5 C22 C23 C24 -0.7(4) . . . . ?
C31 C22 C23 C24 179.1(4) . . . . ?
C8 C14 C24 C23 -162.1(4) . . . . ?
C18 C14 C24 C23 -2.2(4) . . . . ?
C8 C14 C24 C19 -47.4(6) . . . . ?
C18 C14 C24 C19 112.4(4) . . . . ?
N3 C23 C24 C14 2.8(4) . . . . ?
C22 C23 C24 C14 122.3(3) . . . . ?
N3 C23 C24 C19 -114.2(3) . . . . ?
C22 C23 C24 C19 5.3(4) . . . . ?
N1 C19 C24 C14 0.2(5) . . . . ?
C11 C19 C24 C14 111.6(4) . . . . ?
C5 C19 C24 C14 -118.8(3) . . . . ?
N1 C19 C24 C23 111.3(4) . . . . ?
C11 C19 C24 C23 -137.3(3) . . . . ?
C5 C19 C24 C23 -7.6(4) . . . . ?
C14 C8 C25 C10 163.4(4) . . . . ?
C6 C8 C25 C10 3.2(4) . . . . ?
C14 C8 C25 C28 49.2(5) . . . . ?
C6 C8 C25 C28 -110.9(3) . . . . ?
N2 C10 C25 C8 -5.8(4) . . . . ?
C20 C10 C25 C8 -126.8(3) . . . . ?
N2 C10 C25 C28 110.6(3) . . . . ?
C20 C10 C25 C28 -10.4(4) . . . . ?
C17 C13 C26 C12 1.7(6) . . . . ?
C7 C12 C26 C13 -1.2(6) . . . . ?
C19 C11 C27 C28 -0.6(5) . . . . ?
C19 N1 C28 C16 162.1(3) . . . . ?
C19 N1 C28 C27 36.0(4) . . . . ?
C19 N1 C28 C25 -82.8(4) . . . . ?
C20 C16 C28 N1 114.2(4) . . . . ?
C3 C16 C28 N1 -63.9(5) . . . . ?
C20 C16 C28 C27 -131.6(4) . . . . ?
C3 C16 C28 C27 50.2(5) . . . . ?
C20 C16 C28 C25 -8.5(4) . . . . ?
C3 C16 C28 C25 173.4(4) . . . . ?
C11 C27 C28 N1 -21.6(4) . . . . ?
C11 C27 C28 C16 -142.0(4) . . . . ?
C11 C27 C28 C25 99.6(4) . . . . ?
C8 C25 C28 N1 2.1(4) . . . . ?
C10 C25 C28 N1 -108.7(3) . . . . ?
C8 C25 C28 C16 122.2(3) . . . . ?
C10 C25 C28 C16 11.4(4) . . . . ?
C8 C25 C28 C27 -109.7(4) . . . . ?
C10 C25 C28 C27 139.6(3) . . . . ?
C20 C21 C29 C15 0.9(6) . . . . ?
C3 C15 C29 C21 -0.8(6) . . . . ?
C22 C5 C30 C32 -0.7(6) . . . . ?
C19 C5 C30 C32 -175.8(4) . . . . ?
C5 C22 C31 C33 0.2(6) . . . . ?
C23 C22 C31 C33 -179.6(4) . . . . ?
C5 C30 C32 C33 1.4(7) . . . . ?
C22 C31 C33 C32 0.5(6) . . . . ?
C30 C32 C33 C31 -1.3(7) . . . . ?

_refine_diff_density_max         0.819
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.098



_exptl_crystal_recrystallization_method 'Vapour deposition'
