# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_SQ201031_2_a
_database_code_depnum_ccdc_archive 'CCDC 2041853'
loop_
_audit_author_name
_audit_author_address
'Qiang Sha'
;Nanjing Agricultural University
China
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2021-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H25 Br N2 O3'
_chemical_formula_sum            'C32 H25 Br N2 O3'
_chemical_formula_weight         565.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   11.305(3)
_cell_length_b                   13.363(3)
_cell_length_c                   19.885(5)
_cell_angle_alpha                92.405(9)
_cell_angle_beta                 105.012(8)
_cell_angle_gamma                111.457(7)
_cell_volume                     2669.0(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9967
_cell_measurement_theta_min      4.948
_cell_measurement_theta_max      51.101

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.577
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4733
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_source.type              microfocus
_diffrn_radiation_type           MoK\a
_diffrn_source.source            'Ius 2.0'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            38991
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             12200
_reflns_number_gt                7032
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0534P)²+1.0580P] 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         12200
_refine_ls_number_parameters     687
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1101
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.002
_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
Br1 Br 1.25004(3) 0.72556(3) 0.30529(2) 0.07089(13) Uani 1 1 d . . . . .
C1 C 0.7358(2) 0.4883(2) 0.26680(14) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.7060(2) 0.5176(2) 0.32587(14) 0.0374(6) Uani 1 1 d . . . . .
C3 C 0.5643(2) 0.4740(2) 0.31024(14) 0.0394(6) Uani 1 1 d . . . . .
C4 C 0.5119(2) 0.4204(2) 0.24249(14) 0.0390(6) Uani 1 1 d . . . . .
C5 C 0.5975(3) 0.3910(2) 0.14357(14) 0.0400(6) Uani 1 1 d . . . . .
C6 C 0.5365(3) 0.2811(2) 0.11882(16) 0.0489(7) Uani 1 1 d . . . . .
H6 H 0.510235 0.231680 0.148925 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5149(3) 0.2452(2) 0.04924(18) 0.0614(9) Uani 1 1 d . . . . .
H7 H 0.474014 0.171046 0.032424 0.074 Uiso 1 1 calc R U . . .
C8 C 0.5522(4) 0.3165(3) 0.00477(18) 0.0733(10) Uani 1 1 d . . . . .
H8 H 0.536273 0.291401 -0.042344 0.088 Uiso 1 1 calc R U . . .
C9 C 0.6136(4) 0.4258(3) 0.02953(19) 0.0831(12) Uani 1 1 d . . . . .
H9 H 0.640322 0.474768 -0.000744 0.100 Uiso 1 1 calc R U . . .
C10 C 0.6361(4) 0.4634(2) 0.09940(17) 0.0638(9) Uani 1 1 d . . . . .
H10 H 0.677141 0.537647 0.116123 0.077 Uiso 1 1 calc R U . . .
C11 C 0.8647(2) 0.4958(2) 0.25786(14) 0.0391(6) Uani 1 1 d . . . . .
C12 C 0.9755(2) 0.5936(2) 0.27741(14) 0.0403(6) Uani 1 1 d . . . . .
H12 H 0.968150 0.657578 0.291906 0.048 Uiso 1 1 calc R U . . .
C13 C 1.0967(2) 0.5941(2) 0.27494(14) 0.0423(6) Uani 1 1 d . . . . .
C14 C 1.1111(3) 0.5028(3) 0.25265(17) 0.0552(8) Uani 1 1 d . . . . .
H14 H 1.194031 0.504983 0.252074 0.066 Uiso 1 1 calc R U . . .
C15 C 1.0000(3) 0.4068(3) 0.2309(2) 0.0659(9) Uani 1 1 d . . . . .
H15 H 1.007267 0.343838 0.214260 0.079 Uiso 1 1 calc R U . . .
C16 C 0.8785(3) 0.4039(2) 0.23376(18) 0.0559(8) Uani 1 1 d . . . . .
H16 H 0.804414 0.338632 0.219144 0.067 Uiso 1 1 calc R U . . .
C17 C 0.8030(3) 0.5745(3) 0.39440(16) 0.0510(7) Uani 1 1 d . . . . .
C18 C 0.8314(4) 0.6107(3) 0.51815(18) 0.0756(10) Uani 1 1 d . . . . .
H18A H 0.902626 0.675699 0.513800 0.091 Uiso 1 1 calc R U . . .
H18B H 0.773974 0.632628 0.538649 0.091 Uiso 1 1 calc R U . . .
C19 C 0.8874(4) 0.5444(4) 0.5637(2) 0.1022(14) Uani 1 1 d . . . . .
H19A H 0.816489 0.479569 0.567015 0.153 Uiso 1 1 calc R U . . .
H19B H 0.935698 0.585639 0.609868 0.153 Uiso 1 1 calc R U . . .
H19C H 0.946368 0.525003 0.543872 0.153 Uiso 1 1 calc R U . . .
C20 C 0.4821(3) 0.4864(2) 0.35442(15) 0.0448(7) Uani 1 1 d . . . . .
C21 C 0.5155(3) 0.5949(2) 0.39318(14) 0.0429(7) Uani 1 1 d . . . . .
C22 C 0.4693(3) 0.6023(3) 0.45084(17) 0.0584(8) Uani 1 1 d . . . . .
H22 H 0.416766 0.539448 0.464197 0.070 Uiso 1 1 calc R U . . .
C23 C 0.5009(4) 0.7022(3) 0.48814(19) 0.0736(10) Uani 1 1 d . . . . .
H23 H 0.470972 0.706398 0.527134 0.088 Uiso 1 1 calc R U . . .
C24 C 0.5752(4) 0.7943(3) 0.4685(2) 0.0763(11) Uani 1 1 d . . . . .
H24 H 0.595067 0.861529 0.493658 0.092 Uiso 1 1 calc R U . . .
C25 C 0.6215(3) 0.7893(3) 0.4117(2) 0.0672(9) Uani 1 1 d . . . . .
H25 H 0.673385 0.852988 0.398798 0.081 Uiso 1 1 calc R U . . .
C26 C 0.5910(3) 0.6901(2) 0.37371(16) 0.0522(7) Uani 1 1 d . . . . .
H26 H 0.621456 0.686938 0.334778 0.063 Uiso 1 1 calc R U . . .
C27 C 0.3182(2) 0.4372(2) 0.16204(13) 0.0392(6) Uani 1 1 d . . . . .
C28 C 0.1904(3) 0.3853(2) 0.11615(15) 0.0509(7) Uani 1 1 d . . . . .
H28 H 0.149010 0.309839 0.109012 0.061 Uiso 1 1 calc R U . . .
C29 C 0.1254(3) 0.4457(3) 0.08133(17) 0.0668(9) Uani 1 1 d . . . . .
H29 H 0.039937 0.410307 0.050649 0.080 Uiso 1 1 calc R U . . .
C30 C 0.1844(4) 0.5575(3) 0.09102(18) 0.0700(10) Uani 1 1 d . . . . .
H30 H 0.139328 0.597745 0.067461 0.084 Uiso 1 1 calc R U . . .
C31 C 0.3102(3) 0.6084(3) 0.13587(17) 0.0607(8) Uani 1 1 d . . . . .
H31 H 0.350662 0.683890 0.142933 0.073 Uiso 1 1 calc R U . . .
C32 C 0.3782(3) 0.5499(2) 0.17078(15) 0.0479(7) Uani 1 1 d . . . . .
H32 H 0.464521 0.585942 0.200310 0.057 Uiso 1 1 calc R U . . .
N1 N 0.6169(2) 0.42960(16) 0.21594(11) 0.0376(5) Uani 1 1 d . . . . .
N2 N 0.3810(2) 0.37509(18) 0.19878(12) 0.0447(6) Uani 1 1 d . . . . .
H2 H 0.337337 0.306069 0.194355 0.054 Uiso 1 1 calc R U . . .
O1 O 0.75440(19) 0.54444(17) 0.44782(10) 0.0564(5) Uani 1 1 d . . . . .
O2 O 0.9125(2) 0.6417(2) 0.40272(13) 0.0979(10) Uani 1 1 d . . . . .
O3 O 0.3858(2) 0.40730(17) 0.35684(13) 0.0683(6) Uani 1 1 d . . . . .
Br2 Br 0.74882(4) -0.24256(3) 0.22223(2) 0.07903(15) Uani 1 1 d . . . . .
C33 C 0.5076(2) 0.0311(2) 0.22980(14) 0.0400(6) Uani 1 1 d . . . . .
C34 C 0.3936(2) 0.0047(2) 0.17399(14) 0.0378(6) Uani 1 1 d . . . . .
C35 C 0.3132(2) 0.05475(19) 0.19398(14) 0.0387(6) Uani 1 1 d . . . . .
C36 C 0.3791(3) 0.1081(2) 0.26142(15) 0.0413(6) Uani 1 1 d . . . . .
C37 C 0.5930(3) 0.1345(2) 0.35222(15) 0.0470(7) Uani 1 1 d . . . . .
C38 C 0.6715(3) 0.2427(2) 0.36942(17) 0.0613(8) Uani 1 1 d . . . . .
H38 H 0.662849 0.290041 0.337294 0.074 Uiso 1 1 calc R U . . .
C39 C 0.7644(4) 0.2814(3) 0.4354(2) 0.0769(11) Uani 1 1 d . . . . .
H39 H 0.818454 0.355066 0.447647 0.092 Uiso 1 1 calc R U . . .
C40 C 0.7767(4) 0.2130(3) 0.4817(2) 0.0886(13) Uani 1 1 d . . . . .
H40 H 0.841313 0.239113 0.525227 0.106 Uiso 1 1 calc R U . . .
C41 C 0.6955(5) 0.1060(4) 0.4655(2) 0.1162(19) Uani 1 1 d . . . . .
H41 H 0.702143 0.059620 0.498531 0.139 Uiso 1 1 calc R U . . .
C42 C 0.6023(4) 0.0657(3) 0.3994(2) 0.0873(13) Uani 1 1 d . . . . .
H42 H 0.547019 -0.007793 0.387841 0.105 Uiso 1 1 calc R U . . .
C43 C 0.6306(3) 0.0136(2) 0.23296(15) 0.0438(7) Uani 1 1 d . . . . .
C44 C 0.6325(3) -0.0887(2) 0.22990(14) 0.0425(6) Uani 1 1 d . . . . .
H44 H 0.556842 -0.148707 0.229084 0.051 Uiso 1 1 calc R U . . .
C45 C 0.7469(3) -0.1018(2) 0.22803(15) 0.0444(7) Uani 1 1 d . . . . .
C46 C 0.8598(3) -0.0165(3) 0.22949(19) 0.0646(9) Uani 1 1 d . . . . .
H46 H 0.935796 -0.027104 0.227617 0.078 Uiso 1 1 calc R U . . .
C47 C 0.8588(4) 0.0855(3) 0.2338(3) 0.1002(15) Uani 1 1 d . . . . .
H47 H 0.935072 0.145277 0.235183 0.120 Uiso 1 1 calc R U . . .
C48 C 0.7460(3) 0.1003(3) 0.2361(2) 0.0852(13) Uani 1 1 d . . . . .
H48 H 0.747561 0.170386 0.239754 0.102 Uiso 1 1 calc R U . . .
C49 C 0.3756(3) -0.0503(2) 0.10435(15) 0.0472(7) Uani 1 1 d . U . . .
C50 C 0.2791(3) -0.0699(3) -0.01975(17) 0.0663(9) Uani 1 1 d . U . . .
H50A H 0.256463 -0.023917 -0.052981 0.080 Uiso 1 1 calc R U . . .
H50B H 0.360766 -0.075007 -0.023194 0.080 Uiso 1 1 calc R U . . .
C51 C 0.1727(4) -0.1778(3) -0.0371(2) 0.0875(12) Uani 1 1 d . . . . .
H51A H 0.198119 -0.224636 -0.006279 0.131 Uiso 1 1 calc R U . . .
H51B H 0.156702 -0.207083 -0.085025 0.131 Uiso 1 1 calc R U . . .
H51C H 0.093075 -0.172985 -0.031418 0.131 Uiso 1 1 calc R U . . .
C52 C 0.1793(3) 0.0484(2) 0.15492(15) 0.0452(7) Uani 1 1 d . . . . .
C53 C 0.0730(2) -0.0595(2) 0.12153(14) 0.0405(6) Uani 1 1 d . . . . .
C54 C 0.0798(3) -0.1557(2) 0.14134(16) 0.0503(7) Uani 1 1 d . . . . .
H54 H 0.153874 -0.154435 0.175915 0.060 Uiso 1 1 calc R U . . .
C55 C -0.0238(4) -0.2539(3) 0.10963(19) 0.0652(9) Uani 1 1 d . . . . .
H55 H -0.019910 -0.318545 0.123384 0.078 Uiso 1 1 calc R U . . .
C56 C -0.1323(3) -0.2559(3) 0.05793(19) 0.0728(11) Uani 1 1 d . . . . .
H56 H -0.201274 -0.322184 0.036434 0.087 Uiso 1 1 calc R U . . .
C57 C -0.1398(3) -0.1619(3) 0.03788(18) 0.0716(10) Uani 1 1 d . . . . .
H57 H -0.213316 -0.164104 0.002483 0.086 Uiso 1 1 calc R U . . .
C58 C -0.0390(3) -0.0636(3) 0.06975(16) 0.0560(8) Uani 1 1 d . . . . .
H58 H -0.045597 0.000601 0.056629 0.067 Uiso 1 1 calc R U . . .
C59 C 0.2393(3) 0.0992(2) 0.33755(15) 0.0474(7) Uani 1 1 d . . . . .
C60 C 0.2014(3) -0.0112(3) 0.33744(16) 0.0562(8) Uani 1 1 d . . . . .
H60 H 0.241172 -0.048251 0.316451 0.067 Uiso 1 1 calc R U . . .
C61 C 0.1053(4) -0.0674(3) 0.36800(18) 0.0712(10) Uani 1 1 d . . . . .
H61 H 0.079827 -0.142103 0.366909 0.085 Uiso 1 1 calc R U . . .
C62 C 0.0473(4) -0.0138(4) 0.3999(2) 0.0866(12) Uani 1 1 d . . . . .
H62 H -0.016755 -0.051584 0.421139 0.104 Uiso 1 1 calc R U . . .
C63 C 0.0843(4) 0.0961(3) 0.4004(2) 0.0915(13) Uani 1 1 d . . . . .
H63 H 0.044571 0.132709 0.421822 0.110 Uiso 1 1 calc R U . . .
C64 C 0.1789(3) 0.1526(3) 0.36968(19) 0.0700(10) Uani 1 1 d . . . . .
H64 H 0.202913 0.227107 0.370340 0.084 Uiso 1 1 calc R U . . .
N3 N 0.4975(2) 0.09343(17) 0.28311(12) 0.0432(5) Uani 1 1 d . . . . .
N4 N 0.3385(2) 0.15929(18) 0.30857(12) 0.0493(6) Uani 1 1 d . . . . .
H4 H 0.375259 0.228888 0.319896 0.059 Uiso 1 1 calc R U . . .
O4 O 0.29895(19) -0.02143(16) 0.05211(10) 0.0517(5) Uani 1 1 d . U . . .
O5 O 0.4256(2) -0.1126(2) 0.09432(12) 0.0788(8) Uani 1 1 d . U . . .
O6 O 0.1570(2) 0.13063(17) 0.15302(13) 0.0720(7) Uani 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
Br1 C13 1.897(3) . ?
C1 N1 1.380(3) . ?
C1 C2 1.381(4) . ?
C1 C11 1.482(3) . ?
C2 C3 1.431(4) . ?
C2 C17 1.472(4) . ?
C3 C4 1.369(4) . ?
C3 C20 1.479(4) . ?
C4 N1 1.387(3) . ?
C4 N2 1.395(3) . ?
C5 C10 1.363(4) . ?
C5 C6 1.378(4) . ?
C5 N1 1.441(3) . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.383(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C16 1.376(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(4) . ?
C14 C15 1.379(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O2 1.198(3) . ?
C17 O1 1.329(4) . ?
C18 C19 1.478(6) . ?
C18 O1 1.483(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 O3 1.222(3) . ?
C20 C21 1.482(4) . ?
C21 C26 1.383(4) . ?
C21 C22 1.391(4) . ?
C22 C23 1.374(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.352(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.389(4) . ?
C27 C28 1.390(4) . ?
C27 N2 1.392(3) . ?
C28 C29 1.374(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.377(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.366(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.375(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
N2 H2 0.8600 . ?
Br2 C45 1.887(3) . ?
C33 N3 1.374(3) . ?
C33 C34 1.382(4) . ?
C33 C43 1.479(4) . ?
C34 C35 1.429(3) . ?
C34 C49 1.469(4) . ?
C35 C36 1.370(4) . ?
C35 C52 1.481(4) . ?
C36 N3 1.385(3) . ?
C36 N4 1.398(3) . ?
C37 C42 1.353(5) . ?
C37 C38 1.362(4) . ?
C37 N3 1.446(3) . ?
C38 C39 1.388(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.341(5) . ?
C39 H39 0.9300 . ?
C40 C41 1.355(5) . ?
C40 H40 0.9300 . ?
C41 C42 1.391(5) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C44 1.373(4) . ?
C43 C48 1.377(4) . ?
C44 C45 1.378(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.358(4) . ?
C46 C47 1.366(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.370(5) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 O5 1.200(3) . ?
C49 O4 1.339(3) . ?
C50 C51 1.456(5) . ?
C50 O4 1.470(4) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 O6 1.214(3) . ?
C52 C53 1.484(4) . ?
C53 C54 1.384(4) . ?
C53 C58 1.391(4) . ?
C54 C55 1.383(4) . ?
C54 H54 0.9300 . ?
C55 C56 1.372(5) . ?
C55 H55 0.9300 . ?
C56 C57 1.359(5) . ?
C56 H56 0.9300 . ?
C57 C58 1.374(4) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 C60 1.377(4) . ?
C59 C64 1.388(4) . ?
C59 N4 1.396(4) . ?
C60 C61 1.377(5) . ?
C60 H60 0.9300 . ?
C61 C62 1.366(5) . ?
C61 H61 0.9300 . ?
C62 C63 1.371(6) . ?
C62 H62 0.9300 . ?
C63 C64 1.369(5) . ?
C63 H63 0.9300 . ?
C64 H64 0.9300 . ?
N4 H4 0.8600 . ?

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 107.4(2) . . ?
N1 C1 C11 121.6(2) . . ?
C2 C1 C11 130.1(2) . . ?
C1 C2 C3 107.6(2) . . ?
C1 C2 C17 125.9(2) . . ?
C3 C2 C17 126.3(2) . . ?
C4 C3 C2 107.5(2) . . ?
C4 C3 C20 123.4(2) . . ?
C2 C3 C20 129.0(2) . . ?
C3 C4 N1 107.9(2) . . ?
C3 C4 N2 131.0(2) . . ?
N1 C4 N2 120.6(2) . . ?
C10 C5 C6 120.3(3) . . ?
C10 C5 N1 120.0(2) . . ?
C6 C5 N1 119.7(2) . . ?
C7 C6 C5 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C6 120.9(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 119.5(3) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C16 C11 C12 118.8(2) . . ?
C16 C11 C1 120.1(2) . . ?
C12 C11 C1 121.1(2) . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 122.4(3) . . ?
C14 C13 Br1 118.3(2) . . ?
C12 C13 Br1 119.3(2) . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C11 C16 C15 121.2(3) . . ?
C11 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
O2 C17 O1 122.5(3) . . ?
O2 C17 C2 125.3(3) . . ?
O1 C17 C2 112.1(2) . . ?
C19 C18 O1 108.5(3) . . ?
C19 C18 H18A 110.0 . . ?
O1 C18 H18A 110.0 . . ?
C19 C18 H18B 110.0 . . ?
O1 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C3 119.2(2) . . ?
O3 C20 C21 121.3(2) . . ?
C3 C20 C21 119.5(2) . . ?
C26 C21 C22 118.5(3) . . ?
C26 C21 C20 122.1(2) . . ?
C22 C21 C20 119.4(3) . . ?
C23 C22 C21 120.3(3) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C24 C23 C22 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.3(3) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C32 C27 C28 118.7(3) . . ?
C32 C27 N2 122.1(2) . . ?
C28 C27 N2 119.3(2) . . ?
C29 C28 C27 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 121.2(3) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C31 C30 C29 118.8(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 H30 120.6 . . ?
C30 C31 C32 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C31 C32 C27 120.2(3) . . ?
C31 C32 H32 119.9 . . ?
C27 C32 H32 119.9 . . ?
C1 N1 C4 109.6(2) . . ?
C1 N1 C5 127.5(2) . . ?
C4 N1 C5 122.7(2) . . ?
C27 N2 C4 122.6(2) . . ?
C27 N2 H2 118.7 . . ?
C4 N2 H2 118.7 . . ?
C17 O1 C18 117.2(2) . . ?
N3 C33 C34 107.4(2) . . ?
N3 C33 C43 122.5(2) . . ?
C34 C33 C43 129.5(2) . . ?
C33 C34 C35 107.7(2) . . ?
C33 C34 C49 123.1(2) . . ?
C35 C34 C49 128.5(2) . . ?
C36 C35 C34 107.1(2) . . ?
C36 C35 C52 123.2(2) . . ?
C34 C35 C52 129.6(2) . . ?
C35 C36 N3 108.1(2) . . ?
C35 C36 N4 130.7(2) . . ?
N3 C36 N4 120.8(2) . . ?
C42 C37 C38 120.7(3) . . ?
C42 C37 N3 119.8(3) . . ?
C38 C37 N3 119.5(3) . . ?
C37 C38 C39 119.2(3) . . ?
C37 C38 H38 120.4 . . ?
C39 C38 H38 120.4 . . ?
C40 C39 C38 120.3(3) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 120.4(3) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C40 C41 C42 120.0(4) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
C37 C42 C41 119.2(3) . . ?
C37 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C44 C43 C48 118.1(3) . . ?
C44 C43 C33 121.7(2) . . ?
C48 C43 C33 120.2(2) . . ?
C43 C44 C45 119.7(2) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 122.2(3) . . ?
C46 C45 Br2 118.1(2) . . ?
C44 C45 Br2 119.7(2) . . ?
C45 C46 C47 118.2(3) . . ?
C45 C46 H46 120.9 . . ?
C47 C46 H46 120.9 . . ?
C46 C47 C48 120.5(3) . . ?
C46 C47 H47 119.8 . . ?
C48 C47 H47 119.8 . . ?
C47 C48 C43 121.4(3) . . ?
C47 C48 H48 119.3 . . ?
C43 C48 H48 119.3 . . ?
O5 C49 O4 122.9(3) . . ?
O5 C49 C34 124.6(3) . . ?
O4 C49 C34 112.4(2) . . ?
C51 C50 O4 110.0(3) . . ?
C51 C50 H50A 109.7 . . ?
O4 C50 H50A 109.7 . . ?
C51 C50 H50B 109.7 . . ?
O4 C50 H50B 109.7 . . ?
H50A C50 H50B 108.2 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O6 C52 C35 119.6(2) . . ?
O6 C52 C53 121.2(2) . . ?
C35 C52 C53 119.2(2) . . ?
C54 C53 C58 119.0(3) . . ?
C54 C53 C52 122.3(2) . . ?
C58 C53 C52 118.7(3) . . ?
C55 C54 C53 119.9(3) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C56 C55 C54 120.1(3) . . ?
C56 C55 H55 120.0 . . ?
C54 C55 H55 120.0 . . ?
C57 C56 C55 120.5(3) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C56 C57 C58 120.2(3) . . ?
C56 C57 H57 119.9 . . ?
C58 C57 H57 119.9 . . ?
C57 C58 C53 120.4(3) . . ?
C57 C58 H58 119.8 . . ?
C53 C58 H58 119.8 . . ?
C60 C59 C64 118.3(3) . . ?
C60 C59 N4 122.5(3) . . ?
C64 C59 N4 119.2(3) . . ?
C59 C60 C61 120.9(3) . . ?
C59 C60 H60 119.6 . . ?
C61 C60 H60 119.6 . . ?
C62 C61 C60 120.3(4) . . ?
C62 C61 H61 119.9 . . ?
C60 C61 H61 119.9 . . ?
C61 C62 C63 119.4(4) . . ?
C61 C62 H62 120.3 . . ?
C63 C62 H62 120.3 . . ?
C64 C63 C62 120.8(4) . . ?
C64 C63 H63 119.6 . . ?
C62 C63 H63 119.6 . . ?
C63 C64 C59 120.3(3) . . ?
C63 C64 H64 119.8 . . ?
C59 C64 H64 119.8 . . ?
C33 N3 C36 109.5(2) . . ?
C33 N3 C37 125.6(2) . . ?
C36 N3 C37 124.8(2) . . ?
C59 N4 C36 121.1(2) . . ?
C59 N4 H4 119.5 . . ?
C36 N4 H4 119.5 . . ?
C49 O4 C50 116.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.6(3) . . . . ?
C11 C1 C2 C3 -168.6(3) . . . . ?
N1 C1 C2 C17 175.4(3) . . . . ?
C11 C1 C2 C17 6.2(5) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C17 C2 C3 C4 -175.2(3) . . . . ?
C1 C2 C3 C20 -176.9(3) . . . . ?
C17 C2 C3 C20 8.3(5) . . . . ?
C2 C3 C4 N1 0.0(3) . . . . ?
C20 C3 C4 N1 176.8(2) . . . . ?
C2 C3 C4 N2 -171.3(3) . . . . ?
C20 C3 C4 N2 5.5(5) . . . . ?
C10 C5 C6 C7 0.0(4) . . . . ?
N1 C5 C6 C7 178.1(3) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C6 C5 C10 C9 -0.1(5) . . . . ?
N1 C5 C10 C9 -178.2(3) . . . . ?
C8 C9 C10 C5 0.5(6) . . . . ?
N1 C1 C11 C16 -45.3(4) . . . . ?
C2 C1 C11 C16 122.6(3) . . . . ?
N1 C1 C11 C12 138.6(3) . . . . ?
C2 C1 C11 C12 -53.6(4) . . . . ?
C16 C11 C12 C13 -2.9(4) . . . . ?
C1 C11 C12 C13 173.3(3) . . . . ?
C11 C12 C13 C14 1.4(4) . . . . ?
C11 C12 C13 Br1 -177.3(2) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
Br1 C13 C14 C15 179.6(3) . . . . ?
C13 C14 C15 C16 -1.7(5) . . . . ?
C12 C11 C16 C15 2.0(5) . . . . ?
C1 C11 C16 C15 -174.2(3) . . . . ?
C14 C15 C16 C11 0.3(5) . . . . ?
C1 C2 C17 O2 33.9(5) . . . . ?
C3 C2 C17 O2 -152.3(3) . . . . ?
C1 C2 C17 O1 -147.4(3) . . . . ?
C3 C2 C17 O1 26.4(4) . . . . ?
C4 C3 C20 O3 46.3(4) . . . . ?
C2 C3 C20 O3 -137.6(3) . . . . ?
C4 C3 C20 C21 -131.8(3) . . . . ?
C2 C3 C20 C21 44.2(4) . . . . ?
O3 C20 C21 C26 -157.2(3) . . . . ?
C3 C20 C21 C26 20.9(4) . . . . ?
O3 C20 C21 C22 22.4(4) . . . . ?
C3 C20 C21 C22 -159.4(3) . . . . ?
C26 C21 C22 C23 -1.3(5) . . . . ?
C20 C21 C22 C23 179.0(3) . . . . ?
C21 C22 C23 C24 1.2(5) . . . . ?
C22 C23 C24 C25 -0.9(6) . . . . ?
C23 C24 C25 C26 0.7(6) . . . . ?
C24 C25 C26 C21 -0.9(5) . . . . ?
C22 C21 C26 C25 1.2(4) . . . . ?
C20 C21 C26 C25 -179.1(3) . . . . ?
C32 C27 C28 C29 -1.0(4) . . . . ?
N2 C27 C28 C29 177.8(3) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
C28 C29 C30 C31 0.4(5) . . . . ?
C29 C30 C31 C32 0.3(5) . . . . ?
C30 C31 C32 C27 -1.4(5) . . . . ?
C28 C27 C32 C31 1.7(4) . . . . ?
N2 C27 C32 C31 -177.0(3) . . . . ?
C2 C1 N1 C4 -0.6(3) . . . . ?
C11 C1 N1 C4 169.7(2) . . . . ?
C2 C1 N1 C5 173.6(2) . . . . ?
C11 C1 N1 C5 -16.2(4) . . . . ?
C3 C4 N1 C1 0.4(3) . . . . ?
N2 C4 N1 C1 172.7(2) . . . . ?
C3 C4 N1 C5 -174.1(2) . . . . ?
N2 C4 N1 C5 -1.8(4) . . . . ?
C10 C5 N1 C1 -62.0(4) . . . . ?
C6 C5 N1 C1 119.9(3) . . . . ?
C10 C5 N1 C4 111.5(3) . . . . ?
C6 C5 N1 C4 -66.6(3) . . . . ?
C32 C27 N2 C4 -5.3(4) . . . . ?
C28 C27 N2 C4 176.0(2) . . . . ?
C3 C4 N2 C27 80.3(4) . . . . ?
N1 C4 N2 C27 -90.1(3) . . . . ?
O2 C17 O1 C18 10.4(5) . . . . ?
C2 C17 O1 C18 -168.3(3) . . . . ?
C19 C18 O1 C17 -111.6(3) . . . . ?
N3 C33 C34 C35 1.1(3) . . . . ?
C43 C33 C34 C35 -170.3(3) . . . . ?
N3 C33 C34 C49 172.4(2) . . . . ?
C43 C33 C34 C49 1.0(4) . . . . ?
C33 C34 C35 C36 -1.0(3) . . . . ?
C49 C34 C35 C36 -171.7(3) . . . . ?
C33 C34 C35 C52 -177.1(3) . . . . ?
C49 C34 C35 C52 12.2(5) . . . . ?
C34 C35 C36 N3 0.6(3) . . . . ?
C52 C35 C36 N3 176.9(2) . . . . ?
C34 C35 C36 N4 -171.8(3) . . . . ?
C52 C35 C36 N4 4.6(5) . . . . ?
C42 C37 C38 C39 1.9(5) . . . . ?
N3 C37 C38 C39 -179.0(3) . . . . ?
C37 C38 C39 C40 0.0(6) . . . . ?
C38 C39 C40 C41 -2.2(7) . . . . ?
C39 C40 C41 C42 2.6(8) . . . . ?
C38 C37 C42 C41 -1.6(6) . . . . ?
N3 C37 C42 C41 179.3(4) . . . . ?
C40 C41 C42 C37 -0.7(8) . . . . ?
N3 C33 C43 C44 120.2(3) . . . . ?
C34 C33 C43 C44 -69.6(4) . . . . ?
N3 C33 C43 C48 -62.7(4) . . . . ?
C34 C33 C43 C48 107.6(4) . . . . ?
C48 C43 C44 C45 -1.8(5) . . . . ?
C33 C43 C44 C45 175.4(3) . . . . ?
C43 C44 C45 C46 0.4(5) . . . . ?
C43 C44 C45 Br2 -178.9(2) . . . . ?
C44 C45 C46 C47 0.8(5) . . . . ?
Br2 C45 C46 C47 -179.9(3) . . . . ?
C45 C46 C47 C48 -0.4(7) . . . . ?
C46 C47 C48 C43 -1.0(7) . . . . ?
C44 C43 C48 C47 2.2(6) . . . . ?
C33 C43 C48 C47 -175.1(4) . . . . ?
C33 C34 C49 O5 29.7(5) . . . . ?
C35 C34 C49 O5 -160.9(3) . . . . ?
C33 C34 C49 O4 -148.8(3) . . . . ?
C35 C34 C49 O4 20.6(4) . . . . ?
C36 C35 C52 O6 48.9(4) . . . . ?
C34 C35 C52 O6 -135.6(3) . . . . ?
C36 C35 C52 C53 -128.2(3) . . . . ?
C34 C35 C52 C53 47.3(4) . . . . ?
O6 C52 C53 C54 -158.0(3) . . . . ?
C35 C52 C53 C54 19.2(4) . . . . ?
O6 C52 C53 C58 20.4(4) . . . . ?
C35 C52 C53 C58 -162.5(3) . . . . ?
C58 C53 C54 C55 0.1(4) . . . . ?
C52 C53 C54 C55 178.4(3) . . . . ?
C53 C54 C55 C56 0.9(5) . . . . ?
C54 C55 C56 C57 -0.7(5) . . . . ?
C55 C56 C57 C58 -0.6(5) . . . . ?
C56 C57 C58 C53 1.6(5) . . . . ?
C54 C53 C58 C57 -1.3(4) . . . . ?
C52 C53 C58 C57 -179.7(3) . . . . ?
C64 C59 C60 C61 0.4(5) . . . . ?
N4 C59 C60 C61 178.5(3) . . . . ?
C59 C60 C61 C62 -0.9(5) . . . . ?
C60 C61 C62 C63 0.9(6) . . . . ?
C61 C62 C63 C64 -0.4(7) . . . . ?
C62 C63 C64 C59 -0.1(6) . . . . ?
C60 C59 C64 C63 0.1(5) . . . . ?
N4 C59 C64 C63 -178.0(3) . . . . ?
C34 C33 N3 C36 -0.8(3) . . . . ?
C43 C33 N3 C36 171.4(2) . . . . ?
C34 C33 N3 C37 177.2(2) . . . . ?
C43 C33 N3 C37 -10.6(4) . . . . ?
C35 C36 N3 C33 0.1(3) . . . . ?
N4 C36 N3 C33 173.3(2) . . . . ?
C35 C36 N3 C37 -177.9(2) . . . . ?
N4 C36 N3 C37 -4.7(4) . . . . ?
C42 C37 N3 C33 -72.9(4) . . . . ?
C38 C37 N3 C33 108.0(3) . . . . ?
C42 C37 N3 C36 104.8(4) . . . . ?
C38 C37 N3 C36 -74.3(4) . . . . ?
C60 C59 N4 C36 17.7(4) . . . . ?
C64 C59 N4 C36 -164.2(3) . . . . ?
C35 C36 N4 C59 68.2(4) . . . . ?
N3 C36 N4 C59 -103.3(3) . . . . ?
O5 C49 O4 C50 -0.5(4) . . . . ?
C34 C49 O4 C50 178.1(2) . . . . ?
C51 C50 O4 C49 83.1(3) . . . . ?

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
_geom_hbond_publ_flag
C28 H28 O6 0.93 2.61 3.417(4) 145.7 . yes
C32 H32 Br2 0.93 3.09 3.916(3) 148.3 1_565 yes
N2 H2 O6 0.86 2.41 3.228(3) 159.3 . yes
C60 H60 Br1 0.93 3.06 3.807(3) 138.4 1_445 yes
C64 H64 O3 0.93 2.62 3.417(4) 144.6 . yes
N4 H4 O3 0.86 2.42 3.219(3) 155.6 . yes

_refine_diff_density_max         0.461
_refine_diff_density_min         -0.780
_refine_diff_density_rms         0.053



