# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_mo_d8v20086_0m
_database_code_depnum_ccdc_archive 'CCDC 2008510'
loop_
_audit_author_name
_audit_author_address
'Hua Deng'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Br N3 O4'
_chemical_formula_weight         494.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   9.1040(4)
_cell_length_b                   18.5010(7)
_cell_length_c                   13.3317(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.6690(10)
_cell_angle_gamma                90
_cell_volume                     2240.90(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9890
_cell_measurement_theta_min      4.995
_cell_measurement_theta_max      49.059

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.870
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3477
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33837
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_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 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8745
_reflns_number_gt                6291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.990

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0120P)²+0.1668P] 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     SHELXL
_refine_ls_extinction_coef       0.0065(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2461 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.022(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         8745
_refine_ls_number_parameters     588
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.021
_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 0.22416(5) 0.31196(4) 0.89175(4) 0.0801(2) Uani 1 1 d . . . . .
O1 O 0.8871(4) 0.5773(2) 0.7126(3) 0.0828(12) Uani 1 1 d . . . . .
O2 O 1.1316(4) 0.5769(2) 0.7380(3) 0.0738(11) Uani 1 1 d . . . . .
O3 O 0.7169(5) 0.3075(3) 0.1450(3) 0.0926(13) Uani 1 1 d . . . . .
O4 O 0.7700(6) 0.4193(3) 0.1167(3) 0.1108(17) Uani 1 1 d . . . . .
N1 N 0.8932(5) 0.4398(3) 0.8015(3) 0.0581(12) Uani 1 1 d . . . . .
N2 N 0.8848(4) 0.36202(19) 0.6572(3) 0.0437(8) Uani 1 1 d . . . . .
N3 N 0.7528(5) 0.3687(3) 0.1736(3) 0.0688(12) Uani 1 1 d . . . . .
C1 C 0.8520(5) 0.3678(3) 0.7642(3) 0.0469(11) Uani 1 1 d . . . . .
H1 H 0.9167 0.3333 0.8013 0.056 Uiso 1 1 calc R U . . .
C2 C 1.0126(5) 0.4644(3) 0.7406(3) 0.0505(11) Uani 1 1 d . . . . .
H2 H 1.1079 0.4523 0.7747 0.061 Uiso 1 1 calc R U . . .
C3 C 0.9914(4) 0.4213(2) 0.6414(3) 0.0435(10) Uani 1 1 d . . . . .
C4 C 0.8387(5) 0.4241(2) 0.5934(3) 0.0461(11) Uani 1 1 d . . . . .
H4A H 0.7711 0.4586 0.6219 0.055 Uiso 1 1 calc R U . . .
C5 C 0.8127(4) 0.4080(2) 0.4842(3) 0.0428(10) Uani 1 1 d . . . . .
C6 C 0.8583(6) 0.4576(3) 0.4147(4) 0.0650(14) Uani 1 1 d . . . . .
H6 H 0.9027 0.5003 0.4376 0.078 Uiso 1 1 calc R U . . .
C7 C 0.8396(6) 0.4454(3) 0.3132(4) 0.0688(15) Uani 1 1 d . . . . .
H7 H 0.8714 0.4788 0.2672 0.083 Uiso 1 1 calc R U . . .
C8 C 0.7728(5) 0.3824(3) 0.2817(3) 0.0496(11) Uani 1 1 d . . . . .
C9 C 0.7276(5) 0.3311(3) 0.3469(3) 0.0527(12) Uani 1 1 d . . . . .
H9 H 0.6835 0.2885 0.3234 0.063 Uiso 1 1 calc R U . . .
C10 C 0.7496(5) 0.3447(2) 0.4489(3) 0.0507(12) Uani 1 1 d . . . . .
H10 H 0.7210 0.3102 0.4946 0.061 Uiso 1 1 calc R U . . .
C11 C 1.1201(5) 0.4048(3) 0.5812(3) 0.0449(11) Uani 1 1 d . . . . .
C12 C 1.1383(5) 0.3366(3) 0.5414(4) 0.0565(13) Uani 1 1 d . . . . .
H12 H 1.0721 0.3000 0.5541 0.068 Uiso 1 1 calc R U . . .
C13 C 1.2553(6) 0.3230(3) 0.4824(4) 0.0695(14) Uani 1 1 d . . . . .
H13 H 1.2665 0.2772 0.4551 0.083 Uiso 1 1 calc R U . . .
C14 C 1.3544(6) 0.3763(4) 0.4637(4) 0.0735(16) Uani 1 1 d . . . . .
H14 H 1.4320 0.3668 0.4236 0.088 Uiso 1 1 calc R U . . .
C15 C 1.3390(6) 0.4438(4) 0.5046(5) 0.0821(18) Uani 1 1 d . . . . .
H15 H 1.4068 0.4800 0.4928 0.099 Uiso 1 1 calc R U . . .
C16 C 1.2223(6) 0.4579(3) 0.5633(4) 0.0687(15) Uani 1 1 d . . . . .
H16 H 1.2125 0.5036 0.5911 0.082 Uiso 1 1 calc R U . . .
C17 C 1.0004(6) 0.5456(3) 0.7278(4) 0.0575(13) Uani 1 1 d . . . . .
C18 C 1.1348(7) 0.6549(3) 0.7289(5) 0.0908(19) Uani 1 1 d . . . . .
H18A H 1.1526 0.6679 0.6610 0.136 Uiso 1 1 calc R U . . .
H18B H 1.2119 0.6740 0.7737 0.136 Uiso 1 1 calc R U . . .
H18C H 1.0420 0.6745 0.7460 0.136 Uiso 1 1 calc R U . . .
C19 C 0.6967(5) 0.3504(2) 0.7897(3) 0.0437(11) Uani 1 1 d . . . . .
C20 C 0.6687(5) 0.3495(2) 0.8901(3) 0.0467(11) Uani 1 1 d . . . . .
H20 H 0.7458 0.3572 0.9381 0.056 Uiso 1 1 calc R U . . .
C21 C 0.5290(5) 0.3375(2) 0.9211(3) 0.0477(11) Uani 1 1 d . . . . .
H21 H 0.5110 0.3373 0.9889 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4177(4) 0.3259(2) 0.8489(3) 0.0482(11) Uani 1 1 d . . . . .
C23 C 0.4415(5) 0.3245(3) 0.7490(3) 0.0617(13) Uani 1 1 d . . . . .
H23 H 0.3644 0.3155 0.7014 0.074 Uiso 1 1 calc R U . . .
C24 C 0.5823(5) 0.3366(3) 0.7195(3) 0.0580(13) Uani 1 1 d . . . . .
H24 H 0.6001 0.3354 0.6516 0.070 Uiso 1 1 calc R U . . .
Br2 Br 1.14992(6) 0.65650(3) 0.41909(5) 0.0818(2) Uani 1 1 d . . . . .
O5 O 0.4306(4) 0.4069(2) 0.1974(3) 0.0793(11) Uani 1 1 d . . . . .
O6 O 0.1891(4) 0.4162(2) 0.2145(3) 0.0698(10) Uani 1 1 d . . . . .
O7 O 0.5422(7) 0.5794(3) -0.3770(3) 0.127(2) Uani 1 1 d . . . . .
O8 O 0.5606(7) 0.6923(3) -0.3441(4) 0.130(2) Uani 1 1 d . . . . .
N4 N 0.4599(5) 0.5405(3) 0.2995(3) 0.0603(11) Uani 1 1 d . . . . .
N5 N 0.4569(4) 0.6247(2) 0.1630(3) 0.0491(9) Uani 1 1 d . . . . .
N6 N 0.5457(6) 0.6298(4) -0.3187(4) 0.0838(15) Uani 1 1 d . . . . .
C25 C 0.5010(5) 0.6138(3) 0.2706(4) 0.0554(12) Uani 1 1 d . . . . .
H25 H 0.4421 0.6472 0.3085 0.066 Uiso 1 1 calc R U . . .
C26 C 0.3288(5) 0.5229(3) 0.2338(4) 0.0546(12) Uani 1 1 d . . . . .
H26 H 0.2404 0.5367 0.2675 0.066 Uiso 1 1 calc R U . . .
C27 C 0.3410(5) 0.5708(2) 0.1383(3) 0.0471(11) Uani 1 1 d . . . . .
C28 C 0.4890(5) 0.5650(3) 0.0948(3) 0.0476(11) Uani 1 1 d . . . . .
H28 H 0.5542 0.5271 0.1234 0.057 Uiso 1 1 calc R U . . .
C29 C 0.5084(5) 0.5839(2) -0.0112(3) 0.0426(10) Uani 1 1 d . . . . .
C30 C 0.5055(7) 0.5297(3) -0.0821(4) 0.0720(17) Uani 1 1 d . . . . .
H30 H 0.4943 0.4821 -0.0615 0.086 Uiso 1 1 calc R U . . .
C31 C 0.5185(7) 0.5436(3) -0.1820(4) 0.0778(17) Uani 1 1 d . . . . .
H31 H 0.5165 0.5062 -0.2287 0.093 Uiso 1 1 calc R U . . .
C32 C 0.5347(5) 0.6140(3) -0.2114(3) 0.0554(12) Uani 1 1 d . . . . .
C33 C 0.5381(5) 0.6691(3) -0.1440(4) 0.0578(13) Uani 1 1 d . . . . .
H33 H 0.5497 0.7165 -0.1654 0.069 Uiso 1 1 calc R U . . .
C34 C 0.5244(5) 0.6544(3) -0.0437(3) 0.0521(11) Uani 1 1 d . . . . .
H34 H 0.5259 0.6920 0.0025 0.063 Uiso 1 1 calc R U . . .
C35 C 0.2052(5) 0.5950(3) 0.0804(3) 0.0480(11) Uani 1 1 d . . . . .
C36 C 0.1833(5) 0.6671(3) 0.0584(4) 0.0614(13) Uani 1 1 d . . . . .
H36 H 0.2548 0.7008 0.0792 0.074 Uiso 1 1 calc R U . . .
C37 C 0.0558(6) 0.6898(3) 0.0059(5) 0.0750(16) Uani 1 1 d . . . . .
H37 H 0.0421 0.7386 -0.0086 0.090 Uiso 1 1 calc R U . . .
C38 C -0.0505(6) 0.6408(4) -0.0252(4) 0.0790(18) Uani 1 1 d . . . . .
H38 H -0.1365 0.6563 -0.0601 0.095 Uiso 1 1 calc R U . . .
C39 C -0.0296(7) 0.5692(4) -0.0044(5) 0.0800(17) Uani 1 1 d . . . . .
H39 H -0.1017 0.5358 -0.0252 0.096 Uiso 1 1 calc R U . . .
C40 C 0.0976(6) 0.5461(3) 0.0471(4) 0.0685(15) Uani 1 1 d . . . . .
H40 H 0.1114 0.4971 0.0598 0.082 Uiso 1 1 calc R U . . .
C41 C 0.3247(6) 0.4428(3) 0.2127(4) 0.0570(13) Uani 1 1 d . . . . .
C42 C 0.1743(8) 0.3393(3) 0.1961(6) 0.098(2) Uani 1 1 d . . . . .
H42A H 0.2048 0.3283 0.1302 0.147 Uiso 1 1 calc R U . . .
H42B H 0.0734 0.3253 0.2006 0.147 Uiso 1 1 calc R U . . .
H42C H 0.2350 0.3133 0.2454 0.147 Uiso 1 1 calc R U . . .
C43 C 0.6605(5) 0.6286(3) 0.3021(3) 0.0512(12) Uani 1 1 d . . . . .
C44 C 0.7686(6) 0.6352(3) 0.2357(4) 0.0637(14) Uani 1 1 d . . . . .
H44 H 0.7440 0.6330 0.1669 0.076 Uiso 1 1 calc R U . . .
C45 C 0.9146(5) 0.6453(3) 0.2698(4) 0.0622(13) Uani 1 1 d . . . . .
H45 H 0.9874 0.6501 0.2244 0.075 Uiso 1 1 calc R U . . .
C46 C 0.9500(5) 0.6479(3) 0.3711(4) 0.0566(12) Uani 1 1 d . . . . .
C47 C 0.8424(5) 0.6430(3) 0.4391(4) 0.0591(13) Uani 1 1 d . . . . .
H47 H 0.8667 0.6462 0.5078 0.071 Uiso 1 1 calc R U . . .
C48 C 0.6995(6) 0.6333(3) 0.4039(4) 0.0592(14) Uani 1 1 d . . . . .
H48 H 0.6267 0.6299 0.4495 0.071 Uiso 1 1 calc R U . . .
H4 H 0.529(7) 0.509(3) 0.282(5) 0.09(2) Uiso 1 1 d . . . . .
H1A H 0.824(6) 0.466(3) 0.790(4) 0.057(18) 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
Br1 C22 1.904(4) . ?
O1 C17 1.192(6) . ?
O2 C17 1.327(6) . ?
O2 C18 1.449(7) . ?
O3 N3 1.232(6) . ?
O4 N3 1.221(6) . ?
N1 C1 1.463(6) . ?
N1 C2 1.469(6) . ?
N1 H1A 0.80(5) . ?
N2 C4 1.475(6) . ?
N2 C1 1.479(6) . ?
N2 C3 1.488(5) . ?
N3 C8 1.464(6) . ?
C1 C19 1.510(6) . ?
C1 H1 0.9800 . ?
C2 C17 1.515(7) . ?
C2 C3 1.546(6) . ?
C2 H2 0.9800 . ?
C3 C4 1.494(6) . ?
C3 C11 1.495(6) . ?
C4 C5 1.489(6) . ?
C4 H4A 0.9800 . ?
C5 C10 1.374(6) . ?
C5 C6 1.386(7) . ?
C6 C7 1.373(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(6) . ?
C9 C10 1.385(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.382(6) . ?
C11 C16 1.384(7) . ?
C12 C13 1.387(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.378(6) . ?
C19 C20 1.379(6) . ?
C20 C21 1.380(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.364(6) . ?
C23 C24 1.383(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
Br2 C46 1.896(5) . ?
O5 C41 1.198(6) . ?
O6 C41 1.332(6) . ?
O6 C42 1.448(7) . ?
O7 N6 1.213(7) . ?
O8 N6 1.214(7) . ?
N4 C25 1.464(7) . ?
N4 C26 1.471(6) . ?
N4 H4 0.89(6) . ?
N5 C28 1.471(6) . ?
N5 C27 1.473(6) . ?
N5 C25 1.479(6) . ?
N6 C32 1.470(7) . ?
C25 C43 1.510(7) . ?
C25 H25 0.9800 . ?
C26 C41 1.509(7) . ?
C26 C27 1.561(6) . ?
C26 H26 0.9800 . ?
C27 C35 1.484(6) . ?
C27 C28 1.504(6) . ?
C28 C29 1.477(6) . ?
C28 H28 0.9800 . ?
C29 C30 1.377(7) . ?
C29 C34 1.384(6) . ?
C30 C31 1.368(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.370(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.359(7) . ?
C33 C34 1.379(6) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C36 1.378(7) . ?
C35 C40 1.384(7) . ?
C36 C37 1.382(7) . ?
C36 H36 0.9300 . ?
C37 C38 1.370(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.364(9) . ?
C38 H38 0.9300 . ?
C39 C40 1.376(8) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 C44 1.372(6) . ?
C43 C48 1.383(6) . ?
C44 C45 1.390(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.369(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.380(6) . ?
C47 C48 1.366(7) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 C18 116.7(4) . . ?
C1 N1 C2 106.1(4) . . ?
C1 N1 H1A 107(4) . . ?
C2 N1 H1A 108(4) . . ?
C4 N2 C1 115.7(3) . . ?
C4 N2 C3 60.6(3) . . ?
C1 N2 C3 104.9(3) . . ?
O4 N3 O3 123.6(5) . . ?
O4 N3 C8 117.8(5) . . ?
O3 N3 C8 118.6(5) . . ?
N1 C1 N2 109.3(4) . . ?
N1 C1 C19 109.9(4) . . ?
N2 C1 C19 116.8(4) . . ?
N1 C1 H1 106.8 . . ?
N2 C1 H1 106.8 . . ?
C19 C1 H1 106.8 . . ?
N1 C2 C17 108.5(4) . . ?
N1 C2 C3 104.8(3) . . ?
C17 C2 C3 114.3(4) . . ?
N1 C2 H2 109.7 . . ?
C17 C2 H2 109.7 . . ?
C3 C2 H2 109.7 . . ?
N2 C3 C4 59.3(3) . . ?
N2 C3 C11 117.8(4) . . ?
C4 C3 C11 121.1(4) . . ?
N2 C3 C2 107.8(3) . . ?
C4 C3 C2 114.3(4) . . ?
C11 C3 C2 120.4(4) . . ?
N2 C4 C5 115.5(4) . . ?
N2 C4 C3 60.2(3) . . ?
C5 C4 C3 119.8(4) . . ?
N2 C4 H4A 116.4 . . ?
C5 C4 H4A 116.4 . . ?
C3 C4 H4A 116.4 . . ?
C10 C5 C6 118.2(4) . . ?
C10 C5 C4 122.8(4) . . ?
C6 C5 C4 119.0(4) . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 117.9(5) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C9 122.9(4) . . ?
C7 C8 N3 118.3(5) . . ?
C9 C8 N3 118.8(4) . . ?
C8 C9 C10 117.8(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C5 C10 C9 121.5(4) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C16 118.9(4) . . ?
C12 C11 C3 120.7(4) . . ?
C16 C11 C3 120.4(4) . . ?
C11 C12 C13 119.9(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.8(5) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 119.8(5) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 120.9(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
O1 C17 O2 124.5(5) . . ?
O1 C17 C2 124.3(4) . . ?
O2 C17 C2 111.2(5) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.6(4) . . ?
C24 C19 C1 124.4(4) . . ?
C20 C19 C1 117.1(4) . . ?
C19 C20 C21 121.6(4) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 H20 119.2 . . ?
C22 C21 C20 118.0(4) . . ?
C22 C21 H21 121.0 . . ?
C20 C21 H21 121.0 . . ?
C23 C22 C21 122.2(4) . . ?
C23 C22 Br1 119.9(3) . . ?
C21 C22 Br1 117.9(3) . . ?
C22 C23 C24 118.8(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C19 C24 C23 120.7(4) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C41 O6 C42 115.9(5) . . ?
C25 N4 C26 105.1(4) . . ?
C25 N4 H4 109(4) . . ?
C26 N4 H4 105(4) . . ?
C28 N5 C27 61.5(3) . . ?
C28 N5 C25 116.4(4) . . ?
C27 N5 C25 105.7(3) . . ?
O7 N6 O8 123.5(6) . . ?
O7 N6 C32 118.0(6) . . ?
O8 N6 C32 118.5(6) . . ?
N4 C25 N5 108.9(4) . . ?
N4 C25 C43 110.6(4) . . ?
N5 C25 C43 116.3(4) . . ?
N4 C25 H25 106.9 . . ?
N5 C25 H25 106.9 . . ?
C43 C25 H25 106.9 . . ?
N4 C26 C41 109.8(4) . . ?
N4 C26 C27 105.2(4) . . ?
C41 C26 C27 114.0(4) . . ?
N4 C26 H26 109.2 . . ?
C41 C26 H26 109.2 . . ?
C27 C26 H26 109.2 . . ?
N5 C27 C35 118.3(4) . . ?
N5 C27 C28 59.2(3) . . ?
C35 C27 C28 123.9(4) . . ?
N5 C27 C26 106.8(4) . . ?
C35 C27 C26 119.6(4) . . ?
C28 C27 C26 112.8(4) . . ?
N5 C28 C29 117.1(4) . . ?
N5 C28 C27 59.3(3) . . ?
C29 C28 C27 121.1(4) . . ?
N5 C28 H28 115.8 . . ?
C29 C28 H28 115.8 . . ?
C27 C28 H28 115.8 . . ?
C30 C29 C34 118.0(4) . . ?
C30 C29 C28 119.1(4) . . ?
C34 C29 C28 122.9(4) . . ?
C31 C30 C29 122.1(5) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C32 118.4(5) . . ?
C30 C31 H31 120.8 . . ?
C32 C31 H31 120.8 . . ?
C33 C32 C31 121.5(5) . . ?
C33 C32 N6 119.5(5) . . ?
C31 C32 N6 118.9(5) . . ?
C32 C33 C34 119.5(5) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C29 120.5(5) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?
C36 C35 C40 118.3(5) . . ?
C36 C35 C27 120.4(4) . . ?
C40 C35 C27 121.3(4) . . ?
C35 C36 C37 120.4(5) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?
C38 C37 C36 120.5(6) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C39 C38 C37 119.6(5) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.3(6) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 C35 120.9(5) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
O5 C41 O6 123.7(5) . . ?
O5 C41 C26 124.5(5) . . ?
O6 C41 C26 111.8(4) . . ?
O6 C42 H42A 109.5 . . ?
O6 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
O6 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C48 118.5(5) . . ?
C44 C43 C25 123.6(4) . . ?
C48 C43 C25 117.9(4) . . ?
C43 C44 C45 120.8(5) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C46 C45 C44 119.2(4) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 120.9(4) . . ?
C45 C46 Br2 119.7(4) . . ?
C47 C46 Br2 119.4(4) . . ?
C48 C47 C46 118.9(4) . . ?
C48 C47 H47 120.5 . . ?
C46 C47 H47 120.5 . . ?
C47 C48 C43 121.7(5) . . ?
C47 C48 H48 119.2 . . ?
C43 C48 H48 119.2 . . ?

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
C2 N1 C1 N2 -27.6(5) . . . . ?
C2 N1 C1 C19 -157.1(4) . . . . ?
C4 N2 C1 N1 -45.3(5) . . . . ?
C3 N2 C1 N1 18.8(5) . . . . ?
C4 N2 C1 C19 80.2(5) . . . . ?
C3 N2 C1 C19 144.4(4) . . . . ?
C1 N1 C2 C17 146.7(4) . . . . ?
C1 N1 C2 C3 24.2(5) . . . . ?
C1 N2 C3 C4 -111.4(4) . . . . ?
C4 N2 C3 C11 -111.5(4) . . . . ?
C1 N2 C3 C11 137.1(4) . . . . ?
C4 N2 C3 C2 108.2(4) . . . . ?
C1 N2 C3 C2 -3.2(4) . . . . ?
N1 C2 C3 N2 -13.0(5) . . . . ?
C17 C2 C3 N2 -131.7(4) . . . . ?
N1 C2 C3 C4 50.6(5) . . . . ?
C17 C2 C3 C4 -68.0(5) . . . . ?
N1 C2 C3 C11 -152.1(4) . . . . ?
C17 C2 C3 C11 89.2(5) . . . . ?
C1 N2 C4 C5 -155.5(4) . . . . ?
C3 N2 C4 C5 111.2(4) . . . . ?
C1 N2 C4 C3 93.2(4) . . . . ?
C11 C3 C4 N2 105.9(4) . . . . ?
C2 C3 C4 N2 -97.0(4) . . . . ?
N2 C3 C4 C5 -104.1(4) . . . . ?
C11 C3 C4 C5 1.8(6) . . . . ?
C2 C3 C4 C5 158.9(4) . . . . ?
N2 C4 C5 C10 37.6(6) . . . . ?
C3 C4 C5 C10 106.4(5) . . . . ?
N2 C4 C5 C6 -140.2(4) . . . . ?
C3 C4 C5 C6 -71.4(6) . . . . ?
C10 C5 C6 C7 1.1(8) . . . . ?
C4 C5 C6 C7 178.9(5) . . . . ?
C5 C6 C7 C8 0.6(8) . . . . ?
C6 C7 C8 C9 -1.5(8) . . . . ?
C6 C7 C8 N3 -179.8(5) . . . . ?
O4 N3 C8 C7 -13.9(7) . . . . ?
O3 N3 C8 C7 167.5(5) . . . . ?
O4 N3 C8 C9 167.8(5) . . . . ?
O3 N3 C8 C9 -10.9(7) . . . . ?
C7 C8 C9 C10 0.8(7) . . . . ?
N3 C8 C9 C10 179.1(4) . . . . ?
C6 C5 C10 C9 -1.9(7) . . . . ?
C4 C5 C10 C9 -179.6(4) . . . . ?
C8 C9 C10 C5 1.0(7) . . . . ?
N2 C3 C11 C12 0.3(6) . . . . ?
C4 C3 C11 C12 -68.7(6) . . . . ?
C2 C3 C11 C12 135.6(5) . . . . ?
N2 C3 C11 C16 179.5(4) . . . . ?
C4 C3 C11 C16 110.4(5) . . . . ?
C2 C3 C11 C16 -45.3(6) . . . . ?
C16 C11 C12 C13 -1.7(7) . . . . ?
C3 C11 C12 C13 177.5(4) . . . . ?
C11 C12 C13 C14 0.7(8) . . . . ?
C12 C13 C14 C15 0.6(9) . . . . ?
C13 C14 C15 C16 -0.8(9) . . . . ?
C14 C15 C16 C11 -0.3(9) . . . . ?
C12 C11 C16 C15 1.5(8) . . . . ?
C3 C11 C16 C15 -177.6(5) . . . . ?
C18 O2 C17 O1 -0.5(8) . . . . ?
C18 O2 C17 C2 -179.1(4) . . . . ?
N1 C2 C17 O1 -40.6(7) . . . . ?
C3 C2 C17 O1 76.0(6) . . . . ?
N1 C2 C17 O2 138.0(4) . . . . ?
C3 C2 C17 O2 -105.4(4) . . . . ?
N1 C1 C19 C24 118.8(5) . . . . ?
N2 C1 C19 C24 -6.4(7) . . . . ?
N1 C1 C19 C20 -60.3(5) . . . . ?
N2 C1 C19 C20 174.5(4) . . . . ?
C24 C19 C20 C21 -2.1(7) . . . . ?
C1 C19 C20 C21 177.0(4) . . . . ?
C19 C20 C21 C22 0.4(7) . . . . ?
C20 C21 C22 C23 1.3(7) . . . . ?
C20 C21 C22 Br1 -178.3(3) . . . . ?
C21 C22 C23 C24 -1.3(8) . . . . ?
Br1 C22 C23 C24 178.3(4) . . . . ?
C20 C19 C24 C23 2.2(7) . . . . ?
C1 C19 C24 C23 -176.9(5) . . . . ?
C22 C23 C24 C19 -0.5(8) . . . . ?
C26 N4 C25 N5 -30.0(5) . . . . ?
C26 N4 C25 C43 -158.9(4) . . . . ?
C28 N5 C25 N4 -43.8(5) . . . . ?
C27 N5 C25 N4 21.7(5) . . . . ?
C28 N5 C25 C43 81.9(5) . . . . ?
C27 N5 C25 C43 147.4(4) . . . . ?
C25 N4 C26 C41 148.6(4) . . . . ?
C25 N4 C26 C27 25.5(5) . . . . ?
C28 N5 C27 C35 -114.6(4) . . . . ?
C25 N5 C27 C35 133.4(4) . . . . ?
C25 N5 C27 C28 -111.9(4) . . . . ?
C28 N5 C27 C26 106.9(4) . . . . ?
C25 N5 C27 C26 -5.0(4) . . . . ?
N4 C26 C27 N5 -12.8(5) . . . . ?
C41 C26 C27 N5 -133.1(4) . . . . ?
N4 C26 C27 C35 -150.6(4) . . . . ?
C41 C26 C27 C35 89.1(5) . . . . ?
N4 C26 C27 C28 50.3(5) . . . . ?
C41 C26 C27 C28 -70.0(5) . . . . ?
C27 N5 C28 C29 111.8(4) . . . . ?
C25 N5 C28 C29 -153.9(4) . . . . ?
C25 N5 C28 C27 94.2(4) . . . . ?
C35 C27 C28 N5 105.3(5) . . . . ?
C26 C27 C28 N5 -96.6(4) . . . . ?
N5 C27 C28 C29 -105.1(5) . . . . ?
C35 C27 C28 C29 0.2(7) . . . . ?
C26 C27 C28 C29 158.3(4) . . . . ?
N5 C28 C29 C30 -165.5(4) . . . . ?
C27 C28 C29 C30 -96.7(6) . . . . ?
N5 C28 C29 C34 12.2(6) . . . . ?
C27 C28 C29 C34 81.0(6) . . . . ?
C34 C29 C30 C31 0.3(8) . . . . ?
C28 C29 C30 C31 178.1(5) . . . . ?
C29 C30 C31 C32 -0.1(9) . . . . ?
C30 C31 C32 C33 0.1(9) . . . . ?
C30 C31 C32 N6 -178.7(5) . . . . ?
O7 N6 C32 C33 -179.9(6) . . . . ?
O8 N6 C32 C33 1.4(8) . . . . ?
O7 N6 C32 C31 -1.1(8) . . . . ?
O8 N6 C32 C31 -179.7(6) . . . . ?
C31 C32 C33 C34 -0.3(8) . . . . ?
N6 C32 C33 C34 178.5(4) . . . . ?
C32 C33 C34 C29 0.5(7) . . . . ?
C30 C29 C34 C33 -0.5(7) . . . . ?
C28 C29 C34 C33 -178.2(4) . . . . ?
N5 C27 C35 C36 -5.7(6) . . . . ?
C28 C27 C35 C36 -75.9(6) . . . . ?
C26 C27 C35 C36 127.4(5) . . . . ?
N5 C27 C35 C40 174.3(4) . . . . ?
C28 C27 C35 C40 104.1(6) . . . . ?
C26 C27 C35 C40 -52.6(6) . . . . ?
C40 C35 C36 C37 1.0(7) . . . . ?
C27 C35 C36 C37 -179.0(4) . . . . ?
C35 C36 C37 C38 0.0(8) . . . . ?
C36 C37 C38 C39 -0.4(8) . . . . ?
C37 C38 C39 C40 -0.1(9) . . . . ?
C38 C39 C40 C35 1.2(9) . . . . ?
C36 C35 C40 C39 -1.6(8) . . . . ?
C27 C35 C40 C39 178.5(5) . . . . ?
C42 O6 C41 O5 -0.3(8) . . . . ?
C42 O6 C41 C26 -179.3(5) . . . . ?
N4 C26 C41 O5 -39.6(6) . . . . ?
C27 C26 C41 O5 78.1(6) . . . . ?
N4 C26 C41 O6 139.5(4) . . . . ?
C27 C26 C41 O6 -102.8(5) . . . . ?
N4 C25 C43 C44 109.9(5) . . . . ?
N5 C25 C43 C44 -14.9(7) . . . . ?
N4 C25 C43 C48 -68.0(6) . . . . ?
N5 C25 C43 C48 167.1(4) . . . . ?
C48 C43 C44 C45 1.2(8) . . . . ?
C25 C43 C44 C45 -176.7(5) . . . . ?
C43 C44 C45 C46 0.4(8) . . . . ?
C44 C45 C46 C47 -2.0(8) . . . . ?
C44 C45 C46 Br2 176.7(4) . . . . ?
C45 C46 C47 C48 1.8(8) . . . . ?
Br2 C46 C47 C48 -176.9(4) . . . . ?
C46 C47 C48 C43 -0.2(8) . . . . ?
C44 C43 C48 C47 -1.3(8) . . . . ?
C25 C43 C48 C47 176.7(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
N1 H1A O1 0.80(5) 2.39(5) 2.805(7) 113(5) .
N4 H4 O5 0.89(6) 2.35(6) 2.826(6) 113(5) .
C25 H25 Br2 0.98 3.13 3.946(5) 142.0 1_455
C1 H1 Br1 0.98 3.00 3.834(5) 143.4 1_655
C1 H1 Br1 0.98 3.00 3.834(5) 143.4 1_655
C25 H25 Br2 0.98 3.13 3.946(5) 142.0 1_455
N4 H4 O5 0.89(6) 2.35(6) 2.826(6) 113(5) .
N1 H1A O1 0.80(5) 2.39(5) 2.805(7) 113(5) .

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4



