# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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. 
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data_d8v18592
_database_code_depnum_ccdc_archive 'CCDC 1914517'
loop_
_audit_author_name
_audit_author_address
'Hua Deng'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Br N3 O4'
_chemical_formula_weight         450.33

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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

_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'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.2024(3)
_cell_length_b                   31.7463(10)
_cell_length_c                   6.5544(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2122.89(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4386
_cell_measurement_theta_min      5.133
_cell_measurement_theta_max      49.157

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.966
_shelx_estimated_absorpt_T_min   0.695
_shelx_estimated_absorpt_T_max   0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5520
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            11503
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             4090
_reflns_number_gt                3140
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.972
_reflns_Friedel_fraction_full    0.971

_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)+(0.0231P)²+0.4792P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1093 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4090
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0905
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.017
_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 0.11800(6) 0.57032(2) -0.06914(8) 0.0848(3) Uani 1 1 d . . . . .
O1 O 0.5782(3) 0.40628(11) 0.2906(5) 0.0752(10) Uani 1 1 d . . . . .
O2 O 0.6863(3) 0.36463(11) 0.5030(5) 0.0738(10) Uani 1 1 d . . . . .
O3 O 0.3829(4) 0.31477(10) 1.2361(4) 0.0766(10) Uani 1 1 d . . . . .
O4 O 0.4541(3) 0.26921(8) 0.9911(4) 0.0594(8) Uani 1 1 d . . . . .
N1 N 0.4660(4) 0.44884(12) 0.6272(8) 0.0680(12) Uani 1 1 d D . . . .
N2 N 0.3843(5) 0.33184(11) 0.9051(5) 0.0754(12) Uani 1 1 d . . . . .
N3 N 0.0634(4) 0.37569(14) 0.5744(9) 0.0811(12) Uani 1 1 d . . . . .
C1 C 0.3253(4) 0.44591(11) 0.5788(7) 0.0477(9) Uani 1 1 d . . . . .
H1A H 0.2772 0.4522 0.7045 0.057 Uiso 1 1 calc R U . . .
C2 C 0.3055(4) 0.39841(11) 0.5336(6) 0.0403(9) Uani 1 1 d . . . . .
H2 H 0.3344 0.3925 0.3939 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4012(4) 0.37850(11) 0.6818(5) 0.0434(9) Uani 1 1 d . . . . .
C4 C 0.5227(4) 0.40658(13) 0.6459(7) 0.0555(11) Uani 1 1 d . . . . .
H4 H 0.5802 0.4054 0.7655 0.067 Uiso 1 1 calc R U . . .
C5 C 0.5972(4) 0.39322(13) 0.4597(7) 0.0540(10) Uani 1 1 d . . . . .
C6 C 0.7603(6) 0.34771(19) 0.3337(9) 0.0867(17) Uani 1 1 d . . . . .
H6A H 0.7011 0.3378 0.2305 0.130 Uiso 1 1 calc R U . . .
H6B H 0.8136 0.3247 0.3804 0.130 Uiso 1 1 calc R U . . .
H6C H 0.8155 0.3693 0.2778 0.130 Uiso 1 1 calc R U . . .
C7 C 0.4216(4) 0.33038(11) 0.6908(5) 0.0468(10) Uani 1 1 d . . . . .
H7A H 0.3613 0.3146 0.6057 0.056 Uiso 1 1 calc R U . . .
H7B H 0.5114 0.3216 0.6678 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3584(5) 0.37650(12) 0.9109(6) 0.0568(11) Uani 1 1 d . . . . .
H8A H 0.4152 0.3920 1.0026 0.068 Uiso 1 1 calc R U . . .
H8B H 0.2670 0.3835 0.9336 0.068 Uiso 1 1 calc R U . . .
C9 C 0.1697(4) 0.38500(12) 0.5561(7) 0.0503(10) Uani 1 1 d . . . . .
C10 C 0.2778(4) 0.47626(10) 0.4186(7) 0.0466(9) Uani 1 1 d . . . . .
C11 C 0.1779(4) 0.50383(13) 0.4634(7) 0.0589(11) Uani 1 1 d . . . . .
H11 H 0.1411 0.5034 0.5932 0.071 Uiso 1 1 calc R U . . .
C12 C 0.1308(5) 0.53215(13) 0.3207(7) 0.0638(12) Uani 1 1 d . . . . .
H12 H 0.0633 0.5506 0.3539 0.077 Uiso 1 1 calc R U . . .
C13 C 0.1849(5) 0.53255(12) 0.1307(7) 0.0577(11) Uani 1 1 d . . . . .
C14 C 0.2888(5) 0.50642(12) 0.0816(7) 0.0594(11) Uani 1 1 d . . . . .
H14 H 0.3277 0.5077 -0.0466 0.071 Uiso 1 1 calc R U . . .
C15 C 0.3339(5) 0.47830(12) 0.2269(6) 0.0542(11) Uani 1 1 d . . . . .
H15 H 0.4031 0.4604 0.1949 0.065 Uiso 1 1 calc R U . . .
C16 C 0.4056(5) 0.30576(13) 1.0616(6) 0.0575(10) Uani 1 1 d . . . . .
C17 C 0.4695(5) 0.23214(13) 1.1250(7) 0.0613(12) Uani 1 1 d . . . . .
C18 C 0.5678(7) 0.24080(17) 1.2918(9) 0.0917(19) Uani 1 1 d . . . . .
H18A H 0.6461 0.2524 1.2332 0.138 Uiso 1 1 calc R U . . .
H18B H 0.5886 0.2150 1.3609 0.138 Uiso 1 1 calc R U . . .
H18C H 0.5313 0.2605 1.3874 0.138 Uiso 1 1 calc R U . . .
C19 C 0.5254(6) 0.19976(15) 0.9797(8) 0.0759(15) Uani 1 1 d . . . . .
H19A H 0.4661 0.1958 0.8677 0.114 Uiso 1 1 calc R U . . .
H19B H 0.5372 0.1735 1.0503 0.114 Uiso 1 1 calc R U . . .
H19C H 0.6084 0.2094 0.9290 0.114 Uiso 1 1 calc R U . . .
C20 C 0.3384(6) 0.21909(19) 1.2048(11) 0.101(2) Uani 1 1 d . . . . .
H20A H 0.3088 0.2392 1.3038 0.152 Uiso 1 1 calc R U . . .
H20B H 0.3454 0.1919 1.2676 0.152 Uiso 1 1 calc R U . . .
H20C H 0.2768 0.2178 1.0942 0.152 Uiso 1 1 calc R U . . .
H1 H 0.498(5) 0.4621(15) 0.533(6) 0.071(18) Uiso 1 1 d 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 1.902(4) . ?
O1 C5 1.199(5) . ?
O2 C5 1.316(5) . ?
O2 C6 1.446(6) . ?
O3 C16 1.201(5) . ?
O4 C16 1.344(5) . ?
O4 C17 1.476(4) . ?
N1 C4 1.466(6) . ?
N1 C1 1.472(6) . ?
N1 H1 0.82(2) . ?
N2 C16 1.336(5) . ?
N2 C8 1.443(5) . ?
N2 C7 1.456(5) . ?
N3 C9 1.131(5) . ?
C1 C10 1.505(6) . ?
C1 C2 1.550(5) . ?
C1 H1A 0.9800 . ?
C2 C9 1.457(6) . ?
C2 C3 1.516(5) . ?
C2 H2 0.9800 . ?
C3 C7 1.543(5) . ?
C3 C4 1.544(6) . ?
C3 C8 1.565(5) . ?
C4 C5 1.499(6) . ?
C4 H4 0.9800 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.375(6) . ?
C10 C15 1.382(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.362(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C14 C15 1.384(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 C20 1.494(8) . ?
C17 C18 1.509(7) . ?
C17 C19 1.513(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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 O2 C6 116.9(4) . . ?
C16 O4 C17 121.5(3) . . ?
C4 N1 C1 110.2(3) . . ?
C4 N1 H1 112(4) . . ?
C1 N1 H1 105(4) . . ?
C16 N2 C8 128.2(3) . . ?
C16 N2 C7 132.7(4) . . ?
C8 N2 C7 96.0(3) . . ?
N1 C1 C10 115.1(4) . . ?
N1 C1 C2 103.3(3) . . ?
C10 C1 C2 116.6(3) . . ?
N1 C1 H1A 107.1 . . ?
C10 C1 H1A 107.1 . . ?
C2 C1 H1A 107.1 . . ?
C9 C2 C3 115.2(3) . . ?
C9 C2 C1 112.9(3) . . ?
C3 C2 C1 101.5(3) . . ?
C9 C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
C2 C3 C7 121.6(3) . . ?
C2 C3 C4 100.3(3) . . ?
C7 C3 C4 118.0(3) . . ?
C2 C3 C8 116.9(3) . . ?
C7 C3 C8 87.8(3) . . ?
C4 C3 C8 113.2(3) . . ?
N1 C4 C5 113.0(4) . . ?
N1 C4 C3 103.0(4) . . ?
C5 C4 C3 111.6(3) . . ?
N1 C4 H4 109.7 . . ?
C5 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
O1 C5 O2 123.3(4) . . ?
O1 C5 C4 125.0(4) . . ?
O2 C5 C4 111.7(4) . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 C3 88.3(3) . . ?
N2 C7 H7A 113.9 . . ?
C3 C7 H7A 113.9 . . ?
N2 C7 H7B 113.9 . . ?
C3 C7 H7B 113.9 . . ?
H7A C7 H7B 111.1 . . ?
N2 C8 C3 87.9(3) . . ?
N2 C8 H8A 114.0 . . ?
C3 C8 H8A 114.0 . . ?
N2 C8 H8B 114.0 . . ?
C3 C8 H8B 114.0 . . ?
H8A C8 H8B 111.2 . . ?
N3 C9 C2 178.2(5) . . ?
C11 C10 C15 118.1(4) . . ?
C11 C10 C1 119.8(4) . . ?
C15 C10 C1 122.1(4) . . ?
C10 C11 C12 121.8(4) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.1(4) . . ?
C12 C13 Br1 119.3(4) . . ?
C14 C13 Br1 119.5(4) . . ?
C15 C14 C13 118.8(4) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C10 C15 C14 121.2(4) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
O3 C16 N2 123.5(4) . . ?
O3 C16 O4 127.2(4) . . ?
N2 C16 O4 109.4(3) . . ?
O4 C17 C20 109.5(4) . . ?
O4 C17 C18 110.8(4) . . ?
C20 C17 C18 113.1(5) . . ?
O4 C17 C19 102.0(3) . . ?
C20 C17 C19 111.7(5) . . ?
C18 C17 C19 109.2(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N1 C1 C10 -137.3(4) . . . . ?
C4 N1 C1 C2 -9.2(5) . . . . ?
N1 C1 C2 C9 158.4(4) . . . . ?
C10 C1 C2 C9 -74.3(5) . . . . ?
N1 C1 C2 C3 34.5(4) . . . . ?
C10 C1 C2 C3 161.8(3) . . . . ?
C9 C2 C3 C7 59.7(5) . . . . ?
C1 C2 C3 C7 -178.0(4) . . . . ?
C9 C2 C3 C4 -168.1(3) . . . . ?
C1 C2 C3 C4 -45.7(4) . . . . ?
C9 C2 C3 C8 -45.3(5) . . . . ?
C1 C2 C3 C8 77.0(4) . . . . ?
C1 N1 C4 C5 101.1(5) . . . . ?
C1 N1 C4 C3 -19.4(5) . . . . ?
C2 C3 C4 N1 40.4(4) . . . . ?
C7 C3 C4 N1 174.9(3) . . . . ?
C8 C3 C4 N1 -84.8(4) . . . . ?
C2 C3 C4 C5 -81.0(4) . . . . ?
C7 C3 C4 C5 53.4(5) . . . . ?
C8 C3 C4 C5 153.7(3) . . . . ?
C6 O2 C5 O1 -2.2(7) . . . . ?
C6 O2 C5 C4 177.0(4) . . . . ?
N1 C4 C5 O1 -25.5(6) . . . . ?
C3 C4 C5 O1 90.0(5) . . . . ?
N1 C4 C5 O2 155.4(4) . . . . ?
C3 C4 C5 O2 -89.2(4) . . . . ?
C16 N2 C7 C3 -158.9(6) . . . . ?
C8 N2 C7 C3 1.8(4) . . . . ?
C2 C3 C7 N2 -122.1(4) . . . . ?
C4 C3 C7 N2 113.5(4) . . . . ?
C8 C3 C7 N2 -1.7(4) . . . . ?
C16 N2 C8 C3 160.2(6) . . . . ?
C7 N2 C8 C3 -1.8(4) . . . . ?
C2 C3 C8 N2 126.3(4) . . . . ?
C7 C3 C8 N2 1.7(4) . . . . ?
C4 C3 C8 N2 -118.0(4) . . . . ?
N1 C1 C10 C11 -122.8(4) . . . . ?
C2 C1 C10 C11 116.0(4) . . . . ?
N1 C1 C10 C15 55.5(5) . . . . ?
C2 C1 C10 C15 -65.7(5) . . . . ?
C15 C10 C11 C12 1.9(7) . . . . ?
C1 C10 C11 C12 -179.7(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 C14 -2.6(7) . . . . ?
C11 C12 C13 Br1 178.4(4) . . . . ?
C12 C13 C14 C15 2.8(7) . . . . ?
Br1 C13 C14 C15 -178.2(3) . . . . ?
C11 C10 C15 C14 -1.7(6) . . . . ?
C1 C10 C15 C14 -180.0(4) . . . . ?
C13 C14 C15 C10 -0.6(6) . . . . ?
C8 N2 C16 O3 14.0(9) . . . . ?
C7 N2 C16 O3 169.2(6) . . . . ?
C8 N2 C16 O4 -166.4(5) . . . . ?
C7 N2 C16 O4 -11.1(8) . . . . ?
C17 O4 C16 O3 8.6(7) . . . . ?
C17 O4 C16 N2 -171.0(4) . . . . ?
C16 O4 C17 C20 61.3(6) . . . . ?
C16 O4 C17 C18 -64.1(6) . . . . ?
C16 O4 C17 C19 179.7(4) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v19133_0m
_database_code_depnum_ccdc_archive 'CCDC 1914518'
loop_
_audit_author_name
_audit_author_address
'Hua Deng'
;East China University of Science and Technology
China
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H24 Br N3 O4'
_chemical_formula_weight         450.33

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4829(2)
_cell_length_b                   12.2525(3)
_cell_length_c                   26.9553(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2141.11(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5429
_cell_measurement_theta_min      4.493
_cell_measurement_theta_max      54.962

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.949
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3565
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            10450
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4108
_reflns_number_gt                3670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.973
_reflns_Friedel_fraction_full    0.972

_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)+(0.0182P)²+0.1645P] 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       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1389 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.021(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4108
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.001
_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 0.52021(6) 0.64635(3) 0.32460(2) 0.05020(17) Uani 1 1 d . . . . .
O1 O 0.0749(5) 0.2229(2) 0.54903(11) 0.0538(8) Uani 1 1 d . . . . .
O2 O 0.1662(5) 0.3208(2) 0.61432(11) 0.0618(9) Uani 1 1 d . . . . .
O3 O 0.6046(4) 0.5202(2) 0.63303(9) 0.0391(7) Uani 1 1 d . . . . .
O4 O 0.3664(3) 0.5769(2) 0.68998(8) 0.0336(6) Uani 1 1 d . . . . .
N1 N -0.0920(5) 0.4031(2) 0.50335(12) 0.0377(8) Uani 1 1 d D . . . .
N2 N 0.2815(4) 0.5716(2) 0.61125(9) 0.0259(6) Uani 1 1 d . . . . .
N3 N 0.0369(4) 0.7834(2) 0.52023(10) 0.0332(7) Uani 1 1 d . . . . .
C1 C -0.1208(5) 0.5145(3) 0.48380(12) 0.0315(8) Uani 1 1 d . . . . .
H1A H -0.2637 0.5221 0.4702 0.038 Uiso 1 1 calc R U . . .
C2 C -0.0994(5) 0.5853(2) 0.53157(12) 0.0240(7) Uani 1 1 d . . . . .
H2 H -0.2392 0.5905 0.5471 0.029 Uiso 1 1 calc R U . . .
C3 C 0.0360(5) 0.5169(2) 0.56608(11) 0.0235(6) Uani 1 1 d . . . . .
C4 C -0.0582(5) 0.4043(2) 0.55685(12) 0.0275(7) Uani 1 1 d . . . . .
H4 H -0.1949 0.4003 0.5740 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2748(5) 0.5291(3) 0.56027(11) 0.0247(7) Uani 1 1 d . . . . .
H5A H 0.3483 0.4589 0.5559 0.030 Uiso 1 1 calc R U . . .
H5B H 0.3169 0.5827 0.5347 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0586(4) 0.5593(3) 0.61983(11) 0.0249(7) Uani 1 1 d . . . . .
H6A H -0.0139 0.6290 0.6261 0.030 Uiso 1 1 calc R U . . .
H6B H 0.0236 0.5044 0.6454 0.030 Uiso 1 1 calc R U . . .
C7 C -0.0238(5) 0.6970(3) 0.52430(11) 0.0253(7) Uani 1 1 d . . . . .
C8 C 0.0339(5) 0.5416(3) 0.44372(11) 0.0306(7) Uani 1 1 d . . . . .
C9 C 0.2137(6) 0.4822(3) 0.43661(13) 0.0359(9) Uani 1 1 d . . . . .
H9 H 0.2389 0.4195 0.4564 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3563(6) 0.5125(3) 0.40134(13) 0.0377(9) Uani 1 1 d . . . . .
H10 H 0.4788 0.4710 0.3970 0.045 Uiso 1 1 calc R U . . .
C11 C 0.3208(6) 0.6028(3) 0.37252(13) 0.0353(9) Uani 1 1 d . . . . .
C12 C 0.1420(6) 0.6633(3) 0.37785(13) 0.0394(9) Uani 1 1 d . . . . .
H12 H 0.1172 0.7251 0.3574 0.047 Uiso 1 1 calc R U . . .
C13 C 0.0008(5) 0.6323(3) 0.41322(11) 0.0352(8) Uani 1 1 d . . . . .
H13 H -0.1223 0.6735 0.4170 0.042 Uiso 1 1 calc R U . . .
C14 C 0.0685(5) 0.3064(3) 0.57160(13) 0.0348(8) Uani 1 1 d . . . . .
C15 C 0.2957(10) 0.2317(4) 0.6310(2) 0.096(2) Uani 1 1 d . . . . .
H15A H 0.3912 0.2582 0.6565 0.144 Uiso 1 1 calc R U . . .
H15B H 0.3744 0.2028 0.6029 0.144 Uiso 1 1 calc R U . . .
H15C H 0.2092 0.1737 0.6450 0.144 Uiso 1 1 calc R U . . .
C16 C 0.4337(5) 0.5524(3) 0.64406(12) 0.0274(7) Uani 1 1 d . . . . .
C17 C 0.4862(6) 0.5478(3) 0.73453(11) 0.0345(8) Uani 1 1 d . . . . .
C18 C 0.3490(7) 0.5897(4) 0.77588(13) 0.0482(11) Uani 1 1 d . . . . .
H18A H 0.2150 0.5529 0.7743 0.072 Uiso 1 1 calc R U . . .
H18B H 0.3293 0.6686 0.7720 0.072 Uiso 1 1 calc R U . . .
H18C H 0.4142 0.5748 0.8080 0.072 Uiso 1 1 calc R U . . .
C19 C 0.6935(6) 0.6056(3) 0.73503(14) 0.0453(10) Uani 1 1 d . . . . .
H19A H 0.6726 0.6840 0.7297 0.068 Uiso 1 1 calc R U . . .
H19B H 0.7808 0.5762 0.7085 0.068 Uiso 1 1 calc R U . . .
H19C H 0.7608 0.5939 0.7672 0.068 Uiso 1 1 calc R U . . .
C20 C 0.5085(8) 0.4249(3) 0.73685(15) 0.0545(11) Uani 1 1 d . . . . .
H20A H 0.5981 0.4001 0.7098 0.082 Uiso 1 1 calc R U . . .
H20B H 0.3724 0.3908 0.7335 0.082 Uiso 1 1 calc R U . . .
H20C H 0.5695 0.4041 0.7688 0.082 Uiso 1 1 calc R U . . .
H1 H -0.192(5) 0.366(3) 0.4979(17) 0.064(14) Uiso 1 1 d 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 C11 1.904(4) . ?
O1 C14 1.191(4) . ?
O2 C14 1.326(4) . ?
O2 C15 1.449(5) . ?
O3 C16 1.213(4) . ?
O4 C16 1.346(4) . ?
O4 C17 1.474(4) . ?
N1 C4 1.459(4) . ?
N1 C1 1.476(5) . ?
N1 H1 0.81(2) . ?
N2 C16 1.346(4) . ?
N2 C5 1.470(4) . ?
N2 C6 1.471(4) . ?
N3 C7 1.134(4) . ?
C1 C8 1.511(5) . ?
C1 C2 1.559(4) . ?
C1 H1A 1.0000 . ?
C2 C7 1.467(4) . ?
C2 C3 1.529(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.530(4) . ?
C3 C6 1.546(4) . ?
C3 C5 1.563(4) . ?
C4 C14 1.507(5) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.388(5) . ?
C8 C13 1.399(5) . ?
C9 C10 1.377(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(5) . ?
C12 C13 1.375(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C17 C20 1.514(5) . ?
C17 C18 1.516(5) . ?
C17 C19 1.519(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C14 O2 C15 116.5(3) . . ?
C16 O4 C17 121.6(3) . . ?
C4 N1 C1 111.3(3) . . ?
C4 N1 H1 108(3) . . ?
C1 N1 H1 111(3) . . ?
C16 N2 C5 125.0(3) . . ?
C16 N2 C6 126.8(3) . . ?
C5 N2 C6 94.7(2) . . ?
N1 C1 C8 112.0(3) . . ?
N1 C1 C2 102.1(3) . . ?
C8 C1 C2 114.1(3) . . ?
N1 C1 H1A 109.5 . . ?
C8 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C7 C2 C3 113.6(3) . . ?
C7 C2 C1 116.0(3) . . ?
C3 C2 C1 104.4(2) . . ?
C7 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C2 C3 C4 99.6(2) . . ?
C2 C3 C6 116.1(3) . . ?
C4 C3 C6 119.5(3) . . ?
C2 C3 C5 117.1(3) . . ?
C4 C3 C5 117.7(3) . . ?
C6 C3 C5 88.2(2) . . ?
N1 C4 C14 109.5(3) . . ?
N1 C4 C3 103.3(3) . . ?
C14 C4 C3 117.2(3) . . ?
N1 C4 H4 108.8 . . ?
C14 C4 H4 108.8 . . ?
C3 C4 H4 108.8 . . ?
N2 C5 C3 88.2(2) . . ?
N2 C5 H5A 113.9 . . ?
C3 C5 H5A 113.9 . . ?
N2 C5 H5B 113.9 . . ?
C3 C5 H5B 113.9 . . ?
H5A C5 H5B 111.1 . . ?
N2 C6 C3 88.9(2) . . ?
N2 C6 H6A 113.8 . . ?
C3 C6 H6A 113.8 . . ?
N2 C6 H6B 113.8 . . ?
C3 C6 H6B 113.8 . . ?
H6A C6 H6B 111.1 . . ?
N3 C7 C2 177.8(3) . . ?
C9 C8 C13 117.7(3) . . ?
C9 C8 C1 122.8(3) . . ?
C13 C8 C1 119.5(3) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 119.7(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 Br1 119.8(3) . . ?
C12 C11 Br1 119.3(3) . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
O1 C14 O2 122.8(3) . . ?
O1 C14 C4 124.6(3) . . ?
O2 C14 C4 112.5(3) . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C16 N2 124.4(3) . . ?
O3 C16 O4 126.4(3) . . ?
N2 C16 O4 109.1(3) . . ?
O4 C17 C20 108.9(3) . . ?
O4 C17 C18 102.0(3) . . ?
C20 C17 C18 111.3(3) . . ?
O4 C17 C19 111.1(3) . . ?
C20 C17 C19 112.3(4) . . ?
C18 C17 C19 110.8(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N1 C1 C8 122.9(3) . . . . ?
C4 N1 C1 C2 0.4(4) . . . . ?
N1 C1 C2 C7 152.2(3) . . . . ?
C8 C1 C2 C7 31.1(4) . . . . ?
N1 C1 C2 C3 26.3(3) . . . . ?
C8 C1 C2 C3 -94.7(3) . . . . ?
C7 C2 C3 C4 -169.0(3) . . . . ?
C1 C2 C3 C4 -41.7(3) . . . . ?
C7 C2 C3 C6 61.2(4) . . . . ?
C1 C2 C3 C6 -171.4(3) . . . . ?
C7 C2 C3 C5 -41.0(4) . . . . ?
C1 C2 C3 C5 86.4(3) . . . . ?
C1 N1 C4 C14 -152.4(3) . . . . ?
C1 N1 C4 C3 -26.8(4) . . . . ?
C2 C3 C4 N1 41.4(3) . . . . ?
C6 C3 C4 N1 168.9(3) . . . . ?
C5 C3 C4 N1 -86.3(3) . . . . ?
C2 C3 C4 C14 161.9(3) . . . . ?
C6 C3 C4 C14 -70.6(4) . . . . ?
C5 C3 C4 C14 34.3(4) . . . . ?
C16 N2 C5 C3 143.9(3) . . . . ?
C6 N2 C5 C3 1.6(3) . . . . ?
C2 C3 C5 N2 117.1(3) . . . . ?
C4 C3 C5 N2 -124.2(3) . . . . ?
C6 C3 C5 N2 -1.5(2) . . . . ?
C16 N2 C6 C3 -142.9(3) . . . . ?
C5 N2 C6 C3 -1.6(3) . . . . ?
C2 C3 C6 N2 -118.0(3) . . . . ?
C4 C3 C6 N2 122.7(3) . . . . ?
C5 C3 C6 N2 1.5(2) . . . . ?
N1 C1 C8 C9 -17.1(4) . . . . ?
C2 C1 C8 C9 98.2(4) . . . . ?
N1 C1 C8 C13 165.2(3) . . . . ?
C2 C1 C8 C13 -79.5(4) . . . . ?
C13 C8 C9 C10 1.0(5) . . . . ?
C1 C8 C9 C10 -176.7(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C9 C10 C11 Br1 178.8(3) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
Br1 C11 C12 C13 -178.8(3) . . . . ?
C11 C12 C13 C8 0.0(5) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C1 C8 C13 C12 176.8(3) . . . . ?
C15 O2 C14 O1 4.4(6) . . . . ?
C15 O2 C14 C4 -178.7(4) . . . . ?
N1 C4 C14 O1 -25.8(5) . . . . ?
C3 C4 C14 O1 -142.9(4) . . . . ?
N1 C4 C14 O2 157.4(3) . . . . ?
C3 C4 C14 O2 40.2(4) . . . . ?
C5 N2 C16 O3 18.2(5) . . . . ?
C6 N2 C16 O3 148.6(3) . . . . ?
C5 N2 C16 O4 -163.2(3) . . . . ?
C6 N2 C16 O4 -32.8(4) . . . . ?
C17 O4 C16 O3 -11.4(5) . . . . ?
C17 O4 C16 N2 170.0(3) . . . . ?
C16 O4 C17 C20 -61.5(4) . . . . ?
C16 O4 C17 C18 -179.2(3) . . . . ?
C16 O4 C17 C19 62.7(4) . . . . ?

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 H1 O1 0.81(2) 2.25(3) 3.006(4) 156(4) 4_456
C20 H20C Br1 0.98 3.12 3.961(5) 145.0 2_665
C20 H20A O3 0.98 2.54 3.096(5) 115.9 .
C19 H19B O3 0.98 2.43 2.998(5) 116.2 .
C6 H6A Br1 0.99 3.06 3.913(3) 144.6 4_466
C5 H5B N3 0.99 2.63 3.588(4) 162.8 4_566
C4 H4 O3 1.00 2.53 3.319(4) 135.9 1_455
N1 H1 O1 0.81(2) 2.25(3) 3.006(4) 156(4) 4_456
C20 H20C Br1 0.98 3.12 3.961(5) 145.0 2_665
C20 H20A O3 0.98 2.54 3.096(5) 115.9 .
C19 H19B O3 0.98 2.43 2.998(5) 116.2 .
C6 H6A Br1 0.99 3.06 3.913(3) 144.6 4_466
C5 H5B N3 0.99 2.63 3.588(4) 162.8 4_566
C4 H4 O3 1.00 2.53 3.319(4) 135.9 1_455

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.043

_shelxl_version_number           2013-4



