# 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. 
# 
#######################################################################

data_ga_80607a_a
_database_code_depnum_ccdc_archive 'CCDC 1906923'
loop_
_audit_author_name
_audit_author_address
'Jian Li'
;Shanghai university
China
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N2 O4'
_chemical_formula_weight         302.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   9.2327(3)
_cell_length_b                   14.7102(5)
_cell_length_c                   11.8386(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.1880(10)
_cell_angle_gamma                90
_cell_volume                     1536.05(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7840
_cell_measurement_theta_min      5.09
_cell_measurement_theta_max      55.87

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.499
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            13874
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.290
_diffrn_reflns_theta_max         55.920
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3027
_reflns_number_gt                2474
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0503P)²+0.3666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.37549(14) 0.41291(8) 0.42784(10) 0.0482(3) Uani 1 1 d . . . . .
N2 N 0.46698(16) 0.26402(10) 0.56424(12) 0.0577(4) Uani 1 1 d . . . . .
O1 O 0.44107(13) 0.53054(7) 0.26309(9) 0.0557(3) Uani 1 1 d . . . . .
O2 O 0.65129(15) 0.45519(9) 0.27914(12) 0.0749(4) Uani 1 1 d . . . . .
O3 O 0.74113(13) 0.15895(8) 0.46013(10) 0.0645(3) Uani 1 1 d . . . . .
O4 O 0.76041(16) 0.16470(9) 0.65197(11) 0.0760(4) Uani 1 1 d . . . . .
C1 C 0.53882(19) 0.46134(10) 0.30914(13) 0.0520(4) Uani 1 1 d . . . . .
C2 C 0.49715(17) 0.39917(9) 0.39464(12) 0.0455(3) Uani 1 1 d . . . . .
C3 C 0.27896(17) 0.48369(10) 0.37720(12) 0.0476(3) Uani 1 1 d . . . . .
C4 C 0.1457(2) 0.49782(13) 0.40590(15) 0.0630(4) Uani 1 1 d . . . . .
H4 H 0.1217 0.4601 0.4608 0.076 Uiso 1 1 calc R U . . .
C5 C 0.0485(2) 0.56690(14) 0.35427(17) 0.0728(5) Uani 1 1 d . . . . .
H5 H -0.0412 0.5750 0.3736 0.087 Uiso 1 1 calc R U . . .
C6 C 0.0832(2) 0.62420(13) 0.27399(16) 0.0673(5) Uani 1 1 d . . . . .
H6 H 0.0178 0.6715 0.2404 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2135(2) 0.61176(11) 0.24364(14) 0.0598(4) Uani 1 1 d . . . . .
H7 H 0.2369 0.6501 0.1891 0.072 Uiso 1 1 calc R U . . .
C8 C 0.30976(18) 0.54170(10) 0.29485(12) 0.0483(4) Uani 1 1 d . . . . .
C9 C 0.59745(17) 0.32532(10) 0.43600(12) 0.0487(4) Uani 1 1 d . . . . .
H9 H 0.6807 0.3200 0.4075 0.058 Uiso 1 1 calc R U . . .
C10 C 0.58032(17) 0.26062(10) 0.51569(12) 0.0478(3) Uani 1 1 d . . . . .
C11 C 0.4102(2) 0.20097(12) 0.63960(16) 0.0635(5) Uani 1 1 d . . . . .
C12 C 0.4960(2) 0.21494(14) 0.76920(16) 0.0721(5) Uani 1 1 d . . . . .
H12A H 0.6007 0.1994 0.7826 0.108 Uiso 1 1 calc R U . . .
H12B H 0.4532 0.1768 0.8169 0.108 Uiso 1 1 calc R U . . .
H12C H 0.4882 0.2774 0.7901 0.108 Uiso 1 1 calc R U . . .
C13 C 0.2458(2) 0.2298(2) 0.6184(2) 0.1081(9) Uani 1 1 d . . . . .
H13A H 0.2003 0.1930 0.6656 0.162 Uiso 1 1 calc R U . . .
H13B H 0.1912 0.2221 0.5364 0.162 Uiso 1 1 calc R U . . .
H13C H 0.2424 0.2925 0.6400 0.162 Uiso 1 1 calc R U . . .
C14 C 0.4193(3) 0.10212(14) 0.60435(18) 0.0908(7) Uani 1 1 d . . . . .
H14A H 0.5236 0.0838 0.6241 0.136 Uiso 1 1 calc R U . . .
H14B H 0.3729 0.0957 0.5207 0.136 Uiso 1 1 calc R U . . .
H14C H 0.3671 0.0645 0.6460 0.136 Uiso 1 1 calc R U . . .
C15 C 0.70205(18) 0.18945(10) 0.55259(14) 0.0521(4) Uani 1 1 d . . . . .
C16 C 0.8619(2) 0.09309(14) 0.48431(19) 0.0755(5) Uani 1 1 d . . . . .
H16A H 0.9539 0.1205 0.5323 0.113 Uiso 1 1 calc R U . . .
H16B H 0.8759 0.0727 0.4112 0.113 Uiso 1 1 calc R U . . .
H16C H 0.8364 0.0422 0.5255 0.113 Uiso 1 1 calc R U . . .
H2 H 0.405(2) 0.3097(14) 0.5376(17) 0.072(6) 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
N1 C2 1.3108(19) . ?
N1 C3 1.3864(19) . ?
N2 C10 1.335(2) . ?
N2 C11 1.486(2) . ?
N2 H2 0.88(2) . ?
O1 C1 1.3627(19) . ?
O1 C8 1.3811(19) . ?
O2 C1 1.1960(19) . ?
O3 C15 1.3278(19) . ?
O3 C16 1.441(2) . ?
O4 C15 1.1969(19) . ?
C1 C2 1.496(2) . ?
C2 C9 1.418(2) . ?
C3 C4 1.386(2) . ?
C3 C8 1.387(2) . ?
C4 C5 1.374(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(2) . ?
C7 H7 0.9300 . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 C15 1.503(2) . ?
C11 C12 1.518(3) . ?
C11 C14 1.522(3) . ?
C11 C13 1.524(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C2 N1 C3 118.98(12) . . ?
C10 N2 C11 134.06(15) . . ?
C10 N2 H2 112.6(13) . . ?
C11 N2 H2 112.6(13) . . ?
C1 O1 C8 120.71(11) . . ?
C15 O3 C16 116.52(13) . . ?
O2 C1 O1 117.91(14) . . ?
O2 C1 C2 125.03(15) . . ?
O1 C1 C2 117.06(13) . . ?
N1 C2 C9 123.01(13) . . ?
N1 C2 C1 121.53(13) . . ?
C9 C2 C1 115.45(13) . . ?
C4 C3 N1 120.71(14) . . ?
C4 C3 C8 117.48(14) . . ?
N1 C3 C8 121.80(14) . . ?
C5 C4 C3 120.83(16) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.34(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.15(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.22(16) . . ?
C6 C7 H7 120.4 . . ?
C8 C7 H7 120.4 . . ?
C7 C8 O1 118.23(14) . . ?
C7 C8 C3 121.96(15) . . ?
O1 C8 C3 119.80(13) . . ?
C10 C9 C2 124.67(14) . . ?
C10 C9 H9 117.7 . . ?
C2 C9 H9 117.7 . . ?
N2 C10 C9 122.04(14) . . ?
N2 C10 C15 120.97(13) . . ?
C9 C10 C15 116.84(14) . . ?
N2 C11 C12 110.56(14) . . ?
N2 C11 C14 111.97(15) . . ?
C12 C11 C14 110.60(15) . . ?
N2 C11 C13 103.79(14) . . ?
C12 C11 C13 108.97(18) . . ?
C14 C11 C13 110.73(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 123.67(15) . . ?
O4 C15 C10 125.33(15) . . ?
O3 C15 C10 110.96(13) . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C8 O1 C1 O2 -179.55(14) . . . . ?
C8 O1 C1 C2 -0.1(2) . . . . ?
C3 N1 C2 C9 -176.05(13) . . . . ?
C3 N1 C2 C1 3.8(2) . . . . ?
O2 C1 C2 N1 176.52(16) . . . . ?
O1 C1 C2 N1 -2.9(2) . . . . ?
O2 C1 C2 C9 -3.7(2) . . . . ?
O1 C1 C2 C9 176.90(12) . . . . ?
C2 N1 C3 C4 177.00(14) . . . . ?
C2 N1 C3 C8 -1.8(2) . . . . ?
N1 C3 C4 C5 -178.83(16) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 O1 -179.82(14) . . . . ?
C6 C7 C8 C3 -0.5(2) . . . . ?
C1 O1 C8 C7 -178.68(13) . . . . ?
C1 O1 C8 C3 2.0(2) . . . . ?
C4 C3 C8 C7 0.7(2) . . . . ?
N1 C3 C8 C7 179.51(14) . . . . ?
C4 C3 C8 O1 -179.98(14) . . . . ?
N1 C3 C8 O1 -1.2(2) . . . . ?
N1 C2 C9 C10 -0.7(2) . . . . ?
C1 C2 C9 C10 179.53(14) . . . . ?
C11 N2 C10 C9 171.87(16) . . . . ?
C11 N2 C10 C15 -12.7(3) . . . . ?
C2 C9 C10 N2 -2.1(2) . . . . ?
C2 C9 C10 C15 -177.66(13) . . . . ?
C10 N2 C11 C12 86.2(2) . . . . ?
C10 N2 C11 C14 -37.7(3) . . . . ?
C10 N2 C11 C13 -157.1(2) . . . . ?
C16 O3 C15 O4 -0.6(2) . . . . ?
C16 O3 C15 C10 177.36(14) . . . . ?
N2 C10 C15 O4 -41.1(2) . . . . ?
C9 C10 C15 O4 134.53(17) . . . . ?
N2 C10 C15 O3 140.95(15) . . . . ?
C9 C10 C15 O3 -43.40(18) . . . . ?

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
N2 H2 N1 0.88(2) 1.96(2) 2.7040(18) 140.9(17) .

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_ga_80607b_1_a
_database_code_depnum_ccdc_archive 'CCDC 1906924'
loop_
_audit_author_name
_audit_author_address
'Jian Li'
;Shanghai university
China
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H17 Br N2 O4'
_chemical_formula_weight         429.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   10.4647(3)
_cell_length_b                   13.4623(4)
_cell_length_c                   14.0577(4)
_cell_angle_alpha                94.6090(10)
_cell_angle_beta                 105.3440(10)
_cell_angle_gamma                96.0880(10)
_cell_volume                     1886.89(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9894
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      57.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    2.117
_shelx_estimated_absorpt_T_min   0.620
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\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            25232
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.890
_diffrn_reflns_theta_max         57.100
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7729
_reflns_number_gt                6705
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0375P)²+0.9326P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7729
_refine_ls_number_parameters     501
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.003
_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 0.34998(3) 0.35905(2) 0.05593(2) 0.06561(10) Uani 1 1 d . . . . .
N1 N 0.28708(14) 0.92353(10) 0.32580(10) 0.0313(3) Uani 1 1 d . . . . .
N2 N 0.26523(15) 0.78670(11) 0.16755(11) 0.0334(3) Uani 1 1 d D . . . .
H2 H 0.256(2) 0.7987(18) 0.2294(17) 0.056(7) Uiso 1 1 d D . . . .
O1 O 0.37858(13) 1.12395(9) 0.40893(9) 0.0378(3) Uani 1 1 d . . . . .
O2 O 0.39135(15) 1.16371(10) 0.26256(11) 0.0470(3) Uani 1 1 d . . . . .
O3 O 0.36172(15) 0.92436(11) -0.01169(10) 0.0479(3) Uani 1 1 d . . . . .
O4 O 0.22404(15) 0.77938(10) -0.03870(9) 0.0460(3) Uani 1 1 d . . . . .
C1 C 0.36491(17) 1.09863(13) 0.31059(13) 0.0345(4) Uani 1 1 d . . . . .
C2 C 0.31744(16) 0.99090(12) 0.27067(13) 0.0310(3) Uani 1 1 d . . . . .
C3 C 0.30410(16) 0.95285(13) 0.42588(12) 0.0314(3) Uani 1 1 d . . . . .
C4 C 0.27613(18) 0.88225(14) 0.48798(13) 0.0369(4) Uani 1 1 d . . . . .
H4A H 0.2440 0.8143 0.4613 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2950(2) 0.91087(16) 0.58770(14) 0.0424(4) Uani 1 1 d . . . . .
H5 H 0.2752 0.8627 0.6294 0.051 Uiso 1 1 calc R U . . .
C6 C 0.3428(2) 1.01006(16) 0.62739(14) 0.0441(4) Uani 1 1 d . . . . .
H6 H 0.3557 1.0293 0.6961 0.053 Uiso 1 1 calc R U . . .
C7 C 0.37180(19) 1.08086(15) 0.56734(14) 0.0413(4) Uani 1 1 d . . . . .
H7 H 0.4056 1.1485 0.5944 0.050 Uiso 1 1 calc R U . . .
C8 C 0.35068(17) 1.05147(13) 0.46771(13) 0.0331(4) Uani 1 1 d . . . . .
C9 C 0.31119(17) 0.96581(13) 0.16874(13) 0.0331(4) Uani 1 1 d . . . . .
H9 H 0.3216 1.0193 0.1301 0.040 Uiso 1 1 calc R U . . .
C10 C 0.29112(17) 0.86959(13) 0.12342(12) 0.0313(3) Uani 1 1 d . . . . .
C11 C 0.28537(17) 0.68710(12) 0.13730(12) 0.0302(3) Uani 1 1 d . . . . .
C12 C 0.17681(17) 0.61108(13) 0.11682(12) 0.0306(3) Uani 1 1 d . . . . .
C13 C 0.19723(18) 0.51280(13) 0.09324(13) 0.0343(4) Uani 1 1 d . . . . .
H13 H 0.1253 0.4597 0.0795 0.041 Uiso 1 1 calc R U . . .
C14 C 0.3230(2) 0.49288(13) 0.08990(14) 0.0377(4) Uani 1 1 d . . . . .
C15 C 0.43014(19) 0.56758(14) 0.11077(14) 0.0373(4) Uani 1 1 d . . . . .
H15 H 0.5155 0.5518 0.1080 0.045 Uiso 1 1 calc R U . . .
C16 C 0.41289(18) 0.66646(13) 0.13599(13) 0.0342(4) Uani 1 1 d . . . . .
C17 C 0.04198(18) 0.63511(14) 0.12209(14) 0.0380(4) Uani 1 1 d . . . . .
H17A H -0.0218 0.5733 0.1055 0.057 Uiso 1 1 calc R U . . .
H17B H 0.0114 0.6830 0.0748 0.057 Uiso 1 1 calc R U . . .
H17C H 0.0482 0.6647 0.1894 0.057 Uiso 1 1 calc R U . . .
C18 C 0.5326(2) 0.74638(15) 0.16460(17) 0.0464(5) Uani 1 1 d . . . . .
H18A H 0.5332 0.7850 0.1085 0.070 Uiso 1 1 calc R U . . .
H18B H 0.6145 0.7147 0.1823 0.070 Uiso 1 1 calc R U . . .
H18C H 0.5282 0.7915 0.2216 0.070 Uiso 1 1 calc R U . . .
C19 C 0.28748(18) 0.85114(13) 0.01569(13) 0.0345(4) Uani 1 1 d . . . . .
C20 C 0.3620(2) 0.91266(19) -0.11500(15) 0.0552(6) Uani 1 1 d . . . . .
H20A H 0.4097 0.8561 -0.1269 0.083 Uiso 1 1 calc R U . . .
H20B H 0.4068 0.9744 -0.1307 0.083 Uiso 1 1 calc R U . . .
H20C H 0.2697 0.8996 -0.1573 0.083 Uiso 1 1 calc R U . . .
Br2 Br -0.11609(3) -0.15240(2) 0.21167(3) 0.09628(15) Uani 1 1 d . U . . .
N3 N 0.35976(15) 0.42083(11) 0.35640(11) 0.0340(3) Uani 1 1 d . . . . .
N4 N 0.13470(16) 0.28312(11) 0.30580(13) 0.0381(3) Uani 1 1 d D . . . .
H4 H 0.219(2) 0.2964(19) 0.3247(18) 0.059(7) Uiso 1 1 d D . . . .
O5 O 0.45957(15) 0.62577(9) 0.36960(10) 0.0448(3) Uani 1 1 d . . . . .
O6 O 0.25463(16) 0.66348(9) 0.34745(10) 0.0474(3) Uani 1 1 d . . . . .
O7 O -0.12514(14) 0.41785(10) 0.20038(10) 0.0447(3) Uani 1 1 d . . . . .
O8 O -0.14715(13) 0.28346(10) 0.28257(10) 0.0422(3) Uani 1 1 d . . . . .
C21 C 0.3258(2) 0.59835(13) 0.35264(12) 0.0381(4) Uani 1 1 d . . . . .
C22 C 0.27735(19) 0.48812(12) 0.34075(12) 0.0338(4) Uani 1 1 d . . . . .
C23 C 0.49684(19) 0.45317(13) 0.38044(12) 0.0357(4) Uani 1 1 d . . . . .
C24 C 0.5884(2) 0.38433(15) 0.40068(14) 0.0415(4) Uani 1 1 d . . . . .
H24 H 0.5575 0.3151 0.3989 0.050 Uiso 1 1 calc R U . . .
C25 C 0.7238(2) 0.41646(18) 0.42327(15) 0.0487(5) Uani 1 1 d . . . . .
H25 H 0.7858 0.3694 0.4380 0.058 Uiso 1 1 calc R U . . .
C26 C 0.7699(2) 0.51721(19) 0.42454(15) 0.0535(6) Uani 1 1 d . . . . .
H26 H 0.8632 0.5386 0.4395 0.064 Uiso 1 1 calc R U . . .
C27 C 0.6813(2) 0.58615(17) 0.40429(15) 0.0521(5) Uani 1 1 d . . . . .
H27 H 0.7126 0.6550 0.4040 0.062 Uiso 1 1 calc R U . . .
C28 C 0.5460(2) 0.55388(14) 0.38433(13) 0.0401(4) Uani 1 1 d . . . . .
C29 C 0.13629(19) 0.46162(13) 0.31026(12) 0.0346(4) Uani 1 1 d . . . . .
H29 H 0.0828 0.5148 0.3020 0.042 Uiso 1 1 calc R U . . .
C30 C 0.07165(18) 0.36520(13) 0.29192(12) 0.0329(4) Uani 1 1 d . . . . .
C31 C 0.07315(17) 0.18051(12) 0.28231(13) 0.0328(4) Uani 1 1 d . . . . .
C32 C 0.04229(17) 0.13037(13) 0.35805(14) 0.0350(4) Uani 1 1 d . . . . .
C33 C -0.01347(18) 0.03003(14) 0.33558(17) 0.0425(5) Uani 1 1 d . . . . .
H33 H -0.0349 -0.0065 0.3856 0.051 Uiso 1 1 calc R U . . .
C34 C -0.03744(19) -0.01605(14) 0.24079(19) 0.0491(5) Uani 1 1 d . . . . .
C35 C -0.0072(2) 0.03360(16) 0.16596(17) 0.0500(5) Uani 1 1 d . . . . .
H35 H -0.0251 -0.0003 0.1010 0.060 Uiso 1 1 calc R U . . .
C36 C 0.04966(18) 0.13383(15) 0.18632(15) 0.0402(4) Uani 1 1 d . . . . .
C37 C 0.0651(2) 0.18320(16) 0.45987(15) 0.0478(5) Uani 1 1 d . . . . .
H37A H 0.1607 0.2060 0.4886 0.072 Uiso 1 1 calc R U . . .
H37B H 0.0338 0.1369 0.5018 0.072 Uiso 1 1 calc R U . . .
H37C H 0.0156 0.2413 0.4561 0.072 Uiso 1 1 calc R U . . .
C38 C 0.0871(3) 0.1889(2) 0.10656(18) 0.0608(6) Uani 1 1 d . . . . .
H38A H 0.0410 0.2487 0.0982 0.091 Uiso 1 1 calc R U . . .
H38B H 0.0607 0.1446 0.0439 0.091 Uiso 1 1 calc R U . . .
H38C H 0.1839 0.2094 0.1256 0.091 Uiso 1 1 calc R U . . .
C39 C -0.07890(19) 0.34886(13) 0.25854(13) 0.0347(4) Uani 1 1 d . . . . .
C40 C -0.2687(2) 0.41304(18) 0.16480(16) 0.0509(5) Uani 1 1 d . . . . .
H40A H -0.3073 0.3454 0.1321 0.076 Uiso 1 1 calc R U . . .
H40B H -0.2910 0.4622 0.1173 0.076 Uiso 1 1 calc R U . . .
H40C H -0.3053 0.4282 0.2209 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.8961(18) . ?
N1 C2 1.306(2) . ?
N1 C3 1.389(2) . ?
N2 C10 1.356(2) . ?
N2 C11 1.428(2) . ?
N2 H2 0.90(2) . ?
O1 C1 1.363(2) . ?
O1 C8 1.385(2) . ?
O2 C1 1.201(2) . ?
O3 C19 1.334(2) . ?
O3 C20 1.449(2) . ?
O4 C19 1.198(2) . ?
C1 C2 1.495(2) . ?
C2 C9 1.428(2) . ?
C3 C8 1.390(2) . ?
C3 C4 1.400(3) . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C9 C10 1.366(2) . ?
C9 H9 0.9500 . ?
C10 C19 1.505(2) . ?
C11 C16 1.396(2) . ?
C11 C12 1.398(2) . ?
C12 C13 1.390(2) . ?
C12 C17 1.500(2) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(3) . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C18 1.506(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Br2 C34 1.8960(18) . ?
N3 C22 1.308(2) . ?
N3 C23 1.396(2) . ?
N4 C30 1.347(2) . ?
N4 C31 1.434(2) . ?
N4 H4 0.85(2) . ?
O5 C21 1.361(2) . ?
O5 C28 1.384(3) . ?
O6 C21 1.204(2) . ?
O7 C39 1.332(2) . ?
O7 C40 1.445(2) . ?
O8 C39 1.201(2) . ?
C21 C22 1.498(2) . ?
C22 C29 1.421(3) . ?
C23 C28 1.390(3) . ?
C23 C24 1.394(3) . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.373(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9500 . ?
C29 C30 1.370(2) . ?
C29 H29 0.9500 . ?
C30 C39 1.506(3) . ?
C31 C36 1.390(3) . ?
C31 C32 1.395(2) . ?
C32 C33 1.390(3) . ?
C32 C37 1.494(3) . ?
C33 C34 1.371(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(3) . ?
C35 C36 1.391(3) . ?
C35 H35 0.9500 . ?
C36 C38 1.505(3) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
C2 N1 C3 118.50(14) . . ?
C10 N2 C11 125.52(15) . . ?
C10 N2 H2 115.5(15) . . ?
C11 N2 H2 116.9(15) . . ?
C1 O1 C8 120.39(13) . . ?
C19 O3 C20 115.35(15) . . ?
O2 C1 O1 118.18(16) . . ?
O2 C1 C2 124.91(17) . . ?
O1 C1 C2 116.91(15) . . ?
N1 C2 C9 122.10(15) . . ?
N1 C2 C1 122.38(16) . . ?
C9 C2 C1 115.49(15) . . ?
N1 C3 C8 121.71(16) . . ?
N1 C3 C4 120.21(15) . . ?
C8 C3 C4 118.08(16) . . ?
C5 C4 C3 120.31(18) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 120.16(19) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.41(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 118.75(18) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 O1 117.67(16) . . ?
C7 C8 C3 122.28(17) . . ?
O1 C8 C3 120.05(15) . . ?
C10 C9 C2 123.99(16) . . ?
C10 C9 H9 118.0 . . ?
C2 C9 H9 118.0 . . ?
N2 C10 C9 124.18(16) . . ?
N2 C10 C19 115.84(15) . . ?
C9 C10 C19 119.84(15) . . ?
C16 C11 C12 121.74(15) . . ?
C16 C11 N2 120.03(15) . . ?
C12 C11 N2 118.05(15) . . ?
C13 C12 C11 118.56(16) . . ?
C13 C12 C17 120.91(15) . . ?
C11 C12 C17 120.52(15) . . ?
C14 C13 C12 119.56(16) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 121.91(17) . . ?
C15 C14 Br1 118.62(14) . . ?
C13 C14 Br1 119.47(14) . . ?
C14 C15 C16 119.71(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 118.49(16) . . ?
C15 C16 C18 119.11(17) . . ?
C11 C16 C18 122.36(16) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O3 124.46(17) . . ?
O4 C19 C10 123.51(16) . . ?
O3 C19 C10 112.02(15) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 N3 C23 118.51(15) . . ?
C30 N4 C31 126.20(16) . . ?
C30 N4 H4 113.6(17) . . ?
C31 N4 H4 119.9(17) . . ?
C21 O5 C28 120.10(14) . . ?
C39 O7 C40 116.70(16) . . ?
O6 C21 O5 118.36(16) . . ?
O6 C21 C22 124.48(19) . . ?
O5 C21 C22 117.16(17) . . ?
N3 C22 C29 122.36(15) . . ?
N3 C22 C21 122.03(17) . . ?
C29 C22 C21 115.61(16) . . ?
C28 C23 C24 118.18(18) . . ?
C28 C23 N3 121.41(18) . . ?
C24 C23 N3 120.41(16) . . ?
C25 C24 C23 120.23(19) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C28 119.0(2) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C27 C28 O5 117.77(18) . . ?
C27 C28 C23 121.8(2) . . ?
O5 C28 C23 120.38(18) . . ?
C30 C29 C22 124.91(16) . . ?
C30 C29 H29 117.5 . . ?
C22 C29 H29 117.5 . . ?
N4 C30 C29 123.79(17) . . ?
N4 C30 C39 117.34(15) . . ?
C29 C30 C39 118.82(16) . . ?
C36 C31 C32 122.37(16) . . ?
C36 C31 N4 119.29(16) . . ?
C32 C31 N4 118.32(16) . . ?
C33 C32 C31 118.07(18) . . ?
C33 C32 C37 120.68(17) . . ?
C31 C32 C37 121.24(16) . . ?
C34 C33 C32 119.68(18) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C35 122.22(17) . . ?
C33 C34 Br2 118.82(16) . . ?
C35 C34 Br2 118.96(17) . . ?
C34 C35 C36 119.46(19) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C31 C36 C35 118.21(18) . . ?
C31 C36 C38 121.29(18) . . ?
C35 C36 C38 120.5(2) . . ?
C32 C37 H37A 109.5 . . ?
C32 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C32 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O8 C39 O7 125.01(17) . . ?
O8 C39 C30 124.39(16) . . ?
O7 C39 C30 110.58(15) . . ?
O7 C40 H40A 109.5 . . ?
O7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C8 O1 C1 O2 -179.34(16) . . . . ?
C8 O1 C1 C2 0.8(2) . . . . ?
C3 N1 C2 C9 175.87(15) . . . . ?
C3 N1 C2 C1 -2.2(2) . . . . ?
O2 C1 C2 N1 -178.37(17) . . . . ?
O1 C1 C2 N1 1.5(2) . . . . ?
O2 C1 C2 C9 3.4(3) . . . . ?
O1 C1 C2 C9 -176.71(15) . . . . ?
C2 N1 C3 C8 0.8(2) . . . . ?
C2 N1 C3 C4 -178.26(16) . . . . ?
N1 C3 C4 C5 178.97(16) . . . . ?
C8 C3 C4 C5 -0.1(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 O1 179.10(16) . . . . ?
C6 C7 C8 C3 -1.4(3) . . . . ?
C1 O1 C8 C7 177.31(16) . . . . ?
C1 O1 C8 C3 -2.2(2) . . . . ?
N1 C3 C8 C7 -178.00(16) . . . . ?
C4 C3 C8 C7 1.1(3) . . . . ?
N1 C3 C8 O1 1.5(2) . . . . ?
C4 C3 C8 O1 -179.48(15) . . . . ?
N1 C2 C9 C10 -9.1(3) . . . . ?
C1 C2 C9 C10 169.15(16) . . . . ?
C11 N2 C10 C9 -158.81(17) . . . . ?
C11 N2 C10 C19 25.4(2) . . . . ?
C2 C9 C10 N2 4.9(3) . . . . ?
C2 C9 C10 C19 -179.42(16) . . . . ?
C10 N2 C11 C16 59.8(2) . . . . ?
C10 N2 C11 C12 -124.97(18) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
N2 C11 C12 C13 -176.10(15) . . . . ?
C16 C11 C12 C17 177.97(16) . . . . ?
N2 C11 C12 C17 2.8(2) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C17 C12 C13 C14 -179.37(16) . . . . ?
C12 C13 C14 C15 1.0(3) . . . . ?
C12 C13 C14 Br1 -179.13(13) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
Br1 C14 C15 C16 -179.95(13) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C14 C15 C16 C18 176.35(17) . . . . ?
C12 C11 C16 C15 1.8(2) . . . . ?
N2 C11 C16 C15 176.90(15) . . . . ?
C12 C11 C16 C18 -175.76(17) . . . . ?
N2 C11 C16 C18 -0.7(3) . . . . ?
C20 O3 C19 O4 0.1(3) . . . . ?
C20 O3 C19 C10 -179.26(17) . . . . ?
N2 C10 C19 O4 25.3(3) . . . . ?
C9 C10 C19 O4 -150.67(19) . . . . ?
N2 C10 C19 O3 -155.33(16) . . . . ?
C9 C10 C19 O3 28.7(2) . . . . ?
C28 O5 C21 O6 174.59(15) . . . . ?
C28 O5 C21 C22 -6.0(2) . . . . ?
C23 N3 C22 C29 176.22(15) . . . . ?
C23 N3 C22 C21 -3.0(2) . . . . ?
O6 C21 C22 N3 -173.34(17) . . . . ?
O5 C21 C22 N3 7.2(2) . . . . ?
O6 C21 C22 C29 7.4(3) . . . . ?
O5 C21 C22 C29 -172.02(15) . . . . ?
C22 N3 C23 C28 -2.4(2) . . . . ?
C22 N3 C23 C24 178.05(16) . . . . ?
C28 C23 C24 C25 -0.4(3) . . . . ?
N3 C23 C24 C25 179.23(17) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C24 C25 C26 C27 0.6(3) . . . . ?
C25 C26 C27 C28 1.1(3) . . . . ?
C26 C27 C28 O5 176.50(17) . . . . ?
C26 C27 C28 C23 -2.5(3) . . . . ?
C21 O5 C28 C27 -178.06(16) . . . . ?
C21 O5 C28 C23 1.0(2) . . . . ?
C24 C23 C28 C27 2.1(3) . . . . ?
N3 C23 C28 C27 -177.45(17) . . . . ?
C24 C23 C28 O5 -176.85(16) . . . . ?
N3 C23 C28 O5 3.6(3) . . . . ?
N3 C22 C29 C30 -1.5(3) . . . . ?
C21 C22 C29 C30 177.72(16) . . . . ?
C31 N4 C30 C29 -175.98(17) . . . . ?
C31 N4 C30 C39 6.8(3) . . . . ?
C22 C29 C30 N4 3.7(3) . . . . ?
C22 C29 C30 C39 -179.11(16) . . . . ?
C30 N4 C31 C36 84.8(2) . . . . ?
C30 N4 C31 C32 -96.9(2) . . . . ?
C36 C31 C32 C33 0.2(3) . . . . ?
N4 C31 C32 C33 -178.02(16) . . . . ?
C36 C31 C32 C37 -178.26(17) . . . . ?
N4 C31 C32 C37 3.5(2) . . . . ?
C31 C32 C33 C34 -0.6(3) . . . . ?
C37 C32 C33 C34 177.92(18) . . . . ?
C32 C33 C34 C35 0.4(3) . . . . ?
C32 C33 C34 Br2 -179.05(14) . . . . ?
C33 C34 C35 C36 0.1(3) . . . . ?
Br2 C34 C35 C36 179.57(15) . . . . ?
C32 C31 C36 C35 0.3(3) . . . . ?
N4 C31 C36 C35 178.51(17) . . . . ?
C32 C31 C36 C38 -178.45(18) . . . . ?
N4 C31 C36 C38 -0.2(3) . . . . ?
C34 C35 C36 C31 -0.4(3) . . . . ?
C34 C35 C36 C38 178.31(19) . . . . ?
C40 O7 C39 O8 0.5(3) . . . . ?
C40 O7 C39 C30 -178.39(15) . . . . ?
N4 C30 C39 O8 33.7(3) . . . . ?
C29 C30 C39 O8 -143.69(19) . . . . ?
N4 C30 C39 O7 -147.37(16) . . . . ?
C29 C30 C39 O7 35.2(2) . . . . ?

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
N2 H2 N1 0.90(2) 2.01(2) 2.716(2) 134(2) .
N4 H4 N3 0.85(2) 2.05(2) 2.732(2) 138(2) .

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.048

