# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_smi1new
_audit_block_doi                 10.5517/ccdc.csd.cc1yt6nm
_database_code_depnum_ccdc_archive 'CCDC 1811691'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C8QO00982A 2018
loop_
_audit_author_name
_audit_author_address
'Galina L.Starova' 'State Saint-Petersberg university'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H22 Br N O9'
_chemical_formula_sum            'C26 H22 Br N O9'
_chemical_formula_weight         572.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 h20 n1 o6 br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2685(6)
_cell_length_b                   18.6581(7)
_cell_length_c                   12.8795(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.426(7)
_cell_angle_gamma                90
_cell_volume                     2520.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2472
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0130
_cell_measurement_theta_min      3.0040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10736
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.766
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00    4.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -26.00   -1.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   19.0000  -60.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0375685000
_diffrn_orient_matrix_UB_12      -0.0245418000
_diffrn_orient_matrix_UB_13      -0.0409788000
_diffrn_orient_matrix_UB_21      0.0224324000
_diffrn_orient_matrix_UB_22      -0.0285163000
_diffrn_orient_matrix_UB_23      0.0385551000
_diffrn_orient_matrix_UB_31      -0.0515901000
_diffrn_orient_matrix_UB_32      0.0053550000
_diffrn_orient_matrix_UB_33      0.0182695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4439
_reflns_number_total             5709
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5709
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0284P)²+1.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C7(H7), C6(H6), C22(H22), C9(H9), C23(H23), C24(H24), C26(H26),
 C8(H8), C25(H25)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.32104(2) 0.69427(2) 0.61167(2) 0.02285(8) Uani 1 1 d . . . . .
O1 O 0.69831(15) 0.55837(9) 0.82676(14) 0.0183(4) Uani 1 1 d . . . . .
O9 O 0.87501(15) 0.72529(9) 0.82963(14) 0.0182(4) Uani 1 1 d . . . . .
O7 O 0.72585(15) 0.65451(9) 0.46987(13) 0.0185(4) Uani 1 1 d . . . . .
O6 O 0.98107(15) 0.58454(8) 0.84126(13) 0.0162(3) Uani 1 1 d . . . . .
O2 O 0.38918(18) 0.53996(9) 0.70319(18) 0.0312(5) Uani 1 1 d . . . . .
O5 O 1.00146(16) 0.48953(9) 0.73580(14) 0.0202(4) Uani 1 1 d . . . . .
O4 O 0.80463(16) 0.48885(8) 0.60351(14) 0.0199(4) Uani 1 1 d . . . . .
O8 O 0.93108(15) 0.62064(8) 0.55614(13) 0.0163(3) Uani 1 1 d . . . . .
O3 O 0.52480(15) 0.52311(8) 0.61355(14) 0.0174(4) Uani 1 1 d . . . . .
N1 N 0.69630(17) 0.63772(10) 0.68222(16) 0.0127(4) Uani 1 1 d . . . . .
C1 C 0.7425(2) 0.58657(12) 0.76570(19) 0.0140(5) Uani 1 1 d . . . . .
C11 C 0.4718(2) 0.64069(12) 0.63673(19) 0.0160(5) Uani 1 1 d . . . . .
C4 C 0.5790(2) 0.67431(12) 0.64135(19) 0.0125(5) Uani 1 1 d . . . . .
C15 C 1.0747(2) 0.53518(13) 0.8288(2) 0.0187(5) Uani 1 1 d . . . . .
C20 C 0.8910(2) 0.71618(12) 0.74248(19) 0.0138(5) Uani 1 1 d . . . . .
C3 C 0.8199(2) 0.65110(12) 0.67080(18) 0.0119(5) Uani 1 1 d . . . . .
C18 C 0.8173(2) 0.64340(12) 0.55262(19) 0.0134(5) Uani 1 1 d . . . . .
C10 C 0.5372(2) 0.77066(14) 0.4979(2) 0.0225(6) Uani 1 1 d . . . . .
H10 H 0.5105 0.7355 0.4431 0.027 Uiso 1 1 calc R . . . .
C5 C 0.5814(2) 0.75134(12) 0.6101(2) 0.0149(5) Uani 1 1 d . . . . .
C7 C 0.6157(3) 0.87559(14) 0.6614(3) 0.0301(7) Uani 1 1 d . . . . .
H7 H 0.6418 0.9110 0.7158 0.036 Uiso 1 1 calc R . . . .
C6 C 0.6210(2) 0.80422(12) 0.6922(2) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.6507 0.7916 0.7673 0.025 Uiso 1 1 calc R . . . .
C12 C 0.4561(2) 0.56275(13) 0.6566(2) 0.0182(5) Uani 1 1 d . . . . .
C2 C 0.8701(2) 0.58192(12) 0.74786(19) 0.0127(5) Uani 1 1 d . . . . .
C22 C 1.0968(2) 0.77842(13) 0.8003(2) 0.0190(5) Uani 1 1 d . . . . .
H22 H 1.1095 0.7638 0.8726 0.023 Uiso 1 1 calc R . . . .
C14 C 0.8834(2) 0.51507(12) 0.6840(2) 0.0159(5) Uani 1 1 d . . . . .
C9 C 0.5328(3) 0.84228(15) 0.4676(3) 0.0309(7) Uani 1 1 d . . . . .
H9 H 0.5039 0.8552 0.3927 0.037 Uiso 1 1 calc R . . . .
C23 C 1.1883(2) 0.81908(13) 0.7800(2) 0.0231(6) Uani 1 1 d . . . . .
H23 H 1.2633 0.8311 0.8383 0.028 Uiso 1 1 calc R . . . .
C24 C 1.1679(2) 0.84206(13) 0.6723(2) 0.0232(6) Uani 1 1 d . . . . .
H24 H 1.2292 0.8698 0.6586 0.028 Uiso 1 1 calc R . . . .
C13 C 0.5259(2) 0.44695(12) 0.6360(2) 0.0246(6) Uani 1 1 d . . . . .
H13A H 0.4415 0.4279 0.6007 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.5541 0.4393 0.7150 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.5829 0.4232 0.6071 0.037 Uiso 1 1 calc GR . . . .
C26 C 0.9649(2) 0.78217(12) 0.6045(2) 0.0192(5) Uani 1 1 d . . . . .
H26 H 0.8905 0.7697 0.5458 0.023 Uiso 1 1 calc R . . . .
C8 C 0.5715(3) 0.89437(14) 0.5496(3) 0.0331(7) Uani 1 1 d . . . . .
H8 H 0.5679 0.9424 0.5295 0.040 Uiso 1 1 calc R . . . .
C21 C 0.9855(2) 0.75923(12) 0.7127(2) 0.0148(5) Uani 1 1 d . . . . .
C25 C 1.0567(3) 0.82372(13) 0.5854(2) 0.0228(6) Uani 1 1 d . . . . .
H25 H 1.0435 0.8395 0.5135 0.027 Uiso 1 1 calc R . . . .
C19 C 0.9405(3) 0.60368(14) 0.4488(2) 0.0245(6) Uani 1 1 d . . . . .
H19A H 0.9168 0.6449 0.4011 0.037 Uiso 1 1 calc GR . . . .
H19B H 0.8842 0.5646 0.4148 0.037 Uiso 1 1 calc GR . . . .
H19C H 1.0265 0.5903 0.4600 0.037 Uiso 1 1 calc GR . . . .
C16 C 1.1260(3) 0.49040(14) 0.9321(2) 0.0251(6) Uani 1 1 d . . . . .
H16A H 1.1702 0.5206 0.9947 0.038 Uiso 1 1 calc GR . . . .
H16B H 1.1838 0.4553 0.9232 0.038 Uiso 1 1 calc GR . . . .
H16C H 1.0568 0.4667 0.9446 0.038 Uiso 1 1 calc GR . . . .
C17 C 1.1735(2) 0.57539(15) 0.7998(2) 0.0283(6) Uani 1 1 d . . . . .
H17A H 1.1327 0.6030 0.7334 0.042 Uiso 1 1 calc GR . . . .
H17B H 1.2318 0.5420 0.7873 0.042 Uiso 1 1 calc GR . . . .
H17C H 1.2193 0.6068 0.8601 0.042 Uiso 1 1 calc GR . . . .


_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 1.895(2) . ?
O1 C1 1.196(3) . ?
O9 C20 1.212(3) . ?
O7 C18 1.199(3) . ?
O6 C15 1.453(3) . ?
O6 C2 1.383(3) . ?
O2 C12 1.200(3) . ?
O5 C15 1.455(3) . ?
O5 C14 1.339(3) . ?
O4 C14 1.196(3) . ?
O8 C18 1.335(3) . ?
O8 C19 1.459(3) . ?
O3 C12 1.330(3) . ?
O3 C13 1.449(3) . ?
N1 C1 1.389(3) . ?
N1 C4 1.408(3) . ?
N1 C3 1.474(3) . ?
C1 C2 1.539(3) . ?
C11 C4 1.343(3) . ?
C11 C12 1.498(3) . ?
C4 C5 1.495(3) . ?
C15 C16 1.497(3) . ?
C15 C17 1.498(3) . ?
C20 C3 1.558(3) . ?
C20 C21 1.491(3) . ?
C3 C18 1.518(3) . ?
C3 C2 1.600(3) . ?
C10 H10 0.9300 . ?
C10 C5 1.394(3) . ?
C10 C9 1.388(4) . ?
C5 C6 1.395(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(4) . ?
C7 C8 1.386(4) . ?
C6 H6 0.9300 . ?
C2 C14 1.531(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(3) . ?
C22 C21 1.393(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.383(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.384(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C26 H26 0.9300 . ?
C26 C21 1.394(3) . ?
C26 C25 1.384(3) . ?
C8 H8 0.9300 . ?
C25 H25 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 O6 C15 110.08(17) . . ?
C14 O5 C15 111.29(17) . . ?
C18 O8 C19 115.96(19) . . ?
C12 O3 C13 115.23(18) . . ?
C1 N1 C4 131.14(19) . . ?
C1 N1 C3 95.33(17) . . ?
C4 N1 C3 132.29(18) . . ?
O1 C1 N1 133.1(2) . . ?
O1 C1 C2 135.2(2) . . ?
N1 C1 C2 91.70(17) . . ?
C4 C11 Br1 119.81(17) . . ?
C4 C11 C12 127.4(2) . . ?
C12 C11 Br1 112.73(16) . . ?
N1 C4 C5 117.34(19) . . ?
C11 C4 N1 119.8(2) . . ?
C11 C4 C5 122.8(2) . . ?
O6 C15 O5 104.22(17) . . ?
O6 C15 C16 108.37(19) . . ?
O6 C15 C17 110.2(2) . . ?
O5 C15 C16 108.9(2) . . ?
O5 C15 C17 109.8(2) . . ?
C16 C15 C17 114.8(2) . . ?
O9 C20 C3 116.1(2) . . ?
O9 C20 C21 121.6(2) . . ?
C21 C20 C3 121.87(19) . . ?
N1 C3 C20 111.88(17) . . ?
N1 C3 C18 114.27(18) . . ?
N1 C3 C2 86.24(15) . . ?
C20 C3 C2 105.80(17) . . ?
C18 C3 C20 119.02(18) . . ?
C18 C3 C2 114.73(18) . . ?
O7 C18 O8 126.0(2) . . ?
O7 C18 C3 124.7(2) . . ?
O8 C18 C3 109.23(19) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C5 120.2(3) . . ?
C10 C5 C4 119.5(2) . . ?
C10 C5 C6 119.9(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 H7 119.9 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
O2 C12 O3 125.4(2) . . ?
O2 C12 C11 124.4(2) . . ?
O3 C12 C11 110.19(19) . . ?
O6 C2 C1 117.71(18) . . ?
O6 C2 C3 120.89(18) . . ?
O6 C2 C14 105.14(18) . . ?
C1 C2 C3 84.78(16) . . ?
C14 C2 C1 113.96(18) . . ?
C14 C2 C3 113.94(18) . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
O5 C14 C2 107.3(2) . . ?
O4 C14 O5 125.0(2) . . ?
O4 C14 C2 127.7(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C24 119.8(2) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C25 C26 C21 119.2(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C22 C21 C20 116.5(2) . . ?
C22 C21 C26 120.1(2) . . ?
C26 C21 C20 123.3(2) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
Br1 C11 C4 N1 166.98(16) . . . . ?
Br1 C11 C4 C5 -9.8(3) . . . . ?
Br1 C11 C12 O2 -33.6(3) . . . . ?
Br1 C11 C12 O3 145.32(16) . . . . ?
O1 C1 C2 O6 -47.0(4) . . . . ?
O1 C1 C2 C3 -169.3(3) . . . . ?
O1 C1 C2 C14 76.8(3) . . . . ?
O9 C20 C3 N1 33.1(3) . . . . ?
O9 C20 C3 C18 170.0(2) . . . . ?
O9 C20 C3 C2 -59.2(2) . . . . ?
O9 C20 C21 C22 34.8(3) . . . . ?
O9 C20 C21 C26 -143.0(2) . . . . ?
O6 C2 C14 O5 -6.6(2) . . . . ?
O6 C2 C14 O4 172.7(2) . . . . ?
N1 C1 C2 O6 132.63(19) . . . . ?
N1 C1 C2 C3 10.33(16) . . . . ?
N1 C1 C2 C14 -103.6(2) . . . . ?
N1 C4 C5 C10 106.4(3) . . . . ?
N1 C4 C5 C6 -77.2(3) . . . . ?
N1 C3 C18 O7 29.4(3) . . . . ?
N1 C3 C18 O8 -148.98(18) . . . . ?
N1 C3 C2 O6 -129.0(2) . . . . ?
N1 C3 C2 C1 -9.74(15) . . . . ?
N1 C3 C2 C14 104.19(19) . . . . ?
C1 N1 C4 C11 -34.8(4) . . . . ?
C1 N1 C4 C5 142.1(2) . . . . ?
C1 N1 C3 C20 -94.7(2) . . . . ?
C1 N1 C3 C18 126.30(19) . . . . ?
C1 N1 C3 C2 10.81(17) . . . . ?
C1 C2 C14 O5 -136.92(19) . . . . ?
C1 C2 C14 O4 42.4(3) . . . . ?
C11 C4 C5 C10 -76.8(3) . . . . ?
C11 C4 C5 C6 99.7(3) . . . . ?
C4 N1 C1 O1 0.3(4) . . . . ?
C4 N1 C1 C2 -179.4(2) . . . . ?
C4 N1 C3 C20 73.2(3) . . . . ?
C4 N1 C3 C18 -65.7(3) . . . . ?
C4 N1 C3 C2 178.8(2) . . . . ?
C4 C11 C12 O2 142.4(3) . . . . ?
C4 C11 C12 O3 -38.7(3) . . . . ?
C4 C5 C6 C7 -176.4(2) . . . . ?
C15 O6 C2 C1 141.24(19) . . . . ?
C15 O6 C2 C3 -117.5(2) . . . . ?
C15 O6 C2 C14 13.1(2) . . . . ?
C15 O5 C14 O4 178.1(2) . . . . ?
C15 O5 C14 C2 -2.5(2) . . . . ?
C20 C3 C18 O7 -106.5(3) . . . . ?
C20 C3 C18 O8 75.2(2) . . . . ?
C20 C3 C2 O6 -17.4(3) . . . . ?
C20 C3 C2 C1 101.94(17) . . . . ?
C20 C3 C2 C14 -144.13(19) . . . . ?
C3 N1 C1 O1 168.4(3) . . . . ?
C3 N1 C1 C2 -11.23(17) . . . . ?
C3 N1 C4 C11 161.2(2) . . . . ?
C3 N1 C4 C5 -21.9(3) . . . . ?
C3 C20 C21 C22 -137.5(2) . . . . ?
C3 C20 C21 C26 44.7(3) . . . . ?
C3 C2 C14 O5 128.00(19) . . . . ?
C3 C2 C14 O4 -52.7(3) . . . . ?
C18 C3 C2 O6 115.9(2) . . . . ?
C18 C3 C2 C1 -124.79(19) . . . . ?
C18 C3 C2 C14 -10.9(3) . . . . ?
C10 C5 C6 C7 0.1(4) . . . . ?
C10 C9 C8 C7 0.6(4) . . . . ?
C5 C10 C9 C8 -0.6(4) . . . . ?
C6 C7 C8 C9 -0.3(4) . . . . ?
C12 C11 C4 N1 -8.8(4) . . . . ?
C12 C11 C4 C5 174.5(2) . . . . ?
C2 O6 C15 O5 -14.6(2) . . . . ?
C2 O6 C15 C16 -130.4(2) . . . . ?
C2 O6 C15 C17 103.1(2) . . . . ?
C2 C3 C18 O7 126.7(2) . . . . ?
C2 C3 C18 O8 -51.6(2) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C14 O5 C15 O6 10.2(2) . . . . ?
C14 O5 C15 C16 125.7(2) . . . . ?
C14 O5 C15 C17 -107.8(2) . . . . ?
C9 C10 C5 C4 176.7(2) . . . . ?
C9 C10 C5 C6 0.2(4) . . . . ?
C23 C22 C21 C20 -179.1(2) . . . . ?
C23 C22 C21 C26 -1.2(4) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C13 O3 C12 O2 -6.2(4) . . . . ?
C13 O3 C12 C11 174.91(19) . . . . ?
C8 C7 C6 C5 -0.1(4) . . . . ?
C21 C20 C3 N1 -154.16(19) . . . . ?
C21 C20 C3 C18 -17.3(3) . . . . ?
C21 C20 C3 C2 113.5(2) . . . . ?
C21 C22 C23 C24 1.3(4) . . . . ?
C21 C26 C25 C24 0.4(4) . . . . ?
C25 C26 C21 C20 178.1(2) . . . . ?
C25 C26 C21 C22 0.3(4) . . . . ?
C19 O8 C18 O7 -4.2(3) . . . . ?
C19 O8 C18 C3 174.12(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_smi7
_database_code_depnum_ccdc_archive 'CCDC 1890947'
loop_
_audit_author_name
_audit_author_address
'galina starova'
;Saint-Petersburg state university
Russia
;
_audit_update_record             
;
2019-01-15 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Br N O10'
_chemical_formula_sum            'C22 H20 Br N O10'
_chemical_formula_weight         538.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'br1 c22 o9 n1 h16'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.6963(3)
_cell_length_b                   12.8666(3)
_cell_length_c                   18.3433(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.842(3)
_cell_angle_gamma                90
_cell_volume                     2247.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7153
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.6160
_cell_measurement_theta_min      3.2130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.888
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22363
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.600
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   21.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000    0.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   10.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  3 omega   12.00   38.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -2.00   79.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000   90.0000 81

#__ type_ start__ end____ width___ exp.time_
  5 omega  -44.00   45.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -19.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega  -89.00  -51.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega  -18.00    8.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -104.0000  -96.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega    7.00   77.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega  -18.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   19.0000  -30.0000 101
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0500086000
_diffrn_orient_matrix_UB_12      0.0363421000
_diffrn_orient_matrix_UB_13      -0.0180257000
_diffrn_orient_matrix_UB_21      -0.0289841000
_diffrn_orient_matrix_UB_22      -0.0387063000
_diffrn_orient_matrix_UB_23      -0.0259154000
_diffrn_orient_matrix_UB_31      -0.0469474000
_diffrn_orient_matrix_UB_32      -0.0148085000
_diffrn_orient_matrix_UB_33      0.0235342000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4245
_reflns_number_total             5104
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.188
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         5104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+2.5590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0743
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C10(H10), C8(H8)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.40428(3) 0.36517(2) 0.02094(2) 0.02507(8) Uani 1 1 d . . . . .
O2 O 0.22285(16) 0.18046(13) -0.12641(8) 0.0179(3) Uani 1 1 d . . . . .
O9 O 0.24680(16) -0.03597(12) -0.18360(9) 0.0173(3) Uani 1 1 d . . . . .
O7 O 0.42249(17) 0.23001(12) -0.23190(9) 0.0186(4) Uani 1 1 d . . . . .
O6 O 0.57897(16) -0.09759(12) -0.16435(9) 0.0164(3) Uani 1 1 d . . . . .
O3 O 0.20767(17) 0.17561(15) -0.00648(9) 0.0239(4) Uani 1 1 d . . . . .
O10 O 0.36579(16) -0.02576(13) -0.06873(9) 0.0183(4) Uani 1 1 d . . . . .
O4 O 0.63647(19) 0.09796(14) -0.28527(10) 0.0244(4) Uani 1 1 d . . . . .
N1 N 0.54883(19) 0.12940(14) -0.10194(10) 0.0140(4) Uani 1 1 d . . . . .
O8 O 0.26591(17) 0.10599(12) -0.26600(9) 0.0185(4) Uani 1 1 d . . . . .
O5 O 0.66983(18) -0.07342(13) -0.26935(9) 0.0206(4) Uani 1 1 d . . . . .
C11 C 0.4137(2) 0.24371(17) -0.03660(12) 0.0156(5) Uani 1 1 d . . . . .
O1 O 0.78612(17) 0.07219(14) -0.07654(10) 0.0241(4) Uani 1 1 d . . . . .
C12 C 0.2720(2) 0.19607(17) -0.06180(13) 0.0157(5) Uani 1 1 d . . . . .
C21 C 0.0614(3) 0.0022(2) -0.28095(15) 0.0250(6) Uani 1 1 d . . . . .
H21A H 0.025708 -0.067155 -0.278979 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.034509 0.028949 -0.330439 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.023391 0.045743 -0.247094 0.038 Uiso 1 1 calc GR . . . .
C18 C 0.3815(2) 0.14435(18) -0.22236(12) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.5861(2) 0.00955(17) -0.17440(12) 0.0144(5) Uani 1 1 d . . . . .
C22 C 0.3523(2) 0.00045(17) -0.13195(13) 0.0141(5) Uani 1 1 d . . . . .
C14 C 0.6334(2) 0.02119(19) -0.24906(13) 0.0179(5) Uani 1 1 d . . . . .
C1 C 0.6674(2) 0.07321(18) -0.10886(13) 0.0166(5) Uani 1 1 d . . . . .
C7 C 0.8614(2) 0.31470(19) 0.07109(13) 0.0194(5) Uani 1 1 d . . . . .
H7 H 0.904753 0.310754 0.120743 0.023 Uiso 1 1 calc R . . . .
C15 C 0.6661(2) -0.14794(18) -0.20968(13) 0.0182(5) Uani 1 1 d . . . . .
C5 C 0.6707(2) 0.26947(17) -0.02747(12) 0.0150(5) Uani 1 1 d . . . . .
C3 C 0.4531(2) 0.07321(17) -0.16066(12) 0.0127(4) Uani 1 1 d . . . . .
C6 C 0.7345(2) 0.26455(18) 0.04687(13) 0.0168(5) Uani 1 1 d . . . . .
H6 H 0.692187 0.227679 0.080342 0.020 Uiso 1 1 calc R . . . .
C4 C 0.5347(2) 0.21434(17) -0.05471(12) 0.0143(5) Uani 1 1 d . . . . .
C19 C 0.2191(2) 0.00063(18) -0.25953(13) 0.0182(5) Uani 1 1 d . . . . .
C9 C 0.8591(3) 0.3766(2) -0.05294(14) 0.0264(6) Uani 1 1 d . . . . .
H9 H 0.900269 0.414876 -0.086137 0.032 Uiso 1 1 calc R . . . .
C16 C 0.5947(3) -0.24573(19) -0.24127(15) 0.0254(6) Uani 1 1 d . . . . .
H16A H 0.585844 -0.292452 -0.201611 0.038 Uiso 1 1 calc GR . . . .
H16B H 0.649505 -0.278085 -0.273448 0.038 Uiso 1 1 calc GR . . . .
H16C H 0.503178 -0.229291 -0.268986 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.7331(3) 0.32521(19) -0.07747(13) 0.0206(5) Uani 1 1 d . . . . .
H10 H 0.690557 0.328074 -0.127287 0.025 Uiso 1 1 calc R . . . .
C17 C 0.8137(3) -0.16278(19) -0.16788(14) 0.0215(5) Uani 1 1 d . . . . .
H17A H 0.851600 -0.096952 -0.149307 0.032 Uiso 1 1 calc GR . . . .
H17B H 0.870470 -0.191384 -0.200539 0.032 Uiso 1 1 calc GR . . . .
H17C H 0.813224 -0.209484 -0.127114 0.032 Uiso 1 1 calc GR . . . .
C20 C 0.2867(3) -0.06925(19) -0.30831(14) 0.0234(5) Uani 1 1 d . . . . .
H20A H 0.386835 -0.067338 -0.292417 0.035 Uiso 1 1 calc GR . . . .
H20B H 0.262656 -0.045918 -0.358819 0.035 Uiso 1 1 calc GR . . . .
H20C H 0.253842 -0.139133 -0.304852 0.035 Uiso 1 1 calc GR . . . .
C13 C 0.0690(2) 0.1289(2) -0.02898(14) 0.0261(6) Uani 1 1 d . . . . .
H13A H 0.011859 0.172915 -0.064768 0.039 Uiso 1 1 calc GR . . . .
H13B H 0.025693 0.121192 0.013653 0.039 Uiso 1 1 calc GR . . . .
H13C H 0.078303 0.061959 -0.050626 0.039 Uiso 1 1 calc GR . . . .
C8 C 0.9238(3) 0.3707(2) 0.02146(14) 0.0234(5) Uani 1 1 d . . . . .
H8 H 1.008847 0.404349 0.037840 0.028 Uiso 1 1 calc R . . . .


_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 1.898(2) . ?
O2 C12 1.208(3) . ?
O9 C22 1.341(3) . ?
O9 C19 1.447(3) . ?
O7 C18 1.196(3) . ?
O6 C2 1.394(3) . ?
O6 C15 1.445(3) . ?
O3 C12 1.314(3) . ?
O3 C13 1.459(3) . ?
O10 C22 1.191(3) . ?
O4 C14 1.194(3) . ?
N1 C1 1.384(3) . ?
N1 C3 1.472(3) . ?
N1 C4 1.417(3) . ?
O8 C18 1.343(3) . ?
O8 C19 1.442(3) . ?
O5 C14 1.340(3) . ?
O5 C15 1.461(3) . ?
C11 C12 1.496(3) . ?
C11 C4 1.333(3) . ?
O1 C1 1.191(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 C19 1.505(3) . ?
C18 C3 1.518(3) . ?
C2 C14 1.531(3) . ?
C2 C1 1.543(3) . ?
C2 C3 1.588(3) . ?
C22 C3 1.518(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.386(3) . ?
C7 C8 1.386(3) . ?
C15 C16 1.499(3) . ?
C15 C17 1.503(3) . ?
C5 C6 1.389(3) . ?
C5 C4 1.498(3) . ?
C5 C10 1.390(3) . ?
C6 H6 0.9300 . ?
C19 C20 1.504(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(3) . ?
C9 C8 1.393(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C10 H10 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8 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
C22 O9 C19 123.05(17) . . ?
C2 O6 C15 108.55(17) . . ?
C12 O3 C13 114.20(18) . . ?
C1 N1 C3 95.55(17) . . ?
C1 N1 C4 129.50(19) . . ?
C4 N1 C3 134.90(18) . . ?
C18 O8 C19 122.49(18) . . ?
C14 O5 C15 110.07(17) . . ?
C12 C11 Br1 111.84(15) . . ?
C4 C11 Br1 120.57(17) . . ?
C4 C11 C12 127.4(2) . . ?
O2 C12 O3 124.6(2) . . ?
O2 C12 C11 122.8(2) . . ?
O3 C12 C11 112.66(19) . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
O7 C18 O8 121.0(2) . . ?
O7 C18 C3 123.1(2) . . ?
O8 C18 C3 115.87(19) . . ?
O6 C2 C14 104.23(18) . . ?
O6 C2 C1 116.91(19) . . ?
O6 C2 C3 115.27(18) . . ?
C14 C2 C1 116.76(18) . . ?
C14 C2 C3 118.70(18) . . ?
C1 C2 C3 85.05(16) . . ?
O9 C22 C3 115.21(19) . . ?
O10 C22 O9 121.2(2) . . ?
O10 C22 C3 123.5(2) . . ?
O4 C14 O5 124.2(2) . . ?
O4 C14 C2 128.4(2) . . ?
O5 C14 C2 107.38(19) . . ?
N1 C1 C2 92.13(17) . . ?
O1 C1 N1 134.6(2) . . ?
O1 C1 C2 133.3(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.1(2) . . ?
O6 C15 O5 103.68(17) . . ?
O6 C15 C16 108.76(19) . . ?
O6 C15 C17 111.53(19) . . ?
O5 C15 C16 109.63(19) . . ?
O5 C15 C17 108.06(19) . . ?
C16 C15 C17 114.6(2) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 C10 120.2(2) . . ?
C10 C5 C4 119.3(2) . . ?
N1 C3 C18 112.72(18) . . ?
N1 C3 C2 87.15(15) . . ?
N1 C3 C22 114.06(18) . . ?
C18 C3 C2 117.65(18) . . ?
C22 C3 C18 113.34(18) . . ?
C22 C3 C2 109.42(17) . . ?
C7 C6 C5 119.9(2) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C4 C5 112.91(18) . . ?
C11 C4 N1 124.2(2) . . ?
C11 C4 C5 122.9(2) . . ?
O9 C19 C21 104.56(19) . . ?
O9 C19 C20 110.82(19) . . ?
O8 C19 O9 112.40(18) . . ?
O8 C19 C21 106.64(19) . . ?
O8 C19 C20 109.50(19) . . ?
C20 C19 C21 112.8(2) . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 119.9(2) . . ?
C8 C9 H9 120.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C10 H10 120.1 . . ?
C9 C10 C5 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 C9 120.0(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?

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
Br1 C11 C12 O2 123.4(2) . . . . ?
Br1 C11 C12 O3 -55.3(2) . . . . ?
Br1 C11 C4 N1 -175.10(16) . . . . ?
Br1 C11 C4 C5 4.1(3) . . . . ?
O9 C22 C3 N1 167.52(18) . . . . ?
O9 C22 C3 C18 36.7(3) . . . . ?
O9 C22 C3 C2 -96.8(2) . . . . ?
O7 C18 C3 N1 17.2(3) . . . . ?
O7 C18 C3 C2 -81.9(3) . . . . ?
O7 C18 C3 C22 148.6(2) . . . . ?
O6 C2 C14 O4 169.3(2) . . . . ?
O6 C2 C14 O5 -9.4(2) . . . . ?
O6 C2 C1 N1 -118.4(2) . . . . ?
O6 C2 C1 O1 60.5(4) . . . . ?
O6 C2 C3 N1 119.89(19) . . . . ?
O6 C2 C3 C18 -125.9(2) . . . . ?
O6 C2 C3 C22 5.4(3) . . . . ?
O10 C22 C3 N1 -14.4(3) . . . . ?
O10 C22 C3 C18 -145.2(2) . . . . ?
O10 C22 C3 C2 81.3(3) . . . . ?
O8 C18 C3 N1 -161.85(18) . . . . ?
O8 C18 C3 C2 99.0(2) . . . . ?
O8 C18 C3 C22 -30.4(3) . . . . ?
C12 C11 C4 N1 -0.7(4) . . . . ?
C12 C11 C4 C5 178.5(2) . . . . ?
C18 O8 C19 O9 34.6(3) . . . . ?
C18 O8 C19 C21 148.6(2) . . . . ?
C18 O8 C19 C20 -89.1(2) . . . . ?
C2 O6 C15 O5 -25.4(2) . . . . ?
C2 O6 C15 C16 -142.0(2) . . . . ?
C2 O6 C15 C17 90.6(2) . . . . ?
C22 O9 C19 O8 -27.4(3) . . . . ?
C22 O9 C19 C21 -142.6(2) . . . . ?
C22 O9 C19 C20 95.5(2) . . . . ?
C14 O5 C15 O6 19.2(2) . . . . ?
C14 O5 C15 C16 135.2(2) . . . . ?
C14 O5 C15 C17 -99.2(2) . . . . ?
C14 C2 C1 N1 117.2(2) . . . . ?
C14 C2 C1 O1 -63.9(4) . . . . ?
C14 C2 C3 N1 -115.5(2) . . . . ?
C14 C2 C3 C18 -1.2(3) . . . . ?
C14 C2 C3 C22 130.0(2) . . . . ?
C1 N1 C3 C18 -121.57(19) . . . . ?
C1 N1 C3 C2 -2.69(17) . . . . ?
C1 N1 C3 C22 107.3(2) . . . . ?
C1 N1 C4 C11 -159.8(2) . . . . ?
C1 N1 C4 C5 20.9(3) . . . . ?
C1 C2 C14 O4 -60.1(3) . . . . ?
C1 C2 C14 O5 121.2(2) . . . . ?
C1 C2 C3 N1 2.41(15) . . . . ?
C1 C2 C3 C18 116.7(2) . . . . ?
C1 C2 C3 C22 -112.12(18) . . . . ?
C15 O6 C2 C14 21.6(2) . . . . ?
C15 O6 C2 C1 -108.9(2) . . . . ?
C15 O6 C2 C3 153.47(18) . . . . ?
C15 O5 C14 O4 174.9(2) . . . . ?
C15 O5 C14 C2 -6.4(2) . . . . ?
C3 N1 C1 O1 -176.2(3) . . . . ?
C3 N1 C1 C2 2.77(17) . . . . ?
C3 N1 C4 C11 23.3(4) . . . . ?
C3 N1 C4 C5 -156.0(2) . . . . ?
C3 C2 C14 O4 39.4(3) . . . . ?
C3 C2 C14 O5 -139.26(19) . . . . ?
C3 C2 C1 N1 -2.56(16) . . . . ?
C3 C2 C1 O1 176.4(3) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C6 C5 C4 N1 -111.5(2) . . . . ?
C6 C5 C4 C11 69.2(3) . . . . ?
C6 C5 C10 C9 -0.4(4) . . . . ?
C4 N1 C1 O1 6.1(4) . . . . ?
C4 N1 C1 C2 -175.0(2) . . . . ?
C4 N1 C3 C18 56.0(3) . . . . ?
C4 N1 C3 C2 174.9(2) . . . . ?
C4 N1 C3 C22 -75.1(3) . . . . ?
C4 C11 C12 O2 -51.4(4) . . . . ?
C4 C11 C12 O3 129.9(3) . . . . ?
C4 C5 C6 C7 179.0(2) . . . . ?
C4 C5 C10 C9 -180.0(2) . . . . ?
C19 O9 C22 O10 174.3(2) . . . . ?
C19 O9 C22 C3 -7.6(3) . . . . ?
C19 O8 C18 O7 175.5(2) . . . . ?
C19 O8 C18 C3 -5.5(3) . . . . ?
C10 C5 C6 C7 -0.5(3) . . . . ?
C10 C5 C4 N1 68.0(3) . . . . ?
C10 C5 C4 C11 -111.3(3) . . . . ?
C10 C9 C8 C7 -0.8(4) . . . . ?
C13 O3 C12 O2 1.3(3) . . . . ?
C13 O3 C12 C11 -179.9(2) . . . . ?
C8 C7 C6 C5 0.8(4) . . . . ?
C8 C9 C10 C5 1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10681-11733_agf2
_database_code_depnum_ccdc_archive 'CCDC 1893280'
loop_
_audit_author_name
_audit_author_address
'galina starova'
;Saint-Petersburg state university
Russia
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 Br N2 O11'
_chemical_formula_sum            'C26 H21 Br N2 O11'
_chemical_formula_weight         617.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c26 h21 b'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.9781(2)
_cell_length_b                   10.33117(14)
_cell_length_c                   27.7978(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.5433(12)
_cell_angle_gamma                90
_cell_volume                     5153.15(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    21217
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7510
_cell_measurement_theta_min      4.7380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             2512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34103
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.151
_diffrn_reflns_theta_min         3.186
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  27.00   1.00    1.00    --  -40.38  38.00-150.00   88
  2  ω     72.00 113.00   1.00    1.00    --   40.38 178.00 -60.00   41
  3  ω    118.00 167.00   1.00    2.29    --  113.00 112.00  60.00   49
  4  ω    131.00 177.00   1.00    2.29    --  113.00 112.00  90.00   46
  5  ω     82.00 176.00   1.00    2.29    --  113.00  30.00 120.00   94
  6  ω     57.00 104.00   1.00    2.29    --  113.00 -95.00  90.00   47
  7  ω     36.00 122.00   1.00    2.29    --  113.00 -30.00 -60.00   86
  8  ω     69.00 143.00   1.00    2.29    --  113.00  15.00-120.00   74
  9  ω     51.00 107.00   1.00    2.29    --  113.00 -95.00 -90.00   56
 10  ω     38.00  76.00   1.00    2.29    --  113.00 -45.00-180.00   38
 11  ω    -94.00   4.00   1.00    1.00    --  -40.38 -19.00   0.00   98
 12  ω   -113.00 -88.00   1.00    1.00    --  -40.38-139.00 119.00   25
 13  ω   -111.00 -12.00   1.00    1.00    --  -40.38 -57.00-150.00   99
 14  ω    -92.00 -27.00   1.00    1.00    --  -40.38 -38.00 120.00   65
 15  ω    -76.00 -34.00   1.00    1.00    --  -40.38 -38.00-120.00   42
 16  ω     81.00 107.00   1.00    2.29    --  113.00  68.00-102.54   26
 17  ω     86.00 111.00   1.00    2.29    --  113.00  45.00-104.11   25
 18  ω     84.00 110.00   1.00    2.29    --  113.00  52.00-130.94   26
 19  ω    129.00 155.00   1.00    2.29    --  113.00  39.00-104.26   26
 20  ω     86.00 164.00   1.00    2.29    --  113.00  46.00 -95.39   78
 21  ω     83.00 108.00   1.00    2.29    --  113.00  66.00 -89.01   25
 22  ω     81.00 108.00   1.00    2.29    --  113.00  73.00-105.70   27
 23  ω     84.00 110.00   1.00    2.29    --  113.00  55.00-103.89   26
 24  ω     32.00  79.00   1.00    2.29    --  113.00 -15.00 150.00   47
 25  ω     84.00 109.00   1.00    2.29    --  113.00  61.00-120.00   25
 26  ω     83.00 116.00   1.00    2.29    --  113.00  61.00 -60.00   33
 27  ω    135.00 161.00   1.00    2.29    --  113.00  30.00 -30.00   26
 28  ω     86.00 111.00   1.00    2.29    --  113.00  61.00 -90.00   25
 29  ω     84.00 110.00   1.00    2.29    --  113.00  61.00-150.00   26
 30  ω     79.00 106.00   1.00    2.29    --  113.00  77.00 -90.00   27
 31  ω     83.00 110.00   1.00    2.29    --  113.00  61.00-180.00   27
 32  ω     79.00 105.00   1.00    2.29    --  113.00  77.00-150.00   26
 33  ω    141.00 168.00   1.00    2.29    --  113.00  77.00-150.00   27
 34  ω     79.00 105.00   1.00    2.29    --  113.00  77.00-180.00   26
 35  ω     79.00 106.00   1.00    2.29    --  113.00  77.00-120.00   27
 36  ω     86.00 111.00   1.00    2.29    --  113.00  45.00-150.00   25
 37  ω     42.00  67.00   1.00    2.29    --  113.00 -95.00  60.00   25
 38  ω     87.00 150.00   1.00    2.29    --  113.00  45.00 -60.00   63
 39  ω     84.00 111.00   1.00    2.29    --  113.00  55.00 -79.51   27
 40  ω     80.00 107.00   1.00    2.29    --  113.00  77.00 -60.00   27
 41  ω     87.00 114.00   1.00    2.29    --  113.00  45.00-180.00   27
 42  ω     90.00 115.00   1.00    2.29    --  113.00  45.00-120.00   25
 43  ω     89.00 116.00   1.00    2.29    --  113.00  39.00-104.26   27
 44  ω     83.00 110.00   1.00    2.29    --  113.00  30.00-120.00   27
 45  ω     86.00 124.00   1.00    2.29    --  113.00  30.00 -90.00   38
 46  ω    146.00 172.00   1.00    2.29    --  113.00  48.00-174.02   26
 47  ω     85.00 112.00   1.00    2.29    --  113.00  48.00-174.02   27
 48  ω   -119.00 -93.00   1.00    1.00    --  -40.38 -77.00 150.00   26
 49  ω      2.00  56.00   1.00    1.00    --   40.38 -99.00   0.00   54
 50  ω     60.00 106.00   1.00    1.00    --   40.38-141.00 121.00   46
 51  ω     57.00 114.00   1.00    2.29    --  113.00-112.00  30.00   57
 52  ω    117.00 177.00   1.00    2.29    --  113.00 112.00 -90.00   60
 53  ω    134.00 178.00   1.00    2.29    --  113.00 112.00 -30.00   44
 54  ω     90.00 115.00   1.00    2.29    --  113.00-112.00 120.00   25
 55  ω    153.00 178.00   1.00    2.29    --  113.00  61.00 120.00   25
 56  ω     73.00 106.00   1.00    2.29    --  113.00 -77.00 -90.00   33
 57  ω    122.00 147.00   1.00    2.29    --  113.00 -77.00 -90.00   25
 58  ω     55.00  80.00   1.00    2.29    --  113.00-112.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0442568000
_diffrn_orient_matrix_UB_12      -0.0261664000
_diffrn_orient_matrix_UB_13      -0.0482667000
_diffrn_orient_matrix_UB_21      -0.0647636000
_diffrn_orient_matrix_UB_22      -0.0553174000
_diffrn_orient_matrix_UB_23      0.0274189000
_diffrn_orient_matrix_UB_31      -0.0348525000
_diffrn_orient_matrix_UB_32      0.1359683000
_diffrn_orient_matrix_UB_33      0.0018794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5150
_reflns_number_total             5332
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.932
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         5332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+9.8360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.0988
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C23(H23), C6(H6), C22(H22), C26(H26), C25(H25), C10(H10), C7(H7), C9(H9),
 C8(H8)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57469(2) -0.01847(2) 0.69755(2) 0.02317(9) Uani 1 1 d . . . . .
O5 O 0.62566(8) 0.73992(13) 0.61693(5) 0.0182(3) Uani 1 1 d . . . . .
O1 O 0.67712(7) 0.34806(13) 0.61342(5) 0.0176(3) Uani 1 1 d . . . . .
O6 O 0.58477(7) 0.57784(12) 0.56576(5) 0.0155(3) Uani 1 1 d . . . . .
O3 O 0.66197(7) 0.32290(13) 0.71956(5) 0.0175(3) Uani 1 1 d . . . . .
O9 O 0.48524(7) 0.37878(13) 0.54926(5) 0.0169(3) Uani 1 1 d . . . . .
O11 O 0.11349(8) 0.57938(16) 0.57793(6) 0.0263(3) Uani 1 1 d . . . . .
O8 O 0.45607(7) 0.64613(14) 0.66021(5) 0.0191(3) Uani 1 1 d . . . . .
O2 O 0.72115(7) 0.13851(14) 0.70231(5) 0.0205(3) Uani 1 1 d . . . . .
O4 O 0.62797(8) 0.63299(14) 0.68731(5) 0.0213(3) Uani 1 1 d . . . . .
O7 O 0.45358(8) 0.46389(15) 0.70503(5) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.55517(8) 0.34908(15) 0.64121(5) 0.0134(3) Uani 1 1 d . . . . .
O10 O 0.14088(8) 0.65801(17) 0.50928(6) 0.0315(4) Uani 1 1 d . . . . .
N2 N 0.15774(9) 0.60528(16) 0.54779(6) 0.0201(3) Uani 1 1 d . . . . .
C15 C 0.59739(11) 0.71589(18) 0.56768(7) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.53745(10) 0.22612(17) 0.65925(6) 0.0132(3) Uani 1 1 d . . . . .
C24 C 0.23629(10) 0.56709(18) 0.55812(7) 0.0168(4) Uani 1 1 d . . . . .
C23 C 0.28615(10) 0.58819(18) 0.52288(7) 0.0172(4) Uani 1 1 d . . . . .
H23 H 0.271159 0.628668 0.494012 0.021 Uiso 1 1 calc R . . . .
C5 C 0.46082(10) 0.17618(18) 0.64638(7) 0.0146(3) Uani 1 1 d . . . . .
C11 C 0.58980(10) 0.15768(18) 0.68431(6) 0.0141(3) Uani 1 1 d . . . . .
C21 C 0.38006(10) 0.48709(17) 0.57568(7) 0.0141(3) Uani 1 1 d . . . . .
C20 C 0.45781(10) 0.43595(17) 0.58151(6) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.61816(10) 0.39553(18) 0.62114(6) 0.0134(3) Uani 1 1 d . . . . .
C6 C 0.44259(10) 0.12383(19) 0.60112(7) 0.0172(4) Uani 1 1 d . . . . .
H6 H 0.477167 0.124739 0.577582 0.021 Uiso 1 1 calc R . . . .
C22 C 0.35919(10) 0.54704(19) 0.53199(7) 0.0156(3) Uani 1 1 d . . . . .
H22 H 0.394034 0.559426 0.509047 0.019 Uiso 1 1 calc R . . . .
C12 C 0.66566(10) 0.20351(18) 0.70214(6) 0.0143(3) Uani 1 1 d . . . . .
C26 C 0.32843(11) 0.46749(19) 0.61059(7) 0.0180(4) Uani 1 1 d . . . . .
H26 H 0.343098 0.427939 0.639697 0.022 Uiso 1 1 calc R . . . .
C25 C 0.25498(11) 0.5075(2) 0.60153(7) 0.0185(4) Uani 1 1 d . . . . .
H25 H 0.219616 0.494392 0.624086 0.022 Uiso 1 1 calc R . . . .
C10 C 0.40829(11) 0.1774(2) 0.68139(7) 0.0199(4) Uani 1 1 d . . . . .
H10 H 0.420491 0.212468 0.711676 0.024 Uiso 1 1 calc R . . . .
C3 C 0.50796(10) 0.46097(17) 0.62811(6) 0.0130(3) Uani 1 1 d . . . . .
C14 C 0.61391(10) 0.63717(18) 0.64489(7) 0.0158(4) Uani 1 1 d . . . . .
C17 C 0.52530(12) 0.7889(2) 0.55792(8) 0.0237(4) Uani 1 1 d . . . . .
H17A H 0.490255 0.763015 0.580779 0.036 Uiso 1 1 calc GR . . . .
H17B H 0.505270 0.769847 0.525881 0.036 Uiso 1 1 calc GR . . . .
H17C H 0.534518 0.880127 0.560876 0.036 Uiso 1 1 calc GR . . . .
C7 C 0.37229(11) 0.0700(2) 0.59119(7) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.360288 0.033156 0.561188 0.027 Uiso 1 1 calc R . . . .
C2 C 0.58212(10) 0.52953(17) 0.61186(6) 0.0133(3) Uani 1 1 d . . . . .
C9 C 0.33762(11) 0.1260(2) 0.67074(8) 0.0234(4) Uani 1 1 d . . . . .
H9 H 0.302161 0.128486 0.693702 0.028 Uiso 1 1 calc R . . . .
C18 C 0.46985(10) 0.52131(19) 0.67005(7) 0.0160(4) Uani 1 1 d . . . . .
C16 C 0.65739(11) 0.7463(2) 0.53388(7) 0.0217(4) Uani 1 1 d . . . . .
H16A H 0.667928 0.837377 0.534902 0.032 Uiso 1 1 calc GR . . . .
H16B H 0.640738 0.722010 0.501659 0.032 Uiso 1 1 calc GR . . . .
H16C H 0.701743 0.698842 0.543538 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.73202(12) 0.3786(2) 0.73759(8) 0.0254(4) Uani 1 1 d . . . . .
H13A H 0.764254 0.388210 0.711549 0.038 Uiso 1 1 calc GR . . . .
H13B H 0.755160 0.322693 0.761714 0.038 Uiso 1 1 calc GR . . . .
H13C H 0.723168 0.461825 0.751482 0.038 Uiso 1 1 calc GR . . . .
C8 C 0.32000(11) 0.0712(2) 0.62599(8) 0.0235(4) Uani 1 1 d . . . . .
H8 H 0.273119 0.035149 0.619231 0.028 Uiso 1 1 calc R . . . .
C19 C 0.41308(12) 0.7143(2) 0.69504(9) 0.0294(5) Uani 1 1 d . . . . .
H19A H 0.413024 0.805332 0.688063 0.044 Uiso 1 1 calc GR . . . .
H19B H 0.435092 0.699935 0.726934 0.044 Uiso 1 1 calc GR . . . .
H19C H 0.362783 0.682626 0.693052 0.044 Uiso 1 1 calc GR . . . .


_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 1.8798(18) . ?
O5 C15 1.452(2) . ?
O5 C14 1.340(2) . ?
O1 C1 1.199(2) . ?
O6 C15 1.445(2) . ?
O6 C2 1.379(2) . ?
O3 C12 1.328(2) . ?
O3 C13 1.446(2) . ?
O9 C20 1.204(2) . ?
O11 N2 1.220(2) . ?
O8 C18 1.338(2) . ?
O8 C19 1.457(2) . ?
O2 C12 1.202(2) . ?
O4 C14 1.191(2) . ?
O7 C18 1.191(3) . ?
N1 C4 1.409(2) . ?
N1 C1 1.379(2) . ?
N1 C3 1.467(2) . ?
O10 N2 1.223(2) . ?
N2 C24 1.477(2) . ?
C15 C17 1.509(3) . ?
C15 C16 1.507(3) . ?
C4 C5 1.494(2) . ?
C4 C11 1.338(3) . ?
C24 C23 1.385(3) . ?
C24 C25 1.378(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.389(3) . ?
C5 C6 1.390(3) . ?
C5 C10 1.397(3) . ?
C11 C12 1.499(2) . ?
C21 C20 1.494(2) . ?
C21 C22 1.394(3) . ?
C21 C26 1.398(3) . ?
C20 C3 1.553(2) . ?
C1 C2 1.543(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(3) . ?
C22 H22 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.392(3) . ?
C25 H25 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.392(3) . ?
C3 C2 1.599(2) . ?
C3 C18 1.522(2) . ?
C14 C2 1.530(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.386(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C8 H8 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C14 O5 C15 110.65(14) . . ?
C2 O6 C15 109.72(13) . . ?
C12 O3 C13 115.71(16) . . ?
C18 O8 C19 115.42(16) . . ?
C4 N1 C3 131.20(14) . . ?
C1 N1 C4 131.83(15) . . ?
C1 N1 C3 95.88(14) . . ?
O11 N2 O10 124.21(17) . . ?
O11 N2 C24 117.65(17) . . ?
O10 N2 C24 118.12(17) . . ?
O5 C15 C17 109.32(16) . . ?
O5 C15 C16 109.27(15) . . ?
O6 C15 O5 104.40(14) . . ?
O6 C15 C17 110.81(15) . . ?
O6 C15 C16 107.43(15) . . ?
C16 C15 C17 115.06(17) . . ?
N1 C4 C5 116.84(15) . . ?
C11 C4 N1 119.63(16) . . ?
C11 C4 C5 123.43(17) . . ?
C23 C24 N2 118.24(17) . . ?
C25 C24 N2 117.91(17) . . ?
C25 C24 C23 123.79(17) . . ?
C24 C23 H23 121.0 . . ?
C24 C23 C22 117.96(17) . . ?
C22 C23 H23 121.0 . . ?
C6 C5 C4 120.91(16) . . ?
C6 C5 C10 120.16(17) . . ?
C10 C5 C4 118.87(16) . . ?
C4 C11 Br1 120.53(14) . . ?
C4 C11 C12 126.99(17) . . ?
C12 C11 Br1 112.38(13) . . ?
C22 C21 C20 116.83(16) . . ?
C22 C21 C26 120.96(17) . . ?
C26 C21 C20 122.03(17) . . ?
O9 C20 C21 121.08(16) . . ?
O9 C20 C3 117.32(15) . . ?
C21 C20 C3 121.51(15) . . ?
O1 C1 N1 133.40(18) . . ?
O1 C1 C2 134.70(17) . . ?
N1 C1 C2 91.89(14) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.67(17) . . ?
C7 C6 H6 120.2 . . ?
C23 C22 C21 119.70(17) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O3 C12 C11 110.43(15) . . ?
O2 C12 O3 125.26(17) . . ?
O2 C12 C11 124.24(17) . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.64(18) . . ?
C25 C26 H26 120.2 . . ?
C24 C25 C26 117.93(18) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.70(18) . . ?
C9 C10 H10 120.2 . . ?
N1 C3 C20 111.90(14) . . ?
N1 C3 C2 86.53(12) . . ?
N1 C3 C18 114.44(15) . . ?
C20 C3 C2 106.81(14) . . ?
C18 C3 C20 116.19(15) . . ?
C18 C3 C2 117.23(15) . . ?
O5 C14 C2 107.11(15) . . ?
O4 C14 O5 124.83(17) . . ?
O4 C14 C2 128.03(18) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.20(18) . . ?
C8 C7 H7 119.9 . . ?
O6 C2 C1 116.22(15) . . ?
O6 C2 C3 120.01(15) . . ?
O6 C2 C14 105.16(14) . . ?
C1 C2 C3 84.50(13) . . ?
C14 C2 C1 114.47(15) . . ?
C14 C2 C3 116.06(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.14(18) . . ?
C8 C9 H9 119.9 . . ?
O8 C18 C3 108.95(16) . . ?
O7 C18 O8 126.52(18) . . ?
O7 C18 C3 124.50(18) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.10(18) . . ?
C9 C8 H8 120.0 . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br1 C11 C12 O3 -142.09(12) . . . . ?
Br1 C11 C12 O2 35.1(2) . . . . ?
O5 C14 C2 O6 5.39(19) . . . . ?
O5 C14 C2 C1 134.16(15) . . . . ?
O5 C14 C2 C3 -129.79(16) . . . . ?
O1 C1 C2 O6 49.9(3) . . . . ?
O1 C1 C2 C3 170.7(2) . . . . ?
O1 C1 C2 C14 -73.1(3) . . . . ?
O9 C20 C3 N1 -40.1(2) . . . . ?
O9 C20 C3 C2 52.9(2) . . . . ?
O9 C20 C3 C18 -174.13(16) . . . . ?
O11 N2 C24 C23 175.82(17) . . . . ?
O11 N2 C24 C25 -1.5(3) . . . . ?
O4 C14 C2 O6 -172.93(18) . . . . ?
O4 C14 C2 C1 -44.2(3) . . . . ?
O4 C14 C2 C3 51.9(3) . . . . ?
N1 C4 C5 C6 78.1(2) . . . . ?
N1 C4 C5 C10 -104.7(2) . . . . ?
N1 C4 C11 Br1 -167.04(12) . . . . ?
N1 C4 C11 C12 9.1(3) . . . . ?
N1 C1 C2 O6 -128.95(15) . . . . ?
N1 C1 C2 C3 -8.11(13) . . . . ?
N1 C1 C2 C14 108.07(16) . . . . ?
N1 C3 C2 O6 124.83(16) . . . . ?
N1 C3 C2 C1 7.63(12) . . . . ?
N1 C3 C2 C14 -106.96(16) . . . . ?
N1 C3 C18 O8 153.84(15) . . . . ?
N1 C3 C18 O7 -28.1(3) . . . . ?
O10 N2 C24 C23 -2.6(3) . . . . ?
O10 N2 C24 C25 -179.88(18) . . . . ?
N2 C24 C23 C22 -177.29(17) . . . . ?
N2 C24 C25 C26 177.84(17) . . . . ?
C15 O5 C14 O4 -175.86(18) . . . . ?
C15 O5 C14 C2 5.75(19) . . . . ?
C15 O6 C2 C1 -142.16(15) . . . . ?
C15 O6 C2 C3 118.57(17) . . . . ?
C15 O6 C2 C14 -14.44(18) . . . . ?
C4 N1 C1 O1 -1.3(3) . . . . ?
C4 N1 C1 C2 177.59(18) . . . . ?
C4 N1 C3 C20 -70.7(2) . . . . ?
C4 N1 C3 C2 -177.40(18) . . . . ?
C4 N1 C3 C18 64.2(2) . . . . ?
C4 C5 C6 C7 175.65(18) . . . . ?
C4 C5 C10 C9 -177.16(18) . . . . ?
C4 C11 C12 O3 41.5(2) . . . . ?
C4 C11 C12 O2 -141.3(2) . . . . ?
C24 C23 C22 C21 -0.2(3) . . . . ?
C23 C24 C25 C26 0.7(3) . . . . ?
C5 C4 C11 Br1 9.1(2) . . . . ?
C5 C4 C11 C12 -174.75(17) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C5 C10 C9 C8 1.5(3) . . . . ?
C11 C4 C5 C6 -98.2(2) . . . . ?
C11 C4 C5 C10 79.0(2) . . . . ?
C21 C20 C3 N1 143.28(16) . . . . ?
C21 C20 C3 C2 -123.66(17) . . . . ?
C21 C20 C3 C18 9.3(2) . . . . ?
C21 C26 C25 C24 -0.8(3) . . . . ?
C20 C21 C22 C23 175.30(17) . . . . ?
C20 C21 C26 C25 -174.50(17) . . . . ?
C20 C3 C2 O6 13.0(2) . . . . ?
C20 C3 C2 C1 -104.21(14) . . . . ?
C20 C3 C2 C14 141.20(16) . . . . ?
C20 C3 C18 O8 -73.30(19) . . . . ?
C20 C3 C18 O7 104.8(2) . . . . ?
C1 N1 C4 C5 -137.54(19) . . . . ?
C1 N1 C4 C11 38.9(3) . . . . ?
C1 N1 C3 C20 98.18(16) . . . . ?
C1 N1 C3 C2 -8.55(13) . . . . ?
C1 N1 C3 C18 -126.98(16) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C22 C21 C20 O9 -42.5(3) . . . . ?
C22 C21 C20 C3 133.92(18) . . . . ?
C22 C21 C26 C25 0.5(3) . . . . ?
C26 C21 C20 O9 132.6(2) . . . . ?
C26 C21 C20 C3 -50.9(2) . . . . ?
C26 C21 C22 C23 0.1(3) . . . . ?
C25 C24 C23 C22 -0.2(3) . . . . ?
C10 C5 C6 C7 -1.4(3) . . . . ?
C10 C9 C8 C7 -1.5(3) . . . . ?
C3 N1 C4 C5 27.5(3) . . . . ?
C3 N1 C4 C11 -156.07(18) . . . . ?
C3 N1 C1 O1 -170.0(2) . . . . ?
C3 N1 C1 C2 8.85(14) . . . . ?
C14 O5 C15 O6 -14.25(19) . . . . ?
C14 O5 C15 C17 104.35(18) . . . . ?
C14 O5 C15 C16 -128.92(16) . . . . ?
C2 O6 C15 O5 17.80(19) . . . . ?
C2 O6 C15 C17 -99.78(18) . . . . ?
C2 O6 C15 C16 133.76(16) . . . . ?
C2 C3 C18 O8 54.7(2) . . . . ?
C2 C3 C18 O7 -127.2(2) . . . . ?
C18 C3 C2 O6 -119.39(18) . . . . ?
C18 C3 C2 C1 123.41(16) . . . . ?
C18 C3 C2 C14 8.8(2) . . . . ?
C13 O3 C12 O2 3.4(3) . . . . ?
C13 O3 C12 C11 -179.50(15) . . . . ?
C19 O8 C18 O7 -3.8(3) . . . . ?
C19 O8 C18 C3 174.29(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_10681-11733_agf1
_database_code_depnum_ccdc_archive 'CCDC 1893285'
loop_
_audit_author_name
_audit_author_address
'galina starova'
;Saint-Petersburg state university
Russia
;
_audit_update_record             
;
2019-01-24 deposited with the CCDC.	2019-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H22 Br N O9'
_chemical_formula_sum            'C23 H22 Br N O9'
_chemical_formula_weight         536.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H22 Br N O9'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.66080(10)
_cell_length_b                   15.21840(10)
_cell_length_c                   13.20380(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.1330(10)
_cell_angle_gamma                90
_cell_volume                     2342.67(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18645
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.7170
_cell_measurement_theta_min      2.8660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.867
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23811
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.901
_diffrn_reflns_theta_min         4.434
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00 -16.00   0.50    0.20    --  -38.70 -68.00 -25.00  160
  2  ω     19.00  52.00   0.50    0.20    --   38.70 -68.00 -25.00   66
  3  ω     16.00  42.00   0.50    0.20    --   38.70  68.00 107.00   52
  4  ω     61.00  96.00   0.50    0.20    --   38.70  68.00 107.00   70
  5  ω     73.00 128.00   0.50    0.20    --  104.92 -68.00 -25.00  110
  6  ω     81.00 157.00   0.50    0.20    --  104.92  68.00 107.00  152
  7  ω    -62.00 -21.00   0.50    0.20    --  -38.70  68.00 107.00   82
  8  ω    -26.00  32.00   0.50    0.20    --  -38.70  21.00  60.00  116
  9  ω    -26.00   5.00   0.50    0.20    --  -38.70  32.00 -30.00   62
 10  ω   -110.00 -19.00   0.50    0.20    --  -38.70 -21.00 150.00  182
 11  ω     20.00  65.00   0.50    0.20    --   38.70  54.00-150.00   90
 12  ω     73.00 101.00   0.50    0.20    --   38.70  54.00-150.00   56
 13  ω     20.00  55.00   0.50    0.20    --   38.70  54.00-120.00   70
 14  ω     31.00 106.00   0.50    0.20    --   38.70  32.00 150.00  150
 15  ω     22.00  50.00   0.50    0.20    --   38.70  21.00  90.00   56
 16  ω     64.00 111.00   0.50    0.20    --   38.70  21.00  90.00   94
 17  ω     -7.00  58.00   0.50    0.20    --   38.70 -21.00   0.00  130
 18  ω     46.00  71.00   0.50    0.20    --   38.70  32.00   0.00   50
 19  ω     60.00  92.00   0.50    0.20    --   38.70  54.00-120.00   64
 20  ω     42.00 121.00   0.50    0.20    --  104.92 -53.00 -60.00  158
 21  ω    132.00 157.00   0.50    0.20    --  104.92  22.00-120.00   50
 22  ω     41.00 111.00   0.50    0.20    --  104.92 -45.00-180.00  140
 23  ω    114.00 155.00   0.50    0.20    --  104.92  30.00-150.00   82
 24  ω     41.00 118.00   0.50    0.20    --  104.92-133.00   0.00  154
 25  ω     39.00 114.00   0.50    0.20    --  104.92-111.00   0.00  150
 26  ω     42.00 123.00   0.50    0.20    --  104.92-133.00-150.00  162
 27  ω     92.00 151.00   0.50    0.20    --  104.92  30.00  90.00  118
 28  ω     87.00 152.00   0.50    0.20    --  104.92  61.00  90.00  130
 29  ω     84.00 121.00   0.50    0.20    --  104.92 -53.00  90.00   74
 30  ω     84.00 130.00   0.50    0.20    --  104.92  77.00  60.00   92
 31  ω     38.00 123.00   0.50    0.20    --  104.92 -22.00 120.00  170
 32  ω     60.00  85.00   0.50    0.20    --  104.92 -68.00 -25.00   50
 33  ω   -107.00 -81.00   0.50    0.20    --  -38.70 -32.00   0.00   52
 34  ω    -89.00 -63.00   0.50    0.20    --  -38.70 -43.00 150.00   52
 35  ω    -66.00 -40.00   0.50    0.20    --  -38.70 -32.00   0.00   52
 36  ω    -25.00  12.00   0.50    0.20    --  -38.70 104.00-120.00   74
 37  ω    -77.00 -41.00   0.50    0.20    --  -38.70 104.00-120.00   72
 38  ω     37.00  63.00   0.50    0.20    --   38.70 -77.00-120.00   52
 39  ω     80.00 106.00   0.50    0.20    --   38.70  32.00-120.00   52
 40  ω     15.00  46.00   0.50    0.20    --   38.70  11.00  60.00   62
 41  ω     -3.00  41.00   0.50    0.20    --   38.70 -32.00-180.00   88
 42  ω      7.00  36.00   0.50    0.20    --   38.70 -77.00-120.00   58
 43  ω     25.00  51.00   0.50    0.20    --   38.70  54.00 -90.00   52
 44  ω     76.00 101.00   0.50    0.20    --   38.70  11.00  60.00   50
 45  ω    129.00 156.00   0.50    0.20    --  104.92  77.00-120.00   54
 46  ω     80.00 106.00   0.50    0.20    --  104.92  77.00-120.00   52
 47  ω     40.00 119.00   0.50    0.20    --  104.92 -30.00 -30.00  158
 48  ω    132.00 157.00   0.50    0.20    --  104.92  22.00  30.00   50
 49  ω     49.00 104.00   0.50    0.20    --  104.92 -86.00   0.00  110
 50  ω     85.00 152.00   0.50    0.20    --  104.92  53.00 -90.00  134
 51  ω     81.00 114.00   0.50    0.20    --  104.92  69.00-150.00   66
 52  ω     78.00 112.00   0.50    0.20    --  104.92  77.00-180.00   68
 53  ω     92.00 122.00   0.50    0.20    --  104.92 -45.00 -30.00   60
 54  ω     79.00 152.00   0.50    0.20    --  104.92  77.00 150.00  146
 55  ω     87.00 113.00   0.50    0.20    --  104.92  53.00-180.00   52
 56  ω    125.00 150.00   0.50    0.20    --  104.92  53.00-180.00   50
 57  ω     41.00  66.00   0.50    0.20    --  104.92 -45.00 -30.00   50
 58  ω     78.00 104.00   0.50    0.20    --  104.92  77.00-150.00   52
 59  ω    115.00 145.00   0.50    0.20    --  104.92 111.00 120.00   60
 60  ω     85.00 150.00   0.50    0.20    --  104.92  53.00-120.00  130
 61  ω     83.00 125.00   0.50    0.20    --  104.92 111.00 -30.00   84
 62  ω     88.00 124.00   0.50    0.20    --  104.92 111.00   0.00   72
 63  ω     86.00 112.00   0.50    0.20    --  104.92  61.00-180.00   52
 64  ω    116.00 142.00   0.50    0.20    --  104.92  75.00-163.69   52
 65  ω     85.00 111.00   0.50    0.20    --  104.92  53.00-150.00   52
 66  ω     81.00 106.00   0.50    0.20    --  104.92  69.00-120.00   50
 67  ω     79.00 104.00   0.50    0.20    --  104.92  75.00-163.69   50
 68  ω     89.00 144.00   0.50    0.20    --  104.92  93.00 120.00  110
 69  ω    127.00 152.00   0.50    0.20    --  104.92  69.00-150.00   50
 70  ω     82.00 117.00   0.50    0.20    --  104.92  69.00-180.00   70
 71  ω     83.00 108.00   0.50    0.20    --  104.92  61.00-120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698815000
_diffrn_orient_matrix_UB_12      0.0596089000
_diffrn_orient_matrix_UB_13      0.0700695000
_diffrn_orient_matrix_UB_21      -0.0456241000
_diffrn_orient_matrix_UB_22      0.0514839000
_diffrn_orient_matrix_UB_23      -0.0928312000
_diffrn_orient_matrix_UB_31      -0.1024297000
_diffrn_orient_matrix_UB_32      -0.0636225000
_diffrn_orient_matrix_UB_33      -0.0094274000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4579
_reflns_number_total             4641
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.545
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.00271(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0661P)²+3.5162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C9(H9), C10(H10), C8(H8)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C17(H17A,H17B,H17C), C13(H13A,H13B,
 H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.53255(2) 0.62091(2) 0.52420(2) 0.02259(13) Uani 1 1 d . . . . .
O8 O 0.20922(14) 0.46350(10) 0.33496(12) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.43897(14) 0.66903(11) 0.15918(12) 0.0181(4) Uani 1 1 d . . . . .
O6 O 0.18953(14) 0.67399(10) 0.06739(11) 0.0131(3) Uani 1 1 d . . . . .
O5 O 0.18196(15) 0.54307(10) -0.01767(12) 0.0164(3) Uani 1 1 d . . . . .
O9 O 0.13520(15) 0.74550(11) 0.25970(13) 0.0191(4) Uani 1 1 d . . . . .
O7 O 0.06832(15) 0.47269(11) 0.21694(13) 0.0212(4) Uani 1 1 d . . . . .
O3 O 0.50288(15) 0.50813(11) 0.25904(12) 0.0198(4) Uani 1 1 d . . . . .
O4 O 0.29375(16) 0.46170(11) 0.08631(13) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.65137(15) 0.58672(14) 0.32123(15) 0.0277(4) Uani 1 1 d . . . . .
N1 N 0.30724(16) 0.61716(12) 0.27940(14) 0.0111(4) Uani 1 1 d . . . . .
C1 C 0.34938(19) 0.63873(15) 0.18603(16) 0.0128(4) Uani 1 1 d . . . . .
C3 C 0.18990(18) 0.59698(14) 0.24381(15) 0.0109(4) Uani 1 1 d . . . . .
C2 C 0.23755(19) 0.61147(14) 0.13146(17) 0.0117(4) Uani 1 1 d . . . . .
C5 C 0.27751(18) 0.64750(15) 0.46010(16) 0.0125(4) Uani 1 1 d . . . . .
C20 C 0.10211(19) 0.67125(15) 0.26747(16) 0.0135(4) Uani 1 1 d . . . . .
C18 C 0.14863(19) 0.50351(15) 0.26348(16) 0.0129(4) Uani 1 1 d . . . . .
C4 C 0.3561(2) 0.61976(13) 0.37854(17) 0.0119(4) Uani 1 1 d . . . . .
C7 C 0.1732(2) 0.76049(16) 0.54665(18) 0.0193(5) Uani 1 1 d . . . . .
H7 H 0.150129 0.818781 0.552131 0.023 Uiso 1 1 calc R . . . .
C11 C 0.4666(2) 0.60142(15) 0.39495(16) 0.0129(4) Uani 1 1 d . . . . .
C6 C 0.2431(2) 0.73489(15) 0.46797(17) 0.0151(4) Uani 1 1 d . . . . .
H6 H 0.266903 0.775970 0.420662 0.018 Uiso 1 1 calc R . . . .
C12 C 0.5519(2) 0.56632(16) 0.32079(18) 0.0172(5) Uani 1 1 d . . . . .
C9 C 0.1721(2) 0.61201(17) 0.60970(18) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.148409 0.571096 0.657241 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2436(2) 0.52804(15) 0.06727(17) 0.0152(5) Uani 1 1 d . . . . .
C10 C 0.2422(2) 0.58577(16) 0.53108(17) 0.0164(5) Uani 1 1 d . . . . .
H10 H 0.265373 0.527483 0.525938 0.020 Uiso 1 1 calc R . . . .
C15 C 0.1281(2) 0.62979(14) -0.01368(17) 0.0143(5) Uani 1 1 d . . . . .
C8 C 0.1375(2) 0.69876(18) 0.61738(18) 0.0207(5) Uani 1 1 d . . . . .
H8 H 0.090357 0.715870 0.669851 0.025 Uiso 1 1 calc R . . . .
C16 C 0.1502(2) 0.67569(17) -0.11175(17) 0.0215(5) Uani 1 1 d . . . . .
H16A H 0.121817 0.734816 -0.108532 0.032 Uiso 1 1 calc GR . . . .
H16B H 0.111791 0.644969 -0.166105 0.032 Uiso 1 1 calc GR . . . .
H16C H 0.231190 0.676701 -0.123467 0.032 Uiso 1 1 calc GR . . . .
C19 C 0.1748(2) 0.37305(16) 0.3548(2) 0.0242(6) Uani 1 1 d . . . . .
H19A H 0.179211 0.339365 0.293507 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.097526 0.372265 0.378432 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.225159 0.348004 0.405447 0.036 Uiso 1 1 calc GR . . . .
C21 C -0.0162(2) 0.64824(19) 0.2947(2) 0.0280(6) Uani 1 1 d . . . . .
H21 H -0.036285 0.585783 0.298062 0.034 Uiso 1 1 calc R . . . .
C17 C 0.0029(2) 0.62040(16) 0.01102(19) 0.0188(5) Uani 1 1 d . . . . .
H17A H -0.004722 0.582923 0.068984 0.028 Uiso 1 1 calc GR . . . .
H17B H -0.037738 0.595114 -0.045826 0.028 Uiso 1 1 calc GR . . . .
H17C H -0.028595 0.677199 0.025612 0.028 Uiso 1 1 calc GR . . . .
C22 C -0.1092(2) 0.7123(2) 0.2613(2) 0.0303(6) Uani 1 1 d . . . . .
H22A H -0.086453 0.762609 0.221419 0.036 Uiso 1 1 calc R . . . .
H22B H -0.183989 0.688327 0.243423 0.036 Uiso 1 1 calc R . . . .
C13 C 0.5765(3) 0.4728(2) 0.1814(2) 0.0331(7) Uani 1 1 d . . . . .
H13A H 0.533016 0.433740 0.138399 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.638998 0.441305 0.212800 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.606164 0.520161 0.141547 0.050 Uiso 1 1 calc GR . . . .
C23 C -0.0739(3) 0.7105(3) 0.3679(2) 0.0407(8) Uani 1 1 d . . . . .
H23A H -0.126826 0.685427 0.415758 0.049 Uiso 1 1 calc R . . . .
H23B H -0.029273 0.759723 0.393750 0.049 Uiso 1 1 calc R . . . .


_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 1.882(2) . ?
O8 C18 1.317(3) . ?
O8 C19 1.459(3) . ?
O1 C1 1.202(3) . ?
O6 C2 1.384(3) . ?
O6 C15 1.443(3) . ?
O5 C14 1.340(3) . ?
O5 C15 1.463(3) . ?
O9 C20 1.199(3) . ?
O7 C18 1.205(3) . ?
O3 C12 1.326(3) . ?
O3 C13 1.454(3) . ?
O4 C14 1.191(3) . ?
O2 C12 1.200(3) . ?
N1 C1 1.376(3) . ?
N1 C3 1.470(3) . ?
N1 C4 1.418(3) . ?
C1 C2 1.534(3) . ?
C3 C2 1.610(3) . ?
C3 C20 1.561(3) . ?
C3 C18 1.525(3) . ?
C2 C14 1.529(3) . ?
C5 C4 1.489(3) . ?
C5 C6 1.394(3) . ?
C5 C10 1.395(3) . ?
C20 C21 1.475(3) . ?
C4 C11 1.332(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.389(3) . ?
C7 C8 1.394(4) . ?
C11 C12 1.508(3) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.393(3) . ?
C9 C8 1.385(4) . ?
C10 H10 0.9300 . ?
C15 C16 1.498(3) . ?
C15 C17 1.509(3) . ?
C8 H8 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21 H21 0.9800 . ?
C21 C22 1.516(4) . ?
C21 C23 1.520(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.459(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?

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
C18 O8 C19 114.80(19) . . ?
C2 O6 C15 108.78(16) . . ?
C14 O5 C15 110.33(17) . . ?
C12 O3 C13 115.3(2) . . ?
C1 N1 C3 96.31(17) . . ?
C1 N1 C4 132.58(19) . . ?
C4 N1 C3 130.94(18) . . ?
O1 C1 N1 133.1(2) . . ?
O1 C1 C2 134.5(2) . . ?
N1 C1 C2 92.35(17) . . ?
N1 C3 C2 85.98(15) . . ?
N1 C3 C20 113.25(17) . . ?
N1 C3 C18 115.79(17) . . ?
C20 C3 C2 108.97(17) . . ?
C18 C3 C2 113.61(17) . . ?
C18 C3 C20 115.52(18) . . ?
O6 C2 C1 115.53(18) . . ?
O6 C2 C3 120.97(18) . . ?
O6 C2 C14 104.76(17) . . ?
C1 C2 C3 84.83(16) . . ?
C14 C2 C1 115.88(19) . . ?
C14 C2 C3 114.69(17) . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 C10 120.2(2) . . ?
C10 C5 C4 119.3(2) . . ?
O9 C20 C3 116.9(2) . . ?
O9 C20 C21 123.3(2) . . ?
C21 C20 C3 119.8(2) . . ?
O8 C18 C3 112.74(18) . . ?
O7 C18 O8 125.9(2) . . ?
O7 C18 C3 121.4(2) . . ?
N1 C4 C5 115.72(19) . . ?
C11 C4 N1 120.9(2) . . ?
C11 C4 C5 123.3(2) . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C4 C11 Br1 119.44(17) . . ?
C4 C11 C12 128.1(2) . . ?
C12 C11 Br1 112.43(16) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.8(2) . . ?
C7 C6 H6 120.1 . . ?
O3 C12 C11 110.72(19) . . ?
O2 C12 O3 125.5(2) . . ?
O2 C12 C11 123.7(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(2) . . ?
O5 C14 C2 107.00(19) . . ?
O4 C14 O5 125.0(2) . . ?
O4 C14 C2 128.0(2) . . ?
C5 C10 H10 120.2 . . ?
C9 C10 C5 119.5(2) . . ?
C9 C10 H10 120.2 . . ?
O6 C15 O5 103.90(17) . . ?
O6 C15 C16 109.43(18) . . ?
O6 C15 C17 110.61(18) . . ?
O5 C15 C16 107.95(19) . . ?
O5 C15 C17 109.89(18) . . ?
C16 C15 C17 114.5(2) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 119.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O8 C19 H19A 109.5 . . ?
O8 C19 H19B 109.5 . . ?
O8 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C21 H21 117.8 . . ?
C20 C21 C22 116.3(2) . . ?
C20 C21 C23 115.8(3) . . ?
C22 C21 H21 117.8 . . ?
C22 C21 C23 57.43(19) . . ?
C23 C21 H21 117.8 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C22 H22A 117.6 . . ?
C21 C22 H22B 117.6 . . ?
H22A C22 H22B 114.7 . . ?
C23 C22 C21 61.4(2) . . ?
C23 C22 H22A 117.6 . . ?
C23 C22 H22B 117.6 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C21 C23 H23A 117.7 . . ?
C21 C23 H23B 117.7 . . ?
C22 C23 C21 61.2(2) . . ?
C22 C23 H23A 117.7 . . ?
C22 C23 H23B 117.7 . . ?
H23A C23 H23B 114.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C11 C12 O3 143.14(16) . . . . ?
Br1 C11 C12 O2 -34.4(3) . . . . ?
O1 C1 C2 O6 -51.3(4) . . . . ?
O1 C1 C2 C3 -173.3(3) . . . . ?
O1 C1 C2 C14 71.8(3) . . . . ?
O6 C2 C14 O5 -11.2(2) . . . . ?
O6 C2 C14 O4 168.1(2) . . . . ?
O9 C20 C21 C22 30.7(4) . . . . ?
O9 C20 C21 C23 -34.0(4) . . . . ?
N1 C1 C2 O6 127.32(19) . . . . ?
N1 C1 C2 C3 5.35(16) . . . . ?
N1 C1 C2 C14 -109.6(2) . . . . ?
N1 C3 C2 O6 -121.8(2) . . . . ?
N1 C3 C2 C1 -5.02(15) . . . . ?
N1 C3 C2 C14 111.1(2) . . . . ?
N1 C3 C20 O9 37.9(3) . . . . ?
N1 C3 C20 C21 -144.0(2) . . . . ?
N1 C3 C18 O8 19.4(3) . . . . ?
N1 C3 C18 O7 -161.0(2) . . . . ?
N1 C4 C11 Br1 171.49(15) . . . . ?
N1 C4 C11 C12 -7.7(4) . . . . ?
C1 N1 C3 C2 5.61(16) . . . . ?
C1 N1 C3 C20 -103.32(19) . . . . ?
C1 N1 C3 C18 119.94(19) . . . . ?
C1 N1 C4 C5 142.0(2) . . . . ?
C1 N1 C4 C11 -35.6(3) . . . . ?
C1 C2 C14 O5 -139.72(19) . . . . ?
C1 C2 C14 O4 39.5(3) . . . . ?
C3 N1 C1 O1 172.8(3) . . . . ?
C3 N1 C1 C2 -5.87(17) . . . . ?
C3 N1 C4 C5 -32.2(3) . . . . ?
C3 N1 C4 C11 150.2(2) . . . . ?
C3 C2 C14 O5 123.80(19) . . . . ?
C3 C2 C14 O4 -57.0(3) . . . . ?
C3 C20 C21 C22 -147.3(2) . . . . ?
C3 C20 C21 C23 148.0(2) . . . . ?
C2 O6 C15 O5 -23.3(2) . . . . ?
C2 O6 C15 C16 -138.4(2) . . . . ?
C2 O6 C15 C17 94.6(2) . . . . ?
C2 C3 C20 O9 -56.0(2) . . . . ?
C2 C3 C20 C21 122.2(2) . . . . ?
C2 C3 C18 O8 116.6(2) . . . . ?
C2 C3 C18 O7 -63.7(3) . . . . ?
C5 C4 C11 Br1 -5.9(3) . . . . ?
C5 C4 C11 C12 174.9(2) . . . . ?
C20 C3 C2 O6 -8.6(3) . . . . ?
C20 C3 C2 C1 108.20(18) . . . . ?
C20 C3 C2 C14 -135.6(2) . . . . ?
C20 C3 C18 O8 -116.4(2) . . . . ?
C20 C3 C18 O7 63.3(3) . . . . ?
C20 C21 C22 C23 -105.0(3) . . . . ?
C20 C21 C23 C22 106.0(3) . . . . ?
C18 C3 C2 O6 121.8(2) . . . . ?
C18 C3 C2 C1 -121.46(18) . . . . ?
C18 C3 C2 C14 -5.3(3) . . . . ?
C18 C3 C20 O9 174.75(19) . . . . ?
C18 C3 C20 C21 -7.1(3) . . . . ?
C4 N1 C1 O1 -2.8(4) . . . . ?
C4 N1 C1 C2 178.6(2) . . . . ?
C4 N1 C3 C2 -178.7(2) . . . . ?
C4 N1 C3 C20 72.3(3) . . . . ?
C4 N1 C3 C18 -64.4(3) . . . . ?
C4 C5 C6 C7 -177.6(2) . . . . ?
C4 C5 C10 C9 177.7(2) . . . . ?
C4 C11 C12 O3 -37.6(3) . . . . ?
C4 C11 C12 O2 144.9(3) . . . . ?
C6 C5 C4 N1 -72.4(3) . . . . ?
C6 C5 C4 C11 105.2(3) . . . . ?
C6 C5 C10 C9 0.2(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C14 O5 C15 O6 15.9(2) . . . . ?
C14 O5 C15 C16 132.0(2) . . . . ?
C14 O5 C15 C17 -102.5(2) . . . . ?
C10 C5 C4 N1 110.2(2) . . . . ?
C10 C5 C4 C11 -72.3(3) . . . . ?
C10 C5 C6 C7 -0.2(3) . . . . ?
C10 C9 C8 C7 -0.3(4) . . . . ?
C15 O6 C2 C1 150.10(18) . . . . ?
C15 O6 C2 C3 -110.1(2) . . . . ?
C15 O6 C2 C14 21.3(2) . . . . ?
C15 O5 C14 O4 177.4(2) . . . . ?
C15 O5 C14 C2 -3.3(2) . . . . ?
C8 C7 C6 C5 -0.1(4) . . . . ?
C8 C9 C10 C5 0.1(4) . . . . ?
C19 O8 C18 O7 1.9(3) . . . . ?
C19 O8 C18 C3 -178.52(19) . . . . ?
C13 O3 C12 O2 -5.1(4) . . . . ?
C13 O3 C12 C11 177.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.683
_oxdiff_exptl_absorpt_empirical_full_min 0.697
