# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_sj_05
_database_code_depnum_ccdc_archive 'CCDC 2528101'
loop_
_audit_author_name
_audit_author_address
shanjing
;Zunyi Medical University
China
;
_audit_update_record             
;
2026-02-03 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2025-03-21
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 Br N2 O5'
_chemical_formula_sum            'C26 H23 Br N2 O5'
_chemical_formula_weight         523.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.13710(10)
_cell_length_b                   12.75540(10)
_cell_length_c                   14.93530(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2312.19(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19521
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.5130
_cell_measurement_theta_min      3.6210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.771
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.690
_diffrn_reflns_theta_min         4.559
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00 -29.00   0.50    0.05    -- -103.00  77.00 -60.00   86
  2  ω    -15.00  34.00   0.50    0.05    --  -43.18  38.00   0.00   98
  3  ω    -15.00  34.00   0.50    0.05    --  -43.18  38.00 -30.00   98
  4  ω    -13.00  35.00   0.50    0.05    --  -43.18  36.00-120.00   96
  5  ω    -92.00 -30.00   0.50    0.05    -- -103.00  98.00 -11.00  124
  6  ω    -92.00 -29.00   0.50    0.05    -- -103.00 100.00  84.00  126
  7  ω   -101.00 -30.00   0.50    0.05    -- -103.00 126.00 150.00  142
  8  ω    -76.00   6.00   0.50    0.05    --  -43.18 100.00  84.00  164
  9  ω     33.00  92.00   0.50    0.05    --  107.26 -95.00-180.00  118
 10  ω     34.00  93.00   0.50    0.05    --  107.26 -98.00-118.00  118
 11  ω     35.00 101.00   0.50    0.05    --  107.26-126.00 150.00  132
 12  ω     35.00 101.00   0.50    0.05    --  107.26-126.00 150.00  132
 13  ω     35.00 101.00   0.50    0.05    --  107.26-126.00  60.00  132
 14  ω     35.00 101.00   0.50    0.05    --  107.26-126.00  30.00  132
 15  ω     33.00  78.00   0.50    0.05    --  107.26 -77.00 -30.00   90
 16  ω    -34.00  22.00   0.50    0.05    --   43.18 -38.00  30.00  112
 17  ω    -34.00  22.00   0.50    0.05    --   43.18 -38.00 -30.00  112
 18  ω     33.00  78.00   0.50    0.05    --  107.26 -77.00-120.00   90
 19  ω     92.00 139.00   0.50    0.05    --  107.26  15.00-150.00   94
 20  ω     94.00 175.00   0.50    0.05    --  107.26 126.00 -90.00  162
 21  ω     94.00 175.00   0.50    0.05    --  107.26 126.00 -90.00  162
 22  ω    106.00 175.00   0.50    0.05    --  107.26  77.00-180.00  138
 23  ω   -174.00 -99.00   0.50    0.05    -- -103.00 -77.00 -60.00  150
 24  ω   -120.00 -29.00   0.50    0.05    --  -43.18 -38.00 -60.00  182
 25  ω   -169.00 -89.00   0.50    0.05    -- -103.00 -36.00  83.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1026512000
_diffrn_orient_matrix_UB_12      0.0524507000
_diffrn_orient_matrix_UB_13      0.0409527000
_diffrn_orient_matrix_UB_21      0.0631950000
_diffrn_orient_matrix_UB_22      -0.0175953000
_diffrn_orient_matrix_UB_23      -0.0882252000
_diffrn_orient_matrix_UB_31      -0.0398025000
_diffrn_orient_matrix_UB_32      0.1073287000
_diffrn_orient_matrix_UB_33      -0.0343723000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                4599
_reflns_number_total             4616
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0170
_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)+(0.0286P)²+0.6268P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0454
_refine_ls_wR_factor_ref         0.0455
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19), C29(H29)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.71380(2) 1.14543(2) 0.58573(2) 0.02088(6) Uani 1 1 d . . . . .
O1 O 0.62607(13) 0.57877(11) 0.73789(10) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.79317(14) 0.76966(11) 0.43545(10) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.80487(12) 0.61272(10) 0.36685(9) 0.0224(3) Uani 1 1 d . . . . .
O4 O 0.55446(11) 0.64561(12) 0.37223(9) 0.0228(3) Uani 1 1 d . . . . .
O5 O 0.71414(14) 0.37553(10) 0.52798(10) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.62872(14) 0.74741(13) 0.79275(11) 0.0188(3) Uani 1 1 d . . . . .
N2 N 0.64883(13) 0.53136(12) 0.46435(10) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.65194(14) 0.84872(16) 0.75853(12) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.63679(17) 0.94652(16) 0.79770(13) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.65829(16) 1.03334(15) 0.74338(13) 0.0190(4) Uani 1 1 d . . . . .
H3 H 0.648048 1.101775 0.767060 0.023 Uiso 1 1 calc R U . . .
C4 C 0.69427(15) 1.02207(15) 0.65557(12) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.71355(17) 0.92402(14) 0.61787(12) 0.0177(3) Uani 1 1 d . . . . .
H5 H 0.740967 0.916784 0.558609 0.021 Uiso 1 1 calc R U . . .
C6 C 0.69102(14) 0.83787(15) 0.67050(12) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.69672(16) 0.72364(14) 0.64605(12) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.64673(17) 0.67180(15) 0.72886(13) 0.0198(4) Uani 1 1 d . . . . .
C9 C 0.81512(15) 0.68071(15) 0.63293(13) 0.0199(4) Uani 1 1 d . . . . .
H9A H 0.861689 0.731989 0.600618 0.024 Uiso 1 1 calc R U . . .
H9B H 0.849832 0.664396 0.691268 0.024 Uiso 1 1 calc R U . . .
C10 C 0.79891(16) 0.58103(14) 0.57731(13) 0.0190(4) Uani 1 1 d . . . . .
H10 H 0.762637 0.527907 0.616753 0.023 Uiso 1 1 calc R U . . .
C11 C 0.63497(16) 0.69150(15) 0.55946(12) 0.0184(4) Uani 1 1 d . . . . .
H11A H 0.617462 0.754308 0.523212 0.022 Uiso 1 1 calc R U . . .
H11B H 0.565205 0.655409 0.574601 0.022 Uiso 1 1 calc R U . . .
C12 C 0.71184(17) 0.61688(13) 0.50634(12) 0.0169(3) Uani 1 1 d . . . . .
C13 C 0.77269(16) 0.67738(15) 0.43213(13) 0.0200(4) Uani 1 1 d . . . . .
C14 C 0.65756(17) 0.42174(15) 0.47451(12) 0.0190(4) Uani 1 1 d . . . . .
C15 C 0.58105(15) 0.37600(14) 0.40704(13) 0.0191(4) Uani 1 1 d . . . . .
C16 C 0.55757(18) 0.27151(16) 0.38915(14) 0.0235(4) Uani 1 1 d . . . . .
H16 H 0.591148 0.216365 0.422056 0.028 Uiso 1 1 calc R U . . .
C17 C 0.48241(18) 0.25125(17) 0.32064(15) 0.0245(4) Uani 1 1 d . . . . .
H17 H 0.464156 0.180745 0.306501 0.029 Uiso 1 1 calc R U . . .
C18 C 0.43375(16) 0.33231(17) 0.27271(13) 0.0240(4) Uani 1 1 d . . . . .
H18 H 0.383026 0.316040 0.226300 0.029 Uiso 1 1 calc R U . . .
C19 C 0.45767(17) 0.43693(17) 0.29117(13) 0.0213(4) Uani 1 1 d . . . . .
H19 H 0.424460 0.492420 0.258440 0.026 Uiso 1 1 calc R U . . .
C20 C 0.53197(16) 0.45619(15) 0.35933(13) 0.0179(4) Uani 1 1 d . . . . .
C21 C 0.57491(16) 0.55695(15) 0.39506(12) 0.0171(4) Uani 1 1 d . . . . .
C22 C 0.8696(2) 0.65966(17) 0.29619(16) 0.0326(5) Uani 1 1 d . . . . .
H22A H 0.822318 0.704876 0.259584 0.049 Uiso 1 1 calc R U . . .
H22B H 0.901239 0.604375 0.258600 0.049 Uiso 1 1 calc R U . . .
H22C H 0.929003 0.701570 0.322489 0.049 Uiso 1 1 calc R U . . .
C23 C 0.59372(19) 0.96661(17) 0.89128(13) 0.0250(4) Uani 1 1 d . . . . .
H23A H 0.606766 1.040024 0.907448 0.038 Uiso 1 1 calc R U . . .
H23B H 0.632023 0.920807 0.933783 0.038 Uiso 1 1 calc R U . . .
H23C H 0.514483 0.951983 0.893177 0.038 Uiso 1 1 calc R U . . .
C24 C 0.5817(2) 0.72078(18) 0.87963(14) 0.0274(5) Uani 1 1 d . . . . .
H24A H 0.634657 0.737927 0.926958 0.041 Uiso 1 1 calc R U . . .
H24B H 0.565077 0.645628 0.881456 0.041 Uiso 1 1 calc R U . . .
H24C H 0.513786 0.760881 0.888896 0.041 Uiso 1 1 calc R U . . .
C29 C 0.90280(18) 0.53238(16) 0.54137(15) 0.0255(4) Uani 1 1 d . . . . .
H29 H 0.894884 0.470153 0.507017 0.031 Uiso 1 1 calc R U . . .
C30 C 1.00331(19) 0.56774(18) 0.55297(15) 0.0281(4) Uani 1 1 d . . . . .
H30A H 1.022(2) 0.634(2) 0.5896(18) 0.031(6) Uiso 1 1 d . . . . .
H30B H 1.071(2) 0.529(2) 0.5279(19) 0.037(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.9026(18) . ?
O1 C8 1.220(2) . ?
O2 C13 1.204(2) . ?
O3 C13 1.335(2) . ?
O3 C22 1.445(2) . ?
O4 C21 1.207(2) . ?
O5 C14 1.207(2) . ?
N1 C1 1.418(2) . ?
N1 C8 1.374(3) . ?
N1 C24 1.458(3) . ?
N2 C12 1.472(2) . ?
N2 C14 1.410(2) . ?
N2 C21 1.408(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.404(2) . ?
C2 C3 1.397(3) . ?
C2 C23 1.514(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 C5 1.391(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(3) . ?
C6 C7 1.504(2) . ?
C7 C8 1.528(3) . ?
C7 C9 1.550(3) . ?
C7 C11 1.550(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.531(2) . ?
C10 H10 1.0000 . ?
C10 C12 1.565(3) . ?
C10 C29 1.504(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.551(3) . ?
C12 C13 1.539(3) . ?
C14 C15 1.489(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.395(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.382(3) . ?
C20 C21 1.486(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C29 H29 0.9500 . ?
C29 C30 1.312(3) . ?
C30 H30A 1.03(3) . ?
C30 H30B 1.03(3) . ?

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
C13 O3 C22 115.85(15) . . ?
C1 N1 C24 127.67(16) . . ?
C8 N1 C1 110.96(15) . . ?
C8 N1 C24 121.12(16) . . ?
C14 N2 C12 130.51(16) . . ?
C21 N2 C12 118.18(15) . . ?
C21 N2 C14 110.91(15) . . ?
C2 C1 N1 129.79(16) . . ?
C2 C1 C6 121.80(18) . . ?
C6 C1 N1 108.35(16) . . ?
C1 C2 C3 116.25(17) . . ?
C1 C2 C23 125.87(18) . . ?
C3 C2 C23 117.80(18) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.64(18) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 Br1 118.10(14) . . ?
C3 C4 C5 121.85(17) . . ?
C5 C4 Br1 120.03(14) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.89(16) . . ?
C6 C5 H5 121.6 . . ?
C1 C6 C7 109.78(16) . . ?
C5 C6 C1 121.49(17) . . ?
C5 C6 C7 128.66(17) . . ?
C6 C7 C8 101.79(15) . . ?
C6 C7 C9 114.56(15) . . ?
C6 C7 C11 115.90(15) . . ?
C8 C7 C9 108.51(15) . . ?
C8 C7 C11 111.65(16) . . ?
C11 C7 C9 104.44(15) . . ?
O1 C8 N1 124.96(19) . . ?
O1 C8 C7 126.28(18) . . ?
N1 C8 C7 108.76(16) . . ?
C7 C9 H9A 110.9 . . ?
C7 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 C7 104.05(15) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 H10 107.4 . . ?
C9 C10 C12 102.21(14) . . ?
C12 C10 H10 107.4 . . ?
C29 C10 C9 115.36(16) . . ?
C29 C10 H10 107.4 . . ?
C29 C10 C12 116.41(16) . . ?
C7 C11 H11A 110.2 . . ?
C7 C11 H11B 110.2 . . ?
C7 C11 C12 107.35(15) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
N2 C12 C10 115.01(14) . . ?
N2 C12 C11 111.10(16) . . ?
N2 C12 C13 108.30(14) . . ?
C11 C12 C10 103.83(14) . . ?
C13 C12 C10 108.07(16) . . ?
C13 C12 C11 110.44(15) . . ?
O2 C13 O3 125.00(18) . . ?
O2 C13 C12 124.02(17) . . ?
O3 C13 C12 110.87(15) . . ?
O5 C14 N2 126.73(18) . . ?
O5 C14 C15 127.67(17) . . ?
N2 C14 C15 105.59(16) . . ?
C16 C15 C14 129.36(18) . . ?
C20 C15 C14 109.13(16) . . ?
C20 C15 C16 121.51(19) . . ?
C15 C16 H16 121.5 . . ?
C15 C16 C17 116.9(2) . . ?
C17 C16 H16 121.5 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.20(19) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.48(19) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 H19 121.6 . . ?
C20 C19 C18 116.88(19) . . ?
C20 C19 H19 121.6 . . ?
C15 C20 C19 121.98(18) . . ?
C15 C20 C21 107.69(16) . . ?
C19 C20 C21 130.33(18) . . ?
O4 C21 N2 123.78(17) . . ?
O4 C21 C20 129.55(17) . . ?
N2 C21 C20 106.67(15) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 C23 H23A 109.5 . . ?
C2 C23 H23B 109.5 . . ?
C2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 C29 H29 116.9 . . ?
C30 C29 C10 126.18(19) . . ?
C30 C29 H29 116.9 . . ?
C29 C30 H30A 124.1(14) . . ?
C29 C30 H30B 121.6(16) . . ?
H30A C30 H30B 114(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 -175.97(14) . . . . ?
O5 C14 C15 C16 -0.7(4) . . . . ?
O5 C14 C15 C20 179.8(2) . . . . ?
N1 C1 C2 C3 -174.17(19) . . . . ?
N1 C1 C2 C23 2.4(3) . . . . ?
N1 C1 C6 C5 175.63(17) . . . . ?
N1 C1 C6 C7 -1.5(2) . . . . ?
N2 C12 C13 O2 148.83(19) . . . . ?
N2 C12 C13 O3 -34.8(2) . . . . ?
N2 C14 C15 C16 -179.5(2) . . . . ?
N2 C14 C15 C20 0.9(2) . . . . ?
C1 N1 C8 O1 -174.6(2) . . . . ?
C1 N1 C8 C7 5.6(2) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C6 C7 C8 4.52(19) . . . . ?
C1 C6 C7 C9 -112.36(17) . . . . ?
C1 C6 C7 C11 125.87(17) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C1 C6 C7 -178.86(17) . . . . ?
C2 C3 C4 Br1 176.84(15) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 C6 2.6(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 175.67(18) . . . . ?
C5 C6 C7 C8 -172.37(19) . . . . ?
C5 C6 C7 C9 70.8(2) . . . . ?
C5 C6 C7 C11 -51.0(3) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C6 C1 C2 C23 179.08(18) . . . . ?
C6 C7 C8 O1 174.1(2) . . . . ?
C6 C7 C8 N1 -6.1(2) . . . . ?
C6 C7 C9 C10 -160.06(15) . . . . ?
C6 C7 C11 C12 135.87(16) . . . . ?
C7 C9 C10 C12 42.88(18) . . . . ?
C7 C9 C10 C29 170.19(17) . . . . ?
C7 C11 C12 N2 141.31(15) . . . . ?
C7 C11 C12 C10 17.15(19) . . . . ?
C7 C11 C12 C13 -98.49(17) . . . . ?
C8 N1 C1 C2 174.42(19) . . . . ?
C8 N1 C1 C6 -2.6(2) . . . . ?
C8 C7 C9 C10 86.99(18) . . . . ?
C8 C7 C11 C12 -108.21(17) . . . . ?
C9 C7 C8 O1 -64.7(3) . . . . ?
C9 C7 C8 N1 115.11(17) . . . . ?
C9 C7 C11 C12 8.85(19) . . . . ?
C9 C10 C12 N2 -158.37(16) . . . . ?
C9 C10 C12 C11 -36.77(18) . . . . ?
C9 C10 C12 C13 80.52(17) . . . . ?
C9 C10 C29 C30 -0.4(3) . . . . ?
C10 C12 C13 O2 -86.0(2) . . . . ?
C10 C12 C13 O3 90.39(18) . . . . ?
C11 C7 C8 O1 49.9(3) . . . . ?
C11 C7 C8 N1 -130.32(17) . . . . ?
C11 C7 C9 C10 -32.22(18) . . . . ?
C11 C12 C13 O2 27.0(3) . . . . ?
C11 C12 C13 O3 -156.66(15) . . . . ?
C12 N2 C14 O5 7.6(3) . . . . ?
C12 N2 C14 C15 -173.54(17) . . . . ?
C12 N2 C21 O4 -5.3(3) . . . . ?
C12 N2 C21 C20 174.38(15) . . . . ?
C12 C10 C29 C30 119.3(2) . . . . ?
C14 N2 C12 C10 -3.4(3) . . . . ?
C14 N2 C12 C11 -120.9(2) . . . . ?
C14 N2 C12 C13 117.6(2) . . . . ?
C14 N2 C21 O4 -178.79(18) . . . . ?
C14 N2 C21 C20 0.9(2) . . . . ?
C14 C15 C16 C17 -179.32(19) . . . . ?
C14 C15 C20 C19 179.21(17) . . . . ?
C14 C15 C20 C21 -0.4(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C15 C20 C21 O4 179.4(2) . . . . ?
C15 C20 C21 N2 -0.3(2) . . . . ?
C16 C15 C20 C19 -0.4(3) . . . . ?
C16 C15 C20 C21 -179.96(18) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C18 C19 C20 C21 179.76(19) . . . . ?
C19 C20 C21 O4 -0.2(3) . . . . ?
C19 C20 C21 N2 -179.85(19) . . . . ?
C20 C15 C16 C17 0.2(3) . . . . ?
C21 N2 C12 C10 -175.31(16) . . . . ?
C21 N2 C12 C11 67.1(2) . . . . ?
C21 N2 C12 C13 -54.3(2) . . . . ?
C21 N2 C14 O5 179.97(19) . . . . ?
C21 N2 C14 C15 -1.1(2) . . . . ?
C22 O3 C13 O2 0.4(3) . . . . ?
C22 O3 C13 C12 -175.97(18) . . . . ?
C23 C2 C3 C4 -177.71(18) . . . . ?
C24 N1 C1 C2 0.2(3) . . . . ?
C24 N1 C1 C6 -176.84(19) . . . . ?
C24 N1 C8 O1 0.0(3) . . . . ?
C24 N1 C8 C7 -179.75(18) . . . . ?
C29 C10 C12 N2 75.0(2) . . . . ?
C29 C10 C12 C11 -163.42(16) . . . . ?
C29 C10 C12 C13 -46.1(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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.841

# start Validation Reply Form
_vrf_PLAT431_sj_05               
;
PROBLEM: Short Inter HL..A Contact  Br1      ..O5       .       3.06 Ang.  
RESPONSE: No intermolecular hydrogen bonds were observed between Br and
 O5 in this crystal structure. O5 is located on the carbon base, not the hydroxyl group.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_sj_03
_database_code_depnum_ccdc_archive 'CCDC 2528103'
loop_
_audit_author_name
_audit_author_address
shanjing
;Zunyi Medical University
China
;
_audit_update_record             
;
2026-02-03 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-26
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 Br N2 O5'
_chemical_formula_sum            'C26 H23 Br N2 O5'
_chemical_formula_weight         523.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   11.22494(5)
_cell_length_b                   11.22494(5)
_cell_length_c                   40.1510(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5059.00(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    29901
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      72.3640
_cell_measurement_theta_min      4.0660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            54525
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.213
_diffrn_reflns_theta_min         4.089
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     99.00 124.00   0.50    0.07    --  110.04 139.00  84.00   50
  2  ω    104.00 129.00   0.50    0.07    --  110.04 132.00 -90.00   50
  3  ω     62.00  91.00   0.50    0.07    --  110.04-112.00 -30.00   58
  4  ω    110.00 135.00   0.50    0.07    --  110.04 127.00   2.00   50
  5  ω     42.00  67.00   0.50    0.07    --  110.04-127.00 -73.00   50
  6  ω     23.00  49.00   0.50    0.05    --   37.08-132.00-160.00   52
  7  ω     23.00 119.00   0.50    0.05    --   37.08  19.00 -60.00  192
  8  ω     42.00  71.00   0.50    0.05    --   37.08  19.00 -30.00   58
  9  ω      8.00  36.00   0.50    0.05    --   37.08  70.00 -66.57   56
 10  ω      7.00  32.00   0.50    0.05    --   37.08  72.00  17.20   50
 11  ω    -53.00  -9.00   0.50    0.05    --  -37.08 -38.00 150.00   88
 12  ω    -55.00 -11.00   0.50    0.05    --  -37.08 -57.00 120.00   88
 13  ω    -56.00 -31.00   0.50    0.05    --  -37.08 -57.00  60.00   50
 14  ω    -56.00 -13.00   0.50    0.05    --  -37.08 -57.00   0.00   86
 15  ω    -42.00 -16.00   0.50    0.05    --  -37.08 -57.00-120.00   52
 16  ω    -92.00 -67.00   0.50    0.07    -- -103.00  96.00 -38.68   50
 17  ω    -61.00 -35.00   0.50    0.07    -- -103.00  96.00 -38.68   52
 18  ω   -103.00 -49.00   0.50    0.07    -- -103.00 132.00 -90.00  108
 19  ω    -93.00 -23.00   0.50    0.07    -- -103.00 101.00 -76.43  140
 20  ω    -87.00 -62.00   0.50    0.07    -- -103.00 127.00   2.00   50
 21  ω    -91.00 -66.00   0.50    0.07    -- -103.00 139.00  84.00   50
 22  ω    -71.00 -25.00   0.50    0.07    -- -103.00  77.00 120.00   92
 23  ω    -72.00 -24.00   0.50    0.07    -- -103.00  77.00  90.00   96
 24  ω    -97.00 -24.00   0.50    0.05    --  -37.08 139.00  84.00  146
 25  ω    -81.00 -56.00   0.50    0.05    --  -37.08 132.00 -90.00   50
 26  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -46.00 -43.24   52
 27  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -54.00 -49.95   52
 28  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -54.00 -56.61   52
 29  ω   -118.00 -75.00   0.50    0.07    -- -103.00 -54.00 -63.35   86
 30  ω   -158.00-132.00   0.50    0.07    -- -103.00 -54.00 -36.39   52
 31  ω   -174.00 -76.00   0.50    0.07    -- -103.00 -54.00 -94.04  196
 32  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -54.00-105.66   52
 33  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -53.00-101.01   50
 34  ω   -105.00 -79.00   0.50    0.07    -- -103.00 -56.00-120.72   52
 35  ω   -103.00 -77.00   0.50    0.07    -- -103.00 -54.00 -36.39   52
 36  ω   -172.00 -74.00   0.50    0.07    -- -103.00 -53.00 -73.92  196
 37  ω   -153.00 -76.00   0.50    0.07    -- -103.00 -53.00 -67.32  154
 38  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -53.00 -29.55   50
 39  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -53.00 -79.37   50
 40  ω   -171.00 -74.00   0.50    0.07    -- -103.00 -53.00 -87.69  194
 41  ω   -163.00-137.00   0.50    0.07    -- -103.00 -53.00-101.01   52
 42  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -52.00 -84.10   50
 43  ω   -100.00 -74.00   0.50    0.07    -- -103.00 -52.00-120.01   52
 44  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -52.00 -63.09   50
 45  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -52.00 -93.88   50
 46  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -52.00 -44.80   50
 47  ω   -102.00 -75.00   0.50    0.07    -- -103.00 -51.00 -52.11   54
 48  ω   -154.00 -74.00   0.50    0.07    -- -103.00 -52.00 -56.33  160
 49  ω   -173.00-148.00   0.50    0.07    -- -103.00 -52.00 -44.80   50
 50  ω   -163.00-108.00   0.50    0.07    -- -103.00 -51.00 -52.11  110
 51  ω   -100.00 -74.00   0.50    0.07    -- -103.00 -49.00 -26.31   52
 52  ω    -99.00 -74.00   0.50    0.07    -- -103.00 -50.00 -28.37   50
 53  ω   -100.00 -74.00   0.50    0.07    -- -103.00 -47.00 -35.51   52
 54  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -50.00 -36.20   52
 55  ω   -101.00 -74.00   0.50    0.07    -- -103.00 -49.00 -51.96   54
 56  ω   -111.00 -74.00   0.50    0.07    -- -103.00 -47.00 -66.10   74
 57  ω   -101.00 -75.00   0.50    0.07    -- -103.00 -50.00 -93.67   52
 58  ω   -100.00 -74.00   0.50    0.07    -- -103.00 -50.00-119.94   52
 59  ω   -144.00-119.00   0.50    0.07    -- -103.00-139.00  24.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0801901000
_diffrn_orient_matrix_UB_12      -0.1112499000
_diffrn_orient_matrix_UB_13      -0.0014478000
_diffrn_orient_matrix_UB_21      -0.1113423000
_diffrn_orient_matrix_UB_22      0.0798512000
_diffrn_orient_matrix_UB_23      0.0022611000
_diffrn_orient_matrix_UB_31      -0.0035916000
_diffrn_orient_matrix_UB_32      0.0089120000
_diffrn_orient_matrix_UB_33      -0.0382745000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4611
_reflns_number_total             4812
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.121a 64-bit (release 24-04-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.021
_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)+(0.0486P)²+0.9665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0794
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.23420(3) 0.69738(3) 0.53948(2) 0.07305(13) Uani 1 1 d . . . . .
O1 O 0.6948(2) 0.2019(2) 0.56355(8) 0.0913(8) Uani 1 1 d . . . . .
O2 O 0.5696(2) -0.0469(2) 0.59056(6) 0.0759(6) Uani 1 1 d . . . . .
O3 O 0.5038(2) 0.05753(19) 0.63438(5) 0.0636(5) Uani 1 1 d . . . . .
O4 O 0.3299(2) -0.1115(2) 0.61480(7) 0.0770(7) Uani 1 1 d . . . . .
O5 O 0.1944(2) 0.23382(18) 0.56732(6) 0.0690(6) Uani 1 1 d . . . . .
N1 N 0.6791(2) 0.4035(3) 0.55587(7) 0.0657(6) Uani 1 1 d . . . . .
N2 N 0.2958(2) 0.07522(19) 0.59158(6) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.5865(3) 0.4878(3) 0.55258(7) 0.0548(6) Uani 1 1 d . . . . .
C2 C 0.5928(3) 0.6117(3) 0.54872(8) 0.0622(7) Uani 1 1 d . . . . .
C3 C 0.4852(3) 0.6704(3) 0.54542(8) 0.0633(8) Uani 1 1 d . . . . .
H3 H 0.485151 0.752688 0.542771 0.076 Uiso 1 1 calc R U . . .
C4 C 0.3779(3) 0.6107(2) 0.54594(7) 0.0556(6) Uani 1 1 d . . . . .
C5 C 0.3718(3) 0.4881(2) 0.55086(7) 0.0513(6) Uani 1 1 d . . . . .
H5 H 0.299187 0.448371 0.551780 0.062 Uiso 1 1 calc R U . . .
C6 C 0.4773(2) 0.4288(2) 0.55427(7) 0.0517(6) Uani 1 1 d . . . . .
C7 C 0.4979(3) 0.2968(3) 0.55865(7) 0.0547(6) Uani 1 1 d . . . . .
C8 C 0.6350(3) 0.2916(3) 0.55938(8) 0.0654(7) Uani 1 1 d . . . . .
C9 C 0.4463(3) 0.2197(3) 0.53055(7) 0.0557(6) Uani 1 1 d . . . . .
H9A H 0.366612 0.245953 0.524750 0.067 Uiso 1 1 calc R U . . .
H9B H 0.496194 0.224031 0.510861 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4437(3) 0.0935(2) 0.54424(7) 0.0556(6) Uani 1 1 d . . . . .
H10 H 0.524304 0.061075 0.541810 0.067 Uiso 1 1 calc R U . . .
C11 C 0.4454(3) 0.2413(2) 0.59048(7) 0.0546(6) Uani 1 1 d . . . . .
H11A H 0.372399 0.281798 0.596720 0.066 Uiso 1 1 calc R U . . .
H11B H 0.501625 0.247907 0.608745 0.066 Uiso 1 1 calc R U . . .
C12 C 0.4199(3) 0.1078(2) 0.58248(7) 0.0500(6) Uani 1 1 d . . . . .
C13 C 0.5058(3) 0.0276(3) 0.60221(8) 0.0560(6) Uani 1 1 d . . . . .
C14 C 0.5771(4) -0.0136(4) 0.65608(10) 0.0829(11) Uani 1 1 d . . . . .
H14A H 0.655012 -0.022138 0.646505 0.124 Uiso 1 1 calc R U . . .
H14B H 0.541675 -0.090794 0.658837 0.124 Uiso 1 1 calc R U . . .
H14C H 0.583539 0.024760 0.677380 0.124 Uiso 1 1 calc R U . . .
C15 C 0.3610(3) 0.0087(3) 0.52751(8) 0.0667(8) Uani 1 1 d . . . . .
H15 H 0.358463 -0.067942 0.536312 0.080 Uiso 1 1 calc R U . . .
C16 C 0.2921(4) 0.0285(4) 0.50220(10) 0.0854(11) Uani 1 1 d . . . . .
H16A H 0.291(4) 0.100(4) 0.4900(9) 0.086(13) Uiso 1 1 d . . . . .
H16B H 0.239(5) -0.030(4) 0.4907(10) 0.104(14) Uiso 1 1 d . . . . .
C17 C 0.1938(3) 0.1387(2) 0.58129(7) 0.0527(6) Uani 1 1 d . . . . .
C18 C 0.0893(3) 0.0650(3) 0.59047(7) 0.0534(6) Uani 1 1 d . . . . .
C19 C -0.0304(3) 0.0856(3) 0.58580(8) 0.0664(8) Uani 1 1 d . . . . .
H19 H -0.057305 0.155458 0.575852 0.080 Uiso 1 1 calc R U . . .
C20 C -0.1098(3) -0.0018(4) 0.59651(9) 0.0764(9) Uani 1 1 d . . . . .
H20 H -0.191255 0.009246 0.593616 0.092 Uiso 1 1 calc R U . . .
C21 C -0.0684(3) -0.1050(4) 0.61142(9) 0.0765(10) Uani 1 1 d . . . . .
H21 H -0.122938 -0.161623 0.618768 0.092 Uiso 1 1 calc R U . . .
C22 C 0.0517(3) -0.1260(3) 0.61565(8) 0.0671(8) Uani 1 1 d . . . . .
H22 H 0.079023 -0.195998 0.625390 0.081 Uiso 1 1 calc R U . . .
C23 C 0.1302(3) -0.0391(3) 0.60488(7) 0.0540(6) Uani 1 1 d . . . . .
C24 C 0.2620(3) -0.0359(2) 0.60518(7) 0.0537(6) Uani 1 1 d . . . . .
C25 C 0.7063(4) 0.6845(4) 0.54910(13) 0.0960(13) Uani 1 1 d . . . . .
H25A H 0.746548 0.673097 0.569944 0.144 Uiso 1 1 calc R U . . .
H25B H 0.687134 0.767284 0.546381 0.144 Uiso 1 1 calc R U . . .
H25C H 0.757067 0.659272 0.531203 0.144 Uiso 1 1 calc R U . . .
C26 C 0.8064(3) 0.4242(4) 0.55396(12) 0.0898(12) Uani 1 1 d . . . . .
H26A H 0.827080 0.448356 0.531762 0.135 Uiso 1 1 calc R U . . .
H26B H 0.848085 0.352189 0.559460 0.135 Uiso 1 1 calc R U . . .
H26C H 0.828229 0.485803 0.569375 0.135 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.902(3) . ?
O1 C8 1.222(4) . ?
O2 C13 1.196(4) . ?
O3 C13 1.335(4) . ?
O3 C14 1.440(4) . ?
O4 C24 1.204(4) . ?
O5 C17 1.206(3) . ?
N1 C1 1.412(4) . ?
N1 C8 1.357(4) . ?
N1 C26 1.449(4) . ?
N2 C12 1.486(4) . ?
N2 C17 1.410(3) . ?
N2 C24 1.413(3) . ?
C1 C2 1.401(4) . ?
C1 C6 1.395(4) . ?
C2 C3 1.382(5) . ?
C2 C25 1.513(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(5) . ?
C4 C5 1.392(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(4) . ?
C6 C7 1.510(4) . ?
C7 C8 1.541(4) . ?
C7 C9 1.536(4) . ?
C7 C11 1.539(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.519(4) . ?
C10 H10 0.9800 . ?
C10 C12 1.567(4) . ?
C10 C15 1.490(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.559(4) . ?
C12 C13 1.539(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.296(5) . ?
C16 H16A 0.94(4) . ?
C16 H16B 1.00(5) . ?
C17 C18 1.483(4) . ?
C18 C19 1.376(4) . ?
C18 C23 1.382(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.380(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.383(4) . ?
C23 C24 1.480(4) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
C13 O3 C14 115.9(3) . . ?
C1 N1 C26 127.8(3) . . ?
C8 N1 C1 111.2(3) . . ?
C8 N1 C26 120.9(3) . . ?
C17 N2 C12 124.4(2) . . ?
C17 N2 C24 110.0(2) . . ?
C24 N2 C12 124.3(2) . . ?
C2 C1 N1 129.7(3) . . ?
C6 C1 N1 108.9(3) . . ?
C6 C1 C2 121.4(3) . . ?
C1 C2 C25 125.3(3) . . ?
C3 C2 C1 116.1(3) . . ?
C3 C2 C25 118.6(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 Br1 119.4(2) . . ?
C3 C4 C5 121.7(3) . . ?
C5 C4 Br1 118.9(2) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 C4 117.0(3) . . ?
C6 C5 H5 121.5 . . ?
C1 C6 C7 109.7(3) . . ?
C5 C6 C1 121.7(3) . . ?
C5 C6 C7 128.5(2) . . ?
C6 C7 C8 101.1(2) . . ?
C6 C7 C9 114.2(2) . . ?
C6 C7 C11 115.8(2) . . ?
C8 C7 C11 110.6(2) . . ?
C9 C7 C8 111.7(3) . . ?
C9 C7 C11 103.8(2) . . ?
O1 C8 N1 125.2(3) . . ?
O1 C8 C7 125.7(3) . . ?
N1 C8 C7 109.1(3) . . ?
C7 C9 H9A 110.6 . . ?
C7 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C7 105.5(2) . . ?
C10 C9 H9A 110.6 . . ?
C10 C9 H9B 110.6 . . ?
C9 C10 H10 107.0 . . ?
C9 C10 C12 105.2(2) . . ?
C12 C10 H10 107.0 . . ?
C15 C10 C9 116.4(3) . . ?
C15 C10 H10 107.0 . . ?
C15 C10 C12 113.6(3) . . ?
C7 C11 H11A 110.4 . . ?
C7 C11 H11B 110.4 . . ?
C7 C11 C12 106.7(2) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
N2 C12 C10 112.0(2) . . ?
N2 C12 C11 111.0(2) . . ?
N2 C12 C13 108.4(2) . . ?
C11 C12 C10 105.6(2) . . ?
C13 C12 C10 109.7(2) . . ?
C13 C12 C11 110.0(2) . . ?
O2 C13 O3 124.3(3) . . ?
O2 C13 C12 125.7(3) . . ?
O3 C13 C12 109.9(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15 116.0 . . ?
C16 C15 C10 127.9(3) . . ?
C16 C15 H15 116.0 . . ?
C15 C16 H16A 124(3) . . ?
C15 C16 H16B 127(3) . . ?
H16A C16 H16B 108(4) . . ?
O5 C17 N2 125.4(3) . . ?
O5 C17 C18 127.9(3) . . ?
N2 C17 C18 106.7(2) . . ?
C19 C18 C17 130.1(3) . . ?
C19 C18 C23 121.6(3) . . ?
C23 C18 C17 108.2(3) . . ?
C18 C19 H19 121.2 . . ?
C18 C19 C20 117.6(3) . . ?
C20 C19 H19 121.2 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 121.2 . . ?
C21 C22 C23 117.7(3) . . ?
C23 C22 H22 121.2 . . ?
C18 C23 C22 121.0(3) . . ?
C18 C23 C24 108.4(3) . . ?
C22 C23 C24 130.7(3) . . ?
O4 C24 N2 125.2(3) . . ?
O4 C24 C23 128.2(3) . . ?
N2 C24 C23 106.7(2) . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 C4 C5 C6 177.8(2) . . . . ?
O5 C17 C18 C19 -0.5(5) . . . . ?
O5 C17 C18 C23 177.6(3) . . . . ?
N1 C1 C2 C3 178.7(3) . . . . ?
N1 C1 C2 C25 -3.5(6) . . . . ?
N1 C1 C6 C5 -178.1(3) . . . . ?
N1 C1 C6 C7 -0.5(3) . . . . ?
N2 C12 C13 O2 113.0(3) . . . . ?
N2 C12 C13 O3 -70.4(3) . . . . ?
N2 C17 C18 C19 -179.5(3) . . . . ?
N2 C17 C18 C23 -1.4(3) . . . . ?
C1 N1 C8 O1 -178.0(3) . . . . ?
C1 N1 C8 C7 -0.3(4) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C6 C7 C8 0.4(3) . . . . ?
C1 C6 C7 C9 -119.7(3) . . . . ?
C1 C6 C7 C11 119.9(3) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
C2 C3 C4 Br1 -177.5(2) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C4 C5 C6 C7 -177.7(3) . . . . ?
C5 C6 C7 C8 177.7(3) . . . . ?
C5 C6 C7 C9 57.7(4) . . . . ?
C5 C6 C7 C11 -62.7(4) . . . . ?
C6 C1 C2 C3 -2.4(4) . . . . ?
C6 C1 C2 C25 175.4(3) . . . . ?
C6 C7 C8 O1 177.7(4) . . . . ?
C6 C7 C8 N1 -0.1(3) . . . . ?
C6 C7 C9 C10 -163.9(2) . . . . ?
C6 C7 C11 C12 152.6(2) . . . . ?
C7 C9 C10 C12 32.6(3) . . . . ?
C7 C9 C10 C15 159.4(3) . . . . ?
C7 C11 C12 N2 -128.7(2) . . . . ?
C7 C11 C12 C10 -7.1(3) . . . . ?
C7 C11 C12 C13 111.3(3) . . . . ?
C8 N1 C1 C2 179.5(3) . . . . ?
C8 N1 C1 C6 0.5(4) . . . . ?
C8 C7 C9 C10 82.2(3) . . . . ?
C8 C7 C11 C12 -93.1(3) . . . . ?
C9 C7 C8 O1 -60.5(4) . . . . ?
C9 C7 C8 N1 121.8(3) . . . . ?
C9 C7 C11 C12 26.7(3) . . . . ?
C9 C10 C12 N2 105.4(3) . . . . ?
C9 C10 C12 C11 -15.5(3) . . . . ?
C9 C10 C12 C13 -134.1(3) . . . . ?
C9 C10 C15 C16 1.4(5) . . . . ?
C10 C12 C13 O2 -9.6(4) . . . . ?
C10 C12 C13 O3 166.9(2) . . . . ?
C11 C7 C8 O1 54.5(5) . . . . ?
C11 C7 C8 N1 -123.3(3) . . . . ?
C11 C7 C9 C10 -36.9(3) . . . . ?
C11 C12 C13 O2 -125.4(3) . . . . ?
C11 C12 C13 O3 51.1(3) . . . . ?
C12 N2 C17 O5 -9.1(4) . . . . ?
C12 N2 C17 C18 169.9(2) . . . . ?
C12 N2 C24 O4 9.6(5) . . . . ?
C12 N2 C24 C23 -170.2(2) . . . . ?
C12 C10 C15 C16 123.9(4) . . . . ?
C14 O3 C13 O2 -5.6(5) . . . . ?
C14 O3 C13 C12 177.8(3) . . . . ?
C15 C10 C12 N2 -23.0(3) . . . . ?
C15 C10 C12 C11 -144.0(3) . . . . ?
C15 C10 C12 C13 97.5(3) . . . . ?
C17 N2 C12 C10 -66.2(3) . . . . ?
C17 N2 C12 C11 51.6(3) . . . . ?
C17 N2 C12 C13 172.5(2) . . . . ?
C17 N2 C24 O4 176.8(3) . . . . ?
C17 N2 C24 C23 -3.0(3) . . . . ?
C17 C18 C19 C20 178.7(3) . . . . ?
C17 C18 C23 C22 -179.3(3) . . . . ?
C17 C18 C23 C24 -0.4(3) . . . . ?
C18 C19 C20 C21 0.3(5) . . . . ?
C18 C23 C24 O4 -177.7(3) . . . . ?
C18 C23 C24 N2 2.1(3) . . . . ?
C19 C18 C23 C22 -1.0(4) . . . . ?
C19 C18 C23 C24 177.9(3) . . . . ?
C19 C20 C21 C22 -1.2(6) . . . . ?
C20 C21 C22 C23 0.9(6) . . . . ?
C21 C22 C23 C18 0.1(5) . . . . ?
C21 C22 C23 C24 -178.5(3) . . . . ?
C22 C23 C24 O4 1.0(6) . . . . ?
C22 C23 C24 N2 -179.2(3) . . . . ?
C23 C18 C19 C20 0.8(5) . . . . ?
C24 N2 C12 C10 99.2(3) . . . . ?
C24 N2 C12 C11 -143.0(3) . . . . ?
C24 N2 C12 C13 -22.1(3) . . . . ?
C24 N2 C17 O5 -176.3(3) . . . . ?
C24 N2 C17 C18 2.7(3) . . . . ?
C25 C2 C3 C4 -177.9(3) . . . . ?
C26 N1 C1 C2 -4.3(6) . . . . ?
C26 N1 C1 C6 176.7(4) . . . . ?
C26 N1 C8 O1 5.4(6) . . . . ?
C26 N1 C8 C7 -176.8(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.121 0.121 0.000 153.0 37.2 ?
2 -0.121 -0.121 0.500 153.0 37.1 ?
3 -0.379 0.379 0.250 153.0 36.9 ?
4 0.379 0.621 0.750 153.0 36.6 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 1.887
_oxdiff_exptl_absorpt_empirical_full_min 0.694
####################################################################### 
# 
# 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_sj_dj_04
_database_code_depnum_ccdc_archive 'CCDC 2528102'
loop_
_audit_author_name
_audit_author_address
shanjing
;Zunyi Medical University
China
;
_audit_update_record             
;
2026-02-03 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;
_audit_creation_date             2025-02-26
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H23 Br N2 O5'
_chemical_formula_sum            'C26 H23 Br N2 O5'
_chemical_formula_weight         523.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.6564(2)
_cell_length_b                   10.6915(3)
_cell_length_c                   21.0319(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2396.23(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12214
_cell_measurement_temperature    293.01(10)
_cell_measurement_theta_max      69.3070
_cell_measurement_theta_min      4.1030
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.121a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25238
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.958
_diffrn_reflns_theta_min         4.204
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00 -26.00   0.50    0.07    -- -103.00  73.00  63.00   78
  2  ω    -97.00 -24.00   0.50    0.07    -- -103.00 116.00 139.00  146
  3  ω    -87.00  -5.00   0.50    0.05    --  -36.61 116.00 139.00  164
  4  ω    -16.00  46.00   0.50    0.05    --  -36.61  38.00  30.00  124
  5  ω    -16.00  46.00   0.50    0.05    --  -36.61  38.00 -60.00  124
  6  ω     30.00  93.00   0.50    0.07    --  109.42-112.00-120.00  126
  7  ω     30.00  93.00   0.50    0.07    --  109.42-112.00 150.00  126
  8  ω    -56.00  -9.00   0.50    0.05    --  -36.61 -57.00   0.00   94
  9  ω    -56.00  -9.00   0.50    0.05    --  -36.61 -57.00  60.00   94
 10  ω    -56.00  -9.00   0.50    0.05    --  -36.61 -57.00 120.00   94
 11  ω    -56.00  -9.00   0.50    0.05    --  -36.61 -57.00 -60.00   94
 12  ω    -56.00  -9.00   0.50    0.05    --  -36.61 -57.00 -90.00   94
 13  ω    -51.00 -16.00   0.50    0.05    --   36.61 -19.00-150.00   70
 14  ω    -51.00 -16.00   0.50    0.05    --   36.61 -19.00-180.00   70
 15  ω    -51.00 -16.00   0.50    0.05    --   36.61 -19.00-120.00   70
 16  ω    -25.00  67.00   0.50    0.05    --   36.61 -73.00 -65.00  184
 17  ω    -51.00 -16.00   0.50    0.05    --   36.61 -19.00 150.00   70
 18  ω     33.00  71.00   0.50    0.08    --  109.42 -73.00 -65.00   76
 19  ω     31.00  78.00   0.50    0.08    --  109.42 -77.00-180.00   94
 20  ω     31.00  78.00   0.50    0.08    --  109.42 -77.00-120.00   94
 21  ω     31.00  78.00   0.50    0.08    --  109.42 -77.00  60.00   94
 22  ω     77.00 169.00   0.50    0.08    --  109.42  30.00-120.00  184
 23  ω    106.00 175.00   0.50    0.08    --  109.42  73.00  63.00  138
 24  ω    106.00 175.00   0.50    0.08    --  109.42  77.00 120.00  138
 25  ω     77.00 169.00   0.50    0.08    --  109.42  30.00-120.00  184
 26  ω      9.00 117.00   0.50    0.05    --   36.61  49.00 -88.00  216
 27  ω   -133.00 -65.00   0.50    0.08    -- -103.00 -15.00  30.00  136
 28  ω   -163.00 -71.00   0.50    0.08    -- -103.00 -30.00 -30.00  184
 29  ω   -174.00 -99.00   0.50    0.08    -- -103.00 -77.00-180.00  150
 30  ω   -174.00-100.00   0.50    0.08    -- -103.00 -73.00 -65.00  148
 31  ω   -174.00 -93.00   0.50    0.08    -- -103.00-116.00  51.00  162
 32  ω   -174.00 -93.00   0.50    0.08    -- -103.00-116.00  51.00  162
 33  ω   -174.00 -99.00   0.50    0.08    -- -103.00 -95.00  60.00  150
 34  ω    -40.00 -14.00   0.50    0.05    --  -36.94 -57.00-180.00   52
 35  ω    -19.00  18.00   0.50    0.05    --  -36.94  77.00 150.00   74
 36  ω    -56.00 -31.00   0.50    0.05    --  -36.94 -57.00  30.00   50
 37  ω    -66.00 -32.00   0.50    0.05    --  -36.94  77.00 150.00   68
 38  ω    -51.00 -25.00   0.50    0.08    -- -103.00  98.00-140.36   52
 39  ω    -93.00 -67.00   0.50    0.08    -- -103.00  98.00-140.36   52
 40  ω    -93.00 -67.00   0.50    0.08    -- -103.00  94.00 140.88   52
 41  ω    -97.00 -71.00   0.50    0.08    -- -103.00 115.00 173.59   52
 42  ω    -97.00 -60.00   0.50    0.08    -- -103.00 115.00 -17.81   74
 43  ω   -172.00-137.00   0.50    0.08    -- -103.00 -77.00 150.00   70
 44  ω   -146.00-109.00   0.50    0.08    -- -103.00 -77.00-120.00   74
 45  ω    -97.00 -58.50   0.50    0.08    -- -103.00 115.00-128.32   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1181105000
_diffrn_orient_matrix_UB_12      -0.0826519000
_diffrn_orient_matrix_UB_13      -0.0044383000
_diffrn_orient_matrix_UB_21      -0.0064749000
_diffrn_orient_matrix_UB_22      -0.0243295000
_diffrn_orient_matrix_UB_23      0.0721428000
_diffrn_orient_matrix_UB_31      -0.0830390000
_diffrn_orient_matrix_UB_32      -0.1155246000
_diffrn_orient_matrix_UB_33      -0.0119367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                4056
_reflns_number_total             4569
_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 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.121a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.684
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1556 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.039(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4569
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²+0.4577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1233
_refine_ls_wR_factor_ref         0.1276
_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. Restrained distances
 C14-C13
 1.4 with sigma of 0.01
3. Others
 Sof(H13A)=Sof(C27)=Sof(H27A)=Sof(H27B)=1-FVAR(1)
 Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C11(H11)
4.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C13(H13), C13(H13A), C17(H17), C18(H18), C19(H19), C20(H20)
4.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B), C27(H27A,H27B)
4.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_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 0.11635(8) 0.45378(9) 0.19611(4) 0.1337(4) Uani 1 1 d . . . . .
O1 O 0.4213(4) 0.5524(5) 0.52290(16) 0.1065(12) Uani 1 1 d . . . . .
O2 O 0.7321(4) 0.4055(4) 0.44610(14) 0.1018(11) Uani 1 1 d . . . . .
O3 O 0.7991(3) 0.3370(3) 0.35196(14) 0.0761(7) Uani 1 1 d . . . . .
O4 O 0.5346(4) 0.2624(3) 0.23527(16) 0.0946(10) Uani 1 1 d . . . . .
O5 O 0.7337(3) 0.6100(3) 0.31062(16) 0.0822(8) Uani 1 1 d . . . . .
N1 N 0.2425(3) 0.5960(4) 0.46620(19) 0.0794(10) Uani 1 1 d . . . . .
N2 N 0.6145(3) 0.4347(3) 0.28910(13) 0.0583(7) Uani 1 1 d . . . . .
C1 C 0.1951(4) 0.5705(4) 0.4049(2) 0.0705(10) Uani 1 1 d . . . . .
C2 C 0.0813(4) 0.6054(5) 0.3774(3) 0.0877(13) Uani 1 1 d . . . . .
C3 C 0.0626(4) 0.5680(5) 0.3148(3) 0.0902(13) Uani 1 1 d . . . . .
H3 H -0.012143 0.589293 0.294727 0.108 Uiso 1 1 calc R U . . .
C4 C 0.1499(5) 0.5012(5) 0.2819(2) 0.0833(12) Uani 1 1 d . . . . .
C5 C 0.2630(4) 0.4658(4) 0.3092(2) 0.0740(10) Uani 1 1 d . . . . .
H5 H 0.322348 0.420626 0.286235 0.089 Uiso 1 1 calc R U . . .
C6 C 0.2843(3) 0.4999(4) 0.37152(19) 0.0657(9) Uani 1 1 d . . . . .
C7 C 0.3959(4) 0.4778(4) 0.41355(18) 0.0669(9) Uani 1 1 d . . . . .
C8 C 0.3578(4) 0.5446(5) 0.4744(2) 0.0801(11) Uani 1 1 d . . . . .
C9 C 0.5212(3) 0.5256(4) 0.38698(19) 0.0662(9) Uani 1 1 d . . . . .
H9A H 0.571535 0.561463 0.420809 0.079 Uiso 1 1 calc R U . . .
H9B H 0.506522 0.589501 0.355120 0.079 Uiso 1 1 calc R U . . .
C10 C 0.5901(3) 0.4128(4) 0.35705(15) 0.0583(8) Uani 1 1 d . . . . .
C11 C 0.5037(4) 0.2965(4) 0.37098(19) 0.0670(9) Uani 1 1 d . . . . .
H11 H 0.446351 0.287063 0.334867 0.080 Uiso 1 1 calc R U . . .
C12 C 0.4265(4) 0.3401(5) 0.4277(2) 0.0760(11) Uani 1 1 d . . . . .
H12A H 0.474291 0.332617 0.466729 0.091 Uiso 1 1 calc R U . . .
H12B H 0.350225 0.291269 0.431588 0.091 Uiso 1 1 calc R U . . .
C13 C 0.5709(5) 0.1759(5) 0.3792(3) 0.0891(13) Uani 1 1 d D . . . .
H13 H 0.602430 0.137810 0.342773 0.107 Uiso 0.745(14) 1 calc R U P A 1
H13A H 0.604192 0.167349 0.419822 0.107 Uiso 0.255(14) 1 calc R U P A 2
C14 C 0.5893(15) 0.1196(10) 0.4328(5) 0.163(6) Uani 0.745(14) 1 d D . P A 1
H14A H 0.559260 0.154614 0.470283 0.195 Uiso 0.745(14) 1 calc R U P A 1
H14B H 0.632478 0.044039 0.433814 0.195 Uiso 0.745(14) 1 calc R U P A 1
C15 C 0.6932(3) 0.5358(4) 0.27274(19) 0.0668(9) Uani 1 1 d . . . . .
C16 C 0.7172(4) 0.5256(4) 0.2039(2) 0.0719(10) Uani 1 1 d . . . . .
C17 C 0.7870(5) 0.6020(6) 0.1641(3) 0.0911(14) Uani 1 1 d . . . . .
H17 H 0.826486 0.673710 0.179199 0.109 Uiso 1 1 calc R U . . .
C18 C 0.7953(6) 0.5664(8) 0.1006(3) 0.109(2) Uani 1 1 d . . . . .
H18 H 0.842070 0.614434 0.072351 0.131 Uiso 1 1 calc R U . . .
C19 C 0.7346(8) 0.4601(7) 0.0791(3) 0.116(2) Uani 1 1 d . . . . .
H19 H 0.740342 0.439476 0.036267 0.139 Uiso 1 1 calc R U . . .
C20 C 0.6661(6) 0.3839(6) 0.1186(2) 0.0999(16) Uani 1 1 d . . . . .
H20 H 0.626435 0.312225 0.103637 0.120 Uiso 1 1 calc R U . . .
C21 C 0.6591(4) 0.4193(5) 0.18196(18) 0.0742(11) Uani 1 1 d . . . . .
C22 C 0.5938(4) 0.3574(4) 0.23594(18) 0.0674(9) Uani 1 1 d . . . . .
C23 C 0.7161(4) 0.3877(4) 0.39037(19) 0.0698(10) Uani 1 1 d . . . . .
C24 C 0.9135(5) 0.2924(6) 0.3814(3) 0.1059(18) Uani 1 1 d . . . . .
H24A H 0.977192 0.282390 0.349491 0.159 Uiso 1 1 calc R U . . .
H24B H 0.897952 0.213370 0.401576 0.159 Uiso 1 1 calc R U . . .
H24C H 0.941279 0.351815 0.412572 0.159 Uiso 1 1 calc R U . . .
C25 C -0.0206(6) 0.6773(8) 0.4109(4) 0.123(2) Uani 1 1 d . . . . .
H25A H -0.036051 0.640383 0.451798 0.185 Uiso 1 1 calc R U . . .
H25B H -0.095986 0.674786 0.386012 0.185 Uiso 1 1 calc R U . . .
H25C H 0.005418 0.762611 0.416390 0.185 Uiso 1 1 calc R U . . .
C26 C 0.1835(6) 0.6727(6) 0.5152(3) 0.1068(18) Uani 1 1 d . . . . .
H26A H 0.167143 0.754661 0.498444 0.160 Uiso 1 1 calc R U . . .
H26B H 0.238662 0.679255 0.551107 0.160 Uiso 1 1 calc R U . . .
H26C H 0.106031 0.634746 0.528129 0.160 Uiso 1 1 calc R U . . .
C27 C 0.5954(17) 0.0769(15) 0.3427(10) 0.078(6) Uani 0.255(14) 1 d . . P A 2
H27A H 0.566875 0.074631 0.300890 0.094 Uiso 0.255(14) 1 calc R U P A 2
H27B H 0.641071 0.010017 0.358974 0.094 Uiso 0.255(14) 1 calc R U P A 2


_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 C4 1.909(5) . ?
O1 C8 1.227(6) . ?
O2 C23 1.200(5) . ?
O3 C23 1.315(5) . ?
O3 C24 1.448(5) . ?
O4 C22 1.195(6) . ?
O5 C15 1.204(5) . ?
N1 C1 1.412(6) . ?
N1 C8 1.357(6) . ?
N1 C26 1.459(6) . ?
N2 C10 1.471(4) . ?
N2 C15 1.410(5) . ?
N2 C22 1.408(5) . ?
C1 C2 1.395(7) . ?
C1 C6 1.402(6) . ?
C2 C3 1.390(8) . ?
C2 C25 1.505(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(7) . ?
C4 C5 1.388(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(6) . ?
C6 C7 1.501(6) . ?
C7 C8 1.521(6) . ?
C7 C9 1.535(6) . ?
C7 C12 1.536(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.545(6) . ?
C10 C11 1.575(6) . ?
C10 C23 1.538(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.522(6) . ?
C11 C13 1.485(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13 0.9300 . ?
C13 H13A 0.9300 . ?
C13 C14 1.293(9) . ?
C13 C27 1.334(19) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?
C15 C16 1.474(6) . ?
C16 C17 1.385(7) . ?
C16 C21 1.374(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.393(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(10) . ?
C19 H19 0.9300 . ?
C19 C20 1.373(9) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(6) . ?
C21 C22 1.487(6) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9300 . ?
C27 H27B 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
C23 O3 C24 116.1(4) . . ?
C1 N1 C26 126.8(4) . . ?
C8 N1 C1 111.2(4) . . ?
C8 N1 C26 121.9(4) . . ?
C15 N2 C10 117.7(3) . . ?
C22 N2 C10 130.5(3) . . ?
C22 N2 C15 110.5(3) . . ?
C2 C1 N1 129.6(4) . . ?
C2 C1 C6 121.8(4) . . ?
C6 C1 N1 108.6(4) . . ?
C1 C2 C25 124.7(5) . . ?
C3 C2 C1 116.1(4) . . ?
C3 C2 C25 119.2(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 C2 122.3(4) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 Br1 119.5(4) . . ?
C3 C4 C5 121.8(5) . . ?
C5 C4 Br1 118.7(4) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 C4 117.5(4) . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C7 109.1(4) . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 C7 130.4(4) . . ?
C6 C7 C8 102.1(3) . . ?
C6 C7 C9 115.0(3) . . ?
C6 C7 C12 115.7(4) . . ?
C8 C7 C9 112.5(4) . . ?
C8 C7 C12 110.1(4) . . ?
C9 C7 C12 101.8(3) . . ?
O1 C8 N1 125.3(4) . . ?
O1 C8 C7 125.8(4) . . ?
N1 C8 C7 109.0(4) . . ?
C7 C9 H9A 110.2 . . ?
C7 C9 H9B 110.2 . . ?
C7 C9 C10 107.6(3) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.2 . . ?
C10 C9 H9B 110.2 . . ?
N2 C10 C9 110.8(3) . . ?
N2 C10 C11 114.2(3) . . ?
N2 C10 C23 108.4(3) . . ?
C9 C10 C11 105.2(3) . . ?
C23 C10 C9 111.4(3) . . ?
C23 C10 C11 106.7(3) . . ?
C10 C11 H11 107.6 . . ?
C12 C11 C10 102.7(3) . . ?
C12 C11 H11 107.6 . . ?
C13 C11 C10 115.2(4) . . ?
C13 C11 H11 107.6 . . ?
C13 C11 C12 115.9(4) . . ?
C7 C12 H12A 110.8 . . ?
C7 C12 H12B 110.8 . . ?
C11 C12 C7 104.9(3) . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
C11 C13 H13 117.3 . . ?
C11 C13 H13A 112.1 . . ?
C14 C13 C11 125.4(7) . . ?
C14 C13 H13 117.3 . . ?
C27 C13 C11 135.8(10) . . ?
C27 C13 H13A 112.1 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
O5 C15 N2 123.8(4) . . ?
O5 C15 C16 129.5(4) . . ?
N2 C15 C16 106.6(3) . . ?
C17 C16 C15 130.0(5) . . ?
C21 C16 C15 108.2(4) . . ?
C21 C16 C17 121.8(5) . . ?
C16 C17 H17 121.6 . . ?
C16 C17 C18 116.9(6) . . ?
C18 C17 H17 121.6 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 118.7 . . ?
C20 C19 C18 122.6(5) . . ?
C20 C19 H19 118.7 . . ?
C19 C20 H20 121.7 . . ?
C19 C20 C21 116.6(6) . . ?
C21 C20 H20 121.7 . . ?
C16 C21 C20 121.6(5) . . ?
C16 C21 C22 108.9(3) . . ?
C20 C21 C22 129.6(5) . . ?
O4 C22 N2 126.2(4) . . ?
O4 C22 C21 128.0(4) . . ?
N2 C22 C21 105.7(4) . . ?
O2 C23 O3 124.8(4) . . ?
O2 C23 C10 122.8(4) . . ?
O3 C23 C10 112.3(3) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C25 H25A 109.5 . . ?
C2 C25 H25B 109.5 . . ?
C2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C13 C27 H27A 120.0 . . ?
C13 C27 H27B 120.0 . . ?
H27A C27 H27B 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 C4 C5 C6 -179.2(3) . . . . ?
O5 C15 C16 C17 -3.8(8) . . . . ?
O5 C15 C16 C21 174.6(4) . . . . ?
N1 C1 C2 C3 178.6(5) . . . . ?
N1 C1 C2 C25 -2.4(9) . . . . ?
N1 C1 C6 C5 -177.8(4) . . . . ?
N1 C1 C6 C7 0.2(5) . . . . ?
N2 C10 C11 C12 -143.8(3) . . . . ?
N2 C10 C11 C13 89.4(4) . . . . ?
N2 C10 C23 O2 155.8(4) . . . . ?
N2 C10 C23 O3 -28.8(5) . . . . ?
N2 C15 C16 C17 179.0(4) . . . . ?
N2 C15 C16 C21 -2.6(4) . . . . ?
C1 N1 C8 O1 179.6(5) . . . . ?
C1 N1 C8 C7 0.4(5) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
C1 C6 C7 C8 0.1(4) . . . . ?
C1 C6 C7 C9 -122.0(4) . . . . ?
C1 C6 C7 C12 119.7(4) . . . . ?
C2 C1 C6 C5 2.0(6) . . . . ?
C2 C1 C6 C7 180.0(4) . . . . ?
C2 C3 C4 Br1 -180.0(4) . . . . ?
C2 C3 C4 C5 0.4(8) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C1 -1.6(6) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C5 C6 C7 C8 177.8(4) . . . . ?
C5 C6 C7 C9 55.7(6) . . . . ?
C5 C6 C7 C12 -62.6(6) . . . . ?
C6 C1 C2 C3 -1.1(7) . . . . ?
C6 C1 C2 C25 177.9(6) . . . . ?
C6 C7 C8 O1 -179.5(5) . . . . ?
C6 C7 C8 N1 -0.3(5) . . . . ?
C6 C7 C9 C10 -98.8(4) . . . . ?
C6 C7 C12 C11 83.7(4) . . . . ?
C7 C9 C10 N2 120.6(3) . . . . ?
C7 C9 C10 C11 -3.3(4) . . . . ?
C7 C9 C10 C23 -118.6(3) . . . . ?
C8 N1 C1 C2 179.8(5) . . . . ?
C8 N1 C1 C6 -0.4(5) . . . . ?
C8 C7 C9 C10 144.9(4) . . . . ?
C8 C7 C12 C11 -161.2(3) . . . . ?
C9 C7 C8 O1 -55.6(7) . . . . ?
C9 C7 C8 N1 123.5(4) . . . . ?
C9 C7 C12 C11 -41.7(4) . . . . ?
C9 C10 C11 C12 -22.0(4) . . . . ?
C9 C10 C11 C13 -148.8(4) . . . . ?
C9 C10 C23 O2 33.6(6) . . . . ?
C9 C10 C23 O3 -150.9(3) . . . . ?
C10 N2 C15 O5 -5.7(6) . . . . ?
C10 N2 C15 C16 171.7(3) . . . . ?
C10 N2 C22 O4 11.3(7) . . . . ?
C10 N2 C22 C21 -169.3(3) . . . . ?
C10 C11 C12 C7 39.8(4) . . . . ?
C10 C11 C13 C14 105.4(10) . . . . ?
C10 C11 C13 C27 -99.2(12) . . . . ?
C11 C10 C23 O2 -80.7(5) . . . . ?
C11 C10 C23 O3 94.7(4) . . . . ?
C12 C7 C8 O1 57.1(6) . . . . ?
C12 C7 C8 N1 -123.7(4) . . . . ?
C12 C7 C9 C10 27.1(4) . . . . ?
C12 C11 C13 C14 -14.4(11) . . . . ?
C12 C11 C13 C27 141.0(12) . . . . ?
C13 C11 C12 C7 166.1(4) . . . . ?
C15 N2 C10 C9 62.6(4) . . . . ?
C15 N2 C10 C11 -178.8(3) . . . . ?
C15 N2 C10 C23 -59.9(4) . . . . ?
C15 N2 C22 O4 177.4(4) . . . . ?
C15 N2 C22 C21 -3.2(4) . . . . ?
C15 C16 C17 C18 178.4(5) . . . . ?
C15 C16 C21 C20 -179.3(5) . . . . ?
C15 C16 C21 C22 0.6(5) . . . . ?
C16 C17 C18 C19 0.8(9) . . . . ?
C16 C21 C22 O4 -179.1(4) . . . . ?
C16 C21 C22 N2 1.6(5) . . . . ?
C17 C16 C21 C20 -0.8(7) . . . . ?
C17 C16 C21 C22 179.2(4) . . . . ?
C17 C18 C19 C20 -1.3(10) . . . . ?
C18 C19 C20 C21 0.7(10) . . . . ?
C19 C20 C21 C16 0.3(8) . . . . ?
C19 C20 C21 C22 -179.6(5) . . . . ?
C20 C21 C22 O4 0.8(8) . . . . ?
C20 C21 C22 N2 -178.5(5) . . . . ?
C21 C16 C17 C18 0.2(7) . . . . ?
C22 N2 C10 C9 -132.1(4) . . . . ?
C22 N2 C10 C11 -13.5(5) . . . . ?
C22 N2 C10 C23 105.3(4) . . . . ?
C22 N2 C15 O5 -173.8(4) . . . . ?
C22 N2 C15 C16 3.6(4) . . . . ?
C23 C10 C11 C12 96.5(4) . . . . ?
C23 C10 C11 C13 -30.4(5) . . . . ?
C24 O3 C23 O2 4.5(7) . . . . ?
C24 O3 C23 C10 -170.8(4) . . . . ?
C25 C2 C3 C4 -179.1(6) . . . . ?
C26 N1 C1 C2 -3.6(8) . . . . ?
C26 N1 C1 C6 176.2(5) . . . . ?
C26 N1 C8 O1 2.8(8) . . . . ?
C26 N1 C8 C7 -176.3(4) . . . . ?

_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 3.973
_oxdiff_exptl_absorpt_empirical_full_min 0.437
