# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_audit_block_doi                 10.5517/ccdc.csd.cc1yzwb4
_database_code_depnum_ccdc_archive 'CCDC 1817137'
_audit_update_record             
;
2018-01-15 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H19 Br N2 O3'
_chemical_formula_weight         463.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '
_chemical_absolute_configuration rmad

loop_
_symmetry_equiv_pos_as_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                   11.4032(17)
_cell_length_b                   16.0552(14)
_cell_length_c                   21.7377(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3979.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2366
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      21.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888
_exptl_absorpt_coefficient_mu    2.096
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5817
_exptl_absorpt_correction_T_max  0.6673
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20016
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6986
_reflns_number_gt                4047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6986
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35331(6) -0.15803(4) 0.16170(3) 0.0673(2) Uani 1 1 d . . .
Br2 Br 0.91209(6) 0.33847(4) 0.14785(3) 0.0689(2) Uani 1 1 d . . .
O1 O 0.2197(4) 0.5602(2) 0.19827(17) 0.0556(12) Uani 1 1 d . . .
O2 O 0.7444(3) 0.1729(2) 0.11725(18) 0.0578(11) Uani 1 1 d . . .
O3 O 0.3939(3) 0.2467(2) 0.03722(16) 0.0508(11) Uani 1 1 d . . .
O4 O 1.0451(3) 1.0512(2) 0.19657(17) 0.0506(11) Uani 1 1 d . . .
O5 O 0.8639(3) 0.7435(2) 0.03186(17) 0.0492(10) Uani 1 1 d . . .
O6 O 0.5115(3) 0.6729(2) 0.11067(16) 0.0518(10) Uani 1 1 d . . .
N1 N 0.5739(4) 0.1967(2) 0.0655(2) 0.0364(11) Uani 1 1 d . . .
N2 N 0.4730(4) 0.2061(3) 0.18755(19) 0.0397(12) Uani 1 1 d . . .
N3 N 0.7849(4) 0.7000(3) 0.1817(2) 0.0384(12) Uani 1 1 d . . .
N4 N 0.6847(4) 0.6935(2) 0.06038(19) 0.0339(11) Uani 1 1 d . . .
C1 C 0.2608(5) 0.6406(3) 0.1802(3) 0.0614(18) Uani 1 1 d . . .
H1A H 0.2083 0.6825 0.1954 0.092 Uiso 1 1 calc R . .
H1B H 0.2639 0.6437 0.1361 0.092 Uiso 1 1 calc R . .
H1C H 0.3377 0.6497 0.1968 0.092 Uiso 1 1 calc R . .
C2 C 0.2842(5) 0.4929(3) 0.1817(2) 0.0379(15) Uani 1 1 d . . .
C3 C 0.3906(5) 0.4964(3) 0.1515(2) 0.0369(15) Uani 1 1 d . . .
H3A H 0.4226 0.5474 0.1402 0.044 Uiso 1 1 calc R . .
C4 C 0.4486(5) 0.4234(3) 0.1383(2) 0.0373(14) Uani 1 1 d . . .
H4A H 0.5200 0.4257 0.1178 0.045 Uiso 1 1 calc R . .
C5 C 0.4034(4) 0.3468(4) 0.1549(2) 0.0361(14) Uani 1 1 d . . .
C6 C 0.2957(5) 0.3448(4) 0.1842(2) 0.0438(14) Uani 1 1 d . . .
H6A H 0.2628 0.2939 0.1950 0.053 Uiso 1 1 calc R . .
C7 C 0.2369(5) 0.4172(3) 0.1976(2) 0.0436(15) Uani 1 1 d . . .
H7A H 0.1648 0.4150 0.2176 0.052 Uiso 1 1 calc R . .
C8 C 0.4661(5) 0.2692(3) 0.1403(2) 0.0338(13) Uani 1 1 d . . .
C9 C 0.5823(5) 0.2431(3) 0.1671(2) 0.0406(14) Uani 1 1 d . . .
H9A H 0.6251 0.2811 0.1944 0.049 Uiso 1 1 calc R . .
C10 C 0.6459(5) 0.1997(3) 0.1158(3) 0.0399(14) Uani 1 1 d . . .
C11 C 0.4690(5) 0.2373(3) 0.0750(2) 0.0345(13) Uani 1 1 d . . .
C12 C 0.6105(5) 0.1614(4) 0.0072(2) 0.0468(15) Uani 1 1 d . . .
H12A H 0.6864 0.1844 -0.0036 0.056 Uiso 1 1 calc R . .
H12B H 0.5552 0.1785 -0.0243 0.056 Uiso 1 1 calc R . .
C13 C 0.6195(5) 0.0662(4) 0.0066(2) 0.0382(16) Uani 1 1 d . . .
C14 C 0.7159(6) 0.0308(4) -0.0169(2) 0.0490(17) Uani 1 1 d . . .
H14A H 0.7779 0.0639 -0.0301 0.059 Uiso 1 1 calc R . .
C15 C 0.7235(7) -0.0559(4) -0.0215(3) 0.066(2) Uani 1 1 d . . .
H15A H 0.7912 -0.0813 -0.0364 0.080 Uiso 1 1 calc R . .
C16 C 0.6297(7) -0.1020(4) -0.0038(3) 0.054(2) Uani 1 1 d . . .
H16A H 0.6325 -0.1595 -0.0089 0.065 Uiso 1 1 calc R . .
C17 C 0.5325(6) -0.0677(4) 0.0209(3) 0.0570(18) Uani 1 1 d . . .
H17A H 0.4704 -0.1008 0.0340 0.068 Uiso 1 1 calc R . .
C18 C 0.5279(5) 0.0193(4) 0.0262(2) 0.0479(17) Uani 1 1 d . . .
H18A H 0.4621 0.0448 0.0432 0.057 Uiso 1 1 calc R . .
C19 C 0.4466(5) 0.1205(3) 0.1765(2) 0.0347(15) Uani 1 1 d . . .
C20 C 0.5254(5) 0.0603(3) 0.1958(2) 0.0420(15) Uani 1 1 d . . .
H20A H 0.5979 0.0759 0.2116 0.050 Uiso 1 1 calc R . .
C21 C 0.4961(5) -0.0227(3) 0.1915(2) 0.0442(16) Uani 1 1 d . . .
H21A H 0.5478 -0.0638 0.2047 0.053 Uiso 1 1 calc R . .
C22 C 0.3894(6) -0.0434(3) 0.1674(3) 0.0412(15) Uani 1 1 d . . .
C23 C 0.3111(5) 0.0144(3) 0.1484(2) 0.0451(15) Uani 1 1 d . . .
H23A H 0.2387 -0.0016 0.1325 0.054 Uiso 1 1 calc R . .
C24 C 0.3408(5) 0.0979(3) 0.1529(2) 0.0405(15) Uani 1 1 d . . .
H24A H 0.2884 0.1385 0.1398 0.049 Uiso 1 1 calc R . .
C25 C 0.9959(5) 1.1313(3) 0.1931(3) 0.0565(18) Uani 1 1 d . . .
H25A H 1.0533 1.1718 0.2052 0.085 Uiso 1 1 calc R . .
H25B H 0.9294 1.1346 0.2201 0.085 Uiso 1 1 calc R . .
H25C H 0.9713 1.1422 0.1516 0.085 Uiso 1 1 calc R . .
C26 C 0.9764(5) 0.9861(3) 0.1808(2) 0.0350(15) Uani 1 1 d . . .
C27 C 0.8648(5) 0.9897(3) 0.1568(2) 0.0395(15) Uani 1 1 d . . .
H27A H 0.8288 1.0411 0.1508 0.047 Uiso 1 1 calc R . .
C28 C 0.8070(5) 0.9183(3) 0.1417(2) 0.0340(14) Uani 1 1 d . . .
H28A H 0.7324 0.9215 0.1246 0.041 Uiso 1 1 calc R . .
C29 C 0.8570(5) 0.8422(4) 0.1514(2) 0.0350(13) Uani 1 1 d . . .
C30 C 0.9653(5) 0.8379(4) 0.1760(2) 0.0450(14) Uani 1 1 d . . .
H30A H 0.9987 0.7859 0.1831 0.054 Uiso 1 1 calc R . .
C31 C 1.0280(5) 0.9085(3) 0.1910(2) 0.0401(15) Uani 1 1 d . . .
H31A H 1.1030 0.9045 0.2075 0.048 Uiso 1 1 calc R . .
C32 C 0.7911(5) 0.7646(3) 0.1351(2) 0.0330(14) Uani 1 1 d . . .
C33 C 0.7897(5) 0.7347(3) 0.0695(2) 0.0333(13) Uani 1 1 d . . .
C34 C 0.6761(4) 0.7381(3) 0.1611(2) 0.0398(14) Uani 1 1 d . . .
H34A H 0.6338 0.7758 0.1889 0.048 Uiso 1 1 calc R . .
C35 C 0.6119(5) 0.6973(3) 0.1101(3) 0.0396(14) Uani 1 1 d . . .
C36 C 0.6492(5) 0.6599(4) 0.0016(2) 0.0468(14) Uani 1 1 d . . .
H36A H 0.7058 0.6769 -0.0293 0.056 Uiso 1 1 calc R . .
H36B H 0.5741 0.6840 -0.0096 0.056 Uiso 1 1 calc R . .
C37 C 0.6384(5) 0.5651(3) 0.0002(2) 0.0356(15) Uani 1 1 d . . .
C38 C 0.5384(5) 0.5299(4) -0.0236(2) 0.0463(16) Uani 1 1 d . . .
H38A H 0.4755 0.5631 -0.0354 0.056 Uiso 1 1 calc R . .
C39 C 0.5328(6) 0.4445(4) -0.0297(3) 0.0544(18) Uani 1 1 d . . .
H39A H 0.4664 0.4202 -0.0468 0.065 Uiso 1 1 calc R . .
C40 C 0.6221(7) 0.3962(4) -0.0112(3) 0.056(2) Uani 1 1 d . . .
H40A H 0.6169 0.3386 -0.0152 0.067 Uiso 1 1 calc R . .
C41 C 0.7190(6) 0.4306(4) 0.0130(3) 0.0559(19) Uani 1 1 d . . .
H41A H 0.7802 0.3966 0.0261 0.067 Uiso 1 1 calc R . .
C42 C 0.7286(5) 0.5160(4) 0.0187(3) 0.0489(16) Uani 1 1 d . . .
H42A H 0.7963 0.5396 0.0351 0.059 Uiso 1 1 calc R . .
C43 C 0.8117(5) 0.6154(3) 0.1691(2) 0.0331(13) Uani 1 1 d . . .
C44 C 0.9197(5) 0.5949(3) 0.1460(2) 0.0430(15) Uani 1 1 d . . .
H44A H 0.9718 0.6367 0.1347 0.052 Uiso 1 1 calc R . .
C45 C 0.9518(5) 0.5119(3) 0.1395(2) 0.0437(15) Uani 1 1 d . . .
H45A H 1.0250 0.4971 0.1241 0.052 Uiso 1 1 calc R . .
C46 C 0.8711(6) 0.4521(3) 0.1567(3) 0.0450(16) Uani 1 1 d . . .
C47 C 0.7640(6) 0.4717(4) 0.1804(2) 0.0440(16) Uani 1 1 d . . .
H47A H 0.7120 0.4300 0.1921 0.053 Uiso 1 1 calc R . .
C48 C 0.7337(5) 0.5546(3) 0.1870(2) 0.0423(15) Uani 1 1 d . . .
H48A H 0.6612 0.5691 0.2034 0.051 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 C22 1.890(5) . ?
Br2 C46 1.893(5) . ?
O1 C2 1.356(6) . ?
O1 C1 1.429(6) . ?
O2 C10 1.203(6) . ?
O3 C11 1.196(5) . ?
O4 C26 1.351(6) . ?
O4 C25 1.404(6) . ?
O5 C33 1.186(5) . ?
O6 C35 1.210(5) . ?
N1 C10 1.367(6) . ?
N1 C11 1.377(6) . ?
N1 C12 1.450(6) . ?
N2 C19 1.426(6) . ?
N2 C8 1.446(6) . ?
N2 C9 1.452(7) . ?
N3 C43 1.419(6) . ?
N3 C32 1.452(6) . ?
N3 C34 1.454(6) . ?
N4 C35 1.364(6) . ?
N4 C33 1.382(6) . ?
N4 C36 1.446(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.374(7) . ?
C2 C3 1.380(7) . ?
C3 C4 1.376(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.384(6) . ?
C5 C8 1.471(7) . ?
C6 C7 1.374(7) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.507(7) . ?
C8 C11 1.510(7) . ?
C9 C10 1.503(7) . ?
C9 H9A 0.9800 . ?
C12 C13 1.532(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.339(7) . ?
C13 C18 1.357(7) . ?
C14 C15 1.398(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.356(9) . ?
C15 H15A 0.9300 . ?
C16 C17 1.349(8) . ?
C16 H16A 0.9300 . ?
C17 C18 1.402(8) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C24 1.360(7) . ?
C19 C20 1.384(7) . ?
C20 C21 1.378(7) . ?
C20 H20A 0.9300 . ?
C21 C22 1.365(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.352(7) . ?
C23 C24 1.386(6) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.377(7) . ?
C26 C31 1.395(7) . ?
C27 C28 1.362(6) . ?
C27 H27A 0.9300 . ?
C28 C29 1.365(7) . ?
C28 H28A 0.9300 . ?
C29 C30 1.347(7) . ?
C29 C32 1.498(7) . ?
C30 C31 1.379(7) . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9300 . ?
C32 C34 1.490(7) . ?
C32 C33 1.505(7) . ?
C34 C35 1.482(7) . ?
C34 H34A 0.9800 . ?
C36 C37 1.527(8) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C42 1.358(7) . ?
C37 C38 1.373(7) . ?
C38 C39 1.379(8) . ?
C38 H38A 0.9300 . ?
C39 C40 1.342(8) . ?
C39 H39A 0.9300 . ?
C40 C41 1.344(8) . ?
C40 H40A 0.9300 . ?
C41 C42 1.381(7) . ?
C41 H41A 0.9300 . ?
C42 H42A 0.9300 . ?
C43 C44 1.370(7) . ?
C43 C48 1.378(7) . ?
C44 C45 1.389(6) . ?
C44 H44A 0.9300 . ?
C45 C46 1.382(7) . ?
C45 H45A 0.9300 . ?
C46 C47 1.363(8) . ?
C47 C48 1.381(7) . ?
C47 H47A 0.9300 . ?
C48 H48A 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
C2 O1 C1 118.0(4) . . ?
C26 O4 C25 117.6(4) . . ?
C10 N1 C11 112.7(5) . . ?
C10 N1 C12 122.6(5) . . ?
C11 N1 C12 124.5(5) . . ?
C19 N2 C8 123.0(4) . . ?
C19 N2 C9 121.7(5) . . ?
C8 N2 C9 62.7(3) . . ?
C43 N3 C32 122.6(4) . . ?
C43 N3 C34 121.8(5) . . ?
C32 N3 C34 61.7(3) . . ?
C35 N4 C33 113.1(4) . . ?
C35 N4 C36 123.2(4) . . ?
C33 N4 C36 123.3(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 115.1(5) . . ?
O1 C2 C3 124.8(5) . . ?
C7 C2 C3 120.1(5) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 121.7(5) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C6 118.1(5) . . ?
C4 C5 C8 121.1(5) . . ?
C6 C5 C8 120.8(5) . . ?
C7 C6 C5 120.8(6) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C6 C7 C2 120.2(5) . . ?
C6 C7 H7A 119.9 . . ?
C2 C7 H7A 119.9 . . ?
N2 C8 C5 117.8(4) . . ?
N2 C8 C9 58.9(3) . . ?
C5 C8 C9 125.4(4) . . ?
N2 C8 C11 115.3(4) . . ?
C5 C8 C11 120.1(5) . . ?
C9 C8 C11 104.5(4) . . ?
N2 C9 C10 116.8(4) . . ?
N2 C9 C8 58.5(3) . . ?
C10 C9 C8 105.4(4) . . ?
N2 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
O2 C10 N1 124.7(5) . . ?
O2 C10 C9 126.6(5) . . ?
N1 C10 C9 108.6(5) . . ?
O3 C11 N1 125.3(5) . . ?
O3 C11 C8 126.0(5) . . ?
N1 C11 C8 108.7(5) . . ?
N1 C12 C13 114.6(4) . . ?
N1 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
N1 C12 H12B 108.6 . . ?
C13 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
C14 C13 C18 121.1(6) . . ?
C14 C13 C12 118.8(6) . . ?
C18 C13 C12 120.0(6) . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C16 C15 C14 118.2(7) . . ?
C16 C15 H15A 120.9 . . ?
C14 C15 H15A 120.9 . . ?
C17 C16 C15 122.6(6) . . ?
C17 C16 H16A 118.7 . . ?
C15 C16 H16A 118.7 . . ?
C16 C17 C18 118.1(6) . . ?
C16 C17 H17A 121.0 . . ?
C18 C17 H17A 121.0 . . ?
C13 C18 C17 119.8(6) . . ?
C13 C18 H18A 120.1 . . ?
C17 C18 H18A 120.1 . . ?
C24 C19 C20 120.2(5) . . ?
C24 C19 N2 120.5(5) . . ?
C20 C19 N2 119.0(6) . . ?
C21 C20 C19 119.9(6) . . ?
C21 C20 H20A 120.1 . . ?
C19 C20 H20A 120.1 . . ?
C22 C21 C20 118.5(5) . . ?
C22 C21 H21A 120.8 . . ?
C20 C21 H21A 120.8 . . ?
C23 C22 C21 122.7(5) . . ?
C23 C22 Br1 120.2(5) . . ?
C21 C22 Br1 117.1(4) . . ?
C22 C23 C24 118.6(5) . . ?
C22 C23 H23A 120.7 . . ?
C24 C23 H23A 120.7 . . ?
C19 C24 C23 120.2(5) . . ?
C19 C24 H24A 119.9 . . ?
C23 C24 H24A 119.9 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 C27 126.8(5) . . ?
O4 C26 C31 114.0(5) . . ?
C27 C26 C31 119.2(5) . . ?
C28 C27 C26 120.2(5) . . ?
C28 C27 H27A 119.9 . . ?
C26 C27 H27A 119.9 . . ?
C27 C28 C29 120.9(5) . . ?
C27 C28 H28A 119.6 . . ?
C29 C28 H28A 119.6 . . ?
C30 C29 C28 119.4(5) . . ?
C30 C29 C32 120.8(6) . . ?
C28 C29 C32 119.9(5) . . ?
C29 C30 C31 121.8(6) . . ?
C29 C30 H30A 119.1 . . ?
C31 C30 H30A 119.1 . . ?
C30 C31 C26 118.6(5) . . ?
C30 C31 H31A 120.7 . . ?
C26 C31 H31A 120.7 . . ?
N3 C32 C34 59.2(3) . . ?
N3 C32 C29 117.0(4) . . ?
C34 C32 C29 126.1(4) . . ?
N3 C32 C33 115.6(4) . . ?
C34 C32 C33 105.0(4) . . ?
C29 C32 C33 119.7(4) . . ?
O5 C33 N4 125.1(5) . . ?
O5 C33 C32 127.5(5) . . ?
N4 C33 C32 107.4(5) . . ?
N3 C34 C35 117.7(4) . . ?
N3 C34 C32 59.1(3) . . ?
C35 C34 C32 106.0(5) . . ?
N3 C34 H34A 119.3 . . ?
C35 C34 H34A 119.4 . . ?
C32 C34 H34A 119.3 . . ?
O6 C35 N4 124.7(5) . . ?
O6 C35 C34 127.1(5) . . ?
N4 C35 C34 108.2(5) . . ?
N4 C36 C37 114.3(4) . . ?
N4 C36 H36A 108.7 . . ?
C37 C36 H36A 108.7 . . ?
N4 C36 H36B 108.7 . . ?
C37 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
C42 C37 C38 120.1(5) . . ?
C42 C37 C36 120.8(6) . . ?
C38 C37 C36 119.0(6) . . ?
C37 C38 C39 118.9(6) . . ?
C37 C38 H38A 120.5 . . ?
C39 C38 H38A 120.5 . . ?
C40 C39 C38 120.8(6) . . ?
C40 C39 H39A 119.6 . . ?
C38 C39 H39A 119.6 . . ?
C39 C40 C41 120.2(6) . . ?
C39 C40 H40A 119.9 . . ?
C41 C40 H40A 119.9 . . ?
C40 C41 C42 120.6(6) . . ?
C40 C41 H41A 119.7 . . ?
C42 C41 H41A 119.7 . . ?
C37 C42 C41 119.4(6) . . ?
C37 C42 H42A 120.3 . . ?
C41 C42 H42A 120.3 . . ?
C44 C43 C48 120.9(5) . . ?
C44 C43 N3 119.7(5) . . ?
C48 C43 N3 119.0(5) . . ?
C43 C44 C45 120.3(5) . . ?
C43 C44 H44A 119.8 . . ?
C45 C44 H44A 119.8 . . ?
C46 C45 C44 117.6(5) . . ?
C46 C45 H45A 121.2 . . ?
C44 C45 H45A 121.2 . . ?
C47 C46 C45 122.6(5) . . ?
C47 C46 Br2 118.9(5) . . ?
C45 C46 Br2 118.5(5) . . ?
C46 C47 C48 119.1(5) . . ?
C46 C47 H47A 120.4 . . ?
C48 C47 H47A 120.4 . . ?
C43 C48 C47 119.4(6) . . ?
C43 C48 H48A 120.3 . . ?
C47 C48 H48A 120.3 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc1zn650
_database_code_depnum_ccdc_archive 'CCDC 1836662'
_audit_update_record             
;
2018-04-12 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 Br N2 O3'
_chemical_formula_weight         479.36

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pbca  '

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

_cell_length_a                   10.532(6)
_cell_length_b                   9.624(5)
_cell_length_c                   43.850(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4445(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1600
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      18.82

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    1.879
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_T_max  0.6937
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20739
_diffrn_reflns_av_R_equivalents  0.1547
_diffrn_reflns_av_sigmaI/netI    0.1266
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3916
_reflns_number_gt                1686
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0100P)²+10.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3916
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38297(10) 0.31446(10) 0.02634(2) 0.0902(4) Uani 1 1 d . . .
O1 O 0.6948(4) 0.3681(5) 0.12645(10) 0.0486(13) Uani 1 1 d . . .
O2 O 0.3697(6) 0.2035(6) 0.20263(11) 0.0791(16) Uani 1 1 d . . .
O3 O 0.5351(6) 0.3117(7) 0.22301(13) 0.107(2) Uani 1 1 d . . .
N1 N 0.4360(5) 0.2625(5) 0.14372(12) 0.0423(14) Uani 1 1 d . . .
N2 N 0.7314(5) 0.1441(5) 0.11435(12) 0.0457(15) Uani 1 1 d . . .
H2B H 0.7016 0.0609 0.1144 0.055 Uiso 1 1 calc R . .
C1 C 0.3794(7) 0.3843(8) 0.06561(16) 0.055(2) Uani 1 1 d . . .
C2 C 0.3357(7) 0.5181(9) 0.0713(2) 0.066(2) Uani 1 1 d . . .
H2A H 0.3105 0.5750 0.0552 0.079 Uiso 1 1 calc R . .
C3 C 0.3301(7) 0.5649(8) 0.1005(2) 0.068(2) Uani 1 1 d . . .
H3A H 0.3009 0.6546 0.1041 0.081 Uiso 1 1 calc R . .
C4 C 0.3664(6) 0.4837(7) 0.12473(18) 0.0532(19) Uani 1 1 d . . .
H4A H 0.3603 0.5172 0.1446 0.064 Uiso 1 1 calc R . .
C5 C 0.4118(6) 0.3520(7) 0.11922(16) 0.0438(18) Uani 1 1 d . . .
C6 C 0.4183(6) 0.3026(7) 0.08984(16) 0.0471(18) Uani 1 1 d . . .
H6A H 0.4491 0.2136 0.0862 0.057 Uiso 1 1 calc R . .
C7 C 0.5106(6) 0.3093(7) 0.16972(15) 0.0491(18) Uani 1 1 d . . .
H7A H 0.5505 0.4005 0.1669 0.059 Uiso 1 1 calc R . .
C8 C 0.5617(6) 0.1972(6) 0.14889(13) 0.0364(15) Uani 1 1 d . . .
C9 C 0.6667(6) 0.2439(8) 0.12885(15) 0.0393(16) Uani 1 1 d . . .
C10 C 0.8496(6) 0.1708(7) 0.09851(15) 0.055(2) Uani 1 1 d . . .
H10A H 0.8784 0.0841 0.0896 0.066 Uiso 1 1 calc R . .
H10B H 0.9123 0.1983 0.1135 0.066 Uiso 1 1 calc R . .
C11 C 0.8483(7) 0.2788(6) 0.07378(15) 0.0433(18) Uani 1 1 d . . .
C12 C 0.9578(7) 0.3540(7) 0.06864(17) 0.060(2) Uani 1 1 d . . .
H12A H 1.0288 0.3393 0.0808 0.072 Uiso 1 1 calc R . .
C13 C 0.9623(9) 0.4502(9) 0.0456(2) 0.075(3) Uani 1 1 d . . .
H13A H 1.0373 0.4984 0.0420 0.090 Uiso 1 1 calc R . .
C14 C 0.8595(10) 0.4762(9) 0.0281(2) 0.080(3) Uani 1 1 d . . .
H14A H 0.8635 0.5432 0.0128 0.096 Uiso 1 1 calc R . .
C15 C 0.7495(9) 0.4036(8) 0.03283(17) 0.069(2) Uani 1 1 d . . .
H15A H 0.6783 0.4203 0.0209 0.082 Uiso 1 1 calc R . .
C16 C 0.7461(7) 0.3044(8) 0.05590(16) 0.059(2) Uani 1 1 d . . .
H16A H 0.6718 0.2544 0.0591 0.071 Uiso 1 1 calc R . .
C17 C 0.5556(6) 0.0488(6) 0.15972(14) 0.0376(16) Uani 1 1 d . . .
C18 C 0.6491(7) -0.0003(7) 0.17915(14) 0.0483(18) Uani 1 1 d . . .
H18A H 0.7174 0.0564 0.1842 0.058 Uiso 1 1 calc R . .
C19 C 0.6416(8) -0.1324(8) 0.19095(16) 0.063(2) Uani 1 1 d . . .
H19A H 0.7049 -0.1654 0.2038 0.076 Uiso 1 1 calc R . .
C20 C 0.5386(9) -0.2165(8) 0.18348(19) 0.071(2) Uani 1 1 d . . .
H20A H 0.5317 -0.3052 0.1917 0.085 Uiso 1 1 calc R . .
C21 C 0.4486(8) -0.1684(8) 0.16419(18) 0.071(2) Uani 1 1 d . . .
H21A H 0.3810 -0.2254 0.1587 0.086 Uiso 1 1 calc R . .
C22 C 0.4563(7) -0.0367(7) 0.15264(16) 0.0511(19) Uani 1 1 d . . .
H22A H 0.3927 -0.0047 0.1397 0.061 Uiso 1 1 calc R . .
C23 C 0.4748(9) 0.2784(8) 0.20109(19) 0.062(2) Uani 1 1 d . . .
C24 C 0.3340(11) 0.1489(13) 0.2325(2) 0.124(4) Uani 1 1 d . . .
H24A H 0.4070 0.1045 0.2418 0.149 Uiso 1 1 calc R . .
H24B H 0.3079 0.2250 0.2455 0.149 Uiso 1 1 calc R . .
C25 C 0.2366(15) 0.0544(14) 0.2302(3) 0.167(6) Uani 1 1 d . . .
H25A H 0.2163 0.0192 0.2501 0.250 Uiso 1 1 calc R . .
H25B H 0.2622 -0.0210 0.2172 0.250 Uiso 1 1 calc R . .
H25C H 0.1633 0.0990 0.2216 0.250 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 C1 1.849(7) . ?
O1 C9 1.236(7) . ?
O2 C23 1.322(9) . ?
O2 C24 1.459(10) . ?
O3 C23 1.196(9) . ?
N1 C5 1.400(8) . ?
N1 C7 1.456(8) . ?
N1 C8 1.483(7) . ?
N2 C9 1.338(7) . ?
N2 C10 1.449(7) . ?
N2 H2B 0.8600 . ?
C1 C6 1.384(8) . ?
C1 C2 1.389(10) . ?
C2 C3 1.359(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.375(10) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(9) . ?
C6 H6A 0.9300 . ?
C7 C23 1.457(9) . ?
C7 C8 1.512(8) . ?
C7 H7A 0.9800 . ?
C8 C9 1.483(8) . ?
C8 C17 1.506(8) . ?
C10 C11 1.502(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.354(9) . ?
C11 C12 1.380(9) . ?
C12 C13 1.371(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.352(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.369(11) . ?
C14 H14A 0.9300 . ?
C15 C16 1.391(9) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C22 1.366(8) . ?
C17 C18 1.386(9) . ?
C18 C19 1.375(9) . ?
C18 H18A 0.9300 . ?
C19 C20 1.392(10) . ?
C19 H19A 0.9300 . ?
C20 C21 1.352(10) . ?
C20 H20A 0.9300 . ?
C21 C22 1.368(9) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C24 C25 1.374(13) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C23 O2 C24 117.3(7) . . ?
C5 N1 C7 120.6(5) . . ?
C5 N1 C8 122.7(5) . . ?
C7 N1 C8 61.9(4) . . ?
C9 N2 C10 122.5(6) . . ?
C9 N2 H2B 118.7 . . ?
C10 N2 H2B 118.7 . . ?
C6 C1 C2 119.2(7) . . ?
C6 C1 Br1 120.1(6) . . ?
C2 C1 Br1 120.6(6) . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 121.9(7) . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 119.0(7) . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 H4A 120.5 . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 N1 119.8(6) . . ?
C4 C5 N1 119.7(7) . . ?
C5 C6 C1 120.5(7) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
N1 C7 C23 122.4(7) . . ?
N1 C7 C8 59.9(4) . . ?
C23 C7 C8 121.1(6) . . ?
N1 C7 H7A 114.3 . . ?
C23 C7 H7A 114.3 . . ?
C8 C7 H7A 114.3 . . ?
N1 C8 C9 116.6(5) . . ?
N1 C8 C17 114.3(5) . . ?
C9 C8 C17 120.4(5) . . ?
N1 C8 C7 58.2(4) . . ?
C9 C8 C7 114.0(5) . . ?
C17 C8 C7 118.1(5) . . ?
O1 C9 N2 122.2(6) . . ?
O1 C9 C8 121.5(6) . . ?
N2 C9 C8 116.3(6) . . ?
N2 C10 C11 117.5(6) . . ?
N2 C10 H10A 107.9 . . ?
C11 C10 H10A 107.9 . . ?
N2 C10 H10B 107.9 . . ?
C11 C10 H10B 107.9 . . ?
H10A C10 H10B 107.2 . . ?
C16 C11 C12 118.3(6) . . ?
C16 C11 C10 123.4(7) . . ?
C12 C11 C10 118.2(6) . . ?
C13 C12 C11 120.2(8) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 121.2(8) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 119.7(8) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C14 C15 C16 118.9(8) . . ?
C14 C15 H15A 120.5 . . ?
C16 C15 H15A 120.5 . . ?
C11 C16 C15 121.7(7) . . ?
C11 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C22 C17 C18 118.6(6) . . ?
C22 C17 C8 122.2(6) . . ?
C18 C17 C8 119.1(6) . . ?
C19 C18 C17 120.4(7) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 119.6(7) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
C21 C20 C19 119.6(7) . . ?
C21 C20 H20A 120.2 . . ?
C19 C20 H20A 120.2 . . ?
C20 C21 C22 120.5(7) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C17 C22 C21 121.3(7) . . ?
C17 C22 H22A 119.4 . . ?
C21 C22 H22A 119.4 . . ?
O3 C23 O2 123.3(8) . . ?
O3 C23 C7 124.5(8) . . ?
O2 C23 C7 112.1(7) . . ?
C25 C24 O2 111.5(9) . . ?
C25 C24 H24A 109.3 . . ?
O2 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
O2 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.080
