# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1956830'
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2019-12-16 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 H14 F N O2'
_chemical_formula_weight         367.36

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'I4(1)/a  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   22.6155(5)
_cell_length_b                   22.6155(5)
_cell_length_c                   13.8933(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7105.9(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2181
_cell_measurement_theta_min      2.4905
_cell_measurement_theta_max      25.7285

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3040
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23218
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4412
_reflns_number_gt                2348
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0449P)²+3.4904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4412
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
O1 O 0.82458(6) 0.41498(6) 0.05217(10) 0.0287(4) Uani 1 1 d . . .
C2 C 0.73971(10) 0.47934(9) 0.05502(14) 0.0259(5) Uani 1 1 d . . .
F F 0.85478(7) 0.61900(6) 0.06692(12) 0.0581(5) Uani 1 1 d . . .
C4 C 0.69963(10) 0.42811(10) 0.05458(15) 0.0280(5) Uani 1 1 d . . .
C5 C 0.67743(9) 0.28861(9) -0.04121(15) 0.0264(5) Uani 1 1 d . . .
C6 C 0.63765(11) 0.24037(10) -0.04019(16) 0.0334(5) Uani 1 1 d . . .
C7 C 0.84030(11) 0.51718(10) 0.05658(15) 0.0335(6) Uani 1 1 d . . .
H7A H 0.8818 0.5106 0.0553 0.040 Uiso 1 1 calc R . .
C8 C 0.80019(10) 0.47055(9) 0.05405(14) 0.0267(5) Uani 1 1 d . . .
C9 C 0.71905(11) 0.53761(10) 0.05721(15) 0.0316(5) Uani 1 1 d . . .
H9A H 0.6777 0.5447 0.0565 0.038 Uiso 1 1 calc R . .
C10 C 0.82427(9) 0.31212(10) 0.05171(14) 0.0268(5) Uani 1 1 d . . .
O2 O 0.64560(7) 0.43368(7) 0.05688(12) 0.0389(4) Uani 1 1 d . . .
N N 0.66833(9) 0.29904(8) 0.13130(13) 0.0335(5) Uani 1 1 d . . .
C13 C 0.78837(10) 0.36670(9) 0.05149(14) 0.0256(5) Uani 1 1 d . . .
C14 C 0.72893(9) 0.37063(9) 0.05173(14) 0.0246(5) Uani 1 1 d . . .
C15 C 0.81713(11) 0.57269(10) 0.06098(16) 0.0362(6) Uani 1 1 d . . .
C16 C 0.75714(11) 0.58454(11) 0.06030(16) 0.0368(6) Uani 1 1 d . . .
H16A H 0.7428 0.6240 0.0619 0.044 Uiso 1 1 calc R . .
C17 C 0.81416(10) 0.26779(10) 0.11926(15) 0.0321(5) Uani 1 1 d . . .
H17A H 0.7819 0.2710 0.1627 0.039 Uiso 1 1 calc R . .
C18 C 0.63104(11) 0.25145(11) 0.12988(17) 0.0408(6) Uani 1 1 d . . .
H18A H 0.6155 0.2381 0.1895 0.049 Uiso 1 1 calc R . .
C19 C 0.61491(11) 0.22223(11) 0.04938(17) 0.0402(6) Uani 1 1 d . . .
H19A H 0.5884 0.1897 0.0531 0.048 Uiso 1 1 calc R . .
C20 C 0.69054(9) 0.31674(9) 0.04860(15) 0.0257(5) Uani 1 1 d . . .
C21 C 0.70207(10) 0.30708(10) -0.13001(15) 0.0321(5) Uani 1 1 d . . .
H21A H 0.7299 0.3386 -0.1315 0.039 Uiso 1 1 calc R . .
C22 C 0.64608(13) 0.23235(12) -0.21245(18) 0.0489(7) Uani 1 1 d . . .
H22A H 0.6352 0.2139 -0.2713 0.059 Uiso 1 1 calc R . .
C23 C 0.62278(12) 0.21237(12) -0.12828(19) 0.0463(7) Uani 1 1 d . . .
H23A H 0.5965 0.1796 -0.1285 0.056 Uiso 1 1 calc R . .
C24 C 0.89792(11) 0.21430(11) 0.06008(16) 0.0362(6) Uani 1 1 d . . .
H24A H 0.9236 0.1812 0.0637 0.043 Uiso 1 1 calc R . .
C25 C 0.87141(10) 0.30672(10) -0.01220(15) 0.0318(5) Uani 1 1 d . . .
H25A H 0.8787 0.3368 -0.0584 0.038 Uiso 1 1 calc R . .
C26 C 0.68583(11) 0.27960(11) -0.21350(17) 0.0411(6) Uani 1 1 d . . .
H26A H 0.7018 0.2928 -0.2730 0.049 Uiso 1 1 calc R . .
C27 C 0.85113(11) 0.21901(10) 0.12325(17) 0.0353(6) Uani 1 1 d . . .
H27A H 0.8442 0.1888 0.1695 0.042 Uiso 1 1 calc R . .
C28 C 0.90758(11) 0.25747(11) -0.00839(16) 0.0364(6) Uani 1 1 d . . .
H28A H 0.9391 0.2533 -0.0530 0.044 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
O1 C13 1.365(2) . ?
O1 C8 1.373(3) . ?
C2 C8 1.382(3) . ?
C2 C9 1.399(3) . ?
C2 C4 1.471(3) . ?
F C15 1.352(2) . ?
C4 O2 1.229(3) . ?
C4 C14 1.460(3) . ?
C5 C6 1.414(3) . ?
C5 C21 1.417(3) . ?
C5 C20 1.432(3) . ?
C6 C19 1.408(3) . ?
C6 C23 1.418(3) . ?
C7 C15 1.362(3) . ?
C7 C8 1.392(3) . ?
C7 H7A 0.9500 . ?
C9 C16 1.368(3) . ?
C9 H9A 0.9500 . ?
C10 C17 1.392(3) . ?
C10 C25 1.393(3) . ?
C10 C13 1.478(3) . ?
N C20 1.316(3) . ?
N C18 1.367(3) . ?
C13 C14 1.347(3) . ?
C14 C20 1.497(3) . ?
C15 C16 1.383(3) . ?
C16 H16A 0.9500 . ?
C17 C27 1.385(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.349(3) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C21 C26 1.366(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.360(4) . ?
C22 C26 1.396(4) . ?
C22 H22A 0.9500 . ?
C23 H23A 0.9500 . ?
C24 C27 1.379(3) . ?
C24 C28 1.381(3) . ?
C24 H24A 0.9500 . ?
C25 C28 1.383(3) . ?
C25 H25A 0.9500 . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?
C28 H28A 0.9500 . ?

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 O1 C8 119.42(17) . . ?
C8 C2 C9 117.8(2) . . ?
C8 C2 C4 119.8(2) . . ?
C9 C2 C4 122.4(2) . . ?
O2 C4 C14 122.9(2) . . ?
O2 C4 C2 122.1(2) . . ?
C14 C4 C2 114.94(19) . . ?
C6 C5 C21 119.1(2) . . ?
C6 C5 C20 117.76(19) . . ?
C21 C5 C20 123.1(2) . . ?
C19 C6 C5 117.8(2) . . ?
C19 C6 C23 123.1(2) . . ?
C5 C6 C23 119.1(2) . . ?
C15 C7 C8 116.7(2) . . ?
C15 C7 H7A 121.7 . . ?
C8 C7 H7A 121.7 . . ?
O1 C8 C2 121.98(19) . . ?
O1 C8 C7 115.6(2) . . ?
C2 C8 C7 122.4(2) . . ?
C16 C9 C2 121.4(2) . . ?
C16 C9 H9A 119.3 . . ?
C2 C9 H9A 119.3 . . ?
C17 C10 C25 119.5(2) . . ?
C17 C10 C13 120.84(19) . . ?
C25 C10 C13 119.5(2) . . ?
C20 N C18 117.52(19) . . ?
C14 C13 O1 123.1(2) . . ?
C14 C13 C10 127.1(2) . . ?
O1 C13 C10 109.78(18) . . ?
C13 C14 C4 120.8(2) . . ?
C13 C14 C20 121.68(19) . . ?
C4 C14 C20 117.54(18) . . ?
F C15 C7 118.3(2) . . ?
F C15 C16 117.9(2) . . ?
C7 C15 C16 123.8(2) . . ?
C9 C16 C15 117.9(2) . . ?
C9 C16 H16A 121.1 . . ?
C15 C16 H16A 121.1 . . ?
C27 C17 C10 120.1(2) . . ?
C27 C17 H17A 120.0 . . ?
C10 C17 H17A 120.0 . . ?
C19 C18 N 124.3(2) . . ?
C19 C18 H18A 117.8 . . ?
N C18 H18A 117.8 . . ?
C18 C19 C6 119.4(2) . . ?
C18 C19 H19A 120.3 . . ?
C6 C19 H19A 120.3 . . ?
N C20 C5 123.14(19) . . ?
N C20 C14 116.33(18) . . ?
C5 C20 C14 120.47(18) . . ?
C26 C21 C5 120.0(2) . . ?
C26 C21 H21A 120.0 . . ?
C5 C21 H21A 120.0 . . ?
C23 C22 C26 120.9(2) . . ?
C23 C22 H22A 119.6 . . ?
C26 C22 H22A 119.6 . . ?
C22 C23 C6 120.1(2) . . ?
C22 C23 H23A 119.9 . . ?
C6 C23 H23A 119.9 . . ?
C27 C24 C28 120.4(2) . . ?
C27 C24 H24A 119.8 . . ?
C28 C24 H24A 119.8 . . ?
C28 C25 C10 119.9(2) . . ?
C28 C25 H25A 120.0 . . ?
C10 C25 H25A 120.0 . . ?
C21 C26 C22 120.8(2) . . ?
C21 C26 H26A 119.6 . . ?
C22 C26 H26A 119.6 . . ?
C24 C27 C17 119.9(2) . . ?
C24 C27 H27A 120.0 . . ?
C17 C27 H27A 120.0 . . ?
C24 C28 C25 120.1(2) . . ?
C24 C28 H28A 119.9 . . ?
C25 C28 H28A 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1956831'
_audit_update_record             
;
2019-09-30 deposited with the CCDC.	2019-12-16 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 H15 Cl3 F N O2'
_chemical_formula_weight         486.73

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1531(2)
_cell_length_b                   11.9242(3)
_cell_length_c                   12.1940(3)
_cell_angle_alpha                103.1080(10)
_cell_angle_beta                 101.7440(10)
_cell_angle_gamma                104.1880(10)
_cell_volume                     1076.41(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6604
_cell_measurement_theta_min      2.9135
_cell_measurement_theta_max      28.253

_exptl_crystal_description       schistose
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.2000
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17027
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28.30
_reflns_number_total             5327
_reflns_number_gt                4240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0384P)²+0.7702P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5327
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Cl1 Cl 0.42494(8) 0.00720(5) 0.33846(6) 0.04987(17) Uani 1 1 d . . .
Cl2 Cl 0.10125(8) 0.02271(5) 0.39067(6) 0.05109(17) Uani 1 1 d . . .
Cl3 Cl 0.31983(10) 0.22030(6) 0.33505(6) 0.05374(18) Uani 1 1 d . . .
O1 O 0.56497(18) 0.52999(12) 0.70263(11) 0.0295(3) Uani 1 1 d . . .
N N 0.63588(19) 0.40421(13) 1.00316(12) 0.0217(3) Uani 1 1 d . . .
O2 O 0.39625(19) 0.22219(13) 0.65892(11) 0.0355(3) Uani 1 1 d . . .
C4 C 0.6937(2) 0.44958(15) 0.91712(14) 0.0197(3) Uani 1 1 d . . .
C5 C 0.8351(2) 0.56532(15) 0.95846(14) 0.0204(3) Uani 1 1 d . . .
C6 C 0.7942(2) 0.58981(17) 1.15412(15) 0.0258(4) Uani 1 1 d . . .
H6A H 0.8173 0.6384 1.2323 0.031 Uiso 1 1 calc R . .
F F 0.9137(2) 0.27970(15) 0.34415(12) 0.0600(4) Uani 1 1 d . . .
C8 C 0.4818(2) 0.27290(16) 0.76309(15) 0.0244(4) Uani 1 1 d . . .
C9 C 0.6824(2) 0.47813(16) 1.11865(14) 0.0242(4) Uani 1 1 d . . .
H9A H 0.6324 0.4475 1.1738 0.029 Uiso 1 1 calc R . .
C10 C 0.6270(2) 0.44668(16) 0.70359(14) 0.0223(3) Uani 1 1 d . . .
C11 C 0.4453(2) 0.21929(16) 0.85564(15) 0.0246(4) Uani 1 1 d . . .
C12 C 0.8799(2) 0.63746(16) 1.07570(15) 0.0233(3) Uani 1 1 d . . .
C13 C 0.5193(2) 0.28587(16) 0.97358(15) 0.0243(4) Uani 1 1 d . . .
C14 C 0.7054(2) 0.40084(16) 0.60947(14) 0.0230(3) Uani 1 1 d . . .
C15 C 0.6153(2) 0.38696(15) 0.79979(14) 0.0213(3) Uani 1 1 d . . .
C16 C 0.7158(2) 0.45942(18) 0.52298(16) 0.0292(4) Uani 1 1 d . . .
H16A H 0.6738 0.5273 0.5254 0.035 Uiso 1 1 calc R . .
C17 C 1.0586(3) 0.71878(17) 0.92362(16) 0.0295(4) Uani 1 1 d . . .
H17A H 1.1216 0.7459 0.8723 0.035 Uiso 1 1 calc R . .
C18 C 1.0074(3) 0.75128(17) 1.11305(16) 0.0299(4) Uani 1 1 d . . .
H18A H 1.0334 0.8007 1.1912 0.036 Uiso 1 1 calc R . .
C19 C 0.3276(3) 0.10260(17) 0.82540(17) 0.0312(4) Uani 1 1 d . . .
H19A H 0.2767 0.0580 0.7452 0.037 Uiso 1 1 calc R . .
C20 C 0.9317(2) 0.60736(16) 0.88475(15) 0.0238(3) Uani 1 1 d . . .
H20A H 0.9092 0.5582 0.8069 0.029 Uiso 1 1 calc R . .
C21 C 0.3170(3) 0.10526(17) 0.40124(16) 0.0307(4) Uani 1 1 d . . .
H21A H 0.3814 0.1429 0.4861 0.037 Uiso 1 1 calc R . .
C22 C 0.7690(3) 0.30247(18) 0.60611(16) 0.0298(4) Uani 1 1 d . . .
H22A H 0.7638 0.2634 0.6657 0.036 Uiso 1 1 calc R . .
C23 C 0.7872(3) 0.4189(2) 0.43389(17) 0.0369(5) Uani 1 1 d . . .
H23A H 0.7956 0.4585 0.3749 0.044 Uiso 1 1 calc R . .
C24 C 0.4755(3) 0.23295(19) 1.06001(17) 0.0362(5) Uani 1 1 d . . .
H24A H 0.5254 0.2765 1.1406 0.043 Uiso 1 1 calc R . .
C25 C 1.0949(3) 0.79195(18) 1.03794(17) 0.0331(4) Uani 1 1 d . . .
H25A H 1.1799 0.8697 1.0637 0.040 Uiso 1 1 calc R . .
C26 C 0.8398(3) 0.2607(2) 0.51661(18) 0.0373(5) Uani 1 1 d . . .
H26A H 0.8828 0.1932 0.5135 0.045 Uiso 1 1 calc R . .
C27 C 0.2851(3) 0.05198(19) 0.9101(2) 0.0419(5) Uani 1 1 d . . .
H27A H 0.2053 -0.0273 0.8891 0.050 Uiso 1 1 calc R . .
C28 C 0.8457(3) 0.3202(2) 0.43255(17) 0.0375(5) Uani 1 1 d . . .
C29 C 0.3601(3) 0.1180(2) 1.02728(19) 0.0451(6) Uani 1 1 d . . .
H29A H 0.3310 0.0829 1.0861 0.054 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
Cl1 C21 1.761(2) . ?
Cl2 C21 1.755(2) . ?
Cl3 C21 1.740(2) . ?
O1 C10 1.221(2) . ?
N C4 1.396(2) . ?
N C9 1.400(2) . ?
N C13 1.413(2) . ?
O2 C8 1.245(2) . ?
C4 C15 1.386(2) . ?
C4 C5 1.468(2) . ?
C5 C20 1.407(2) . ?
C5 C12 1.412(2) . ?
C6 C9 1.332(3) . ?
C6 C12 1.431(2) . ?
C6 H6A 0.9500 . ?
F C28 1.357(2) . ?
C8 C15 1.426(2) . ?
C8 C11 1.463(2) . ?
C9 H9A 0.9500 . ?
C10 C14 1.487(2) . ?
C10 C15 1.511(2) . ?
C11 C13 1.399(2) . ?
C11 C19 1.400(3) . ?
C12 C18 1.402(3) . ?
C13 C24 1.408(2) . ?
C14 C22 1.389(3) . ?
C14 C16 1.396(2) . ?
C16 C23 1.382(3) . ?
C16 H16A 0.9500 . ?
C17 C20 1.379(3) . ?
C17 C25 1.395(3) . ?
C17 H17A 0.9500 . ?
C18 C25 1.371(3) . ?
C18 H18A 0.9500 . ?
C19 C27 1.371(3) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 H21A 1.0000 . ?
C22 C26 1.387(3) . ?
C22 H22A 0.9500 . ?
C23 C28 1.372(3) . ?
C23 H23A 0.9500 . ?
C24 C29 1.374(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C28 1.375(3) . ?
C26 H26A 0.9500 . ?
C27 C29 1.390(3) . ?
C27 H27A 0.9500 . ?
C29 H29A 0.9500 . ?

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
C4 N C9 120.47(15) . . ?
C4 N C13 120.58(14) . . ?
C9 N C13 118.80(14) . . ?
C15 C4 N 119.92(15) . . ?
C15 C4 C5 123.62(15) . . ?
N C4 C5 116.45(14) . . ?
C20 C5 C12 117.81(16) . . ?
C20 C5 C4 121.95(15) . . ?
C12 C5 C4 120.23(15) . . ?
C9 C6 C12 120.70(16) . . ?
C9 C6 H6A 119.6 . . ?
C12 C6 H6A 119.6 . . ?
O2 C8 C15 122.66(16) . . ?
O2 C8 C11 121.01(17) . . ?
C15 C8 C11 116.30(15) . . ?
C6 C9 N 122.49(16) . . ?
C6 C9 H9A 118.8 . . ?
N C9 H9A 118.8 . . ?
O1 C10 C14 121.02(15) . . ?
O1 C10 C15 118.61(15) . . ?
C14 C10 C15 120.31(15) . . ?
C13 C11 C19 119.85(16) . . ?
C13 C11 C8 120.60(16) . . ?
C19 C11 C8 119.46(16) . . ?
C18 C12 C5 120.10(16) . . ?
C18 C12 C6 121.81(16) . . ?
C5 C12 C6 118.08(16) . . ?
C11 C13 C24 118.95(17) . . ?
C11 C13 N 119.43(15) . . ?
C24 C13 N 121.62(16) . . ?
C22 C14 C16 119.61(16) . . ?
C22 C14 C10 121.81(15) . . ?
C16 C14 C10 118.58(16) . . ?
C4 C15 C8 121.97(15) . . ?
C4 C15 C10 122.39(15) . . ?
C8 C15 C10 113.70(14) . . ?
C23 C16 C14 120.14(18) . . ?
C23 C16 H16A 119.9 . . ?
C14 C16 H16A 119.9 . . ?
C20 C17 C25 120.38(17) . . ?
C20 C17 H17A 119.8 . . ?
C25 C17 H17A 119.8 . . ?
C25 C18 C12 120.69(17) . . ?
C25 C18 H18A 119.7 . . ?
C12 C18 H18A 119.7 . . ?
C27 C19 C11 120.80(19) . . ?
C27 C19 H19A 119.6 . . ?
C11 C19 H19A 119.6 . . ?
C17 C20 C5 121.08(16) . . ?
C17 C20 H20A 119.5 . . ?
C5 C20 H20A 119.5 . . ?
Cl3 C21 Cl2 111.47(12) . . ?
Cl3 C21 Cl1 110.69(11) . . ?
Cl2 C21 Cl1 109.78(10) . . ?
Cl3 C21 H21A 108.3 . . ?
Cl2 C21 H21A 108.3 . . ?
Cl1 C21 H21A 108.3 . . ?
C26 C22 C14 120.65(18) . . ?
C26 C22 H22A 119.7 . . ?
C14 C22 H22A 119.7 . . ?
C28 C23 C16 118.46(18) . . ?
C28 C23 H23A 120.8 . . ?
C16 C23 H23A 120.8 . . ?
C29 C24 C13 119.68(19) . . ?
C29 C24 H24A 120.2 . . ?
C13 C24 H24A 120.2 . . ?
C18 C25 C17 119.76(18) . . ?
C18 C25 H25A 120.1 . . ?
C17 C25 H25A 120.1 . . ?
C28 C26 C22 117.81(19) . . ?
C28 C26 H26A 121.1 . . ?
C22 C26 H26A 121.1 . . ?
C19 C27 C29 119.2(2) . . ?
C19 C27 H27A 120.4 . . ?
C29 C27 H27A 120.4 . . ?
F C28 C23 118.33(18) . . ?
F C28 C26 118.4(2) . . ?
C23 C28 C26 123.31(18) . . ?
C24 C29 C27 121.54(19) . . ?
C24 C29 H29A 119.2 . . ?
C27 C29 H29A 119.2 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.873
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1959692'
_audit_update_record             
;
2019-10-16 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_audit_creation_date             2019-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 Br N O2'
_chemical_formula_sum            'C25 H18 Br N O2'
_chemical_formula_weight         444.31
_chemical_melting_point          ?
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.411(2)
_cell_length_b                   12.752(4)
_cell_length_c                   21.926(6)
_cell_angle_alpha                77.759(8)
_cell_angle_beta                 88.648(9)
_cell_angle_gamma                85.507(8)
_cell_volume                     2018.8(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    2.057
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8137. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31422
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         2.233
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4350
_reflns_number_total             9993
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9993
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.038
_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)+(0.0801P)²+0.1978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1901
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C4', C5'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5', C6'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2', C1'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C5') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C2')
\\sim Ueq, Uanis(C1') \\sim Ueq, Uanis(C6') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), N1(H1), C2'(H2'),
 C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'),
 C18'(H18'), C19'(H19'), C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'),
 N1'(H1')
4.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16'(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.53899(7) 0.42943(5) 0.23916(3) 0.0798(2) Uani 1 1 d . . . . .
C1 C 0.3191(6) 0.3611(4) 0.2522(2) 0.0497(11) Uani 1 1 d . . . . .
C2 C 0.1764(7) 0.4110(4) 0.2797(2) 0.0562(12) Uani 1 1 d . . . . .
H2 H 0.1913 0.4742 0.2932 0.067 Uiso 1 1 calc R . . . .
C3 C 0.0138(7) 0.3666(4) 0.2868(2) 0.0608(13) Uani 1 1 d . . . . .
H3 H -0.0834 0.4009 0.3043 0.073 Uiso 1 1 calc R . . . .
C4 C -0.0081(6) 0.2717(4) 0.2684(2) 0.0581(12) Uani 1 1 d . . . . .
H4 H -0.1202 0.2429 0.2737 0.070 Uiso 1 1 calc R . . . .
C5 C 0.1320(6) 0.2189(4) 0.24255(18) 0.0453(10) Uani 1 1 d . . . . .
H5 H 0.1171 0.1534 0.2318 0.054 Uiso 1 1 calc R . . . .
C6 C 0.3007(6) 0.2664(3) 0.23239(18) 0.0426(10) Uani 1 1 d . . . . .
C7 C 0.4570(6) 0.2106(3) 0.2032(2) 0.0439(10) Uani 1 1 d . . . . .
C8 C 0.4391(5) 0.2011(3) 0.14004(18) 0.0406(10) Uani 1 1 d . . . . .
C9 C 0.2594(6) 0.2384(3) 0.11011(19) 0.0423(10) Uani 1 1 d . . . . .
C10 C 0.1999(6) 0.3558(3) 0.09759(19) 0.0418(10) Uani 1 1 d . . . . .
C11 C 0.3246(6) 0.4327(3) 0.0854(2) 0.0517(11) Uani 1 1 d . . . . .
H11 H 0.4476 0.4114 0.0880 0.062 Uiso 1 1 calc R . . . .
C12 C 0.2684(7) 0.5412(4) 0.0692(2) 0.0594(13) Uani 1 1 d . . . . .
H12 H 0.3549 0.5914 0.0600 0.071 Uiso 1 1 calc R . . . .
C13 C 0.0863(7) 0.5768(4) 0.0665(2) 0.0535(12) Uani 1 1 d . . . . .
C14 C -0.0361(7) 0.4991(4) 0.0803(2) 0.0578(13) Uani 1 1 d . . . . .
H14 H -0.1590 0.5206 0.0796 0.069 Uiso 1 1 calc R . . . .
C15 C 0.0171(6) 0.3899(4) 0.0953(2) 0.0506(11) Uani 1 1 d . . . . .
H15 H -0.0696 0.3397 0.1038 0.061 Uiso 1 1 calc R . . . .
C16 C 0.0287(8) 0.6943(4) 0.0478(2) 0.0758(16) Uani 1 1 d . . . . .
H16A H 0.0504 0.7189 0.0039 0.114 Uiso 1 1 calc GR . . . .
H16B H 0.0966 0.7338 0.0708 0.114 Uiso 1 1 calc GR . . . .
H16C H -0.0980 0.7057 0.0566 0.114 Uiso 1 1 calc GR . . . .
C17 C 0.5723(6) 0.1409(3) 0.11172(19) 0.0434(10) Uani 1 1 d . . . . .
C18 C 0.8289(6) 0.0100(4) 0.1284(3) 0.0588(13) Uani 1 1 d . . . . .
H18 H 0.9167 -0.0274 0.1560 0.071 Uiso 1 1 calc R . . . .
C19 C 0.8249(6) -0.0063(4) 0.0704(2) 0.0581(13) Uani 1 1 d . . . . .
H19 H 0.9015 -0.0603 0.0589 0.070 Uiso 1 1 calc R . . . .
C20 C 0.7052(6) 0.0579(4) 0.0265(2) 0.0507(11) Uani 1 1 d . . . . .
C21 C 0.5824(6) 0.1360(3) 0.0455(2) 0.0446(10) Uani 1 1 d . . . . .
C22 C 0.4787(6) 0.2083(4) -0.0005(2) 0.0514(11) Uani 1 1 d . . . . .
H22 H 0.4034 0.2629 0.0109 0.062 Uiso 1 1 calc R . . . .
C23 C 0.4872(7) 0.1993(4) -0.0622(2) 0.0642(13) Uani 1 1 d . . . . .
H23 H 0.4189 0.2477 -0.0922 0.077 Uiso 1 1 calc R . . . .
C24 C 0.5992(8) 0.1168(5) -0.0789(2) 0.0693(15) Uani 1 1 d . . . . .
H24 H 0.6011 0.1088 -0.1201 0.083 Uiso 1 1 calc R . . . .
C25 C 0.7054(7) 0.0481(4) -0.0364(3) 0.0611(13) Uani 1 1 d . . . . .
H25 H 0.7792 -0.0061 -0.0489 0.073 Uiso 1 1 calc R . . . .
N1 N 0.7051(5) 0.0811(3) 0.14744(17) 0.0499(9) Uani 1 1 d . . . . .
H1 H 0.7117 0.0886 0.1854 0.060 Uiso 1 1 calc R . . . .
O1 O 0.5871(4) 0.1697(3) 0.23807(15) 0.0601(9) Uani 1 1 d . . . . .
O2 O 0.1639(4) 0.1757(2) 0.09433(14) 0.0532(8) Uani 1 1 d . . . . .
Br1' Br -0.29139(9) 0.10950(6) 0.73812(3) 0.1008(3) Uani 1 1 d . . . . .
C1' C -0.1043(8) 0.1950(4) 0.7485(2) 0.0717(15) Uani 1 1 d . U . . .
C2' C -0.1450(12) 0.2784(5) 0.7823(3) 0.098(2) Uani 1 1 d . U . . .
H2' H -0.2603 0.2909 0.7981 0.118 Uiso 1 1 calc R . . . .
C3' C -0.0078(14) 0.3384(5) 0.7901(3) 0.107(2) Uani 1 1 d . U . . .
H3' H -0.0330 0.3942 0.8111 0.129 Uiso 1 1 calc R . . . .
C4' C 0.1663(13) 0.3222(5) 0.7690(3) 0.104(2) Uani 1 1 d . U . . .
H4' H 0.2547 0.3643 0.7782 0.125 Uiso 1 1 calc R . . . .
C5' C 0.2125(10) 0.2459(4) 0.7351(2) 0.0844(16) Uani 1 1 d . U . . .
H5' H 0.3294 0.2361 0.7199 0.101 Uiso 1 1 calc R . . . .
C6' C 0.0668(8) 0.1799(4) 0.7241(2) 0.0615(12) Uani 1 1 d . U . . .
C7' C 0.1154(6) 0.0898(3) 0.6906(2) 0.0440(10) Uani 1 1 d . . . . .
C8' C 0.1666(5) 0.1140(3) 0.62761(19) 0.0396(9) Uani 1 1 d . . . . .
C9' C 0.1988(6) 0.2266(3) 0.59586(19) 0.0420(10) Uani 1 1 d . . . . .
C10' C 0.0513(6) 0.3142(3) 0.59282(18) 0.0414(10) Uani 1 1 d . . . . .
C11' C -0.1283(6) 0.2940(3) 0.5933(2) 0.0499(11) Uani 1 1 d . . . . .
H11' H -0.1591 0.2234 0.5984 0.060 Uiso 1 1 calc R . . . .
C12' C -0.2643(6) 0.3763(4) 0.5863(2) 0.0540(12) Uani 1 1 d . . . . .
H12' H -0.3847 0.3604 0.5865 0.065 Uiso 1 1 calc R . . . .
C13' C -0.2221(7) 0.4823(4) 0.5788(2) 0.0557(12) Uani 1 1 d . . . . .
C14' C -0.0425(7) 0.5020(4) 0.5784(2) 0.0555(12) Uani 1 1 d . . . . .
H14' H -0.0121 0.5727 0.5735 0.067 Uiso 1 1 calc R . . . .
C15' C 0.0939(6) 0.4213(3) 0.5847(2) 0.0496(11) Uani 1 1 d . . . . .
H15' H 0.2141 0.4377 0.5837 0.060 Uiso 1 1 calc R . . . .
C16' C -0.3687(8) 0.5724(4) 0.5704(3) 0.0750(16) Uani 1 1 d . . . . .
H16D H -0.3943 0.5970 0.5267 0.112 Uiso 1 1 calc GR . . . .
H16E H -0.3293 0.6307 0.5869 0.112 Uiso 1 1 calc GR . . . .
H16F H -0.4761 0.5470 0.5921 0.112 Uiso 1 1 calc GR . . . .
C17' C 0.2258(5) 0.0298(3) 0.59550(19) 0.0385(9) Uani 1 1 d . . . . .
C18' C 0.3503(6) -0.1542(3) 0.6079(2) 0.0523(11) Uani 1 1 d . . . . .
H18' H 0.3856 -0.2186 0.6352 0.063 Uiso 1 1 calc R . . . .
C19' C 0.3671(6) -0.1474(3) 0.5470(2) 0.0509(11) Uani 1 1 d . . . . .
H19' H 0.4206 -0.2052 0.5317 0.061 Uiso 1 1 calc R . . . .
C20' C 0.3030(5) -0.0514(3) 0.5048(2) 0.0429(10) Uani 1 1 d . . . . .
C21' C 0.2264(5) 0.0365(3) 0.52932(18) 0.0381(9) Uani 1 1 d . . . . .
C22' C 0.1452(5) 0.1262(3) 0.4877(2) 0.0462(10) Uani 1 1 d . . . . .
H22' H 0.0896 0.1833 0.5032 0.055 Uiso 1 1 calc R . . . .
C23' C 0.1468(6) 0.1308(4) 0.4244(2) 0.0536(12) Uani 1 1 d . . . . .
H23' H 0.0915 0.1902 0.3974 0.064 Uiso 1 1 calc R . . . .
C24' C 0.2317(6) 0.0460(4) 0.4007(2) 0.0577(13) Uani 1 1 d . . . . .
H24' H 0.2369 0.0505 0.3578 0.069 Uiso 1 1 calc R . . . .
C25' C 0.3062(6) -0.0423(4) 0.4396(2) 0.0514(11) Uani 1 1 d . . . . .
H25' H 0.3609 -0.0984 0.4231 0.062 Uiso 1 1 calc R . . . .
N1' N 0.2815(5) -0.0675(3) 0.63132(16) 0.0469(9) Uani 1 1 d . . . . .
H1' H 0.2730 -0.0752 0.6712 0.056 Uiso 1 1 calc R . . . .
O1' O 0.1151(4) -0.0036(2) 0.72400(14) 0.0554(8) Uani 1 1 d . . . . .
O2' O 0.3447(4) 0.2474(2) 0.57099(15) 0.0554(8) Uani 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 C1 1.895(5) . ?
C1 C2 1.383(6) . ?
C1 C6 1.385(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.363(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.424(6) . ?
C6 C7 1.513(6) . ?
C7 C8 1.425(6) . ?
C7 O1 1.254(5) . ?
C8 C9 1.496(6) . ?
C8 C17 1.416(6) . ?
C9 C10 1.496(6) . ?
C9 O2 1.216(5) . ?
C10 C11 1.380(6) . ?
C10 C15 1.389(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(7) . ?
C13 C14 1.378(7) . ?
C13 C16 1.498(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.389(6) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C21 1.466(6) . ?
C17 N1 1.352(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.333(7) . ?
C18 N1 1.360(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.405(7) . ?
C20 C21 1.417(6) . ?
C20 C25 1.413(6) . ?
C21 C22 1.411(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.381(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.394(7) . ?
C24 H24 0.9300 . ?
C24 C25 1.355(7) . ?
C25 H25 0.9300 . ?
N1 H1 0.8600 . ?
Br1' C1' 1.876(6) . ?
C1' C2' 1.430(8) . ?
C1' C6' 1.381(7) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.354(10) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.376(10) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.363(8) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.475(8) . ?
C6' C7' 1.506(6) . ?
C7' C8' 1.400(6) . ?
C7' O1' 1.258(5) . ?
C8' C9' 1.492(6) . ?
C8' C17' 1.439(5) . ?
C9' C10' 1.492(6) . ?
C9' O2' 1.222(5) . ?
C10' C11' 1.375(6) . ?
C10' C15' 1.399(6) . ?
C11' H11' 0.9300 . ?
C11' C12' 1.383(6) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.386(6) . ?
C13' C14' 1.373(7) . ?
C13' C16' 1.503(6) . ?
C14' H14' 0.9300 . ?
C14' C15' 1.372(6) . ?
C15' H15' 0.9300 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17' C21' 1.435(6) . ?
C17' N1' 1.360(5) . ?
C18' H18' 0.9300 . ?
C18' C19' 1.324(6) . ?
C18' N1' 1.374(5) . ?
C19' H19' 0.9300 . ?
C19' C20' 1.425(6) . ?
C20' C21' 1.417(5) . ?
C20' C25' 1.410(6) . ?
C21' C22' 1.406(6) . ?
C22' H22' 0.9300 . ?
C22' C23' 1.378(6) . ?
C23' H23' 0.9300 . ?
C23' C24' 1.396(6) . ?
C24' H24' 0.9300 . ?
C24' C25' 1.349(6) . ?
C25' H25' 0.9300 . ?
N1' H1' 0.8600 . ?

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 C1 Br1 117.9(3) . . ?
C2 C1 C6 121.4(4) . . ?
C6 C1 Br1 120.7(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.3(5) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.7(4) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.5(4) . . ?
C1 C6 C7 121.6(4) . . ?
C5 C6 C7 119.9(4) . . ?
C8 C7 C6 117.8(4) . . ?
O1 C7 C6 116.9(4) . . ?
O1 C7 C8 125.1(4) . . ?
C7 C8 C9 116.7(4) . . ?
C17 C8 C7 120.7(4) . . ?
C17 C8 C9 121.5(4) . . ?
C10 C9 C8 119.0(4) . . ?
O2 C9 C8 121.3(4) . . ?
O2 C9 C10 119.7(4) . . ?
C11 C10 C9 121.0(4) . . ?
C11 C10 C15 118.4(4) . . ?
C15 C10 C9 120.5(4) . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.2 . . ?
C11 C12 C13 121.7(5) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 C16 120.8(5) . . ?
C14 C13 C12 116.8(4) . . ?
C14 C13 C16 122.4(5) . . ?
C13 C14 H14 118.8 . . ?
C13 C14 C15 122.5(4) . . ?
C15 C14 H14 118.8 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.9(4) . . ?
C14 C15 H15 120.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 C17 C21 126.1(4) . . ?
N1 C17 C8 119.1(4) . . ?
N1 C17 C21 114.8(4) . . ?
C19 C18 H18 119.9 . . ?
C19 C18 N1 120.3(5) . . ?
N1 C18 H18 119.9 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(4) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 C25 121.9(4) . . ?
C25 C20 C21 118.8(5) . . ?
C20 C21 C17 118.9(4) . . ?
C22 C21 C17 122.5(4) . . ?
C22 C21 C20 118.5(4) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22 119.5 . . ?
C22 C23 H23 120.4 . . ?
C22 C23 C24 119.2(5) . . ?
C24 C23 H23 120.4 . . ?
C23 C24 H24 119.3 . . ?
C25 C24 C23 121.4(5) . . ?
C25 C24 H24 119.3 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.7(5) . . ?
C24 C25 H25 119.6 . . ?
C17 N1 C18 125.5(4) . . ?
C17 N1 H1 117.3 . . ?
C18 N1 H1 117.3 . . ?
C2' C1' Br1' 117.7(5) . . ?
C6' C1' Br1' 121.9(4) . . ?
C6' C1' C2' 120.4(6) . . ?
C1' C2' H2' 121.5 . . ?
C3' C2' C1' 116.9(7) . . ?
C3' C2' H2' 121.5 . . ?
C2' C3' H3' 117.9 . . ?
C2' C3' C4' 124.2(7) . . ?
C4' C3' H3' 117.9 . . ?
C3' C4' H4' 119.2 . . ?
C5' C4' C3' 121.7(7) . . ?
C5' C4' H4' 119.2 . . ?
C4' C5' H5' 121.9 . . ?
C4' C5' C6' 116.2(7) . . ?
C6' C5' H5' 121.9 . . ?
C1' C6' C5' 120.5(5) . . ?
C1' C6' C7' 121.5(5) . . ?
C5' C6' C7' 117.8(5) . . ?
C8' C7' C6' 119.6(4) . . ?
O1' C7' C6' 115.3(4) . . ?
O1' C7' C8' 125.0(4) . . ?
C7' C8' C9' 120.6(3) . . ?
C7' C8' C17' 120.9(4) . . ?
C17' C8' C9' 117.3(4) . . ?
C8' C9' C10' 120.2(4) . . ?
O2' C9' C8' 120.3(4) . . ?
O2' C9' C10' 119.5(4) . . ?
C11' C10' C9' 121.8(4) . . ?
C11' C10' C15' 118.0(4) . . ?
C15' C10' C9' 120.1(4) . . ?
C10' C11' H11' 119.2 . . ?
C10' C11' C12' 121.6(4) . . ?
C12' C11' H11' 119.2 . . ?
C11' C12' H12' 119.8 . . ?
C11' C12' C13' 120.4(5) . . ?
C13' C12' H12' 119.8 . . ?
C12' C13' C16' 120.8(5) . . ?
C14' C13' C12' 117.8(4) . . ?
C14' C13' C16' 121.4(5) . . ?
C13' C14' H14' 118.8 . . ?
C15' C14' C13' 122.5(4) . . ?
C15' C14' H14' 118.8 . . ?
C10' C15' H15' 120.1 . . ?
C14' C15' C10' 119.8(4) . . ?
C14' C15' H15' 120.1 . . ?
C13' C16' H16D 109.5 . . ?
C13' C16' H16E 109.5 . . ?
C13' C16' H16F 109.5 . . ?
H16D C16' H16E 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C21' C17' C8' 126.7(4) . . ?
N1' C17' C8' 117.1(4) . . ?
N1' C17' C21' 116.2(3) . . ?
C19' C18' H18' 119.6 . . ?
C19' C18' N1' 120.8(4) . . ?
N1' C18' H18' 119.6 . . ?
C18' C19' H19' 120.1 . . ?
C18' C19' C20' 119.8(4) . . ?
C20' C19' H19' 120.1 . . ?
C21' C20' C19' 118.9(4) . . ?
C25' C20' C19' 122.3(4) . . ?
C25' C20' C21' 118.8(4) . . ?
C20' C21' C17' 119.6(4) . . ?
C22' C21' C17' 121.9(4) . . ?
C22' C21' C20' 118.4(4) . . ?
C21' C22' H22' 119.5 . . ?
C23' C22' C21' 120.9(4) . . ?
C23' C22' H22' 119.5 . . ?
C22' C23' H23' 120.0 . . ?
C22' C23' C24' 119.9(4) . . ?
C24' C23' H23' 120.0 . . ?
C23' C24' H24' 119.8 . . ?
C25' C24' C23' 120.4(4) . . ?
C25' C24' H24' 119.8 . . ?
C20' C25' H25' 119.3 . . ?
C24' C25' C20' 121.5(4) . . ?
C24' C25' H25' 119.3 . . ?
C17' N1' C18' 124.2(4) . . ?
C17' N1' H1' 117.9 . . ?
C18' N1' H1' 117.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.86 1.89 2.590(5) 137.7 .
N1' H1' O1' 0.86 1.94 2.596(5) 132.1 .

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 C1 C2 C3 176.7(3) . . . . ?
Br1 C1 C6 C5 -179.2(3) . . . . ?
Br1 C1 C6 C7 3.5(6) . . . . ?
C1 C2 C3 C4 1.7(7) . . . . ?
C1 C6 C7 C8 -116.7(4) . . . . ?
C1 C6 C7 O1 68.2(5) . . . . ?
C2 C1 C6 C5 -1.7(6) . . . . ?
C2 C1 C6 C7 -179.1(4) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -2.6(7) . . . . ?
C4 C5 C6 C1 3.4(6) . . . . ?
C4 C5 C6 C7 -179.3(4) . . . . ?
C5 C6 C7 C8 66.0(5) . . . . ?
C5 C6 C7 O1 -109.1(5) . . . . ?
C6 C1 C2 C3 -0.8(7) . . . . ?
C6 C7 C8 C9 -5.4(5) . . . . ?
C6 C7 C8 C17 -173.8(4) . . . . ?
C7 C8 C9 C10 67.5(5) . . . . ?
C7 C8 C9 O2 -114.5(4) . . . . ?
C7 C8 C17 C21 -171.7(4) . . . . ?
C7 C8 C17 N1 8.4(6) . . . . ?
C8 C9 C10 C11 30.0(6) . . . . ?
C8 C9 C10 C15 -152.8(4) . . . . ?
C8 C17 C21 C20 -169.2(4) . . . . ?
C8 C17 C21 C22 12.9(6) . . . . ?
C8 C17 N1 C18 171.9(4) . . . . ?
C9 C8 C17 C21 20.5(6) . . . . ?
C9 C8 C17 N1 -159.4(4) . . . . ?
C9 C10 C11 C12 175.2(4) . . . . ?
C9 C10 C15 C14 -176.6(4) . . . . ?
C10 C11 C12 C13 1.9(7) . . . . ?
C11 C10 C15 C14 0.6(6) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C11 C12 C13 C16 -178.8(4) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C13 C14 C15 C10 0.9(7) . . . . ?
C15 C10 C11 C12 -2.0(6) . . . . ?
C16 C13 C14 C15 177.4(4) . . . . ?
C17 C8 C9 C10 -124.2(4) . . . . ?
C17 C8 C9 O2 53.8(6) . . . . ?
C17 C21 C22 C23 -177.9(4) . . . . ?
C18 C19 C20 C21 -3.4(7) . . . . ?
C18 C19 C20 C25 175.6(4) . . . . ?
C19 C18 N1 C17 -0.7(7) . . . . ?
C19 C20 C21 C17 -5.5(6) . . . . ?
C19 C20 C21 C22 172.5(4) . . . . ?
C19 C20 C25 C24 -174.5(4) . . . . ?
C20 C21 C22 C23 4.2(6) . . . . ?
C21 C17 N1 C18 -8.0(6) . . . . ?
C21 C20 C25 C24 4.5(7) . . . . ?
C21 C22 C23 C24 0.5(7) . . . . ?
C22 C23 C24 C25 -2.7(7) . . . . ?
C23 C24 C25 C20 0.2(7) . . . . ?
C25 C20 C21 C17 175.4(4) . . . . ?
C25 C20 C21 C22 -6.6(6) . . . . ?
N1 C17 C21 C20 10.7(6) . . . . ?
N1 C17 C21 C22 -167.2(4) . . . . ?
N1 C18 C19 C20 6.8(7) . . . . ?
O1 C7 C8 C9 169.2(4) . . . . ?
O1 C7 C8 C17 0.8(7) . . . . ?
O2 C9 C10 C11 -147.9(4) . . . . ?
O2 C9 C10 C15 29.2(6) . . . . ?
Br1' C1' C2' C3' 179.1(5) . . . . ?
Br1' C1' C6' C5' -177.7(3) . . . . ?
Br1' C1' C6' C7' -3.3(7) . . . . ?
C1' C2' C3' C4' -1.6(10) . . . . ?
C1' C6' C7' C8' 117.6(5) . . . . ?
C1' C6' C7' O1' -66.1(6) . . . . ?
C2' C1' C6' C5' 3.1(7) . . . . ?
C2' C1' C6' C7' 177.5(4) . . . . ?
C2' C3' C4' C5' 3.4(11) . . . . ?
C3' C4' C5' C6' -1.8(9) . . . . ?
C4' C5' C6' C1' -1.3(7) . . . . ?
C4' C5' C6' C7' -175.9(5) . . . . ?
C5' C6' C7' C8' -67.9(5) . . . . ?
C5' C6' C7' O1' 108.4(5) . . . . ?
C6' C1' C2' C3' -1.7(8) . . . . ?
C6' C7' C8' C9' 8.7(6) . . . . ?
C6' C7' C8' C17' 175.7(4) . . . . ?
C7' C8' C9' C10' -58.9(5) . . . . ?
C7' C8' C9' O2' 122.7(4) . . . . ?
C7' C8' C17' C21' 158.4(4) . . . . ?
C7' C8' C17' N1' -19.2(6) . . . . ?
C8' C9' C10' C11' -28.1(6) . . . . ?
C8' C9' C10' C15' 156.6(4) . . . . ?
C8' C17' C21' C20' 174.9(4) . . . . ?
C8' C17' C21' C22' -8.2(6) . . . . ?
C8' C17' N1' C18' -176.6(4) . . . . ?
C9' C8' C17' C21' -34.2(6) . . . . ?
C9' C8' C17' N1' 148.1(4) . . . . ?
C9' C10' C11' C12' -175.6(4) . . . . ?
C9' C10' C15' C14' 176.2(4) . . . . ?
C10' C11' C12' C13' -0.3(7) . . . . ?
C11' C10' C15' C14' 0.8(6) . . . . ?
C11' C12' C13' C14' 0.4(7) . . . . ?
C11' C12' C13' C16' 179.2(4) . . . . ?
C12' C13' C14' C15' 0.2(7) . . . . ?
C13' C14' C15' C10' -0.8(7) . . . . ?
C15' C10' C11' C12' -0.3(6) . . . . ?
C16' C13' C14' C15' -178.7(5) . . . . ?
C17' C8' C9' C10' 133.7(4) . . . . ?
C17' C8' C9' O2' -44.7(5) . . . . ?
C17' C21' C22' C23' -179.8(4) . . . . ?
C18' C19' C20' C21' 1.7(6) . . . . ?
C18' C19' C20' C25' -175.6(4) . . . . ?
C19' C18' N1' C17' 0.1(7) . . . . ?
C19' C20' C21' C17' 4.1(6) . . . . ?
C19' C20' C21' C22' -172.9(4) . . . . ?
C19' C20' C25' C24' 174.6(4) . . . . ?
C20' C21' C22' C23' -2.8(6) . . . . ?
C21' C17' N1' C18' 5.5(6) . . . . ?
C21' C20' C25' C24' -2.8(6) . . . . ?
C21' C22' C23' C24' -0.7(6) . . . . ?
C22' C23' C24' C25' 2.5(7) . . . . ?
C23' C24' C25' C20' -0.8(7) . . . . ?
C25' C20' C21' C17' -178.5(4) . . . . ?
C25' C20' C21' C22' 4.5(6) . . . . ?
N1' C17' C21' C20' -7.4(5) . . . . ?
N1' C17' C21' C22' 169.5(4) . . . . ?
N1' C18' C19' C20' -3.9(7) . . . . ?
O1' C7' C8' C9' -167.2(4) . . . . ?
O1' C7' C8' C17' -0.3(7) . . . . ?
O2' C9' C10' C11' 150.3(4) . . . . ?
O2' C9' C10' C15' -25.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
