# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1842259'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 F2 N O'
_chemical_formula_weight         337.36

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'

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

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

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

_cell_length_a                   10.143(4)
_cell_length_b                   9.497(3)
_cell_length_c                   19.050(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.453(11)
_cell_angle_gamma                90
_cell_volume                     1810.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      304(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23003
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.403
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3302
_reflns_number_gt                1967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1142P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1998
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8206(2) 0.08604(15) 0.27797(10) 0.0863(7) Uani 1 1 d . . . . .
N1 N 0.7525(2) 0.28873(16) 0.22356(10) 0.0551(6) Uani 1 1 d . . . . .
H1A H 0.7422 0.3778 0.2287 0.066 Uiso 1 1 calc R U . . .
F1 F 0.64278(18) 0.07091(15) -0.04725(8) 0.0946(6) Uani 1 1 d . . . . .
C1 C 0.7212(2) 0.2313(2) 0.15433(12) 0.0523(6) Uani 1 1 d . . . . .
F2 F 0.88897(17) 0.04459(17) 0.02924(10) 0.1018(6) Uani 1 1 d . . . . .
C2 C 0.5919(2) 0.24378(19) 0.11593(11) 0.0496(6) Uani 1 1 d . . . . .
C3 C 0.5674(3) 0.1880(2) 0.04745(13) 0.0579(7) Uani 1 1 d . . . . .
H3A H 0.4825 0.1954 0.0205 0.070 Uiso 1 1 calc R U . . .
C4 C 0.6670(3) 0.1225(2) 0.01958(14) 0.0670(7) Uani 1 1 d . . . . .
C5 C 0.7923(3) 0.1091(2) 0.05821(15) 0.0681(8) Uani 1 1 d . . . . .
C6 C 0.8212(3) 0.1638(2) 0.12504(14) 0.0634(7) Uani 1 1 d . . . . .
H6A H 0.9070 0.1560 0.1509 0.076 Uiso 1 1 calc R U . . .
C7 C 0.4483(2) 0.2444(3) 0.21235(13) 0.0642(7) Uani 1 1 d . . . . .
C8 C 0.4078(3) 0.3253(4) 0.26550(16) 0.1040(11) Uani 1 1 d . . . . .
H8A H 0.4075 0.4230 0.2623 0.125 Uiso 1 1 calc R U . . .
C9 C 0.3676(5) 0.2591(8) 0.3240(2) 0.1472(19) Uani 1 1 d . . . . .
H9A H 0.3400 0.3122 0.3599 0.177 Uiso 1 1 calc R U . . .
C10 C 0.3692(5) 0.1151(9) 0.3278(3) 0.151(2) Uani 1 1 d . . . . .
H10A H 0.3424 0.0713 0.3668 0.181 Uiso 1 1 calc R U . . .
C11 C 0.4085(4) 0.0354(5) 0.2769(3) 0.1263(15) Uani 1 1 d . . . . .
H11A H 0.4088 -0.0623 0.2805 0.152 Uiso 1 1 calc R U . . .
C12 C 0.4485(3) 0.1006(3) 0.21861(16) 0.0882(9) Uani 1 1 d . . . . .
H12A H 0.4760 0.0457 0.1832 0.106 Uiso 1 1 calc R U . . .
C13 C 0.3620(2) 0.3517(2) 0.09258(11) 0.0510(6) Uani 1 1 d . . . . .
C14 C 0.2521(3) 0.2648(2) 0.08003(14) 0.0679(7) Uani 1 1 d . . . . .
H14A H 0.2492 0.1846 0.1077 0.082 Uiso 1 1 calc R U . . .
C15 C 0.1460(3) 0.2950(3) 0.02682(15) 0.0772(8) Uani 1 1 d . . . . .
H15A H 0.0728 0.2347 0.0190 0.093 Uiso 1 1 calc R U . . .
C16 C 0.1474(3) 0.4122(3) -0.01441(14) 0.0711(8) Uani 1 1 d . . . . .
H16A H 0.0758 0.4323 -0.0501 0.085 Uiso 1 1 calc R U . . .
C17 C 0.2556(3) 0.4996(3) -0.00243(14) 0.0732(8) Uani 1 1 d . . . . .
H17A H 0.2575 0.5798 -0.0302 0.088 Uiso 1 1 calc R U . . .
C18 C 0.3614(3) 0.4704(2) 0.05020(13) 0.0621(7) Uani 1 1 d . . . . .
H18A H 0.4342 0.5313 0.0576 0.074 Uiso 1 1 calc R U . . .
C19 C 0.4844(2) 0.3195(2) 0.14783(11) 0.0511(6) Uani 1 1 d . . . . .
H19A H 0.5223 0.4106 0.1648 0.061 Uiso 1 1 calc R U . . .
C20 C 0.8166(4) 0.2888(3) 0.35048(14) 0.0924(10) Uani 1 1 d . . . . .
H20A H 0.7932 0.3860 0.3422 0.139 Uiso 1 1 calc R U . . .
H20B H 0.7607 0.2479 0.3811 0.139 Uiso 1 1 calc R U . . .
H20C H 0.9085 0.2820 0.3727 0.139 Uiso 1 1 calc R U . . .
C21 C 0.7973(3) 0.2121(2) 0.28151(13) 0.0623(7) 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
O1 C21 1.224(2) . ?
N1 C21 1.338(3) . ?
N1 C1 1.414(3) . ?
N1 H1A 0.8600 . ?
F1 C4 1.349(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.398(3) . ?
F2 C5 1.349(3) . ?
C2 C3 1.392(3) . ?
C2 C19 1.514(3) . ?
C3 C4 1.365(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.366(4) . ?
C5 C6 1.362(4) . ?
C6 H6A 0.9300 . ?
C7 C12 1.371(3) . ?
C7 C8 1.385(4) . ?
C7 C19 1.517(3) . ?
C8 C9 1.397(6) . ?
C8 H8A 0.9300 . ?
C9 C10 1.370(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.342(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(5) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(3) . ?
C13 C18 1.386(3) . ?
C13 C19 1.521(3) . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9300 . ?
C15 C16 1.364(3) . ?
C15 H15A 0.9300 . ?
C16 C17 1.364(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.372(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9800 . ?
C20 C21 1.487(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C21 N1 C1 123.59(17) . . ?
C21 N1 H1A 118.2 . . ?
C1 N1 H1A 118.2 . . ?
C6 C1 C2 120.8(2) . . ?
C6 C1 N1 119.0(2) . . ?
C2 C1 N1 120.2(2) . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 C19 121.8(2) . . ?
C1 C2 C19 120.4(2) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
F1 C4 C3 120.1(3) . . ?
F1 C4 C5 118.9(2) . . ?
C3 C4 C5 121.0(2) . . ?
F2 C5 C6 119.8(3) . . ?
F2 C5 C4 119.8(2) . . ?
C6 C5 C4 120.4(2) . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 H6A 120.3 . . ?
C1 C6 H6A 120.3 . . ?
C12 C7 C8 119.0(3) . . ?
C12 C7 C19 122.8(2) . . ?
C8 C7 C19 118.1(3) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 119.3(5) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 H10A 119.1 . . ?
C9 C10 H10A 119.1 . . ?
C10 C11 C12 119.1(5) . . ?
C10 C11 H11A 120.4 . . ?
C12 C11 H11A 120.4 . . ?
C7 C12 C11 121.1(4) . . ?
C7 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C14 C13 C18 117.4(2) . . ?
C14 C13 C19 123.05(19) . . ?
C18 C13 C19 119.4(2) . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C16 C15 C14 120.7(2) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 119.0(2) . . ?
C15 C16 H16A 120.5 . . ?
C17 C16 H16A 120.5 . . ?
C16 C17 C18 120.7(2) . . ?
C16 C17 H17A 119.6 . . ?
C18 C17 H17A 119.6 . . ?
C17 C18 C13 121.2(2) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
C2 C19 C7 112.81(18) . . ?
C2 C19 C13 112.18(18) . . ?
C7 C19 C13 112.12(19) . . ?
C2 C19 H19A 106.4 . . ?
C7 C19 H19A 106.4 . . ?
C13 C19 H19A 106.4 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 N1 121.9(2) . . ?
O1 C21 C20 122.0(2) . . ?
N1 C21 C20 116.1(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
C21 N1 C1 C6 -60.4(3) . . . . ?
C21 N1 C1 C2 120.2(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 178.65(17) . . . . ?
C6 C1 C2 C19 -179.03(18) . . . . ?
N1 C1 C2 C19 0.4(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C19 C2 C3 C4 178.78(19) . . . . ?
C2 C3 C4 F1 -178.9(2) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
F1 C4 C5 F2 -0.2(3) . . . . ?
C3 C4 C5 F2 -179.6(2) . . . . ?
F1 C4 C5 C6 177.99(19) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
F2 C5 C6 C1 179.4(2) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
N1 C1 C6 C5 -179.51(18) . . . . ?
C12 C7 C8 C9 -0.3(5) . . . . ?
C19 C7 C8 C9 176.9(3) . . . . ?
C7 C8 C9 C10 0.2(6) . . . . ?
C8 C9 C10 C11 0.0(8) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C8 C7 C12 C11 0.3(4) . . . . ?
C19 C7 C12 C11 -176.8(3) . . . . ?
C10 C11 C12 C7 -0.2(6) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C19 C13 C14 C15 -176.8(2) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 0.1(4) . . . . ?
C14 C13 C18 C17 -0.3(4) . . . . ?
C19 C13 C18 C17 176.9(2) . . . . ?
C3 C2 C19 C7 116.2(2) . . . . ?
C1 C2 C19 C7 -65.6(2) . . . . ?
C3 C2 C19 C13 -11.6(3) . . . . ?
C1 C2 C19 C13 166.66(18) . . . . ?
C12 C7 C19 C2 -34.4(3) . . . . ?
C8 C7 C19 C2 148.5(2) . . . . ?
C12 C7 C19 C13 93.4(3) . . . . ?
C8 C7 C19 C13 -83.7(3) . . . . ?
C14 C13 C19 C2 94.1(3) . . . . ?
C18 C13 C19 C2 -83.0(2) . . . . ?
C14 C13 C19 C7 -34.1(3) . . . . ?
C18 C13 C19 C7 148.9(2) . . . . ?
C1 N1 C21 O1 3.6(4) . . . . ?
C1 N1 C21 C20 -176.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.08 2.918(2) 166.5 2_655

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.101

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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 1842260'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H28 Cl N O'
_chemical_formula_sum            'C34 H28 Cl N O'
_chemical_formula_weight         502.02

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   13.5024(11)
_cell_length_b                   9.0647(8)
_cell_length_c                   22.691(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.115(2)
_cell_angle_gamma                90
_cell_volume                     2755.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      24.69

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.450
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      304(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50395
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.214
_diffrn_reflns_theta_max         25.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5020
_reflns_number_gt                3673
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+0.5572P] 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     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5020
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1254
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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_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
O1 O -0.04798(10) 0.66379(14) 0.27970(7) 0.0578(4) Uani 1 1 d . . . . .
N1 N 0.04563(11) 0.86232(16) 0.26325(7) 0.0443(4) Uani 1 1 d . . . . .
H1A H 0.0443 0.9532 0.2524 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl 0.37193(4) 0.70977(8) 0.19151(2) 0.0731(2) Uani 1 1 d . . . . .
C1 C 0.17018(13) 0.74024(19) 0.33629(8) 0.0402(4) Uani 1 1 d . . . . .
C2 C 0.14049(13) 0.79546(18) 0.27923(8) 0.0403(4) Uani 1 1 d . . . . .
C3 C 0.20419(14) 0.7860(2) 0.23595(8) 0.0459(4) Uani 1 1 d . . . . .
H3A H 0.1853 0.8271 0.1987 0.055 Uiso 1 1 calc R U . . .
C4 C 0.29522(14) 0.7164(2) 0.24763(8) 0.0447(4) Uani 1 1 d . . . . .
C5 C 0.32500(13) 0.6504(2) 0.30219(8) 0.0430(4) Uani 1 1 d . . . . .
C6 C 0.26099(13) 0.6659(2) 0.34503(8) 0.0432(4) Uani 1 1 d . . . . .
H6A H 0.2800 0.6239 0.3821 0.052 Uiso 1 1 calc R U . . .
C7 C 0.15771(15) 0.6967(2) 0.44548(8) 0.0510(5) Uani 1 1 d . . . . .
C8 C 0.23554(18) 0.7735(3) 0.47750(9) 0.0657(6) Uani 1 1 d . . . . .
H8A H 0.2537 0.8653 0.4641 0.079 Uiso 1 1 calc R U . . .
C9 C 0.2864(2) 0.7161(4) 0.52886(11) 0.0870(8) Uani 1 1 d . . . . .
H9A H 0.3387 0.7690 0.5494 0.104 Uiso 1 1 calc R U . . .
C10 C 0.2609(3) 0.5850(4) 0.54916(13) 0.1051(11) Uani 1 1 d . . . . .
H10A H 0.2957 0.5467 0.5837 0.126 Uiso 1 1 calc R U . . .
C11 C 0.1843(3) 0.5071(4) 0.51967(15) 0.1078(11) Uani 1 1 d . . . . .
H11A H 0.1666 0.4163 0.5343 0.129 Uiso 1 1 calc R U . . .
C12 C 0.1316(2) 0.5629(3) 0.46718(11) 0.0776(7) Uani 1 1 d . . . . .
H12A H 0.0791 0.5093 0.4472 0.093 Uiso 1 1 calc R U . . .
C13 C 0.06613(14) 0.9102(2) 0.39446(8) 0.0489(5) Uani 1 1 d . . . . .
C14 C 0.12117(19) 1.0345(2) 0.38719(11) 0.0681(6) Uani 1 1 d . . . . .
H14A H 0.1843 1.0250 0.3752 0.082 Uiso 1 1 calc R U . . .
C15 C 0.0850(3) 1.1737(3) 0.39734(14) 0.0918(9) Uani 1 1 d . . . . .
H15A H 0.1238 1.2566 0.3927 0.110 Uiso 1 1 calc R U . . .
C16 C -0.0085(3) 1.1888(4) 0.41433(15) 0.1018(10) Uani 1 1 d . . . . .
H16A H -0.0337 1.2821 0.4209 0.122 Uiso 1 1 calc R U . . .
C17 C -0.0639(2) 1.0670(4) 0.42145(15) 0.0992(10) Uani 1 1 d . . . . .
H17A H -0.1274 1.0773 0.4328 0.119 Uiso 1 1 calc R U . . .
C18 C -0.02757(17) 0.9281(3) 0.41213(11) 0.0723(7) Uani 1 1 d . . . . .
H18A H -0.0663 0.8457 0.4178 0.087 Uiso 1 1 calc R U . . .
C19 C 0.51123(14) 0.6644(3) 0.33627(10) 0.0603(6) Uani 1 1 d . . . . .
C20 C 0.50279(19) 0.7868(3) 0.37155(13) 0.0825(8) Uani 1 1 d . . . . .
H20A H 0.4406 0.8131 0.3819 0.099 Uiso 1 1 calc R U . . .
C21 C 0.5861(3) 0.8711(4) 0.39188(18) 0.1161(12) Uani 1 1 d . . . . .
H21A H 0.5798 0.9526 0.4160 0.139 Uiso 1 1 calc R U . . .
C22 C 0.6771(3) 0.8336(5) 0.3762(2) 0.1324(18) Uani 1 1 d . . . . .
H22A H 0.7324 0.8919 0.3888 0.159 Uiso 1 1 calc R U . . .
C23 C 0.6880(2) 0.7139(5) 0.34293(19) 0.1136(14) Uani 1 1 d . . . . .
H23A H 0.7510 0.6874 0.3340 0.136 Uiso 1 1 calc R U . . .
C24 C 0.60482(16) 0.6289(3) 0.32166(13) 0.0824(8) Uani 1 1 d . . . . .
H24A H 0.6125 0.5479 0.2975 0.099 Uiso 1 1 calc R U . . .
C25 C 0.41460(13) 0.4339(2) 0.35509(9) 0.0496(5) Uani 1 1 d . . . . .
C26 C 0.42829(17) 0.4431(3) 0.41653(10) 0.0655(6) Uani 1 1 d . . . . .
H26A H 0.4463 0.5326 0.4348 0.079 Uiso 1 1 calc R U . . .
C27 C 0.4153(2) 0.3201(3) 0.45082(13) 0.0838(8) Uani 1 1 d . . . . .
H27A H 0.4228 0.3282 0.4920 0.101 Uiso 1 1 calc R U . . .
C28 C 0.3916(2) 0.1871(3) 0.42489(17) 0.0915(9) Uani 1 1 d . . . . .
H28A H 0.3842 0.1045 0.4483 0.110 Uiso 1 1 calc R U . . .
C29 C 0.3788(2) 0.1753(3) 0.36404(17) 0.0866(8) Uani 1 1 d . . . . .
H29A H 0.3625 0.0848 0.3461 0.104 Uiso 1 1 calc R U . . .
C30 C 0.39007(16) 0.2978(3) 0.32992(12) 0.0656(6) Uani 1 1 d . . . . .
H30A H 0.3810 0.2890 0.2888 0.079 Uiso 1 1 calc R U . . .
C31 C 0.10510(14) 0.7546(2) 0.38676(8) 0.0451(4) Uani 1 1 d . . . . .
H31A H 0.0466 0.6917 0.3762 0.054 Uiso 1 1 calc R U . . .
C32 C 0.42298(14) 0.5659(2) 0.31461(9) 0.0507(5) Uani 1 1 d . . . . .
H32A H 0.4367 0.5256 0.2764 0.061 Uiso 1 1 calc R U . . .
C33 C -0.13240(15) 0.8850(2) 0.24540(11) 0.0669(6) Uani 1 1 d . . . . .
H33A H -0.1121 0.9820 0.2349 0.100 Uiso 1 1 calc R U . . .
H33B H -0.1711 0.8403 0.2117 0.100 Uiso 1 1 calc R U . . .
H33C H -0.1721 0.8919 0.2776 0.100 Uiso 1 1 calc R U . . .
C34 C -0.04182(14) 0.7926(2) 0.26410(8) 0.0457(4) 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
O1 C34 1.226(2) . ?
N1 C34 1.342(2) . ?
N1 C2 1.423(2) . ?
N1 H1A 0.8600 . ?
Cl1 C4 1.7392(18) . ?
C1 C6 1.392(2) . ?
C1 C2 1.400(2) . ?
C1 C31 1.533(2) . ?
C2 C3 1.386(3) . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.389(3) . ?
C5 C6 1.386(2) . ?
C5 C32 1.524(2) . ?
C6 H6A 0.9300 . ?
C7 C12 1.371(3) . ?
C7 C8 1.388(3) . ?
C7 C31 1.524(3) . ?
C8 C9 1.379(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.336(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.358(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.404(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.371(3) . ?
C13 C18 1.383(3) . ?
C13 C31 1.523(3) . ?
C14 C15 1.383(3) . ?
C14 H14A 0.9300 . ?
C15 C16 1.372(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.355(5) . ?
C16 H16A 0.9300 . ?
C17 C18 1.377(4) . ?
C17 H17A 0.9300 . ?
C18 H18A 0.9300 . ?
C19 C20 1.381(4) . ?
C19 C24 1.383(3) . ?
C19 C32 1.521(3) . ?
C20 C21 1.391(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.364(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.340(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.398(4) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 C30 1.382(3) . ?
C25 C26 1.386(3) . ?
C25 C32 1.521(3) . ?
C26 C27 1.384(3) . ?
C26 H26A 0.9300 . ?
C27 C28 1.362(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.374(4) . ?
C28 H28A 0.9300 . ?
C29 C30 1.373(4) . ?
C29 H29A 0.9300 . ?
C30 H30A 0.9300 . ?
C31 H31A 0.9800 . ?
C32 H32A 0.9800 . ?
C33 C34 1.500(3) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 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
C34 N1 C2 124.17(15) . . ?
C34 N1 H1A 117.9 . . ?
C2 N1 H1A 117.9 . . ?
C6 C1 C2 116.83(16) . . ?
C6 C1 C31 120.74(15) . . ?
C2 C1 C31 122.39(15) . . ?
C3 C2 C1 120.11(16) . . ?
C3 C2 N1 117.63(15) . . ?
C1 C2 N1 122.26(15) . . ?
C4 C3 C2 120.60(16) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C3 C4 C5 121.44(16) . . ?
C3 C4 Cl1 118.23(14) . . ?
C5 C4 Cl1 120.31(14) . . ?
C6 C5 C4 116.40(16) . . ?
C6 C5 C32 121.58(16) . . ?
C4 C5 C32 122.01(16) . . ?
C5 C6 C1 124.36(16) . . ?
C5 C6 H6A 117.8 . . ?
C1 C6 H6A 117.8 . . ?
C12 C7 C8 117.8(2) . . ?
C12 C7 C31 120.4(2) . . ?
C8 C7 C31 121.72(19) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8A 119.4 . . ?
C7 C8 H8A 119.4 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C7 C12 C11 119.9(3) . . ?
C7 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C14 C13 C18 117.9(2) . . ?
C14 C13 C31 123.17(17) . . ?
C18 C13 C31 118.90(19) . . ?
C13 C14 C15 121.5(2) . . ?
C13 C14 H14A 119.3 . . ?
C15 C14 H14A 119.3 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15A 120.2 . . ?
C14 C15 H15A 120.2 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C17 C18 C13 120.5(3) . . ?
C17 C18 H18A 119.7 . . ?
C13 C18 H18A 119.7 . . ?
C20 C19 C24 118.0(2) . . ?
C20 C19 C32 122.76(19) . . ?
C24 C19 C32 119.2(2) . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20A 119.6 . . ?
C21 C20 H20A 119.6 . . ?
C22 C21 C20 119.6(4) . . ?
C22 C21 H21A 120.2 . . ?
C20 C21 H21A 120.2 . . ?
C23 C22 C21 120.9(3) . . ?
C23 C22 H22A 119.6 . . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C24 120.1(3) . . ?
C22 C23 H23A 119.9 . . ?
C24 C23 H23A 119.9 . . ?
C19 C24 C23 120.5(3) . . ?
C19 C24 H24A 119.7 . . ?
C23 C24 H24A 119.7 . . ?
C30 C25 C26 117.7(2) . . ?
C30 C25 C32 118.98(19) . . ?
C26 C25 C32 123.31(18) . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C28 C27 C26 120.7(3) . . ?
C28 C27 H27A 119.7 . . ?
C26 C27 H27A 119.7 . . ?
C27 C28 C29 119.8(3) . . ?
C27 C28 H28A 120.1 . . ?
C29 C28 H28A 120.1 . . ?
C30 C29 C28 119.6(3) . . ?
C30 C29 H29A 120.2 . . ?
C28 C29 H29A 120.2 . . ?
C29 C30 C25 121.8(3) . . ?
C29 C30 H30A 119.1 . . ?
C25 C30 H30A 119.1 . . ?
C13 C31 C7 110.43(15) . . ?
C13 C31 C1 113.73(15) . . ?
C7 C31 C1 112.07(15) . . ?
C13 C31 H31A 106.7 . . ?
C7 C31 H31A 106.7 . . ?
C1 C31 H31A 106.7 . . ?
C25 C32 C19 112.37(15) . . ?
C25 C32 C5 112.28(15) . . ?
C19 C32 C5 113.08(16) . . ?
C25 C32 H32A 106.2 . . ?
C19 C32 H32A 106.2 . . ?
C5 C32 H32A 106.2 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O1 C34 N1 122.98(16) . . ?
O1 C34 C33 122.11(18) . . ?
N1 C34 C33 114.90(17) . . ?

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
C6 C1 C2 C3 -5.4(2) . . . . ?
C31 C1 C2 C3 176.83(16) . . . . ?
C6 C1 C2 N1 174.54(16) . . . . ?
C31 C1 C2 N1 -3.2(3) . . . . ?
C34 N1 C2 C3 118.1(2) . . . . ?
C34 N1 C2 C1 -61.9(2) . . . . ?
C1 C2 C3 C4 3.0(3) . . . . ?
N1 C2 C3 C4 -176.93(16) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C2 C3 C4 Cl1 -179.52(14) . . . . ?
C3 C4 C5 C6 -3.6(3) . . . . ?
Cl1 C4 C5 C6 177.62(14) . . . . ?
C3 C4 C5 C32 176.66(18) . . . . ?
Cl1 C4 C5 C32 -2.1(3) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C32 C5 C6 C1 -179.31(17) . . . . ?
C2 C1 C6 C5 3.5(3) . . . . ?
C31 C1 C6 C5 -178.74(17) . . . . ?
C12 C7 C8 C9 1.2(3) . . . . ?
C31 C7 C8 C9 -176.3(2) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C9 C10 C11 C12 0.6(5) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
C31 C7 C12 C11 176.5(2) . . . . ?
C10 C11 C12 C7 0.1(5) . . . . ?
C18 C13 C14 C15 0.3(4) . . . . ?
C31 C13 C14 C15 -176.9(2) . . . . ?
C13 C14 C15 C16 -0.9(4) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C13 -0.9(5) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C31 C13 C18 C17 177.8(2) . . . . ?
C24 C19 C20 C21 -0.2(4) . . . . ?
C32 C19 C20 C21 178.0(2) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C23 -2.0(6) . . . . ?
C21 C22 C23 C24 2.7(6) . . . . ?
C20 C19 C24 C23 0.9(3) . . . . ?
C32 C19 C24 C23 -177.4(2) . . . . ?
C22 C23 C24 C19 -2.1(4) . . . . ?
C30 C25 C26 C27 -1.5(3) . . . . ?
C32 C25 C26 C27 177.1(2) . . . . ?
C25 C26 C27 C28 1.9(4) . . . . ?
C26 C27 C28 C29 -1.2(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C25 0.2(4) . . . . ?
C26 C25 C30 C29 0.4(3) . . . . ?
C32 C25 C30 C29 -178.2(2) . . . . ?
C14 C13 C31 C7 89.7(2) . . . . ?
C18 C13 C31 C7 -87.4(2) . . . . ?
C14 C13 C31 C1 -37.3(3) . . . . ?
C18 C13 C31 C1 145.62(19) . . . . ?
C12 C7 C31 C13 127.6(2) . . . . ?
C8 C7 C31 C13 -54.9(2) . . . . ?
C12 C7 C31 C1 -104.5(2) . . . . ?
C8 C7 C31 C1 73.0(2) . . . . ?
C6 C1 C31 C13 133.05(18) . . . . ?
C2 C1 C31 C13 -49.3(2) . . . . ?
C6 C1 C31 C7 6.9(2) . . . . ?
C2 C1 C31 C7 -175.43(16) . . . . ?
C30 C25 C32 C19 -139.05(19) . . . . ?
C26 C25 C32 C19 42.4(3) . . . . ?
C30 C25 C32 C5 92.1(2) . . . . ?
C26 C25 C32 C5 -86.4(2) . . . . ?
C20 C19 C32 C25 -94.3(2) . . . . ?
C24 C19 C32 C25 83.9(2) . . . . ?
C20 C19 C32 C5 34.1(3) . . . . ?
C24 C19 C32 C5 -147.70(19) . . . . ?
C6 C5 C32 C25 35.5(2) . . . . ?
C4 C5 C32 C25 -144.80(18) . . . . ?
C6 C5 C32 C19 -92.9(2) . . . . ?
C4 C5 C32 C19 86.8(2) . . . . ?
C2 N1 C34 O1 1.0(3) . . . . ?
C2 N1 C34 C33 -179.95(17) . . . . ?

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1842262'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Br N O'
_chemical_formula_sum            'C21 H18 Br N O'
_chemical_formula_weight         380.27

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5843(5)
_cell_length_b                   10.5582(5)
_cell_length_c                   19.2410(9)
_cell_angle_alpha                77.8330(10)
_cell_angle_beta                 83.4690(10)
_cell_angle_gamma                66.8000(10)
_cell_volume                     1748.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.13

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    2.358
_shelx_estimated_absorpt_T_min   0.452
_shelx_estimated_absorpt_T_max   0.613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_T_max  0.581
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40862
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         25.344
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6413
_reflns_number_gt                5052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²] 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         6413
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.26903(3) 0.88347(3) 0.37651(2) 0.02115(10) Uani 1 1 d . . . . .
Br2 Br 0.25349(3) 0.85214(3) 0.13654(2) 0.02335(10) Uani 1 1 d . . . . .
O1 O 0.2180(2) 0.5794(3) 0.28168(11) 0.0311(6) Uani 1 1 d . . . . .
O2 O 0.6972(2) 0.6299(3) 0.28468(12) 0.0296(6) Uani 1 1 d . . . . .
N2 N 0.4912(3) 0.6255(2) 0.24062(12) 0.0179(6) Uani 1 1 d . . . . .
H2A H 0.4030 0.6174 0.2512 0.022 Uiso 1 1 calc R U . . .
N1 N -0.0213(3) 0.6234(3) 0.32731(12) 0.0175(5) Uani 1 1 d . . . . .
H1A H -0.1126 0.6289 0.3198 0.021 Uiso 1 1 calc R U . . .
C6 C -0.0926(3) 0.7543(3) 0.42477(15) 0.0153(6) Uani 1 1 d . . . . .
C34 C 0.8403(3) 0.7365(3) -0.05704(16) 0.0196(7) Uani 1 1 d . . . . .
C27 C 0.4526(3) 0.7292(3) 0.11479(16) 0.0189(7) Uani 1 1 d . . . . .
C4 C 0.0632(3) 0.6855(3) 0.52615(15) 0.0164(6) Uani 1 1 d . . . . .
C42 C 0.5682(3) 0.6304(3) 0.29381(16) 0.0198(7) Uani 1 1 d . . . . .
C38 C 1.0244(3) 0.8082(3) -0.13337(17) 0.0248(7) Uani 1 1 d . . . . .
H38A H 1.0708 0.8215 -0.1792 0.030 Uiso 1 1 calc R U . . .
C25 C 0.6511(3) 0.6571(3) 0.02598(15) 0.0190(7) Uani 1 1 d . . . . .
C26 C 0.5046(3) 0.7423(3) 0.04481(16) 0.0216(7) Uani 1 1 d . . . . .
H26A H 0.4401 0.8099 0.0093 0.026 Uiso 1 1 calc R U . . .
C2 C 0.1337(3) 0.5484(3) 0.43228(16) 0.0192(7) Uani 1 1 d . . . . .
H2B H 0.2021 0.4691 0.4135 0.023 Uiso 1 1 calc R U . . .
C22 C 0.5446(3) 0.6328(3) 0.16855(15) 0.0165(6) Uani 1 1 d . . . . .
C21 C 0.0864(3) 0.5972(3) 0.27400(16) 0.0210(7) Uani 1 1 d . . . . .
C39 C 0.9106(3) 0.7565(3) -0.12413(16) 0.0225(7) Uani 1 1 d . . . . .
H39A H 0.8795 0.7343 -0.1636 0.027 Uiso 1 1 calc R U . . .
C35 C 0.8863(4) 0.7727(4) -0.00093(17) 0.0289(8) Uani 1 1 d . . . . .
H35A H 0.8382 0.7624 0.0447 0.035 Uiso 1 1 calc R U . . .
C1 C 0.0068(3) 0.6423(3) 0.39452(15) 0.0160(6) Uani 1 1 d . . . . .
C5 C -0.0651(3) 0.7770(3) 0.48970(15) 0.0177(6) Uani 1 1 d . . . . .
H5A H -0.1344 0.8553 0.5089 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1602(3) 0.5704(3) 0.49696(15) 0.0183(7) Uani 1 1 d . . . . .
H3A H 0.2470 0.5051 0.5222 0.022 Uiso 1 1 calc R U . . .
C24 C 0.7405(3) 0.5558(3) 0.07875(16) 0.0226(7) Uani 1 1 d . . . . .
H24A H 0.8389 0.4935 0.0665 0.027 Uiso 1 1 calc R U . . .
C23 C 0.6880(3) 0.5444(3) 0.14901(16) 0.0201(7) Uani 1 1 d . . . . .
H23A H 0.7513 0.4749 0.1844 0.024 Uiso 1 1 calc R U . . .
C40 C 0.7177(3) 0.6739(3) -0.05014(16) 0.0216(7) Uani 1 1 d . . . . .
H40A H 0.7695 0.5774 -0.0613 0.026 Uiso 1 1 calc R U . . .
C41 C 0.4856(3) 0.6370(3) 0.36480(16) 0.0234(7) Uani 1 1 d . . . . .
H41A H 0.3848 0.6363 0.3609 0.035 Uiso 1 1 calc R U . . .
H41B H 0.5433 0.5558 0.3997 0.035 Uiso 1 1 calc R U . . .
H41C H 0.4746 0.7233 0.3802 0.035 Uiso 1 1 calc R U . . .
C36 C 1.0017(4) 0.8237(4) -0.01051(18) 0.0330(8) Uani 1 1 d . . . . .
H36A H 1.0326 0.8470 0.0286 0.040 Uiso 1 1 calc R U . . .
C18 C 0.2793(3) 0.8186(3) 0.51594(16) 0.0208(7) Uani 1 1 d . . . . .
H18A H 0.2105 0.8478 0.4785 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2479(3) 0.7478(3) 0.58100(15) 0.0168(6) Uani 1 1 d . . . . .
C14 C 0.3499(3) 0.7078(3) 0.63527(16) 0.0214(7) Uani 1 1 d . . . . .
H14A H 0.3286 0.6617 0.6807 0.026 Uiso 1 1 calc R U . . .
C12 C -0.1453(3) 0.7763(3) 0.66240(15) 0.0218(7) Uani 1 1 d . . . . .
H12A H -0.1466 0.6888 0.6581 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4105(3) 0.8473(3) 0.50479(17) 0.0254(7) Uani 1 1 d . . . . .
H17A H 0.4299 0.8974 0.4601 0.030 Uiso 1 1 calc R U . . .
C8 C -0.0240(3) 0.9398(3) 0.64042(16) 0.0204(7) Uani 1 1 d . . . . .
H8A H 0.0583 0.9661 0.6209 0.024 Uiso 1 1 calc R U . . .
C7 C -0.0226(3) 0.8120(3) 0.63258(15) 0.0174(6) Uani 1 1 d . . . . .
C33 C 0.5386(4) 0.6827(4) -0.13841(17) 0.0317(8) Uani 1 1 d . . . . .
H33A H 0.5797 0.5832 -0.1289 0.038 Uiso 1 1 calc R U . . .
C11 C -0.2635(4) 0.8648(3) 0.69770(16) 0.0249(7) Uani 1 1 d . . . . .
H11A H -0.3459 0.8386 0.7173 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4817(4) 0.7344(3) 0.62379(18) 0.0270(8) Uani 1 1 d . . . . .
H15A H 0.5509 0.7050 0.6610 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1077(3) 0.7096(3) 0.59507(15) 0.0176(7) Uani 1 1 d . . . . .
H19A H 0.1391 0.6173 0.6283 0.021 Uiso 1 1 calc R U . . .
C16 C 0.5130(3) 0.8035(3) 0.55833(18) 0.0275(8) Uani 1 1 d . . . . .
H16A H 0.6041 0.8208 0.5502 0.033 Uiso 1 1 calc R U . . .
C10 C -0.2631(4) 0.9930(3) 0.70497(16) 0.0246(7) Uani 1 1 d . . . . .
H10A H -0.3450 1.0543 0.7295 0.030 Uiso 1 1 calc R U . . .
C20 C 0.0333(4) 0.5891(4) 0.20533(17) 0.0305(8) Uani 1 1 d . . . . .
H20A H -0.0753 0.6064 0.2101 0.046 Uiso 1 1 calc R U . . .
H20B H 0.0502 0.6600 0.1672 0.046 Uiso 1 1 calc R U . . .
H20C H 0.0902 0.4958 0.1937 0.046 Uiso 1 1 calc R U . . .
C9 C -0.1434(4) 1.0309(3) 0.67636(17) 0.0264(7) Uani 1 1 d . . . . .
H9A H -0.1423 1.1182 0.6811 0.032 Uiso 1 1 calc R U . . .
C37 C 1.0712(4) 0.8407(4) -0.07634(19) 0.0319(8) Uani 1 1 d . . . . .
H37A H 1.1510 0.8745 -0.0827 0.038 Uiso 1 1 calc R U . . .
C31 C 0.3640(4) 0.8966(5) -0.19968(18) 0.0462(12) Uani 1 1 d . . . . .
H31A H 0.2846 0.9447 -0.2324 0.055 Uiso 1 1 calc R U . . .
C30 C 0.4173(4) 0.9726(4) -0.16694(18) 0.0398(10) Uani 1 1 d . . . . .
H30A H 0.3748 1.0722 -0.1767 0.048 Uiso 1 1 calc R U . . .
C32 C 0.4239(4) 0.7529(5) -0.18564(18) 0.0425(11) Uani 1 1 d . . . . .
H32A H 0.3861 0.7020 -0.2085 0.051 Uiso 1 1 calc R U . . .
C28 C 0.5957(3) 0.7547(4) -0.10426(15) 0.0217(7) Uani 1 1 d . . . . .
C29 C 0.5354(4) 0.9004(4) -0.11913(17) 0.0286(8) Uani 1 1 d . . . . .
H29A H 0.5742 0.9513 -0.0968 0.034 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 C6 1.894(3) . ?
Br2 C27 1.896(3) . ?
O1 C21 1.222(3) . ?
O2 C42 1.227(3) . ?
N2 C42 1.348(4) . ?
N2 C22 1.420(3) . ?
N2 H2A 0.8800 . ?
N1 C21 1.360(4) . ?
N1 C1 1.420(4) . ?
N1 H1A 0.8800 . ?
C6 C1 1.386(4) . ?
C6 C5 1.392(4) . ?
C34 C35 1.385(4) . ?
C34 C39 1.401(4) . ?
C34 C40 1.542(4) . ?
C27 C26 1.380(4) . ?
C27 C22 1.393(4) . ?
C4 C5 1.383(4) . ?
C4 C3 1.392(4) . ?
C4 C19 1.537(4) . ?
C42 C41 1.499(4) . ?
C38 C39 1.379(4) . ?
C38 C37 1.384(5) . ?
C38 H38A 0.9500 . ?
C25 C24 1.389(4) . ?
C25 C26 1.392(4) . ?
C25 C40 1.533(4) . ?
C26 H26A 0.9500 . ?
C2 C3 1.381(4) . ?
C2 C1 1.392(4) . ?
C2 H2B 0.9500 . ?
C22 C23 1.386(4) . ?
C21 C20 1.499(4) . ?
C39 H39A 0.9500 . ?
C35 C36 1.389(4) . ?
C35 H35A 0.9500 . ?
C5 H5A 0.9500 . ?
C3 H3A 0.9500 . ?
C24 C23 1.386(4) . ?
C24 H24A 0.9500 . ?
C23 H23A 0.9500 . ?
C40 C28 1.515(4) . ?
C40 H40A 1.0000 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C36 C37 1.374(5) . ?
C36 H36A 0.9500 . ?
C18 C13 1.383(4) . ?
C18 C17 1.390(4) . ?
C18 H18A 0.9500 . ?
C13 C14 1.395(4) . ?
C13 C19 1.529(4) . ?
C14 C15 1.382(4) . ?
C14 H14A 0.9500 . ?
C12 C11 1.370(4) . ?
C12 C7 1.399(4) . ?
C12 H12A 0.9500 . ?
C17 C16 1.383(4) . ?
C17 H17A 0.9500 . ?
C8 C7 1.384(4) . ?
C8 C9 1.395(4) . ?
C8 H8A 0.9500 . ?
C7 C19 1.520(4) . ?
C33 C32 1.373(5) . ?
C33 C28 1.389(4) . ?
C33 H33A 0.9500 . ?
C11 C10 1.391(4) . ?
C11 H11A 0.9500 . ?
C15 C16 1.382(5) . ?
C15 H15A 0.9500 . ?
C19 H19A 1.0000 . ?
C16 H16A 0.9500 . ?
C10 C9 1.380(4) . ?
C10 H10A 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C9 H9A 0.9500 . ?
C37 H37A 0.9500 . ?
C31 C32 1.371(6) . ?
C31 C30 1.383(6) . ?
C31 H31A 0.9500 . ?
C30 C29 1.403(5) . ?
C30 H30A 0.9500 . ?
C32 H32A 0.9500 . ?
C28 C29 1.391(5) . ?
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
C42 N2 C22 123.6(2) . . ?
C42 N2 H2A 118.2 . . ?
C22 N2 H2A 118.2 . . ?
C21 N1 C1 122.9(2) . . ?
C21 N1 H1A 118.5 . . ?
C1 N1 H1A 118.5 . . ?
C1 C6 C5 121.8(3) . . ?
C1 C6 Br1 119.9(2) . . ?
C5 C6 Br1 118.4(2) . . ?
C35 C34 C39 118.2(3) . . ?
C35 C34 C40 124.0(3) . . ?
C39 C34 C40 117.8(3) . . ?
C26 C27 C22 121.5(3) . . ?
C26 C27 Br2 117.9(2) . . ?
C22 C27 Br2 120.6(2) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C19 123.0(3) . . ?
C3 C4 C19 118.7(3) . . ?
O2 C42 N2 122.2(3) . . ?
O2 C42 C41 122.2(3) . . ?
N2 C42 C41 115.6(3) . . ?
C39 C38 C37 120.4(3) . . ?
C39 C38 H38A 119.8 . . ?
C37 C38 H38A 119.8 . . ?
C24 C25 C26 118.4(3) . . ?
C24 C25 C40 119.2(3) . . ?
C26 C25 C40 122.4(3) . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26A 119.8 . . ?
C25 C26 H26A 119.8 . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 H2B 120.0 . . ?
C1 C2 H2B 120.0 . . ?
C23 C22 C27 117.8(3) . . ?
C23 C22 N2 121.7(3) . . ?
C27 C22 N2 120.6(3) . . ?
O1 C21 N1 122.4(3) . . ?
O1 C21 C20 122.2(3) . . ?
N1 C21 C20 115.4(3) . . ?
C38 C39 C34 120.6(3) . . ?
C38 C39 H39A 119.7 . . ?
C34 C39 H39A 119.7 . . ?
C34 C35 C36 120.9(3) . . ?
C34 C35 H35A 119.6 . . ?
C36 C35 H35A 119.6 . . ?
C6 C1 C2 118.1(3) . . ?
C6 C1 N1 120.8(3) . . ?
C2 C1 N1 121.1(3) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3A 119.1 . . ?
C4 C3 H3A 119.1 . . ?
C23 C24 C25 120.7(3) . . ?
C23 C24 H24A 119.6 . . ?
C25 C24 H24A 119.6 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23A 119.5 . . ?
C22 C23 H23A 119.5 . . ?
C28 C40 C25 112.2(2) . . ?
C28 C40 C34 111.9(2) . . ?
C25 C40 C34 112.3(2) . . ?
C28 C40 H40A 106.6 . . ?
C25 C40 H40A 106.6 . . ?
C34 C40 H40A 106.6 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36A 119.8 . . ?
C35 C36 H36A 119.8 . . ?
C13 C18 C17 120.7(3) . . ?
C13 C18 H18A 119.7 . . ?
C17 C18 H18A 119.7 . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 C19 122.6(3) . . ?
C14 C13 C19 119.0(3) . . ?
C15 C14 C13 120.9(3) . . ?
C15 C14 H14A 119.5 . . ?
C13 C14 H14A 119.5 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12A 119.3 . . ?
C7 C12 H12A 119.3 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17A 119.8 . . ?
C18 C17 H17A 119.8 . . ?
C7 C8 C9 121.6(3) . . ?
C7 C8 H8A 119.2 . . ?
C9 C8 H8A 119.2 . . ?
C8 C7 C12 117.7(3) . . ?
C8 C7 C19 122.5(3) . . ?
C12 C7 C19 119.8(3) . . ?
C32 C33 C28 121.2(4) . . ?
C32 C33 H33A 119.4 . . ?
C28 C33 H33A 119.4 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C7 C19 C13 113.2(2) . . ?
C7 C19 C4 113.8(2) . . ?
C13 C19 C4 110.1(2) . . ?
C7 C19 H19A 106.4 . . ?
C13 C19 H19A 106.4 . . ?
C4 C19 H19A 106.4 . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 H16A 120.3 . . ?
C17 C16 H16A 120.3 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10A 120.1 . . ?
C11 C10 H10A 120.1 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C36 C37 C38 119.6(3) . . ?
C36 C37 H37A 120.2 . . ?
C38 C37 H37A 120.2 . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 H31A 119.5 . . ?
C30 C31 H31A 119.5 . . ?
C31 C30 C29 118.9(4) . . ?
C31 C30 H30A 120.5 . . ?
C29 C30 H30A 120.5 . . ?
C31 C32 C33 119.8(4) . . ?
C31 C32 H32A 120.1 . . ?
C33 C32 H32A 120.1 . . ?
C33 C28 C29 118.7(3) . . ?
C33 C28 C40 119.7(3) . . ?
C29 C28 C40 121.5(3) . . ?
C28 C29 C30 120.3(3) . . ?
C28 C29 H29A 119.8 . . ?
C30 C29 H29A 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 N2 C42 O2 -6.2(5) . . . . ?
C22 N2 C42 C41 173.5(3) . . . . ?
C22 C27 C26 C25 1.0(5) . . . . ?
Br2 C27 C26 C25 178.5(2) . . . . ?
C24 C25 C26 C27 2.4(4) . . . . ?
C40 C25 C26 C27 -176.0(3) . . . . ?
C26 C27 C22 C23 -3.6(4) . . . . ?
Br2 C27 C22 C23 179.0(2) . . . . ?
C26 C27 C22 N2 177.1(3) . . . . ?
Br2 C27 C22 N2 -0.4(4) . . . . ?
C42 N2 C22 C23 52.5(4) . . . . ?
C42 N2 C22 C27 -128.1(3) . . . . ?
C1 N1 C21 O1 4.6(5) . . . . ?
C1 N1 C21 C20 -176.3(3) . . . . ?
C37 C38 C39 C34 0.2(5) . . . . ?
C35 C34 C39 C38 1.3(5) . . . . ?
C40 C34 C39 C38 -178.0(3) . . . . ?
C39 C34 C35 C36 -1.7(5) . . . . ?
C40 C34 C35 C36 177.5(3) . . . . ?
C5 C6 C1 C2 2.5(4) . . . . ?
Br1 C6 C1 C2 -178.8(2) . . . . ?
C5 C6 C1 N1 -178.2(3) . . . . ?
Br1 C6 C1 N1 0.4(4) . . . . ?
C3 C2 C1 C6 -1.9(4) . . . . ?
C3 C2 C1 N1 178.8(3) . . . . ?
C21 N1 C1 C6 132.0(3) . . . . ?
C21 N1 C1 C2 -48.8(4) . . . . ?
C3 C4 C5 C6 -1.4(4) . . . . ?
C19 C4 C5 C6 175.2(3) . . . . ?
C1 C6 C5 C4 -0.8(4) . . . . ?
Br1 C6 C5 C4 -179.5(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C5 C4 C3 C2 2.0(4) . . . . ?
C19 C4 C3 C2 -174.7(3) . . . . ?
C26 C25 C24 C23 -3.2(5) . . . . ?
C40 C25 C24 C23 175.3(3) . . . . ?
C25 C24 C23 C22 0.6(5) . . . . ?
C27 C22 C23 C24 2.8(5) . . . . ?
N2 C22 C23 C24 -177.9(3) . . . . ?
C24 C25 C40 C28 162.6(3) . . . . ?
C26 C25 C40 C28 -19.0(4) . . . . ?
C24 C25 C40 C34 -70.3(4) . . . . ?
C26 C25 C40 C34 108.1(3) . . . . ?
C35 C34 C40 C28 127.8(3) . . . . ?
C39 C34 C40 C28 -53.0(4) . . . . ?
C35 C34 C40 C25 0.5(4) . . . . ?
C39 C34 C40 C25 179.7(3) . . . . ?
C34 C35 C36 C37 0.7(5) . . . . ?
C17 C18 C13 C14 0.8(4) . . . . ?
C17 C18 C13 C19 -178.0(3) . . . . ?
C18 C13 C14 C15 -1.9(5) . . . . ?
C19 C13 C14 C15 176.9(3) . . . . ?
C13 C18 C17 C16 1.1(5) . . . . ?
C9 C8 C7 C12 -0.4(4) . . . . ?
C9 C8 C7 C19 -178.6(3) . . . . ?
C11 C12 C7 C8 0.5(4) . . . . ?
C11 C12 C7 C19 178.8(3) . . . . ?
C7 C12 C11 C10 -0.4(5) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C8 C7 C19 C13 11.7(4) . . . . ?
C12 C7 C19 C13 -166.5(3) . . . . ?
C8 C7 C19 C4 -115.0(3) . . . . ?
C12 C7 C19 C4 66.8(3) . . . . ?
C18 C13 C19 C7 -98.3(3) . . . . ?
C14 C13 C19 C7 82.9(3) . . . . ?
C18 C13 C19 C4 30.3(4) . . . . ?
C14 C13 C19 C4 -148.5(3) . . . . ?
C5 C4 C19 C7 19.2(4) . . . . ?
C3 C4 C19 C7 -164.2(3) . . . . ?
C5 C4 C19 C13 -109.1(3) . . . . ?
C3 C4 C19 C13 67.5(3) . . . . ?
C14 C15 C16 C17 0.8(5) . . . . ?
C18 C17 C16 C15 -1.9(5) . . . . ?
C12 C11 C10 C9 0.1(5) . . . . ?
C11 C10 C9 C8 0.0(5) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C35 C36 C37 C38 0.8(5) . . . . ?
C39 C38 C37 C36 -1.2(5) . . . . ?
C32 C31 C30 C29 0.5(5) . . . . ?
C30 C31 C32 C33 0.0(5) . . . . ?
C28 C33 C32 C31 0.0(5) . . . . ?
C32 C33 C28 C29 -0.5(5) . . . . ?
C32 C33 C28 C40 177.4(3) . . . . ?
C25 C40 C28 C33 -93.5(3) . . . . ?
C34 C40 C28 C33 139.2(3) . . . . ?
C25 C40 C28 C29 84.4(3) . . . . ?
C34 C40 C28 C29 -42.9(4) . . . . ?
C33 C28 C29 C30 1.0(5) . . . . ?
C40 C28 C29 C30 -176.9(3) . . . . ?
C31 C30 C29 C28 -1.0(5) . . . . ?

_refine_diff_density_max         0.647
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.086

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1842261'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 Br N O'
_chemical_formula_sum            'C21 H18 Br N O'
_chemical_formula_weight         380.27

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'

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

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

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

_cell_length_a                   11.3526(6)
_cell_length_b                   38.9014(18)
_cell_length_c                   13.5468(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.621(2)
_cell_angle_gamma                90
_cell_volume                     5438.8(5)
_cell_formula_units_Z            12
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9126
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.38

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             2328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.274
_shelx_estimated_absorpt_T_min   0.600
_shelx_estimated_absorpt_T_max   0.659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.635
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            124077
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.237
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9951
_reflns_number_gt                8214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       CrystalClear
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0297P)²+4.7081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9951
_refine_ls_number_parameters     649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.36766(2) 0.03325(2) 0.51959(3) 0.04317(9) Uani 1 1 d . . . . .
Br2 Br -0.24990(3) 0.32578(2) 0.84701(3) 0.06135(12) Uani 1 1 d . . . . .
Br3 Br 0.64413(3) -0.01748(2) 0.79194(3) 0.05425(10) Uani 1 1 d . . . . .
N1 N 0.08626(17) 0.13281(4) 0.65789(15) 0.0203(4) Uani 1 1 d . . . . .
H1A H 0.1575 0.1271 0.7146 0.024 Uiso 1 1 calc R U . . .
N2 N 0.27540(18) 0.35050(5) 0.84455(15) 0.0246(4) Uani 1 1 d . . . . .
H2A H 0.3398 0.3455 0.9072 0.030 Uiso 1 1 calc R U . . .
N3 N 0.51922(17) 0.11171(5) 0.98029(15) 0.0223(4) Uani 1 1 d . . . . .
H3B H 0.5754 0.1194 1.0434 0.027 Uiso 1 1 calc R U . . .
O1 O -0.00634(16) 0.17458(4) 0.53152(14) 0.0335(4) Uani 1 1 d . . . . .
O2 O 0.22522(18) 0.37238(5) 0.67721(14) 0.0404(5) Uani 1 1 d . . . . .
O3 O 0.32420(15) 0.11927(4) 0.84109(13) 0.0301(4) Uani 1 1 d . . . . .
C1 C 0.0040(2) 0.07393(5) 0.63209(17) 0.0194(5) Uani 1 1 d . . . . .
C2 C -0.0195(2) 0.10953(6) 0.62742(17) 0.0193(5) Uani 1 1 d . . . . .
C3 C -0.1459(2) 0.12179(6) 0.59467(18) 0.0227(5) Uani 1 1 d . . . . .
H3A H -0.1610 0.1458 0.5940 0.027 Uiso 1 1 calc R U . . .
C4 C -0.2495(2) 0.09921(6) 0.56314(18) 0.0250(5) Uani 1 1 d . . . . .
H4A H -0.3355 0.1076 0.5398 0.030 Uiso 1 1 calc R U . . .
C5 C -0.2262(2) 0.06444(6) 0.56605(18) 0.0249(5) Uani 1 1 d . . . . .
C6 C -0.1015(2) 0.05173(6) 0.60137(18) 0.0237(5) Uani 1 1 d . . . . .
H6A H -0.0877 0.0276 0.6047 0.028 Uiso 1 1 calc R U . . .
C7 C 0.1617(2) 0.02362(5) 0.71073(18) 0.0204(5) Uani 1 1 d . . . . .
C8 C 0.1415(2) 0.01698(6) 0.80348(19) 0.0269(5) Uani 1 1 d . . . . .
H8A H 0.1089 0.0346 0.8337 0.032 Uiso 1 1 calc R U . . .
C9 C 0.1686(2) -0.01520(6) 0.8522(2) 0.0325(6) Uani 1 1 d . . . . .
H9A H 0.1551 -0.0193 0.9159 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2151(2) -0.04129(6) 0.8087(2) 0.0314(6) Uani 1 1 d . . . . .
H10A H 0.2337 -0.0633 0.8421 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2343(2) -0.03499(6) 0.7163(2) 0.0296(6) Uani 1 1 d . . . . .
H11A H 0.2657 -0.0528 0.6858 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2080(2) -0.00276(6) 0.66730(19) 0.0241(5) Uani 1 1 d . . . . .
H12A H 0.2218 0.0013 0.6037 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1822(2) 0.06434(5) 0.57196(18) 0.0200(5) Uani 1 1 d . . . . .
C14 C 0.3021(2) 0.07827(6) 0.5915(2) 0.0275(5) Uani 1 1 d . . . . .
H14A H 0.3555 0.0868 0.6617 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3446(2) 0.07981(7) 0.5096(2) 0.0344(6) Uani 1 1 d . . . . .
H15A H 0.4267 0.0896 0.5237 0.041 Uiso 1 1 calc R U . . .
C16 C 0.2684(2) 0.06716(6) 0.4074(2) 0.0300(6) Uani 1 1 d . . . . .
H16A H 0.2987 0.0678 0.3518 0.036 Uiso 1 1 calc R U . . .
C17 C 0.1481(2) 0.05357(6) 0.3867(2) 0.0286(5) Uani 1 1 d . . . . .
H17A H 0.0950 0.0450 0.3165 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1049(2) 0.05247(6) 0.46811(18) 0.0241(5) Uani 1 1 d . . . . .
H18A H 0.0213 0.0435 0.4529 0.029 Uiso 1 1 calc R U . . .
C19 C 0.1415(2) 0.06029(5) 0.66477(18) 0.0189(5) Uani 1 1 d . . . . .
H19A H 0.2000 0.0755 0.7247 0.023 Uiso 1 1 calc R U . . .
C20 C 0.2163(2) 0.18113(6) 0.6526(2) 0.0292(6) Uani 1 1 d . . . . .
H20A H 0.2794 0.1679 0.7132 0.044 Uiso 1 1 calc R U . . .
H20B H 0.2472 0.1834 0.5953 0.044 Uiso 1 1 calc R U . . .
H20C H 0.2059 0.2040 0.6783 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0881(2) 0.16277(6) 0.60834(18) 0.0237(5) Uani 1 1 d . . . . .
C22 C 0.1483(2) 0.34417(6) 0.83528(18) 0.0267(5) Uani 1 1 d . . . . .
C23 C 0.0567(2) 0.37024(7) 0.8048(2) 0.0348(6) Uani 1 1 d . . . . .
H23A H 0.0767 0.3920 0.7841 0.042 Uiso 1 1 calc R U . . .
C24 C -0.0639(3) 0.36458(7) 0.8045(2) 0.0418(7) Uani 1 1 d . . . . .
H24A H -0.1274 0.3823 0.7829 0.050 Uiso 1 1 calc R U . . .
C25 C -0.0901(2) 0.33300(8) 0.8359(2) 0.0382(7) Uani 1 1 d . . . . .
C26 C -0.0019(2) 0.30613(7) 0.8624(2) 0.0328(6) Uani 1 1 d . . . . .
H26A H -0.0235 0.2843 0.8818 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1183(2) 0.31124(6) 0.86048(18) 0.0254(5) Uani 1 1 d . . . . .
C28 C 0.1767(2) 0.24967(6) 0.9223(2) 0.0299(6) Uani 1 1 d . . . . .
C29 C 0.2190(3) 0.24416(7) 1.0329(2) 0.0399(7) Uani 1 1 d . . . . .
H29A H 0.2776 0.2599 1.0829 0.048 Uiso 1 1 calc R U . . .
C30 C 0.1764(3) 0.21567(8) 1.0714(3) 0.0514(8) Uani 1 1 d . . . . .
H30A H 0.2056 0.2123 1.1474 0.062 Uiso 1 1 calc R U . . .
C31 C 0.0926(3) 0.19252(8) 1.0003(3) 0.0504(8) Uani 1 1 d . . . . .
H31A H 0.0632 0.1733 1.0269 0.061 Uiso 1 1 calc R U . . .
C32 C 0.0511(3) 0.19729(7) 0.8901(3) 0.0459(7) Uani 1 1 d . . . . .
H32A H -0.0063 0.1812 0.8406 0.055 Uiso 1 1 calc R U . . .
C33 C 0.0930(3) 0.22564(7) 0.8512(2) 0.0373(6) Uani 1 1 d . . . . .
H33A H 0.0643 0.2287 0.7751 0.045 Uiso 1 1 calc R U . . .
C34 C 0.2499(2) 0.27658(5) 0.7857(2) 0.0248(5) Uani 1 1 d . . . . .
C35 C 0.3779(2) 0.27015(6) 0.8029(2) 0.0345(6) Uani 1 1 d . . . . .
H35A H 0.4430 0.2686 0.8750 0.041 Uiso 1 1 calc R U . . .
C36 C 0.4115(3) 0.26597(7) 0.7166(3) 0.0430(7) Uani 1 1 d . . . . .
H36A H 0.4992 0.2617 0.7298 0.052 Uiso 1 1 calc R U . . .
C37 C 0.3185(3) 0.26795(7) 0.6116(3) 0.0432(7) Uani 1 1 d . . . . .
H37A H 0.3418 0.2651 0.5524 0.052 Uiso 1 1 calc R U . . .
C38 C 0.1911(3) 0.27412(6) 0.5927(2) 0.0384(7) Uani 1 1 d . . . . .
H38A H 0.1266 0.2754 0.5203 0.046 Uiso 1 1 calc R U . . .
C39 C 0.1571(2) 0.27845(6) 0.6793(2) 0.0288(6) Uani 1 1 d . . . . .
H39A H 0.0693 0.2828 0.6656 0.035 Uiso 1 1 calc R U . . .
C40 C 0.2174(2) 0.28222(6) 0.88299(19) 0.0254(5) Uani 1 1 d . . . . .
H40A H 0.2990 0.2903 0.9439 0.031 Uiso 1 1 calc R U . . .
C41 C 0.4489(3) 0.36605(8) 0.7955(2) 0.0427(7) Uani 1 1 d . . . . .
H41A H 0.4978 0.3577 0.8697 0.064 Uiso 1 1 calc R U . . .
H41B H 0.4704 0.3521 0.7449 0.064 Uiso 1 1 calc R U . . .
H41C H 0.4716 0.3901 0.7907 0.064 Uiso 1 1 calc R U . . .
C42 C 0.3066(2) 0.36338(6) 0.7665(2) 0.0299(6) Uani 1 1 d . . . . .
C43 C 0.5507(2) 0.08149(6) 0.93645(17) 0.0215(5) Uani 1 1 d . . . . .
C44 C 0.4745(2) 0.05244(6) 0.92094(19) 0.0268(5) Uani 1 1 d . . . . .
H44A H 0.4027 0.0530 0.9397 0.032 Uiso 1 1 calc R U . . .
C45 C 0.5016(2) 0.02273(6) 0.87860(19) 0.0295(6) Uani 1 1 d . . . . .
H45A H 0.4497 0.0027 0.8682 0.035 Uiso 1 1 calc R U . . .
C46 C 0.6063(2) 0.02292(6) 0.8517(2) 0.0308(6) Uani 1 1 d . . . . .
C47 C 0.6845(2) 0.05150(6) 0.86766(19) 0.0268(5) Uani 1 1 d . . . . .
H47A H 0.7562 0.0507 0.8488 0.032 Uiso 1 1 calc R U . . .
C48 C 0.6582(2) 0.08133(6) 0.91126(17) 0.0218(5) Uani 1 1 d . . . . .
C49 C 0.6857(2) 0.13996(6) 0.83977(19) 0.0236(5) Uani 1 1 d . . . . .
C50 C 0.6007(2) 0.13174(6) 0.73444(19) 0.0273(5) Uani 1 1 d . . . . .
H50A H 0.5735 0.1086 0.7166 0.033 Uiso 1 1 calc R U . . .
C51 C 0.5548(2) 0.15700(6) 0.6543(2) 0.0320(6) Uani 1 1 d . . . . .
H51A H 0.4958 0.1510 0.5827 0.038 Uiso 1 1 calc R U . . .
C52 C 0.5940(3) 0.19035(7) 0.6782(2) 0.0407(7) Uani 1 1 d . . . . .
H52A H 0.5624 0.2075 0.6234 0.049 Uiso 1 1 calc R U . . .
C53 C 0.6798(3) 0.19895(7) 0.7823(3) 0.0550(9) Uani 1 1 d . . . . .
H53A H 0.7084 0.2220 0.7989 0.066 Uiso 1 1 calc R U . . .
C54 C 0.7242(3) 0.17415(6) 0.8624(2) 0.0423(7) Uani 1 1 d . . . . .
H54A H 0.7818 0.1805 0.9341 0.051 Uiso 1 1 calc R U . . .
C55 C 0.8838(2) 0.10489(6) 0.95582(18) 0.0221(5) Uani 1 1 d . . . . .
C56 C 0.9626(2) 0.09311(7) 1.0590(2) 0.0350(6) Uani 1 1 d . . . . .
H56A H 0.9272 0.0903 1.1109 0.042 Uiso 1 1 calc R U . . .
C57 C 1.0917(3) 0.08539(8) 1.0879(2) 0.0424(7) Uani 1 1 d . . . . .
H57A H 1.1437 0.0771 1.1588 0.051 Uiso 1 1 calc R U . . .
C58 C 1.1450(2) 0.08971(7) 1.0140(2) 0.0345(6) Uani 1 1 d . . . . .
H58A H 1.2339 0.0847 1.0337 0.041 Uiso 1 1 calc R U . . .
C59 C 1.0679(2) 0.10136(6) 0.9115(2) 0.0284(5) Uani 1 1 d . . . . .
H59A H 1.1040 0.1045 0.8602 0.034 Uiso 1 1 calc R U . . .
C60 C 0.9377(2) 0.10864(6) 0.88185(19) 0.0256(5) Uani 1 1 d . . . . .
H60A H 0.8853 0.1162 0.8102 0.031 Uiso 1 1 calc R U . . .
C61 C 0.7424(2) 0.11348(6) 0.93029(18) 0.0221(5) Uani 1 1 d . . . . .
H61A H 0.7432 0.1246 0.9971 0.027 Uiso 1 1 calc R U . . .
C62 C 0.3915(2) 0.16010(7) 0.9867(2) 0.0396(7) Uani 1 1 d . . . . .
H62A H 0.4685 0.1631 1.0550 0.059 Uiso 1 1 calc R U . . .
H62B H 0.3806 0.1803 0.9406 0.059 Uiso 1 1 calc R U . . .
H62C H 0.3149 0.1574 1.0019 0.059 Uiso 1 1 calc R U . . .
C63 C 0.4077(2) 0.12871(6) 0.92918(19) 0.0238(5) 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 C5 1.899(2) . ?
Br2 C25 1.903(3) . ?
Br3 C46 1.898(2) . ?
N1 C21 1.349(3) . ?
N1 C2 1.421(3) . ?
N1 H1A 0.8800 . ?
N2 C42 1.344(3) . ?
N2 C22 1.416(3) . ?
N2 H2A 0.8800 . ?
N3 C63 1.337(3) . ?
N3 C43 1.428(3) . ?
N3 H3B 0.8800 . ?
O1 C21 1.231(3) . ?
O2 C42 1.229(3) . ?
O3 C63 1.231(3) . ?
C1 C6 1.393(3) . ?
C1 C2 1.407(3) . ?
C1 C19 1.529(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.385(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 C12 1.390(3) . ?
C7 C8 1.392(3) . ?
C7 C19 1.535(3) . ?
C8 C9 1.388(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.385(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.392(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.384(3) . ?
C13 C18 1.391(3) . ?
C13 C19 1.518(3) . ?
C14 C15 1.384(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 1.0000 . ?
C20 C21 1.503(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 C23 1.387(3) . ?
C22 C27 1.403(3) . ?
C23 C24 1.385(4) . ?
C23 H23A 0.9500 . ?
C24 C25 1.372(4) . ?
C24 H24A 0.9500 . ?
C25 C26 1.387(4) . ?
C26 C27 1.390(3) . ?
C26 H26A 0.9500 . ?
C27 C40 1.532(3) . ?
C28 C29 1.386(4) . ?
C28 C33 1.393(4) . ?
C28 C40 1.519(3) . ?
C29 C30 1.395(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.372(5) . ?
C30 H30A 0.9500 . ?
C31 C32 1.378(4) . ?
C31 H31A 0.9500 . ?
C32 C33 1.389(4) . ?
C32 H32A 0.9500 . ?
C33 H33A 0.9500 . ?
C34 C39 1.388(3) . ?
C34 C35 1.395(3) . ?
C34 C40 1.526(3) . ?
C35 C36 1.382(4) . ?
C35 H35A 0.9500 . ?
C36 C37 1.375(4) . ?
C36 H36A 0.9500 . ?
C37 C38 1.380(4) . ?
C37 H37A 0.9500 . ?
C38 C39 1.390(4) . ?
C38 H38A 0.9500 . ?
C39 H39A 0.9500 . ?
C40 H40A 1.0000 . ?
C41 C42 1.499(4) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C43 C44 1.385(3) . ?
C43 C48 1.398(3) . ?
C44 C45 1.381(3) . ?
C44 H44A 0.9500 . ?
C45 C46 1.380(4) . ?
C45 H45A 0.9500 . ?
C46 C47 1.383(3) . ?
C47 C48 1.389(3) . ?
C47 H47A 0.9500 . ?
C48 C61 1.529(3) . ?
C49 C50 1.386(3) . ?
C49 C54 1.394(3) . ?
C49 C61 1.524(3) . ?
C50 C51 1.394(3) . ?
C50 H50A 0.9500 . ?
C51 C52 1.366(4) . ?
C51 H51A 0.9500 . ?
C52 C53 1.380(4) . ?
C52 H52A 0.9500 . ?
C53 C54 1.381(4) . ?
C53 H53A 0.9500 . ?
C54 H54A 0.9500 . ?
C55 C60 1.382(3) . ?
C55 C56 1.386(3) . ?
C55 C61 1.532(3) . ?
C56 C57 1.383(4) . ?
C56 H56A 0.9500 . ?
C57 C58 1.380(4) . ?
C57 H57A 0.9500 . ?
C58 C59 1.374(3) . ?
C58 H58A 0.9500 . ?
C59 C60 1.390(3) . ?
C59 H59A 0.9500 . ?
C60 H60A 0.9500 . ?
C61 H61A 1.0000 . ?
C62 C63 1.500(3) . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N1 C2 126.33(18) . . ?
C21 N1 H1A 116.8 . . ?
C2 N1 H1A 116.8 . . ?
C42 N2 C22 126.0(2) . . ?
C42 N2 H2A 117.0 . . ?
C22 N2 H2A 117.0 . . ?
C63 N3 C43 122.60(19) . . ?
C63 N3 H3B 118.7 . . ?
C43 N3 H3B 118.7 . . ?
C6 C1 C2 118.2(2) . . ?
C6 C1 C19 121.25(19) . . ?
C2 C1 C19 120.44(19) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 N1 120.42(19) . . ?
C1 C2 N1 119.49(19) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3A 119.7 . . ?
C2 C3 H3A 119.7 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 Br1 119.54(17) . . ?
C6 C5 Br1 119.25(18) . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6A 119.6 . . ?
C1 C6 H6A 119.6 . . ?
C12 C7 C8 118.6(2) . . ?
C12 C7 C19 122.2(2) . . ?
C8 C7 C19 119.1(2) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C11 C10 C9 119.3(2) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 120.6(2) . . ?
C10 C11 H11A 119.7 . . ?
C12 C11 H11A 119.7 . . ?
C7 C12 C11 120.5(2) . . ?
C7 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C18 118.6(2) . . ?
C14 C13 C19 119.8(2) . . ?
C18 C13 C19 121.48(19) . . ?
C13 C14 C15 120.5(2) . . ?
C13 C14 H14A 119.8 . . ?
C15 C14 H14A 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17A 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C17 C18 C13 120.9(2) . . ?
C17 C18 H18A 119.6 . . ?
C13 C18 H18A 119.6 . . ?
C13 C19 C1 110.52(17) . . ?
C13 C19 C7 112.77(18) . . ?
C1 C19 C7 113.69(17) . . ?
C13 C19 H19A 106.4 . . ?
C1 C19 H19A 106.4 . . ?
C7 C19 H19A 106.4 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 N1 123.7(2) . . ?
O1 C21 C20 121.2(2) . . ?
N1 C21 C20 115.15(19) . . ?
C23 C22 C27 120.8(2) . . ?
C23 C22 N2 120.6(2) . . ?
C27 C22 N2 118.6(2) . . ?
C24 C23 C22 120.2(3) . . ?
C24 C23 H23A 119.9 . . ?
C22 C23 H23A 119.9 . . ?
C25 C24 C23 118.9(2) . . ?
C25 C24 H24A 120.6 . . ?
C23 C24 H24A 120.6 . . ?
C24 C25 C26 121.9(3) . . ?
C24 C25 Br2 119.6(2) . . ?
C26 C25 Br2 118.5(2) . . ?
C25 C26 C27 119.7(3) . . ?
C25 C26 H26A 120.1 . . ?
C27 C26 H26A 120.1 . . ?
C26 C27 C22 118.3(2) . . ?
C26 C27 C40 122.4(2) . . ?
C22 C27 C40 119.3(2) . . ?
C29 C28 C33 118.2(2) . . ?
C29 C28 C40 119.3(2) . . ?
C33 C28 C40 122.4(2) . . ?
C28 C29 C30 120.6(3) . . ?
C28 C29 H29A 119.7 . . ?
C30 C29 H29A 119.7 . . ?
C31 C30 C29 120.4(3) . . ?
C31 C30 H30A 119.8 . . ?
C29 C30 H30A 119.8 . . ?
C30 C31 C32 119.8(3) . . ?
C30 C31 H31A 120.1 . . ?
C32 C31 H31A 120.1 . . ?
C31 C32 C33 120.1(3) . . ?
C31 C32 H32A 120.0 . . ?
C33 C32 H32A 120.0 . . ?
C32 C33 C28 120.9(3) . . ?
C32 C33 H33A 119.6 . . ?
C28 C33 H33A 119.6 . . ?
C39 C34 C35 118.0(2) . . ?
C39 C34 C40 122.5(2) . . ?
C35 C34 C40 119.5(2) . . ?
C36 C35 C34 121.0(3) . . ?
C36 C35 H35A 119.5 . . ?
C34 C35 H35A 119.5 . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36A 119.9 . . ?
C35 C36 H36A 119.9 . . ?
C36 C37 C38 119.7(3) . . ?
C36 C37 H37A 120.1 . . ?
C38 C37 H37A 120.1 . . ?
C37 C38 C39 120.1(3) . . ?
C37 C38 H38A 119.9 . . ?
C39 C38 H38A 119.9 . . ?
C34 C39 C38 120.8(2) . . ?
C34 C39 H39A 119.6 . . ?
C38 C39 H39A 119.6 . . ?
C28 C40 C34 113.69(19) . . ?
C28 C40 C27 112.3(2) . . ?
C34 C40 C27 110.85(19) . . ?
C28 C40 H40A 106.5 . . ?
C34 C40 H40A 106.5 . . ?
C27 C40 H40A 106.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O2 C42 N2 123.0(2) . . ?
O2 C42 C41 121.6(2) . . ?
N2 C42 C41 115.4(2) . . ?
C44 C43 C48 120.9(2) . . ?
C44 C43 N3 119.1(2) . . ?
C48 C43 N3 120.1(2) . . ?
C45 C44 C43 120.9(2) . . ?
C45 C44 H44A 119.6 . . ?
C43 C44 H44A 119.6 . . ?
C46 C45 C44 118.1(2) . . ?
C46 C45 H45A 121.0 . . ?
C44 C45 H45A 121.0 . . ?
C45 C46 C47 122.1(2) . . ?
C45 C46 Br3 118.77(18) . . ?
C47 C46 Br3 119.2(2) . . ?
C46 C47 C48 120.0(2) . . ?
C46 C47 H47A 120.0 . . ?
C48 C47 H47A 120.0 . . ?
C47 C48 C43 118.1(2) . . ?
C47 C48 C61 121.7(2) . . ?
C43 C48 C61 120.2(2) . . ?
C50 C49 C54 117.8(2) . . ?
C50 C49 C61 123.5(2) . . ?
C54 C49 C61 118.7(2) . . ?
C49 C50 C51 120.8(2) . . ?
C49 C50 H50A 119.6 . . ?
C51 C50 H50A 119.6 . . ?
C52 C51 C50 120.4(2) . . ?
C52 C51 H51A 119.8 . . ?
C50 C51 H51A 119.8 . . ?
C51 C52 C53 119.6(3) . . ?
C51 C52 H52A 120.2 . . ?
C53 C52 H52A 120.2 . . ?
C52 C53 C54 120.3(3) . . ?
C52 C53 H53A 119.8 . . ?
C54 C53 H53A 119.8 . . ?
C53 C54 C49 121.0(3) . . ?
C53 C54 H54A 119.5 . . ?
C49 C54 H54A 119.5 . . ?
C60 C55 C56 118.1(2) . . ?
C60 C55 C61 123.5(2) . . ?
C56 C55 C61 118.4(2) . . ?
C57 C56 C55 121.3(2) . . ?
C57 C56 H56A 119.3 . . ?
C55 C56 H56A 119.3 . . ?
C58 C57 C56 120.1(2) . . ?
C58 C57 H57A 119.9 . . ?
C56 C57 H57A 119.9 . . ?
C59 C58 C57 119.1(2) . . ?
C59 C58 H58A 120.5 . . ?
C57 C58 H58A 120.5 . . ?
C58 C59 C60 120.8(2) . . ?
C58 C59 H59A 119.6 . . ?
C60 C59 H59A 119.6 . . ?
C55 C60 C59 120.5(2) . . ?
C55 C60 H60A 119.7 . . ?
C59 C60 H60A 119.7 . . ?
C49 C61 C48 113.14(18) . . ?
C49 C61 C55 112.35(18) . . ?
C48 C61 C55 112.46(18) . . ?
C49 C61 H61A 106.1 . . ?
C48 C61 H61A 106.1 . . ?
C55 C61 H61A 106.1 . . ?
C63 C62 H62A 109.5 . . ?
C63 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C63 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
O3 C63 N3 122.4(2) . . ?
O3 C63 C62 122.3(2) . . ?
N3 C63 C62 115.3(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
C6 C1 C2 C3 1.2(3) . . . . ?
C19 C1 C2 C3 178.3(2) . . . . ?
C6 C1 C2 N1 -179.8(2) . . . . ?
C19 C1 C2 N1 -2.7(3) . . . . ?
C21 N1 C2 C3 -40.8(3) . . . . ?
C21 N1 C2 C1 140.2(2) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
N1 C2 C3 C4 178.9(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C5 Br1 -178.44(17) . . . . ?
C4 C5 C6 C1 -1.9(4) . . . . ?
Br1 C5 C6 C1 177.55(17) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C19 C1 C6 C5 -176.3(2) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C19 C7 C8 C9 -174.9(2) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
C19 C7 C12 C11 175.1(2) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C18 C13 C14 C15 -1.0(3) . . . . ?
C19 C13 C14 C15 175.2(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C13 -1.2(3) . . . . ?
C14 C13 C18 C17 1.9(3) . . . . ?
C19 C13 C18 C17 -174.2(2) . . . . ?
C14 C13 C19 C1 132.5(2) . . . . ?
C18 C13 C19 C1 -51.4(3) . . . . ?
C14 C13 C19 C7 -99.0(2) . . . . ?
C18 C13 C19 C7 77.1(2) . . . . ?
C6 C1 C19 C13 101.2(2) . . . . ?
C2 C1 C19 C13 -75.7(2) . . . . ?
C6 C1 C19 C7 -26.7(3) . . . . ?
C2 C1 C19 C7 156.3(2) . . . . ?
C12 C7 C19 C13 -2.3(3) . . . . ?
C8 C7 C19 C13 173.27(19) . . . . ?
C12 C7 C19 C1 124.6(2) . . . . ?
C8 C7 C19 C1 -59.9(3) . . . . ?
C2 N1 C21 O1 3.5(4) . . . . ?
C2 N1 C21 C20 -175.7(2) . . . . ?
C42 N2 C22 C23 -55.4(3) . . . . ?
C42 N2 C22 C27 126.3(2) . . . . ?
C27 C22 C23 C24 3.5(4) . . . . ?
N2 C22 C23 C24 -174.7(2) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C26 -3.4(4) . . . . ?
C23 C24 C25 Br2 175.11(19) . . . . ?
C24 C25 C26 C27 1.9(4) . . . . ?
Br2 C25 C26 C27 -176.65(18) . . . . ?
C25 C26 C27 C22 2.3(3) . . . . ?
C25 C26 C27 C40 -176.7(2) . . . . ?
C23 C22 C27 C26 -5.0(3) . . . . ?
N2 C22 C27 C26 173.3(2) . . . . ?
C23 C22 C27 C40 174.1(2) . . . . ?
N2 C22 C27 C40 -7.6(3) . . . . ?
C33 C28 C29 C30 -1.4(4) . . . . ?
C40 C28 C29 C30 175.7(2) . . . . ?
C28 C29 C30 C31 0.5(4) . . . . ?
C29 C30 C31 C32 0.6(5) . . . . ?
C30 C31 C32 C33 -0.7(5) . . . . ?
C31 C32 C33 C28 -0.3(4) . . . . ?
C29 C28 C33 C32 1.3(4) . . . . ?
C40 C28 C33 C32 -175.7(2) . . . . ?
C39 C34 C35 C36 0.4(4) . . . . ?
C40 C34 C35 C36 -178.0(2) . . . . ?
C34 C35 C36 C37 -0.3(4) . . . . ?
C35 C36 C37 C38 -0.1(4) . . . . ?
C36 C37 C38 C39 0.3(4) . . . . ?
C35 C34 C39 C38 -0.1(3) . . . . ?
C40 C34 C39 C38 178.2(2) . . . . ?
C37 C38 C39 C34 -0.2(4) . . . . ?
C29 C28 C40 C34 140.4(2) . . . . ?
C33 C28 C40 C34 -42.6(3) . . . . ?
C29 C28 C40 C27 -92.8(3) . . . . ?
C33 C28 C40 C27 84.2(3) . . . . ?
C39 C34 C40 C28 88.6(3) . . . . ?
C35 C34 C40 C28 -93.1(3) . . . . ?
C39 C34 C40 C27 -38.9(3) . . . . ?
C35 C34 C40 C27 139.4(2) . . . . ?
C26 C27 C40 C28 -8.1(3) . . . . ?
C22 C27 C40 C28 172.9(2) . . . . ?
C26 C27 C40 C34 120.3(2) . . . . ?
C22 C27 C40 C34 -58.7(3) . . . . ?
C22 N2 C42 O2 2.6(4) . . . . ?
C22 N2 C42 C41 -177.3(2) . . . . ?
C63 N3 C43 C44 -63.1(3) . . . . ?
C63 N3 C43 C48 117.8(2) . . . . ?
C48 C43 C44 C45 -1.0(3) . . . . ?
N3 C43 C44 C45 179.9(2) . . . . ?
C43 C44 C45 C46 -0.3(3) . . . . ?
C44 C45 C46 C47 1.1(4) . . . . ?
C44 C45 C46 Br3 -179.33(17) . . . . ?
C45 C46 C47 C48 -0.5(4) . . . . ?
Br3 C46 C47 C48 179.94(17) . . . . ?
C46 C47 C48 C43 -0.9(3) . . . . ?
C46 C47 C48 C61 179.9(2) . . . . ?
C44 C43 C48 C47 1.6(3) . . . . ?
N3 C43 C48 C47 -179.3(2) . . . . ?
C44 C43 C48 C61 -179.2(2) . . . . ?
N3 C43 C48 C61 -0.1(3) . . . . ?
C54 C49 C50 C51 -0.5(4) . . . . ?
C61 C49 C50 C51 -178.3(2) . . . . ?
C49 C50 C51 C52 0.7(4) . . . . ?
C50 C51 C52 C53 0.1(4) . . . . ?
C51 C52 C53 C54 -1.1(5) . . . . ?
C52 C53 C54 C49 1.3(5) . . . . ?
C50 C49 C54 C53 -0.5(4) . . . . ?
C61 C49 C54 C53 177.4(3) . . . . ?
C60 C55 C56 C57 0.3(4) . . . . ?
C61 C55 C56 C57 -179.0(2) . . . . ?
C55 C56 C57 C58 0.7(5) . . . . ?
C56 C57 C58 C59 -0.7(4) . . . . ?
C57 C58 C59 C60 -0.3(4) . . . . ?
C56 C55 C60 C59 -1.2(4) . . . . ?
C61 C55 C60 C59 178.0(2) . . . . ?
C58 C59 C60 C55 1.2(4) . . . . ?
C50 C49 C61 C48 -24.7(3) . . . . ?
C54 C49 C61 C48 157.5(2) . . . . ?
C50 C49 C61 C55 104.0(2) . . . . ?
C54 C49 C61 C55 -73.8(3) . . . . ?
C47 C48 C61 C49 98.0(2) . . . . ?
C43 C48 C61 C49 -81.1(3) . . . . ?
C47 C48 C61 C55 -30.6(3) . . . . ?
C43 C48 C61 C55 150.3(2) . . . . ?
C60 C55 C61 C49 -25.0(3) . . . . ?
C56 C55 C61 C49 154.2(2) . . . . ?
C60 C55 C61 C48 104.0(3) . . . . ?
C56 C55 C61 C48 -76.7(3) . . . . ?
C43 N3 C63 O3 0.5(3) . . . . ?
C43 N3 C63 C62 -179.4(2) . . . . ?

_refine_diff_density_max         0.669
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

