# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_bd_390_0m
_database_code_depnum_ccdc_archive 'CCDC 1867796'
_audit_update_record             
;
2018-09-14 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H36 N8'
_chemical_formula_sum            'C50 H36 N8'
_chemical_formula_weight         748.87

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'

_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                   11.9420(8)
_cell_length_b                   12.7737(9)
_cell_length_c                   12.9601(8)
_cell_angle_alpha                91.778(3)
_cell_angle_beta                 102.372(3)
_cell_angle_gamma                102.443(3)
_cell_volume                     1879.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.81

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(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            31257
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.638
_diffrn_reflns_theta_max         29.083
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10002
_reflns_number_gt                7147
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0833P)²+0.2697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         10002
_refine_ls_number_parameters     534
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C -0.00783(15) 0.51840(15) -0.35519(13) 0.0597(4) Uani 1 1 d . . . . .
H1 H -0.024452 0.547608 -0.420042 0.072 Uiso 1 1 calc R U . . .
C2 C -0.05615(16) 0.41300(15) -0.34549(13) 0.0612(4) Uani 1 1 d . . . . .
H18 H -0.106138 0.370651 -0.403973 0.073 Uiso 1 1 calc R U . . .
C3 C -0.03137(14) 0.36872(14) -0.24940(12) 0.0555(4) Uani 1 1 d . . . . .
H3 H -0.063519 0.296632 -0.243677 0.067 Uiso 1 1 calc R U . . .
C4 C 0.04143(12) 0.43212(12) -0.16191(11) 0.0444(3) Uani 1 1 d . . . . .
C5 C 0.17157(12) 0.40566(12) 0.01120(11) 0.0440(3) Uani 1 1 d . . . . .
C6 C 0.15386(12) 0.33319(12) 0.08934(11) 0.0431(3) Uani 1 1 d . . . . .
C7 C 0.24793(12) 0.33174(11) 0.17563(10) 0.0415(3) Uani 1 1 d . . . . .
C8 C 0.23406(11) 0.25965(11) 0.26255(10) 0.0419(3) Uani 1 1 d . . . . .
C9 C 0.19443(16) 0.29309(15) 0.34720(13) 0.0606(4) Uani 1 1 d . . . . .
H8 H 0.180312 0.361727 0.351461 0.073 Uiso 1 1 calc R U . . .
C10 C 0.17536(19) 0.22525(19) 0.42628(14) 0.0751(6) Uani 1 1 d . . . . .
H7 H 0.146319 0.247892 0.482098 0.090 Uiso 1 1 calc R U . . .
C11 C 0.19901(16) 0.12520(16) 0.42269(14) 0.0671(5) Uani 1 1 d . . . . .
H2 H 0.186901 0.080052 0.476128 0.081 Uiso 1 1 calc R U . . .
C12 C 0.03502(12) 0.27424(12) 0.05416(11) 0.0479(3) Uani 1 1 d . . . . .
C13 C 0.35742(12) 0.47287(12) 0.09013(10) 0.0426(3) Uani 1 1 d . . . . .
C14 C 0.53765(12) 0.51170(12) 0.19929(11) 0.0445(3) Uani 1 1 d . . . . .
C15 C 0.46918(12) 0.42926(12) 0.24451(11) 0.0442(3) Uani 1 1 d . . . . .
C16 C 0.35274(12) 0.40294(11) 0.17486(10) 0.0417(3) Uani 1 1 d . . . . .
C17 C 0.24032(19) 0.09248(15) 0.34039(17) 0.0741(5) Uani 1 1 d . . . . .
H5 H 0.257044 0.024758 0.337852 0.089 Uiso 1 1 calc R U . . .
C18 C 0.25782(18) 0.15907(15) 0.26008(15) 0.0675(5) Uani 1 1 d . . . . .
H6 H 0.285876 0.135488 0.204034 0.081 Uiso 1 1 calc R U . . .
C19 C 0.52101(14) 0.39144(14) 0.33824(12) 0.0555(4) Uani 1 1 d . . . . .
H12 H 0.477645 0.336978 0.369256 0.067 Uiso 1 1 calc R U . . .
C20 C 0.63772(15) 0.43592(16) 0.38453(14) 0.0637(4) Uani 1 1 d . . . . .
H9 H 0.672699 0.411672 0.447664 0.076 Uiso 1 1 calc R U . . .
C21 C 0.70380(14) 0.51648(15) 0.33816(14) 0.0603(4) Uani 1 1 d . . . . .
H11 H 0.782242 0.545299 0.370986 0.072 Uiso 1 1 calc R U . . .
C22 C 0.65525(13) 0.55449(13) 0.24441(13) 0.0517(4) Uani 1 1 d . . . . .
H10 H 0.700134 0.607109 0.212654 0.062 Uiso 1 1 calc R U . . .
C23 C -0.03118(15) 0.18646(15) 0.10580(14) 0.0634(5) Uani 1 1 d . . . . .
H13 H -0.109740 0.161773 0.063493 0.095 Uiso 1 1 calc R U . . .
H15 H -0.034308 0.213172 0.174944 0.095 Uiso 1 1 calc R U . . .
H14 H 0.007867 0.127893 0.112240 0.095 Uiso 1 1 calc R U . . .
C24 C 0.08907(14) 0.53905(13) -0.17120(13) 0.0544(4) Uani 1 1 d . . . . .
H17 H 0.136673 0.582518 -0.112360 0.065 Uiso 1 1 calc R U . . .
C25 C 0.06558(16) 0.58100(15) -0.26838(14) 0.0625(4) Uani 1 1 d . . . . .
H16 H 0.099748 0.652336 -0.275211 0.075 Uiso 1 1 calc R U . . .
C26 C 0.0676(3) 0.12789(19) -0.2710(2) 0.1063(10) Uani 1 1 d . . . . .
H19 H 0.004367 0.122612 -0.328496 0.128 Uiso 1 1 calc R U . . .
C27 C 0.0488(2) 0.09103(17) -0.1763(2) 0.0884(7) Uani 1 1 d . . . . .
H36 H -0.027285 0.061700 -0.169407 0.106 Uiso 1 1 calc R U . . .
C28 C 0.14322(15) 0.09758(14) -0.09136(15) 0.0635(4) Uani 1 1 d . . . . .
H35 H 0.130850 0.073993 -0.026673 0.076 Uiso 1 1 calc R U . . .
C29 C 0.25598(14) 0.13940(11) -0.10329(11) 0.0486(3) Uani 1 1 d . . . . .
C30 C 0.37049(12) 0.06406(11) 0.04946(10) 0.0423(3) Uani 1 1 d . . . . .
C31 C 0.33561(12) -0.08822(11) 0.12499(11) 0.0431(3) Uani 1 1 d . . . . .
C32 C 0.34609(12) -0.22709(12) 0.22642(11) 0.0453(3) Uani 1 1 d . . . . .
C33 C 0.32655(15) -0.32806(12) 0.26506(13) 0.0525(4) Uani 1 1 d . . . . .
H27 H 0.260847 -0.381724 0.233703 0.063 Uiso 1 1 calc R U . . .
C34 C 0.40801(16) -0.34582(14) 0.35151(13) 0.0576(4) Uani 1 1 d . . . . .
H20 H 0.396740 -0.412650 0.379116 0.069 Uiso 1 1 calc R U . . .
C35 C 0.52609(12) 0.20562(11) 0.08306(11) 0.0438(3) Uani 1 1 d . . . . .
C36 C 0.48109(12) 0.10377(11) 0.11955(10) 0.0408(3) Uani 1 1 d . . . . .
C37 C 0.44633(12) -0.14589(12) 0.27145(11) 0.0441(3) Uani 1 1 d . . . . .
C38 C 0.44224(11) -0.05596(11) 0.20569(11) 0.0420(3) Uani 1 1 d . . . . .
C39 C 0.51721(11) 0.04327(11) 0.20395(10) 0.0404(3) Uani 1 1 d . . . . .
C40 C 0.62535(12) 0.08348(11) 0.28928(11) 0.0415(3) Uani 1 1 d . . . . .
C41 C 0.73662(12) 0.08781(12) 0.27203(12) 0.0489(3) Uani 1 1 d . . . . .
H22 H 0.745244 0.066815 0.205357 0.059 Uiso 1 1 calc R U . . .
C42 C 0.83531(14) 0.12335(14) 0.35385(15) 0.0598(4) Uani 1 1 d . . . . .
H26 H 0.909842 0.125036 0.342208 0.072 Uiso 1 1 calc R U . . .
C43 C 0.82318(16) 0.15614(14) 0.45222(14) 0.0649(5) Uani 1 1 d . . . . .
H23 H 0.889608 0.180641 0.506689 0.078 Uiso 1 1 calc R U . . .
C44 C 0.71314(17) 0.15279(15) 0.47024(13) 0.0668(5) Uani 1 1 d . . . . .
H24 H 0.705126 0.174943 0.536782 0.080 Uiso 1 1 calc R U . . .
C45 C 0.61422(15) 0.11631(14) 0.38899(12) 0.0563(4) Uani 1 1 d . . . . .
H25 H 0.539834 0.113813 0.401349 0.068 Uiso 1 1 calc R U . . .
C46 C 0.52703(13) -0.16601(13) 0.35958(12) 0.0519(4) Uani 1 1 d . . . . .
H29 H 0.593139 -0.112993 0.391446 0.062 Uiso 1 1 calc R U . . .
C47 C 0.50671(15) -0.26610(14) 0.39844(13) 0.0583(4) Uani 1 1 d . . . . .
H28 H 0.559922 -0.280450 0.456960 0.070 Uiso 1 1 calc R U . . .
C48 C 0.64200(14) 0.28146(12) 0.12349(13) 0.0545(4) Uani 1 1 d . . . . .
H30 H 0.703655 0.248149 0.112250 0.082 Uiso 1 1 calc R U . . .
H32 H 0.652480 0.299678 0.197900 0.082 Uiso 1 1 calc R U . . .
H31 H 0.644729 0.345557 0.086432 0.082 Uiso 1 1 calc R U . . .
C49 C 0.2751(2) 0.17846(15) -0.19730(13) 0.0674(5) Uani 1 1 d . . . . .
H33 H 0.350970 0.208343 -0.204431 0.081 Uiso 1 1 calc R U . . .
C50 C 0.1800(3) 0.17258(19) -0.28061(16) 0.0968(8) Uani 1 1 d . . . . .
H34 H 0.191914 0.199215 -0.344319 0.116 Uiso 1 1 calc R U . . .
H4A H 0.4913(16) 0.5903(15) 0.0683(14) 0.059(5) Uiso 1 1 d . . . . .
H7A H 0.2068(17) -0.2251(15) 0.1053(15) 0.065(5) Uiso 1 1 d . . . . .
N1 N 0.06719(10) 0.38757(10) -0.06333(9) 0.0489(3) Uani 1 1 d . . . . .
N2 N -0.01566(11) 0.30576(11) -0.03603(10) 0.0508(3) Uani 1 1 d . . . . .
N3 N 0.27095(10) 0.47733(10) 0.00803(9) 0.0470(3) Uani 1 1 d . . . . .
N4 N 0.46871(10) 0.53666(11) 0.10693(10) 0.0470(3) Uani 1 1 d . . . . .
N5 N 0.35349(11) 0.14157(10) -0.01856(9) 0.0476(3) Uani 1 1 d . . . . .
N6 N 0.29472(10) -0.03094(10) 0.04808(9) 0.0468(3) Uani 1 1 d . . . . .
N7 N 0.27944(11) -0.19024(10) 0.13969(10) 0.0503(3) Uani 1 1 d . . . . .
N8 N 0.45052(11) 0.22720(10) 0.00107(10) 0.0487(3) 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
C1 C2 1.367(2) . ?
C1 C25 1.376(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H18 0.9300 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9300 . ?
C4 C24 1.381(2) . ?
C4 N1 1.4153(18) . ?
C5 N3 1.3429(17) . ?
C5 N1 1.3733(17) . ?
C5 C6 1.4116(19) . ?
C6 C7 1.4089(19) . ?
C6 C12 1.4247(19) . ?
C7 C16 1.3818(18) . ?
C7 C8 1.4909(18) . ?
C8 C18 1.375(2) . ?
C8 C9 1.375(2) . ?
C9 C10 1.387(2) . ?
C9 H8 0.9300 . ?
C10 C11 1.369(3) . ?
C10 H7 0.9300 . ?
C11 C17 1.357(3) . ?
C11 H2 0.9300 . ?
C12 N2 1.3137(18) . ?
C12 C23 1.4905(19) . ?
C13 N3 1.3266(17) . ?
C13 N4 1.3696(17) . ?
C13 C16 1.4397(18) . ?
C14 C22 1.382(2) . ?
C14 N4 1.3880(18) . ?
C14 C15 1.412(2) . ?
C15 C19 1.391(2) . ?
C15 C16 1.4502(19) . ?
C17 C18 1.386(2) . ?
C17 H5 0.9300 . ?
C18 H6 0.9300 . ?
C19 C20 1.380(2) . ?
C19 H12 0.9300 . ?
C20 C21 1.391(3) . ?
C20 H9 0.9300 . ?
C21 C22 1.380(2) . ?
C21 H11 0.9300 . ?
C22 H10 0.9300 . ?
C23 H13 0.9600 . ?
C23 H15 0.9600 . ?
C23 H14 0.9600 . ?
C24 C25 1.381(2) . ?
C24 H17 0.9300 . ?
C25 H16 0.9300 . ?
C26 C27 1.372(4) . ?
C26 C50 1.374(4) . ?
C26 H19 0.9300 . ?
C27 C28 1.383(2) . ?
C27 H36 0.9300 . ?
C28 C29 1.381(2) . ?
C28 H35 0.9300 . ?
C29 C49 1.376(2) . ?
C29 N5 1.4137(18) . ?
C30 N6 1.3454(17) . ?
C30 N5 1.3648(17) . ?
C30 C36 1.4126(18) . ?
C31 N6 1.3260(17) . ?
C31 N7 1.3704(17) . ?
C31 C38 1.4358(18) . ?
C32 C33 1.389(2) . ?
C32 N7 1.3890(18) . ?
C32 C37 1.406(2) . ?
C33 C34 1.377(2) . ?
C33 H27 0.9300 . ?
C34 C47 1.390(2) . ?
C34 H20 0.9300 . ?
C35 N8 1.3169(18) . ?
C35 C36 1.4321(18) . ?
C35 C48 1.486(2) . ?
C36 C39 1.4049(18) . ?
C37 C46 1.3974(19) . ?
C37 C38 1.4544(19) . ?
C38 C39 1.3893(18) . ?
C39 C40 1.4905(18) . ?
C40 C41 1.384(2) . ?
C40 C45 1.388(2) . ?
C41 C42 1.387(2) . ?
C41 H22 0.9300 . ?
C42 C43 1.376(3) . ?
C42 H26 0.9300 . ?
C43 C44 1.375(3) . ?
C43 H23 0.9300 . ?
C44 C45 1.386(2) . ?
C44 H24 0.9300 . ?
C45 H25 0.9300 . ?
C46 C47 1.381(2) . ?
C46 H29 0.9300 . ?
C47 H28 0.9300 . ?
C48 H30 0.9600 . ?
C48 H32 0.9600 . ?
C48 H31 0.9600 . ?
C49 C50 1.376(3) . ?
C49 H33 0.9300 . ?
C50 H34 0.9300 . ?
N1 N2 1.3869(16) . ?
N4 H4A 0.890(19) . ?
N5 N8 1.3836(16) . ?
N7 H7A 0.90(2) . ?

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 C25 119.56(15) . . ?
C2 C1 H1 120.2 . . ?
C25 C1 H1 120.2 . . ?
C1 C2 C3 120.60(15) . . ?
C1 C2 H18 119.7 . . ?
C3 C2 H18 119.7 . . ?
C4 C3 C2 119.75(15) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C24 C4 C3 119.74(14) . . ?
C24 C4 N1 120.11(13) . . ?
C3 C4 N1 120.14(13) . . ?
N3 C5 N1 126.02(12) . . ?
N3 C5 C6 127.38(12) . . ?
N1 C5 C6 106.59(11) . . ?
C7 C6 C5 119.36(12) . . ?
C7 C6 C12 135.75(13) . . ?
C5 C6 C12 104.87(12) . . ?
C16 C7 C6 115.36(12) . . ?
C16 C7 C8 122.59(12) . . ?
C6 C7 C8 122.04(12) . . ?
C18 C8 C9 118.46(14) . . ?
C18 C8 C7 121.96(13) . . ?
C9 C8 C7 119.57(14) . . ?
C8 C9 C10 120.51(17) . . ?
C8 C9 H8 119.7 . . ?
C10 C9 H8 119.7 . . ?
C11 C10 C9 120.40(18) . . ?
C11 C10 H7 119.8 . . ?
C9 C10 H7 119.8 . . ?
C17 C11 C10 119.37(16) . . ?
C17 C11 H2 120.3 . . ?
C10 C11 H2 120.3 . . ?
N2 C12 C6 111.22(12) . . ?
N2 C12 C23 120.48(13) . . ?
C6 C12 C23 128.30(13) . . ?
N3 C13 N4 123.96(12) . . ?
N3 C13 C16 127.43(12) . . ?
N4 C13 C16 108.61(12) . . ?
C22 C14 N4 128.85(14) . . ?
C22 C14 C15 121.89(14) . . ?
N4 C14 C15 109.24(12) . . ?
C19 C15 C14 119.04(13) . . ?
C19 C15 C16 134.49(14) . . ?
C14 C15 C16 106.46(12) . . ?
C7 C16 C13 119.10(12) . . ?
C7 C16 C15 134.70(12) . . ?
C13 C16 C15 106.19(11) . . ?
C11 C17 C18 120.63(18) . . ?
C11 C17 H5 119.7 . . ?
C18 C17 H5 119.7 . . ?
C8 C18 C17 120.60(17) . . ?
C8 C18 H6 119.7 . . ?
C17 C18 H6 119.7 . . ?
C20 C19 C15 119.02(15) . . ?
C20 C19 H12 120.5 . . ?
C15 C19 H12 120.5 . . ?
C19 C20 C21 120.98(15) . . ?
C19 C20 H9 119.5 . . ?
C21 C20 H9 119.5 . . ?
C22 C21 C20 121.29(15) . . ?
C22 C21 H11 119.4 . . ?
C20 C21 H11 119.4 . . ?
C21 C22 C14 117.74(15) . . ?
C21 C22 H10 121.1 . . ?
C14 C22 H10 121.1 . . ?
C12 C23 H13 109.5 . . ?
C12 C23 H15 109.5 . . ?
H13 C23 H15 109.5 . . ?
C12 C23 H14 109.5 . . ?
H13 C23 H14 109.5 . . ?
H15 C23 H14 109.5 . . ?
C25 C24 C4 119.61(15) . . ?
C25 C24 H17 120.2 . . ?
C4 C24 H17 120.2 . . ?
C1 C25 C24 120.71(16) . . ?
C1 C25 H16 119.6 . . ?
C24 C25 H16 119.6 . . ?
C27 C26 C50 119.96(19) . . ?
C27 C26 H19 120.0 . . ?
C50 C26 H19 120.0 . . ?
C26 C27 C28 119.9(2) . . ?
C26 C27 H36 120.0 . . ?
C28 C27 H36 120.0 . . ?
C29 C28 C27 119.49(19) . . ?
C29 C28 H35 120.3 . . ?
C27 C28 H35 120.3 . . ?
C49 C29 C28 120.78(16) . . ?
C49 C29 N5 119.27(16) . . ?
C28 C29 N5 119.95(14) . . ?
N6 C30 N5 125.50(12) . . ?
N6 C30 C36 127.88(12) . . ?
N5 C30 C36 106.62(12) . . ?
N6 C31 N7 123.96(12) . . ?
N6 C31 C38 127.15(12) . . ?
N7 C31 C38 108.88(12) . . ?
C33 C32 N7 128.64(14) . . ?
C33 C32 C37 121.90(14) . . ?
N7 C32 C37 109.40(12) . . ?
C34 C33 C32 117.58(15) . . ?
C34 C33 H27 121.2 . . ?
C32 C33 H27 121.2 . . ?
C33 C34 C47 121.49(15) . . ?
C33 C34 H20 119.3 . . ?
C47 C34 H20 119.3 . . ?
N8 C35 C36 110.98(12) . . ?
N8 C35 C48 120.34(13) . . ?
C36 C35 C48 128.65(13) . . ?
C39 C36 C30 118.77(12) . . ?
C39 C36 C35 136.52(13) . . ?
C30 C36 C35 104.64(12) . . ?
C46 C37 C32 119.22(13) . . ?
C46 C37 C38 134.18(13) . . ?
C32 C37 C38 106.52(12) . . ?
C39 C38 C31 119.30(12) . . ?
C39 C38 C37 134.69(12) . . ?
C31 C38 C37 105.95(11) . . ?
C38 C39 C36 115.43(12) . . ?
C38 C39 C40 121.48(12) . . ?
C36 C39 C40 123.03(12) . . ?
C41 C40 C45 119.10(13) . . ?
C41 C40 C39 121.68(13) . . ?
C45 C40 C39 119.21(13) . . ?
C40 C41 C42 120.22(15) . . ?
C40 C41 H22 119.9 . . ?
C42 C41 H22 119.9 . . ?
C43 C42 C41 120.14(16) . . ?
C43 C42 H26 119.9 . . ?
C41 C42 H26 119.9 . . ?
C44 C43 C42 120.21(15) . . ?
C44 C43 H23 119.9 . . ?
C42 C43 H23 119.9 . . ?
C43 C44 C45 119.84(16) . . ?
C43 C44 H24 120.1 . . ?
C45 C44 H24 120.1 . . ?
C44 C45 C40 120.49(16) . . ?
C44 C45 H25 119.8 . . ?
C40 C45 H25 119.8 . . ?
C47 C46 C37 118.71(15) . . ?
C47 C46 H29 120.6 . . ?
C37 C46 H29 120.6 . . ?
C46 C47 C34 121.09(15) . . ?
C46 C47 H28 119.5 . . ?
C34 C47 H28 119.5 . . ?
C35 C48 H30 109.5 . . ?
C35 C48 H32 109.5 . . ?
H30 C48 H32 109.5 . . ?
C35 C48 H31 109.5 . . ?
H30 C48 H31 109.5 . . ?
H32 C48 H31 109.5 . . ?
C29 C49 C50 118.9(2) . . ?
C29 C49 H33 120.5 . . ?
C50 C49 H33 120.5 . . ?
C26 C50 C49 120.9(2) . . ?
C26 C50 H34 119.5 . . ?
C49 C50 H34 119.5 . . ?
C5 N1 N2 110.41(11) . . ?
C5 N1 C4 129.13(12) . . ?
N2 N1 C4 120.13(11) . . ?
C12 N2 N1 106.91(11) . . ?
C13 N3 C5 111.36(11) . . ?
C13 N4 C14 109.49(12) . . ?
C13 N4 H4A 125.2(11) . . ?
C14 N4 H4A 125.1(12) . . ?
C30 N5 N8 110.98(11) . . ?
C30 N5 C29 128.06(12) . . ?
N8 N5 C29 120.88(11) . . ?
C31 N6 C30 111.21(11) . . ?
C31 N7 C32 109.21(12) . . ?
C31 N7 H7A 126.1(12) . . ?
C32 N7 H7A 124.2(12) . . ?
C35 N8 N5 106.70(11) . . ?

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
C25 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C24 -0.2(2) . . . . ?
C2 C3 C4 N1 179.95(15) . . . . ?
N3 C5 C6 C7 -0.3(2) . . . . ?
N1 C5 C6 C7 178.60(13) . . . . ?
N3 C5 C6 C12 -178.71(15) . . . . ?
N1 C5 C6 C12 0.15(17) . . . . ?
C5 C6 C7 C16 -0.8(2) . . . . ?
C12 C6 C7 C16 177.02(17) . . . . ?
C5 C6 C7 C8 178.04(14) . . . . ?
C12 C6 C7 C8 -4.1(3) . . . . ?
C16 C7 C8 C18 -88.8(2) . . . . ?
C6 C7 C8 C18 92.44(19) . . . . ?
C16 C7 C8 C9 92.40(18) . . . . ?
C6 C7 C8 C9 -86.39(19) . . . . ?
C18 C8 C9 C10 -2.1(3) . . . . ?
C7 C8 C9 C10 176.80(16) . . . . ?
C8 C9 C10 C11 1.9(3) . . . . ?
C9 C10 C11 C17 -0.6(3) . . . . ?
C7 C6 C12 N2 -177.72(16) . . . . ?
C5 C6 C12 N2 0.35(18) . . . . ?
C7 C6 C12 C23 1.7(3) . . . . ?
C5 C6 C12 C23 179.75(17) . . . . ?
C22 C14 C15 C19 1.2(2) . . . . ?
N4 C14 C15 C19 179.98(14) . . . . ?
C22 C14 C15 C16 -178.40(14) . . . . ?
N4 C14 C15 C16 0.34(16) . . . . ?
C6 C7 C16 C13 1.4(2) . . . . ?
C8 C7 C16 C13 -177.48(13) . . . . ?
C6 C7 C16 C15 179.89(15) . . . . ?
C8 C7 C16 C15 1.0(3) . . . . ?
N3 C13 C16 C7 -1.1(2) . . . . ?
N4 C13 C16 C7 179.12(13) . . . . ?
N3 C13 C16 C15 -179.95(14) . . . . ?
N4 C13 C16 C15 0.23(16) . . . . ?
C19 C15 C16 C7 1.5(3) . . . . ?
C14 C15 C16 C7 -178.98(16) . . . . ?
C19 C15 C16 C13 -179.90(17) . . . . ?
C14 C15 C16 C13 -0.34(15) . . . . ?
C10 C11 C17 C18 -0.4(3) . . . . ?
C9 C8 C18 C17 1.0(3) . . . . ?
C7 C8 C18 C17 -177.83(16) . . . . ?
C11 C17 C18 C8 0.2(3) . . . . ?
C14 C15 C19 C20 0.3(2) . . . . ?
C16 C15 C19 C20 179.78(17) . . . . ?
C15 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C20 C21 C22 C14 1.6(3) . . . . ?
N4 C14 C22 C21 179.38(15) . . . . ?
C15 C14 C22 C21 -2.1(2) . . . . ?
C3 C4 C24 C25 -1.4(3) . . . . ?
N1 C4 C24 C25 178.46(15) . . . . ?
C2 C1 C25 C24 -1.3(3) . . . . ?
C4 C24 C25 C1 2.1(3) . . . . ?
C50 C26 C27 C28 -0.9(4) . . . . ?
C26 C27 C28 C29 -1.2(3) . . . . ?
C27 C28 C29 C49 2.6(3) . . . . ?
C27 C28 C29 N5 -176.87(16) . . . . ?
N7 C32 C33 C34 178.29(15) . . . . ?
C37 C32 C33 C34 1.5(2) . . . . ?
C32 C33 C34 C47 -0.3(2) . . . . ?
N6 C30 C36 C39 -4.8(2) . . . . ?
N5 C30 C36 C39 175.08(12) . . . . ?
N6 C30 C36 C35 177.65(14) . . . . ?
N5 C30 C36 C35 -2.47(15) . . . . ?
N8 C35 C36 C39 -175.67(16) . . . . ?
C48 C35 C36 C39 6.3(3) . . . . ?
N8 C35 C36 C30 1.21(16) . . . . ?
C48 C35 C36 C30 -176.83(15) . . . . ?
C33 C32 C37 C46 -1.9(2) . . . . ?
N7 C32 C37 C46 -179.32(13) . . . . ?
C33 C32 C37 C38 175.22(14) . . . . ?
N7 C32 C37 C38 -2.15(17) . . . . ?
N6 C31 C38 C39 -3.5(2) . . . . ?
N7 C31 C38 C39 176.98(13) . . . . ?
N6 C31 C38 C37 179.06(14) . . . . ?
N7 C31 C38 C37 -0.50(16) . . . . ?
C46 C37 C38 C39 1.2(3) . . . . ?
C32 C37 C38 C39 -175.31(16) . . . . ?
C46 C37 C38 C31 178.15(16) . . . . ?
C32 C37 C38 C31 1.60(16) . . . . ?
C31 C38 C39 C36 -1.0(2) . . . . ?
C37 C38 C39 C36 175.59(15) . . . . ?
C31 C38 C39 C40 176.33(13) . . . . ?
C37 C38 C39 C40 -7.1(3) . . . . ?
C30 C36 C39 C38 4.5(2) . . . . ?
C35 C36 C39 C38 -178.91(16) . . . . ?
C30 C36 C39 C40 -172.75(13) . . . . ?
C35 C36 C39 C40 3.8(3) . . . . ?
C38 C39 C40 C41 107.60(16) . . . . ?
C36 C39 C40 C41 -75.27(19) . . . . ?
C38 C39 C40 C45 -71.66(19) . . . . ?
C36 C39 C40 C45 105.47(17) . . . . ?
C45 C40 C41 C42 0.7(2) . . . . ?
C39 C40 C41 C42 -178.52(14) . . . . ?
C40 C41 C42 C43 -1.0(2) . . . . ?
C41 C42 C43 C44 0.7(3) . . . . ?
C42 C43 C44 C45 0.0(3) . . . . ?
C43 C44 C45 C40 -0.3(3) . . . . ?
C41 C40 C45 C44 -0.1(2) . . . . ?
C39 C40 C45 C44 179.18(15) . . . . ?
C32 C37 C46 C47 1.2(2) . . . . ?
C38 C37 C46 C47 -174.98(16) . . . . ?
C37 C46 C47 C34 -0.1(2) . . . . ?
C33 C34 C47 C46 -0.3(3) . . . . ?
C28 C29 C49 C50 -1.7(3) . . . . ?
N5 C29 C49 C50 177.72(16) . . . . ?
C27 C26 C50 C49 1.8(4) . . . . ?
C29 C49 C50 C26 -0.4(3) . . . . ?
N3 C5 N1 N2 178.30(14) . . . . ?
C6 C5 N1 N2 -0.58(17) . . . . ?
N3 C5 N1 C4 5.0(3) . . . . ?
C6 C5 N1 C4 -173.85(15) . . . . ?
C24 C4 N1 C5 -39.1(2) . . . . ?
C3 C4 N1 C5 140.79(17) . . . . ?
C24 C4 N1 N2 148.22(15) . . . . ?
C3 C4 N1 N2 -31.9(2) . . . . ?
C6 C12 N2 N1 -0.69(18) . . . . ?
C23 C12 N2 N1 179.85(15) . . . . ?
C5 N1 N2 C12 0.80(17) . . . . ?
C4 N1 N2 C12 174.76(14) . . . . ?
N4 C13 N3 C5 179.78(14) . . . . ?
C16 C13 N3 C5 0.0(2) . . . . ?
N1 C5 N3 C13 -177.97(14) . . . . ?
C6 C5 N3 C13 0.7(2) . . . . ?
N3 C13 N4 C14 -179.85(13) . . . . ?
C16 C13 N4 C14 -0.02(17) . . . . ?
C22 C14 N4 C13 178.42(15) . . . . ?
C15 C14 N4 C13 -0.21(17) . . . . ?
N6 C30 N5 N8 -177.15(14) . . . . ?
C36 C30 N5 N8 2.96(16) . . . . ?
N6 C30 N5 C29 -0.3(2) . . . . ?
C36 C30 N5 C29 179.78(14) . . . . ?
C49 C29 N5 C30 -138.78(17) . . . . ?
C28 C29 N5 C30 40.7(2) . . . . ?
C49 C29 N5 N8 37.8(2) . . . . ?
C28 C29 N5 N8 -142.77(15) . . . . ?
N7 C31 N6 C30 -176.98(14) . . . . ?
C38 C31 N6 C30 3.5(2) . . . . ?
N5 C30 N6 C31 -179.21(14) . . . . ?
C36 C30 N6 C31 0.7(2) . . . . ?
N6 C31 N7 C32 179.60(14) . . . . ?
C38 C31 N7 C32 -0.83(17) . . . . ?
C33 C32 N7 C31 -175.25(15) . . . . ?
C37 C32 N7 C31 1.89(17) . . . . ?
C36 C35 N8 N5 0.54(16) . . . . ?
C48 C35 N8 N5 178.76(13) . . . . ?
C30 N5 N8 C35 -2.22(17) . . . . ?
C29 N5 N8 C35 -179.30(13) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.081

####################################################################### 
# 
# 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_BD_501_0m
_database_code_depnum_ccdc_archive 'CCDC 1867797'
_audit_update_record             
;
2018-09-14 deposited with the CCDC.
2018-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 Br N4'
_chemical_formula_weight         453.33

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7966(6)
_cell_length_b                   14.3031(12)
_cell_length_c                   18.1018(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2018.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4177
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      24.99

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   0.680
_exptl_transmission_factor_max   0.764
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    2.056
_shelx_estimated_absorpt_T_min   0.672
_shelx_estimated_absorpt_T_max   0.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(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            7611
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             4971
_reflns_number_gt                3682
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.691
_reflns_Friedel_fraction_max     0.872
_reflns_Friedel_fraction_full    0.965

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0572P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1232 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4971
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1284
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.7615(6) 0.7491(3) 0.8893(2) 0.0386(11) Uani 1 1 d . . . . .
C2 C 0.6439(6) 0.6770(3) 0.8888(2) 0.0344(10) Uani 1 1 d . . . . .
H2 H 0.662560 0.622508 0.915685 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4946(5) 0.6891(3) 0.8462(2) 0.0302(9) Uani 1 1 d . . . . .
C4 C 0.3503(5) 0.6298(3) 0.8300(2) 0.0282(9) Uani 1 1 d . . . . .
C5 C 0.2443(5) 0.6816(3) 0.7792(2) 0.0291(9) Uani 1 1 d . . . . .
C7 C 0.0561(6) 0.5672(3) 0.7696(2) 0.0311(9) Uani 1 1 d . . . . .
C8 C -0.2060(6) 0.5408(3) 0.6901(2) 0.0328(10) Uani 1 1 d . . . . .
C9 C -0.2838(6) 0.6274(4) 0.6934(3) 0.0394(11) Uani 1 1 d . . . . .
H9 H -0.253447 0.670134 0.729866 0.047 Uiso 1 1 calc R U . . .
C10 C -0.4077(7) 0.6496(4) 0.6416(3) 0.0528(14) Uani 1 1 d . . . . .
H10 H -0.460872 0.707801 0.643218 0.063 Uiso 1 1 calc R U . . .
C11 C -0.4528(8) 0.5865(5) 0.5879(3) 0.0582(15) Uani 1 1 d . . . . .
H11 H -0.536154 0.601937 0.553256 0.070 Uiso 1 1 calc R U . . .
C12 C 0.4700(6) 0.7731(3) 0.8071(2) 0.0312(8) Uani 1 1 d . . . . .
C13 C 0.5896(6) 0.8442(3) 0.8089(3) 0.0405(11) Uani 1 1 d . . . . .
H13 H 0.571471 0.899419 0.782921 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7373(6) 0.8314(4) 0.8503(3) 0.0435(12) Uani 1 1 d . . . . .
H14 H 0.820232 0.878080 0.851970 0.052 Uiso 1 1 calc R U . . .
C15 C -0.3747(9) 0.5006(5) 0.5853(3) 0.0618(17) Uani 1 1 d . . . . .
H15 H -0.406088 0.457680 0.549160 0.074 Uiso 1 1 calc R U . . .
C16 C -0.2502(8) 0.4776(4) 0.6360(3) 0.0460(12) Uani 1 1 d . . . . .
H16 H -0.196209 0.419708 0.633810 0.055 Uiso 1 1 calc R U . . .
C18 C 0.0470(6) 0.4250(3) 0.8221(2) 0.0324(9) Uani 1 1 d . . . . .
C19 C 0.1435(6) 0.5097(3) 0.8203(2) 0.0301(9) Uani 1 1 d . . . . .
C20 C 0.2972(6) 0.5416(3) 0.8523(2) 0.0284(9) Uani 1 1 d . . . . .
C21 C 0.3929(6) 0.4839(3) 0.9074(2) 0.0304(9) Uani 1 1 d . . . . .
C22 C 0.3340(7) 0.4804(5) 0.9790(3) 0.0534(15) Uani 1 1 d . . . . .
H22 H 0.241444 0.517105 0.993525 0.064 Uiso 1 1 calc R U . . .
C23 C 0.4145(9) 0.4214(6) 1.0295(3) 0.077(2) Uani 1 1 d . . . . .
H23 H 0.374307 0.417998 1.077788 0.093 Uiso 1 1 calc R U . . .
C24 C 0.5512(10) 0.3688(4) 1.0087(4) 0.073(2) Uani 1 1 d . . . . .
H24 H 0.602671 0.328524 1.042389 0.088 Uiso 1 1 calc R U . . .
C25 C 0.6138(8) 0.3749(4) 0.9377(4) 0.072(2) Uani 1 1 d . . . . .
H25 H 0.709192 0.339995 0.923753 0.087 Uiso 1 1 calc R U . . .
C26 C 0.5344(8) 0.4330(4) 0.8873(3) 0.0502(13) Uani 1 1 d . . . . .
H26 H 0.577069 0.437582 0.839438 0.060 Uiso 1 1 calc R U . . .
C27 C 0.0785(7) 0.3381(3) 0.8662(3) 0.0486(13) Uani 1 1 d . . . . .
H27A H 0.011201 0.287798 0.846360 0.073 Uiso 1 1 calc R U . . .
H27B H 0.046687 0.348743 0.916699 0.073 Uiso 1 1 calc R U . . .
H27C H 0.197944 0.321999 0.863696 0.073 Uiso 1 1 calc R U . . .
H1A H 0.263(7) 0.809(4) 0.750(2) 0.034(13) Uiso 1 1 d . . . . .
N1 N 0.3176(5) 0.7669(3) 0.7673(2) 0.0363(9) Uani 1 1 d . . . . .
N2 N 0.0988(5) 0.6540(2) 0.74768(19) 0.0333(8) Uani 1 1 d . . . . .
N3 N -0.0807(5) 0.5167(3) 0.74425(19) 0.0345(8) Uani 1 1 d . . . . .
N4 N -0.0842(5) 0.4291(3) 0.7765(2) 0.0356(9) Uani 1 1 d . . . . .
Br1 Br 0.96596(8) 0.73546(5) 0.94576(3) 0.0638(2) 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
C1 C2 1.380(6) . ?
C1 C14 1.385(7) . ?
C1 Br1 1.903(4) . ?
C2 C3 1.407(6) . ?
C2 H2 0.9300 . ?
C3 C12 1.408(6) . ?
C3 C4 1.439(6) . ?
C4 C20 1.387(6) . ?
C4 C5 1.442(6) . ?
C5 N2 1.330(6) . ?
C5 N1 1.364(6) . ?
C7 N2 1.345(6) . ?
C7 N3 1.367(5) . ?
C7 C19 1.408(6) . ?
C8 C16 1.376(6) . ?
C8 C9 1.380(7) . ?
C8 N3 1.426(5) . ?
C9 C10 1.383(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(8) . ?
C10 H10 0.9300 . ?
C11 C15 1.372(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(6) . ?
C12 N1 1.391(6) . ?
C13 C14 1.387(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.376(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 N4 1.316(6) . ?
C18 C19 1.426(6) . ?
C18 C27 1.497(6) . ?
C19 C20 1.408(6) . ?
C20 C21 1.494(6) . ?
C21 C26 1.372(7) . ?
C21 C22 1.376(7) . ?
C22 C23 1.394(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N1 H1A 0.80(5) . ?
N3 N4 1.383(5) . ?

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 C14 122.7(4) . . ?
C2 C1 Br1 118.9(4) . . ?
C14 C1 Br1 118.3(4) . . ?
C1 C2 C3 117.5(4) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C2 C3 C12 119.6(4) . . ?
C2 C3 C4 133.3(4) . . ?
C12 C3 C4 107.1(3) . . ?
C20 C4 C3 135.2(4) . . ?
C20 C4 C5 118.8(4) . . ?
C3 C4 C5 106.0(4) . . ?
N2 C5 N1 123.7(4) . . ?
N2 C5 C4 127.6(4) . . ?
N1 C5 C4 108.6(4) . . ?
N2 C7 N3 125.5(4) . . ?
N2 C7 C19 127.7(4) . . ?
N3 C7 C19 106.7(4) . . ?
C16 C8 C9 120.7(4) . . ?
C16 C8 N3 120.1(4) . . ?
C9 C8 N3 119.2(4) . . ?
C8 C9 C10 118.9(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.5(6) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C15 C11 C10 120.0(5) . . ?
C15 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 N1 129.5(4) . . ?
C13 C12 C3 121.7(4) . . ?
N1 C12 C3 108.8(4) . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C1 C14 C13 120.1(4) . . ?
C1 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C11 C15 C16 120.3(5) . . ?
C11 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C8 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C8 C16 H16 120.2 . . ?
N4 C18 C19 110.9(4) . . ?
N4 C18 C27 119.9(4) . . ?
C19 C18 C27 129.2(4) . . ?
C7 C19 C20 119.4(4) . . ?
C7 C19 C18 104.9(4) . . ?
C20 C19 C18 135.6(4) . . ?
C4 C20 C19 115.4(4) . . ?
C4 C20 C21 123.2(4) . . ?
C19 C20 C21 121.4(4) . . ?
C26 C21 C22 120.0(5) . . ?
C26 C21 C20 121.2(4) . . ?
C22 C21 C20 118.8(4) . . ?
C21 C22 C23 119.3(6) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.5(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 120.1(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 119.7(6) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C21 C26 C25 120.4(6) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C18 C27 H27A 109.5 . . ?
C18 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C18 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C5 N1 C12 109.5(4) . . ?
C5 N1 H1A 121(4) . . ?
C12 N1 H1A 127(4) . . ?
C5 N2 C7 111.0(4) . . ?
C7 N3 N4 110.6(3) . . ?
C7 N3 C8 129.6(4) . . ?
N4 N3 C8 119.7(3) . . ?
C18 N4 N3 106.9(4) . . ?

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
C14 C1 C2 C3 0.4(7) . . . . ?
Br1 C1 C2 C3 -179.6(3) . . . . ?
C1 C2 C3 C12 -0.8(6) . . . . ?
C1 C2 C3 C4 177.0(4) . . . . ?
C2 C3 C4 C20 4.2(8) . . . . ?
C12 C3 C4 C20 -177.9(5) . . . . ?
C2 C3 C4 C5 -176.8(4) . . . . ?
C12 C3 C4 C5 1.2(5) . . . . ?
C20 C4 C5 N2 -2.3(7) . . . . ?
C3 C4 C5 N2 178.5(4) . . . . ?
C20 C4 C5 N1 177.7(4) . . . . ?
C3 C4 C5 N1 -1.5(5) . . . . ?
C16 C8 C9 C10 0.3(7) . . . . ?
N3 C8 C9 C10 -178.7(4) . . . . ?
C8 C9 C10 C11 0.1(8) . . . . ?
C9 C10 C11 C15 0.0(9) . . . . ?
C2 C3 C12 C13 0.5(6) . . . . ?
C4 C3 C12 C13 -177.9(4) . . . . ?
C2 C3 C12 N1 177.8(4) . . . . ?
C4 C3 C12 N1 -0.5(5) . . . . ?
N1 C12 C13 C14 -176.5(4) . . . . ?
C3 C12 C13 C14 0.3(7) . . . . ?
C2 C1 C14 C13 0.4(7) . . . . ?
Br1 C1 C14 C13 -179.6(4) . . . . ?
C12 C13 C14 C1 -0.7(7) . . . . ?
C10 C11 C15 C16 -0.6(9) . . . . ?
C11 C15 C16 C8 0.9(9) . . . . ?
C9 C8 C16 C15 -0.8(8) . . . . ?
N3 C8 C16 C15 178.2(5) . . . . ?
N2 C7 C19 C20 -1.9(7) . . . . ?
N3 C7 C19 C20 176.2(4) . . . . ?
N2 C7 C19 C18 -178.6(4) . . . . ?
N3 C7 C19 C18 -0.5(5) . . . . ?
N4 C18 C19 C7 1.0(5) . . . . ?
C27 C18 C19 C7 180.0(5) . . . . ?
N4 C18 C19 C20 -174.9(5) . . . . ?
C27 C18 C19 C20 4.1(9) . . . . ?
C3 C4 C20 C19 -179.1(4) . . . . ?
C5 C4 C20 C19 2.0(6) . . . . ?
C3 C4 C20 C21 1.9(8) . . . . ?
C5 C4 C20 C21 -177.0(4) . . . . ?
C7 C19 C20 C4 -0.2(6) . . . . ?
C18 C19 C20 C4 175.3(5) . . . . ?
C7 C19 C20 C21 178.8(4) . . . . ?
C18 C19 C20 C21 -5.7(8) . . . . ?
C4 C20 C21 C26 -80.6(6) . . . . ?
C19 C20 C21 C26 100.5(6) . . . . ?
C4 C20 C21 C22 101.2(6) . . . . ?
C19 C20 C21 C22 -77.7(6) . . . . ?
C26 C21 C22 C23 -3.1(9) . . . . ?
C20 C21 C22 C23 175.2(5) . . . . ?
C21 C22 C23 C24 0.9(10) . . . . ?
C22 C23 C24 C25 1.4(10) . . . . ?
C23 C24 C25 C26 -1.6(10) . . . . ?
C22 C21 C26 C25 2.9(8) . . . . ?
C20 C21 C26 C25 -175.3(5) . . . . ?
C24 C25 C26 C21 -0.5(9) . . . . ?
N2 C5 N1 C12 -178.7(4) . . . . ?
C4 C5 N1 C12 1.2(5) . . . . ?
C13 C12 N1 C5 176.6(4) . . . . ?
C3 C12 N1 C5 -0.5(5) . . . . ?
N1 C5 N2 C7 -179.6(4) . . . . ?
C4 C5 N2 C7 0.4(6) . . . . ?
N3 C7 N2 C5 -176.1(4) . . . . ?
C19 C7 N2 C5 1.7(6) . . . . ?
N2 C7 N3 N4 178.1(4) . . . . ?
C19 C7 N3 N4 -0.1(5) . . . . ?
N2 C7 N3 C8 0.9(7) . . . . ?
C19 C7 N3 C8 -177.3(4) . . . . ?
C16 C8 N3 C7 133.8(5) . . . . ?
C9 C8 N3 C7 -47.2(7) . . . . ?
C16 C8 N3 N4 -43.1(6) . . . . ?
C9 C8 N3 N4 135.9(5) . . . . ?
C19 C18 N4 N3 -1.1(5) . . . . ?
C27 C18 N4 N3 179.8(4) . . . . ?
C7 N3 N4 C18 0.7(5) . . . . ?
C8 N3 N4 C18 178.2(4) . . . . ?

_refine_diff_density_max         0.799
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.113

