# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_160513a_0m
_database_code_depnum_ccdc_archive 'CCDC 1496437'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H30 N4 O3'
_chemical_formula_weight         530.61

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   8.902(6)
_cell_length_b                   13.209(9)
_cell_length_c                   12.059(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.650(7)
_cell_angle_gamma                90.00
_cell_volume                     1397.8(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3514
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      27.64

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7296
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         25.05
_reflns_number_total             4801
_reflns_number_gt                4336
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.1455P] 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       0.0210(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_number_reflns         4801
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.72667(19) 0.38606(14) 1.06757(14) 0.0407(4) Uani 1 1 d . . .
C2 C 0.6907(3) 0.49776(15) 1.06550(17) 0.0527(5) Uani 1 1 d . . .
H2A H 0.6198 0.5142 0.9977 0.063 Uiso 1 1 calc R . .
H2B H 0.7832 0.5366 1.0655 0.063 Uiso 1 1 calc R . .
C3 C 0.6209(3) 0.52443(17) 1.16866(18) 0.0614(6) Uani 1 1 d . . .
H3A H 0.6028 0.5968 1.1704 0.074 Uiso 1 1 calc R . .
H3B H 0.5239 0.4900 1.1651 0.074 Uiso 1 1 calc R . .
C4 C 0.7262(3) 0.49326(17) 1.27248(17) 0.0587(6) Uani 1 1 d . . .
C5 C 0.7547(3) 0.5543(2) 1.3673(2) 0.0782(8) Uani 1 1 d . . .
H5 H 0.7005 0.6142 1.3699 0.094 Uiso 1 1 calc R . .
C6 C 0.8628(4) 0.5265(3) 1.4574(2) 0.0941(10) Uani 1 1 d . . .
H6 H 0.8815 0.5681 1.5205 0.113 Uiso 1 1 calc R . .
C7 C 0.9433(4) 0.4383(3) 1.45534(18) 0.0914(10) Uani 1 1 d . . .
H7 H 1.0169 0.4207 1.5165 0.110 Uiso 1 1 calc R . .
C8 C 0.9150(3) 0.3742(2) 1.36103(17) 0.0702(7) Uani 1 1 d . . .
H8 H 0.9694 0.3143 1.3595 0.084 Uiso 1 1 calc R . .
C9 C 0.8048(2) 0.40136(17) 1.26993(15) 0.0539(5) Uani 1 1 d . . .
C10 C 0.7733(2) 0.33864(15) 1.16569(14) 0.0434(4) Uani 1 1 d . . .
C11 C 0.7911(2) 0.22892(15) 1.16765(15) 0.0457(4) Uani 1 1 d . . .
C12 C 0.7843(2) 0.17490(14) 1.07063(15) 0.0433(4) Uani 1 1 d . . .
C13 C 0.70595(19) 0.33041(13) 0.95592(14) 0.0369(4) Uani 1 1 d . . .
C14 C 0.54320(19) 0.33779(13) 0.89518(14) 0.0374(4) Uani 1 1 d . . .
C15 C 0.4132(2) 0.29299(15) 0.91829(16) 0.0472(4) Uani 1 1 d . . .
H15 H 0.4166 0.2495 0.9793 0.057 Uiso 1 1 calc R . .
C16 C 0.2760(2) 0.31404(17) 0.8484(2) 0.0589(6) Uani 1 1 d . . .
H16 H 0.1867 0.2833 0.8615 0.071 Uiso 1 1 calc R . .
C17 C 0.2723(2) 0.38028(18) 0.7598(2) 0.0607(6) Uani 1 1 d . . .
H17 H 0.1796 0.3933 0.7139 0.073 Uiso 1 1 calc R . .
C18 C 0.4021(2) 0.42814(16) 0.73699(16) 0.0527(5) Uani 1 1 d . . .
H18 H 0.3983 0.4733 0.6774 0.063 Uiso 1 1 calc R . .
C19 C 0.53784(18) 0.40569(14) 0.80674(14) 0.0399(4) Uani 1 1 d . . .
C20 C 0.7923(2) 0.39359(14) 0.87750(14) 0.0392(4) Uani 1 1 d . . .
C21 C 0.7255(2) 0.51149(15) 0.71663(16) 0.0513(5) Uani 1 1 d . . .
H21A H 0.6560 0.5011 0.6465 0.062 Uiso 1 1 calc R . .
H21B H 0.8275 0.4958 0.7033 0.062 Uiso 1 1 calc R . .
C22 C 0.7200(2) 0.62119(14) 0.74982(16) 0.0477(5) Uani 1 1 d . . .
C23 C 0.6161(3) 0.6862(2) 0.6913(2) 0.0875(8) Uani 1 1 d . . .
H23 H 0.5451 0.6620 0.6318 0.105 Uiso 1 1 calc R . .
C24 C 0.6159(4) 0.7884(2) 0.7200(3) 0.1125(12) Uani 1 1 d . . .
H24 H 0.5439 0.8317 0.6803 0.135 Uiso 1 1 calc R . .
C25 C 0.7203(3) 0.8250(2) 0.8059(3) 0.0803(7) Uani 1 1 d . . .
H25 H 0.7217 0.8936 0.8235 0.096 Uiso 1 1 calc R . .
C26 C 0.8227(3) 0.76115(19) 0.8660(2) 0.0679(6) Uani 1 1 d . . .
H26 H 0.8932 0.7858 0.9256 0.082 Uiso 1 1 calc R . .
C27 C 0.8218(2) 0.65954(17) 0.8385(2) 0.0587(5) Uani 1 1 d . . .
H27 H 0.8915 0.6162 0.8806 0.070 Uiso 1 1 calc R . .
C28 C 0.8033(2) 0.17268(17) 1.26908(16) 0.0546(5) Uani 1 1 d . . .
C29 C 0.8003(2) 0.17514(15) 0.87097(16) 0.0475(4) Uani 1 1 d . . .
C30 C 0.7581(2) 0.18690(15) 0.66453(15) 0.0455(4) Uani 1 1 d . . .
C31 C 0.7186(3) 0.07716(18) 0.6432(2) 0.0722(7) Uani 1 1 d . . .
H31A H 0.6184 0.0644 0.6594 0.108 Uiso 1 1 calc R . .
H31B H 0.7912 0.0357 0.6908 0.108 Uiso 1 1 calc R . .
H31C H 0.7211 0.0613 0.5659 0.108 Uiso 1 1 calc R . .
C32 C 0.9219(2) 0.2106(2) 0.65802(19) 0.0665(6) Uani 1 1 d . . .
H32A H 0.9873 0.1653 0.7062 0.100 Uiso 1 1 calc R . .
H32B H 0.9441 0.2791 0.6818 0.100 Uiso 1 1 calc R . .
H32C H 0.9386 0.2025 0.5819 0.100 Uiso 1 1 calc R . .
C33 C 0.6527(3) 0.25477(18) 0.58735(16) 0.0643(6) Uani 1 1 d . . .
H33A H 0.6789 0.3242 0.6044 0.096 Uiso 1 1 calc R . .
H33B H 0.5495 0.2428 0.5976 0.096 Uiso 1 1 calc R . .
H33C H 0.6623 0.2407 0.5108 0.096 Uiso 1 1 calc R . .
N1 N 0.76933(17) 0.22598(11) 0.96716(11) 0.0409(4) Uani 1 1 d . . .
N2 N 0.68567(17) 0.44130(11) 0.80099(12) 0.0422(4) Uani 1 1 d . . .
N3 N 0.8142(3) 0.12350(16) 1.34839(15) 0.0756(6) Uani 1 1 d . . .
N4 N 0.7849(2) 0.07237(13) 1.06724(15) 0.0635(5) Uani 1 1 d . . .
H4A H 0.7898 0.0381 1.1284 0.076 Uiso 1 1 calc R . .
H4B H 0.7804 0.0416 1.0039 0.076 Uiso 1 1 calc R . .
O1 O 0.92945(14) 0.40176(11) 0.88679(11) 0.0522(3) Uani 1 1 d . . .
O2 O 0.8827(2) 0.10241(12) 0.87548(12) 0.0770(5) Uani 1 1 d . . .
O3 O 0.72800(14) 0.21837(10) 0.77873(9) 0.0437(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 C10 1.342(3) . ?
C1 C2 1.509(3) . ?
C1 C13 1.518(2) . ?
C2 C3 1.522(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.491(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.387(3) . ?
C4 C9 1.404(3) . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.392(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.492(3) . ?
C10 C11 1.458(3) . ?
C11 C12 1.363(3) . ?
C11 C28 1.420(3) . ?
C12 N4 1.355(3) . ?
C12 N1 1.405(2) . ?
C13 N1 1.488(2) . ?
C13 C14 1.513(2) . ?
C13 C20 1.558(3) . ?
C14 C15 1.369(3) . ?
C14 C19 1.388(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 N2 1.410(2) . ?
C20 O1 1.212(2) . ?
C20 N2 1.362(2) . ?
C21 N2 1.463(2) . ?
C21 C22 1.506(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.368(3) . ?
C22 C27 1.377(3) . ?
C23 C24 1.394(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.360(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.359(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 N3 1.147(3) . ?
C29 O2 1.204(2) . ?
C29 O3 1.318(2) . ?
C29 N1 1.407(2) . ?
C30 C33 1.502(3) . ?
C30 C31 1.503(3) . ?
C30 O3 1.505(2) . ?
C30 C32 1.506(3) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 C1 C2 120.30(17) . . ?
C10 C1 C13 121.99(17) . . ?
C2 C1 C13 117.70(16) . . ?
C1 C2 C3 109.10(17) . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 109.70(19) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C9 119.9(2) . . ?
C5 C4 C3 122.3(2) . . ?
C9 C4 C3 117.76(18) . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 119.6(2) . . ?
C8 C9 C10 122.0(2) . . ?
C4 C9 C10 118.35(18) . . ?
C1 C10 C11 119.68(17) . . ?
C1 C10 C9 118.05(19) . . ?
C11 C10 C9 122.26(17) . . ?
C12 C11 C28 116.84(18) . . ?
C12 C11 C10 121.17(17) . . ?
C28 C11 C10 121.79(18) . . ?
N4 C12 C11 123.32(17) . . ?
N4 C12 N1 116.97(17) . . ?
C11 C12 N1 119.66(16) . . ?
N1 C13 C14 114.93(14) . . ?
N1 C13 C1 112.36(14) . . ?
C14 C13 C1 111.24(14) . . ?
N1 C13 C20 109.50(14) . . ?
C14 C13 C20 101.63(14) . . ?
C1 C13 C20 106.27(14) . . ?
C15 C14 C19 120.94(16) . . ?
C15 C14 C13 130.31(17) . . ?
C19 C14 C13 108.69(15) . . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 120.1(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 122.14(19) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C19 C18 C17 117.0(2) . . ?
C19 C18 H18 121.5 . . ?
C17 C18 H18 121.5 . . ?
C18 C19 C14 121.31(17) . . ?
C18 C19 N2 128.72(17) . . ?
C14 C19 N2 109.94(14) . . ?
O1 C20 N2 126.75(16) . . ?
O1 C20 C13 125.72(16) . . ?
N2 C20 C13 107.46(15) . . ?
N2 C21 C22 113.71(16) . . ?
N2 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N2 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C27 118.0(2) . . ?
C23 C22 C21 121.1(2) . . ?
C27 C22 C21 120.89(18) . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C22 C27 C26 121.3(2) . . ?
C22 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
N3 C28 C11 177.0(2) . . ?
O2 C29 O3 126.24(18) . . ?
O2 C29 N1 123.07(17) . . ?
O3 C29 N1 110.69(15) . . ?
C33 C30 C31 111.46(18) . . ?
C33 C30 O3 102.34(15) . . ?
C31 C30 O3 110.51(16) . . ?
C33 C30 C32 110.67(18) . . ?
C31 C30 C32 113.08(18) . . ?
O3 C30 C32 108.21(15) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C33 H33A 109.5 . . ?
C30 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C30 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C12 N1 C29 120.03(15) . . ?
C12 N1 C13 120.27(14) . . ?
C29 N1 C13 119.42(14) . . ?
C20 N2 C19 111.26(15) . . ?
C20 N2 C21 122.76(16) . . ?
C19 N2 C21 125.63(15) . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C29 O3 C30 121.06(14) . . ?

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
C10 C1 C2 C3 -34.8(3) . . . . ?
C13 C1 C2 C3 144.30(17) . . . . ?
C1 C2 C3 C4 56.1(2) . . . . ?
C2 C3 C4 C5 137.3(2) . . . . ?
C2 C3 C4 C9 -38.9(3) . . . . ?
C9 C4 C5 C6 1.9(3) . . . . ?
C3 C4 C5 C6 -174.2(2) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C8 -0.7(4) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 1.5(3) . . . . ?
C7 C8 C9 C10 177.71(19) . . . . ?
C5 C4 C9 C8 -2.5(3) . . . . ?
C3 C4 C9 C8 173.79(19) . . . . ?
C5 C4 C9 C10 -178.85(18) . . . . ?
C3 C4 C9 C10 -2.5(3) . . . . ?
C2 C1 C10 C11 173.10(18) . . . . ?
C13 C1 C10 C11 -6.0(3) . . . . ?
C2 C1 C10 C9 -6.7(3) . . . . ?
C13 C1 C10 C9 174.20(16) . . . . ?
C8 C9 C10 C1 -148.79(19) . . . . ?
C4 C9 C10 C1 27.4(3) . . . . ?
C8 C9 C10 C11 31.4(3) . . . . ?
C4 C9 C10 C11 -152.34(19) . . . . ?
C1 C10 C11 C12 10.2(3) . . . . ?
C9 C10 C11 C12 -169.97(17) . . . . ?
C1 C10 C11 C28 -164.34(18) . . . . ?
C9 C10 C11 C28 15.4(3) . . . . ?
C28 C11 C12 N4 1.6(3) . . . . ?
C10 C11 C12 N4 -173.20(18) . . . . ?
C28 C11 C12 N1 178.86(17) . . . . ?
C10 C11 C12 N1 4.0(3) . . . . ?
C10 C1 C13 N1 -10.5(2) . . . . ?
C2 C1 C13 N1 170.36(15) . . . . ?
C10 C1 C13 C14 119.95(18) . . . . ?
C2 C1 C13 C14 -59.2(2) . . . . ?
C10 C1 C13 C20 -130.25(18) . . . . ?
C2 C1 C13 C20 50.6(2) . . . . ?
N1 C13 C14 C15 57.5(2) . . . . ?
C1 C13 C14 C15 -71.6(2) . . . . ?
C20 C13 C14 C15 175.65(18) . . . . ?
N1 C13 C14 C19 -125.39(16) . . . . ?
C1 C13 C14 C19 105.50(16) . . . . ?
C20 C13 C14 C19 -7.26(17) . . . . ?
C19 C14 C15 C16 2.4(3) . . . . ?
C13 C14 C15 C16 179.23(17) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
C17 C18 C19 N2 178.35(18) . . . . ?
C15 C14 C19 C18 -1.9(3) . . . . ?
C13 C14 C19 C18 -179.36(16) . . . . ?
C15 C14 C19 N2 179.71(16) . . . . ?
C13 C14 C19 N2 2.29(19) . . . . ?
N1 C13 C20 O1 -51.0(2) . . . . ?
C14 C13 C20 O1 -172.99(17) . . . . ?
C1 C13 C20 O1 70.6(2) . . . . ?
N1 C13 C20 N2 131.93(15) . . . . ?
C14 C13 C20 N2 9.96(17) . . . . ?
C1 C13 C20 N2 -106.49(16) . . . . ?
N2 C21 C22 C23 -114.7(2) . . . . ?
N2 C21 C22 C27 66.9(3) . . . . ?
C27 C22 C23 C24 1.0(4) . . . . ?
C21 C22 C23 C24 -177.5(3) . . . . ?
C22 C23 C24 C25 0.8(5) . . . . ?
C23 C24 C25 C26 -1.9(5) . . . . ?
C24 C25 C26 C27 1.1(4) . . . . ?
C23 C22 C27 C26 -1.8(3) . . . . ?
C21 C22 C27 C26 176.7(2) . . . . ?
C25 C26 C27 C22 0.8(4) . . . . ?
C12 C11 C28 N3 9(5) . . . . ?
C10 C11 C28 N3 -176(5) . . . . ?
N4 C12 N1 C29 -18.6(3) . . . . ?
C11 C12 N1 C29 163.97(18) . . . . ?
N4 C12 N1 C13 155.19(17) . . . . ?
C11 C12 N1 C13 -22.2(2) . . . . ?
O2 C29 N1 C12 -24.1(3) . . . . ?
O3 C29 N1 C12 156.12(16) . . . . ?
O2 C29 N1 C13 162.0(2) . . . . ?
O3 C29 N1 C13 -17.8(2) . . . . ?
C14 C13 N1 C12 -103.94(18) . . . . ?
C1 C13 N1 C12 24.6(2) . . . . ?
C20 C13 N1 C12 142.45(16) . . . . ?
C14 C13 N1 C29 69.9(2) . . . . ?
C1 C13 N1 C29 -161.52(16) . . . . ?
C20 C13 N1 C29 -43.7(2) . . . . ?
O1 C20 N2 C19 173.64(18) . . . . ?
C13 C20 N2 C19 -9.35(18) . . . . ?
O1 C20 N2 C21 0.1(3) . . . . ?
C13 C20 N2 C21 177.07(16) . . . . ?
C18 C19 N2 C20 -173.49(18) . . . . ?
C14 C19 N2 C20 4.70(19) . . . . ?
C18 C19 N2 C21 -0.1(3) . . . . ?
C14 C19 N2 C21 178.06(16) . . . . ?
C22 C21 N2 C20 -97.3(2) . . . . ?
C22 C21 N2 C19 90.1(2) . . . . ?
O2 C29 O3 C30 -7.8(3) . . . . ?
N1 C29 O3 C30 171.95(15) . . . . ?
C33 C30 O3 C29 179.95(17) . . . . ?
C31 C30 O3 C29 61.2(2) . . . . ?
C32 C30 O3 C29 -63.2(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
N4 H4B O2 0.86 2.09 2.634(3) 121.0 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.028
####################################################################### 
# 
# 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_160623a_0m
_database_code_depnum_ccdc_archive 'CCDC 1496438'
_audit_update_record             
;
2016-07-28 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H27 Br N4 O3'
_chemical_formula_weight         583.48

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.662(4)
_cell_length_b                   12.286(6)
_cell_length_c                   24.441(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2901(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4423
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      22.21

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    1.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8114
_exptl_absorpt_correction_T_max  0.8334
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15064
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.05
_reflns_number_total             5120
_reflns_number_gt                4078
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_chemical_absolute_configuration ad
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0197P)²+0.4013P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.012(7)
_refine_ls_number_reflns         5120
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.61654(5) 1.29306(3) 0.231565(18) 0.09165(17) Uani 1 1 d . . .
C1 C 0.6073(4) 1.1506(3) 0.20078(11) 0.0537(8) Uani 1 1 d . . .
C2 C 0.4807(3) 1.1096(3) 0.18554(12) 0.0600(9) Uani 1 1 d . . .
H2 H 0.4002 1.1492 0.1918 0.072 Uiso 1 1 calc R . .
C3 C 0.4750(3) 1.0087(3) 0.16085(11) 0.0488(7) Uani 1 1 d . . .
H3 H 0.3899 0.9815 0.1495 0.059 Uiso 1 1 calc R . .
C4 C 0.5934(3) 0.9467(2) 0.15252(9) 0.0398(6) Uani 1 1 d . . .
C5 C 0.7192(3) 0.9896(3) 0.17043(10) 0.0463(7) Uani 1 1 d . . .
H5 H 0.7998 0.9491 0.1663 0.056 Uiso 1 1 calc R . .
C6 C 0.7256(3) 1.0917(3) 0.19423(11) 0.0506(8) Uani 1 1 d . . .
H6 H 0.8102 1.1198 0.2057 0.061 Uiso 1 1 calc R . .
C7 C 0.5856(3) 0.8415(2) 0.12328(9) 0.0375(6) Uani 1 1 d . . .
C8 C 0.6494(3) 0.7510(2) 0.14153(10) 0.0444(7) Uani 1 1 d . . .
C9 C 0.7262(3) 0.7475(3) 0.19250(12) 0.0529(8) Uani 1 1 d . . .
C10 C 0.6387(4) 0.6471(3) 0.11408(12) 0.0574(8) Uani 1 1 d . . .
C11 C 0.4992(3) 0.8343(2) 0.07161(9) 0.0385(6) Uani 1 1 d . . .
H11A H 0.4056 0.8570 0.0803 0.046 Uiso 1 1 calc R . .
H11B H 0.4951 0.7587 0.0604 0.046 Uiso 1 1 calc R . .
C12 C 0.5508(2) 0.9032(2) 0.02204(9) 0.0313(6) Uani 1 1 d . . .
C13 C 0.5393(3) 1.0244(2) 0.03106(9) 0.0326(6) Uani 1 1 d . . .
C14 C 0.4241(3) 1.0897(2) 0.03460(10) 0.0504(7) Uani 1 1 d . . .
H14 H 0.3358 1.0612 0.0297 0.060 Uiso 1 1 calc R . .
C15 C 0.4435(4) 1.2000(3) 0.04572(12) 0.0631(9) Uani 1 1 d . . .
H15 H 0.3671 1.2458 0.0479 0.076 Uiso 1 1 calc R . .
C16 C 0.5730(4) 1.2414(2) 0.05340(12) 0.0637(9) Uani 1 1 d . . .
H16 H 0.5830 1.3146 0.0622 0.076 Uiso 1 1 calc R . .
C17 C 0.6900(3) 1.1769(2) 0.04841(11) 0.0507(8) Uani 1 1 d . . .
H17 H 0.7782 1.2058 0.0529 0.061 Uiso 1 1 calc R . .
C18 C 0.6709(3) 1.0680(2) 0.03643(9) 0.0353(6) Uani 1 1 d . . .
C19 C 0.9211(3) 1.0045(3) 0.02240(11) 0.0458(7) Uani 1 1 d . . .
H19A H 0.9358 1.0731 0.0037 0.055 Uiso 1 1 calc R . .
H19B H 0.9604 0.9472 -0.0001 0.055 Uiso 1 1 calc R . .
C20 C 0.9955(3) 1.0071(2) 0.07650(11) 0.0413(6) Uani 1 1 d . . .
C21 C 1.0340(3) 1.1037(3) 0.10111(13) 0.0528(8) Uani 1 1 d . . .
H21 H 1.0189 1.1690 0.0828 0.063 Uiso 1 1 calc R . .
C22 C 1.0943(3) 1.1053(3) 0.15209(14) 0.0680(10) Uani 1 1 d . . .
H22 H 1.1195 1.1711 0.1681 0.082 Uiso 1 1 calc R . .
C23 C 1.1167(3) 1.0096(3) 0.17911(13) 0.0656(9) Uani 1 1 d . . .
H23 H 1.1538 1.0106 0.2142 0.079 Uiso 1 1 calc R . .
C24 C 1.0851(3) 0.9122(3) 0.15489(15) 0.0688(10) Uani 1 1 d . . .
H24 H 1.1035 0.8473 0.1731 0.083 Uiso 1 1 calc R . .
C25 C 1.0257(3) 0.9105(2) 0.10341(13) 0.0540(8) Uani 1 1 d . . .
H25 H 1.0060 0.8443 0.0867 0.065 Uiso 1 1 calc R . .
C26 C 0.7090(3) 0.8890(2) 0.01553(9) 0.0304(6) Uani 1 1 d . . .
C27 C 0.5001(3) 0.8890(2) -0.07773(10) 0.0378(6) Uani 1 1 d . . .
C28 C 0.6445(4) 1.0066(3) -0.13452(11) 0.0724(11) Uani 1 1 d . . .
C29 C 0.7461(4) 1.0939(3) -0.11912(14) 0.0831(13) Uani 1 1 d . . .
H29A H 0.7038 1.1429 -0.0935 0.125 Uiso 1 1 calc R . .
H29B H 0.7731 1.1334 -0.1513 0.125 Uiso 1 1 calc R . .
H29C H 0.8263 1.0612 -0.1028 0.125 Uiso 1 1 calc R . .
C30 C 0.7177(8) 0.9138(5) -0.1632(2) 0.170(3) Uani 1 1 d . . .
H30A H 0.7625 0.8686 -0.1365 0.256 Uiso 1 1 calc R . .
H30B H 0.7856 0.9427 -0.1879 0.256 Uiso 1 1 calc R . .
H30C H 0.6515 0.8714 -0.1832 0.256 Uiso 1 1 calc R . .
C31 C 0.5269(7) 1.0542(5) -0.1662(2) 0.173(3) Uani 1 1 d . . .
H31A H 0.4784 0.9971 -0.1850 0.260 Uiso 1 1 calc R . .
H31B H 0.5620 1.1054 -0.1924 0.260 Uiso 1 1 calc R . .
H31C H 0.4647 1.0905 -0.1416 0.260 Uiso 1 1 calc R . .
N1 N 0.7835(3) 0.7421(3) 0.23242(12) 0.0764(8) Uani 1 1 d . . .
N2 N 0.6244(4) 0.5647(3) 0.09286(14) 0.0895(10) Uani 1 1 d . . .
N3 N 0.7703(2) 0.98555(17) 0.02840(8) 0.0343(5) Uani 1 1 d . . .
N4 N 0.4753(2) 0.86133(17) -0.02516(8) 0.0382(5) Uani 1 1 d . . .
H4 H 0.4099 0.8154 -0.0190 0.046 Uiso 1 1 calc R . .
O1 O 0.76722(19) 0.80492(15) 0.00248(7) 0.0453(5) Uani 1 1 d . . .
O2 O 0.59626(19) 0.96675(14) -0.08135(6) 0.0423(4) Uani 1 1 d . . .
O3 O 0.4420(2) 0.84589(17) -0.11585(7) 0.0553(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.908(3) . ?
C1 C6 1.363(4) . ?
C1 C2 1.374(5) . ?
C2 C3 1.380(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(4) . ?
C4 C7 1.478(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.348(4) . ?
C7 C11 1.516(3) . ?
C8 C10 1.445(5) . ?
C8 C9 1.451(4) . ?
C9 N1 1.124(4) . ?
C10 N2 1.146(4) . ?
C11 C12 1.559(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N4 1.459(3) . ?
C12 C13 1.510(4) . ?
C12 C26 1.547(3) . ?
C13 C14 1.375(4) . ?
C13 C18 1.385(4) . ?
C14 C15 1.394(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.409(3) . ?
C19 N3 1.483(3) . ?
C19 C20 1.505(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.381(4) . ?
C20 C25 1.388(4) . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.370(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 O1 1.219(3) . ?
C26 N3 1.363(3) . ?
C27 O3 1.210(3) . ?
C27 O2 1.335(3) . ?
C27 N4 1.351(3) . ?
C28 O2 1.464(3) . ?
C28 C31 1.494(7) . ?
C28 C29 1.502(5) . ?
C28 C30 1.513(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
N4 H4 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.4(3) . . ?
C6 C1 Br1 119.6(2) . . ?
C2 C1 Br1 119.0(3) . . ?
C1 C2 C3 118.8(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.6(2) . . ?
C3 C4 C7 120.5(2) . . ?
C5 C4 C7 121.8(2) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C8 C7 C4 122.5(2) . . ?
C8 C7 C11 118.6(2) . . ?
C4 C7 C11 118.8(2) . . ?
C7 C8 C10 122.8(2) . . ?
C7 C8 C9 122.8(3) . . ?
C10 C8 C9 114.2(3) . . ?
N1 C9 C8 177.9(4) . . ?
N2 C10 C8 177.1(4) . . ?
C7 C11 C12 116.1(2) . . ?
C7 C11 H11A 108.3 . . ?
C12 C11 H11A 108.3 . . ?
C7 C11 H11B 108.3 . . ?
C12 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
N4 C12 C13 115.26(19) . . ?
N4 C12 C26 111.9(2) . . ?
C13 C12 C26 101.4(2) . . ?
N4 C12 C11 105.28(19) . . ?
C13 C12 C11 113.5(2) . . ?
C26 C12 C11 109.56(19) . . ?
C14 C13 C18 120.8(2) . . ?
C14 C13 C12 130.1(2) . . ?
C18 C13 C12 109.1(2) . . ?
C13 C14 C15 118.1(3) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C16 C15 C14 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.5(3) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 117.6(3) . . ?
C18 C17 H17 121.2 . . ?
C16 C17 H17 121.2 . . ?
C17 C18 C13 121.1(3) . . ?
C17 C18 N3 129.3(3) . . ?
C13 C18 N3 109.6(2) . . ?
N3 C19 C20 112.7(2) . . ?
N3 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C25 118.1(3) . . ?
C21 C20 C19 122.0(3) . . ?
C25 C20 C19 119.9(3) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.5(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 119.9(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
O1 C26 N3 126.7(2) . . ?
O1 C26 C12 125.4(2) . . ?
N3 C26 C12 107.9(2) . . ?
O3 C27 O2 125.8(2) . . ?
O3 C27 N4 122.7(2) . . ?
O2 C27 N4 111.5(2) . . ?
O2 C28 C31 110.4(4) . . ?
O2 C28 C29 103.0(2) . . ?
C31 C28 C29 110.3(3) . . ?
O2 C28 C30 107.9(3) . . ?
C31 C28 C30 114.2(4) . . ?
C29 C28 C30 110.4(4) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C26 N3 C18 111.2(2) . . ?
C26 N3 C19 122.7(2) . . ?
C18 N3 C19 124.8(2) . . ?
C27 N4 C12 125.1(2) . . ?
C27 N4 H4 117.5 . . ?
C12 N4 H4 117.5 . . ?
C27 O2 C28 121.3(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 -3.0(5) . . . . ?
Br1 C1 C2 C3 176.9(2) . . . . ?
C1 C2 C3 C4 1.8(5) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C7 -176.7(3) . . . . ?
C3 C4 C5 C6 -1.8(4) . . . . ?
C7 C4 C5 C6 175.4(2) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
Br1 C1 C6 C5 -178.1(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C3 C4 C7 C8 -134.3(3) . . . . ?
C5 C4 C7 C8 48.6(4) . . . . ?
C3 C4 C7 C11 43.9(3) . . . . ?
C5 C4 C7 C11 -133.1(3) . . . . ?
C4 C7 C8 C10 178.0(3) . . . . ?
C11 C7 C8 C10 -0.2(4) . . . . ?
C4 C7 C8 C9 2.8(4) . . . . ?
C11 C7 C8 C9 -175.5(2) . . . . ?
C7 C8 C9 N1 129(10) . . . . ?
C10 C8 C9 N1 -46(10) . . . . ?
C7 C8 C10 N2 -66(7) . . . . ?
C9 C8 C10 N2 110(7) . . . . ?
C8 C7 C11 C12 -116.2(3) . . . . ?
C4 C7 C11 C12 65.5(3) . . . . ?
C7 C11 C12 N4 165.5(2) . . . . ?
C7 C11 C12 C13 -67.6(3) . . . . ?
C7 C11 C12 C26 45.0(3) . . . . ?
N4 C12 C13 C14 52.2(3) . . . . ?
C26 C12 C13 C14 173.3(2) . . . . ?
C11 C12 C13 C14 -69.3(3) . . . . ?
N4 C12 C13 C18 -128.3(2) . . . . ?
C26 C12 C13 C18 -7.3(2) . . . . ?
C11 C12 C13 C18 110.2(2) . . . . ?
C18 C13 C14 C15 -2.3(4) . . . . ?
C12 C13 C14 C15 177.1(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C17 2.5(5) . . . . ?
C15 C16 C17 C18 -1.3(4) . . . . ?
C16 C17 C18 C13 -1.7(4) . . . . ?
C16 C17 C18 N3 179.0(2) . . . . ?
C14 C13 C18 C17 3.5(4) . . . . ?
C12 C13 C18 C17 -176.0(2) . . . . ?
C14 C13 C18 N3 -177.0(2) . . . . ?
C12 C13 C18 N3 3.5(3) . . . . ?
N3 C19 C20 C21 -101.2(3) . . . . ?
N3 C19 C20 C25 78.0(3) . . . . ?
C25 C20 C21 C22 -3.3(4) . . . . ?
C19 C20 C21 C22 175.9(3) . . . . ?
C20 C21 C22 C23 0.0(5) . . . . ?
C21 C22 C23 C24 2.7(5) . . . . ?
C22 C23 C24 C25 -2.1(5) . . . . ?
C23 C24 C25 C20 -1.3(5) . . . . ?
C21 C20 C25 C24 3.9(4) . . . . ?
C19 C20 C25 C24 -175.3(3) . . . . ?
N4 C12 C26 O1 -49.6(3) . . . . ?
C13 C12 C26 O1 -173.0(2) . . . . ?
C11 C12 C26 O1 66.8(3) . . . . ?
N4 C12 C26 N3 132.1(2) . . . . ?
C13 C12 C26 N3 8.7(2) . . . . ?
C11 C12 C26 N3 -111.5(2) . . . . ?
O1 C26 N3 C18 174.4(2) . . . . ?
C12 C26 N3 C18 -7.3(3) . . . . ?
O1 C26 N3 C19 6.7(4) . . . . ?
C12 C26 N3 C19 -175.0(2) . . . . ?
C17 C18 N3 C26 -178.0(2) . . . . ?
C13 C18 N3 C26 2.6(3) . . . . ?
C17 C18 N3 C19 -10.6(4) . . . . ?
C13 C18 N3 C19 169.9(2) . . . . ?
C20 C19 N3 C26 -106.5(3) . . . . ?
C20 C19 N3 C18 87.5(3) . . . . ?
O3 C27 N4 C12 174.1(3) . . . . ?
O2 C27 N4 C12 -4.9(4) . . . . ?
C13 C12 N4 C27 62.5(3) . . . . ?
C26 C12 N4 C27 -52.7(3) . . . . ?
C11 C12 N4 C27 -171.7(2) . . . . ?
O3 C27 O2 C28 -1.6(4) . . . . ?
N4 C27 O2 C28 177.3(3) . . . . ?
C31 C28 O2 C27 60.4(4) . . . . ?
C29 C28 O2 C27 178.2(3) . . . . ?
C30 C28 O2 C27 -65.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.036
