# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_121024t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H34 N4 O3'
_chemical_formula_weight         558.66

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           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   12.5058(11)
_cell_length_b                   10.8672(8)
_cell_length_c                   24.496(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.5240(10)
_cell_angle_gamma                90.00
_cell_volume                     3249.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15873
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.1043
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5666
_reflns_number_gt                2488
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1580P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5666
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1868
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.3220
_refine_ls_wR_factor_gt          0.2816
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6275(3) 0.7186(4) 0.38900(19) 0.0542(12) Uani 1 1 d . . .
H1 H 0.6808 0.7408 0.4156 0.065 Uiso 1 1 calc R . .
N3 N 0.3864(3) 0.6307(4) 0.16001(18) 0.0456(11) Uani 1 1 d . . .
N4 N 0.4470(3) 0.7302(4) 0.14925(18) 0.0523(12) Uani 1 1 d . . .
N5 N 0.3520(3) 0.5209(4) 0.24135(16) 0.0422(10) Uani 1 1 d . . .
H5 H 0.3047 0.4818 0.2139 0.051 Uiso 1 1 d R . .
O1 O 0.2405(3) 0.7765(4) 0.27508(17) 0.0671(12) Uani 1 1 d . . .
O2 O 0.8081(4) 0.6412(6) 0.4707(2) 0.1125(19) Uani 1 1 d . . .
H2 H 0.8598 0.6714 0.4930 0.135 Uiso 1 1 calc R . .
O3 O 0.4819(5) 0.7698(6) 0.0423(2) 0.1108(18) Uani 1 1 d . . .
H3 H 0.4690 0.7638 0.0736 0.133 Uiso 1 1 calc R . .
C1 C 0.6259(4) 0.7290(5) 0.3330(2) 0.0488(13) Uani 1 1 d . . .
C2 C 0.5244(4) 0.6926(5) 0.3027(2) 0.0452(13) Uani 1 1 d . . .
C3 C 0.4638(4) 0.6492(5) 0.3427(2) 0.0439(13) Uani 1 1 d . . .
C4 C 0.5317(4) 0.6676(5) 0.3959(2) 0.0477(13) Uani 1 1 d . . .
C5 C 0.4988(5) 0.6329(5) 0.4443(2) 0.0560(15) Uani 1 1 d . . .
H5A H 0.5447 0.6435 0.4793 0.067 Uiso 1 1 calc R . .
C6 C 0.3975(5) 0.5831(5) 0.4388(2) 0.0548(15) Uani 1 1 d . . .
H6 H 0.3736 0.5620 0.4710 0.066 Uiso 1 1 calc R . .
C7 C 0.3269(4) 0.5620(5) 0.3866(2) 0.0500(14) Uani 1 1 d . . .
C8 C 0.3610(4) 0.5934(5) 0.3381(2) 0.0447(13) Uani 1 1 d . . .
C9 C 0.2894(4) 0.5661(5) 0.2818(2) 0.0427(13) Uani 1 1 d . . .
H9 H 0.2396 0.4998 0.2872 0.051 Uiso 1 1 calc R . .
C10 C 0.2184(4) 0.6740(5) 0.2563(2) 0.0456(13) Uani 1 1 d . . .
C11 C 0.1259(4) 0.6542(5) 0.2075(2) 0.0442(13) Uani 1 1 d . . .
C12 C 0.0797(4) 0.7555(5) 0.1773(2) 0.0539(14) Uani 1 1 d . . .
H12 H 0.1077 0.8336 0.1874 0.065 Uiso 1 1 calc R . .
C13 C -0.0069(5) 0.7420(6) 0.1326(2) 0.0656(17) Uani 1 1 d . . .
H13 H -0.0383 0.8107 0.1128 0.079 Uiso 1 1 calc R . .
C14 C -0.0465(5) 0.6283(7) 0.1175(3) 0.0667(17) Uani 1 1 d . . .
H14 H -0.1064 0.6200 0.0877 0.080 Uiso 1 1 calc R . .
C15 C -0.0008(5) 0.5261(6) 0.1448(2) 0.0630(16) Uani 1 1 d . . .
H15 H -0.0272 0.4484 0.1330 0.076 Uiso 1 1 calc R . .
C16 C 0.0862(4) 0.5390(6) 0.1908(2) 0.0548(14) Uani 1 1 d . . .
H16 H 0.1175 0.4697 0.2102 0.066 Uiso 1 1 calc R . .
C17 C 0.5027(4) 0.7678(5) 0.1987(2) 0.0469(13) Uani 1 1 d . . .
C18 C 0.4833(4) 0.6919(5) 0.2429(2) 0.0435(13) Uani 1 1 d . . .
C19 C 0.4062(4) 0.6086(5) 0.2163(2) 0.0437(13) Uani 1 1 d . . .
C20 C 0.5707(5) 0.8815(5) 0.2022(2) 0.0634(16) Uani 1 1 d . . .
H20A H 0.6444 0.8597 0.2008 0.095 Uiso 1 1 calc R . .
H20B H 0.5705 0.9233 0.2367 0.095 Uiso 1 1 calc R . .
H20C H 0.5408 0.9347 0.1714 0.095 Uiso 1 1 calc R . .
C21 C 0.7251(4) 0.7675(5) 0.3149(2) 0.0510(14) Uani 1 1 d . . .
C22 C 0.7808(5) 0.8735(6) 0.3353(3) 0.0617(16) Uani 1 1 d . . .
H22 H 0.7579 0.9194 0.3627 0.074 Uiso 1 1 calc R . .
C23 C 0.8702(5) 0.9119(6) 0.3153(3) 0.0708(18) Uani 1 1 d . . .
H23 H 0.9047 0.9857 0.3276 0.085 Uiso 1 1 calc R . .
C24 C 0.9078(5) 0.8419(6) 0.2775(3) 0.0669(17) Uani 1 1 d . . .
H24 H 0.9693 0.8667 0.2648 0.080 Uiso 1 1 calc R . .
C25 C 0.8553(5) 0.7348(6) 0.2579(3) 0.0699(17) Uani 1 1 d . . .
H25 H 0.8816 0.6867 0.2323 0.084 Uiso 1 1 calc R . .
C26 C 0.7633(4) 0.6983(6) 0.2762(2) 0.0592(15) Uani 1 1 d . . .
H26 H 0.7270 0.6264 0.2623 0.071 Uiso 1 1 calc R . .
C27 C 0.3128(4) 0.5709(5) 0.1166(2) 0.0495(14) Uani 1 1 d . . .
C28 C 0.3064(5) 0.4444(6) 0.1155(2) 0.0593(15) Uani 1 1 d . . .
H28 H 0.3553 0.3979 0.1415 0.071 Uiso 1 1 calc R . .
C29 C 0.2276(5) 0.3874(6) 0.0761(3) 0.0676(17) Uani 1 1 d . . .
H29 H 0.2209 0.3022 0.0767 0.081 Uiso 1 1 calc R . .
C30 C 0.1600(5) 0.4526(7) 0.0367(3) 0.0685(17) Uani 1 1 d . . .
H30 H 0.1071 0.4125 0.0101 0.082 Uiso 1 1 calc R . .
C31 C 0.1686(5) 0.5769(7) 0.0354(3) 0.0699(18) Uani 1 1 d . . .
H31 H 0.1225 0.6211 0.0073 0.084 Uiso 1 1 calc R . .
C32 C 0.2458(4) 0.6398(6) 0.0757(2) 0.0590(15) Uani 1 1 d . . .
H32 H 0.2517 0.7251 0.0749 0.071 Uiso 1 1 calc R . .
C33 C 0.2170(5) 0.5067(6) 0.3852(3) 0.0692(18) Uani 1 1 d . . .
H33A H 0.1610 0.5664 0.3714 0.104 Uiso 1 1 calc R . .
H33B H 0.2125 0.4821 0.4223 0.104 Uiso 1 1 calc R . .
H33C H 0.2068 0.4361 0.3611 0.104 Uiso 1 1 calc R . .
C34 C 0.8451(7) 0.5354(9) 0.4446(4) 0.125(3) Uani 1 1 d . . .
H34A H 0.8875 0.5620 0.4184 0.187 Uiso 1 1 calc R . .
H34B H 0.7830 0.4891 0.4252 0.187 Uiso 1 1 calc R . .
H34C H 0.8896 0.4846 0.4726 0.187 Uiso 1 1 calc R . .
C35 C 0.5389(9) 0.6702(11) 0.0317(4) 0.141(4) Uani 1 1 d . . .
H35A H 0.6148 0.6803 0.0494 0.212 Uiso 1 1 calc R . .
H35B H 0.5318 0.6617 -0.0079 0.212 Uiso 1 1 calc R . .
H35C H 0.5108 0.5979 0.0462 0.212 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.363(6) . ?
N1 C1 1.373(6) . ?
N1 H1 0.8600 . ?
N3 C19 1.369(6) . ?
N3 N4 1.379(6) . ?
N3 C27 1.406(6) . ?
N4 C17 1.324(6) . ?
N5 C19 1.387(6) . ?
N5 C9 1.475(6) . ?
N5 H5 0.9000 . ?
O1 C10 1.214(6) . ?
O2 C34 1.440(10) . ?
O2 H2 0.8200 . ?
O3 C35 1.352(11) . ?
O3 H3 0.8200 . ?
C1 C2 1.381(7) . ?
C1 C21 1.466(7) . ?
C2 C3 1.441(7) . ?
C2 C18 1.446(7) . ?
C3 C8 1.404(7) . ?
C3 C4 1.406(7) . ?
C4 C5 1.389(7) . ?
C5 C6 1.358(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.408(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(7) . ?
C7 C33 1.494(7) . ?
C8 C9 1.502(7) . ?
C9 C10 1.521(7) . ?
C9 H9 0.9800 . ?
C10 C11 1.487(7) . ?
C11 C16 1.377(7) . ?
C11 C12 1.381(7) . ?
C12 C13 1.371(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.353(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.423(7) . ?
C17 C20 1.491(7) . ?
C18 C19 1.378(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C26 1.374(8) . ?
C21 C22 1.383(8) . ?
C22 C23 1.379(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.371(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.381(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.377(8) . ?
C27 C32 1.380(8) . ?
C28 C29 1.369(8) . ?
C28 H28 0.9300 . ?
C29 C30 1.340(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.357(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.400(8) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 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
C4 N1 C1 109.5(4) . . ?
C4 N1 H1 125.2 . . ?
C1 N1 H1 125.2 . . ?
C19 N3 N4 110.1(4) . . ?
C19 N3 C27 128.9(4) . . ?
N4 N3 C27 121.0(4) . . ?
C17 N4 N3 105.6(4) . . ?
C19 N5 C9 116.7(4) . . ?
C19 N5 H5 107.4 . . ?
C9 N5 H5 107.5 . . ?
C34 O2 H2 109.5 . . ?
C35 O3 H3 109.5 . . ?
N1 C1 C2 109.0(5) . . ?
N1 C1 C21 119.6(5) . . ?
C2 C1 C21 131.3(5) . . ?
C1 C2 C3 106.6(4) . . ?
C1 C2 C18 129.0(5) . . ?
C3 C2 C18 124.4(4) . . ?
C8 C3 C4 119.7(5) . . ?
C8 C3 C2 133.9(5) . . ?
C4 C3 C2 106.4(4) . . ?
N1 C4 C5 130.3(5) . . ?
N1 C4 C3 108.3(5) . . ?
C5 C4 C3 121.4(5) . . ?
C6 C5 C4 117.9(5) . . ?
C6 C5 H5A 121.1 . . ?
C4 C5 H5A 121.1 . . ?
C5 C6 C7 122.8(5) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C8 C7 C6 119.4(5) . . ?
C8 C7 C33 122.1(5) . . ?
C6 C7 C33 118.5(5) . . ?
C7 C8 C3 118.9(5) . . ?
C7 C8 C9 120.3(5) . . ?
C3 C8 C9 120.8(5) . . ?
N5 C9 C8 112.7(4) . . ?
N5 C9 C10 109.2(4) . . ?
C8 C9 C10 113.8(4) . . ?
N5 C9 H9 106.9 . . ?
C8 C9 H9 106.9 . . ?
C10 C9 H9 106.9 . . ?
O1 C10 C11 120.7(5) . . ?
O1 C10 C9 119.2(5) . . ?
C11 C10 C9 120.1(4) . . ?
C16 C11 C12 118.9(5) . . ?
C16 C11 C10 122.6(5) . . ?
C12 C11 C10 118.5(5) . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.7(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 121.5(5) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 119.2(6) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C11 C16 C15 120.1(5) . . ?
C11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
N4 C17 C18 111.9(4) . . ?
N4 C17 C20 119.3(5) . . ?
C18 C17 C20 128.7(5) . . ?
C19 C18 C17 103.9(4) . . ?
C19 C18 C2 122.7(5) . . ?
C17 C18 C2 133.4(5) . . ?
N3 C19 C18 108.4(4) . . ?
N3 C19 N5 124.5(4) . . ?
C18 C19 N5 127.0(5) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.8(5) . . ?
C26 C21 C1 119.7(5) . . ?
C22 C21 C1 121.5(5) . . ?
C23 C22 C21 120.5(6) . . ?
C23 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C22 120.0(6) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C25 120.2(6) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 120.0(6) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C21 C26 C25 120.4(6) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C28 C27 C32 120.3(5) . . ?
C28 C27 N3 120.1(5) . . ?
C32 C27 N3 119.6(5) . . ?
C29 C28 C27 119.7(6) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 121.0(6) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 120.2(6) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 C32 121.1(6) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C27 C32 C31 117.7(6) . . ?
C27 C32 H32 121.2 . . ?
C31 C32 H32 121.2 . . ?
C7 C33 H33A 109.5 . . ?
C7 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C7 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O2 C34 H34A 109.5 . . ?
O2 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O2 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O3 C35 H35A 109.5 . . ?
O3 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
O3 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
C19 N3 N4 C17 0.0(5) . . . . ?
C27 N3 N4 C17 176.9(4) . . . . ?
C4 N1 C1 C2 4.4(6) . . . . ?
C4 N1 C1 C21 -172.7(5) . . . . ?
N1 C1 C2 C3 -4.3(6) . . . . ?
C21 C1 C2 C3 172.2(5) . . . . ?
N1 C1 C2 C18 177.6(5) . . . . ?
C21 C1 C2 C18 -5.8(10) . . . . ?
C1 C2 C3 C8 -174.8(5) . . . . ?
C18 C2 C3 C8 3.4(9) . . . . ?
C1 C2 C3 C4 2.7(6) . . . . ?
C18 C2 C3 C4 -179.1(5) . . . . ?
C1 N1 C4 C5 175.7(5) . . . . ?
C1 N1 C4 C3 -2.6(6) . . . . ?
C8 C3 C4 N1 177.8(4) . . . . ?
C2 C3 C4 N1 -0.2(5) . . . . ?
C8 C3 C4 C5 -0.7(8) . . . . ?
C2 C3 C4 C5 -178.6(5) . . . . ?
N1 C4 C5 C6 -179.6(5) . . . . ?
C3 C4 C5 C6 -1.6(8) . . . . ?
C4 C5 C6 C7 2.1(8) . . . . ?
C5 C6 C7 C8 -0.3(8) . . . . ?
C5 C6 C7 C33 -180.0(5) . . . . ?
C6 C7 C8 C3 -2.0(8) . . . . ?
C33 C7 C8 C3 177.7(5) . . . . ?
C6 C7 C8 C9 177.0(5) . . . . ?
C33 C7 C8 C9 -3.3(8) . . . . ?
C4 C3 C8 C7 2.4(7) . . . . ?
C2 C3 C8 C7 179.7(5) . . . . ?
C4 C3 C8 C9 -176.6(4) . . . . ?
C2 C3 C8 C9 0.7(8) . . . . ?
C19 N5 C9 C8 -79.2(5) . . . . ?
C19 N5 C9 C10 48.3(5) . . . . ?
C7 C8 C9 N5 -139.4(5) . . . . ?
C3 C8 C9 N5 39.6(6) . . . . ?
C7 C8 C9 C10 95.6(6) . . . . ?
C3 C8 C9 C10 -85.4(6) . . . . ?
N5 C9 C10 O1 -110.5(5) . . . . ?
C8 C9 C10 O1 16.3(7) . . . . ?
N5 C9 C10 C11 67.0(5) . . . . ?
C8 C9 C10 C11 -166.2(4) . . . . ?
O1 C10 C11 C16 -168.8(5) . . . . ?
C9 C10 C11 C16 13.8(7) . . . . ?
O1 C10 C11 C12 12.5(7) . . . . ?
C9 C10 C11 C12 -165.0(4) . . . . ?
C16 C11 C12 C13 2.4(8) . . . . ?
C10 C11 C12 C13 -178.8(5) . . . . ?
C11 C12 C13 C14 -1.0(9) . . . . ?
C12 C13 C14 C15 -1.6(10) . . . . ?
C13 C14 C15 C16 2.5(9) . . . . ?
C12 C11 C16 C15 -1.4(8) . . . . ?
C10 C11 C16 C15 179.9(5) . . . . ?
C14 C15 C16 C11 -1.0(9) . . . . ?
N3 N4 C17 C18 2.0(6) . . . . ?
N3 N4 C17 C20 -175.2(4) . . . . ?
N4 C17 C18 C19 -3.1(6) . . . . ?
C20 C17 C18 C19 173.8(5) . . . . ?
N4 C17 C18 C2 178.9(5) . . . . ?
C20 C17 C18 C2 -4.2(9) . . . . ?
C1 C2 C18 C19 150.3(5) . . . . ?
C3 C2 C18 C19 -27.4(8) . . . . ?
C1 C2 C18 C17 -32.0(9) . . . . ?
C3 C2 C18 C17 150.2(6) . . . . ?
N4 N3 C19 C18 -2.0(5) . . . . ?
C27 N3 C19 C18 -178.6(5) . . . . ?
N4 N3 C19 N5 174.9(4) . . . . ?
C27 N3 C19 N5 -1.8(8) . . . . ?
C17 C18 C19 N3 3.0(5) . . . . ?
C2 C18 C19 N3 -178.8(4) . . . . ?
C17 C18 C19 N5 -173.8(5) . . . . ?
C2 C18 C19 N5 4.5(8) . . . . ?
C9 N5 C19 N3 -119.1(5) . . . . ?
C9 N5 C19 C18 57.1(6) . . . . ?
N1 C1 C21 C26 128.3(6) . . . . ?
C2 C1 C21 C26 -48.0(9) . . . . ?
N1 C1 C21 C22 -52.8(7) . . . . ?
C2 C1 C21 C22 130.9(6) . . . . ?
C26 C21 C22 C23 2.8(9) . . . . ?
C1 C21 C22 C23 -176.1(5) . . . . ?
C21 C22 C23 C24 -3.6(9) . . . . ?
C22 C23 C24 C25 1.8(10) . . . . ?
C23 C24 C25 C26 0.6(9) . . . . ?
C22 C21 C26 C25 -0.4(9) . . . . ?
C1 C21 C26 C25 178.6(5) . . . . ?
C24 C25 C26 C21 -1.3(9) . . . . ?
C19 N3 C27 C28 -45.3(8) . . . . ?
N4 N3 C27 C28 138.4(5) . . . . ?
C19 N3 C27 C32 133.4(6) . . . . ?
N4 N3 C27 C32 -42.9(7) . . . . ?
C32 C27 C28 C29 -4.7(8) . . . . ?
N3 C27 C28 C29 173.9(5) . . . . ?
C27 C28 C29 C30 3.4(9) . . . . ?
C28 C29 C30 C31 -0.2(10) . . . . ?
C29 C30 C31 C32 -1.6(10) . . . . ?
C28 C27 C32 C31 3.0(8) . . . . ?
N3 C27 C32 C31 -175.7(5) . . . . ?
C30 C31 C32 C27 0.2(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.864
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 977865'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_130621a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H22 Br2 N4 O'
_chemical_formula_weight         590.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   18.4011(16)
_cell_length_b                   6.1969(5)
_cell_length_c                   23.223(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.394(2)
_cell_angle_gamma                90.00
_cell_volume                     2553.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1146
_cell_measurement_theta_min      3.433
_cell_measurement_theta_max      26.637

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    3.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4784
_exptl_absorpt_correction_T_max  0.8310
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12254
_diffrn_reflns_av_R_equivalents  0.3029
_diffrn_reflns_av_sigmaI/netI    0.2884
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4511
_reflns_number_gt                1317
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4511
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2586
_refine_ls_R_factor_gt           0.1119
_refine_ls_wR_factor_ref         0.2560
_refine_ls_wR_factor_gt          0.2151
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.10170(9) 0.2600(3) 1.08196(7) 0.1027(7) Uani 1 1 d . . .
Br2 Br 0.33657(11) -0.4792(3) 0.63372(8) 0.1205(8) Uani 1 1 d . . .
N1 N 0.4205(6) 0.3164(18) 0.8421(4) 0.063(3) Uani 1 1 d . . .
N2 N 0.4932(6) 0.5689(19) 0.9124(5) 0.069(3) Uani 1 1 d . . .
N3 N 0.4828(6) 0.7424(18) 0.9457(4) 0.071(3) Uani 1 1 d . . .
N4 N 0.2097(5) 0.2717(16) 0.8059(4) 0.059(3) Uani 1 1 d . . .
H4 H 0.1983 0.1519 0.8201 0.071 Uiso 1 1 calc R . .
O1 O 0.2095(5) 0.8207(15) 0.8636(4) 0.073(3) Uani 1 1 d . . .
C1 C 0.3489(7) 0.256(2) 0.8166(5) 0.058(3) Uani 1 1 d . . .
C2 C 0.2846(7) 0.351(2) 0.8301(5) 0.055(3) Uani 1 1 d . . .
C3 C 0.2955(7) 0.527(2) 0.8702(5) 0.056(3) Uani 1 1 d . . .
C4 C 0.3696(7) 0.599(2) 0.8964(5) 0.060(3) Uani 1 1 d . . .
C5 C 0.4279(7) 0.476(2) 0.8820(5) 0.057(3) Uani 1 1 d . . .
C6 C 0.4070(8) 0.758(2) 0.9368(5) 0.067(4) Uani 1 1 d . . .
C7 C 0.3758(6) 0.935(2) 0.9668(5) 0.081(4) Uani 1 1 d . . .
H7A H 0.4147 0.9901 0.9996 0.121 Uiso 1 1 calc R . .
H7B H 0.3352 0.8799 0.9813 0.121 Uiso 1 1 calc R . .
H7C H 0.3573 1.0489 0.9387 0.121 Uiso 1 1 calc R . .
C8 C 0.5721(6) 0.505(2) 0.9137(6) 0.084(4) Uani 1 1 d . . .
H8A H 0.5720 0.3609 0.8982 0.125 Uiso 1 1 calc R . .
H8B H 0.6031 0.5087 0.9541 0.125 Uiso 1 1 calc R . .
H8C H 0.5918 0.6028 0.8897 0.125 Uiso 1 1 calc R . .
C9 C 0.2323(7) 0.651(2) 0.8863(5) 0.057(3) Uani 1 1 d . . .
C10 C 0.2001(6) 0.547(2) 0.9325(5) 0.059(3) Uani 1 1 d . . .
C11 C 0.2234(6) 0.344(2) 0.9578(5) 0.065(4) Uani 1 1 d . . .
H11 H 0.2583 0.2643 0.9440 0.078 Uiso 1 1 calc R . .
C12 C 0.1952(7) 0.261(2) 1.0025(5) 0.075(4) Uani 1 1 d . . .
H12 H 0.2114 0.1273 1.0191 0.090 Uiso 1 1 calc R . .
C13 C 0.1431(7) 0.377(3) 1.0228(5) 0.068(4) Uani 1 1 d . . .
C14 C 0.1189(7) 0.576(2) 0.9989(6) 0.073(4) Uani 1 1 d . . .
H14 H 0.0838 0.6535 1.0129 0.088 Uiso 1 1 calc R . .
C15 C 0.1472(6) 0.659(2) 0.9545(6) 0.070(4) Uani 1 1 d . . .
H15 H 0.1305 0.7932 0.9385 0.084 Uiso 1 1 calc R . .
C16 C 0.3419(7) 0.076(2) 0.7717(5) 0.057(3) Uani 1 1 d . . .
C17 C 0.3986(8) -0.090(2) 0.7832(5) 0.070(4) Uani 1 1 d . . .
H17 H 0.4366 -0.0907 0.8188 0.084 Uiso 1 1 calc R . .
C18 C 0.3961(8) -0.249(2) 0.7412(6) 0.077(4) Uani 1 1 d . . .
H18 H 0.4338 -0.3534 0.7483 0.092 Uiso 1 1 calc R . .
C19 C 0.3407(9) -0.257(2) 0.6906(6) 0.073(4) Uani 1 1 d . . .
C20 C 0.2861(8) -0.093(3) 0.6770(6) 0.078(4) Uani 1 1 d . . .
H20 H 0.2504 -0.0921 0.6402 0.093 Uiso 1 1 calc R . .
C21 C 0.2855(7) 0.068(2) 0.7188(6) 0.066(4) Uani 1 1 d . . .
H21 H 0.2471 0.1706 0.7111 0.079 Uiso 1 1 calc R . .
C22 C 0.1542(7) 0.369(2) 0.7620(5) 0.057(3) Uani 1 1 d . . .
C23 C 0.0842(7) 0.274(2) 0.7387(5) 0.062(3) Uani 1 1 d . . .
H23 H 0.0752 0.1376 0.7521 0.074 Uiso 1 1 calc R . .
C24 C 0.0269(7) 0.376(2) 0.6956(6) 0.068(4) Uani 1 1 d . . .
H24 H -0.0197 0.3090 0.6819 0.081 Uiso 1 1 calc R . .
C25 C 0.0387(8) 0.580(2) 0.6728(6) 0.066(4) Uani 1 1 d . . .
C26 C 0.1078(7) 0.670(2) 0.6948(5) 0.063(3) Uani 1 1 d . . .
H26 H 0.1166 0.8032 0.6797 0.076 Uiso 1 1 calc R . .
C27 C 0.1661(7) 0.577(2) 0.7381(5) 0.063(3) Uani 1 1 d . . .
H27 H 0.2121 0.6474 0.7515 0.075 Uiso 1 1 calc R . .
C28 C -0.0232(7) 0.686(2) 0.6259(6) 0.087(4) Uani 1 1 d . . .
H28A H -0.0156 0.8395 0.6274 0.131 Uiso 1 1 calc R . .
H28B H -0.0710 0.6537 0.6333 0.131 Uiso 1 1 calc R . .
H28C H -0.0226 0.6332 0.5872 0.131 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C13 1.883(12) . ?
Br2 C19 1.894(13) . ?
N1 C5 1.340(14) . ?
N1 C1 1.347(13) . ?
N2 C5 1.348(14) . ?
N2 N3 1.366(13) . ?
N2 C8 1.499(14) . ?
N3 C6 1.359(14) . ?
N4 C22 1.376(14) . ?
N4 C2 1.430(13) . ?
N4 H4 0.8600 . ?
O1 C9 1.203(14) . ?
C1 C2 1.430(15) . ?
C1 C16 1.509(16) . ?
C2 C3 1.411(16) . ?
C3 C4 1.410(15) . ?
C3 C9 1.520(15) . ?
C4 C6 1.408(17) . ?
C4 C5 1.425(16) . ?
C6 C7 1.495(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.501(15) . ?
C10 C15 1.396(15) . ?
C10 C11 1.409(16) . ?
C11 C12 1.378(15) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(17) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(17) . ?
C14 C15 1.374(15) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.382(15) . ?
C16 C17 1.441(16) . ?
C17 C18 1.378(17) . ?
C17 H17 0.9300 . ?
C18 C19 1.337(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.405(17) . ?
C20 C21 1.396(17) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.389(14) . ?
C22 C27 1.442(16) . ?
C23 C24 1.400(15) . ?
C23 H23 0.9300 . ?
C24 C25 1.406(18) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(15) . ?
C25 C28 1.503(16) . ?
C26 C27 1.386(15) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C5 N1 C1 114.7(10) . . ?
C5 N2 N3 113.1(10) . . ?
C5 N2 C8 128.4(12) . . ?
N3 N2 C8 118.5(11) . . ?
C6 N3 N2 105.1(10) . . ?
C22 N4 C2 126.0(11) . . ?
C22 N4 H4 117.0 . . ?
C2 N4 H4 117.0 . . ?
N1 C1 C2 124.0(11) . . ?
N1 C1 C16 113.7(10) . . ?
C2 C1 C16 122.2(12) . . ?
C3 C2 C1 118.8(11) . . ?
C3 C2 N4 118.6(10) . . ?
C1 C2 N4 122.6(11) . . ?
C4 C3 C2 118.8(11) . . ?
C4 C3 C9 116.6(11) . . ?
C2 C3 C9 124.6(11) . . ?
C6 C4 C3 139.1(12) . . ?
C6 C4 C5 105.2(11) . . ?
C3 C4 C5 115.6(12) . . ?
N1 C5 N2 126.1(12) . . ?
N1 C5 C4 127.7(12) . . ?
N2 C5 C4 105.9(11) . . ?
N3 C6 C4 110.7(11) . . ?
N3 C6 C7 119.1(12) . . ?
C4 C6 C7 130.1(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 C10 121.9(11) . . ?
O1 C9 C3 122.5(11) . . ?
C10 C9 C3 115.6(11) . . ?
C15 C10 C11 117.1(11) . . ?
C15 C10 C9 119.8(12) . . ?
C11 C10 C9 123.0(11) . . ?
C12 C11 C10 120.8(11) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C11 120.1(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.6(12) . . ?
C12 C13 Br1 120.2(11) . . ?
C14 C13 Br1 119.2(11) . . ?
C15 C14 C13 119.4(12) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C10 122.0(13) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
C21 C16 C17 118.4(12) . . ?
C21 C16 C1 123.1(13) . . ?
C17 C16 C1 118.4(11) . . ?
C18 C17 C16 119.5(12) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 121.6(14) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 120.2(13) . . ?
C18 C19 Br2 121.4(12) . . ?
C20 C19 Br2 118.4(11) . . ?
C21 C20 C19 120.0(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C16 C21 C20 120.0(13) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
N4 C22 C23 122.1(12) . . ?
N4 C22 C27 121.2(12) . . ?
C23 C22 C27 116.6(12) . . ?
C22 C23 C24 122.1(13) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C23 C24 C25 120.9(12) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 116.7(13) . . ?
C26 C25 C28 123.1(13) . . ?
C24 C25 C28 120.2(13) . . ?
C25 C26 C27 124.7(13) . . ?
C25 C26 H26 117.6 . . ?
C27 C26 H26 117.6 . . ?
C26 C27 C22 118.9(12) . . ?
C26 C27 H27 120.5 . . ?
C22 C27 H27 120.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

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
C5 N2 N3 C6 1.2(14) . . . . ?
C8 N2 N3 C6 -178.6(11) . . . . ?
C5 N1 C1 C2 0.0(17) . . . . ?
C5 N1 C1 C16 179.8(11) . . . . ?
N1 C1 C2 C3 3.2(18) . . . . ?
C16 C1 C2 C3 -176.5(11) . . . . ?
N1 C1 C2 N4 -174.9(11) . . . . ?
C16 C1 C2 N4 5.4(17) . . . . ?
C22 N4 C2 C3 75.1(14) . . . . ?
C22 N4 C2 C1 -106.8(14) . . . . ?
C1 C2 C3 C4 -1.1(17) . . . . ?
N4 C2 C3 C4 177.0(10) . . . . ?
C1 C2 C3 C9 176.8(11) . . . . ?
N4 C2 C3 C9 -5.1(18) . . . . ?
C2 C3 C4 C6 -179.9(15) . . . . ?
C9 C3 C4 C6 2(2) . . . . ?
C2 C3 C4 C5 -3.6(17) . . . . ?
C9 C3 C4 C5 178.4(11) . . . . ?
C1 N1 C5 N2 -178.4(11) . . . . ?
C1 N1 C5 C4 -5.7(19) . . . . ?
N3 N2 C5 N1 173.9(12) . . . . ?
C8 N2 C5 N1 -6(2) . . . . ?
N3 N2 C5 C4 0.0(14) . . . . ?
C8 N2 C5 C4 179.7(12) . . . . ?
C6 C4 C5 N1 -174.9(13) . . . . ?
C3 C4 C5 N1 8(2) . . . . ?
C6 C4 C5 N2 -1.1(14) . . . . ?
C3 C4 C5 N2 -178.6(10) . . . . ?
N2 N3 C6 C4 -1.9(14) . . . . ?
N2 N3 C6 C7 -179.4(12) . . . . ?
C3 C4 C6 N3 178.5(14) . . . . ?
C5 C4 C6 N3 1.9(15) . . . . ?
C3 C4 C6 C7 -4(3) . . . . ?
C5 C4 C6 C7 179.1(14) . . . . ?
C4 C3 C9 O1 79.0(16) . . . . ?
C2 C3 C9 O1 -99.0(17) . . . . ?
C4 C3 C9 C10 -101.0(13) . . . . ?
C2 C3 C9 C10 81.1(15) . . . . ?
O1 C9 C10 C15 -6.3(19) . . . . ?
C3 C9 C10 C15 173.7(11) . . . . ?
O1 C9 C10 C11 177.0(13) . . . . ?
C3 C9 C10 C11 -3.1(17) . . . . ?
C15 C10 C11 C12 -0.5(18) . . . . ?
C9 C10 C11 C12 176.3(11) . . . . ?
C10 C11 C12 C13 0.6(19) . . . . ?
C11 C12 C13 C14 0(2) . . . . ?
C11 C12 C13 Br1 177.8(9) . . . . ?
C12 C13 C14 C15 0(2) . . . . ?
Br1 C13 C14 C15 -178.0(10) . . . . ?
C13 C14 C15 C10 -0.2(19) . . . . ?
C11 C10 C15 C14 0.3(18) . . . . ?
C9 C10 C15 C14 -176.6(12) . . . . ?
N1 C1 C16 C21 -141.0(11) . . . . ?
C2 C1 C16 C21 38.7(17) . . . . ?
N1 C1 C16 C17 36.3(15) . . . . ?
C2 C1 C16 C17 -144.0(11) . . . . ?
C21 C16 C17 C18 1.3(18) . . . . ?
C1 C16 C17 C18 -176.2(12) . . . . ?
C16 C17 C18 C19 -2(2) . . . . ?
C17 C18 C19 C20 5(2) . . . . ?
C17 C18 C19 Br2 -178.9(10) . . . . ?
C18 C19 C20 C21 -6(2) . . . . ?
Br2 C19 C20 C21 177.5(10) . . . . ?
C17 C16 C21 C20 -2.6(18) . . . . ?
C1 C16 C21 C20 174.7(12) . . . . ?
C19 C20 C21 C16 5(2) . . . . ?
C2 N4 C22 C23 176.2(10) . . . . ?
C2 N4 C22 C27 -4.0(17) . . . . ?
N4 C22 C23 C24 177.7(10) . . . . ?
C27 C22 C23 C24 -2.2(17) . . . . ?
C22 C23 C24 C25 1.8(18) . . . . ?
C23 C24 C25 C26 -0.2(18) . . . . ?
C23 C24 C25 C28 179.2(11) . . . . ?
C24 C25 C26 C27 -0.9(18) . . . . ?
C28 C25 C26 C27 179.7(11) . . . . ?
C25 C26 C27 C22 0.5(18) . . . . ?
N4 C22 C27 C26 -178.8(10) . . . . ?
C23 C22 C27 C26 1.1(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.135
_database_code_depnum_ccdc_archive 'CCDC 977866'
