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#  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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data_a30916b

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Br N3 O2'
_chemical_formula_weight         468.39

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

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

_cell_length_a                   10.780(4)
_cell_length_b                   13.453(6)
_cell_length_c                   15.304(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2219.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3784
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.35

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.877
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9621
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.016
_diffrn_reflns_theta_max         25.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4143
_reflns_number_gt                3137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.990

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0080P)²] 
 where P=(Fo²+2Fc²)/3 
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.004(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4143
_refine_ls_number_parameters     281
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0439
_refine_ls_wR_factor_gt          0.0429
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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 0.3228(3) 0.7575(3) 1.0453(2) 0.0381(10) Uani 1 1 d . . . . .
C2 C 0.3712(3) 0.6659(3) 1.0370(2) 0.0384(10) Uani 1 1 d . . . . .
C3 C 0.3868(4) 0.5224(3) 1.1513(3) 0.0622(13) Uani 1 1 d . . . . .
H3A H 0.4290 0.4769 1.1165 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3563(5) 0.4992(3) 1.2357(3) 0.0829(16) Uani 1 1 d . . . . .
H4A H 0.3781 0.4375 1.2582 0.099 Uiso 1 1 calc R U . . .
C5 C 0.2935(5) 0.5663(4) 1.2879(3) 0.0844(17) Uani 1 1 d . . . . .
H5A H 0.2748 0.5485 1.3451 0.101 Uiso 1 1 calc R U . . .
C6 C 0.2581(4) 0.6573(3) 1.2583(3) 0.0656(14) Uani 1 1 d . . . . .
H6A H 0.2142 0.7012 1.2936 0.079 Uiso 1 1 calc R U . . .
C7 C 0.2905(4) 0.6819(3) 1.1731(3) 0.0463(11) Uani 1 1 d . . . . .
C8 C 0.3533(3) 0.6156(3) 1.1181(2) 0.0437(9) Uani 1 1 d . . . . .
C9 C 0.4223(4) 0.6297(3) 0.9527(2) 0.0510(10) Uani 0.261(16) 1 d D . P A 1
H9A H 0.4113 0.5584 0.9481 0.061 Uiso 0.261(16) 1 calc R U P A 1
H9B H 0.5103 0.6443 0.9493 0.061 Uiso 0.261(16) 1 calc R U P A 1
C10 C 0.354(2) 0.6815(12) 0.8790(10) 0.043(6) Uani 0.261(16) 1 d D U P A 1
H10A H 0.3978 0.6694 0.8246 0.052 Uiso 0.261(16) 1 calc R U P A 1
H10B H 0.2717 0.6532 0.8736 0.052 Uiso 0.261(16) 1 calc R U P A 1
C9' C 0.4223(4) 0.6297(3) 0.9527(2) 0.0510(10) Uani 0.739(16) 1 d D . P A 2
H9'1 H 0.3693 0.5774 0.9301 0.061 Uiso 0.739(16) 1 calc R U P A 2
H9'2 H 0.5039 0.6017 0.9626 0.061 Uiso 0.739(16) 1 calc R U P A 2
C10' C 0.4317(10) 0.7108(5) 0.8864(4) 0.054(3) Uani 0.739(16) 1 d D U P A 2
H10C H 0.5136 0.7403 0.8910 0.064 Uiso 0.739(16) 1 calc R U P A 2
H10D H 0.4255 0.6810 0.8288 0.064 Uiso 0.739(16) 1 calc R U P A 2
C11 C 0.3168(3) 0.8347(2) 0.9757(2) 0.0353(9) Uani 1 1 d . . . . .
H11A H 0.2300 0.8561 0.9730 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3942(3) 0.9302(2) 0.9935(2) 0.0375(9) Uani 1 1 d . . . . .
C13 C 0.3843(3) 1.0005(3) 0.9135(2) 0.0365(10) Uani 1 1 d . . . . .
H13A H 0.2967 1.0193 0.9094 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4135(4) 0.9435(2) 0.8301(2) 0.0420(9) Uani 1 1 d . . . . .
H14A H 0.4997 0.9207 0.8335 0.050 Uiso 1 1 calc R U . . .
C15 C 0.3297(3) 0.8515(2) 0.8172(2) 0.0428(10) Uani 1 1 d . . . . .
H15A H 0.3621 0.8151 0.7666 0.051 Uiso 1 1 calc R U . . .
C16 C 0.3541(4) 0.9833(3) 1.0758(2) 0.0522(12) Uani 1 1 d . . . . .
H16A H 0.2695 1.0046 1.0698 0.078 Uiso 1 1 calc R U . . .
H16B H 0.4063 1.0401 1.0852 0.078 Uiso 1 1 calc R U . . .
H16C H 0.3610 0.9389 1.1247 0.078 Uiso 1 1 calc R U . . .
C17 C 0.4561(4) 1.0975(3) 0.9218(2) 0.0473(10) Uani 1 1 d . . . . .
C18 C 0.3939(4) 1.1815(3) 0.9463(3) 0.0606(13) Uani 1 1 d . . . . .
H18A H 0.3095 1.1777 0.9584 0.073 Uiso 1 1 calc R U . . .
C19 C 0.4544(5) 1.2726(3) 0.9534(3) 0.0827(16) Uani 1 1 d . . . . .
H19A H 0.4110 1.3293 0.9699 0.099 Uiso 1 1 calc R U . . .
C20 C 0.5780(7) 1.2773(4) 0.9359(3) 0.0967(19) Uani 1 1 d . . . . .
H20A H 0.6195 1.3377 0.9409 0.116 Uiso 1 1 calc R U . . .
C21 C 0.6412(5) 1.1948(4) 0.9114(3) 0.0858(17) Uani 1 1 d . . . . .
H21A H 0.7258 1.1989 0.9000 0.103 Uiso 1 1 calc R U . . .
C22 C 0.5813(4) 1.1053(3) 0.9031(2) 0.0625(11) Uani 1 1 d . . . . .
H22A H 0.6252 1.0495 0.8848 0.075 Uiso 1 1 calc R U . . .
C23 C 0.1942(3) 0.8779(3) 0.7967(3) 0.0548(11) Uani 1 1 d . . . . .
H23A H 0.1569 0.9080 0.8479 0.066 Uiso 1 1 calc R U . . .
H23B H 0.1924 0.9266 0.7500 0.066 Uiso 1 1 calc R U . . .
C24 C 0.1181(4) 0.7895(3) 0.7700(3) 0.0731(14) Uani 1 1 d . . . . .
H24A H 0.0343 0.8101 0.7589 0.110 Uiso 1 1 calc R U . . .
H24B H 0.1188 0.7411 0.8161 0.110 Uiso 1 1 calc R U . . .
H24C H 0.1525 0.7607 0.7179 0.110 Uiso 1 1 calc R U . . .
N1 N 0.2724(3) 0.7680(2) 1.1277(2) 0.0436(8) Uani 1 1 d . . . . .
H1A H 0.2356 0.8203 1.1472 0.052 Uiso 1 1 calc R U . . .
N2 N 0.3432(3) 0.7875(2) 0.8921(2) 0.0471(9) Uani 1 1 d D . . . .
N3 N 0.4009(4) 1.0084(3) 0.7509(2) 0.0566(10) Uani 1 1 d . . . . .
O1 O 0.3324(3) 1.0802(2) 0.7542(2) 0.0745(10) Uani 1 1 d . . . . .
O2 O 0.4542(3) 0.9815(2) 0.68528(18) 0.0841(10) Uani 1 1 d . . . . .
Br1 Br 0.56872(3) 0.89058(3) 1.01253(3) 0.05396(12) 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 1.343(4) . ?
C1 N1 1.380(4) . ?
C1 C11 1.490(4) . ?
C2 C8 1.427(4) . ?
C2 C9 1.485(5) . ?
C3 C4 1.369(5) . ?
C3 C8 1.400(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.360(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.390(5) . ?
C6 H6A 0.9300 . ?
C7 N1 1.365(5) . ?
C7 C8 1.401(5) . ?
C9 C10 1.516(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.444(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10' N2 1.408(6) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11 N2 1.457(4) . ?
C11 C12 1.556(4) . ?
C11 H11A 0.9800 . ?
C12 C16 1.512(4) . ?
C12 C13 1.551(4) . ?
C12 Br1 1.977(3) . ?
C13 C17 1.522(5) . ?
C13 C14 1.522(4) . ?
C13 H13A 0.9800 . ?
C14 N3 1.500(4) . ?
C14 C15 1.544(4) . ?
C14 H14A 0.9800 . ?
C15 N2 1.442(4) . ?
C15 C23 1.536(4) . ?
C15 H15A 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.366(5) . ?
C17 C22 1.384(5) . ?
C18 C19 1.393(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.361(7) . ?
C19 H19A 0.9300 . ?
C20 C21 1.355(6) . ?
C20 H20A 0.9300 . ?
C21 C22 1.373(5) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C24 1.502(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 H1A 0.8600 . ?
N3 O2 1.212(4) . ?
N3 O1 1.217(4) . ?

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 N1 109.5(3) . . ?
C2 C1 C11 126.1(4) . . ?
N1 C1 C11 124.3(3) . . ?
C1 C2 C8 107.5(3) . . ?
C1 C2 C9 121.8(3) . . ?
C8 C2 C9 130.5(3) . . ?
C4 C3 C8 118.9(4) . . ?
C4 C3 H3A 120.5 . . ?
C8 C3 H3A 120.5 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 122.1(5) . . ?
C6 C5 H5A 118.9 . . ?
C4 C5 H5A 118.9 . . ?
C5 C6 C7 117.2(5) . . ?
C5 C6 H6A 121.4 . . ?
C7 C6 H6A 121.4 . . ?
N1 C7 C6 130.1(4) . . ?
N1 C7 C8 107.7(4) . . ?
C6 C7 C8 122.2(4) . . ?
C3 C8 C7 118.5(4) . . ?
C3 C8 C2 134.9(4) . . ?
C7 C8 C2 106.6(3) . . ?
C2 C9 C10 108.4(7) . . ?
C2 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
C2 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 C9 112.9(13) . . ?
N2 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C10' H10C 108.2 . . ?
N2 C10' H10D 108.2 . . ?
H10C C10' H10D 107.3 . . ?
N2 C11 C1 108.3(3) . . ?
N2 C11 C12 114.1(3) . . ?
C1 C11 C12 115.3(3) . . ?
N2 C11 H11A 106.1 . . ?
C1 C11 H11A 106.1 . . ?
C12 C11 H11A 106.1 . . ?
C16 C12 C13 110.5(2) . . ?
C16 C12 C11 112.5(3) . . ?
C13 C12 C11 109.2(3) . . ?
C16 C12 Br1 106.1(2) . . ?
C13 C12 Br1 110.3(2) . . ?
C11 C12 Br1 108.28(19) . . ?
C17 C13 C14 113.4(3) . . ?
C17 C13 C12 115.0(3) . . ?
C14 C13 C12 109.9(3) . . ?
C17 C13 H13A 106.0 . . ?
C14 C13 H13A 106.0 . . ?
C12 C13 H13A 106.0 . . ?
N3 C14 C13 111.5(3) . . ?
N3 C14 C15 108.0(3) . . ?
C13 C14 C15 113.0(3) . . ?
N3 C14 H14A 108.1 . . ?
C13 C14 H14A 108.1 . . ?
C15 C14 H14A 108.1 . . ?
N2 C15 C23 113.4(3) . . ?
N2 C15 C14 108.5(3) . . ?
C23 C15 C14 113.4(3) . . ?
N2 C15 H15A 107.0 . . ?
C23 C15 H15A 107.0 . . ?
C14 C15 H15A 107.0 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.2(4) . . ?
C18 C17 C13 118.8(4) . . ?
C22 C17 C13 123.0(4) . . ?
C17 C18 C19 121.3(4) . . ?
C17 C18 H18A 119.4 . . ?
C19 C18 H18A 119.4 . . ?
C20 C19 C18 119.0(5) . . ?
C20 C19 H19A 120.5 . . ?
C18 C19 H19A 120.5 . . ?
C21 C20 C19 120.6(5) . . ?
C21 C20 H20A 119.7 . . ?
C19 C20 H20A 119.7 . . ?
C20 C21 C22 120.5(5) . . ?
C20 C21 H21A 119.7 . . ?
C22 C21 H21A 119.7 . . ?
C21 C22 C17 120.4(5) . . ?
C21 C22 H22A 119.8 . . ?
C17 C22 H22A 119.8 . . ?
C24 C23 C15 113.1(3) . . ?
C24 C23 H23A 109.0 . . ?
C15 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C15 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 N1 C1 108.7(3) . . ?
C7 N1 H1A 125.6 . . ?
C1 N1 H1A 125.6 . . ?
C10' N2 C15 117.2(4) . . ?
C15 N2 C10 119.1(7) . . ?
C10' N2 C11 120.5(4) . . ?
C15 N2 C11 114.7(3) . . ?
C10 N2 C11 124.7(7) . . ?
O2 N3 O1 124.0(4) . . ?
O2 N3 C14 116.9(4) . . ?
O1 N3 C14 118.9(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
N1 C1 C2 C8 -1.1(4) . . . . ?
C11 C1 C2 C8 -177.8(3) . . . . ?
N1 C1 C2 C9 174.5(3) . . . . ?
C11 C1 C2 C9 -2.1(6) . . . . ?
C8 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 C7 -1.5(7) . . . . ?
C5 C6 C7 N1 -177.0(4) . . . . ?
C5 C6 C7 C8 2.0(6) . . . . ?
C4 C3 C8 C7 0.5(6) . . . . ?
C4 C3 C8 C2 178.0(4) . . . . ?
N1 C7 C8 C3 177.7(3) . . . . ?
C6 C7 C8 C3 -1.5(6) . . . . ?
N1 C7 C8 C2 -0.5(4) . . . . ?
C6 C7 C8 C2 -179.7(4) . . . . ?
C1 C2 C8 C3 -176.8(4) . . . . ?
C9 C2 C8 C3 8.1(7) . . . . ?
C1 C2 C8 C7 1.0(4) . . . . ?
C9 C2 C8 C7 -174.2(4) . . . . ?
C1 C2 C9 C10 -29.0(11) . . . . ?
C8 C2 C9 C10 145.6(10) . . . . ?
C2 C9 C10 N2 46.8(16) . . . . ?
C2 C1 C11 N2 13.9(5) . . . . ?
N1 C1 C11 N2 -162.3(3) . . . . ?
C2 C1 C11 C12 -115.4(4) . . . . ?
N1 C1 C11 C12 68.4(4) . . . . ?
N2 C11 C12 C16 173.5(3) . . . . ?
C1 C11 C12 C16 -60.0(4) . . . . ?
N2 C11 C12 C13 50.5(3) . . . . ?
C1 C11 C12 C13 177.0(3) . . . . ?
N2 C11 C12 Br1 -69.6(3) . . . . ?
C1 C11 C12 Br1 56.9(3) . . . . ?
C16 C12 C13 C17 55.9(4) . . . . ?
C11 C12 C13 C17 -179.9(3) . . . . ?
Br1 C12 C13 C17 -61.0(3) . . . . ?
C16 C12 C13 C14 -174.8(3) . . . . ?
C11 C12 C13 C14 -50.6(3) . . . . ?
Br1 C12 C13 C14 68.3(3) . . . . ?
C17 C13 C14 N3 -51.6(4) . . . . ?
C12 C13 C14 N3 178.2(3) . . . . ?
C17 C13 C14 C15 -173.5(3) . . . . ?
C12 C13 C14 C15 56.3(4) . . . . ?
N3 C14 C15 N2 178.7(3) . . . . ?
C13 C14 C15 N2 -57.5(4) . . . . ?
N3 C14 C15 C23 -54.4(4) . . . . ?
C13 C14 C15 C23 69.4(4) . . . . ?
C14 C13 C17 C18 133.8(4) . . . . ?
C12 C13 C17 C18 -98.6(4) . . . . ?
C14 C13 C17 C22 -44.2(5) . . . . ?
C12 C13 C17 C22 83.4(4) . . . . ?
C22 C17 C18 C19 -0.8(6) . . . . ?
C13 C17 C18 C19 -178.9(4) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C18 C19 C20 C21 0.4(8) . . . . ?
C19 C20 C21 C22 0.5(8) . . . . ?
C20 C21 C22 C17 -1.6(7) . . . . ?
C18 C17 C22 C21 1.7(6) . . . . ?
C13 C17 C22 C21 179.7(4) . . . . ?
N2 C15 C23 C24 -64.9(4) . . . . ?
C14 C15 C23 C24 170.7(3) . . . . ?
C6 C7 N1 C1 178.9(4) . . . . ?
C8 C7 N1 C1 -0.2(4) . . . . ?
C2 C1 N1 C7 0.8(4) . . . . ?
C11 C1 N1 C7 177.6(3) . . . . ?
C23 C15 N2 C10' 139.4(6) . . . . ?
C14 C15 N2 C10' -93.7(6) . . . . ?
C23 C15 N2 C10 96.0(11) . . . . ?
C14 C15 N2 C10 -137.0(11) . . . . ?
C23 C15 N2 C11 -70.9(4) . . . . ?
C14 C15 N2 C11 56.1(4) . . . . ?
C9 C10 N2 C10' 56.7(13) . . . . ?
C9 C10 N2 C15 154.5(9) . . . . ?
C9 C10 N2 C11 -40.1(19) . . . . ?
C1 C11 N2 C10' -36.7(6) . . . . ?
C12 C11 N2 C10' 93.3(6) . . . . ?
C1 C11 N2 C15 174.6(3) . . . . ?
C12 C11 N2 C15 -55.4(4) . . . . ?
C1 C11 N2 C10 8.6(12) . . . . ?
C12 C11 N2 C10 138.6(12) . . . . ?
C13 C14 N3 O2 159.5(4) . . . . ?
C15 C14 N3 O2 -75.8(4) . . . . ?
C13 C14 N3 O1 -25.2(5) . . . . ?
C15 C14 N3 O1 99.5(4) . . . . ?

_refine_diff_density_max         0.639
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 969089'
#######################################################################
#
#                 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
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# 
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#  data retrieval see:
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#  to carry out CIF format checking respectively.
#
data_a30711a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C56 H70 N6 O4'
_chemical_formula_weight         891.18

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.784(5)
_cell_length_b                   8.872(4)
_cell_length_c                   14.497(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.000(7)
_cell_angle_gamma                90
_cell_volume                     1258.4(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    776
_cell_measurement_theta_min      2.512
_cell_measurement_theta_max      20.286

_exptl_crystal_description       sheet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5689
_diffrn_reflns_av_unetI/netI     0.0929
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.405
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.925
_reflns_number_total             4523
_reflns_number_gt                2207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.831
_reflns_Friedel_fraction_full    0.846

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1050P)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     SHELXL
_refine_ls_extinction_coef       0.017(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 795 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.5(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4523
_refine_ls_number_parameters     304
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.1794
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_restrained_S_all      0.867
_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
N1 N 0.4260(5) 0.8487(6) 0.4906(3) 0.0659(13) Uani 1 1 d D . . . .
H1 H 0.468(6) 0.762(7) 0.487(5) 0.099 Uiso 1 1 d D U . . .
N2 N 0.4091(4) 1.0215(5) 0.2623(3) 0.0600(12) Uani 1 1 d . . . . .
N3 N 0.3767(6) 0.8459(7) 0.0257(3) 0.0772(15) Uani 1 1 d . . . . .
O1 O 0.3302(5) 0.9347(7) -0.0295(3) 0.1134(18) Uani 1 1 d . . . . .
O2 O 0.4532(5) 0.7446(6) 0.0062(3) 0.0956(15) Uani 1 1 d . . . . .
C1 C 0.3843(6) 0.9253(7) 0.5690(3) 0.0674(16) Uani 1 1 d . . . . .
C2 C 0.3936(6) 0.8841(8) 0.6612(3) 0.0779(18) Uani 1 1 d . . . . .
H2 H 0.4345 0.7944 0.6795 0.094 Uiso 1 1 calc R U . . .
C3 C 0.3388(7) 0.9835(10) 0.7238(4) 0.093(2) Uani 1 1 d . . . . .
H3 H 0.3458 0.9614 0.7863 0.111 Uiso 1 1 calc R U . . .
C4 C 0.2743(7) 1.1141(10) 0.6977(4) 0.091(2) Uani 1 1 d . . . . .
H4 H 0.2366 1.1763 0.7426 0.109 Uiso 1 1 calc R U . . .
C5 C 0.2647(6) 1.1541(7) 0.6069(4) 0.0746(17) Uani 1 1 d . . . . .
H5 H 0.2221 1.2436 0.5898 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3198(5) 1.0587(6) 0.5406(3) 0.0597(14) Uani 1 1 d . . . . .
C7 C 0.3234(5) 1.0582(6) 0.4403(3) 0.0598(14) Uani 1 1 d . . . . .
C8 C 0.2754(6) 1.1740(7) 0.3729(3) 0.0685(16) Uani 1 1 d . . . . .
H8A H 0.3298 1.2648 0.3792 0.082 Uiso 1 1 calc R U . . .
H8B H 0.1808 1.1995 0.3856 0.082 Uiso 1 1 calc R U . . .
C9 C 0.2880(6) 1.1134(7) 0.2756(4) 0.0710(16) Uani 1 1 d . . . . .
H9A H 0.2077 1.0537 0.2614 0.085 Uiso 1 1 calc R U . . .
H9B H 0.2907 1.1975 0.2328 0.085 Uiso 1 1 calc R U . . .
C10 C 0.4413(6) 0.9908(7) 0.1648(3) 0.0627(15) Uani 1 1 d . . . . .
H10 H 0.4251 1.0847 0.1309 0.075 Uiso 1 1 calc R U . . .
C11 C 0.3410(6) 0.8738(7) 0.1263(3) 0.0660(15) Uani 1 1 d . . . . .
H11 H 0.2494 0.9184 0.1281 0.079 Uiso 1 1 calc R U . . .
C12 C 0.3356(5) 0.7261(6) 0.1797(3) 0.0599(14) Uani 1 1 d . . . . .
H12 H 0.4262 0.6792 0.1776 0.072 Uiso 1 1 calc R U . . .
C13 C 0.3016(6) 0.7669(7) 0.2825(3) 0.0610(14) Uani 1 1 d . . . . .
H13 H 0.2132 0.8188 0.2819 0.073 Uiso 1 1 calc R U . . .
C14 C 0.4064(6) 0.8805(6) 0.3171(3) 0.0577(13) Uani 1 1 d . . . . .
H14 H 0.4969 0.8337 0.3125 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3874(5) 0.9311(6) 0.4144(3) 0.0565(13) Uani 1 1 d . . . . .
C16 C 0.5893(6) 0.9513(8) 0.1515(3) 0.0733(16) Uani 1 1 d . . . . .
H16A H 0.6053 0.8509 0.1757 0.088 Uiso 1 1 calc R U . . .
H16B H 0.6092 0.9493 0.0860 0.088 Uiso 1 1 calc R U . . .
C17 C 0.6851(7) 1.0589(11) 0.1976(5) 0.106(2) Uani 1 1 d . . . . .
H17A H 0.6570 1.1604 0.1816 0.127 Uiso 1 1 calc R U . . .
H17B H 0.6739 1.0481 0.2637 0.127 Uiso 1 1 calc R U . . .
C18 C 0.8292(9) 1.0443(15) 0.1766(7) 0.153(4) Uani 1 1 d . . . . .
H18A H 0.8445 1.0704 0.1124 0.184 Uiso 1 1 calc R U . . .
H18B H 0.8570 0.9403 0.1852 0.184 Uiso 1 1 calc R U . . .
C19 C 0.9161(10) 1.146(2) 0.2376(9) 0.231(7) Uani 1 1 d . . . . .
H19A H 0.8953 1.2492 0.2247 0.347 Uiso 1 1 calc R U . . .
H19B H 1.0111 1.1271 0.2254 0.347 Uiso 1 1 calc R U . . .
H19C H 0.8968 1.1244 0.3012 0.347 Uiso 1 1 calc R U . . .
C20 C 0.2330(6) 0.6175(7) 0.1391(3) 0.0680(16) Uani 1 1 d . . . . .
C21 C 0.2768(7) 0.4782(8) 0.1072(3) 0.0792(18) Uani 1 1 d . . . . .
H21 H 0.3687 0.4519 0.1105 0.095 Uiso 1 1 calc R U . . .
C22 C 0.1825(10) 0.3788(8) 0.0706(4) 0.098(2) Uani 1 1 d . . . . .
H22 H 0.2115 0.2851 0.0496 0.118 Uiso 1 1 calc R U . . .
C23 C 0.0473(10) 0.4165(13) 0.0647(5) 0.110(3) Uani 1 1 d . . . . .
H23 H -0.0151 0.3497 0.0388 0.132 Uiso 1 1 calc R U . . .
C24 C 0.0051(8) 0.5509(13) 0.0968(5) 0.105(2) Uani 1 1 d . . . . .
H24 H -0.0872 0.5756 0.0940 0.127 Uiso 1 1 calc R U . . .
C25 C 0.0958(7) 0.6524(9) 0.1337(4) 0.0829(19) Uani 1 1 d . . . . .
H25 H 0.0647 0.7450 0.1551 0.099 Uiso 1 1 calc R U . . .
C26 C 0.2848(7) 0.6300(7) 0.3438(4) 0.0846(19) Uani 1 1 d D . . . .
H26A H 0.3673 0.6151 0.3798 0.102 Uiso 1 1 calc R U . . .
H26B H 0.2710 0.5412 0.3059 0.102 Uiso 1 1 calc R U . . .
C27 C 0.1598(10) 0.6504(10) 0.4103(5) 0.148(4) Uani 1 1 d D U . . .
H27A H 0.1740 0.7420 0.4456 0.177 Uiso 1 1 calc R U . . .
H27B H 0.0788 0.6656 0.3728 0.177 Uiso 1 1 calc R U . . .
C28 C 0.1320(18) 0.5291(15) 0.4746(10) 0.262(8) Uani 1 1 d D U . . .
H28A H 0.0805 0.4517 0.4441 0.392 Uiso 1 1 calc R U . . .
H28B H 0.0804 0.5674 0.5258 0.392 Uiso 1 1 calc R U . . .
H28C H 0.2168 0.4879 0.4965 0.392 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C15 1.378(6) . ?
N1 C1 1.386(7) . ?
N1 H1 0.88(5) . ?
N2 C9 1.451(7) . ?
N2 C10 1.474(6) . ?
N2 C14 1.482(7) . ?
N3 O2 1.204(7) . ?
N3 O1 1.212(7) . ?
N3 C11 1.519(7) . ?
C1 C2 1.388(7) . ?
C1 C6 1.404(8) . ?
C2 C3 1.374(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.454(7) . ?
C7 C15 1.344(8) . ?
C7 C8 1.493(8) . ?
C8 C9 1.515(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C16 1.502(7) . ?
C10 C11 1.533(8) . ?
C10 H10 0.9800 . ?
C11 C12 1.523(8) . ?
C11 H11 0.9800 . ?
C12 C20 1.511(8) . ?
C12 C13 1.570(6) . ?
C12 H12 0.9800 . ?
C13 C26 1.514(8) . ?
C13 C14 1.522(8) . ?
C13 H13 0.9800 . ?
C14 C15 1.492(7) . ?
C14 H14 0.9800 . ?
C16 C17 1.495(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.449(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.521(17) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C25 1.379(8) . ?
C20 C21 1.387(9) . ?
C21 C22 1.382(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.345(13) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(10) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.568(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 C28 1.450(10) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
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
C15 N1 C1 108.5(5) . . ?
C15 N1 H1 123(4) . . ?
C1 N1 H1 128(4) . . ?
C9 N2 C10 114.0(4) . . ?
C9 N2 C14 112.9(4) . . ?
C10 N2 C14 111.2(4) . . ?
O2 N3 O1 124.3(5) . . ?
O2 N3 C11 119.3(5) . . ?
O1 N3 C11 116.2(6) . . ?
N1 C1 C2 129.9(6) . . ?
N1 C1 C6 107.8(4) . . ?
C2 C1 C6 122.3(6) . . ?
C3 C2 C1 116.2(6) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C4 C3 C2 122.6(6) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C5 C4 C3 121.1(6) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 118.8(6) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.0(5) . . ?
C5 C6 C7 134.7(6) . . ?
C1 C6 C7 106.3(5) . . ?
C15 C7 C6 107.0(5) . . ?
C15 C7 C8 122.8(4) . . ?
C6 C7 C8 130.1(5) . . ?
C7 C8 C9 109.9(5) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N2 C9 C8 113.0(4) . . ?
N2 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C16 111.8(4) . . ?
N2 C10 C11 109.7(4) . . ?
C16 C10 C11 114.4(5) . . ?
N2 C10 H10 106.8 . . ?
C16 C10 H10 106.8 . . ?
C11 C10 H10 106.8 . . ?
N3 C11 C12 110.8(5) . . ?
N3 C11 C10 108.2(4) . . ?
C12 C11 C10 114.8(4) . . ?
N3 C11 H11 107.6 . . ?
C12 C11 H11 107.6 . . ?
C10 C11 H11 107.6 . . ?
C20 C12 C11 112.0(4) . . ?
C20 C12 C13 112.1(4) . . ?
C11 C12 C13 106.9(4) . . ?
C20 C12 H12 108.6 . . ?
C11 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
C26 C13 C14 114.3(4) . . ?
C26 C13 C12 113.3(5) . . ?
C14 C13 C12 108.8(4) . . ?
C26 C13 H13 106.6 . . ?
C14 C13 H13 106.6 . . ?
C12 C13 H13 106.6 . . ?
N2 C14 C15 104.8(4) . . ?
N2 C14 C13 113.2(4) . . ?
C15 C14 C13 115.2(4) . . ?
N2 C14 H14 107.8 . . ?
C15 C14 H14 107.8 . . ?
C13 C14 H14 107.8 . . ?
C7 C15 N1 110.4(4) . . ?
C7 C15 C14 125.1(5) . . ?
N1 C15 C14 124.4(5) . . ?
C17 C16 C10 113.5(5) . . ?
C17 C16 H16A 108.9 . . ?
C10 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C10 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 117.3(7) . . ?
C18 C17 H17A 108.0 . . ?
C16 C17 H17A 108.0 . . ?
C18 C17 H17B 108.0 . . ?
C16 C17 H17B 108.0 . . ?
H17A C17 H17B 107.2 . . ?
C17 C18 C19 111.6(9) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 118.8(6) . . ?
C25 C20 C12 121.7(6) . . ?
C21 C20 C12 119.5(6) . . ?
C22 C21 C20 119.4(7) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C23 C22 C21 120.9(8) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C24 C23 C22 119.5(8) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 121.2(8) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C20 120.2(7) . . ?
C24 C25 H25 119.9 . . ?
C20 C25 H25 119.9 . . ?
C13 C26 C27 110.6(6) . . ?
C13 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C13 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 117.1(9) . . ?
C28 C27 H27A 108.0 . . ?
C26 C27 H27A 108.0 . . ?
C28 C27 H27B 108.0 . . ?
C26 C27 H27B 108.0 . . ?
H27A C27 H27B 107.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 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
C15 N1 C1 C2 176.3(6) . . . . ?
C15 N1 C1 C6 -0.6(6) . . . . ?
N1 C1 C2 C3 -178.2(6) . . . . ?
C6 C1 C2 C3 -1.6(8) . . . . ?
C1 C2 C3 C4 2.1(10) . . . . ?
C2 C3 C4 C5 -1.9(11) . . . . ?
C3 C4 C5 C6 1.0(10) . . . . ?
C4 C5 C6 C1 -0.5(8) . . . . ?
C4 C5 C6 C7 176.2(6) . . . . ?
N1 C1 C6 C5 178.1(5) . . . . ?
C2 C1 C6 C5 0.9(8) . . . . ?
N1 C1 C6 C7 0.5(6) . . . . ?
C2 C1 C6 C7 -176.7(5) . . . . ?
C5 C6 C7 C15 -177.3(6) . . . . ?
C1 C6 C7 C15 -0.3(6) . . . . ?
C5 C6 C7 C8 5.9(10) . . . . ?
C1 C6 C7 C8 -177.2(5) . . . . ?
C15 C7 C8 C9 9.5(8) . . . . ?
C6 C7 C8 C9 -174.0(5) . . . . ?
C10 N2 C9 C8 -166.5(5) . . . . ?
C14 N2 C9 C8 65.4(6) . . . . ?
C7 C8 C9 N2 -37.3(7) . . . . ?
C9 N2 C10 C16 157.5(5) . . . . ?
C14 N2 C10 C16 -73.5(6) . . . . ?
C9 N2 C10 C11 -74.5(6) . . . . ?
C14 N2 C10 C11 54.5(5) . . . . ?
O2 N3 C11 C12 -34.0(7) . . . . ?
O1 N3 C11 C12 149.9(5) . . . . ?
O2 N3 C11 C10 92.7(6) . . . . ?
O1 N3 C11 C10 -83.4(6) . . . . ?
N2 C10 C11 N3 179.6(5) . . . . ?
C16 C10 C11 N3 -53.8(6) . . . . ?
N2 C10 C11 C12 -56.0(6) . . . . ?
C16 C10 C11 C12 70.6(5) . . . . ?
N3 C11 C12 C20 -58.1(6) . . . . ?
C10 C11 C12 C20 178.9(5) . . . . ?
N3 C11 C12 C13 178.7(4) . . . . ?
C10 C11 C12 C13 55.7(6) . . . . ?
C20 C12 C13 C26 53.7(6) . . . . ?
C11 C12 C13 C26 176.7(5) . . . . ?
C20 C12 C13 C14 -178.0(5) . . . . ?
C11 C12 C13 C14 -55.0(5) . . . . ?
C9 N2 C14 C15 -56.2(5) . . . . ?
C10 N2 C14 C15 174.3(4) . . . . ?
C9 N2 C14 C13 70.2(5) . . . . ?
C10 N2 C14 C13 -59.3(5) . . . . ?
C26 C13 C14 N2 -173.1(4) . . . . ?
C12 C13 C14 N2 59.2(6) . . . . ?
C26 C13 C14 C15 -52.5(7) . . . . ?
C12 C13 C14 C15 179.8(5) . . . . ?
C6 C7 C15 N1 -0.1(6) . . . . ?
C8 C7 C15 N1 177.1(5) . . . . ?
C6 C7 C15 C14 176.2(5) . . . . ?
C8 C7 C15 C14 -6.6(8) . . . . ?
C1 N1 C15 C7 0.4(6) . . . . ?
C1 N1 C15 C14 -175.9(5) . . . . ?
N2 C14 C15 C7 28.2(7) . . . . ?
C13 C14 C15 C7 -96.9(7) . . . . ?
N2 C14 C15 N1 -156.0(5) . . . . ?
C13 C14 C15 N1 78.9(7) . . . . ?
N2 C10 C16 C17 -48.8(7) . . . . ?
C11 C10 C16 C17 -174.3(5) . . . . ?
C10 C16 C17 C18 -170.4(8) . . . . ?
C16 C17 C18 C19 -172.2(10) . . . . ?
C11 C12 C20 C25 -60.8(6) . . . . ?
C13 C12 C20 C25 59.4(6) . . . . ?
C11 C12 C20 C21 119.9(5) . . . . ?
C13 C12 C20 C21 -119.9(5) . . . . ?
C25 C20 C21 C22 0.4(8) . . . . ?
C12 C20 C21 C22 179.7(5) . . . . ?
C20 C21 C22 C23 0.5(9) . . . . ?
C21 C22 C23 C24 -1.3(11) . . . . ?
C22 C23 C24 C25 1.3(12) . . . . ?
C23 C24 C25 C20 -0.4(10) . . . . ?
C21 C20 C25 C24 -0.4(8) . . . . ?
C12 C20 C25 C24 -179.7(5) . . . . ?
C14 C13 C26 C27 96.8(7) . . . . ?
C12 C13 C26 C27 -137.8(6) . . . . ?
C13 C26 C27 C28 -179.0(11) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-2

_database_code_depnum_ccdc_archive 'CCDC 969090'
