# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_Koch7fin
_database_code_depnum_ccdc_archive 'CCDC 1533888'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br3 N6, C H Cl3'
_chemical_formula_sum            'C22 H22 Br3 Cl3 N6'
_chemical_formula_weight         716.53

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8918(4)
_cell_length_b                   16.9233(8)
_cell_length_c                   17.9116(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.758(2)
_cell_angle_gamma                90
_cell_volume                     2670.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9920
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.58

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    4.856
_shelx_estimated_absorpt_T_min   0.183
_shelx_estimated_absorpt_T_max   0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1829
_exptl_absorpt_correction_T_max  0.5105
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25713
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         28.100
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6514
_reflns_number_gt                5311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0283P)²+2.7478P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6514
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22887(3) 0.38368(2) 0.16562(2) 0.03697(8) Uani 1 1 d . . . . .
Br2 Br 0.06052(3) 0.11106(2) -0.14364(2) 0.03945(8) Uani 1 1 d . . . . .
Br3 Br 1.45760(2) 0.13796(2) 0.09635(2) 0.03008(7) Uani 1 1 d . . . . .
N1 N 0.6014(2) 0.40935(11) 0.06540(11) 0.0230(4) Uani 1 1 d . . . . .
N2 N 0.6092(2) 0.47946(11) 0.10209(11) 0.0239(4) Uani 1 1 d . . . . .
N3 N 0.5068(2) 0.11462(12) -0.15424(11) 0.0237(4) Uani 1 1 d . . . . .
N4 N 0.4684(2) 0.06331(12) -0.21120(11) 0.0265(4) Uani 1 1 d . . . . .
N5 N 1.0337(2) 0.11923(11) 0.14633(10) 0.0202(4) Uani 1 1 d . . . . .
N6 N 1.1049(2) 0.08474(14) 0.20961(11) 0.0285(5) Uani 1 1 d . . . . .
C1 C 0.7337(2) 0.29949(13) 0.01162(13) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.6855(2) 0.26209(14) -0.05706(13) 0.0223(5) Uani 1 1 d . . . . .
C3 C 0.7042(2) 0.18067(14) -0.06360(12) 0.0221(5) Uani 1 1 d . . . . .
C4 C 0.7619(2) 0.13494(13) -0.00111(14) 0.0224(5) Uani 1 1 d . . . . .
C5 C 0.8069(2) 0.17271(13) 0.06815(12) 0.0200(4) Uani 1 1 d . . . . .
C6 C 0.7959(2) 0.25533(13) 0.07450(12) 0.0198(4) Uani 1 1 d . . . . .
C7 C 0.6104(3) 0.31042(18) -0.12361(15) 0.0383(6) Uani 1 1 d . . . . .
H7A H 0.5394 0.3482 -0.1061 0.057 Uiso 1 1 calc R U . . .
H7B H 0.5552 0.2750 -0.1610 0.057 Uiso 1 1 calc R U . . .
H7C H 0.6883 0.3391 -0.1465 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7729(3) 0.04589(15) -0.00818(18) 0.0389(6) Uani 1 1 d . . . . .
H8A H 0.6966 0.0208 0.0186 0.058 Uiso 1 1 calc R U . . .
H8B H 0.8744 0.0284 0.0138 0.058 Uiso 1 1 calc R U . . .
H8C H 0.7549 0.0310 -0.0615 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8458(3) 0.29528(17) 0.14922(14) 0.0323(6) Uani 1 1 d . . . . .
H9A H 0.8680 0.3510 0.1407 0.048 Uiso 1 1 calc R U . . .
H9B H 0.9372 0.2692 0.1745 0.048 Uiso 1 1 calc R U . . .
H9C H 0.7645 0.2915 0.1810 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7188(3) 0.38851(14) 0.01830(15) 0.0285(5) Uani 1 1 d . . . . .
H10A H 0.8174 0.4110 0.0408 0.034 Uiso 1 1 calc R U . . .
H10B H 0.6922 0.4117 -0.0325 0.034 Uiso 1 1 calc R U . . .
C11 C 0.4799(3) 0.36636(14) 0.07785(15) 0.0273(5) Uani 1 1 d . . . . .
H11 H 0.4514 0.3158 0.0577 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4056(2) 0.41069(14) 0.12576(13) 0.0243(5) Uani 1 1 d . . . . .
C13 C 0.4892(3) 0.47953(14) 0.13957(13) 0.0245(5) Uani 1 1 d . . . . .
H13 H 0.4644 0.5211 0.1714 0.029 Uiso 1 1 calc R U . . .
C14 C 0.6646(3) 0.14206(18) -0.14030(15) 0.0342(6) Uani 1 1 d . . . . .
H14A H 0.6822 0.1805 -0.1799 0.041 Uiso 1 1 calc R U . . .
H14B H 0.7332 0.0965 -0.1440 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3204(3) 0.05511(15) -0.21496(13) 0.0266(5) Uani 1 1 d . . . . .
H15 H 0.2604 0.0219 -0.2499 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2629(2) 0.10152(14) -0.16088(13) 0.0256(5) Uani 1 1 d . . . . .
C17 C 0.3857(3) 0.13952(15) -0.12261(14) 0.0284(5) Uani 1 1 d . . . . .
H17 H 0.3857 0.1759 -0.0822 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8672(2) 0.12467(15) 0.13661(14) 0.0288(5) Uani 1 1 d . . . . .
H18A H 0.8348 0.1493 0.1820 0.035 Uiso 1 1 calc R U . . .
H18B H 0.8235 0.0708 0.1316 0.035 Uiso 1 1 calc R U . . .
C19 C 1.2514(3) 0.08630(16) 0.20167(13) 0.0277(5) Uani 1 1 d . . . . .
H19 H 1.3305 0.0661 0.2376 0.033 Uiso 1 1 calc R U . . .
C20 C 1.2733(2) 0.12138(13) 0.13390(13) 0.0217(5) Uani 1 1 d . . . . .
C21 C 1.1311(3) 0.14077(14) 0.09868(14) 0.0260(5) Uani 1 1 d . . . . .
H21 H 1.1065 0.1645 0.0505 0.031 Uiso 1 1 calc R U . . .
C1A C 0.8541(3) 0.61734(15) 0.10185(14) 0.0292(5) Uani 1 1 d . . . . .
H1A H 0.7562 0.5887 0.0874 0.035 Uiso 1 1 calc R U . . .
Cl1A Cl 0.87187(10) 0.69030(5) 0.03410(4) 0.0534(2) Uani 1 1 d . . . . .
Cl2A Cl 1.00430(7) 0.54877(4) 0.10592(4) 0.03982(16) Uani 1 1 d . . . . .
Cl3A Cl 0.85154(10) 0.66061(5) 0.19095(4) 0.0531(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.869(2) . ?
Br2 C16 1.874(2) . ?
Br3 C20 1.874(2) . ?
N1 C11 1.346(3) . ?
N1 N2 1.354(3) . ?
N1 C10 1.471(3) . ?
N2 C13 1.335(3) . ?
N3 N4 1.348(3) . ?
N3 C17 1.351(3) . ?
N3 C14 1.467(3) . ?
N4 C15 1.316(3) . ?
N5 C21 1.345(3) . ?
N5 N6 1.354(3) . ?
N5 C18 1.470(3) . ?
N6 C19 1.329(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.402(3) . ?
C1 C10 1.518(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.523(3) . ?
C3 C4 1.400(3) . ?
C3 C14 1.519(3) . ?
C4 C5 1.405(3) . ?
C4 C8 1.517(3) . ?
C5 C6 1.407(3) . ?
C5 C18 1.508(3) . ?
C6 C9 1.512(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.374(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.369(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(3) . ?
C21 H21 0.9500 . ?
C1A Cl1A 1.753(3) . ?
C1A Cl3A 1.759(3) . ?
C1A Cl2A 1.763(3) . ?
C1A H1A 1.0000 . ?

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
C11 N1 N2 112.50(18) . . ?
C11 N1 C10 127.8(2) . . ?
N2 N1 C10 119.67(18) . . ?
C13 N2 N1 104.67(18) . . ?
N4 N3 C17 112.53(19) . . ?
N4 N3 C14 118.14(18) . . ?
C17 N3 C14 129.0(2) . . ?
C15 N4 N3 104.86(19) . . ?
C21 N5 N6 112.32(18) . . ?
C21 N5 C18 129.19(19) . . ?
N6 N5 C18 118.41(18) . . ?
C19 N6 N5 104.84(18) . . ?
C2 C1 C6 120.4(2) . . ?
C2 C1 C10 119.9(2) . . ?
C6 C1 C10 119.7(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 120.6(2) . . ?
C1 C2 C7 119.7(2) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 C14 119.0(2) . . ?
C4 C3 C14 120.0(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 C8 120.2(2) . . ?
C5 C4 C8 120.8(2) . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 C18 120.0(2) . . ?
C6 C5 C18 119.4(2) . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C9 120.6(2) . . ?
C5 C6 C9 120.0(2) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 111.03(18) . . ?
N1 C10 H10A 109.4 . . ?
C1 C10 H10A 109.4 . . ?
N1 C10 H10B 109.4 . . ?
C1 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
N1 C11 C12 105.8(2) . . ?
N1 C11 H11 127.1 . . ?
C12 C11 H11 127.1 . . ?
C11 C12 C13 106.2(2) . . ?
C11 C12 Br1 127.22(19) . . ?
C13 C12 Br1 126.56(18) . . ?
N2 C13 C12 110.8(2) . . ?
N2 C13 H13 124.6 . . ?
C12 C13 H13 124.6 . . ?
N3 C14 C3 112.91(19) . . ?
N3 C14 H14A 109.0 . . ?
C3 C14 H14A 109.0 . . ?
N3 C14 H14B 109.0 . . ?
C3 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
N4 C15 C16 111.2(2) . . ?
N4 C15 H15 124.4 . . ?
C16 C15 H15 124.4 . . ?
C17 C16 C15 105.7(2) . . ?
C17 C16 Br2 126.57(19) . . ?
C15 C16 Br2 127.77(18) . . ?
N3 C17 C16 105.7(2) . . ?
N3 C17 H17 127.1 . . ?
C16 C17 H17 127.1 . . ?
N5 C18 C5 111.83(18) . . ?
N5 C18 H18A 109.3 . . ?
C5 C18 H18A 109.3 . . ?
N5 C18 H18B 109.3 . . ?
C5 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
N6 C19 C20 110.9(2) . . ?
N6 C19 H19 124.5 . . ?
C20 C19 H19 124.5 . . ?
C21 C20 C19 105.90(19) . . ?
C21 C20 Br3 126.45(17) . . ?
C19 C20 Br3 127.64(17) . . ?
N5 C21 C20 106.0(2) . . ?
N5 C21 H21 127.0 . . ?
C20 C21 H21 127.0 . . ?
Cl1A C1A Cl3A 110.38(14) . . ?
Cl1A C1A Cl2A 110.72(14) . . ?
Cl3A C1A Cl2A 109.83(14) . . ?
Cl1A C1A H1A 108.6 . . ?
Cl3A C1A H1A 108.6 . . ?
Cl2A C1A H1A 108.6 . . ?

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
C11 N1 N2 C13 0.9(3) . . . . ?
C10 N1 N2 C13 -179.3(2) . . . . ?
C17 N3 N4 C15 -0.7(3) . . . . ?
C14 N3 N4 C15 -174.3(2) . . . . ?
C21 N5 N6 C19 1.2(3) . . . . ?
C18 N5 N6 C19 178.2(2) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C10 C1 C2 C3 177.80(19) . . . . ?
C6 C1 C2 C7 176.7(2) . . . . ?
C10 C1 C2 C7 -3.4(3) . . . . ?
C1 C2 C3 C4 4.0(3) . . . . ?
C7 C2 C3 C4 -174.8(2) . . . . ?
C1 C2 C3 C14 -174.48(19) . . . . ?
C7 C2 C3 C14 6.7(3) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C14 C3 C4 C5 175.88(19) . . . . ?
C2 C3 C4 C8 176.5(2) . . . . ?
C14 C3 C4 C8 -5.1(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C8 C4 C5 C6 -179.7(2) . . . . ?
C3 C4 C5 C18 179.05(19) . . . . ?
C8 C4 C5 C18 0.1(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C10 C1 C6 C5 178.98(18) . . . . ?
C2 C1 C6 C9 -179.00(19) . . . . ?
C10 C1 C6 C9 1.1(3) . . . . ?
C4 C5 C6 C1 2.5(3) . . . . ?
C18 C5 C6 C1 -177.24(18) . . . . ?
C4 C5 C6 C9 -179.57(19) . . . . ?
C18 C5 C6 C9 0.6(3) . . . . ?
C11 N1 C10 C1 -25.9(4) . . . . ?
N2 N1 C10 C1 154.3(2) . . . . ?
C2 C1 C10 N1 110.1(2) . . . . ?
C6 C1 C10 N1 -70.1(3) . . . . ?
N2 N1 C11 C12 -0.6(3) . . . . ?
C10 N1 C11 C12 179.7(2) . . . . ?
N1 C11 C12 C13 0.0(3) . . . . ?
N1 C11 C12 Br1 -179.27(17) . . . . ?
N1 N2 C13 C12 -0.8(2) . . . . ?
C11 C12 C13 N2 0.5(3) . . . . ?
Br1 C12 C13 N2 179.82(17) . . . . ?
N4 N3 C14 C3 -164.3(2) . . . . ?
C17 N3 C14 C3 23.3(4) . . . . ?
C2 C3 C14 N3 -91.2(3) . . . . ?
C4 C3 C14 N3 90.4(3) . . . . ?
N3 N4 C15 C16 0.5(3) . . . . ?
N4 C15 C16 C17 -0.1(3) . . . . ?
N4 C15 C16 Br2 179.61(18) . . . . ?
N4 N3 C17 C16 0.6(3) . . . . ?
C14 N3 C17 C16 173.4(2) . . . . ?
C15 C16 C17 N3 -0.3(3) . . . . ?
Br2 C16 C17 N3 179.98(17) . . . . ?
C21 N5 C18 C5 -10.2(4) . . . . ?
N6 N5 C18 C5 173.4(2) . . . . ?
C4 C5 C18 N5 93.7(2) . . . . ?
C6 C5 C18 N5 -86.5(3) . . . . ?
N5 N6 C19 C20 -0.1(3) . . . . ?
N6 C19 C20 C21 -1.0(3) . . . . ?
N6 C19 C20 Br3 179.88(18) . . . . ?
N6 N5 C21 C20 -1.8(3) . . . . ?
C18 N5 C21 C20 -178.5(2) . . . . ?
C19 C20 C21 N5 1.7(3) . . . . ?
Br3 C20 C21 N5 -179.21(17) . . . . ?

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
C13 H13 N6 0.95 2.54 3.432(3) 157.0 2_655
C14 H14B Br2 0.99 2.92 3.567(2) 123.8 1_655
C1A H1A N2 1.00 2.30 3.193(3) 148.1 .

_refine_diff_density_max         0.631
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.071

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch6Afin
_database_code_depnum_ccdc_archive 'CCDC 1533897'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H36 N6 O3'
_chemical_formula_sum            'C27 H36 N6 O3'
_chemical_formula_weight         492.62

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

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

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

_cell_length_a                   9.8975(2)
_cell_length_b                   11.8392(2)
_cell_length_c                   12.3994(2)
_cell_angle_alpha                113.589(1)
_cell_angle_beta                 98.570(1)
_cell_angle_gamma                94.846(1)
_cell_volume                     1299.91(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9994
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.62

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24608
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.605
_diffrn_reflns_theta_max         27.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5858
_reflns_number_gt                5200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  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)+(0.0376P)²+0.5761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5858
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0855
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69743(7) 0.33583(7) 0.64039(7) 0.01862(16) Uani 1 1 d . . . . .
O2 O 0.68717(7) -0.10260(7) 0.42398(6) 0.01842(16) Uani 1 1 d . . . . .
O3 O 1.00685(7) 0.12615(7) 0.79913(7) 0.01919(16) Uani 1 1 d . . . . .
N1 N 0.83557(9) 0.42009(8) 0.90522(8) 0.01753(18) Uani 1 1 d . . . . .
N2 N 0.78233(9) 0.36477(9) 0.97044(8) 0.02022(19) Uani 1 1 d . . . . .
N3 N 0.63136(9) 0.09645(8) 0.32309(8) 0.01648(18) Uani 1 1 d . . . . .
N4 N 0.74559(9) 0.17525(8) 0.33235(8) 0.01817(18) Uani 1 1 d . . . . .
N5 N 0.82398(9) -0.20844(8) 0.59118(8) 0.01938(19) Uani 1 1 d . . . . .
N6 N 0.73128(9) -0.18579(9) 0.66495(9) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.85231(10) 0.23265(9) 0.72114(9) 0.0154(2) Uani 1 1 d . . . . .
C2 C 0.74547(10) 0.22672(9) 0.63068(9) 0.01502(19) Uani 1 1 d . . . . .
C3 C 0.69132(10) 0.11546(10) 0.52986(9) 0.01491(19) Uani 1 1 d . . . . .
C4 C 0.74681(10) 0.00829(9) 0.52090(9) 0.01475(19) Uani 1 1 d . . . . .
C5 C 0.85297(10) 0.00914(9) 0.60920(9) 0.01543(19) Uani 1 1 d . . . . .
C6 C 0.90193(10) 0.12232(10) 0.70975(9) 0.0155(2) Uani 1 1 d . . . . .
C7 C 0.57041(11) 0.34913(10) 0.68484(10) 0.0220(2) Uani 1 1 d . . . . .
H7A H 0.5025 0.2734 0.6372 0.033 Uiso 1 1 calc R U . . .
H7B H 0.5339 0.4210 0.6783 0.033 Uiso 1 1 calc R U . . .
H7C H 0.5885 0.3620 0.7692 0.033 Uiso 1 1 calc R U . . .
C8 C 0.76172(11) -0.14287(11) 0.32770(10) 0.0225(2) Uani 1 1 d . . . . .
H8A H 0.7841 -0.0739 0.3054 0.034 Uiso 1 1 calc R U . . .
H8B H 0.7045 -0.2134 0.2582 0.034 Uiso 1 1 calc R U . . .
H8C H 0.8475 -0.1687 0.3538 0.034 Uiso 1 1 calc R U . . .
C9 C 0.95407(12) 0.09598(11) 0.88812(10) 0.0222(2) Uani 1 1 d . . . . .
H9A H 0.8989 0.1589 0.9292 0.033 Uiso 1 1 calc R U . . .
H9B H 1.0315 0.0948 0.9468 0.033 Uiso 1 1 calc R U . . .
H9C H 0.8959 0.0137 0.8489 0.033 Uiso 1 1 calc R U . . .
C10 C 0.92219(10) 0.35607(10) 0.82204(9) 0.0182(2) Uani 1 1 d . . . . .
H10A H 1.0042 0.3414 0.8681 0.022 Uiso 1 1 calc R U . . .
H10B H 0.9556 0.4119 0.7865 0.022 Uiso 1 1 calc R U . . .
C11 C 0.71177(11) 0.44775(11) 1.03776(10) 0.0237(2) Uani 1 1 d . . . . .
C12 C 0.72052(12) 0.55514(11) 1.01566(10) 0.0255(2) Uani 1 1 d . . . . .
H12 H 0.6791 0.6270 1.0521 0.031 Uiso 1 1 calc R U . . .
C13 C 0.80118(11) 0.53518(10) 0.93057(10) 0.0214(2) Uani 1 1 d . . . . .
C14 C 0.63813(13) 0.42035(14) 1.12370(11) 0.0342(3) Uani 1 1 d . . . . .
H14A H 0.6351 0.3320 1.1078 0.051 Uiso 1 1 calc R U . . .
H14B H 0.5436 0.4387 1.1134 0.051 Uiso 1 1 calc R U . . .
H14C H 0.6875 0.4723 1.2062 0.051 Uiso 1 1 calc R U . . .
C15 C 0.85101(14) 0.61622(11) 0.87400(12) 0.0308(3) Uani 1 1 d . . . . .
H15A H 0.9522 0.6358 0.8955 0.046 Uiso 1 1 calc R U . . .
H15B H 0.8117 0.6937 0.9027 0.046 Uiso 1 1 calc R U . . .
H15C H 0.8219 0.5724 0.7865 0.046 Uiso 1 1 calc R U . . .
C16 C 0.57887(10) 0.11152(10) 0.43111(9) 0.0174(2) Uani 1 1 d . . . . .
H16A H 0.5040 0.0412 0.4114 0.021 Uiso 1 1 calc R U . . .
H16B H 0.5391 0.1898 0.4598 0.021 Uiso 1 1 calc R U . . .
C17 C 0.76168(11) 0.14277(11) 0.21960(10) 0.0202(2) Uani 1 1 d . . . . .
C18 C 0.65763(12) 0.04405(11) 0.13854(10) 0.0225(2) Uani 1 1 d . . . . .
H18 H 0.6468 0.0043 0.0536 0.027 Uiso 1 1 calc R U . . .
C19 C 0.57498(11) 0.01700(10) 0.20783(9) 0.0198(2) Uani 1 1 d . . . . .
C20 C 0.87927(12) 0.21020(12) 0.19428(11) 0.0269(3) Uani 1 1 d . . . . .
H20A H 0.9258 0.2821 0.2682 0.040 Uiso 1 1 calc R U . . .
H20B H 0.8437 0.2391 0.1333 0.040 Uiso 1 1 calc R U . . .
H20C H 0.9453 0.1535 0.1647 0.040 Uiso 1 1 calc R U . . .
C21 C 0.44744(12) -0.07626(11) 0.17474(11) 0.0279(3) Uani 1 1 d . . . . .
H21A H 0.4638 -0.1332 0.2132 0.042 Uiso 1 1 calc R U . . .
H21B H 0.4242 -0.1240 0.0873 0.042 Uiso 1 1 calc R U . . .
H21C H 0.3706 -0.0328 0.2020 0.042 Uiso 1 1 calc R U . . .
C22 C 0.91942(10) -0.10453(10) 0.59726(10) 0.0189(2) Uani 1 1 d . . . . .
H22A H 0.9589 -0.1322 0.5238 0.023 Uiso 1 1 calc R U . . .
H22B H 0.9966 -0.0809 0.6668 0.023 Uiso 1 1 calc R U . . .
C23 C 0.66977(12) -0.29872(11) 0.64571(11) 0.0245(2) Uani 1 1 d . . . . .
C24 C 0.72534(13) -0.39287(11) 0.56164(11) 0.0271(2) Uani 1 1 d . . . . .
H24 H 0.6995 -0.4805 0.5335 0.032 Uiso 1 1 calc R U . . .
C25 C 0.82486(12) -0.33208(10) 0.52853(10) 0.0231(2) Uani 1 1 d . . . . .
C26 C 0.55789(13) -0.31046(13) 0.71087(14) 0.0337(3) Uani 1 1 d . . . . .
H26A H 0.5515 -0.2279 0.7714 0.051 Uiso 1 1 calc R U . . .
H26B H 0.5793 -0.3656 0.7504 0.051 Uiso 1 1 calc R U . . .
H26C H 0.4694 -0.3456 0.6536 0.051 Uiso 1 1 calc R U . . .
C27 C 0.92160(15) -0.38100(12) 0.44493(11) 0.0320(3) Uani 1 1 d . . . . .
H27A H 0.9007 -0.3581 0.3772 0.048 Uiso 1 1 calc R U . . .
H27B H 0.9104 -0.4721 0.4149 0.048 Uiso 1 1 calc R U . . .
H27C H 1.0172 -0.3448 0.4879 0.048 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
O1 C2 1.3804(12) . ?
O1 C7 1.4421(13) . ?
O2 C4 1.3825(12) . ?
O2 C8 1.4365(12) . ?
O3 C6 1.3848(12) . ?
O3 C9 1.4401(13) . ?
N1 C13 1.3559(14) . ?
N1 N2 1.3614(13) . ?
N1 C10 1.4563(13) . ?
N2 C11 1.3353(14) . ?
N3 C19 1.3551(14) . ?
N3 N4 1.3635(12) . ?
N3 C16 1.4586(13) . ?
N4 C17 1.3320(14) . ?
N5 C25 1.3566(14) . ?
N5 N6 1.3586(13) . ?
N5 C22 1.4559(13) . ?
N6 C23 1.3338(14) . ?
C1 C6 1.3960(14) . ?
C1 C2 1.3972(14) . ?
C1 C10 1.5123(14) . ?
C2 C3 1.3958(14) . ?
C3 C4 1.3953(14) . ?
C3 C16 1.5098(13) . ?
C4 C5 1.3962(14) . ?
C5 C6 1.3993(14) . ?
C5 C22 1.5115(14) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.4023(17) . ?
C11 C14 1.4967(17) . ?
C12 C13 1.3747(17) . ?
C12 H12 0.9500 . ?
C13 C15 1.4891(17) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.4088(16) . ?
C17 C20 1.4976(15) . ?
C18 C19 1.3766(16) . ?
C18 H18 0.9500 . ?
C19 C21 1.4928(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.4058(17) . ?
C23 C26 1.4930(17) . ?
C24 C25 1.3762(17) . ?
C24 H24 0.9500 . ?
C25 C27 1.4952(17) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C7 113.07(8) . . ?
C4 O2 C8 115.46(8) . . ?
C6 O3 C9 112.14(8) . . ?
C13 N1 N2 112.62(9) . . ?
C13 N1 C10 127.57(9) . . ?
N2 N1 C10 119.79(9) . . ?
C11 N2 N1 104.50(9) . . ?
C19 N3 N4 112.65(9) . . ?
C19 N3 C16 128.05(9) . . ?
N4 N3 C16 119.13(8) . . ?
C17 N4 N3 104.59(9) . . ?
C25 N5 N6 112.76(9) . . ?
C25 N5 C22 127.39(9) . . ?
N6 N5 C22 119.39(9) . . ?
C23 N6 N5 104.62(9) . . ?
C6 C1 C2 117.93(9) . . ?
C6 C1 C10 120.47(9) . . ?
C2 C1 C10 121.34(9) . . ?
O1 C2 C3 119.92(9) . . ?
O1 C2 C1 118.23(9) . . ?
C3 C2 C1 121.80(9) . . ?
C4 C3 C2 118.18(9) . . ?
C4 C3 C16 120.68(9) . . ?
C2 C3 C16 121.11(9) . . ?
O2 C4 C3 117.57(9) . . ?
O2 C4 C5 120.09(9) . . ?
C3 C4 C5 122.23(9) . . ?
C4 C5 C6 117.49(9) . . ?
C4 C5 C22 122.71(9) . . ?
C6 C5 C22 119.74(9) . . ?
O3 C6 C1 118.74(9) . . ?
O3 C6 C5 118.90(9) . . ?
C1 C6 C5 122.31(9) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 115.20(8) . . ?
N1 C10 H10A 108.5 . . ?
C1 C10 H10A 108.5 . . ?
N1 C10 H10B 108.5 . . ?
C1 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 C12 111.01(10) . . ?
N2 C11 C14 120.43(11) . . ?
C12 C11 C14 128.56(11) . . ?
C13 C12 C11 105.99(10) . . ?
C13 C12 H12 127.0 . . ?
C11 C12 H12 127.0 . . ?
N1 C13 C12 105.88(10) . . ?
N1 C13 C15 122.77(11) . . ?
C12 C13 C15 131.33(11) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C3 111.74(8) . . ?
N3 C16 H16A 109.3 . . ?
C3 C16 H16A 109.3 . . ?
N3 C16 H16B 109.3 . . ?
C3 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N4 C17 C18 111.04(10) . . ?
N4 C17 C20 119.84(10) . . ?
C18 C17 C20 129.13(10) . . ?
C19 C18 C17 105.77(9) . . ?
C19 C18 H18 127.1 . . ?
C17 C18 H18 127.1 . . ?
N3 C19 C18 105.96(9) . . ?
N3 C19 C21 122.54(10) . . ?
C18 C19 C21 131.50(10) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C5 113.56(8) . . ?
N5 C22 H22A 108.9 . . ?
C5 C22 H22A 108.9 . . ?
N5 C22 H22B 108.9 . . ?
C5 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
N6 C23 C24 110.93(10) . . ?
N6 C23 C26 119.74(11) . . ?
C24 C23 C26 129.32(11) . . ?
C25 C24 C23 105.92(10) . . ?
C25 C24 H24 127.0 . . ?
C23 C24 H24 127.0 . . ?
N5 C25 C24 105.75(10) . . ?
N5 C25 C27 123.02(11) . . ?
C24 C25 C27 131.22(11) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C13 N1 N2 C11 0.47(12) . . . . ?
C10 N1 N2 C11 178.86(9) . . . . ?
C19 N3 N4 C17 -0.77(11) . . . . ?
C16 N3 N4 C17 -176.37(9) . . . . ?
C25 N5 N6 C23 -1.54(12) . . . . ?
C22 N5 N6 C23 -174.34(9) . . . . ?
C7 O1 C2 C3 82.22(11) . . . . ?
C7 O1 C2 C1 -100.45(10) . . . . ?
C6 C1 C2 O1 -178.97(8) . . . . ?
C10 C1 C2 O1 -4.93(14) . . . . ?
C6 C1 C2 C3 -1.70(14) . . . . ?
C10 C1 C2 C3 172.35(9) . . . . ?
O1 C2 C3 C4 177.25(8) . . . . ?
C1 C2 C3 C4 0.02(14) . . . . ?
O1 C2 C3 C16 -0.88(14) . . . . ?
C1 C2 C3 C16 -178.11(9) . . . . ?
C8 O2 C4 C3 101.79(10) . . . . ?
C8 O2 C4 C5 -82.02(11) . . . . ?
C2 C3 C4 O2 176.51(8) . . . . ?
C16 C3 C4 O2 -5.35(13) . . . . ?
C2 C3 C4 C5 0.41(14) . . . . ?
C16 C3 C4 C5 178.55(9) . . . . ?
O2 C4 C5 C6 -175.15(8) . . . . ?
C3 C4 C5 C6 0.85(14) . . . . ?
O2 C4 C5 C22 7.54(14) . . . . ?
C3 C4 C5 C22 -176.46(9) . . . . ?
C9 O3 C6 C1 93.93(11) . . . . ?
C9 O3 C6 C5 -88.41(11) . . . . ?
C2 C1 C6 O3 -179.36(8) . . . . ?
C10 C1 C6 O3 6.54(14) . . . . ?
C2 C1 C6 C5 3.06(15) . . . . ?
C10 C1 C6 C5 -171.04(9) . . . . ?
C4 C5 C6 O3 179.78(8) . . . . ?
C22 C5 C6 O3 -2.82(14) . . . . ?
C4 C5 C6 C1 -2.65(14) . . . . ?
C22 C5 C6 C1 174.75(9) . . . . ?
C13 N1 C10 C1 -120.39(11) . . . . ?
N2 N1 C10 C1 61.49(12) . . . . ?
C6 C1 C10 N1 -118.46(10) . . . . ?
C2 C1 C10 N1 67.64(13) . . . . ?
N1 N2 C11 C12 -0.17(12) . . . . ?
N1 N2 C11 C14 -179.53(10) . . . . ?
N2 C11 C12 C13 -0.16(13) . . . . ?
C14 C11 C12 C13 179.12(11) . . . . ?
N2 N1 C13 C12 -0.58(12) . . . . ?
C10 N1 C13 C12 -178.81(9) . . . . ?
N2 N1 C13 C15 177.83(10) . . . . ?
C10 N1 C13 C15 -0.40(17) . . . . ?
C11 C12 C13 N1 0.43(12) . . . . ?
C11 C12 C13 C15 -177.79(11) . . . . ?
C19 N3 C16 C3 133.53(10) . . . . ?
N4 N3 C16 C3 -51.63(12) . . . . ?
C4 C3 C16 N3 -70.62(12) . . . . ?
C2 C3 C16 N3 107.45(11) . . . . ?
N3 N4 C17 C18 0.33(12) . . . . ?
N3 N4 C17 C20 -179.84(9) . . . . ?
N4 C17 C18 C19 0.18(13) . . . . ?
C20 C17 C18 C19 -179.63(11) . . . . ?
N4 N3 C19 C18 0.89(12) . . . . ?
C16 N3 C19 C18 176.01(10) . . . . ?
N4 N3 C19 C21 -178.66(10) . . . . ?
C16 N3 C19 C21 -3.54(17) . . . . ?
C17 C18 C19 N3 -0.63(12) . . . . ?
C17 C18 C19 C21 178.87(11) . . . . ?
C25 N5 C22 C5 146.58(10) . . . . ?
N6 N5 C22 C5 -41.77(13) . . . . ?
C4 C5 C22 N5 -63.02(13) . . . . ?
C6 C5 C22 N5 119.72(10) . . . . ?
N5 N6 C23 C24 1.18(13) . . . . ?
N5 N6 C23 C26 -178.81(10) . . . . ?
N6 C23 C24 C25 -0.46(13) . . . . ?
C26 C23 C24 C25 179.54(12) . . . . ?
N6 N5 C25 C24 1.27(12) . . . . ?
C22 N5 C25 C24 173.38(10) . . . . ?
N6 N5 C25 C27 -177.57(10) . . . . ?
C22 N5 C25 C27 -5.46(17) . . . . ?
C23 C24 C25 N5 -0.47(12) . . . . ?
C23 C24 C25 C27 178.24(12) . . . . ?

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
C7 H7A O2 0.98 2.43 3.3770(13) 162.9 2_656
C7 H7C N1 0.98 2.62 3.2731(14) 124.3 .
C8 H8A N3 0.98 2.58 3.2283(14) 123.6 .
C9 H9A N2 0.98 2.68 3.5901(15) 154.5 .
C22 H22B O3 0.99 2.32 2.8208(13) 110.0 .

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.039

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch3acor
_database_code_depnum_ccdc_archive 'CCDC 1533889'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 Br3 N6, C2 H6 O'
_chemical_formula_sum            'C26 H33 Br3 N6 O'
_chemical_formula_weight         685.31

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   9.0593(3)
_cell_length_b                   13.4556(5)
_cell_length_c                   11.5609(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.459(2)
_cell_angle_gamma                90
_cell_volume                     1351.51(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6535
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      29.15

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    4.509
_shelx_estimated_absorpt_T_min   0.266
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2657
_exptl_absorpt_correction_T_max  0.8402
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13602
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_max         28.399
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6350
_reflns_number_gt                5770
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.997

_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       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.026(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6350
_refine_ls_number_parameters     331
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_restrained_S_all      1.192
_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
Br1 Br -0.45826(6) 0.29965(3) 0.48317(4) 0.01917(12) Uani 1 1 d . . . . .
Br2 Br 1.00093(6) 0.25216(4) 0.84300(5) 0.02319(13) Uani 1 1 d . . . . .
Br3 Br 0.94061(6) 0.53449(3) 0.71367(5) 0.01997(12) Uani 1 1 d . . . . .
N1 N -0.0429(4) 0.2945(3) 0.4260(3) 0.0122(8) Uani 1 1 d . . . . .
N2 N -0.1277(5) 0.3017(3) 0.3087(3) 0.0157(8) Uani 1 1 d . . . . .
N3 N 0.5933(5) 0.2059(3) 0.9046(4) 0.0168(9) Uani 1 1 d . . . . .
N4 N 0.6831(6) 0.1852(3) 1.0163(4) 0.0220(10) Uani 1 1 d . . . . .
N5 N 0.5226(5) 0.5790(3) 0.7561(4) 0.0123(8) Uani 1 1 d . . . . .
N6 N 0.5860(5) 0.6661(3) 0.8065(4) 0.0148(9) Uani 1 1 d . . . . .
C1 C 0.2072(5) 0.3191(3) 0.5812(4) 0.0118(10) Uani 1 1 d . . . . .
C2 C 0.2604(5) 0.2486(3) 0.6719(4) 0.0121(9) Uani 1 1 d . . . . .
C3 C 0.3494(6) 0.2785(3) 0.7865(4) 0.0124(10) Uani 1 1 d . . . . .
C4 C 0.3763(5) 0.3806(3) 0.8120(4) 0.0117(10) Uani 1 1 d . . . . .
C5 C 0.3204(6) 0.4508(3) 0.7190(4) 0.0114(10) Uani 1 1 d . . . . .
C6 C 0.2346(6) 0.4207(4) 0.6048(5) 0.0119(9) Uani 1 1 d . . . . .
C7 C 0.2211(6) 0.1387(3) 0.6464(5) 0.0154(11) Uani 1 1 d . . . . .
H7A H 0.2038 0.1089 0.7178 0.019 Uiso 1 1 calc R U . . .
H7B H 0.1258 0.1339 0.5819 0.019 Uiso 1 1 calc R U . . .
C8 C 0.3451(6) 0.0794(3) 0.6110(5) 0.0198(11) Uani 1 1 d . . . . .
H8A H 0.3657 0.1096 0.5420 0.030 Uiso 1 1 calc R U . . .
H8B H 0.3101 0.0125 0.5917 0.030 Uiso 1 1 calc R U . . .
H8C H 0.4375 0.0788 0.6771 0.030 Uiso 1 1 calc R U . . .
C9 C 0.4584(6) 0.4143(4) 0.9387(4) 0.0163(11) Uani 1 1 d . . . . .
H9A H 0.5093 0.4772 0.9352 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5368 0.3659 0.9763 0.020 Uiso 1 1 calc R U . . .
C10 C 0.3467(7) 0.4265(4) 1.0160(5) 0.0248(13) Uani 1 1 d . . . . .
H10A H 0.2655 0.4713 0.9766 0.037 Uiso 1 1 calc R U . . .
H10B H 0.4011 0.4528 1.0935 0.037 Uiso 1 1 calc R U . . .
H10C H 0.3035 0.3630 1.0261 0.037 Uiso 1 1 calc R U . . .
C11 C 0.1683(6) 0.4969(3) 0.5053(4) 0.0141(10) Uani 1 1 d . . . . .
H11A H 0.1321 0.5539 0.5406 0.017 Uiso 1 1 calc R U . . .
H11B H 0.0802 0.4677 0.4470 0.017 Uiso 1 1 calc R U . . .
C12 C 0.2834(6) 0.5327(4) 0.4387(4) 0.0178(10) Uani 1 1 d . . . . .
H12A H 0.3707 0.5625 0.4953 0.027 Uiso 1 1 calc R U . . .
H12B H 0.2345 0.5808 0.3787 0.027 Uiso 1 1 calc R U . . .
H12C H 0.3168 0.4772 0.4004 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1235(6) 0.2870(4) 0.4541(4) 0.0140(10) Uani 1 1 d . . . . .
H13A H 0.1581 0.3279 0.3977 0.017 Uiso 1 1 calc R U . . .
H13B H 0.1508 0.2187 0.4429 0.017 Uiso 1 1 calc R U . . .
C14 C -0.2755(6) 0.3038(4) 0.3105(4) 0.0157(10) Uani 1 1 d . . . . .
H14 H -0.3603 0.3083 0.2429 0.019 Uiso 1 1 calc R U . . .
C15 C -0.2820(5) 0.2982(4) 0.4301(4) 0.0138(10) Uani 1 1 d . . . . .
C16 C -0.1349(6) 0.2930(3) 0.4996(4) 0.0131(10) Uani 1 1 d . . . . .
H16 H -0.1027 0.2890 0.5833 0.016 Uiso 1 1 calc R U . . .
C17 C 0.4251(6) 0.2052(4) 0.8816(5) 0.0166(11) Uani 1 1 d . . . . .
H17A H 0.3998 0.2211 0.9556 0.020 Uiso 1 1 calc R U . . .
H17B H 0.3861 0.1392 0.8564 0.020 Uiso 1 1 calc R U . . .
C18 C 0.8269(7) 0.1961(4) 1.0093(5) 0.0225(12) Uani 1 1 d . . . . .
H18 H 0.9151 0.1868 1.0732 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8262(7) 0.2229(4) 0.8958(5) 0.0204(12) Uani 1 1 d . . . . .
C20 C 0.6806(7) 0.2300(3) 0.8314(5) 0.0184(12) Uani 1 1 d . . . . .
H20 H 0.6448 0.2483 0.7507 0.022 Uiso 1 1 calc R U . . .
C21 C 0.3607(6) 0.5596(3) 0.7467(5) 0.0153(11) Uani 1 1 d . . . . .
H21A H 0.2962 0.6007 0.6834 0.018 Uiso 1 1 calc R U . . .
H21B H 0.3403 0.5774 0.8220 0.018 Uiso 1 1 calc R U . . .
C22 C 0.7303(6) 0.6649(4) 0.7986(4) 0.0160(11) Uani 1 1 d . . . . .
H22 H 0.8021 0.7153 0.8260 0.019 Uiso 1 1 calc R U . . .
C23 C 0.7581(6) 0.5771(3) 0.7431(4) 0.0142(10) Uani 1 1 d . . . . .
C24 C 0.6238(6) 0.5247(4) 0.7165(4) 0.0133(10) Uani 1 1 d . . . . .
H24 H 0.6055 0.4632 0.6783 0.016 Uiso 1 1 calc R U . . .
O1A O 0.0668(5) 0.3732(3) 0.1713(4) 0.0328(10) Uani 1 1 d . . . . .
H1A H 0.0164 0.3507 0.2140 0.049 Uiso 1 1 calc R U . . .
C1A C 0.0202(7) 0.4739(4) 0.1388(6) 0.0299(14) Uani 1 1 d . . . . .
H1A1 H 0.0965 0.5057 0.1069 0.036 Uiso 1 1 calc R U . . .
H1A2 H 0.0165 0.5100 0.2106 0.036 Uiso 1 1 calc R U . . .
C2A C -0.1303(9) 0.4800(5) 0.0491(6) 0.052(2) Uani 1 1 d . . . . .
H2A1 H -0.1275 0.4441 -0.0220 0.079 Uiso 1 1 calc R U . . .
H2A2 H -0.1550 0.5484 0.0288 0.079 Uiso 1 1 calc R U . . .
H2A3 H -0.2071 0.4516 0.0817 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.866(4) . ?
Br2 C19 1.892(6) . ?
Br3 C23 1.870(5) . ?
N1 C16 1.349(5) . ?
N1 N2 1.359(5) . ?
N1 C13 1.452(6) . ?
N2 C14 1.345(6) . ?
N3 N4 1.346(6) . ?
N3 C20 1.351(6) . ?
N3 C17 1.470(7) . ?
N4 C18 1.336(7) . ?
N5 C24 1.350(6) . ?
N5 N6 1.362(5) . ?
N5 C21 1.462(6) . ?
N6 C22 1.337(6) . ?
C1 C2 1.395(7) . ?
C1 C6 1.402(7) . ?
C1 C13 1.513(7) . ?
C2 C3 1.401(7) . ?
C2 C7 1.530(6) . ?
C3 C4 1.411(6) . ?
C3 C17 1.491(7) . ?
C4 C5 1.413(7) . ?
C4 C9 1.513(7) . ?
C5 C6 1.389(7) . ?
C5 C21 1.521(6) . ?
C6 C11 1.531(7) . ?
C7 C8 1.525(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.537(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.539(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.402(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.348(7) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.360(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.322(8) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.401(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.364(7) . ?
C24 H24 0.9300 . ?
O1A C1A 1.437(7) . ?
O1A H1A 0.8200 . ?
C1A C2A 1.463(9) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A H2A1 0.9600 . ?
C2A H2A2 0.9600 . ?
C2A H2A3 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
C16 N1 N2 110.7(4) . . ?
C16 N1 C13 130.2(4) . . ?
N2 N1 C13 119.0(3) . . ?
C14 N2 N1 105.7(4) . . ?
N4 N3 C20 110.4(5) . . ?
N4 N3 C17 119.1(4) . . ?
C20 N3 C17 130.4(5) . . ?
C18 N4 N3 104.7(4) . . ?
C24 N5 N6 111.5(4) . . ?
C24 N5 C21 129.9(4) . . ?
N6 N5 C21 118.5(4) . . ?
C22 N6 N5 105.2(4) . . ?
C2 C1 C6 120.8(5) . . ?
C2 C1 C13 120.5(4) . . ?
C6 C1 C13 118.7(4) . . ?
C1 C2 C3 120.0(4) . . ?
C1 C2 C7 120.0(4) . . ?
C3 C2 C7 120.0(4) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 C17 121.9(4) . . ?
C4 C3 C17 118.2(5) . . ?
C3 C4 C5 119.2(4) . . ?
C3 C4 C9 120.1(4) . . ?
C5 C4 C9 120.6(4) . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 C21 121.2(4) . . ?
C4 C5 C21 118.1(4) . . ?
C5 C6 C1 119.4(5) . . ?
C5 C6 C11 120.9(4) . . ?
C1 C6 C11 119.7(5) . . ?
C8 C7 C2 114.1(4) . . ?
C8 C7 H7A 108.7 . . ?
C2 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C2 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 C10 111.8(4) . . ?
C4 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C4 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C12 114.1(4) . . ?
C6 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C6 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C1 113.6(4) . . ?
N1 C13 H13A 108.8 . . ?
C1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 C15 109.5(4) . . ?
N2 C14 H14 125.2 . . ?
C15 C14 H14 125.2 . . ?
C16 C15 C14 106.3(4) . . ?
C16 C15 Br1 126.7(4) . . ?
C14 C15 Br1 127.0(4) . . ?
C15 C16 N1 107.9(4) . . ?
C15 C16 H16 126.1 . . ?
N1 C16 H16 126.1 . . ?
N3 C17 C3 111.5(4) . . ?
N3 C17 H17A 109.3 . . ?
C3 C17 H17A 109.3 . . ?
N3 C17 H17B 109.3 . . ?
C3 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
N4 C18 C19 110.5(6) . . ?
N4 C18 H18 124.8 . . ?
C19 C18 H18 124.8 . . ?
C20 C19 C18 107.1(5) . . ?
C20 C19 Br2 126.6(4) . . ?
C18 C19 Br2 126.2(5) . . ?
C19 C20 N3 107.3(5) . . ?
C19 C20 H20 126.3 . . ?
N3 C20 H20 126.3 . . ?
N5 C21 C5 111.3(4) . . ?
N5 C21 H21A 109.4 . . ?
C5 C21 H21A 109.4 . . ?
N5 C21 H21B 109.4 . . ?
C5 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N6 C22 C23 110.4(4) . . ?
N6 C22 H22 124.8 . . ?
C23 C22 H22 124.8 . . ?
C24 C23 C22 106.0(4) . . ?
C24 C23 Br3 125.3(4) . . ?
C22 C23 Br3 128.7(4) . . ?
N5 C24 C23 107.0(4) . . ?
N5 C24 H24 126.5 . . ?
C23 C24 H24 126.5 . . ?
C1A O1A H1A 109.5 . . ?
O1A C1A C2A 112.6(5) . . ?
O1A C1A H1A1 109.1 . . ?
C2A C1A H1A1 109.1 . . ?
O1A C1A H1A2 109.1 . . ?
C2A C1A H1A2 109.1 . . ?
H1A1 C1A H1A2 107.8 . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 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
C16 N1 N2 C14 -0.5(5) . . . . ?
C13 N1 N2 C14 177.9(4) . . . . ?
C20 N3 N4 C18 -0.6(5) . . . . ?
C17 N3 N4 C18 -177.2(4) . . . . ?
C24 N5 N6 C22 -0.5(5) . . . . ?
C21 N5 N6 C22 -177.6(4) . . . . ?
C6 C1 C2 C3 -3.5(7) . . . . ?
C13 C1 C2 C3 174.4(4) . . . . ?
C6 C1 C2 C7 176.3(4) . . . . ?
C13 C1 C2 C7 -5.8(6) . . . . ?
C1 C2 C3 C4 4.2(7) . . . . ?
C7 C2 C3 C4 -175.6(4) . . . . ?
C1 C2 C3 C17 -172.2(4) . . . . ?
C7 C2 C3 C17 8.0(6) . . . . ?
C2 C3 C4 C5 -3.7(7) . . . . ?
C17 C3 C4 C5 172.8(4) . . . . ?
C2 C3 C4 C9 173.8(4) . . . . ?
C17 C3 C4 C9 -9.7(6) . . . . ?
C3 C4 C5 C6 2.5(7) . . . . ?
C9 C4 C5 C6 -175.0(4) . . . . ?
C3 C4 C5 C21 -175.8(4) . . . . ?
C9 C4 C5 C21 6.7(7) . . . . ?
C4 C5 C6 C1 -1.8(7) . . . . ?
C21 C5 C6 C1 176.5(4) . . . . ?
C4 C5 C6 C11 177.5(4) . . . . ?
C21 C5 C6 C11 -4.2(7) . . . . ?
C2 C1 C6 C5 2.3(7) . . . . ?
C13 C1 C6 C5 -175.6(4) . . . . ?
C2 C1 C6 C11 -177.1(4) . . . . ?
C13 C1 C6 C11 5.1(6) . . . . ?
C1 C2 C7 C8 95.3(5) . . . . ?
C3 C2 C7 C8 -84.9(5) . . . . ?
C3 C4 C9 C10 -85.4(5) . . . . ?
C5 C4 C9 C10 92.1(5) . . . . ?
C5 C6 C11 C12 82.5(5) . . . . ?
C1 C6 C11 C12 -98.2(5) . . . . ?
C16 N1 C13 C1 -24.5(7) . . . . ?
N2 N1 C13 C1 157.5(4) . . . . ?
C2 C1 C13 N1 99.3(5) . . . . ?
C6 C1 C13 N1 -82.9(5) . . . . ?
N1 N2 C14 C15 0.2(6) . . . . ?
N2 C14 C15 C16 0.2(6) . . . . ?
N2 C14 C15 Br1 179.3(3) . . . . ?
C14 C15 C16 N1 -0.5(5) . . . . ?
Br1 C15 C16 N1 -179.6(4) . . . . ?
N2 N1 C16 C15 0.6(5) . . . . ?
C13 N1 C16 C15 -177.5(4) . . . . ?
N4 N3 C17 C3 148.5(4) . . . . ?
C20 N3 C17 C3 -27.3(7) . . . . ?
C2 C3 C17 N3 109.8(5) . . . . ?
C4 C3 C17 N3 -66.6(5) . . . . ?
N3 N4 C18 C19 -0.1(6) . . . . ?
N4 C18 C19 C20 0.9(6) . . . . ?
N4 C18 C19 Br2 177.3(4) . . . . ?
C18 C19 C20 N3 -1.2(6) . . . . ?
Br2 C19 C20 N3 -177.7(3) . . . . ?
N4 N3 C20 C19 1.2(6) . . . . ?
C17 N3 C20 C19 177.3(4) . . . . ?
C24 N5 C21 C5 18.1(7) . . . . ?
N6 N5 C21 C5 -165.5(4) . . . . ?
C6 C5 C21 N5 -105.6(5) . . . . ?
C4 C5 C21 N5 72.8(5) . . . . ?
N5 N6 C22 C23 0.0(5) . . . . ?
N6 C22 C23 C24 0.5(6) . . . . ?
N6 C22 C23 Br3 -177.7(4) . . . . ?
N6 N5 C24 C23 0.8(5) . . . . ?
C21 N5 C24 C23 177.4(5) . . . . ?
C22 C23 C24 N5 -0.7(5) . . . . ?
Br3 C23 C24 N5 177.5(3) . . . . ?

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
O1A H1A N2 0.82 2.04 2.854(5) 174.2 .
C22 H22 O1A 0.93 2.43 3.315(6) 158.9 2_656
C21 H21B N4 0.97 2.42 3.337(6) 157.1 2_657
C20 H20 Br1 0.93 3.05 3.975(5) 176.6 1_655
C16 H16 Br2 0.93 2.92 3.849(5) 173.5 1_455
C13 H13B Br3 0.97 3.04 3.874(5) 144.6 2_646
C13 H13A O1A 0.97 2.58 3.368(6) 138.0 .

_refine_diff_density_max         0.887
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.098

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch31new
_database_code_depnum_ccdc_archive 'CCDC 1533887'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br3 N6'
_chemical_formula_sum            'C21 H21 Br3 N6'
_chemical_formula_weight         597.14

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

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

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

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

_cell_length_a                   8.4808(2)
_cell_length_b                   11.0938(3)
_cell_length_c                   13.1816(3)
_cell_angle_alpha                68.194(1)
_cell_angle_beta                 79.566(1
_cell_angle_gamma                69.481(10)
_cell_volume                     1076.54(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      33.18

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    5.643
_shelx_estimated_absorpt_T_min   0.161
_shelx_estimated_absorpt_T_max   0.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1610
_exptl_absorpt_correction_T_max  0.3010
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25131
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.188
_diffrn_reflns_theta_max         29.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5944
_reflns_number_gt                5298
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0318P)²+1.4580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5944
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.90758(3) -0.52489(2) 0.33308(2) 0.02704(6) Uani 1 1 d . . . . .
Br2 Br 0.23793(3) 0.31654(2) -0.01051(2) 0.02158(6) Uani 1 1 d . . . . .
Br3 Br 0.73340(3) 0.04488(2) 0.98433(2) 0.02012(5) Uani 1 1 d . . . . .
N1 N 0.9392(2) -0.17139(16) 0.32786(13) 0.0136(3) Uani 1 1 d . . . . .
N2 N 0.8370(2) -0.11979(18) 0.24408(13) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.4754(2) 0.41723(16) 0.16639(13) 0.0152(3) Uani 1 1 d . . . . .
N4 N 0.3309(2) 0.5212(2) 0.15888(16) 0.0259(4) Uani 1 1 d . . . . .
N5 N 0.5788(2) 0.12197(16) 0.69020(12) 0.0128(3) Uani 1 1 d . . . . .
N6 N 0.6023(2) 0.24347(16) 0.66994(13) 0.0157(3) Uani 1 1 d . . . . .
C1 C 0.8464(2) 0.03586(18) 0.38074(15) 0.0123(3) Uani 1 1 d . . . . .
C2 C 0.8028(2) 0.16254(19) 0.29645(15) 0.0128(3) Uani 1 1 d . . . . .
C3 C 0.6665(2) 0.26970(18) 0.31518(15) 0.0127(3) Uani 1 1 d . . . . .
C4 C 0.5736(2) 0.25161(18) 0.41667(14) 0.0124(3) Uani 1 1 d . . . . .
C5 C 0.6159(2) 0.12390(18) 0.49886(14) 0.0117(3) Uani 1 1 d . . . . .
C6 C 0.7538(2) 0.01566(18) 0.48174(14) 0.0121(3) Uani 1 1 d . . . . .
C7 C 0.9037(3) 0.1810(2) 0.18755(16) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.8415 0.2616 0.1332 0.030 Uiso 1 1 calc R U . . .
H7B H 0.9244 0.1029 0.1659 0.030 Uiso 1 1 calc R U . . .
H7C H 1.0093 0.1902 0.1945 0.030 Uiso 1 1 calc R U . . .
C8 C 0.4306(3) 0.3722(2) 0.43360(16) 0.0188(4) Uani 1 1 d . . . . .
H8A H 0.3831 0.3463 0.5074 0.028 Uiso 1 1 calc R U . . .
H8B H 0.3452 0.3999 0.3835 0.028 Uiso 1 1 calc R U . . .
H8C H 0.4729 0.4466 0.4207 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8012(3) -0.12163(19) 0.57106(15) 0.0171(4) Uani 1 1 d . . . . .
H9A H 0.7599 -0.1833 0.5561 0.026 Uiso 1 1 calc R U . . .
H9B H 0.7522 -0.1115 0.6402 0.026 Uiso 1 1 calc R U . . .
H9C H 0.9217 -0.1575 0.5737 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9933(2) -0.0799(2) 0.36058(16) 0.0160(4) Uani 1 1 d . . . . .
H10A H 1.0699 -0.0424 0.3036 0.019 Uiso 1 1 calc R U . . .
H10B H 1.0541 -0.1319 0.4268 0.019 Uiso 1 1 calc R U . . .
C11 C 0.8145(3) -0.2278(2) 0.23460(16) 0.0172(4) Uani 1 1 d . . . . .
H11 H 0.7484 -0.2239 0.1837 0.021 Uiso 1 1 calc R U . . .
C12 C 0.9036(3) -0.3475(2) 0.31137(16) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.9834(2) -0.3085(2) 0.36983(16) 0.0169(4) Uani 1 1 d . . . . .
H13 H 1.0537 -0.3653 0.4269 0.020 Uiso 1 1 calc R U . . .
C14 C 0.6136(3) 0.40647(19) 0.22507(16) 0.0162(4) Uani 1 1 d . . . . .
H14A H 0.5779 0.4789 0.2565 0.019 Uiso 1 1 calc R U . . .
H14B H 0.7093 0.4180 0.1739 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2346(3) 0.5033(2) 0.10028(19) 0.0261(5) Uani 1 1 d . . . . .
H15 H 0.1262 0.5604 0.0815 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3177(3) 0.3876(2) 0.07073(15) 0.0163(4) Uani 1 1 d . . . . .
C17 C 0.4724(3) 0.3348(2) 0.11353(16) 0.0177(4) Uani 1 1 d . . . . .
H17 H 0.5583 0.2576 0.1074 0.021 Uiso 1 1 calc R U . . .
C18 C 0.5117(2) 0.0994(2) 0.60612(15) 0.0147(3) Uani 1 1 d . . . . .
H18A H 0.3971 0.1600 0.5939 0.018 Uiso 1 1 calc R U . . .
H18B H 0.5082 0.0063 0.6324 0.018 Uiso 1 1 calc R U . . .
C19 C 0.6538(2) 0.23393(19) 0.76325(15) 0.0156(3) Uani 1 1 d . . . . .
H19 H 0.6813 0.3023 0.7739 0.019 Uiso 1 1 calc R U . . .
C20 C 0.6607(2) 0.10725(19) 0.84264(15) 0.0142(3) Uani 1 1 d . . . . .
C21 C 0.6113(2) 0.03733(19) 0.79381(15) 0.0142(3) Uani 1 1 d . . . . .
H21 H 0.6021 -0.0503 0.8256 0.017 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.870(2) . ?
Br2 C16 1.8679(19) . ?
Br3 C20 1.8724(18) . ?
N1 C13 1.346(2) . ?
N1 N2 1.352(2) . ?
N1 C10 1.466(2) . ?
N2 C11 1.330(3) . ?
N3 N4 1.345(2) . ?
N3 C17 1.348(2) . ?
N3 C14 1.466(2) . ?
N4 C15 1.326(3) . ?
N5 C21 1.351(2) . ?
N5 N6 1.353(2) . ?
N5 C18 1.466(2) . ?
N6 C19 1.334(2) . ?
C1 C6 1.401(3) . ?
C1 C2 1.404(3) . ?
C1 C10 1.511(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.515(3) . ?
C3 C4 1.407(3) . ?
C3 C14 1.514(3) . ?
C4 C5 1.398(2) . ?
C4 C8 1.515(3) . ?
C5 C6 1.408(2) . ?
C5 C18 1.511(2) . ?
C6 C9 1.509(2) . ?
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 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.395(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(3) . ?
C21 H21 0.9300 . ?

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
C13 N1 N2 112.26(16) . . ?
C13 N1 C10 127.64(16) . . ?
N2 N1 C10 120.07(16) . . ?
C11 N2 N1 105.01(16) . . ?
N4 N3 C17 112.06(16) . . ?
N4 N3 C14 119.88(16) . . ?
C17 N3 C14 128.05(17) . . ?
C15 N4 N3 105.15(17) . . ?
C21 N5 N6 112.45(15) . . ?
C21 N5 C18 127.63(16) . . ?
N6 N5 C18 119.74(15) . . ?
C19 N6 N5 104.91(15) . . ?
C6 C1 C2 120.72(16) . . ?
C6 C1 C10 120.16(16) . . ?
C2 C1 C10 119.11(16) . . ?
C3 C2 C1 119.05(16) . . ?
C3 C2 C7 121.34(17) . . ?
C1 C2 C7 119.61(17) . . ?
C2 C3 C4 120.92(17) . . ?
C2 C3 C14 120.32(17) . . ?
C4 C3 C14 118.74(16) . . ?
C5 C4 C3 119.36(16) . . ?
C5 C4 C8 121.93(16) . . ?
C3 C4 C8 118.70(16) . . ?
C4 C5 C6 120.37(16) . . ?
C4 C5 C18 120.42(16) . . ?
C6 C5 C18 119.20(16) . . ?
C1 C6 C5 119.54(16) . . ?
C1 C6 C9 120.05(16) . . ?
C5 C6 C9 120.41(16) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 112.30(15) . . ?
N1 C10 H10A 109.1 . . ?
C1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C1 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C12 110.62(17) . . ?
N2 C11 H11 124.7 . . ?
C12 C11 H11 124.7 . . ?
C13 C12 C11 106.11(17) . . ?
C13 C12 Br1 127.11(15) . . ?
C11 C12 Br1 126.76(15) . . ?
N1 C13 C12 105.99(17) . . ?
N1 C13 H13 127.0 . . ?
C12 C13 H13 127.0 . . ?
N3 C14 C3 111.41(15) . . ?
N3 C14 H14A 109.3 . . ?
C3 C14 H14A 109.3 . . ?
N3 C14 H14B 109.3 . . ?
C3 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 C16 110.79(19) . . ?
N4 C15 H15 124.6 . . ?
C16 C15 H15 124.6 . . ?
C17 C16 C15 105.76(17) . . ?
C17 C16 Br2 126.26(15) . . ?
C15 C16 Br2 127.97(16) . . ?
N3 C17 C16 106.24(17) . . ?
N3 C17 H17 126.9 . . ?
C16 C17 H17 126.9 . . ?
N5 C18 C5 112.67(15) . . ?
N5 C18 H18A 109.1 . . ?
C5 C18 H18A 109.1 . . ?
N5 C18 H18B 109.1 . . ?
C5 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
N6 C19 C20 110.67(17) . . ?
N6 C19 H19 124.7 . . ?
C20 C19 H19 124.7 . . ?
C21 C20 C19 106.08(16) . . ?
C21 C20 Br3 127.79(14) . . ?
C19 C20 Br3 126.06(14) . . ?
N5 C21 C20 105.89(16) . . ?
N5 C21 H21 127.1 . . ?
C20 C21 H21 127.1 . . ?

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
C13 N1 N2 C11 1.0(2) . . . . ?
C10 N1 N2 C11 179.07(16) . . . . ?
C17 N3 N4 C15 0.2(3) . . . . ?
C14 N3 N4 C15 178.92(19) . . . . ?
C21 N5 N6 C19 1.0(2) . . . . ?
C18 N5 N6 C19 176.39(16) . . . . ?
C6 C1 C2 C3 1.0(3) . . . . ?
C10 C1 C2 C3 179.92(16) . . . . ?
C6 C1 C2 C7 -179.22(17) . . . . ?
C10 C1 C2 C7 -0.3(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C7 C2 C3 C4 -179.93(17) . . . . ?
C1 C2 C3 C14 -178.51(16) . . . . ?
C7 C2 C3 C14 1.7(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C14 C3 C4 C5 176.93(16) . . . . ?
C2 C3 C4 C8 178.23(17) . . . . ?
C14 C3 C4 C8 -3.4(3) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C8 C4 C5 C6 -177.45(17) . . . . ?
C3 C4 C5 C18 -176.36(16) . . . . ?
C8 C4 C5 C18 4.0(3) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C10 C1 C6 C5 -179.15(16) . . . . ?
C2 C1 C6 C9 179.32(16) . . . . ?
C10 C1 C6 C9 0.4(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C18 C5 C6 C1 177.21(16) . . . . ?
C4 C5 C6 C9 179.05(16) . . . . ?
C18 C5 C6 C9 -2.3(2) . . . . ?
C13 N1 C10 C1 -130.23(19) . . . . ?
N2 N1 C10 C1 52.0(2) . . . . ?
C6 C1 C10 N1 82.8(2) . . . . ?
C2 C1 C10 N1 -96.1(2) . . . . ?
N1 N2 C11 C12 -0.6(2) . . . . ?
N2 C11 C12 C13 0.0(2) . . . . ?
N2 C11 C12 Br1 178.25(15) . . . . ?
N2 N1 C13 C12 -1.0(2) . . . . ?
C10 N1 C13 C12 -178.88(18) . . . . ?
C11 C12 C13 N1 0.6(2) . . . . ?
Br1 C12 C13 N1 -177.65(14) . . . . ?
N4 N3 C14 C3 124.06(19) . . . . ?
C17 N3 C14 C3 -57.5(3) . . . . ?
C2 C3 C14 N3 95.9(2) . . . . ?
C4 C3 C14 N3 -82.5(2) . . . . ?
N3 N4 C15 C16 0.2(3) . . . . ?
N4 C15 C16 C17 -0.5(3) . . . . ?
N4 C15 C16 Br2 179.49(17) . . . . ?
N4 N3 C17 C16 -0.6(2) . . . . ?
C14 N3 C17 C16 -179.13(18) . . . . ?
C15 C16 C17 N3 0.7(2) . . . . ?
Br2 C16 C17 N3 -179.37(14) . . . . ?
C21 N5 C18 C5 -129.45(19) . . . . ?
N6 N5 C18 C5 55.9(2) . . . . ?
C4 C5 C18 N5 -93.5(2) . . . . ?
C6 C5 C18 N5 87.9(2) . . . . ?
N5 N6 C19 C20 -0.7(2) . . . . ?
N6 C19 C20 C21 0.2(2) . . . . ?
N6 C19 C20 Br3 177.53(14) . . . . ?
N6 N5 C21 C20 -0.8(2) . . . . ?
C18 N5 C21 C20 -175.81(17) . . . . ?
C19 C20 C21 N5 0.3(2) . . . . ?
Br3 C20 C21 N5 -176.88(14) . . . . ?

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
C19 H19 N4 0.93 2.40 3.289(3) 160.8 2_666
C18 H18A N2 0.97 2.66 3.232(3) 118.0 2_656
C13 H13 Br1 0.93 2.97 3.7873(19) 147.1 2_746
C11 H11 Br2 0.93 2.80 3.5826(19) 142.4 2_655

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.084

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch_29_0m
_database_code_depnum_ccdc_archive 'CCDC 1533894'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br3 N6 O3'
_chemical_formula_sum            'C21 H21 Br3 N6 O3'
_chemical_formula_weight         645.17

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

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

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

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

_cell_length_a                   9.7139(16)
_cell_length_b                   9.0347(15)
_cell_length_c                   26.923(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.855(3)
_cell_angle_gamma                90
_cell_volume                     2340.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      35.94

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    5.207
_shelx_estimated_absorpt_T_min   0.162
_shelx_estimated_absorpt_T_max   0.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1619
_exptl_absorpt_correction_T_max  0.3041
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28246
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.093
_diffrn_reflns_theta_max         29.097
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6281
_reflns_number_gt                5347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0265P)²+2.4486P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6281
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
Br1 Br 0.95150(2) 0.56824(2) 0.43890(2) 0.02124(6) Uani 1 1 d . . . . .
Br2 Br 1.56832(2) 0.23636(2) 0.18142(2) 0.01994(5) Uani 1 1 d . . . . .
Br3 Br 0.32386(2) 0.74974(2) -0.01993(2) 0.02283(6) Uani 1 1 d . . . . .
O1 O 1.24746(14) 0.78526(14) 0.20372(5) 0.0129(3) Uani 1 1 d . . . . .
O2 O 0.93012(15) 0.55418(15) 0.07617(5) 0.0164(3) Uani 1 1 d . . . . .
O3 O 0.77572(15) 0.70858(15) 0.22885(5) 0.0155(3) Uani 1 1 d . . . . .
N1 N 1.03514(17) 0.72892(16) 0.30784(5) 0.0113(3) Uani 1 1 d . . . . .
N2 N 1.12306(17) 0.61216(17) 0.31107(6) 0.0136(3) Uani 1 1 d . . . . .
N3 N 1.27976(17) 0.51745(17) 0.11655(6) 0.0117(3) Uani 1 1 d . . . . .
N4 N 1.26400(18) 0.41198(18) 0.08077(6) 0.0158(3) Uani 1 1 d . . . . .
N5 N 0.62528(17) 0.66551(18) 0.09364(6) 0.0144(3) Uani 1 1 d . . . . .
N6 N 0.6331(2) 0.81427(19) 0.09552(7) 0.0226(4) Uani 1 1 d . . . . .
C1 C 1.0080(2) 0.75762(18) 0.21581(6) 0.0106(3) Uani 1 1 d . . . . .
C2 C 1.11348(19) 0.74201(18) 0.18580(6) 0.0103(3) Uani 1 1 d . . . . .
C3 C 1.08913(19) 0.67619(19) 0.13845(6) 0.0106(3) Uani 1 1 d . . . . .
C4 C 0.9558(2) 0.6265(2) 0.12128(6) 0.0115(3) Uani 1 1 d . . . . .
C5 C 0.84754(19) 0.6391(2) 0.15015(6) 0.0111(3) Uani 1 1 d . . . . .
C6 C 0.8764(2) 0.7045(2) 0.19741(7) 0.0118(3) Uani 1 1 d . . . . .
C7 C 1.2780(2) 0.9369(2) 0.19284(8) 0.0190(4) Uani 1 1 d . . . . .
H7A H 1.2698 0.9507 0.1565 0.028 Uiso 1 1 calc R U . . .
H7B H 1.3728 0.9609 0.2081 0.028 Uiso 1 1 calc R U . . .
H7C H 1.2121 1.0023 0.2066 0.028 Uiso 1 1 calc R U . . .
C8 C 0.8986(2) 0.6498(3) 0.03332(7) 0.0225(4) Uani 1 1 d . . . . .
H8A H 0.8168 0.7099 0.0372 0.034 Uiso 1 1 calc R U . . .
H8B H 0.8794 0.5897 0.0029 0.034 Uiso 1 1 calc R U . . .
H8C H 0.9780 0.7148 0.0307 0.034 Uiso 1 1 calc R U . . .
C9 C 0.6799(2) 0.8311(2) 0.22088(8) 0.0212(4) Uani 1 1 d . . . . .
H9A H 0.7298 0.9239 0.2295 0.032 Uiso 1 1 calc R U . . .
H9B H 0.6064 0.8189 0.2421 0.032 Uiso 1 1 calc R U . . .
H9C H 0.6385 0.8337 0.1856 0.032 Uiso 1 1 calc R U . . .
C10 C 1.0345(2) 0.8322(2) 0.26625(6) 0.013 Uani 1 1 d . . . . .
H10A H 1.1253 0.8836 0.2693 0.015 Uiso 1 1 calc R U . . .
H10B H 0.9618 0.9079 0.2684 0.015 Uiso 1 1 calc R U . . .
C11 C 1.1085(2) 0.5480(2) 0.35454(7) 0.0144(4) Uani 1 1 d . . . . .
H11 H 1.1572 0.4620 0.3674 0.017 Uiso 1 1 calc R U . . .
C12 C 1.0121(2) 0.6240(2) 0.37854(6) 0.0136(4) Uani 1 1 d . . . . .
C13 C 0.9668(2) 0.7406(2) 0.34808(7) 0.0143(4) Uani 1 1 d . . . . .
H13 H 0.9011 0.8141 0.3540 0.017 Uiso 1 1 calc R U . . .
C14 C 1.2058(2) 0.6577(2) 0.10751(7) 0.0129(3) Uani 1 1 d . . . . .
H14A H 1.1675 0.6641 0.0716 0.016 Uiso 1 1 calc R U . . .
H14B H 1.2726 0.7400 0.1151 0.016 Uiso 1 1 calc R U . . .
C15 C 1.3521(2) 0.3050(2) 0.09819(8) 0.0170(4) Uani 1 1 d . . . . .
H15 H 1.3643 0.2149 0.0811 0.020 Uiso 1 1 calc R U . . .
C16 C 1.42394(19) 0.3432(2) 0.14481(7) 0.0136(3) Uani 1 1 d . . . . .
C17 C 1.3751(2) 0.4804(2) 0.15581(7) 0.0129(3) Uani 1 1 d . . . . .
H17 H 1.4028 0.5376 0.1851 0.016 Uiso 1 1 calc R U . . .
C18 C 0.7073(2) 0.5745(2) 0.13197(7) 0.0149(4) Uani 1 1 d . . . . .
H18A H 0.7199 0.4748 0.1179 0.018 Uiso 1 1 calc R U . . .
H18B H 0.6552 0.5627 0.1608 0.018 Uiso 1 1 calc R U . . .
C19 C 0.5380(2) 0.8610(2) 0.05862(8) 0.0230(4) Uani 1 1 d . . . . .
H19 H 0.5196 0.9621 0.0505 0.028 Uiso 1 1 calc R U . . .
C20 C 0.4693(2) 0.7422(2) 0.03350(7) 0.0164(4) Uani 1 1 d . . . . .
C21 C 0.5273(2) 0.6178(2) 0.05681(7) 0.0150(4) Uani 1 1 d . . . . .
H21 H 0.5032 0.5180 0.0486 0.018 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.8717(18) . ?
Br2 C16 1.8687(19) . ?
Br3 C20 1.875(2) . ?
O1 C2 1.381(2) . ?
O1 C7 1.440(2) . ?
O2 C4 1.372(2) . ?
O2 C8 1.440(2) . ?
O3 C6 1.379(2) . ?
O3 C9 1.443(2) . ?
N1 C13 1.350(2) . ?
N1 N2 1.353(2) . ?
N1 C10 1.457(2) . ?
N2 C11 1.331(2) . ?
N3 N4 1.349(2) . ?
N3 C17 1.349(2) . ?
N3 C14 1.460(2) . ?
N4 C15 1.333(3) . ?
N5 N6 1.347(2) . ?
N5 C21 1.348(2) . ?
N5 C18 1.467(2) . ?
N6 C19 1.329(3) . ?
C1 C6 1.391(3) . ?
C1 C2 1.396(3) . ?
C1 C10 1.507(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.389(3) . ?
C3 C14 1.505(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.396(2) . ?
C5 C18 1.501(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.390(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.393(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.370(3) . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C7 114.10(14) . . ?
C4 O2 C8 114.61(15) . . ?
C6 O3 C9 115.25(14) . . ?
C13 N1 N2 112.62(15) . . ?
C13 N1 C10 128.02(15) . . ?
N2 N1 C10 119.04(15) . . ?
C11 N2 N1 104.73(15) . . ?
N4 N3 C17 112.55(15) . . ?
N4 N3 C14 119.25(15) . . ?
C17 N3 C14 127.96(15) . . ?
C15 N4 N3 104.84(15) . . ?
N6 N5 C21 112.13(16) . . ?
N6 N5 C18 120.73(16) . . ?
C21 N5 C18 126.84(16) . . ?
C19 N6 N5 105.04(17) . . ?
C6 C1 C2 118.04(16) . . ?
C6 C1 C10 120.73(17) . . ?
C2 C1 C10 121.22(17) . . ?
O1 C2 C1 120.02(16) . . ?
O1 C2 C3 118.24(16) . . ?
C1 C2 C3 121.66(17) . . ?
C4 C3 C2 118.36(17) . . ?
C4 C3 C14 121.23(16) . . ?
C2 C3 C14 120.40(17) . . ?
O2 C4 C3 119.81(16) . . ?
O2 C4 C5 118.17(16) . . ?
C3 C4 C5 121.88(16) . . ?
C4 C5 C6 117.97(17) . . ?
C4 C5 C18 120.42(16) . . ?
C6 C5 C18 121.48(17) . . ?
O3 C6 C1 117.80(16) . . ?
O3 C6 C5 119.97(17) . . ?
C1 C6 C5 122.07(17) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 112.84(14) . . ?
N1 C10 H10A 109.0 . . ?
C1 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 110.65(16) . . ?
N2 C11 H11 124.7 . . ?
C12 C11 H11 124.7 . . ?
C13 C12 C11 106.46(16) . . ?
C13 C12 Br1 127.84(15) . . ?
C11 C12 Br1 125.61(14) . . ?
N1 C13 C12 105.54(16) . . ?
N1 C13 H13 127.2 . . ?
C12 C13 H13 127.2 . . ?
N3 C14 C3 113.26(15) . . ?
N3 C14 H14A 108.9 . . ?
C3 C14 H14A 108.9 . . ?
N3 C14 H14B 108.9 . . ?
C3 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N4 C15 C16 110.86(17) . . ?
N4 C15 H15 124.6 . . ?
C16 C15 H15 124.6 . . ?
C17 C16 C15 105.80(17) . . ?
C17 C16 Br2 127.48(15) . . ?
C15 C16 Br2 126.49(15) . . ?
N3 C17 C16 105.96(16) . . ?
N3 C17 H17 127.0 . . ?
C16 C17 H17 127.0 . . ?
N5 C18 C5 113.13(15) . . ?
N5 C18 H18A 109.0 . . ?
C5 C18 H18A 109.0 . . ?
N5 C18 H18B 109.0 . . ?
C5 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N6 C19 C20 110.86(19) . . ?
N6 C19 H19 124.6 . . ?
C20 C19 H19 124.6 . . ?
C21 C20 C19 105.72(18) . . ?
C21 C20 Br3 126.92(15) . . ?
C19 C20 Br3 127.34(16) . . ?
N5 C21 C20 106.24(17) . . ?
N5 C21 H21 126.9 . . ?
C20 C21 H21 126.9 . . ?

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
C13 N1 N2 C11 0.5(2) . . . . ?
C10 N1 N2 C11 174.48(16) . . . . ?
C17 N3 N4 C15 0.1(2) . . . . ?
C14 N3 N4 C15 174.91(16) . . . . ?
C21 N5 N6 C19 -0.4(2) . . . . ?
C18 N5 N6 C19 -174.57(18) . . . . ?
C7 O1 C2 C1 -90.37(19) . . . . ?
C7 O1 C2 C3 92.86(19) . . . . ?
C6 C1 C2 O1 -176.21(15) . . . . ?
C10 C1 C2 O1 4.9(2) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C10 C1 C2 C3 -178.43(16) . . . . ?
O1 C2 C3 C4 177.14(15) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
O1 C2 C3 C14 -1.8(2) . . . . ?
C1 C2 C3 C14 -178.52(16) . . . . ?
C8 O2 C4 C3 -86.5(2) . . . . ?
C8 O2 C4 C5 97.7(2) . . . . ?
C2 C3 C4 O2 -176.44(15) . . . . ?
C14 C3 C4 O2 2.5(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C14 C3 C4 C5 178.11(17) . . . . ?
O2 C4 C5 C6 176.02(16) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
O2 C4 C5 C18 0.1(3) . . . . ?
C3 C4 C5 C18 -175.59(16) . . . . ?
C9 O3 C6 C1 99.5(2) . . . . ?
C9 O3 C6 C5 -84.9(2) . . . . ?
C2 C1 C6 O3 174.55(15) . . . . ?
C10 C1 C6 O3 -6.6(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C10 C1 C6 C5 177.91(16) . . . . ?
C4 C5 C6 O3 -174.84(16) . . . . ?
C18 C5 C6 O3 1.0(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C18 C5 C6 C1 176.47(16) . . . . ?
C13 N1 C10 C1 -131.1(2) . . . . ?
N2 N1 C10 C1 56.0(2) . . . . ?
C6 C1 C10 N1 72.5(2) . . . . ?
C2 C1 C10 N1 -108.69(19) . . . . ?
N1 N2 C11 C12 -0.1(2) . . . . ?
N2 C11 C12 C13 -0.3(2) . . . . ?
N2 C11 C12 Br1 176.56(14) . . . . ?
N2 N1 C13 C12 -0.7(2) . . . . ?
C10 N1 C13 C12 -174.03(18) . . . . ?
C11 C12 C13 N1 0.6(2) . . . . ?
Br1 C12 C13 N1 -176.20(14) . . . . ?
N4 N3 C14 C3 108.96(18) . . . . ?
C17 N3 C14 C3 -77.2(2) . . . . ?
C4 C3 C14 N3 -89.0(2) . . . . ?
C2 C3 C14 N3 89.9(2) . . . . ?
N3 N4 C15 C16 -0.3(2) . . . . ?
N4 C15 C16 C17 0.3(2) . . . . ?
N4 C15 C16 Br2 -174.52(14) . . . . ?
N4 N3 C17 C16 0.0(2) . . . . ?
C14 N3 C17 C16 -174.16(17) . . . . ?
C15 C16 C17 N3 -0.2(2) . . . . ?
Br2 C16 C17 N3 174.56(14) . . . . ?
N6 N5 C18 C5 -35.3(2) . . . . ?
C21 N5 C18 C5 151.47(18) . . . . ?
C4 C5 C18 N5 -77.9(2) . . . . ?
C6 C5 C18 N5 106.36(19) . . . . ?
N5 N6 C19 C20 0.4(3) . . . . ?
N6 C19 C20 C21 -0.1(3) . . . . ?
N6 C19 C20 Br3 178.18(16) . . . . ?
N6 N5 C21 C20 0.4(2) . . . . ?
C18 N5 C21 C20 174.05(18) . . . . ?
C19 C20 C21 N5 -0.1(2) . . . . ?
Br3 C20 C21 N5 -178.46(14) . . . . ?

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
C7 H7C O3 0.98 2.54 3.323(2) 136.8 2_755
C8 H8A N5 0.98 2.59 3.299(3) 129.4 .
C8 H8B N4 0.98 2.48 3.304(3) 141.4 3_765
C9 H9A N2 0.98 2.56 3.362(3) 138.9 2_755
C9 H9B Br2 0.98 2.94 3.899(2) 167.0 2_755
C9 H9C N6 0.98 2.42 3.347(3) 156.6 .
C11 H11 N6 0.95 2.52 3.413(3) 155.7 2_745
C13 H13 N4 0.95 2.68 3.503(3) 144.7 2_755

_refine_diff_density_max         0.746
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.079

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch4a
_database_code_depnum_ccdc_archive 'CCDC 1533896'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H33 Br3 N6 O3'
_chemical_formula_sum            'C27 H33 Br3 N6 O3'
_chemical_formula_weight         729.32

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   20.3559(5)
_cell_length_b                   23.6203(6)
_cell_length_c                   12.7536(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.697(1)
_cell_angle_gamma                90
_cell_volume                     6111.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9820
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      30.37

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             2928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    3.999
_shelx_estimated_absorpt_T_min   0.217
_shelx_estimated_absorpt_T_max   0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2169
_exptl_absorpt_correction_T_max  0.7146
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8198
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.354
_diffrn_reflns_theta_max         29.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8195
_reflns_number_gt                7020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0327P)²+5.4886P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8195
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0608
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24501(2) 0.47905(2) 0.60850(2) 0.02782(5) Uani 1 1 d . . . A 1
Br2 Br 0.79570(2) 0.38916(2) 0.63683(2) 0.02678(5) Uani 1 1 d . . . A 1
Br3 Br 0.41699(2) 0.00651(2) 0.61180(2) 0.03281(5) Uani 1 1 d . . . A 1
O1 O 0.57140(6) 0.37689(5) 0.38503(9) 0.0205(2) Uani 1 1 d . . . A 1
O2 O 0.52986(5) 0.17731(5) 0.38980(8) 0.0177(2) Uani 1 1 d . . . A 1
O3 O 0.34944(5) 0.30815(5) 0.37115(8) 0.0184(2) Uani 1 1 d . . . A 1
N1 N 0.39656(7) 0.42260(6) 0.45846(10) 0.0195(3) Uani 1 1 d . . . A 1
N2 N 0.42790(7) 0.42289(6) 0.55690(11) 0.0241(3) Uani 1 1 d . . . A 1
N3 N 0.66606(6) 0.28746(6) 0.47959(9) 0.0163(2) Uani 1 1 d . . . A 1
N4 N 0.65420(7) 0.26961(6) 0.57789(10) 0.0194(3) Uani 1 1 d . . . A 1
N5 N 0.39411(6) 0.15307(6) 0.45747(10) 0.0175(3) Uani 1 1 d . . . A 1
N6 N 0.38370(7) 0.17306(6) 0.55522(10) 0.0215(3) Uani 1 1 d . . . A 1
C1 C 0.45947(8) 0.34344(7) 0.38521(11) 0.0168(3) Uani 1 1 d . . . A 1
C2 C 0.52720(7) 0.33257(7) 0.39058(11) 0.0167(3) Uani 1 1 d . . . A 1
C3 C 0.55229(7) 0.27737(7) 0.39370(11) 0.0158(3) Uani 1 1 d . . . A 1
C4 C 0.50759(7) 0.23273(6) 0.39199(11) 0.0157(3) Uani 1 1 d . . . A 1
C5 C 0.43930(7) 0.24153(7) 0.38532(11) 0.0159(3) Uani 1 1 d . . . A 1
C6 C 0.41653(7) 0.29713(7) 0.38335(11) 0.0158(3) Uani 1 1 d . . . A 1
C7 C 0.58566(9) 0.40629(8) 0.48400(14) 0.0255(3) Uani 1 1 d . . . A 1
H7A H 0.5457 0.4252 0.5039 0.038 Uiso 1 1 calc R U . A 1
H7B H 0.6202 0.4345 0.4763 0.038 Uiso 1 1 calc R U . A 1
H7C H 0.6007 0.3790 0.5387 0.038 Uiso 1 1 calc R U . A 1
C8 C 0.55220(8) 0.15651(7) 0.49351(12) 0.0210(3) Uani 1 1 d . . . A 1
H8A H 0.5909 0.1782 0.5211 0.032 Uiso 1 1 calc R U . A 1
H8B H 0.5640 0.1164 0.4889 0.032 Uiso 1 1 calc R U . A 1
H8C H 0.5169 0.1609 0.5407 0.032 Uiso 1 1 calc R U . A 1
C9 C 0.31775(8) 0.30327(7) 0.46851(13) 0.0218(3) Uani 1 1 d . . . A 1
H9A H 0.3223 0.2644 0.4949 0.033 Uiso 1 1 calc R U . A 1
H9B H 0.2709 0.3127 0.4556 0.033 Uiso 1 1 calc R U . A 1
H9C H 0.3387 0.3294 0.5208 0.033 Uiso 1 1 calc R U . A 1
C10 C 0.43251(8) 0.40270(7) 0.37056(12) 0.0197(3) Uani 1 1 d . . . A 1
H10A H 0.4695 0.4289 0.3613 0.024 Uiso 1 1 calc R U . A 1
H10B H 0.4026 0.4039 0.3053 0.024 Uiso 1 1 calc R U . A 1
C11 C 0.38330(8) 0.44147(7) 0.61974(13) 0.0240(3) Uani 1 1 d . . . A 1
C12 C 0.32407(8) 0.45301(7) 0.56015(13) 0.0203(3) Uani 1 1 d . . . A 1
C13 C 0.33313(8) 0.44051(7) 0.45689(12) 0.0192(3) Uani 1 1 d . . . A 1
C14 C 0.39929(10) 0.44688(10) 0.73598(14) 0.0383(5) Uani 1 1 d . . . A 1
H14A H 0.4353 0.4209 0.7585 0.057 Uiso 1 1 calc R U . A 1
H14B H 0.3603 0.4374 0.7726 0.057 Uiso 1 1 calc R U . A 1
H14C H 0.4128 0.4859 0.7530 0.057 Uiso 1 1 calc R U . A 1
C15 C 0.28578(9) 0.44243(8) 0.36177(13) 0.0259(3) Uani 1 1 d . . . A 1
H15A H 0.3051 0.4641 0.3063 0.039 Uiso 1 1 calc R U . A 1
H15B H 0.2449 0.4607 0.3793 0.039 Uiso 1 1 calc R U . A 1
H15C H 0.2762 0.4038 0.3370 0.039 Uiso 1 1 calc R U . A 1
C16 C 0.62516(7) 0.26621(7) 0.38861(11) 0.0172(3) Uani 1 1 d . . . A 1
H16A H 0.6322 0.2249 0.3828 0.021 Uiso 1 1 calc R U . A 1
H16B H 0.6397 0.2841 0.3242 0.021 Uiso 1 1 calc R U . A 1
C17 C 0.69614(8) 0.29919(7) 0.64329(12) 0.0196(3) Uani 1 1 d . . . A 1
C18 C 0.73402(7) 0.33512(7) 0.58506(12) 0.0184(3) Uani 1 1 d . . . A 1
C19 C 0.71414(7) 0.32697(7) 0.47984(12) 0.0171(3) Uani 1 1 d . . . A 1
C20 C 0.69803(10) 0.29182(9) 0.75971(13) 0.0309(4) Uani 1 1 d . . . A 1
H20A H 0.6556 0.2769 0.7785 0.046 Uiso 1 1 calc R U . A 1
H20B H 0.7065 0.3285 0.7942 0.046 Uiso 1 1 calc R U . A 1
H20C H 0.7332 0.2652 0.7829 0.046 Uiso 1 1 calc R U . A 1
C21 C 0.73645(8) 0.35383(8) 0.38413(13) 0.0241(3) Uani 1 1 d . . . A 1
H21A H 0.7536 0.3247 0.3389 0.036 Uiso 1 1 calc R U . A 1
H21B H 0.7713 0.3814 0.4042 0.036 Uiso 1 1 calc R U . A 1
H21C H 0.6992 0.3732 0.3459 0.036 Uiso 1 1 calc R U . A 1
C22 C 0.39250(8) 0.19224(7) 0.36871(12) 0.0179(3) Uani 1 1 d . . . A 1
H22A H 0.3471 0.2071 0.3551 0.021 Uiso 1 1 calc R U . A 1
H22B H 0.4034 0.1711 0.3054 0.021 Uiso 1 1 calc R U . A 1
C23 C 0.40695(7) 0.09694(7) 0.45678(12) 0.0185(3) Uani 1 1 d . . . A 1
C24 C 0.40437(8) 0.08011(7) 0.55984(13) 0.0211(3) Uani 1 1 d . . . A 1
C25 C 0.39023(8) 0.12786(8) 0.61834(12) 0.0224(3) Uani 1 1 d . . . A 1
C26 C 0.42104(8) 0.06465(7) 0.36134(13) 0.0237(3) Uani 1 1 d . . . A 1
H26A H 0.3820 0.0650 0.3110 0.036 Uiso 1 1 calc R U . A 1
H26B H 0.4323 0.0255 0.3809 0.036 Uiso 1 1 calc R U . A 1
H26C H 0.4581 0.0822 0.3292 0.036 Uiso 1 1 calc R U . A 1
C27 C 0.38492(10) 0.13218(9) 0.73420(14) 0.0337(4) Uani 1 1 d . . . A 1
H27A H 0.3726 0.1709 0.7520 0.051 Uiso 1 1 calc R U . A 1
H27B H 0.4275 0.1227 0.7716 0.051 Uiso 1 1 calc R U . A 1
H27C H 0.3512 0.1057 0.7550 0.051 Uiso 1 1 calc R U . A 1


_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 C12 1.8737(16) . ?
Br2 C18 1.8723(15) . ?
Br3 C24 1.8708(16) . ?
O1 C2 1.3860(18) . ?
O1 C7 1.4490(19) . ?
O2 C4 1.3862(18) . ?
O2 C8 1.4489(18) . ?
O3 C6 1.3864(18) . ?
O3 C9 1.4500(18) . ?
N1 C13 1.357(2) . ?
N1 N2 1.3610(18) . ?
N1 C10 1.465(2) . ?
N2 C11 1.333(2) . ?
N3 C19 1.3523(19) . ?
N3 N4 1.3627(17) . ?
N3 C16 1.4605(18) . ?
N4 C17 1.340(2) . ?
N5 C23 1.351(2) . ?
N5 N6 1.3658(18) . ?
N5 C22 1.4603(19) . ?
N6 C25 1.337(2) . ?
C1 C2 1.398(2) . ?
C1 C6 1.399(2) . ?
C1 C10 1.509(2) . ?
C2 C3 1.400(2) . ?
C3 C4 1.392(2) . ?
C3 C16 1.513(2) . ?
C4 C5 1.401(2) . ?
C5 C6 1.392(2) . ?
C5 C22 1.508(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.398(2) . ?
C11 C14 1.497(2) . ?
C12 C13 1.377(2) . ?
C13 C15 1.487(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.400(2) . ?
C17 C20 1.492(2) . ?
C18 C19 1.383(2) . ?
C19 C21 1.480(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.378(2) . ?
C23 C26 1.484(2) . ?
C24 C25 1.395(2) . ?
C25 C27 1.494(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C7 113.72(12) . . ?
C4 O2 C8 112.37(11) . . ?
C6 O3 C9 113.09(11) . . ?
C13 N1 N2 112.68(13) . . ?
C13 N1 C10 128.52(13) . . ?
N2 N1 C10 118.78(13) . . ?
C11 N2 N1 105.38(13) . . ?
C19 N3 N4 113.20(12) . . ?
C19 N3 C16 127.19(12) . . ?
N4 N3 C16 119.49(12) . . ?
C17 N4 N3 105.04(13) . . ?
C23 N5 N6 112.93(13) . . ?
C23 N5 C22 127.49(13) . . ?
N6 N5 C22 119.55(13) . . ?
C25 N6 N5 104.97(13) . . ?
C2 C1 C6 117.98(14) . . ?
C2 C1 C10 121.56(14) . . ?
C6 C1 C10 120.17(14) . . ?
O1 C2 C1 120.02(14) . . ?
O1 C2 C3 117.91(13) . . ?
C1 C2 C3 121.91(14) . . ?
C4 C3 C2 117.94(13) . . ?
C4 C3 C16 120.63(14) . . ?
C2 C3 C16 121.18(14) . . ?
O2 C4 C3 120.07(13) . . ?
O2 C4 C5 117.60(13) . . ?
C3 C4 C5 122.19(14) . . ?
C6 C5 C4 117.91(14) . . ?
C6 C5 C22 121.34(13) . . ?
C4 C5 C22 120.41(14) . . ?
O3 C6 C5 120.17(13) . . ?
O3 C6 C1 117.60(13) . . ?
C5 C6 C1 122.05(14) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 113.71(12) . . ?
N1 C10 H10A 108.8 . . ?
C1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C1 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 109.68(14) . . ?
N2 C11 C14 121.32(15) . . ?
C12 C11 C14 129.00(16) . . ?
C13 C12 C11 107.52(14) . . ?
C13 C12 Br1 124.83(12) . . ?
C11 C12 Br1 127.64(12) . . ?
N1 C13 C12 104.75(13) . . ?
N1 C13 C15 125.01(14) . . ?
C12 C13 C15 130.18(15) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C3 113.77(12) . . ?
N3 C16 H16A 108.8 . . ?
C3 C16 H16A 108.8 . . ?
N3 C16 H16B 108.8 . . ?
C3 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
N4 C17 C18 109.65(13) . . ?
N4 C17 C20 121.44(15) . . ?
C18 C17 C20 128.91(15) . . ?
C19 C18 C17 107.47(13) . . ?
C19 C18 Br2 124.86(12) . . ?
C17 C18 Br2 127.49(12) . . ?
N3 C19 C18 104.64(13) . . ?
N3 C19 C21 124.40(14) . . ?
C18 C19 C21 130.96(15) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C5 113.98(12) . . ?
N5 C22 H22A 108.8 . . ?
C5 C22 H22A 108.8 . . ?
N5 C22 H22B 108.8 . . ?
C5 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
N5 C23 C24 104.72(14) . . ?
N5 C23 C26 124.05(14) . . ?
C24 C23 C26 131.22(15) . . ?
C23 C24 C25 107.61(14) . . ?
C23 C24 Br3 126.23(13) . . ?
C25 C24 Br3 126.16(12) . . ?
N6 C25 C24 109.76(14) . . ?
N6 C25 C27 121.96(16) . . ?
C24 C25 C27 128.24(16) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C13 N1 N2 C11 -0.01(19) . . . . ?
C10 N1 N2 C11 -178.57(14) . . . . ?
C19 N3 N4 C17 0.37(17) . . . . ?
C16 N3 N4 C17 -175.88(13) . . . . ?
C23 N5 N6 C25 -0.01(17) . . . . ?
C22 N5 N6 C25 -178.22(13) . . . . ?
C7 O1 C2 C1 81.27(17) . . . . ?
C7 O1 C2 C3 -103.35(15) . . . . ?
C6 C1 C2 O1 175.40(12) . . . . ?
C10 C1 C2 O1 1.6(2) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C10 C1 C2 C3 -173.57(13) . . . . ?
O1 C2 C3 C4 -175.69(12) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
O1 C2 C3 C16 -1.41(19) . . . . ?
C1 C2 C3 C16 173.87(13) . . . . ?
C8 O2 C4 C3 82.54(16) . . . . ?
C8 O2 C4 C5 -101.62(15) . . . . ?
C2 C3 C4 O2 176.87(12) . . . . ?
C16 C3 C4 O2 2.6(2) . . . . ?
C2 C3 C4 C5 1.2(2) . . . . ?
C16 C3 C4 C5 -173.08(13) . . . . ?
O2 C4 C5 C6 -177.55(12) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
O2 C4 C5 C22 -4.17(19) . . . . ?
C3 C4 C5 C22 171.57(13) . . . . ?
C9 O3 C6 C5 81.55(16) . . . . ?
C9 O3 C6 C1 -103.27(15) . . . . ?
C4 C5 C6 O3 176.55(12) . . . . ?
C22 C5 C6 O3 3.2(2) . . . . ?
C4 C5 C6 C1 1.6(2) . . . . ?
C22 C5 C6 C1 -171.72(13) . . . . ?
C2 C1 C6 O3 -175.91(12) . . . . ?
C10 C1 C6 O3 -2.0(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C10 C1 C6 C5 173.05(13) . . . . ?
C13 N1 C10 C1 -121.68(17) . . . . ?
N2 N1 C10 C1 56.62(19) . . . . ?
C2 C1 C10 N1 -117.73(16) . . . . ?
C6 C1 C10 N1 68.61(18) . . . . ?
N1 N2 C11 C12 -0.24(19) . . . . ?
N1 N2 C11 C14 179.10(17) . . . . ?
N2 C11 C12 C13 0.4(2) . . . . ?
C14 C11 C12 C13 -178.87(19) . . . . ?
N2 C11 C12 Br1 179.05(12) . . . . ?
C14 C11 C12 Br1 -0.2(3) . . . . ?
N2 N1 C13 C12 0.25(18) . . . . ?
C10 N1 C13 C12 178.63(15) . . . . ?
N2 N1 C13 C15 -177.21(15) . . . . ?
C10 N1 C13 C15 1.2(3) . . . . ?
C11 C12 C13 N1 -0.38(18) . . . . ?
Br1 C12 C13 N1 -179.08(11) . . . . ?
C11 C12 C13 C15 176.90(17) . . . . ?
Br1 C12 C13 C15 -1.8(3) . . . . ?
C19 N3 C16 C3 -118.51(16) . . . . ?
N4 N3 C16 C3 57.16(19) . . . . ?
C4 C3 C16 N3 -120.26(15) . . . . ?
C2 C3 C16 N3 65.62(18) . . . . ?
N3 N4 C17 C18 -0.23(18) . . . . ?
N3 N4 C17 C20 179.61(15) . . . . ?
N4 C17 C18 C19 0.03(19) . . . . ?
C20 C17 C18 C19 -179.80(17) . . . . ?
N4 C17 C18 Br2 175.38(12) . . . . ?
C20 C17 C18 Br2 -4.4(3) . . . . ?
N4 N3 C19 C18 -0.35(17) . . . . ?
C16 N3 C19 C18 175.55(14) . . . . ?
N4 N3 C19 C21 -179.49(15) . . . . ?
C16 N3 C19 C21 -3.6(2) . . . . ?
C17 C18 C19 N3 0.19(17) . . . . ?
Br2 C18 C19 N3 -175.31(11) . . . . ?
C17 C18 C19 C21 179.24(16) . . . . ?
Br2 C18 C19 C21 3.7(3) . . . . ?
C23 N5 C22 C5 -122.59(16) . . . . ?
N6 N5 C22 C5 55.34(18) . . . . ?
C6 C5 C22 N5 -119.70(15) . . . . ?
C4 C5 C22 N5 67.15(18) . . . . ?
N6 N5 C23 C24 0.21(17) . . . . ?
C22 N5 C23 C24 178.26(14) . . . . ?
N6 N5 C23 C26 -179.08(14) . . . . ?
C22 N5 C23 C26 -1.0(2) . . . . ?
N5 C23 C24 C25 -0.33(17) . . . . ?
C26 C23 C24 C25 178.89(16) . . . . ?
N5 C23 C24 Br3 179.30(11) . . . . ?
C26 C23 C24 Br3 -1.5(3) . . . . ?
N5 N6 C25 C24 -0.21(18) . . . . ?
N5 N6 C25 C27 177.67(15) . . . . ?
C23 C24 C25 N6 0.34(19) . . . . ?
Br3 C24 C25 N6 -179.29(12) . . . . ?
C23 C24 C25 C27 -177.36(17) . . . . ?
Br3 C24 C25 C27 3.0(3) . . . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.063

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_nk171cor
_database_code_depnum_ccdc_archive 'CCDC 1533895'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H33 Br3 N6'
_chemical_formula_sum            'C27 H33 Br3 N6'
_chemical_formula_weight         681.32

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.7217(4)
_cell_length_b                   14.0379(4)
_cell_length_c                   16.3771(5)
_cell_angle_alpha                75.925(1)
_cell_angle_beta                 65.816(1)
_cell_angle_gamma                80.705(1)
_cell_volume                     2784.52(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.10

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_F_000             1368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.374
_shelx_estimated_absorpt_T_min   0.396
_shelx_estimated_absorpt_T_max   0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3959
_exptl_absorpt_correction_T_max  0.6688
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            41629
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.631
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             11325
_reflns_number_gt                8933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0378P)²+2.0456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11325
_refine_ls_number_parameters     667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0731
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.08471(2) 0.33554(2) 0.03791(2) 0.02511(8) Uani 1 1 d . . . . .
Br2 Br 0.47369(3) -0.22809(2) 0.22161(2) 0.03667(10) Uani 1 1 d . . . . .
Br3 Br 0.08455(3) 0.68024(2) 0.35277(2) 0.02467(8) Uani 1 1 d . . . . .
N1 N 0.76565(18) 0.35331(16) 0.12490(16) 0.0146(5) Uani 1 1 d . . . . .
N2 N 0.78695(19) 0.39042(17) 0.03460(16) 0.0169(5) Uani 1 1 d . . . . .
N3 N 0.48484(19) 0.05688(17) 0.10209(16) 0.0186(5) Uani 1 1 d . . . . .
N4 N 0.3795(2) 0.05958(18) 0.15880(17) 0.0224(6) Uani 1 1 d . . . . .
N5 N 0.27688(19) 0.50935(17) 0.17866(16) 0.0180(5) Uani 1 1 d . . . . .
N6 N 0.23282(19) 0.43616(17) 0.25088(16) 0.0190(5) Uani 1 1 d . . . . .
C1 C 0.5807(2) 0.3312(2) 0.14578(18) 0.0147(6) Uani 1 1 d . . . . .
C2 C 0.5859(2) 0.2458(2) 0.11482(18) 0.0150(6) Uani 1 1 d . . . . .
C3 C 0.5125(2) 0.2361(2) 0.07877(19) 0.0171(6) Uani 1 1 d . . . . .
C4 C 0.4316(2) 0.3107(2) 0.07584(19) 0.0170(6) Uani 1 1 d . . . . .
C5 C 0.4305(2) 0.3983(2) 0.10268(19) 0.0162(6) Uani 1 1 d . . . . .
C6 C 0.5060(2) 0.4094(2) 0.13701(19) 0.0157(6) Uani 1 1 d . . . . .
C7 C 0.6731(2) 0.1655(2) 0.1171(2) 0.0206(7) Uani 1 1 d . . . . .
H7A H 0.7008 0.1723 0.1604 0.031 Uiso 1 1 calc R U . . .
H7B H 0.7297 0.1708 0.0577 0.031 Uiso 1 1 calc R U . . .
H7C H 0.6441 0.1024 0.1349 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3470(2) 0.2949(2) 0.0438(2) 0.0234(7) Uani 1 1 d . . . . .
H8A H 0.3719 0.3154 -0.0213 0.035 Uiso 1 1 calc R U . . .
H8B H 0.2820 0.3328 0.0720 0.035 Uiso 1 1 calc R U . . .
H8C H 0.3337 0.2263 0.0606 0.035 Uiso 1 1 calc R U . . .
C9 C 0.5094(3) 0.5056(2) 0.1608(2) 0.0224(7) Uani 1 1 d . . . . .
H9A H 0.5825 0.5183 0.1440 0.034 Uiso 1 1 calc R U . . .
H9B H 0.4712 0.5019 0.2253 0.034 Uiso 1 1 calc R U . . .
H9C H 0.4767 0.5578 0.1284 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6556(2) 0.3379(2) 0.19070(19) 0.0173(6) Uani 1 1 d . . . . .
H10A H 0.6294 0.3919 0.2234 0.021 Uiso 1 1 calc R U . . .
H10B H 0.6554 0.2777 0.2349 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8932(2) 0.3912(2) -0.0057(2) 0.0171(6) Uani 1 1 d . . . . .
C12 C 0.9378(2) 0.3550(2) 0.0598(2) 0.0170(6) Uani 1 1 d . . . . .
C13 C 0.8556(2) 0.33163(19) 0.1430(2) 0.0153(6) Uani 1 1 d . . . . .
C14 C 0.9490(2) 0.4258(2) -0.1060(2) 0.0232(7) Uani 1 1 d . . . . .
H14A H 0.9007 0.4692 -0.1293 0.035 Uiso 1 1 calc R U . . .
H14B H 0.9724 0.3702 -0.1355 0.035 Uiso 1 1 calc R U . . .
H14C H 1.0099 0.4602 -0.1177 0.035 Uiso 1 1 calc R U . . .
C15 C 0.8541(2) 0.2928(2) 0.2365(2) 0.0211(7) Uani 1 1 d . . . . .
H15A H 0.8266 0.2287 0.2591 0.032 Uiso 1 1 calc R U . . .
H15B H 0.8091 0.3365 0.2762 0.032 Uiso 1 1 calc R U . . .
H15C H 0.9255 0.2882 0.2346 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5270(3) 0.1468(2) 0.0362(2) 0.0199(7) Uani 1 1 d . . . . .
H16A H 0.4916 0.1628 -0.0065 0.024 Uiso 1 1 calc R U . . .
H16B H 0.6027 0.1338 0.0017 0.024 Uiso 1 1 calc R U . . .
C17 C 0.3619(3) -0.0331(2) 0.2053(2) 0.0243(7) Uani 1 1 d . . . . .
C18 C 0.4558(3) -0.0927(2) 0.1764(2) 0.0239(7) Uani 1 1 d . . . . .
C19 C 0.5347(3) -0.0351(2) 0.1093(2) 0.0225(7) Uani 1 1 d . . . . .
C20 C 0.2538(3) -0.0599(3) 0.2766(2) 0.0375(9) Uani 1 1 d . . . . .
H20A H 0.2011 -0.0079 0.2703 0.056 Uiso 1 1 calc R U . . .
H20B H 0.2553 -0.0692 0.3362 0.056 Uiso 1 1 calc R U . . .
H20C H 0.2360 -0.1197 0.2690 0.056 Uiso 1 1 calc R U . . .
C21 C 0.6479(3) -0.0611(2) 0.0545(2) 0.0304(8) Uani 1 1 d . . . . .
H21A H 0.6937 -0.0301 0.0700 0.046 Uiso 1 1 calc R U . . .
H21B H 0.6616 -0.0389 -0.0093 0.046 Uiso 1 1 calc R U . . .
H21C H 0.6619 -0.1313 0.0670 0.046 Uiso 1 1 calc R U . . .
C22 C 0.3518(2) 0.4842(2) 0.09138(19) 0.0206(7) Uani 1 1 d . . . . .
H22A H 0.3912 0.5412 0.0533 0.025 Uiso 1 1 calc R U . . .
H22B H 0.3115 0.4682 0.0603 0.025 Uiso 1 1 calc R U . . .
C23 C 0.1645(2) 0.4811(2) 0.3176(2) 0.0180(6) Uani 1 1 d . . . . .
C24 C 0.1662(2) 0.5830(2) 0.2865(2) 0.0179(6) Uani 1 1 d . . . . .
C25 C 0.2378(2) 0.6003(2) 0.1973(2) 0.0189(6) Uani 1 1 d . . . . .
C26 C 0.0997(3) 0.4241(2) 0.4093(2) 0.0235(7) Uani 1 1 d . . . . .
H26A H 0.1333 0.3590 0.4180 0.035 Uiso 1 1 calc R U . . .
H26B H 0.0289 0.4200 0.4128 0.035 Uiso 1 1 calc R U . . .
H26C H 0.0955 0.4568 0.4559 0.035 Uiso 1 1 calc R U . . .
C27 C 0.2686(3) 0.6936(2) 0.1307(2) 0.0264(7) Uani 1 1 d . . . . .
H27A H 0.2647 0.6893 0.0746 0.040 Uiso 1 1 calc R U . . .
H27B H 0.3405 0.7051 0.1196 0.040 Uiso 1 1 calc R U . . .
H27C H 0.2207 0.7469 0.1549 0.040 Uiso 1 1 calc R U . . .
Br1A Br -0.06052(2) 0.13756(2) 0.46705(2) 0.02887(9) Uani 1 1 d . . . . .
Br2A Br 0.86436(2) 0.56803(2) 0.36014(2) 0.02422(8) Uani 1 1 d . . . . .
Br3A Br 0.89065(3) -0.17033(2) 0.12638(2) 0.03618(10) Uani 1 1 d . . . . .
N1A N 0.24743(18) 0.18265(16) 0.38873(16) 0.0148(5) Uani 1 1 d . . . . .
N2A N 0.22489(19) 0.15439(17) 0.47999(16) 0.0166(5) Uani 1 1 d . . . . .
N3A N 0.61292(19) 0.41023(16) 0.43479(16) 0.0162(5) Uani 1 1 d . . . . .
N4A N 0.6110(2) 0.46140(17) 0.35306(16) 0.0182(5) Uani 1 1 d . . . . .
N5A N 0.71984(19) -0.01499(16) 0.32025(16) 0.0166(5) Uani 1 1 d . . . . .
N6A N 0.78994(19) 0.05416(17) 0.26461(16) 0.0192(6) Uani 1 1 d . . . . .
C1A C 0.4336(2) 0.2014(2) 0.36836(18) 0.0136(6) Uani 1 1 d . . . . .
C2A C 0.4458(2) 0.27596(19) 0.40588(18) 0.0142(6) Uani 1 1 d . . . . .
C3A C 0.5250(2) 0.26328(19) 0.44177(18) 0.0133(6) Uani 1 1 d . . . . .
C4A C 0.5952(2) 0.17797(19) 0.43627(18) 0.0131(6) Uani 1 1 d . . . . .
C5A C 0.5783(2) 0.10116(19) 0.40342(18) 0.0131(6) Uani 1 1 d . . . . .
C6A C 0.4972(2) 0.11251(19) 0.37007(18) 0.0137(6) Uani 1 1 d . . . . .
C7A C 0.3718(2) 0.3683(2) 0.4110(2) 0.0191(7) Uani 1 1 d . . . . .
H7A1 H 0.3134 0.3610 0.4696 0.029 Uiso 1 1 calc R U . . .
H7A2 H 0.3444 0.3794 0.3639 0.029 Uiso 1 1 calc R U . . .
H7A3 H 0.4105 0.4234 0.4028 0.029 Uiso 1 1 calc R U . . .
C8A C 0.6867(2) 0.1698(2) 0.4669(2) 0.0194(6) Uani 1 1 d . . . . .
H8A1 H 0.7412 0.1223 0.4388 0.029 Uiso 1 1 calc R U . . .
H8A2 H 0.6609 0.1492 0.5321 0.029 Uiso 1 1 calc R U . . .
H8A3 H 0.7162 0.2327 0.4493 0.029 Uiso 1 1 calc R U . . .
C9A C 0.4744(2) 0.0285(2) 0.3388(2) 0.0192(6) Uani 1 1 d . . . . .
H9A1 H 0.4925 -0.0330 0.3723 0.029 Uiso 1 1 calc R U . . .
H9A2 H 0.5165 0.0325 0.2748 0.029 Uiso 1 1 calc R U . . .
H9A3 H 0.3998 0.0329 0.3495 0.029 Uiso 1 1 calc R U . . .
C10A C 0.3529(2) 0.2153(2) 0.32422(19) 0.0159(6) Uani 1 1 d . . . . .
H10C H 0.3453 0.2844 0.2976 0.019 Uiso 1 1 calc R U . . .
H10D H 0.3799 0.1787 0.2752 0.019 Uiso 1 1 calc R U . . .
C11A C 0.1218(2) 0.1338(2) 0.5181(2) 0.0175(6) Uani 1 1 d . . . . .
C12A C 0.0807(2) 0.1502(2) 0.4501(2) 0.0194(7) Uani 1 1 d . . . . .
C13A C 0.1617(2) 0.1811(2) 0.3681(2) 0.0167(6) Uani 1 1 d . . . . .
C14A C 0.0680(2) 0.0961(2) 0.6178(2) 0.0251(7) Uani 1 1 d . . . . .
H14D H 0.0844 0.1351 0.6507 0.038 Uiso 1 1 calc R U . . .
H14E H 0.0930 0.0288 0.6326 0.038 Uiso 1 1 calc R U . . .
H14F H -0.0080 0.1001 0.6345 0.038 Uiso 1 1 calc R U . . .
C15B C 0.1634(3) 0.2099(2) 0.2741(2) 0.0244(7) Uani 1 1 d . . . . .
H15D H 0.2252 0.1780 0.2335 0.037 Uiso 1 1 calc R U . . .
H15E H 0.1662 0.2800 0.2543 0.037 Uiso 1 1 calc R U . . .
H15F H 0.0997 0.1904 0.2736 0.037 Uiso 1 1 calc R U . . .
C16A C 0.5320(2) 0.3388(2) 0.49147(19) 0.0167(6) Uani 1 1 d . . . . .
H16C H 0.4625 0.3743 0.5141 0.020 Uiso 1 1 calc R U . . .
H16D H 0.5483 0.3044 0.5439 0.020 Uiso 1 1 calc R U . . .
C17A C 0.6928(2) 0.51878(19) 0.3176(2) 0.0169(6) Uani 1 1 d . . . . .
C18A C 0.7444(2) 0.5049(2) 0.3782(2) 0.0169(6) Uani 1 1 d . . . . .
C19A C 0.6921(2) 0.4359(2) 0.4531(2) 0.0170(6) Uani 1 1 d . . . . .
C20A C 0.7225(2) 0.5817(2) 0.2243(2) 0.0215(7) Uani 1 1 d . . . . .
H20D H 0.6593 0.6171 0.2177 0.032 Uiso 1 1 calc R U . . .
H20E H 0.7550 0.5409 0.1794 0.032 Uiso 1 1 calc R U . . .
H20F H 0.7722 0.6277 0.2159 0.032 Uiso 1 1 calc R U . . .
C21A C 0.7123(3) 0.3932(2) 0.5377(2) 0.0249(7) Uani 1 1 d . . . . .
H21D H 0.7627 0.4308 0.5411 0.037 Uiso 1 1 calc R U . . .
H21E H 0.7410 0.3262 0.5367 0.037 Uiso 1 1 calc R U . . .
H21F H 0.6463 0.3950 0.5900 0.037 Uiso 1 1 calc R U . . .
C22A C 0.6431(2) 0.0032(2) 0.40875(18) 0.0155(6) Uani 1 1 d . . . . .
H22C H 0.6813 0.0014 0.4476 0.019 Uiso 1 1 calc R U . . .
H22D H 0.5945 -0.0492 0.4370 0.019 Uiso 1 1 calc R U . . .
C23A C 0.8556(2) 0.0132(2) 0.1934(2) 0.0217(7) Uani 1 1 d . . . . .
C24A C 0.8255(3) -0.0817(2) 0.2059(2) 0.0224(7) Uani 1 1 d . . . . .
C25A C 0.7397(2) -0.0993(2) 0.2881(2) 0.0182(6) Uani 1 1 d . . . . .
C26A C 0.9436(3) 0.0664(2) 0.1169(2) 0.0354(9) Uani 1 1 d . . . . .
H26D H 0.9493 0.1272 0.1312 0.053 Uiso 1 1 calc R U . . .
H26E H 0.9291 0.0800 0.0625 0.053 Uiso 1 1 calc R U . . .
H26F H 1.0097 0.0266 0.1075 0.053 Uiso 1 1 calc R U . . .
C27A C 0.6804(3) -0.1891(2) 0.3380(2) 0.0275(8) Uani 1 1 d . . . . .
H27D H 0.6077 -0.1761 0.3423 0.041 Uiso 1 1 calc R U . . .
H27E H 0.6810 -0.2074 0.3982 0.041 Uiso 1 1 calc R U . . .
H27F H 0.7140 -0.2419 0.3057 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C12 1.883(3) . ?
Br2 C18 1.880(3) . ?
Br3 C24 1.878(3) . ?
N1 C13 1.356(4) . ?
N1 N2 1.365(3) . ?
N1 C10 1.465(4) . ?
N2 C11 1.333(4) . ?
N3 N4 1.361(3) . ?
N3 C19 1.362(4) . ?
N3 C16 1.468(4) . ?
N4 C17 1.341(4) . ?
N5 N6 1.358(3) . ?
N5 C25 1.358(4) . ?
N5 C22 1.466(4) . ?
N6 C23 1.332(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.399(4) . ?
C1 C10 1.514(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.512(4) . ?
C3 C4 1.405(4) . ?
C3 C16 1.526(4) . ?
C4 C5 1.399(4) . ?
C4 C8 1.520(4) . ?
C5 C6 1.408(4) . ?
C5 C22 1.513(4) . ?
C6 C9 1.507(4) . ?
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 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.398(4) . ?
C11 C14 1.490(4) . ?
C12 C13 1.371(4) . ?
C13 C15 1.489(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.389(4) . ?
C17 C20 1.501(5) . ?
C18 C19 1.382(4) . ?
C19 C21 1.478(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.398(4) . ?
C23 C26 1.495(4) . ?
C24 C25 1.374(4) . ?
C25 C27 1.480(4) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
Br1A C12A 1.874(3) . ?
Br2A C18A 1.879(3) . ?
Br3A C24A 1.876(3) . ?
N1A C13A 1.355(4) . ?
N1A N2A 1.364(3) . ?
N1A C10A 1.465(4) . ?
N2A C11A 1.339(4) . ?
N3A C19A 1.358(4) . ?
N3A N4A 1.365(3) . ?
N3A C16A 1.471(3) . ?
N4A C17A 1.333(4) . ?
N5A C25A 1.354(4) . ?
N5A N6A 1.361(3) . ?
N5A C22A 1.455(3) . ?
N6A C23A 1.342(4) . ?
C1A C2A 1.398(4) . ?
C1A C6A 1.404(4) . ?
C1A C10A 1.518(4) . ?
C2A C3A 1.402(4) . ?
C2A C7A 1.509(4) . ?
C3A C4A 1.407(4) . ?
C3A C16A 1.520(4) . ?
C4A C5A 1.404(4) . ?
C4A C8A 1.512(4) . ?
C5A C6A 1.400(4) . ?
C5A C22A 1.516(4) . ?
C6A C9A 1.515(4) . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 0.9600 . ?
C9A H9A1 0.9600 . ?
C9A H9A2 0.9600 . ?
C9A H9A3 0.9600 . ?
C10A H10C 0.9700 . ?
C10A H10D 0.9700 . ?
C11A C12A 1.399(4) . ?
C11A C14A 1.488(4) . ?
C12A C13A 1.369(4) . ?
C13A C15B 1.486(4) . ?
C14A H14D 0.9600 . ?
C14A H14E 0.9600 . ?
C14A H14F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16A H16C 0.9700 . ?
C16A H16D 0.9700 . ?
C17A C18A 1.399(4) . ?
C17A C20A 1.493(4) . ?
C18A C19A 1.372(4) . ?
C19A C21A 1.489(4) . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C23A C24A 1.402(4) . ?
C23A C26A 1.477(4) . ?
C24A C25A 1.376(4) . ?
C25A C27A 1.485(4) . ?
C26A H26D 0.9600 . ?
C26A H26E 0.9600 . ?
C26A H26F 0.9600 . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 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
C13 N1 N2 112.6(2) . . ?
C13 N1 C10 126.5(2) . . ?
N2 N1 C10 120.9(2) . . ?
C11 N2 N1 105.3(2) . . ?
N4 N3 C19 113.0(2) . . ?
N4 N3 C16 118.3(2) . . ?
C19 N3 C16 128.4(3) . . ?
C17 N4 N3 105.2(2) . . ?
N6 N5 C25 112.5(2) . . ?
N6 N5 C22 119.4(2) . . ?
C25 N5 C22 127.9(2) . . ?
C23 N6 N5 105.7(2) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 C10 119.2(2) . . ?
C6 C1 C10 120.3(3) . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 C7 120.0(3) . . ?
C3 C2 C7 120.1(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 C16 118.8(3) . . ?
C4 C3 C16 120.6(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C8 121.2(3) . . ?
C3 C4 C8 119.6(3) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 C22 120.7(3) . . ?
C6 C5 C22 118.9(3) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C9 119.9(3) . . ?
C5 C6 C9 120.7(3) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 112.6(2) . . ?
N1 C10 H10A 109.1 . . ?
C1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
C1 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C12 109.4(3) . . ?
N2 C11 C14 122.0(3) . . ?
C12 C11 C14 128.6(3) . . ?
C13 C12 C11 108.0(2) . . ?
C13 C12 Br1 125.5(2) . . ?
C11 C12 Br1 126.5(2) . . ?
N1 C13 C12 104.7(2) . . ?
N1 C13 C15 123.2(3) . . ?
C12 C13 C15 132.1(3) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C3 114.5(2) . . ?
N3 C16 H16A 108.6 . . ?
C3 C16 H16A 108.6 . . ?
N3 C16 H16B 108.6 . . ?
C3 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
N4 C17 C18 109.6(3) . . ?
N4 C17 C20 121.3(3) . . ?
C18 C17 C20 129.2(3) . . ?
C19 C18 C17 108.2(3) . . ?
C19 C18 Br2 125.7(2) . . ?
C17 C18 Br2 126.1(2) . . ?
N3 C19 C18 104.1(3) . . ?
N3 C19 C21 125.2(3) . . ?
C18 C19 C21 130.8(3) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C5 112.8(2) . . ?
N5 C22 H22A 109.0 . . ?
C5 C22 H22A 109.0 . . ?
N5 C22 H22B 109.0 . . ?
C5 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N6 C23 C24 109.4(3) . . ?
N6 C23 C26 121.6(3) . . ?
C24 C23 C26 129.1(3) . . ?
C25 C24 C23 107.7(3) . . ?
C25 C24 Br3 125.5(2) . . ?
C23 C24 Br3 126.8(2) . . ?
N5 C25 C24 104.7(2) . . ?
N5 C25 C27 124.5(3) . . ?
C24 C25 C27 130.8(3) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13A N1A N2A 112.5(2) . . ?
C13A N1A C10A 126.2(2) . . ?
N2A N1A C10A 121.2(2) . . ?
C11A N2A N1A 105.2(2) . . ?
C19A N3A N4A 112.5(2) . . ?
C19A N3A C16A 128.6(2) . . ?
N4A N3A C16A 118.9(2) . . ?
C17A N4A N3A 105.3(2) . . ?
C25A N5A N6A 113.0(2) . . ?
C25A N5A C22A 127.6(2) . . ?
N6A N5A C22A 119.0(2) . . ?
C23A N6A N5A 105.3(2) . . ?
C2A C1A C6A 120.2(3) . . ?
C2A C1A C10A 120.9(2) . . ?
C6A C1A C10A 118.9(2) . . ?
C1A C2A C3A 119.7(2) . . ?
C1A C2A C7A 120.4(2) . . ?
C3A C2A C7A 119.9(2) . . ?
C2A C3A C4A 120.2(2) . . ?
C2A C3A C16A 120.4(2) . . ?
C4A C3A C16A 119.3(2) . . ?
C5A C4A C3A 119.4(2) . . ?
C5A C4A C8A 121.0(2) . . ?
C3A C4A C8A 119.6(2) . . ?
C6A C5A C4A 120.2(2) . . ?
C6A C5A C22A 119.3(2) . . ?
C4A C5A C22A 120.4(2) . . ?
C5A C6A C1A 119.9(3) . . ?
C5A C6A C9A 120.7(2) . . ?
C1A C6A C9A 119.3(3) . . ?
C2A C7A H7A1 109.5 . . ?
C2A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C2A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
C4A C8A H8A1 109.5 . . ?
C4A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C4A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C6A C9A H9A1 109.5 . . ?
C6A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C6A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
N1A C10A C1A 112.9(2) . . ?
N1A C10A H10C 109.0 . . ?
C1A C10A H10C 109.0 . . ?
N1A C10A H10D 109.0 . . ?
C1A C10A H10D 109.0 . . ?
H10C C10A H10D 107.8 . . ?
N2A C11A C12A 109.5(3) . . ?
N2A C11A C14A 121.5(3) . . ?
C12A C11A C14A 129.0(3) . . ?
C13A C12A C11A 107.6(3) . . ?
C13A C12A Br1A 125.5(2) . . ?
C11A C12A Br1A 126.8(2) . . ?
N1A C13A C12A 105.1(2) . . ?
N1A C13A C15B 123.8(3) . . ?
C12A C13A C15B 131.0(3) . . ?
C11A C14A H14D 109.5 . . ?
C11A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C11A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C13A C15B H15D 109.5 . . ?
C13A C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13A C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N3A C16A C3A 114.1(2) . . ?
N3A C16A H16C 108.7 . . ?
C3A C16A H16C 108.7 . . ?
N3A C16A H16D 108.7 . . ?
C3A C16A H16D 108.7 . . ?
H16C C16A H16D 107.6 . . ?
N4A C17A C18A 109.6(3) . . ?
N4A C17A C20A 121.7(3) . . ?
C18A C17A C20A 128.6(3) . . ?
C19A C18A C17A 107.7(3) . . ?
C19A C18A Br2A 125.9(2) . . ?
C17A C18A Br2A 126.4(2) . . ?
N3A C19A C18A 104.8(2) . . ?
N3A C19A C21A 124.3(3) . . ?
C18A C19A C21A 130.8(3) . . ?
C17A C20A H20D 109.5 . . ?
C17A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C17A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C19A C21A H21D 109.5 . . ?
C19A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
C19A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
N5A C22A C5A 113.5(2) . . ?
N5A C22A H22C 108.9 . . ?
C5A C22A H22C 108.9 . . ?
N5A C22A H22D 108.9 . . ?
C5A C22A H22D 108.9 . . ?
H22C C22A H22D 107.7 . . ?
N6A C23A C24A 109.3(3) . . ?
N6A C23A C26A 121.7(3) . . ?
C24A C23A C26A 129.0(3) . . ?
C25A C24A C23A 107.7(3) . . ?
C25A C24A Br3A 125.7(2) . . ?
C23A C24A Br3A 126.6(2) . . ?
N5A C25A C24A 104.7(2) . . ?
N5A C25A C27A 124.3(3) . . ?
C24A C25A C27A 130.9(3) . . ?
C23A C26A H26D 109.5 . . ?
C23A C26A H26E 109.5 . . ?
H26D C26A H26E 109.5 . . ?
C23A C26A H26F 109.5 . . ?
H26D C26A H26F 109.5 . . ?
H26E C26A H26F 109.5 . . ?
C25A C27A H27D 109.5 . . ?
C25A C27A H27E 109.5 . . ?
H27D C27A H27E 109.5 . . ?
C25A C27A H27F 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 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
C13 N1 N2 C11 0.7(3) . . . . ?
C10 N1 N2 C11 -177.6(2) . . . . ?
C19 N3 N4 C17 1.4(3) . . . . ?
C16 N3 N4 C17 175.1(2) . . . . ?
C25 N5 N6 C23 -0.4(3) . . . . ?
C22 N5 N6 C23 -176.4(2) . . . . ?
C6 C1 C2 C3 -3.1(4) . . . . ?
C10 C1 C2 C3 175.7(2) . . . . ?
C6 C1 C2 C7 174.7(3) . . . . ?
C10 C1 C2 C7 -6.4(4) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C7 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C16 173.6(2) . . . . ?
C7 C2 C3 C16 -4.2(4) . . . . ?
C2 C3 C4 C5 5.0(4) . . . . ?
C16 C3 C4 C5 -170.3(3) . . . . ?
C2 C3 C4 C8 -174.8(3) . . . . ?
C16 C3 C4 C8 9.9(4) . . . . ?
C3 C4 C5 C6 -3.5(4) . . . . ?
C8 C4 C5 C6 176.4(3) . . . . ?
C3 C4 C5 C22 173.7(3) . . . . ?
C8 C4 C5 C22 -6.4(4) . . . . ?
C2 C1 C6 C5 4.7(4) . . . . ?
C10 C1 C6 C5 -174.2(2) . . . . ?
C2 C1 C6 C9 -173.0(3) . . . . ?
C10 C1 C6 C9 8.1(4) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
C22 C5 C6 C1 -178.5(3) . . . . ?
C4 C5 C6 C9 176.4(3) . . . . ?
C22 C5 C6 C9 -0.9(4) . . . . ?
C13 N1 C10 C1 -157.4(3) . . . . ?
N2 N1 C10 C1 20.7(3) . . . . ?
C2 C1 C10 N1 74.8(3) . . . . ?
C6 C1 C10 N1 -106.3(3) . . . . ?
N1 N2 C11 C12 -0.2(3) . . . . ?
N1 N2 C11 C14 179.1(2) . . . . ?
N2 C11 C12 C13 -0.3(3) . . . . ?
C14 C11 C12 C13 -179.6(3) . . . . ?
N2 C11 C12 Br1 177.13(19) . . . . ?
C14 C11 C12 Br1 -2.2(4) . . . . ?
N2 N1 C13 C12 -0.8(3) . . . . ?
C10 N1 C13 C12 177.4(2) . . . . ?
N2 N1 C13 C15 178.2(2) . . . . ?
C10 N1 C13 C15 -3.5(4) . . . . ?
C11 C12 C13 N1 0.6(3) . . . . ?
Br1 C12 C13 N1 -176.77(19) . . . . ?
C11 C12 C13 C15 -178.3(3) . . . . ?
Br1 C12 C13 C15 4.3(5) . . . . ?
N4 N3 C16 C3 57.4(3) . . . . ?
C19 N3 C16 C3 -130.0(3) . . . . ?
C2 C3 C16 N3 81.8(3) . . . . ?
C4 C3 C16 N3 -102.8(3) . . . . ?
N3 N4 C17 C18 -0.7(3) . . . . ?
N3 N4 C17 C20 179.0(3) . . . . ?
N4 C17 C18 C19 -0.2(4) . . . . ?
C20 C17 C18 C19 -179.9(3) . . . . ?
N4 C17 C18 Br2 179.0(2) . . . . ?
C20 C17 C18 Br2 -0.7(5) . . . . ?
N4 N3 C19 C18 -1.5(3) . . . . ?
C16 N3 C19 C18 -174.4(3) . . . . ?
N4 N3 C19 C21 178.1(3) . . . . ?
C16 N3 C19 C21 5.1(5) . . . . ?
C17 C18 C19 N3 1.0(3) . . . . ?
Br2 C18 C19 N3 -178.2(2) . . . . ?
C17 C18 C19 C21 -178.6(3) . . . . ?
Br2 C18 C19 C21 2.2(5) . . . . ?
N6 N5 C22 C5 -42.4(4) . . . . ?
C25 N5 C22 C5 142.3(3) . . . . ?
C4 C5 C22 N5 117.0(3) . . . . ?
C6 C5 C22 N5 -65.7(3) . . . . ?
N5 N6 C23 C24 0.0(3) . . . . ?
N5 N6 C23 C26 -180.0(3) . . . . ?
N6 C23 C24 C25 0.4(3) . . . . ?
C26 C23 C24 C25 -179.6(3) . . . . ?
N6 C23 C24 Br3 179.6(2) . . . . ?
C26 C23 C24 Br3 -0.4(5) . . . . ?
N6 N5 C25 C24 0.6(3) . . . . ?
C22 N5 C25 C24 176.2(3) . . . . ?
N6 N5 C25 C27 -178.0(3) . . . . ?
C22 N5 C25 C27 -2.5(5) . . . . ?
C23 C24 C25 N5 -0.6(3) . . . . ?
Br3 C24 C25 N5 -179.9(2) . . . . ?
C23 C24 C25 C27 177.9(3) . . . . ?
Br3 C24 C25 C27 -1.3(5) . . . . ?
C13A N1A N2A C11A 0.4(3) . . . . ?
C10A N1A N2A C11A 177.3(2) . . . . ?
C19A N3A N4A C17A 1.7(3) . . . . ?
C16A N3A N4A C17A -179.5(2) . . . . ?
C25A N5A N6A C23A 1.3(3) . . . . ?
C22A N5A N6A C23A 174.4(2) . . . . ?
C6A C1A C2A C3A 2.7(4) . . . . ?
C10A C1A C2A C3A -176.5(2) . . . . ?
C6A C1A C2A C7A -175.1(3) . . . . ?
C10A C1A C2A C7A 5.7(4) . . . . ?
C1A C2A C3A C4A 3.0(4) . . . . ?
C7A C2A C3A C4A -179.2(2) . . . . ?
C1A C2A C3A C16A -173.7(2) . . . . ?
C7A C2A C3A C16A 4.1(4) . . . . ?
C2A C3A C4A C5A -6.7(4) . . . . ?
C16A C3A C4A C5A 170.0(2) . . . . ?
C2A C3A C4A C8A 174.1(3) . . . . ?
C16A C3A C4A C8A -9.2(4) . . . . ?
C3A C4A C5A C6A 4.8(4) . . . . ?
C8A C4A C5A C6A -176.0(3) . . . . ?
C3A C4A C5A C22A -171.7(2) . . . . ?
C8A C4A C5A C22A 7.5(4) . . . . ?
C4A C5A C6A C1A 0.8(4) . . . . ?
C22A C5A C6A C1A 177.3(2) . . . . ?
C4A C5A C6A C9A -176.9(2) . . . . ?
C22A C5A C6A C9A -0.5(4) . . . . ?
C2A C1A C6A C5A -4.6(4) . . . . ?
C10A C1A C6A C5A 174.6(2) . . . . ?
C2A C1A C6A C9A 173.2(3) . . . . ?
C10A C1A C6A C9A -7.6(4) . . . . ?
C13A N1A C10A C1A -176.2(2) . . . . ?
N2A N1A C10A C1A 7.2(3) . . . . ?
C2A C1A C10A N1A -90.4(3) . . . . ?
C6A C1A C10A N1A 90.3(3) . . . . ?
N1A N2A C11A C12A -0.5(3) . . . . ?
N1A N2A C11A C14A 177.5(3) . . . . ?
N2A C11A C12A C13A 0.4(3) . . . . ?
C14A C11A C12A C13A -177.4(3) . . . . ?
N2A C11A C12A Br1A -177.3(2) . . . . ?
C14A C11A C12A Br1A 4.9(5) . . . . ?
N2A N1A C13A C12A -0.1(3) . . . . ?
C10A N1A C13A C12A -176.9(2) . . . . ?
N2A N1A C13A C15B 179.0(3) . . . . ?
C10A N1A C13A C15B 2.2(4) . . . . ?
C11A C12A C13A N1A -0.2(3) . . . . ?
Br1A C12A C13A N1A 177.6(2) . . . . ?
C11A C12A C13A C15B -179.2(3) . . . . ?
Br1A C12A C13A C15B -1.4(5) . . . . ?
C19A N3A C16A C3A -128.5(3) . . . . ?
N4A N3A C16A C3A 53.0(3) . . . . ?
C2A C3A C16A N3A -98.4(3) . . . . ?
C4A C3A C16A N3A 84.9(3) . . . . ?
N3A N4A C17A C18A -1.3(3) . . . . ?
N3A N4A C17A C20A 175.7(2) . . . . ?
N4A C17A C18A C19A 0.4(3) . . . . ?
C20A C17A C18A C19A -176.2(3) . . . . ?
N4A C17A C18A Br2A 179.8(2) . . . . ?
C20A C17A C18A Br2A 3.1(4) . . . . ?
N4A N3A C19A C18A -1.5(3) . . . . ?
C16A N3A C19A C18A 179.9(3) . . . . ?
N4A N3A C19A C21A 179.2(3) . . . . ?
C16A N3A C19A C21A 0.6(4) . . . . ?
C17A C18A C19A N3A 0.6(3) . . . . ?
Br2A C18A C19A N3A -178.7(2) . . . . ?
C17A C18A C19A C21A 179.9(3) . . . . ?
Br2A C18A C19A C21A 0.5(5) . . . . ?
C25A N5A C22A C5A -135.4(3) . . . . ?
N6A N5A C22A C5A 52.6(3) . . . . ?
C6A C5A C22A N5A 73.8(3) . . . . ?
C4A C5A C22A N5A -109.7(3) . . . . ?
N5A N6A C23A C24A -0.2(3) . . . . ?
N5A N6A C23A C26A 179.7(3) . . . . ?
N6A C23A C24A C25A -0.9(4) . . . . ?
C26A C23A C24A C25A 179.2(3) . . . . ?
N6A C23A C24A Br3A 179.8(2) . . . . ?
C26A C23A C24A Br3A -0.1(5) . . . . ?
N6A N5A C25A C24A -1.8(3) . . . . ?
C22A N5A C25A C24A -174.2(3) . . . . ?
N6A N5A C25A C27A 175.7(3) . . . . ?
C22A N5A C25A C27A 3.3(5) . . . . ?
C23A C24A C25A N5A 1.6(3) . . . . ?
Br3A C24A C25A N5A -179.1(2) . . . . ?
C23A C24A C25A C27A -175.7(3) . . . . ?
Br3A C24A C25A C27A 3.6(5) . . . . ?

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
C10 H10A N4A 0.97 2.45 3.319(4) 148.5 .
C15 H15A N6A 0.96 2.55 3.476(4) 161.2 .
C21 H21C Br2 0.96 3.01 3.468(3) 111.1 .
C27 H27C Br3 0.96 3.00 3.454(3) 110.5 .
C10A H10C N6 0.97 2.57 3.454(3) 151.1 .
C15B H15D N4 0.96 2.54 3.484(4) 166.3 .
C15B H15E N6 0.96 2.49 3.352(4) 149.7 .
C20A H20F Br2A 0.96 3.00 3.463(3) 110.8 .
C22A H22C N2A 0.97 2.63 3.308(4) 127.1 2_656
C27A H27F Br3A 0.96 3.00 3.466(3) 111.0 .

_refine_diff_density_max         0.837
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.087

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch39new
_database_code_depnum_ccdc_archive 'CCDC 1533892'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N6'
_chemical_formula_sum            'C24 H30 N6'
_chemical_formula_weight         402.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6138(3)
_cell_length_b                   22.9808(8)
_cell_length_c                   19.5255(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.863(1)
_cell_angle_gamma                90
_cell_volume                     4304.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7526
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.38

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53296
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         26.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8859
_reflns_number_gt                6041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS.97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0485P)²+0.9307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8859
_refine_ls_number_parameters     547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 0.78732(13) 0.51997(6) 0.36862(6) 0.0171(3) Uani 1 1 d . . . . .
N2 N 0.88213(14) 0.50192(6) 0.41882(7) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.39287(14) 0.62531(6) 0.13639(7) 0.0174(3) Uani 1 1 d . . . . .
N4 N 0.45596(15) 0.66825(7) 0.17418(7) 0.0243(4) Uani 1 1 d . . . . .
N5 N 0.72427(13) 0.39615(6) 0.09819(6) 0.0168(3) Uani 1 1 d . . . . .
N6 N 0.80563(15) 0.34988(7) 0.08543(7) 0.0219(3) Uani 1 1 d . . . . .
C1 C 0.59133(16) 0.48861(7) 0.28774(8) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.49815(16) 0.53200(7) 0.26361(8) 0.0154(4) Uani 1 1 d . . . . .
C3 C 0.43978(15) 0.52901(7) 0.19565(8) 0.0146(4) Uani 1 1 d . . . . .
C4 C 0.47265(16) 0.48251(7) 0.15309(8) 0.0157(4) Uani 1 1 d . . . . .
C5 C 0.56431(16) 0.43916(7) 0.17841(8) 0.0155(4) Uani 1 1 d . . . . .
C6 C 0.62686(16) 0.44250(7) 0.24541(8) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.45680(16) 0.58074(8) 0.31065(8) 0.0178(4) Uani 1 1 d . . . . .
H7A H 0.4399 0.6166 0.2833 0.021 Uiso 1 1 calc R U . . .
H7B H 0.5347 0.5885 0.3452 0.021 Uiso 1 1 calc R U . . .
C8 C 0.32551(17) 0.56587(8) 0.34747(8) 0.0213(4) Uani 1 1 d . . . . .
H8A H 0.2465 0.5610 0.3135 0.032 Uiso 1 1 calc R U . . .
H8B H 0.3055 0.5974 0.3791 0.032 Uiso 1 1 calc R U . . .
H8C H 0.3406 0.5296 0.3733 0.032 Uiso 1 1 calc R U . . .
C9 C 0.40571(16) 0.47820(8) 0.08057(8) 0.0182(4) Uani 1 1 d . . . . .
H9A H 0.4707 0.4581 0.0513 0.022 Uiso 1 1 calc R U . . .
H9B H 0.3901 0.5179 0.0620 0.022 Uiso 1 1 calc R U . . .
C10 C 0.26654(17) 0.44540(9) 0.07672(9) 0.0243(4) Uani 1 1 d . . . . .
H10A H 0.2813 0.4059 0.0945 0.036 Uiso 1 1 calc R U . . .
H10B H 0.2289 0.4435 0.0289 0.036 Uiso 1 1 calc R U . . .
H10C H 0.2005 0.4658 0.1043 0.036 Uiso 1 1 calc R U . . .
C11 C 0.72617(17) 0.39584(7) 0.27280(8) 0.0189(4) Uani 1 1 d . . . . .
H11A H 0.7952 0.4133 0.3067 0.023 Uiso 1 1 calc R U . . .
H11B H 0.7775 0.3801 0.2346 0.023 Uiso 1 1 calc R U . . .
C12 C 0.65069(19) 0.34587(8) 0.30696(9) 0.0258(4) Uani 1 1 d . . . . .
H12A H 0.5989 0.3613 0.3445 0.039 Uiso 1 1 calc R U . . .
H12B H 0.7192 0.3173 0.3252 0.039 Uiso 1 1 calc R U . . .
H12C H 0.5857 0.3271 0.2730 0.039 Uiso 1 1 calc R U . . .
C13 C 0.65264(16) 0.49041(8) 0.36141(8) 0.0169(4) Uani 1 1 d . . . . .
H13A H 0.5866 0.5106 0.3901 0.020 Uiso 1 1 calc R U . . .
H13B H 0.6640 0.4501 0.3788 0.020 Uiso 1 1 calc R U . . .
C14 C 0.98425(17) 0.54100(8) 0.41820(8) 0.0201(4) Uani 1 1 d . . . . .
H14 H 1.0668 0.5398 0.4478 0.024 Uiso 1 1 calc R U . . .
C15 C 0.95536(17) 0.58393(8) 0.36892(9) 0.0229(4) Uani 1 1 d . . . . .
H15 H 1.0116 0.6164 0.3588 0.027 Uiso 1 1 calc R U . . .
C16 C 0.82779(17) 0.56892(8) 0.33824(9) 0.0216(4) Uani 1 1 d . . . . .
H16 H 0.7775 0.5894 0.3022 0.026 Uiso 1 1 calc R U . . .
C17 C 0.33455(16) 0.57464(7) 0.16981(8) 0.0176(4) Uani 1 1 d . . . . .
H17A H 0.2658 0.5559 0.1368 0.021 Uiso 1 1 calc R U . . .
H17B H 0.2836 0.5884 0.2091 0.021 Uiso 1 1 calc R U . . .
C18 C 0.48249(18) 0.70895(8) 0.12832(9) 0.0252(4) Uani 1 1 d . . . . .
H18 H 0.5278 0.7448 0.1395 0.030 Uiso 1 1 calc R U . . .
C19 C 0.43601(19) 0.69279(8) 0.06209(9) 0.0265(4) Uani 1 1 d . . . . .
H19 H 0.4426 0.7144 0.0209 0.032 Uiso 1 1 calc R U . . .
C20 C 0.37892(18) 0.63909(8) 0.06941(8) 0.0230(4) Uani 1 1 d . . . . .
H20 H 0.3369 0.6156 0.0337 0.028 Uiso 1 1 calc R U . . .
C21 C 0.59664(16) 0.38737(8) 0.13415(8) 0.0184(4) Uani 1 1 d . . . . .
H21A H 0.6075 0.3523 0.1634 0.022 Uiso 1 1 calc R U . . .
H21B H 0.5174 0.3806 0.1000 0.022 Uiso 1 1 calc R U . . .
C22 C 0.90658(18) 0.37213(9) 0.04966(8) 0.0233(4) Uani 1 1 d . . . . .
H22 H 0.9811 0.3500 0.0335 0.028 Uiso 1 1 calc R U . . .
C23 C 0.88955(18) 0.43145(9) 0.03902(9) 0.0245(4) Uani 1 1 d . . . . .
H23 H 0.9472 0.4568 0.0149 0.029 Uiso 1 1 calc R U . . .
C24 C 0.77153(17) 0.44550(8) 0.07081(8) 0.0212(4) Uani 1 1 d . . . . .
H24 H 0.7306 0.4830 0.0731 0.025 Uiso 1 1 calc R U . . .
N1A N 0.22142(14) 0.28778(6) 0.16670(7) 0.0189(3) Uani 1 1 d . . . . .
N2A N 0.25134(19) 0.28684(8) 0.10054(8) 0.0424(5) Uani 1 1 d . . . . .
N3A N 0.03504(14) 0.15545(6) 0.38278(7) 0.0197(3) Uani 1 1 d . . . . .
N4A N -0.00453(15) 0.10388(7) 0.35525(8) 0.0293(4) Uani 1 1 d . . . . .
N5A N 0.29679(14) 0.39511(6) 0.44714(7) 0.0183(3) Uani 1 1 d . . . . .
N6A N 0.37309(15) 0.44240(6) 0.46619(7) 0.0222(3) Uani 1 1 d . . . . .
C1A C 0.07469(16) 0.31293(8) 0.26069(8) 0.0169(4) Uani 1 1 d . . . . .
C2A C 0.01186(16) 0.26338(7) 0.28595(8) 0.0163(4) Uani 1 1 d . . . . .
C3A C -0.00487(16) 0.25883(8) 0.35662(8) 0.0175(4) Uani 1 1 d . . . . .
C4A C 0.03982(16) 0.30390(8) 0.40141(8) 0.0177(4) Uani 1 1 d . . . . .
C5A C 0.10191(16) 0.35349(8) 0.37484(8) 0.0172(4) Uani 1 1 d . . . . .
C6A C 0.12283(16) 0.35779(7) 0.30470(8) 0.0172(4) Uani 1 1 d . . . . .
C7A C -0.03741(17) 0.21512(8) 0.23730(8) 0.0195(4) Uani 1 1 d . . . . .
H7A1 H -0.0285 0.1774 0.2617 0.023 Uiso 1 1 calc R U . . .
H7A2 H 0.0235 0.2139 0.1984 0.023 Uiso 1 1 calc R U . . .
C8A C -0.18889(17) 0.22312(8) 0.20929(9) 0.0239(4) Uani 1 1 d . . . . .
H8A1 H -0.2501 0.2232 0.2475 0.036 Uiso 1 1 calc R U . . .
H8A2 H -0.2153 0.1911 0.1779 0.036 Uiso 1 1 calc R U . . .
H8A3 H -0.1982 0.2602 0.1846 0.036 Uiso 1 1 calc R U . . .
C9A C 0.01909(18) 0.29920(8) 0.47754(8) 0.0228(4) Uani 1 1 d . . . . .
H9A1 H 0.0884 0.3241 0.5034 0.027 Uiso 1 1 calc R U . . .
H9A2 H 0.0353 0.2585 0.4926 0.027 Uiso 1 1 calc R U . . .
C10A C -0.12758(19) 0.31776(10) 0.49413(9) 0.0324(5) Uani 1 1 d . . . . .
H10D H -0.1427 0.3585 0.4809 0.049 Uiso 1 1 calc R U . . .
H10E H -0.1376 0.3135 0.5435 0.049 Uiso 1 1 calc R U . . .
H10F H -0.1965 0.2932 0.4687 0.049 Uiso 1 1 calc R U . . .
C11A C 0.19375(17) 0.41052(8) 0.27618(9) 0.0209(4) Uani 1 1 d . . . . .
H11C H 0.2485 0.3983 0.2375 0.025 Uiso 1 1 calc R U . . .
H11D H 0.2593 0.4272 0.3123 0.025 Uiso 1 1 calc R U . . .
C12A C 0.08895(18) 0.45731(8) 0.25123(9) 0.0251(4) Uani 1 1 d . . . . .
H12D H 0.0226 0.4408 0.2162 0.038 Uiso 1 1 calc R U . . .
H12E H 0.1387 0.4899 0.2315 0.038 Uiso 1 1 calc R U . . .
H12F H 0.0385 0.4712 0.2900 0.038 Uiso 1 1 calc R U . . .
C13A C 0.09399(17) 0.31702(8) 0.18474(8) 0.0189(4) Uani 1 1 d . . . . .
H13C H 0.0128 0.2991 0.1589 0.023 Uiso 1 1 calc R U . . .
H13D H 0.0980 0.3585 0.1713 0.023 Uiso 1 1 calc R U . . .
C14A C 0.3690(2) 0.25623(10) 0.10121(11) 0.0452(6) Uani 1 1 d . . . . .
H14A H 0.4164 0.2480 0.0612 0.054 Uiso 1 1 calc R U . . .
C15A C 0.4145(2) 0.23791(9) 0.16542(11) 0.0361(5) Uani 1 1 d . . . . .
H15A H 0.4954 0.2158 0.1785 0.043 Uiso 1 1 calc R U . . .
C16A C 0.31662(19) 0.25880(10) 0.20612(10) 0.0349(5) Uani 1 1 d . . . . .
H16A H 0.3161 0.2536 0.2544 0.042 Uiso 1 1 calc R U . . .
C17A C -0.06530(17) 0.20328(8) 0.38362(8) 0.0199(4) Uani 1 1 d . . . . .
H17C H -0.0918 0.2096 0.4312 0.024 Uiso 1 1 calc R U . . .
H17D H -0.1506 0.1928 0.3550 0.024 Uiso 1 1 calc R U . . .
C18A C 0.1118(2) 0.07289(9) 0.35589(10) 0.0307(5) Uani 1 1 d . . . . .
H18A H 0.1165 0.0340 0.3396 0.037 Uiso 1 1 calc R U . . .
C19A C 0.22562(19) 0.10422(9) 0.38321(10) 0.0328(5) Uani 1 1 d . . . . .
H19A H 0.3199 0.0918 0.3891 0.039 Uiso 1 1 calc R U . . .
C20A C 0.17234(18) 0.15669(9) 0.39969(10) 0.0312(5) Uani 1 1 d . . . . .
H20A H 0.2233 0.1886 0.4196 0.037 Uiso 1 1 calc R U . . .
C21A C 0.15067(16) 0.40260(8) 0.42202(8) 0.0197(4) Uani 1 1 d . . . . .
H21C H 0.1401 0.4400 0.3970 0.024 Uiso 1 1 calc R U . . .
H21D H 0.0915 0.4041 0.4616 0.024 Uiso 1 1 calc R U . . .
C22A C 0.49499(18) 0.42089(8) 0.49094(8) 0.0214(4) Uani 1 1 d . . . . .
H22A H 0.5712 0.4440 0.5085 0.026 Uiso 1 1 calc R U . . .
C23A C 0.49682(19) 0.36086(9) 0.48787(10) 0.0294(5) Uani 1 1 d . . . . .
H23A H 0.5713 0.3356 0.5023 0.035 Uiso 1 1 calc R U . . .
C24A C 0.36787(18) 0.34577(9) 0.45946(10) 0.0314(5) Uani 1 1 d . . . . .
H24A H 0.3350 0.3074 0.4502 0.038 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 C16 1.341(2) . ?
N1 N2 1.3576(18) . ?
N1 C13 1.461(2) . ?
N2 C14 1.331(2) . ?
N3 C20 1.344(2) . ?
N3 N4 1.3511(19) . ?
N3 C17 1.465(2) . ?
N4 C18 1.331(2) . ?
N5 C24 1.346(2) . ?
N5 N6 1.3532(19) . ?
N5 C21 1.468(2) . ?
N6 C22 1.335(2) . ?
C1 C6 1.400(2) . ?
C1 C2 1.401(2) . ?
C1 C13 1.518(2) . ?
C2 C3 1.407(2) . ?
C2 C7 1.518(2) . ?
C3 C4 1.403(2) . ?
C3 C17 1.519(2) . ?
C4 C5 1.398(2) . ?
C4 C9 1.519(2) . ?
C5 C6 1.405(2) . ?
C5 C21 1.515(2) . ?
C6 C11 1.509(2) . ?
C7 C8 1.533(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.533(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.535(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.372(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.362(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1A C16A 1.334(2) . ?
N1A N2A 1.3424(19) . ?
N1A C13A 1.461(2) . ?
N2A C14A 1.331(3) . ?
N3A C20A 1.339(2) . ?
N3A N4A 1.346(2) . ?
N3A C17A 1.463(2) . ?
N4A C18A 1.325(2) . ?
N5A C24A 1.337(2) . ?
N5A N6A 1.3494(19) . ?
N5A C21A 1.467(2) . ?
N6A C22A 1.332(2) . ?
C1A C2A 1.395(2) . ?
C1A C6A 1.401(2) . ?
C1A C13A 1.510(2) . ?
C2A C3A 1.404(2) . ?
C2A C7A 1.515(2) . ?
C3A C4A 1.404(2) . ?
C3A C17A 1.512(2) . ?
C4A C5A 1.402(2) . ?
C4A C9A 1.517(2) . ?
C5A C6A 1.401(2) . ?
C5A C21A 1.511(2) . ?
C6A C11A 1.515(2) . ?
C7A C8A 1.532(2) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A C10A 1.529(2) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A C12A 1.531(2) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.366(3) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.359(3) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A C19A 1.387(3) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.357(3) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C22A C23A 1.381(3) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.368(3) . ?
C23A H23A 0.9500 . ?
C24A H24A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 N2 112.02(13) . . ?
C16 N1 C13 128.98(14) . . ?
N2 N1 C13 118.36(13) . . ?
C14 N2 N1 104.30(13) . . ?
C20 N3 N4 111.79(14) . . ?
C20 N3 C17 127.22(14) . . ?
N4 N3 C17 120.57(13) . . ?
C18 N4 N3 104.19(14) . . ?
C24 N5 N6 111.98(14) . . ?
C24 N5 C21 128.41(14) . . ?
N6 N5 C21 119.48(14) . . ?
C22 N6 N5 104.17(15) . . ?
C6 C1 C2 121.08(14) . . ?
C6 C1 C13 119.04(14) . . ?
C2 C1 C13 119.86(14) . . ?
C1 C2 C3 119.19(15) . . ?
C1 C2 C7 120.62(14) . . ?
C3 C2 C7 120.16(14) . . ?
C4 C3 C2 120.29(15) . . ?
C4 C3 C17 120.03(14) . . ?
C2 C3 C17 119.59(14) . . ?
C5 C4 C3 119.68(14) . . ?
C5 C4 C9 120.04(15) . . ?
C3 C4 C9 120.25(14) . . ?
C4 C5 C6 120.70(15) . . ?
C4 C5 C21 120.44(14) . . ?
C6 C5 C21 118.86(14) . . ?
C1 C6 C5 119.01(15) . . ?
C1 C6 C11 120.14(14) . . ?
C5 C6 C11 120.80(15) . . ?
C2 C7 C8 112.13(14) . . ?
C2 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C2 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 C10 113.04(13) . . ?
C4 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C4 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C12 112.28(14) . . ?
C6 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
C6 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C1 112.90(13) . . ?
N1 C13 H13A 109.0 . . ?
C1 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C1 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N2 C14 C15 111.79(14) . . ?
N2 C14 H14 124.1 . . ?
C15 C14 H14 124.1 . . ?
C16 C15 C14 104.73(16) . . ?
C16 C15 H15 127.6 . . ?
C14 C15 H15 127.6 . . ?
N1 C16 C15 107.16(15) . . ?
N1 C16 H16 126.4 . . ?
C15 C16 H16 126.4 . . ?
N3 C17 C3 115.49(13) . . ?
N3 C17 H17A 108.4 . . ?
C3 C17 H17A 108.4 . . ?
N3 C17 H17B 108.4 . . ?
C3 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?
N4 C18 C19 111.96(17) . . ?
N4 C18 H18 124.0 . . ?
C19 C18 H18 124.0 . . ?
C20 C19 C18 104.53(16) . . ?
C20 C19 H19 127.7 . . ?
C18 C19 H19 127.7 . . ?
N3 C20 C19 107.52(16) . . ?
N3 C20 H20 126.2 . . ?
C19 C20 H20 126.2 . . ?
N5 C21 C5 112.01(14) . . ?
N5 C21 H21A 109.2 . . ?
C5 C21 H21A 109.2 . . ?
N5 C21 H21B 109.2 . . ?
C5 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
N6 C22 C23 111.86(16) . . ?
N6 C22 H22 124.1 . . ?
C23 C22 H22 124.1 . . ?
C24 C23 C22 104.90(16) . . ?
C24 C23 H23 127.6 . . ?
C22 C23 H23 127.6 . . ?
N5 C24 C23 107.09(16) . . ?
N5 C24 H24 126.5 . . ?
C23 C24 H24 126.5 . . ?
C16A N1A N2A 111.36(15) . . ?
C16A N1A C13A 130.13(14) . . ?
N2A N1A C13A 118.48(14) . . ?
C14A N2A N1A 103.65(16) . . ?
C20A N3A N4A 111.40(15) . . ?
C20A N3A C17A 128.37(15) . . ?
N4A N3A C17A 119.81(13) . . ?
C18A N4A N3A 104.71(14) . . ?
C24A N5A N6A 111.82(14) . . ?
C24A N5A C21A 128.76(15) . . ?
N6A N5A C21A 119.22(14) . . ?
C22A N6A N5A 104.46(14) . . ?
C2A C1A C6A 121.13(15) . . ?
C2A C1A C13A 118.89(15) . . ?
C6A C1A C13A 119.95(15) . . ?
C1A C2A C3A 119.32(15) . . ?
C1A C2A C7A 120.02(14) . . ?
C3A C2A C7A 120.66(15) . . ?
C2A C3A C4A 120.44(16) . . ?
C2A C3A C17A 118.54(15) . . ?
C4A C3A C17A 120.95(14) . . ?
C5A C4A C3A 119.28(15) . . ?
C5A C4A C9A 120.51(15) . . ?
C3A C4A C9A 120.20(15) . . ?
C6A C5A C4A 120.78(15) . . ?
C6A C5A C21A 118.95(15) . . ?
C4A C5A C21A 120.25(14) . . ?
C1A C6A C5A 118.98(15) . . ?
C1A C6A C11A 120.11(14) . . ?
C5A C6A C11A 120.90(15) . . ?
C2A C7A C8A 112.68(14) . . ?
C2A C7A H7A1 109.1 . . ?
C8A C7A H7A1 109.1 . . ?
C2A C7A H7A2 109.1 . . ?
C8A C7A H7A2 109.1 . . ?
H7A1 C7A H7A2 107.8 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C4A C9A C10A 111.83(14) . . ?
C4A C9A H9A1 109.2 . . ?
C10A C9A H9A1 109.2 . . ?
C4A C9A H9A2 109.2 . . ?
C10A C9A H9A2 109.2 . . ?
H9A1 C9A H9A2 107.9 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C6A C11A C12A 112.10(14) . . ?
C6A C11A H11C 109.2 . . ?
C12A C11A H11C 109.2 . . ?
C6A C11A H11D 109.2 . . ?
C12A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
N1A C13A C1A 111.64(13) . . ?
N1A C13A H13C 109.3 . . ?
C1A C13A H13C 109.3 . . ?
N1A C13A H13D 109.3 . . ?
C1A C13A H13D 109.3 . . ?
H13C C13A H13D 108.0 . . ?
N2A C14A C15A 113.01(18) . . ?
N2A C14A H14A 123.5 . . ?
C15A C14A H14A 123.5 . . ?
C16A C15A C14A 103.68(18) . . ?
C16A C15A H15A 128.2 . . ?
C14A C15A H15A 128.2 . . ?
N1A C16A C15A 108.29(17) . . ?
N1A C16A H16A 125.9 . . ?
C15A C16A H16A 125.9 . . ?
N3A C17A C3A 111.18(13) . . ?
N3A C17A H17C 109.4 . . ?
C3A C17A H17C 109.4 . . ?
N3A C17A H17D 109.4 . . ?
C3A C17A H17D 109.4 . . ?
H17C C17A H17D 108.0 . . ?
N4A C18A C19A 111.61(18) . . ?
N4A C18A H18A 124.2 . . ?
C19A C18A H18A 124.2 . . ?
C20A C19A C18A 104.58(17) . . ?
C20A C19A H19A 127.7 . . ?
C18A C19A H19A 127.7 . . ?
N3A C20A C19A 107.70(17) . . ?
N3A C20A H20A 126.1 . . ?
C19A C20A H20A 126.1 . . ?
N5A C21A C5A 111.53(13) . . ?
N5A C21A H21C 109.3 . . ?
C5A C21A H21C 109.3 . . ?
N5A C21A H21D 109.3 . . ?
C5A C21A H21D 109.3 . . ?
H21C C21A H21D 108.0 . . ?
N6A C22A C23A 111.61(16) . . ?
N6A C22A H22A 124.2 . . ?
C23A C22A H22A 124.2 . . ?
C24A C23A C22A 104.89(17) . . ?
C24A C23A H23A 127.6 . . ?
C22A C23A H23A 127.6 . . ?
N5A C24A C23A 107.23(17) . . ?
N5A C24A H24A 126.4 . . ?
C23A C24A H24A 126.4 . . ?

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
C16 N1 N2 C14 -0.71(18) . . . . ?
C13 N1 N2 C14 -172.36(14) . . . . ?
C20 N3 N4 C18 -0.78(18) . . . . ?
C17 N3 N4 C18 -173.84(14) . . . . ?
C24 N5 N6 C22 0.67(17) . . . . ?
C21 N5 N6 C22 176.84(13) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C13 C1 C2 C3 -178.58(14) . . . . ?
C6 C1 C2 C7 178.03(14) . . . . ?
C13 C1 C2 C7 -0.5(2) . . . . ?
C1 C2 C3 C4 1.2(2) . . . . ?
C7 C2 C3 C4 -176.94(14) . . . . ?
C1 C2 C3 C17 177.77(14) . . . . ?
C7 C2 C3 C17 -0.4(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C17 C3 C4 C5 -176.84(14) . . . . ?
C2 C3 C4 C9 177.86(14) . . . . ?
C17 C3 C4 C9 1.3(2) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C9 C4 C5 C6 -179.90(14) . . . . ?
C3 C4 C5 C21 177.58(14) . . . . ?
C9 C4 C5 C21 -0.6(2) . . . . ?
C2 C1 C6 C5 -1.9(2) . . . . ?
C13 C1 C6 C5 176.61(14) . . . . ?
C2 C1 C6 C11 -179.26(14) . . . . ?
C13 C1 C6 C11 -0.8(2) . . . . ?
C4 C5 C6 C1 2.8(2) . . . . ?
C21 C5 C6 C1 -176.52(14) . . . . ?
C4 C5 C6 C11 -179.82(15) . . . . ?
C21 C5 C6 C11 0.8(2) . . . . ?
C1 C2 C7 C8 -91.42(18) . . . . ?
C3 C2 C7 C8 86.67(18) . . . . ?
C5 C4 C9 C10 89.88(19) . . . . ?
C3 C4 C9 C10 -88.24(19) . . . . ?
C1 C6 C11 C12 88.44(19) . . . . ?
C5 C6 C11 C12 -88.87(18) . . . . ?
C16 N1 C13 C1 41.7(2) . . . . ?
N2 N1 C13 C1 -148.33(14) . . . . ?
C6 C1 C13 N1 87.86(18) . . . . ?
C2 C1 C13 N1 -93.61(18) . . . . ?
N1 N2 C14 C15 0.59(19) . . . . ?
N2 C14 C15 C16 -0.3(2) . . . . ?
N2 N1 C16 C15 0.6(2) . . . . ?
C13 N1 C16 C15 171.09(15) . . . . ?
C14 C15 C16 N1 -0.17(19) . . . . ?
C20 N3 C17 C3 110.03(18) . . . . ?
N4 N3 C17 C3 -78.07(18) . . . . ?
C4 C3 C17 N3 -91.33(18) . . . . ?
C2 C3 C17 N3 92.08(18) . . . . ?
N3 N4 C18 C19 0.6(2) . . . . ?
N4 C18 C19 C20 -0.2(2) . . . . ?
N4 N3 C20 C19 0.68(19) . . . . ?
C17 N3 C20 C19 173.17(15) . . . . ?
C18 C19 C20 N3 -0.28(19) . . . . ?
C24 N5 C21 C5 -37.0(2) . . . . ?
N6 N5 C21 C5 147.57(14) . . . . ?
C4 C5 C21 N5 95.04(17) . . . . ?
C6 C5 C21 N5 -85.60(18) . . . . ?
N5 N6 C22 C23 -0.64(18) . . . . ?
N6 C22 C23 C24 0.39(19) . . . . ?
N6 N5 C24 C23 -0.44(18) . . . . ?
C21 N5 C24 C23 -176.19(14) . . . . ?
C22 C23 C24 N5 0.03(18) . . . . ?
C16A N1A N2A C14A -0.2(2) . . . . ?
C13A N1A N2A C14A -178.30(17) . . . . ?
C20A N3A N4A C18A 0.4(2) . . . . ?
C17A N3A N4A C18A 173.57(15) . . . . ?
C24A N5A N6A C22A 0.03(18) . . . . ?
C21A N5A N6A C22A 175.39(13) . . . . ?
C6A C1A C2A C3A 0.8(2) . . . . ?
C13A C1A C2A C3A 179.16(14) . . . . ?
C6A C1A C2A C7A -179.12(14) . . . . ?
C13A C1A C2A C7A -0.8(2) . . . . ?
C1A C2A C3A C4A 0.6(2) . . . . ?
C7A C2A C3A C4A -179.42(14) . . . . ?
C1A C2A C3A C17A -176.39(14) . . . . ?
C7A C2A C3A C17A 3.5(2) . . . . ?
C2A C3A C4A C5A -0.2(2) . . . . ?
C17A C3A C4A C5A 176.72(15) . . . . ?
C2A C3A C4A C9A 178.89(15) . . . . ?
C17A C3A C4A C9A -4.1(2) . . . . ?
C3A C4A C5A C6A -1.6(2) . . . . ?
C9A C4A C5A C6A 179.25(15) . . . . ?
C3A C4A C5A C21A 179.92(14) . . . . ?
C9A C4A C5A C21A 0.8(2) . . . . ?
C2A C1A C6A C5A -2.6(2) . . . . ?
C13A C1A C6A C5A 179.04(14) . . . . ?
C2A C1A C6A C11A 178.57(15) . . . . ?
C13A C1A C6A C11A 0.2(2) . . . . ?
C4A C5A C6A C1A 3.0(2) . . . . ?
C21A C5A C6A C1A -178.49(14) . . . . ?
C4A C5A C6A C11A -178.17(15) . . . . ?
C21A C5A C6A C11A 0.3(2) . . . . ?
C1A C2A C7A C8A -90.48(18) . . . . ?
C3A C2A C7A C8A 89.58(19) . . . . ?
C5A C4A C9A C10A 96.08(19) . . . . ?
C3A C4A C9A C10A -83.0(2) . . . . ?
C1A C6A C11A C12A 86.41(19) . . . . ?
C5A C6A C11A C12A -92.37(18) . . . . ?
C16A N1A C13A C1A 1.1(3) . . . . ?
N2A N1A C13A C1A 178.78(15) . . . . ?
C2A C1A C13A N1A -84.48(18) . . . . ?
C6A C1A C13A N1A 93.89(18) . . . . ?
N1A N2A C14A C15A -0.1(3) . . . . ?
N2A C14A C15A C16A 0.3(3) . . . . ?
N2A N1A C16A C15A 0.4(2) . . . . ?
C13A N1A C16A C15A 178.23(17) . . . . ?
C14A C15A C16A N1A -0.4(2) . . . . ?
C20A N3A C17A C3A 41.0(2) . . . . ?
N4A N3A C17A C3A -130.89(15) . . . . ?
C2A C3A C17A N3A 72.46(18) . . . . ?
C4A C3A C17A N3A -104.56(17) . . . . ?
N3A N4A C18A C19A -0.3(2) . . . . ?
N4A C18A C19A C20A 0.2(2) . . . . ?
N4A N3A C20A C19A -0.3(2) . . . . ?
C17A N3A C20A C19A -172.74(16) . . . . ?
C18A C19A C20A N3A 0.1(2) . . . . ?
C24A N5A C21A C5A -31.3(2) . . . . ?
N6A N5A C21A C5A 154.20(14) . . . . ?
C6A C5A C21A N5A -87.21(18) . . . . ?
C4A C5A C21A N5A 91.28(18) . . . . ?
N5A N6A C22A C23A -0.05(19) . . . . ?
N6A C22A C23A C24A 0.0(2) . . . . ?
N6A N5A C24A C23A 0.0(2) . . . . ?
C21A N5A C24A C23A -174.81(16) . . . . ?
C22A C23A C24A N5A 0.0(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
C13A H13C N6 0.99 2.65 3.360(2) 129.2 1_455
C20 H20 N5 0.95 2.62 3.451(2) 146.9 3_665

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch13fin
_database_code_depnum_ccdc_archive 'CCDC 1533893'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H42 N6'
_chemical_formula_sum            'C30 H42 N6'
_chemical_formula_weight         486.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

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

_cell_length_a                   11.1233(4)
_cell_length_b                   20.7068(7)
_cell_length_c                   23.8883(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.454(2)
_cell_angle_gamma                90
_cell_volume                     5455.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      29.60

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50336
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.351
_diffrn_reflns_theta_max         28.447
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             13476
_reflns_number_gt                12568
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+1.4913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13476
_refine_ls_number_parameters     668
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.52227(14) 0.09963(8) 0.24336(7) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.41819(14) 0.06416(7) 0.23602(7) 0.0175(3) Uani 1 1 d . . . . .
N3 N 0.24462(14) 0.37436(7) 0.19517(7) 0.0163(3) Uani 1 1 d . . . . .
N4 N 0.18220(14) 0.33203(8) 0.22394(7) 0.0194(3) Uani 1 1 d . . . . .
N5 N 0.27976(14) 0.18284(7) -0.01362(7) 0.0157(3) Uani 1 1 d . . . . .
N6 N 0.34789(14) 0.23461(8) -0.02567(7) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.45942(16) 0.18144(8) 0.16749(8) 0.0143(3) Uani 1 1 d . . . . .
C2 C 0.44568(15) 0.24337(9) 0.19008(8) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.36782(15) 0.28762(9) 0.15965(8) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.29726(15) 0.26922(8) 0.10911(7) 0.0139(3) Uani 1 1 d . . . . .
C5 C 0.30450(15) 0.20544(9) 0.08949(7) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.38855(16) 0.16194(8) 0.11780(7) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.51441(16) 0.26038(9) 0.24722(8) 0.0172(3) Uani 1 1 d . . . . .
H7A H 0.5279 0.2203 0.2698 0.021 Uiso 1 1 calc R U . . .
H7B H 0.4631 0.2893 0.2671 0.021 Uiso 1 1 calc R U . . .
C8 C 0.63736(18) 0.29334(10) 0.24507(9) 0.0237(4) Uani 1 1 d . . . . .
H8A H 0.6879 0.2660 0.2241 0.036 Uiso 1 1 calc R U . . .
H8B H 0.6780 0.2998 0.2836 0.036 Uiso 1 1 calc R U . . .
H8C H 0.6247 0.3353 0.2262 0.036 Uiso 1 1 calc R U . . .
C9 C 0.21769(16) 0.31812(9) 0.07426(8) 0.0153(3) Uani 1 1 d . . . . .
H9A H 0.2239 0.3100 0.0339 0.018 Uiso 1 1 calc R U . . .
H9B H 0.2513 0.3617 0.0834 0.018 Uiso 1 1 calc R U . . .
C10 C 0.08236(16) 0.31894(9) 0.08191(9) 0.0194(4) Uani 1 1 d . . . . .
H10A H 0.0437 0.2792 0.0663 0.029 Uiso 1 1 calc R U . . .
H10B H 0.0430 0.3563 0.0621 0.029 Uiso 1 1 calc R U . . .
H10C H 0.0742 0.3219 0.1222 0.029 Uiso 1 1 calc R U . . .
C11 C 0.40321(17) 0.09468(9) 0.09423(8) 0.0169(4) Uani 1 1 d . . . . .
H11A H 0.3242 0.0803 0.0743 0.020 Uiso 1 1 calc R U . . .
H11B H 0.4262 0.0645 0.1260 0.020 Uiso 1 1 calc R U . . .
C12 C 0.49878(19) 0.09088(10) 0.05337(9) 0.0222(4) Uani 1 1 d . . . . .
H12A H 0.4779 0.1214 0.0223 0.033 Uiso 1 1 calc R U . . .
H12B H 0.5009 0.0470 0.0382 0.033 Uiso 1 1 calc R U . . .
H12C H 0.5786 0.1019 0.0735 0.033 Uiso 1 1 calc R U . . .
C13 C 0.55713(16) 0.13702(9) 0.19618(8) 0.0163(3) Uani 1 1 d . . . . .
H13A H 0.5814 0.1066 0.1677 0.020 Uiso 1 1 calc R U . . .
H13B H 0.6291 0.1634 0.2101 0.020 Uiso 1 1 calc R U . . .
C14 C 0.41938(17) 0.03142(9) 0.28430(8) 0.0176(4) Uani 1 1 d . . . . .
C15 C 0.52341(18) 0.04536(10) 0.32159(8) 0.0214(4) Uani 1 1 d . . . . .
H15 H 0.5448 0.0282 0.3584 0.026 Uiso 1 1 calc R U . . .
C16 C 0.58892(17) 0.08914(10) 0.29417(8) 0.0201(4) Uani 1 1 d . . . . .
C17 C 0.31910(19) -0.01430(10) 0.29272(9) 0.0235(4) Uani 1 1 d . . . . .
H17A H 0.2459 0.0103 0.2977 0.035 Uiso 1 1 calc R U . . .
H17B H 0.3432 -0.0407 0.3263 0.035 Uiso 1 1 calc R U . . .
H17C H 0.3024 -0.0424 0.2596 0.035 Uiso 1 1 calc R U . . .
C18 C 0.70868(19) 0.12073(12) 0.31217(10) 0.0294(5) Uani 1 1 d . . . . .
H18A H 0.7646 0.1106 0.2849 0.044 Uiso 1 1 calc R U . . .
H18B H 0.7422 0.1047 0.3495 0.044 Uiso 1 1 calc R U . . .
H18C H 0.6977 0.1676 0.3138 0.044 Uiso 1 1 calc R U . . .
C19 C 0.36343(16) 0.35660(9) 0.18065(8) 0.0160(3) Uani 1 1 d . . . . .
H19A H 0.4245 0.3620 0.2143 0.019 Uiso 1 1 calc R U . . .
H19B H 0.3851 0.3863 0.1510 0.019 Uiso 1 1 calc R U . . .
C20 C 0.07845(17) 0.36246(10) 0.22927(8) 0.0213(4) Uani 1 1 d . . . . .
C21 C 0.07588(17) 0.42418(10) 0.20515(9) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.0128 0.4553 0.2042 0.027 Uiso 1 1 calc R U . . .
C22 C 0.18370(17) 0.43045(9) 0.18311(8) 0.0182(4) Uani 1 1 d . . . . .
C23 C -0.01940(19) 0.32860(12) 0.25556(10) 0.0306(5) Uani 1 1 d . . . . .
H23A H -0.0854 0.3167 0.2261 0.046 Uiso 1 1 calc R U . . .
H23B H -0.0506 0.3574 0.2828 0.046 Uiso 1 1 calc R U . . .
H23C H 0.0139 0.2895 0.2749 0.046 Uiso 1 1 calc R U . . .
C24 C 0.23267(19) 0.48429(10) 0.15148(10) 0.0250(4) Uani 1 1 d . . . . .
H24A H 0.3101 0.4988 0.1718 0.037 Uiso 1 1 calc R U . . .
H24B H 0.1749 0.5203 0.1480 0.037 Uiso 1 1 calc R U . . .
H24C H 0.2452 0.4693 0.1138 0.037 Uiso 1 1 calc R U . . .
C25 C 0.22077(16) 0.18435(9) 0.03765(8) 0.0154(3) Uani 1 1 d . . . . .
H25A H 0.1891 0.1407 0.0444 0.018 Uiso 1 1 calc R U . . .
H25B H 0.1508 0.2143 0.0318 0.018 Uiso 1 1 calc R U . . .
C26 C 0.37912(17) 0.22183(9) -0.07655(8) 0.0184(4) Uani 1 1 d . . . . .
C27 C 0.33006(18) 0.16237(10) -0.09709(8) 0.0213(4) Uani 1 1 d . . . . .
H27 H 0.3393 0.1426 -0.1322 0.026 Uiso 1 1 calc R U . . .
C28 C 0.26587(17) 0.13882(9) -0.05576(8) 0.0185(4) Uani 1 1 d . . . . .
C29 C 0.4558(2) 0.26839(10) -0.10413(9) 0.0248(4) Uani 1 1 d . . . . .
H29A H 0.4604 0.3094 -0.0835 0.037 Uiso 1 1 calc R U . . .
H29B H 0.4197 0.2757 -0.1433 0.037 Uiso 1 1 calc R U . . .
H29C H 0.5375 0.2506 -0.1037 0.037 Uiso 1 1 calc R U . . .
C30 C 0.19272(19) 0.07852(10) -0.05381(10) 0.0252(4) Uani 1 1 d . . . . .
H30A H 0.2311 0.0503 -0.0237 0.038 Uiso 1 1 calc R U . . .
H30B H 0.1884 0.0561 -0.0901 0.038 Uiso 1 1 calc R U . . .
H30C H 0.1107 0.0896 -0.0463 0.038 Uiso 1 1 calc R U . . .
N1A N 0.34365(14) 0.64418(8) -0.04246(7) 0.0169(3) Uani 1 1 d . . . . .
N2A N 0.44423(14) 0.68250(8) -0.03537(7) 0.0181(3) Uani 1 1 d . . . . .
N3A N 0.58188(14) 0.56355(7) 0.21900(7) 0.0167(3) Uani 1 1 d . . . . .
N4A N 0.51531(15) 0.51141(8) 0.23133(7) 0.0196(3) Uani 1 1 d . . . . .
N5A N 0.59340(14) 0.36652(7) 0.00933(7) 0.0156(3) Uani 1 1 d . . . . .
N6A N 0.63868(15) 0.40354(8) -0.03034(7) 0.0199(3) Uani 1 1 d . . . . .
C1A C 0.40046(16) 0.56508(8) 0.03694(8) 0.0144(3) Uani 1 1 d . . . . .
C2A C 0.47234(15) 0.58527(8) 0.08644(7) 0.0141(3) Uani 1 1 d . . . . .
C3A C 0.55409(15) 0.54126(9) 0.11575(8) 0.0147(3) Uani 1 1 d . . . . .
C4A C 0.55859(15) 0.47678(9) 0.09772(7) 0.0141(3) Uani 1 1 d . . . . .
C5A C 0.48427(15) 0.45701(8) 0.04867(7) 0.0141(3) Uani 1 1 d . . . . .
C6A C 0.40857(15) 0.50149(9) 0.01707(7) 0.0143(3) Uani 1 1 d . . . . .
C7A C 0.45993(17) 0.65305(9) 0.10866(8) 0.0177(4) Uani 1 1 d . . . . .
H7C H 0.4363 0.6825 0.0765 0.021 Uiso 1 1 calc R U . . .
H7D H 0.5396 0.6675 0.1279 0.021 Uiso 1 1 calc R U . . .
C8A C 0.36562(18) 0.65781(10) 0.15014(9) 0.0221(4) Uani 1 1 d . . . . .
H8D H 0.2869 0.6427 0.1316 0.033 Uiso 1 1 calc R U . . .
H8E H 0.3585 0.7028 0.1619 0.033 Uiso 1 1 calc R U . . .
H8F H 0.3913 0.6309 0.1833 0.033 Uiso 1 1 calc R U . . .
C9A C 0.64187(16) 0.42892(9) 0.13138(8) 0.0178(4) Uani 1 1 d . . . . .
H9C H 0.6061 0.3852 0.1259 0.021 Uiso 1 1 calc R U . . .
H9D H 0.6461 0.4397 0.1720 0.021 Uiso 1 1 calc R U . . .
C10A C 0.77144(17) 0.42724(10) 0.11547(9) 0.0225(4) Uani 1 1 d . . . . .
H10D H 0.7681 0.4219 0.0745 0.034 Uiso 1 1 calc R U . . .
H10E H 0.8159 0.3910 0.1347 0.034 Uiso 1 1 calc R U . . .
H10F H 0.8129 0.4678 0.1270 0.034 Uiso 1 1 calc R U . . .
C11A C 0.33409(17) 0.48119(9) -0.03764(8) 0.0174(4) Uani 1 1 d . . . . .
H11C H 0.3800 0.4484 -0.0564 0.021 Uiso 1 1 calc R U . . .
H11D H 0.3218 0.5191 -0.0630 0.021 Uiso 1 1 calc R U . . .
C12A C 0.21009(18) 0.45316(10) -0.02934(9) 0.0216(4) Uani 1 1 d . . . . .
H12D H 0.2213 0.4166 -0.0032 0.032 Uiso 1 1 calc R U . . .
H12E H 0.1683 0.4385 -0.0658 0.032 Uiso 1 1 calc R U . . .
H12F H 0.1614 0.4865 -0.0138 0.032 Uiso 1 1 calc R U . . .
C13A C 0.30653(16) 0.61040(9) 0.00616(8) 0.0165(3) Uani 1 1 d . . . . .
H13C H 0.2326 0.5851 -0.0067 0.020 Uiso 1 1 calc R U . . .
H13D H 0.2846 0.6430 0.0334 0.020 Uiso 1 1 calc R U . . .
C14A C 0.44383(17) 0.71245(9) -0.08491(8) 0.0201(4) Uani 1 1 d . . . . .
C15A C 0.34298(18) 0.69424(10) -0.12314(9) 0.0223(4) Uani 1 1 d . . . . .
H15A H 0.3226 0.7088 -0.1609 0.027 Uiso 1 1 calc R U . . .
C16A C 0.27961(18) 0.65085(10) -0.09441(8) 0.0201(4) Uani 1 1 d . . . . .
C17A C 0.54236(19) 0.75911(11) -0.09367(10) 0.0265(4) Uani 1 1 d . . . . .
H17D H 0.5798 0.7755 -0.0570 0.040 Uiso 1 1 calc R U . . .
H17E H 0.5080 0.7952 -0.1170 0.040 Uiso 1 1 calc R U . . .
H17F H 0.6038 0.7372 -0.1127 0.040 Uiso 1 1 calc R U . . .
C18A C 0.1633(2) 0.61700(11) -0.11324(10) 0.0278(4) Uani 1 1 d . . . . .
H18D H 0.1737 0.5705 -0.1065 0.042 Uiso 1 1 calc R U . . .
H18E H 0.1395 0.6248 -0.1536 0.042 Uiso 1 1 calc R U . . .
H18F H 0.1001 0.6334 -0.0920 0.042 Uiso 1 1 calc R U . . .
C19A C 0.63871(16) 0.56316(9) 0.16709(8) 0.0171(4) Uani 1 1 d . . . . .
H19C H 0.7101 0.5342 0.1723 0.020 Uiso 1 1 calc R U . . .
H19D H 0.6680 0.6072 0.1602 0.020 Uiso 1 1 calc R U . . .
C20A C 0.48833(18) 0.52293(10) 0.28328(9) 0.0225(4) Uani 1 1 d . . . . .
C21A C 0.53758(18) 0.58187(11) 0.30404(9) 0.0239(4) Uani 1 1 d . . . . .
H21A H 0.5304 0.6008 0.3397 0.029 Uiso 1 1 calc R U . . .
C22A C 0.59846(17) 0.60667(9) 0.26217(8) 0.0200(4) Uani 1 1 d . . . . .
C23A C 0.4145(2) 0.47523(12) 0.31140(10) 0.0315(5) Uani 1 1 d . . . . .
H23D H 0.3283 0.4815 0.2978 0.047 Uiso 1 1 calc R U . . .
H23E H 0.4284 0.4817 0.3524 0.047 Uiso 1 1 calc R U . . .
H23F H 0.4385 0.4313 0.3024 0.047 Uiso 1 1 calc R U . . .
C24A C 0.6719(2) 0.66682(10) 0.26020(10) 0.0275(4) Uani 1 1 d . . . . .
H24D H 0.7556 0.6554 0.2557 0.041 Uiso 1 1 calc R U . . .
H24E H 0.6709 0.6911 0.2954 0.041 Uiso 1 1 calc R U . . .
H24F H 0.6373 0.6935 0.2282 0.041 Uiso 1 1 calc R U . . .
C25A C 0.48239(16) 0.38674(9) 0.03061(8) 0.0156(3) Uani 1 1 d . . . . .
H25C H 0.4696 0.3593 0.0633 0.019 Uiso 1 1 calc R U . . .
H25D H 0.4130 0.3798 0.0008 0.019 Uiso 1 1 calc R U . . .
C26A C 0.73632(18) 0.37129(10) -0.04183(8) 0.0227(4) Uani 1 1 d . . . . .
C27A C 0.75235(17) 0.31374(10) -0.01053(9) 0.0223(4) Uani 1 1 d . . . . .
H27A H 0.8148 0.2826 -0.0115 0.027 Uiso 1 1 calc R U . . .
C28A C 0.65865(17) 0.31193(9) 0.02190(8) 0.0179(4) Uani 1 1 d . . . . .
C29A C 0.8130(2) 0.39764(12) -0.08343(10) 0.0335(5) Uani 1 1 d . . . . .
H29D H 0.8161 0.3664 -0.1140 0.050 Uiso 1 1 calc R U . . .
H29E H 0.8952 0.4056 -0.0645 0.050 Uiso 1 1 calc R U . . .
H29F H 0.7779 0.4382 -0.0991 0.050 Uiso 1 1 calc R U . . .
C30A C 0.62580(19) 0.26285(10) 0.06311(9) 0.0231(4) Uani 1 1 d . . . . .
H30D H 0.6397 0.2808 0.1013 0.035 Uiso 1 1 calc R U . . .
H30E H 0.6760 0.2242 0.0611 0.035 Uiso 1 1 calc R U . . .
H30F H 0.5401 0.2512 0.0539 0.035 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 C16 1.355(3) . ?
N1 N2 1.363(2) . ?
N1 C13 1.461(2) . ?
N2 C14 1.336(2) . ?
N3 C22 1.357(2) . ?
N3 N4 1.359(2) . ?
N3 C19 1.456(2) . ?
N4 C20 1.335(2) . ?
N5 C28 1.352(2) . ?
N5 N6 1.365(2) . ?
N5 C25 1.463(2) . ?
N6 C26 1.333(2) . ?
C1 C6 1.397(3) . ?
C1 C2 1.407(2) . ?
C1 C13 1.518(2) . ?
C2 C3 1.398(3) . ?
C2 C7 1.517(3) . ?
C3 C4 1.405(3) . ?
C3 C19 1.517(2) . ?
C4 C5 1.407(2) . ?
C4 C9 1.520(2) . ?
C5 C6 1.407(3) . ?
C5 C25 1.514(3) . ?
C6 C11 1.519(2) . ?
C7 C8 1.535(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.540(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.535(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.396(3) . ?
C14 C17 1.496(3) . ?
C15 C16 1.380(3) . ?
C15 H15 0.9500 . ?
C16 C18 1.496(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.401(3) . ?
C20 C23 1.499(3) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C24 1.489(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.409(3) . ?
C26 C29 1.496(3) . ?
C27 C28 1.380(3) . ?
C27 H27 0.9500 . ?
C28 C30 1.494(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N1A C16A 1.356(3) . ?
N1A N2A 1.364(2) . ?
N1A C13A 1.460(2) . ?
N2A C14A 1.336(2) . ?
N3A C22A 1.359(2) . ?
N3A N4A 1.363(2) . ?
N3A C19A 1.463(2) . ?
N4A C20A 1.336(2) . ?
N5A C28A 1.356(2) . ?
N5A N6A 1.365(2) . ?
N5A C25A 1.457(2) . ?
N6A C26A 1.333(2) . ?
C1A C2A 1.402(3) . ?
C1A C6A 1.407(2) . ?
C1A C13A 1.521(2) . ?
C2A C3A 1.408(2) . ?
C2A C7A 1.513(2) . ?
C3A C4A 1.406(2) . ?
C3A C19A 1.515(3) . ?
C4A C5A 1.404(3) . ?
C4A C9A 1.515(3) . ?
C5A C6A 1.401(3) . ?
C5A C25A 1.517(2) . ?
C6A C11A 1.513(3) . ?
C7A C8A 1.537(3) . ?
C7A H7C 0.9900 . ?
C7A H7D 0.9900 . ?
C8A H8D 0.9800 . ?
C8A H8E 0.9800 . ?
C8A H8F 0.9800 . ?
C9A C10A 1.538(3) . ?
C9A H9C 0.9900 . ?
C9A H9D 0.9900 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A C12A 1.533(3) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.403(3) . ?
C14A C17A 1.496(3) . ?
C15A C16A 1.379(3) . ?
C15A H15A 0.9500 . ?
C16A C18A 1.489(3) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A C21A 1.402(3) . ?
C20A C23A 1.498(3) . ?
C21A C22A 1.378(3) . ?
C21A H21A 0.9500 . ?
C22A C24A 1.493(3) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C26A C27A 1.406(3) . ?
C26A C29A 1.494(3) . ?
C27A C28A 1.377(3) . ?
C27A H27A 0.9500 . ?
C28A C30A 1.493(3) . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N1 N2 112.69(15) . . ?
C16 N1 C13 127.37(16) . . ?
N2 N1 C13 119.49(15) . . ?
C14 N2 N1 104.42(16) . . ?
C22 N3 N4 112.69(15) . . ?
C22 N3 C19 127.55(16) . . ?
N4 N3 C19 119.76(15) . . ?
C20 N4 N3 104.38(15) . . ?
C28 N5 N6 112.66(15) . . ?
C28 N5 C25 128.13(15) . . ?
N6 N5 C25 118.78(14) . . ?
C26 N6 N5 104.71(15) . . ?
C6 C1 C2 120.79(16) . . ?
C6 C1 C13 120.05(16) . . ?
C2 C1 C13 119.08(17) . . ?
C3 C2 C1 119.24(17) . . ?
C3 C2 C7 121.44(16) . . ?
C1 C2 C7 119.31(16) . . ?
C2 C3 C4 120.57(16) . . ?
C2 C3 C19 119.31(16) . . ?
C4 C3 C19 120.09(16) . . ?
C3 C4 C5 119.41(16) . . ?
C3 C4 C9 120.71(16) . . ?
C5 C4 C9 119.83(16) . . ?
C6 C5 C4 120.28(16) . . ?
C6 C5 C25 120.55(16) . . ?
C4 C5 C25 119.17(16) . . ?
C1 C6 C5 119.35(16) . . ?
C1 C6 C11 120.27(16) . . ?
C5 C6 C11 120.37(16) . . ?
C2 C7 C8 114.84(15) . . ?
C2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 C10 116.81(15) . . ?
C4 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C4 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C12 113.52(16) . . ?
C6 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C6 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C1 115.06(14) . . ?
N1 C13 H13A 108.5 . . ?
C1 C13 H13A 108.5 . . ?
N1 C13 H13B 108.5 . . ?
C1 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
N2 C14 C15 111.13(17) . . ?
N2 C14 C17 120.86(18) . . ?
C15 C14 C17 128.00(18) . . ?
C16 C15 C14 106.13(17) . . ?
C16 C15 H15 126.9 . . ?
C14 C15 H15 126.9 . . ?
N1 C16 C15 105.61(17) . . ?
N1 C16 C18 123.39(18) . . ?
C15 C16 C18 130.99(19) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C3 112.70(15) . . ?
N3 C19 H19A 109.1 . . ?
C3 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C3 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N4 C20 C21 111.29(17) . . ?
N4 C20 C23 120.16(19) . . ?
C21 C20 C23 128.45(18) . . ?
C22 C21 C20 105.72(17) . . ?
C22 C21 H21 127.1 . . ?
C20 C21 H21 127.1 . . ?
N3 C22 C21 105.90(17) . . ?
N3 C22 C24 122.90(16) . . ?
C21 C22 C24 131.19(18) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C5 113.32(14) . . ?
N5 C25 H25A 108.9 . . ?
C5 C25 H25A 108.9 . . ?
N5 C25 H25B 108.9 . . ?
C5 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
N6 C26 C27 110.85(17) . . ?
N6 C26 C29 120.30(17) . . ?
C27 C26 C29 128.84(17) . . ?
C28 C27 C26 105.82(17) . . ?
C28 C27 H27 127.1 . . ?
C26 C27 H27 127.1 . . ?
N5 C28 C27 105.94(17) . . ?
N5 C28 C30 123.38(17) . . ?
C27 C28 C30 130.68(18) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 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 . . ?
C16A N1A N2A 112.30(16) . . ?
C16A N1A C13A 127.42(16) . . ?
N2A N1A C13A 119.46(15) . . ?
C14A N2A N1A 104.58(16) . . ?
C22A N3A N4A 112.37(15) . . ?
C22A N3A C19A 128.02(16) . . ?
N4A N3A C19A 119.05(15) . . ?
C20A N4A N3A 104.67(16) . . ?
C28A N5A N6A 112.76(14) . . ?
C28A N5A C25A 128.03(15) . . ?
N6A N5A C25A 119.13(14) . . ?
C26A N6A N5A 104.20(15) . . ?
C2A C1A C6A 120.60(16) . . ?
C2A C1A C13A 120.29(16) . . ?
C6A C1A C13A 118.98(16) . . ?
C1A C2A C3A 119.16(16) . . ?
C1A C2A C7A 120.28(16) . . ?
C3A C2A C7A 120.55(16) . . ?
C4A C3A C2A 120.58(17) . . ?
C4A C3A C19A 119.29(16) . . ?
C2A C3A C19A 120.14(16) . . ?
C5A C4A C3A 119.47(16) . . ?
C5A C4A C9A 120.36(16) . . ?
C3A C4A C9A 120.16(17) . . ?
C6A C5A C4A 120.37(16) . . ?
C6A C5A C25A 119.48(16) . . ?
C4A C5A C25A 120.12(16) . . ?
C5A C6A C1A 119.60(16) . . ?
C5A C6A C11A 120.42(16) . . ?
C1A C6A C11A 119.96(16) . . ?
C2A C7A C8A 112.75(15) . . ?
C2A C7A H7C 109.0 . . ?
C8A C7A H7C 109.0 . . ?
C2A C7A H7D 109.0 . . ?
C8A C7A H7D 109.0 . . ?
H7C C7A H7D 107.8 . . ?
C7A C8A H8D 109.5 . . ?
C7A C8A H8E 109.5 . . ?
H8D C8A H8E 109.5 . . ?
C7A C8A H8F 109.5 . . ?
H8D C8A H8F 109.5 . . ?
H8E C8A H8F 109.5 . . ?
C4A C9A C10A 114.32(15) . . ?
C4A C9A H9C 108.7 . . ?
C10A C9A H9C 108.7 . . ?
C4A C9A H9D 108.7 . . ?
C10A C9A H9D 108.7 . . ?
H9C C9A H9D 107.6 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C6A C11A C12A 113.24(15) . . ?
C6A C11A H11C 108.9 . . ?
C12A C11A H11C 108.9 . . ?
C6A C11A H11D 108.9 . . ?
C12A C11A H11D 108.9 . . ?
H11C C11A H11D 107.7 . . ?
C11A C12A H12D 109.5 . . ?
C11A C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C11A C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
N1A C13A C1A 115.63(14) . . ?
N1A C13A H13C 108.4 . . ?
C1A C13A H13C 108.4 . . ?
N1A C13A H13D 108.4 . . ?
C1A C13A H13D 108.4 . . ?
H13C C13A H13D 107.4 . . ?
N2A C14A C15A 111.24(17) . . ?
N2A C14A C17A 120.37(19) . . ?
C15A C14A C17A 128.39(18) . . ?
C16A C15A C14A 105.57(18) . . ?
C16A C15A H15A 127.2 . . ?
C14A C15A H15A 127.2 . . ?
N1A C16A C15A 106.27(17) . . ?
N1A C16A C18A 124.17(18) . . ?
C15A C16A C18A 129.55(19) . . ?
C14A C17A H17D 109.5 . . ?
C14A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
C14A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
C16A C18A H18D 109.5 . . ?
C16A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C16A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3A C19A C3A 113.34(14) . . ?
N3A C19A H19C 108.9 . . ?
C3A C19A H19C 108.9 . . ?
N3A C19A H19D 108.9 . . ?
C3A C19A H19D 108.9 . . ?
H19C C19A H19D 107.7 . . ?
N4A C20A C21A 111.08(18) . . ?
N4A C20A C23A 120.08(18) . . ?
C21A C20A C23A 128.84(19) . . ?
C22A C21A C20A 105.90(17) . . ?
C22A C21A H21A 127.0 . . ?
C20A C21A H21A 127.0 . . ?
N3A C22A C21A 105.97(17) . . ?
N3A C22A C24A 123.03(18) . . ?
C21A C22A C24A 131.00(19) . . ?
C20A C23A H23D 109.5 . . ?
C20A C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C20A C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C22A C24A H24D 109.5 . . ?
C22A C24A H24E 109.5 . . ?
H24D C24A H24E 109.5 . . ?
C22A C24A H24F 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
N5A C25A C5A 113.20(14) . . ?
N5A C25A H25C 108.9 . . ?
C5A C25A H25C 108.9 . . ?
N5A C25A H25D 108.9 . . ?
C5A C25A H25D 108.9 . . ?
H25C C25A H25D 107.8 . . ?
N6A C26A C27A 111.44(16) . . ?
N6A C26A C29A 120.28(18) . . ?
C27A C26A C29A 128.27(18) . . ?
C28A C27A C26A 105.61(16) . . ?
C28A C27A H27A 127.2 . . ?
C26A C27A H27A 127.2 . . ?
N5A C28A C27A 105.97(16) . . ?
N5A C28A C30A 122.95(16) . . ?
C27A C28A C30A 131.08(17) . . ?
C26A C29A H29D 109.5 . . ?
C26A C29A H29E 109.5 . . ?
H29D C29A H29E 109.5 . . ?
C26A C29A H29F 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
C28A C30A H30D 109.5 . . ?
C28A C30A H30E 109.5 . . ?
H30D C30A H30E 109.5 . . ?
C28A C30A H30F 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 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
C16 N1 N2 C14 1.1(2) . . . . ?
C13 N1 N2 C14 173.96(15) . . . . ?
C22 N3 N4 C20 0.8(2) . . . . ?
C19 N3 N4 C20 -178.92(16) . . . . ?
C28 N5 N6 C26 -1.1(2) . . . . ?
C25 N5 N6 C26 -174.23(15) . . . . ?
C6 C1 C2 C3 -5.7(2) . . . . ?
C13 C1 C2 C3 171.15(15) . . . . ?
C6 C1 C2 C7 173.54(15) . . . . ?
C13 C1 C2 C7 -9.6(2) . . . . ?
C1 C2 C3 C4 4.6(2) . . . . ?
C7 C2 C3 C4 -174.61(15) . . . . ?
C1 C2 C3 C19 -173.24(15) . . . . ?
C7 C2 C3 C19 7.5(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C19 C3 C4 C5 178.50(15) . . . . ?
C2 C3 C4 C9 -176.65(15) . . . . ?
C19 C3 C4 C9 1.2(2) . . . . ?
C3 C4 C5 C6 -5.0(2) . . . . ?
C9 C4 C5 C6 172.36(15) . . . . ?
C3 C4 C5 C25 175.00(15) . . . . ?
C9 C4 C5 C25 -7.7(2) . . . . ?
C2 C1 C6 C5 1.4(2) . . . . ?
C13 C1 C6 C5 -175.38(15) . . . . ?
C2 C1 C6 C11 -179.27(16) . . . . ?
C13 C1 C6 C11 3.9(2) . . . . ?
C4 C5 C6 C1 3.9(2) . . . . ?
C25 C5 C6 C1 -176.05(15) . . . . ?
C4 C5 C6 C11 -175.36(15) . . . . ?
C25 C5 C6 C11 4.7(2) . . . . ?
C3 C2 C7 C8 -87.5(2) . . . . ?
C1 C2 C7 C8 93.3(2) . . . . ?
C3 C4 C9 C10 -98.3(2) . . . . ?
C5 C4 C9 C10 84.4(2) . . . . ?
C1 C6 C11 C12 -89.5(2) . . . . ?
C5 C6 C11 C12 89.8(2) . . . . ?
C16 N1 C13 C1 -136.35(19) . . . . ?
N2 N1 C13 C1 51.9(2) . . . . ?
C6 C1 C13 N1 -98.32(19) . . . . ?
C2 C1 C13 N1 84.8(2) . . . . ?
N1 N2 C14 C15 -0.6(2) . . . . ?
N1 N2 C14 C17 -179.39(16) . . . . ?
N2 C14 C15 C16 0.0(2) . . . . ?
C17 C14 C15 C16 178.66(19) . . . . ?
N2 N1 C16 C15 -1.1(2) . . . . ?
C13 N1 C16 C15 -173.29(17) . . . . ?
N2 N1 C16 C18 178.34(18) . . . . ?
C13 N1 C16 C18 6.1(3) . . . . ?
C14 C15 C16 N1 0.6(2) . . . . ?
C14 C15 C16 C18 -178.7(2) . . . . ?
C22 N3 C19 C3 -137.28(19) . . . . ?
N4 N3 C19 C3 42.4(2) . . . . ?
C2 C3 C19 N3 -117.61(17) . . . . ?
C4 C3 C19 N3 64.5(2) . . . . ?
N3 N4 C20 C21 -1.2(2) . . . . ?
N3 N4 C20 C23 175.59(18) . . . . ?
N4 C20 C21 C22 1.2(2) . . . . ?
C23 C20 C21 C22 -175.3(2) . . . . ?
N4 N3 C22 C21 -0.1(2) . . . . ?
C19 N3 C22 C21 179.64(17) . . . . ?
N4 N3 C22 C24 -179.50(18) . . . . ?
C19 N3 C22 C24 0.2(3) . . . . ?
C20 C21 C22 N3 -0.7(2) . . . . ?
C20 C21 C22 C24 178.7(2) . . . . ?
C28 N5 C25 C5 140.56(19) . . . . ?
N6 N5 C25 C5 -47.5(2) . . . . ?
C6 C5 C25 N5 -78.7(2) . . . . ?
C4 C5 C25 N5 101.30(18) . . . . ?
N5 N6 C26 C27 0.6(2) . . . . ?
N5 N6 C26 C29 -179.82(17) . . . . ?
N6 C26 C27 C28 0.1(2) . . . . ?
C29 C26 C27 C28 -179.5(2) . . . . ?
N6 N5 C28 C27 1.1(2) . . . . ?
C25 N5 C28 C27 173.51(18) . . . . ?
N6 N5 C28 C30 -178.42(18) . . . . ?
C25 N5 C28 C30 -6.0(3) . . . . ?
C26 C27 C28 N5 -0.7(2) . . . . ?
C26 C27 C28 C30 178.8(2) . . . . ?
C16A N1A N2A C14A -1.6(2) . . . . ?
C13A N1A N2A C14A -171.98(15) . . . . ?
C22A N3A N4A C20A 0.9(2) . . . . ?
C19A N3A N4A C20A 172.99(17) . . . . ?
C28A N5A N6A C26A -1.1(2) . . . . ?
C25A N5A N6A C26A -178.13(17) . . . . ?
C6A C1A C2A C3A 0.8(2) . . . . ?
C13A C1A C2A C3A 176.67(15) . . . . ?
C6A C1A C2A C7A -177.85(15) . . . . ?
C13A C1A C2A C7A -2.0(2) . . . . ?
C1A C2A C3A C4A -3.9(2) . . . . ?
C7A C2A C3A C4A 174.76(15) . . . . ?
C1A C2A C3A C19A 175.87(15) . . . . ?
C7A C2A C3A C19A -5.5(2) . . . . ?
C2A C3A C4A C5A 2.6(2) . . . . ?
C19A C3A C4A C5A -177.10(15) . . . . ?
C2A C3A C4A C9A -176.61(15) . . . . ?
C19A C3A C4A C9A 3.6(2) . . . . ?
C3A C4A C5A C6A 1.7(2) . . . . ?
C9A C4A C5A C6A -179.05(15) . . . . ?
C3A C4A C5A C25A -176.28(15) . . . . ?
C9A C4A C5A C25A 3.0(2) . . . . ?
C4A C5A C6A C1A -4.7(2) . . . . ?
C25A C5A C6A C1A 173.25(15) . . . . ?
C4A C5A C6A C11A 176.33(15) . . . . ?
C25A C5A C6A C11A -5.7(2) . . . . ?
C2A C1A C6A C5A 3.5(2) . . . . ?
C13A C1A C6A C5A -172.44(15) . . . . ?
C2A C1A C6A C11A -177.57(15) . . . . ?
C13A C1A C6A C11A 6.5(2) . . . . ?
C1A C2A C7A C8A 90.4(2) . . . . ?
C3A C2A C7A C8A -88.2(2) . . . . ?
C5A C4A C9A C10A 93.5(2) . . . . ?
C3A C4A C9A C10A -87.2(2) . . . . ?
C5A C6A C11A C12A 87.8(2) . . . . ?
C1A C6A C11A C12A -91.1(2) . . . . ?
C16A N1A C13A C1A 133.07(19) . . . . ?
N2A N1A C13A C1A -58.1(2) . . . . ?
C2A C1A C13A N1A 98.91(19) . . . . ?
C6A C1A C13A N1A -85.1(2) . . . . ?
N1A N2A C14A C15A 0.9(2) . . . . ?
N1A N2A C14A C17A -179.71(17) . . . . ?
N2A C14A C15A C16A 0.1(2) . . . . ?
C17A C14A C15A C16A -179.28(19) . . . . ?
N2A N1A C16A C15A 1.6(2) . . . . ?
C13A N1A C16A C15A 171.12(17) . . . . ?
N2A N1A C16A C18A -177.52(18) . . . . ?
C13A N1A C16A C18A -8.0(3) . . . . ?
C14A C15A C16A N1A -1.0(2) . . . . ?
C14A C15A C16A C18A 178.1(2) . . . . ?
C22A N3A C19A C3A -142.78(19) . . . . ?
N4A N3A C19A C3A 46.5(2) . . . . ?
C4A C3A C19A N3A -97.71(19) . . . . ?
C2A C3A C19A N3A 82.5(2) . . . . ?
N3A N4A C20A C21A -0.2(2) . . . . ?
N3A N4A C20A C23A 179.97(19) . . . . ?
N4A C20A C21A C22A -0.6(2) . . . . ?
C23A C20A C21A C22A 179.3(2) . . . . ?
N4A N3A C22A C21A -1.3(2) . . . . ?
C19A N3A C22A C21A -172.48(18) . . . . ?
N4A N3A C22A C24A 177.80(18) . . . . ?
C19A N3A C22A C24A 6.6(3) . . . . ?
C20A C21A C22A N3A 1.1(2) . . . . ?
C20A C21A C22A C24A -177.9(2) . . . . ?
C28A N5A C25A C5A 134.43(19) . . . . ?
N6A N5A C25A C5A -49.1(2) . . . . ?
C6A C5A C25A N5A 110.83(18) . . . . ?
C4A C5A C25A N5A -71.2(2) . . . . ?
N5A N6A C26A C27A 0.9(2) . . . . ?
N5A N6A C26A C29A -178.92(19) . . . . ?
N6A C26A C27A C28A -0.4(2) . . . . ?
C29A C26A C27A C28A 179.4(2) . . . . ?
N6A N5A C28A C27A 0.9(2) . . . . ?
C25A N5A C28A C27A 177.57(18) . . . . ?
N6A N5A C28A C30A -178.62(18) . . . . ?
C25A N5A C28A C30A -2.0(3) . . . . ?
C26A C27A C28A N5A -0.3(2) . . . . ?
C26A C27A C28A C30A 179.2(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
C27A H27A N2A 0.95 2.63 3.553(2) 164.5 3_545
C19A H19C N2 0.99 2.67 3.324(2) 123.5 3
C24 H24A N4A 0.98 2.54 3.505(3) 167.8 .
C21 H21 N2 0.95 2.64 3.515(2) 153.1 3_455
C17 H17A N3A 0.98 2.68 3.385(3) 128.9 3_445

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.038

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_koch18cor
_database_code_depnum_ccdc_archive 'CCDC 1533898'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27 H36 N6 O3), C2 H6 O'
_chemical_formula_sum            'C56 H78 N12 O7'
_chemical_formula_weight         1031.30

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

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

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

_cell_length_a                   9.9852(2)
_cell_length_b                   12.5431(3)
_cell_length_c                   12.9192(3)
_cell_angle_alpha                118.483(1)
_cell_angle_beta                 93.506(1)
_cell_angle_gamma                102.774(1)
_cell_volume                     1360.57(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8785
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      29.21

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_F_000             554
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9564
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25181
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         28.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6601
_reflns_number_gt                5343
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0486P)²+1.2437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6601
_refine_ls_number_parameters     353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24354(10) 0.51325(9) 0.72644(9) 0.0194(2) Uani 1 1 d . . . A 2
O2 O 0.02659(10) 0.28178(9) 0.31016(8) 0.0184(2) Uani 1 1 d . . . A 2
O3 O -0.25383(10) 0.37914(9) 0.61396(9) 0.0179(2) Uani 1 1 d . . . A 2
N1 N -0.07848(12) 0.42123(11) 0.84442(10) 0.0184(2) Uani 1 1 d . . . A 2
N2 N -0.01255(13) 0.33447(11) 0.83738(11) 0.0204(2) Uani 1 1 d . . . A 2
N3 N 0.32538(12) 0.30468(11) 0.41900(10) 0.0171(2) Uani 1 1 d . . . A 2
N4 N 0.32045(12) 0.22411(11) 0.46221(11) 0.0194(2) Uani 1 1 d . . . A 2
N5 N -0.28408(11) 0.13784(10) 0.27649(10) 0.0163(2) Uani 1 1 d . . . A 2
N6 N -0.30179(12) 0.05227(11) 0.31424(11) 0.0201(2) Uani 1 1 d . . . A 2
C1 C -0.00653(14) 0.43813(12) 0.67054(12) 0.0161(3) Uani 1 1 d . . . A 2
C2 C 0.12389(14) 0.44484(12) 0.63735(12) 0.0159(3) Uani 1 1 d . . . A 2
C3 C 0.13773(13) 0.39264(12) 0.51716(12) 0.0158(3) Uani 1 1 d . . . A 2
C4 C 0.01554(14) 0.32969(12) 0.42943(11) 0.0151(2) Uani 1 1 d . . . A 2
C5 C -0.11735(13) 0.32140(12) 0.45830(11) 0.0151(2) Uani 1 1 d . . . A 2
C6 C -0.12532(13) 0.37635(12) 0.57964(12) 0.0154(2) Uani 1 1 d . . . A 2
C7 C 0.29905(15) 0.43505(15) 0.76057(14) 0.0237(3) Uani 1 1 d . . . A 2
H7A H 0.3217 0.3684 0.6902 0.036 Uiso 1 1 calc R U . A 2
H7B H 0.2291 0.3965 0.7921 0.036 Uiso 1 1 calc R U . A 2
H7C H 0.3840 0.4872 0.8226 0.036 Uiso 1 1 calc R U . A 2
C8 C 0.02751(15) 0.15048(13) 0.25106(13) 0.0225(3) Uani 1 1 d . . . A 2
H8A H -0.0598 0.0984 0.2537 0.034 Uiso 1 1 calc R U . A 2
H8B H 0.1072 0.1425 0.2923 0.034 Uiso 1 1 calc R U . A 2
H8C H 0.0357 0.1218 0.1673 0.034 Uiso 1 1 calc R U . A 2
C9 C -0.33260(15) 0.26079(13) 0.60185(13) 0.0218(3) Uani 1 1 d . . . A 2
H9A H -0.2851 0.2457 0.6602 0.033 Uiso 1 1 calc R U . A 2
H9B H -0.3392 0.1915 0.5204 0.033 Uiso 1 1 calc R U . A 2
H9C H -0.4269 0.2650 0.6168 0.033 Uiso 1 1 calc R U . A 2
C10 C -0.01970(15) 0.50605(12) 0.80059(12) 0.0182(3) Uani 1 1 d . . . A 2
H10A H 0.0741 0.5601 0.8503 0.022 Uiso 1 1 calc R U . A 2
H10B H -0.0798 0.5621 0.8110 0.022 Uiso 1 1 calc R U . A 2
C11 C -0.08968(15) 0.27236(13) 0.88308(13) 0.0217(3) Uani 1 1 d . . . A 2
C12 C -0.20387(15) 0.31920(14) 0.91931(13) 0.0222(3) Uani 1 1 d . . . A 2
H12 H -0.2740 0.2904 0.9540 0.027 Uiso 1 1 calc R U . A 2
C13 C -0.19351(15) 0.41551(14) 0.89426(12) 0.0201(3) Uani 1 1 d . . . A 2
C14 C -0.04628(18) 0.16918(15) 0.89127(15) 0.0296(3) Uani 1 1 d . . . A 2
H14A H 0.0290 0.1494 0.8465 0.044 Uiso 1 1 calc R U . A 2
H14B H -0.1266 0.0934 0.8571 0.044 Uiso 1 1 calc R U . A 2
H14C H -0.0129 0.1972 0.9756 0.044 Uiso 1 1 calc R U . A 2
C15 C -0.28402(16) 0.50058(15) 0.91344(14) 0.0255(3) Uani 1 1 d . . . A 2
H15A H -0.3169 0.4940 0.8370 0.038 Uiso 1 1 calc R U . A 2
H15B H -0.2301 0.5882 0.9711 0.038 Uiso 1 1 calc R U . A 2
H15C H -0.3647 0.4756 0.9448 0.038 Uiso 1 1 calc R U . A 2
C16 C 0.27989(14) 0.41758(12) 0.48518(12) 0.0175(3) Uani 1 1 d . . . A 2
H16A H 0.2776 0.4589 0.4364 0.021 Uiso 1 1 calc R U . A 2
H16B H 0.3498 0.4775 0.5601 0.021 Uiso 1 1 calc R U . A 2
C17 C 0.35914(14) 0.12814(13) 0.37946(13) 0.0200(3) Uani 1 1 d . . . A 2
C18 C 0.39025(14) 0.14776(14) 0.28418(13) 0.0211(3) Uani 1 1 d . . . A 2
H18 H 0.4208 0.0935 0.2148 0.025 Uiso 1 1 calc R U . A 2
C19 C 0.36726(14) 0.26180(13) 0.31221(12) 0.0189(3) Uani 1 1 d . . . A 2
C20 C 0.36077(16) 0.01680(14) 0.39340(15) 0.0262(3) Uani 1 1 d . . . A 2
H20A H 0.2862 -0.0574 0.3329 0.039 Uiso 1 1 calc R U . A 2
H20B H 0.3456 0.0351 0.4738 0.039 Uiso 1 1 calc R U . A 2
H20C H 0.4516 -0.0004 0.3827 0.039 Uiso 1 1 calc R U . A 2
C21 C 0.37613(17) 0.33071(15) 0.24402(14) 0.0256(3) Uani 1 1 d . . . A 2
H21A H 0.4264 0.4202 0.2981 0.038 Uiso 1 1 calc R U . A 2
H21B H 0.2815 0.3232 0.2106 0.038 Uiso 1 1 calc R U . A 2
H21C H 0.4264 0.2939 0.1786 0.038 Uiso 1 1 calc R U . A 2
C22 C -0.24670(14) 0.27252(12) 0.36387(12) 0.0164(3) Uani 1 1 d . . . A 2
H22A H -0.3265 0.2907 0.4045 0.020 Uiso 1 1 calc R U . A 2
H22B H -0.2324 0.3199 0.3204 0.020 Uiso 1 1 calc R U . A 2
C23 C -0.33933(15) -0.06014(13) 0.21358(13) 0.0229(3) Uani 1 1 d . . . A 2
C24 C -0.34652(15) -0.04588(14) 0.11216(13) 0.0244(3) Uani 1 1 d . . . A 2
H24 H -0.3711 -0.1114 0.0304 0.029 Uiso 1 1 calc R U . A 2
C25 C -0.31060(14) 0.08241(14) 0.15536(12) 0.0197(3) Uani 1 1 d . . . A 2
C26 C -0.36726(19) -0.17892(15) 0.21969(17) 0.0342(4) Uani 1 1 d . . . A 2
H26A H -0.4678 -0.2110 0.2143 0.051 Uiso 1 1 calc R U . A 2
H26B H -0.3158 -0.1610 0.2959 0.051 Uiso 1 1 calc R U . A 2
H26C H -0.3365 -0.2426 0.1529 0.051 Uiso 1 1 calc R U . A 2
C27 C -0.29612(18) 0.15595(15) 0.09191(13) 0.0280(3) Uani 1 1 d . . . A 2
H27A H -0.1986 0.2069 0.1116 0.042 Uiso 1 1 calc R U . A 2
H27B H -0.3569 0.2118 0.1174 0.042 Uiso 1 1 calc R U . A 2
H27C H -0.3233 0.0975 0.0051 0.042 Uiso 1 1 calc R U . A 2
O1A O 0.0230(3) 0.1031(2) 0.6379(2) 0.0414(6) Uani 0.5 1 d . . P B 2
H1A H 0.0287 0.1803 0.6791 0.062 Uiso 0.5 1 calc DR U P B 2
C1A C 0.0039(2) 0.0705(2) 0.5309(2) 0.0460(5) Uani 1 1 d D . . B 1
H1A1 H 0.0825 0.1183 0.5126 0.069 Uiso 1 1 calc R U . B 1
H1A2 H -0.0845 0.0824 0.5059 0.069 Uiso 1 1 calc R U . B 1
H1A3 H 0.0189 0.1040 0.6161 0.069 Uiso 0.5 1 calc R U . B 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3874(15) . ?
O1 C7 1.4445(17) . ?
O2 C4 1.3836(15) . ?
O2 C8 1.4505(16) . ?
O3 C6 1.3853(16) . ?
O3 C9 1.4470(16) . ?
N1 C13 1.3553(18) . ?
N1 N2 1.3621(16) . ?
N1 C10 1.4616(17) . ?
N2 C11 1.3334(18) . ?
N3 C19 1.3527(18) . ?
N3 N4 1.3618(16) . ?
N3 C16 1.4560(17) . ?
N4 C17 1.3304(19) . ?
N5 C25 1.3537(17) . ?
N5 N6 1.3590(16) . ?
N5 C22 1.4554(17) . ?
N6 C23 1.3333(19) . ?
C1 C2 1.3933(19) . ?
C1 C6 1.3935(18) . ?
C1 C10 1.5090(18) . ?
C2 C3 1.3983(18) . ?
C3 C4 1.3957(18) . ?
C3 C16 1.5107(18) . ?
C4 C5 1.3955(18) . ?
C5 C6 1.3956(18) . ?
C5 C22 1.5087(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.401(2) . ?
C11 C14 1.499(2) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9500 . ?
C13 C15 1.490(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.405(2) . ?
C17 C20 1.4942(19) . ?
C18 C19 1.375(2) . ?
C18 H18 0.9500 . ?
C19 C21 1.494(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.404(2) . ?
C23 C26 1.495(2) . ?
C24 C25 1.376(2) . ?
C24 H24 0.9500 . ?
C25 C27 1.490(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O1A C1A 1.228(3) . ?
O1A H1A 0.8400 . ?
C1A H1A1 0.9800 . ?
C1A H1A2 0.9800 . ?
C1A H1A3 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
C2 O1 C7 112.56(10) . . ?
C4 O2 C8 113.05(10) . . ?
C6 O3 C9 113.47(10) . . ?
C13 N1 N2 112.41(11) . . ?
C13 N1 C10 128.92(12) . . ?
N2 N1 C10 118.66(11) . . ?
C11 N2 N1 104.66(12) . . ?
C19 N3 N4 112.33(11) . . ?
C19 N3 C16 128.47(11) . . ?
N4 N3 C16 119.10(11) . . ?
C17 N4 N3 104.80(11) . . ?
C25 N5 N6 112.65(11) . . ?
C25 N5 C22 127.32(11) . . ?
N6 N5 C22 119.97(11) . . ?
C23 N6 N5 104.73(11) . . ?
C2 C1 C6 117.95(12) . . ?
C2 C1 C10 121.33(12) . . ?
C6 C1 C10 120.46(12) . . ?
O1 C2 C1 118.90(12) . . ?
O1 C2 C3 118.93(12) . . ?
C1 C2 C3 122.00(12) . . ?
C4 C3 C2 117.82(12) . . ?
C4 C3 C16 121.36(12) . . ?
C2 C3 C16 120.43(12) . . ?
O2 C4 C5 118.78(11) . . ?
O2 C4 C3 118.83(12) . . ?
C5 C4 C3 122.23(12) . . ?
C4 C5 C6 117.63(12) . . ?
C4 C5 C22 121.24(12) . . ?
C6 C5 C22 120.51(12) . . ?
O3 C6 C5 120.14(11) . . ?
O3 C6 C1 117.35(12) . . ?
C5 C6 C1 122.34(12) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C1 113.77(11) . . ?
N1 C10 H10A 108.8 . . ?
C1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C1 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 111.08(13) . . ?
N2 C11 C14 119.51(14) . . ?
C12 C11 C14 129.40(14) . . ?
C13 C12 C11 105.85(13) . . ?
C13 C12 H12 127.1 . . ?
C11 C12 H12 127.1 . . ?
N1 C13 C12 105.99(13) . . ?
N1 C13 C15 123.41(13) . . ?
C12 C13 C15 130.60(13) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C3 114.21(11) . . ?
N3 C16 H16A 108.7 . . ?
C3 C16 H16A 108.7 . . ?
N3 C16 H16B 108.7 . . ?
C3 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
N4 C17 C18 110.99(12) . . ?
N4 C17 C20 120.43(13) . . ?
C18 C17 C20 128.55(14) . . ?
C19 C18 C17 105.68(13) . . ?
C19 C18 H18 127.2 . . ?
C17 C18 H18 127.2 . . ?
N3 C19 C18 106.20(12) . . ?
N3 C19 C21 122.67(13) . . ?
C18 C19 C21 131.07(13) . . ?
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 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N5 C22 C5 115.11(11) . . ?
N5 C22 H22A 108.5 . . ?
C5 C22 H22A 108.5 . . ?
N5 C22 H22B 108.5 . . ?
C5 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
N6 C23 C24 110.82(13) . . ?
N6 C23 C26 120.14(14) . . ?
C24 C23 C26 129.04(14) . . ?
C25 C24 C23 105.96(13) . . ?
C25 C24 H24 127.0 . . ?
C23 C24 H24 127.0 . . ?
N5 C25 C24 105.84(12) . . ?
N5 C25 C27 122.93(13) . . ?
C24 C25 C27 131.20(13) . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1A C1A H1A1 111.0 2_556 . ?
C1A C1A H1A2 111.0 2_556 . ?
H1A1 C1A H1A2 109.5 . . ?
C1A C1A H1A3 108.0 2_556 . ?
H1A1 C1A H1A3 108.0 . . ?
H1A2 C1A H1A3 108.0 . . ?

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
C13 N1 N2 C11 0.61(15) . . . . ?
C10 N1 N2 C11 -179.84(11) . . . . ?
C19 N3 N4 C17 -0.54(15) . . . . ?
C16 N3 N4 C17 176.10(11) . . . . ?
C25 N5 N6 C23 0.57(15) . . . . ?
C22 N5 N6 C23 177.99(11) . . . . ?
C7 O1 C2 C1 93.89(14) . . . . ?
C7 O1 C2 C3 -90.71(14) . . . . ?
C6 C1 C2 O1 175.67(11) . . . . ?
C10 C1 C2 O1 1.47(18) . . . . ?
C6 C1 C2 C3 0.41(19) . . . . ?
C10 C1 C2 C3 -173.79(12) . . . . ?
O1 C2 C3 C4 -176.85(11) . . . . ?
C1 C2 C3 C4 -1.60(19) . . . . ?
O1 C2 C3 C16 -3.96(18) . . . . ?
C1 C2 C3 C16 171.30(12) . . . . ?
C8 O2 C4 C5 -91.21(14) . . . . ?
C8 O2 C4 C3 93.36(14) . . . . ?
C2 C3 C4 O2 177.39(11) . . . . ?
C16 C3 C4 O2 4.57(18) . . . . ?
C2 C3 C4 C5 2.12(19) . . . . ?
C16 C3 C4 C5 -170.71(12) . . . . ?
O2 C4 C5 C6 -176.70(11) . . . . ?
C3 C4 C5 C6 -1.42(19) . . . . ?
O2 C4 C5 C22 -5.64(18) . . . . ?
C3 C4 C5 C22 169.63(12) . . . . ?
C9 O3 C6 C5 79.93(14) . . . . ?
C9 O3 C6 C1 -104.70(13) . . . . ?
C4 C5 C6 O3 175.29(11) . . . . ?
C22 C5 C6 O3 4.17(18) . . . . ?
C4 C5 C6 C1 0.16(19) . . . . ?
C22 C5 C6 C1 -170.97(12) . . . . ?
C2 C1 C6 O3 -174.94(11) . . . . ?
C10 C1 C6 O3 -0.68(18) . . . . ?
C2 C1 C6 C5 0.33(19) . . . . ?
C10 C1 C6 C5 174.59(12) . . . . ?
C13 N1 C10 C1 -122.71(15) . . . . ?
N2 N1 C10 C1 57.82(16) . . . . ?
C2 C1 C10 N1 -114.24(14) . . . . ?
C6 C1 C10 N1 71.70(16) . . . . ?
N1 N2 C11 C12 -0.13(15) . . . . ?
N1 N2 C11 C14 -179.16(13) . . . . ?
N2 C11 C12 C13 -0.36(16) . . . . ?
C14 C11 C12 C13 178.55(15) . . . . ?
N2 N1 C13 C12 -0.84(15) . . . . ?
C10 N1 C13 C12 179.67(13) . . . . ?
N2 N1 C13 C15 179.48(13) . . . . ?
C10 N1 C13 C15 0.0(2) . . . . ?
C11 C12 C13 N1 0.70(15) . . . . ?
C11 C12 C13 C15 -179.64(14) . . . . ?
C19 N3 C16 C3 125.35(14) . . . . ?
N4 N3 C16 C3 -50.68(16) . . . . ?
C4 C3 C16 N3 -69.89(16) . . . . ?
C2 C3 C16 N3 117.47(13) . . . . ?
N3 N4 C17 C18 0.65(15) . . . . ?
N3 N4 C17 C20 -177.47(12) . . . . ?
N4 C17 C18 C19 -0.53(16) . . . . ?
C20 C17 C18 C19 177.40(13) . . . . ?
N4 N3 C19 C18 0.22(15) . . . . ?
C16 N3 C19 C18 -176.02(12) . . . . ?
N4 N3 C19 C21 177.69(12) . . . . ?
C16 N3 C19 C21 1.4(2) . . . . ?
C17 C18 C19 N3 0.17(15) . . . . ?
C17 C18 C19 C21 -177.00(14) . . . . ?
C25 N5 C22 C5 -128.34(14) . . . . ?
N6 N5 C22 C5 54.66(16) . . . . ?
C4 C5 C22 N5 69.92(16) . . . . ?
C6 C5 C22 N5 -119.28(13) . . . . ?
N5 N6 C23 C24 -0.49(16) . . . . ?
N5 N6 C23 C26 179.53(13) . . . . ?
N6 C23 C24 C25 0.25(17) . . . . ?
C26 C23 C24 C25 -179.77(15) . . . . ?
N6 N5 C25 C24 -0.42(16) . . . . ?
C22 N5 C25 C24 -177.61(12) . . . . ?
N6 N5 C25 C27 -178.88(13) . . . . ?
C22 N5 C25 C27 3.9(2) . . . . ?
C23 C24 C25 N5 0.10(16) . . . . ?
C23 C24 C25 C27 178.38(15) . . . . ?

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
O1A H1A N2 0.84 2.19 2.937(2) 149.0 .
C7 H7A N4 0.98 2.62 3.539(2) 156.7 .
C7 H7B N2 0.98 2.56 3.4775(19) 156.1 .
C8 H8A N5 0.98 2.40 3.1257(18) 130.0 .
C8 H8A N6 0.98 2.61 3.5344(19) 156.6 .
C8 H8B N3 0.98 2.45 3.1558(18) 128.8 .
C8 H8B N4 0.98 2.59 3.5038(19) 154.6 .
C9 H9A N1 0.98 2.68 3.3262(18) 124.1 .
C9 H9B N6 0.98 2.50 3.4594(19) 165.6 .

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_nk23cor
_database_code_depnum_ccdc_archive 'CCDC 1533890'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H27 Br3 N6, 2(C2 H3 N)'
_chemical_formula_sum            'C28 H33 Br3 N8'
_chemical_formula_weight         721.35

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   10.3117(3)
_cell_length_b                   19.6259(7)
_cell_length_c                   14.9856(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3032.73(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      31.53

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.330
_exptl_absorpt_coefficient_mu    4.023
_shelx_estimated_absorpt_T_min   0.224
_shelx_estimated_absorpt_T_max   0.350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2243
_exptl_absorpt_correction_T_max  0.3503
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31589
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         29.399
_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 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4304
_reflns_number_gt                3785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0256P)²+2.8501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0573
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.56730(2) 0.2500 0.63505(2) 0.02016(6) Uani 1 2 d S T P . .
Br2 Br 0.84396(2) 0.57320(2) 0.07564(2) 0.02723(6) Uani 1 1 d . . . . .
N1 N 0.43862(17) 0.2500 0.38407(12) 0.0139(3) Uani 1 2 d S T P . .
N2 N 0.5653(2) 0.2500 0.36452(14) 0.0355(6) Uani 1 2 d S T P . .
N3 N 0.61140(12) 0.41146(7) 0.05628(9) 0.0145(2) Uani 1 1 d . . . . .
N4 N 0.72320(12) 0.37788(7) 0.03978(9) 0.0185(3) Uani 1 1 d . . . . .
C1 C 0.39701(19) 0.2500 0.22186(14) 0.0132(4) Uani 1 2 d S T P . .
C2 C 0.42203(13) 0.31183(7) 0.17904(9) 0.0130(3) Uani 1 1 d . . . . .
C3 C 0.47012(14) 0.31149(7) 0.09165(9) 0.0127(3) Uani 1 1 d . . . . .
C4 C 0.49565(19) 0.2500 0.04751(13) 0.0125(4) Uani 1 2 d S T P . .
C5 C 0.3385(2) 0.2500 0.31426(14) 0.0151(4) Uani 1 2 d S T P . .
H5A H 0.2841 0.2900 0.3212 0.018 Uiso 0.5 1 calc R U P . .
H5B H 0.2841 0.2100 0.3212 0.018 Uiso 0.5 1 calc R U P . .
C6 C 0.6255(2) 0.2500 0.44282(17) 0.0368(7) Uani 1 2 d S T P . .
H6 H 0.7150 0.2500 0.4503 0.044 Uiso 1 2 calc R U P . .
C7 C 0.5359(2) 0.2500 0.51196(14) 0.0153(4) Uani 1 2 d S T P . .
C8 C 0.4167(2) 0.2500 0.47213(14) 0.0166(4) Uani 1 2 d S T P . .
H8 H 0.3365 0.2500 0.5005 0.020 Uiso 1 2 calc R U P . .
C9 C 0.39326(15) 0.37844(8) 0.22582(10) 0.0166(3) Uani 1 1 d . . . . .
H9A H 0.4516 0.4133 0.2035 0.020 Uiso 1 1 calc R U . . .
H9B H 0.4093 0.3732 0.2892 0.020 Uiso 1 1 calc R U . . .
C10 C 0.25270(16) 0.40172(9) 0.21169(12) 0.0227(3) Uani 1 1 d . . . . .
H10A H 0.2385 0.4108 0.1495 0.034 Uiso 1 1 calc R U . . .
H10B H 0.2371 0.4424 0.2456 0.034 Uiso 1 1 calc R U . . .
H10C H 0.1946 0.3665 0.2312 0.034 Uiso 1 1 calc R U . . .
C11 C 0.48603(14) 0.37813(8) 0.04268(10) 0.0144(3) Uani 1 1 d . . . . .
H11A H 0.4744 0.3700 -0.0207 0.017 Uiso 1 1 calc R U . . .
H11B H 0.4180 0.4090 0.0617 0.017 Uiso 1 1 calc R U . . .
C12 C 0.81514(15) 0.42568(9) 0.04437(11) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.9033 0.4177 0.0363 0.024 Uiso 1 1 calc R U . . .
C13 C 0.76082(15) 0.48899(8) 0.06293(10) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.62983(15) 0.47844(8) 0.07014(10) 0.0163(3) Uani 1 1 d . . . . .
H14 H 0.5666 0.5110 0.0822 0.020 Uiso 1 1 calc R U . . .
C15 C 0.5447(2) 0.2500 -0.04765(14) 0.0164(4) Uani 1 2 d S T P . .
H15A H 0.5984 0.2100 -0.0571 0.020 Uiso 0.5 1 calc R U P . .
H15B H 0.5984 0.2900 -0.0571 0.020 Uiso 0.5 1 calc R U P . .
C16 C 0.4340(2) 0.2500 -0.11563(15) 0.0231(5) Uani 1 2 d S T P . .
H16A H 0.3796 0.2110 -0.1058 0.035 Uiso 0.5 1 calc R U P . .
H16B H 0.4693 0.2481 -0.1749 0.035 Uiso 0.5 1 calc R U P . .
H16C H 0.3837 0.2908 -0.1089 0.035 Uiso 0.5 1 calc R U P . .
N1A N 0.41270(17) 0.57838(10) 0.16592(12) 0.0374(4) Uani 1 1 d . . . . .
C1A C 0.30816(19) 0.58995(10) 0.17997(12) 0.0285(4) Uani 1 1 d . . . . .
C2A C 0.1726(2) 0.60414(19) 0.19853(18) 0.0596(8) Uani 1 1 d . . . . .
H2A1 H 0.1192 0.5712 0.1687 0.089 Uiso 1 1 calc R U . . .
H2A2 H 0.1513 0.6490 0.1775 0.089 Uiso 1 1 calc R U . . .
H2A3 H 0.1577 0.6017 0.2617 0.089 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.873(2) . ?
Br2 C13 1.8714(16) . ?
N1 C8 1.339(3) . ?
N1 N2 1.339(3) . ?
N1 C5 1.470(3) . ?
N2 C6 1.327(3) . ?
N3 C14 1.344(2) . ?
N3 N4 1.3508(18) . ?
N3 C11 1.4630(19) . ?
N4 C12 1.336(2) . ?
C1 C2 1.3967(17) 7_565 ?
C1 C2 1.3968(17) . ?
C1 C5 1.510(3) . ?
C2 C3 1.400(2) . ?
C2 C9 1.513(2) . ?
C3 C4 1.4012(17) . ?
C3 C11 1.509(2) . ?
C4 C3 1.4012(17) 7_565 ?
C4 C15 1.513(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.388(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.534(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.391(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.530(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1A C1A 1.122(3) . ?
C1A C2A 1.452(3) . ?
C2A H2A1 0.9600 . ?
C2A H2A2 0.9600 . ?
C2A H2A3 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
C8 N1 N2 112.36(18) . . ?
C8 N1 C5 125.67(18) . . ?
N2 N1 C5 121.97(18) . . ?
C6 N2 N1 105.21(19) . . ?
C14 N3 N4 112.63(13) . . ?
C14 N3 C11 125.70(13) . . ?
N4 N3 C11 120.70(12) . . ?
C12 N4 N3 104.69(13) . . ?
C2 C1 C2 120.63(18) 7_565 . ?
C2 C1 C5 119.67(9) 7_565 . ?
C2 C1 C5 119.67(9) . . ?
C1 C2 C3 119.41(14) . . ?
C1 C2 C9 120.11(13) . . ?
C3 C2 C9 120.46(13) . . ?
C2 C3 C4 120.80(14) . . ?
C2 C3 C11 119.29(13) . . ?
C4 C3 C11 119.78(13) . . ?
C3 C4 C3 118.93(18) 7_565 . ?
C3 C4 C15 120.51(9) 7_565 . ?
C3 C4 C15 120.51(9) . . ?
N1 C5 C1 111.85(17) . . ?
N1 C5 H5A 109.2 . . ?
C1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
C1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N2 C6 C7 110.4(2) . . ?
N2 C6 H6 124.8 . . ?
C7 C6 H6 124.8 . . ?
C8 C7 C6 105.81(19) . . ?
C8 C7 Br1 125.85(16) . . ?
C6 C7 Br1 128.33(18) . . ?
N1 C8 C7 106.18(18) . . ?
N1 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
C2 C9 C10 112.24(13) . . ?
C2 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
C2 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 C3 114.58(12) . . ?
N3 C11 H11A 108.6 . . ?
C3 C11 H11A 108.6 . . ?
N3 C11 H11B 108.6 . . ?
C3 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N4 C12 C13 110.61(14) . . ?
N4 C12 H12 124.7 . . ?
C13 C12 H12 124.7 . . ?
C14 C13 C12 106.12(14) . . ?
C14 C13 Br2 125.23(13) . . ?
C12 C13 Br2 128.66(12) . . ?
N3 C14 C13 105.95(14) . . ?
N3 C14 H14 127.0 . . ?
C13 C14 H14 127.0 . . ?
C4 C15 C16 112.21(18) . . ?
C4 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C4 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1A C1A C2A 179.4(3) . . ?
C1A C2A H2A1 109.5 . . ?
C1A C2A H2A2 109.5 . . ?
H2A1 C2A H2A2 109.5 . . ?
C1A C2A H2A3 109.5 . . ?
H2A1 C2A H2A3 109.5 . . ?
H2A2 C2A H2A3 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
C8 N1 N2 C6 0.000(0) . . . . ?
C5 N1 N2 C6 180.000(0) . . . . ?
C14 N3 N4 C12 0.59(17) . . . . ?
C11 N3 N4 C12 169.93(13) . . . . ?
C2 C1 C2 C3 1.3(3) 7_565 . . . ?
C5 C1 C2 C3 -176.79(15) . . . . ?
C2 C1 C2 C9 179.40(12) 7_565 . . . ?
C5 C1 C2 C9 1.3(2) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
C9 C2 C3 C4 -179.29(15) . . . . ?
C1 C2 C3 C11 174.70(15) . . . . ?
C9 C2 C3 C11 -3.4(2) . . . . ?
C2 C3 C4 C3 1.1(3) . . . 7_565 ?
C11 C3 C4 C3 -174.79(11) . . . 7_565 ?
C2 C3 C4 C15 178.61(16) . . . . ?
C11 C3 C4 C15 2.7(2) . . . . ?
C8 N1 C5 C1 180.000(0) . . . . ?
N2 N1 C5 C1 0.000(0) . . . . ?
C2 C1 C5 N1 90.93(16) 7_565 . . . ?
C2 C1 C5 N1 -90.93(16) . . . . ?
N1 N2 C6 C7 0.000(0) . . . . ?
N2 C6 C7 C8 0.000(0) . . . . ?
N2 C6 C7 Br1 180.000(0) . . . . ?
N2 N1 C8 C7 0.000(0) . . . . ?
C5 N1 C8 C7 180.000(0) . . . . ?
C6 C7 C8 N1 0.000(0) . . . . ?
Br1 C7 C8 N1 180.000(0) . . . . ?
C1 C2 C9 C10 -86.97(18) . . . . ?
C3 C2 C9 C10 91.08(17) . . . . ?
C14 N3 C11 C3 -137.58(15) . . . . ?
N4 N3 C11 C3 54.55(18) . . . . ?
C2 C3 C11 N3 88.34(16) . . . . ?
C4 C3 C11 N3 -95.69(17) . . . . ?
N3 N4 C12 C13 -0.50(17) . . . . ?
N4 C12 C13 C14 0.24(19) . . . . ?
N4 C12 C13 Br2 -179.45(12) . . . . ?
N4 N3 C14 C13 -0.45(18) . . . . ?
C11 N3 C14 C13 -169.15(13) . . . . ?
C12 C13 C14 N3 0.12(18) . . . . ?
Br2 C13 C14 N3 179.82(11) . . . . ?
C3 C4 C15 C16 88.72(16) 7_565 . . . ?
C3 C4 C15 C16 -88.72(16) . . . . ?

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
C11 H11A N1A 0.97 2.67 3.405(2) 133.0 5_665
C14 H14 N1A 0.93 2.42 3.305(2) 159.5 .

_refine_diff_density_max         0.760
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.082

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_Koch_24_0m
_database_code_depnum_ccdc_archive 'CCDC 1533891'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H39 Br3 N6'
_chemical_formula_sum            'C30 H39 Br3 N6'
_chemical_formula_weight         723.40

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

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

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

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

_cell_length_a                   11.5273(4)
_cell_length_b                   11.6453(4)
_cell_length_c                   11.7944(4)
_cell_angle_alpha                89.069(2)
_cell_angle_beta                 82.606(2)
_cell_angle_gamma                86.469(1)
_cell_volume                     1567.07(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9952
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.36

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    3.891
_shelx_estimated_absorpt_T_min   0.292
_shelx_estimated_absorpt_T_max   0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2918
_exptl_absorpt_correction_T_max  0.6970
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31196
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.785
_diffrn_reflns_theta_max         28.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7601
_reflns_number_gt                6632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart APEX 2 (Bruker AXS)'
_computing_cell_refinement       'SAINT-NT (Sheldrick, 2008)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  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)+(0.0279P)²+0.5178P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7601
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0290
_refine_ls_R_factor_gt           0.0221
_refine_ls_wR_factor_ref         0.0560
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.01855(2) 1.53204(2) 0.82488(2) 0.03294(5) Uani 1 1 d . . . . .
Br2 Br 0.83288(2) 0.68249(2) 0.60142(2) 0.03025(5) Uani 1 1 d . . . . .
Br3 Br 0.38505(2) 0.65291(2) 1.47232(2) 0.02703(5) Uani 1 1 d . . . . .
N1 N 0.09285(10) 1.19357(10) 0.83331(11) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.18829(11) 1.22091(11) 0.75944(12) 0.0198(3) Uani 1 1 d . . . . .
N3 N 0.49835(10) 0.76236(10) 0.72311(11) 0.0150(2) Uani 1 1 d . . . . .
N4 N 0.51694(10) 0.85877(10) 0.65842(11) 0.0159(2) Uani 1 1 d . . . . .
N5 N 0.33010(10) 0.88915(11) 1.23191(11) 0.0161(2) Uani 1 1 d . . . . .
N6 N 0.21753(10) 0.85572(12) 1.25343(11) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.17995(11) 1.00371(12) 0.89222(13) 0.0136(3) Uani 1 1 d . . . . .
C2 C 0.23781(11) 0.91923(12) 0.81803(12) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.32766(12) 0.84725(12) 0.85581(12) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.36516(12) 0.86455(12) 0.96251(13) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.31188(11) 0.95419(12) 1.03252(12) 0.0138(3) Uani 1 1 d . . . . .
C6 C 0.21663(12) 1.02219(12) 0.99917(13) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.20557(12) 0.90697(13) 0.69853(13) 0.0172(3) Uani 1 1 d . . . . .
H7A H 0.2752 0.8806 0.6484 0.021 Uiso 1 1 calc R U . . .
H7B H 0.1800 0.9822 0.6713 0.021 Uiso 1 1 calc R U . . .
C8 C 0.10926(14) 0.82389(15) 0.68935(15) 0.0243(3) Uani 1 1 d . . . . .
H8A H 0.1366 0.7474 0.7087 0.037 Uiso 1 1 calc R U . . .
H8B H 0.0900 0.8251 0.6125 0.037 Uiso 1 1 calc R U . . .
H8C H 0.0409 0.8471 0.7411 0.037 Uiso 1 1 calc R U . . .
C9 C 0.46287(12) 0.78586(12) 1.00016(13) 0.0168(3) Uani 1 1 d . . . . .
H9A H 0.5042 0.8279 1.0512 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5181 0.7649 0.9335 0.020 Uiso 1 1 calc R U . . .
C10 C 0.42135(14) 0.67532(13) 1.06103(14) 0.0213(3) Uani 1 1 d . . . . .
H10A H 0.3650 0.6949 1.1261 0.032 Uiso 1 1 calc R U . . .
H10B H 0.4872 0.6320 1.0859 0.032 Uiso 1 1 calc R U . . .
H10C H 0.3859 0.6299 1.0092 0.032 Uiso 1 1 calc R U . . .
C11 C 0.15454(12) 1.11460(12) 1.07779(13) 0.0167(3) Uani 1 1 d . . . . .
H11A H 0.1519 1.0874 1.1562 0.020 Uiso 1 1 calc R U . . .
H11B H 0.0744 1.1268 1.0613 0.020 Uiso 1 1 calc R U . . .
C12 C 0.21234(13) 1.22983(13) 1.06706(15) 0.0209(3) Uani 1 1 d . . . . .
H12A H 0.2874 1.2213 1.0944 0.031 Uiso 1 1 calc R U . . .
H12B H 0.1634 1.2866 1.1117 0.031 Uiso 1 1 calc R U . . .
H12C H 0.2225 1.2539 0.9883 0.031 Uiso 1 1 calc R U . . .
C13 C 0.07316(12) 1.07254(12) 0.85746(13) 0.0152(3) Uani 1 1 d . . . . .
H13A H 0.0504 1.0381 0.7900 0.018 Uiso 1 1 calc R U . . .
H13B H 0.0086 1.0675 0.9184 0.018 Uiso 1 1 calc R U . . .
C14 C 0.17837(13) 1.33536(13) 0.74919(14) 0.0211(3) Uani 1 1 d . . . . .
C15 C 0.07648(13) 1.37818(12) 0.81589(14) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.02183(12) 1.28662(12) 0.86896(13) 0.0173(3) Uani 1 1 d . . . . .
C17 C 0.26764(15) 1.40112(15) 0.67640(17) 0.0318(4) Uani 1 1 d . . . . .
H17A H 0.3207 1.4309 0.7234 0.048 Uiso 1 1 calc R U . . .
H17B H 0.2290 1.4637 0.6391 0.048 Uiso 1 1 calc R U . . .
H17C H 0.3106 1.3510 0.6199 0.048 Uiso 1 1 calc R U . . .
C18 C -0.09059(13) 1.28129(13) 0.94558(14) 0.0212(3) Uani 1 1 d . . . . .
H18A H -0.1388 1.2280 0.9154 0.032 Uiso 1 1 calc R U . . .
H18B H -0.1305 1.3562 0.9504 0.032 Uiso 1 1 calc R U . . .
H18C H -0.0751 1.2562 1.0204 0.032 Uiso 1 1 calc R U . . .
C19 C 0.38083(12) 0.74604(12) 0.78251(13) 0.0158(3) Uani 1 1 d . . . . .
H19A H 0.3844 0.6781 0.8309 0.019 Uiso 1 1 calc R U . . .
H19B H 0.3293 0.7318 0.7261 0.019 Uiso 1 1 calc R U . . .
C20 C 0.62789(12) 0.84525(13) 0.60933(13) 0.0172(3) Uani 1 1 d . . . . .
C21 C 0.67763(12) 0.73962(13) 0.64273(13) 0.0184(3) Uani 1 1 d . . . . .
C22 C 0.59330(13) 0.68675(13) 0.71442(13) 0.0176(3) Uani 1 1 d . . . . .
C23 C 0.68339(14) 0.93375(14) 0.53115(14) 0.0229(3) Uani 1 1 d . . . . .
H23A H 0.6247 0.9912 0.5139 0.034 Uiso 1 1 calc R U . . .
H23B H 0.7195 0.8979 0.4616 0.034 Uiso 1 1 calc R U . . .
H23C H 0.7418 0.9692 0.5675 0.034 Uiso 1 1 calc R U . . .
C24 C 0.59736(14) 0.57255(13) 0.77296(15) 0.0248(3) Uani 1 1 d . . . . .
H24A H 0.5786 0.5828 0.8540 0.037 Uiso 1 1 calc R U . . .
H24B H 0.6746 0.5361 0.7566 0.037 Uiso 1 1 calc R U . . .
H24C H 0.5415 0.5252 0.7460 0.037 Uiso 1 1 calc R U . . .
C25 C 0.35692(12) 0.97782(12) 1.14526(13) 0.0156(3) Uani 1 1 d . . . . .
H25A H 0.4412 0.9835 1.1314 0.019 Uiso 1 1 calc R U . . .
H25B H 0.3224 1.0513 1.1743 0.019 Uiso 1 1 calc R U . . .
C26 C 0.22024(13) 0.77471(14) 1.33467(13) 0.0217(3) Uani 1 1 d . . . . .
C27 C 0.33394(14) 0.75866(13) 1.36424(13) 0.0197(3) Uani 1 1 d . . . . .
C28 C 0.40316(13) 0.83302(13) 1.29829(13) 0.0174(3) Uani 1 1 d . . . . .
C29 C 0.11388(15) 0.71211(17) 1.37829(15) 0.0315(4) Uani 1 1 d . . . . .
H29A H 0.0448 0.7597 1.3686 0.047 Uiso 1 1 calc R U . . .
H29B H 0.1147 0.6942 1.4579 0.047 Uiso 1 1 calc R U . . .
H29C H 0.1138 0.6422 1.3363 0.047 Uiso 1 1 calc R U . . .
C30 C 0.52994(13) 0.85303(14) 1.29505(15) 0.0219(3) Uani 1 1 d . . . . .
H30A H 0.5732 0.8164 1.2291 0.033 Uiso 1 1 calc R U . . .
H30B H 0.5578 0.8214 1.3629 0.033 Uiso 1 1 calc R U . . .
H30C H 0.5405 0.9342 1.2911 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C15 1.8731(15) . ?
Br2 C21 1.8768(14) . ?
Br3 C27 1.8818(15) . ?
N1 C16 1.3558(19) . ?
N1 N2 1.3631(17) . ?
N1 C13 1.4591(18) . ?
N2 C14 1.336(2) . ?
N3 C22 1.3562(18) . ?
N3 N4 1.3595(16) . ?
N3 C19 1.4647(18) . ?
N4 C20 1.3355(19) . ?
N5 C28 1.3545(19) . ?
N5 N6 1.3690(16) . ?
N5 C25 1.4595(19) . ?
N6 C26 1.335(2) . ?
C1 C6 1.405(2) . ?
C1 C2 1.406(2) . ?
C1 C13 1.5243(19) . ?
C2 C3 1.4048(19) . ?
C2 C7 1.514(2) . ?
C3 C4 1.404(2) . ?
C3 C19 1.523(2) . ?
C4 C5 1.403(2) . ?
C4 C9 1.5145(19) . ?
C5 C6 1.4076(19) . ?
C5 C25 1.523(2) . ?
C6 C11 1.516(2) . ?
C7 C8 1.532(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.536(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.531(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.396(2) . ?
C14 C17 1.494(2) . ?
C15 C16 1.373(2) . ?
C16 C18 1.485(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.397(2) . ?
C20 C23 1.490(2) . ?
C21 C22 1.373(2) . ?
C22 C24 1.489(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.400(2) . ?
C26 C29 1.495(2) . ?
C27 C28 1.377(2) . ?
C28 C30 1.490(2) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C16 N1 N2 113.15(12) . . ?
C16 N1 C13 127.81(12) . . ?
N2 N1 C13 118.84(12) . . ?
C14 N2 N1 104.90(12) . . ?
C22 N3 N4 112.75(12) . . ?
C22 N3 C19 127.88(12) . . ?
N4 N3 C19 119.05(11) . . ?
C20 N4 N3 105.17(11) . . ?
C28 N5 N6 112.80(12) . . ?
C28 N5 C25 128.45(12) . . ?
N6 N5 C25 118.75(11) . . ?
C26 N6 N5 105.08(12) . . ?
C6 C1 C2 120.86(13) . . ?
C6 C1 C13 119.91(13) . . ?
C2 C1 C13 119.18(13) . . ?
C3 C2 C1 118.92(13) . . ?
C3 C2 C7 120.33(13) . . ?
C1 C2 C7 120.74(12) . . ?
C4 C3 C2 120.71(13) . . ?
C4 C3 C19 119.72(12) . . ?
C2 C3 C19 119.50(13) . . ?
C5 C4 C3 119.68(13) . . ?
C5 C4 C9 121.02(13) . . ?
C3 C4 C9 119.30(13) . . ?
C4 C5 C6 120.23(13) . . ?
C4 C5 C25 119.92(12) . . ?
C6 C5 C25 119.85(13) . . ?
C1 C6 C5 119.34(13) . . ?
C1 C6 C11 120.38(12) . . ?
C5 C6 C11 120.28(13) . . ?
C2 C7 C8 114.56(12) . . ?
C2 C7 H7A 108.6 . . ?
C8 C7 H7A 108.6 . . ?
C2 C7 H7B 108.6 . . ?
C8 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 C10 114.21(12) . . ?
C4 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C4 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C12 114.01(12) . . ?
C6 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C6 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C1 113.63(11) . . ?
N1 C13 H13A 108.8 . . ?
C1 C13 H13A 108.8 . . ?
N1 C13 H13B 108.8 . . ?
C1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
N2 C14 C15 109.63(13) . . ?
N2 C14 C17 122.19(15) . . ?
C15 C14 C17 128.18(15) . . ?
C16 C15 C14 107.97(13) . . ?
C16 C15 Br1 125.54(12) . . ?
C14 C15 Br1 126.38(12) . . ?
N1 C16 C15 104.34(13) . . ?
N1 C16 C18 124.49(13) . . ?
C15 C16 C18 131.14(14) . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C3 114.52(11) . . ?
N3 C19 H19A 108.6 . . ?
C3 C19 H19A 108.6 . . ?
N3 C19 H19B 108.6 . . ?
C3 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
N4 C20 C21 109.70(13) . . ?
N4 C20 C23 122.12(14) . . ?
C21 C20 C23 128.18(14) . . ?
C22 C21 C20 107.52(13) . . ?
C22 C21 Br2 126.12(12) . . ?
C20 C21 Br2 126.33(11) . . ?
N3 C22 C21 104.83(13) . . ?
N3 C22 C24 124.64(13) . . ?
C21 C22 C24 130.53(14) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C5 113.14(11) . . ?
N5 C25 H25A 109.0 . . ?
C5 C25 H25A 109.0 . . ?
N5 C25 H25B 109.0 . . ?
C5 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
N6 C26 C27 109.69(13) . . ?
N6 C26 C29 121.52(14) . . ?
C27 C26 C29 128.75(15) . . ?
C28 C27 C26 107.67(14) . . ?
C28 C27 Br3 125.70(12) . . ?
C26 C27 Br3 126.62(12) . . ?
N5 C28 C27 104.76(13) . . ?
N5 C28 C30 124.69(13) . . ?
C27 C28 C30 130.55(14) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 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 . . ?

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
C16 N1 N2 C14 0.91(16) . . . . ?
C13 N1 N2 C14 176.10(12) . . . . ?
C22 N3 N4 C20 -1.49(16) . . . . ?
C19 N3 N4 C20 -175.56(12) . . . . ?
C28 N5 N6 C26 -0.96(17) . . . . ?
C25 N5 N6 C26 179.67(13) . . . . ?
C6 C1 C2 C3 4.76(19) . . . . ?
C13 C1 C2 C3 -172.84(12) . . . . ?
C6 C1 C2 C7 -174.22(12) . . . . ?
C13 C1 C2 C7 8.18(19) . . . . ?
C1 C2 C3 C4 -4.6(2) . . . . ?
C7 C2 C3 C4 174.34(12) . . . . ?
C1 C2 C3 C19 172.49(12) . . . . ?
C7 C2 C3 C19 -8.53(19) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C19 C3 C4 C5 -176.71(12) . . . . ?
C2 C3 C4 C9 -179.54(12) . . . . ?
C19 C3 C4 C9 3.33(19) . . . . ?
C3 C4 C5 C6 3.8(2) . . . . ?
C9 C4 C5 C6 -176.25(12) . . . . ?
C3 C4 C5 C25 -176.43(12) . . . . ?
C9 C4 C5 C25 3.5(2) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C13 C1 C6 C5 176.94(12) . . . . ?
C2 C1 C6 C11 179.20(12) . . . . ?
C13 C1 C6 C11 -3.22(19) . . . . ?
C4 C5 C6 C1 -3.7(2) . . . . ?
C25 C5 C6 C1 176.55(12) . . . . ?
C4 C5 C6 C11 176.49(12) . . . . ?
C25 C5 C6 C11 -3.29(19) . . . . ?
C3 C2 C7 C8 90.79(16) . . . . ?
C1 C2 C7 C8 -90.24(16) . . . . ?
C5 C4 C9 C10 93.29(16) . . . . ?
C3 C4 C9 C10 -86.75(17) . . . . ?
C1 C6 C11 C12 -94.75(15) . . . . ?
C5 C6 C11 C12 85.09(17) . . . . ?
C16 N1 C13 C1 -134.49(15) . . . . ?
N2 N1 C13 C1 51.11(18) . . . . ?
C6 C1 C13 N1 70.68(17) . . . . ?
C2 C1 C13 N1 -111.70(14) . . . . ?
N1 N2 C14 C15 -0.51(17) . . . . ?
N1 N2 C14 C17 178.90(14) . . . . ?
N2 C14 C15 C16 -0.03(18) . . . . ?
C17 C14 C15 C16 -179.39(16) . . . . ?
N2 C14 C15 Br1 -176.47(11) . . . . ?
C17 C14 C15 Br1 4.2(2) . . . . ?
N2 N1 C16 C15 -0.93(17) . . . . ?
C13 N1 C16 C15 -175.59(13) . . . . ?
N2 N1 C16 C18 177.29(13) . . . . ?
C13 N1 C16 C18 2.6(2) . . . . ?
C14 C15 C16 N1 0.56(17) . . . . ?
Br1 C15 C16 N1 177.04(11) . . . . ?
C14 C15 C16 C18 -177.48(15) . . . . ?
Br1 C15 C16 C18 -1.0(2) . . . . ?
C22 N3 C19 C3 134.66(15) . . . . ?
N4 N3 C19 C3 -52.27(17) . . . . ?
C4 C3 C19 N3 -76.87(16) . . . . ?
C2 C3 C19 N3 105.97(15) . . . . ?
N3 N4 C20 C21 0.67(16) . . . . ?
N3 N4 C20 C23 -179.61(13) . . . . ?
N4 C20 C21 C22 0.33(18) . . . . ?
C23 C20 C21 C22 -179.37(15) . . . . ?
N4 C20 C21 Br2 -177.72(11) . . . . ?
C23 C20 C21 Br2 2.6(2) . . . . ?
N4 N3 C22 C21 1.68(17) . . . . ?
C19 N3 C22 C21 175.11(13) . . . . ?
N4 N3 C22 C24 -178.21(14) . . . . ?
C19 N3 C22 C24 -4.8(2) . . . . ?
C20 C21 C22 N3 -1.18(17) . . . . ?
Br2 C21 C22 N3 176.87(11) . . . . ?
C20 C21 C22 C24 178.71(16) . . . . ?
Br2 C21 C22 C24 -3.2(3) . . . . ?
C28 N5 C25 C5 130.92(15) . . . . ?
N6 N5 C25 C5 -49.84(17) . . . . ?
C4 C5 C25 N5 -70.81(16) . . . . ?
C6 C5 C25 N5 108.97(14) . . . . ?
N5 N6 C26 C27 0.54(17) . . . . ?
N5 N6 C26 C29 -177.17(15) . . . . ?
N6 C26 C27 C28 0.02(19) . . . . ?
C29 C26 C27 C28 177.53(17) . . . . ?
N6 C26 C27 Br3 -178.88(11) . . . . ?
C29 C26 C27 Br3 -1.4(3) . . . . ?
N6 N5 C28 C27 0.97(17) . . . . ?
C25 N5 C28 C27 -179.74(14) . . . . ?
N6 N5 C28 C30 -178.95(14) . . . . ?
C25 N5 C28 C30 0.3(2) . . . . ?
C26 C27 C28 N5 -0.59(17) . . . . ?
Br3 C27 C28 N5 178.33(11) . . . . ?
C26 C27 C28 C30 179.33(16) . . . . ?
Br3 C27 C28 C30 -1.8(3) . . . . ?

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
C30 H30C N4 0.96 2.52 3.408(2) 153.7 2_677
C24 H24B Br2 0.96 3.00 3.4689(17) 111.4 .
C18 H18B Br1 0.96 3.00 3.4631(16) 110.9 .
C18 H18A N6 0.96 2.53 3.390(2) 149.8 2_577

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.055

_shelxl_version_number           2014/7

