# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_syn-benzimidazole[3]arene
_database_code_depnum_ccdc_archive 'CCDC 1585798'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C42 H30 N6), 2(C H2 Cl2), 1.5(H2 O)'
_chemical_formula_sum            'C44 H37 Cl4 N6 O1.50'
_chemical_formula_weight         815.59

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'-y+2/3, -x+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'
'-y+1/3, -x+2/3, z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'x-y, -y, -z-1/2'
'-x, -x+y, -z-1/2'
'y, x, -z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z-1/6'
'-x+2/3, -x+y+1/3, -z-1/6'
'y+2/3, x+1/3, -z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+1/6'
'-x+1/3, -x+y+2/3, -z+1/6'
'y+1/3, x+2/3, -z+1/6'

_cell_length_a                   16.5210(5)
_cell_length_b                   16.5210(5)
_cell_length_c                   49.1998(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11629.6(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    30483
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             5076
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.352
_shelx_estimated_absorpt_T_min   0.844
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.916
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            34693
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -63
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_theta_min         3.294
_diffrn_reflns_theta_max         27.479
_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             2970
_reflns_number_gt                2575
_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+46.3930P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2970
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Cl1 Cl 0.23143(4) 0.34882(4) 0.41811(2) 0.02887(17) Uani 1 1 d . . . . .
Cl2 Cl 0.3333 0.6667 0.44612(4) 0.0828(6) Uani 1 3 d S T P . .
O1 O 0.39416(14) 0.3333 0.5833 0.0300(5) Uani 1 2 d S T P . .
H1 H 0.355(2) 0.319(2) 0.5953(6) 0.037(8) Uiso 1 1 d . . . . .
N1 N 0.19706(11) 0.36683(11) 0.50705(3) 0.0138(3) Uani 1 1 d . . . . .
N2 N 0.28020(11) 0.35717(11) 0.54192(3) 0.0159(3) Uani 1 1 d . . . . .
C1 C 0.13490(13) 0.29031(12) 0.52239(4) 0.0142(4) Uani 1 1 d . . . . .
C2 C 0.04025(14) 0.22614(14) 0.51903(4) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.0055 0.2305 0.5043 0.023 Uiso 1 1 calc R U . . .
C3 C -0.00075(14) 0.15557(14) 0.53826(5) 0.0219(4) Uani 1 1 d . . . . .
H3 H -0.0650 0.1099 0.5366 0.026 Uiso 1 1 calc R U . . .
C4 C 0.05076(15) 0.15015(14) 0.56023(4) 0.0215(4) Uani 1 1 d . . . . .
H4 H 0.0201 0.1017 0.5733 0.026 Uiso 1 1 calc R U . . .
C5 C 0.14526(14) 0.21376(14) 0.56339(4) 0.0192(4) Uani 1 1 d . . . . .
H5 H 0.1798 0.2092 0.5782 0.023 Uiso 1 1 calc R U . . .
C6 C 0.18768(13) 0.28482(13) 0.54402(4) 0.0149(4) Uani 1 1 d . . . . .
C7 C 0.28230(13) 0.40442(13) 0.52000(4) 0.0145(4) Uani 1 1 d . . . . .
C8 C 0.36557(13) 0.49236(13) 0.51125(4) 0.0154(4) Uani 1 1 d . . . . .
C9 C 0.41286(14) 0.56229(13) 0.53045(4) 0.0174(4) Uani 1 1 d . . . . .
H9 H 0.3940 0.5513 0.5490 0.021 Uiso 1 1 calc R U . . .
C10 C 0.48770(14) 0.64837(13) 0.52270(4) 0.0174(4) Uani 1 1 d . . . . .
H10 H 0.5195 0.6958 0.5359 0.021 Uiso 1 1 calc R U . . .
C11 C 0.51613(13) 0.66526(13) 0.49569(4) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.47210(14) 0.59330(14) 0.47679(4) 0.0200(4) Uani 1 1 d . . . . .
H12 H 0.4937 0.6030 0.4585 0.024 Uiso 1 1 calc R U . . .
C13 C 0.39707(14) 0.50756(14) 0.48438(4) 0.0198(4) Uani 1 1 d . . . . .
H13 H 0.3671 0.4592 0.4713 0.024 Uiso 1 1 calc R U . . .
C14 C 0.16840(14) 0.40825(13) 0.48553(4) 0.0163(4) Uani 1 1 d . . . . .
H14A H 0.1113 0.3583 0.4767 0.020 Uiso 1 1 calc R U . . .
H14B H 0.2182 0.4354 0.4716 0.020 Uiso 1 1 calc R U . . .
C15 C 0.3333 0.3387(2) 0.4167 0.0306(7) Uani 1 2 d S T P . .
H15A H 0.3306 0.3021 0.4004 0.037 Uiso 0.5 1 calc R U P . .
H15B H 0.3361 0.3048 0.4329 0.037 Uiso 0.5 1 calc R U P . .
C16 C 0.373(2) 0.7394(14) 0.4141(4) 0.071(9) Uani 0.1667 1 d . . P A -1
H16A H 0.3486 0.7830 0.4137 0.085 Uiso 0.1667 1 calc R U P A -1
H16B H 0.4424 0.7766 0.4137 0.085 Uiso 0.1667 1 calc R U P 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
Cl1 C15 1.775(2) . ?
Cl2 C16 1.89(2) . ?
O1 H1 0.81(3) . ?
N1 C7 1.378(2) . ?
N1 C1 1.387(2) . ?
N1 C14 1.462(2) . ?
N2 C7 1.322(3) . ?
N2 C6 1.396(2) . ?
C1 C2 1.392(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.480(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.397(3) . ?
C9 C10 1.392(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 C14 1.520(3) 2_665 ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C11 1.520(3) 3_565 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 Cl1 1.775(2) 29_556 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 Cl2 1.69(2) 28_566 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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
C7 N1 C1 106.45(15) . . ?
C7 N1 C14 128.38(16) . . ?
C1 N1 C14 123.72(16) . . ?
C7 N2 C6 105.07(16) . . ?
N1 C1 C2 131.85(18) . . ?
N1 C1 C6 105.66(16) . . ?
C2 C1 C6 122.48(18) . . ?
C3 C2 C1 116.71(18) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.42(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.70(19) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 117.48(19) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
N2 C6 C5 130.07(18) . . ?
N2 C6 C1 109.73(16) . . ?
C5 C6 C1 120.20(18) . . ?
N2 C7 N1 113.07(16) . . ?
N2 C7 C8 123.65(17) . . ?
N1 C7 C8 123.15(17) . . ?
C9 C8 C13 119.29(17) . . ?
C9 C8 C7 118.58(17) . . ?
C13 C8 C7 122.13(17) . . ?
C8 C9 C10 120.38(18) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.33(18) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.11(18) . . ?
C10 C11 C14 122.83(17) . 2_665 ?
C12 C11 C14 118.04(17) . 2_665 ?
C13 C12 C11 120.67(19) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 120.03(18) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
N1 C14 C11 113.37(15) . 3_565 ?
N1 C14 H14A 108.9 . . ?
C11 C14 H14A 108.9 3_565 . ?
N1 C14 H14B 108.9 . . ?
C11 C14 H14B 108.9 3_565 . ?
H14A C14 H14B 107.7 . . ?
Cl1 C15 Cl1 110.66(18) . 29_556 ?
Cl1 C15 H15A 109.5 . . ?
Cl1 C15 H15A 109.5 29_556 . ?
Cl1 C15 H15B 109.5 . . ?
Cl1 C15 H15B 109.5 29_556 . ?
H15A C15 H15B 108.1 . . ?
Cl2 C16 Cl2 108.3(10) 28_566 . ?
Cl2 C16 H16A 110.0 28_566 . ?
Cl2 C16 H16A 110.0 . . ?
Cl2 C16 H16B 110.0 28_566 . ?
Cl2 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?

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
C7 N1 C1 C2 -179.6(2) . . . . ?
C14 N1 C1 C2 13.2(3) . . . . ?
C7 N1 C1 C6 -1.02(19) . . . . ?
C14 N1 C1 C6 -168.26(16) . . . . ?
N1 C1 C2 C3 178.62(19) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C7 N2 C6 C5 -179.6(2) . . . . ?
C7 N2 C6 C1 0.5(2) . . . . ?
C4 C5 C6 N2 -179.62(19) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
N1 C1 C6 N2 0.4(2) . . . . ?
C2 C1 C6 N2 179.07(17) . . . . ?
N1 C1 C6 C5 -179.54(17) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
C6 N2 C7 N1 -1.2(2) . . . . ?
C6 N2 C7 C8 174.77(17) . . . . ?
C1 N1 C7 N2 1.4(2) . . . . ?
C14 N1 C7 N2 167.88(17) . . . . ?
C1 N1 C7 C8 -174.54(17) . . . . ?
C14 N1 C7 C8 -8.1(3) . . . . ?
N2 C7 C8 C9 -47.9(3) . . . . ?
N1 C7 C8 C9 127.7(2) . . . . ?
N2 C7 C8 C13 133.1(2) . . . . ?
N1 C7 C8 C13 -51.4(3) . . . . ?
C13 C8 C9 C10 3.4(3) . . . . ?
C7 C8 C9 C10 -175.70(18) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 -3.5(3) . . . . ?
C9 C10 C11 C14 174.67(18) . . . 2_665 ?
C10 C11 C12 C13 3.9(3) . . . . ?
C14 C11 C12 C13 -174.34(19) 2_665 . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C9 C8 C13 C12 -3.0(3) . . . . ?
C7 C8 C13 C12 176.09(19) . . . . ?
C7 N1 C14 C11 -75.4(2) . . . 3_565 ?
C1 N1 C14 C11 89.0(2) . . . 3_565 ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -1.304
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile-dichloromethane'
####################################################################### 
# 
# 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_anti-benzimidazole[3]arene
_database_code_depnum_ccdc_archive 'CCDC 1585799'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C42 H30 N6), 2(C H Cl3)'
_chemical_formula_sum            'C44 H32 Cl6 N6'
_chemical_formula_weight         857.45

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'
Cl Cl 0.1484 0.1585 '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                   5.7565(5)
_cell_length_b                   25.735(2)
_cell_length_c                   26.340(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.020(2)
_cell_angle_gamma                90
_cell_volume                     3901.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10242
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.483
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15995
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         25.499
_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 0.883
_diffrn_reflns_point_group_measured_fraction_full 0.884
_reflns_number_total             6373
_reflns_number_gt                4159
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.766
_reflns_Friedel_fraction_full    0.770

_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       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.1 (Rigaku, 2014)'
_computing_publication_material  'CrystalStructure 4.1'

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1806P)²+4.4625P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.00(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6373
_refine_ls_number_parameters     505
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0911
_refine_ls_wR_factor_ref         0.2893
_refine_ls_wR_factor_gt          0.2388
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cl1 Cl 0.5187(6) 0.49159(12) 0.30618(15) 0.0684(9) Uani 1 1 d . . . . .
Cl2 Cl 0.1015(6) 0.43210(15) 0.32206(18) 0.0799(11) Uani 1 1 d . . . . .
Cl3 Cl 0.5294(7) 0.39968(16) 0.3681(2) 0.0950(14) Uani 1 1 d . . . . .
Cl4 Cl -0.0956(10) 0.2867(2) 0.3242(2) 0.1090(17) Uani 1 1 d . . . . .
Cl5 Cl 0.0015(11) 0.3220(2) 0.4250(3) 0.1211(18) Uani 1 1 d . . . . .
Cl6 Cl -0.3766(10) 0.2509(2) 0.4039(2) 0.1172(18) Uani 1 1 d . . . . .
N1 N 0.391(2) 0.4084(4) 0.6476(4) 0.063(3) Uani 1 1 d . . . . .
N2 N 0.1759(19) 0.3954(4) 0.5765(4) 0.060(3) Uani 1 1 d . . . . .
N3 N -0.420(2) 0.6185(4) 0.7108(4) 0.062(3) Uani 1 1 d . . . . .
N4 N -0.1329(17) 0.6604(4) 0.6709(4) 0.053(2) Uani 1 1 d . . . . .
N5 N -0.3250(15) 0.6575(3) 0.4030(4) 0.045(2) Uani 1 1 d . . . . .
N6 N -0.0025(16) 0.6082(3) 0.3894(4) 0.051(2) Uani 1 1 d . . . . .
C1 C 0.491(3) 0.3671(5) 0.6195(5) 0.061(3) Uani 1 1 d . . . . .
C2 C 0.688(2) 0.3378(5) 0.6307(5) 0.061(3) Uani 1 1 d . . . . .
H2 H 0.7789 0.3437 0.6605 0.073 Uiso 1 1 calc R U . . .
C3 C 0.742(3) 0.3000(5) 0.5964(6) 0.065(4) Uani 1 1 d . . . . .
H3 H 0.8741 0.2786 0.6029 0.077 Uiso 1 1 calc R U . . .
C4 C 0.609(3) 0.2919(5) 0.5515(7) 0.069(4) Uani 1 1 d . . . . .
H4 H 0.6535 0.2654 0.5285 0.083 Uiso 1 1 calc R U . . .
C5 C 0.418(2) 0.3213(5) 0.5405(6) 0.064(3) Uani 1 1 d . . . . .
H5 H 0.3288 0.3164 0.5101 0.077 Uiso 1 1 calc R U . . .
C6 C 0.359(2) 0.3589(4) 0.5763(5) 0.057(3) Uani 1 1 d . . . . .
C7 C 0.213(2) 0.4248(5) 0.6204(5) 0.058(3) Uani 1 1 d . . . . .
C8 C 0.075(2) 0.4711(5) 0.6351(4) 0.052(3) Uani 1 1 d . . . . .
C9 C 0.170(5) 0.5007(11) 0.6722(9) 0.167(14) Uani 1 1 d . . . . .
H9 H 0.3049 0.4883 0.6898 0.200 Uiso 1 1 calc R U . . .
C10 C 0.079(6) 0.5486(11) 0.6857(9) 0.173(15) Uani 1 1 d . . . . .
H10 H 0.1653 0.5708 0.7078 0.207 Uiso 1 1 calc R U . . .
C11 C -0.132(2) 0.5638(4) 0.6672(5) 0.052(3) Uani 1 1 d . . . . .
C12 C -0.232(4) 0.5336(9) 0.6316(11) 0.156(13) Uani 1 1 d . . . . .
H12 H -0.3803 0.5423 0.6177 0.187 Uiso 1 1 calc R U . . .
C13 C -0.113(4) 0.4882(10) 0.6147(13) 0.180(16) Uani 1 1 d . . . . .
H13 H -0.1771 0.4697 0.5866 0.216 Uiso 1 1 calc R U . . .
C14 C -0.2307(19) 0.6147(4) 0.6834(4) 0.048(3) Uani 1 1 d . . . . .
C15 C -0.441(3) 0.6732(5) 0.7191(5) 0.061(3) Uani 1 1 d . . . . .
C16 C -0.608(3) 0.7003(5) 0.7438(6) 0.069(4) Uani 1 1 d . . . . .
H16 H -0.7351 0.6827 0.7585 0.083 Uiso 1 1 calc R U . . .
C17 C -0.589(3) 0.7535(6) 0.7471(6) 0.078(4) Uani 1 1 d . . . . .
H17 H -0.6930 0.7727 0.7676 0.094 Uiso 1 1 calc R U . . .
C18 C -0.412(3) 0.7798(5) 0.7196(6) 0.071(4) Uani 1 1 d . . . . .
H18 H -0.4083 0.8167 0.7200 0.085 Uiso 1 1 calc R U . . .
C19 C -0.250(2) 0.7538(5) 0.6930(6) 0.061(3) Uani 1 1 d . . . . .
H19 H -0.1299 0.7713 0.6756 0.074 Uiso 1 1 calc R U . . .
C20 C -0.269(2) 0.6999(4) 0.6926(4) 0.049(3) Uani 1 1 d . . . . .
C21 C 0.063(2) 0.6697(5) 0.6390(4) 0.054(3) Uani 1 1 d . . . . .
H21A H 0.1911 0.6462 0.6495 0.065 Uiso 1 1 calc R U . . .
H21B H 0.1169 0.7059 0.6443 0.065 Uiso 1 1 calc R U . . .
C22 C 0.010(2) 0.6616(4) 0.5831(5) 0.057(3) Uani 1 1 d . . . . .
C23 C 0.182(2) 0.6426(6) 0.5526(5) 0.064(3) Uani 1 1 d . . . . .
H23 H 0.3297 0.6341 0.5672 0.077 Uiso 1 1 calc R U . . .
C24 C 0.143(2) 0.6355(6) 0.4990(6) 0.074(4) Uani 1 1 d . . . . .
H24 H 0.2650 0.6241 0.4780 0.088 Uiso 1 1 calc R U . . .
C25 C -0.069(2) 0.6452(4) 0.4787(5) 0.051(3) Uani 1 1 d . . . . .
C26 C -0.248(3) 0.6675(6) 0.5092(6) 0.076(4) Uani 1 1 d . . . . .
H26 H -0.3926 0.6774 0.4943 0.091 Uiso 1 1 calc R U . . .
C27 C -0.205(3) 0.6744(7) 0.5604(6) 0.074(4) Uani 1 1 d . . . . .
H27 H -0.3249 0.6881 0.5809 0.089 Uiso 1 1 calc R U . . .
C28 C -0.134(2) 0.6374(4) 0.4245(5) 0.051(3) Uani 1 1 d . . . . .
C29 C -0.323(2) 0.6403(4) 0.3524(5) 0.055(3) Uani 1 1 d . . . . .
C30 C -0.486(2) 0.6476(4) 0.3139(5) 0.053(3) Uani 1 1 d . . . . .
H30 H -0.6214 0.6680 0.3192 0.064 Uiso 1 1 calc R U . . .
C31 C -0.447(2) 0.6244(5) 0.2671(6) 0.059(3) Uani 1 1 d . . . . .
H31 H -0.5579 0.6281 0.2402 0.071 Uiso 1 1 calc R U . . .
C32 C -0.243(2) 0.5952(5) 0.2595(5) 0.061(3) Uani 1 1 d . . . . .
H32 H -0.2178 0.5808 0.2269 0.073 Uiso 1 1 calc R U . . .
C33 C -0.081(2) 0.5870(4) 0.2972(5) 0.054(3) Uani 1 1 d . . . . .
H33 H 0.0556 0.5672 0.2916 0.065 Uiso 1 1 calc R U . . .
C34 C -0.1263(19) 0.6091(4) 0.3443(5) 0.047(3) Uani 1 1 d . . . . .
C35 C 0.1950(19) 0.5746(5) 0.4004(5) 0.052(3) Uani 1 1 d . . . . .
H35A H 0.3221 0.5959 0.4152 0.063 Uiso 1 1 calc R U . . .
H35B H 0.2508 0.5601 0.3680 0.063 Uiso 1 1 calc R U . . .
C36 C 0.147(2) 0.5305(5) 0.4357(5) 0.055(3) Uani 1 1 d . . . . .
C37 C -0.060(2) 0.5026(5) 0.4330(6) 0.062(3) Uani 1 1 d . . . . .
H37 H -0.1750 0.5119 0.4084 0.074 Uiso 1 1 calc R U . . .
C38 C -0.100(2) 0.4620(5) 0.4651(5) 0.059(3) Uani 1 1 d . . . . .
H38 H -0.2449 0.4445 0.4635 0.071 Uiso 1 1 calc R U . . .
C39 C 0.065(2) 0.4463(4) 0.4995(5) 0.060(3) Uani 1 1 d . . . . .
C40 C 0.277(2) 0.4726(5) 0.5030(6) 0.071(4) Uani 1 1 d . . . . .
H40 H 0.3933 0.4630 0.5274 0.085 Uiso 1 1 calc R U . . .
C41 C 0.312(3) 0.5132(5) 0.4694(7) 0.080(4) Uani 1 1 d . . . . .
H41 H 0.4588 0.5299 0.4698 0.095 Uiso 1 1 calc R U . . .
C42 C 0.014(2) 0.4012(4) 0.5361(5) 0.056(3) Uani 1 1 d . . . . .
H42A H -0.1416 0.4066 0.5504 0.068 Uiso 1 1 calc R U . . .
H42B H 0.0095 0.3685 0.5163 0.068 Uiso 1 1 calc R U . . .
C43 C 0.397(2) 0.4299(4) 0.3165(5) 0.052(3) Uani 1 1 d . . . . .
H43 H 0.4301 0.4083 0.2860 0.063 Uiso 1 1 calc R U . . .
C44 C -0.104(3) 0.2707(7) 0.3914(7) 0.091(5) Uani 1 1 d . . . . .
H44 H 0.0030 0.2407 0.3975 0.109 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
Cl1 C43 1.759(11) . ?
Cl2 C43 1.708(13) . ?
Cl3 C43 1.732(13) . ?
Cl4 C44 1.819(19) . ?
Cl5 C44 1.69(2) . ?
Cl6 C44 1.689(18) . ?
N1 C7 1.310(18) . ?
N1 C1 1.424(17) . ?
N2 C7 1.397(18) . ?
N2 C42 1.409(18) . ?
N2 C6 1.412(15) . ?
N3 C14 1.324(15) . ?
N3 C15 1.428(16) . ?
N4 C14 1.347(15) . ?
N4 C20 1.413(15) . ?
N4 C21 1.437(15) . ?
N5 C28 1.331(16) . ?
N5 C29 1.403(16) . ?
N6 C34 1.375(16) . ?
N6 C28 1.421(15) . ?
N6 C35 1.454(14) . ?
C1 C6 1.37(2) . ?
C1 C2 1.386(19) . ?
C2 C3 1.37(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.41(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.36(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.40(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.488(18) . ?
C8 C13 1.28(2) . ?
C8 C9 1.35(3) . ?
C9 C10 1.39(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.36(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.34(2) . ?
C11 C14 1.492(16) . ?
C12 C13 1.43(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.363(18) . ?
C15 C20 1.400(18) . ?
C16 C17 1.38(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.43(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.36(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(17) . ?
C19 H19 0.9500 . ?
C21 C22 1.515(17) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.380(18) . ?
C22 C27 1.40(2) . ?
C23 C24 1.44(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.343(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.439(18) . ?
C25 C28 1.483(17) . ?
C26 C27 1.38(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 C30 1.384(18) . ?
C29 C34 1.407(16) . ?
C30 C31 1.392(19) . ?
C30 H30 0.9500 . ?
C31 C32 1.41(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.370(19) . ?
C32 H32 0.9500 . ?
C33 C34 1.393(18) . ?
C33 H33 0.9500 . ?
C35 C36 1.497(17) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C41 1.36(2) . ?
C36 C37 1.392(17) . ?
C37 C38 1.365(18) . ?
C37 H37 0.9500 . ?
C38 C39 1.359(19) . ?
C38 H38 0.9500 . ?
C39 C40 1.401(19) . ?
C39 C42 1.538(17) . ?
C40 C41 1.39(2) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43 1.0000 . ?
C44 H44 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
C7 N1 C1 106.0(12) . . ?
C7 N2 C42 131.1(11) . . ?
C7 N2 C6 105.0(12) . . ?
C42 N2 C6 123.5(11) . . ?
C14 N3 C15 103.1(10) . . ?
C14 N4 C20 107.0(10) . . ?
C14 N4 C21 128.6(11) . . ?
C20 N4 C21 124.2(10) . . ?
C28 N5 C29 105.1(9) . . ?
C34 N6 C28 106.2(9) . . ?
C34 N6 C35 124.9(10) . . ?
C28 N6 C35 127.6(10) . . ?
C6 C1 C2 122.0(12) . . ?
C6 C1 N1 108.9(12) . . ?
C2 C1 N1 129.1(14) . . ?
C3 C2 C1 116.3(15) . . ?
C3 C2 H2 121.9 . . ?
C1 C2 H2 121.9 . . ?
C2 C3 C4 121.9(13) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.4(14) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 116.4(15) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C1 C6 C5 122.0(12) . . ?
C1 C6 N2 107.3(11) . . ?
C5 C6 N2 130.7(14) . . ?
N1 C7 N2 112.7(11) . . ?
N1 C7 C8 122.2(12) . . ?
N2 C7 C8 125.1(12) . . ?
C13 C8 C9 116.3(14) . . ?
C13 C8 C7 128.2(14) . . ?
C9 C8 C7 115.3(13) . . ?
C8 C9 C10 122.4(19) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C11 C10 C9 120(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 116.9(14) . . ?
C12 C11 C14 123.1(13) . . ?
C10 C11 C14 119.7(14) . . ?
C11 C12 C13 119.3(16) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C8 C13 C12 123.8(18) . . ?
C8 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?
N3 C14 N4 114.9(10) . . ?
N3 C14 C11 122.9(10) . . ?
N4 C14 C11 122.2(10) . . ?
C16 C15 C20 119.7(12) . . ?
C16 C15 N3 129.6(13) . . ?
C20 C15 N3 110.4(11) . . ?
C15 C16 C17 119.0(14) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C16 C17 C18 119.6(12) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 122.2(13) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 116.1(12) . . ?
C18 C19 H19 121.9 . . ?
C20 C19 H19 121.9 . . ?
C19 C20 C15 123.0(11) . . ?
C19 C20 N4 132.6(11) . . ?
C15 C20 N4 104.4(10) . . ?
N4 C21 C22 113.5(10) . . ?
N4 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N4 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C23 C22 C27 118.4(13) . . ?
C23 C22 C21 118.7(12) . . ?
C27 C22 C21 122.9(12) . . ?
C22 C23 C24 120.8(12) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 119.7(13) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.2(13) . . ?
C24 C25 C28 124.9(12) . . ?
C26 C25 C28 114.8(12) . . ?
C27 C26 C25 118.9(14) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C22 121.7(13) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
N5 C28 N6 112.0(10) . . ?
N5 C28 C25 123.5(11) . . ?
N6 C28 C25 124.5(11) . . ?
C30 C29 N5 129.4(11) . . ?
C30 C29 C34 120.3(12) . . ?
N5 C29 C34 110.2(11) . . ?
C29 C30 C31 118.1(12) . . ?
C29 C30 H30 120.9 . . ?
C31 C30 H30 120.9 . . ?
C30 C31 C32 120.2(13) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C31 122.6(13) . . ?
C33 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
C32 C33 C34 116.4(12) . . ?
C32 C33 H33 121.8 . . ?
C34 C33 H33 121.8 . . ?
N6 C34 C33 131.2(11) . . ?
N6 C34 C29 106.5(10) . . ?
C33 C34 C29 122.2(12) . . ?
N6 C35 C36 115.1(9) . . ?
N6 C35 H35A 108.5 . . ?
C36 C35 H35A 108.5 . . ?
N6 C35 H35B 108.5 . . ?
C36 C35 H35B 108.5 . . ?
H35A C35 H35B 107.5 . . ?
C41 C36 C37 116.7(12) . . ?
C41 C36 C35 121.4(12) . . ?
C37 C36 C35 121.7(12) . . ?
C38 C37 C36 121.1(13) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C39 C38 C37 121.1(13) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 119.8(12) . . ?
C38 C39 C42 120.3(11) . . ?
C40 C39 C42 119.8(13) . . ?
C41 C40 C39 117.2(14) . . ?
C41 C40 H40 121.4 . . ?
C39 C40 H40 121.4 . . ?
C36 C41 C40 123.9(14) . . ?
C36 C41 H41 118.0 . . ?
C40 C41 H41 118.0 . . ?
N2 C42 C39 115.2(11) . . ?
N2 C42 H42A 108.5 . . ?
C39 C42 H42A 108.5 . . ?
N2 C42 H42B 108.5 . . ?
C39 C42 H42B 108.5 . . ?
H42A C42 H42B 107.5 . . ?
Cl2 C43 Cl3 111.9(7) . . ?
Cl2 C43 Cl1 112.6(7) . . ?
Cl3 C43 Cl1 110.8(7) . . ?
Cl2 C43 H43 107.0 . . ?
Cl3 C43 H43 107.0 . . ?
Cl1 C43 H43 107.0 . . ?
Cl6 C44 Cl5 117.4(13) . . ?
Cl6 C44 Cl4 107.3(10) . . ?
Cl5 C44 Cl4 108.5(9) . . ?
Cl6 C44 H44 107.8 . . ?
Cl5 C44 H44 107.8 . . ?
Cl4 C44 H44 107.8 . . ?

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
C7 N1 C1 C6 -2.6(14) . . . . ?
C7 N1 C1 C2 177.5(12) . . . . ?
C6 C1 C2 C3 -0.3(18) . . . . ?
N1 C1 C2 C3 179.6(12) . . . . ?
C1 C2 C3 C4 1.2(18) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C3 C4 C5 C6 -1.1(19) . . . . ?
C2 C1 C6 C5 -1.3(18) . . . . ?
N1 C1 C6 C5 178.8(11) . . . . ?
C2 C1 C6 N2 -179.4(11) . . . . ?
N1 C1 C6 N2 0.7(13) . . . . ?
C4 C5 C6 C1 2.0(18) . . . . ?
C4 C5 C6 N2 179.6(12) . . . . ?
C7 N2 C6 C1 1.4(12) . . . . ?
C42 N2 C6 C1 175.1(10) . . . . ?
C7 N2 C6 C5 -176.5(12) . . . . ?
C42 N2 C6 C5 -2.8(19) . . . . ?
C1 N1 C7 N2 3.7(14) . . . . ?
C1 N1 C7 C8 -174.6(10) . . . . ?
C42 N2 C7 N1 -176.3(11) . . . . ?
C6 N2 C7 N1 -3.3(13) . . . . ?
C42 N2 C7 C8 2.0(19) . . . . ?
C6 N2 C7 C8 174.9(11) . . . . ?
N1 C7 C8 C13 -173(3) . . . . ?
N2 C7 C8 C13 9(3) . . . . ?
N1 C7 C8 C9 13(2) . . . . ?
N2 C7 C8 C9 -165(2) . . . . ?
C13 C8 C9 C10 -4(5) . . . . ?
C7 C8 C9 C10 171(3) . . . . ?
C8 C9 C10 C11 10(5) . . . . ?
C9 C10 C11 C12 -8(5) . . . . ?
C9 C10 C11 C14 178(3) . . . . ?
C10 C11 C12 C13 -1(5) . . . . ?
C14 C11 C12 C13 173(3) . . . . ?
C9 C8 C13 C12 -5(5) . . . . ?
C7 C8 C13 C12 -179(3) . . . . ?
C11 C12 C13 C8 8(6) . . . . ?
C15 N3 C14 N4 -3.0(14) . . . . ?
C15 N3 C14 C11 177.1(12) . . . . ?
C20 N4 C14 N3 0.6(15) . . . . ?
C21 N4 C14 N3 -175.5(12) . . . . ?
C20 N4 C14 C11 -179.4(11) . . . . ?
C21 N4 C14 C11 4(2) . . . . ?
C12 C11 C14 N3 72(2) . . . . ?
C10 C11 C14 N3 -114(2) . . . . ?
C12 C11 C14 N4 -108(2) . . . . ?
C10 C11 C14 N4 66(2) . . . . ?
C14 N3 C15 C16 177.9(15) . . . . ?
C14 N3 C15 C20 4.3(14) . . . . ?
C20 C15 C16 C17 -7(2) . . . . ?
N3 C15 C16 C17 179.6(15) . . . . ?
C15 C16 C17 C18 7(2) . . . . ?
C16 C17 C18 C19 -5(3) . . . . ?
C17 C18 C19 C20 2(2) . . . . ?
C18 C19 C20 C15 -2(2) . . . . ?
C18 C19 C20 N4 -178.0(14) . . . . ?
C16 C15 C20 C19 4(2) . . . . ?
N3 C15 C20 C19 178.8(12) . . . . ?
C16 C15 C20 N4 -178.4(13) . . . . ?
N3 C15 C20 N4 -4.0(14) . . . . ?
C14 N4 C20 C19 178.9(14) . . . . ?
C21 N4 C20 C19 -5(2) . . . . ?
C14 N4 C20 C15 2.1(14) . . . . ?
C21 N4 C20 C15 178.4(11) . . . . ?
C14 N4 C21 C22 72.9(16) . . . . ?
C20 N4 C21 C22 -102.6(13) . . . . ?
N4 C21 C22 C23 -146.4(11) . . . . ?
N4 C21 C22 C27 36.0(17) . . . . ?
C27 C22 C23 C24 -1(2) . . . . ?
C21 C22 C23 C24 -178.3(13) . . . . ?
C22 C23 C24 C25 -3(2) . . . . ?
C23 C24 C25 C26 6(2) . . . . ?
C23 C24 C25 C28 -177.4(12) . . . . ?
C24 C25 C26 C27 -6(2) . . . . ?
C28 C25 C26 C27 177.6(14) . . . . ?
C25 C26 C27 C22 2(2) . . . . ?
C23 C22 C27 C26 1(2) . . . . ?
C21 C22 C27 C26 178.7(14) . . . . ?
C29 N5 C28 N6 1.4(11) . . . . ?
C29 N5 C28 C25 -179.1(9) . . . . ?
C34 N6 C28 N5 -2.5(11) . . . . ?
C35 N6 C28 N5 -170.1(10) . . . . ?
C34 N6 C28 C25 178.0(10) . . . . ?
C35 N6 C28 C25 10.4(16) . . . . ?
C24 C25 C28 N5 -164.7(13) . . . . ?
C26 C25 C28 N5 11.7(16) . . . . ?
C24 C25 C28 N6 14.8(18) . . . . ?
C26 C25 C28 N6 -168.8(11) . . . . ?
C28 N5 C29 C30 176.4(11) . . . . ?
C28 N5 C29 C34 0.2(11) . . . . ?
N5 C29 C30 C31 -177.3(10) . . . . ?
C34 C29 C30 C31 -1.4(15) . . . . ?
C29 C30 C31 C32 -1.3(15) . . . . ?
C30 C31 C32 C33 2.2(17) . . . . ?
C31 C32 C33 C34 -0.2(16) . . . . ?
C28 N6 C34 C33 -179.7(11) . . . . ?
C35 N6 C34 C33 -11.7(17) . . . . ?
C28 N6 C34 C29 2.5(10) . . . . ?
C35 N6 C34 C29 170.5(9) . . . . ?
C32 C33 C34 N6 179.8(10) . . . . ?
C32 C33 C34 C29 -2.7(15) . . . . ?
C30 C29 C34 N6 -178.3(9) . . . . ?
N5 C29 C34 N6 -1.8(11) . . . . ?
C30 C29 C34 C33 3.6(15) . . . . ?
N5 C29 C34 C33 -179.8(9) . . . . ?
C34 N6 C35 C36 -106.4(12) . . . . ?
C28 N6 C35 C36 59.0(15) . . . . ?
N6 C35 C36 C41 -145.4(14) . . . . ?
N6 C35 C36 C37 39.9(18) . . . . ?
C41 C36 C37 C38 4(2) . . . . ?
C35 C36 C37 C38 179.2(12) . . . . ?
C36 C37 C38 C39 -3(2) . . . . ?
C37 C38 C39 C40 1(2) . . . . ?
C37 C38 C39 C42 178.8(12) . . . . ?
C38 C39 C40 C41 -2(2) . . . . ?
C42 C39 C40 C41 -179.4(13) . . . . ?
C37 C36 C41 C40 -5(2) . . . . ?
C35 C36 C41 C40 179.9(14) . . . . ?
C39 C40 C41 C36 4(3) . . . . ?
C7 N2 C42 C39 73.1(16) . . . . ?
C6 N2 C42 C39 -98.7(13) . . . . ?
C38 C39 C42 N2 -167.4(11) . . . . ?
C40 C39 C42 N2 10.0(18) . . . . ?

_refine_diff_density_max         0.796
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.095

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform-acetone'
####################################################################### 
# 
# 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_protonated_anti-benzimidazole[3]arene
_database_code_depnum_ccdc_archive 'CCDC 1585801'
_audit_update_record             
;
2017-11-15 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '(C42 H30 N6), 3(C7 H8 S O3), 3(O H2)'
_chemical_formula_sum            'C63 H60 N6 O12 S3'
_chemical_formula_weight         1189.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   9.9758(3)
_cell_length_b                   14.1235(3)
_cell_length_c                   21.6617(4)
_cell_angle_alpha                98.632(2)
_cell_angle_beta                 94.107(2)
_cell_angle_gamma                107.170(2)
_cell_volume                     2861.14(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    10031
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      73.87

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.079
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    1.768
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            32111
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.329
_diffrn_reflns_theta_max         74.436
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             11270
_reflns_number_gt                8644
_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       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+1.3566P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11270
_refine_ls_number_parameters     800
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1332
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.051
_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
S1 S 0.33084(7) 0.64434(5) 0.58515(3) 0.03504(15) Uani 1 1 d . . . . .
S2 S 0.82203(6) 0.97165(4) 0.23985(3) 0.03124(14) Uani 1 1 d . . . . .
S3 S 0.20112(6) 0.51246(4) -0.09675(3) 0.02950(13) Uani 1 1 d . . . . .
O1 O 0.3337(2) 0.71429(14) 0.64198(8) 0.0445(4) Uani 1 1 d . . . . .
O2 O 0.4010(2) 0.57039(15) 0.59412(10) 0.0482(5) Uani 1 1 d . . . . .
O3 O 0.18743(18) 0.59828(13) 0.55275(8) 0.0360(4) Uani 1 1 d . . . . .
O4 O 0.87956(19) 1.00387(14) 0.30536(8) 0.0389(4) Uani 1 1 d . . . . .
O5 O 0.7767(2) 1.04612(14) 0.21307(9) 0.0447(5) Uani 1 1 d . . . . .
O6 O 0.71152(18) 0.87333(13) 0.22876(9) 0.0382(4) Uani 1 1 d . . . . .
O7 O 0.32004(18) 0.52344(12) -0.04940(8) 0.0333(4) Uani 1 1 d . . . . .
O8 O 0.07836(18) 0.42960(12) -0.09153(9) 0.0379(4) Uani 1 1 d . . . . .
O9 O 0.24329(19) 0.51034(13) -0.15943(8) 0.0362(4) Uani 1 1 d . . . . .
O10 O 0.6282(3) 1.19256(17) 0.22398(9) 0.0508(5) Uani 1 1 d D . . . .
H10A H 0.667(3) 1.146(2) 0.2213(15) 0.061 Uiso 1 1 d D U . . .
H10B H 0.638(4) 1.216(2) 0.2626(9) 0.061 Uiso 1 1 d D U . . .
O11 O 0.1899(2) 0.26131(17) 0.69981(10) 0.0498(5) Uani 1 1 d D . . . .
H11A H 0.230(3) 0.220(2) 0.7141(16) 0.060 Uiso 1 1 d D U . . .
H11B H 0.259(3) 0.3121(18) 0.6941(16) 0.060 Uiso 1 1 d D U . . .
O12A O 0.4092(4) 0.4358(3) 0.67506(17) 0.0842(10) Uani 0.89 1 d D . P A 1
H12A H 0.403(6) 0.481(3) 0.653(2) 0.101 Uiso 0.89 1 d D U P B 1
H12B H 0.408(6) 0.391(2) 0.6424(19) 0.101 Uiso 0.6153 1 d D U P C 1
H12C H 0.497(4) 0.452(9) 0.687(7) 0.101 Uiso 0.2747 1 d D U P C 1
O12B O 0.3264(19) 0.4566(14) 0.7043(8) 0.045(4) Uani 0.11 1 d . . P D 2
N1 N 0.2193(2) 0.78165(14) 0.25486(9) 0.0281(4) Uani 1 1 d . . . . .
N2 N 0.4422(2) 0.85791(15) 0.25075(9) 0.0305(4) Uani 1 1 d D . . . .
H2N H 0.530(2) 0.867(2) 0.2406(13) 0.037 Uiso 1 1 d D U . . .
N3 N 0.4218(2) 0.34113(14) 0.10644(9) 0.0278(4) Uani 1 1 d . . . . .
N4 N 0.3609(2) 0.39463(14) 0.02209(9) 0.0277(4) Uani 1 1 d D . . . .
H4N H 0.337(3) 0.4353(18) -0.0019(11) 0.033 Uiso 1 1 d D U . . .
N5 N 0.0241(2) 0.30544(14) 0.38925(8) 0.0284(4) Uani 1 1 d . . . . .
N6 N 0.1100(2) 0.42526(15) 0.47167(9) 0.0301(4) Uani 1 1 d D . . . .
H6N H 0.139(3) 0.4888(15) 0.4957(12) 0.036 Uiso 1 1 d D U . . .
C1 C 0.2507(3) 0.87814(17) 0.29034(11) 0.0290(5) Uani 1 1 d . . . . .
C2 C 0.1659(3) 0.92587(18) 0.32294(11) 0.0324(5) Uani 1 1 d . . . . .
H2 H 0.0687 0.8929 0.3245 0.039 Uiso 1 1 calc R U . . .
C3 C 0.2324(3) 1.02387(19) 0.35270(12) 0.0375(6) Uani 1 1 d . . . . .
H3 H 0.1792 1.0596 0.3756 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3760(3) 1.07267(19) 0.35025(12) 0.0392(6) Uani 1 1 d . . . . .
H4 H 0.4170 1.1403 0.3716 0.047 Uiso 1 1 calc R U . . .
C5 C 0.4593(3) 1.02555(18) 0.31787(12) 0.0347(5) Uani 1 1 d . . . . .
H5 H 0.5565 1.0586 0.3162 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3927(3) 0.92677(17) 0.28776(11) 0.0305(5) Uani 1 1 d . . . . .
C7 C 0.3361(3) 0.77226(17) 0.23138(11) 0.0288(5) Uani 1 1 d . . . . .
C8 C 0.3514(3) 0.68261(17) 0.19247(11) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.4692(3) 0.65246(18) 0.20670(11) 0.0334(5) Uani 1 1 d . . . . .
H9 H 0.5384 0.6907 0.2409 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4867(3) 0.56776(18) 0.17183(11) 0.0326(5) Uani 1 1 d . . . . .
H10 H 0.5675 0.5478 0.1818 0.039 Uiso 1 1 calc R U . . .
C11 C 0.3843(3) 0.51154(17) 0.12168(11) 0.0290(5) Uani 1 1 d . . . . .
C12 C 0.2689(3) 0.54366(18) 0.10618(11) 0.0315(5) Uani 1 1 d . . . . .
H12 H 0.2010 0.5067 0.0713 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2524(3) 0.62844(18) 0.14096(11) 0.0333(5) Uani 1 1 d . . . . .
H13 H 0.1738 0.6501 0.1299 0.040 Uiso 1 1 calc R U . . .
C14 C 0.3920(2) 0.41832(17) 0.08479(10) 0.0269(5) Uani 1 1 d . . . . .
C15 C 0.3722(2) 0.29984(17) 0.00160(10) 0.0282(5) Uani 1 1 d . . . . .
C16 C 0.3530(3) 0.24336(19) -0.05840(11) 0.0341(5) Uani 1 1 d . . . . .
H16 H 0.3304 0.2685 -0.0948 0.041 Uiso 1 1 calc R U . . .
C17 C 0.3686(3) 0.1486(2) -0.06246(12) 0.0377(6) Uani 1 1 d . . . . .
H17 H 0.3551 0.1069 -0.1026 0.045 Uiso 1 1 calc R U . . .
C18 C 0.4039(3) 0.11272(19) -0.00845(12) 0.0369(6) Uani 1 1 d . . . . .
H18 H 0.4126 0.0469 -0.0131 0.044 Uiso 1 1 calc R U . . .
C19 C 0.4264(3) 0.17012(18) 0.05132(12) 0.0327(5) Uani 1 1 d . . . . .
H19 H 0.4522 0.1461 0.0876 0.039 Uiso 1 1 calc R U . . .
C20 C 0.4090(2) 0.26500(17) 0.05507(11) 0.0281(5) Uani 1 1 d . . . . .
C21 C 0.4550(3) 0.33307(18) 0.17228(10) 0.0304(5) Uani 1 1 d . . . . .
H21A H 0.5297 0.3954 0.1932 0.037 Uiso 1 1 calc R U . . .
H21B H 0.4937 0.2762 0.1730 0.037 Uiso 1 1 calc R U . . .
C22 C 0.3303(3) 0.31710(17) 0.20990(10) 0.0288(5) Uani 1 1 d . . . . .
C23 C 0.3562(3) 0.30604(19) 0.27218(11) 0.0341(5) Uani 1 1 d . . . . .
H23 H 0.4492 0.3113 0.2892 0.041 Uiso 1 1 calc R U . . .
C24 C 0.2471(3) 0.28736(19) 0.30932(11) 0.0349(5) Uani 1 1 d . . . . .
H24 H 0.2657 0.2788 0.3514 0.042 Uiso 1 1 calc R U . . .
C25 C 0.1113(3) 0.28098(17) 0.28595(10) 0.0300(5) Uani 1 1 d . . . . .
C26 C 0.0861(3) 0.29456(18) 0.22473(11) 0.0323(5) Uani 1 1 d . . . . .
H26 H -0.0059 0.2924 0.2085 0.039 Uiso 1 1 calc R U . . .
C27 C 0.1946(3) 0.31129(18) 0.18684(11) 0.0318(5) Uani 1 1 d . . . . .
H27 H 0.1753 0.3188 0.1446 0.038 Uiso 1 1 calc R U . . .
C28 C -0.0112(3) 0.25162(18) 0.32376(11) 0.0329(5) Uani 1 1 d . . . . .
H28A H -0.0932 0.2667 0.3039 0.039 Uiso 1 1 calc R U . . .
H28B H -0.0388 0.1782 0.3233 0.039 Uiso 1 1 calc R U . . .
C29 C 0.0171(3) 0.25865(17) 0.44189(10) 0.0287(5) Uani 1 1 d . . . . .
C30 C -0.0341(3) 0.15753(18) 0.44718(11) 0.0331(5) Uani 1 1 d . . . . .
H30 H -0.0676 0.1053 0.4114 0.040 Uiso 1 1 calc R U . . .
C31 C -0.0330(3) 0.13818(19) 0.50819(12) 0.0366(6) Uani 1 1 d . . . . .
H31 H -0.0683 0.0706 0.5146 0.044 Uiso 1 1 calc R U . . .
C32 C 0.0189(3) 0.2158(2) 0.56045(12) 0.0385(6) Uani 1 1 d . . . . .
H32 H 0.0176 0.1990 0.6013 0.046 Uiso 1 1 calc R U . . .
C33 C 0.0717(3) 0.3153(2) 0.55485(11) 0.0351(5) Uani 1 1 d . . . . .
H33 H 0.1070 0.3675 0.5906 0.042 Uiso 1 1 calc R U . . .
C34 C 0.0703(3) 0.33493(18) 0.49402(11) 0.0292(5) Uani 1 1 d . . . . .
C35 C 0.0765(3) 0.40554(17) 0.40909(11) 0.0288(5) Uani 1 1 d . . . . .
C36 C 0.0856(3) 0.48233(17) 0.36946(11) 0.0309(5) Uani 1 1 d . . . . .
C37 C 0.2028(3) 0.56798(18) 0.37733(11) 0.0328(5) Uani 1 1 d . . . . .
H37 H 0.2804 0.5771 0.4082 0.039 Uiso 1 1 calc R U . . .
C38 C 0.2060(3) 0.64040(18) 0.33967(12) 0.0333(5) Uani 1 1 d . . . . .
H38 H 0.2857 0.6992 0.3451 0.040 Uiso 1 1 calc R U . . .
C39 C 0.0933(3) 0.62700(17) 0.29428(10) 0.0297(5) Uani 1 1 d . . . . .
C40 C -0.0251(3) 0.54197(18) 0.28779(11) 0.0350(5) Uani 1 1 d . . . . .
H40 H -0.1034 0.5334 0.2575 0.042 Uiso 1 1 calc R U . . .
C41 C -0.0296(3) 0.47040(18) 0.32490(11) 0.0349(5) Uani 1 1 d . . . . .
H41 H -0.1109 0.4129 0.3203 0.042 Uiso 1 1 calc R U . . .
C42 C 0.0850(3) 0.70122(17) 0.25212(11) 0.0309(5) Uani 1 1 d . . . . .
H42A H 0.0559 0.6647 0.2082 0.037 Uiso 1 1 calc R U . . .
H42B H 0.0114 0.7320 0.2643 0.037 Uiso 1 1 calc R U . . .
C43 C 0.6561(4) 0.9041(3) 0.41231(15) 0.0537(8) Uani 1 1 d . . . . .
H43A H 0.6181 0.8755 0.3682 0.064 Uiso 1 1 calc R U . . .
H43B H 0.7557 0.9073 0.4189 0.064 Uiso 1 1 calc R U . . .
H43C H 0.6482 0.9720 0.4226 0.064 Uiso 1 1 calc R U . . .
C44 C 0.5734(3) 0.8385(2) 0.45424(12) 0.0412(6) Uani 1 1 d . . . . .
C45 C 0.4481(3) 0.8499(2) 0.47363(13) 0.0405(6) Uani 1 1 d . . . . .
H45 H 0.4128 0.8997 0.4598 0.049 Uiso 1 1 calc R U . . .
C46 C 0.3745(3) 0.7901(2) 0.51253(13) 0.0393(6) Uani 1 1 d . . . . .
H46 H 0.2893 0.7991 0.5254 0.047 Uiso 1 1 calc R U . . .
C47 C 0.4241(3) 0.71687(18) 0.53304(11) 0.0336(5) Uani 1 1 d . . . . .
C48 C 0.5462(3) 0.7024(2) 0.51296(14) 0.0447(6) Uani 1 1 d . . . . .
H48 H 0.5798 0.6512 0.5258 0.054 Uiso 1 1 calc R U . . .
C49 C 0.6187(3) 0.7630(2) 0.47410(15) 0.0513(7) Uani 1 1 d . . . . .
H49 H 0.7025 0.7526 0.4605 0.062 Uiso 1 1 calc R U . . .
C50 C 1.3120(3) 0.9098(2) 0.10537(13) 0.0410(6) Uani 1 1 d . . . . .
H50A H 1.3017 0.9234 0.0625 0.049 Uiso 1 1 calc R U . . .
H50B H 1.3137 0.8404 0.1036 0.049 Uiso 1 1 calc R U . . .
H50C H 1.4005 0.9565 0.1286 0.049 Uiso 1 1 calc R U . . .
C51 C 1.1895(3) 0.92353(19) 0.13822(11) 0.0340(5) Uani 1 1 d . . . . .
C52 C 1.1935(3) 1.01856(19) 0.16930(12) 0.0379(6) Uani 1 1 d . . . . .
H52 H 1.2754 1.0745 0.1703 0.045 Uiso 1 1 calc R U . . .
C53 C 1.0811(3) 1.03283(18) 0.19859(12) 0.0360(5) Uani 1 1 d . . . . .
H53 H 1.0853 1.0983 0.2188 0.043 Uiso 1 1 calc R U . . .
C54 C 0.9614(3) 0.95159(18) 0.19864(11) 0.0307(5) Uani 1 1 d . . . . .
C55 C 0.9564(3) 0.85608(18) 0.16887(11) 0.0312(5) Uani 1 1 d . . . . .
H55 H 0.8758 0.7999 0.1692 0.037 Uiso 1 1 calc R U . . .
C56 C 1.0694(3) 0.84310(18) 0.13860(11) 0.0316(5) Uani 1 1 d . . . . .
H56 H 1.0645 0.7778 0.1177 0.038 Uiso 1 1 calc R U . . .
C57 C 0.0312(3) 0.8927(2) -0.03731(13) 0.0426(6) Uani 1 1 d . . . . .
H57A H 0.0718 0.9395 -0.0651 0.051 Uiso 1 1 calc R U . . .
H57B H 0.0637 0.9256 0.0066 0.051 Uiso 1 1 calc R U . . .
H57C H -0.0722 0.8733 -0.0446 0.051 Uiso 1 1 calc R U . . .
C58 C 0.0775(3) 0.80042(18) -0.05085(11) 0.0331(5) Uani 1 1 d . . . . .
C59 C 0.0277(3) 0.71985(19) -0.01957(12) 0.0348(5) Uani 1 1 d . . . . .
H59 H -0.0352 0.7242 0.0109 0.042 Uiso 1 1 calc R U . . .
C60 C 0.0678(3) 0.63364(18) -0.03193(11) 0.0321(5) Uani 1 1 d . . . . .
H60 H 0.0358 0.5808 -0.0089 0.039 Uiso 1 1 calc R U . . .
C61 C 0.1554(3) 0.62496(17) -0.07833(11) 0.0301(5) Uani 1 1 d . . . . .
C62 C 0.2062(3) 0.70462(18) -0.10999(11) 0.0326(5) Uani 1 1 d . . . . .
H62 H 0.2667 0.6994 -0.1414 0.039 Uiso 1 1 calc R U . . .
C63 C 0.1686(3) 0.79132(18) -0.09563(12) 0.0350(5) Uani 1 1 d . . . . .
H63 H 0.2058 0.8459 -0.1167 0.042 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
S1 O2 1.4459(19) . ?
S1 O1 1.4510(19) . ?
S1 O3 1.4602(18) . ?
S1 C47 1.767(3) . ?
S2 O5 1.4398(18) . ?
S2 O4 1.4442(18) . ?
S2 O6 1.4695(18) . ?
S2 C54 1.773(2) . ?
S3 O8 1.4475(18) . ?
S3 O9 1.4486(17) . ?
S3 O7 1.4671(17) . ?
S3 C61 1.776(2) . ?
O10 H10A 0.853(18) . ?
O10 H10B 0.841(18) . ?
O11 H11A 0.874(18) . ?
O11 H11B 0.865(18) . ?
O12A H12A 0.863(19) . ?
O12A H12B 0.87(2) . ?
O12A H12C 0.85(2) . ?
N1 C7 1.338(3) . ?
N1 C1 1.395(3) . ?
N1 C42 1.469(3) . ?
N2 C7 1.337(3) . ?
N2 C6 1.393(3) . ?
N2 H2N 0.895(17) . ?
N3 C14 1.350(3) . ?
N3 C20 1.396(3) . ?
N3 C21 1.470(3) . ?
N4 C14 1.340(3) . ?
N4 C15 1.385(3) . ?
N4 H4N 0.897(17) . ?
N5 C35 1.344(3) . ?
N5 C29 1.397(3) . ?
N5 C28 1.470(3) . ?
N6 C35 1.339(3) . ?
N6 C34 1.390(3) . ?
N6 H6N 0.919(17) . ?
C1 C6 1.389(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.466(3) . ?
C8 C9 1.393(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 C14 1.460(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 C16 1.387(3) . ?
C15 C20 1.391(3) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.405(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(3) . ?
C19 H19 0.9500 . ?
C21 C22 1.515(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.383(3) . ?
C22 C23 1.396(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(3) . ?
C25 C28 1.511(3) . ?
C26 C27 1.392(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C34 1.389(3) . ?
C29 C30 1.393(3) . ?
C30 C31 1.389(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.400(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.375(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C35 C36 1.468(3) . ?
C36 C37 1.391(3) . ?
C36 C41 1.400(3) . ?
C37 C38 1.396(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.388(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(3) . ?
C39 C42 1.506(3) . ?
C40 C41 1.376(3) . ?
C40 H40 0.9500 . ?
C41 H41 0.9500 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.507(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 C49 1.386(4) . ?
C44 C45 1.393(4) . ?
C45 C46 1.378(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.385(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.383(4) . ?
C48 C49 1.379(4) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C51 1.504(4) . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
C51 C56 1.388(4) . ?
C51 C52 1.396(4) . ?
C52 C53 1.378(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.390(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(3) . ?
C55 C56 1.388(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?
C57 C58 1.503(3) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 C63 1.394(4) . ?
C58 C59 1.395(3) . ?
C59 C60 1.386(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.393(3) . ?
C60 H60 0.9500 . ?
C61 C62 1.392(3) . ?
C62 C63 1.382(3) . ?
C62 H62 0.9500 . ?
C63 H63 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
O2 S1 O1 114.38(12) . . ?
O2 S1 O3 112.28(11) . . ?
O1 S1 O3 111.40(11) . . ?
O2 S1 C47 106.51(12) . . ?
O1 S1 C47 106.60(11) . . ?
O3 S1 C47 104.92(11) . . ?
O5 S2 O4 113.71(11) . . ?
O5 S2 O6 112.29(12) . . ?
O4 S2 O6 111.79(11) . . ?
O5 S2 C54 106.69(11) . . ?
O4 S2 C54 106.31(11) . . ?
O6 S2 C54 105.36(11) . . ?
O8 S3 O9 114.20(11) . . ?
O8 S3 O7 111.98(10) . . ?
O9 S3 O7 111.71(10) . . ?
O8 S3 C61 107.12(11) . . ?
O9 S3 C61 106.09(10) . . ?
O7 S3 C61 105.02(10) . . ?
H10A O10 H10B 105(3) . . ?
H11A O11 H11B 106(3) . . ?
H12A O12A H12B 95(3) . . ?
H12A O12A H12C 103(5) . . ?
H12B O12A H12C 96(10) . . ?
C7 N1 C1 108.65(19) . . ?
C7 N1 C42 126.66(19) . . ?
C1 N1 C42 124.18(19) . . ?
C7 N2 C6 109.1(2) . . ?
C7 N2 H2N 123.0(18) . . ?
C6 N2 H2N 127.8(18) . . ?
C14 N3 C20 108.17(18) . . ?
C14 N3 C21 127.51(19) . . ?
C20 N3 C21 124.26(18) . . ?
C14 N4 C15 109.19(18) . . ?
C14 N4 H4N 124.0(17) . . ?
C15 N4 H4N 126.8(17) . . ?
C35 N5 C29 108.30(18) . . ?
C35 N5 C28 127.05(19) . . ?
C29 N5 C28 124.53(19) . . ?
C35 N6 C34 108.6(2) . . ?
C35 N6 H6N 124.3(17) . . ?
C34 N6 H6N 126.3(17) . . ?
C6 C1 N1 106.76(19) . . ?
C6 C1 C2 122.0(2) . . ?
N1 C1 C2 131.3(2) . . ?
C3 C2 C1 115.7(2) . . ?
C3 C2 H2 122.1 . . ?
C1 C2 H2 122.1 . . ?
C2 C3 C4 122.2(2) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 116.0(2) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 H5 122.0 . . ?
C1 C6 C5 122.1(2) . . ?
C1 C6 N2 106.2(2) . . ?
C5 C6 N2 131.6(2) . . ?
N2 C7 N1 109.2(2) . . ?
N2 C7 C8 123.8(2) . . ?
N1 C7 C8 126.9(2) . . ?
C9 C8 C13 119.5(2) . . ?
C9 C8 C7 119.0(2) . . ?
C13 C8 C7 121.5(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.4(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 C14 117.9(2) . . ?
C10 C11 C14 122.4(2) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
N4 C14 N3 109.19(19) . . ?
N4 C14 C11 123.2(2) . . ?
N3 C14 C11 127.5(2) . . ?
N4 C15 C16 131.1(2) . . ?
N4 C15 C20 106.58(19) . . ?
C16 C15 C20 122.3(2) . . ?
C17 C16 C15 116.4(2) . . ?
C17 C16 H16 121.8 . . ?
C15 C16 H16 121.8 . . ?
C16 C17 C18 121.3(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 122.2(2) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C18 C19 C20 116.1(2) . . ?
C18 C19 H19 121.9 . . ?
C20 C19 H19 121.9 . . ?
C15 C20 C19 121.6(2) . . ?
C15 C20 N3 106.86(19) . . ?
C19 C20 N3 131.6(2) . . ?
N3 C21 C22 114.59(19) . . ?
N3 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
N3 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C27 C22 C23 118.5(2) . . ?
C27 C22 C21 125.0(2) . . ?
C23 C22 C21 116.5(2) . . ?
C24 C23 C22 120.3(2) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.9(2) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 118.8(2) . . ?
C24 C25 C28 121.6(2) . . ?
C26 C25 C28 119.4(2) . . ?
C25 C26 C27 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 120.9(2) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
N5 C28 C25 112.0(2) . . ?
N5 C28 H28A 109.2 . . ?
C25 C28 H28A 109.2 . . ?
N5 C28 H28B 109.2 . . ?
C25 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?
C34 C29 C30 122.3(2) . . ?
C34 C29 N5 106.60(19) . . ?
C30 C29 N5 131.1(2) . . ?
C31 C30 C29 115.6(2) . . ?
C31 C30 H30 122.2 . . ?
C29 C30 H30 122.2 . . ?
C30 C31 C32 121.6(2) . . ?
C30 C31 H31 119.2 . . ?
C32 C31 H31 119.2 . . ?
C33 C32 C31 122.5(2) . . ?
C33 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
C32 C33 C34 116.1(2) . . ?
C32 C33 H33 122.0 . . ?
C34 C33 H33 122.0 . . ?
C33 C34 C29 121.9(2) . . ?
C33 C34 N6 131.1(2) . . ?
C29 C34 N6 106.87(19) . . ?
N6 C35 N5 109.54(19) . . ?
N6 C35 C36 124.7(2) . . ?
N5 C35 C36 125.6(2) . . ?
C37 C36 C41 119.9(2) . . ?
C37 C36 C35 121.4(2) . . ?
C41 C36 C35 118.6(2) . . ?
C36 C37 C38 119.7(2) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 120.3(2) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C38 C39 C40 119.5(2) . . ?
C38 C39 C42 124.5(2) . . ?
C40 C39 C42 115.9(2) . . ?
C41 C40 C39 120.6(2) . . ?
C41 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C40 C41 C36 120.0(2) . . ?
C40 C41 H41 120.0 . . ?
C36 C41 H41 120.0 . . ?
N1 C42 C39 113.27(19) . . ?
N1 C42 H42A 108.9 . . ?
C39 C42 H42A 108.9 . . ?
N1 C42 H42B 108.9 . . ?
C39 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C49 C44 C45 117.4(3) . . ?
C49 C44 C43 120.9(3) . . ?
C45 C44 C43 121.7(3) . . ?
C46 C45 C44 121.0(2) . . ?
C46 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?
C45 C46 C47 120.4(2) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C48 C47 C46 119.6(2) . . ?
C48 C47 S1 121.1(2) . . ?
C46 C47 S1 119.3(2) . . ?
C49 C48 C47 119.3(3) . . ?
C49 C48 H48 120.3 . . ?
C47 C48 H48 120.3 . . ?
C48 C49 C44 122.3(3) . . ?
C48 C49 H49 118.9 . . ?
C44 C49 H49 118.9 . . ?
C51 C50 H50A 109.5 . . ?
C51 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C51 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C56 C51 C52 118.0(2) . . ?
C56 C51 C50 121.5(2) . . ?
C52 C51 C50 120.5(2) . . ?
C53 C52 C51 121.3(2) . . ?
C53 C52 H52 119.4 . . ?
C51 C52 H52 119.4 . . ?
C52 C53 C54 120.2(2) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C55 C54 C53 119.4(2) . . ?
C55 C54 S2 121.55(19) . . ?
C53 C54 S2 118.98(18) . . ?
C56 C55 C54 119.8(2) . . ?
C56 C55 H55 120.1 . . ?
C54 C55 H55 120.1 . . ?
C51 C56 C55 121.4(2) . . ?
C51 C56 H56 119.3 . . ?
C55 C56 H56 119.3 . . ?
C58 C57 H57A 109.5 . . ?
C58 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C58 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C63 C58 C59 117.8(2) . . ?
C63 C58 C57 121.5(2) . . ?
C59 C58 C57 120.6(2) . . ?
C60 C59 C58 121.5(2) . . ?
C60 C59 H59 119.2 . . ?
C58 C59 H59 119.2 . . ?
C59 C60 C61 119.6(2) . . ?
C59 C60 H60 120.2 . . ?
C61 C60 H60 120.2 . . ?
C62 C61 C60 119.6(2) . . ?
C62 C61 S3 120.51(18) . . ?
C60 C61 S3 119.85(18) . . ?
C63 C62 C61 119.9(2) . . ?
C63 C62 H62 120.0 . . ?
C61 C62 H62 120.0 . . ?
C62 C63 C58 121.5(2) . . ?
C62 C63 H63 119.3 . . ?
C58 C63 H63 119.3 . . ?

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
C7 N1 C1 C6 -0.5(2) . . . . ?
C42 N1 C1 C6 171.7(2) . . . . ?
C7 N1 C1 C2 178.3(2) . . . . ?
C42 N1 C1 C2 -9.5(4) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
N1 C1 C2 C3 -179.1(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
N1 C1 C6 N2 0.0(2) . . . . ?
C2 C1 C6 N2 -178.9(2) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 N2 179.0(2) . . . . ?
C7 N2 C6 C1 0.4(3) . . . . ?
C7 N2 C6 C5 -178.9(2) . . . . ?
C6 N2 C7 N1 -0.8(3) . . . . ?
C6 N2 C7 C8 -178.7(2) . . . . ?
C1 N1 C7 N2 0.8(2) . . . . ?
C42 N1 C7 N2 -171.2(2) . . . . ?
C1 N1 C7 C8 178.7(2) . . . . ?
C42 N1 C7 C8 6.7(4) . . . . ?
N2 C7 C8 C9 43.3(3) . . . . ?
N1 C7 C8 C9 -134.3(2) . . . . ?
N2 C7 C8 C13 -135.3(2) . . . . ?
N1 C7 C8 C13 47.1(3) . . . . ?
C13 C8 C9 C10 -2.3(4) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C12 2.3(3) . . . . ?
C9 C10 C11 C14 -176.8(2) . . . . ?
C10 C11 C12 C13 -2.0(4) . . . . ?
C14 C11 C12 C13 177.1(2) . . . . ?
C11 C12 C13 C8 -0.4(4) . . . . ?
C9 C8 C13 C12 2.5(4) . . . . ?
C7 C8 C13 C12 -178.9(2) . . . . ?
C15 N4 C14 N3 -0.8(3) . . . . ?
C15 N4 C14 C11 -177.3(2) . . . . ?
C20 N3 C14 N4 0.0(3) . . . . ?
C21 N3 C14 N4 -177.0(2) . . . . ?
C20 N3 C14 C11 176.3(2) . . . . ?
C21 N3 C14 C11 -0.7(4) . . . . ?
C12 C11 C14 N4 42.2(3) . . . . ?
C10 C11 C14 N4 -138.7(2) . . . . ?
C12 C11 C14 N3 -133.6(2) . . . . ?
C10 C11 C14 N3 45.5(4) . . . . ?
C14 N4 C15 C16 -178.9(3) . . . . ?
C14 N4 C15 C20 1.2(3) . . . . ?
N4 C15 C16 C17 -178.1(2) . . . . ?
C20 C15 C16 C17 1.8(4) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C20 1.3(4) . . . . ?
N4 C15 C20 C19 178.7(2) . . . . ?
C16 C15 C20 C19 -1.2(4) . . . . ?
N4 C15 C20 N3 -1.2(2) . . . . ?
C16 C15 C20 N3 178.9(2) . . . . ?
C18 C19 C20 C15 -0.4(4) . . . . ?
C18 C19 C20 N3 179.5(2) . . . . ?
C14 N3 C20 C15 0.7(3) . . . . ?
C21 N3 C20 C15 177.9(2) . . . . ?
C14 N3 C20 C19 -179.2(2) . . . . ?
C21 N3 C20 C19 -2.0(4) . . . . ?
C14 N3 C21 C22 71.6(3) . . . . ?
C20 N3 C21 C22 -105.0(2) . . . . ?
N3 C21 C22 C27 -0.8(3) . . . . ?
N3 C21 C22 C23 178.2(2) . . . . ?
C27 C22 C23 C24 1.4(4) . . . . ?
C21 C22 C23 C24 -177.6(2) . . . . ?
C22 C23 C24 C25 -1.1(4) . . . . ?
C23 C24 C25 C26 -0.6(4) . . . . ?
C23 C24 C25 C28 174.5(2) . . . . ?
C24 C25 C26 C27 1.9(4) . . . . ?
C28 C25 C26 C27 -173.3(2) . . . . ?
C23 C22 C27 C26 -0.1(3) . . . . ?
C21 C22 C27 C26 178.8(2) . . . . ?
C25 C26 C27 C22 -1.6(4) . . . . ?
C35 N5 C28 C25 53.4(3) . . . . ?
C29 N5 C28 C25 -122.0(2) . . . . ?
C24 C25 C28 N5 45.7(3) . . . . ?
C26 C25 C28 N5 -139.2(2) . . . . ?
C35 N5 C29 C34 -1.3(3) . . . . ?
C28 N5 C29 C34 174.9(2) . . . . ?
C35 N5 C29 C30 177.0(3) . . . . ?
C28 N5 C29 C30 -6.8(4) . . . . ?
C34 C29 C30 C31 2.1(4) . . . . ?
N5 C29 C30 C31 -175.9(2) . . . . ?
C29 C30 C31 C32 -1.1(4) . . . . ?
C30 C31 C32 C33 0.0(4) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
C32 C33 C34 C29 0.8(4) . . . . ?
C32 C33 C34 N6 177.4(2) . . . . ?
C30 C29 C34 C33 -2.1(4) . . . . ?
N5 C29 C34 C33 176.4(2) . . . . ?
C30 C29 C34 N6 -179.4(2) . . . . ?
N5 C29 C34 N6 -0.9(3) . . . . ?
C35 N6 C34 C33 -174.2(3) . . . . ?
C35 N6 C34 C29 2.8(3) . . . . ?
C34 N6 C35 N5 -3.6(3) . . . . ?
C34 N6 C35 C36 172.0(2) . . . . ?
C29 N5 C35 N6 3.0(3) . . . . ?
C28 N5 C35 N6 -173.0(2) . . . . ?
C29 N5 C35 C36 -172.5(2) . . . . ?
C28 N5 C35 C36 11.4(4) . . . . ?
N6 C35 C36 C37 44.9(4) . . . . ?
N5 C35 C36 C37 -140.2(3) . . . . ?
N6 C35 C36 C41 -132.2(3) . . . . ?
N5 C35 C36 C41 42.8(3) . . . . ?
C41 C36 C37 C38 -1.5(4) . . . . ?
C35 C36 C37 C38 -178.5(2) . . . . ?
C36 C37 C38 C39 -0.4(4) . . . . ?
C37 C38 C39 C40 1.9(4) . . . . ?
C37 C38 C39 C42 178.9(2) . . . . ?
C38 C39 C40 C41 -1.5(4) . . . . ?
C42 C39 C40 C41 -178.8(2) . . . . ?
C39 C40 C41 C36 -0.3(4) . . . . ?
C37 C36 C41 C40 1.8(4) . . . . ?
C35 C36 C41 C40 178.9(2) . . . . ?
C7 N1 C42 C39 71.4(3) . . . . ?
C1 N1 C42 C39 -99.4(2) . . . . ?
C38 C39 C42 N1 10.9(3) . . . . ?
C40 C39 C42 N1 -172.1(2) . . . . ?
C49 C44 C45 C46 1.8(4) . . . . ?
C43 C44 C45 C46 -179.3(3) . . . . ?
C44 C45 C46 C47 -0.2(4) . . . . ?
C45 C46 C47 C48 -1.6(4) . . . . ?
C45 C46 C47 S1 177.8(2) . . . . ?
O2 S1 C47 C48 -4.8(3) . . . . ?
O1 S1 C47 C48 117.7(2) . . . . ?
O3 S1 C47 C48 -124.1(2) . . . . ?
O2 S1 C47 C46 175.8(2) . . . . ?
O1 S1 C47 C46 -61.7(2) . . . . ?
O3 S1 C47 C46 56.6(2) . . . . ?
C46 C47 C48 C49 1.7(4) . . . . ?
S1 C47 C48 C49 -177.7(2) . . . . ?
C47 C48 C49 C44 0.0(5) . . . . ?
C45 C44 C49 C48 -1.7(5) . . . . ?
C43 C44 C49 C48 179.3(3) . . . . ?
C56 C51 C52 C53 -1.1(4) . . . . ?
C50 C51 C52 C53 178.7(2) . . . . ?
C51 C52 C53 C54 1.2(4) . . . . ?
C52 C53 C54 C55 -0.1(4) . . . . ?
C52 C53 C54 S2 177.14(19) . . . . ?
O5 S2 C54 C55 -124.4(2) . . . . ?
O4 S2 C54 C55 113.9(2) . . . . ?
O6 S2 C54 C55 -4.9(2) . . . . ?
O5 S2 C54 C53 58.4(2) . . . . ?
O4 S2 C54 C53 -63.3(2) . . . . ?
O6 S2 C54 C53 177.95(19) . . . . ?
C53 C54 C55 C56 -1.1(3) . . . . ?
S2 C54 C55 C56 -178.20(17) . . . . ?
C52 C51 C56 C55 0.0(4) . . . . ?
C50 C51 C56 C55 -179.9(2) . . . . ?
C54 C55 C56 C51 1.1(3) . . . . ?
C63 C58 C59 C60 0.5(4) . . . . ?
C57 C58 C59 C60 179.2(2) . . . . ?
C58 C59 C60 C61 -2.6(4) . . . . ?
C59 C60 C61 C62 2.6(4) . . . . ?
C59 C60 C61 S3 -177.31(19) . . . . ?
O8 S3 C61 C62 -143.6(2) . . . . ?
O9 S3 C61 C62 -21.3(2) . . . . ?
O7 S3 C61 C62 97.2(2) . . . . ?
O8 S3 C61 C60 36.3(2) . . . . ?
O9 S3 C61 C60 158.64(19) . . . . ?
O7 S3 C61 C60 -82.9(2) . . . . ?
C60 C61 C62 C63 -0.6(4) . . . . ?
S3 C61 C62 C63 179.35(19) . . . . ?
C61 C62 C63 C58 -1.6(4) . . . . ?
C59 C58 C63 C62 1.6(4) . . . . ?
C57 C58 C63 C62 -177.1(2) . . . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.055

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
