# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_20170531iwashimizu_aza9helicene
_database_code_depnum_ccdc_archive 'CCDC 1569975'
loop_
_audit_author_name
_audit_author_address
'Takuma Sasayama'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C30 H16 N6'
_chemical_formula_moiety         'C30 H16 N6'
_chemical_formula_weight         460.50
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      tetragonal
_space_group_name_H-M_alt        'I -4 2 d'
_space_group_name_Hall           'I -4 2bw'
_space_group_IT_number           122
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/4'
'-x, -y, z'
'x, -y+1/2, -z+1/4'
'-y, x, -z'
'y, x+1/2, z+1/4'
'y, -x, -z'
'-y, -x+1/2, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1, -z+3/4'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1, -z+3/4'
'-y+1/2, x+1/2, -z+1/2'
'y+1/2, x+1, z+3/4'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, -x+1, z+3/4'
#------------------------------------------------------------------------------
_cell_length_a                   22.3365(5)
_cell_length_b                   22.3365(5)
_cell_length_c                   9.9167(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4947.62(18)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    21630
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            unknown
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    2.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3808.00
_exptl_absorpt_coefficient_mu    1.212
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.785

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            28498
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_theta_max         68.232
_diffrn_reflns_theta_min         3.958
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2257
_reflns_number_gt                2225
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# REFINEMENT DATA

_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_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1996
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2257
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1800P)²+1.5410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.55
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 978 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.79224(14) 0.14915(14) 0.6148(3) 0.0323(7) Uani 1 1 d . . . . .
N2 N 0.78815(12) 0.06075(12) 0.7260(3) 0.0238(7) Uani 1 1 d . . . . .
N3 N 0.82832(13) 0.01484(13) 0.9775(3) 0.0280(7) Uani 1 1 d . . . . .
C4 C 0.81987(14) -0.02304(15) 0.8729(4) 0.0263(8) Uani 1 1 d . . . . .
C6 C 0.76522(12) 0.10382(14) 0.8130(3) 0.0210(7) Uani 1 1 d . . . . .
C7 C 0.83051(16) -0.08576(15) 0.8827(4) 0.0319(8) Uani 1 1 d . . . . .
C8 C 0.77252(14) 0.15869(15) 0.7453(3) 0.0254(7) Uani 1 1 d . . . . .
C9 C 0.76003(16) 0.21396(15) 0.8105(4) 0.0310(8) Uani 1 1 d . . . . .
H9 H 0.7656 0.2499 0.7650 0.037 Uiso 1 1 calc R U . . .
C10 C 0.84406(19) -0.00859(18) 1.0943(4) 0.0374(9) Uani 1 1 d . . . . .
H10 H 0.8501 0.0173 1.1664 0.045 Uiso 1 1 calc R U . . .
C11 C 0.82015(18) -0.09691(18) 0.6418(4) 0.0390(9) Uani 1 1 d . . . . .
H11 H 0.8214 -0.1210 0.5655 0.047 Uiso 1 1 calc R U . . .
C12 C 0.79935(15) 0.09082(16) 0.6050(3) 0.0285(8) Uani 1 1 d . . . . .
C13 C 0.8105(2) 0.05521(18) 0.4883(4) 0.0381(9) Uani 1 1 d . . . . .
H13 H 0.8172 0.0734 0.4053 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8522(2) -0.06994(19) 1.1168(5) 0.0454(10) Uani 1 1 d . . . . .
H14 H 0.8620 -0.0842 1.2021 0.055 Uiso 1 1 calc R U . . .
C15 C 0.81022(16) -0.03405(17) 0.6273(4) 0.0327(9) Uani 1 1 d . . . . .
C16 C 0.82770(17) -0.12192(18) 0.7650(5) 0.0392(10) Uani 1 1 d . . . . .
H16 H 0.8311 -0.1633 0.7727 0.047 Uiso 1 1 calc R U . . .
C17 C 0.84559(19) -0.10824(18) 1.0108(4) 0.0407(10) Uani 1 1 d . . . . .
H17 H 0.8510 -0.1492 1.0231 0.049 Uiso 1 1 calc R U . . .
C18 C 0.8113(2) -0.00522(19) 0.4990(4) 0.0401(9) Uani 1 1 d . . . . .
H18 H 0.8126 -0.0284 0.4212 0.048 Uiso 1 1 calc R U . . .
C19 C 0.80410(15) 0.00075(15) 0.7448(4) 0.0259(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C12 1.316(5) . ?
N1 C8 1.384(5) . ?
N2 C6 1.390(4) . ?
N2 C12 1.397(4) . ?
N2 C19 1.399(4) . ?
N3 C10 1.319(5) . ?
N3 C4 1.352(4) . ?
C4 C19 1.422(5) . ?
C4 C7 1.424(4) . ?
C6 C6 1.406(6) 10_646 ?
C6 C8 1.407(4) . ?
C7 C17 1.406(6) . ?
C7 C16 1.421(6) . ?
C8 C9 1.421(5) . ?
C9 C9 1.355(7) 10_646 ?
C9 H9 0.9300 . ?
C10 C14 1.400(6) . ?
C10 H10 0.9300 . ?
C11 C16 1.354(6) . ?
C11 C15 1.429(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.427(5) . ?
C13 C18 1.354(6) . ?
C13 H13 0.9300 . ?
C14 C17 1.364(6) . ?
C14 H14 0.9300 . ?
C15 C19 1.406(5) . ?
C15 C18 1.426(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 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
C12 N1 C8 105.0(3) . . ?
C6 N2 C12 105.4(3) . . ?
C6 N2 C19 132.4(3) . . ?
C12 N2 C19 121.9(3) . . ?
C10 N3 C4 117.6(3) . . ?
N3 C4 C19 119.1(3) . . ?
N3 C4 C7 122.7(3) . . ?
C19 C4 C7 118.0(3) . . ?
N2 C6 C6 136.17(17) . 10_646 ?
N2 C6 C8 105.3(3) . . ?
C6 C6 C8 118.2(2) 10_646 . ?
C17 C7 C16 123.3(3) . . ?
C17 C7 C4 116.9(4) . . ?
C16 C7 C4 119.7(4) . . ?
N1 C8 C6 110.4(3) . . ?
N1 C8 C9 128.4(3) . . ?
C6 C8 C9 121.1(3) . . ?
C9 C9 C8 119.6(2) 10_646 . ?
C9 C9 H9 120.2 10_646 . ?
C8 C9 H9 120.2 . . ?
N3 C10 C14 124.3(4) . . ?
N3 C10 H10 117.9 . . ?
C14 C10 H10 117.9 . . ?
C16 C11 C15 121.0(4) . . ?
C16 C11 H11 119.5 . . ?
C15 C11 H11 119.5 . . ?
N1 C12 N2 113.0(3) . . ?
N1 C12 C13 129.2(3) . . ?
N2 C12 C13 117.4(3) . . ?
C18 C13 C12 119.6(4) . . ?
C18 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C17 C14 C10 118.5(4) . . ?
C17 C14 H14 120.8 . . ?
C10 C14 H14 120.8 . . ?
C19 C15 C18 119.4(3) . . ?
C19 C15 C11 118.3(3) . . ?
C18 C15 C11 122.1(3) . . ?
C11 C16 C7 120.8(3) . . ?
C11 C16 H16 119.6 . . ?
C7 C16 H16 119.6 . . ?
C14 C17 C7 119.9(3) . . ?
C14 C17 H17 120.1 . . ?
C7 C17 H17 120.1 . . ?
C13 C18 C15 121.3(4) . . ?
C13 C18 H18 119.3 . . ?
C15 C18 H18 119.3 . . ?
N2 C19 C15 116.4(3) . . ?
N2 C19 C4 122.7(3) . . ?
C15 C19 C4 120.6(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
C10 N3 C4 C19 -178.7(3) . . . . ?
C10 N3 C4 C7 -3.6(5) . . . . ?
C12 N2 C6 C6 165.4(5) . . . 10_646 ?
C19 N2 C6 C6 -20.3(7) . . . 10_646 ?
C12 N2 C6 C8 -8.6(3) . . . . ?
C19 N2 C6 C8 165.7(3) . . . . ?
N3 C4 C7 C17 5.3(5) . . . . ?
C19 C4 C7 C17 -179.5(3) . . . . ?
N3 C4 C7 C16 -172.5(3) . . . . ?
C19 C4 C7 C16 2.7(5) . . . . ?
C12 N1 C8 C6 -2.7(4) . . . . ?
C12 N1 C8 C9 177.5(3) . . . . ?
N2 C6 C8 N1 7.3(4) . . . . ?
C6 C6 C8 N1 -168.0(3) 10_646 . . . ?
N2 C6 C8 C9 -172.9(3) . . . . ?
C6 C6 C8 C9 11.8(5) 10_646 . . . ?
N1 C8 C9 C9 178.9(4) . . . 10_646 ?
C6 C8 C9 C9 -0.9(6) . . . 10_646 ?
C4 N3 C10 C14 -0.3(6) . . . . ?
C8 N1 C12 N2 -3.1(4) . . . . ?
C8 N1 C12 C13 169.9(4) . . . . ?
C6 N2 C12 N1 7.6(4) . . . . ?
C19 N2 C12 N1 -167.4(3) . . . . ?
C6 N2 C12 C13 -166.3(3) . . . . ?
C19 N2 C12 C13 18.7(5) . . . . ?
N1 C12 C13 C18 -174.3(4) . . . . ?
N2 C12 C13 C18 -1.6(6) . . . . ?
N3 C10 C14 C17 2.3(7) . . . . ?
C16 C11 C15 C19 -4.6(6) . . . . ?
C16 C11 C15 C18 170.2(4) . . . . ?
C15 C11 C16 C7 -4.8(6) . . . . ?
C17 C7 C16 C11 -171.9(4) . . . . ?
C4 C7 C16 C11 5.7(5) . . . . ?
C10 C14 C17 C7 -0.4(6) . . . . ?
C16 C7 C17 C14 174.5(4) . . . . ?
C4 C7 C17 C14 -3.1(6) . . . . ?
C12 C13 C18 C15 -9.5(7) . . . . ?
C19 C15 C18 C13 4.4(6) . . . . ?
C11 C15 C18 C13 -170.3(4) . . . . ?
C6 N2 C19 C15 163.0(3) . . . . ?
C12 N2 C19 C15 -23.5(5) . . . . ?
C6 N2 C19 C4 -23.8(5) . . . . ?
C12 N2 C19 C4 149.7(3) . . . . ?
C18 C15 C19 N2 11.7(5) . . . . ?
C11 C15 C19 N2 -173.4(3) . . . . ?
C18 C15 C19 C4 -161.7(4) . . . . ?
C11 C15 C19 C4 13.2(5) . . . . ?
N3 C4 C19 N2 -9.8(5) . . . . ?
C7 C4 C19 N2 174.9(3) . . . . ?
N3 C4 C19 C15 163.2(3) . . . . ?
C7 C4 C19 C15 -12.2(5) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_20181115-5helicene-2
_database_code_depnum_ccdc_archive 'CCDC 1979567'
loop_
_audit_author_name
_audit_author_address
'Takuma Sasayama'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H10 N4'
_chemical_formula_moiety         'C16 H10 N4'
_chemical_formula_weight         258.28
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.6524(7)
_cell_length_b                   4.0000(2)
_cell_length_c                   14.3571(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.273(7)
_cell_angle_gamma                90.0000
_cell_volume                     668.66(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6834
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      68.05
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    2.565
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536.00
_exptl_absorpt_coefficient_mu    1.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_T_max  0.880

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            6812
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_theta_max         68.045
_diffrn_reflns_theta_min         4.796
_diffrn_reflns_theta_full        67.687
_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 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2366
_reflns_number_gt                2181
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_max     0.946
_reflns_Friedel_fraction_full    0.949

#==============================================================================
# REFINEMENT DATA

_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_R_factor_all          0.1641
_refine_ls_R_factor_gt           0.1609
_refine_ls_wR_factor_ref         0.4065
_refine_ls_wR_factor_gt          0.4010
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2366
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.892
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         2.11
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 941 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.8456(8) 0.234(2) 0.4266(6) 0.047(2) Uani 1 1 d . . . . .
N2 N 0.4580(9) 0.233(2) 0.5505(7) 0.047(2) Uani 1 1 d . . . . .
N3 N 0.3885(9) 0.531(3) 0.4295(6) 0.053(2) Uani 1 1 d . . . . .
N4 N 0.7534(8) 0.073(2) 0.5547(6) 0.046(2) Uani 1 1 d . . . . .
C5 C 0.8551(9) 0.076(3) 0.5047(7) 0.044(2) Uani 1 1 d . . . . .
C6 C 0.7338(9) 0.346(3) 0.4201(7) 0.042(2) Uani 1 1 d . . . . .
C7 C 0.5493(9) 0.315(2) 0.4981(6) 0.039(2) Uani 1 1 d . . . . .
C8 C 0.5682(9) 0.614(3) 0.3475(6) 0.043(2) Uani 1 1 d . . . . .
H8 H 0.5349 0.7409 0.2993 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6815(10) 0.531(3) 0.3488(7) 0.047(2) Uani 1 1 d . . . . .
H9 H 0.7255 0.6018 0.2999 0.056 Uiso 1 1 calc R U . . .
C10 C 0.5025(9) 0.499(3) 0.4225(7) 0.044(2) Uani 1 1 d . . . . .
C11 C 0.3600(9) 0.367(3) 0.5030(7) 0.045(2) Uani 1 1 d . . . . .
C12 C 0.4511(11) 0.056(3) 0.6325(8) 0.056(3) Uani 1 1 d . . . . .
H12 H 0.5172 -0.0269 0.6629 0.067 Uiso 1 1 calc R U . . .
C13 C 0.6750(8) 0.243(3) 0.4975(6) 0.038(2) Uani 1 1 d . . . . .
C14 C 0.7488(12) -0.050(3) 0.6423(7) 0.057(3) Uani 1 1 d . . . . .
H14 H 0.6833 -0.0289 0.6769 0.069 Uiso 1 1 calc R U . . .
C15 C 0.3467(12) 0.003(4) 0.6682(8) 0.058(3) Uani 1 1 d . . . . .
H15 H 0.3419 -0.1153 0.7237 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2440(12) 0.124(4) 0.6227(11) 0.071(4) Uani 1 1 d . . . . .
H16 H 0.1731 0.0771 0.6472 0.085 Uiso 1 1 calc R U . . .
C17 C 0.9437(12) -0.229(3) 0.6302(10) 0.061(3) Uani 1 1 d . . . . .
H17 H 1.0062 -0.3439 0.6567 0.073 Uiso 1 1 calc R U . . .
C18 C 0.9535(12) -0.089(3) 0.5473(11) 0.063(3) Uani 1 1 d . . . . .
H18 H 1.0227 -0.0968 0.5172 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2502(11) 0.308(4) 0.5428(10) 0.060(3) Uani 1 1 d . . . . .
H19 H 0.1837 0.3958 0.5143 0.072 Uiso 1 1 calc R U . . .
C20 C 0.8462(15) -0.210(4) 0.6777(9) 0.069(4) Uani 1 1 d . . . . .
H20 H 0.8446 -0.3073 0.7364 0.083 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.287(14) . ?
N1 C6 1.377(14) . ?
N2 C7 1.367(14) . ?
N2 C12 1.380(15) . ?
N2 C11 1.413(15) . ?
N3 C11 1.298(15) . ?
N3 C10 1.341(14) . ?
N4 C14 1.354(14) . ?
N4 C13 1.384(14) . ?
N4 C5 1.409(14) . ?
C5 C18 1.439(16) . ?
C6 C9 1.384(15) . ?
C6 C13 1.391(14) . ?
C7 C10 1.404(15) . ?
C7 C13 1.493(14) . ?
C8 C9 1.360(16) . ?
C8 C10 1.422(14) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C19 1.441(16) . ?
C12 C15 1.355(17) . ?
C12 H12 0.9300 . ?
C14 C20 1.38(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.42(2) . ?
C15 H15 0.9300 . ?
C16 C19 1.37(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.32(2) . ?
C17 C20 1.35(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20 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
C5 N1 C6 105.5(8) . . ?
C7 N2 C12 131.7(10) . . ?
C7 N2 C11 106.0(9) . . ?
C12 N2 C11 122.3(10) . . ?
C11 N3 C10 107.3(9) . . ?
C14 N4 C13 132.9(10) . . ?
C14 N4 C5 122.9(10) . . ?
C13 N4 C5 104.0(8) . . ?
N1 C5 N4 113.9(9) . . ?
N1 C5 C18 129.4(12) . . ?
N4 C5 C18 116.8(10) . . ?
N1 C6 C9 127.8(10) . . ?
N1 C6 C13 110.1(9) . . ?
C9 C6 C13 122.1(10) . . ?
N2 C7 C10 105.3(9) . . ?
N2 C7 C13 137.9(9) . . ?
C10 C7 C13 116.6(8) . . ?
C9 C8 C10 117.5(10) . . ?
C9 C8 H8 121.2 . . ?
C10 C8 H8 121.2 . . ?
C8 C9 C6 122.7(10) . . ?
C8 C9 H9 118.7 . . ?
C6 C9 H9 118.7 . . ?
N3 C10 C7 110.4(9) . . ?
N3 C10 C8 126.1(10) . . ?
C7 C10 C8 123.4(10) . . ?
N3 C11 N2 110.9(9) . . ?
N3 C11 C19 131.7(11) . . ?
N2 C11 C19 117.4(10) . . ?
C15 C12 N2 119.1(13) . . ?
C15 C12 H12 120.5 . . ?
N2 C12 H12 120.5 . . ?
N4 C13 C6 106.6(9) . . ?
N4 C13 C7 135.8(9) . . ?
C6 C13 C7 117.5(9) . . ?
N4 C14 C20 116.6(12) . . ?
N4 C14 H14 121.7 . . ?
C20 C14 H14 121.7 . . ?
C12 C15 C16 121.7(12) . . ?
C12 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C19 C16 C15 119.7(11) . . ?
C19 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C20 122.3(13) . . ?
C18 C17 H17 118.9 . . ?
C20 C17 H17 118.9 . . ?
C17 C18 C5 118.7(13) . . ?
C17 C18 H18 120.6 . . ?
C5 C18 H18 120.6 . . ?
C16 C19 C11 119.8(13) . . ?
C16 C19 H19 120.1 . . ?
C11 C19 H19 120.1 . . ?
C17 C20 C14 122.4(12) . . ?
C17 C20 H20 118.8 . . ?
C14 C20 H20 118.8 . . ?

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
C6 N1 C5 N4 -0.2(12) . . . . ?
C6 N1 C5 C18 -179.2(11) . . . . ?
C14 N4 C5 N1 -173.1(10) . . . . ?
C13 N4 C5 N1 1.4(11) . . . . ?
C14 N4 C5 C18 6.1(15) . . . . ?
C13 N4 C5 C18 -179.4(9) . . . . ?
C5 N1 C6 C9 179.6(10) . . . . ?
C5 N1 C6 C13 -1.1(11) . . . . ?
C12 N2 C7 C10 -179.9(11) . . . . ?
C11 N2 C7 C10 0.9(10) . . . . ?
C12 N2 C7 C13 5.4(19) . . . . ?
C11 N2 C7 C13 -173.7(11) . . . . ?
C10 C8 C9 C6 -0.8(15) . . . . ?
N1 C6 C9 C8 176.5(10) . . . . ?
C13 C6 C9 C8 -2.6(15) . . . . ?
C11 N3 C10 C7 -2.6(11) . . . . ?
C11 N3 C10 C8 173.9(10) . . . . ?
N2 C7 C10 N3 0.9(10) . . . . ?
C13 C7 C10 N3 176.9(8) . . . . ?
N2 C7 C10 C8 -175.7(9) . . . . ?
C13 C7 C10 C8 0.3(13) . . . . ?
C9 C8 C10 N3 -174.2(10) . . . . ?
C9 C8 C10 C7 1.9(15) . . . . ?
C10 N3 C11 N2 3.2(12) . . . . ?
C10 N3 C11 C19 -178.2(12) . . . . ?
C7 N2 C11 N3 -2.6(11) . . . . ?
C12 N2 C11 N3 178.1(10) . . . . ?
C7 N2 C11 C19 178.5(9) . . . . ?
C12 N2 C11 C19 -0.7(15) . . . . ?
C7 N2 C12 C15 -178.0(11) . . . . ?
C11 N2 C12 C15 1.0(16) . . . . ?
C14 N4 C13 C6 171.7(11) . . . . ?
C5 N4 C13 C6 -1.9(10) . . . . ?
C14 N4 C13 C7 -12.7(19) . . . . ?
C5 N4 C13 C7 173.6(10) . . . . ?
N1 C6 C13 N4 2.0(11) . . . . ?
C9 C6 C13 N4 -178.7(8) . . . . ?
N1 C6 C13 C7 -174.5(8) . . . . ?
C9 C6 C13 C7 4.8(14) . . . . ?
N2 C7 C13 N4 -4.5(19) . . . . ?
C10 C7 C13 N4 -178.7(10) . . . . ?
N2 C7 C13 C6 170.7(10) . . . . ?
C10 C7 C13 C6 -3.5(13) . . . . ?
C13 N4 C14 C20 -179.9(11) . . . . ?
C5 N4 C14 C20 -7.2(16) . . . . ?
N2 C12 C15 C16 0.5(18) . . . . ?
C12 C15 C16 C19 -2.4(19) . . . . ?
C20 C17 C18 C5 -2.8(19) . . . . ?
N1 C5 C18 C17 178.2(12) . . . . ?
N4 C5 C18 C17 -0.9(16) . . . . ?
C15 C16 C19 C11 2.7(19) . . . . ?
N3 C11 C19 C16 -179.8(12) . . . . ?
N2 C11 C19 C16 -1.2(17) . . . . ?
C18 C17 C20 C14 2(2) . . . . ?
N4 C14 C20 C17 3.3(19) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_d0610-sasayama
_database_code_depnum_ccdc_archive 'CCDC 1979582'
loop_
_audit_author_name
_audit_author_address
'Takuma Sasayama'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-01-23 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H15 Cl3 N4'
_chemical_formula_moiety         'C25 H15 Cl3 N4'
_chemical_formula_weight         477.78
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.2100
_cell_length_b                   17.1917
_cell_length_c                   19.6180
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     3780.7647
_cell_formula_units_Z            8
_cell_measurement_reflns_used    43085
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1952.00
_exptl_absorpt_coefficient_mu    4.585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.392
_exptl_absorpt_correction_T_max  0.632

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            43243
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         3.418
_diffrn_reflns_theta_full        67.687
_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 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6904
_reflns_number_gt                6478
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.991

#==============================================================================
# REFINEMENT DATA

_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_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1696
_refine_ls_wR_factor_gt          0.1660
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         6904
_refine_ls_number_parameters     532
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0943P)²+4.0205P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.08
_refine_diff_density_min         -0.66
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2684 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.054(6)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl7 Cl 0.6870(4) 0.3282(2) 0.6666(4) 0.245(4) Uani 1 1 d . . . . .
Cl61 Cl 0.49808(16) 0.40348(11) 0.59523(10) 0.0719(5) Uani 1 1 d . . . . .
N2 N 0.8367(3) 0.2387(2) 0.91705(18) 0.0264(7) Uani 1 1 d . . . . .
N3 N 0.0561(4) 0.0848(2) 0.77920(19) 0.0341(9) Uani 1 1 d . . . . .
N4 N 0.0304(3) 0.1915(2) 0.63232(19) 0.0309(8) Uani 1 1 d . . . . .
N5 N 0.5954(3) 0.3586(2) 0.8854(2) 0.0335(8) Uani 1 1 d . . . . .
N6 N 0.7932(4) 0.1257(2) 0.9708(2) 0.0381(10) Uani 1 1 d . . . . .
N8 N 0.1728(4) 0.2832(3) 0.6154(2) 0.0422(10) Uani 1 1 d . . . . .
N9 N 0.2424(4) 0.0734(3) 0.8227(2) 0.0449(11) Uani 1 1 d . . . . .
N60 N 0.4177(4) 0.2961(3) 0.8740(2) 0.0465(11) Uani 1 1 d . . . . .
C11 C 1.0350(4) 0.2678(3) 0.8779(2) 0.0314(10) Uani 1 1 d . . . . .
C12 C -0.0613(4) 0.0620(3) 0.6243(2) 0.0303(9) Uani 1 1 d . . . . .
H12 H -0.0095 0.0422 0.6571 0.036 Uiso 1 1 calc R U . . .
C13 C 0.8792(4) 0.1714(3) 0.9498(2) 0.0307(10) Uani 1 1 d . . . . .
C14 C 0.9117(4) 0.2815(2) 0.8734(2) 0.0288(9) Uani 1 1 d . . . . .
C15 C 0.7129(4) 0.2338(3) 0.9212(2) 0.0301(9) Uani 1 1 d . . . . .
C16 C -0.0547(4) 0.1399(3) 0.6046(2) 0.0301(9) Uani 1 1 d . . . . .
C17 C 0.6904(5) 0.1613(3) 0.9517(3) 0.0373(11) Uani 1 1 d . . . . .
C18 C -0.1276(4) 0.1686(3) 0.5521(3) 0.0359(10) Uani 1 1 d . . . . .
C19 C 0.1158(4) 0.1805(3) 0.6827(2) 0.0312(9) Uani 1 1 d . . . . .
C20 C 0.8665(4) 0.3314(3) 0.8237(2) 0.0318(10) Uani 1 1 d . . . . .
H20 H 0.7846 0.3386 0.8194 0.038 Uiso 1 1 calc R U . . .
C21 C -0.0687(5) 0.0823(3) 0.7867(2) 0.0342(10) Uani 1 1 d . . . . .
C22 C 0.1281(4) 0.1330(3) 0.7407(2) 0.0327(10) Uani 1 1 d . . . . .
C23 C 0.6578(4) 0.4259(3) 0.9064(2) 0.0342(10) Uani 1 1 d . . . . .
C24 C 0.1317(5) 0.0488(3) 0.8270(3) 0.0399(12) Uani 1 1 d . . . . .
C25 C 0.2062(5) 0.2351(3) 0.6685(2) 0.0380(11) Uani 1 1 d . . . . .
C26 C 0.7574(4) 0.4228(3) 0.9478(2) 0.0330(10) Uani 1 1 d . . . . .
H26 H 0.7884 0.3751 0.9614 0.040 Uiso 1 1 calc R U . . .
C27 C -0.1464(5) 0.0146(3) 0.5942(2) 0.0367(11) Uani 1 1 d . . . . .
H27 H -0.1518 -0.0373 0.6074 0.044 Uiso 1 1 calc R U . . .
C28 C 0.6150(4) 0.2803(3) 0.9025(2) 0.0317(10) Uani 1 1 d . . . . .
C29 C 0.0677(5) 0.2567(3) 0.5952(2) 0.0371(11) Uani 1 1 d . . . . .
C30 C 1.0800(4) 0.2076(3) 0.9216(2) 0.0358(11) Uani 1 1 d . . . . .
H30 H 1.1619 0.2018 0.9272 0.043 Uiso 1 1 calc R U . . .
C31 C -0.1446(5) 0.1368(3) 0.7568(2) 0.0361(10) Uani 1 1 d . . . . .
H31 H -0.1133 0.1785 0.7326 0.043 Uiso 1 1 calc R U . . .
C32 C 0.2428(5) 0.1282(3) 0.7712(2) 0.0392(11) Uani 1 1 d . . . . .
C33 C 0.5023(4) 0.2447(3) 0.8992(3) 0.0390(11) Uani 1 1 d . . . . .
C34 C 0.6073(5) 0.4979(3) 0.8873(3) 0.0403(11) Uani 1 1 d . . . . .
C35 C 1.0050(5) 0.1596(3) 0.9545(2) 0.0363(11) Uani 1 1 d . . . . .
H35 H 1.0351 0.1187 0.9804 0.044 Uiso 1 1 calc R U . . .
C36 C 0.8105(4) 0.4908(3) 0.9688(3) 0.0384(11) Uani 1 1 d . . . . .
H36 H 0.8777 0.4887 0.9965 0.046 Uiso 1 1 calc R U . . .
C37 C 1.1110(4) 0.3089(3) 0.8340(3) 0.0379(11) Uani 1 1 d . . . . .
H37 H 1.1931 0.3023 0.8375 0.046 Uiso 1 1 calc R U . . .
C38 C -0.2229(5) 0.0428(3) 0.5452(3) 0.0421(12) Uani 1 1 d . . . . .
H38 H -0.2811 0.0105 0.5268 0.051 Uiso 1 1 calc R U . . .
C39 C -0.2136(5) 0.1189(3) 0.5234(3) 0.0399(11) Uani 1 1 d . . . . .
H39 H -0.2644 0.1373 0.4896 0.048 Uiso 1 1 calc R U . . .
C40 C 0.9437(5) 0.3700(3) 0.7810(3) 0.0397(11) Uani 1 1 d . . . . .
H40 H 0.9137 0.4040 0.7483 0.048 Uiso 1 1 calc R U . . .
C41 C 0.5731(5) 0.1296(3) 0.9533(3) 0.0433(12) Uani 1 1 d . . . . .
H41 H 0.5595 0.0819 0.9744 0.052 Uiso 1 1 calc R U . . .
C42 C -0.0065(5) 0.2848(3) 0.5422(3) 0.0441(12) Uani 1 1 d . . . . .
H42 H 0.0115 0.3315 0.5206 0.053 Uiso 1 1 calc R U . . .
C43 C -0.1155(5) 0.0227(3) 0.8286(3) 0.0434(12) Uani 1 1 d . . . . .
C44 C 0.7653(5) 0.5626(3) 0.9493(3) 0.0451(12) Uani 1 1 d . . . . .
H44 H 0.8022 0.6082 0.9637 0.054 Uiso 1 1 calc R U . . .
C45 C -0.2654(5) 0.1285(3) 0.7634(3) 0.0459(13) Uani 1 1 d . . . . .
H45 H -0.3157 0.1649 0.7433 0.055 Uiso 1 1 calc R U . . .
C46 C 0.3163(5) 0.2338(3) 0.7030(3) 0.0442(13) Uani 1 1 d . . . . .
H46 H 0.3748 0.2704 0.6930 0.053 Uiso 1 1 calc R U . . .
C47 C 0.3362(5) 0.1779(3) 0.7513(3) 0.0464(13) Uani 1 1 d . . . . .
H47 H 0.4113 0.1728 0.7710 0.056 Uiso 1 1 calc R U . . .
C48 C 0.6658(5) 0.5658(3) 0.9087(3) 0.0485(13) Uani 1 1 d . . . . .
H48 H 0.6365 0.6140 0.8950 0.058 Uiso 1 1 calc R U . . .
C49 C 0.4812(5) 0.1689(3) 0.9242(3) 0.0450(13) Uani 1 1 d . . . . .
H49 H 0.4060 0.1464 0.9208 0.054 Uiso 1 1 calc R U . . .
C50 C -0.1029(5) 0.2438(3) 0.5234(3) 0.0444(12) Uani 1 1 d . . . . .
H50 H -0.1547 0.2645 0.4911 0.053 Uiso 1 1 calc R U . . .
C51 C 0.4744(4) 0.3628(3) 0.8665(3) 0.0415(12) Uani 1 1 d . . . . .
C52 C 1.0656(5) 0.3589(3) 0.7860(3) 0.0433(12) Uani 1 1 d . . . . .
H52 H 1.1168 0.3853 0.7568 0.052 Uiso 1 1 calc R U . . .
C53 C -0.0368(6) -0.0227(3) 0.8691(3) 0.0521(15) Uani 1 1 d . . . . .
H53 H -0.0677 -0.0634 0.8948 0.063 Uiso 1 1 calc R U . . .
C54 C -0.2400(6) 0.0155(4) 0.8327(3) 0.0508(15) Uani 1 1 d . . . . .
H54 H -0.2729 -0.0247 0.8583 0.061 Uiso 1 1 calc R U . . .
C55 C 0.0799(6) -0.0086(3) 0.8713(3) 0.0511(15) Uani 1 1 d . . . . .
H55 H 0.1281 -0.0360 0.9016 0.061 Uiso 1 1 calc R U . . .
C56 C 0.4953(6) 0.5008(4) 0.8524(3) 0.0562(15) Uani 1 1 d . . . . .
H56 H 0.4678 0.5481 0.8355 0.067 Uiso 1 1 calc R U . . .
C57 C -0.3143(6) 0.0665(4) 0.7996(3) 0.0533(15) Uani 1 1 d . . . . .
H57 H -0.3966 0.0598 0.8013 0.064 Uiso 1 1 calc R U . . .
C58 C 0.4291(5) 0.4365(4) 0.8436(3) 0.0557(15) Uani 1 1 d . . . . .
H58 H 0.3546 0.4396 0.8229 0.067 Uiso 1 1 calc R U . . .
C59 C 0.5859(10) 0.4051(6) 0.6807(12) 0.199(10) Uani 1 1 d . . . . .
H59A H 0.6268 0.4543 0.6874 0.239 Uiso 1 1 calc R U . . .
H59B H 0.5343 0.3949 0.7193 0.239 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl7 C59 1.763(13) . ?
Cl61 C59 1.944(18) . ?
N2 C15 1.393(6) . ?
N2 C13 1.407(6) . ?
N2 C14 1.408(6) . ?
N3 C22 1.382(6) . ?
N3 C21 1.408(7) . ?
N3 C24 1.407(6) . ?
N4 C19 1.389(6) . ?
N4 C29 1.401(6) . ?
N4 C16 1.412(6) . ?
N5 C28 1.405(6) . ?
N5 C51 1.409(6) . ?
N5 C23 1.413(6) . ?
N6 C13 1.310(6) . ?
N6 C17 1.358(7) . ?
N8 C29 1.324(7) . ?
N8 C25 1.382(7) . ?
N9 C24 1.314(7) . ?
N9 C32 1.381(7) . ?
N60 C51 1.321(7) . ?
N60 C33 1.386(7) . ?
C11 C37 1.403(7) . ?
C11 C14 1.405(6) . ?
C11 C30 1.436(7) . ?
C12 C27 1.387(7) . ?
C12 C16 1.397(6) . ?
C12 H12 0.9300 . ?
C13 C35 1.429(7) . ?
C14 C20 1.395(7) . ?
C15 C17 1.404(7) . ?
C15 C28 1.406(6) . ?
C16 C18 1.405(7) . ?
C17 C41 1.424(7) . ?
C18 C39 1.406(7) . ?
C18 C50 1.437(7) . ?
C19 C25 1.408(7) . ?
C19 C22 1.407(7) . ?
C20 C40 1.375(7) . ?
C20 H20 0.9300 . ?
C21 C31 1.395(7) . ?
C21 C43 1.414(7) . ?
C22 C32 1.421(7) . ?
C23 C26 1.383(7) . ?
C23 C34 1.412(7) . ?
C24 C55 1.437(8) . ?
C25 C46 1.408(7) . ?
C26 C36 1.375(7) . ?
C26 H26 0.9300 . ?
C27 C38 1.377(7) . ?
C27 H27 0.9300 . ?
C28 C33 1.405(7) . ?
C29 C42 1.416(8) . ?
C30 C35 1.343(7) . ?
C30 H30 0.9300 . ?
C31 C45 1.367(8) . ?
C31 H31 0.9300 . ?
C32 C47 1.407(8) . ?
C33 C49 1.413(8) . ?
C34 C48 1.403(8) . ?
C34 C56 1.431(8) . ?
C35 H35 0.9300 . ?
C36 C44 1.387(7) . ?
C36 H36 0.9300 . ?
C37 C52 1.372(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.380(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 C52 1.383(8) . ?
C40 H40 0.9300 . ?
C41 C49 1.359(8) . ?
C41 H41 0.9300 . ?
C42 C50 1.343(8) . ?
C42 H42 0.9300 . ?
C43 C54 1.404(9) . ?
C43 C53 1.420(8) . ?
C44 C48 1.373(8) . ?
C44 H44 0.9300 . ?
C45 C57 1.393(8) . ?
C45 H45 0.9300 . ?
C46 C47 1.369(8) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C58 1.436(8) . ?
C52 H52 0.9300 . ?
C53 C55 1.331(10) . ?
C53 H53 0.9300 . ?
C54 C57 1.373(9) . ?
C54 H54 0.9300 . ?
C55 H55 0.9300 . ?
C56 C58 1.343(9) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 N2 C13 105.1(4) . . ?
C15 N2 C14 131.5(4) . . ?
C13 N2 C14 120.4(4) . . ?
C22 N3 C21 131.0(4) . . ?
C22 N3 C24 106.1(4) . . ?
C21 N3 C24 121.0(4) . . ?
C19 N4 C29 105.8(4) . . ?
C19 N4 C16 130.9(4) . . ?
C29 N4 C16 120.3(4) . . ?
C28 N5 C51 105.3(4) . . ?
C28 N5 C23 129.7(4) . . ?
C51 N5 C23 120.7(4) . . ?
C13 N6 C17 105.5(4) . . ?
C29 N8 C25 105.1(4) . . ?
C24 N9 C32 105.7(4) . . ?
C51 N60 C33 105.3(4) . . ?
C37 C11 C14 118.3(5) . . ?
C37 C11 C30 121.1(4) . . ?
C14 C11 C30 120.3(4) . . ?
C27 C12 C16 118.8(4) . . ?
C27 C12 H12 120.6 . . ?
C16 C12 H12 120.6 . . ?
N6 C13 N2 112.8(4) . . ?
N6 C13 C35 128.4(4) . . ?
N2 C13 C35 118.7(4) . . ?
C20 C14 C11 120.3(4) . . ?
C20 C14 N2 122.0(4) . . ?
C11 C14 N2 117.5(4) . . ?
N2 C15 C17 104.9(4) . . ?
N2 C15 C28 136.7(4) . . ?
C17 C15 C28 118.4(4) . . ?
C12 C16 C18 120.6(4) . . ?
C12 C16 N4 122.1(4) . . ?
C18 C16 N4 117.1(4) . . ?
N6 C17 C15 111.4(4) . . ?
N6 C17 C41 127.2(5) . . ?
C15 C17 C41 121.1(5) . . ?
C39 C18 C16 118.6(4) . . ?
C39 C18 C50 121.6(4) . . ?
C16 C18 C50 119.4(4) . . ?
N4 C19 C25 105.3(4) . . ?
N4 C19 C22 136.2(4) . . ?
C25 C19 C22 118.4(4) . . ?
C40 C20 C14 119.6(5) . . ?
C40 C20 H20 120.2 . . ?
C14 C20 H20 120.2 . . ?
C31 C21 N3 122.8(4) . . ?
C31 C21 C43 120.3(5) . . ?
N3 C21 C43 116.8(5) . . ?
N3 C22 C19 137.1(4) . . ?
N3 C22 C32 105.2(4) . . ?
C19 C22 C32 117.6(5) . . ?
C26 C23 N5 122.7(4) . . ?
C26 C23 C34 120.9(5) . . ?
N5 C23 C34 116.3(4) . . ?
N9 C24 N3 112.5(5) . . ?
N9 C24 C55 129.9(5) . . ?
N3 C24 C55 117.5(5) . . ?
N8 C25 C46 127.5(5) . . ?
N8 C25 C19 110.7(4) . . ?
C46 C25 C19 121.7(5) . . ?
C36 C26 C23 119.6(4) . . ?
C36 C26 H26 120.2 . . ?
C23 C26 H26 120.2 . . ?
C38 C27 C12 121.3(4) . . ?
C38 C27 H27 119.3 . . ?
C12 C27 H27 119.3 . . ?
N5 C28 C33 105.4(4) . . ?
N5 C28 C15 136.8(4) . . ?
C33 C28 C15 117.8(4) . . ?
N8 C29 N4 112.7(4) . . ?
N8 C29 C42 128.7(5) . . ?
N4 C29 C42 118.6(4) . . ?
C35 C30 C11 120.6(4) . . ?
C35 C30 H30 119.7 . . ?
C11 C30 H30 119.7 . . ?
C45 C31 C21 119.6(5) . . ?
C45 C31 H31 120.2 . . ?
C21 C31 H31 120.2 . . ?
N9 C32 C47 128.3(5) . . ?
N9 C32 C22 110.1(5) . . ?
C47 C32 C22 121.4(5) . . ?
N60 C33 C28 110.8(5) . . ?
N60 C33 C49 126.6(5) . . ?
C28 C33 C49 122.4(5) . . ?
C48 C34 C23 117.6(5) . . ?
C48 C34 C56 121.6(5) . . ?
C23 C34 C56 120.6(5) . . ?
C30 C35 C13 120.0(4) . . ?
C30 C35 H35 120.0 . . ?
C13 C35 H35 120.0 . . ?
C26 C36 C44 121.1(5) . . ?
C26 C36 H36 119.5 . . ?
C44 C36 H36 119.5 . . ?
C52 C37 C11 120.7(5) . . ?
C52 C37 H37 119.6 . . ?
C11 C37 H37 119.6 . . ?
C27 C38 C39 120.2(5) . . ?
C27 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C38 C39 C18 120.3(5) . . ?
C38 C39 H39 119.8 . . ?
C18 C39 H39 119.8 . . ?
C20 C40 C52 120.8(5) . . ?
C20 C40 H40 119.6 . . ?
C52 C40 H40 119.6 . . ?
C49 C41 C17 120.0(5) . . ?
C49 C41 H41 120.0 . . ?
C17 C41 H41 120.0 . . ?
C50 C42 C29 119.7(4) . . ?
C50 C42 H42 120.1 . . ?
C29 C42 H42 120.1 . . ?
C54 C43 C21 117.8(5) . . ?
C54 C43 C53 122.5(5) . . ?
C21 C43 C53 119.5(6) . . ?
C48 C44 C36 119.5(5) . . ?
C48 C44 H44 120.2 . . ?
C36 C44 H44 120.2 . . ?
C31 C45 C57 121.2(6) . . ?
C31 C45 H45 119.4 . . ?
C57 C45 H45 119.4 . . ?
C47 C46 C25 119.2(5) . . ?
C47 C46 H46 120.4 . . ?
C25 C46 H46 120.4 . . ?
C46 C47 C32 119.8(5) . . ?
C46 C47 H47 120.1 . . ?
C32 C47 H47 120.1 . . ?
C44 C48 C34 121.3(5) . . ?
C44 C48 H48 119.3 . . ?
C34 C48 H48 119.3 . . ?
C41 C49 C33 118.5(5) . . ?
C41 C49 H49 120.7 . . ?
C33 C49 H49 120.7 . . ?
C42 C50 C18 121.3(5) . . ?
C42 C50 H50 119.3 . . ?
C18 C50 H50 119.3 . . ?
N60 C51 N5 112.9(5) . . ?
N60 C51 C58 129.2(5) . . ?
N5 C51 C58 117.9(5) . . ?
C37 C52 C40 120.1(5) . . ?
C37 C52 H52 119.9 . . ?
C40 C52 H52 119.9 . . ?
C55 C53 C43 121.9(5) . . ?
C55 C53 H53 119.0 . . ?
C43 C53 H53 119.0 . . ?
C57 C54 C43 121.3(5) . . ?
C57 C54 H54 119.4 . . ?
C43 C54 H54 119.4 . . ?
C53 C55 C24 120.1(5) . . ?
C53 C55 H55 119.9 . . ?
C24 C55 H55 119.9 . . ?
C58 C56 C34 121.1(5) . . ?
C58 C56 H56 119.4 . . ?
C34 C56 H56 119.4 . . ?
C54 C57 C45 119.4(5) . . ?
C54 C57 H57 120.3 . . ?
C45 C57 H57 120.3 . . ?
C56 C58 C51 119.4(5) . . ?
C56 C58 H58 120.3 . . ?
C51 C58 H58 120.3 . . ?
Cl7 C59 Cl61 100.3(9) . . ?
Cl7 C59 H59A 111.7 . . ?
Cl61 C59 H59A 111.7 . . ?
Cl7 C59 H59B 111.7 . . ?
Cl61 C59 H59B 111.7 . . ?
H59A C59 H59B 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
C17 N6 C13 N2 0.8(5) . . . . ?
C17 N6 C13 C35 -177.3(5) . . . . ?
C15 N2 C13 N6 2.3(5) . . . . ?
C14 N2 C13 N6 -160.3(4) . . . . ?
C15 N2 C13 C35 -179.4(4) . . . . ?
C14 N2 C13 C35 18.0(6) . . . . ?
C37 C11 C14 C20 3.9(7) . . . . ?
C30 C11 C14 C20 -170.2(4) . . . . ?
C37 C11 C14 N2 179.0(4) . . . . ?
C30 C11 C14 N2 4.9(6) . . . . ?
C15 N2 C14 C20 1.2(7) . . . . ?
C13 N2 C14 C20 158.5(4) . . . . ?
C15 N2 C14 C11 -173.8(4) . . . . ?
C13 N2 C14 C11 -16.5(6) . . . . ?
C13 N2 C15 C17 -4.1(5) . . . . ?
C14 N2 C15 C17 155.6(4) . . . . ?
C13 N2 C15 C28 177.1(5) . . . . ?
C14 N2 C15 C28 -23.1(8) . . . . ?
C27 C12 C16 C18 -4.0(7) . . . . ?
C27 C12 C16 N4 -179.2(4) . . . . ?
C19 N4 C16 C12 -3.0(7) . . . . ?
C29 N4 C16 C12 154.4(4) . . . . ?
C19 N4 C16 C18 -178.4(5) . . . . ?
C29 N4 C16 C18 -20.9(6) . . . . ?
C13 N6 C17 C15 -3.6(5) . . . . ?
C13 N6 C17 C41 169.5(5) . . . . ?
N2 C15 C17 N6 5.0(5) . . . . ?
C28 C15 C17 N6 -176.0(4) . . . . ?
N2 C15 C17 C41 -168.7(4) . . . . ?
C28 C15 C17 C41 10.3(7) . . . . ?
C12 C16 C18 C39 4.7(7) . . . . ?
N4 C16 C18 C39 -179.8(4) . . . . ?
C12 C16 C18 C50 -167.5(5) . . . . ?
N4 C16 C18 C50 8.0(7) . . . . ?
C29 N4 C19 C25 -6.0(5) . . . . ?
C16 N4 C19 C25 153.9(5) . . . . ?
C29 N4 C19 C22 171.4(5) . . . . ?
C16 N4 C19 C22 -28.7(9) . . . . ?
C11 C14 C20 C40 -3.1(7) . . . . ?
N2 C14 C20 C40 -177.9(4) . . . . ?
C22 N3 C21 C31 -4.8(7) . . . . ?
C24 N3 C21 C31 157.1(4) . . . . ?
C22 N3 C21 C43 177.5(4) . . . . ?
C24 N3 C21 C43 -20.7(6) . . . . ?
C21 N3 C22 C19 -22.0(9) . . . . ?
C24 N3 C22 C19 174.1(5) . . . . ?
C21 N3 C22 C32 159.3(5) . . . . ?
C24 N3 C22 C32 -4.6(5) . . . . ?
N4 C19 C22 N3 -11.7(10) . . . . ?
C25 C19 C22 N3 165.4(5) . . . . ?
N4 C19 C22 C32 166.9(5) . . . . ?
C25 C19 C22 C32 -16.0(7) . . . . ?
C28 N5 C23 C26 2.7(7) . . . . ?
C51 N5 C23 C26 155.7(5) . . . . ?
C28 N5 C23 C34 -172.2(5) . . . . ?
C51 N5 C23 C34 -19.2(6) . . . . ?
C32 N9 C24 N3 0.7(6) . . . . ?
C32 N9 C24 C55 179.4(5) . . . . ?
C22 N3 C24 N9 2.6(5) . . . . ?
C21 N3 C24 N9 -163.3(4) . . . . ?
C22 N3 C24 C55 -176.3(4) . . . . ?
C21 N3 C24 C55 17.9(6) . . . . ?
C29 N8 C25 C46 173.1(5) . . . . ?
C29 N8 C25 C19 -3.0(6) . . . . ?
N4 C19 C25 N8 5.7(5) . . . . ?
C22 C19 C25 N8 -172.2(4) . . . . ?
N4 C19 C25 C46 -170.6(4) . . . . ?
C22 C19 C25 C46 11.4(7) . . . . ?
N5 C23 C26 C36 -177.0(4) . . . . ?
C34 C23 C26 C36 -2.3(7) . . . . ?
C16 C12 C27 C38 0.5(7) . . . . ?
C51 N5 C28 C33 -5.8(5) . . . . ?
C23 N5 C28 C33 150.4(5) . . . . ?
C51 N5 C28 C15 175.2(5) . . . . ?
C23 N5 C28 C15 -28.6(9) . . . . ?
N2 C15 C28 N5 -18.1(10) . . . . ?
C17 C15 C28 N5 163.3(5) . . . . ?
N2 C15 C28 C33 163.0(5) . . . . ?
C17 C15 C28 C33 -15.6(6) . . . . ?
C25 N8 C29 N4 -1.0(6) . . . . ?
C25 N8 C29 C42 -179.9(5) . . . . ?
C19 N4 C29 N8 4.5(5) . . . . ?
C16 N4 C29 N8 -157.9(4) . . . . ?
C19 N4 C29 C42 -176.4(5) . . . . ?
C16 N4 C29 C42 21.1(7) . . . . ?
C37 C11 C30 C35 -168.5(4) . . . . ?
C14 C11 C30 C35 5.5(7) . . . . ?
N3 C21 C31 C45 176.7(5) . . . . ?
C43 C21 C31 C45 -5.7(7) . . . . ?
C24 N9 C32 C47 172.5(5) . . . . ?
C24 N9 C32 C22 -3.7(5) . . . . ?
N3 C22 C32 N9 5.3(5) . . . . ?
C19 C22 C32 N9 -173.7(4) . . . . ?
N3 C22 C32 C47 -171.2(4) . . . . ?
C19 C22 C32 C47 9.8(7) . . . . ?
C51 N60 C33 C28 -4.1(6) . . . . ?
C51 N60 C33 C49 170.8(5) . . . . ?
N5 C28 C33 N60 6.3(5) . . . . ?
C15 C28 C33 N60 -174.5(4) . . . . ?
N5 C28 C33 C49 -168.8(4) . . . . ?
C15 C28 C33 C49 10.4(7) . . . . ?
C26 C23 C34 C48 3.5(7) . . . . ?
N5 C23 C34 C48 178.6(5) . . . . ?
C26 C23 C34 C56 -171.3(5) . . . . ?
N5 C23 C34 C56 3.7(7) . . . . ?
C11 C30 C35 C13 -4.1(7) . . . . ?
N6 C13 C35 C30 170.6(5) . . . . ?
N2 C13 C35 C30 -7.4(7) . . . . ?
C23 C26 C36 C44 0.3(8) . . . . ?
C14 C11 C37 C52 -2.8(7) . . . . ?
C30 C11 C37 C52 171.3(4) . . . . ?
C12 C27 C38 C39 2.2(8) . . . . ?
C27 C38 C39 C18 -1.4(8) . . . . ?
C16 C18 C39 C38 -2.0(8) . . . . ?
C50 C18 C39 C38 170.0(5) . . . . ?
C14 C20 C40 C52 1.1(8) . . . . ?
N6 C17 C41 C49 -171.4(5) . . . . ?
C15 C17 C41 C49 1.1(8) . . . . ?
N8 C29 C42 C50 171.1(5) . . . . ?
N4 C29 C42 C50 -7.8(8) . . . . ?
C31 C21 C43 C54 6.9(7) . . . . ?
N3 C21 C43 C54 -175.3(4) . . . . ?
C31 C21 C43 C53 -167.7(4) . . . . ?
N3 C21 C43 C53 10.1(7) . . . . ?
C26 C36 C44 C48 0.3(8) . . . . ?
C21 C31 C45 C57 0.2(8) . . . . ?
N8 C25 C46 C47 -175.4(5) . . . . ?
C19 C25 C46 C47 0.3(8) . . . . ?
C25 C46 C47 C32 -6.9(8) . . . . ?
N9 C32 C47 C46 -173.9(5) . . . . ?
C22 C32 C47 C46 1.9(8) . . . . ?
C36 C44 C48 C34 1.1(9) . . . . ?
C23 C34 C48 C44 -3.0(8) . . . . ?
C56 C34 C48 C44 171.9(5) . . . . ?
C17 C41 C49 C33 -6.7(8) . . . . ?
N60 C33 C49 C41 -173.4(5) . . . . ?
C28 C33 C49 C41 1.0(7) . . . . ?
C29 C42 C50 C18 -5.0(9) . . . . ?
C39 C18 C50 C42 -167.1(5) . . . . ?
C16 C18 C50 C42 4.9(8) . . . . ?
C33 N60 C51 N5 0.2(6) . . . . ?
C33 N60 C51 C58 -178.4(5) . . . . ?
C28 N5 C51 N60 3.6(6) . . . . ?
C23 N5 C51 N60 -155.2(4) . . . . ?
C28 N5 C51 C58 -177.6(5) . . . . ?
C23 N5 C51 C58 23.6(7) . . . . ?
C11 C37 C52 C40 0.9(8) . . . . ?
C20 C40 C52 C37 0.0(8) . . . . ?
C54 C43 C53 C55 -171.2(5) . . . . ?
C21 C43 C53 C55 3.1(8) . . . . ?
C21 C43 C54 C57 -2.8(8) . . . . ?
C53 C43 C54 C57 171.6(5) . . . . ?
C43 C53 C55 C24 -6.2(9) . . . . ?
N9 C24 C55 C53 177.3(5) . . . . ?
N3 C24 C55 C53 -4.1(8) . . . . ?
C48 C34 C56 C58 -167.2(6) . . . . ?
C23 C34 C56 C58 7.5(9) . . . . ?
C43 C54 C57 C45 -2.5(8) . . . . ?
C31 C45 C57 C54 3.9(8) . . . . ?
C34 C56 C58 C51 -3.3(9) . . . . ?
N60 C51 C58 C56 166.7(6) . . . . ?
N5 C51 C58 C56 -11.8(8) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


