# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_bluexyzA
_database_code_depnum_ccdc_archive 'CCDC 1951224'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J D WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2019-09-03 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 9.(I3)2
;
_chemical_name_common            ?
_chemical_melting_point          533
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 I3 N2'
_chemical_formula_weight         577.95

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'
I I -0.4742 1.8119 '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                   9.0754(6)
_cell_length_b                   9.9135(7)
_cell_length_c                   9.9267(6)
_cell_angle_alpha                69.799(6)
_cell_angle_beta                 77.933(6)
_cell_angle_gamma                67.701(6)
_cell_volume                     772.34(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2078
_cell_measurement_theta_min      3.8860
_cell_measurement_theta_max      28.2930

_exptl_crystal_description       'thick needle'
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.485
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.454
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    6.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.209
_exptl_absorpt_correction_T_max  0.508
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            6229
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.423
_diffrn_reflns_theta_max         29.388
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3560
_reflns_number_gt                2697
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3560
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
I1 I 0.12718(5) 0.30382(5) 0.19765(4) 0.02912(12) Uani 1 1 d . . . . .
I2 I 0.38367(5) 0.25378(4) 0.36992(4) 0.02482(12) Uani 1 1 d . . . . .
I3 I 0.61990(5) 0.22279(5) 0.54037(5) 0.03287(13) Uani 1 1 d . . . . .
N1 N 0.0634(5) 0.1639(5) 0.7051(5) 0.0180(10) Uani 1 1 d . . . . .
N2 N 0.4330(6) 0.2820(5) 0.8845(5) 0.0177(10) Uani 1 1 d . . . . .
C1 C 0.1716(7) 0.1204(6) 0.7981(6) 0.0174(12) Uani 1 1 d . . . . .
C2 C 0.2367(7) 0.2242(7) 0.8052(6) 0.0214(13) Uani 1 1 d . . . . .
H2 H 0.1919 0.3287 0.7535 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3639(7) 0.1810(6) 0.8845(6) 0.0175(12) Uani 1 1 d . . . . .
C4 C 0.4354(6) 0.0228(6) 0.9619(6) 0.0157(12) Uani 1 1 d . . . . .
C5 C 0.3632(6) -0.0827(6) 0.9654(6) 0.0163(12) Uani 1 1 d . . . . .
C6 C 0.5745(7) 0.2344(6) 0.9482(6) 0.0160(12) Uani 1 1 d . . . . .
C7 C 0.6592(7) 0.3347(6) 0.9241(6) 0.0201(13) Uani 1 1 d . . . . .
H7 H 0.6205 0.4368 0.8644 0.024 Uiso 1 1 calc R U . . .
C8 C 0.7980(7) 0.2835(6) 0.9876(6) 0.0211(13) Uani 1 1 d . . . . .
H8 H 0.8560 0.3512 0.9690 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8574(7) 0.1365(6) 1.0782(6) 0.0205(13) Uani 1 1 d . . . . .
H9 H 0.9549 0.1042 1.1199 0.025 Uiso 1 1 calc R U . . .
C10 C 0.7731(6) 0.0371(6) 1.1072(6) 0.0152(12) Uani 1 1 d . . . . .
C11 C 0.0484(7) 0.0619(7) 0.6348(6) 0.0291(15) Uani 1 1 d . . . . .
H11A H 0.1413 -0.0320 0.6509 0.044 Uiso 1 1 calc R U . . .
H11B H 0.0434 0.1128 0.5310 0.044 Uiso 1 1 calc R U . . .
H11C H -0.0493 0.0368 0.6754 0.044 Uiso 1 1 calc R U . . .
C12 C -0.0146(7) 0.3242(7) 0.6322(6) 0.0271(14) Uani 1 1 d . . . . .
H12A H -0.0352 0.3845 0.6985 0.041 Uiso 1 1 calc R U . . .
H12B H -0.1161 0.3374 0.6010 0.041 Uiso 1 1 calc R U . . .
H12C H 0.0549 0.3588 0.5479 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3559(7) 0.4442(6) 0.8115(7) 0.0284(15) Uani 1 1 d . . . . .
H13A H 0.3916 0.4658 0.7084 0.043 Uiso 1 1 calc R U . . .
H13B H 0.3850 0.5063 0.8528 0.043 Uiso 1 1 calc R U . . .
H13C H 0.2396 0.4687 0.8246 0.043 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
I1 I2 2.9649(6) . ?
I2 I3 2.8656(6) . ?
N1 C1 1.337(7) . ?
N1 C12 1.455(7) . ?
N1 C11 1.469(7) . ?
N2 C3 1.368(7) . ?
N2 C6 1.394(7) . ?
N2 C13 1.467(7) . ?
C1 C2 1.394(8) . ?
C1 C10 1.470(8) 2_657 ?
C2 C3 1.381(8) . ?
C3 C4 1.441(7) . ?
C4 C4 1.372(11) 2_657 ?
C4 C5 1.418(7) . ?
C5 C10 1.406(7) 2_657 ?
C5 C6 1.409(7) 2_657 ?
C6 C7 1.406(7) . ?
C6 C5 1.409(7) 2_657 ?
C7 C8 1.366(8) . ?
C8 C9 1.388(8) . ?
C9 C10 1.386(7) . ?
C10 C5 1.406(7) 2_657 ?
C10 C1 1.470(8) 2_657 ?

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
I3 I2 I1 176.448(18) . . ?
C1 N1 C12 121.3(5) . . ?
C1 N1 C11 123.5(5) . . ?
C12 N1 C11 112.7(4) . . ?
C3 N2 C6 122.0(5) . . ?
C3 N2 C13 117.9(5) . . ?
C6 N2 C13 120.1(4) . . ?
N1 C1 C2 120.1(5) . . ?
N1 C1 C10 121.3(5) . 2_657 ?
C2 C1 C10 118.6(5) . 2_657 ?
C3 C2 C1 122.5(6) . . ?
N2 C3 C2 122.2(5) . . ?
N2 C3 C4 117.9(5) . . ?
C2 C3 C4 119.7(5) . . ?
C4 C4 C5 120.8(7) 2_657 . ?
C4 C4 C3 120.5(6) 2_657 . ?
C5 C4 C3 118.6(5) . . ?
C10 C5 C6 120.1(5) 2_657 2_657 ?
C10 C5 C4 121.7(5) 2_657 . ?
C6 C5 C4 118.1(5) 2_657 . ?
N2 C6 C7 120.9(5) . . ?
N2 C6 C5 120.0(5) . 2_657 ?
C7 C6 C5 119.1(5) . 2_657 ?
C8 C7 C6 119.2(5) . . ?
C7 C8 C9 122.5(5) . . ?
C10 C9 C8 119.3(6) . . ?
C9 C10 C5 119.4(5) . 2_657 ?
C9 C10 C1 122.5(5) . 2_657 ?
C5 C10 C1 117.9(5) 2_657 2_657 ?

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
C12 N1 C1 C2 -13.4(7) . . . . ?
C11 N1 C1 C2 147.3(5) . . . . ?
C12 N1 C1 C10 167.8(5) . . . 2_657 ?
C11 N1 C1 C10 -31.5(8) . . . 2_657 ?
N1 C1 C2 C3 -171.0(5) . . . . ?
C10 C1 C2 C3 7.9(8) 2_657 . . . ?
C6 N2 C3 C2 -171.0(5) . . . . ?
C13 N2 C3 C2 7.5(8) . . . . ?
C6 N2 C3 C4 4.4(7) . . . . ?
C13 N2 C3 C4 -177.2(5) . . . . ?
C1 C2 C3 N2 176.2(5) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
N2 C3 C4 C4 2.8(9) . . . 2_657 ?
C2 C3 C4 C4 178.3(6) . . . 2_657 ?
N2 C3 C4 C5 178.7(5) . . . . ?
C2 C3 C4 C5 -5.9(7) . . . . ?
C4 C4 C5 C10 177.4(6) 2_657 . . 2_657 ?
C3 C4 C5 C10 1.6(8) . . . 2_657 ?
C4 C4 C5 C6 1.4(9) 2_657 . . 2_657 ?
C3 C4 C5 C6 -174.5(4) . . . 2_657 ?
C3 N2 C6 C7 168.0(5) . . . . ?
C13 N2 C6 C7 -10.5(7) . . . . ?
C3 N2 C6 C5 -10.1(7) . . . 2_657 ?
C13 N2 C6 C5 171.5(5) . . . 2_657 ?
N2 C6 C7 C8 -179.5(5) . . . . ?
C5 C6 C7 C8 -1.4(7) 2_657 . . . ?
C6 C7 C8 C9 -1.5(8) . . . . ?
C7 C8 C9 C10 -0.6(8) . . . . ?
C8 C9 C10 C5 5.6(7) . . . 2_657 ?
C8 C9 C10 C1 179.9(4) . . . 2_657 ?

_refine_diff_density_max         0.857
_refine_diff_density_min         -1.059
_refine_diff_density_rms         0.194

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DMF/ether'
####################################################################### 
# 
# 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_TCNQJW
_database_code_depnum_ccdc_archive 'CCDC 1951225'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2019-10-06 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
9(TCNQ)4
;
_chemical_name_common            ?
_chemical_melting_point          448-451
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H21 N10'
_chemical_formula_weight         605.64

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

_space_group_crystal_system      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                   7.2711(4)
_cell_length_b                   13.2126(7)
_cell_length_c                   15.6117(7)
_cell_angle_alpha                86.844(4)
_cell_angle_beta                 77.551(4)
_cell_angle_gamma                80.640(4)
_cell_volume                     1444.74(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      2.6690
_cell_measurement_theta_max      28.4650


_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             626
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            13806
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.673
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             5898
_reflns_number_gt                3626
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+0.0014P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5898
_refine_ls_number_parameters     427
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3444(2) 0.53214(14) 0.07472(12) 0.0336(5) Uani 1 1 d . . . . .
N2 N -0.1289(2) 0.20787(14) 0.19506(12) 0.0365(5) Uani 1 1 d . U . . .
C1 C -0.4596(3) 0.70495(18) 0.02643(15) 0.0356(6) Uani 1 1 d . . . . .
H1 H -0.5842 0.7011 0.0598 0.043 Uiso 1 1 calc R U . . .
C2 C -0.4213(3) 0.79224(19) -0.02011(16) 0.0395(6) Uani 1 1 d . . . . .
H2 H -0.5193 0.8499 -0.0164 0.047 Uiso 1 1 calc R U . . .
C3 C -0.2435(3) 0.79938(18) -0.07272(15) 0.0362(6) Uani 1 1 d . . . . .
H3 H -0.2205 0.8619 -0.1031 0.043 Uiso 1 1 calc R U . . .
C4 C -0.0987(3) 0.71515(17) -0.08098(14) 0.0293(5) Uani 1 1 d . . . . .
C5 C -0.1321(3) 0.62618(17) -0.02883(14) 0.0273(5) Uani 1 1 d . . . . .
C6 C 0.0163(3) 0.54254(16) -0.02633(13) 0.0252(5) Uani 1 1 d . . . . .
C7 C -0.3134(3) 0.62084(17) 0.02467(14) 0.0287(5) Uani 1 1 d . . . . .
C8 C -0.5341(3) 0.5237(2) 0.12921(19) 0.0585(8) Uani 1 1 d . . . . .
H8A H -0.5306 0.5283 0.1913 0.088 Uiso 1 1 calc R U . . .
H8B H -0.5698 0.4576 0.1192 0.088 Uiso 1 1 calc R U . . .
H8C H -0.6281 0.5796 0.1134 0.088 Uiso 1 1 calc R U . . .
C9 C -0.2038(3) 0.45032(17) 0.07746(14) 0.0281(5) Uani 1 1 d . . . . .
C10 C -0.2376(3) 0.36458(17) 0.12935(14) 0.0322(5) Uani 1 1 d . . . . .
H10 H -0.3635 0.3600 0.1607 0.039 Uiso 1 1 calc R U . . .
C11 C -0.0906(3) 0.28453(17) 0.13667(14) 0.0296(5) Uani 1 1 d . . . . .
C12 C -0.3263(3) 0.19694(19) 0.23621(17) 0.0481(7) Uani 1 1 d . U . . .
H12A H -0.3778 0.2499 0.2803 0.072 Uiso 1 1 calc R U . . .
H12B H -0.3293 0.1289 0.2644 0.072 Uiso 1 1 calc R U . . .
H12C H -0.4036 0.2047 0.1913 0.072 Uiso 1 1 calc R U . . .
C13 C 0.0096(3) 0.1496(2) 0.24125(18) 0.0563(8) Uani 1 1 d . U . . .
H13A H 0.0458 0.0799 0.2185 0.084 Uiso 1 1 calc R U . . .
H13B H -0.0470 0.1464 0.3041 0.084 Uiso 1 1 calc R U . . .
H13C H 0.1230 0.1833 0.2322 0.084 Uiso 1 1 calc R U . . .
N3 N 0.0660(3) 0.65308(15) 0.13429(13) 0.0392(5) Uani 1 1 d . . . . .
N4 N -0.5148(3) 0.71038(17) 0.26729(14) 0.0463(6) Uani 1 1 d . . . . .
N5 N 0.4001(3) 0.56189(17) 0.63152(14) 0.0503(6) Uani 1 1 d . . . . .
N6 N -0.2044(3) 0.62221(17) 0.75379(14) 0.0520(6) Uani 1 1 d . . . . .
C14 C -0.0348(3) 0.65542(16) 0.20234(15) 0.0293(5) Uani 1 1 d . . . . .
C15 C -0.1660(3) 0.66291(16) 0.28416(14) 0.0282(5) Uani 1 1 d . . . . .
C16 C -0.3603(3) 0.68827(17) 0.27706(15) 0.0324(5) Uani 1 1 d . . . . .
C17 C -0.1107(3) 0.64758(16) 0.36519(14) 0.0281(5) Uani 1 1 d . . . . .
C18 C 0.0853(3) 0.62435(16) 0.37046(14) 0.0281(5) Uani 1 1 d . . . . .
H18 H 0.1803 0.6179 0.3179 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1388(3) 0.61130(16) 0.44851(14) 0.0307(5) Uani 1 1 d . . . . .
H19 H 0.2706 0.5959 0.4496 0.037 Uiso 1 1 calc R U . . .
C20 C 0.0020(3) 0.62014(16) 0.52929(15) 0.0301(5) Uani 1 1 d . . . . .
C21 C -0.1946(3) 0.64338(17) 0.52372(15) 0.0319(5) Uani 1 1 d . . . . .
H21 H -0.2898 0.6498 0.5762 0.038 Uiso 1 1 calc R U . . .
C22 C -0.2478(3) 0.65642(17) 0.44553(14) 0.0311(5) Uani 1 1 d . . . . .
H22 H -0.3795 0.6718 0.4443 0.037 Uiso 1 1 calc R U . . .
C23 C 0.0536(3) 0.60534(17) 0.61093(15) 0.0322(5) Uani 1 1 d . . . . .
C24 C 0.2466(3) 0.58162(18) 0.62113(15) 0.0373(6) Uani 1 1 d . . . . .
C25 C -0.0880(3) 0.61417(18) 0.69029(16) 0.0376(6) Uani 1 1 d . . . . .
N7 N 0.1049(3) 0.88302(17) 0.01391(14) 0.0482(6) Uani 1 1 d . . . . .
N8 N -0.5113(3) 0.97486(17) 0.12832(14) 0.0476(6) Uani 1 1 d . . . . .
N9 N 0.3094(3) 0.83510(16) 0.52052(14) 0.0437(5) Uani 1 1 d . . . . .
N10 N -0.3003(3) 0.91383(17) 0.62772(14) 0.0493(6) Uani 1 1 d . . . . .
C26 C -0.0179(3) 0.89638(18) 0.07460(16) 0.0367(6) Uani 1 1 d . . . . .
C27 C -0.1691(3) 0.91359(17) 0.15044(15) 0.0334(6) Uani 1 1 d . . . . .
C28 C -0.3587(3) 0.94741(18) 0.13626(15) 0.0375(6) Uani 1 1 d . . . . .
C29 C -0.1361(3) 0.90049(16) 0.23485(15) 0.0291(5) Uani 1 1 d . . . . .
C30 C 0.0537(3) 0.87246(16) 0.25032(15) 0.0309(5) Uani 1 1 d . . . . .
H30 H 0.1577 0.8593 0.2017 0.037 Uiso 1 1 calc R U . . .
C31 C 0.0874(3) 0.86444(16) 0.33171(14) 0.0290(5) Uani 1 1 d . . . . .
H31 H 0.2146 0.8463 0.3396 0.035 Uiso 1 1 calc R U . . .
C32 C -0.0653(3) 0.88278(16) 0.40692(15) 0.0280(5) Uani 1 1 d . . . . .
C33 C -0.2561(3) 0.90904(16) 0.39239(15) 0.0310(5) Uani 1 1 d . . . . .
H33 H -0.3604 0.9205 0.4411 0.037 Uiso 1 1 calc R U . . .
C34 C -0.2881(3) 0.91751(16) 0.31032(15) 0.0308(5) Uani 1 1 d . . . . .
H34 H -0.4153 0.9353 0.3023 0.037 Uiso 1 1 calc R U . . .
C35 C -0.0304(3) 0.87609(16) 0.49113(15) 0.0296(5) Uani 1 1 d . . . . .
C36 C 0.1588(3) 0.85227(17) 0.50711(15) 0.0326(5) Uani 1 1 d . . . . .
C37 C -0.1807(3) 0.89642(18) 0.56684(16) 0.0345(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.367(3) . ?
N1 C7 1.394(3) . ?
N1 C8 1.474(3) . ?
N2 C11 1.347(3) . ?
N2 C13 1.458(3) . ?
N2 C12 1.468(3) . ?
C1 C2 1.364(3) . ?
C1 C7 1.405(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(3) . ?
C4 C11 1.462(3) 2_565 ?
C5 C7 1.410(3) . ?
C5 C6 1.419(3) . ?
C6 C6 1.377(4) 2_565 ?
C6 C9 1.439(3) 2_565 ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.380(3) . ?
C9 C6 1.439(3) 2_565 ?
C10 C11 1.395(3) . ?
C10 H10 0.9500 . ?
C11 C4 1.462(3) 2_565 ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N3 C14 1.152(3) . ?
N4 C16 1.154(2) . ?
N5 C24 1.148(3) . ?
N6 C25 1.154(3) . ?
C14 C15 1.418(3) . ?
C15 C17 1.403(3) . ?
C15 C16 1.425(3) . ?
C17 C22 1.421(3) . ?
C17 C18 1.427(3) . ?
C18 C19 1.351(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.425(3) . ?
C19 H19 0.9500 . ?
C20 C23 1.400(3) . ?
C20 C21 1.433(3) . ?
C21 C22 1.352(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C25 1.427(3) . ?
C23 C24 1.428(3) . ?
N7 C26 1.153(3) . ?
N8 C28 1.141(3) . ?
N9 C36 1.143(3) . ?
N10 C37 1.147(3) . ?
C26 C27 1.432(3) . ?
C27 C29 1.386(3) . ?
C27 C28 1.439(3) . ?
C29 C34 1.431(3) . ?
C29 C30 1.437(3) . ?
C30 C31 1.341(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.432(3) . ?
C31 H31 0.9500 . ?
C32 C35 1.387(3) . ?
C32 C33 1.438(3) . ?
C33 C34 1.347(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C37 1.431(3) . ?
C35 C36 1.433(3) . ?

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
C9 N1 C7 122.89(17) . . ?
C9 N1 C8 116.69(19) . . ?
C7 N1 C8 120.41(17) . . ?
C11 N2 C13 124.13(19) . . ?
C11 N2 C12 120.74(18) . . ?
C13 N2 C12 112.85(19) . . ?
C2 C1 C7 119.4(2) . . ?
C2 C1 H1 120.3 . . ?
C7 C1 H1 120.3 . . ?
C1 C2 C3 122.0(2) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.5(2) . . ?
C3 C4 C11 123.6(2) . 2_565 ?
C5 C4 C11 117.84(18) . 2_565 ?
C7 C5 C4 120.23(18) . . ?
C7 C5 C6 118.51(19) . . ?
C4 C5 C6 121.22(18) . . ?
C6 C6 C5 120.8(2) 2_565 . ?
C6 C6 C9 120.4(2) 2_565 2_565 ?
C5 C6 C9 118.76(18) . 2_565 ?
N1 C7 C1 121.16(19) . . ?
N1 C7 C5 119.46(18) . . ?
C1 C7 C5 119.4(2) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 121.60(19) . . ?
N1 C9 C6 117.82(19) . 2_565 ?
C10 C9 C6 120.55(18) . 2_565 ?
C9 C10 C11 121.30(19) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
N2 C11 C10 118.39(19) . . ?
N2 C11 C4 121.72(19) . 2_565 ?
C10 C11 C4 119.9(2) . 2_565 ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 176.7(2) . . ?
C17 C15 C14 123.35(17) . . ?
C17 C15 C16 122.64(19) . . ?
C14 C15 C16 114.01(19) . . ?
N4 C16 C15 176.8(3) . . ?
C15 C17 C22 121.23(18) . . ?
C15 C17 C18 121.49(19) . . ?
C22 C17 C18 117.3(2) . . ?
C19 C18 C17 121.5(2) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 121.45(19) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C23 C20 C19 122.54(19) . . ?
C23 C20 C21 120.6(2) . . ?
C19 C20 C21 116.9(2) . . ?
C22 C21 C20 121.6(2) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C17 121.30(19) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C20 C23 C25 120.8(2) . . ?
C20 C23 C24 123.5(2) . . ?
C25 C23 C24 115.8(2) . . ?
N5 C24 C23 178.3(3) . . ?
N6 C25 C23 179.0(3) . . ?
N7 C26 C27 179.3(3) . . ?
C29 C27 C26 121.97(19) . . ?
C29 C27 C28 120.5(2) . . ?
C26 C27 C28 117.5(2) . . ?
N8 C28 C27 177.4(3) . . ?
C27 C29 C34 121.61(18) . . ?
C27 C29 C30 121.3(2) . . ?
C34 C29 C30 117.0(2) . . ?
C31 C30 C29 121.6(2) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C32 121.08(19) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C35 C32 C31 121.15(18) . . ?
C35 C32 C33 121.0(2) . . ?
C31 C32 C33 117.9(2) . . ?
C34 C33 C32 120.5(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C33 C34 C29 121.89(19) . . ?
C33 C34 H34 119.1 . . ?
C29 C34 H34 119.1 . . ?
C32 C35 C37 121.86(19) . . ?
C32 C35 C36 121.96(19) . . ?
C37 C35 C36 116.1(2) . . ?
N9 C36 C35 178.7(3) . . ?
N10 C37 C35 179.1(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 C1 C2 C3 2.9(4) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 -5.5(3) . . . . ?
C2 C3 C4 C11 178.4(2) . . . 2_565 ?
C3 C4 C5 C7 5.1(3) . . . . ?
C11 C4 C5 C7 -178.61(19) 2_565 . . . ?
C3 C4 C5 C6 -172.4(2) . . . . ?
C11 C4 C5 C6 3.9(3) 2_565 . . . ?
C7 C5 C6 C6 0.8(4) . . . 2_565 ?
C4 C5 C6 C6 178.3(2) . . . 2_565 ?
C7 C5 C6 C9 -176.99(19) . . . 2_565 ?
C4 C5 C6 C9 0.5(3) . . . 2_565 ?
C9 N1 C7 C1 -177.3(2) . . . . ?
C8 N1 C7 C1 1.6(3) . . . . ?
C9 N1 C7 C5 2.8(3) . . . . ?
C8 N1 C7 C5 -178.3(2) . . . . ?
C2 C1 C7 N1 176.8(2) . . . . ?
C2 C1 C7 C5 -3.3(3) . . . . ?
C4 C5 C7 N1 179.2(2) . . . . ?
C6 C5 C7 N1 -3.3(3) . . . . ?
C4 C5 C7 C1 -0.7(3) . . . . ?
C6 C5 C7 C1 176.9(2) . . . . ?
C7 N1 C9 C10 178.3(2) . . . . ?
C8 N1 C9 C10 -0.6(3) . . . . ?
C7 N1 C9 C6 0.2(3) . . . 2_565 ?
C8 N1 C9 C6 -178.7(2) . . . 2_565 ?
N1 C9 C10 C11 -175.4(2) . . . . ?
C6 C9 C10 C11 2.7(3) 2_565 . . . ?
C13 N2 C11 C10 -148.8(2) . . . . ?
C12 N2 C11 C10 12.8(3) . . . . ?
C13 N2 C11 C4 31.8(3) . . . 2_565 ?
C12 N2 C11 C4 -166.6(2) . . . 2_565 ?
C9 C10 C11 N2 173.4(2) . . . . ?
C9 C10 C11 C4 -7.3(3) . . . 2_565 ?
C14 C15 C17 C22 179.7(2) . . . . ?
C16 C15 C17 C22 0.2(3) . . . . ?
C14 C15 C17 C18 0.9(3) . . . . ?
C16 C15 C17 C18 -178.7(2) . . . . ?
C15 C17 C18 C19 178.9(2) . . . . ?
C22 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C23 178.9(2) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C23 C20 C21 C22 -179.0(2) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C17 0.0(3) . . . . ?
C15 C17 C22 C21 -178.9(2) . . . . ?
C18 C17 C22 C21 0.0(3) . . . . ?
C19 C20 C23 C25 -179.5(2) . . . . ?
C21 C20 C23 C25 -0.7(3) . . . . ?
C19 C20 C23 C24 0.9(4) . . . . ?
C21 C20 C23 C24 179.7(2) . . . . ?
C26 C27 C29 C34 -179.8(2) . . . . ?
C28 C27 C29 C34 1.5(3) . . . . ?
C26 C27 C29 C30 2.3(3) . . . . ?
C28 C27 C29 C30 -176.4(2) . . . . ?
C27 C29 C30 C31 176.8(2) . . . . ?
C34 C29 C30 C31 -1.2(3) . . . . ?
C29 C30 C31 C32 0.5(3) . . . . ?
C30 C31 C32 C35 -179.0(2) . . . . ?
C30 C31 C32 C33 0.6(3) . . . . ?
C35 C32 C33 C34 178.6(2) . . . . ?
C31 C32 C33 C34 -1.1(3) . . . . ?
C32 C33 C34 C29 0.3(3) . . . . ?
C27 C29 C34 C33 -177.2(2) . . . . ?
C30 C29 C34 C33 0.8(3) . . . . ?
C31 C32 C35 C37 178.6(2) . . . . ?
C33 C32 C35 C37 -1.0(3) . . . . ?
C31 C32 C35 C36 1.0(3) . . . . ?
C33 C32 C35 C36 -178.6(2) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'evaporation of reaction mixture'
####################################################################### 
# 
# 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_4FJW
_database_code_depnum_ccdc_archive 'CCDC 1951226'
loop_
_audit_author_name
_audit_author_address
'PROFESSOR J WALLIS'
;Nottingham Trent University, UK
United Kingdom
;
_audit_update_record             
;
2019-10-06 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
10.TCNQ-F4
;
_chemical_name_common            ?
_chemical_melting_point          '> 603 K'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H29 F4 N8'
_chemical_formula_weight         685.70

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   11.4701(4)
_cell_length_b                   11.7251(4)
_cell_length_c                   13.1590(4)
_cell_angle_alpha                74.899(3)
_cell_angle_beta                 67.021(3)
_cell_angle_gamma                86.962(2)
_cell_volume                     1570.67(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7586
_cell_measurement_theta_min      2.5590
_cell_measurement_theta_max      30.6260

_exptl_crystal_description       parallelopipeds
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             710
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.246
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.994

_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Sapphire3
_diffrn_detector_area_resol_mean 15.9832
_diffrn_reflns_number            39739
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7821
_reflns_number_gt                5110
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+0.1110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7821
_refine_ls_number_parameters     467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
F1 F 0.97252(9) 0.50307(8) 0.29969(8) 0.0263(2) Uani 1 1 d . . . . .
F2 F 0.76744(9) 0.48942(8) 0.48258(8) 0.0277(2) Uani 1 1 d . . . . .
F3 F 0.96284(10) 0.75526(8) 0.59301(8) 0.0262(2) Uani 1 1 d . . . . .
F4 F 1.16513(9) 0.77363(8) 0.40780(8) 0.0278(2) Uani 1 1 d . . . . .
N3 N 0.80393(13) 0.69031(12) 0.10500(11) 0.0199(3) Uani 1 1 d . . . . .
N4 N 0.52630(14) 0.76267(12) 0.47575(12) 0.0246(3) Uani 1 1 d . . . . .
N1 N 1.07918(14) 0.95271(12) 0.19383(12) 0.0243(3) Uani 1 1 d . . . . .
N7 N 0.53132(15) 0.49711(14) 0.70410(13) 0.0325(4) Uani 1 1 d . . . . .
N2 N 1.36435(15) 0.88053(13) -0.16927(13) 0.0312(4) Uani 1 1 d . . . . .
N8 N 0.71771(15) 0.71698(14) 0.80511(14) 0.0336(4) Uani 1 1 d . . . . .
N5 N 1.20589(16) 0.56257(14) 0.07479(13) 0.0353(4) Uani 1 1 d . . . . .
N6 N 1.39183(16) 0.77959(14) 0.18362(14) 0.0369(4) Uani 1 1 d . . . . .
C33 C 0.86433(16) 0.56159(14) 0.46579(14) 0.0203(4) Uani 1 1 d . . . . .
C35 C 0.96177(17) 0.69295(14) 0.52060(14) 0.0201(4) Uani 1 1 d . . . . .
C36 C 1.06748(16) 0.70224(13) 0.42436(14) 0.0204(4) Uani 1 1 d . . . . .
C5 C 0.86180(16) 0.86670(13) 0.28810(14) 0.0200(4) Uani 1 1 d . . . . .
C8 C 0.88305(16) 0.81557(13) 0.19523(14) 0.0192(3) Uani 1 1 d . . . . .
C23 C 0.78750(16) 0.74512(14) 0.20130(14) 0.0201(4) Uani 1 1 d . . . . .
C34 C 0.85110(16) 0.62193(13) 0.54937(14) 0.0191(3) Uani 1 1 d . . . . .
C9 C 1.00376(16) 0.84000(14) 0.10098(14) 0.0200(4) Uani 1 1 d . . . . .
C32 C 0.97108(16) 0.57000(14) 0.36985(14) 0.0198(4) Uani 1 1 d . . . . .
C31 C 1.08064(16) 0.64167(13) 0.34033(14) 0.0198(4) Uani 1 1 d . . . . .
C37 C 0.74184(16) 0.61070(14) 0.65077(14) 0.0215(4) Uani 1 1 d . . . . .
C20 C 1.02323(16) 0.79523(14) 0.00579(14) 0.0205(4) Uani 1 1 d . . . . .
C24 C 0.66952(16) 0.72412(14) 0.29440(14) 0.0224(4) Uani 1 1 d . . . . .
H24 H 0.6061 0.6736 0.2966 0.027 Uiso 1 1 calc R U . . .
C19 C 0.92672(16) 0.72840(14) 0.00215(14) 0.0210(4) Uani 1 1 d . . . . .
C38 C 0.62749(17) 0.54643(15) 0.67665(14) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.74368(16) 0.84744(14) 0.38242(14) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.96205(17) 0.93567(14) 0.28607(14) 0.0214(4) Uani 1 1 d . . . . .
C29 C 1.19012(16) 0.65073(14) 0.23950(14) 0.0221(4) Uani 1 1 d . . . . .
C25 C 0.64543(17) 0.77626(14) 0.38227(14) 0.0218(4) Uani 1 1 d . . . . .
C39 C 0.73207(16) 0.67121(15) 0.73444(15) 0.0241(4) Uani 1 1 d . . . . .
C3 C 0.72731(18) 0.89506(15) 0.47500(15) 0.0255(4) Uani 1 1 d . . . . .
H3 H 0.6494 0.8809 0.5400 0.031 Uiso 1 1 calc R U . . .
C15 C 1.14035(16) 0.81790(14) -0.08999(14) 0.0226(4) Uani 1 1 d . . . . .
C10 C 1.10028(17) 0.90664(14) 0.10116(14) 0.0228(4) Uani 1 1 d . . . . .
C30 C 1.30099(18) 0.72243(15) 0.21108(15) 0.0263(4) Uani 1 1 d . . . . .
C11 C 1.22087(17) 0.92042(15) 0.00951(15) 0.0265(4) Uani 1 1 d . . . . .
H11 H 1.2880 0.9627 0.0115 0.032 Uiso 1 1 calc R U . . .
C12 C 1.24343(17) 0.87448(15) -0.08181(15) 0.0245(4) Uani 1 1 d . . . . .
C28 C 1.19623(17) 0.59980(15) 0.15018(15) 0.0248(4) Uani 1 1 d . . . . .
C16 C 1.15196(17) 0.78496(15) -0.18873(15) 0.0265(4) Uani 1 1 d . . . . .
H16 H 1.2277 0.8066 -0.2556 0.032 Uiso 1 1 calc R U . . .
C1 C 0.94017(18) 0.98325(15) 0.37785(16) 0.0277(4) Uani 1 1 d . . . . .
H1 H 1.0050 1.0309 0.3772 0.033 Uiso 1 1 calc R U . . .
C21 C 0.69334(17) 0.72218(17) 0.06927(15) 0.0273(4) Uani 1 1 d . . . . .
H21A H 0.6143 0.6873 0.1331 0.041 Uiso 1 1 calc R U . . .
H21B H 0.7048 0.6915 0.0037 0.041 Uiso 1 1 calc R U . . .
H21C H 0.6894 0.8084 0.0480 0.041 Uiso 1 1 calc R U . . .
C22 C 0.80044(18) 0.55673(14) 0.14861(15) 0.0271(4) Uani 1 1 d . . . . .
H22A H 0.8746 0.5343 0.1674 0.041 Uiso 1 1 calc R U . . .
H22B H 0.8016 0.5200 0.0894 0.041 Uiso 1 1 calc R U . . .
H22C H 0.7229 0.5297 0.2172 0.041 Uiso 1 1 calc R U . . .
C17 C 1.05559(18) 0.72223(16) -0.18962(15) 0.0276(4) Uani 1 1 d . . . . .
H17 H 1.0650 0.7003 -0.2569 0.033 Uiso 1 1 calc R U . . .
C2 C 0.82416(18) 0.96160(15) 0.47048(16) 0.0285(4) Uani 1 1 d . . . . .
H2 H 0.8118 0.9942 0.5327 0.034 Uiso 1 1 calc R U . . .
C18 C 0.94357(17) 0.69012(15) -0.09263(15) 0.0250(4) Uani 1 1 d . . . . .
H18 H 0.8791 0.6420 -0.0920 0.030 Uiso 1 1 calc R U . . .
C26 C 0.44522(19) 0.66078(16) 0.49640(16) 0.0328(4) Uani 1 1 d . . . . .
H26A H 0.4165 0.6716 0.4336 0.049 Uiso 1 1 calc R U . . .
H26B H 0.3715 0.6530 0.5685 0.049 Uiso 1 1 calc R U . . .
H26C H 0.4930 0.5891 0.5009 0.049 Uiso 1 1 calc R U . . .
C7 C 1.17879(19) 1.02195(16) 0.19847(16) 0.0331(5) Uani 1 1 d . . . . .
H7A H 1.1504 1.1014 0.2031 0.050 Uiso 1 1 calc R U . . .
H7B H 1.2560 1.0278 0.1294 0.050 Uiso 1 1 calc R U . . .
H7C H 1.1966 0.9829 0.2660 0.050 Uiso 1 1 calc R U . . .
C14 C 1.41664(19) 0.76528(18) -0.18167(18) 0.0397(5) Uani 1 1 d . . . . .
H14A H 1.4584 0.7367 -0.1282 0.060 Uiso 1 1 calc R U . . .
H14B H 1.4785 0.7740 -0.2601 0.060 Uiso 1 1 calc R U . . .
H14C H 1.3478 0.7084 -0.1650 0.060 Uiso 1 1 calc R U . . .
C27 C 0.45429(19) 0.86939(16) 0.47169(17) 0.0353(5) Uani 1 1 d . . . . .
H27A H 0.5127 0.9395 0.4405 0.053 Uiso 1 1 calc R U . . .
H27B H 0.3943 0.8688 0.5491 0.053 Uiso 1 1 calc R U . . .
H27C H 0.4077 0.8714 0.4228 0.053 Uiso 1 1 calc R U . . .
C13 C 1.4599(2) 0.9600(2) -0.17253(18) 0.0457(6) Uani 1 1 d . . . . .
H13A H 1.4277 1.0394 -0.1748 0.069 Uiso 1 1 calc R U . . .
H13B H 1.5373 0.9634 -0.2409 0.069 Uiso 1 1 calc R U . . .
H13C H 1.4790 0.9308 -0.1041 0.069 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
F1 C32 1.3538(17) . ?
F2 C33 1.3456(18) . ?
F3 C35 1.3472(17) . ?
F4 C36 1.3477(18) . ?
N3 C19 1.509(2) . ?
N3 C23 1.5098(19) . ?
N3 C21 1.514(2) . ?
N3 C22 1.518(2) . ?
N4 C25 1.419(2) . ?
N4 C26 1.455(2) . ?
N4 C27 1.463(2) . ?
N1 C10 1.392(2) . ?
N1 C6 1.395(2) . ?
N1 C7 1.465(2) . ?
N7 C38 1.153(2) . ?
N2 C12 1.405(2) . ?
N2 C13 1.457(2) . ?
N2 C14 1.471(2) . ?
N8 C39 1.145(2) . ?
N5 C28 1.150(2) . ?
N6 C30 1.149(2) . ?
C33 C32 1.358(2) . ?
C33 C34 1.413(2) . ?
C35 C36 1.352(2) . ?
C35 C34 1.421(2) . ?
C36 C31 1.420(2) . ?
C5 C4 1.414(2) . ?
C5 C6 1.428(2) . ?
C5 C8 1.430(2) . ?
C8 C23 1.372(2) . ?
C8 C9 1.433(2) . ?
C23 C24 1.406(2) . ?
C34 C37 1.410(2) . ?
C9 C10 1.390(2) . ?
C9 C20 1.416(2) . ?
C32 C31 1.413(2) . ?
C31 C29 1.410(2) . ?
C37 C38 1.424(2) . ?
C37 C39 1.425(2) . ?
C20 C19 1.412(2) . ?
C20 C15 1.416(2) . ?
C24 C25 1.374(2) . ?
C19 C18 1.374(2) . ?
C4 C3 1.413(2) . ?
C4 C25 1.438(2) . ?
C6 C1 1.390(2) . ?
C29 C28 1.428(2) . ?
C29 C30 1.429(2) . ?
C3 C2 1.365(2) . ?
C15 C16 1.406(2) . ?
C15 C12 1.438(2) . ?
C10 C11 1.419(2) . ?
C11 C12 1.371(2) . ?
C16 C17 1.365(2) . ?
C1 C2 1.389(3) . ?
C17 C18 1.394(2) . ?

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
C19 N3 C23 114.16(12) . . ?
C19 N3 C21 109.43(12) . . ?
C23 N3 C21 108.14(12) . . ?
C19 N3 C22 107.65(12) . . ?
C23 N3 C22 108.85(12) . . ?
C21 N3 C22 108.49(13) . . ?
C25 N4 C26 115.96(13) . . ?
C25 N4 C27 113.11(14) . . ?
C26 N4 C27 109.58(15) . . ?
C10 N1 C6 121.50(14) . . ?
C10 N1 C7 121.44(15) . . ?
C6 N1 C7 117.06(14) . . ?
C12 N2 C13 116.47(15) . . ?
C12 N2 C14 114.91(15) . . ?
C13 N2 C14 110.44(16) . . ?
F2 C33 C32 117.60(14) . . ?
F2 C33 C34 118.72(15) . . ?
C32 C33 C34 123.65(15) . . ?
F3 C35 C36 117.25(15) . . ?
F3 C35 C34 118.64(14) . . ?
C36 C35 C34 124.11(14) . . ?
F4 C36 C35 117.67(14) . . ?
F4 C36 C31 118.62(15) . . ?
C35 C36 C31 123.71(15) . . ?
C4 C5 C6 120.03(14) . . ?
C4 C5 C8 120.57(15) . . ?
C6 C5 C8 119.39(15) . . ?
C23 C8 C5 118.47(15) . . ?
C23 C8 C9 123.45(14) . . ?
C5 C8 C9 118.08(15) . . ?
C8 C23 C24 122.02(14) . . ?
C8 C23 N3 120.76(15) . . ?
C24 C23 N3 117.19(14) . . ?
C37 C34 C33 123.84(15) . . ?
C37 C34 C35 124.00(14) . . ?
C33 C34 C35 112.14(15) . . ?
C10 C9 C20 119.99(16) . . ?
C10 C9 C8 121.52(15) . . ?
C20 C9 C8 118.49(15) . . ?
F1 C32 C33 117.28(15) . . ?
F1 C32 C31 118.40(14) . . ?
C33 C32 C31 124.31(14) . . ?
C29 C31 C32 123.61(14) . . ?
C29 C31 C36 124.33(15) . . ?
C32 C31 C36 112.06(15) . . ?
C34 C37 C38 124.36(14) . . ?
C34 C37 C39 122.57(15) . . ?
C38 C37 C39 112.90(15) . . ?
C19 C20 C15 117.80(15) . . ?
C19 C20 C9 121.49(16) . . ?
C15 C20 C9 120.70(15) . . ?
C25 C24 C23 120.40(16) . . ?
C18 C19 C20 121.41(16) . . ?
C18 C19 N3 117.44(15) . . ?
C20 C19 N3 121.05(14) . . ?
N7 C38 C37 175.40(18) . . ?
C3 C4 C5 119.24(16) . . ?
C3 C4 C25 122.20(16) . . ?
C5 C4 C25 118.53(14) . . ?
C1 C6 N1 121.58(16) . . ?
C1 C6 C5 118.55(16) . . ?
N1 C6 C5 119.87(14) . . ?
C31 C29 C28 123.31(15) . . ?
C31 C29 C30 123.17(15) . . ?
C28 C29 C30 113.18(15) . . ?
C24 C25 N4 122.89(15) . . ?
C24 C25 C4 119.91(16) . . ?
N4 C25 C4 117.19(14) . . ?
N8 C39 C37 176.26(19) . . ?
C2 C3 C4 119.56(17) . . ?
C16 C15 C20 119.43(16) . . ?
C16 C15 C12 122.54(16) . . ?
C20 C15 C12 118.02(15) . . ?
C9 C10 N1 119.56(16) . . ?
C9 C10 C11 119.01(15) . . ?
N1 C10 C11 121.33(15) . . ?
N6 C30 C29 177.12(19) . . ?
C12 C11 C10 121.98(16) . . ?
C11 C12 N2 122.56(16) . . ?
C11 C12 C15 119.52(16) . . ?
N2 C12 C15 117.92(15) . . ?
N5 C28 C29 176.75(19) . . ?
C17 C16 C15 120.70(17) . . ?
C2 C1 C6 120.46(17) . . ?
C16 C17 C18 120.52(16) . . ?
C3 C2 C1 122.12(16) . . ?
C19 C18 C17 119.72(16) . . ?

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
F3 C35 C36 F4 -0.5(2) . . . . ?
C34 C35 C36 F4 179.56(14) . . . . ?
F3 C35 C36 C31 179.76(14) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C4 C5 C8 C23 -1.7(2) . . . . ?
C6 C5 C8 C23 177.03(14) . . . . ?
C4 C5 C8 C9 178.83(14) . . . . ?
C6 C5 C8 C9 -2.5(2) . . . . ?
C5 C8 C23 C24 1.3(2) . . . . ?
C9 C8 C23 C24 -179.19(15) . . . . ?
C5 C8 C23 N3 179.09(13) . . . . ?
C9 C8 C23 N3 -1.4(2) . . . . ?
C19 N3 C23 C8 -4.8(2) . . . . ?
C21 N3 C23 C8 -126.84(16) . . . . ?
C22 N3 C23 C8 115.49(16) . . . . ?
C19 N3 C23 C24 173.06(14) . . . . ?
C21 N3 C23 C24 51.02(18) . . . . ?
C22 N3 C23 C24 -66.66(18) . . . . ?
F2 C33 C34 C37 0.4(2) . . . . ?
C32 C33 C34 C37 -178.02(16) . . . . ?
F2 C33 C34 C35 178.99(13) . . . . ?
C32 C33 C34 C35 0.6(2) . . . . ?
F3 C35 C34 C37 -1.1(2) . . . . ?
C36 C35 C34 C37 178.80(16) . . . . ?
F3 C35 C34 C33 -179.71(13) . . . . ?
C36 C35 C34 C33 0.2(2) . . . . ?
C23 C8 C9 C10 -176.47(15) . . . . ?
C5 C8 C9 C10 3.0(2) . . . . ?
C23 C8 C9 C20 4.0(2) . . . . ?
C5 C8 C9 C20 -176.53(14) . . . . ?
F2 C33 C32 F1 -1.3(2) . . . . ?
C34 C33 C32 F1 177.10(14) . . . . ?
F2 C33 C32 C31 -179.90(14) . . . . ?
C34 C33 C32 C31 -1.5(3) . . . . ?
F1 C32 C31 C29 2.4(2) . . . . ?
C33 C32 C31 C29 -179.05(16) . . . . ?
F1 C32 C31 C36 -177.17(13) . . . . ?
C33 C32 C31 C36 1.4(2) . . . . ?
F4 C36 C31 C29 0.1(2) . . . . ?
C35 C36 C31 C29 179.84(15) . . . . ?
F4 C36 C31 C32 179.69(13) . . . . ?
C35 C36 C31 C32 -0.6(2) . . . . ?
C33 C34 C37 C38 -6.1(3) . . . . ?
C35 C34 C37 C38 175.44(15) . . . . ?
C33 C34 C37 C39 178.93(15) . . . . ?
C35 C34 C37 C39 0.5(3) . . . . ?
C10 C9 C20 C19 -179.22(15) . . . . ?
C8 C9 C20 C19 0.3(2) . . . . ?
C10 C9 C20 C15 -0.2(2) . . . . ?
C8 C9 C20 C15 179.35(14) . . . . ?
C8 C23 C24 C25 1.3(2) . . . . ?
N3 C23 C24 C25 -176.55(14) . . . . ?
C15 C20 C19 C18 -2.4(2) . . . . ?
C9 C20 C19 C18 176.67(15) . . . . ?
C15 C20 C19 N3 174.00(13) . . . . ?
C9 C20 C19 N3 -6.9(2) . . . . ?
C23 N3 C19 C18 -174.58(14) . . . . ?
C21 N3 C19 C18 -53.24(18) . . . . ?
C22 N3 C19 C18 64.47(17) . . . . ?
C23 N3 C19 C20 8.9(2) . . . . ?
C21 N3 C19 C20 130.22(15) . . . . ?
C22 N3 C19 C20 -112.07(16) . . . . ?
C6 C5 C4 C3 -1.3(2) . . . . ?
C8 C5 C4 C3 177.41(14) . . . . ?
C6 C5 C4 C25 -179.20(14) . . . . ?
C8 C5 C4 C25 -0.5(2) . . . . ?
C10 N1 C6 C1 -178.93(15) . . . . ?
C7 N1 C6 C1 0.7(2) . . . . ?
C10 N1 C6 C5 1.8(2) . . . . ?
C7 N1 C6 C5 -178.57(15) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C8 C5 C6 C1 -179.11(14) . . . . ?
C4 C5 C6 N1 178.85(14) . . . . ?
C8 C5 C6 N1 0.1(2) . . . . ?
C32 C31 C29 C28 7.8(2) . . . . ?
C36 C31 C29 C28 -172.68(15) . . . . ?
C32 C31 C29 C30 -179.26(15) . . . . ?
C36 C31 C29 C30 0.2(3) . . . . ?
C23 C24 C25 N4 177.03(15) . . . . ?
C23 C24 C25 C4 -3.5(2) . . . . ?
C26 N4 C25 C24 20.6(2) . . . . ?
C27 N4 C25 C24 -107.20(18) . . . . ?
C26 N4 C25 C4 -158.86(15) . . . . ?
C27 N4 C25 C4 73.33(19) . . . . ?
C3 C4 C25 C24 -174.75(15) . . . . ?
C5 C4 C25 C24 3.1(2) . . . . ?
C3 C4 C25 N4 4.7(2) . . . . ?
C5 C4 C25 N4 -177.41(14) . . . . ?
C5 C4 C3 C2 1.9(2) . . . . ?
C25 C4 C3 C2 179.75(15) . . . . ?
C19 C20 C15 C16 6.8(2) . . . . ?
C9 C20 C15 C16 -172.28(14) . . . . ?
C19 C20 C15 C12 -173.28(14) . . . . ?
C9 C20 C15 C12 7.6(2) . . . . ?
C20 C9 C10 N1 178.41(14) . . . . ?
C8 C9 C10 N1 -1.1(2) . . . . ?
C20 C9 C10 C11 -5.2(2) . . . . ?
C8 C9 C10 C11 175.25(14) . . . . ?
C6 N1 C10 C9 -1.4(2) . . . . ?
C7 N1 C10 C9 179.06(15) . . . . ?
C6 N1 C10 C11 -177.64(15) . . . . ?
C7 N1 C10 C11 2.8(2) . . . . ?
C9 C10 C11 C12 3.0(2) . . . . ?
N1 C10 C11 C12 179.32(15) . . . . ?
C10 C11 C12 N2 -175.60(16) . . . . ?
C10 C11 C12 C15 4.6(2) . . . . ?
C13 N2 C12 C11 -13.0(2) . . . . ?
C14 N2 C12 C11 118.42(19) . . . . ?
C13 N2 C12 C15 166.82(16) . . . . ?
C14 N2 C12 C15 -61.8(2) . . . . ?
C16 C15 C12 C11 170.14(15) . . . . ?
C20 C15 C12 C11 -9.8(2) . . . . ?
C16 C15 C12 N2 -9.7(2) . . . . ?
C20 C15 C12 N2 170.41(14) . . . . ?
C20 C15 C16 C17 -5.9(2) . . . . ?
C12 C15 C16 C17 174.22(16) . . . . ?
N1 C6 C1 C2 -177.76(15) . . . . ?
C5 C6 C1 C2 1.5(2) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C20 C19 C18 C17 -3.1(2) . . . . ?
N3 C19 C18 C17 -179.62(14) . . . . ?
C16 C17 C18 C19 4.2(3) . . . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 'evaporation of reaction mixture'
