# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_2TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503299'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N5'
_chemical_formula_weight         348.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.5189(7)
_cell_length_b                   8.8078(7)
_cell_length_c                   13.1350(10)
_cell_angle_alpha                87.752(6)
_cell_angle_beta                 89.740(7)
_cell_angle_gamma                80.065(7)
_cell_volume                     856.16(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2368
_cell_measurement_theta_min      3.3645
_cell_measurement_theta_max      73.5031

_exptl_crystal_description       Plate
_exptl_crystal_colour            Purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             362
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3244
_exptl_crystal_size_mid          0.1772
_exptl_crystal_size_min          0.0219
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_diffrn_ambient_temperature      130.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            5644
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.367
_diffrn_reflns_theta_max         69.990
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3211
_reflns_number_gt                2688
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0972P)²+0.6175P] 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         3211
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1793
_refine_ls_wR_factor_gt          0.1713
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C22 C 0.2265(3) 0.7090(3) 0.86619(19) 0.0384(6) Uani 1 1 d . . . . .
H22A H 0.1989 0.7908 0.8130 0.058 Uiso 1 1 calc R U . . .
H22B H 0.3573 0.6857 0.8775 0.058 Uiso 1 1 calc R U . . .
H22C H 0.1659 0.7434 0.9295 0.058 Uiso 1 1 calc R U . . .
C1 C 0.1413(3) 0.0111(2) 0.36603(15) 0.0243(4) Uani 1 1 d . . . . .
C2 C 0.1859(3) -0.2020(2) 0.48871(14) 0.0247(4) Uani 1 1 d . . . . .
C3 C 0.2140(3) -0.0494(2) 0.46152(15) 0.0227(4) Uani 1 1 d . . . . .
C4 C 0.2978(2) 0.0385(2) 0.52839(14) 0.0210(4) Uani 1 1 d . . . . .
C5 C 0.3168(3) 0.1940(2) 0.50164(14) 0.0219(4) Uani 1 1 d . . . . .
H5 H 0.2726 0.2387 0.4377 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3668(3) -0.0239(2) 0.62443(14) 0.0227(4) Uani 1 1 d . . . . .
H6 H 0.3568 -0.1270 0.6441 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3974(3) 0.2792(2) 0.56633(15) 0.0231(4) Uani 1 1 d . . . . .
H7 H 0.4079 0.3822 0.5466 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4471(3) 0.0614(2) 0.68885(14) 0.0225(4) Uani 1 1 d . . . . .
H8 H 0.4916 0.0166 0.7527 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4658(3) 0.2170(2) 0.66252(14) 0.0222(4) Uani 1 1 d . . . . .
C10 C 0.5427(3) 0.3071(2) 0.73170(15) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.5529(3) 0.4652(2) 0.71120(15) 0.0258(4) Uani 1 1 d . . . . .
C12 C 0.6101(3) 0.2466(2) 0.82801(15) 0.0266(5) Uani 1 1 d . . . . .
N1 N 0.1591(3) -0.3246(2) 0.50959(14) 0.0311(4) Uani 1 1 d . . . . .
N2 N 0.0801(3) 0.0579(2) 0.28789(13) 0.0317(4) Uani 1 1 d . . . . .
N3 N 0.5604(3) 0.5947(2) 0.69980(14) 0.0353(5) Uani 1 1 d . . . . .
N4 N 0.6650(3) 0.1997(2) 0.90737(14) 0.0371(5) Uani 1 1 d . . . . .
C13 C 0.1380(3) 0.1755(3) 0.9302(2) 0.0459(7) Uani 1 1 d . . . . .
H13 H 0.1019 0.0846 0.9071 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2068(4) 0.1774(3) 1.0273(2) 0.0479(7) Uani 1 1 d . . . . .
H14 H 0.2182 0.0881 1.0714 0.058 Uiso 1 1 calc R U . . .
C15 C 0.2594(3) 0.3122(3) 1.0603(2) 0.0435(6) Uani 1 1 d . . . . .
H15 H 0.3050 0.3136 1.1275 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2471(3) 0.4419(3) 0.99846(19) 0.0376(5) Uani 1 1 d . . . . .
H16 H 0.2847 0.5318 1.0223 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1795(3) 0.4408(3) 0.90100(18) 0.0335(5) Uani 1 1 d . . . . .
C18 C 0.1213(3) 0.3100(3) 0.86455(18) 0.0363(5) Uani 1 1 d . . . . .
C19 C 0.0474(3) 0.3114(3) 0.7657(2) 0.0413(6) Uani 1 1 d . . . . .
H19 H 0.0075 0.2222 0.7422 0.050 Uiso 1 1 calc R U . . .
C20 C 0.0338(3) 0.4409(3) 0.70419(19) 0.0406(6) Uani 1 1 d . . . . .
H20 H -0.0160 0.4442 0.6376 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0961(3) 0.5709(3) 0.74226(16) 0.0323(5) Uani 1 1 d . . . . .
H21 H 0.0889 0.6614 0.6996 0.039 Uiso 1 1 calc R U . . .
N5 N 0.1633(3) 0.5708(2) 0.83421(14) 0.0333(5) 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
C22 N5 1.459(3) . ?
C1 N2 1.158(3) . ?
C1 C3 1.418(3) . ?
C2 N1 1.154(3) . ?
C2 C3 1.427(3) . ?
C3 C4 1.412(3) . ?
C4 C6 1.420(3) . ?
C4 C5 1.432(3) . ?
C5 C7 1.365(3) . ?
C6 C8 1.362(3) . ?
C7 C9 1.420(3) . ?
C8 C9 1.431(3) . ?
C9 C10 1.418(3) . ?
C10 C12 1.415(3) . ?
C10 C11 1.423(3) . ?
C11 N3 1.155(3) . ?
C12 N4 1.157(3) . ?
C13 C14 1.381(4) . ?
C13 C18 1.425(4) . ?
C14 C15 1.399(4) . ?
C15 C16 1.365(4) . ?
C16 C17 1.380(3) . ?
C17 C18 1.402(3) . ?
C17 N5 1.403(3) . ?
C18 C19 1.414(3) . ?
C19 C20 1.361(4) . ?
C20 C21 1.419(4) . ?
C21 N5 1.311(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
N2 C1 C3 178.5(2) . . ?
N1 C2 C3 178.3(2) . . ?
C4 C3 C1 122.43(18) . . ?
C4 C3 C2 122.03(18) . . ?
C1 C3 C2 115.41(17) . . ?
C3 C4 C6 121.39(18) . . ?
C3 C4 C5 121.16(18) . . ?
C6 C4 C5 117.45(17) . . ?
C7 C5 C4 121.22(18) . . ?
C8 C6 C4 121.21(18) . . ?
C5 C7 C9 121.32(18) . . ?
C6 C8 C9 121.49(18) . . ?
C10 C9 C7 121.50(18) . . ?
C10 C9 C8 121.13(18) . . ?
C7 C9 C8 117.31(17) . . ?
C12 C10 C9 121.97(18) . . ?
C12 C10 C11 115.13(17) . . ?
C9 C10 C11 122.88(18) . . ?
N3 C11 C10 176.5(2) . . ?
N4 C12 C10 178.8(2) . . ?
C14 C13 C18 120.0(2) . . ?
C13 C14 C15 119.3(2) . . ?
C16 C15 C14 121.8(2) . . ?
C15 C16 C17 119.3(2) . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 N5 121.8(2) . . ?
C18 C17 N5 116.8(2) . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 C13 118.1(2) . . ?
C19 C18 C13 120.8(2) . . ?
C20 C19 C18 119.7(2) . . ?
C19 C20 C21 118.1(2) . . ?
N5 C21 C20 122.4(2) . . ?
C21 N5 C17 121.9(2) . . ?
C21 N5 C22 118.5(2) . . ?
C17 N5 C22 119.59(19) . . ?

_refine_diff_density_max         1.026
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_1TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503300'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 N5'
_chemical_formula_weight         348.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.3571(3)
_cell_length_b                   15.9841(5)
_cell_length_c                   12.6113(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.225(3)
_cell_angle_gamma                90
_cell_volume                     1681.96(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4491
_cell_measurement_theta_min      3.5073
_cell_measurement_theta_max      72.1460

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2002
_exptl_crystal_size_mid          0.1438
_exptl_crystal_size_min          0.0781
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_diffrn_ambient_temperature      130.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_detector_area_resol_mean 16.0711
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            11463
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.470
_diffrn_reflns_theta_max         72.294
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3287
_reflns_number_gt                2748
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0628P)²+0.2949P] 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         3287
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
C18 C 0.2033(2) 0.16732(9) 0.66028(14) 0.0413(4) Uani 1 1 d . . . . .
H18A H 0.2915 0.2007 0.6928 0.062 Uiso 1 1 calc R U . . .
H18B H 0.1140 0.1666 0.7074 0.062 Uiso 1 1 calc R U . . .
H18C H 0.1676 0.1921 0.5919 0.062 Uiso 1 1 calc R U . . .
C4 C 0.99246(16) 0.03372(8) 0.88400(10) 0.0269(3) Uani 1 1 d . . . . .
C8 C 1.25833(16) -0.02863(9) 0.89401(11) 0.0285(3) Uani 1 1 d . . . . .
H8 H 1.3712 -0.0221 0.9033 0.034 Uiso 1 1 calc R U . . .
N3 N 0.58561(15) 0.10418(8) 0.86208(10) 0.0372(3) Uani 1 1 d . . . . .
N4 N 1.01314(15) 0.25281(8) 0.91282(11) 0.0391(3) Uani 1 1 d . . . . .
C5 C 0.92695(16) -0.04763(8) 0.86460(10) 0.0276(3) Uani 1 1 d . . . . .
H5 H 0.8141 -0.0541 0.8546 0.033 Uiso 1 1 calc R U . . .
C7 C 1.16251(17) 0.04007(8) 0.89866(11) 0.0281(3) Uani 1 1 d . . . . .
H7 H 1.2099 0.0933 0.9119 0.034 Uiso 1 1 calc R U . . .
N1 N 1.19163(16) -0.33234(8) 0.85480(11) 0.0382(3) Uani 1 1 d . . . . .
C9 C 1.19300(17) -0.10998(8) 0.87560(10) 0.0280(3) Uani 1 1 d . . . . .
C1 C 0.72352(17) 0.10255(8) 0.87387(11) 0.0290(3) Uani 1 1 d . . . . .
C3 C 0.89363(17) 0.10511(8) 0.88939(11) 0.0283(3) Uani 1 1 d . . . . .
C2 C 0.96005(17) 0.18638(9) 0.90319(11) 0.0300(3) Uani 1 1 d . . . . .
C6 C 1.02309(17) -0.11613(9) 0.86020(11) 0.0290(3) Uani 1 1 d . . . . .
H6 H 0.9758 -0.1694 0.8465 0.035 Uiso 1 1 calc R U . . .
C12 C 1.46383(18) -0.17252(9) 0.88222(12) 0.0339(3) Uani 1 1 d . . . . .
N2 N 1.60190(16) -0.16583(8) 0.89065(12) 0.0441(3) Uani 1 1 d . . . . .
C11 C 1.23588(17) -0.26377(9) 0.86102(11) 0.0311(3) Uani 1 1 d . . . . .
C10 C 1.29481(17) -0.18085(9) 0.87140(11) 0.0302(3) Uani 1 1 d . . . . .
N5 N 0.25900(14) 0.08098(8) 0.64336(10) 0.0327(3) Uani 1 1 d . . . . .
C15 C 0.35692(18) -0.08240(9) 0.61224(11) 0.0326(3) Uani 1 1 d . . . . .
C19 C 0.41447(17) 0.06400(9) 0.64713(11) 0.0314(3) Uani 1 1 d . . . . .
H19 H 0.4894 0.1080 0.6601 0.038 Uiso 1 1 calc R U . . .
C20 C 0.47063(17) -0.01759(9) 0.63237(11) 0.0306(3) Uani 1 1 d . . . . .
C21 C 0.63664(18) -0.03514(10) 0.63745(12) 0.0347(3) Uani 1 1 d . . . . .
H21 H 0.7125 0.0084 0.6506 0.042 Uiso 1 1 calc R U . . .
C22 C 0.68668(19) -0.11544(10) 0.62327(12) 0.0391(4) Uani 1 1 d . . . . .
H22 H 0.7981 -0.1278 0.6269 0.047 Uiso 1 1 calc R U . . .
C14 C 0.4134(2) -0.16455(10) 0.59807(12) 0.0381(4) Uani 1 1 d . . . . .
H14 H 0.3395 -0.2090 0.5850 0.046 Uiso 1 1 calc R U . . .
C16 C 0.19227(18) -0.06061(10) 0.60791(12) 0.0355(3) Uani 1 1 d . . . . .
H16 H 0.1134 -0.1026 0.5940 0.043 Uiso 1 1 calc R U . . .
C17 C 0.14623(18) 0.01950(10) 0.62345(12) 0.0354(3) Uani 1 1 d . . . . .
H17 H 0.0355 0.0333 0.6206 0.043 Uiso 1 1 calc R U . . .
C13 C 0.5744(2) -0.18033(10) 0.60319(12) 0.0403(4) Uani 1 1 d . . . . .
H13 H 0.6113 -0.2358 0.5931 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C18 N5 1.4756(19) . ?
C4 C3 1.4125(19) . ?
C4 C7 1.4263(19) . ?
C4 C5 1.4267(19) . ?
C8 C7 1.362(2) . ?
C8 C9 1.4242(19) . ?
N3 C1 1.1541(19) . ?
N4 C2 1.1544(19) . ?
C5 C6 1.3610(19) . ?
N1 C11 1.1580(19) . ?
C9 C10 1.4196(19) . ?
C9 C6 1.426(2) . ?
C1 C3 1.4247(19) . ?
C3 C2 1.4196(19) . ?
C12 N2 1.158(2) . ?
C12 C10 1.418(2) . ?
C11 C10 1.417(2) . ?
N5 C19 1.3255(18) . ?
N5 C17 1.3749(19) . ?
C15 C14 1.410(2) . ?
C15 C16 1.417(2) . ?
C15 C20 1.419(2) . ?
C19 C20 1.402(2) . ?
C20 C21 1.413(2) . ?
C21 C22 1.365(2) . ?
C22 C13 1.412(2) . ?
C14 C13 1.367(2) . ?
C16 C17 1.354(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
C3 C4 C7 121.15(12) . . ?
C3 C4 C5 121.65(12) . . ?
C7 C4 C5 117.19(12) . . ?
C7 C8 C9 121.47(13) . . ?
C6 C5 C4 121.23(12) . . ?
C8 C7 C4 121.39(12) . . ?
C10 C9 C8 120.64(13) . . ?
C10 C9 C6 122.29(12) . . ?
C8 C9 C6 117.06(12) . . ?
N3 C1 C3 177.02(15) . . ?
C4 C3 C2 121.30(12) . . ?
C4 C3 C1 123.49(12) . . ?
C2 C3 C1 115.05(12) . . ?
N4 C2 C3 178.91(16) . . ?
C5 C6 C9 121.64(12) . . ?
N2 C12 C10 179.73(18) . . ?
N1 C11 C10 177.82(16) . . ?
C11 C10 C12 115.84(12) . . ?
C11 C10 C9 122.95(13) . . ?
C12 C10 C9 121.16(13) . . ?
C19 N5 C17 121.37(13) . . ?
C19 N5 C18 120.17(12) . . ?
C17 N5 C18 118.46(12) . . ?
C14 C15 C16 123.72(14) . . ?
C14 C15 C20 118.47(14) . . ?
C16 C15 C20 117.80(13) . . ?
N5 C19 C20 121.36(13) . . ?
C19 C20 C21 120.91(13) . . ?
C19 C20 C15 118.49(13) . . ?
C21 C20 C15 120.59(13) . . ?
C22 C21 C20 119.21(14) . . ?
C21 C22 C13 120.59(14) . . ?
C13 C14 C15 120.11(14) . . ?
C17 C16 C15 120.65(14) . . ?
C16 C17 N5 120.32(14) . . ?
C14 C13 C22 121.02(14) . . ?

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_2F4TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503301'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H10 F4 N5'
_chemical_formula_weight         420.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.9675(3)
_cell_length_b                   10.4959(3)
_cell_length_c                   14.5659(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.307(2)
_cell_angle_gamma                90
_cell_volume                     1828.14(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2869
_cell_measurement_theta_min      3.0337
_cell_measurement_theta_max      73.5182

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_F_000             852
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4168
_exptl_crystal_size_mid          0.2274
_exptl_crystal_size_min          0.0174
_exptl_absorpt_coefficient_mu    1.063
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.00(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6589
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.696
_diffrn_reflns_theta_max         67.495
_diffrn_reflns_theta_full        67.495
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3295
_reflns_number_gt                2827
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1069P)²+1.2738P] 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         3295
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1891
_refine_ls_wR_factor_gt          0.1812
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
F4 F 0.85004(12) 0.05087(14) 0.18778(9) 0.0303(4) Uani 1 1 d . . . . .
F1 F 0.71878(11) 0.01836(15) 0.04286(9) 0.0308(4) Uani 1 1 d . . . . .
F2 F 1.12407(11) -0.21224(15) 0.05789(10) 0.0323(4) Uani 1 1 d . . . . .
F3 F 0.99255(12) -0.24430(14) -0.08861(9) 0.0323(4) Uani 1 1 d . . . . .
C7 C 1.02239(19) -0.1568(2) 0.05670(16) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.84865(19) -0.1149(2) -0.03168(15) 0.0232(5) Uani 1 1 d . . . . .
C6 C 0.9549(2) -0.1725(2) -0.01997(16) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.99369(19) -0.0816(2) 0.13280(15) 0.0246(5) Uani 1 1 d . . . . .
C8 C 0.88678(19) -0.0237(2) 0.12068(15) 0.0240(5) Uani 1 1 d . . . . .
C5 C 0.81928(19) -0.0397(2) 0.04495(15) 0.0238(5) Uani 1 1 d . . . . .
C12 C 1.1635(2) -0.1353(3) 0.23105(18) 0.0347(6) Uani 1 1 d . . . . .
N1 N 1.01402(19) 0.0745(3) 0.35067(15) 0.0394(6) Uani 1 1 d . . . . .
C1 C 0.6758(2) -0.0630(3) -0.12582(17) 0.0344(6) Uani 1 1 d . . . . .
C10 C 1.0627(2) -0.0661(2) 0.21289(16) 0.0282(5) Uani 1 1 d . . . . .
N4 N 0.8026(2) -0.2824(2) -0.24644(16) 0.0406(6) Uani 1 1 d . . . . .
C2 C 0.7986(2) -0.2143(2) -0.18521(16) 0.0286(5) Uani 1 1 d . . . . .
N2 N 1.2454(2) -0.1879(3) 0.25021(19) 0.0483(7) Uani 1 1 d . . . . .
C11 C 1.0325(2) 0.0123(3) 0.28788(17) 0.0312(6) Uani 1 1 d . . . . .
C3 C 0.7795(2) -0.1273(2) -0.11213(16) 0.0266(5) Uani 1 1 d . . . . .
N3 N 0.5909(2) -0.0145(3) -0.14312(18) 0.0544(8) Uani 1 1 d . . . . .
N5 N 0.3446(2) 0.0048(2) 0.63220(16) 0.0398(6) Uani 1 1 d . . . . .
C17 C 0.4101(2) 0.0909(3) 0.58203(19) 0.0392(6) Uani 1 1 d . . . . .
C16 C 0.3645(2) 0.1329(3) 0.4987(2) 0.0398(7) Uani 1 1 d . . . . .
C22 C 0.3893(2) -0.0396(3) 0.7199(2) 0.0446(7) Uani 1 1 d . . . . .
H22A H 0.3947 0.0319 0.7631 0.067 Uiso 1 1 calc R U . . .
H22B H 0.4638 -0.0760 0.7124 0.067 Uiso 1 1 calc R U . . .
H22C H 0.3398 -0.1050 0.7439 0.067 Uiso 1 1 calc R U . . .
C14 C 0.1965(2) 0.0098(3) 0.51562(19) 0.0366(6) Uani 1 1 d . . . . .
H14 H 0.1249 -0.0192 0.4944 0.044 Uiso 1 1 calc R U . . .
C18 C 0.5126(3) 0.1306(3) 0.6154(2) 0.0440(7) Uani 1 1 d . . . . .
H18 H 0.5417 0.1021 0.6735 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5718(2) 0.2120(3) 0.5632(2) 0.0429(7) Uani 1 1 d . . . . .
H19 H 0.6432 0.2394 0.5864 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2464(2) -0.0324(3) 0.6021(2) 0.0431(7) Uani 1 1 d . . . . .
H13 H 0.2058 -0.0898 0.6385 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2565(2) 0.0925(3) 0.46620(19) 0.0423(7) Uani 1 1 d . . . . .
H15 H 0.2262 0.1240 0.4093 0.051 Uiso 1 1 calc R U . . .
C20 C 0.5336(3) 0.2572(3) 0.4782(2) 0.0462(7) Uani 1 1 d . . . . .
H20 H 0.5787 0.3123 0.4436 0.055 Uiso 1 1 calc R U . . .
C21 C 0.4284(3) 0.2206(3) 0.4443(2) 0.0496(8) Uani 1 1 d . . . . .
H21 H 0.3990 0.2520 0.3872 0.060 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
F4 C8 1.340(3) . ?
F1 C5 1.347(3) . ?
F2 C7 1.348(3) . ?
F3 C6 1.344(3) . ?
C7 C6 1.361(4) . ?
C7 C9 1.414(3) . ?
C4 C6 1.412(3) . ?
C4 C3 1.413(3) . ?
C4 C5 1.423(3) . ?
C9 C10 1.411(3) . ?
C9 C8 1.421(3) . ?
C8 C5 1.351(3) . ?
C12 N2 1.150(4) . ?
C12 C10 1.424(4) . ?
N1 C11 1.152(4) . ?
C1 N3 1.155(4) . ?
C1 C3 1.420(4) . ?
C10 C11 1.426(4) . ?
N4 C2 1.145(3) . ?
C2 C3 1.428(3) . ?
N5 C13 1.297(4) . ?
N5 C17 1.418(4) . ?
N5 C22 1.443(4) . ?
C17 C18 1.366(4) . ?
C17 C16 1.382(4) . ?
C16 C15 1.423(4) . ?
C16 C21 1.452(5) . ?
C14 C15 1.352(4) . ?
C14 C13 1.442(4) . ?
C18 C19 1.362(4) . ?
C19 C20 1.387(4) . ?
C20 C21 1.388(5) . ?

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
F2 C7 C6 117.6(2) . . ?
F2 C7 C9 118.6(2) . . ?
C6 C7 C9 123.8(2) . . ?
C6 C4 C3 123.7(2) . . ?
C6 C4 C5 113.1(2) . . ?
C3 C4 C5 123.1(2) . . ?
F3 C6 C7 118.2(2) . . ?
F3 C6 C4 118.5(2) . . ?
C7 C6 C4 123.3(2) . . ?
C10 C9 C7 124.1(2) . . ?
C10 C9 C8 123.2(2) . . ?
C7 C9 C8 112.8(2) . . ?
F4 C8 C5 117.7(2) . . ?
F4 C8 C9 118.6(2) . . ?
C5 C8 C9 123.6(2) . . ?
F1 C5 C8 117.8(2) . . ?
F1 C5 C4 118.8(2) . . ?
C8 C5 C4 123.4(2) . . ?
N2 C12 C10 176.3(3) . . ?
N3 C1 C3 175.1(3) . . ?
C9 C10 C12 123.9(2) . . ?
C9 C10 C11 122.8(2) . . ?
C12 C10 C11 113.0(2) . . ?
N4 C2 C3 173.0(3) . . ?
N1 C11 C10 176.1(3) . . ?
C4 C3 C1 123.5(2) . . ?
C4 C3 C2 124.8(2) . . ?
C1 C3 C2 111.4(2) . . ?
C13 N5 C17 121.9(3) . . ?
C13 N5 C22 120.0(3) . . ?
C17 N5 C22 118.0(2) . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 N5 121.2(3) . . ?
C16 C17 N5 116.6(3) . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 C21 118.9(3) . . ?
C15 C16 C21 119.9(3) . . ?
C15 C14 C13 116.9(3) . . ?
C19 C18 C17 118.2(3) . . ?
C18 C19 C20 123.5(3) . . ?
N5 C13 C14 122.7(3) . . ?
C14 C15 C16 120.5(3) . . ?
C19 C20 C21 119.0(3) . . ?
C20 C21 C16 118.2(3) . . ?

_refine_diff_density_max         1.266
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_5F4TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503302'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 F4 N6 O2'
_chemical_formula_weight         513.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.1083(2)
_cell_length_b                   25.3703(5)
_cell_length_c                   12.9159(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.474(2)
_cell_angle_gamma                90
_cell_volume                     2290.44(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4130
_cell_measurement_theta_min      3.4770
_cell_measurement_theta_max      73.6852

_exptl_crystal_description       'Small Shard'
_exptl_crystal_colour            'Dark Blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1060
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3493
_exptl_crystal_size_mid          0.1463
_exptl_crystal_size_min          0.0754
_exptl_absorpt_coefficient_mu    1.030
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            9341
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.484
_diffrn_reflns_theta_max         73.849
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4535
_reflns_number_gt                3860
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0451P)²+0.5353P] 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         4535
_refine_ls_number_parameters     337
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.028
_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
F5 F 0.19347(11) -0.02893(3) 0.59075(6) 0.02334(17) Uani 1 1 d . . . . .
C30 C -0.4802(2) -0.25886(5) 0.86501(11) 0.0285(3) Uani 1 1 d . . . . .
H30A H -0.3443 -0.2679 0.8842 0.043 Uiso 1 1 calc R U . . .
H30B H -0.5240 -0.2651 0.7896 0.043 Uiso 1 1 calc R U . . .
H30C H -0.5544 -0.2808 0.9054 0.043 Uiso 1 1 calc R U . . .
C31 C -0.4235(2) -0.10408(6) 1.12134(11) 0.0302(3) Uani 1 1 d . . . . .
H31A H -0.4855 -0.1239 1.1709 0.045 Uiso 1 1 calc R U . . .
H31B H -0.4640 -0.0671 1.1204 0.045 Uiso 1 1 calc R U . . .
H31C H -0.2843 -0.1061 1.1434 0.045 Uiso 1 1 calc R U . . .
F3 F 0.43071(12) 0.08295(3) 0.28095(6) 0.02517(17) Uani 1 1 d . . . . .
F4 F 0.28956(12) -0.01146(3) 0.23792(6) 0.02562(18) Uani 1 1 d . . . . .
F1 F 0.33776(11) 0.06495(3) 0.63376(6) 0.02293(17) Uani 1 1 d . . . . .
C6 C 0.37191(18) 0.05587(5) 0.35874(9) 0.0192(2) Uani 1 1 d . . . . .
C1 C 0.07433(18) -0.10735(5) 0.46288(10) 0.0207(3) Uani 1 1 d . . . . .
C7 C 0.39013(17) 0.07953(5) 0.45965(9) 0.0178(2) Uani 1 1 d . . . . .
C4 C 0.23034(17) -0.02560(5) 0.41131(9) 0.0184(2) Uani 1 1 d . . . . .
N5 N 0.12841(17) -0.02785(5) 0.90095(10) 0.0294(3) Uani 1 1 d . . . . .
N6 N -0.41451(15) -0.18370(4) 0.99945(8) 0.0188(2) Uani 1 1 d . . . . .
C11 C 0.32405(17) 0.04707(5) 0.53473(9) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.24956(18) -0.00182(5) 0.51199(9) 0.0182(2) Uani 1 1 d . . . . .
C5 C 0.29762(18) 0.00697(5) 0.33605(9) 0.0193(2) Uani 1 1 d . . . . .
O1 O 0.19148(17) -0.01707(4) 0.99348(9) 0.0400(3) Uani 1 1 d . . . . .
C18 C -0.0883(2) -0.18072(5) 0.83841(11) 0.0248(3) Uani 1 1 d . . . . .
H18 H -0.1307 -0.2160 0.8253 0.030 Uiso 1 1 calc R U . . .
N4 N 0.00484(17) -0.13450(4) 0.51697(9) 0.0257(2) Uani 1 1 d . . . . .
N2 N 0.60704(19) 0.19100(5) 0.35775(9) 0.0298(3) Uani 1 1 d . . . . .
C10 C 0.46074(18) 0.15784(5) 0.57970(10) 0.0216(3) Uani 1 1 d . . . . .
C9 C 0.54192(19) 0.16229(5) 0.41086(10) 0.0217(3) Uani 1 1 d . . . . .
C2 C 0.13368(18) -0.10111(5) 0.28868(10) 0.0222(3) Uani 1 1 d . . . . .
O2 O 0.13329(18) 0.00174(4) 0.82662(10) 0.0437(3) Uani 1 1 d . . . . .
N3 N 0.11141(19) -0.12418(5) 0.21075(9) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.46104(19) 0.18424(5) 0.65239(9) 0.0298(3) Uani 1 1 d . . . . .
C14 C 0.0589(2) -0.10306(6) 0.78218(11) 0.0270(3) Uani 1 1 d . . . . .
H14 H 0.1119 -0.0841 0.7309 0.032 Uiso 1 1 calc R U . . .
C15 C 0.04446(19) -0.08054(5) 0.87761(11) 0.0236(3) Uani 1 1 d . . . . .
C16 C -0.03825(18) -0.10559(5) 0.95376(10) 0.0217(3) Uani 1 1 d . . . . .
H16 H -0.0460 -0.0886 1.0184 0.026 Uiso 1 1 calc R U . . .
C8 C 0.46741(18) 0.13029(5) 0.48414(10) 0.0195(2) Uani 1 1 d . . . . .
C19 C -0.19658(18) -0.18624(5) 1.01360(10) 0.0201(2) Uani 1 1 d . . . . .
H19A H -0.1417 -0.1722 1.0842 0.024 Uiso 1 1 calc R U . . .
H19B H -0.1581 -0.2237 1.0119 0.024 Uiso 1 1 calc R U . . .
C3 C 0.15416(18) -0.07670(5) 0.38934(10) 0.0194(2) Uani 1 1 d . . . . .
C25 C -0.47074(19) -0.22007(5) 1.08246(10) 0.0226(3) Uani 1 1 d . . . . .
H25A H -0.4219 -0.2559 1.0723 0.027 Uiso 1 1 calc R U . . .
H25B H -0.4073 -0.2076 1.1528 0.027 Uiso 1 1 calc R U . . .
C17 C -0.10963(18) -0.15643(5) 0.93257(10) 0.0200(3) Uani 1 1 d . . . . .
C13 C -0.0065(2) -0.15436(6) 0.76355(11) 0.0281(3) Uani 1 1 d . . . . .
H13 H 0.0047 -0.1714 0.6995 0.034 Uiso 1 1 calc R U . . .
C28 C -0.47993(19) -0.12729(5) 1.01226(11) 0.0240(3) Uani 1 1 d . . . . .
H28A H -0.4271 -0.1046 0.9621 0.029 Uiso 1 1 calc R U . . .
H28B H -0.6211 -0.1261 0.9923 0.029 Uiso 1 1 calc R U . . .
C26 C -0.6840(2) -0.22349(6) 1.08066(11) 0.0273(3) Uani 1 1 d . . . . .
H26A H -0.7332 -0.1885 1.0936 0.041 Uiso 1 1 calc R U . . .
H26B H -0.7084 -0.2479 1.1355 0.041 Uiso 1 1 calc R U . . .
H26C H -0.7483 -0.2363 1.0117 0.041 Uiso 1 1 calc R U . . .
C27 C -0.50793(19) -0.20129(5) 0.88952(10) 0.0229(3) Uani 1 1 d . . . . .
H27A H -0.6469 -0.1941 0.8802 0.027 Uiso 1 1 calc R U . . .
H27B H -0.4561 -0.1796 0.8375 0.027 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
F5 C12 1.3470(14) . ?
C30 C27 1.5149(18) . ?
C31 C28 1.5123(19) . ?
F3 C6 1.3449(14) . ?
F4 C5 1.3423(14) . ?
F1 C11 1.3438(14) . ?
C6 C5 1.3593(18) . ?
C6 C7 1.4193(17) . ?
C1 N4 1.1541(18) . ?
C1 C3 1.4230(18) . ?
C7 C8 1.4132(17) . ?
C7 C11 1.4159(17) . ?
C4 C3 1.4139(17) . ?
C4 C12 1.4174(17) . ?
C4 C5 1.4231(18) . ?
N5 O2 1.2243(17) . ?
N5 O1 1.2285(17) . ?
N5 C15 1.4726(17) . ?
N6 C27 1.5209(16) . ?
N6 C25 1.5220(16) . ?
N6 C28 1.5232(16) . ?
N6 C19 1.5279(16) . ?
C11 C12 1.3597(18) . ?
C18 C13 1.3875(19) . ?
C18 C17 1.3960(18) . ?
N2 C9 1.1535(18) . ?
C10 N1 1.1528(18) . ?
C10 C8 1.4267(18) . ?
C9 C8 1.4206(18) . ?
C2 N3 1.1501(18) . ?
C2 C3 1.4235(18) . ?
C14 C15 1.379(2) . ?
C14 C13 1.388(2) . ?
C15 C16 1.3882(19) . ?
C16 C17 1.3949(18) . ?
C19 C17 1.5114(17) . ?
C25 C26 1.5141(18) . ?

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
F3 C6 C5 117.80(11) . . ?
F3 C6 C7 118.76(11) . . ?
C5 C6 C7 123.44(11) . . ?
N4 C1 C3 175.34(13) . . ?
C8 C7 C11 122.71(11) . . ?
C8 C7 C6 123.91(11) . . ?
C11 C7 C6 113.38(11) . . ?
C3 C4 C12 122.95(12) . . ?
C3 C4 C5 124.01(11) . . ?
C12 C4 C5 113.03(11) . . ?
O2 N5 O1 124.68(13) . . ?
O2 N5 C15 117.66(12) . . ?
O1 N5 C15 117.64(12) . . ?
C27 N6 C25 110.72(10) . . ?
C27 N6 C28 106.68(9) . . ?
C25 N6 C28 111.63(10) . . ?
C27 N6 C19 111.13(10) . . ?
C25 N6 C19 106.30(9) . . ?
C28 N6 C19 110.45(10) . . ?
F1 C11 C12 118.13(11) . . ?
F1 C11 C7 118.69(11) . . ?
C12 C11 C7 123.18(11) . . ?
F5 C12 C11 117.38(11) . . ?
F5 C12 C4 118.89(11) . . ?
C11 C12 C4 123.73(11) . . ?
F4 C5 C6 118.01(11) . . ?
F4 C5 C4 118.74(11) . . ?
C6 C5 C4 123.24(11) . . ?
C13 C18 C17 121.32(13) . . ?
N1 C10 C8 173.54(14) . . ?
N2 C9 C8 174.63(13) . . ?
N3 C2 C3 174.67(14) . . ?
C15 C14 C13 117.78(12) . . ?
C14 C15 C16 123.62(12) . . ?
C14 C15 N5 117.75(12) . . ?
C16 C15 N5 118.58(12) . . ?
C15 C16 C17 118.03(12) . . ?
C7 C8 C9 123.26(11) . . ?
C7 C8 C10 124.58(11) . . ?
C9 C8 C10 111.80(11) . . ?
C17 C19 N6 115.43(10) . . ?
C4 C3 C1 123.50(11) . . ?
C4 C3 C2 123.65(12) . . ?
C1 C3 C2 112.64(11) . . ?
C26 C25 N6 114.47(10) . . ?
C16 C17 C18 119.08(12) . . ?
C16 C17 C19 120.45(11) . . ?
C18 C17 C19 120.33(11) . . ?
C18 C13 C14 120.05(13) . . ?
C31 C28 N6 115.63(11) . . ?
C30 C27 N6 115.26(10) . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_7TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503303'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N6 O2'
_chemical_formula_weight         433.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.0880(3)
_cell_length_b                   12.1413(6)
_cell_length_c                   13.3964(7)
_cell_angle_alpha                110.968(5)
_cell_angle_beta                 93.792(4)
_cell_angle_gamma                103.933(4)
_cell_volume                     1029.99(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4951
_cell_measurement_theta_min      3.5813
_cell_measurement_theta_max      73.7517

_exptl_crystal_description       'Large Block'
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             450
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6850
_exptl_crystal_size_mid          0.4186
_exptl_crystal_size_min          0.3742
_exptl_absorpt_coefficient_mu    0.759
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.821
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6745
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.584
_diffrn_reflns_theta_max         73.915
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4009
_reflns_number_gt                3693
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0781P)²+0.2846P] 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         4009
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1263
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
N5 N 0.21072(16) 0.12585(10) 0.37740(9) 0.0202(2) Uani 1 1 d . . . . .
N6 N 0.20663(18) -0.00925(12) -0.12478(10) 0.0282(3) Uani 1 1 d . . . . .
C17 C 0.25700(19) 0.24864(12) 0.40412(11) 0.0228(3) Uani 1 1 d . . . . .
H17 H 0.3800 0.2905 0.3926 0.027 Uiso 1 1 calc R U . . .
C16 C 0.03908(19) 0.06495(12) 0.39528(10) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.0086 -0.0213 0.3766 0.026 Uiso 1 1 calc R U . . .
O1 O 0.09907(18) -0.10871(10) -0.18832(9) 0.0388(3) Uani 1 1 d . . . . .
C20 C 0.32172(18) 0.03903(12) 0.20340(11) 0.0222(3) Uani 1 1 d . . . . .
C22 C 0.16445(19) -0.08918(12) 0.01889(11) 0.0229(3) Uani 1 1 d . . . . .
H22 H 0.0830 -0.1650 -0.0336 0.027 Uiso 1 1 calc R U . . .
C15 C -0.09199(19) 0.12738(12) 0.44052(10) 0.0215(3) Uani 1 1 d . . . . .
H15 H -0.2110 0.0843 0.4548 0.026 Uiso 1 1 calc R U . . .
C18 C 0.12876(19) 0.31330(12) 0.44755(11) 0.0234(3) Uani 1 1 d . . . . .
H18 H 0.1628 0.3995 0.4655 0.028 Uiso 1 1 calc R U . . .
O2 O 0.27736(18) 0.07771(12) -0.15003(10) 0.0440(3) Uani 1 1 d . . . . .
C19 C 0.3483(2) 0.05815(13) 0.32209(11) 0.0249(3) Uani 1 1 d . . . . .
H19A H 0.3216 -0.0225 0.3289 0.030 Uiso 1 1 calc R U . . .
H19B H 0.4861 0.1057 0.3570 0.030 Uiso 1 1 calc R U . . .
C14 C -0.05165(19) 0.25336(12) 0.46557(10) 0.0213(3) Uani 1 1 d . . . . .
C23 C 0.24988(19) 0.00712(13) -0.01074(11) 0.0227(3) Uani 1 1 d . . . . .
C13 C -0.1960(2) 0.32309(13) 0.50787(11) 0.0267(3) Uani 1 1 d . . . . .
H13A H -0.2538 0.3438 0.4508 0.040 Uiso 1 1 calc R U . . .
H13B H -0.1283 0.3988 0.5704 0.040 Uiso 1 1 calc R U . . .
H13C H -0.3007 0.2723 0.5301 0.040 Uiso 1 1 calc R U . . .
C24 C 0.3731(2) 0.11794(13) 0.06275(12) 0.0264(3) Uani 1 1 d . . . . .
H24 H 0.4305 0.1823 0.0400 0.032 Uiso 1 1 calc R U . . .
C25 C 0.41084(19) 0.13289(13) 0.17034(12) 0.0260(3) Uani 1 1 d . . . . .
H25 H 0.4978 0.2074 0.2218 0.031 Uiso 1 1 calc R U . . .
C21 C 0.20076(19) -0.07212(12) 0.12708(11) 0.0221(3) Uani 1 1 d . . . . .
H21 H 0.1427 -0.1367 0.1494 0.027 Uiso 1 1 calc R U . . .
C4 C 0.20933(17) 0.49466(11) 0.93414(10) 0.0178(3) Uani 1 1 d . . . . .
N1 N -0.04959(17) 0.22731(10) 0.70886(9) 0.0249(3) Uani 1 1 d . . . . .
C7 C 0.39536(17) 0.57551(11) 1.15337(10) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.28005(18) 0.62188(11) 1.00241(11) 0.0192(3) Uani 1 1 d . . . . .
H5 H 0.2640 0.6812 0.9742 0.023 Uiso 1 1 calc R U . . .
C8 C 0.32094(18) 0.44847(12) 1.08604(11) 0.0195(3) Uani 1 1 d . . . . .
H8 H 0.3332 0.3891 1.1150 0.023 Uiso 1 1 calc R U . . .
N3 N 0.5099(2) 0.46209(12) 1.35075(10) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.02794(18) 0.32988(12) 0.76015(10) 0.0196(3) Uani 1 1 d . . . . .
C9 C 0.23242(18) 0.40941(11) 0.98105(10) 0.0187(3) Uani 1 1 d . . . . .
H9 H 0.1853 0.3237 0.9384 0.022 Uiso 1 1 calc R U . . .
N2 N 0.0970(2) 0.61228(13) 0.74021(12) 0.0427(4) Uani 1 1 d . . . . .
N4 N 0.61891(19) 0.84521(11) 1.38577(10) 0.0305(3) Uani 1 1 d . . . . .
C11 C 0.50236(19) 0.53101(12) 1.31078(10) 0.0237(3) Uani 1 1 d . . . . .
C12 C 0.56243(19) 0.74215(12) 1.32959(10) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.36995(17) 0.66092(11) 1.10692(10) 0.0190(3) Uani 1 1 d . . . . .
H6 H 0.4166 0.7466 1.1497 0.023 Uiso 1 1 calc R U . . .
C2 C 0.11917(18) 0.45580(12) 0.82547(10) 0.0193(3) Uani 1 1 d . . . . .
C3 C 0.1044(2) 0.54158(12) 0.77812(11) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.48997(18) 0.61546(12) 1.26165(10) 0.0201(3) 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
N5 C16 1.3477(17) . ?
N5 C17 1.3511(16) . ?
N5 C19 1.4904(17) . ?
N6 O1 1.2244(17) . ?
N6 O2 1.2262(17) . ?
N6 C23 1.4693(18) . ?
C17 C18 1.3667(19) . ?
C16 C15 1.3746(19) . ?
C20 C21 1.3932(18) . ?
C20 C25 1.3947(19) . ?
C20 C19 1.5142(19) . ?
C22 C23 1.3835(19) . ?
C22 C21 1.3856(19) . ?
C15 C14 1.3940(18) . ?
C18 C14 1.3933(19) . ?
C14 C13 1.4954(19) . ?
C23 C24 1.384(2) . ?
C24 C25 1.386(2) . ?
C4 C2 1.4109(17) . ?
C4 C9 1.4235(17) . ?
C4 C5 1.4244(17) . ?
N1 C1 1.1546(17) . ?
C7 C10 1.4143(18) . ?
C7 C8 1.4214(17) . ?
C7 C6 1.4255(17) . ?
C5 C6 1.3610(18) . ?
C8 C9 1.3636(18) . ?
N3 C11 1.1524(18) . ?
C1 C2 1.4187(18) . ?
N2 C3 1.1523(19) . ?
N4 C12 1.1564(18) . ?
C11 C10 1.4181(18) . ?
C12 C10 1.4192(18) . ?
C2 C3 1.4194(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 N5 C17 120.71(12) . . ?
C16 N5 C19 120.66(11) . . ?
C17 N5 C19 118.55(11) . . ?
O1 N6 O2 124.16(13) . . ?
O1 N6 C23 117.60(12) . . ?
O2 N6 C23 118.23(13) . . ?
N5 C17 C18 120.70(12) . . ?
N5 C16 C15 120.15(12) . . ?
C21 C20 C25 119.80(13) . . ?
C21 C20 C19 119.40(12) . . ?
C25 C20 C19 120.76(12) . . ?
C23 C22 C21 118.28(13) . . ?
C16 C15 C14 120.53(12) . . ?
C17 C18 C14 120.31(12) . . ?
N5 C19 C20 109.85(10) . . ?
C18 C14 C15 117.53(12) . . ?
C18 C14 C13 120.24(12) . . ?
C15 C14 C13 122.21(12) . . ?
C22 C23 C24 122.61(13) . . ?
C22 C23 N6 118.43(12) . . ?
C24 C23 N6 118.95(12) . . ?
C23 C24 C25 118.45(12) . . ?
C24 C25 C20 120.29(13) . . ?
C22 C21 C20 120.51(12) . . ?
C2 C4 C9 121.94(12) . . ?
C2 C4 C5 121.16(11) . . ?
C9 C4 C5 116.90(11) . . ?
C10 C7 C8 121.54(11) . . ?
C10 C7 C6 121.47(11) . . ?
C8 C7 C6 116.99(11) . . ?
C6 C5 C4 121.88(11) . . ?
C9 C8 C7 121.82(12) . . ?
N1 C1 C2 178.25(14) . . ?
C8 C9 C4 121.23(12) . . ?
N3 C11 C10 179.12(15) . . ?
N4 C12 C10 178.91(15) . . ?
C5 C6 C7 121.17(12) . . ?
C4 C2 C1 121.85(11) . . ?
C4 C2 C3 121.48(12) . . ?
C1 C2 C3 116.55(11) . . ?
N2 C3 C2 178.46(16) . . ?
C7 C10 C11 121.64(12) . . ?
C7 C10 C12 121.75(11) . . ?
C11 C10 C12 116.40(11) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_6TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503304'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N6 O2'
_chemical_formula_weight         441.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.3694(3)
_cell_length_b                   11.4503(5)
_cell_length_c                   14.4977(8)
_cell_angle_alpha                66.999(4)
_cell_angle_beta                 82.796(4)
_cell_angle_gamma                88.216(3)
_cell_volume                     1116.98(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    4749
_cell_measurement_theta_min      3.3343
_cell_measurement_theta_max      76.8836

_exptl_crystal_description       Shard
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             466
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1064
_exptl_crystal_size_mid          0.0791
_exptl_crystal_size_min          0.0554
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            10359
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.337
_diffrn_reflns_theta_max         77.089
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4679
_reflns_number_gt                4022
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0758P)²+0.5285P] 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         4679
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1572
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_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
N6 N -0.39830(19) -0.16661(13) 0.88217(10) 0.0187(3) Uani 1 1 d . . . . .
C24 C -0.5287(2) -0.13730(18) 0.95991(13) 0.0239(4) Uani 1 1 d . . . . .
H24A H -0.4702 -0.1611 1.0224 0.029 Uiso 1 1 calc R U . . .
H24B H -0.5479 -0.0446 0.9340 0.029 Uiso 1 1 calc R U . . .
C23 C -0.5471(2) 0.00598(16) 0.74212(13) 0.0233(4) Uani 1 1 d . . . . .
H23A H -0.6627 0.0107 0.7819 0.035 Uiso 1 1 calc R U . . .
H23B H -0.5667 0.0305 0.6714 0.035 Uiso 1 1 calc R U . . .
H23C H -0.4565 0.0638 0.7466 0.035 Uiso 1 1 calc R U . . .
C22 C -0.4781(2) -0.12831(15) 0.78283(12) 0.0191(3) Uani 1 1 d . . . . .
H22A H -0.3830 -0.1380 0.7318 0.023 Uiso 1 1 calc R U . . .
H22B H -0.5805 -0.1875 0.7924 0.023 Uiso 1 1 calc R U . . .
C20 C -0.3658(2) -0.30841(16) 0.91664(13) 0.0234(4) Uani 1 1 d . . . . .
H20A H -0.4846 -0.3519 0.9256 0.028 Uiso 1 1 calc R U . . .
H20B H -0.2863 -0.3234 0.8622 0.028 Uiso 1 1 calc R U . . .
C21 C -0.2794(3) -0.36910(19) 1.01344(15) 0.0335(4) Uani 1 1 d . . . . .
H21A H -0.1572 -0.3318 1.0041 0.050 Uiso 1 1 calc R U . . .
H21B H -0.2696 -0.4606 1.0308 0.050 Uiso 1 1 calc R U . . .
H21C H -0.3555 -0.3542 1.0681 0.050 Uiso 1 1 calc R U . . .
C25 C -0.7136(3) -0.2043(2) 0.98628(15) 0.0318(4) Uani 1 1 d . . . . .
H25A H -0.7684 -0.1877 0.9243 0.048 Uiso 1 1 calc R U . . .
H25B H -0.7937 -0.1726 1.0303 0.048 Uiso 1 1 calc R U . . .
H25C H -0.6982 -0.2958 1.0213 0.048 Uiso 1 1 calc R U . . .
O2 O 0.3156(2) 0.06336(14) 0.45439(10) 0.0342(3) Uani 1 1 d . . . . .
O1 O 0.3151(2) -0.14160(14) 0.50261(11) 0.0342(3) Uani 1 1 d . . . . .
N5 N 0.2671(2) -0.04418(16) 0.51457(12) 0.0258(3) Uani 1 1 d . . . . .
C19 C -0.2219(2) -0.09104(16) 0.86807(12) 0.0203(3) Uani 1 1 d . . . . .
H19A H -0.2546 -0.0042 0.8626 0.024 Uiso 1 1 calc R U . . .
H19B H -0.1591 -0.1313 0.9291 0.024 Uiso 1 1 calc R U . . .
C18 C -0.0900(2) -0.08140(16) 0.77677(13) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.1433(2) -0.05650(17) 0.60529(13) 0.0212(3) Uani 1 1 d . . . . .
C17 C -0.0628(2) 0.03652(16) 0.69589(13) 0.0210(3) Uani 1 1 d . . . . .
H17 H -0.1262 0.1082 0.7000 0.025 Uiso 1 1 calc R U . . .
C15 C 0.0552(2) 0.05025(16) 0.60985(13) 0.0219(3) Uani 1 1 d . . . . .
H15 H 0.0752 0.1306 0.5555 0.026 Uiso 1 1 calc R U . . .
C16 C 0.0079(2) -0.18565(16) 0.77090(13) 0.0223(3) Uani 1 1 d . . . . .
H16 H -0.0043 -0.2650 0.8269 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1221(2) -0.17424(17) 0.68435(14) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.1847 -0.2457 0.6793 0.028 Uiso 1 1 calc R U . . .
C9 C 0.8209(2) 0.59410(16) 0.34711(12) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.6761(2) 0.51048(16) 0.55499(12) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.6496(2) 0.23988(15) 0.78373(11) 0.0273(3) Uani 1 1 d . . . . .
C5 C 0.7654(2) 0.42553(16) 0.51443(13) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.7759 0.3389 0.5575 0.025 Uiso 1 1 calc R U . . .
C12 C 0.8769(2) 0.76309(17) 0.17571(13) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.6296(2) 0.34219(16) 0.72705(12) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.4469(2) 0.61224(15) 0.74143(12) 0.0294(4) Uani 1 1 d . . . . .
C2 C 0.5192(2) 0.54973(16) 0.70246(12) 0.0217(3) Uani 1 1 d . . . . .
C11 C 0.9972(2) 0.55550(16) 0.20470(13) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.7285(2) 0.67817(15) 0.38750(13) 0.0199(3) Uani 1 1 d . . . . .
H7 H 0.7145 0.7641 0.3439 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6598(2) 0.63880(16) 0.48689(13) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.6000 0.6978 0.5111 0.024 Uiso 1 1 calc R U . . .
N3 N 1.0799(2) 0.49099(16) 0.17111(13) 0.0309(4) Uani 1 1 d . . . . .
C8 C 0.8359(2) 0.46589(16) 0.41516(13) 0.0212(3) Uani 1 1 d . . . . .
H8 H 0.8965 0.4071 0.3909 0.025 Uiso 1 1 calc R U . . .
N4 N 0.8585(3) 0.86607(16) 0.11906(12) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.6067(2) 0.46840(16) 0.65820(12) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.8971(2) 0.63654(16) 0.24451(13) 0.0210(3) 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
N6 C24 1.520(2) . ?
N6 C22 1.522(2) . ?
N6 C20 1.522(2) . ?
N6 C19 1.532(2) . ?
C24 C25 1.515(3) . ?
C23 C22 1.513(2) . ?
C20 C21 1.514(2) . ?
O2 N5 1.231(2) . ?
O1 N5 1.229(2) . ?
N5 C13 1.464(2) . ?
C19 C18 1.510(2) . ?
C18 C17 1.399(2) . ?
C18 C16 1.401(2) . ?
C13 C14 1.384(2) . ?
C13 C15 1.387(2) . ?
C17 C15 1.386(2) . ?
C16 C14 1.384(2) . ?
C9 C10 1.417(2) . ?
C9 C8 1.423(2) . ?
C9 C7 1.426(2) . ?
C4 C3 1.412(2) . ?
C4 C6 1.426(2) . ?
C4 C5 1.426(2) . ?
N1 C1 1.156(2) . ?
C5 C8 1.365(2) . ?
C12 N4 1.159(3) . ?
C12 C10 1.418(2) . ?
C1 C3 1.419(2) . ?
N2 C2 1.154(2) . ?
C2 C3 1.421(2) . ?
C11 N3 1.154(2) . ?
C11 C10 1.417(2) . ?
C7 C6 1.364(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
C24 N6 C22 111.18(12) . . ?
C24 N6 C20 111.21(13) . . ?
C22 N6 C20 105.54(12) . . ?
C24 N6 C19 105.93(12) . . ?
C22 N6 C19 110.87(12) . . ?
C20 N6 C19 112.21(13) . . ?
C25 C24 N6 114.78(14) . . ?
C23 C22 N6 114.57(13) . . ?
C21 C20 N6 115.76(15) . . ?
O1 N5 O2 123.92(16) . . ?
O1 N5 C13 118.14(16) . . ?
O2 N5 C13 117.94(15) . . ?
C18 C19 N6 114.62(13) . . ?
C17 C18 C16 119.01(16) . . ?
C17 C18 C19 118.63(15) . . ?
C16 C18 C19 122.35(15) . . ?
C14 C13 C15 122.50(16) . . ?
C14 C13 N5 118.47(15) . . ?
C15 C13 N5 119.01(16) . . ?
C15 C17 C18 120.94(16) . . ?
C17 C15 C13 118.20(16) . . ?
C14 C16 C18 120.65(16) . . ?
C16 C14 C13 118.59(16) . . ?
C10 C9 C8 121.49(15) . . ?
C10 C9 C7 121.62(15) . . ?
C8 C9 C7 116.88(15) . . ?
C3 C4 C6 121.77(15) . . ?
C3 C4 C5 121.06(15) . . ?
C6 C4 C5 117.18(15) . . ?
C8 C5 C4 121.47(15) . . ?
N4 C12 C10 179.1(2) . . ?
N1 C1 C3 179.20(19) . . ?
N2 C2 C3 177.68(19) . . ?
N3 C11 C10 179.0(2) . . ?
C6 C7 C9 121.91(15) . . ?
C7 C6 C4 121.06(15) . . ?
C5 C8 C9 121.49(15) . . ?
C4 C3 C1 121.92(15) . . ?
C4 C3 C2 123.16(15) . . ?
C1 C3 C2 114.82(15) . . ?
C9 C10 C11 122.15(15) . . ?
C9 C10 C12 121.62(15) . . ?
C11 C10 C12 116.22(15) . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_3TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503305'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_vrf_PLAT410_shelx               
;
PROBLEM: Short Intra H...H Contact  H26A   ..  H23B    ..       1.53 Ang.  
RESPONSE: The quinuclidinol unit is disorded over two sites.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N6 O3'
_chemical_formula_weight         467.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.8219(4)
_cell_length_b                   12.4540(5)
_cell_length_c                   13.5137(6)
_cell_angle_alpha                117.204(4)
_cell_angle_beta                 90.126(4)
_cell_angle_gamma                104.916(5)
_cell_volume                     1120.29(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3568
_cell_measurement_theta_min      3.7109
_cell_measurement_theta_max      74.3539

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             490
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5618
_exptl_crystal_size_mid          0.1701
_exptl_crystal_size_min          0.0430
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_diffrn_ambient_temperature      130.00(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7635
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.714
_diffrn_reflns_theta_max         74.525
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4407
_reflns_number_gt                3715
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0601P)²+0.7129P] 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         4407
_refine_ls_number_parameters     344
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.096
_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
C21 C 1.0846(4) 0.7353(3) 0.8360(3) 0.0279(7) Uani 0.6 1 d . U P A 1
H21A H 1.1892 0.8016 0.8385 0.034 Uiso 0.6 1 calc R U P A 1
H21B H 1.0747 0.6559 0.7663 0.034 Uiso 0.6 1 calc R U P A 1
C23 C 1.0775(4) 0.8334(3) 1.0423(3) 0.0254(6) Uani 0.6 1 d . U P A 1
H23 H 1.1101 0.8309 1.1126 0.030 Uiso 0.6 1 calc R U P A 1
O3 O 1.1838(3) 0.9491(2) 1.0525(2) 0.0311(5) Uani 0.6 1 d . U P A 1
H3 H 1.2479 0.9352 1.0008 0.047 Uiso 0.6 1 calc R U P A 1
C21A C 1.1152(8) 0.7942(4) 0.8946(5) 0.0458(13) Uani 0.4 1 d D U P A 2
H21C H 1.1907 0.7698 0.8329 0.055 Uiso 0.4 1 calc R U P A 2
C23A C 1.0383(8) 0.7693(8) 1.0612(5) 0.0529(16) Uani 0.4 1 d . U P A 2
H23A H 1.1340 0.8384 1.1207 0.063 Uiso 0.4 1 calc R U P A 2
H23B H 0.9898 0.7026 1.0827 0.063 Uiso 0.4 1 calc R U P A 2
O3A O 1.1949(6) 0.9212(4) 0.9734(4) 0.0549(10) Uani 0.4 1 d D U P A 2
H3A H 1.2198 0.9266 1.0363 0.082 Uiso 0.4 1 calc R U P A 2
C13 C 0.3032(3) 0.53421(18) 0.57527(16) 0.0312(4) Uani 1 1 d . . . . .
C16 C 0.3845(3) 0.55702(18) 0.75462(17) 0.0305(4) Uani 1 1 d . . . . .
H16 H 0.3716 0.5260 0.8075 0.037 Uiso 1 1 calc R U . . .
O2 O 0.0676(2) 0.36997(16) 0.44727(14) 0.0515(4) Uani 1 1 d . . . . .
N5 N 0.1903(3) 0.46341(18) 0.46541(15) 0.0386(4) Uani 1 1 d . . . . .
O1 O 0.2241(3) 0.50168(17) 0.39645(13) 0.0504(7) Uani 0.995(6) 1 d . . P . .
N6 N 0.7943(2) 0.73627(15) 0.91238(13) 0.0299(4) Uani 1 1 d . . . . .
C15 C 0.2795(3) 0.48621(19) 0.65000(17) 0.0320(4) Uani 1 1 d . . . . .
H15 H 0.1943 0.4074 0.6306 0.038 Uiso 1 1 calc R U . . .
C18 C 0.5081(2) 0.67258(18) 0.78289(16) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.5280(3) 0.71757(18) 0.70467(17) 0.0328(4) Uani 1 1 d . . . . .
H17 H 0.6122 0.7965 0.7236 0.039 Uiso 1 1 calc R U . . .
C19 C 0.6117(3) 0.75305(19) 0.89959(17) 0.0338(4) Uani 1 1 d . . . . .
H19A H 0.5402 0.7333 0.9527 0.041 Uiso 1 1 calc R U . . .
H19B H 0.6270 0.8428 0.9214 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4257(3) 0.64762(19) 0.59985(17) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.4397 0.6772 0.5460 0.040 Uiso 1 1 calc R U . . .
C20 C 0.9159(3) 0.7744(2) 0.84000(19) 0.0350(5) Uani 1 1 d . . . . .
H20A H 0.8520 0.7344 0.7628 0.042 Uiso 1 1 calc R U . A 1
H20B H 0.9478 0.8670 0.8704 0.042 Uiso 1 1 calc R U . A 1
C25 C 0.7808(3) 0.60152(19) 0.88284(19) 0.0342(4) Uani 1 1 d . . . . .
H25A H 0.6945 0.5730 0.9255 0.041 Uiso 1 1 calc R U . . .
H25B H 0.7386 0.5455 0.8016 0.041 Uiso 1 1 calc R U . . .
C22 C 1.1051(3) 0.7157(2) 0.94334(18) 0.0349(4) Uani 1 1 d . . . . .
H22 H 1.2260 0.7072 0.9557 0.042 Uiso 1 1 calc R U . A 1
C24 C 0.8774(3) 0.8224(2) 1.03328(18) 0.0466(6) Uani 1 1 d . . . . .
H24A H 0.8195 0.7875 1.0816 0.056 Uiso 1 1 calc R U . A 1
H24B H 0.8607 0.9067 1.0587 0.056 Uiso 1 1 calc R U . A 1
C26 C 0.9635(3) 0.5960(3) 0.9121(4) 0.0754(11) Uani 1 1 d . . . . .
H26A H 0.9614 0.5767 0.9756 0.090 Uiso 1 1 calc R U . . .
H26B H 0.9926 0.5266 0.8470 0.090 Uiso 1 1 calc R U . . .
C5 C 0.2363(3) 0.83947(19) 0.47354(18) 0.0343(4) Uani 1 1 d . . . . .
H5 H 0.1114 0.8286 0.4716 0.041 Uiso 1 1 calc R U . . .
C4 C 0.3473(3) 0.90404(18) 0.57906(18) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.3882(3) 0.9998(2) 0.78472(19) 0.0362(5) Uani 1 1 d . . . . .
C11 C 0.4628(3) 0.69484(19) 0.16541(18) 0.0342(4) Uani 1 1 d . . . . .
C6 C 0.5331(3) 0.91747(19) 0.57799(18) 0.0331(4) Uani 1 1 d . . . . .
H6 H 0.6107 0.9606 0.6472 0.040 Uiso 1 1 calc R U . . .
C9 C 0.4920(3) 0.80554(18) 0.37423(17) 0.0318(4) Uani 1 1 d . . . . .
N3 N 0.3840(3) 0.64297(19) 0.07589(17) 0.0444(5) Uani 1 1 d . . . . .
C8 C 0.3054(3) 0.79271(19) 0.37499(18) 0.0334(4) Uani 1 1 d . . . . .
H8 H 0.2281 0.7509 0.3057 0.040 Uiso 1 1 calc R U . . .
N2 N 0.4819(3) 1.03585(19) 0.86658(16) 0.0444(5) Uani 1 1 d . . . . .
N4 N 0.8902(3) 0.7461(2) 0.26762(19) 0.0501(5) Uani 1 1 d . . . . .
C7 C 0.6024(3) 0.86994(19) 0.47993(18) 0.0333(4) Uani 1 1 d . . . . .
H7 H 0.7272 0.8800 0.4822 0.040 Uiso 1 1 calc R U . . .
C2 C 0.0925(3) 0.9436(2) 0.68712(18) 0.0374(5) Uani 1 1 d . . . . .
C12 C 0.7457(3) 0.7536(2) 0.27106(18) 0.0373(5) Uani 1 1 d . . . . .
C10 C 0.5655(3) 0.7566(2) 0.27299(18) 0.0341(4) Uani 1 1 d . . . . .
C3 C 0.2769(3) 0.95132(19) 0.68221(18) 0.0350(4) Uani 1 1 d . . . . .
N1 N -0.0560(3) 0.9386(2) 0.69167(17) 0.0475(5) 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
C21 C20 1.512(4) . ?
C21 C22 1.591(4) . ?
C23 O3 1.409(4) . ?
C23 C22 1.535(4) . ?
C23 C24 1.534(4) . ?
C21A C22 1.394(7) . ?
C21A O3A 1.405(2) . ?
C21A C20 1.633(6) . ?
C23A C22 1.570(6) . ?
C23A C24 1.678(7) . ?
C13 C14 1.377(3) . ?
C13 C15 1.381(3) . ?
C13 N5 1.469(3) . ?
C16 C18 1.390(3) . ?
C16 C15 1.390(3) . ?
O2 N5 1.224(3) . ?
N5 O1 1.228(2) . ?
N6 C24 1.509(3) . ?
N6 C25 1.511(3) . ?
N6 C20 1.511(3) . ?
N6 C19 1.516(2) . ?
C18 C17 1.397(3) . ?
C18 C19 1.510(3) . ?
C17 C14 1.383(3) . ?
C25 C26 1.510(3) . ?
C22 C26 1.484(3) . ?
C5 C8 1.364(3) . ?
C5 C4 1.421(3) . ?
C4 C3 1.419(3) . ?
C4 C6 1.421(3) . ?
C1 N2 1.156(3) . ?
C1 C3 1.414(3) . ?
C11 N3 1.156(3) . ?
C11 C10 1.416(3) . ?
C6 C7 1.361(3) . ?
C9 C10 1.413(3) . ?
C9 C7 1.421(3) . ?
C9 C8 1.427(3) . ?
N4 C12 1.157(3) . ?
C2 N1 1.150(3) . ?
C2 C3 1.425(3) . ?
C12 C10 1.420(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
C20 C21 C22 106.1(2) . . ?
O3 C23 C22 114.8(3) . . ?
O3 C23 C24 112.2(2) . . ?
C22 C23 C24 108.0(2) . . ?
C22 C21A O3A 111.1(5) . . ?
C22 C21A C20 109.8(4) . . ?
O3A C21A C20 110.8(4) . . ?
C22 C23A C24 99.7(4) . . ?
C14 C13 C15 122.96(19) . . ?
C14 C13 N5 118.01(18) . . ?
C15 C13 N5 119.01(18) . . ?
C18 C16 C15 120.88(18) . . ?
O2 N5 O1 123.39(19) . . ?
O2 N5 C13 118.67(18) . . ?
O1 N5 C13 117.94(19) . . ?
C24 N6 C25 109.47(17) . . ?
C24 N6 C20 107.60(17) . . ?
C25 N6 C20 109.07(15) . . ?
C24 N6 C19 107.66(15) . . ?
C25 N6 C19 111.45(15) . . ?
C20 N6 C19 111.49(16) . . ?
C13 C15 C16 117.77(18) . . ?
C16 C18 C17 119.49(18) . . ?
C16 C18 C19 120.41(18) . . ?
C17 C18 C19 119.98(18) . . ?
C14 C17 C18 120.30(18) . . ?
C18 C19 N6 114.86(15) . . ?
C13 C14 C17 118.58(19) . . ?
C21 C20 N6 111.34(19) . . ?
N6 C20 C21A 103.6(3) . . ?
C26 C25 N6 108.27(17) . . ?
C21A C22 C26 126.2(3) . . ?
C26 C22 C23 115.5(2) . . ?
C21A C22 C23A 112.3(4) . . ?
C26 C22 C23A 87.1(4) . . ?
C26 C22 C21 102.5(2) . . ?
C23 C22 C21 105.4(2) . . ?
N6 C24 C23 108.67(19) . . ?
N6 C24 C23A 108.3(3) . . ?
C22 C26 C25 112.55(19) . . ?
C8 C5 C4 121.40(19) . . ?
C3 C4 C6 120.58(19) . . ?
C3 C4 C5 122.02(19) . . ?
C6 C4 C5 117.39(19) . . ?
N2 C1 C3 177.4(2) . . ?
N3 C11 C10 177.5(2) . . ?
C7 C6 C4 121.42(19) . . ?
C10 C9 C7 120.84(18) . . ?
C10 C9 C8 121.81(18) . . ?
C7 C9 C8 117.36(19) . . ?
C5 C8 C9 121.06(19) . . ?
C6 C7 C9 121.37(19) . . ?
N1 C2 C3 179.3(3) . . ?
N4 C12 C10 177.4(2) . . ?
C9 C10 C11 123.25(19) . . ?
C9 C10 C12 122.22(19) . . ?
C11 C10 C12 114.20(19) . . ?
C1 C3 C4 120.00(19) . . ?
C1 C3 C2 117.44(19) . . ?
C4 C3 C2 122.38(19) . . ?

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_8TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503306'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H15 N6 O2'
_chemical_formula_weight         419.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/a

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

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

_cell_length_a                   7.3613(2)
_cell_length_b                   37.7897(7)
_cell_length_c                   7.9918(2)
_cell_angle_alpha                90
_cell_angle_beta                 115.710(4)
_cell_angle_gamma                90
_cell_volume                     2003.08(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3964
_cell_measurement_theta_min      3.5058
_cell_measurement_theta_max      73.6991

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5110
_exptl_crystal_size_mid          0.2175
_exptl_crystal_size_min          0.0347
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7538
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         4.681
_diffrn_reflns_theta_max         73.861
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3890
_reflns_number_gt                3378
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0350P)²+0.9182P] 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         3890
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
O2 O 0.5758(2) 0.23739(3) 0.52242(17) 0.0406(3) Uani 1 1 d . . . . .
N6 N 0.5950(2) 0.26490(4) 0.45050(18) 0.0291(3) Uani 1 1 d . . . . .
N3 N -0.2465(2) 0.44051(4) 0.00903(19) 0.0293(3) Uani 1 1 d . . . . .
C6 C 0.0704(2) 0.56593(4) 0.50642(19) 0.0193(3) Uani 1 1 d . . . . .
H6 H 0.1742 0.5814 0.5846 0.023 Uiso 1 1 calc R U . . .
C21 C 0.5668(2) 0.26358(4) 0.25714(19) 0.0222(3) Uani 1 1 d . . . . .
C7 C -0.1315(2) 0.57198(4) 0.47988(18) 0.0190(3) Uani 1 1 d . . . . .
N4 N 0.3731(2) 0.47316(4) 0.25133(19) 0.0287(3) Uani 1 1 d . . . . .
N5 N 0.36235(19) 0.35031(3) -0.12896(16) 0.0233(3) Uani 1 1 d . . . . .
C11 C -0.3833(2) 0.61043(4) 0.5231(2) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.0800(2) 0.64741(4) 0.7608(2) 0.0368(3) Uani 1 1 d . . . . .
C5 C 0.1182(2) 0.53847(4) 0.42245(19) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.2543 0.5352 0.4432 0.023 Uiso 1 1 calc R U . . .
C8 C -0.2817(2) 0.54814(4) 0.36162(19) 0.0205(3) Uani 1 1 d . . . . .
H8 H -0.4178 0.5515 0.3408 0.025 Uiso 1 1 calc R U . . .
C2 C 0.0155(2) 0.48577(4) 0.21916(19) 0.0199(3) Uani 1 1 d . . . . .
C9 C -0.2347(2) 0.52058(4) 0.27750(19) 0.0197(3) Uani 1 1 d . . . . .
H9 H -0.3386 0.5051 0.1997 0.024 Uiso 1 1 calc R U . . .
C4 C -0.0329(2) 0.51457(4) 0.30385(18) 0.0189(3) Uani 1 1 d . . . . .
C12 C -0.0362(2) 0.62648(4) 0.6718(2) 0.0252(3) Uani 1 1 d . . . . .
C10 C -0.1824(2) 0.60188(4) 0.5594(2) 0.0217(3) Uani 1 1 d . . . . .
C20 C 0.5639(2) 0.29509(4) 0.1684(2) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.5818 0.3171 0.2309 0.028 Uiso 1 1 calc R U . . .
O1 O 0.6367(3) 0.29314(4) 0.53257(19) 0.0520(4) Uani 1 1 d . . . . .
C1 C -0.1318(2) 0.46119(4) 0.10284(19) 0.0222(3) Uani 1 1 d . . . . .
C3 C 0.2145(2) 0.47940(4) 0.23894(19) 0.0216(3) Uani 1 1 d . . . . .
C24 C 0.5111(2) 0.26068(5) -0.1018(2) 0.0301(4) Uani 1 1 d . . . . .
H24 H 0.4921 0.2595 -0.2270 0.036 Uiso 1 1 calc R U . . .
N2 N -0.5446(2) 0.61901(4) 0.4937(3) 0.0424(4) Uani 1 1 d . . . . .
C22 C 0.5435(2) 0.23069(4) 0.1744(2) 0.0265(3) Uani 1 1 d . . . . .
H22 H 0.5464 0.2096 0.2403 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1709(2) 0.34119(4) -0.2409(2) 0.0262(3) Uani 1 1 d . . . . .
H16 H 0.1457 0.3212 -0.3198 0.031 Uiso 1 1 calc R U . . .
C25 C 0.5336(2) 0.29341(4) -0.0167(2) 0.0256(3) Uani 1 1 d . . . . .
C23 C 0.5156(2) 0.22968(5) -0.0083(2) 0.0311(4) Uani 1 1 d . . . . .
H23 H 0.4996 0.2076 -0.0697 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5271(3) 0.32683(5) -0.1220(2) 0.0333(4) Uani 1 1 d . . . . .
H19A H 0.6578 0.3394 -0.0606 0.040 Uiso 1 1 calc R U . . .
H19B H 0.5052 0.3208 -0.2499 0.040 Uiso 1 1 calc R U . . .
C15 C 0.0125(3) 0.36018(5) -0.2430(3) 0.0381(4) Uani 1 1 d . . . . .
H15 H -0.1222 0.3536 -0.3227 0.046 Uiso 1 1 calc R U . . .
C14 C 0.0518(4) 0.38907(5) -0.1270(3) 0.0524(6) Uani 1 1 d . . . . .
H14 H -0.0561 0.4024 -0.1235 0.063 Uiso 1 1 calc R U . . .
C17 C 0.4038(3) 0.37888(5) -0.0196(2) 0.0403(4) Uani 1 1 d . . . . .
H17 H 0.5399 0.3854 0.0550 0.048 Uiso 1 1 calc R U . . .
C13 C 0.2502(5) 0.39862(5) -0.0153(3) 0.0576(7) Uani 1 1 d . . . . .
H13 H 0.2790 0.4187 0.0634 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
O2 N6 1.2258(18) . ?
N6 O1 1.2199(19) . ?
N6 C21 1.4680(19) . ?
N3 C1 1.156(2) . ?
C6 C5 1.362(2) . ?
C6 C7 1.426(2) . ?
C21 C20 1.381(2) . ?
C21 C22 1.383(2) . ?
C7 C8 1.422(2) . ?
C7 C10 1.424(2) . ?
N4 C3 1.153(2) . ?
N5 C17 1.338(2) . ?
N5 C16 1.346(2) . ?
N5 C19 1.484(2) . ?
C11 N2 1.153(2) . ?
C11 C10 1.415(2) . ?
N1 C12 1.156(2) . ?
C5 C4 1.4269(19) . ?
C8 C9 1.363(2) . ?
C2 C4 1.407(2) . ?
C2 C1 1.424(2) . ?
C2 C3 1.424(2) . ?
C9 C4 1.426(2) . ?
C12 C10 1.411(2) . ?
C20 C25 1.399(2) . ?
C24 C23 1.382(3) . ?
C24 C25 1.387(2) . ?
C22 C23 1.384(2) . ?
C16 C15 1.363(2) . ?
C25 C19 1.507(2) . ?
C15 C14 1.379(3) . ?
C14 C13 1.388(4) . ?
C17 C13 1.367(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
O1 N6 O2 122.90(14) . . ?
O1 N6 C21 118.92(13) . . ?
O2 N6 C21 118.18(13) . . ?
C5 C6 C7 121.60(13) . . ?
C20 C21 C22 123.93(14) . . ?
C20 C21 N6 118.32(13) . . ?
C22 C21 N6 117.75(13) . . ?
C8 C7 C10 121.32(13) . . ?
C8 C7 C6 117.22(13) . . ?
C10 C7 C6 121.35(13) . . ?
C17 N5 C16 121.14(15) . . ?
C17 N5 C19 120.44(15) . . ?
C16 N5 C19 118.34(14) . . ?
N2 C11 C10 176.87(17) . . ?
C6 C5 C4 121.08(13) . . ?
C9 C8 C7 121.43(13) . . ?
C4 C2 C1 122.60(13) . . ?
C4 C2 C3 122.70(13) . . ?
C1 C2 C3 114.67(13) . . ?
C8 C9 C4 121.34(13) . . ?
C2 C4 C9 121.16(13) . . ?
C2 C4 C5 121.49(13) . . ?
C9 C4 C5 117.34(13) . . ?
N1 C12 C10 178.02(17) . . ?
C12 C10 C11 114.87(13) . . ?
C12 C10 C7 122.08(13) . . ?
C11 C10 C7 122.94(14) . . ?
C21 C20 C25 117.62(14) . . ?
N3 C1 C2 177.82(16) . . ?
N4 C3 C2 177.56(16) . . ?
C23 C24 C25 121.44(14) . . ?
C21 C22 C23 117.40(15) . . ?
N5 C16 C15 121.10(16) . . ?
C24 C25 C20 119.31(15) . . ?
C24 C25 C19 120.37(14) . . ?
C20 C25 C19 120.32(15) . . ?
C24 C23 C22 120.29(15) . . ?
N5 C19 C25 110.44(12) . . ?
C16 C15 C14 118.66(19) . . ?
C15 C14 C13 119.56(18) . . ?
N5 C17 C13 119.98(19) . . ?
C17 C13 C14 119.51(18) . . ?

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_10TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503307'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_vrf_PLAT353_shelx               
;
PROBLEM: Long    N-H (N0.87,N1.01A)  N5     -   H1     ..       1.36 Ang.  
RESPONSE: Hydrogen sits between the two nitrogens in protonated proton sponge, long N-H bond lengths seen in other reported protonated proton sponge examples.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 N6'
_chemical_formula_weight         419.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

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

_cell_length_a                   9.6649(3)
_cell_length_b                   7.0560(2)
_cell_length_c                   16.1763(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.103(3)
_cell_angle_gamma                90
_cell_volume                     1096.90(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2965
_cell_measurement_theta_min      4.5974
_cell_measurement_theta_max      73.8172

_exptl_crystal_description       'Thin Plate'
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             442
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2176
_exptl_crystal_size_mid          0.1666
_exptl_crystal_size_min          0.0192
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            7220
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.601
_diffrn_reflns_theta_max         73.981
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2362
_reflns_number_gt                2000
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0986P)²+0.0320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2362
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1452
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C10 C 0.95749(17) 0.2500 0.86827(11) 0.0276(4) Uani 1 2 d S T P . .
N3 N 0.60905(19) 0.2500 0.62727(11) 0.0430(4) Uani 1 2 d S T P . .
N1 N 0.82430(15) 0.2500 0.81580(9) 0.0289(3) Uani 1 2 d S T P . .
C24 C 0.6507(2) 0.2500 0.10662(13) 0.0373(4) Uani 1 2 d S T P . .
C23 C 0.7246(2) 0.2500 0.18733(11) 0.0321(4) Uani 1 2 d S T P . .
C25 C 0.8708(2) 0.2500 0.19134(11) 0.0321(4) Uani 1 2 d S T P . .
C19 C 0.6729(2) 0.2500 0.41208(12) 0.0335(4) Uani 1 2 d S T P . .
H19 H 0.7286 0.2500 0.4641 0.040 Uiso 1 2 calc R U P . .
N6 N 0.99165(18) 0.2500 0.19804(11) 0.0400(4) Uani 1 2 d S T P . .
N5 N 0.5926(2) 0.2500 0.04053(12) 0.0543(5) Uani 1 2 d S T P . .
C12 C 0.74055(13) 0.07792(19) 0.82679(8) 0.0353(3) Uani 1 1 d . . . . .
H12A H 0.7969 -0.0350 0.8192 0.053 Uiso 1 1 calc R U . . .
H12B H 0.6585 0.0776 0.7856 0.053 Uiso 1 1 calc R U . . .
H12C H 0.7108 0.0772 0.8829 0.053 Uiso 1 1 calc R U . . .
C13 C 0.93991(14) 0.07678(19) 0.63379(8) 0.0364(3) Uani 1 1 d . . . . .
H13C H 0.8460 0.0751 0.6042 0.055 Uiso 1 1 calc R U . . .
H13A H 0.9533 -0.0357 0.6693 0.055 Uiso 1 1 calc R U . . .
H13B H 1.0086 0.0766 0.5934 0.055 Uiso 1 1 calc R U . . .
H1 H 0.877(3) 0.2500 0.7401(19) 0.064(8) Uiso 1 2 d S . P . .
N2 N 0.95784(15) 0.2500 0.68597(9) 0.0288(3) Uani 1 2 d S T P . .
C4 C 1.33881(18) 0.2500 0.84428(11) 0.0310(4) Uani 1 2 d S T P . .
H4 H 1.4244 0.2500 0.8791 0.037 Uiso 1 2 calc R U P . .
C2 C 1.21337(19) 0.2500 0.70778(12) 0.0321(4) Uani 1 2 d S T P . .
H2 H 1.2145 0.2500 0.6491 0.039 Uiso 1 2 calc R U P . .
C6 C 1.08235(16) 0.2500 0.82830(10) 0.0258(4) Uani 1 2 d S T P . .
C7 C 1.21192(19) 0.2500 0.96785(12) 0.0330(4) Uani 1 2 d S T P . .
H7 H 1.2979 0.2500 1.0023 0.040 Uiso 1 2 calc R U P . .
C5 C 1.21182(18) 0.2500 0.88061(11) 0.0281(4) Uani 1 2 d S T P . .
C9 C 0.96124(19) 0.2500 0.95276(11) 0.0332(4) Uani 1 2 d S T P . .
H9 H 0.8767 0.2500 0.9779 0.040 Uiso 1 2 calc R U P . .
C8 C 1.0897(2) 0.2500 1.00326(12) 0.0362(4) Uani 1 2 d S T P . .
H8 H 1.0912 0.2500 1.0621 0.043 Uiso 1 2 calc R U P . .
C1 C 1.08950(18) 0.2500 0.74107(11) 0.0279(4) Uani 1 2 d S T P . .
C3 C 1.34010(18) 0.2500 0.76017(12) 0.0331(4) Uani 1 2 d S T P . .
H3 H 1.4261 0.2500 0.7367 0.040 Uiso 1 2 calc R U P . .
C21 C 0.73590(19) 0.2500 0.34053(12) 0.0326(4) Uani 1 2 d S T P . .
H21 H 0.8346 0.2500 0.3440 0.039 Uiso 1 2 calc R U P . .
N4 N 0.19530(18) 0.2500 0.48611(10) 0.0414(4) Uani 1 2 d S T P . .
C15 C 0.3154(2) 0.2500 0.48580(11) 0.0336(4) Uani 1 2 d S T P . .
C20 C 0.51140(19) 0.2500 0.25926(11) 0.0315(4) Uani 1 2 d S T P . .
H20 H 0.4558 0.2500 0.2072 0.038 Uiso 1 2 calc R U P . .
C22 C 0.65798(18) 0.2500 0.26100(11) 0.0294(4) Uani 1 2 d S T P . .
C18 C 0.44773(19) 0.2500 0.33093(11) 0.0317(4) Uani 1 2 d S T P . .
H18 H 0.3490 0.2500 0.3274 0.038 Uiso 1 2 calc R U P . .
C16 C 0.4613(2) 0.2500 0.48501(11) 0.0328(4) Uani 1 2 d S T P . .
C14 C 0.5414(2) 0.2500 0.56388(12) 0.0342(4) Uani 1 2 d S T P . .
C17 C 0.52595(19) 0.2500 0.41037(11) 0.0307(4) Uani 1 2 d S T P . .


_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
C10 C9 1.363(3) . ?
C10 C6 1.428(2) . ?
C10 N1 1.465(2) . ?
N3 C14 1.156(3) . ?
N1 C12 1.4804(15) 4_565 ?
N1 C12 1.4804(15) . ?
C24 N5 1.154(3) . ?
C24 C23 1.420(3) . ?
C23 C25 1.408(3) . ?
C23 C22 1.414(3) . ?
C25 N6 1.161(3) . ?
C19 C21 1.364(3) . ?
C19 C17 1.418(3) . ?
C13 N2 1.4850(15) . ?
N2 C1 1.474(2) . ?
N2 C13 1.4851(15) 4_565 ?
C4 C3 1.362(3) . ?
C4 C5 1.416(2) . ?
C2 C1 1.364(3) . ?
C2 C3 1.413(3) . ?
C6 C1 1.420(2) . ?
C6 C5 1.434(2) . ?
C7 C8 1.367(3) . ?
C7 C5 1.411(3) . ?
C9 C8 1.412(3) . ?
C21 C22 1.420(3) . ?
N4 C15 1.161(3) . ?
C15 C16 1.412(3) . ?
C20 C18 1.369(3) . ?
C20 C22 1.414(3) . ?
C18 C17 1.420(3) . ?
C16 C17 1.417(3) . ?
C16 C14 1.420(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 C10 C6 121.34(16) . . ?
C9 C10 N1 120.60(16) . . ?
C6 C10 N1 118.06(15) . . ?
C10 N1 C12 112.86(9) . 4_565 ?
C10 N1 C12 112.86(9) . . ?
C12 N1 C12 110.20(14) 4_565 . ?
N5 C24 C23 178.9(2) . . ?
C25 C23 C22 120.41(16) . . ?
C25 C23 C24 116.54(17) . . ?
C22 C23 C24 123.05(18) . . ?
N6 C25 C23 177.30(19) . . ?
C21 C19 C17 121.34(18) . . ?
C1 N2 C13 112.63(9) . . ?
C1 N2 C13 112.63(9) . 4_565 ?
C13 N2 C13 110.78(14) . 4_565 ?
C3 C4 C5 120.99(16) . . ?
C1 C2 C3 120.28(18) . . ?
C1 C6 C10 125.63(16) . . ?
C1 C6 C5 117.04(15) . . ?
C10 C6 C5 117.33(16) . . ?
C8 C7 C5 120.69(17) . . ?
C7 C5 C4 120.43(16) . . ?
C7 C5 C6 119.86(16) . . ?
C4 C5 C6 119.71(16) . . ?
C10 C9 C8 120.54(17) . . ?
C7 C8 C9 120.25(18) . . ?
C2 C1 C6 122.00(16) . . ?
C2 C1 N2 119.92(16) . . ?
C6 C1 N2 118.08(15) . . ?
C4 C3 C2 119.98(17) . . ?
C19 C21 C22 121.82(17) . . ?
N4 C15 C16 179.7(2) . . ?
C18 C20 C22 121.52(17) . . ?
C23 C22 C20 121.90(16) . . ?
C23 C22 C21 121.23(17) . . ?
C20 C22 C21 116.86(16) . . ?
C20 C18 C17 121.49(17) . . ?
C15 C16 C17 122.60(17) . . ?
C15 C16 C14 116.20(17) . . ?
C17 C16 C14 121.20(18) . . ?
N3 C14 C16 178.6(2) . . ?
C16 C17 C19 120.97(17) . . ?
C16 C17 C18 122.06(17) . . ?
C19 C17 C18 116.97(17) . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_9TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503308'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H28 N12'
_chemical_formula_weight         676.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.6808(2)
_cell_length_b                   13.9762(5)
_cell_length_c                   18.9142(7)
_cell_angle_alpha                96.805(3)
_cell_angle_beta                 100.163(3)
_cell_angle_gamma                95.734(3)
_cell_volume                     1712.86(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5141
_cell_measurement_theta_min      3.2064
_cell_measurement_theta_max      73.7448

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1989
_exptl_crystal_size_mid          0.1264
_exptl_crystal_size_min          0.0530
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_reflns_number            10746
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         67.474
_diffrn_reflns_theta_full        67.474
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6146
_reflns_number_gt                5115
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0562P)²+0.0757P] 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         6146
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C40 C -0.2765(3) 0.20502(10) 0.38023(8) 0.0435(4) Uani 1 1 d . . . . .
H40A H -0.1865 0.2600 0.3709 0.065 Uiso 1 1 calc R U . . .
H40B H -0.3197 0.2215 0.4266 0.065 Uiso 1 1 calc R U . . .
H40C H -0.3974 0.1906 0.3412 0.065 Uiso 1 1 calc R U . . .
N9 N 0.04376(17) 0.01712(7) 0.36186(6) 0.0318(2) Uani 1 1 d . . . . .
N10 N -0.29981(16) -0.39591(7) 0.10453(6) 0.0294(2) Uani 1 1 d . . . . .
N11 N -0.16573(18) 0.11981(7) 0.38324(6) 0.0327(2) Uani 1 1 d . . . . .
N12 N -0.46778(17) -0.49937(7) 0.15487(6) 0.0330(2) Uani 1 1 d . . . . .
C30 C 0.1619(2) -0.24609(9) 0.18685(7) 0.0308(3) Uani 1 1 d . . . . .
H30 H 0.2491 -0.2910 0.1718 0.037 Uiso 1 1 calc R U . . .
C31 C -0.0397(2) -0.25367(9) 0.15079(7) 0.0291(3) Uani 1 1 d . . . . .
C37 C -0.4985(2) -0.40985(9) 0.06666(7) 0.0340(3) Uani 1 1 d . . . . .
H37 H -0.5517 -0.3797 0.0261 0.041 Uiso 1 1 calc R U . . .
C27 C 0.2377(2) -0.17334(9) 0.24493(7) 0.0324(3) Uani 1 1 d . . . . .
H27 H 0.3759 -0.1691 0.2695 0.039 Uiso 1 1 calc R U . . .
C35 C -0.2097(2) 0.04219(9) 0.41879(7) 0.0325(3) Uani 1 1 d . . . . .
H35 H -0.3124 0.0353 0.4474 0.039 Uiso 1 1 calc R U . . .
C38 C -0.6034(2) -0.47478(9) 0.09838(8) 0.0364(3) Uani 1 1 d . . . . .
H38 H -0.7447 -0.4990 0.0843 0.044 Uiso 1 1 calc R U . . .
C34 C -0.0785(2) -0.02229(9) 0.40521(7) 0.0328(3) Uani 1 1 d . . . . .
H34 H -0.0719 -0.0833 0.4224 0.039 Uiso 1 1 calc R U . . .
C28 C -0.0883(2) -0.11329(9) 0.23043(7) 0.0325(3) Uani 1 1 d . . . . .
H28 H -0.1745 -0.0675 0.2447 0.039 Uiso 1 1 calc R U . . .
C32 C -0.1238(2) -0.33463(10) 0.08907(7) 0.0351(3) Uani 1 1 d . . . . .
H32A H -0.1675 -0.3064 0.0441 0.042 Uiso 1 1 calc R U . . .
H32B H -0.0146 -0.3753 0.0811 0.042 Uiso 1 1 calc R U . . .
C26 C 0.1126(2) -0.10697(9) 0.26725(7) 0.0304(3) Uani 1 1 d . . . . .
C36 C -0.2866(2) -0.45081(9) 0.15716(7) 0.0327(3) Uani 1 1 d . . . . .
H36 H -0.1657 -0.4546 0.1912 0.039 Uiso 1 1 calc R U . . .
C33 C -0.0136(2) 0.10287(9) 0.34920(7) 0.0341(3) Uani 1 1 d . . . . .
H33 H 0.0451 0.1450 0.3204 0.041 Uiso 1 1 calc R U . . .
C29 C -0.1634(2) -0.18638(9) 0.17284(7) 0.0327(3) Uani 1 1 d . . . . .
H29 H -0.3014 -0.1905 0.1482 0.039 Uiso 1 1 calc R U . . .
C25 C 0.2021(2) -0.02967(10) 0.33136(8) 0.0388(3) Uani 1 1 d . . . . .
H25A H 0.2851 -0.0596 0.3695 0.047 Uiso 1 1 calc R U . . .
H25B H 0.2942 0.0202 0.3157 0.047 Uiso 1 1 calc R U . . .
C39 C -0.5088(3) -0.56791(10) 0.20473(8) 0.0447(4) Uani 1 1 d . . . . .
H39A H -0.4181 -0.6186 0.2022 0.067 Uiso 1 1 calc R U . . .
H39B H -0.6519 -0.5976 0.1911 0.067 Uiso 1 1 calc R U . . .
H39C H -0.4840 -0.5335 0.2543 0.067 Uiso 1 1 calc R U . . .
C9 C 0.22108(17) 0.52202(8) 0.43163(7) 0.0257(2) Uani 1 1 d . . . . .
C5 C 0.29187(18) 0.46876(8) 0.55034(7) 0.0266(2) Uani 1 1 d . . . . .
H5 H 0.3099 0.4837 0.6016 0.032 Uiso 1 1 calc R U . . .
C7 C 0.23309(18) 0.42520(8) 0.40000(7) 0.0272(3) Uani 1 1 d . . . . .
H7 H 0.2109 0.4100 0.3487 0.033 Uiso 1 1 calc R U . . .
C8 C 0.24937(17) 0.53976(8) 0.50825(7) 0.0264(2) Uani 1 1 d . . . . .
H8 H 0.2384 0.6029 0.5310 0.032 Uiso 1 1 calc R U . . .
C4 C 0.30986(17) 0.37284(8) 0.51922(7) 0.0253(2) Uani 1 1 d . . . . .
N3 N 0.12353(17) 0.76826(8) 0.43941(7) 0.0359(3) Uani 1 1 d . . . . .
C6 C 0.27577(18) 0.35439(8) 0.44196(7) 0.0270(3) Uani 1 1 d . . . . .
H6 H 0.2831 0.2909 0.4191 0.032 Uiso 1 1 calc R U . . .
C11 C 0.15103(18) 0.69134(9) 0.41642(7) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.39327(19) 0.12917(8) 0.50203(7) 0.0388(3) Uani 1 1 d . . . . .
N2 N 0.36360(19) 0.32888(9) 0.70033(7) 0.0409(3) Uani 1 1 d . . . . .
C1 C 0.37608(19) 0.20510(9) 0.53056(7) 0.0298(3) Uani 1 1 d . . . . .
C12 C 0.1608(2) 0.57518(9) 0.31179(7) 0.0318(3) Uani 1 1 d . . . . .
C3 C 0.35680(18) 0.29987(9) 0.56282(7) 0.0277(3) Uani 1 1 d . . . . .
C2 C 0.36298(19) 0.31487(9) 0.63894(7) 0.0309(3) Uani 1 1 d . . . . .
N4 N 0.1483(2) 0.55340(9) 0.25019(7) 0.0420(3) Uani 1 1 d . . . . .
C10 C 0.18159(18) 0.59622(9) 0.38814(7) 0.0283(3) Uani 1 1 d . . . . .
C17 C 0.77725(18) 0.97664(8) 0.03140(7) 0.0262(2) Uani 1 1 d . . . . .
H17 H 0.7858 0.9143 0.0462 0.031 Uiso 1 1 calc R U . . .
C15 C 0.60400(19) 0.90132(9) -0.09278(7) 0.0277(3) Uani 1 1 d . . . . .
C19 C 0.85359(18) 1.05753(9) 0.08023(7) 0.0267(2) Uani 1 1 d . . . . .
H19 H 0.9137 1.0503 0.1284 0.032 Uiso 1 1 calc R U . . .
N6 N 0.91341(18) 1.40586(8) 0.06682(6) 0.0362(3) Uani 1 1 d . . . . .
C20 C 0.75567(18) 1.15910(9) -0.01251(7) 0.0273(3) Uani 1 1 d . . . . .
H20 H 0.7495 1.2214 -0.0276 0.033 Uiso 1 1 calc R U . . .
C21 C 0.84505(18) 1.15246(9) 0.06052(7) 0.0264(2) Uani 1 1 d . . . . .
C18 C 0.67899(18) 1.07879(8) -0.06119(7) 0.0269(2) Uani 1 1 d . . . . .
H18 H 0.6201 1.0861 -0.1095 0.032 Uiso 1 1 calc R U . . .
C16 C 0.68529(17) 0.98368(8) -0.04118(7) 0.0251(2) Uani 1 1 d . . . . .
C13 C 0.60547(19) 0.80514(9) -0.07577(7) 0.0292(3) Uani 1 1 d . . . . .
C24 C 0.91897(19) 1.33101(9) 0.08676(7) 0.0299(3) Uani 1 1 d . . . . .
N5 N 1.1218(2) 1.23692(9) 0.23910(7) 0.0488(3) Uani 1 1 d . . . . .
N7 N 0.60572(18) 0.72700(8) -0.06214(7) 0.0371(3) Uani 1 1 d . . . . .
N8 N 0.4538(2) 0.92393(9) -0.22402(7) 0.0432(3) Uani 1 1 d . . . . .
C22 C 0.92656(19) 1.23806(9) 0.10945(7) 0.0290(3) Uani 1 1 d . . . . .
C23 C 1.0319(2) 1.23631(9) 0.18092(7) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.5200(2) 0.91179(9) -0.16557(7) 0.0317(3) 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
C40 N11 1.4651(17) . ?
N9 C33 1.3296(17) . ?
N9 C34 1.3772(17) . ?
N9 C25 1.4640(17) . ?
N10 C36 1.3233(17) . ?
N10 C37 1.3760(17) . ?
N10 C32 1.4768(17) . ?
N11 C33 1.3216(18) . ?
N11 C35 1.3761(16) . ?
N12 C36 1.3184(18) . ?
N12 C38 1.3741(19) . ?
N12 C39 1.4612(18) . ?
C30 C31 1.3863(19) . ?
C30 C27 1.3902(19) . ?
C31 C29 1.3877(18) . ?
C31 C32 1.5124(18) . ?
C37 C38 1.351(2) . ?
C27 C26 1.3869(18) . ?
C35 C34 1.3521(19) . ?
C28 C29 1.3866(19) . ?
C28 C26 1.3882(19) . ?
C26 C25 1.5165(18) . ?
C9 C10 1.4150(17) . ?
C9 C8 1.4164(17) . ?
C9 C7 1.4291(16) . ?
C5 C8 1.3648(17) . ?
C5 C4 1.4241(16) . ?
C7 C6 1.3613(17) . ?
C4 C3 1.4108(17) . ?
C4 C6 1.4266(17) . ?
N3 C11 1.1556(17) . ?
C11 C10 1.4210(17) . ?
N1 C1 1.1581(17) . ?
N2 C2 1.1535(18) . ?
C1 C3 1.4191(17) . ?
C12 N4 1.1549(18) . ?
C12 C10 1.4183(18) . ?
C3 C2 1.4228(18) . ?
C17 C19 1.3647(17) . ?
C17 C16 1.4205(17) . ?
C15 C16 1.4123(17) . ?
C15 C13 1.4193(17) . ?
C15 C14 1.4224(18) . ?
C19 C21 1.4239(17) . ?
N6 C24 1.1552(17) . ?
C20 C18 1.3580(17) . ?
C20 C21 1.4225(17) . ?
C21 C22 1.4191(17) . ?
C18 C16 1.4272(16) . ?
C13 N7 1.1516(17) . ?
C24 C22 1.4185(18) . ?
N5 C23 1.1555(19) . ?
N8 C14 1.1549(18) . ?
C22 C23 1.4138(19) . ?

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
C33 N9 C34 108.40(11) . . ?
C33 N9 C25 125.62(12) . . ?
C34 N9 C25 125.90(11) . . ?
C36 N10 C37 108.54(11) . . ?
C36 N10 C32 123.95(11) . . ?
C37 N10 C32 127.45(12) . . ?
C33 N11 C35 108.90(11) . . ?
C33 N11 C40 125.36(12) . . ?
C35 N11 C40 125.67(12) . . ?
C36 N12 C38 108.36(12) . . ?
C36 N12 C39 123.99(13) . . ?
C38 N12 C39 127.64(12) . . ?
C31 C30 C27 120.52(11) . . ?
C30 C31 C29 118.85(11) . . ?
C30 C31 C32 120.49(11) . . ?
C29 C31 C32 120.66(12) . . ?
C38 C37 N10 106.63(12) . . ?
C26 C27 C30 120.36(12) . . ?
C34 C35 N11 106.81(12) . . ?
C37 C38 N12 107.30(12) . . ?
C35 C34 N9 107.12(11) . . ?
C29 C28 C26 120.11(12) . . ?
N10 C32 C31 111.40(10) . . ?
C27 C26 C28 119.27(12) . . ?
C27 C26 C25 118.28(12) . . ?
C28 C26 C25 122.45(11) . . ?
N12 C36 N10 109.18(12) . . ?
N11 C33 N9 108.78(12) . . ?
C28 C29 C31 120.88(12) . . ?
N9 C25 C26 112.42(11) . . ?
C10 C9 C8 121.82(11) . . ?
C10 C9 C7 121.31(11) . . ?
C8 C9 C7 116.86(11) . . ?
C8 C5 C4 121.50(11) . . ?
C6 C7 C9 121.26(11) . . ?
C5 C8 C9 121.87(11) . . ?
C3 C4 C5 121.46(11) . . ?
C3 C4 C6 121.98(11) . . ?
C5 C4 C6 116.56(11) . . ?
C7 C6 C4 121.90(11) . . ?
N3 C11 C10 179.10(14) . . ?
N1 C1 C3 177.51(13) . . ?
N4 C12 C10 176.26(14) . . ?
C4 C3 C1 120.41(11) . . ?
C4 C3 C2 121.61(11) . . ?
C1 C3 C2 117.59(11) . . ?
N2 C2 C3 177.95(14) . . ?
C9 C10 C12 119.48(11) . . ?
C9 C10 C11 123.43(11) . . ?
C12 C10 C11 117.01(11) . . ?
C19 C17 C16 121.36(11) . . ?
C16 C15 C13 122.50(11) . . ?
C16 C15 C14 120.65(11) . . ?
C13 C15 C14 116.83(11) . . ?
C17 C19 C21 121.42(11) . . ?
C18 C20 C21 121.73(11) . . ?
C22 C21 C20 120.04(11) . . ?
C22 C21 C19 122.92(11) . . ?
C20 C21 C19 117.01(11) . . ?
C20 C18 C16 121.23(11) . . ?
C15 C16 C17 122.63(11) . . ?
C15 C16 C18 120.14(11) . . ?
C17 C16 C18 117.23(11) . . ?
N7 C13 C15 179.67(17) . . ?
N6 C24 C22 178.53(13) . . ?
C23 C22 C24 116.13(11) . . ?
C23 C22 C21 122.86(11) . . ?
C24 C22 C21 120.86(11) . . ?
N5 C23 C22 178.16(14) . . ?
N8 C14 C15 177.48(14) . . ?

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_10F4TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503309'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_vrf_PLAT353_shelx               
;
PROBLEM: Long    N-H (N0.87,N1.01A)  N5     -   H1     ..       1.36 Ang.  
RESPONSE: Hydrogen sits between the two nitrogens in protonated proton sponge, long N-H bond lengths seen in other reported protonated proton sponge examples.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H19 F4 N6'
_chemical_formula_weight         491.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   7.1455(4)
_cell_length_b                   9.8840(7)
_cell_length_c                   16.2700(9)
_cell_angle_alpha                82.795(5)
_cell_angle_beta                 89.046(5)
_cell_angle_gamma                82.020(6)
_cell_volume                     1128.97(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    3150
_cell_measurement_theta_min      4.5489
_cell_measurement_theta_max      74.5482

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1934
_exptl_crystal_size_mid          0.1371
_exptl_crystal_size_min          0.0406
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            7692
_diffrn_reflns_av_unetI/netI     0.0696
_diffrn_reflns_av_R_equivalents  0.0808
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.553
_diffrn_reflns_theta_max         74.720
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4442
_reflns_number_gt                3499
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1462P)²+1.2512P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4442
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.3038
_refine_ls_wR_factor_gt          0.2886
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_restrained_S_all      1.245
_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
C25 C 0.4343(5) 1.4182(4) -0.1388(2) 0.0340(8) Uani 1 1 d . . . . .
H25A H 0.5437 1.4323 -0.1744 0.051 Uiso 1 1 calc R U . . .
H25B H 0.4459 1.3216 -0.1143 0.051 Uiso 1 1 calc R U . . .
H25C H 0.4294 1.4774 -0.0946 0.051 Uiso 1 1 calc R U . . .
C26 C 0.0869(5) 1.4438(4) -0.1361(2) 0.0353(8) Uani 1 1 d . . . . .
H26A H 0.0821 1.5093 -0.0953 0.053 Uiso 1 1 calc R U . . .
H26B H 0.0922 1.3502 -0.1072 0.053 Uiso 1 1 calc R U . . .
H26C H -0.0263 1.4656 -0.1710 0.053 Uiso 1 1 calc R U . . .
H1 H 0.260(8) 1.371(6) -0.242(4) 0.059(15) Uiso 1 1 d . . . . .
F2 F 0.1856(3) 0.8203(2) 0.18000(13) 0.0349(5) Uani 1 1 d . . . . .
F1 F 0.1849(3) 0.9384(2) 0.31625(13) 0.0326(5) Uani 1 1 d . . . . .
F4 F 0.3083(3) 1.3517(2) 0.15655(13) 0.0353(5) Uani 1 1 d . . . . .
F3 F 0.3035(3) 1.2371(2) 0.02216(13) 0.0375(6) Uani 1 1 d . . . . .
N5 N 0.2665(4) 1.3309(3) -0.31905(18) 0.0281(6) Uani 1 1 d . . . . .
C8 C 0.2738(5) 1.2211(4) 0.1644(2) 0.0281(7) Uani 1 1 d . . . . .
N6 N 0.2586(4) 1.4535(3) -0.18885(18) 0.0280(7) Uani 1 1 d . . . . .
C22 C 0.2483(4) 1.5848(3) -0.32950(19) 0.0251(7) Uani 1 1 d . . . . .
C7 C 0.2467(5) 1.1522(4) 0.2450(2) 0.0271(7) Uani 1 1 d . . . . .
C4 C 0.2401(5) 1.0227(4) 0.0925(2) 0.0268(7) Uani 1 1 d . . . . .
C2 C 0.2598(5) 1.0336(4) -0.0616(2) 0.0321(8) Uani 1 1 d . . . . .
C17 C 0.2423(5) 1.7148(4) -0.3798(2) 0.0276(7) Uani 1 1 d . . . . .
C12 C 0.2622(5) 1.3585(4) 0.3162(2) 0.0306(8) Uani 1 1 d . . . . .
C6 C 0.2161(5) 1.0139(4) 0.2436(2) 0.0270(7) Uani 1 1 d . . . . .
C1 C 0.2116(5) 0.8218(4) 0.0161(2) 0.0331(8) Uani 1 1 d . . . . .
C18 C 0.2403(5) 1.8368(4) -0.3424(2) 0.0311(8) Uani 1 1 d . . . . .
H18 H 0.2370 1.9226 -0.3763 0.037 Uiso 1 1 calc R U . . .
C20 C 0.2478(5) 1.7059(4) -0.2078(2) 0.0306(8) Uani 1 1 d . . . . .
H20 H 0.2490 1.7034 -0.1492 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2510(5) 1.2152(4) 0.3175(2) 0.0286(7) Uani 1 1 d . . . . .
N2 N 0.1927(6) 0.7106(4) 0.0070(2) 0.0437(9) Uani 1 1 d . . . . .
C11 C 0.2449(6) 1.1454(4) 0.3995(2) 0.0344(8) Uani 1 1 d . . . . .
C9 C 0.2709(5) 1.1607(4) 0.0942(2) 0.0285(8) Uani 1 1 d . . . . .
C16 C 0.2396(5) 1.7196(4) -0.4675(2) 0.0327(8) Uani 1 1 d . . . . .
H16 H 0.2349 1.8057 -0.5013 0.039 Uiso 1 1 calc R U . . .
C14 C 0.2511(5) 1.4735(4) -0.4547(2) 0.0324(8) Uani 1 1 d . . . . .
H14 H 0.2542 1.3924 -0.4807 0.039 Uiso 1 1 calc R U . . .
N4 N 0.2704(5) 1.4735(4) 0.3163(2) 0.0396(8) Uani 1 1 d . . . . .
C5 C 0.2133(5) 0.9530(4) 0.1730(2) 0.0277(7) Uani 1 1 d . . . . .
C15 C 0.2436(6) 1.6023(4) -0.5036(2) 0.0339(8) Uani 1 1 d . . . . .
H15 H 0.2413 1.6073 -0.5623 0.041 Uiso 1 1 calc R U . . .
N1 N 0.2775(5) 1.0857(4) -0.1282(2) 0.0413(8) Uani 1 1 d . . . . .
C3 C 0.2380(5) 0.9612(4) 0.0187(2) 0.0303(8) Uani 1 1 d . . . . .
C21 C 0.2507(5) 1.5864(4) -0.2417(2) 0.0282(7) Uani 1 1 d . . . . .
N3 N 0.2435(6) 1.0971(4) 0.4676(2) 0.0506(10) Uani 1 1 d . . . . .
C19 C 0.2431(5) 1.8327(4) -0.2582(2) 0.0337(8) Uani 1 1 d . . . . .
H19 H 0.2418 1.9153 -0.2338 0.040 Uiso 1 1 calc R U . . .
C13 C 0.2541(5) 1.4644(4) -0.3703(2) 0.0270(7) Uani 1 1 d . . . . .
C24 C 0.1061(5) 1.2551(4) -0.3311(2) 0.0343(8) Uani 1 1 d . . . . .
H24A H -0.0130 1.3131 -0.3215 0.051 Uiso 1 1 calc R U . . .
H24B H 0.1171 1.1706 -0.2919 0.051 Uiso 1 1 calc R U . . .
H24C H 0.1083 1.2314 -0.3878 0.051 Uiso 1 1 calc R U . . .
C23 C 0.4478(5) 1.2433(4) -0.3294(2) 0.0359(8) Uani 1 1 d . . . . .
H23A H 0.4551 1.2165 -0.3855 0.054 Uiso 1 1 calc R U . . .
H23B H 0.4565 1.1606 -0.2889 0.054 Uiso 1 1 calc R U . . .
H23C H 0.5524 1.2945 -0.3209 0.054 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
C25 N6 1.484(4) . ?
C26 N6 1.493(4) . ?
F2 C5 1.344(4) . ?
F1 C6 1.349(4) . ?
F4 C8 1.338(4) . ?
F3 C9 1.347(4) . ?
N5 C13 1.462(4) . ?
N5 C23 1.475(5) . ?
N5 C24 1.482(5) . ?
C8 C9 1.356(5) . ?
C8 C7 1.423(5) . ?
N6 C21 1.472(4) . ?
C22 C13 1.429(5) . ?
C22 C17 1.430(5) . ?
C22 C21 1.431(5) . ?
C7 C10 1.404(5) . ?
C7 C6 1.417(5) . ?
C4 C3 1.414(5) . ?
C4 C9 1.415(5) . ?
C4 C5 1.425(5) . ?
C2 N1 1.152(5) . ?
C2 C3 1.426(5) . ?
C17 C18 1.415(5) . ?
C17 C16 1.422(5) . ?
C12 N4 1.146(5) . ?
C12 C10 1.427(5) . ?
C6 C5 1.364(5) . ?
C1 N2 1.154(5) . ?
C1 C3 1.422(5) . ?
C18 C19 1.365(5) . ?
C20 C21 1.363(5) . ?
C20 C19 1.406(5) . ?
C10 C11 1.425(5) . ?
C11 N3 1.151(5) . ?
C16 C15 1.360(6) . ?
C14 C13 1.366(5) . ?
C14 C15 1.409(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N5 C23 112.5(3) . . ?
C13 N5 C24 113.4(3) . . ?
C23 N5 C24 110.4(3) . . ?
F4 C8 C9 117.3(3) . . ?
F4 C8 C7 119.1(3) . . ?
C9 C8 C7 123.6(3) . . ?
C21 N6 C25 112.8(3) . . ?
C21 N6 C26 112.7(3) . . ?
C25 N6 C26 111.5(3) . . ?
C13 C22 C17 117.9(3) . . ?
C13 C22 C21 125.4(3) . . ?
C17 C22 C21 116.7(3) . . ?
C10 C7 C6 124.2(3) . . ?
C10 C7 C8 123.2(3) . . ?
C6 C7 C8 112.6(3) . . ?
C3 C4 C9 123.3(3) . . ?
C3 C4 C5 124.0(3) . . ?
C9 C4 C5 112.7(3) . . ?
N1 C2 C3 176.4(4) . . ?
C18 C17 C16 120.7(3) . . ?
C18 C17 C22 120.1(3) . . ?
C16 C17 C22 119.2(3) . . ?
N4 C12 C10 179.0(4) . . ?
F1 C6 C5 117.9(3) . . ?
F1 C6 C7 118.2(3) . . ?
C5 C6 C7 123.9(3) . . ?
N2 C1 C3 174.4(4) . . ?
C19 C18 C17 120.9(3) . . ?
C21 C20 C19 120.9(3) . . ?
C7 C10 C11 124.6(3) . . ?
C7 C10 C12 122.7(3) . . ?
C11 C10 C12 112.8(3) . . ?
N3 C11 C10 175.2(4) . . ?
F3 C9 C8 117.3(3) . . ?
F3 C9 C4 118.7(3) . . ?
C8 C9 C4 124.0(3) . . ?
C15 C16 C17 120.8(3) . . ?
C13 C14 C15 120.5(3) . . ?
F2 C5 C6 118.2(3) . . ?
F2 C5 C4 118.5(3) . . ?
C6 C5 C4 123.2(3) . . ?
C16 C15 C14 120.6(3) . . ?
C4 C3 C1 124.1(3) . . ?
C4 C3 C2 123.2(3) . . ?
C1 C3 C2 112.7(3) . . ?
C20 C21 C22 121.6(3) . . ?
C20 C21 N6 120.8(3) . . ?
C22 C21 N6 117.5(3) . . ?
C18 C19 C20 119.7(4) . . ?
C14 C13 C22 121.0(3) . . ?
C14 C13 N5 120.9(3) . . ?
C22 C13 N5 118.1(3) . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_4TCNQ
_database_code_depnum_ccdc_archive 'CCDC 1503310'
_audit_update_record             
;
2016-10-24 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H30 N10'
_chemical_formula_weight         770.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.7053(5)
_cell_length_b                   10.2744(7)
_cell_length_c                   12.1391(9)
_cell_angle_alpha                90.196(6)
_cell_angle_beta                 97.753(6)
_cell_angle_gamma                97.100(6)
_cell_volume                     944.74(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2059
_cell_measurement_theta_min      3.6725
_cell_measurement_theta_max      73.6924

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Dark Purple'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3249
_exptl_crystal_size_mid          0.1971
_exptl_crystal_size_min          0.0419
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      130.01(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            6227
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.676
_diffrn_reflns_theta_max         69.983
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3568
_reflns_number_gt                2829
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0738P)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         3568
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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
N5 N 0.51348(18) 0.04477(13) 0.80369(11) 0.0265(3) Uani 1 1 d . . . . .
C16 C 0.5972(2) -0.14367(15) 0.90043(12) 0.0248(3) Uani 1 1 d . . . . .
C15 C 0.4955(2) -0.08411(15) 0.81517(13) 0.0267(3) Uani 1 1 d . . . . .
H15 H 0.4116 -0.1375 0.7643 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7319(2) 0.07635(16) 0.96263(14) 0.0289(4) Uani 1 1 d . . . . .
H14 H 0.8113 0.1334 1.0132 0.035 Uiso 1 1 calc R U . . .
C17 C 0.7200(2) -0.06072(15) 0.97647(13) 0.0255(3) Uani 1 1 d . . . . .
C21 C 0.5793(2) -0.28098(16) 0.91204(13) 0.0282(4) Uani 1 1 d . . . . .
H21 H 0.4968 -0.3359 0.8615 0.034 Uiso 1 1 calc R U . . .
C13 C 0.6300(2) 0.12702(16) 0.87713(14) 0.0299(4) Uani 1 1 d . . . . .
H13 H 0.6391 0.2193 0.8679 0.036 Uiso 1 1 calc R U . . .
C18 C 0.8237(2) -0.11964(17) 1.06280(14) 0.0311(4) Uani 1 1 d . . . . .
H18 H 0.9069 -0.0665 1.1143 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3255(2) -0.00469(16) 0.51691(14) 0.0288(4) Uani 1 1 d . . . . .
H24 H 0.2054 -0.0084 0.5282 0.035 Uiso 1 1 calc R U . . .
C22 C 0.4107(2) 0.10108(16) 0.70648(13) 0.0309(4) Uani 1 1 d . . . . .
H22A H 0.4366 0.1979 0.7097 0.037 Uiso 1 1 calc R U . . .
H22B H 0.2828 0.0776 0.7092 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3669(2) -0.05337(16) 0.41836(14) 0.0287(4) Uani 1 1 d . . . . .
H25 H 0.2752 -0.0897 0.3625 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6815(2) -0.33447(17) 0.99658(14) 0.0325(4) Uani 1 1 d . . . . .
H20 H 0.6701 -0.4270 1.0046 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4576(2) 0.04935(15) 0.59914(13) 0.0263(3) Uani 1 1 d . . . . .
C19 C 0.8041(2) -0.25312(18) 1.07215(14) 0.0323(4) Uani 1 1 d . . . . .
H19 H 0.8742 -0.2918 1.1305 0.039 Uiso 1 1 calc R U . . .
C7 C 0.2424(2) 0.39442(15) 0.57669(13) 0.0242(3) Uani 1 1 d . . . . .
H7 H 0.3662 0.4020 0.5750 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0585(2) 0.31828(15) 0.49444(13) 0.0243(3) Uani 1 1 d . . . . .
H8 H -0.1401 0.2739 0.4367 0.029 Uiso 1 1 calc R U . . .
C4 C -0.00428(19) 0.43909(14) 0.67078(12) 0.0227(3) Uani 1 1 d . . . . .
N2 N -0.39945(18) 0.43610(13) 0.78065(12) 0.0302(3) Uani 1 1 d . . . . .
C9 C 0.12583(19) 0.32778(14) 0.48737(13) 0.0229(3) Uani 1 1 d . . . . .
C5 C 0.18076(19) 0.44734(15) 0.66411(13) 0.0237(3) Uani 1 1 d . . . . .
H5 H 0.2624 0.4909 0.7222 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3700(2) 0.28606(15) 0.38458(13) 0.0247(3) Uani 1 1 d . . . . .
N4 N -0.0251(2) 0.11858(15) 0.25716(13) 0.0408(4) Uani 1 1 d . . . . .
N3 N 0.51843(18) 0.29749(14) 0.37660(12) 0.0306(3) Uani 1 1 d . . . . .
C3 C -0.0708(2) 0.49399(15) 0.76102(13) 0.0247(3) Uani 1 1 d . . . . .
N1 N 0.13329(19) 0.62720(15) 0.91873(13) 0.0363(4) Uani 1 1 d . . . . .
C10 C 0.1875(2) 0.27309(14) 0.39550(13) 0.0243(3) Uani 1 1 d . . . . .
C12 C 0.0726(2) 0.18922(15) 0.31706(14) 0.0283(4) Uani 1 1 d . . . . .
C1 C 0.0413(2) 0.56785(15) 0.84842(13) 0.0263(3) Uani 1 1 d . . . . .
C6 C -0.11989(19) 0.37142(15) 0.58219(13) 0.0241(3) Uani 1 1 d . . . . .
H6 H -0.2436 0.3630 0.5842 0.029 Uiso 1 1 calc R U . . .
C2 C -0.2519(2) 0.46550(14) 0.77289(12) 0.0237(3) 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
N5 C15 1.324(2) . ?
N5 C13 1.381(2) . ?
N5 C22 1.490(2) . ?
C16 C15 1.401(2) . ?
C16 C21 1.410(2) . ?
C16 C17 1.426(2) . ?
C14 C13 1.360(2) . ?
C14 C17 1.412(2) . ?
C17 C18 1.415(2) . ?
C21 C20 1.367(2) . ?
C18 C19 1.368(2) . ?
C24 C25 1.386(2) . ?
C24 C23 1.387(2) . ?
C22 C23 1.510(2) . ?
C25 C23 1.392(2) 2_656 ?
C20 C19 1.414(2) . ?
C23 C25 1.392(2) 2_656 ?
C7 C5 1.358(2) . ?
C7 C9 1.425(2) . ?
C8 C6 1.361(2) . ?
C8 C9 1.425(2) . ?
C4 C3 1.414(2) . ?
C4 C6 1.420(2) . ?
C4 C5 1.431(2) . ?
N2 C2 1.157(2) . ?
C9 C10 1.411(2) . ?
C11 N3 1.152(2) . ?
C11 C10 1.420(2) . ?
N4 C12 1.156(2) . ?
C3 C2 1.416(2) . ?
C3 C1 1.426(2) . ?
N1 C1 1.153(2) . ?
C10 C12 1.418(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
C15 N5 C13 121.46(14) . . ?
C15 N5 C22 118.90(14) . . ?
C13 N5 C22 119.59(14) . . ?
C15 C16 C21 121.66(15) . . ?
C15 C16 C17 117.85(14) . . ?
C21 C16 C17 120.50(15) . . ?
N5 C15 C16 121.65(15) . . ?
C13 C14 C17 120.22(15) . . ?
C14 C17 C18 122.99(15) . . ?
C14 C17 C16 118.60(15) . . ?
C18 C17 C16 118.41(15) . . ?
C20 C21 C16 119.49(15) . . ?
C14 C13 N5 120.20(15) . . ?
C19 C18 C17 119.99(16) . . ?
C25 C24 C23 120.68(16) . . ?
N5 C22 C23 110.39(12) . . ?
C24 C25 C23 120.31(16) . 2_656 ?
C21 C20 C19 120.46(16) . . ?
C24 C23 C25 119.01(15) . 2_656 ?
C24 C23 C22 120.12(15) . . ?
C25 C23 C22 120.87(16) 2_656 . ?
C18 C19 C20 121.16(16) . . ?
C5 C7 C9 121.54(14) . . ?
C6 C8 C9 121.38(14) . . ?
C3 C4 C6 120.97(14) . . ?
C3 C4 C5 122.34(14) . . ?
C6 C4 C5 116.69(13) . . ?
C10 C9 C7 122.29(13) . . ?
C10 C9 C8 120.75(14) . . ?
C7 C9 C8 116.96(14) . . ?
C7 C5 C4 121.58(14) . . ?
N3 C11 C10 179.31(18) . . ?
C4 C3 C2 120.07(14) . . ?
C4 C3 C1 122.24(14) . . ?
C2 C3 C1 117.39(13) . . ?
C9 C10 C12 121.22(14) . . ?
C9 C10 C11 121.66(14) . . ?
C12 C10 C11 116.69(14) . . ?
N4 C12 C10 176.80(18) . . ?
N1 C1 C3 179.40(17) . . ?
C8 C6 C4 121.85(14) . . ?
N2 C2 C3 176.65(16) . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.050

