# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_ds722
_database_code_depnum_ccdc_archive 'CCDC 2035879'
loop_
_audit_author_name
_audit_author_address
'Daniel Scott'
;University of Regensburg
Germany
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-10-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'tris(4-phenyl)phenylaminium hexafluorophosphate'
_chemical_formula_moiety         'F6 P, C36 H27 N'
_chemical_formula_sum            'C36 H27 F6 N P'
_chemical_formula_weight         618.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H27 F6 N P'
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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.9242(2)
_cell_length_b                   24.0647(4)
_cell_length_c                   12.6848(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.769(2)
_cell_angle_gamma                90
_cell_volume                     2942.36(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10633
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      65.8520
_cell_measurement_theta_min      3.9940
_shelx_estimated_absorpt_T_max   0.862
_shelx_estimated_absorpt_T_min   0.623
_exptl_absorpt_coefficient_mu    1.400
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.21a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark purple'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -2 -7 0.0334
6 1 -2 0.1657
0 16 0 0.0952
-6 0 5 0.1755
0 15 2 0.0978
3 14 -1 0.1178
1 8 6 0.0736
3 -6 6 0.0639
6 -3 -2 0.1645
0 -5 8 0.0661
2 -12 4 0.0738
0 -12 5 0.0736
0 -15 1 0.0727
-5 -5 5 0.1683
3 -14 -2 0.1196
-1 11 -6 0.0804
4 1 4 0.0919
1 1 8 0.0648

_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.171
_exptl_crystal_size_min          0.109
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.6791 -2.4560 -7.1088 0.9519 -0.2281 0.2045
6.4331 0.5798 -1.7348 -0.4688 0.1127 0.8761
-0.1449 15.6032 -0.2922 0.1300 0.9906 -0.0426
-5.7639 0.2268 5.3207 0.0047 -0.0277 -0.9996
0.1743 14.9982 2.1749 -0.1808 0.9733 -0.1416
3.0515 13.7461 -0.6583 -0.1695 0.9133 0.3704
0.8677 8.2872 6.4317 -0.7618 0.5841 -0.2801
2.8287 -5.6765 5.7105 -0.9581 -0.2842 0.0354
6.2899 -3.3437 -1.7828 -0.4694 -0.1396 0.8719
0.1953 -4.9588 7.5216 -0.8837 -0.2619 -0.3879
1.9433 -12.1899 3.7882 -0.6871 -0.7246 0.0540
-0.0371 -11.5002 5.4232 -0.6607 -0.6964 -0.2802
0.1048 -15.4119 1.2642 -0.2331 -0.9723 -0.0177
-5.2062 -5.3892 5.3989 -0.0913 -0.3775 -0.9215
2.9795 -13.7834 -1.5977 -0.2030 -0.8489 0.4880
-0.6177 10.6925 -5.5915 0.7428 0.6349 0.2125
4.0008 1.0092 4.0029 -0.8538 0.1462 0.2561
0.9988 1.0089 8.0007 -0.9885 0.1327 -0.3335

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15020
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        65.900
_diffrn_reflns_theta_max         65.900
_diffrn_reflns_theta_min         3.673
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  32.00   0.25    0.36    --  -42.05  37.00-120.00  296
  2  ω    -32.00  42.00   0.25    0.36    --   42.05 -37.00  30.00  296
  3  ω     17.00 112.00   0.25    1.49    --   90.36-125.00-120.00  380
  4  ω     82.00 158.00   0.25    1.49    --   90.36  77.00 120.00  304
  5  ω      8.00 106.00   0.25    1.49    --   90.36 -94.00 -90.00  392
  6  ω     18.00  71.00   0.25    1.49    --   90.36 -61.00 -30.00  212
  7  ω     65.00 158.00   0.25    1.49    --   90.36  45.00  60.00  372
  8  ω   -115.00 -14.00   0.25    0.36    --  -42.05 -57.00 -60.00  404
  9  ω   -115.00 -14.00   0.25    0.36    --  -42.05 -57.00 150.00  404
 10  ω     17.00  51.00   0.25    1.49    --   90.36 -45.00  60.00  136
 11  ω     61.00  86.00   0.25    1.49    --   90.36  61.00-150.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1033738000
_diffrn_orient_matrix_UB_12      0.0052892000
_diffrn_orient_matrix_UB_13      -0.1113179000
_diffrn_orient_matrix_UB_21      0.0136263000
_diffrn_orient_matrix_UB_22      0.0637415000
_diffrn_orient_matrix_UB_23      0.0068457000
_diffrn_orient_matrix_UB_31      0.1211903000
_diffrn_orient_matrix_UB_32      -0.0026603000
_diffrn_orient_matrix_UB_33      -0.0564724000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4595
_reflns_number_total             4989
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     62.30
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4989
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+1.7364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C24(H24), C27(H27), C12(H12), C23(H23), C26(H26), C35(H35), C3(H3),
 C15(H15), C6(H6), C2(H2), C36(H36), C14(H14), C10(H10), C34(H34), C9(H9),
 C18(H18), C22(H22), C7(H7), C30(H30), C8(H8), C33(H33), C21(H21), C31(H31),
 C32(H32), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P1 P -0.12805(5) 0.60955(2) 0.76512(4) 0.03029(14) Uani 1 1 d . . . . .
F2 F -0.07005(12) 0.57669(5) 0.67592(10) 0.0415(3) Uani 1 1 d . . . . .
F1 F 0.01646(11) 0.64019(5) 0.80557(9) 0.0405(3) Uani 1 1 d . . . . .
F4 F -0.18859(12) 0.64349(5) 0.85251(10) 0.0471(3) Uani 1 1 d . . . . .
F6 F -0.27398(12) 0.57883(5) 0.72536(11) 0.0511(3) Uani 1 1 d . . . . .
F5 F -0.18084(14) 0.65781(5) 0.67936(10) 0.0548(4) Uani 1 1 d . . . . .
F3 F -0.07809(13) 0.56176(5) 0.85057(11) 0.0528(3) Uani 1 1 d . . . . .
N1 N 0.22065(14) 0.71786(6) 0.76273(11) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.18714(16) 0.71161(7) 0.64821(13) 0.0220(3) Uani 1 1 d . . . . .
C4 C 0.11412(16) 0.70207(7) 0.42159(13) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.30960(16) 0.68133(7) 0.82999(13) 0.0228(3) Uani 1 1 d . . . . .
C11 C 0.12033(17) 0.65519(7) 0.48844(13) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.099063 0.619688 0.455994 0.029 Uiso 1 1 calc R U . . .
C5 C 0.07433(16) 0.69741(7) 0.30150(13) 0.0233(3) Uani 1 1 d . . . . .
C24 C 0.30064(17) 0.67298(7) 0.93786(13) 0.0245(3) Uani 1 1 d . . . . .
H24 H 0.232505 0.692243 0.965085 0.029 Uiso 1 1 calc R U . . .
C27 C 0.15670(17) 0.83962(7) 0.92381(13) 0.0244(4) Uani 1 1 d . . . . .
H27 H 0.206259 0.863281 0.979685 0.029 Uiso 1 1 calc R U . . .
C12 C 0.15664(17) 0.65942(7) 0.60034(13) 0.0243(4) Uani 1 1 d . . . . .
H12 H 0.160791 0.627168 0.644185 0.029 Uiso 1 1 calc R U . . .
C25 C 0.15326(17) 0.76191(7) 0.80471(13) 0.0223(3) Uani 1 1 d . . . . .
C23 C 0.39007(17) 0.63709(7) 1.00378(13) 0.0254(4) Uani 1 1 d . . . . .
H23 H 0.382107 0.631728 1.076253 0.030 Uiso 1 1 calc R U . . .
C26 C 0.22554(17) 0.79645(7) 0.88731(13) 0.0238(3) Uani 1 1 d . . . . .
H26 H 0.321379 0.790354 0.918253 0.029 Uiso 1 1 calc R U . . .
C35 C -0.05507(17) 0.81337(7) 0.79750(13) 0.0243(3) Uani 1 1 d . . . . .
H35 H -0.151300 0.818857 0.767172 0.029 Uiso 1 1 calc R U . . .
C16 C 0.49351(17) 0.60791(7) 0.96724(13) 0.0237(4) Uani 1 1 d . . . . .
C28 C 0.01477(17) 0.84913(7) 0.87977(13) 0.0236(3) Uani 1 1 d . . . . .
C3 C 0.14672(17) 0.75375(7) 0.47211(14) 0.0249(4) Uani 1 1 d . . . . .
H3 H 0.144802 0.786024 0.428644 0.030 Uiso 1 1 calc R U . . .
C17 C 0.59470(17) 0.57205(7) 1.04043(14) 0.0264(4) Uani 1 1 d . . . . .
C15 C 0.49823(17) 0.61567(7) 0.85807(14) 0.0256(4) Uani 1 1 d . . . . .
H15 H 0.564645 0.595640 0.830214 0.031 Uiso 1 1 calc R U . . .
C6 C 0.10970(17) 0.73940(7) 0.23650(14) 0.0269(4) Uani 1 1 d . . . . .
H6 H 0.158053 0.771351 0.269684 0.032 Uiso 1 1 calc R U . . .
C2 C 0.18147(17) 0.75874(7) 0.58344(14) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.201562 0.794263 0.616061 0.029 Uiso 1 1 calc R U . . .
C36 C 0.01228(17) 0.77050(7) 0.75955(13) 0.0243(3) Uani 1 1 d . . . . .
H36 H -0.036767 0.746998 0.703169 0.029 Uiso 1 1 calc R U . . .
C29 C -0.06140(18) 0.89490(7) 0.91724(14) 0.0258(4) Uani 1 1 d . . . . .
C14 C 0.40956(17) 0.65136(7) 0.79099(14) 0.0254(4) Uani 1 1 d . . . . .
H14 H 0.415588 0.655880 0.717850 0.030 Uiso 1 1 calc R U . . .
C10 C 0.00287(18) 0.65110(8) 0.24956(14) 0.0293(4) Uani 1 1 d . . . . .
H10 H -0.023339 0.622307 0.291890 0.035 Uiso 1 1 calc R U . . .
C34 C -0.16992(19) 0.92185(7) 0.84482(15) 0.0303(4) Uani 1 1 d . . . . .
H34 H -0.193480 0.911085 0.770639 0.036 Uiso 1 1 calc R U . . .
C9 C -0.03040(19) 0.64649(9) 0.13735(15) 0.0348(4) Uani 1 1 d . . . . .
H9 H -0.077839 0.614488 0.103543 0.042 Uiso 1 1 calc R U . . .
C18 C 0.67231(18) 0.53218(7) 1.00016(16) 0.0327(4) Uani 1 1 d . . . . .
H18 H 0.658829 0.527593 0.923975 0.039 Uiso 1 1 calc R U . . .
C22 C 0.61836(19) 0.57766(8) 1.15326(15) 0.0323(4) Uani 1 1 d . . . . .
H22 H 0.567747 0.604628 1.182730 0.039 Uiso 1 1 calc R U . . .
C7 C 0.07498(18) 0.73489(8) 0.12420(14) 0.0326(4) Uani 1 1 d . . . . .
H7 H 0.099106 0.763863 0.081237 0.039 Uiso 1 1 calc R U . . .
C30 C -0.0283(2) 0.91162(7) 1.02571(15) 0.0307(4) Uani 1 1 d . . . . .
H30 H 0.045718 0.893995 1.075956 0.037 Uiso 1 1 calc R U . . .
C8 C 0.00553(19) 0.68854(9) 0.07444(14) 0.0351(4) Uani 1 1 d . . . . .
H8 H -0.017471 0.685502 -0.002439 0.042 Uiso 1 1 calc R U . . .
C33 C -0.2434(2) 0.96399(7) 0.87989(17) 0.0359(4) Uani 1 1 d . . . . .
H33 H -0.317034 0.981989 0.829916 0.043 Uiso 1 1 calc R U . . .
C21 C 0.7141(2) 0.54461(9) 1.22232(17) 0.0397(5) Uani 1 1 d . . . . .
H21 H 0.728337 0.548939 1.298624 0.048 Uiso 1 1 calc R U . . .
C31 C -0.1025(2) 0.95378(8) 1.06079(16) 0.0375(4) Uani 1 1 d . . . . .
H31 H -0.079715 0.964695 1.134892 0.045 Uiso 1 1 calc R U . . .
C32 C -0.2097(2) 0.97993(8) 0.98784(18) 0.0392(5) Uani 1 1 d . . . . .
H32 H -0.260196 1.008875 1.011905 0.047 Uiso 1 1 calc R U . . .
C19 C 0.7686(2) 0.49930(8) 1.07020(18) 0.0399(5) Uani 1 1 d . . . . .
H19 H 0.820668 0.472537 1.041583 0.048 Uiso 1 1 calc R U . . .
C20 C 0.7894(2) 0.50520(8) 1.18111(18) 0.0412(5) Uani 1 1 d . . . . .
H20 H 0.854909 0.482398 1.228837 0.049 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
P1 F2 1.5959(12) . ?
P1 F1 1.5855(11) . ?
P1 F4 1.6044(12) . ?
P1 F6 1.5971(12) . ?
P1 F5 1.5922(13) . ?
P1 F3 1.5772(13) . ?
N1 C1 1.419(2) . ?
N1 C13 1.386(2) . ?
N1 C25 1.423(2) . ?
C1 C12 1.397(2) . ?
C1 C2 1.394(2) . ?
C4 C11 1.404(2) . ?
C4 C5 1.484(2) . ?
C4 C3 1.401(2) . ?
C13 C24 1.407(2) . ?
C13 C14 1.408(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C5 C6 1.401(2) . ?
C5 C10 1.399(2) . ?
C24 H24 0.9500 . ?
C24 C23 1.371(2) . ?
C27 H27 0.9500 . ?
C27 C26 1.382(2) . ?
C27 C28 1.405(2) . ?
C12 H12 0.9500 . ?
C25 C26 1.395(2) . ?
C25 C36 1.395(2) . ?
C23 H23 0.9500 . ?
C23 C16 1.410(2) . ?
C26 H26 0.9500 . ?
C35 H35 0.9500 . ?
C35 C28 1.402(2) . ?
C35 C36 1.377(2) . ?
C16 C17 1.473(2) . ?
C16 C15 1.409(2) . ?
C28 C29 1.477(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.377(2) . ?
C17 C18 1.401(3) . ?
C17 C22 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.371(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.388(2) . ?
C2 H2 0.9500 . ?
C36 H36 0.9500 . ?
C29 C34 1.398(3) . ?
C29 C30 1.396(2) . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C10 C9 1.387(3) . ?
C34 H34 0.9500 . ?
C34 C33 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.387(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C21 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.382(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.388(3) . ?
C8 H8 0.9500 . ?
C33 H33 0.9500 . ?
C33 C32 1.384(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.385(3) . ?
C31 H31 0.9500 . ?
C31 C32 1.384(3) . ?
C32 H32 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F2 P1 F4 178.62(7) . . ?
F2 P1 F6 89.99(6) . . ?
F1 P1 F2 90.50(6) . . ?
F1 P1 F4 89.90(6) . . ?
F1 P1 F6 179.49(7) . . ?
F1 P1 F5 90.41(7) . . ?
F6 P1 F4 89.61(6) . . ?
F5 P1 F2 89.57(7) . . ?
F5 P1 F4 89.10(7) . . ?
F5 P1 F6 89.75(8) . . ?
F3 P1 F2 91.06(7) . . ?
F3 P1 F1 90.26(7) . . ?
F3 P1 F4 90.26(7) . . ?
F3 P1 F6 89.58(8) . . ?
F3 P1 F5 179.07(8) . . ?
C1 N1 C25 116.47(13) . . ?
C13 N1 C1 121.52(13) . . ?
C13 N1 C25 121.96(13) . . ?
C12 C1 N1 120.95(15) . . ?
C2 C1 N1 118.95(14) . . ?
C2 C1 C12 120.09(15) . . ?
C11 C4 C5 121.46(15) . . ?
C3 C4 C11 117.70(15) . . ?
C3 C4 C5 120.84(15) . . ?
N1 C13 C24 120.73(14) . . ?
N1 C13 C14 120.48(15) . . ?
C24 C13 C14 118.78(15) . . ?
C4 C11 H11 119.2 . . ?
C12 C11 C4 121.61(15) . . ?
C12 C11 H11 119.2 . . ?
C6 C5 C4 120.46(15) . . ?
C10 C5 C4 121.65(15) . . ?
C10 C5 C6 117.88(15) . . ?
C13 C24 H24 119.9 . . ?
C23 C24 C13 120.12(15) . . ?
C23 C24 H24 119.9 . . ?
C26 C27 H27 119.4 . . ?
C26 C27 C28 121.19(15) . . ?
C28 C27 H27 119.4 . . ?
C1 C12 H12 120.4 . . ?
C11 C12 C1 119.29(15) . . ?
C11 C12 H12 120.4 . . ?
C26 C25 N1 121.45(14) . . ?
C26 C25 C36 120.41(15) . . ?
C36 C25 N1 118.13(14) . . ?
C24 C23 H23 119.0 . . ?
C24 C23 C16 121.97(16) . . ?
C16 C23 H23 119.0 . . ?
C27 C26 C25 119.52(15) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C28 C35 H35 119.2 . . ?
C36 C35 H35 119.2 . . ?
C36 C35 C28 121.67(16) . . ?
C23 C16 C17 121.66(15) . . ?
C15 C16 C23 117.00(15) . . ?
C15 C16 C17 121.31(15) . . ?
C27 C28 C29 122.34(15) . . ?
C35 C28 C27 117.85(15) . . ?
C35 C28 C29 119.81(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 C4 121.38(16) . . ?
C2 C3 H3 119.3 . . ?
C18 C17 C16 121.53(16) . . ?
C22 C17 C16 120.71(16) . . ?
C22 C17 C18 117.75(16) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 C16 121.77(15) . . ?
C14 C15 H15 119.1 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.80(17) . . ?
C7 C6 H6 119.6 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.92(15) . . ?
C3 C2 H2 120.0 . . ?
C25 C36 H36 120.3 . . ?
C35 C36 C25 119.36(15) . . ?
C35 C36 H36 120.3 . . ?
C34 C29 C28 120.52(16) . . ?
C30 C29 C28 120.91(16) . . ?
C30 C29 C34 118.56(16) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.31(15) . . ?
C15 C14 H14 119.8 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.15(17) . . ?
C9 C10 H10 119.4 . . ?
C29 C34 H34 119.6 . . ?
C33 C34 C29 120.78(18) . . ?
C33 C34 H34 119.6 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.07(18) . . ?
C8 C9 H9 120.0 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.80(18) . . ?
C19 C18 H18 119.6 . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.03(18) . . ?
C21 C22 H22 119.5 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.45(17) . . ?
C8 C7 H7 119.8 . . ?
C29 C30 H30 119.7 . . ?
C31 C30 C29 120.55(18) . . ?
C31 C30 H30 119.7 . . ?
C9 C8 H8 120.2 . . ?
C7 C8 C9 119.64(17) . . ?
C7 C8 H8 120.2 . . ?
C34 C33 H33 120.0 . . ?
C34 C33 C32 119.95(18) . . ?
C32 C33 H33 120.0 . . ?
C22 C21 H21 119.8 . . ?
C22 C21 C20 120.45(19) . . ?
C20 C21 H21 119.8 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.02(18) . . ?
C32 C31 H31 120.0 . . ?
C33 C32 H32 119.9 . . ?
C31 C32 C33 120.13(17) . . ?
C31 C32 H32 119.9 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.49(19) . . ?
C20 C19 H19 119.8 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.47(18) . . ?
C19 C20 H20 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C12 C11 178.04(14) . . . . ?
N1 C1 C2 C3 -178.83(14) . . . . ?
N1 C13 C24 C23 -179.44(15) . . . . ?
N1 C13 C14 C15 179.37(15) . . . . ?
N1 C25 C26 C27 178.39(14) . . . . ?
N1 C25 C36 C35 -179.02(14) . . . . ?
C1 N1 C13 C24 -154.24(15) . . . . ?
C1 N1 C13 C14 25.0(2) . . . . ?
C1 N1 C25 C26 -136.39(16) . . . . ?
C1 N1 C25 C36 42.5(2) . . . . ?
C4 C11 C12 C1 0.4(2) . . . . ?
C4 C5 C6 C7 178.87(15) . . . . ?
C4 C5 C10 C9 -178.19(16) . . . . ?
C4 C3 C2 C1 1.2(2) . . . . ?
C13 N1 C1 C12 43.4(2) . . . . ?
C13 N1 C1 C2 -138.22(16) . . . . ?
C13 N1 C25 C26 46.4(2) . . . . ?
C13 N1 C25 C36 -134.73(16) . . . . ?
C13 C24 C23 C16 0.5(3) . . . . ?
C11 C4 C5 C6 -159.70(16) . . . . ?
C11 C4 C5 C10 19.3(2) . . . . ?
C11 C4 C3 C2 -1.1(2) . . . . ?
C5 C4 C11 C12 -179.65(15) . . . . ?
C5 C4 C3 C2 178.87(15) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C5 C10 C9 C8 -0.9(3) . . . . ?
C24 C13 C14 C15 -1.4(2) . . . . ?
C24 C23 C16 C17 176.20(15) . . . . ?
C24 C23 C16 C15 -2.2(2) . . . . ?
C27 C28 C29 C34 146.67(17) . . . . ?
C27 C28 C29 C30 -34.3(2) . . . . ?
C12 C1 C2 C3 -0.5(2) . . . . ?
C25 N1 C1 C12 -133.77(16) . . . . ?
C25 N1 C1 C2 44.6(2) . . . . ?
C25 N1 C13 C24 22.8(2) . . . . ?
C25 N1 C13 C14 -158.00(15) . . . . ?
C23 C16 C17 C18 162.80(16) . . . . ?
C23 C16 C17 C22 -18.5(2) . . . . ?
C23 C16 C15 C14 2.1(2) . . . . ?
C26 C27 C28 C35 0.0(2) . . . . ?
C26 C27 C28 C29 179.97(15) . . . . ?
C26 C25 C36 C35 -0.2(2) . . . . ?
C35 C28 C29 C34 -33.4(2) . . . . ?
C35 C28 C29 C30 145.58(17) . . . . ?
C16 C17 C18 C19 179.05(17) . . . . ?
C16 C17 C22 C21 -179.31(17) . . . . ?
C16 C15 C14 C13 -0.4(3) . . . . ?
C28 C27 C26 C25 0.5(2) . . . . ?
C28 C35 C36 C25 0.7(2) . . . . ?
C28 C29 C34 C33 178.71(16) . . . . ?
C28 C29 C30 C31 -178.47(16) . . . . ?
C3 C4 C11 C12 0.3(2) . . . . ?
C3 C4 C5 C6 20.4(2) . . . . ?
C3 C4 C5 C10 -160.64(16) . . . . ?
C17 C16 C15 C14 -176.27(15) . . . . ?
C17 C18 C19 C20 0.2(3) . . . . ?
C17 C22 C21 C20 0.3(3) . . . . ?
C15 C16 C17 C18 -18.9(2) . . . . ?
C15 C16 C17 C22 159.79(16) . . . . ?
C6 C5 C10 C9 0.8(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C2 C1 C12 C11 -0.3(2) . . . . ?
C36 C25 C26 C27 -0.4(2) . . . . ?
C36 C35 C28 C27 -0.7(2) . . . . ?
C36 C35 C28 C29 179.42(15) . . . . ?
C29 C34 C33 C32 0.0(3) . . . . ?
C29 C30 C31 C32 -0.5(3) . . . . ?
C14 C13 C24 C23 1.4(2) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C10 C9 C8 C7 0.2(3) . . . . ?
C34 C29 C30 C31 0.5(3) . . . . ?
C34 C33 C32 C31 0.0(3) . . . . ?
C18 C17 C22 C21 -0.6(3) . . . . ?
C18 C19 C20 C21 -0.5(3) . . . . ?
C22 C17 C18 C19 0.3(3) . . . . ?
C22 C21 C20 C19 0.3(3) . . . . ?
C30 C29 C34 C33 -0.3(3) . . . . ?
C30 C31 C32 C33 0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.231
_oxdiff_exptl_absorpt_empirical_full_min 0.850
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, diethyl ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ds729
_database_code_depnum_ccdc_archive 'CCDC 2035880'
loop_
_audit_author_name
_audit_author_address
'Daniel Scott'
;University of Regensburg
Germany
;
_audit_update_record             
;
2020-10-07 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-10-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
'tris(4-(4-cyanophenyl)phenyl)aminium hexafluorophosphate'
_chemical_formula_moiety         'F6 P, C39 H24 N4, C2 H3 N'
_chemical_formula_sum            'C41 H27 F6 N5 P'
_chemical_formula_weight         734.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C41 H27 N5 P F6'
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'
F F 0.0727 0.0534 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.0127(2)
_cell_length_b                   27.7882(5)
_cell_length_c                   12.2929(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.730(2)
_cell_angle_gamma                90
_cell_volume                     3420.04(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6413
_cell_measurement_temperature    123
_cell_measurement_theta_max      71.4950
_cell_measurement_theta_min      4.4290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.21a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -18 0 0.1431
-6 2 1 0.0216
6 -2 0 0.0383
-6 -4 0 0.0437
5 -10 0 0.0883
5 12 0 0.1050
-5 12 0 0.0601
4 -14 -2 0.1344
-1 -17 2 0.1920
-1 -2 -8 0.2498
-1 18 0 0.1051
1 4 8 0.3084
1 -18 0 0.1407
0 -17 -2 0.1711

_exptl_crystal_size_max          0.605
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.065
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.4729 -17.9948 -0.0340 0.9930 0.0787 -0.0880
-6.4604 1.5591 0.6475 -0.0780 0.9839 0.1607
6.4669 -1.5919 -0.4927 0.0777 -0.9806 -0.1800
-6.3533 -3.7840 -0.1086 0.2263 0.9497 0.2165
5.3553 -10.2260 -0.0140 0.5497 -0.7968 -0.2509
4.7444 12.3203 -0.3121 -0.6868 -0.7247 -0.0563
-4.9438 11.6939 0.3941 -0.6368 0.7450 0.1989
3.7803 -14.1485 -1.7908 0.7939 -0.6081 -0.0026
-0.6268 -17.1138 2.4096 0.9119 0.1686 -0.3743
-1.2335 -1.6342 -7.7790 0.1983 -0.0289 0.9797
-0.9616 17.8307 -0.2897 -0.9759 0.1271 0.1774
1.0852 4.0709 7.6399 -0.3302 0.0460 -0.9428
0.9002 -17.8686 -0.0840 0.9832 -0.1282 -0.1300
0.4698 -17.1585 -2.4116 0.9766 -0.1283 0.1725

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12436
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.255
_diffrn_reflns_theta_min         3.932
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2548
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     27.00 114.00   1.00   35.00    --   40.47  57.00  60.00   87
  2  ω      1.00  86.00   1.00   35.00    --   40.47-125.00   0.00   85
  3  ω    -16.00  23.00   1.00   35.00    --   40.47 -19.00 -60.00   39
  4  ω     76.00 103.00   1.00  155.00    --  104.78  45.00-150.00   27
  5  ω     83.00 151.00   1.00  155.00    --  104.78 111.00  30.00   68
  6  ω     29.00  71.00   1.00  155.00    --  104.78 -61.00 120.00   42
  7  ω     79.00 158.00   1.00  155.00    --  104.78  45.00   0.00   79
  8  ω    110.00 178.00   1.00  155.00    --  104.78  45.00-150.00   68
  9  ω     62.00 107.00   1.00  155.00    --  104.78 -88.00 -95.70   45
 10  ω    118.00 143.00   1.00  155.00    --  104.78 -88.00 -95.70   25
 11  ω     22.00 143.00   1.00  155.00    --  104.78 -88.00 -39.18  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0025819000
_diffrn_orient_matrix_UB_12      -0.0550895000
_diffrn_orient_matrix_UB_13      -0.0135060000
_diffrn_orient_matrix_UB_21      -0.1496571000
_diffrn_orient_matrix_UB_22      -0.0004933000
_diffrn_orient_matrix_UB_23      0.0275453000
_diffrn_orient_matrix_UB_31      -0.0355995000
_diffrn_orient_matrix_UB_32      0.0060557000
_diffrn_orient_matrix_UB_33      -0.1215715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5284
_reflns_number_total             6419
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.21a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+1.9753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1325
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C39(H39), C28(H28), C2(H2), C15(H15), C13(H13), C24(H24), C26(H26),
 C23(H23), C37(H37), C32(H32), C16(H16), C12(H12), C25(H25), C19(H19), C38(H38),
  C33(H33), C3(H3), C20(H20), C36(H36), C6(H6), C11(H11), C7(H7), C10(H10)
2.b Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
P1 P 0.97332(6) 0.42147(2) 1.14259(5) 0.03169(17) Uani 1 1 d . . . . .
F6 F 1.05272(17) 0.37221(5) 1.14076(14) 0.0481(4) Uani 1 1 d . . . . .
F4 F 1.08512(16) 0.44655(6) 1.07142(16) 0.0506(4) Uani 1 1 d . . . . .
F3 F 0.89505(18) 0.40557(6) 1.03506(15) 0.0521(4) Uani 1 1 d . . . . .
F1 F 0.89300(17) 0.47097(6) 1.1440(2) 0.0659(6) Uani 1 1 d . . . . .
F2 F 0.8605(2) 0.39685(7) 1.21375(17) 0.0696(6) Uani 1 1 d . . . . .
N1 N 0.65363(17) 0.75458(6) 0.91859(14) 0.0195(4) Uani 1 1 d . . . . .
F5 F 1.0518(2) 0.43760(7) 1.25031(16) 0.0679(6) Uani 1 1 d . . . . .
N3 N 1.3612(2) 0.75118(8) 0.23425(18) 0.0394(5) Uani 1 1 d . . . . .
N5 N 1.2038(2) 0.62962(7) 1.23314(18) 0.0352(5) Uani 1 1 d . . . . .
N4 N 0.4297(2) 0.38947(7) 1.21088(18) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.5830(2) 0.79782(7) 0.93576(17) 0.0203(4) Uani 1 1 d . . . . .
C18 C 1.0323(2) 0.74725(7) 0.57701(17) 0.0202(4) Uani 1 1 d . . . . .
C14 C 0.7499(2) 0.75249(7) 0.83499(16) 0.0195(4) Uani 1 1 d . . . . .
C29 C 0.4682(2) 0.65791(7) 1.05836(17) 0.0212(4) Uani 1 1 d . . . . .
H29 H 0.380531 0.651279 1.082864 0.025 Uiso 1 1 calc R U . . .
C27 C 0.6251(2) 0.71221(7) 0.97659(16) 0.0193(4) Uani 1 1 d . . . . .
C39 C 0.7272(2) 0.67816(7) 0.99216(17) 0.0215(4) Uani 1 1 d . . . . .
H39 H 0.816051 0.685503 0.971513 0.026 Uiso 1 1 calc R U . . .
C30 C 0.5679(2) 0.62243(7) 1.06811(16) 0.0194(4) Uani 1 1 d . . . . .
C31 C 0.5346(2) 0.57292(7) 1.10441(16) 0.0195(4) Uani 1 1 d . . . . .
C28 C 0.4966(2) 0.70235(7) 1.01348(17) 0.0213(4) Uani 1 1 d . . . . .
H28 H 0.428700 0.726142 1.007761 0.026 Uiso 1 1 calc R U . . .
C17 C 0.9368(2) 0.74843(7) 0.66795(17) 0.0206(4) Uani 1 1 d . . . . .
C2 C 0.5338(2) 0.80961(7) 1.03818(17) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.549542 0.788851 1.098391 0.027 Uiso 1 1 calc R U . . .
C15 C 0.8406(2) 0.79031(7) 0.82137(17) 0.0211(4) Uani 1 1 d . . . . .
H15 H 0.838705 0.817443 0.868338 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5602(2) 0.82870(7) 0.84730(17) 0.0222(4) Uani 1 1 d . . . . .
H13 H 0.593073 0.820817 0.777373 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4390(2) 0.88326(7) 0.96452(17) 0.0219(4) Uani 1 1 d . . . . .
C24 C 1.0817(2) 0.70376(7) 0.53581(18) 0.0232(4) Uani 1 1 d . . . . .
H24 H 1.057222 0.674279 0.569204 0.028 Uiso 1 1 calc R U . . .
C26 C 0.7533(2) 0.71246(7) 0.76572(17) 0.0216(4) Uani 1 1 d . . . . .
H26 H 0.692188 0.686696 0.775188 0.026 Uiso 1 1 calc R U . . .
C23 C 1.1658(2) 0.70318(8) 0.44708(18) 0.0247(5) Uani 1 1 d . . . . .
H23 H 1.199141 0.673506 0.420302 0.030 Uiso 1 1 calc R U . . .
C37 C 0.6310(2) 0.54390(7) 1.15538(17) 0.0228(4) Uani 1 1 d . . . . .
H37 H 0.717321 0.556627 1.170638 0.027 Uiso 1 1 calc R U . . .
C32 C 0.4085(2) 0.55356(7) 1.08257(17) 0.0220(4) Uani 1 1 d . . . . .
H32 H 0.342221 0.572929 1.048114 0.026 Uiso 1 1 calc R U . . .
C16 C 0.9326(2) 0.78780(7) 0.73933(18) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.994740 0.813322 0.730808 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4894(2) 0.87073(7) 0.86304(17) 0.0237(4) Uani 1 1 d . . . . .
H12 H 0.474527 0.891705 0.803068 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3619(2) 0.92826(7) 0.97853(17) 0.0229(4) Uani 1 1 d . . . . .
C34 C 0.4760(2) 0.47833(7) 1.16040(17) 0.0234(4) Uani 1 1 d . . . . .
C25 C 0.8460(2) 0.71071(7) 0.68364(17) 0.0213(4) Uani 1 1 d . . . . .
H25 H 0.848311 0.683475 0.636977 0.026 Uiso 1 1 calc R U . . .
C19 C 1.0716(2) 0.79027(7) 0.52667(17) 0.0216(4) Uani 1 1 d . . . . .
H19 H 1.040477 0.820098 0.554341 0.026 Uiso 1 1 calc R U . . .
C38 C 0.6983(2) 0.63400(7) 1.03756(16) 0.0212(4) Uani 1 1 d . . . . .
H38 H 0.767735 0.611142 1.048222 0.025 Uiso 1 1 calc R U . . .
C21 C 1.2012(2) 0.74636(8) 0.39731(17) 0.0234(4) Uani 1 1 d . . . . .
C33 C 0.3786(2) 0.50650(7) 1.11042(17) 0.0237(4) Uani 1 1 d . . . . .
H33 H 0.292324 0.493660 1.095485 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4620(2) 0.85167(7) 1.05140(17) 0.0233(4) Uani 1 1 d . . . . .
H3 H 0.427610 0.859287 1.120966 0.028 Uiso 1 1 calc R U . . .
C20 C 1.1541(2) 0.79008(8) 0.43823(18) 0.0233(4) Uani 1 1 d . . . . .
H20 H 1.179097 0.819537 0.404967 0.028 Uiso 1 1 calc R U . . .
C36 C 0.6021(2) 0.49687(7) 1.18383(17) 0.0239(4) Uani 1 1 d . . . . .
H36 H 0.667741 0.477467 1.218998 0.029 Uiso 1 1 calc R U . . .
C22 C 1.2889(2) 0.74775(8) 0.30518(19) 0.0279(5) Uani 1 1 d . . . . .
C35 C 0.4489(2) 0.42866(8) 1.18803(18) 0.0280(5) Uani 1 1 d . . . . .
C6 C 0.2617(2) 0.93228(8) 1.05519(18) 0.0269(5) Uani 1 1 d . . . . .
H6 H 0.240180 0.905218 1.098798 0.032 Uiso 1 1 calc R U . . .
N2 N 0.1097(3) 1.09710(8) 1.0402(2) 0.0503(6) Uani 1 1 d . . . . .
C40 C 1.1397(2) 0.59610(8) 1.2266(2) 0.0305(5) Uani 1 1 d . . . . .
C8 C 0.2238(3) 1.01483(8) 1.00569(19) 0.0293(5) Uani 1 1 d . . . . .
C11 C 0.3895(3) 0.96845(8) 0.9135(2) 0.0317(5) Uani 1 1 d . . . . .
H11 H 0.455601 0.966190 0.859024 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1925(2) 0.97506(8) 1.06932(19) 0.0305(5) Uani 1 1 d . . . . .
H7 H 0.124248 0.977179 1.122067 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3217(3) 1.01135(8) 0.9277(2) 0.0360(6) Uani 1 1 d . . . . .
H10 H 0.342433 1.038424 0.883872 0.043 Uiso 1 1 calc R U . . .
C9 C 0.1586(3) 1.06053(9) 1.0235(2) 0.0370(6) Uani 1 1 d . . . . .
C41 C 1.0575(3) 0.55311(10) 1.2165(3) 0.0515(8) Uani 1 1 d . . . . .
H41A H 1.045326 0.545037 1.139379 0.077 Uiso 1 1 calc R U . . .
H41B H 0.970152 0.559050 1.249034 0.077 Uiso 1 1 calc R U . . .
H41C H 1.101514 0.526281 1.254226 0.077 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
P1 F6 1.5832(15) . ?
P1 F4 1.5904(17) . ?
P1 F3 1.5907(18) . ?
P1 F1 1.5937(16) . ?
P1 F2 1.5923(19) . ?
P1 F5 1.595(2) . ?
N1 C1 1.412(3) . ?
N1 C14 1.419(3) . ?
N1 C27 1.408(3) . ?
N3 C22 1.145(3) . ?
N5 C40 1.134(3) . ?
N4 C35 1.141(3) . ?
C1 C2 1.397(3) . ?
C1 C13 1.402(3) . ?
C18 C17 1.481(3) . ?
C18 C24 1.403(3) . ?
C18 C19 1.405(3) . ?
C14 C15 1.401(3) . ?
C14 C26 1.402(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.407(3) . ?
C29 C28 1.384(3) . ?
C27 C39 1.405(3) . ?
C27 C28 1.397(3) . ?
C39 H39 0.9500 . ?
C39 C38 1.380(3) . ?
C30 C31 1.486(3) . ?
C30 C38 1.400(3) . ?
C31 C37 1.400(3) . ?
C31 C32 1.395(3) . ?
C28 H28 0.9500 . ?
C17 C16 1.403(3) . ?
C17 C25 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.381(3) . ?
C4 C12 1.396(3) . ?
C4 C5 1.481(3) . ?
C4 C3 1.399(3) . ?
C24 H24 0.9500 . ?
C24 C23 1.386(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.380(3) . ?
C23 H23 0.9500 . ?
C23 C21 1.395(3) . ?
C37 H37 0.9500 . ?
C37 C36 1.384(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.386(3) . ?
C16 H16 0.9500 . ?
C12 H12 0.9500 . ?
C5 C6 1.389(3) . ?
C5 C11 1.403(3) . ?
C34 C33 1.388(3) . ?
C34 C36 1.391(3) . ?
C34 C35 1.448(3) . ?
C25 H25 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.374(3) . ?
C38 H38 0.9500 . ?
C21 C20 1.399(3) . ?
C21 C22 1.442(3) . ?
C33 H33 0.9500 . ?
C3 H3 0.9500 . ?
C20 H20 0.9500 . ?
C36 H36 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.388(3) . ?
N2 C9 1.148(3) . ?
C40 C41 1.455(4) . ?
C8 C7 1.392(3) . ?
C8 C10 1.383(4) . ?
C8 C9 1.446(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(3) . ?
C7 H7 0.9500 . ?
C10 H10 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F6 P1 F4 90.80(9) . . ?
F6 P1 F3 89.45(9) . . ?
F6 P1 F1 179.74(12) . . ?
F6 P1 F2 89.80(10) . . ?
F6 P1 F5 90.73(10) . . ?
F4 P1 F3 90.42(10) . . ?
F4 P1 F1 89.21(10) . . ?
F4 P1 F2 179.40(11) . . ?
F4 P1 F5 89.47(11) . . ?
F3 P1 F1 90.30(11) . . ?
F3 P1 F2 89.52(11) . . ?
F3 P1 F5 179.80(11) . . ?
F1 P1 F5 89.53(11) . . ?
F2 P1 F1 90.19(11) . . ?
F2 P1 F5 90.58(12) . . ?
C1 N1 C14 119.31(16) . . ?
C27 N1 C1 122.05(17) . . ?
C27 N1 C14 118.47(16) . . ?
C2 C1 N1 121.17(18) . . ?
C2 C1 C13 120.00(19) . . ?
C13 C1 N1 118.81(18) . . ?
C24 C18 C17 121.72(18) . . ?
C24 C18 C19 118.17(19) . . ?
C19 C18 C17 120.06(18) . . ?
C15 C14 N1 120.23(18) . . ?
C15 C14 C26 120.13(19) . . ?
C26 C14 N1 119.64(18) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.70(19) . . ?
C39 C27 N1 118.69(19) . . ?
C28 C27 N1 121.49(18) . . ?
C28 C27 C39 119.73(18) . . ?
C27 C39 H39 120.1 . . ?
C38 C39 C27 119.81(19) . . ?
C38 C39 H39 120.1 . . ?
C29 C30 C31 120.85(19) . . ?
C38 C30 C29 118.60(18) . . ?
C38 C30 C31 120.46(18) . . ?
C37 C31 C30 120.78(19) . . ?
C32 C31 C30 120.35(18) . . ?
C32 C31 C37 118.77(18) . . ?
C29 C28 C27 119.93(19) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C16 C17 C18 120.94(18) . . ?
C25 C17 C18 120.89(18) . . ?
C25 C17 C16 118.16(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.60(19) . . ?
C3 C2 H2 120.2 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.39(18) . . ?
C16 C15 H15 120.3 . . ?
C1 C13 H13 120.4 . . ?
C12 C13 C1 119.19(19) . . ?
C12 C13 H13 120.4 . . ?
C12 C4 C5 120.64(19) . . ?
C12 C4 C3 117.89(19) . . ?
C3 C4 C5 121.47(19) . . ?
C18 C24 H24 119.5 . . ?
C23 C24 C18 120.97(19) . . ?
C23 C24 H24 119.5 . . ?
C14 C26 H26 120.2 . . ?
C25 C26 C14 119.60(19) . . ?
C25 C26 H26 120.2 . . ?
C24 C23 H23 120.2 . . ?
C24 C23 C21 119.69(19) . . ?
C21 C23 H23 120.2 . . ?
C31 C37 H37 119.6 . . ?
C36 C37 C31 120.8(2) . . ?
C36 C37 H37 119.6 . . ?
C31 C32 H32 119.5 . . ?
C33 C32 C31 121.0(2) . . ?
C33 C32 H32 119.5 . . ?
C17 C16 H16 119.2 . . ?
C15 C16 C17 121.56(19) . . ?
C15 C16 H16 119.2 . . ?
C13 C12 C4 121.88(19) . . ?
C13 C12 H12 119.1 . . ?
C4 C12 H12 119.1 . . ?
C6 C5 C4 121.93(19) . . ?
C6 C5 C11 118.1(2) . . ?
C11 C5 C4 119.9(2) . . ?
C33 C34 C36 120.93(19) . . ?
C33 C34 C35 120.6(2) . . ?
C36 C34 C35 118.5(2) . . ?
C17 C25 H25 119.4 . . ?
C26 C25 C17 121.15(19) . . ?
C26 C25 H25 119.4 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.33(19) . . ?
C20 C19 H19 119.3 . . ?
C39 C38 C30 120.95(19) . . ?
C39 C38 H38 119.5 . . ?
C30 C38 H38 119.5 . . ?
C23 C21 C20 120.1(2) . . ?
C23 C21 C22 121.9(2) . . ?
C20 C21 C22 118.1(2) . . ?
C32 C33 C34 119.2(2) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C2 C3 C4 121.4(2) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C37 C36 C34 119.3(2) . . ?
C37 C36 H36 120.3 . . ?
C34 C36 H36 120.3 . . ?
N3 C22 C21 176.2(3) . . ?
N4 C35 C34 178.7(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
N5 C40 C41 179.2(3) . . ?
C7 C8 C9 120.4(2) . . ?
C10 C8 C7 120.0(2) . . ?
C10 C8 C9 119.5(2) . . ?
C5 C11 H11 119.6 . . ?
C10 C11 C5 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C8 C10 C11 120.0(2) . . ?
C8 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N2 C9 C8 177.8(3) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.33(19) . . . . ?
N1 C1 C13 C12 179.02(19) . . . . ?
N1 C14 C15 C16 -179.52(19) . . . . ?
N1 C14 C26 C25 179.27(18) . . . . ?
N1 C27 C39 C38 -172.56(18) . . . . ?
N1 C27 C28 C29 172.11(19) . . . . ?
C1 N1 C14 C15 44.2(3) . . . . ?
C1 N1 C14 C26 -135.5(2) . . . . ?
C1 N1 C27 C39 -153.20(19) . . . . ?
C1 N1 C27 C28 30.2(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C13 C12 C4 -0.4(3) . . . . ?
C18 C17 C16 C15 177.22(19) . . . . ?
C18 C17 C25 C26 -177.47(19) . . . . ?
C18 C24 C23 C21 -0.5(3) . . . . ?
C18 C19 C20 C21 -0.4(3) . . . . ?
C14 N1 C1 C2 -152.13(19) . . . . ?
C14 N1 C1 C13 29.1(3) . . . . ?
C14 N1 C27 C39 31.4(3) . . . . ?
C14 N1 C27 C28 -145.1(2) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C14 C26 C25 C17 -0.2(3) . . . . ?
C29 C30 C31 C37 -154.2(2) . . . . ?
C29 C30 C31 C32 29.5(3) . . . . ?
C29 C30 C38 C39 -4.2(3) . . . . ?
C27 N1 C1 C2 32.5(3) . . . . ?
C27 N1 C1 C13 -146.2(2) . . . . ?
C27 N1 C14 C15 -140.30(19) . . . . ?
C27 N1 C14 C26 40.0(3) . . . . ?
C27 C39 C38 C30 0.3(3) . . . . ?
C39 C27 C28 C29 -4.4(3) . . . . ?
C30 C29 C28 C27 0.5(3) . . . . ?
C30 C31 C37 C36 -176.44(19) . . . . ?
C30 C31 C32 C33 176.28(19) . . . . ?
C31 C30 C38 C39 172.61(19) . . . . ?
C31 C37 C36 C34 0.6(3) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C28 C29 C30 C31 -172.96(19) . . . . ?
C28 C29 C30 C38 3.8(3) . . . . ?
C28 C27 C39 C38 4.1(3) . . . . ?
C17 C18 C24 C23 176.71(19) . . . . ?
C17 C18 C19 C20 -176.29(19) . . . . ?
C2 C1 C13 C12 0.3(3) . . . . ?
C15 C14 C26 C25 -0.4(3) . . . . ?
C13 C1 C2 C3 0.4(3) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C4 C5 C11 C10 -177.8(2) . . . . ?
C24 C18 C17 C16 151.4(2) . . . . ?
C24 C18 C17 C25 -30.1(3) . . . . ?
C24 C18 C19 C20 1.2(3) . . . . ?
C24 C23 C21 C20 1.3(3) . . . . ?
C24 C23 C21 C22 179.6(2) . . . . ?
C26 C14 C15 C16 0.2(3) . . . . ?
C23 C21 C20 C19 -0.8(3) . . . . ?
C37 C31 C32 C33 -0.1(3) . . . . ?
C32 C31 C37 C36 -0.1(3) . . . . ?
C16 C17 C25 C26 1.1(3) . . . . ?
C12 C4 C5 C6 149.5(2) . . . . ?
C12 C4 C5 C11 -30.7(3) . . . . ?
C12 C4 C3 C2 0.8(3) . . . . ?
C5 C4 C12 C13 -179.2(2) . . . . ?
C5 C4 C3 C2 179.8(2) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C5 C11 C10 C8 -1.0(4) . . . . ?
C25 C17 C16 C15 -1.4(3) . . . . ?
C19 C18 C17 C16 -31.2(3) . . . . ?
C19 C18 C17 C25 147.3(2) . . . . ?
C19 C18 C24 C23 -0.7(3) . . . . ?
C38 C30 C31 C37 29.1(3) . . . . ?
C38 C30 C31 C32 -147.2(2) . . . . ?
C33 C34 C36 C37 -0.9(3) . . . . ?
C3 C4 C12 C13 -0.2(3) . . . . ?
C3 C4 C5 C6 -29.5(3) . . . . ?
C3 C4 C5 C11 150.3(2) . . . . ?
C36 C34 C33 C32 0.7(3) . . . . ?
C22 C21 C20 C19 -179.3(2) . . . . ?
C35 C34 C33 C32 -178.4(2) . . . . ?
C35 C34 C36 C37 178.3(2) . . . . ?
C6 C5 C11 C10 2.0(4) . . . . ?
C11 C5 C6 C7 -1.5(3) . . . . ?
C7 C8 C10 C11 -0.6(4) . . . . ?
C10 C8 C7 C6 1.1(4) . . . . ?
C9 C8 C7 C6 -176.3(2) . . . . ?
C9 C8 C10 C11 176.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.650
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile, diethyl ether'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_t099
_database_code_depnum_ccdc_archive 'CCDC 2038665'
_audit_update_record             
;
2020-10-15 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
Jonas.Zurauskas@chemie.uni-regensburg.de
?
Birgit.Hischa@chemie.uni-regensburg.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C39 H24 N4'
_chemical_formula_sum            'C39 H24 N4'
_chemical_formula_weight         548.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C39 H24 N4'
_chemical_oxdiff_usercomment     Zurauskas_Koenig_r-CN
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.7013(2)
_cell_length_b                   25.4439(5)
_cell_length_c                   11.5990(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.924(2)
_cell_angle_gamma                90
_cell_volume                     2778.95(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7040
_cell_measurement_temperature    122.97(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      4.2760
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1144
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 16 -1 0.0309
2 -16 -2 0.0337
2 9 5 0.0601
4 11 -4 0.0372
-4 12 2 0.0556
-1 7 7 0.0734
-5 -2 5 0.0494
3 1 5 0.0566
5 2 -5 0.0385
0 1 -7 0.0904
-4 -11 3 0.0335
-5 -10 -1 0.0530
5 11 -1 0.0331
-2 -16 0 0.0333
2 16 0 0.0280
-6 -2 -1 0.0617
-1 -16 2 0.0238
2 -15 1 0.0278
4 -7 -5 0.0353
-3 11 5 0.0618
6 -7 0 0.0303
-5 9 -2 0.0558

_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.057
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.8305 16.2238 -1.2026 -0.2324 -0.9696 -0.0763
1.5610 -15.6575 -1.9027 -0.2321 0.9651 -0.1214
2.1652 8.5815 5.0937 -0.1212 -0.5053 0.8544
3.9878 11.4424 -3.6642 -0.7540 -0.6444 -0.1271
-4.4870 11.5760 1.5327 0.6390 -0.7476 -0.1812
-0.9979 7.2433 6.7513 0.3926 -0.4594 0.7967
-5.4028 -2.3326 5.1615 0.9758 0.0771 0.2048
3.4810 0.7990 5.0806 -0.2722 -0.0217 0.9620
5.4442 2.3410 -5.0876 -0.9784 -0.0773 -0.1917
0.4030 0.7616 -7.4015 -0.3704 -0.0291 -0.9284
-4.0824 -11.4974 3.4239 0.7573 0.6472 0.0876
-4.6499 -9.9183 -0.9038 0.6474 0.5535 -0.5239
4.6422 11.1213 -0.9413 -0.7289 -0.6231 0.2836
-1.9526 -15.6047 -0.1985 0.3265 0.9232 -0.2025
1.9669 15.5759 0.2579 -0.3259 -0.9215 0.2115
-5.7169 -1.9016 -1.3053 0.7455 0.0591 -0.6639
-1.4280 -15.8386 1.6469 0.3324 0.9395 0.0829
2.3398 -14.8570 1.0061 -0.2210 0.9196 0.3248
4.4382 -7.3033 -5.3291 -0.8095 0.4955 -0.3150
-2.8857 10.6023 5.3210 0.5803 -0.6791 0.4495
5.6256 -6.7935 -0.2892 -0.7642 0.4681 0.4438
-4.5170 9.2799 -1.7158 0.5159 -0.6035 -0.6079

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16698
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.756
_diffrn_reflns_theta_min         3.474
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 4.2047
_diffrn_detector_type            TitanS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  33.00   1.00   20.00    --  -44.62  19.00 -60.00   38
  2  ω     -5.00  33.00   1.00   20.00    --  -44.62  19.00 -90.00   38
  3  ω     -5.00  33.00   1.00   20.00    --  -44.62  19.00  30.00   38
  4  ω     -5.00  33.00   1.00   20.00    --  -44.62  19.00  60.00   38
  5  ω     27.00  98.00   1.00   20.00    --   44.62-125.00 -60.00   71
  6  ω     78.00 174.00   1.00   75.00    --  104.50  61.00  30.00   96
  7  ω     35.00  93.00   1.00   75.00    --  104.50 -61.00  90.00   58
  8  ω     76.00 175.00   1.00   75.00    --  104.50  68.00 143.97   99
  9  ω     35.00  93.00   1.00   75.00    --  104.50 -61.00 -30.00   58
 10  ω     35.00 125.00   1.00   75.00    --  104.50-141.00 133.04   90
 11  ω     -5.00  33.00   1.00   20.00    --  -44.62  19.00  90.00   38
 12  ω   -114.00 -19.00   1.00   20.00    --  -44.62 -57.00 -60.00   95
 13  ω     13.00  42.00   1.00   20.00    --   44.62  76.00 160.85   29
 14  ω     34.00  60.00   1.00   75.00    --  104.50 -45.00 150.00   26
 15  ω     65.00 178.00   1.00   75.00    --  104.50  15.00 -30.00  113
 16  ω     31.00  57.00   1.00   75.00    --  104.50 -30.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1386379000
_diffrn_orient_matrix_UB_12      -0.0041104000
_diffrn_orient_matrix_UB_13      0.0420676000
_diffrn_orient_matrix_UB_21      0.0101568000
_diffrn_orient_matrix_UB_22      -0.0604137000
_diffrn_orient_matrix_UB_23      -0.0017349000
_diffrn_orient_matrix_UB_31      0.0862279000
_diffrn_orient_matrix_UB_32      0.0005316000
_diffrn_orient_matrix_UB_33      0.1301879000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'gradient vaccum rotating-anode X-ray tube'
_diffrn_source_type              'GV1000 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4455
_reflns_number_total             5374
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.41.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.41.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+1.0171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C4(H4), C8(H8), C7(H7), C10(H10), C12(H12), C34(H34), C19(H19),
 C11(H11), C36(H36), C33(H33), C16(H16), C25(H25), C3(H3), C17(H17), C20(H20),
 C37(H37), C22(H22), C38(H38), C23(H23), C13(H13), C39(H39), C30(H30), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
N4 N 0.85271(14) 0.21419(5) 0.32044(12) 0.0237(3) Uani 1 1 d . . . . .
N1 N 1.22152(18) 0.15349(7) 1.29452(14) 0.0388(4) Uani 1 1 d . . . . .
C29 C 0.28884(18) 0.00164(7) 0.01035(16) 0.0292(4) Uani 1 1 d . . . . .
H29 H 0.251009 -0.027060 0.045175 0.035 Uiso 1 1 calc R U . . .
C4 C 1.01676(18) 0.22345(7) 0.90411(15) 0.0269(4) Uani 1 1 d . . . . .
H4 H 0.992121 0.257822 0.874170 0.032 Uiso 1 1 calc R U . . .
C8 C 0.93693(17) 0.15673(6) 0.49215(15) 0.0251(3) Uani 1 1 d . . . . .
H8 H 0.943354 0.128404 0.440343 0.030 Uiso 1 1 calc R U . . .
C7 C 0.97104(17) 0.14890(6) 0.61410(15) 0.0248(3) Uani 1 1 d . . . . .
H7 H 1.001269 0.115074 0.644687 0.030 Uiso 1 1 calc R U . . .
C10 C 0.88767(17) 0.24748(6) 0.52309(15) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.861204 0.281590 0.492295 0.029 Uiso 1 1 calc R U . . .
C6 C 0.96201(16) 0.18972(6) 0.69350(14) 0.0220(3) Uani 1 1 d . . . . .
C12 C 1.03043(19) 0.13098(7) 0.87347(16) 0.0304(4) Uani 1 1 d . . . . .
H12 H 1.015886 0.101342 0.822149 0.037 Uiso 1 1 calc R U . . .
C32 C 0.54766(16) 0.11334(6) 0.10681(14) 0.0221(3) Uani 1 1 d . . . . .
C34 C 0.64801(17) 0.15599(6) 0.29546(14) 0.0228(3) Uani 1 1 d . . . . .
H34 H 0.646166 0.161739 0.376001 0.027 Uiso 1 1 calc R U . . .
C19 C 1.03854(18) 0.41003(7) 0.01930(15) 0.0267(4) Uani 1 1 d . . . . .
H19 H 0.960373 0.392934 -0.032143 0.032 Uiso 1 1 calc R U . . .
C31 C 0.44240(16) 0.07793(6) 0.03209(14) 0.0237(3) Uani 1 1 d . . . . .
C18 C 1.08627(17) 0.39278(6) 0.13645(14) 0.0230(3) Uani 1 1 d . . . . .
C11 C 0.92044(16) 0.23910(6) 0.64450(15) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.914524 0.267639 0.695897 0.029 Uiso 1 1 calc R U . . .
C36 C 0.75191(16) 0.17109(6) 0.13016(14) 0.0237(3) Uani 1 1 d . . . . .
H36 H 0.821212 0.187413 0.096559 0.028 Uiso 1 1 calc R U . . .
C33 C 0.54828(16) 0.12320(6) 0.22539(14) 0.0225(3) Uani 1 1 d . . . . .
H33 H 0.478561 0.107012 0.258728 0.027 Uiso 1 1 calc R U . . .
C16 C 1.26226(19) 0.46275(7) 0.16982(15) 0.0288(4) Uani 1 1 d . . . . .
H16 H 1.337114 0.481216 0.221968 0.035 Uiso 1 1 calc R U . . .
C2 C 1.10041(17) 0.16615(7) 1.07145(15) 0.0260(3) Uani 1 1 d . . . . .
C28 C 0.24637(17) 0.01008(7) -0.11199(16) 0.0290(4) Uani 1 1 d . . . . .
C21 C 1.02416(17) 0.34607(6) 0.18069(14) 0.0217(3) Uani 1 1 d . . . . .
C25 C 1.05131(17) 0.27147(6) 0.31518(14) 0.0226(3) Uani 1 1 d . . . . .
H25 H 1.109984 0.250900 0.376021 0.027 Uiso 1 1 calc R U . . .
C14 C 1.2869(2) 0.51978(7) 0.00443(16) 0.0317(4) Uani 1 1 d . . . . .
C1 C 1.16423(18) 0.15873(7) 1.19639(16) 0.0300(4) Uani 1 1 d . . . . .
C3 C 1.06602(18) 0.21620(7) 1.02565(15) 0.0273(4) Uani 1 1 d . . . . .
H3 H 1.076259 0.245536 1.077685 0.033 Uiso 1 1 calc R U . . .
C17 C 1.19752(18) 0.42065(7) 0.21103(15) 0.0277(4) Uani 1 1 d . . . . .
H17 H 1.229213 0.410374 0.291829 0.033 Uiso 1 1 calc R U . . .
C20 C 1.10397(19) 0.45178(7) -0.02265(15) 0.0294(4) Uani 1 1 d . . . . .
H20 H 1.071317 0.462726 -0.102905 0.035 Uiso 1 1 calc R U . . .
C24 C 0.90880(16) 0.25801(6) 0.27169(14) 0.0220(3) Uani 1 1 d . . . . .
C37 C 0.65258(17) 0.13811(6) 0.06173(14) 0.0235(3) Uani 1 1 d . . . . .
H37 H 0.655247 0.131956 -0.018489 0.028 Uiso 1 1 calc R U . . .
C22 C 0.88189(17) 0.33176(6) 0.13659(14) 0.0238(3) Uani 1 1 d . . . . .
H22 H 0.823400 0.351919 0.074835 0.029 Uiso 1 1 calc R U . . .
C38 C 0.39744(17) 0.08599(7) -0.09050(15) 0.0269(3) Uani 1 1 d . . . . .
H38 H 0.433562 0.115115 -0.125246 0.032 Uiso 1 1 calc R U . . .
C15 C 1.21699(18) 0.47779(6) 0.05173(15) 0.0268(4) Uani 1 1 d . . . . .
C23 C 0.82497(17) 0.28852(6) 0.18182(14) 0.0239(3) Uani 1 1 d . . . . .
H23 H 0.727922 0.279652 0.151171 0.029 Uiso 1 1 calc R U . . .
C13 C 1.07875(19) 0.12315(7) 0.99489(16) 0.0328(4) Uani 1 1 d . . . . .
H13 H 1.096994 0.088579 1.025709 0.039 Uiso 1 1 calc R U . . .
C39 C 0.30168(18) 0.05251(7) -0.16214(16) 0.0298(4) Uani 1 1 d . . . . .
H39 H 0.273575 0.058400 -0.245395 0.036 Uiso 1 1 calc R U . . .
C5 C 1.00251(16) 0.18117(6) 0.82443(14) 0.0230(3) Uani 1 1 d . . . . .
C35 C 0.75154(16) 0.18077(6) 0.24903(14) 0.0216(3) Uani 1 1 d . . . . .
C30 C 0.38600(17) 0.03511(6) 0.08076(15) 0.0258(3) Uani 1 1 d . . . . .
H30 H 0.415023 0.028887 0.163852 0.031 Uiso 1 1 calc R U . . .
C9 C 0.89340(16) 0.20600(6) 0.44582(14) 0.0224(3) Uani 1 1 d . . . . .
C26 C 1.10758(16) 0.31464(6) 0.27009(14) 0.0224(3) Uani 1 1 d . . . . .
H26 H 1.204913 0.323175 0.300398 0.027 Uiso 1 1 calc R U . . .
N2 N 1.33893(19) 0.55258(7) -0.03754(15) 0.0430(4) Uani 1 1 d . . . . .
N3 N 0.0577(2) -0.05163(8) -0.23943(18) 0.0562(5) Uani 1 1 d . . . . .
C27 C 0.1430(2) -0.02447(8) -0.18430(18) 0.0377(4) 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
N4 C24 1.417(2) . ?
N4 C35 1.408(2) . ?
N4 C9 1.428(2) . ?
N1 C1 1.148(2) . ?
C29 H29 0.9500 . ?
C29 C28 1.396(3) . ?
C29 C30 1.382(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.388(2) . ?
C4 C5 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.387(2) . ?
C8 C9 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.405(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C10 C9 1.395(2) . ?
C6 C11 1.398(2) . ?
C6 C5 1.490(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(3) . ?
C12 C5 1.398(2) . ?
C32 C31 1.476(2) . ?
C32 C33 1.397(2) . ?
C32 C37 1.401(2) . ?
C34 H34 0.9500 . ?
C34 C33 1.384(2) . ?
C34 C35 1.399(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.397(2) . ?
C19 C20 1.385(2) . ?
C31 C38 1.398(2) . ?
C31 C30 1.398(2) . ?
C18 C21 1.479(2) . ?
C18 C17 1.402(2) . ?
C11 H11 0.9500 . ?
C36 H36 0.9500 . ?
C36 C37 1.376(2) . ?
C36 C35 1.401(2) . ?
C33 H33 0.9500 . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C16 C15 1.388(2) . ?
C2 C1 1.445(2) . ?
C2 C3 1.389(2) . ?
C2 C13 1.393(2) . ?
C28 C39 1.394(3) . ?
C28 C27 1.441(3) . ?
C21 C22 1.400(2) . ?
C21 C26 1.402(2) . ?
C25 H25 0.9500 . ?
C25 C24 1.396(2) . ?
C25 C26 1.384(2) . ?
C14 C15 1.443(2) . ?
C14 N2 1.143(2) . ?
C3 H3 0.9500 . ?
C17 H17 0.9500 . ?
C20 H20 0.9500 . ?
C20 C15 1.389(2) . ?
C24 C23 1.394(2) . ?
C37 H37 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C38 H38 0.9500 . ?
C38 C39 1.381(2) . ?
C23 H23 0.9500 . ?
C13 H13 0.9500 . ?
C39 H39 0.9500 . ?
C30 H30 0.9500 . ?
C26 H26 0.9500 . ?
N3 C27 1.147(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
C24 N4 C9 118.88(13) . . ?
C35 N4 C24 121.40(13) . . ?
C35 N4 C9 119.60(13) . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C30 C29 C28 119.90(16) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.49(16) . . ?
C5 C4 H4 119.3 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.99(15) . . ?
C9 C8 H8 120.0 . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C6 121.67(15) . . ?
C6 C7 H7 119.2 . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.17(15) . . ?
C9 C10 H10 119.9 . . ?
C7 C6 C5 121.15(15) . . ?
C11 C6 C7 117.09(15) . . ?
C11 C6 C5 121.68(14) . . ?
C13 C12 H12 119.0 . . ?
C13 C12 C5 121.96(16) . . ?
C5 C12 H12 119.0 . . ?
C33 C32 C31 121.75(14) . . ?
C33 C32 C37 117.09(15) . . ?
C37 C32 C31 121.16(14) . . ?
C33 C34 H34 119.6 . . ?
C33 C34 C35 120.74(15) . . ?
C35 C34 H34 119.6 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C20 C19 C18 120.68(16) . . ?
C38 C31 C32 120.65(14) . . ?
C30 C31 C32 121.42(15) . . ?
C30 C31 C38 117.93(15) . . ?
C19 C18 C21 121.51(15) . . ?
C19 C18 C17 117.84(15) . . ?
C17 C18 C21 120.64(15) . . ?
C10 C11 C6 121.71(15) . . ?
C10 C11 H11 119.1 . . ?
C6 C11 H11 119.1 . . ?
C37 C36 H36 119.8 . . ?
C37 C36 C35 120.48(14) . . ?
C35 C36 H36 119.8 . . ?
C32 C33 H33 119.2 . . ?
C34 C33 C32 121.57(14) . . ?
C34 C33 H33 119.2 . . ?
C17 C16 H16 120.3 . . ?
C17 C16 C15 119.48(16) . . ?
C15 C16 H16 120.3 . . ?
C3 C2 C1 120.59(16) . . ?
C3 C2 C13 119.39(16) . . ?
C13 C2 C1 119.96(16) . . ?
C29 C28 C27 119.45(16) . . ?
C39 C28 C29 119.63(16) . . ?
C39 C28 C27 120.89(17) . . ?
C22 C21 C18 122.04(15) . . ?
C22 C21 C26 117.70(14) . . ?
C26 C21 C18 120.26(14) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C26 C25 C24 120.31(15) . . ?
N2 C14 C15 177.2(2) . . ?
N1 C1 C2 176.49(18) . . ?
C4 C3 C2 120.18(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C18 C17 H17 119.2 . . ?
C16 C17 C18 121.62(16) . . ?
C16 C17 H17 119.2 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C15 120.49(16) . . ?
C15 C20 H20 119.8 . . ?
C25 C24 N4 119.42(15) . . ?
C23 C24 N4 121.72(14) . . ?
C23 C24 C25 118.86(14) . . ?
C32 C37 H37 119.0 . . ?
C36 C37 C32 121.99(14) . . ?
C36 C37 H37 119.0 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 120.97(15) . . ?
C23 C22 H22 119.5 . . ?
C31 C38 H38 119.3 . . ?
C39 C38 C31 121.43(16) . . ?
C39 C38 H38 119.3 . . ?
C16 C15 C14 120.90(16) . . ?
C16 C15 C20 119.79(15) . . ?
C20 C15 C14 119.31(15) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.67(15) . . ?
C22 C23 H23 119.7 . . ?
C12 C13 C2 119.78(16) . . ?
C12 C13 H13 120.1 . . ?
C2 C13 H13 120.1 . . ?
C28 C39 H39 120.1 . . ?
C38 C39 C28 119.83(16) . . ?
C38 C39 H39 120.1 . . ?
C4 C5 C6 121.28(15) . . ?
C12 C5 C4 116.98(15) . . ?
C12 C5 C6 121.74(15) . . ?
C34 C35 N4 120.62(14) . . ?
C34 C35 C36 118.14(14) . . ?
C36 C35 N4 121.24(14) . . ?
C29 C30 C31 121.28(16) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C8 C9 N4 120.65(14) . . ?
C8 C9 C10 119.33(15) . . ?
C10 C9 N4 120.01(15) . . ?
C21 C26 H26 119.3 . . ?
C25 C26 C21 121.48(15) . . ?
C25 C26 H26 119.3 . . ?
N3 C27 C28 177.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C24 C23 C22 179.07(14) . . . . ?
C29 C28 C39 C38 -0.3(3) . . . . ?
C8 C7 C6 C11 -1.5(2) . . . . ?
C8 C7 C6 C5 -178.41(14) . . . . ?
C7 C8 C9 N4 -177.57(14) . . . . ?
C7 C8 C9 C10 1.5(2) . . . . ?
C7 C6 C11 C10 0.8(2) . . . . ?
C7 C6 C5 C4 169.10(15) . . . . ?
C7 C6 C5 C12 -9.8(2) . . . . ?
C32 C31 C38 C39 178.41(15) . . . . ?
C32 C31 C30 C29 -179.17(15) . . . . ?
C19 C18 C21 C22 -31.2(2) . . . . ?
C19 C18 C21 C26 149.21(15) . . . . ?
C19 C18 C17 C16 -2.3(2) . . . . ?
C19 C20 C15 C16 -1.7(3) . . . . ?
C19 C20 C15 C14 177.51(16) . . . . ?
C31 C32 C33 C34 179.33(15) . . . . ?
C31 C32 C37 C36 -179.76(15) . . . . ?
C31 C38 C39 C28 0.9(3) . . . . ?
C18 C19 C20 C15 -1.0(3) . . . . ?
C18 C21 C22 C23 -178.25(14) . . . . ?
C18 C21 C26 C25 178.39(14) . . . . ?
C11 C10 C9 N4 176.87(14) . . . . ?
C11 C10 C9 C8 -2.2(2) . . . . ?
C11 C6 C5 C4 -7.6(2) . . . . ?
C11 C6 C5 C12 173.53(15) . . . . ?
C33 C32 C31 C38 149.92(16) . . . . ?
C33 C32 C31 C30 -30.9(2) . . . . ?
C33 C32 C37 C36 -0.4(2) . . . . ?
C33 C34 C35 N4 179.88(14) . . . . ?
C33 C34 C35 C36 -0.5(2) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C21 C18 C17 C16 176.52(15) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C25 C24 C23 C22 -0.3(2) . . . . ?
C1 C2 C3 C4 174.16(15) . . . . ?
C1 C2 C13 C12 -173.71(16) . . . . ?
C3 C4 C5 C6 -174.46(14) . . . . ?
C3 C4 C5 C12 4.4(2) . . . . ?
C3 C2 C13 C12 3.4(3) . . . . ?
C17 C18 C21 C22 149.96(16) . . . . ?
C17 C18 C21 C26 -29.6(2) . . . . ?
C17 C16 C15 C14 -176.84(17) . . . . ?
C17 C16 C15 C20 2.4(3) . . . . ?
C20 C19 C18 C21 -175.85(15) . . . . ?
C20 C19 C18 C17 3.0(2) . . . . ?
C24 N4 C35 C34 -148.07(15) . . . . ?
C24 N4 C35 C36 32.3(2) . . . . ?
C24 N4 C9 C8 -132.43(16) . . . . ?
C24 N4 C9 C10 48.5(2) . . . . ?
C24 C25 C26 C21 0.3(2) . . . . ?
C37 C32 C31 C38 -30.8(2) . . . . ?
C37 C32 C31 C30 148.38(16) . . . . ?
C37 C32 C33 C34 0.0(2) . . . . ?
C37 C36 C35 N4 179.70(15) . . . . ?
C37 C36 C35 C34 0.1(2) . . . . ?
C22 C21 C26 C25 -1.2(2) . . . . ?
C38 C31 C30 C29 0.0(2) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C13 C12 C5 C4 -4.0(2) . . . . ?
C13 C12 C5 C6 174.92(15) . . . . ?
C13 C2 C3 C4 -3.0(2) . . . . ?
C5 C4 C3 C2 -1.1(2) . . . . ?
C5 C6 C11 C10 177.67(14) . . . . ?
C5 C12 C13 C2 0.1(3) . . . . ?
C35 N4 C24 C25 -143.15(15) . . . . ?
C35 N4 C24 C23 37.5(2) . . . . ?
C35 N4 C9 C8 51.5(2) . . . . ?
C35 N4 C9 C10 -127.51(16) . . . . ?
C35 C34 C33 C32 0.5(2) . . . . ?
C35 C36 C37 C32 0.4(2) . . . . ?
C30 C29 C28 C39 -0.5(3) . . . . ?
C30 C29 C28 C27 -178.83(16) . . . . ?
C30 C31 C38 C39 -0.8(2) . . . . ?
C9 N4 C24 C25 40.9(2) . . . . ?
C9 N4 C24 C23 -138.50(15) . . . . ?
C9 N4 C35 C34 27.9(2) . . . . ?
C9 N4 C35 C36 -151.75(15) . . . . ?
C9 C8 C7 C6 0.4(2) . . . . ?
C9 C10 C11 C6 1.0(2) . . . . ?
C26 C21 C22 C23 1.3(2) . . . . ?
C26 C25 C24 N4 -178.95(13) . . . . ?
C26 C25 C24 C23 0.5(2) . . . . ?
C27 C28 C39 C38 178.06(17) . . . . ?

_olex2_date_sample_data_collection 2020-08-04
_olex2_date_sample_submission    2020-07-31
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id r-CN
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.999
_oxdiff_exptl_absorpt_empirical_full_min 0.623
