# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

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

data_TCPy
_database_code_depnum_ccdc_archive 'CCDC 1948629'
loop_
_audit_author_name
_audit_author_address
'Bingjia Xu'
;South China Normal University
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-03-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        TCPy
_chemical_formula_moiety         'C40 H28 N2'
_chemical_formula_sum            'C40 H28 N2'
_chemical_formula_weight         536.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     P4PPyCN
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/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                   28.245(3)
_cell_length_b                   5.6181(4)
_cell_length_c                   18.2359(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.631(8)
_cell_angle_gamma                90
_cell_volume                     2844.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3514
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.7690
_cell_measurement_theta_min      4.7340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.557
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8473
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.696
_diffrn_reflns_theta_min         4.779
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -18.00   1.00    4.50    --  -38.50 -37.00 -30.00   89
  2  ω   -109.00 -26.00   1.00    4.50    --  -38.50 -37.00  60.00   83
  3  ω     87.00 173.00   1.00   18.00    --  108.95  45.00 -90.00   86
  4  ω     39.00  93.00   1.00   18.00    --  108.95 -94.00   0.00   54
  5  ω     73.00 177.00   1.00   18.00    --  108.95  15.00  30.00  104
  6  ω     40.00 131.00   1.00   18.00    --  108.95 -45.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0456316000
_diffrn_orient_matrix_UB_12      0.0507048000
_diffrn_orient_matrix_UB_13      -0.0324172000
_diffrn_orient_matrix_UB_21      -0.0315864000
_diffrn_orient_matrix_UB_22      0.0803981000
_diffrn_orient_matrix_UB_23      -0.0739698000
_diffrn_orient_matrix_UB_31      0.0004610000
_diffrn_orient_matrix_UB_32      0.2574765000
_diffrn_orient_matrix_UB_33      0.0291058000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                4407
_reflns_number_total             5571
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         5571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1280
_refine_ls_R_factor_gt           0.1115
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1120P)²+8.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2983
_refine_ls_wR_factor_ref         0.3099
_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:
 C10(H10), C27(H27), C39(H39), C11(H11), C20(H20), C33(H33), C32(H32),
 C14(H14), C5(H5), C13(H13), C41(H41), C12(H12), C6(H6), C16(H16), C36(H36),
 C19(H19), C35(H35), C38(H38), C42(H42), C18(H18), C17(H17), C3(H3), C2(H2),
 C26(H26), C24(H24), C25(H25), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N37 N 0.34501(14) 0.5370(8) 0.1710(2) 0.0510(10) Uani 1 1 d . . . . .
N30 N 0.61534(16) 0.8388(7) 0.5943(2) 0.0545(10) Uani 1 1 d . . . . .
C34 C 0.56065(15) 0.4962(7) 0.4467(2) 0.0348(9) Uani 1 1 d . . . . .
C28 C 0.60671(15) 0.4909(7) 0.5007(2) 0.0374(9) Uani 1 1 d . . . . .
C31 C 0.47331(14) 0.5121(7) 0.3402(2) 0.0341(8) Uani 1 1 d . . . . .
C15 C 0.86869(15) 0.1593(8) 0.6045(2) 0.0385(9) Uani 1 1 d . . . . .
C40 C 0.42856(15) 0.5167(7) 0.2831(2) 0.0365(9) Uani 1 1 d . . . . .
C9 C 0.89837(16) 0.0653(8) 0.7677(2) 0.0392(9) Uani 1 1 d . . . . .
C29 C 0.61290(16) 0.6826(8) 0.5544(2) 0.0398(9) Uani 1 1 d . . . . .
C10 C 0.93317(16) 0.2397(8) 0.7647(2) 0.0395(9) Uani 1 1 d . . . . .
H10 H 0.9248 0.3728 0.7348 0.047 Uiso 1 1 calc R . . . .
C4 C 0.68809(15) 0.2839(8) 0.5450(2) 0.0407(9) Uani 1 1 d . . . . .
C27 C 0.64119(15) 0.3233(8) 0.4992(2) 0.0406(9) Uani 1 1 d . . . . .
H27 H 0.6330 0.2120 0.4612 0.049 Uiso 1 1 calc R . . . .
C39 C 0.41815(16) 0.3436(8) 0.2276(3) 0.0441(10) Uani 1 1 d . . . . .
H39 H 0.4393 0.2172 0.2264 0.053 Uiso 1 1 calc R . . . .
C11 C 0.97916(17) 0.2219(8) 0.8041(2) 0.0433(10) Uani 1 1 d . . . . .
H11 H 1.0014 0.3414 0.8006 0.052 Uiso 1 1 calc R . . . .
C20 C 0.90150(15) -0.0174(8) 0.5958(2) 0.0417(10) Uani 1 1 d . . . . .
H20 H 0.9042 -0.1506 0.6266 0.050 Uiso 1 1 calc R . . . .
C33 C 0.52817(17) 0.6851(8) 0.4437(3) 0.0455(10) Uani 1 1 d . . . . .
H33 H 0.5353 0.8101 0.4773 0.055 Uiso 1 1 calc R . . . .
C8 C 0.84785(16) 0.0899(8) 0.7297(3) 0.0429(10) Uani 1 1 d . . . . .
C32 C 0.48589(17) 0.6910(8) 0.3921(3) 0.0452(10) Uani 1 1 d . . . . .
H32 H 0.4651 0.8195 0.3922 0.054 Uiso 1 1 calc R . . . .
C7 C 0.83488(17) 0.1391(8) 0.6580(3) 0.0445(10) Uani 1 1 d . . . . .
C14 C 0.91271(18) -0.1303(8) 0.8149(3) 0.0471(11) Uani 1 1 d . . . . .
H14 H 0.8906 -0.2488 0.8199 0.056 Uiso 1 1 calc R . . . .
C5 C 0.71657(16) 0.1057(9) 0.5213(3) 0.0485(11) Uani 1 1 d . . . . .
H5 H 0.7038 0.0158 0.4795 0.058 Uiso 1 1 calc R . . . .
C21 C 0.81086(17) 0.0475(9) 0.7788(3) 0.0482(11) Uani 1 1 d . . . . .
C13 C 0.95937(18) -0.1472(9) 0.8537(3) 0.0488(11) Uani 1 1 d . . . . .
H13 H 0.9685 -0.2795 0.8836 0.059 Uiso 1 1 calc R . . . .
C41 C 0.39499(18) 0.6994(8) 0.2801(3) 0.0487(11) Uani 1 1 d . . . . .
H41 H 0.3996 0.8201 0.3157 0.058 Uiso 1 1 calc R . . . .
C12 C 0.99255(17) 0.0275(9) 0.8490(2) 0.0471(11) Uani 1 1 d . . . . .
H12 H 1.0238 0.0147 0.8758 0.057 Uiso 1 1 calc R . . . .
C1 C 0.78266(17) 0.1803(8) 0.6214(3) 0.0468(10) Uani 1 1 d . . . . .
C6 C 0.76254(17) 0.0595(9) 0.5576(3) 0.0510(11) Uani 1 1 d . . . . .
H6 H 0.7806 -0.0563 0.5388 0.061 Uiso 1 1 calc R . . . .
C16 C 0.86623(18) 0.3557(9) 0.5573(3) 0.0505(11) Uani 1 1 d . . . . .
H16 H 0.8446 0.4774 0.5615 0.061 Uiso 1 1 calc R . . . .
C36 C 0.50542(17) 0.3212(8) 0.3438(3) 0.0517(12) Uani 1 1 d . . . . .
H36 H 0.4980 0.1956 0.3104 0.062 Uiso 1 1 calc R . . . .
C19 C 0.93019(18) -0.0001(10) 0.5424(3) 0.0512(11) Uani 1 1 d . . . . .
H19 H 0.9517 -0.1219 0.5377 0.061 Uiso 1 1 calc R . . . .
C35 C 0.54740(17) 0.3137(8) 0.3951(3) 0.0529(12) Uani 1 1 d . . . . .
H35 H 0.5677 0.1832 0.3955 0.063 Uiso 1 1 calc R . . . .
C38 C 0.37710(18) 0.3592(9) 0.1752(3) 0.0492(11) Uani 1 1 d . . . . .
H38 H 0.3709 0.2383 0.1398 0.059 Uiso 1 1 calc R . . . .
C42 C 0.35487(19) 0.7001(9) 0.2243(3) 0.0566(13) Uani 1 1 d . . . . .
H42 H 0.3330 0.8242 0.2238 0.068 Uiso 1 1 calc R . . . .
C18 C 0.92743(19) 0.1924(10) 0.4964(3) 0.0538(12) Uani 1 1 d . . . . .
H18 H 0.9468 0.2017 0.4604 0.065 Uiso 1 1 calc R . . . .
C17 C 0.8957(2) 0.3733(10) 0.5038(3) 0.0597(14) Uani 1 1 d . . . . .
H17 H 0.8939 0.5067 0.4732 0.072 Uiso 1 1 calc R . . . .
C3 C 0.70756(19) 0.4002(9) 0.6110(3) 0.0570(13) Uani 1 1 d . . . . .
H3 H 0.6894 0.5137 0.6306 0.068 Uiso 1 1 calc R . . . .
C2 C 0.75358(19) 0.3482(10) 0.6474(3) 0.0610(14) Uani 1 1 d . . . . .
H2 H 0.7657 0.4290 0.6914 0.073 Uiso 1 1 calc R . . . .
C26 C 0.8108(2) 0.1837(15) 0.8390(3) 0.079(2) Uani 1 1 d . . . . .
H26 H 0.8313 0.3140 0.8486 0.094 Uiso 1 1 calc R . . . .
C24 C 0.7486(2) -0.0658(18) 0.8734(5) 0.097(3) Uani 1 1 d . . . . .
H24 H 0.7287 -0.1102 0.9064 0.116 Uiso 1 1 calc R . . . .
C25 C 0.7789(2) 0.126(2) 0.8879(3) 0.115(4) Uani 1 1 d . . . . .
H25 H 0.7785 0.2185 0.9300 0.138 Uiso 1 1 calc R . . . .
C22 C 0.7784(4) -0.1348(13) 0.7642(7) 0.132(4) Uani 1 1 d . . . . .
H22 H 0.7770 -0.2251 0.7211 0.158 Uiso 1 1 calc R . . . .
C23 C 0.7485(4) -0.1848(16) 0.8114(9) 0.169(7) Uani 1 1 d . . . . .
H23 H 0.7267 -0.3093 0.7996 0.202 Uiso 1 1 calc R . . . .


_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
N37 C38 1.342(6) . ?
N37 C42 1.327(7) . ?
N30 C29 1.134(6) . ?
C34 C28 1.480(6) . ?
C34 C33 1.397(6) . ?
C34 C35 1.396(6) . ?
C28 C29 1.444(6) . ?
C28 C27 1.359(6) . ?
C31 C40 1.482(6) . ?
C31 C32 1.382(6) . ?
C31 C36 1.398(6) . ?
C15 C20 1.387(6) . ?
C15 C7 1.490(6) . ?
C15 C16 1.394(6) . ?
C40 C39 1.395(6) . ?
C40 C41 1.392(6) . ?
C9 C10 1.396(6) . ?
C9 C8 1.473(6) . ?
C9 C14 1.409(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(6) . ?
C4 C27 1.447(6) . ?
C4 C5 1.402(6) . ?
C4 C3 1.390(6) . ?
C27 H27 0.9300 . ?
C39 H39 0.9300 . ?
C39 C38 1.363(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.375(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.380(6) . ?
C33 H33 0.9300 . ?
C33 C32 1.378(7) . ?
C8 C7 1.320(7) . ?
C8 C21 1.515(6) . ?
C32 H32 0.9300 . ?
C7 C1 1.520(7) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(7) . ?
C21 C26 1.339(8) . ?
C21 C22 1.368(8) . ?
C13 H13 0.9300 . ?
C13 C12 1.371(7) . ?
C41 H41 0.9300 . ?
C41 C42 1.377(7) . ?
C12 H12 0.9300 . ?
C1 C6 1.375(7) . ?
C1 C2 1.391(7) . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.398(7) . ?
C36 H36 0.9300 . ?
C36 C35 1.368(7) . ?
C19 H19 0.9300 . ?
C19 C18 1.361(7) . ?
C35 H35 0.9300 . ?
C38 H38 0.9300 . ?
C42 H42 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.378(8) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.378(7) . ?
C2 H2 0.9300 . ?
C26 H26 0.9300 . ?
C26 C25 1.416(9) . ?
C24 H24 0.9300 . ?
C24 C25 1.371(13) . ?
C24 C23 1.313(15) . ?
C25 H25 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.342(12) . ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C42 N37 C38 115.1(4) . . ?
C33 C34 C28 122.1(4) . . ?
C35 C34 C28 121.8(4) . . ?
C35 C34 C33 116.0(4) . . ?
C29 C28 C34 114.7(4) . . ?
C27 C28 C34 123.1(4) . . ?
C27 C28 C29 122.2(4) . . ?
C32 C31 C40 123.2(4) . . ?
C32 C31 C36 116.3(4) . . ?
C36 C31 C40 120.6(4) . . ?
C20 C15 C7 122.9(4) . . ?
C20 C15 C16 117.0(4) . . ?
C16 C15 C7 120.0(4) . . ?
C39 C40 C31 122.4(4) . . ?
C41 C40 C31 121.8(4) . . ?
C41 C40 C39 115.8(4) . . ?
C10 C9 C8 122.9(4) . . ?
C10 C9 C14 116.5(4) . . ?
C14 C9 C8 120.3(4) . . ?
N30 C29 C28 176.0(5) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 H10 118.8 . . ?
C5 C4 C27 116.6(4) . . ?
C3 C4 C27 127.0(4) . . ?
C3 C4 C5 116.4(4) . . ?
C28 C27 C4 132.6(4) . . ?
C28 C27 H27 113.7 . . ?
C4 C27 H27 113.7 . . ?
C40 C39 H39 119.9 . . ?
C38 C39 C40 120.1(4) . . ?
C38 C39 H39 119.9 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.1(4) . . ?
C12 C11 H11 119.9 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.5(4) . . ?
C19 C20 H20 119.3 . . ?
C34 C33 H33 119.1 . . ?
C32 C33 C34 121.7(4) . . ?
C32 C33 H33 119.1 . . ?
C9 C8 C21 114.9(4) . . ?
C7 C8 C9 123.6(4) . . ?
C7 C8 C21 121.5(4) . . ?
C31 C32 H32 119.0 . . ?
C33 C32 C31 122.1(4) . . ?
C33 C32 H32 119.0 . . ?
C15 C7 C1 112.8(4) . . ?
C8 C7 C15 124.7(4) . . ?
C8 C7 C1 122.5(4) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 C9 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C26 C21 C8 120.1(5) . . ?
C26 C21 C22 118.9(6) . . ?
C22 C21 C8 120.9(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.5(4) . . ?
C42 C41 H41 120.3 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(4) . . ?
C13 C12 H12 120.3 . . ?
C6 C1 C7 120.8(4) . . ?
C6 C1 C2 116.5(4) . . ?
C2 C1 C7 122.6(4) . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.3(5) . . ?
C17 C16 H16 119.3 . . ?
C31 C36 H36 119.0 . . ?
C35 C36 C31 121.9(4) . . ?
C35 C36 H36 119.0 . . ?
C20 C19 H19 119.5 . . ?
C18 C19 C20 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C34 C35 H35 119.0 . . ?
C36 C35 C34 121.9(4) . . ?
C36 C35 H35 119.0 . . ?
N37 C38 C39 124.5(4) . . ?
N37 C38 H38 117.8 . . ?
C39 C38 H38 117.8 . . ?
N37 C42 C41 124.9(4) . . ?
N37 C42 H42 117.5 . . ?
C41 C42 H42 117.5 . . ?
C19 C18 H18 120.3 . . ?
C19 C18 C17 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(5) . . ?
C18 C17 H17 120.1 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C1 C2 H2 118.6 . . ?
C3 C2 C1 122.9(5) . . ?
C3 C2 H2 118.6 . . ?
C21 C26 H26 120.6 . . ?
C21 C26 C25 118.9(7) . . ?
C25 C26 H26 120.6 . . ?
C25 C24 H24 121.1 . . ?
C23 C24 H24 121.1 . . ?
C23 C24 C25 117.9(6) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 C26 120.4(7) . . ?
C24 C25 H25 119.8 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.8(9) . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 122.9(9) . . ?
C24 C23 H23 118.5 . . ?
C22 C23 H23 118.5 . . ?

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
C34 C28 C27 C4 179.7(4) . . . . ?
C34 C33 C32 C31 -0.5(7) . . . . ?
C28 C34 C33 C32 178.5(4) . . . . ?
C28 C34 C35 C36 -178.3(5) . . . . ?
C31 C40 C39 C38 -178.3(4) . . . . ?
C31 C40 C41 C42 177.6(4) . . . . ?
C31 C36 C35 C34 0.0(8) . . . . ?
C15 C20 C19 C18 0.3(7) . . . . ?
C15 C7 C1 C6 50.9(6) . . . . ?
C15 C7 C1 C2 -125.7(5) . . . . ?
C15 C16 C17 C18 0.9(8) . . . . ?
C40 C31 C32 C33 -178.6(4) . . . . ?
C40 C31 C36 C35 178.9(5) . . . . ?
C40 C39 C38 N37 1.7(8) . . . . ?
C40 C41 C42 N37 -0.1(9) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C9 C8 C7 C15 4.6(7) . . . . ?
C9 C8 C7 C1 -175.7(4) . . . . ?
C9 C8 C21 C26 59.8(7) . . . . ?
C9 C8 C21 C22 -117.7(7) . . . . ?
C9 C14 C13 C12 1.7(7) . . . . ?
C29 C28 C27 C4 1.5(7) . . . . ?
C10 C9 C8 C7 53.3(6) . . . . ?
C10 C9 C8 C21 -128.3(4) . . . . ?
C10 C9 C14 C13 -1.9(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C4 C5 C6 C1 2.5(8) . . . . ?
C4 C3 C2 C1 -0.2(9) . . . . ?
C27 C4 C5 C6 176.6(5) . . . . ?
C27 C4 C3 C2 -178.0(5) . . . . ?
C39 C40 C41 C42 -0.4(7) . . . . ?
C20 C15 C7 C8 53.1(6) . . . . ?
C20 C15 C7 C1 -126.7(4) . . . . ?
C20 C15 C16 C17 -0.2(7) . . . . ?
C20 C19 C18 C17 0.4(7) . . . . ?
C33 C34 C28 C29 6.0(5) . . . . ?
C33 C34 C28 C27 -172.3(4) . . . . ?
C33 C34 C35 C36 0.9(7) . . . . ?
C8 C9 C10 C11 175.6(4) . . . . ?
C8 C9 C14 C13 -176.4(4) . . . . ?
C8 C7 C1 C6 -128.8(5) . . . . ?
C8 C7 C1 C2 54.5(7) . . . . ?
C8 C21 C26 C25 -174.0(6) . . . . ?
C8 C21 C22 C23 174.1(9) . . . . ?
C32 C31 C40 C39 175.1(4) . . . . ?
C32 C31 C40 C41 -2.8(6) . . . . ?
C32 C31 C36 C35 -1.1(7) . . . . ?
C7 C15 C20 C19 175.8(4) . . . . ?
C7 C15 C16 C17 -176.5(4) . . . . ?
C7 C8 C21 C26 -121.8(6) . . . . ?
C7 C8 C21 C22 60.7(8) . . . . ?
C7 C1 C6 C5 -175.7(5) . . . . ?
C7 C1 C2 C3 174.5(5) . . . . ?
C14 C9 C10 C11 1.2(6) . . . . ?
C14 C9 C8 C7 -132.5(5) . . . . ?
C14 C9 C8 C21 45.9(6) . . . . ?
C14 C13 C12 C11 -0.7(7) . . . . ?
C5 C4 C27 C28 -172.8(5) . . . . ?
C5 C4 C3 C2 3.5(8) . . . . ?
C21 C8 C7 C15 -173.6(4) . . . . ?
C21 C8 C7 C1 6.1(7) . . . . ?
C21 C26 C25 C24 -0.3(12) . . . . ?
C21 C22 C23 C24 0(2) . . . . ?
C41 C40 C39 C38 -0.3(6) . . . . ?
C6 C1 C2 C3 -2.2(9) . . . . ?
C16 C15 C20 C19 -0.4(6) . . . . ?
C16 C15 C7 C8 -130.9(5) . . . . ?
C16 C15 C7 C1 49.4(5) . . . . ?
C36 C31 C40 C39 -4.9(6) . . . . ?
C36 C31 C40 C41 177.2(4) . . . . ?
C36 C31 C32 C33 1.4(7) . . . . ?
C19 C18 C17 C16 -1.0(8) . . . . ?
C35 C34 C28 C29 -174.8(4) . . . . ?
C35 C34 C28 C27 6.9(6) . . . . ?
C35 C34 C33 C32 -0.7(7) . . . . ?
C38 N37 C42 C41 1.4(8) . . . . ?
C42 N37 C38 C39 -2.1(7) . . . . ?
C3 C4 C27 C28 8.7(8) . . . . ?
C3 C4 C5 C6 -4.7(7) . . . . ?
C2 C1 C6 C5 1.1(8) . . . . ?
C26 C21 C22 C23 -3.4(15) . . . . ?
C25 C24 C23 C22 3.7(18) . . . . ?
C22 C21 C26 C25 3.6(11) . . . . ?
C23 C24 C25 C26 -3.4(14) . . . . ?


_olex2_date_sample_data_collection 2018-03-29
_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 1.599
_oxdiff_exptl_absorpt_empirical_full_min 0.742
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_TCPyP
_database_code_depnum_ccdc_archive 'CCDC 1948630'
loop_
_audit_author_name
_audit_author_address
'Bingjia Xu'
;South China Normal University
China
;
_audit_update_record             
;
2019-08-22 deposited with the CCDC.	2020-01-22 downloaded from the CCDC.
;
_audit_creation_date             2018-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        TCPyP
_chemical_formula_moiety         'F6 P, C41 H31 N2'
_chemical_formula_sum            'C41 H31 F6 N2 P'
_chemical_formula_weight         696.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N P F'
_chemical_oxdiff_usercomment     P4PPyCNPF
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                   31.7616(9)
_cell_length_b                   9.2797(2)
_cell_length_c                   12.6007(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.471(3)
_cell_angle_gamma                90
_cell_volume                     3690.24(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5667
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.5600
_cell_measurement_theta_min      4.2130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12818
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.908
_diffrn_reflns_theta_min         4.203
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -19.00   1.00   16.50    --  -38.50 -37.00 -90.00   89
  2  ω   -109.00 -18.00   1.00   16.50    --  -38.50 -37.00   0.00   91
  3  ω    128.00 178.00   1.00   66.00    --  107.70 106.00 -64.00   50
  4  ω     40.00 136.00   1.00   66.00    --  107.70 -77.00 -90.00   96
  5  ω     82.00 169.00   1.00   66.00    --  107.70  77.00  30.00   87
  6  ω    106.00 170.00   1.00   66.00    --  107.70  30.00 -60.00   64
  7  ω     82.00 150.00   1.00   66.00    --  107.70  61.00   0.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0196610000
_diffrn_orient_matrix_UB_12      -0.1504437000
_diffrn_orient_matrix_UB_13      0.0213177000
_diffrn_orient_matrix_UB_21      0.0429432000
_diffrn_orient_matrix_UB_22      0.0571413000
_diffrn_orient_matrix_UB_23      -0.0279410000
_diffrn_orient_matrix_UB_31      0.0123576000
_diffrn_orient_matrix_UB_32      0.0407834000
_diffrn_orient_matrix_UB_33      0.1178992000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                6250
_reflns_number_total             7240
_reflns_odcompleteness_completeness 98.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.065
_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     452
_refine_ls_number_reflns         7240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0790
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1068P)²+4.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2157
_refine_ls_wR_factor_ref         0.2223
_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:
 C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016),
 C017(H017), C018(H018), C019(H019), C01A(H01A)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
P001 P 0.44670(3) 0.74120(9) 0.58691(7) 0.0502(2) Uani 1 1 d . . . . .
F002 F 0.40529(8) 0.6430(3) 0.5662(2) 0.0842(8) Uani 1 1 d . . . . .
N003 N 0.55797(8) 0.7200(3) 0.7840(2) 0.0453(6) Uani 1 1 d . . . . .
C004 C 0.91015(9) 0.4041(3) -0.1432(2) 0.0361(6) Uani 1 1 d . . . . .
C005 C 0.89420(9) 0.7030(3) -0.0516(2) 0.0353(6) Uani 1 1 d . . . . .
F006 F 0.48799(9) 0.8340(3) 0.6105(3) 0.1107(12) Uani 1 1 d . . . . .
C007 C 0.69120(9) 0.7424(3) 0.3715(2) 0.0371(6) Uani 1 1 d . . . . .
C008 C 0.87448(8) 0.4415(3) -0.0815(2) 0.0345(5) Uani 1 1 d . . . . .
C009 C 0.86896(9) 0.5703(3) -0.0346(2) 0.0351(6) Uani 1 1 d . . . . .
C00A C 0.84416(9) 0.3216(3) -0.0675(2) 0.0359(6) Uani 1 1 d . . . . .
C00B C 0.60890(9) 0.7306(3) 0.6197(2) 0.0378(6) Uani 1 1 d . . . . .
C00C C 0.72096(9) 0.7480(3) 0.2892(2) 0.0376(6) Uani 1 1 d . . . . .
C00D C 0.83662(9) 0.5900(3) 0.0414(2) 0.0351(6) Uani 1 1 d . . . . .
N00E N 0.72901(11) 0.9992(3) 0.2064(3) 0.0606(8) Uani 1 1 d . . . . .
C00F C 0.65564(9) 0.6102(3) 0.5009(2) 0.0397(6) Uani 1 1 d . . . . .
H00F H 0.6504 0.5229 0.5333 0.048 Uiso 1 1 calc R . . . .
C00G C 0.80597(9) 0.6985(3) 0.0261(2) 0.0399(6) Uani 1 1 d . . . . .
H00G H 0.8060 0.7603 -0.0320 0.048 Uiso 1 1 calc R . . . .
C00H C 0.63656(9) 0.7357(3) 0.5333(2) 0.0374(6) Uani 1 1 d . . . . .
C00I C 0.91554(10) 0.7733(3) 0.0358(2) 0.0409(6) Uani 1 1 d . . . . .
H00I H 0.9141 0.7369 0.1041 0.049 Uiso 1 1 calc R . . . .
C00J C 0.68224(9) 0.6137(3) 0.4213(2) 0.0406(6) Uani 1 1 d . . . . .
H00J H 0.6944 0.5285 0.4005 0.049 Uiso 1 1 calc R . . . .
C00K C 0.83613(9) 0.5013(3) 0.1302(2) 0.0407(6) Uani 1 1 d . . . . .
H00K H 0.8564 0.4290 0.1425 0.049 Uiso 1 1 calc R . . . .
C00L C 0.80069(10) 0.3382(3) -0.0967(3) 0.0438(7) Uani 1 1 d . . . . .
H00L H 0.7906 0.4207 -0.1330 0.053 Uiso 1 1 calc R . . . .
C00M C 0.89573(10) 0.7617(3) -0.1527(2) 0.0403(6) Uani 1 1 d . . . . .
H00M H 0.8814 0.7168 -0.2123 0.048 Uiso 1 1 calc R . . . .
C00N C 0.85859(10) 0.1929(3) -0.0196(2) 0.0421(6) Uani 1 1 d . . . . .
H00N H 0.8875 0.1764 -0.0052 0.050 Uiso 1 1 calc R . . . .
C00P C 0.77536(10) 0.6259(3) 0.1854(2) 0.0418(6) Uani 1 1 d . . . . .
C00Q C 0.90320(9) 0.3137(3) -0.2315(2) 0.0408(6) Uani 1 1 d . . . . .
H00Q H 0.8757 0.2837 -0.2545 0.049 Uiso 1 1 calc R . . . .
C00R C 0.91856(10) 0.8872(3) -0.1649(3) 0.0456(7) Uani 1 1 d . . . . .
H00R H 0.9190 0.9267 -0.2326 0.055 Uiso 1 1 calc R . . . .
C00S C 0.97724(10) 0.3112(4) -0.2531(3) 0.0468(7) Uani 1 1 d . . . . .
H00S H 0.9996 0.2794 -0.2886 0.056 Uiso 1 1 calc R . . . .
C00T C 0.95158(10) 0.4481(3) -0.1120(2) 0.0444(7) Uani 1 1 d . . . . .
H00T H 0.9572 0.5090 -0.0534 0.053 Uiso 1 1 calc R . . . .
C00U C 0.72551(10) 0.8864(3) 0.2412(2) 0.0428(6) Uani 1 1 d . . . . .
C00V C 0.77571(10) 0.7157(3) 0.0955(2) 0.0426(6) Uani 1 1 d . . . . .
H00V H 0.7553 0.7875 0.0828 0.051 Uiso 1 1 calc R . . . .
C00W C 0.94048(10) 0.9535(3) -0.0781(3) 0.0457(7) Uani 1 1 d . . . . .
H00W H 0.9562 1.0361 -0.0873 0.055 Uiso 1 1 calc R . . . .
C00X C 0.64469(10) 0.8634(3) 0.4825(3) 0.0462(7) Uani 1 1 d . . . . .
H00X H 0.6320 0.9482 0.5021 0.055 Uiso 1 1 calc R . . . .
C00Y C 0.80624(10) 0.5184(3) 0.2003(2) 0.0455(7) Uani 1 1 d . . . . .
H00Y H 0.8066 0.4572 0.2588 0.055 Uiso 1 1 calc R . . . .
C00Z C 0.98459(10) 0.4024(4) -0.1672(3) 0.0514(8) Uani 1 1 d . . . . .
H00Z H 1.0120 0.4339 -0.1457 0.062 Uiso 1 1 calc R . . . .
C010 C 0.93635(10) 0.2671(3) -0.2862(2) 0.0439(7) Uani 1 1 d . . . . .
H010 H 0.9310 0.2065 -0.3450 0.053 Uiso 1 1 calc R . . . .
C011 C 0.93904(10) 0.8970(3) 0.0231(3) 0.0448(7) Uani 1 1 d . . . . .
H011 H 0.9537 0.9416 0.0822 0.054 Uiso 1 1 calc R . . . .
C012 C 0.58673(10) 0.6059(3) 0.6416(2) 0.0432(6) Uani 1 1 d . . . . .
H012 H 0.5889 0.5240 0.6001 0.052 Uiso 1 1 calc R . . . .
C013 C 0.67135(10) 0.8670(3) 0.4029(3) 0.0452(7) Uani 1 1 d . . . . .
H013 H 0.6761 0.9541 0.3698 0.054 Uiso 1 1 calc R . . . .
C014 C 0.83021(11) 0.0893(3) 0.0066(3) 0.0492(7) Uani 1 1 d . . . . .
H014 H 0.8402 0.0054 0.0411 0.059 Uiso 1 1 calc R . . . .
C015 C 0.74464(10) 0.6359(4) 0.2631(3) 0.0473(7) Uani 1 1 d . . . . .
H015 H 0.7409 0.5514 0.3005 0.057 Uiso 1 1 calc R . . . .
C016 C 0.77243(10) 0.2325(4) -0.0720(3) 0.0501(8) Uani 1 1 d . . . . .
H016 H 0.7435 0.2444 -0.0918 0.060 Uiso 1 1 calc R . . . .
C017 C 0.78712(11) 0.1098(4) -0.0182(3) 0.0518(8) Uani 1 1 d . . . . .
H017 H 0.7681 0.0411 0.0014 0.062 Uiso 1 1 calc R . . . .
C018 C 0.60356(10) 0.8497(3) 0.6843(3) 0.0487(7) Uani 1 1 d . . . . .
H018 H 0.6174 0.9355 0.6724 0.058 Uiso 1 1 calc R . . . .
C019 C 0.57820(11) 0.8418(4) 0.7650(3) 0.0511(8) Uani 1 1 d . . . . .
H019 H 0.5750 0.9224 0.8072 0.061 Uiso 1 1 calc R . . . .
C01A C 0.56176(10) 0.6033(4) 0.7234(3) 0.0464(7) Uani 1 1 d . . . . .
H01A H 0.5473 0.5194 0.7370 0.056 Uiso 1 1 calc R . . . .
F01B F 0.44765(14) 0.7436(8) 0.4663(3) 0.205(3) Uani 1 1 d . . . . .
F01C F 0.41873(11) 0.8734(4) 0.5876(5) 0.179(3) Uani 1 1 d . . . . .
F01F F 0.44585(16) 0.7238(7) 0.7069(3) 0.179(2) Uani 1 1 d . . . . .
F01G F 0.47467(12) 0.6043(5) 0.5908(6) 0.195(3) Uani 1 1 d . . . . .
C1 C 0.53109(11) 0.7132(5) 0.8728(3) 0.0587(9) Uani 1 1 d . . . . .
H1A H 0.5429 0.6452 0.9253 0.088 Uiso 1 1 calc GR . . . .
H1B H 0.5030 0.6833 0.8455 0.088 Uiso 1 1 calc GR . . . .
H1C H 0.5299 0.8067 0.9050 0.088 Uiso 1 1 calc GR . . . .


_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
P001 F002 1.597(2) . ?
P001 F006 1.569(3) . ?
P001 F01B 1.524(4) . ?
P001 F01C 1.515(3) . ?
P001 F01F 1.524(4) . ?
P001 F01G 1.548(4) . ?
N003 C019 1.335(4) . ?
N003 C01A 1.339(4) . ?
N003 C1 1.483(4) . ?
C004 C008 1.485(4) . ?
C004 C00Q 1.392(4) . ?
C004 C00T 1.392(4) . ?
C005 C009 1.497(4) . ?
C005 C00I 1.389(4) . ?
C005 C00M 1.392(4) . ?
C007 C00C 1.481(4) . ?
C007 C00J 1.393(4) . ?
C007 C013 1.396(4) . ?
C008 C009 1.354(4) . ?
C008 C00A 1.495(4) . ?
C009 C00D 1.493(4) . ?
C00A C00L 1.397(4) . ?
C00A C00N 1.392(4) . ?
C00B C00H 1.475(4) . ?
C00B C012 1.398(4) . ?
C00B C018 1.393(4) . ?
C00C C00U 1.435(4) . ?
C00C C015 1.345(4) . ?
C00D C00G 1.398(4) . ?
C00D C00K 1.391(4) . ?
N00E C00U 1.145(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.395(4) . ?
C00F C00J 1.383(4) . ?
C00G H00G 0.9300 . ?
C00G C00V 1.380(4) . ?
C00H C00X 1.386(4) . ?
C00I H00I 0.9300 . ?
C00I C011 1.388(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00Y 1.377(4) . ?
C00L H00L 0.9300 . ?
C00L C016 1.388(4) . ?
C00M H00M 0.9300 . ?
C00M C00R 1.390(4) . ?
C00N H00N 0.9300 . ?
C00N C014 1.383(4) . ?
C00P C00V 1.407(4) . ?
C00P C00Y 1.396(4) . ?
C00P C015 1.461(4) . ?
C00Q H00Q 0.9300 . ?
C00Q C010 1.391(4) . ?
C00R H00R 0.9300 . ?
C00R C00W 1.374(5) . ?
C00S H00S 0.9300 . ?
C00S C00Z 1.373(5) . ?
C00S C010 1.380(5) . ?
C00T H00T 0.9300 . ?
C00T C00Z 1.389(4) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00W C011 1.385(5) . ?
C00X H00X 0.9300 . ?
C00X C013 1.383(4) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C012 H012 0.9300 . ?
C012 C01A 1.370(4) . ?
C013 H013 0.9300 . ?
C014 H014 0.9300 . ?
C014 C017 1.382(5) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C017 1.380(5) . ?
C017 H017 0.9300 . ?
C018 H018 0.9300 . ?
C018 C019 1.369(5) . ?
C019 H019 0.9300 . ?
C01A H01A 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
F006 P001 F002 177.99(17) . . ?
F01B P001 F002 87.3(2) . . ?
F01B P001 F006 94.1(2) . . ?
F01B P001 F01F 174.8(4) . . ?
F01B P001 F01G 88.1(4) . . ?
F01C P001 F002 89.44(18) . . ?
F01C P001 F006 91.88(19) . . ?
F01C P001 F01B 94.1(4) . . ?
F01C P001 F01F 90.2(4) . . ?
F01C P001 F01G 177.6(4) . . ?
F01F P001 F002 89.8(2) . . ?
F01F P001 F006 88.7(2) . . ?
F01F P001 F01G 87.5(4) . . ?
F01G P001 F002 89.78(19) . . ?
F01G P001 F006 88.8(2) . . ?
C019 N003 C01A 120.4(3) . . ?
C019 N003 C1 120.1(3) . . ?
C01A N003 C1 119.5(3) . . ?
C00Q C004 C008 119.8(3) . . ?
C00Q C004 C00T 117.6(3) . . ?
C00T C004 C008 122.4(3) . . ?
C00I C005 C009 119.7(2) . . ?
C00I C005 C00M 118.5(3) . . ?
C00M C005 C009 121.8(3) . . ?
C00J C007 C00C 121.6(2) . . ?
C00J C007 C013 117.5(3) . . ?
C013 C007 C00C 120.9(3) . . ?
C004 C008 C00A 115.3(2) . . ?
C009 C008 C004 125.3(2) . . ?
C009 C008 C00A 119.2(2) . . ?
C008 C009 C005 124.5(2) . . ?
C008 C009 C00D 121.4(2) . . ?
C00D C009 C005 114.1(2) . . ?
C00L C00A C008 121.2(3) . . ?
C00N C00A C008 120.3(3) . . ?
C00N C00A C00L 118.4(3) . . ?
C012 C00B C00H 121.8(3) . . ?
C018 C00B C00H 121.8(3) . . ?
C018 C00B C012 116.4(3) . . ?
C00U C00C C007 115.4(2) . . ?
C015 C00C C007 124.3(3) . . ?
C015 C00C C00U 120.2(3) . . ?
C00G C00D C009 121.2(2) . . ?
C00K C00D C009 121.0(2) . . ?
C00K C00D C00G 117.8(2) . . ?
C00H C00F H00F 119.5 . . ?
C00J C00F H00F 119.5 . . ?
C00J C00F C00H 120.9(3) . . ?
C00D C00G H00G 119.3 . . ?
C00V C00G C00D 121.3(3) . . ?
C00V C00G H00G 119.3 . . ?
C00F C00H C00B 120.3(3) . . ?
C00X C00H C00B 121.8(3) . . ?
C00X C00H C00F 118.0(3) . . ?
C005 C00I H00I 119.4 . . ?
C011 C00I C005 121.2(3) . . ?
C011 C00I H00I 119.4 . . ?
C007 C00J H00J 119.4 . . ?
C00F C00J C007 121.3(3) . . ?
C00F C00J H00J 119.4 . . ?
C00D C00K H00K 119.4 . . ?
C00Y C00K C00D 121.3(3) . . ?
C00Y C00K H00K 119.4 . . ?
C00A C00L H00L 119.7 . . ?
C016 C00L C00A 120.5(3) . . ?
C016 C00L H00L 119.7 . . ?
C005 C00M H00M 119.9 . . ?
C00R C00M C005 120.1(3) . . ?
C00R C00M H00M 119.9 . . ?
C00A C00N H00N 119.7 . . ?
C014 C00N C00A 120.5(3) . . ?
C014 C00N H00N 119.7 . . ?
C00V C00P C015 124.6(3) . . ?
C00Y C00P C00V 117.5(3) . . ?
C00Y C00P C015 117.9(3) . . ?
C004 C00Q H00Q 119.2 . . ?
C010 C00Q C004 121.5(3) . . ?
C010 C00Q H00Q 119.2 . . ?
C00M C00R H00R 119.6 . . ?
C00W C00R C00M 120.7(3) . . ?
C00W C00R H00R 119.6 . . ?
C00Z C00S H00S 120.3 . . ?
C00Z C00S C010 119.5(3) . . ?
C010 C00S H00S 120.3 . . ?
C004 C00T H00T 119.6 . . ?
C00Z C00T C004 120.8(3) . . ?
C00Z C00T H00T 119.6 . . ?
N00E C00U C00C 177.5(3) . . ?
C00G C00V C00P 120.7(3) . . ?
C00G C00V H00V 119.6 . . ?
C00P C00V H00V 119.6 . . ?
C00R C00W H00W 120.1 . . ?
C00R C00W C011 119.8(3) . . ?
C011 C00W H00W 120.1 . . ?
C00H C00X H00X 119.4 . . ?
C013 C00X C00H 121.1(3) . . ?
C013 C00X H00X 119.4 . . ?
C00K C00Y C00P 121.4(3) . . ?
C00K C00Y H00Y 119.3 . . ?
C00P C00Y H00Y 119.3 . . ?
C00S C00Z C00T 120.8(3) . . ?
C00S C00Z H00Z 119.6 . . ?
C00T C00Z H00Z 119.6 . . ?
C00Q C010 H010 120.1 . . ?
C00S C010 C00Q 119.8(3) . . ?
C00S C010 H010 120.1 . . ?
C00I C011 H011 120.2 . . ?
C00W C011 C00I 119.5(3) . . ?
C00W C011 H011 120.2 . . ?
C00B C012 H012 119.7 . . ?
C01A C012 C00B 120.7(3) . . ?
C01A C012 H012 119.7 . . ?
C007 C013 H013 119.4 . . ?
C00X C013 C007 121.2(3) . . ?
C00X C013 H013 119.4 . . ?
C00N C014 H014 119.8 . . ?
C017 C014 C00N 120.4(3) . . ?
C017 C014 H014 119.8 . . ?
C00C C015 C00P 130.3(3) . . ?
C00C C015 H015 114.8 . . ?
C00P C015 H015 114.8 . . ?
C00L C016 H016 119.9 . . ?
C017 C016 C00L 120.2(3) . . ?
C017 C016 H016 119.9 . . ?
C014 C017 H017 120.1 . . ?
C016 C017 C014 119.7(3) . . ?
C016 C017 H017 120.1 . . ?
C00B C018 H018 119.6 . . ?
C019 C018 C00B 120.8(3) . . ?
C019 C018 H018 119.6 . . ?
N003 C019 C018 120.9(3) . . ?
N003 C019 H019 119.5 . . ?
C018 C019 H019 119.5 . . ?
N003 C01A C012 120.8(3) . . ?
N003 C01A H01A 119.6 . . ?
C012 C01A H01A 119.6 . . ?
N003 C1 H1A 109.5 . . ?
N003 C1 H1B 109.5 . . ?
N003 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
C004 C008 C009 C005 10.0(4) . . . . ?
C004 C008 C009 C00D -169.1(2) . . . . ?
C004 C008 C00A C00L -126.1(3) . . . . ?
C004 C008 C00A C00N 57.1(3) . . . . ?
C004 C00Q C010 C00S -0.2(5) . . . . ?
C004 C00T C00Z C00S -0.8(5) . . . . ?
C005 C009 C00D C00G 55.0(3) . . . . ?
C005 C009 C00D C00K -124.7(3) . . . . ?
C005 C00I C011 C00W 1.5(4) . . . . ?
C005 C00M C00R C00W 1.2(5) . . . . ?
C007 C00C C015 C00P -179.2(3) . . . . ?
C008 C004 C00Q C010 -174.9(3) . . . . ?
C008 C004 C00T C00Z 175.3(3) . . . . ?
C008 C009 C00D C00G -125.9(3) . . . . ?
C008 C009 C00D C00K 54.4(4) . . . . ?
C008 C00A C00L C016 -172.5(3) . . . . ?
C008 C00A C00N C014 171.3(3) . . . . ?
C009 C005 C00I C011 -179.6(3) . . . . ?
C009 C005 C00M C00R 178.2(3) . . . . ?
C009 C008 C00A C00L 56.9(4) . . . . ?
C009 C008 C00A C00N -119.8(3) . . . . ?
C009 C00D C00G C00V 179.2(3) . . . . ?
C009 C00D C00K C00Y -179.7(3) . . . . ?
C00A C008 C009 C005 -173.4(2) . . . . ?
C00A C008 C009 C00D 7.6(4) . . . . ?
C00A C00L C016 C017 0.0(5) . . . . ?
C00A C00N C014 C017 2.5(5) . . . . ?
C00B C00H C00X C013 178.7(3) . . . . ?
C00B C012 C01A N003 0.2(5) . . . . ?
C00B C018 C019 N003 0.0(5) . . . . ?
C00C C007 C00J C00F 177.6(3) . . . . ?
C00C C007 C013 C00X -177.7(3) . . . . ?
C00D C00G C00V C00P 1.3(5) . . . . ?
C00D C00K C00Y C00P -0.3(5) . . . . ?
C00F C00H C00X C013 -0.9(5) . . . . ?
C00G C00D C00K C00Y 0.7(4) . . . . ?
C00H C00B C012 C01A 179.0(3) . . . . ?
C00H C00B C018 C019 -179.1(3) . . . . ?
C00H C00F C00J C007 0.6(5) . . . . ?
C00H C00X C013 C007 -0.4(5) . . . . ?
C00I C005 C009 C008 -124.4(3) . . . . ?
C00I C005 C009 C00D 54.7(3) . . . . ?
C00I C005 C00M C00R 0.6(4) . . . . ?
C00J C007 C00C C00U 177.0(3) . . . . ?
C00J C007 C00C C015 -6.8(5) . . . . ?
C00J C007 C013 C00X 1.7(5) . . . . ?
C00J C00F C00H C00B -178.9(3) . . . . ?
C00J C00F C00H C00X 0.7(4) . . . . ?
C00K C00D C00G C00V -1.1(4) . . . . ?
C00L C00A C00N C014 -5.5(4) . . . . ?
C00L C016 C017 C014 -3.1(5) . . . . ?
C00M C005 C009 C008 58.0(4) . . . . ?
C00M C005 C009 C00D -123.0(3) . . . . ?
C00M C005 C00I C011 -1.9(4) . . . . ?
C00M C00R C00W C011 -1.6(5) . . . . ?
C00N C00A C00L C016 4.2(4) . . . . ?
C00N C014 C017 C016 1.8(5) . . . . ?
C00Q C004 C008 C009 -144.6(3) . . . . ?
C00Q C004 C008 C00A 38.6(4) . . . . ?
C00Q C004 C00T C00Z -0.3(5) . . . . ?
C00R C00W C011 C00I 0.3(5) . . . . ?
C00T C004 C008 C009 39.9(4) . . . . ?
C00T C004 C008 C00A -136.9(3) . . . . ?
C00T C004 C00Q C010 0.8(4) . . . . ?
C00U C00C C015 C00P -3.2(5) . . . . ?
C00V C00P C00Y C00K 0.4(5) . . . . ?
C00V C00P C015 C00C -24.0(6) . . . . ?
C00Y C00P C00V C00G -0.8(5) . . . . ?
C00Y C00P C015 C00C 156.9(4) . . . . ?
C00Z C00S C010 C00Q -0.9(5) . . . . ?
C010 C00S C00Z C00T 1.4(5) . . . . ?
C012 C00B C00H C00F -27.1(4) . . . . ?
C012 C00B C00H C00X 153.4(3) . . . . ?
C012 C00B C018 C019 0.8(5) . . . . ?
C013 C007 C00C C00U -3.6(4) . . . . ?
C013 C007 C00C C015 172.6(3) . . . . ?
C013 C007 C00J C00F -1.8(4) . . . . ?
C015 C00P C00V C00G -180.0(3) . . . . ?
C015 C00P C00Y C00K 179.5(3) . . . . ?
C018 C00B C00H C00F 152.8(3) . . . . ?
C018 C00B C00H C00X -26.8(5) . . . . ?
C018 C00B C012 C01A -0.9(5) . . . . ?
C019 N003 C01A C012 0.7(5) . . . . ?
C01A N003 C019 C018 -0.8(5) . . . . ?
C1 N003 C019 C018 179.2(3) . . . . ?
C1 N003 C01A C012 -179.3(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.179 0.055 0.770 11.2 0.0 ?
2 0.179 0.445 0.270 11.2 0.0 ?
3 0.325 0.750 -0.027 193.7 58.5 ?
4 0.675 0.250 -0.150 193.7 57.8 ?
5 0.821 0.555 0.730 11.2 0.0 ?
6 0.821 0.945 0.230 11.2 0.0 ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2018-03-29
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.801
_exptl_crystal_preparation       Luminescent
