# Electronic Supplementary Material (ESI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_CUNY2021
_audit_block_doi                 10.5517/ccdc.csd.cc2brwww
_database_code_depnum_ccdc_archive 'CCDC 2167919'
loop_
_audit_author_name
_audit_author_address
'Andrey A. Bardin'
;Arizona State University
United States of America
;
_audit_update_record             
;
2022-04-21 deposited with the CCDC.	2022-07-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_CUNY2021            
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: electron diffraction data
;
_vrf_PLAT020_CUNY2021            
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.319 Report
RESPONSE: electron diffraction data
;
_vrf_PLAT082_CUNY2021            
;
PROBLEM: High R1 Value ..................................       0.22 Report
RESPONSE: electron diffraction data
;
_vrf_PLAT084_CUNY2021            
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.47 Report
RESPONSE: electron diffraction data
;
_vrf_PLAT183_CUNY2021            
;
PROBLEM: Missing _cell_measurement_reflns_used Value ....     Please Do !
RESPONSE: electron diffraction data
;
_vrf_PLAT184_CUNY2021            
;
PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do !
RESPONSE: electron diffraction data
;
_vrf_PLAT185_CUNY2021            
;
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do !
RESPONSE: electron diffraction data
;
# Added during the CSD deposition process: Thursday 21 April 2022 11:56 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16'
_chemical_formula_weight         304.39

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

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

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

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

_cell_length_a                   7.720(2)
_cell_length_b                   4.780(2)
_cell_length_c                   19.850(4)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 92.22(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     731.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Micro/Nanocrystals
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             137
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.019687
_diffrn_radiation_type           '300 keV electrons'
_diffrn_source                   ?
_diffrn_measurement_device_type  Titan_Krios
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12893
_diffrn_reflns_av_unetI/netI     0.2345
_diffrn_reflns_av_R_equivalents  0.3186
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.040
_diffrn_reflns_theta_max         38.509
_diffrn_reflns_theta_full        36.870
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             1348
_reflns_number_gt                750
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1348
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2738
_refine_ls_R_factor_gt           0.2174
_refine_ls_wR_factor_ref         0.4720
_refine_ls_wR_factor_gt          0.4281
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_restrained_S_all      1.376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6381(10) 0.4094(13) 0.3033(5) 0.056(3) Uani 1 1 d . . . . .
H1 H 0.743(6) 0.475(9) 0.262(3) 0.084 Uiso 1 1 d . U . . .
C2 C 0.0699(9) 0.4971(13) 0.3911(5) 0.052(3) Uani 1 1 d . . . . .
C3 C 0.5481(9) 0.1311(12) 0.3940(4) 0.042(2) Uani 1 1 d . . . . .
C4 C 0.3653(7) -0.0401(11) 0.4803(4) 0.040(2) Uani 1 1 d . . . . .
H2 H 0.302418 -0.217164 0.484159 0.049 Uiso 1 1 calc R U . . .
C5 C 0.6750(10) 0.2019(14) 0.3522(5) 0.052(3) Uani 1 1 d . . . . .
H3 H 0.800(6) 0.104(10) 0.358(3) 0.078 Uiso 1 1 d . U . . .
C6 C 0.1802(10) 0.5876(13) 0.3442(5) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.124(7) 0.733(9) 0.302(3) 0.077 Uiso 1 1 d . U . . .
C7 C 0.2750(8) 0.1723(12) 0.4371(5) 0.042(2) Uani 1 1 d . . . . .
C8 C 0.3906(9) 0.2666(11) 0.3890(5) 0.046(2) Uani 1 1 d . . . . .
C9 C 0.5525(8) -0.0702(10) 0.4519(4) 0.035(2) Uani 1 1 d . . . . .
H5 H 0.585397 -0.261740 0.440332 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3472(10) 0.4709(13) 0.3414(5) 0.055(3) Uani 1 1 d . . . . .
C11 C 0.4813(11) 0.5417(14) 0.2978(5) 0.060(3) Uani 1 1 d . . . . .
H6 H 0.463(7) 0.696(12) 0.260(4) 0.090 Uiso 1 1 d . U . . .
C12 C 0.1146(9) 0.2886(12) 0.4372(5) 0.049(3) Uani 1 1 d . . . . .
H7 H 0.004(6) 0.235(8) 0.478(3) 0.074 Uiso 1 1 d . U . . .
H8 H -0.063(8) 0.603(11) 0.386(4) 0.097(15) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.065(5) 0.035(3) 0.070(8) 0.006(4) 0.032(5) -0.001(3)
C2 0.048(4) 0.038(3) 0.069(8) 0.008(4) 0.005(5) -0.005(3)
C3 0.050(4) 0.030(3) 0.048(7) 0.002(3) 0.013(4) 0.001(3)
C4 0.034(3) 0.029(3) 0.059(7) 0.010(3) 0.009(4) -0.001(2)
C5 0.054(5) 0.047(3) 0.059(7) -0.007(4) 0.033(5) -0.011(3)
C6 0.052(4) 0.039(3) 0.062(8) 0.004(4) 0.000(5) 0.003(3)
C7 0.039(4) 0.034(3) 0.055(7) 0.005(3) 0.015(4) 0.001(3)
C8 0.042(4) 0.030(3) 0.067(7) -0.004(3) 0.013(4) 0.001(2)
C9 0.048(4) 0.022(2) 0.034(6) 0.005(3) 0.002(4) 0.001(2)
C10 0.063(5) 0.032(3) 0.070(8) 0.007(3) 0.021(5) 0.000(3)
C11 0.077(6) 0.032(3) 0.073(8) 0.004(4) 0.027(5) -0.004(3)
C12 0.044(4) 0.033(3) 0.072(8) -0.001(3) 0.009(5) -0.004(3)

_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
C1 C11 1.367(11) . ?
C1 C5 1.409(12) . ?
C2 C6 1.357(11) . ?
C2 C12 1.387(11) . ?
C3 C5 1.351(9) . ?
C3 C8 1.378(9) . ?
C3 C9 1.499(10) . ?
C4 C7 1.486(10) . ?
C4 C9 1.557(11) 3_656 ?
C4 C9 1.578(8) . ?
C6 C10 1.408(10) . ?
C7 C12 1.357(9) . ?
C7 C8 1.406(9) . ?
C8 C10 1.390(12) . ?
C10 C11 1.417(11) . ?

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
C11 C1 C5 122.4(7) . . ?
C6 C2 C12 122.3(6) . . ?
C5 C3 C8 119.8(8) . . ?
C5 C3 C9 129.5(7) . . ?
C8 C3 C9 110.5(6) . . ?
C7 C4 C9 115.7(5) . 3_656 ?
C7 C4 C9 105.8(5) . . ?
C9 C4 C9 89.5(5) 3_656 . ?
C3 C5 C1 117.8(7) . . ?
C2 C6 C10 120.0(8) . . ?
C12 C7 C8 118.2(8) . . ?
C12 C7 C4 133.4(6) . . ?
C8 C7 C4 108.4(5) . . ?
C3 C8 C10 124.6(7) . . ?
C3 C8 C7 112.5(8) . . ?
C10 C8 C7 123.0(7) . . ?
C3 C9 C4 116.2(5) . 3_656 ?
C3 C9 C4 102.8(5) . . ?
C4 C9 C4 90.5(5) 3_656 . ?
C8 C10 C6 116.7(7) . . ?
C8 C10 C11 114.9(7) . . ?
C6 C10 C11 128.4(9) . . ?
C1 C11 C10 120.4(9) . . ?
C7 C12 C2 119.8(7) . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.074

_shelx_res_file                  
;
TITL allmerge_a.res in P2(1)/n
    CUNY2021.res
    created by SHELXL-2018/3 at 19:03:13 on 09-Feb-2022
REM Old TITL all merge
REM SHELXT solution in P2(1)/n: R1 0.449, Rweak 0.467, Alpha 0.156
REM <I/s>   0.946 for  141 systematic absences,  Orientation as input
REM Formula found by SHELXT:  C11 N
CELL  1.00000   7.7200   4.7800  19.8500   90.000   92.219   90.000
ZERR    1.000   0.0020   0.0020   0.0040    0.030    0.030    0.030
LATT  1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC H  0.042  0.991  0.103  3.924  0.205 11.597  0.170 31.984  0.006 =
  0.0 0.0 0.000 0.310 1.008
SFAC C  0.208  0.922  0.702  5.018  1.144 16.523  0.425 47.300  0.030 =
  0.0 0.0 0.000 0.770 12.011
UNIT 32 48
L.S. 50
ACTA
BOND
LIST 6
FMAP 2
PLAN 20
WGHT    0.200000
FVAR      27.17382
C1    2    0.638134    0.409442    0.303335    11.00000    0.06501    0.03527 =
         0.06996    0.00613    0.03176   -0.00133
H1    1    0.743448    0.475187    0.261834    11.00000   -1.50000
C2    2    0.069892    0.497060    0.391140    11.00000    0.04818    0.03798 =
         0.06863    0.00758    0.00495   -0.00501
C3    2    0.548096    0.131074    0.393975    11.00000    0.04974    0.02980 =
         0.04757    0.00211    0.01282    0.00129
C4    2    0.365286   -0.040112    0.480339    11.00000    0.03412    0.02854 =
         0.05927    0.00951    0.00860   -0.00062
AFIX  13
H2    1    0.302418   -0.217164    0.484159    11.00000   -1.20000
AFIX   0
C5    2    0.675019    0.201870    0.352173    11.00000    0.05371    0.04666 =
         0.05905   -0.00652    0.03347   -0.01138
H3    1    0.799580    0.103643    0.358367    11.00000   -1.50000
C6    2    0.180153    0.587637    0.344215    11.00000    0.05229    0.03910 =
         0.06191    0.00436   -0.00002    0.00254
H4    1    0.124275    0.733061    0.301610    11.00000   -1.50000
C7    2    0.274963    0.172305    0.437123    11.00000    0.03939    0.03421 =
         0.05463    0.00457    0.01463    0.00071
C8    2    0.390551    0.266647    0.389003    11.00000    0.04239    0.03013 =
         0.06689   -0.00434    0.01281    0.00124
C9    2    0.552485   -0.070169    0.451908    11.00000    0.04845    0.02212 =
         0.03436    0.00464    0.00238    0.00082
AFIX  13
H5    1    0.585397   -0.261740    0.440332    11.00000   -1.20000
AFIX   0
C10   2    0.347192    0.470933    0.341446    11.00000    0.06345    0.03223 =
         0.06995    0.00696    0.02059   -0.00035
C11   2    0.481311    0.541722    0.297781    11.00000    0.07712    0.03202 =
         0.07314    0.00358    0.02667   -0.00357
H6    1    0.462873    0.695934    0.259628    11.00000   -1.50000
C12   2    0.114617    0.288593    0.437207    11.00000    0.04367    0.03334 =
         0.07152   -0.00085    0.00928   -0.00371
H7    1    0.004302    0.234696    0.477949    11.00000   -1.50000
H8    1   -0.062574    0.602550    0.385853    11.00000    0.09656
HKLF 4




REM  allmerge_a.res in P2(1)/n
REM wR2 = 0.4720, GooF = S = 1.376, Restrained GooF = 1.376 for all data
REM R1 = 0.2174 for 750 Fo > 4sig(Fo) and 0.2738 for all 1348 data
REM 128 parameters refined using 0 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.256,  deepest hole -0.241,  1-sigma level  0.074
Q1    1   0.3827 -0.4790  0.5002  11.00000  0.05    0.26
Q2    1   0.3999  0.9889  0.2818  11.00000  0.05    0.23
Q3    1   0.3226 -0.0145  0.3202  11.00000  0.05    0.21
Q4    1   0.1610  0.8998  0.3412  11.00000  0.05    0.21
Q5    1   0.0520  0.8627  0.3822  11.00000  0.05    0.21
Q6    1   0.3797  0.7602  0.3723  11.00000  0.05    0.19
Q7    1   0.3080  0.4545  0.4748  11.00000  0.05    0.19
Q8    1   0.5622 -0.5325  0.4224  11.00000  0.05    0.18
Q9    1   0.3890 -0.0574  0.3949  11.00000  0.05    0.17
Q10   1   0.6239  0.7682  0.3227  11.00000  0.05    0.17
Q11   1   0.2062  1.0189  0.2979  11.00000  0.05    0.17
Q12   1   0.6529 -0.0590  0.3377  11.00000  0.05    0.15
Q13   1   0.1121  0.2381  0.4053  11.00000  0.05    0.14
Q14   1  -0.1355  0.0658  0.4968  11.00000  0.05    0.13
Q15   1   0.3606  0.1480  0.3559  11.00000  0.05    0.13
Q16   1   0.8778  0.5381  0.2403  11.00000  0.05    0.12
Q17   1   0.6654 -0.3448  0.4338  11.00000  0.05    0.12
Q18   1  -0.1406  0.7832  0.4163  11.00000  0.05    0.12
Q19   1   0.6146 -0.3727  0.4432  11.00000  0.05    0.12
Q20   1   0.4926  0.1518  0.2975  11.00000  0.05    0.12
;
_shelx_res_checksum              97906
