# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 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_n5616-lt_sq
_database_code_depnum_ccdc_archive 'CCDC 2023139'
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N2, I'
_chemical_formula_sum            'C24 H23 I N2'
_chemical_formula_weight         466.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   11.2655(13)
_cell_length_b                   13.6748(16)
_cell_length_c                   15.7542(19)
_cell_angle_alpha                87.413(6)
_cell_angle_beta                 74.285(5)
_cell_angle_gamma                66.856(6)
_cell_volume                     2143.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      32.35

_exptl_crystal_description       rhombic
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.579
_exptl_crystal_size_mid          0.446
_exptl_crystal_size_min          0.365
_exptl_absorpt_coefficient_mu    1.504
_shelx_estimated_absorpt_T_min   0.476
_shelx_estimated_absorpt_T_max   0.610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5139
_exptl_absorpt_correction_T_max  0.5658
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40269
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         33.321
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             16359
_reflns_number_gt                11386
_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. 
  
 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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.5199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         16359
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.56086(5) 0.67824(5) 0.03925(4) 0.05287(15) Uani 0.790(6) 1 d . . P A 1
I2 I 0.95036(12) 0.22109(6) 0.29322(3) 0.05200(11) Uani 0.970(4) 1 d . . P B 1
I1' I 0.5592(3) 0.7017(6) 0.0288(3) 0.0919(9) Uani 0.210(6) 1 d . . P A 2
I2' I 0.992(3) 0.2019(14) 0.2852(7) 0.05200(11) Uani 0.030(4) 1 d . . P B 2
N1 N 1.06702(15) 0.19971(13) 0.00593(10) 0.0413(3) Uani 1 1 d . . . . .
N2 N 0.96943(19) 0.70925(14) 0.41803(10) 0.0502(4) Uani 1 1 d . . . . .
C1 C 1.03660(19) 0.13560(15) -0.04652(11) 0.0408(4) Uani 1 1 d . . . . .
C2 C 1.1170(2) 0.03507(16) -0.08709(13) 0.0493(4) Uani 1 1 d . . . . .
H2 H 1.2061 -0.0021 -0.0828 0.059 Uiso 1 1 calc R U . . .
C3 C 1.0601(3) -0.00828(17) -0.13449(13) 0.0548(5) Uani 1 1 d . . . . .
H3 H 1.1119 -0.0770 -0.1641 0.066 Uiso 1 1 calc R U . . .
C4 C 0.9309(3) 0.04533(17) -0.13977(14) 0.0545(5) Uani 1 1 d . . . . .
H4 H 0.8946 0.0125 -0.1720 0.065 Uiso 1 1 calc R U . . .
C5 C 0.8519(2) 0.14713(17) -0.09875(13) 0.0497(4) Uani 1 1 d . . . . .
H5 H 0.7627 0.1842 -0.1028 0.060 Uiso 1 1 calc R U . . .
C6 C 0.90728(18) 0.19240(14) -0.05214(11) 0.0403(3) Uani 1 1 d . . . . .
C7 C 0.85031(17) 0.29989(14) -0.00287(11) 0.0391(3) Uani 1 1 d . . . . .
C8 C 0.96753(18) 0.29316(15) 0.03042(11) 0.0394(3) Uani 1 1 d . . . . .
C9 C 1.1928(2) 0.1607(2) 0.03184(16) 0.0563(5) Uani 1 1 d . . . . .
H9A H 1.2475 0.0869 0.0079 0.084 Uiso 1 1 calc R U . . .
H9B H 1.1724 0.1637 0.0965 0.084 Uiso 1 1 calc R U . . .
H9C H 1.2425 0.2055 0.0085 0.084 Uiso 1 1 calc R U . . .
C10 C 0.7281(2) 0.3129(2) 0.07621(13) 0.0537(5) Uani 1 1 d . . . . .
H10A H 0.6631 0.2957 0.0561 0.081 Uiso 1 1 calc R U . . .
H10B H 0.6859 0.3867 0.1016 0.081 Uiso 1 1 calc R U . . .
H10C H 0.7576 0.2647 0.1211 0.081 Uiso 1 1 calc R U . . .
C11 C 0.8142(2) 0.38861(17) -0.06667(14) 0.0539(5) Uani 1 1 d . . . . .
H11A H 0.8937 0.3785 -0.1160 0.081 Uiso 1 1 calc R U . . .
H11B H 0.7830 0.4582 -0.0351 0.081 Uiso 1 1 calc R U . . .
H11C H 0.7429 0.3856 -0.0895 0.081 Uiso 1 1 calc R U . . .
C12 C 0.9751(2) 0.36990(16) 0.08549(12) 0.0447(4) Uani 1 1 d . . . . .
H12 H 1.0533 0.3487 0.1057 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8824(2) 0.46867(16) 0.11113(12) 0.0443(4) Uani 1 1 d . . . . .
H13 H 0.8068 0.4936 0.0880 0.053 Uiso 1 1 calc R U . . .
C14 C 0.89168(19) 0.53990(15) 0.17281(11) 0.0409(4) Uani 1 1 d . . . . .
C15 C 0.8150(2) 0.64927(17) 0.17815(13) 0.0493(4) Uani 1 1 d . . . . .
H15 H 0.7546 0.6767 0.1427 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8257(2) 0.71849(16) 0.23440(13) 0.0478(4) Uani 1 1 d . . . . .
H16 H 0.7740 0.7929 0.2362 0.057 Uiso 1 1 calc R U . . .
C17 C 0.91186(19) 0.67967(15) 0.28845(11) 0.0399(3) Uani 1 1 d . . . . .
C18 C 0.9845(2) 0.57084(15) 0.28496(11) 0.0427(4) Uani 1 1 d . . . . .
H18 H 1.0419 0.5432 0.3224 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9757(2) 0.50138(15) 0.22830(12) 0.0432(4) Uani 1 1 d . . . . .
H19 H 1.0270 0.4270 0.2271 0.052 Uiso 1 1 calc R U . . .
C20 C 0.92830(19) 0.75250(15) 0.34728(11) 0.0415(4) Uani 1 1 d . . . . .
C21 C 0.9082(3) 0.85613(18) 0.32793(15) 0.0583(5) Uani 1 1 d . . . . .
H21 H 0.8775 0.8845 0.2780 0.070 Uiso 1 1 calc R U . . .
C22 C 0.9333(3) 0.9187(2) 0.38227(18) 0.0725(7) Uani 1 1 d . . . . .
H22 H 0.9213 0.9901 0.3700 0.087 Uiso 1 1 calc R U . . .
C23 C 0.9760(3) 0.8744(2) 0.45421(16) 0.0672(6) Uani 1 1 d . . . . .
H23 H 0.9946 0.9146 0.4926 0.081 Uiso 1 1 calc R U . . .
C24 C 0.9914(3) 0.77121(19) 0.46968(14) 0.0587(5) Uani 1 1 d . . . . .
H24 H 1.0194 0.7421 0.5203 0.070 Uiso 1 1 calc R U . . .
N1' N 0.71998(17) 0.48831(13) 0.54420(10) 0.0435(3) Uani 1 1 d . . . . .
N2' N 0.5401(3) -0.0187(3) 0.26621(19) 0.0991(10) Uani 1 1 d . . . . .
C1' C 0.71768(19) 0.55304(16) 0.61347(12) 0.0432(4) Uani 1 1 d . . . . .
C2' C 0.7745(2) 0.62664(17) 0.60673(15) 0.0520(5) Uani 1 1 d . . . . .
H2' H 0.8233 0.6405 0.5515 0.062 Uiso 1 1 calc R U . . .
C3' C 0.7563(3) 0.67935(19) 0.68544(18) 0.0616(6) Uani 1 1 d . . . . .
H3' H 0.7924 0.7317 0.6844 0.074 Uiso 1 1 calc R U . . .
C4' C 0.6864(3) 0.6571(2) 0.76536(17) 0.0654(6) Uani 1 1 d . . . . .
H4' H 0.6759 0.6944 0.8181 0.078 Uiso 1 1 calc R U . . .
C5' C 0.6315(2) 0.5819(2) 0.77042(14) 0.0587(5) Uani 1 1 d . . . . .
H5' H 0.5845 0.5665 0.8256 0.070 Uiso 1 1 calc R U . . .
C6' C 0.6472(2) 0.52983(18) 0.69232(13) 0.0485(4) Uani 1 1 d . . . . .
C7' C 0.6001(2) 0.44521(18) 0.67532(12) 0.0488(4) Uani 1 1 d . . . . .
C8' C 0.65369(19) 0.42778(16) 0.57469(12) 0.0434(4) Uani 1 1 d . . . . .
C9' C 0.7925(2) 0.4923(2) 0.45277(13) 0.0569(5) Uani 1 1 d . . . . .
H9'A H 0.7430 0.5592 0.4297 0.085 Uiso 1 1 calc R U . . .
H9'B H 0.8010 0.4320 0.4168 0.085 Uiso 1 1 calc R U . . .
H9'C H 0.8821 0.4882 0.4506 0.085 Uiso 1 1 calc R U . . .
C10' C 0.4459(2) 0.4881(2) 0.70899(17) 0.0704(7) Uani 1 1 d . . . . .
H10D H 0.4064 0.5547 0.6819 0.106 Uiso 1 1 calc R U . . .
H10E H 0.4179 0.5014 0.7734 0.106 Uiso 1 1 calc R U . . .
H10F H 0.4151 0.4354 0.6931 0.106 Uiso 1 1 calc R U . . .
C11' C 0.6685(3) 0.3430(2) 0.71781(16) 0.0656(6) Uani 1 1 d . . . . .
H11D H 0.6430 0.2869 0.7021 0.098 Uiso 1 1 calc R U . . .
H11E H 0.6400 0.3566 0.7822 0.098 Uiso 1 1 calc R U . . .
H11F H 0.7662 0.3201 0.6963 0.098 Uiso 1 1 calc R U . . .
C12' C 0.6392(2) 0.35731(17) 0.51789(13) 0.0501(4) Uani 1 1 d . . . . .
H12' H 0.6858 0.3499 0.4569 0.060 Uiso 1 1 calc R U . . .
C13' C 0.5629(2) 0.30051(18) 0.54579(14) 0.0533(5) Uani 1 1 d . . . . .
H13' H 0.5211 0.3062 0.6075 0.064 Uiso 1 1 calc R U . . .
C14' C 0.5384(2) 0.23204(17) 0.49154(14) 0.0505(4) Uani 1 1 d . . . . .
C15' C 0.4417(2) 0.19112(19) 0.53010(14) 0.0547(5) Uani 1 1 d . . . . .
H15' H 0.3962 0.2070 0.5913 0.066 Uiso 1 1 calc R U . . .
C16' C 0.4114(2) 0.12843(18) 0.48106(15) 0.0537(5) Uani 1 1 d . . . . .
H16' H 0.3436 0.1032 0.5083 0.064 Uiso 1 1 calc R U . . .
C17' C 0.4786(2) 0.10149(17) 0.39219(14) 0.0499(4) Uani 1 1 d . . . . .
C18' C 0.5761(2) 0.1406(2) 0.35348(16) 0.0648(6) Uani 1 1 d . . . . .
H18' H 0.6237 0.1222 0.2928 0.078 Uiso 1 1 calc R U . . .
C19' C 0.6047(2) 0.2057(2) 0.40176(16) 0.0647(6) Uani 1 1 d . . . . .
H19' H 0.6702 0.2330 0.3738 0.078 Uiso 1 1 calc R U . . .
C20' C 0.4455(2) 0.03441(18) 0.33812(15) 0.0540(5) Uani 1 1 d . . . . .
C21' C 0.3239(3) 0.0290(3) 0.3605(2) 0.0851(9) Uani 1 1 d . . . . .
H21' H 0.2578 0.0669 0.4127 0.102 Uiso 1 1 calc R U . . .
C22' C 0.2961(4) -0.0319(3) 0.3073(3) 0.0990(11) Uani 1 1 d . . . . .
H22' H 0.2103 -0.0352 0.3224 0.119 Uiso 1 1 calc R U . . .
C23' C 0.3896(3) -0.0859(3) 0.2348(2) 0.0842(9) Uani 1 1 d . . . . .
H23' H 0.3729 -0.1290 0.1977 0.101 Uiso 1 1 calc R U . . .
C24' C 0.5098(4) -0.0768(3) 0.2160(3) 0.1060(13) Uani 1 1 d . . . . .
H24' H 0.5765 -0.1140 0.1638 0.127 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
N1 C8 1.312(2) . ?
N1 C1 1.423(2) . ?
N1 C9 1.469(2) . ?
N2 C24 1.333(2) . ?
N2 C20 1.346(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.381(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(2) . ?
C7 C8 1.518(2) . ?
C7 C11 1.540(3) . ?
C7 C10 1.542(3) . ?
C8 C12 1.433(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.338(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.458(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C14 C19 1.397(2) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(3) . ?
C17 C20 1.485(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.378(3) . ?
C21 C22 1.390(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.371(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1' C8' 1.315(2) . ?
N1' C1' 1.424(2) . ?
N1' C9' 1.461(2) . ?
N2' C20' 1.326(3) . ?
N2' C24' 1.338(4) . ?
C1' C2' 1.376(3) . ?
C1' C6' 1.379(3) . ?
C2' C3' 1.388(3) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.384(4) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.384(4) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.383(3) . ?
C5' H5' 0.9500 . ?
C6' C7' 1.510(3) . ?
C7' C8' 1.529(2) . ?
C7' C11' 1.531(3) . ?
C7' C10' 1.540(3) . ?
C8' C12' 1.427(3) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C12' C13' 1.350(3) . ?
C12' H12' 0.9500 . ?
C13' C14' 1.445(3) . ?
C13' H13' 0.9500 . ?
C14' C19' 1.397(3) . ?
C14' C15' 1.400(3) . ?
C15' C16' 1.371(3) . ?
C15' H15' 0.9500 . ?
C16' C17' 1.387(3) . ?
C16' H16' 0.9500 . ?
C17' C18' 1.391(3) . ?
C17' C20' 1.489(3) . ?
C18' C19' 1.376(3) . ?
C18' H18' 0.9500 . ?
C19' H19' 0.9500 . ?
C20' C21' 1.350(3) . ?
C21' C22' 1.380(4) . ?
C21' H21' 0.9500 . ?
C22' C23' 1.331(5) . ?
C22' H22' 0.9500 . ?
C23' C24' 1.360(5) . ?
C23' H23' 0.9500 . ?
C24' H24' 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
C8 N1 C1 111.65(15) . . ?
C8 N1 C9 125.78(16) . . ?
C1 N1 C9 122.50(16) . . ?
C24 N2 C20 117.01(18) . . ?
C2 C1 C6 123.54(17) . . ?
C2 C1 N1 128.74(18) . . ?
C6 C1 N1 107.71(15) . . ?
C1 C2 C3 116.0(2) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C4 C3 C2 121.80(19) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 121.16(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C5 C6 C1 119.50(17) . . ?
C5 C6 C7 130.80(18) . . ?
C1 C6 C7 109.70(15) . . ?
C6 C7 C8 100.81(14) . . ?
C6 C7 C11 109.88(14) . . ?
C8 C7 C11 113.08(16) . . ?
C6 C7 C10 111.61(16) . . ?
C8 C7 C10 109.73(14) . . ?
C11 C7 C10 111.32(17) . . ?
N1 C8 C12 121.20(16) . . ?
N1 C8 C7 110.09(15) . . ?
C12 C8 C7 128.59(17) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 126.06(17) . . ?
C13 C12 H12 117.0 . . ?
C8 C12 H12 117.0 . . ?
C12 C13 C14 123.18(17) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C19 118.24(16) . . ?
C15 C14 C13 120.21(16) . . ?
C19 C14 C13 121.54(17) . . ?
C16 C15 C14 120.99(17) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.45(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 118.35(16) . . ?
C18 C17 C20 120.13(16) . . ?
C16 C17 C20 121.51(17) . . ?
C19 C18 C17 121.54(17) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C14 120.37(18) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
N2 C20 C21 122.61(17) . . ?
N2 C20 C17 115.66(16) . . ?
C21 C20 C17 121.67(17) . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C23 C22 C21 118.2(2) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
C24 C23 C22 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
N2 C24 C23 124.0(2) . . ?
N2 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
C8' N1' C1' 111.49(15) . . ?
C8' N1' C9' 127.73(17) . . ?
C1' N1' C9' 120.76(16) . . ?
C20' N2' C24' 117.4(3) . . ?
C2' C1' C6' 123.84(18) . . ?
C2' C1' N1' 127.97(18) . . ?
C6' C1' N1' 108.19(16) . . ?
C1' C2' C3' 116.0(2) . . ?
C1' C2' H2' 122.0 . . ?
C3' C2' H2' 122.0 . . ?
C4' C3' C2' 121.2(2) . . ?
C4' C3' H3' 119.4 . . ?
C2' C3' H3' 119.4 . . ?
C5' C4' C3' 121.7(2) . . ?
C5' C4' H4' 119.2 . . ?
C3' C4' H4' 119.2 . . ?
C6' C5' C4' 117.7(2) . . ?
C6' C5' H5' 121.1 . . ?
C4' C5' H5' 121.1 . . ?
C1' C6' C5' 119.6(2) . . ?
C1' C6' C7' 109.67(16) . . ?
C5' C6' C7' 130.7(2) . . ?
C6' C7' C8' 100.62(15) . . ?
C6' C7' C11' 110.27(18) . . ?
C8' C7' C11' 109.87(18) . . ?
C6' C7' C10' 109.72(18) . . ?
C8' C7' C10' 113.58(17) . . ?
C11' C7' C10' 112.2(2) . . ?
N1' C8' C12' 122.13(17) . . ?
N1' C8' C7' 110.01(15) . . ?
C12' C8' C7' 127.86(17) . . ?
N1' C9' H9'A 109.5 . . ?
N1' C9' H9'B 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
N1' C9' H9'C 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
C7' C10' H10D 109.5 . . ?
C7' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C7' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C7' C11' H11D 109.5 . . ?
C7' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C7' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C13' C12' C8' 123.79(19) . . ?
C13' C12' H12' 118.1 . . ?
C8' C12' H12' 118.1 . . ?
C12' C13' C14' 126.7(2) . . ?
C12' C13' H13' 116.6 . . ?
C14' C13' H13' 116.6 . . ?
C19' C14' C15' 117.92(19) . . ?
C19' C14' C13' 123.39(19) . . ?
C15' C14' C13' 118.68(19) . . ?
C16' C15' C14' 121.1(2) . . ?
C16' C15' H15' 119.4 . . ?
C14' C15' H15' 119.4 . . ?
C15' C16' C17' 120.70(19) . . ?
C15' C16' H16' 119.6 . . ?
C17' C16' H16' 119.6 . . ?
C16' C17' C18' 118.62(19) . . ?
C16' C17' C20' 121.14(19) . . ?
C18' C17' C20' 120.2(2) . . ?
C19' C18' C17' 121.0(2) . . ?
C19' C18' H18' 119.5 . . ?
C17' C18' H18' 119.5 . . ?
C18' C19' C14' 120.6(2) . . ?
C18' C19' H19' 119.7 . . ?
C14' C19' H19' 119.7 . . ?
N2' C20' C21' 121.4(2) . . ?
N2' C20' C17' 117.1(2) . . ?
C21' C20' C17' 121.5(2) . . ?
C20' C21' C22' 119.7(3) . . ?
C20' C21' H21' 120.2 . . ?
C22' C21' H21' 120.2 . . ?
C23' C22' C21' 120.0(3) . . ?
C23' C22' H22' 120.0 . . ?
C21' C22' H22' 120.0 . . ?
C22' C23' C24' 117.3(3) . . ?
C22' C23' H23' 121.3 . . ?
C24' C23' H23' 121.3 . . ?
N2' C24' C23' 124.2(3) . . ?
N2' C24' H24' 117.9 . . ?
C23' C24' H24' 117.9 . . ?

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
C8 N1 C1 C2 177.21(19) . . . . ?
C9 N1 C1 C2 -5.8(3) . . . . ?
C8 N1 C1 C6 -2.2(2) . . . . ?
C9 N1 C1 C6 174.84(17) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 -179.95(18) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 178.64(19) . . . . ?
C2 C1 C6 C5 1.5(3) . . . . ?
N1 C1 C6 C5 -179.05(17) . . . . ?
C2 C1 C6 C7 -178.17(17) . . . . ?
N1 C1 C6 C7 1.2(2) . . . . ?
C5 C6 C7 C8 -179.7(2) . . . . ?
C1 C6 C7 C8 -0.06(19) . . . . ?
C5 C6 C7 C11 -60.1(3) . . . . ?
C1 C6 C7 C11 119.51(17) . . . . ?
C5 C6 C7 C10 63.8(3) . . . . ?
C1 C6 C7 C10 -116.50(17) . . . . ?
C1 N1 C8 C12 178.57(16) . . . . ?
C9 N1 C8 C12 1.7(3) . . . . ?
C1 N1 C8 C7 2.2(2) . . . . ?
C9 N1 C8 C7 -174.74(18) . . . . ?
C6 C7 C8 N1 -1.28(19) . . . . ?
C11 C7 C8 N1 -118.51(17) . . . . ?
C10 C7 C8 N1 116.55(18) . . . . ?
C6 C7 C8 C12 -177.35(18) . . . . ?
C11 C7 C8 C12 65.4(2) . . . . ?
C10 C7 C8 C12 -59.5(2) . . . . ?
N1 C8 C12 C13 177.00(19) . . . . ?
C7 C8 C12 C13 -7.3(3) . . . . ?
C8 C12 C13 C14 175.10(18) . . . . ?
C12 C13 C14 C15 161.9(2) . . . . ?
C12 C13 C14 C19 -18.6(3) . . . . ?
C19 C14 C15 C16 2.5(3) . . . . ?
C13 C14 C15 C16 -178.00(19) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C15 C16 C17 C20 178.06(18) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C20 C17 C18 C19 -177.31(17) . . . . ?
C17 C18 C19 C14 -0.3(3) . . . . ?
C15 C14 C19 C18 -1.7(3) . . . . ?
C13 C14 C19 C18 178.77(18) . . . . ?
C24 N2 C20 C21 -0.4(3) . . . . ?
C24 N2 C20 C17 176.82(19) . . . . ?
C18 C17 C20 N2 -25.7(2) . . . . ?
C16 C17 C20 N2 155.56(19) . . . . ?
C18 C17 C20 C21 151.6(2) . . . . ?
C16 C17 C20 C21 -27.2(3) . . . . ?
N2 C20 C21 C22 1.2(4) . . . . ?
C17 C20 C21 C22 -175.9(2) . . . . ?
C20 C21 C22 C23 -0.8(4) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C20 N2 C24 C23 -0.8(4) . . . . ?
C22 C23 C24 N2 1.1(4) . . . . ?
C8' N1' C1' C2' -179.2(2) . . . . ?
C9' N1' C1' C2' 2.1(3) . . . . ?
C8' N1' C1' C6' 1.1(2) . . . . ?
C9' N1' C1' C6' -177.58(19) . . . . ?
C6' C1' C2' C3' -0.6(3) . . . . ?
N1' C1' C2' C3' 179.7(2) . . . . ?
C1' C2' C3' C4' 0.8(3) . . . . ?
C2' C3' C4' C5' -0.2(4) . . . . ?
C3' C4' C5' C6' -0.7(4) . . . . ?
C2' C1' C6' C5' -0.3(3) . . . . ?
N1' C1' C6' C5' 179.45(19) . . . . ?
C2' C1' C6' C7' -179.60(19) . . . . ?
N1' C1' C6' C7' 0.1(2) . . . . ?
C4' C5' C6' C1' 0.9(3) . . . . ?
C4' C5' C6' C7' -179.9(2) . . . . ?
C1' C6' C7' C8' -1.1(2) . . . . ?
C5' C6' C7' C8' 179.7(2) . . . . ?
C1' C6' C7' C11' 114.9(2) . . . . ?
C5' C6' C7' C11' -64.3(3) . . . . ?
C1' C6' C7' C10' -121.0(2) . . . . ?
C5' C6' C7' C10' 59.7(3) . . . . ?
C1' N1' C8' C12' 178.69(18) . . . . ?
C9' N1' C8' C12' -2.8(3) . . . . ?
C1' N1' C8' C7' -1.8(2) . . . . ?
C9' N1' C8' C7' 176.7(2) . . . . ?
C6' C7' C8' N1' 1.7(2) . . . . ?
C11' C7' C8' N1' -114.5(2) . . . . ?
C10' C7' C8' N1' 118.9(2) . . . . ?
C6' C7' C8' C12' -178.8(2) . . . . ?
C11' C7' C8' C12' 64.9(3) . . . . ?
C10' C7' C8' C12' -61.6(3) . . . . ?
N1' C8' C12' C13' -174.4(2) . . . . ?
C7' C8' C12' C13' 6.2(4) . . . . ?
C8' C12' C13' C14' 176.7(2) . . . . ?
C12' C13' C14' C19' 7.7(4) . . . . ?
C12' C13' C14' C15' -171.1(2) . . . . ?
C19' C14' C15' C16' -1.0(4) . . . . ?
C13' C14' C15' C16' 178.0(2) . . . . ?
C14' C15' C16' C17' 1.8(4) . . . . ?
C15' C16' C17' C18' -0.9(4) . . . . ?
C15' C16' C17' C20' -179.4(2) . . . . ?
C16' C17' C18' C19' -0.7(4) . . . . ?
C20' C17' C18' C19' 177.8(2) . . . . ?
C17' C18' C19' C14' 1.5(4) . . . . ?
C15' C14' C19' C18' -0.6(4) . . . . ?
C13' C14' C19' C18' -179.5(3) . . . . ?
C24' N2' C20' C21' 0.9(5) . . . . ?
C24' N2' C20' C17' -178.2(3) . . . . ?
C16' C17' C20' N2' -156.6(3) . . . . ?
C18' C17' C20' N2' 25.0(4) . . . . ?
C16' C17' C20' C21' 24.3(4) . . . . ?
C18' C17' C20' C21' -154.1(3) . . . . ?
N2' C20' C21' C22' -0.8(5) . . . . ?
C17' C20' C21' C22' 178.3(3) . . . . ?
C20' C21' C22' C23' 0.8(6) . . . . ?
C21' C22' C23' C24' -0.9(6) . . . . ?
C20' N2' C24' C23' -1.1(7) . . . . ?
C22' C23' C24' N2' 1.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#C9 H9B I2  0.98 3.31 4.188(3) 150.1 . 
#C9 H9C I1  0.98 3.12 4.087(2) 167.5 2_765 
C9 H9B I2' 0.98 3.05 3.960(15) 155.6 .
C9 H9C I1' 0.98 2.90 3.844(6) 162.6 2_765
#C24 H24 I2  0.95 3.13 3.976(2) 148.9 2_766 
#C24 H24 I2'  0.95 3.15 3.959(9) 144.0 2_766 
#C2' H2' N2  0.95 2.68 3.612(3) 167.2 . 
#C9' H9'B I2  0.98 3.14 4.058(3) 156.7 . 
#C12' H12' I2  0.95 3.28 4.126(2) 149.5 . 
#C23' H23' I1  0.95 3.32 4.050(3) 135.5 1_545 
#C23' H23' I1'  0.95 3.25 3.968(5) 134.1 1_545 

_refine_diff_density_max         0.651
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_R12117
_database_code_depnum_ccdc_archive 'CCDC 2023140'
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N2, P F6'
_chemical_formula_sum            'C24 H23 F6 N2 P'
_chemical_formula_weight         484.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.7668(4)
_cell_length_b                   9.7052(5)
_cell_length_c                   15.0202(8)
_cell_angle_alpha                98.578(3)
_cell_angle_beta                 99.776(3)
_cell_angle_gamma                90.498(3)
_cell_volume                     1102.60(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7317
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      35.54

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.142
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8810
_exptl_absorpt_correction_T_max  0.9282
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 8
_diffrn_reflns_number            24286
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.123
_diffrn_reflns_theta_max         36.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9455
_reflns_number_gt                6810
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.4508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9455
_refine_ls_number_parameters     301
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.92130(13) 0.08855(11) 0.17493(7) 0.01515(18) Uani 1 1 d . . . . .
N2 N -0.09191(14) 0.11513(12) 0.42826(7) 0.0184(2) Uani 1 1 d . . . . .
C1 C 1.04878(16) 0.12424(13) 0.12370(8) 0.0163(2) Uani 1 1 d . . . . .
C2 C 1.17334(17) 0.04061(15) 0.08959(9) 0.0219(2) Uani 1 1 d . . . . .
H2 H 1.1832 -0.0543 0.0978 0.026 Uiso 1 1 calc R U . . .
C3 C 1.28318(18) 0.10421(17) 0.04246(10) 0.0265(3) Uani 1 1 d . . . . .
H3 H 1.3709 0.0512 0.0177 0.032 Uiso 1 1 calc R U . . .
C4 C 1.26805(18) 0.24319(17) 0.03061(10) 0.0266(3) Uani 1 1 d . . . . .
H4 H 1.3448 0.2831 -0.0022 0.032 Uiso 1 1 calc R U . . .
C5 C 1.14184(18) 0.32460(16) 0.06627(9) 0.0231(3) Uani 1 1 d . . . . .
H5 H 1.1324 0.4199 0.0589 0.028 Uiso 1 1 calc R U . . .
C6 C 1.03066(16) 0.26277(13) 0.11271(8) 0.0169(2) Uani 1 1 d . . . . .
C7 C 0.88367(16) 0.32169(12) 0.15838(8) 0.0152(2) Uani 1 1 d . . . . .
C8 C 0.82419(15) 0.19557(12) 0.19569(8) 0.0145(2) Uani 1 1 d . . . . .
C9 C 0.90442(18) -0.05092(13) 0.20014(9) 0.0198(2) Uani 1 1 d . . . . .
H9A H 0.8075 -0.1036 0.1583 0.030 Uiso 1 1 calc R U . . .
H9B H 0.8813 -0.0421 0.2628 0.030 Uiso 1 1 calc R U . . .
H9C H 1.0132 -0.1000 0.1961 0.030 Uiso 1 1 calc R U . . .
C10 C 0.95330(18) 0.44349(13) 0.23449(9) 0.0205(2) Uani 1 1 d . . . . .
H10A H 1.0361 0.4087 0.2822 0.031 Uiso 1 1 calc R U . . .
H10B H 0.8555 0.4855 0.2610 0.031 Uiso 1 1 calc R U . . .
H10C H 1.0126 0.5138 0.2087 0.031 Uiso 1 1 calc R U . . .
C11 C 0.73527(17) 0.36654(14) 0.08776(9) 0.0197(2) Uani 1 1 d . . . . .
H11A H 0.7775 0.4440 0.0613 0.030 Uiso 1 1 calc R U . . .
H11B H 0.6364 0.3964 0.1179 0.030 Uiso 1 1 calc R U . . .
H11C H 0.6975 0.2877 0.0392 0.030 Uiso 1 1 calc R U . . .
C12 C 0.68241(16) 0.18173(13) 0.24345(8) 0.0161(2) Uani 1 1 d . . . . .
H12 H 0.6502 0.0904 0.2516 0.019 Uiso 1 1 calc R U . . .
C13 C 0.59037(16) 0.28847(13) 0.27797(8) 0.0167(2) Uani 1 1 d . . . . .
H13 H 0.6193 0.3802 0.2692 0.020 Uiso 1 1 calc R U . . .
C14 C 0.44924(16) 0.26931(12) 0.32792(8) 0.0153(2) Uani 1 1 d . . . . .
C15 C 0.40071(17) 0.38112(13) 0.38820(9) 0.0176(2) Uani 1 1 d . . . . .
H15 H 0.4591 0.4695 0.3954 0.021 Uiso 1 1 calc R U . . .
C16 C 0.26804(17) 0.36374(13) 0.43748(9) 0.0186(2) Uani 1 1 d . . . . .
H16 H 0.2391 0.4397 0.4793 0.022 Uiso 1 1 calc R U . . .
C17 C 0.17676(16) 0.23601(12) 0.42623(8) 0.0157(2) Uani 1 1 d . . . . .
C18 C 0.22627(16) 0.12473(13) 0.36626(8) 0.0163(2) Uani 1 1 d . . . . .
H18 H 0.1666 0.0367 0.3583 0.020 Uiso 1 1 calc R U . . .
C19 C 0.36013(16) 0.14065(13) 0.31847(8) 0.0167(2) Uani 1 1 d . . . . .
H19 H 0.3922 0.0633 0.2787 0.020 Uiso 1 1 calc R U . . .
C20 C 0.02452(17) 0.21673(13) 0.47126(8) 0.0171(2) Uani 1 1 d . . . . .
C21 C 0.0026(2) 0.29949(16) 0.55255(11) 0.0288(3) Uani 1 1 d . . . . .
H21 H 0.0890 0.3684 0.5829 0.035 Uiso 1 1 calc R U . . .
C22 C -0.1474(2) 0.27968(16) 0.58849(11) 0.0305(3) Uani 1 1 d . . . . .
H22 H -0.1654 0.3352 0.6436 0.037 Uiso 1 1 calc R U . . .
C23 C -0.26977(19) 0.17839(15) 0.54323(10) 0.0239(3) Uani 1 1 d . . . . .
H23 H -0.3752 0.1643 0.5653 0.029 Uiso 1 1 calc R U . . .
C24 C -0.23469(17) 0.09755(15) 0.46459(9) 0.0210(2) Uani 1 1 d . . . . .
H24 H -0.3170 0.0253 0.4347 0.025 Uiso 1 1 calc R U . . .
P1 P 0.47731(5) 0.72587(3) 0.20736(2) 0.01947(8) Uani 1 1 d D . . . .
F1 F 0.28795(14) 0.77588(12) 0.22180(9) 0.0440(3) Uani 1 1 d D . . . .
F2 F 0.66916(12) 0.67964(9) 0.19473(7) 0.0314(2) Uani 1 1 d D . . . .
F3 F 0.47281(16) 0.62015(11) 0.27840(8) 0.0439(3) Uani 1 1 d D . . . .
F4 F 0.56309(16) 0.84602(10) 0.28902(7) 0.0399(2) Uani 1 1 d D . . . .
F5 F 0.48297(12) 0.83441(10) 0.13677(6) 0.0290(2) Uani 1 1 d D . . . .
F6 F 0.39697(16) 0.60836(12) 0.12576(8) 0.0458(3) Uani 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.3198(15) . ?
N1 C1 1.4230(16) . ?
N1 C9 1.4695(16) . ?
N2 C24 1.3367(16) . ?
N2 C20 1.3429(17) . ?
C1 C2 1.3838(17) . ?
C1 C6 1.3842(17) . ?
C2 C3 1.391(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3830(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.5037(17) . ?
C7 C8 1.5192(16) . ?
C7 C10 1.5403(18) . ?
C7 C11 1.5409(17) . ?
C8 C12 1.4282(16) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3534(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.4548(17) . ?
C13 H13 0.9500 . ?
C14 C19 1.3989(18) . ?
C14 C15 1.4033(17) . ?
C15 C16 1.3897(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3963(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.4000(16) . ?
C17 C20 1.4820(17) . ?
C18 C19 1.3797(17) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3947(18) . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3862(19) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
P1 F6 1.5821(11) . ?
P1 F3 1.5910(9) . ?
P1 F1 1.5922(10) . ?
P1 F2 1.5936(9) . ?
P1 F5 1.6074(9) . ?
P1 F4 1.6095(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
C8 N1 C1 111.28(10) . . ?
C8 N1 C9 125.89(10) . . ?
C1 N1 C9 122.83(10) . . ?
C24 N2 C20 117.68(11) . . ?
C2 C1 C6 123.51(12) . . ?
C2 C1 N1 128.31(12) . . ?
C6 C1 N1 108.17(10) . . ?
C1 C2 C3 115.86(13) . . ?
C1 C2 H2 122.1 . . ?
C3 C2 H2 122.1 . . ?
C4 C3 C2 121.80(13) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.85(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.11(13) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 119.86(12) . . ?
C5 C6 C7 130.74(12) . . ?
C1 C6 C7 109.39(10) . . ?
C6 C7 C8 101.15(9) . . ?
C6 C7 C10 109.99(10) . . ?
C8 C7 C10 112.55(10) . . ?
C6 C7 C11 110.77(10) . . ?
C8 C7 C11 110.21(10) . . ?
C10 C7 C11 111.70(10) . . ?
N1 C8 C12 120.94(11) . . ?
N1 C8 C7 110.00(10) . . ?
C12 C8 C7 129.02(10) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C8 125.14(11) . . ?
C13 C12 H12 117.4 . . ?
C8 C12 H12 117.4 . . ?
C12 C13 C14 123.08(11) . . ?
C12 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C19 C14 C15 118.32(11) . . ?
C19 C14 C13 121.68(11) . . ?
C15 C14 C13 119.99(11) . . ?
C16 C15 C14 120.62(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.83(11) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 118.23(11) . . ?
C16 C17 C20 122.44(11) . . ?
C18 C17 C20 119.24(11) . . ?
C19 C18 C17 121.17(12) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 120.79(11) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
N2 C20 C21 122.13(12) . . ?
N2 C20 C17 115.64(11) . . ?
C21 C20 C17 122.24(12) . . ?
C22 C21 C20 119.00(14) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C23 C22 C21 119.11(13) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
C22 C23 C24 118.10(13) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
N2 C24 C23 123.91(13) . . ?
N2 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
F6 P1 F3 90.50(7) . . ?
F6 P1 F1 91.62(7) . . ?
F3 P1 F1 90.10(6) . . ?
F6 P1 F2 89.95(6) . . ?
F3 P1 F2 90.22(6) . . ?
F1 P1 F2 178.40(7) . . ?
F6 P1 F5 90.32(6) . . ?
F3 P1 F5 179.18(6) . . ?
F1 P1 F5 89.86(5) . . ?
F2 P1 F5 89.80(5) . . ?
F6 P1 F4 178.54(7) . . ?
F3 P1 F4 90.36(6) . . ?
F1 P1 F4 89.56(7) . . ?
F2 P1 F4 88.87(6) . . ?
F5 P1 F4 88.82(6) . . ?

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
C8 N1 C1 C2 -179.89(13) . . . . ?
C9 N1 C1 C2 0.1(2) . . . . ?
C8 N1 C1 C6 0.60(14) . . . . ?
C9 N1 C1 C6 -179.36(11) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C2 C3 -179.29(12) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 179.94(13) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C1 C6 C5 178.89(11) . . . . ?
C2 C1 C6 C7 -179.82(12) . . . . ?
N1 C1 C6 C7 -0.29(14) . . . . ?
C5 C6 C7 C8 -179.13(13) . . . . ?
C1 C6 C7 C8 -0.07(13) . . . . ?
C5 C6 C7 C10 -59.94(17) . . . . ?
C1 C6 C7 C10 119.12(11) . . . . ?
C5 C6 C7 C11 64.04(18) . . . . ?
C1 C6 C7 C11 -116.90(12) . . . . ?
C1 N1 C8 C12 177.13(11) . . . . ?
C9 N1 C8 C12 -2.91(19) . . . . ?
C1 N1 C8 C7 -0.65(14) . . . . ?
C9 N1 C8 C7 179.31(11) . . . . ?
C6 C7 C8 N1 0.44(13) . . . . ?
C10 C7 C8 N1 -116.90(11) . . . . ?
C11 C7 C8 N1 117.68(11) . . . . ?
C6 C7 C8 C12 -177.11(12) . . . . ?
C10 C7 C8 C12 65.55(16) . . . . ?
C11 C7 C8 C12 -59.87(16) . . . . ?
N1 C8 C12 C13 170.99(12) . . . . ?
C7 C8 C12 C13 -11.7(2) . . . . ?
C8 C12 C13 C14 -178.62(12) . . . . ?
C12 C13 C14 C19 -21.68(19) . . . . ?
C12 C13 C14 C15 157.60(12) . . . . ?
C19 C14 C15 C16 0.34(18) . . . . ?
C13 C14 C15 C16 -178.96(12) . . . . ?
C14 C15 C16 C17 -1.85(19) . . . . ?
C15 C16 C17 C18 2.05(19) . . . . ?
C15 C16 C17 C20 -174.51(12) . . . . ?
C16 C17 C18 C19 -0.80(18) . . . . ?
C20 C17 C18 C19 175.87(11) . . . . ?
C17 C18 C19 C14 -0.68(19) . . . . ?
C15 C14 C19 C18 0.91(18) . . . . ?
C13 C14 C19 C18 -179.80(11) . . . . ?
C24 N2 C20 C21 1.92(19) . . . . ?
C24 N2 C20 C17 -177.51(11) . . . . ?
C16 C17 C20 N2 153.22(12) . . . . ?
C18 C17 C20 N2 -23.30(16) . . . . ?
C16 C17 C20 C21 -26.20(19) . . . . ?
C18 C17 C20 C21 157.27(13) . . . . ?
N2 C20 C21 C22 -2.4(2) . . . . ?
C17 C20 C21 C22 177.01(14) . . . . ?
C20 C21 C22 C23 0.4(2) . . . . ?
C21 C22 C23 C24 1.8(2) . . . . ?
C20 N2 C24 C23 0.51(19) . . . . ?
C22 C23 C24 N2 -2.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F5 0.95 2.59 3.1967(16) 122.2 1_645
C9 H9A F2 0.98 2.53 3.1602(16) 122.3 1_545
C9 H9A F5 0.98 2.54 3.3796(17) 143.5 1_545
C9 H9B N2 0.98 2.69 3.5577(17) 147.9 1_655
C9 H9C F1 0.98 2.46 3.4243(16) 167.5 1_645
C12 H12 F4 0.95 2.63 3.5736(17) 175.2 1_545
C24 H24 F4 0.95 2.61 3.4622(18) 149.0 1_445

_refine_diff_density_max         0.860
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.068

