# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ANH-BRM-1LT-100K
_database_code_depnum_ccdc_archive 'CCDC 2022170'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.0179(5)
_cell_length_b                   13.6325(5)
_cell_length_c                   22.7651(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.5360(10)
_cell_angle_gamma                90
_cell_volume                     4148.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9696
_cell_measurement_theta_min      2.4596
_cell_measurement_theta_max      30.4294

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            148821
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.809
_diffrn_reflns_theta_max         30.448
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             23303
_reflns_number_gt                22562
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0573P)²+0.5621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 10398 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         23303
_refine_ls_number_parameters     1201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
F1 F -0.04488(8) 0.58257(10) 0.36115(5) 0.0296(2) Uani 1 1 d . . . . .
F2 F -0.07267(8) 0.67486(10) 0.15848(5) 0.0306(3) Uani 1 1 d . . . . .
F3 F 0.67457(9) 0.50626(10) -0.01495(5) 0.0320(3) Uani 1 1 d . . . . .
F4 F 0.37800(8) 0.68971(9) -0.06313(5) 0.0286(2) Uani 1 1 d . . . . .
C1 C 0.42316(12) 0.63609(13) 0.37993(7) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.462941 0.640679 0.421786 0.022 Uiso 1 1 calc R U . . .
C2 C 0.31986(12) 0.63536(12) 0.36394(7) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.288886 0.640852 0.395609 0.021 Uiso 1 1 calc R U . . .
C3 C 0.25861(11) 0.62675(12) 0.30220(7) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.30409(11) 0.62012(12) 0.25545(7) 0.0148(3) Uani 1 1 d . . . . .
H4 H 0.264219 0.613518 0.213739 0.018 Uiso 1 1 calc R U . . .
C5 C 0.46600(11) 0.61585(12) 0.17126(7) 0.0147(3) Uani 1 1 d . . . . .
H5 H 0.401165 0.613777 0.142182 0.018 Uiso 1 1 calc R U . . .
C6 C 0.55113(11) 0.61510(12) 0.15138(7) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.64704(11) 0.61973(12) 0.19515(7) 0.0166(3) Uani 1 1 d . . . . .
H7 H 0.704376 0.619663 0.181124 0.020 Uiso 1 1 calc R U . . .
C8 C 0.66008(11) 0.62437(12) 0.25796(7) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.725007 0.627525 0.286880 0.020 Uiso 1 1 calc R U . . .
N9 N 0.56688(10) 0.63067(11) 0.33600(6) 0.0170(2) Uani 1 1 d . . . . .
H9 H 0.6145(17) 0.6251(18) 0.3722(10) 0.020 Uiso 1 1 d . U . . .
C10 C 0.46717(11) 0.62986(12) 0.33249(7) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.40774(11) 0.62319(12) 0.27014(7) 0.0147(3) Uani 1 1 d . . . . .
C12 C 0.47724(11) 0.61968(12) 0.23424(7) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.57466(11) 0.62425(12) 0.27715(7) 0.0150(3) Uani 1 1 d . . . . .
C14 C 0.14833(11) 0.62651(12) 0.28784(7) 0.0149(3) Uani 1 1 d . . . . .
C15 C 0.10188(12) 0.60297(12) 0.33246(7) 0.0177(3) Uani 1 1 d . . . . .
H15 H 0.140960 0.585880 0.373029 0.021 Uiso 1 1 calc R U . . .
C16 C -0.00112(12) 0.60476(13) 0.31708(8) 0.0192(3) Uani 1 1 d . . . . .
C17 C -0.06326(12) 0.62789(13) 0.25910(8) 0.0208(3) Uani 1 1 d . . . . .
H17 H -0.134059 0.628605 0.249600 0.025 Uiso 1 1 calc R U . . .
C18 C -0.01539(12) 0.64989(13) 0.21597(8) 0.0198(3) Uani 1 1 d . . . . .
C19 C 0.08714(12) 0.65096(13) 0.22857(7) 0.0180(3) Uani 1 1 d . . . . .
H19 H 0.116232 0.668143 0.197315 0.022 Uiso 1 1 calc R U . . .
C20 C 0.54214(11) 0.61019(12) 0.08484(7) 0.0157(3) Uani 1 1 d . . . . .
C21 C 0.61413(12) 0.55993(13) 0.06500(7) 0.0183(3) Uani 1 1 d . . . . .
H21 H 0.669099 0.528959 0.094058 0.022 Uiso 1 1 calc R U . . .
C22 C 0.60445(13) 0.55584(14) 0.00300(8) 0.0216(3) Uani 1 1 d . . . . .
C23 C 0.52667(13) 0.59895(14) -0.04180(8) 0.0223(3) Uani 1 1 d . . . . .
H23 H 0.521313 0.595357 -0.084353 0.027 Uiso 1 1 calc R U . . .
C24 C 0.45722(12) 0.64761(13) -0.02064(7) 0.0204(3) Uani 1 1 d . . . . .
C25 C 0.46205(12) 0.65493(12) 0.04065(7) 0.0177(3) Uani 1 1 d . . . . .
H25 H 0.412119 0.689572 0.052631 0.021 Uiso 1 1 calc R U . . .
N31 N 0.71416(10) 0.60790(11) 0.45222(6) 0.0169(2) Uani 1 1 d . . . . .
C31 C 0.81351(12) 0.60604(13) 0.44266(7) 0.0184(3) Uani 1 1 d . . . . .
H31A H 0.821294 0.664004 0.418309 0.022 Uiso 1 1 calc R U . . .
H31B H 0.820091 0.546372 0.419404 0.022 Uiso 1 1 calc R U . . .
C32 C 0.89589(11) 0.60673(13) 0.50581(7) 0.0186(3) Uani 1 1 d . . . . .
H32A H 0.939699 0.548778 0.508913 0.022 Uiso 1 1 calc R U . . .
H32B H 0.937560 0.666325 0.509182 0.022 Uiso 1 1 calc R U . . .
C33 C 0.70323(13) 0.51995(13) 0.48723(8) 0.0223(3) Uani 1 1 d . . . . .
H33A H 0.707450 0.460377 0.463266 0.027 Uiso 1 1 calc R U . . .
H33B H 0.636903 0.520601 0.494275 0.027 Uiso 1 1 calc R U . . .
C34 C 0.78655(13) 0.51750(13) 0.54984(8) 0.0210(3) Uani 1 1 d . . . . .
H34A H 0.756023 0.515575 0.583782 0.025 Uiso 1 1 calc R U . . .
H34B H 0.827513 0.457583 0.552415 0.025 Uiso 1 1 calc R U . . .
C35 C 0.70677(13) 0.69561(13) 0.48839(8) 0.0198(3) Uani 1 1 d . . . . .
H35A H 0.639432 0.698633 0.493916 0.024 Uiso 1 1 calc R U . . .
H35B H 0.716107 0.755244 0.465917 0.024 Uiso 1 1 calc R U . . .
C36 C 0.78712(12) 0.69242(13) 0.55207(7) 0.0185(3) Uani 1 1 d . . . . .
H36A H 0.828840 0.752338 0.557877 0.022 Uiso 1 1 calc R U . . .
H36B H 0.754293 0.690453 0.584939 0.022 Uiso 1 1 calc R U . . .
N32 N 0.85085(10) 0.60501(11) 0.55651(6) 0.0175(3) Uani 1 1 d . . . . .
F41 F 1.62627(9) 0.57893(11) 0.63570(5) 0.0320(3) Uani 1 1 d . . . . .
F42 F 1.66351(8) 0.64894(10) 0.84281(5) 0.0309(3) Uani 1 1 d . . . . .
F43 F 0.89672(10) 0.60167(12) 1.02016(6) 0.0387(3) Uani 1 1 d . . . . .
F44 F 1.21968(10) 0.73241(12) 1.06033(6) 0.0428(3) Uani 1 1 d . . . . .
C41 C 1.16279(12) 0.62449(13) 0.62155(7) 0.0180(3) Uani 1 1 d . . . . .
H41 H 1.122778 0.623888 0.579636 0.022 Uiso 1 1 calc R U . . .
C42 C 1.26600(11) 0.62622(13) 0.63714(7) 0.0173(3) Uani 1 1 d . . . . .
H42 H 1.296569 0.628478 0.605163 0.021 Uiso 1 1 calc R U . . .
C43 C 1.32773(11) 0.62475(12) 0.69910(7) 0.0149(3) Uani 1 1 d . . . . .
C44 C 1.28248(11) 0.62387(11) 0.74606(7) 0.0144(3) Uani 1 1 d . . . . .
H44 H 1.322601 0.622534 0.787943 0.017 Uiso 1 1 calc R U . . .
C45 C 1.12022(11) 0.63467(12) 0.83041(7) 0.0156(3) Uani 1 1 d . . . . .
H45 H 1.184973 0.633647 0.859616 0.019 Uiso 1 1 calc R U . . .
C46 C 1.03507(12) 0.64258(12) 0.85021(7) 0.0163(3) Uani 1 1 d . . . . .
C47 C 0.93947(12) 0.64327(13) 0.80605(7) 0.0182(3) Uani 1 1 d . . . . .
H47 H 0.882062 0.649318 0.819733 0.022 Uiso 1 1 calc R U . . .
C48 C 0.92660(11) 0.63545(13) 0.74355(7) 0.0176(3) Uani 1 1 d . . . . .
H48 H 0.861698 0.635065 0.714502 0.021 Uiso 1 1 calc R U . . .
N49 N 1.01915(10) 0.62464(11) 0.66556(6) 0.0168(2) Uani 1 1 d . . . . .
H49 H 0.9640(18) 0.6209(18) 0.6325(10) 0.020 Uiso 1 1 d . U . . .
C50 C 1.11909(11) 0.62364(12) 0.66891(7) 0.0158(3) Uani 1 1 d . . . . .
C51 C 1.17868(11) 0.62495(11) 0.73150(7) 0.0139(3) Uani 1 1 d . . . . .
C52 C 1.10939(11) 0.62829(12) 0.76760(7) 0.0143(3) Uani 1 1 d . . . . .
C53 C 1.01239(11) 0.62811(12) 0.72462(7) 0.0153(3) Uani 1 1 d . . . . .
C54 C 1.43847(11) 0.62307(11) 0.71321(7) 0.0146(3) Uani 1 1 d . . . . .
C55 C 1.48277(12) 0.60209(12) 0.66686(7) 0.0179(3) Uani 1 1 d . . . . .
H55 H 1.442280 0.589761 0.625856 0.021 Uiso 1 1 calc R U . . .
C56 C 1.58567(13) 0.59958(13) 0.68156(8) 0.0200(3) Uani 1 1 d . . . . .
C57 C 1.64979(12) 0.61471(13) 0.73995(8) 0.0203(3) Uani 1 1 d . . . . .
H57 H 1.720460 0.611910 0.748952 0.024 Uiso 1 1 calc R U . . .
C58 C 1.60386(12) 0.63419(13) 0.78432(7) 0.0198(3) Uani 1 1 d . . . . .
C59 C 1.50194(12) 0.64011(12) 0.77303(7) 0.0175(3) Uani 1 1 d . . . . .
H59 H 1.474777 0.655596 0.805416 0.021 Uiso 1 1 calc R U . . .
C60 C 1.04351(12) 0.65096(13) 0.91650(7) 0.0185(3) Uani 1 1 d . . . . .
C61 C 0.96454(13) 0.62148(14) 0.93850(8) 0.0223(3) Uani 1 1 d . . . . .
H61 H 0.905060 0.594941 0.911061 0.027 Uiso 1 1 calc R U . . .
C62 C 0.97413(15) 0.63143(16) 1.00043(8) 0.0282(4) Uani 1 1 d . . . . .
C63 C 1.05815(17) 0.66818(18) 1.04311(8) 0.0323(4) Uani 1 1 d . . . . .
H63 H 1.063114 0.674071 1.085512 0.039 Uiso 1 1 calc R U . . .
C64 C 1.13494(15) 0.69599(16) 1.02016(8) 0.0288(4) Uani 1 1 d . . . . .
C65 C 1.13041(14) 0.68918(14) 0.95879(8) 0.0232(3) Uani 1 1 d . . . . .
H65 H 1.185145 0.709992 0.945422 0.028 Uiso 1 1 calc R U . . .
F71 F 0.93023(8) 0.42116(12) 0.85538(6) 0.0386(3) Uani 1 1 d . . . . .
F72 F 0.76295(9) 0.35607(9) 0.64787(5) 0.0284(2) Uani 1 1 d . . . . .
F73 F -0.17299(8) 0.27501(10) 0.48237(5) 0.0308(3) Uani 1 1 d . . . . .
F74 F 0.08808(9) 0.42656(9) 0.42679(5) 0.0278(2) Uani 1 1 d . . . . .
C71 C 0.48180(12) 0.37799(14) 0.87075(7) 0.0195(3) Uani 1 1 d . . . . .
H71 H 0.483168 0.379224 0.912724 0.023 Uiso 1 1 calc R U . . .
C72 C 0.56921(12) 0.37741(13) 0.85478(7) 0.0188(3) Uani 1 1 d . . . . .
H72 H 0.631271 0.377847 0.886629 0.023 Uiso 1 1 calc R U . . .
C73 C 0.56998(11) 0.37617(12) 0.79269(7) 0.0148(3) Uani 1 1 d . . . . .
C74 C 0.47850(11) 0.37397(12) 0.74610(7) 0.0143(3) Uani 1 1 d . . . . .
H74 H 0.477246 0.372725 0.704154 0.017 Uiso 1 1 calc R U . . .
C75 C 0.23274(11) 0.36617(12) 0.66263(7) 0.0150(3) Uani 1 1 d . . . . .
H75 H 0.268384 0.364096 0.633167 0.018 Uiso 1 1 calc R U . . .
C76 C 0.12812(11) 0.36452(12) 0.64341(7) 0.0153(3) Uani 1 1 d . . . . .
C77 C 0.07655(11) 0.36921(13) 0.68806(7) 0.0171(3) Uani 1 1 d . . . . .
H77 H 0.005475 0.369229 0.674624 0.020 Uiso 1 1 calc R U . . .
C78 C 0.12561(12) 0.37373(13) 0.75026(7) 0.0176(3) Uani 1 1 d . . . . .
H78 H 0.089706 0.376899 0.779562 0.021 Uiso 1 1 calc R U . . .
N79 N 0.29546(10) 0.37692(12) 0.82740(6) 0.0180(3) Uani 1 1 d . . . . .
H79 H 0.2796(17) 0.3787(18) 0.8639(11) 0.022 Uiso 1 1 d . U . . .
C80 C 0.39138(12) 0.37672(12) 0.82347(7) 0.0160(3) Uani 1 1 d . . . . .
C81 C 0.38910(11) 0.37358(12) 0.76095(7) 0.0147(3) Uani 1 1 d . . . . .
C82 C 0.28434(11) 0.37089(12) 0.72536(7) 0.0139(3) Uani 1 1 d . . . . .
C83 C 0.22997(11) 0.37350(12) 0.76871(7) 0.0152(3) Uani 1 1 d . . . . .
C84 C 0.66651(11) 0.37904(11) 0.77843(7) 0.0152(3) Uani 1 1 d . . . . .
C85 C 0.75636(12) 0.39897(13) 0.82463(8) 0.0209(3) Uani 1 1 d . . . . .
H85 H 0.756645 0.409293 0.865954 0.025 Uiso 1 1 calc R U . . .
C86 C 0.84417(13) 0.40339(15) 0.80935(9) 0.0250(4) Uani 1 1 d . . . . .
C87 C 0.85044(13) 0.39108(14) 0.75076(9) 0.0245(4) Uani 1 1 d . . . . .
H87 H 0.911920 0.396316 0.741466 0.029 Uiso 1 1 calc R U . . .
C88 C 0.76101(13) 0.37052(13) 0.70626(8) 0.0205(3) Uani 1 1 d . . . . .
C89 C 0.67068(12) 0.36343(12) 0.71845(7) 0.0180(3) Uani 1 1 d . . . . .
H89 H 0.611501 0.348015 0.686283 0.022 Uiso 1 1 calc R U . . .
C90 C 0.06990(11) 0.35898(12) 0.57733(7) 0.0158(3) Uani 1 1 d . . . . .
C91 C -0.02566(12) 0.31636(13) 0.55947(8) 0.0190(3) Uani 1 1 d . . . . .
H91 H -0.052490 0.288877 0.589459 0.023 Uiso 1 1 calc R U . . .
C92 C -0.08036(12) 0.31477(14) 0.49779(8) 0.0218(3) Uani 1 1 d . . . . .
C93 C -0.04556(13) 0.35054(14) 0.45140(8) 0.0233(3) Uani 1 1 d . . . . .
H93 H -0.083995 0.347661 0.409213 0.028 Uiso 1 1 calc R U . . .
C94 C 0.04921(13) 0.39087(13) 0.47070(7) 0.0204(3) Uani 1 1 d . . . . .
C95 C 0.10759(12) 0.39704(12) 0.53140(7) 0.0181(3) Uani 1 1 d . . . . .
H95 H 0.171979 0.426435 0.541915 0.022 Uiso 1 1 calc R U . . .
N101 N 0.25360(10) 0.37417(11) 0.94131(6) 0.0171(2) Uani 1 1 d . . . . .
C101 C 0.14599(12) 0.38873(13) 0.93296(7) 0.0188(3) Uani 1 1 d . . . . .
H101 H 0.107398 0.333123 0.909404 0.023 Uiso 1 1 calc R U . . .
H102 H 0.122877 0.449684 0.909324 0.023 Uiso 1 1 calc R U . . .
C102 C 0.12779(12) 0.39578(13) 0.99658(8) 0.0198(3) Uani 1 1 d . . . . .
H103 H 0.097346 0.460048 1.000449 0.024 Uiso 1 1 calc R U . . .
H104 H 0.080661 0.343692 1.000185 0.024 Uiso 1 1 calc R U . . .
C103 C 0.28564(13) 0.28258(13) 0.97578(8) 0.0217(3) Uani 1 1 d . . . . .
H105 H 0.357404 0.270831 0.980973 0.026 Uiso 1 1 calc R U . . .
H106 H 0.246996 0.226767 0.952503 0.026 Uiso 1 1 calc R U . . .
C104 C 0.26862(13) 0.28964(13) 1.03976(8) 0.0215(3) Uani 1 1 d . . . . .
H107 H 0.224031 0.235806 1.044395 0.026 Uiso 1 1 calc R U . . .
H108 H 0.333336 0.282426 1.072468 0.026 Uiso 1 1 calc R U . . .
C105 C 0.30956(13) 0.45667(14) 0.97687(8) 0.0212(3) Uani 1 1 d . . . . .
H109 H 0.287799 0.518570 0.954017 0.025 Uiso 1 1 calc R U . . .
H110 H 0.381854 0.447946 0.982381 0.025 Uiso 1 1 calc R U . . .
C106 C 0.29193(13) 0.46298(13) 1.04063(7) 0.0204(3) Uani 1 1 d . . . . .
H111 H 0.356475 0.456133 1.073541 0.025 Uiso 1 1 calc R U . . .
H112 H 0.263111 0.527745 1.045334 0.025 Uiso 1 1 calc R U . . .
N102 N 0.22325(10) 0.38481(11) 1.04655(6) 0.0181(3) Uani 1 1 d . . . . .
F111 F -0.46333(8) 0.33103(9) 1.13559(5) 0.0265(2) Uani 1 1 d . . . . .
F112 F -0.29359(8) 0.40914(9) 1.34090(5) 0.0272(2) Uani 1 1 d . . . . .
F113 F 0.63133(9) 0.27977(12) 1.50750(6) 0.0391(3) Uani 1 1 d . . . . .
F114 F 0.37351(10) 0.45361(10) 1.55285(5) 0.0344(3) Uani 1 1 d . . . . .
C111 C -0.01833(12) 0.41126(13) 1.11570(7) 0.0177(3) Uani 1 1 d . . . . .
H113 H -0.020341 0.422507 1.074157 0.021 Uiso 1 1 calc R U . . .
C112 C -0.10537(12) 0.40800(12) 1.13252(7) 0.0170(3) Uani 1 1 d . . . . .
H114 H -0.167651 0.418233 1.101815 0.020 Uiso 1 1 calc R U . . .
C113 C -0.10476(11) 0.38996(11) 1.19382(7) 0.0143(3) Uani 1 1 d . . . . .
C114 C -0.01313(11) 0.37877(12) 1.23950(7) 0.0140(3) Uani 1 1 d . . . . .
H115 H -0.011178 0.367552 1.281029 0.017 Uiso 1 1 calc R U . . .
C115 C 0.23109(11) 0.36791(12) 1.32129(7) 0.0142(3) Uani 1 1 d . . . . .
H116 H 0.195183 0.363677 1.350551 0.017 Uiso 1 1 calc R U . . .
C116 C 0.33587(11) 0.36644(12) 1.34068(7) 0.0148(3) Uani 1 1 d . . . . .
C117 C 0.38765(11) 0.37154(13) 1.29625(7) 0.0174(3) Uani 1 1 d . . . . .
H117 H 0.458697 0.369838 1.309706 0.021 Uiso 1 1 calc R U . . .
C118 C 0.33839(12) 0.37893(13) 1.23372(7) 0.0171(3) Uani 1 1 d . . . . .
H118 H 0.374358 0.381657 1.204441 0.021 Uiso 1 1 calc R U . . .
N119 N 0.16846(10) 0.39569(11) 1.15706(6) 0.0174(3) Uani 1 1 d . . . . .
H119 H 0.1886(17) 0.3951(18) 1.1241(11) 0.021 Uiso 1 1 d . U . . .
C120 C 0.07224(12) 0.39751(12) 1.16162(7) 0.0155(3) Uani 1 1 d . . . . .
C121 C 0.07549(11) 0.38414(11) 1.22378(7) 0.0138(3) Uani 1 1 d . . . . .
C122 C 0.18006(11) 0.37564(12) 1.25870(7) 0.0137(3) Uani 1 1 d . . . . .
C123 C 0.23442(11) 0.38221(12) 1.21538(7) 0.0149(3) Uani 1 1 d . . . . .
C124 C -0.20018(11) 0.38250(11) 1.20925(7) 0.0147(3) Uani 1 1 d . . . . .
C125 C -0.28949(12) 0.35742(12) 1.16413(7) 0.0166(3) Uani 1 1 d . . . . .
H125 H -0.289801 0.343383 1.123194 0.020 Uiso 1 1 calc R U . . .
C126 C -0.37700(12) 0.35341(12) 1.18000(8) 0.0191(3) Uani 1 1 d . . . . .
C127 C -0.38205(12) 0.36905(13) 1.23889(8) 0.0197(3) Uani 1 1 d . . . . .
H127 H -0.443061 0.364531 1.248805 0.024 Uiso 1 1 calc R U . . .
C128 C -0.29242(13) 0.39171(13) 1.28238(8) 0.0191(3) Uani 1 1 d . . . . .
C129 C -0.20272(12) 0.40019(12) 1.26951(7) 0.0171(3) Uani 1 1 d . . . . .
H129 H -0.143458 0.417761 1.301002 0.021 Uiso 1 1 calc R U . . .
C130 C 0.39313(11) 0.36456(12) 1.40691(7) 0.0160(3) Uani 1 1 d . . . . .
C131 C 0.48728(12) 0.31980(14) 1.42718(8) 0.0205(3) Uani 1 1 d . . . . .
H131 H 0.514207 0.287426 1.398777 0.025 Uiso 1 1 calc R U . . .
C132 C 0.54044(13) 0.32334(15) 1.48895(8) 0.0250(4) Uani 1 1 d . . . . .
C133 C 0.50603(14) 0.36830(16) 1.53289(8) 0.0267(4) Uani 1 1 d . . . . .
H133 H 0.544204 0.370308 1.575147 0.032 Uiso 1 1 calc R U . . .
C134 C 0.41231(14) 0.41019(14) 1.51129(8) 0.0231(3) Uani 1 1 d . . . . .
C135 C 0.35530(13) 0.41035(12) 1.45037(7) 0.0186(3) Uani 1 1 d . . . . .
H135 H 0.291448 0.440952 1.437982 0.022 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
F1 C16 1.3584(18) . ?
F2 C18 1.3565(19) . ?
F3 C22 1.353(2) . ?
F4 C24 1.3604(19) . ?
C1 C2 1.383(2) . ?
C1 C10 1.399(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.414(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(2) . ?
C3 C14 1.481(2) . ?
C4 C11 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.395(2) . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(2) . ?
C6 C20 1.483(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.393(2) . ?
C8 H8 0.9500 . ?
N9 C10 1.3757(19) . ?
N9 C13 1.3792(19) . ?
N9 H9 0.89(2) . ?
C10 C11 1.416(2) . ?
C11 C12 1.449(2) . ?
C12 C13 1.421(2) . ?
C14 C15 1.399(2) . ?
C14 C19 1.403(2) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(2) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(2) . ?
C19 H19 0.9500 . ?
C20 C25 1.401(2) . ?
C20 C21 1.402(2) . ?
C21 C22 1.378(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(3) . ?
C23 C24 1.379(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(2) . ?
C25 H25 0.9500 . ?
N31 C35 1.473(2) . ?
N31 C33 1.473(2) . ?
N31 C31 1.473(2) . ?
C31 C32 1.549(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.473(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.547(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.475(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.545(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.474(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
F41 C56 1.3605(18) . ?
F42 C58 1.3572(18) . ?
F43 C62 1.356(2) . ?
F44 C64 1.356(2) . ?
C41 C42 1.382(2) . ?
C41 C50 1.391(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.415(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.398(2) . ?
C43 C54 1.488(2) . ?
C44 C51 1.392(2) . ?
C44 H44 0.9500 . ?
C45 C52 1.394(2) . ?
C45 C46 1.401(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.412(2) . ?
C46 C60 1.482(2) . ?
C47 C48 1.383(2) . ?
C47 H47 0.9500 . ?
C48 C53 1.398(2) . ?
C48 H48 0.9500 . ?
N49 C53 1.3768(19) . ?
N49 C50 1.3800(19) . ?
N49 H49 0.90(2) . ?
C50 C51 1.4179(19) . ?
C51 C52 1.450(2) . ?
C52 C53 1.4158(19) . ?
C54 C59 1.404(2) . ?
C54 C55 1.406(2) . ?
C55 C56 1.379(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.377(2) . ?
C57 C58 1.377(2) . ?
C57 H57 0.9500 . ?
C58 C59 1.376(2) . ?
C59 H59 0.9500 . ?
C60 C61 1.404(2) . ?
C60 C65 1.406(2) . ?
C61 C62 1.382(2) . ?
C61 H61 0.9500 . ?
C62 C63 1.376(3) . ?
C63 C64 1.384(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.382(2) . ?
C65 H65 0.9500 . ?
F71 C86 1.360(2) . ?
F72 C88 1.3521(19) . ?
F73 C92 1.352(2) . ?
F74 C94 1.3642(19) . ?
C71 C72 1.379(2) . ?
C71 C80 1.394(2) . ?
C71 H71 0.9500 . ?
C72 C73 1.417(2) . ?
C72 H72 0.9500 . ?
C73 C74 1.397(2) . ?
C73 C84 1.484(2) . ?
C74 C81 1.393(2) . ?
C74 H74 0.9500 . ?
C75 C82 1.394(2) . ?
C75 C76 1.399(2) . ?
C75 H75 0.9500 . ?
C76 C77 1.415(2) . ?
C76 C90 1.481(2) . ?
C77 C78 1.377(2) . ?
C77 H77 0.9500 . ?
C78 C83 1.395(2) . ?
C78 H78 0.9500 . ?
N79 C80 1.374(2) . ?
N79 C83 1.3752(19) . ?
N79 H79 0.92(2) . ?
C80 C81 1.414(2) . ?
C81 C82 1.448(2) . ?
C82 C83 1.418(2) . ?
C84 C89 1.400(2) . ?
C84 C85 1.403(2) . ?
C85 C86 1.378(2) . ?
C85 H85 0.9500 . ?
C86 C87 1.373(3) . ?
C87 C88 1.382(3) . ?
C87 H87 0.9500 . ?
C88 C89 1.379(2) . ?
C89 H89 0.9500 . ?
C90 C91 1.403(2) . ?
C90 C95 1.405(2) . ?
C91 C92 1.382(2) . ?
C91 H91 0.9500 . ?
C92 C93 1.379(3) . ?
C93 C94 1.381(3) . ?
C93 H93 0.9500 . ?
C94 C95 1.380(2) . ?
C95 H95 0.9500 . ?
N101 C105 1.467(2) . ?
N101 C103 1.471(2) . ?
N101 C101 1.476(2) . ?
C101 C102 1.547(2) . ?
C101 H101 0.9900 . ?
C101 H102 0.9900 . ?
C102 N102 1.480(2) . ?
C102 H103 0.9900 . ?
C102 H104 0.9900 . ?
C103 C104 1.548(2) . ?
C103 H105 0.9900 . ?
C103 H106 0.9900 . ?
C104 N102 1.473(2) . ?
C104 H107 0.9900 . ?
C104 H108 0.9900 . ?
C105 C106 1.547(2) . ?
C105 H109 0.9900 . ?
C105 H110 0.9900 . ?
C106 N102 1.469(2) . ?
C106 H111 0.9900 . ?
C106 H112 0.9900 . ?
F111 C126 1.3574(19) . ?
F112 C128 1.3582(18) . ?
F113 C132 1.353(2) . ?
F114 C134 1.361(2) . ?
C111 C112 1.385(2) . ?
C111 C120 1.393(2) . ?
C111 H113 0.9500 . ?
C112 C113 1.414(2) . ?
C112 H114 0.9500 . ?
C113 C114 1.396(2) . ?
C113 C124 1.485(2) . ?
C114 C121 1.395(2) . ?
C114 H115 0.9500 . ?
C115 C122 1.3924(19) . ?
C115 C116 1.401(2) . ?
C115 H116 0.9500 . ?
C116 C117 1.413(2) . ?
C116 C130 1.479(2) . ?
C117 C118 1.386(2) . ?
C117 H117 0.9500 . ?
C118 C123 1.391(2) . ?
C118 H118 0.9500 . ?
N119 C123 1.3826(19) . ?
N119 C120 1.384(2) . ?
N119 H119 0.88(2) . ?
C120 C121 1.414(2) . ?
C121 C122 1.446(2) . ?
C122 C123 1.419(2) . ?
C124 C125 1.402(2) . ?
C124 C129 1.404(2) . ?
C125 C126 1.380(2) . ?
C125 H125 0.9500 . ?
C126 C127 1.380(2) . ?
C127 C128 1.380(2) . ?
C127 H127 0.9500 . ?
C128 C129 1.379(2) . ?
C129 H129 0.9500 . ?
C130 C131 1.400(2) . ?
C130 C135 1.402(2) . ?
C131 C132 1.380(2) . ?
C131 H131 0.9500 . ?
C132 C133 1.378(3) . ?
C133 C134 1.380(3) . ?
C133 H133 0.9500 . ?
C134 C135 1.376(2) . ?
C135 H135 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
C2 C1 C10 117.83(14) . . ?
C2 C1 H1 121.1 . . ?
C10 C1 H1 121.1 . . ?
C1 C2 C3 122.44(14) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.83(14) . . ?
C4 C3 C14 121.12(13) . . ?
C2 C3 C14 120.04(14) . . ?
C11 C4 C3 119.88(13) . . ?
C11 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C12 C5 C6 119.33(13) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.67(14) . . ?
C5 C6 C20 120.85(13) . . ?
C7 C6 C20 119.48(13) . . ?
C8 C7 C6 122.05(14) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.68(14) . . ?
C7 C8 H8 121.2 . . ?
C13 C8 H8 121.2 . . ?
C10 N9 C13 108.62(12) . . ?
C10 N9 H9 121.0(15) . . ?
C13 N9 H9 129.4(15) . . ?
N9 C10 C1 129.16(14) . . ?
N9 C10 C11 109.85(13) . . ?
C1 C10 C11 120.99(14) . . ?
C4 C11 C10 119.99(14) . . ?
C4 C11 C12 134.04(14) . . ?
C10 C11 C12 105.97(13) . . ?
C5 C12 C13 119.71(14) . . ?
C5 C12 C11 133.95(14) . . ?
C13 C12 C11 106.32(12) . . ?
N9 C13 C8 129.17(14) . . ?
N9 C13 C12 109.25(13) . . ?
C8 C13 C12 121.56(14) . . ?
C15 C14 C19 117.98(14) . . ?
C15 C14 C3 121.57(14) . . ?
C19 C14 C3 120.45(14) . . ?
C16 C15 C14 119.48(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F1 C16 C15 118.66(15) . . ?
F1 C16 C17 117.49(14) . . ?
C15 C16 C17 123.85(15) . . ?
C18 C17 C16 115.34(15) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
F2 C18 C19 118.37(15) . . ?
F2 C18 C17 117.90(15) . . ?
C19 C18 C17 123.69(15) . . ?
C18 C19 C14 119.64(15) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C25 C20 C21 118.69(14) . . ?
C25 C20 C6 121.11(14) . . ?
C21 C20 C6 120.20(14) . . ?
C22 C21 C20 119.44(15) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
F3 C22 C21 118.24(16) . . ?
F3 C22 C23 118.26(15) . . ?
C21 C22 C23 123.50(16) . . ?
C24 C23 C22 115.49(15) . . ?
C24 C23 H23 122.3 . . ?
C22 C23 H23 122.3 . . ?
F4 C24 C23 117.74(15) . . ?
F4 C24 C25 117.98(16) . . ?
C23 C24 C25 124.27(15) . . ?
C24 C25 C20 118.62(15) . . ?
C24 C25 H25 120.7 . . ?
C20 C25 H25 120.7 . . ?
C35 N31 C33 108.78(13) . . ?
C35 N31 C31 108.99(13) . . ?
C33 N31 C31 108.85(13) . . ?
N31 C31 C32 109.66(12) . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N32 C32 C31 110.56(12) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 110.08(13) . . ?
N31 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
N31 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.2 . . ?
N32 C34 C33 110.22(13) . . ?
N32 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.32(13) . . ?
N31 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N31 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 110.02(13) . . ?
N32 C36 H36A 109.7 . . ?
C35 C36 H36A 109.7 . . ?
N32 C36 H36B 109.7 . . ?
C35 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C32 N32 C36 109.10(13) . . ?
C32 N32 C34 108.97(13) . . ?
C36 N32 C34 107.92(12) . . ?
C42 C41 C50 118.18(14) . . ?
C42 C41 H41 120.9 . . ?
C50 C41 H41 120.9 . . ?
C41 C42 C43 122.28(14) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C44 C43 C42 118.70(14) . . ?
C44 C43 C54 121.28(13) . . ?
C42 C43 C54 120.02(13) . . ?
C51 C44 C43 120.03(13) . . ?
C51 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C52 C45 C46 119.63(14) . . ?
C52 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C45 C46 C47 119.28(14) . . ?
C45 C46 C60 121.26(14) . . ?
C47 C46 C60 119.45(14) . . ?
C48 C47 C46 122.23(14) . . ?
C48 C47 H47 118.9 . . ?
C46 C47 H47 118.9 . . ?
C47 C48 C53 117.70(14) . . ?
C47 C48 H48 121.1 . . ?
C53 C48 H48 121.1 . . ?
C53 N49 C50 108.29(12) . . ?
C53 N49 H49 121.4(15) . . ?
C50 N49 H49 130.2(15) . . ?
N49 C50 C41 129.33(14) . . ?
N49 C50 C51 109.65(13) . . ?
C41 C50 C51 120.99(14) . . ?
C44 C51 C50 119.76(13) . . ?
C44 C51 C52 134.12(13) . . ?
C50 C51 C52 106.11(13) . . ?
C45 C52 C53 119.60(14) . . ?
C45 C52 C51 134.32(14) . . ?
C53 C52 C51 106.03(12) . . ?
N49 C53 C48 128.48(14) . . ?
N49 C53 C52 109.91(13) . . ?
C48 C53 C52 121.54(14) . . ?
C59 C54 C55 117.89(14) . . ?
C59 C54 C43 121.48(13) . . ?
C55 C54 C43 120.62(14) . . ?
C56 C55 C54 119.29(14) . . ?
C56 C55 H55 120.4 . . ?
C54 C55 H55 120.4 . . ?
F41 C56 C57 117.98(15) . . ?
F41 C56 C55 117.88(15) . . ?
C57 C56 C55 124.12(15) . . ?
C58 C57 C56 115.04(15) . . ?
C58 C57 H57 122.5 . . ?
C56 C57 H57 122.5 . . ?
F42 C58 C59 118.21(15) . . ?
F42 C58 C57 117.53(14) . . ?
C59 C58 C57 124.26(15) . . ?
C58 C59 C54 119.39(14) . . ?
C58 C59 H59 120.3 . . ?
C54 C59 H59 120.3 . . ?
C61 C60 C65 118.39(15) . . ?
C61 C60 C46 120.76(15) . . ?
C65 C60 C46 120.85(15) . . ?
C62 C61 C60 119.41(17) . . ?
C62 C61 H61 120.3 . . ?
C60 C61 H61 120.3 . . ?
F43 C62 C63 118.39(16) . . ?
F43 C62 C61 117.85(18) . . ?
C63 C62 C61 123.75(18) . . ?
C62 C63 C64 115.53(16) . . ?
C62 C63 H63 122.2 . . ?
C64 C63 H63 122.2 . . ?
F44 C64 C65 118.04(19) . . ?
F44 C64 C63 117.95(17) . . ?
C65 C64 C63 124.01(19) . . ?
C64 C65 C60 118.91(18) . . ?
C64 C65 H65 120.5 . . ?
C60 C65 H65 120.5 . . ?
C72 C71 C80 118.01(14) . . ?
C72 C71 H71 121.0 . . ?
C80 C71 H71 121.0 . . ?
C71 C72 C73 122.51(14) . . ?
C71 C72 H72 118.7 . . ?
C73 C72 H72 118.7 . . ?
C74 C73 C72 118.46(14) . . ?
C74 C73 C84 121.57(13) . . ?
C72 C73 C84 119.96(13) . . ?
C81 C74 C73 120.21(13) . . ?
C81 C74 H74 119.9 . . ?
C73 C74 H74 119.9 . . ?
C82 C75 C76 119.52(13) . . ?
C82 C75 H75 120.2 . . ?
C76 C75 H75 120.2 . . ?
C75 C76 C77 119.27(14) . . ?
C75 C76 C90 121.56(13) . . ?
C77 C76 C90 119.17(13) . . ?
C78 C77 C76 122.40(14) . . ?
C78 C77 H77 118.8 . . ?
C76 C77 H77 118.8 . . ?
C77 C78 C83 117.60(14) . . ?
C77 C78 H78 121.2 . . ?
C83 C78 H78 121.2 . . ?
C80 N79 C83 108.45(12) . . ?
C80 N79 H79 124.4(14) . . ?
C83 N79 H79 127.2(14) . . ?
N79 C80 C71 129.01(14) . . ?
N79 C80 C81 109.86(13) . . ?
C71 C80 C81 121.13(14) . . ?
C74 C81 C80 119.66(14) . . ?
C74 C81 C82 134.35(14) . . ?
C80 C81 C82 105.99(13) . . ?
C75 C82 C83 119.49(13) . . ?
C75 C82 C81 134.42(14) . . ?
C83 C82 C81 106.08(12) . . ?
N79 C83 C78 128.68(14) . . ?
N79 C83 C82 109.62(13) . . ?
C78 C83 C82 121.70(14) . . ?
C89 C84 C85 117.95(14) . . ?
C89 C84 C73 121.19(14) . . ?
C85 C84 C73 120.85(14) . . ?
C86 C85 C84 119.20(16) . . ?
C86 C85 H85 120.4 . . ?
C84 C85 H85 120.4 . . ?
F71 C86 C87 117.94(16) . . ?
F71 C86 C85 117.77(17) . . ?
C87 C86 C85 124.30(17) . . ?
C86 C87 C88 115.30(15) . . ?
C86 C87 H87 122.4 . . ?
C88 C87 H87 122.4 . . ?
F72 C88 C89 118.64(15) . . ?
F72 C88 C87 117.88(15) . . ?
C89 C88 C87 123.48(16) . . ?
C88 C89 C84 119.75(15) . . ?
C88 C89 H89 120.1 . . ?
C84 C89 H89 120.1 . . ?
C91 C90 C95 118.51(14) . . ?
C91 C90 C76 120.06(14) . . ?
C95 C90 C76 121.42(14) . . ?
C92 C91 C90 119.32(16) . . ?
C92 C91 H91 120.3 . . ?
C90 C91 H91 120.3 . . ?
F73 C92 C93 118.46(15) . . ?
F73 C92 C91 117.74(16) . . ?
C93 C92 C91 123.80(16) . . ?
C92 C93 C94 115.18(15) . . ?
C92 C93 H93 122.4 . . ?
C94 C93 H93 122.4 . . ?
F74 C94 C95 117.69(16) . . ?
F74 C94 C93 117.85(15) . . ?
C95 C94 C93 124.46(16) . . ?
C94 C95 C90 118.70(15) . . ?
C94 C95 H95 120.7 . . ?
C90 C95 H95 120.7 . . ?
C105 N101 C103 109.25(13) . . ?
C105 N101 C101 108.89(13) . . ?
C103 N101 C101 108.58(13) . . ?
N101 C101 C102 109.77(12) . . ?
N101 C101 H101 109.7 . . ?
C102 C101 H101 109.7 . . ?
N101 C101 H102 109.7 . . ?
C102 C101 H102 109.7 . . ?
H101 C101 H102 108.2 . . ?
N102 C102 C101 110.32(13) . . ?
N102 C102 H103 109.6 . . ?
C101 C102 H103 109.6 . . ?
N102 C102 H104 109.6 . . ?
C101 C102 H104 109.6 . . ?
H103 C102 H104 108.1 . . ?
N101 C103 C104 109.89(13) . . ?
N101 C103 H105 109.7 . . ?
C104 C103 H105 109.7 . . ?
N101 C103 H106 109.7 . . ?
C104 C103 H106 109.7 . . ?
H105 C103 H106 108.2 . . ?
N102 C104 C103 110.32(13) . . ?
N102 C104 H107 109.6 . . ?
C103 C104 H107 109.6 . . ?
N102 C104 H108 109.6 . . ?
C103 C104 H108 109.6 . . ?
H107 C104 H108 108.1 . . ?
N101 C105 C106 110.51(13) . . ?
N101 C105 H109 109.5 . . ?
C106 C105 H109 109.5 . . ?
N101 C105 H110 109.5 . . ?
C106 C105 H110 109.5 . . ?
H109 C105 H110 108.1 . . ?
N102 C106 C105 109.89(13) . . ?
N102 C106 H111 109.7 . . ?
C105 C106 H111 109.7 . . ?
N102 C106 H112 109.7 . . ?
C105 C106 H112 109.7 . . ?
H111 C106 H112 108.2 . . ?
C106 N102 C104 108.27(13) . . ?
C106 N102 C102 108.78(13) . . ?
C104 N102 C102 109.10(13) . . ?
C112 C111 C120 117.88(14) . . ?
C112 C111 H113 121.1 . . ?
C120 C111 H113 121.1 . . ?
C111 C112 C113 122.30(14) . . ?
C111 C112 H114 118.9 . . ?
C113 C112 H114 118.9 . . ?
C114 C113 C112 118.98(14) . . ?
C114 C113 C124 120.55(13) . . ?
C112 C113 C124 120.47(13) . . ?
C121 C114 C113 119.60(13) . . ?
C121 C114 H115 120.2 . . ?
C113 C114 H115 120.2 . . ?
C122 C115 C116 119.36(13) . . ?
C122 C115 H116 120.3 . . ?
C116 C115 H116 120.3 . . ?
C115 C116 C117 119.31(14) . . ?
C115 C116 C130 121.13(13) . . ?
C117 C116 C130 119.50(13) . . ?
C118 C117 C116 122.30(14) . . ?
C118 C117 H117 118.9 . . ?
C116 C117 H117 118.9 . . ?
C117 C118 C123 117.61(14) . . ?
C117 C118 H118 121.2 . . ?
C123 C118 H118 121.2 . . ?
C123 N119 C120 108.38(13) . . ?
C123 N119 H119 121.7(15) . . ?
C120 N119 H119 129.5(15) . . ?
N119 C120 C111 129.39(14) . . ?
N119 C120 C121 109.54(13) . . ?
C111 C120 C121 121.06(14) . . ?
C114 C121 C120 120.06(13) . . ?
C114 C121 C122 133.51(13) . . ?
C120 C121 C122 106.39(13) . . ?
C115 C122 C123 119.87(13) . . ?
C115 C122 C121 133.76(13) . . ?
C123 C122 C121 106.29(12) . . ?
N119 C123 C118 129.03(14) . . ?
N119 C123 C122 109.39(13) . . ?
C118 C123 C122 121.53(14) . . ?
C125 C124 C129 118.56(14) . . ?
C125 C124 C113 120.84(14) . . ?
C129 C124 C113 120.61(14) . . ?
C126 C125 C124 119.06(14) . . ?
C126 C125 H125 120.5 . . ?
C124 C125 H125 120.5 . . ?
F111 C126 C127 117.58(14) . . ?
F111 C126 C125 118.49(15) . . ?
C127 C126 C125 123.91(15) . . ?
C126 C127 C128 115.42(15) . . ?
C126 C127 H127 122.3 . . ?
C128 C127 H127 122.3 . . ?
F112 C128 C129 118.34(15) . . ?
F112 C128 C127 117.74(14) . . ?
C129 C128 C127 123.90(15) . . ?
C128 C129 C124 119.09(15) . . ?
C128 C129 H129 120.5 . . ?
C124 C129 H129 120.5 . . ?
C131 C130 C135 118.75(15) . . ?
C131 C130 C116 120.76(14) . . ?
C135 C130 C116 120.46(14) . . ?
C132 C131 C130 119.12(16) . . ?
C132 C131 H131 120.4 . . ?
C130 C131 H131 120.4 . . ?
F113 C132 C133 118.13(16) . . ?
F113 C132 C131 118.13(18) . . ?
C133 C132 C131 123.75(17) . . ?
C132 C133 C134 115.42(15) . . ?
C132 C133 H133 122.3 . . ?
C134 C133 H133 122.3 . . ?
F114 C134 C135 117.87(17) . . ?
F114 C134 C133 117.99(15) . . ?
C135 C134 C133 124.14(17) . . ?
C134 C135 C130 118.82(16) . . ?
C134 C135 H135 120.6 . . ?
C130 C135 H135 120.6 . . ?

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
C10 C1 C2 C3 1.2(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C1 C2 C3 C14 -179.93(15) . . . . ?
C2 C3 C4 C11 -0.7(2) . . . . ?
C14 C3 C4 C11 178.26(14) . . . . ?
C12 C5 C6 C7 -1.0(2) . . . . ?
C12 C5 C6 C20 179.46(14) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C20 C6 C7 C8 -179.96(15) . . . . ?
C6 C7 C8 C13 0.1(2) . . . . ?
C13 N9 C10 C1 -179.12(17) . . . . ?
C13 N9 C10 C11 -0.25(19) . . . . ?
C2 C1 C10 N9 178.87(16) . . . . ?
C2 C1 C10 C11 0.1(2) . . . . ?
C3 C4 C11 C10 2.0(2) . . . . ?
C3 C4 C11 C12 -179.03(17) . . . . ?
N9 C10 C11 C4 179.29(15) . . . . ?
C1 C10 C11 C4 -1.7(2) . . . . ?
N9 C10 C11 C12 0.08(18) . . . . ?
C1 C10 C11 C12 179.06(15) . . . . ?
C6 C5 C12 C13 0.9(2) . . . . ?
C6 C5 C12 C11 178.72(17) . . . . ?
C4 C11 C12 C5 3.1(3) . . . . ?
C10 C11 C12 C5 -177.87(17) . . . . ?
C4 C11 C12 C13 -178.93(18) . . . . ?
C10 C11 C12 C13 0.12(17) . . . . ?
C10 N9 C13 C8 178.65(16) . . . . ?
C10 N9 C13 C12 0.33(18) . . . . ?
C7 C8 C13 N9 -178.23(16) . . . . ?
C7 C8 C13 C12 -0.1(2) . . . . ?
C5 C12 C13 N9 178.06(14) . . . . ?
C11 C12 C13 N9 -0.27(18) . . . . ?
C5 C12 C13 C8 -0.4(2) . . . . ?
C11 C12 C13 C8 -178.75(15) . . . . ?
C4 C3 C14 C15 160.05(16) . . . . ?
C2 C3 C14 C15 -21.0(2) . . . . ?
C4 C3 C14 C19 -20.5(2) . . . . ?
C2 C3 C14 C19 158.50(16) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C3 C14 C15 C16 179.30(15) . . . . ?
C14 C15 C16 F1 -179.39(16) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
F1 C16 C17 C18 179.98(16) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 F2 -178.87(16) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
F2 C18 C19 C14 179.30(15) . . . . ?
C17 C18 C19 C14 1.5(3) . . . . ?
C15 C14 C19 C18 -0.8(2) . . . . ?
C3 C14 C19 C18 179.70(15) . . . . ?
C5 C6 C20 C25 33.5(2) . . . . ?
C7 C6 C20 C25 -146.11(16) . . . . ?
C5 C6 C20 C21 -146.28(16) . . . . ?
C7 C6 C20 C21 34.1(2) . . . . ?
C25 C20 C21 C22 0.0(2) . . . . ?
C6 C20 C21 C22 179.80(15) . . . . ?
C20 C21 C22 F3 -179.53(16) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
F3 C22 C23 C24 179.44(16) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 F4 -178.73(15) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
F4 C24 C25 C20 178.71(15) . . . . ?
C23 C24 C25 C20 -0.2(3) . . . . ?
C21 C20 C25 C24 0.1(2) . . . . ?
C6 C20 C25 C24 -179.69(15) . . . . ?
C35 N31 C31 C32 57.78(17) . . . . ?
C33 N31 C31 C32 -60.72(17) . . . . ?
N31 C31 C32 N32 2.27(19) . . . . ?
C35 N31 C33 C34 -59.81(17) . . . . ?
C31 N31 C33 C34 58.82(17) . . . . ?
N31 C33 C34 N32 1.25(19) . . . . ?
C33 N31 C35 C36 57.50(17) . . . . ?
C31 N31 C35 C36 -61.05(17) . . . . ?
N31 C35 C36 N32 2.97(19) . . . . ?
C31 C32 N32 C36 -60.13(17) . . . . ?
C31 C32 N32 C34 57.47(17) . . . . ?
C35 C36 N32 C32 56.96(17) . . . . ?
C35 C36 N32 C34 -61.31(16) . . . . ?
C33 C34 N32 C32 -59.40(17) . . . . ?
C33 C34 N32 C36 58.95(16) . . . . ?
C50 C41 C42 C43 1.6(3) . . . . ?
C41 C42 C43 C44 -1.6(2) . . . . ?
C41 C42 C43 C54 177.78(16) . . . . ?
C42 C43 C44 C51 -0.3(2) . . . . ?
C54 C43 C44 C51 -179.65(14) . . . . ?
C52 C45 C46 C47 0.4(2) . . . . ?
C52 C45 C46 C60 -179.11(15) . . . . ?
C45 C46 C47 C48 0.6(3) . . . . ?
C60 C46 C47 C48 -179.82(16) . . . . ?
C46 C47 C48 C53 -0.9(3) . . . . ?
C53 N49 C50 C41 -177.03(17) . . . . ?
C53 N49 C50 C51 0.93(19) . . . . ?
C42 C41 C50 N49 178.03(17) . . . . ?
C42 C41 C50 C51 0.3(3) . . . . ?
C43 C44 C51 C50 2.1(2) . . . . ?
C43 C44 C51 C52 -177.16(16) . . . . ?
N49 C50 C51 C44 179.75(15) . . . . ?
C41 C50 C51 C44 -2.1(2) . . . . ?
N49 C50 C51 C52 -0.81(18) . . . . ?
C41 C50 C51 C52 177.35(15) . . . . ?
C46 C45 C52 C53 -1.1(2) . . . . ?
C46 C45 C52 C51 175.98(17) . . . . ?
C44 C51 C52 C45 2.3(3) . . . . ?
C50 C51 C52 C45 -176.99(18) . . . . ?
C44 C51 C52 C53 179.72(17) . . . . ?
C50 C51 C52 C53 0.39(17) . . . . ?
C50 N49 C53 C48 176.27(17) . . . . ?
C50 N49 C53 C52 -0.67(19) . . . . ?
C47 C48 C53 N49 -176.41(16) . . . . ?
C47 C48 C53 C52 0.2(2) . . . . ?
C45 C52 C53 N49 178.01(15) . . . . ?
C51 C52 C53 N49 0.16(18) . . . . ?
C45 C52 C53 C48 0.8(2) . . . . ?
C51 C52 C53 C48 -177.03(15) . . . . ?
C44 C43 C54 C59 -12.9(2) . . . . ?
C42 C43 C54 C59 167.83(15) . . . . ?
C44 C43 C54 C55 165.74(15) . . . . ?
C42 C43 C54 C55 -13.6(2) . . . . ?
C59 C54 C55 C56 -0.4(2) . . . . ?
C43 C54 C55 C56 -179.01(15) . . . . ?
C54 C55 C56 F41 179.91(15) . . . . ?
C54 C55 C56 C57 1.3(3) . . . . ?
F41 C56 C57 C58 -179.30(16) . . . . ?
C55 C56 C57 C58 -0.7(3) . . . . ?
C56 C57 C58 F42 179.50(16) . . . . ?
C56 C57 C58 C59 -0.9(3) . . . . ?
F42 C58 C59 C54 -178.63(15) . . . . ?
C57 C58 C59 C54 1.7(3) . . . . ?
C55 C54 C59 C58 -1.1(2) . . . . ?
C43 C54 C59 C58 177.58(15) . . . . ?
C45 C46 C60 C61 -155.18(16) . . . . ?
C47 C46 C60 C61 25.3(2) . . . . ?
C45 C46 C60 C65 25.3(2) . . . . ?
C47 C46 C60 C65 -154.30(17) . . . . ?
C65 C60 C61 C62 0.4(3) . . . . ?
C46 C60 C61 C62 -179.13(16) . . . . ?
C60 C61 C62 F43 -179.59(16) . . . . ?
C60 C61 C62 C63 -0.7(3) . . . . ?
F43 C62 C63 C64 179.15(18) . . . . ?
C61 C62 C63 C64 0.3(3) . . . . ?
C62 C63 C64 F44 -179.77(19) . . . . ?
C62 C63 C64 C65 0.4(3) . . . . ?
F44 C64 C65 C60 179.54(17) . . . . ?
C63 C64 C65 C60 -0.7(3) . . . . ?
C61 C60 C65 C64 0.2(3) . . . . ?
C46 C60 C65 C64 179.77(16) . . . . ?
C80 C71 C72 C73 0.4(3) . . . . ?
C71 C72 C73 C74 -1.0(3) . . . . ?
C71 C72 C73 C84 177.91(16) . . . . ?
C72 C73 C74 C81 0.4(2) . . . . ?
C84 C73 C74 C81 -178.52(15) . . . . ?
C82 C75 C76 C77 1.0(2) . . . . ?
C82 C75 C76 C90 -179.65(14) . . . . ?
C75 C76 C77 C78 -1.1(3) . . . . ?
C90 C76 C77 C78 179.50(16) . . . . ?
C76 C77 C78 C83 -0.1(3) . . . . ?
C83 N79 C80 C71 -178.93(18) . . . . ?
C83 N79 C80 C81 0.3(2) . . . . ?
C72 C71 C80 N79 179.97(18) . . . . ?
C72 C71 C80 C81 0.8(3) . . . . ?
C73 C74 C81 C80 0.8(2) . . . . ?
C73 C74 C81 C82 -179.48(17) . . . . ?
N79 C80 C81 C74 179.27(15) . . . . ?
C71 C80 C81 C74 -1.4(3) . . . . ?
N79 C80 C81 C82 -0.51(19) . . . . ?
C71 C80 C81 C82 178.77(16) . . . . ?
C76 C75 C82 C83 0.3(2) . . . . ?
C76 C75 C82 C81 179.88(17) . . . . ?
C74 C81 C82 C75 1.2(3) . . . . ?
C80 C81 C82 C75 -179.11(18) . . . . ?
C74 C81 C82 C83 -179.20(18) . . . . ?
C80 C81 C82 C83 0.53(18) . . . . ?
C80 N79 C83 C78 -179.05(17) . . . . ?
C80 N79 C83 C82 0.07(19) . . . . ?
C77 C78 C83 N79 -179.62(17) . . . . ?
C77 C78 C83 C82 1.4(3) . . . . ?
C75 C82 C83 N79 179.32(14) . . . . ?
C81 C82 C83 N79 -0.38(18) . . . . ?
C75 C82 C83 C78 -1.5(2) . . . . ?
C81 C82 C83 C78 178.81(15) . . . . ?
C74 C73 C84 C89 -10.6(2) . . . . ?
C72 C73 C84 C89 170.49(16) . . . . ?
C74 C73 C84 C85 168.40(16) . . . . ?
C72 C73 C84 C85 -10.5(2) . . . . ?
C89 C84 C85 C86 0.7(2) . . . . ?
C73 C84 C85 C86 -178.42(16) . . . . ?
C84 C85 C86 F71 -178.88(17) . . . . ?
C84 C85 C86 C87 1.1(3) . . . . ?
F71 C86 C87 C88 178.27(17) . . . . ?
C85 C86 C87 C88 -1.8(3) . . . . ?
C86 C87 C88 F72 -178.93(16) . . . . ?
C86 C87 C88 C89 0.6(3) . . . . ?
F72 C88 C89 C84 -179.37(15) . . . . ?
C87 C88 C89 C84 1.1(3) . . . . ?
C85 C84 C89 C88 -1.7(2) . . . . ?
C73 C84 C89 C88 177.37(15) . . . . ?
C75 C76 C90 C91 152.58(16) . . . . ?
C77 C76 C90 C91 -28.0(2) . . . . ?
C75 C76 C90 C95 -28.4(2) . . . . ?
C77 C76 C90 C95 151.00(16) . . . . ?
C95 C90 C91 C92 -1.3(2) . . . . ?
C76 C90 C91 C92 177.82(15) . . . . ?
C90 C91 C92 F73 -178.62(15) . . . . ?
C90 C91 C92 C93 1.9(3) . . . . ?
F73 C92 C93 C94 179.41(16) . . . . ?
C91 C92 C93 C94 -1.1(3) . . . . ?
C92 C93 C94 F74 179.33(15) . . . . ?
C92 C93 C94 C95 -0.3(3) . . . . ?
F74 C94 C95 C90 -178.75(15) . . . . ?
C93 C94 C95 C90 0.9(3) . . . . ?
C91 C90 C95 C94 -0.1(2) . . . . ?
C76 C90 C95 C94 -179.12(15) . . . . ?
C105 N101 C101 C102 -58.75(17) . . . . ?
C103 N101 C101 C102 60.12(17) . . . . ?
N101 C101 C102 N102 -0.6(2) . . . . ?
C105 N101 C103 C104 57.99(17) . . . . ?
C101 N101 C103 C104 -60.64(17) . . . . ?
N101 C103 C104 N102 1.36(19) . . . . ?
C103 N101 C105 C106 -58.68(18) . . . . ?
C101 N101 C105 C106 59.76(18) . . . . ?
N101 C105 C106 N102 -0.6(2) . . . . ?
C105 C106 N102 C104 59.72(17) . . . . ?
C105 C106 N102 C102 -58.72(18) . . . . ?
C103 C104 N102 C106 -60.31(17) . . . . ?
C103 C104 N102 C102 57.92(17) . . . . ?
C101 C102 N102 C106 59.55(18) . . . . ?
C101 C102 N102 C104 -58.37(17) . . . . ?
C120 C111 C112 C113 -0.9(3) . . . . ?
C111 C112 C113 C114 2.5(2) . . . . ?
C111 C112 C113 C124 -177.14(16) . . . . ?
C112 C113 C114 C121 -0.9(2) . . . . ?
C124 C113 C114 C121 178.75(14) . . . . ?
C122 C115 C116 C117 -0.8(2) . . . . ?
C122 C115 C116 C130 176.15(14) . . . . ?
C115 C116 C117 C118 0.6(3) . . . . ?
C130 C116 C117 C118 -176.39(16) . . . . ?
C116 C117 C118 C123 0.6(3) . . . . ?
C123 N119 C120 C111 178.54(17) . . . . ?
C123 N119 C120 C121 -0.53(19) . . . . ?
C112 C111 C120 N119 178.82(17) . . . . ?
C112 C111 C120 C121 -2.2(2) . . . . ?
C113 C114 C121 C120 -2.1(2) . . . . ?
C113 C114 C121 C122 -179.72(17) . . . . ?
N119 C120 C121 C114 -177.05(14) . . . . ?
C111 C120 C121 C114 3.8(2) . . . . ?
N119 C120 C121 C122 1.11(18) . . . . ?
C111 C120 C121 C122 -178.05(15) . . . . ?
C116 C115 C122 C123 -0.2(2) . . . . ?
C116 C115 C122 C121 -176.28(17) . . . . ?
C114 C121 C122 C115 -7.0(3) . . . . ?
C120 C121 C122 C115 175.22(17) . . . . ?
C114 C121 C122 C123 176.56(17) . . . . ?
C120 C121 C122 C123 -1.24(18) . . . . ?
C120 N119 C123 C118 -177.62(17) . . . . ?
C120 N119 C123 C122 -0.29(19) . . . . ?
C117 C118 C123 N119 175.40(17) . . . . ?
C117 C118 C123 C122 -1.6(2) . . . . ?
C115 C122 C123 N119 -176.10(14) . . . . ?
C121 C122 C123 N119 0.96(18) . . . . ?
C115 C122 C123 C118 1.5(2) . . . . ?
C121 C122 C123 C118 178.53(15) . . . . ?
C114 C113 C124 C125 -156.23(15) . . . . ?
C112 C113 C124 C125 23.4(2) . . . . ?
C114 C113 C124 C129 23.6(2) . . . . ?
C112 C113 C124 C129 -156.77(15) . . . . ?
C129 C124 C125 C126 1.6(2) . . . . ?
C113 C124 C125 C126 -178.55(15) . . . . ?
C124 C125 C126 F111 178.65(15) . . . . ?
C124 C125 C126 C127 -2.6(3) . . . . ?
F111 C126 C127 C128 -179.91(15) . . . . ?
C125 C126 C127 C128 1.3(3) . . . . ?
C126 C127 C128 F112 179.10(15) . . . . ?
C126 C127 C128 C129 0.9(3) . . . . ?
F112 C128 C129 C124 -179.95(15) . . . . ?
C127 C128 C129 C124 -1.8(3) . . . . ?
C125 C124 C129 C128 0.4(2) . . . . ?
C113 C124 C129 C128 -179.39(15) . . . . ?
C115 C116 C130 C131 150.56(16) . . . . ?
C117 C116 C130 C131 -32.5(2) . . . . ?
C115 C116 C130 C135 -31.4(2) . . . . ?
C117 C116 C130 C135 145.53(17) . . . . ?
C135 C130 C131 C132 -0.9(3) . . . . ?
C116 C130 C131 C132 177.10(16) . . . . ?
C130 C131 C132 F113 -179.88(17) . . . . ?
C130 C131 C132 C133 0.5(3) . . . . ?
F113 C132 C133 C134 -179.11(17) . . . . ?
C131 C132 C133 C134 0.5(3) . . . . ?
C132 C133 C134 F114 178.47(16) . . . . ?
C132 C133 C134 C135 -1.1(3) . . . . ?
F114 C134 C135 C130 -178.93(15) . . . . ?
C133 C134 C135 C130 0.7(3) . . . . ?
C131 C130 C135 C134 0.4(2) . . . . ?
C116 C130 C135 C134 -177.65(15) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.89(2) 1.95(2) 2.8402(18) 177(2) . yes
C34 H34A F41 0.99 2.60 3.495(2) 150.8 1_455 yes
C34 H34A F72 0.99 2.60 3.221(2) 120.5 . yes
C36 H36A F74 0.99 2.62 3.602(2) 170.4 2_656 yes
N49 H49 N32 0.90(2) 1.98(2) 2.8760(18) 175(2) . yes
C55 H55 F114 0.95 2.48 3.284(2) 141.8 1_654 yes
N79 H79 N101 0.92(2) 1.90(2) 2.8260(18) 176(2) . yes
C101 H101 F2 0.99 2.61 3.550(2) 157.9 2_546 yes
C104 H107 F43 0.99 2.62 3.449(2) 141.2 2_647 yes
N119 H119 N102 0.88(2) 1.97(2) 2.8469(19) 174(2) . yes
C125 H125 F4 0.95 2.60 3.2146(19) 122.6 2_546 yes

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-1HT-300K
_database_code_depnum_ccdc_archive 'CCDC 2022173'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.9524(6)
_cell_length_b                   14.0942(5)
_cell_length_c                   22.7794(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.4326(15)
_cell_angle_gamma                90
_cell_volume                     4296.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9628
_cell_measurement_theta_min      2.5276
_cell_measurement_theta_max      29.9371

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.876
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            5794
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.498
_diffrn_reflns_point_group_measured_fraction_full 0.498
_reflns_number_total             5794
_reflns_number_gt                4894
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.1055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.4(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5794
_refine_ls_number_parameters     602
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0993
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
F1 F 0.5369(3) -0.16416(17) 0.64658(13) 0.1058(9) Uani 1 1 d . . . . .
F2 F 0.7117(2) -0.09221(17) 0.84831(11) 0.1036(9) Uani 1 1 d . . . . .
F3 F 0.6830(4) 0.7542(2) 1.01370(14) 0.1339(14) Uani 1 1 d . . . . .
F4 F 0.8614(3) 0.4697(3) 1.05828(11) 0.1355(14) Uani 1 1 d . . . . .
C1 C 0.5724(3) 0.2887(2) 0.62540(10) 0.0592(7) Uani 1 1 d . . . . .
H1 H 0.555263 0.306183 0.584380 0.071 Uiso 1 1 calc R U . . .
C2 C 0.5816(3) 0.1946(2) 0.64210(11) 0.0587(7) Uani 1 1 d . . . . .
H2 H 0.572101 0.148615 0.611696 0.070 Uiso 1 1 calc R U . . .
C3 C 0.6049(2) 0.16551(18) 0.70368(10) 0.0476(5) Uani 1 1 d . . . . .
C4 C 0.62201(19) 0.23473(17) 0.74918(9) 0.0447(4) Uani 1 1 d . . . . .
H4 H 0.638062 0.216944 0.790133 0.054 Uiso 1 1 calc R U . . .
C5 C 0.6605(2) 0.43920(19) 0.83060(10) 0.0484(5) Uani 1 1 d . . . . .
H5 H 0.673095 0.391005 0.859673 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6714(2) 0.53374(19) 0.84888(10) 0.0516(5) Uani 1 1 d . . . . .
C7 C 0.6505(3) 0.6055(2) 0.80408(13) 0.0607(7) Uani 1 1 d . . . . .
H7 H 0.657277 0.668520 0.816630 0.073 Uiso 1 1 calc R U . . .
C8 C 0.6205(3) 0.5859(2) 0.74278(12) 0.0613(7) Uani 1 1 d . . . . .
H8 H 0.606738 0.634572 0.714017 0.074 Uiso 1 1 calc R U . . .
N9 N 0.5859(2) 0.45466(18) 0.66675(9) 0.0569(6) Uani 1 1 d . . . . .
H9 H 0.556(3) 0.480(3) 0.6327(19) 0.068 Uiso 1 1 d . U . . .
C10 C 0.5893(2) 0.35679(19) 0.67106(10) 0.0507(5) Uani 1 1 d . . . . .
C11 C 0.61512(19) 0.33019(17) 0.73347(9) 0.0438(4) Uani 1 1 d . . . . .
C12 C 0.6305(2) 0.41715(18) 0.76810(9) 0.0446(5) Uani 1 1 d . . . . .
C13 C 0.6112(2) 0.49225(19) 0.72478(10) 0.0502(5) Uani 1 1 d . . . . .
C14 C 0.6113(2) 0.06245(19) 0.71913(11) 0.0483(5) Uani 1 1 d . . . . .
C15 C 0.5700(3) -0.0056(2) 0.67483(13) 0.0596(6) Uani 1 1 d . . . . .
H15 H 0.536989 0.012505 0.634980 0.072 Uiso 1 1 calc R U . . .
C16 C 0.5789(3) -0.0996(3) 0.69088(16) 0.0702(8) Uani 1 1 d . . . . .
C17 C 0.6250(3) -0.1323(2) 0.74836(18) 0.0725(8) Uani 1 1 d . . . . .
H17 H 0.629266 -0.196525 0.758109 0.087 Uiso 1 1 calc R U . . .
C18 C 0.6642(3) -0.0636(2) 0.79036(15) 0.0676(8) Uani 1 1 d . . . . .
C19 C 0.6609(2) 0.0317(2) 0.77831(12) 0.0561(6) Uani 1 1 d . . . . .
H19 H 0.690818 0.074983 0.808792 0.067 Uiso 1 1 calc R U . . .
C20 C 0.7061(3) 0.5607(2) 0.91458(12) 0.0591(7) Uani 1 1 d . . . . .
C21 C 0.6771(3) 0.6463(2) 0.93472(14) 0.0715(9) Uani 1 1 d . . . . .
H21 H 0.634475 0.687055 0.907217 0.086 Uiso 1 1 calc R U . . .
C22 C 0.7123(4) 0.6706(3) 0.99605(17) 0.0955(16) Uani 1 1 d . . . . .
C23 C 0.7747(5) 0.6139(4) 1.03870(15) 0.1000(17) Uani 1 1 d . . . . .
H23 H 0.798168 0.631414 1.079624 0.120 Uiso 1 1 calc R U . . .
C24 C 0.8005(4) 0.5298(4) 1.01763(15) 0.0896(14) Uani 1 1 d . . . . .
C25 C 0.7698(3) 0.5004(3) 0.95692(12) 0.0711(9) Uani 1 1 d . . . . .
H25 H 0.790779 0.442863 0.944894 0.085 Uiso 1 1 calc R U . . .
N31 N 0.5194(2) 0.56536(16) 0.55618(9) 0.0572(5) Uani 1 1 d . . . . .
C31 C 0.5994(3) 0.6270(3) 0.55156(14) 0.0682(7) Uani 1 1 d . . . . .
H31A H 0.659752 0.590111 0.556230 0.082 Uiso 1 1 calc R U . . .
H31B H 0.612441 0.673701 0.584166 0.082 Uiso 1 1 calc R U . . .
C32 C 0.5717(3) 0.6778(3) 0.48930(15) 0.0736(8) Uani 1 1 d . . . . .
H32A H 0.575566 0.745937 0.495585 0.088 Uiso 1 1 calc R U . . .
H32B H 0.618815 0.660347 0.466944 0.088 Uiso 1 1 calc R U . . .
C33 C 0.4301(3) 0.6241(3) 0.55013(15) 0.0765(8) Uani 1 1 d . . . . .
H33A H 0.443194 0.670580 0.582869 0.092 Uiso 1 1 calc R U . . .
H33B H 0.374933 0.584496 0.553299 0.092 Uiso 1 1 calc R U . . .
C34 C 0.4020(3) 0.6752(3) 0.48768(17) 0.0762(9) Uani 1 1 d . . . . .
H34A H 0.335170 0.656668 0.464332 0.091 Uiso 1 1 calc R U . . .
H34B H 0.402278 0.743244 0.494063 0.091 Uiso 1 1 calc R U . . .
C35 C 0.4981(3) 0.49707(19) 0.50540(13) 0.0680(7) Uani 1 1 d . . . . .
H35A H 0.444716 0.454908 0.508416 0.082 Uiso 1 1 calc R U . . .
H35B H 0.557028 0.458953 0.508063 0.082 Uiso 1 1 calc R U . . .
C36 C 0.4671(3) 0.54891(19) 0.44359(11) 0.0623(7) Uani 1 1 d . . . . .
H36A H 0.511834 0.531538 0.419583 0.075 Uiso 1 1 calc R U . . .
H36B H 0.399852 0.530456 0.420972 0.075 Uiso 1 1 calc R U . . .
N32 N 0.4712(2) 0.65181(15) 0.45396(9) 0.0562(5) Uani 1 1 d . . . . .
F41 F 0.1410(3) 0.4675(2) -0.00898(13) 0.1214(12) Uani 1 1 d . . . . .
F42 F 0.2893(3) 0.7419(2) -0.05847(10) 0.1099(9) Uani 1 1 d . . . . .
F43 F 0.4103(4) 1.36585(17) 0.36502(14) 0.1380(16) Uani 1 1 d . . . . .
F44 F 0.3368(3) 1.29594(17) 0.15802(11) 0.1064(9) Uani 1 1 d . . . . .
C41 C 0.3850(2) 0.61565(18) 0.26036(11) 0.0538(6) Uani 1 1 d . . . . .
H41 H 0.402256 0.566257 0.288446 0.065 Uiso 1 1 calc R U . . .
C42 C 0.3497(2) 0.59824(18) 0.19832(11) 0.0541(6) Uani 1 1 d . . . . .
H42 H 0.343092 0.535754 0.184637 0.065 Uiso 1 1 calc R U . . .
C43 C 0.3236(2) 0.67193(17) 0.15520(10) 0.0487(5) Uani 1 1 d . . . . .
C44 C 0.3335(2) 0.76626(18) 0.17471(10) 0.0473(5) Uani 1 1 d . . . . .
H44 H 0.317032 0.815518 0.146473 0.057 Uiso 1 1 calc R U . . .
C45 C 0.3776(2) 0.96826(17) 0.25779(10) 0.0461(5) Uani 1 1 d . . . . .
H45 H 0.351733 0.986901 0.217210 0.055 Uiso 1 1 calc R U . . .
C46 C 0.4047(2) 1.03630(18) 0.30348(11) 0.0485(5) Uani 1 1 d . . . . .
C47 C 0.4442(2) 1.0054(2) 0.36452(11) 0.0612(7) Uani 1 1 d . . . . .
H47 H 0.464762 1.050590 0.395250 0.073 Uiso 1 1 calc R U . . .
C48 C 0.4535(3) 0.9111(2) 0.38025(11) 0.0646(8) Uani 1 1 d . . . . .
H48 H 0.477961 0.892666 0.420961 0.078 Uiso 1 1 calc R U . . .
N49 N 0.4287(2) 0.74611(18) 0.33751(9) 0.0576(6) Uani 1 1 d . . . . .
H49 H 0.447(3) 0.705(3) 0.3723(18) 0.069 Uiso 1 1 d . U . . .
C50 C 0.3936(2) 0.71027(19) 0.27932(10) 0.0477(5) Uani 1 1 d . . . . .
C51 C 0.3682(2) 0.78537(17) 0.23703(10) 0.0446(5) Uani 1 1 d . . . . .
C52 C 0.3889(2) 0.87230(18) 0.27232(9) 0.0453(4) Uani 1 1 d . . . . .
C53 C 0.4255(2) 0.84384(19) 0.33402(10) 0.0503(6) Uani 1 1 d . . . . .
C54 C 0.2861(2) 0.6483(2) 0.08889(11) 0.0534(5) Uani 1 1 d . . . . .
C55 C 0.2289(3) 0.5670(2) 0.06990(14) 0.0678(7) Uani 1 1 d . . . . .
H55 H 0.213565 0.527132 0.098508 0.081 Uiso 1 1 calc R U . . .
C56 C 0.1954(4) 0.5461(3) 0.00845(16) 0.0815(11) Uani 1 1 d . . . . .
C57 C 0.2143(4) 0.6019(3) -0.03624(14) 0.0851(12) Uani 1 1 d . . . . .
H57 H 0.190961 0.586645 -0.077561 0.102 Uiso 1 1 calc R U . . .
C58 C 0.2702(3) 0.6821(3) -0.01591(14) 0.0737(9) Uani 1 1 d . . . . .
C59 C 0.3067(3) 0.7071(2) 0.04478(12) 0.0601(7) Uani 1 1 d . . . . .
H59 H 0.344247 0.762028 0.056104 0.072 Uiso 1 1 calc R U . . .
C60 C 0.3940(2) 1.13933(18) 0.28912(11) 0.0477(5) Uani 1 1 d . . . . .
C61 C 0.4081(3) 1.2071(2) 0.33515(14) 0.0669(8) Uani 1 1 d . . . . .
H61 H 0.424618 1.188694 0.375991 0.080 Uiso 1 1 calc R U . . .
C62 C 0.3972(3) 1.3021(2) 0.31967(17) 0.0745(9) Uani 1 1 d . . . . .
C63 C 0.3747(3) 1.3345(2) 0.26102(18) 0.0682(8) Uani 1 1 d . . . . .
H63 H 0.369672 1.398901 0.251839 0.082 Uiso 1 1 calc R U . . .
C64 C 0.3601(3) 1.2677(2) 0.21714(15) 0.0652(7) Uani 1 1 d . . . . .
C65 C 0.3695(3) 1.1719(2) 0.22918(13) 0.0617(7) Uani 1 1 d . . . . .
H65 H 0.359418 1.128884 0.197058 0.074 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
F1 C16 1.361(4) . ?
F2 C18 1.360(3) . ?
F3 C22 1.346(6) . ?
F4 C24 1.361(6) . ?
C1 C2 1.376(4) . ?
C1 C10 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.408(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.394(3) . ?
C3 C14 1.491(4) . ?
C4 C11 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(4) . ?
C5 C12 1.401(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(4) . ?
C6 C20 1.486(3) . ?
C7 C8 1.368(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.378(4) . ?
C8 H8 0.9300 . ?
N9 C13 1.374(3) . ?
N9 C10 1.383(4) . ?
N9 H9 0.85(4) . ?
C10 C11 1.415(3) . ?
C11 C12 1.440(3) . ?
C12 C13 1.420(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.399(3) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C17 C18 1.362(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.391(5) . ?
C20 C25 1.399(5) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.365(8) . ?
C23 C24 1.365(8) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(4) . ?
C25 H25 0.9300 . ?
N31 C31 1.442(4) . ?
N31 C35 1.469(4) . ?
N31 C33 1.470(5) . ?
C31 C32 1.537(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.453(5) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.543(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N32 1.432(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.536(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.468(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
F41 C56 1.338(5) . ?
F42 C58 1.366(5) . ?
F43 C62 1.342(4) . ?
F44 C64 1.353(4) . ?
C41 C42 1.381(4) . ?
C41 C50 1.397(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.405(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.396(3) . ?
C43 C54 1.490(3) . ?
C44 C51 1.391(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.387(3) . ?
C45 C52 1.391(3) . ?
C45 H45 0.9300 . ?
C46 C47 1.412(3) . ?
C46 C60 1.487(3) . ?
C47 C48 1.373(4) . ?
C47 H47 0.9300 . ?
C48 C53 1.388(4) . ?
C48 H48 0.9300 . ?
N49 C50 1.373(3) . ?
N49 C53 1.380(3) . ?
N49 H49 0.96(4) . ?
C50 C51 1.407(3) . ?
C51 C52 1.449(3) . ?
C52 C53 1.411(3) . ?
C54 C59 1.393(4) . ?
C54 C55 1.394(5) . ?
C55 C56 1.376(4) . ?
C55 H55 0.9300 . ?
C56 C57 1.370(7) . ?
C57 C58 1.377(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.377(4) . ?
C59 H59 0.9300 . ?
C60 C65 1.389(3) . ?
C60 C61 1.391(4) . ?
C61 C62 1.381(4) . ?
C61 H61 0.9300 . ?
C62 C63 1.362(5) . ?
C63 C64 1.346(5) . ?
C63 H63 0.9300 . ?
C64 C65 1.376(4) . ?
C65 H65 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
C2 C1 C10 118.5(2) . . ?
C2 C1 H1 120.7 . . ?
C10 C1 H1 120.7 . . ?
C1 C2 C3 122.2(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.7(2) . . ?
C4 C3 C14 121.3(2) . . ?
C2 C3 C14 120.0(2) . . ?
C11 C4 C3 120.11(19) . . ?
C11 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C12 119.5(2) . . ?
C6 C5 H5 120.2 . . ?
C12 C5 H5 120.2 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 C20 121.5(2) . . ?
C7 C6 C20 119.2(2) . . ?
C8 C7 C6 122.4(3) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C13 118.2(2) . . ?
C7 C8 H8 120.9 . . ?
C13 C8 H8 120.9 . . ?
C13 N9 C10 108.79(19) . . ?
C13 N9 H9 130(3) . . ?
C10 N9 H9 119(3) . . ?
N9 C10 C1 130.0(2) . . ?
N9 C10 C11 109.2(2) . . ?
C1 C10 C11 120.8(2) . . ?
C4 C11 C10 119.7(2) . . ?
C4 C11 C12 134.00(19) . . ?
C10 C11 C12 106.3(2) . . ?
C5 C12 C13 119.0(2) . . ?
C5 C12 C11 134.5(2) . . ?
C13 C12 C11 106.50(19) . . ?
N9 C13 C8 129.2(2) . . ?
N9 C13 C12 109.1(2) . . ?
C8 C13 C12 121.6(2) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C3 121.0(2) . . ?
C19 C14 C3 120.6(2) . . ?
C16 C15 C14 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
F1 C16 C17 118.2(3) . . ?
F1 C16 C15 117.4(3) . . ?
C17 C16 C15 124.3(3) . . ?
C18 C17 C16 114.9(3) . . ?
C18 C17 H17 122.6 . . ?
C16 C17 H17 122.6 . . ?
F2 C18 C17 117.4(3) . . ?
F2 C18 C19 117.7(3) . . ?
C17 C18 C19 124.9(3) . . ?
C18 C19 C14 118.5(3) . . ?
C18 C19 H19 120.8 . . ?
C14 C19 H19 120.8 . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C6 120.8(3) . . ?
C25 C20 C6 120.1(3) . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
F3 C22 C23 119.1(3) . . ?
F3 C22 C21 117.8(5) . . ?
C23 C22 C21 123.1(4) . . ?
C22 C23 C24 115.9(3) . . ?
C22 C23 H23 122.0 . . ?
C24 C23 H23 122.0 . . ?
F4 C24 C23 118.5(3) . . ?
F4 C24 C25 116.7(5) . . ?
C23 C24 C25 124.8(4) . . ?
C24 C25 C20 117.6(4) . . ?
C24 C25 H25 121.2 . . ?
C20 C25 H25 121.2 . . ?
C31 N31 C35 109.0(3) . . ?
C31 N31 C33 107.8(2) . . ?
C35 N31 C33 108.5(3) . . ?
N31 C31 C32 110.5(2) . . ?
N31 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
N32 C32 C31 110.2(3) . . ?
N32 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 109.7(3) . . ?
N31 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
N31 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
N32 C34 C33 110.7(3) . . ?
N32 C34 H34A 109.5 . . ?
C33 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.6(2) . . ?
N31 C35 H35A 109.5 . . ?
C36 C35 H35A 109.5 . . ?
N31 C35 H35B 109.5 . . ?
C36 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 109.5(2) . . ?
N32 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C34 N32 C32 109.6(2) . . ?
C34 N32 C36 108.2(3) . . ?
C32 N32 C36 109.0(3) . . ?
C42 C41 C50 117.5(2) . . ?
C42 C41 H41 121.3 . . ?
C50 C41 H41 121.3 . . ?
C41 C42 C43 122.1(2) . . ?
C41 C42 H42 119.0 . . ?
C43 C42 H42 119.0 . . ?
C44 C43 C42 119.9(2) . . ?
C44 C43 C54 120.7(2) . . ?
C42 C43 C54 119.4(2) . . ?
C51 C44 C43 118.9(2) . . ?
C51 C44 H44 120.5 . . ?
C43 C44 H44 120.5 . . ?
C46 C45 C52 120.4(2) . . ?
C46 C45 H45 119.8 . . ?
C52 C45 H45 119.8 . . ?
C45 C46 C47 118.2(2) . . ?
C45 C46 C60 121.4(2) . . ?
C47 C46 C60 120.3(2) . . ?
C48 C47 C46 122.5(2) . . ?
C48 C47 H47 118.7 . . ?
C46 C47 H47 118.7 . . ?
C47 C48 C53 118.5(2) . . ?
C47 C48 H48 120.7 . . ?
C53 C48 H48 120.7 . . ?
C50 N49 C53 108.35(19) . . ?
C50 N49 H49 121(2) . . ?
C53 N49 H49 130(2) . . ?
N49 C50 C41 128.8(2) . . ?
N49 C50 C51 109.6(2) . . ?
C41 C50 C51 121.6(2) . . ?
C44 C51 C50 120.0(2) . . ?
C44 C51 C52 133.4(2) . . ?
C50 C51 C52 106.51(19) . . ?
C45 C52 C53 119.9(2) . . ?
C45 C52 C51 134.3(2) . . ?
C53 C52 C51 105.7(2) . . ?
N49 C53 C48 129.8(2) . . ?
N49 C53 C52 109.8(2) . . ?
C48 C53 C52 120.4(2) . . ?
C59 C54 C55 118.8(3) . . ?
C59 C54 C43 120.9(3) . . ?
C55 C54 C43 120.3(3) . . ?
C56 C55 C54 119.4(3) . . ?
C56 C55 H55 120.3 . . ?
C54 C55 H55 120.3 . . ?
F41 C56 C57 117.9(3) . . ?
F41 C56 C55 118.7(4) . . ?
C57 C56 C55 123.5(4) . . ?
C56 C57 C58 115.6(3) . . ?
C56 C57 H57 122.2 . . ?
C58 C57 H57 122.2 . . ?
F42 C58 C59 117.7(4) . . ?
F42 C58 C57 118.2(3) . . ?
C59 C58 C57 124.1(4) . . ?
C58 C59 C54 118.6(3) . . ?
C58 C59 H59 120.7 . . ?
C54 C59 H59 120.7 . . ?
C65 C60 C61 117.2(2) . . ?
C65 C60 C46 121.4(2) . . ?
C61 C60 C46 121.4(2) . . ?
C62 C61 C60 119.4(3) . . ?
C62 C61 H61 120.3 . . ?
C60 C61 H61 120.3 . . ?
F43 C62 C63 118.3(3) . . ?
F43 C62 C61 118.1(3) . . ?
C63 C62 C61 123.6(3) . . ?
C64 C63 C62 116.0(3) . . ?
C64 C63 H63 122.0 . . ?
C62 C63 H63 122.0 . . ?
C63 C64 F44 118.5(3) . . ?
C63 C64 C65 123.5(3) . . ?
F44 C64 C65 118.0(3) . . ?
C64 C65 C60 120.2(3) . . ?
C64 C65 H65 119.9 . . ?
C60 C65 H65 119.9 . . ?

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
C10 C1 C2 C3 1.7(5) . . . . ?
C1 C2 C3 C4 -1.9(5) . . . . ?
C1 C2 C3 C14 178.4(3) . . . . ?
C2 C3 C4 C11 0.5(4) . . . . ?
C14 C3 C4 C11 -179.7(3) . . . . ?
C12 C5 C6 C7 1.0(5) . . . . ?
C12 C5 C6 C20 -178.1(3) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C20 C6 C7 C8 178.5(3) . . . . ?
C6 C7 C8 C13 -0.3(6) . . . . ?
C13 N9 C10 C1 -178.1(3) . . . . ?
C13 N9 C10 C11 1.4(4) . . . . ?
C2 C1 C10 N9 179.3(3) . . . . ?
C2 C1 C10 C11 -0.1(5) . . . . ?
C3 C4 C11 C10 0.9(4) . . . . ?
C3 C4 C11 C12 -178.0(3) . . . . ?
N9 C10 C11 C4 179.3(3) . . . . ?
C1 C10 C11 C4 -1.1(5) . . . . ?
N9 C10 C11 C12 -1.5(3) . . . . ?
C1 C10 C11 C12 178.0(3) . . . . ?
C6 C5 C12 C13 -0.4(4) . . . . ?
C6 C5 C12 C11 177.6(3) . . . . ?
C4 C11 C12 C5 2.0(6) . . . . ?
C10 C11 C12 C5 -177.0(3) . . . . ?
C4 C11 C12 C13 -179.9(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C10 N9 C13 C8 178.0(4) . . . . ?
C10 N9 C13 C12 -0.7(4) . . . . ?
C7 C8 C13 N9 -177.6(4) . . . . ?
C7 C8 C13 C12 0.9(5) . . . . ?
C5 C12 C13 N9 178.2(3) . . . . ?
C11 C12 C13 N9 -0.3(3) . . . . ?
C5 C12 C13 C8 -0.6(5) . . . . ?
C11 C12 C13 C8 -179.1(3) . . . . ?
C4 C3 C14 C15 163.3(3) . . . . ?
C2 C3 C14 C15 -17.0(5) . . . . ?
C4 C3 C14 C19 -18.0(4) . . . . ?
C2 C3 C14 C19 161.7(3) . . . . ?
C19 C14 C15 C16 0.4(5) . . . . ?
C3 C14 C15 C16 179.1(3) . . . . ?
C14 C15 C16 F1 179.5(3) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
F1 C16 C17 C18 -179.4(4) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 F2 -179.5(4) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
F2 C18 C19 C14 -179.3(3) . . . . ?
C17 C18 C19 C14 1.9(6) . . . . ?
C15 C14 C19 C18 -1.7(5) . . . . ?
C3 C14 C19 C18 179.6(3) . . . . ?
C5 C6 C20 C21 -151.7(3) . . . . ?
C7 C6 C20 C21 29.2(5) . . . . ?
C5 C6 C20 C25 29.3(5) . . . . ?
C7 C6 C20 C25 -149.8(3) . . . . ?
C25 C20 C21 C22 0.4(5) . . . . ?
C6 C20 C21 C22 -178.6(3) . . . . ?
C20 C21 C22 F3 179.8(4) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
F3 C22 C23 C24 179.3(5) . . . . ?
C21 C22 C23 C24 -0.6(7) . . . . ?
C22 C23 C24 F4 -179.1(4) . . . . ?
C22 C23 C24 C25 1.5(7) . . . . ?
F4 C24 C25 C20 179.2(4) . . . . ?
C23 C24 C25 C20 -1.4(6) . . . . ?
C21 C20 C25 C24 0.4(5) . . . . ?
C6 C20 C25 C24 179.4(3) . . . . ?
C35 N31 C31 C32 57.3(4) . . . . ?
C33 N31 C31 C32 -60.3(3) . . . . ?
N31 C31 C32 N32 2.2(4) . . . . ?
C31 N31 C33 C34 59.7(3) . . . . ?
C35 N31 C33 C34 -58.3(4) . . . . ?
N31 C33 C34 N32 -0.7(4) . . . . ?
C31 N31 C35 C36 -59.7(4) . . . . ?
C33 N31 C35 C36 57.5(4) . . . . ?
N31 C35 C36 N32 1.7(5) . . . . ?
C33 C34 N32 C32 -58.1(3) . . . . ?
C33 C34 N32 C36 60.7(4) . . . . ?
C31 C32 N32 C34 57.7(3) . . . . ?
C31 C32 N32 C36 -60.6(4) . . . . ?
C35 C36 N32 C34 -61.3(4) . . . . ?
C35 C36 N32 C32 57.9(4) . . . . ?
C50 C41 C42 C43 0.3(5) . . . . ?
C41 C42 C43 C44 0.3(5) . . . . ?
C41 C42 C43 C54 -180.0(3) . . . . ?
C42 C43 C44 C51 -0.7(5) . . . . ?
C54 C43 C44 C51 179.6(3) . . . . ?
C52 C45 C46 C47 0.4(4) . . . . ?
C52 C45 C46 C60 179.6(3) . . . . ?
C45 C46 C47 C48 -2.2(5) . . . . ?
C60 C46 C47 C48 178.5(3) . . . . ?
C46 C47 C48 C53 1.9(5) . . . . ?
C53 N49 C50 C41 178.6(3) . . . . ?
C53 N49 C50 C51 0.7(4) . . . . ?
C42 C41 C50 N49 -178.1(3) . . . . ?
C42 C41 C50 C51 -0.4(5) . . . . ?
C43 C44 C51 C50 0.5(4) . . . . ?
C43 C44 C51 C52 178.6(3) . . . . ?
N49 C50 C51 C44 178.1(3) . . . . ?
C41 C50 C51 C44 0.0(5) . . . . ?
N49 C50 C51 C52 -0.4(3) . . . . ?
C41 C50 C51 C52 -178.5(3) . . . . ?
C46 C45 C52 C53 1.7(4) . . . . ?
C46 C45 C52 C51 179.6(3) . . . . ?
C44 C51 C52 C45 3.6(6) . . . . ?
C50 C51 C52 C45 -178.2(3) . . . . ?
C44 C51 C52 C53 -178.3(3) . . . . ?
C50 C51 C52 C53 -0.1(3) . . . . ?
C50 N49 C53 C48 -179.6(3) . . . . ?
C50 N49 C53 C52 -0.8(4) . . . . ?
C47 C48 C53 N49 179.0(3) . . . . ?
C47 C48 C53 C52 0.3(5) . . . . ?
C45 C52 C53 N49 178.9(3) . . . . ?
C51 C52 C53 N49 0.5(3) . . . . ?
C45 C52 C53 C48 -2.1(5) . . . . ?
C51 C52 C53 C48 179.5(3) . . . . ?
C44 C43 C54 C59 32.9(5) . . . . ?
C42 C43 C54 C59 -146.9(3) . . . . ?
C44 C43 C54 C55 -146.7(3) . . . . ?
C42 C43 C54 C55 33.6(5) . . . . ?
C59 C54 C55 C56 0.8(5) . . . . ?
C43 C54 C55 C56 -179.6(3) . . . . ?
C54 C55 C56 F41 179.7(4) . . . . ?
C54 C55 C56 C57 -0.6(6) . . . . ?
F41 C56 C57 C58 179.8(4) . . . . ?
C55 C56 C57 C58 0.0(7) . . . . ?
C56 C57 C58 F42 -178.3(4) . . . . ?
C56 C57 C58 C59 0.4(7) . . . . ?
F42 C58 C59 C54 178.5(3) . . . . ?
C57 C58 C59 C54 -0.2(6) . . . . ?
C55 C54 C59 C58 -0.4(5) . . . . ?
C43 C54 C59 C58 180.0(3) . . . . ?
C45 C46 C60 C65 -8.9(5) . . . . ?
C47 C46 C60 C65 170.3(3) . . . . ?
C45 C46 C60 C61 171.1(3) . . . . ?
C47 C46 C60 C61 -9.7(5) . . . . ?
C65 C60 C61 C62 0.1(6) . . . . ?
C46 C60 C61 C62 -179.9(3) . . . . ?
C60 C61 C62 F43 179.3(4) . . . . ?
C60 C61 C62 C63 -1.1(7) . . . . ?
F43 C62 C63 C64 -178.6(5) . . . . ?
C61 C62 C63 C64 1.9(7) . . . . ?
C62 C63 C64 F44 179.5(4) . . . . ?
C62 C63 C64 C65 -1.7(6) . . . . ?
C63 C64 C65 C60 0.8(6) . . . . ?
F44 C64 C65 C60 179.6(4) . . . . ?
C61 C60 C65 C64 0.1(5) . . . . ?
C46 C60 C65 C64 -180.0(3) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.85(4) 2.06(4) 2.884(3) 163(4) . yes
C15 H15 F4 0.93 2.59 3.377(4) 143.0 4_454 yes
C33 H33A F44 0.97 2.61 3.288(5) 127.5 2_575 yes
N49 H49 N32 0.96(4) 1.94(4) 2.875(3) 164(4) . yes

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.029


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3I-300K
_database_code_depnum_ccdc_archive 'CCDC 2022181'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

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'

_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                   6.8240(8)
_cell_length_b                   14.6816(18)
_cell_length_c                   21.469(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.400(4)
_cell_angle_gamma                90
_cell_volume                     2141.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5052
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      30.06

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            28587
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.357
_diffrn_reflns_theta_max         27.934
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5098
_reflns_number_gt                2398
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0449P)²+0.5368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5098
_refine_ls_number_parameters     356
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1405
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.013
_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
F3 F 1.4333(2) 0.55450(16) 0.40612(9) 0.1125(8) Uani 0.899(3) 1 d D . P A 1
F4 F 1.5285(3) 0.63012(18) 0.51607(10) 0.1473(9) Uani 1 1 d D . . B 1
F3B F 0.777(2) 0.6477(16) 0.4219(8) 0.147(9) Uani 0.101(3) 1 d D . P A 2
F2 F 0.0511(2) 0.15944(12) 0.40749(8) 0.0992(6) Uani 1 1 d D . . . .
F1 F 0.3497(2) 0.24410(12) 0.36623(7) 0.0799(6) Uani 0.899(3) 1 d D . P A 1
F1B F 0.001(2) 0.2587(11) 0.1640(4) 0.096(6) Uani 0.101(3) 1 d D . P A 2
C1 C 0.5261(4) 0.34832(16) 0.14999(11) 0.0630(7) Uani 1 1 d . . . . .
H1 H 0.541474 0.341950 0.107625 0.076 Uiso 1 1 calc R U . . .
C2 C 0.3745(4) 0.30628(16) 0.17653(11) 0.0590(6) Uani 1 1 d . . . . .
H2 H 0.287911 0.269955 0.151386 0.071 Uiso 1 1 calc R U . . .
C3 C 0.3449(3) 0.31579(14) 0.23980(11) 0.0493(6) Uani 1 1 d . . . . .
C4 C 0.4743(3) 0.36987(14) 0.27719(10) 0.0484(6) Uani 1 1 d . . . . .
H4 H 0.455365 0.377967 0.319164 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8589(3) 0.49640(14) 0.33830(10) 0.0498(6) Uani 1 1 d . . . . .
H5 H 0.782606 0.485048 0.371145 0.060 Uiso 1 1 calc R U . . .
C6 C 1.0327(3) 0.54462(15) 0.34933(11) 0.0525(6) Uani 1 1 d . . . . .
C7 C 1.1470(4) 0.55945(15) 0.29896(12) 0.0587(6) Uani 1 1 d . . . . .
H7 H 1.265015 0.591077 0.306120 0.070 Uiso 1 1 calc R U . . .
C8 C 1.0898(4) 0.52878(16) 0.23975(12) 0.0593(7) Uani 1 1 d . . . . .
H8 H 1.167189 0.539287 0.207057 0.071 Uiso 1 1 calc R U . . .
N9 N 0.8256(3) 0.44462(13) 0.17542(10) 0.0588(6) Uani 1 1 d . . . . .
H9 H 0.874(3) 0.4480(15) 0.1383(12) 0.071 Uiso 1 1 d . U . . .
C10 C 0.6556(3) 0.40073(15) 0.18885(11) 0.0527(6) Uani 1 1 d . . . . .
C11 C 0.6315(3) 0.41191(14) 0.25267(10) 0.0463(5) Uani 1 1 d . . . . .
C12 C 0.7970(3) 0.46482(14) 0.27892(10) 0.0457(5) Uani 1 1 d . . . . .
C13 C 0.9148(3) 0.48197(15) 0.22998(11) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.1778(3) 0.26696(14) 0.26491(12) 0.0510(6) Uani 1 1 d . . . . .
C15 C 0.1856(3) 0.23505(16) 0.32549(12) 0.0576(6) Uani 1 1 d D . . . .
H15 H 0.298552 0.245182 0.352350 0.069 Uiso 0.101(3) 1 calc R U P A 2
C16 C 0.0314(4) 0.18882(17) 0.34716(13) 0.0652(7) Uani 1 1 d D . . . .
C17 C -0.1362(4) 0.17169(18) 0.31097(15) 0.0731(8) Uani 1 1 d . . . . .
H17 H -0.239671 0.140771 0.326775 0.088 Uiso 1 1 calc R U . . .
C18 C -0.1501(4) 0.20089(18) 0.25050(15) 0.0725(8) Uani 1 1 d . . . . .
H18 H -0.263435 0.189011 0.224220 0.087 Uiso 1 1 calc R U . . .
C19 C 0.0033(4) 0.24799(16) 0.22816(13) 0.0616(7) Uani 1 1 d D . . . .
H19 H -0.009386 0.267694 0.186811 0.074 Uiso 0.899(3) 1 d R U P A 1
C20 C 1.0928(3) 0.58285(16) 0.41183(11) 0.0550(6) Uani 1 1 d . . . . .
C21 C 1.2849(4) 0.58795(19) 0.43742(13) 0.0724(8) Uani 1 1 d D . . . .
H21 H 1.383634 0.564420 0.415051 0.087 Uiso 0.101(3) 1 calc R U P A 2
C22 C 1.3358(4) 0.6265(2) 0.49477(15) 0.0851(9) Uani 1 1 d D . . . .
C23 C 1.2006(5) 0.6602(2) 0.52999(14) 0.0857(9) Uani 1 1 d . . . . .
H23 H 1.237579 0.686265 0.568821 0.103 Uiso 1 1 calc R U . . .
C24 C 1.0063(5) 0.6552(2) 0.50713(14) 0.0893(9) Uani 1 1 d . . . . .
H24 H 0.909006 0.677114 0.530749 0.107 Uiso 1 1 calc R U . . .
C25 C 0.9563(4) 0.6178(2) 0.44939(13) 0.0723(8) Uani 1 1 d D . . . .
H25 H 0.823719 0.615438 0.434715 0.087 Uiso 0.899(3) 1 d R U P A 1
N31 N 0.951(5) 0.468(2) 0.0536(12) 0.073(7) Uani 0.5 1 d . . P C -1
C31 C 0.9199(13) 0.5769(5) 0.0442(3) 0.091(2) Uani 0.5 1 d . . P C -1
H31A H 0.782923 0.591833 0.047814 0.110 Uiso 0.5 1 calc R U P C -1
H31B H 0.998971 0.608821 0.077219 0.110 Uiso 0.5 1 calc R U P C -1
C32 C 0.9770(14) 0.6097(5) -0.0194(3) 0.094(2) Uani 0.5 1 d . . P C -1
H32A H 1.080787 0.653819 -0.012527 0.112 Uiso 0.5 1 d R U P C -1
H32B H 0.866669 0.637305 -0.043257 0.112 Uiso 0.5 1 d R U P C -1
C33 C 0.8243(13) 0.4344(7) 0.0004(3) 0.099(2) Uani 0.5 1 d . . P C -1
H33A H 0.687978 0.449150 0.005192 0.119 Uiso 0.5 1 d R U P C -1
H33B H 0.837882 0.368661 0.001592 0.119 Uiso 0.5 1 d R U P C -1
C34 C 0.8860(12) 0.4679(6) -0.0634(3) 0.0855(19) Uani 0.5 1 d . . P C -1
H34A H 0.777600 0.501171 -0.084166 0.103 Uiso 0.5 1 d R U P C -1
H34B H 0.916624 0.417982 -0.089686 0.103 Uiso 0.5 1 d R U P C -1
C35 C 1.1507(12) 0.4571(7) 0.0443(3) 0.107(2) Uani 0.5 1 d . . P C -1
H35A H 1.183576 0.392957 0.048363 0.128 Uiso 0.5 1 calc R U P C -1
H35B H 1.229028 0.489295 0.077328 0.128 Uiso 0.5 1 calc R U P C -1
C36 C 1.2098(13) 0.4911(7) -0.0192(4) 0.101(2) Uani 0.5 1 d . . P C -1
H36A H 1.264704 0.442595 -0.041972 0.121 Uiso 0.5 1 d R U P C -1
H36B H 1.306875 0.538197 -0.012082 0.121 Uiso 0.5 1 d R U P C -1
N32 N 1.049(5) 0.521(2) -0.0520(10) 0.079(8) Uani 0.5 1 d . . P C -1


_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
F3 C21 1.359(3) . ?
F4 C22 1.352(3) . ?
F3B C25 1.376(8) . ?
F2 C16 1.360(3) . ?
F1 C15 1.361(3) . ?
F1B C19 1.386(8) . ?
C1 C2 1.374(3) . ?
C1 C10 1.389(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.399(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(3) . ?
C3 C14 1.490(3) . ?
C4 C11 1.384(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C5 C12 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(3) . ?
C6 C20 1.477(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.377(3) . ?
C8 H8 0.9300 . ?
N9 C10 1.381(3) . ?
N9 C13 1.382(3) . ?
N9 H9 0.89(2) . ?
C10 C11 1.405(3) . ?
C11 C12 1.441(3) . ?
C12 C13 1.405(3) . ?
C14 C15 1.379(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.370(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.345(3) . ?
C17 C18 1.362(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 C25 1.387(3) . ?
C21 C22 1.370(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.341(4) . ?
C23 C24 1.372(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N31 C35 1.41(3) . ?
N31 C33 1.45(3) . ?
N31 C31 1.62(3) . ?
C31 C32 1.532(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.58(3) . ?
C32 H32A 0.9602 . ?
C32 H32B 0.9601 . ?
C33 C34 1.550(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9701 . ?
C34 N32 1.36(3) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C35 C36 1.541(9) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.32(3) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9599 . ?

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
C2 C1 C10 117.4(2) . . ?
C2 C1 H1 121.3 . . ?
C10 C1 H1 121.3 . . ?
C1 C2 C3 122.8(2) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 C14 122.2(2) . . ?
C2 C3 C14 119.3(2) . . ?
C11 C4 C3 120.6(2) . . ?
C11 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C12 120.8(2) . . ?
C6 C5 H5 119.6 . . ?
C12 C5 H5 119.6 . . ?
C5 C6 C7 118.4(2) . . ?
C5 C6 C20 120.7(2) . . ?
C7 C6 C20 120.8(2) . . ?
C8 C7 C6 122.1(2) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C13 118.2(2) . . ?
C7 C8 H8 120.9 . . ?
C13 C8 H8 120.9 . . ?
C10 N9 C13 108.66(19) . . ?
C10 N9 H9 127.0(16) . . ?
C13 N9 H9 124.3(16) . . ?
N9 C10 C1 129.2(2) . . ?
N9 C10 C11 109.1(2) . . ?
C1 C10 C11 121.6(2) . . ?
C4 C11 C10 119.0(2) . . ?
C4 C11 C12 134.3(2) . . ?
C10 C11 C12 106.56(19) . . ?
C5 C12 C13 118.8(2) . . ?
C5 C12 C11 134.5(2) . . ?
C13 C12 C11 106.66(19) . . ?
C8 C13 N9 129.3(2) . . ?
C8 C13 C12 121.7(2) . . ?
N9 C13 C12 109.0(2) . . ?
C15 C14 C19 114.9(2) . . ?
C15 C14 C3 122.8(2) . . ?
C19 C14 C3 122.2(2) . . ?
F1 C15 C16 116.2(2) . . ?
F1 C15 C14 122.0(2) . . ?
C16 C15 C14 121.7(2) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 F2 119.6(2) . . ?
C17 C16 C15 122.4(3) . . ?
F2 C16 C15 118.1(2) . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 F1B 117.7(7) . . ?
C18 C19 C14 122.7(3) . . ?
F1B C19 C14 118.1(7) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.4 . . ?
C21 C20 C25 114.5(2) . . ?
C21 C20 C6 123.8(2) . . ?
C25 C20 C6 121.6(2) . . ?
F3 C21 C22 117.2(3) . . ?
F3 C21 C20 120.6(2) . . ?
C22 C21 C20 122.2(2) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C23 C22 F4 119.6(3) . . ?
C23 C22 C21 122.0(3) . . ?
F4 C22 C21 118.4(3) . . ?
C22 C23 C24 118.1(3) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 F3B 113.3(8) . . ?
C24 C25 C20 123.4(3) . . ?
F3B C25 C20 119.1(8) . . ?
C24 C25 H25 118.2 . . ?
C20 C25 H25 118.3 . . ?
C35 N31 C33 111.3(17) . . ?
C35 N31 C31 102(2) . . ?
C33 N31 C31 100.1(16) . . ?
C32 C31 N31 112.3(10) . . ?
C32 C31 H31A 109.1 . . ?
N31 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
N31 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 N32 104.6(10) . . ?
C31 C32 H32A 108.8 . . ?
N32 C32 H32A 111.6 . . ?
C31 C32 H32B 110.9 . . ?
N32 C32 H32B 111.7 . . ?
H32A C32 H32B 109.1 . . ?
N31 C33 C34 113.4(12) . . ?
N31 C33 H33A 110.2 . . ?
C34 C33 H33A 111.5 . . ?
N31 C33 H33B 105.5 . . ?
C34 C33 H33B 107.9 . . ?
H33A C33 H33B 108.0 . . ?
N32 C34 C33 107.9(11) . . ?
N32 C34 H34A 111.8 . . ?
C33 C34 H34A 108.0 . . ?
N32 C34 H34B 109.0 . . ?
C33 C34 H34B 111.6 . . ?
H34A C34 H34B 108.5 . . ?
N31 C35 C36 115.3(12) . . ?
N31 C35 H35A 108.4 . . ?
C36 C35 H35A 108.4 . . ?
N31 C35 H35B 108.4 . . ?
C36 C35 H35B 108.4 . . ?
H35A C35 H35B 107.5 . . ?
N32 C36 C35 107.8(12) . . ?
N32 C36 H36A 108.7 . . ?
C35 C36 H36A 111.0 . . ?
N32 C36 H36B 111.8 . . ?
C35 C36 H36B 109.1 . . ?
H36A C36 H36B 108.6 . . ?
C36 N32 C34 122(2) . . ?
C36 N32 C32 108.3(18) . . ?
C34 N32 C32 106(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C14 -179.4(2) . . . . ?
C2 C3 C4 C11 -1.3(3) . . . . ?
C14 C3 C4 C11 177.96(19) . . . . ?
C12 C5 C6 C7 -1.1(3) . . . . ?
C12 C5 C6 C20 176.4(2) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C20 C6 C7 C8 -176.6(2) . . . . ?
C6 C7 C8 C13 -0.1(4) . . . . ?
C13 N9 C10 C1 -175.0(2) . . . . ?
C13 N9 C10 C11 1.6(3) . . . . ?
C2 C1 C10 N9 175.2(2) . . . . ?
C2 C1 C10 C11 -1.1(3) . . . . ?
C3 C4 C11 C10 1.5(3) . . . . ?
C3 C4 C11 C12 -174.1(2) . . . . ?
N9 C10 C11 C4 -177.15(19) . . . . ?
C1 C10 C11 C4 -0.2(3) . . . . ?
N9 C10 C11 C12 -0.4(2) . . . . ?
C1 C10 C11 C12 176.5(2) . . . . ?
C6 C5 C12 C13 0.5(3) . . . . ?
C6 C5 C12 C11 178.0(2) . . . . ?
C4 C11 C12 C5 -2.6(4) . . . . ?
C10 C11 C12 C5 -178.5(2) . . . . ?
C4 C11 C12 C13 175.1(2) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C7 C8 C13 N9 179.9(2) . . . . ?
C7 C8 C13 C12 -0.6(3) . . . . ?
C10 N9 C13 C8 177.4(2) . . . . ?
C10 N9 C13 C12 -2.2(2) . . . . ?
C5 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 C8 -177.8(2) . . . . ?
C5 C12 C13 N9 179.96(19) . . . . ?
C11 C12 C13 N9 1.8(2) . . . . ?
C4 C3 C14 C15 -31.4(3) . . . . ?
C2 C3 C14 C15 147.9(2) . . . . ?
C4 C3 C14 C19 150.4(2) . . . . ?
C2 C3 C14 C19 -30.4(3) . . . . ?
C19 C14 C15 F1 176.6(2) . . . . ?
C3 C14 C15 F1 -1.7(3) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C3 C14 C15 C16 -178.7(2) . . . . ?
F1 C15 C16 C17 -177.2(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
F1 C15 C16 F2 2.7(3) . . . . ?
C14 C15 C16 F2 179.9(2) . . . . ?
F2 C16 C17 C18 -179.1(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 F1B 166.2(8) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C3 C14 C19 C18 178.3(2) . . . . ?
C15 C14 C19 F1B -165.4(8) . . . . ?
C3 C14 C19 F1B 13.0(9) . . . . ?
C5 C6 C20 C21 144.6(2) . . . . ?
C7 C6 C20 C21 -37.9(4) . . . . ?
C5 C6 C20 C25 -36.1(3) . . . . ?
C7 C6 C20 C25 141.4(2) . . . . ?
C25 C20 C21 F3 178.7(2) . . . . ?
C6 C20 C21 F3 -2.0(4) . . . . ?
C25 C20 C21 C22 -1.5(4) . . . . ?
C6 C20 C21 C22 177.9(3) . . . . ?
F3 C21 C22 C23 -178.9(3) . . . . ?
C20 C21 C22 C23 1.3(5) . . . . ?
F3 C21 C22 F4 0.9(5) . . . . ?
C20 C21 C22 F4 -179.0(3) . . . . ?
F4 C22 C23 C24 -179.7(3) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -1.0(5) . . . . ?
C23 C24 C25 F3B -155.9(12) . . . . ?
C23 C24 C25 C20 0.7(5) . . . . ?
C21 C20 C25 C24 0.5(4) . . . . ?
C6 C20 C25 C24 -178.9(3) . . . . ?
C21 C20 C25 F3B 155.9(12) . . . . ?
C6 C20 C25 F3B -23.5(13) . . . . ?
C35 N31 C31 C32 56(2) . . . . ?
C33 N31 C31 C32 -58.3(19) . . . . ?
N31 C31 C32 N32 -0.5(9) . . . . ?
C35 N31 C33 C34 -47(2) . . . . ?
C31 N31 C33 C34 60.2(17) . . . . ?
N31 C33 C34 N32 0.4(12) . . . . ?
C33 N31 C35 C36 49(2) . . . . ?
C31 N31 C35 C36 -57(2) . . . . ?
N31 C35 C36 N32 -2.0(15) . . . . ?
C35 C36 N32 C34 -55(2) . . . . ?
C35 C36 N32 C32 68(2) . . . . ?
C33 C34 N32 C36 56(2) . . . . ?
C33 C34 N32 C32 -68.5(17) . . . . ?
C31 C32 N32 C36 -64.9(19) . . . . ?
C31 C32 N32 C34 67.2(16) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.89(2) 1.96(3) 2.85(2) 172(2) . yes
N9 H9 N32 0.89(2) 2.02(3) 2.90(2) 168(2) 3_765 yes

_refine_diff_density_max         0.158
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.032


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-1LT-200K
_database_code_depnum_ccdc_archive 'CCDC 2022172'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-20183
_shelx_SHELXL_version_number     20183
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.0444(4)
_cell_length_b                   13.7744(4)
_cell_length_c                   22.8418(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.5900(10)
_cell_angle_gamma                90
_cell_volume                     4212.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9235
_cell_measurement_theta_min      2.4452
_cell_measurement_theta_max      29.9631

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            144945
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.794
_diffrn_reflns_theta_max         30.005
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             22733
_reflns_number_gt                21380
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0725P)²+0.4683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 9543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         22733
_refine_ls_number_parameters     1201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
F1 F -0.04726(12) 0.58410(15) 0.36072(8) 0.0615(4) Uani 1 1 d . . . . .
F2 F -0.07683(11) 0.66973(16) 0.15793(7) 0.0629(5) Uani 1 1 d . . . . .
F3 F 0.66919(14) 0.50704(17) -0.01348(7) 0.0675(5) Uani 1 1 d . . . . .
F4 F 0.37555(12) 0.69038(15) -0.06153(7) 0.0629(5) Uani 1 1 d . . . . .
C1 C 0.41851(15) 0.63812(16) 0.37923(9) 0.0357(4) Uani 1 1 d . . . . .
H1 H 0.458134 0.643127 0.420965 0.043 Uiso 1 1 calc R U . . .
C2 C 0.31544(15) 0.63728(16) 0.36319(8) 0.0337(4) Uani 1 1 d . . . . .
H2 H 0.284353 0.642839 0.394649 0.040 Uiso 1 1 calc R U . . .
C3 C 0.25471(13) 0.62845(14) 0.30161(8) 0.0291(3) Uani 1 1 d . . . . .
C4 C 0.30024(13) 0.62185(14) 0.25550(8) 0.0285(3) Uani 1 1 d . . . . .
H4 H 0.260441 0.615307 0.213896 0.034 Uiso 1 1 calc R U . . .
C5 C 0.46193(13) 0.61663(14) 0.17184(8) 0.0290(3) Uani 1 1 d . . . . .
H5 H 0.397200 0.614607 0.142814 0.035 Uiso 1 1 calc R U . . .
C6 C 0.54688(13) 0.61549(14) 0.15208(8) 0.0294(3) Uani 1 1 d . . . . .
C7 C 0.64251(13) 0.61986(16) 0.19587(8) 0.0323(4) Uani 1 1 d . . . . .
H7 H 0.699899 0.619669 0.182068 0.039 Uiso 1 1 calc R U . . .
C8 C 0.65504(13) 0.62439(16) 0.25817(9) 0.0333(4) Uani 1 1 d . . . . .
H8 H 0.719846 0.627202 0.287068 0.040 Uiso 1 1 calc R U . . .
N9 N 0.56237(12) 0.63155(14) 0.33591(7) 0.0337(3) Uani 1 1 d . . . . .
H9 H 0.612(2) 0.631(2) 0.3716(12) 0.040 Uiso 1 1 d . U . . .
C10 C 0.46246(13) 0.63139(14) 0.33231(8) 0.0301(3) Uani 1 1 d . . . . .
C11 C 0.40360(13) 0.62477(14) 0.26997(8) 0.0279(3) Uani 1 1 d . . . . .
C12 C 0.47303(12) 0.62076(14) 0.23444(8) 0.0271(3) Uani 1 1 d . . . . .
C13 C 0.57000(13) 0.62472(14) 0.27736(8) 0.0292(3) Uani 1 1 d . . . . .
C14 C 0.14439(13) 0.62725(14) 0.28725(8) 0.0290(3) Uani 1 1 d . . . . .
C15 C 0.09833(15) 0.60505(16) 0.33190(9) 0.0354(4) Uani 1 1 d . . . . .
H15 H 0.137614 0.589770 0.372587 0.043 Uiso 1 1 calc R U . . .
C16 C -0.00426(16) 0.60544(18) 0.31664(10) 0.0393(4) Uani 1 1 d . . . . .
C17 C -0.06640(15) 0.62663(18) 0.25886(11) 0.0410(4) Uani 1 1 d . . . . .
H17 H -0.137071 0.626937 0.249456 0.049 Uiso 1 1 calc R U . . .
C18 C -0.01917(16) 0.64733(17) 0.21568(10) 0.0399(4) Uani 1 1 d . . . . .
C19 C 0.08287(15) 0.64894(16) 0.22806(9) 0.0356(4) Uani 1 1 d . . . . .
H19 H 0.111515 0.664722 0.196539 0.043 Uiso 1 1 calc R U . . .
C20 C 0.53815(14) 0.61071(15) 0.08595(8) 0.0312(3) Uani 1 1 d . . . . .
C21 C 0.60943(17) 0.56077(17) 0.06610(10) 0.0376(4) Uani 1 1 d . . . . .
H21 H 0.664053 0.529643 0.095019 0.045 Uiso 1 1 calc R U . . .
C22 C 0.59990(19) 0.5570(2) 0.00436(11) 0.0449(5) Uani 1 1 d . . . . .
C23 C 0.52272(19) 0.6004(2) -0.04005(10) 0.0467(5) Uani 1 1 d . . . . .
H23 H 0.517446 0.597053 -0.082457 0.056 Uiso 1 1 calc R U . . .
C24 C 0.45421(17) 0.64851(19) -0.01926(10) 0.0429(5) Uani 1 1 d . . . . .
C25 C 0.45872(15) 0.65582(17) 0.04196(9) 0.0369(4) Uani 1 1 d . . . . .
H25 H 0.409142 0.690596 0.053862 0.044 Uiso 1 1 calc R U . . .
N31 N 0.71148(12) 0.61080(14) 0.45170(7) 0.0337(3) Uani 1 1 d . . . . .
C31 C 0.81009(14) 0.60969(18) 0.44197(8) 0.0354(4) Uani 1 1 d . . . . .
H31A H 0.817539 0.667642 0.418098 0.043 Uiso 1 1 calc R U . . .
H31B H 0.816402 0.551230 0.418200 0.043 Uiso 1 1 calc R U . . .
C32 C 0.89254(14) 0.60927(18) 0.50421(9) 0.0370(4) Uani 1 1 d . . . . .
H32A H 0.935517 0.551459 0.506851 0.044 Uiso 1 1 calc R U . . .
H32B H 0.934763 0.667801 0.507538 0.044 Uiso 1 1 calc R U . . .
C33 C 0.70153(19) 0.52415(18) 0.48651(12) 0.0453(5) Uani 1 1 d . . . . .
H33A H 0.705819 0.465329 0.462527 0.054 Uiso 1 1 calc R U . . .
H33B H 0.635436 0.524392 0.493661 0.054 Uiso 1 1 calc R U . . .
C34 C 0.78435(19) 0.52161(17) 0.54842(10) 0.0422(5) Uani 1 1 d . . . . .
H34A H 0.754037 0.519898 0.582309 0.051 Uiso 1 1 calc R U . . .
H34B H 0.824993 0.462143 0.550957 0.051 Uiso 1 1 calc R U . . .
C35 C 0.70428(17) 0.69706(17) 0.48810(10) 0.0399(4) Uani 1 1 d . . . . .
H35A H 0.637587 0.699169 0.494390 0.048 Uiso 1 1 calc R U . . .
H35B H 0.712210 0.756406 0.465575 0.048 Uiso 1 1 calc R U . . .
C36 C 0.78582(16) 0.69426(16) 0.55087(10) 0.0366(4) Uani 1 1 d . . . . .
H36A H 0.827551 0.753436 0.555980 0.044 Uiso 1 1 calc R U . . .
H36B H 0.754258 0.692901 0.584189 0.044 Uiso 1 1 calc R U . . .
N32 N 0.84881(12) 0.60785(14) 0.55501(7) 0.0342(3) Uani 1 1 d . . . . .
F41 F 1.62257(12) 0.58356(17) 0.63662(8) 0.0689(5) Uani 1 1 d . . . . .
F42 F 1.65849(11) 0.64732(16) 0.84283(7) 0.0650(5) Uani 1 1 d . . . . .
F43 F 0.89346(16) 0.5912(2) 1.01743(9) 0.0834(7) Uani 1 1 d . . . . .
F44 F 1.21220(17) 0.7289(2) 1.05824(8) 0.0900(7) Uani 1 1 d . . . . .
C41 C 1.15992(15) 0.62513(18) 0.62154(8) 0.0364(4) Uani 1 1 d . . . . .
H41 H 1.120271 0.624753 0.579684 0.044 Uiso 1 1 calc R U . . .
C42 C 1.26291(15) 0.62675(17) 0.63743(8) 0.0349(4) Uani 1 1 d . . . . .
H42 H 1.293656 0.629498 0.605695 0.042 Uiso 1 1 calc R U . . .
C43 C 1.32403(13) 0.62449(14) 0.69895(8) 0.0283(3) Uani 1 1 d . . . . .
C44 C 1.27860(13) 0.62341(14) 0.74569(8) 0.0276(3) Uani 1 1 d . . . . .
H44 H 1.318495 0.621620 0.787484 0.033 Uiso 1 1 calc R U . . .
C45 C 1.11614(14) 0.63267(14) 0.82918(8) 0.0298(3) Uani 1 1 d . . . . .
H45 H 1.180734 0.631904 0.858387 0.036 Uiso 1 1 calc R U . . .
C46 C 1.03134(15) 0.63897(15) 0.84876(8) 0.0328(4) Uani 1 1 d . . . . .
C47 C 0.93602(15) 0.63956(17) 0.80470(9) 0.0370(4) Uani 1 1 d . . . . .
H47 H 0.878594 0.644546 0.818268 0.044 Uiso 1 1 calc R U . . .
C48 C 0.92349(14) 0.63313(17) 0.74245(9) 0.0358(4) Uani 1 1 d . . . . .
H48 H 0.858754 0.632802 0.713391 0.043 Uiso 1 1 calc R U . . .
N49 N 1.01618(12) 0.62489(14) 0.66501(7) 0.0338(3) Uani 1 1 d . . . . .
H49 H 0.967(2) 0.623(2) 0.6329(13) 0.041 Uiso 1 1 d . U . . .
C50 C 1.11577(13) 0.62405(15) 0.66848(8) 0.0301(3) Uani 1 1 d . . . . .
C51 C 1.17514(13) 0.62496(13) 0.73094(8) 0.0271(3) Uani 1 1 d . . . . .
C52 C 1.10569(13) 0.62752(14) 0.76664(8) 0.0278(3) Uani 1 1 d . . . . .
C53 C 1.00903(13) 0.62715(14) 0.72373(8) 0.0297(3) Uani 1 1 d . . . . .
C54 C 1.43457(13) 0.62286(14) 0.71338(8) 0.0283(3) Uani 1 1 d . . . . .
C55 C 1.47917(15) 0.60436(17) 0.66727(9) 0.0361(4) Uani 1 1 d . . . . .
H55 H 1.439154 0.593312 0.626143 0.043 Uiso 1 1 calc R U . . .
C56 C 1.58203(17) 0.60243(19) 0.68247(11) 0.0419(5) Uani 1 1 d . . . . .
C57 C 1.64504(15) 0.61652(18) 0.74021(11) 0.0415(4) Uani 1 1 d . . . . .
H57 H 1.715632 0.614912 0.749176 0.050 Uiso 1 1 calc R U . . .
C58 C 1.59924(15) 0.63322(18) 0.78457(10) 0.0397(4) Uani 1 1 d . . . . .
C59 C 1.49773(15) 0.63844(16) 0.77309(9) 0.0351(4) Uani 1 1 d . . . . .
H59 H 1.470400 0.652537 0.805437 0.042 Uiso 1 1 calc R U . . .
C60 C 1.03923(16) 0.64654(17) 0.91498(9) 0.0378(4) Uani 1 1 d . . . . .
C61 C 0.96121(19) 0.6149(2) 0.93642(10) 0.0478(6) Uani 1 1 d . . . . .
H61 H 0.902541 0.587689 0.908833 0.057 Uiso 1 1 calc R U . . .
C62 C 0.9703(2) 0.6236(3) 0.99810(12) 0.0595(8) Uani 1 1 d . . . . .
C63 C 1.0525(3) 0.6618(3) 1.04043(12) 0.0694(10) Uani 1 1 d . . . . .
H63 H 1.056874 0.667542 1.082596 0.083 Uiso 1 1 calc R U . . .
C64 C 1.1286(2) 0.6913(3) 1.01816(11) 0.0617(8) Uani 1 1 d . . . . .
C65 C 1.1246(2) 0.6859(2) 0.95703(10) 0.0472(5) Uani 1 1 d . . . . .
H65 H 1.178711 0.708354 0.943836 0.057 Uiso 1 1 calc R U . . .
F71 F 0.92921(13) 0.4080(3) 0.85500(10) 0.0990(9) Uani 1 1 d . . . . .
F72 F 0.75884(13) 0.36305(15) 0.64740(8) 0.0607(4) Uani 1 1 d . . . . .
F73 F -0.17112(11) 0.27569(16) 0.48345(8) 0.0668(5) Uani 1 1 d . . . . .
F74 F 0.08873(14) 0.42832(14) 0.42933(7) 0.0600(4) Uani 1 1 d . . . . .
C71 C 0.48140(16) 0.3802(2) 0.87088(9) 0.0404(5) Uani 1 1 d . . . . .
H71 H 0.483059 0.381979 0.912750 0.049 Uiso 1 1 calc R U . . .
C72 C 0.56850(15) 0.37982(18) 0.85482(9) 0.0383(4) Uani 1 1 d . . . . .
H72 H 0.630607 0.381720 0.886447 0.046 Uiso 1 1 calc R U . . .
C73 C 0.56865(13) 0.37674(14) 0.79292(8) 0.0291(3) Uani 1 1 d . . . . .
C74 C 0.47735(13) 0.37355(14) 0.74682(8) 0.0282(3) Uani 1 1 d . . . . .
H74 H 0.475828 0.371299 0.704978 0.034 Uiso 1 1 calc R U . . .
C75 C 0.23222(14) 0.36656(15) 0.66400(8) 0.0293(3) Uani 1 1 d . . . . .
H75 H 0.267755 0.364088 0.634629 0.035 Uiso 1 1 calc R U . . .
C76 C 0.12798(14) 0.36554(15) 0.64478(8) 0.0301(3) Uani 1 1 d . . . . .
C77 C 0.07683(14) 0.37061(16) 0.68918(9) 0.0342(4) Uani 1 1 d . . . . .
H77 H 0.005876 0.371359 0.675752 0.041 Uiso 1 1 calc R U . . .
C78 C 0.12578(15) 0.37451(17) 0.75123(9) 0.0349(4) Uani 1 1 d . . . . .
H78 H 0.089885 0.377298 0.780401 0.042 Uiso 1 1 calc R U . . .
N79 N 0.29534(13) 0.37828(16) 0.82795(7) 0.0366(4) Uani 1 1 d . . . . .
H79 H 0.280(2) 0.382(2) 0.8631(13) 0.044 Uiso 1 1 d . U . . .
C80 C 0.39101(15) 0.37779(16) 0.82402(8) 0.0321(4) Uani 1 1 d . . . . .
C81 C 0.38822(13) 0.37364(14) 0.76175(8) 0.0279(3) Uani 1 1 d . . . . .
C82 C 0.28389(13) 0.37123(14) 0.72644(8) 0.0276(3) Uani 1 1 d . . . . .
C83 C 0.23003(14) 0.37422(15) 0.76975(8) 0.0306(3) Uani 1 1 d . . . . .
C84 C 0.66477(14) 0.37819(14) 0.77862(9) 0.0301(3) Uani 1 1 d . . . . .
C85 C 0.75515(16) 0.3914(2) 0.82458(11) 0.0455(5) Uani 1 1 d . . . . .
H85 H 0.756442 0.398020 0.866208 0.055 Uiso 1 1 calc R U . . .
C86 C 0.84265(17) 0.3948(3) 0.80913(13) 0.0557(7) Uani 1 1 d . . . . .
C87 C 0.84775(17) 0.3864(2) 0.75085(13) 0.0493(6) Uani 1 1 d . . . . .
H87 H 0.909298 0.389792 0.741683 0.059 Uiso 1 1 calc R U . . .
C88 C 0.75816(17) 0.37287(17) 0.70607(10) 0.0396(4) Uani 1 1 d . . . . .
C89 C 0.66829(16) 0.36820(17) 0.71829(9) 0.0370(4) Uani 1 1 d . . . . .
H89 H 0.608368 0.358150 0.685721 0.044 Uiso 1 1 calc R U . . .
C90 C 0.06971(14) 0.36030(15) 0.57888(8) 0.0319(4) Uani 1 1 d . . . . .
C91 C -0.02538(16) 0.31777(17) 0.56085(10) 0.0386(4) Uani 1 1 d . . . . .
H91 H -0.052458 0.290494 0.590562 0.046 Uiso 1 1 calc R U . . .
C92 C -0.07920(17) 0.3161(2) 0.49926(11) 0.0459(5) Uani 1 1 d . . . . .
C93 C -0.04435(19) 0.3519(2) 0.45357(10) 0.0487(6) Uani 1 1 d . . . . .
H93 H -0.082496 0.348935 0.411452 0.058 Uiso 1 1 calc R U . . .
C94 C 0.04936(18) 0.39222(18) 0.47278(10) 0.0431(5) Uani 1 1 d . . . . .
C95 C 0.10757(16) 0.39871(16) 0.53357(9) 0.0368(4) Uani 1 1 d . . . . .
H95 H 0.171569 0.428442 0.544301 0.044 Uiso 1 1 calc R U . . .
N101 N 0.25514(12) 0.37329(15) 0.94265(7) 0.0354(3) Uani 1 1 d . . . . .
C101 C 0.14705(16) 0.3859(2) 0.93373(9) 0.0414(5) Uani 1 1 d . . . . .
H101 H 0.109638 0.330646 0.909873 0.050 Uiso 1 1 calc R U . . .
H102 H 0.123327 0.446254 0.910277 0.050 Uiso 1 1 calc R U . . .
C102 C 0.12765(16) 0.3915(2) 0.99658(10) 0.0426(5) Uani 1 1 d . . . . .
H103 H 0.095753 0.454319 1.000340 0.051 Uiso 1 1 calc R U . . .
H104 H 0.081570 0.338786 0.999792 0.051 Uiso 1 1 calc R U . . .
C103 C 0.2874(2) 0.2834(2) 0.97659(12) 0.0487(5) Uani 1 1 d . . . . .
H105 H 0.359377 0.272807 0.982303 0.058 Uiso 1 1 calc R U . . .
H106 H 0.249928 0.227971 0.952944 0.058 Uiso 1 1 calc R U . . .
C104 C 0.2691(2) 0.2888(2) 1.03980(11) 0.0474(5) Uani 1 1 d . . . . .
H107 H 0.224677 0.234961 1.043672 0.057 Uiso 1 1 calc R U . . .
H108 H 0.333335 0.281588 1.072757 0.057 Uiso 1 1 calc R U . . .
C105 C 0.30764(19) 0.4554(2) 0.97814(11) 0.0473(5) Uani 1 1 d . . . . .
H109 H 0.284217 0.516271 0.955307 0.057 Uiso 1 1 calc R U . . .
H110 H 0.380123 0.449023 0.983926 0.057 Uiso 1 1 calc R U . . .
C106 C 0.28957(19) 0.46034(19) 1.04116(10) 0.0445(5) Uani 1 1 d . . . . .
H111 H 0.354014 0.454566 1.074101 0.053 Uiso 1 1 calc R U . . .
H112 H 0.259426 0.523736 1.045798 0.053 Uiso 1 1 calc R U . . .
N102 N 0.22302(13) 0.38206(15) 1.04681(7) 0.0358(3) Uani 1 1 d . . . . .
F111 F -0.46128(10) 0.33051(14) 1.13668(7) 0.0565(4) Uani 1 1 d . . . . .
F112 F -0.29172(12) 0.40854(14) 1.34111(7) 0.0560(4) Uani 1 1 d . . . . .
F113 F 0.63099(12) 0.2808(2) 1.50603(9) 0.0804(7) Uani 1 1 d . . . . .
F114 F 0.37655(16) 0.45479(16) 1.55216(7) 0.0716(5) Uani 1 1 d . . . . .
C111 C -0.01805(16) 0.40758(17) 1.11646(8) 0.0361(4) Uani 1 1 d . . . . .
H113 H -0.020376 0.417704 1.074911 0.043 Uiso 1 1 calc R U . . .
C112 C -0.10462(15) 0.40489(16) 1.13323(9) 0.0344(4) Uani 1 1 d . . . . .
H114 H -0.166882 0.414645 1.102595 0.041 Uiso 1 1 calc R U . . .
C113 C -0.10364(13) 0.38807(14) 1.19462(8) 0.0287(3) Uani 1 1 d . . . . .
C114 C -0.01211(13) 0.37804(14) 1.23987(8) 0.0278(3) Uani 1 1 d . . . . .
H115 H -0.009829 0.367819 1.281406 0.033 Uiso 1 1 calc R U . . .
C115 C 0.23182(13) 0.36946(14) 1.32132(8) 0.0274(3) Uani 1 1 d . . . . .
H116 H 0.196185 0.365650 1.350588 0.033 Uiso 1 1 calc R U . . .
C116 C 0.33636(13) 0.36867(14) 1.34047(8) 0.0289(3) Uani 1 1 d . . . . .
C117 C 0.38752(14) 0.37366(17) 1.29605(9) 0.0343(4) Uani 1 1 d . . . . .
H117 H 0.458470 0.372581 1.309368 0.041 Uiso 1 1 calc R U . . .
C118 C 0.33812(15) 0.38008(17) 1.23383(9) 0.0344(4) Uani 1 1 d . . . . .
H118 H 0.373853 0.383077 1.204585 0.041 Uiso 1 1 calc R U . . .
N119 N 0.16842(13) 0.39415(14) 1.15763(7) 0.0348(4) Uani 1 1 d . . . . .
H119 H 0.181(2) 0.391(2) 1.1245(13) 0.042 Uiso 1 1 d . U . . .
C120 C 0.07254(14) 0.39506(14) 1.16202(8) 0.0308(4) Uani 1 1 d . . . . .
C121 C 0.07591(13) 0.38301(14) 1.22417(8) 0.0272(3) Uani 1 1 d . . . . .
C122 C 0.18071(13) 0.37590(14) 1.25898(8) 0.0266(3) Uani 1 1 d . . . . .
C123 C 0.23472(14) 0.38197(15) 1.21568(8) 0.0296(3) Uani 1 1 d . . . . .
C124 C -0.19910(13) 0.38112(14) 1.20983(8) 0.0293(3) Uani 1 1 d . . . . .
C125 C -0.28815(15) 0.35671(15) 1.16511(9) 0.0333(4) Uani 1 1 d . . . . .
H125 H -0.288781 0.342968 1.124240 0.040 Uiso 1 1 calc R U . . .
C126 C -0.37477(16) 0.35287(16) 1.18106(10) 0.0385(4) Uani 1 1 d . . . . .
C127 C -0.38002(16) 0.36857(18) 1.23951(11) 0.0403(4) Uani 1 1 d . . . . .
H127 H -0.440959 0.364183 1.249330 0.048 Uiso 1 1 calc R U . . .
C128 C -0.29094(17) 0.39103(17) 1.28262(10) 0.0383(4) Uani 1 1 d . . . . .
C129 C -0.20156(15) 0.39902(15) 1.26991(9) 0.0332(4) Uani 1 1 d . . . . .
H129 H -0.142352 0.416398 1.301298 0.040 Uiso 1 1 calc R U . . .
C130 C 0.39410(14) 0.36703(15) 1.40638(8) 0.0314(4) Uani 1 1 d . . . . .
C131 C 0.48720(16) 0.32160(19) 1.42623(10) 0.0406(5) Uani 1 1 d . . . . .
H131 H 0.513339 0.288911 1.397825 0.049 Uiso 1 1 calc R U . . .
C132 C 0.54073(17) 0.3249(2) 1.48787(11) 0.0500(6) Uani 1 1 d . . . . .
C133 C 0.50759(19) 0.3689(2) 1.53168(10) 0.0539(7) Uani 1 1 d . . . . .
H133 H 0.545971 0.370031 1.573785 0.065 Uiso 1 1 calc R U . . .
C134 C 0.4147(2) 0.41145(19) 1.51061(10) 0.0464(5) Uani 1 1 d . . . . .
C135 C 0.35738(17) 0.41253(16) 1.44986(9) 0.0377(4) Uani 1 1 d . . . . .
H135 H 0.294053 0.443641 1.437744 0.045 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
F1 C16 1.354(2) . ?
F2 C18 1.358(2) . ?
F3 C22 1.352(3) . ?
F4 C24 1.357(3) . ?
C1 C2 1.382(3) . ?
C1 C10 1.392(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(3) . ?
C3 C14 1.484(2) . ?
C4 C11 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.392(2) . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(2) . ?
C6 C20 1.480(2) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.391(3) . ?
C8 H8 0.9500 . ?
N9 C13 1.377(2) . ?
N9 C10 1.380(2) . ?
N9 H9 0.90(3) . ?
C10 C11 1.417(2) . ?
C11 C12 1.446(2) . ?
C12 C13 1.418(2) . ?
C14 C15 1.397(3) . ?
C14 C19 1.399(3) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(3) . ?
C20 C25 1.401(3) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.377(4) . ?
C23 C24 1.366(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C25 H25 0.9500 . ?
N31 C33 1.464(3) . ?
N31 C31 1.468(2) . ?
N31 C35 1.471(3) . ?
C31 C32 1.538(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.468(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.536(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.473(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.541(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.469(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
F41 C56 1.360(3) . ?
F42 C58 1.354(2) . ?
F43 C62 1.359(4) . ?
F44 C64 1.354(4) . ?
C41 C42 1.381(3) . ?
C41 C50 1.391(3) . ?
C41 H41 0.9500 . ?
C42 C43 1.408(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.400(2) . ?
C43 C54 1.487(2) . ?
C44 C51 1.389(2) . ?
C44 H44 0.9500 . ?
C45 C52 1.393(2) . ?
C45 C46 1.396(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.411(3) . ?
C46 C60 1.487(3) . ?
C47 C48 1.382(3) . ?
C47 H47 0.9500 . ?
C48 C53 1.394(3) . ?
C48 H48 0.9500 . ?
N49 C53 1.375(2) . ?
N49 C50 1.377(2) . ?
N49 H49 0.84(3) . ?
C50 C51 1.419(2) . ?
C51 C52 1.448(2) . ?
C52 C53 1.414(2) . ?
C54 C59 1.401(3) . ?
C54 C55 1.402(3) . ?
C55 C56 1.380(3) . ?
C55 H55 0.9500 . ?
C56 C57 1.362(3) . ?
C57 C58 1.374(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.371(3) . ?
C59 H59 0.9500 . ?
C60 C61 1.398(3) . ?
C60 C65 1.399(3) . ?
C61 C62 1.381(3) . ?
C61 H61 0.9500 . ?
C62 C63 1.367(5) . ?
C63 C64 1.377(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.382(3) . ?
C65 H65 0.9500 . ?
F71 C86 1.356(3) . ?
F72 C88 1.350(3) . ?
F73 C92 1.351(3) . ?
F74 C94 1.367(3) . ?
C71 C72 1.379(3) . ?
C71 C80 1.392(3) . ?
C71 H71 0.9500 . ?
C72 C73 1.415(3) . ?
C72 H72 0.9500 . ?
C73 C74 1.392(3) . ?
C73 C84 1.482(3) . ?
C74 C81 1.393(2) . ?
C74 H74 0.9500 . ?
C75 C82 1.393(2) . ?
C75 C76 1.396(3) . ?
C75 H75 0.9500 . ?
C76 C77 1.411(2) . ?
C76 C90 1.482(2) . ?
C77 C78 1.377(3) . ?
C77 H77 0.9500 . ?
C78 C83 1.396(3) . ?
C78 H78 0.9500 . ?
N79 C83 1.369(2) . ?
N79 C80 1.373(2) . ?
N79 H79 0.89(3) . ?
C80 C81 1.412(2) . ?
C81 C82 1.444(2) . ?
C82 C83 1.416(2) . ?
C84 C85 1.393(3) . ?
C84 C89 1.401(3) . ?
C85 C86 1.378(3) . ?
C85 H85 0.9500 . ?
C86 C87 1.360(4) . ?
C87 C88 1.374(4) . ?
C87 H87 0.9500 . ?
C88 C89 1.374(3) . ?
C89 H89 0.9500 . ?
C90 C91 1.401(3) . ?
C90 C95 1.402(3) . ?
C91 C92 1.381(3) . ?
C91 H91 0.9500 . ?
C92 C93 1.371(4) . ?
C93 C94 1.373(4) . ?
C93 H93 0.9500 . ?
C94 C95 1.385(3) . ?
C95 H95 0.9500 . ?
N101 C105 1.455(3) . ?
N101 C103 1.458(3) . ?
N101 C101 1.480(3) . ?
C101 C102 1.542(3) . ?
C101 H101 0.9900 . ?
C101 H102 0.9900 . ?
C102 N102 1.483(3) . ?
C102 H103 0.9900 . ?
C102 H104 0.9900 . ?
C103 C104 1.543(4) . ?
C103 H105 0.9900 . ?
C103 H106 0.9900 . ?
C104 N102 1.469(3) . ?
C104 H107 0.9900 . ?
C104 H108 0.9900 . ?
C105 C106 1.537(3) . ?
C105 H109 0.9900 . ?
C105 H110 0.9900 . ?
C106 N102 1.458(3) . ?
C106 H111 0.9900 . ?
C106 H112 0.9900 . ?
F111 C126 1.362(2) . ?
F112 C128 1.361(2) . ?
F113 C132 1.353(3) . ?
F114 C134 1.361(3) . ?
C111 C112 1.381(3) . ?
C111 C120 1.390(3) . ?
C111 H113 0.9500 . ?
C112 C113 1.417(2) . ?
C112 H114 0.9500 . ?
C113 C114 1.392(2) . ?
C113 C124 1.486(3) . ?
C114 C121 1.389(2) . ?
C114 H115 0.9500 . ?
C115 C122 1.390(2) . ?
C115 C116 1.400(2) . ?
C115 H116 0.9500 . ?
C116 C117 1.411(2) . ?
C116 C130 1.479(2) . ?
C117 C118 1.383(3) . ?
C117 H117 0.9500 . ?
C118 C123 1.385(3) . ?
C118 H118 0.9500 . ?
N119 C120 1.380(2) . ?
N119 C123 1.381(2) . ?
N119 H119 0.83(3) . ?
C120 C121 1.416(2) . ?
C121 C122 1.450(2) . ?
C122 C123 1.419(2) . ?
C124 C125 1.396(3) . ?
C124 C129 1.405(3) . ?
C125 C126 1.372(3) . ?
C125 H125 0.9500 . ?
C126 C127 1.376(3) . ?
C127 C128 1.373(3) . ?
C127 H127 0.9500 . ?
C128 C129 1.376(3) . ?
C129 H129 0.9500 . ?
C130 C131 1.396(3) . ?
C130 C135 1.398(3) . ?
C131 C132 1.382(3) . ?
C131 H131 0.9500 . ?
C132 C133 1.366(4) . ?
C133 C134 1.378(4) . ?
C133 H133 0.9500 . ?
C134 C135 1.378(3) . ?
C135 H135 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
C2 C1 C10 117.90(17) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C1 C2 C3 122.26(18) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.83(17) . . ?
C4 C3 C14 121.36(16) . . ?
C2 C3 C14 119.80(17) . . ?
C11 C4 C3 120.31(16) . . ?
C11 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C12 C5 C6 119.39(15) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.51(16) . . ?
C5 C6 C20 120.98(16) . . ?
C7 C6 C20 119.50(16) . . ?
C8 C7 C6 121.94(17) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 118.07(16) . . ?
C7 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
C13 N9 C10 108.55(15) . . ?
C13 N9 H9 128.0(18) . . ?
C10 N9 H9 123.3(18) . . ?
N9 C10 C1 129.28(16) . . ?
N9 C10 C11 109.50(16) . . ?
C1 C10 C11 121.20(17) . . ?
C4 C11 C10 119.45(17) . . ?
C4 C11 C12 134.35(16) . . ?
C10 C11 C12 106.19(15) . . ?
C5 C12 C13 119.85(16) . . ?
C5 C12 C11 133.86(15) . . ?
C13 C12 C11 106.27(14) . . ?
N9 C13 C8 129.24(16) . . ?
N9 C13 C12 109.49(16) . . ?
C8 C13 C12 121.23(16) . . ?
C15 C14 C19 117.73(18) . . ?
C15 C14 C3 121.61(17) . . ?
C19 C14 C3 120.66(17) . . ?
C16 C15 C14 119.65(19) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
F1 C16 C17 117.61(19) . . ?
F1 C16 C15 118.6(2) . . ?
C17 C16 C15 123.8(2) . . ?
C18 C17 C16 115.38(19) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
F2 C18 C19 118.3(2) . . ?
F2 C18 C17 117.94(19) . . ?
C19 C18 C17 123.7(2) . . ?
C18 C19 C14 119.76(19) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C21 C20 C25 118.59(18) . . ?
C21 C20 C6 120.42(17) . . ?
C25 C20 C6 120.99(18) . . ?
C22 C21 C20 119.5(2) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
F3 C22 C21 118.2(2) . . ?
F3 C22 C23 118.5(2) . . ?
C21 C22 C23 123.3(2) . . ?
C24 C23 C22 115.8(2) . . ?
C24 C23 H23 122.1 . . ?
C22 C23 H23 122.1 . . ?
F4 C24 C23 117.8(2) . . ?
F4 C24 C25 117.8(2) . . ?
C23 C24 C25 124.4(2) . . ?
C24 C25 C20 118.4(2) . . ?
C24 C25 H25 120.8 . . ?
C20 C25 H25 120.8 . . ?
C33 N31 C31 108.84(18) . . ?
C33 N31 C35 108.50(17) . . ?
C31 N31 C35 108.86(17) . . ?
N31 C31 C32 109.96(15) . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N32 C32 C31 110.64(15) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 110.40(17) . . ?
N31 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
N31 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N32 C34 C33 110.27(17) . . ?
N32 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.30(16) . . ?
N31 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N31 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 110.11(16) . . ?
N32 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N32 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.2 . . ?
C32 N32 C36 109.03(17) . . ?
C32 N32 C34 108.72(17) . . ?
C36 N32 C34 107.89(16) . . ?
C42 C41 C50 118.23(17) . . ?
C42 C41 H41 120.9 . . ?
C50 C41 H41 120.9 . . ?
C41 C42 C43 122.41(17) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C44 C43 C42 118.71(16) . . ?
C44 C43 C54 121.14(15) . . ?
C42 C43 C54 120.15(16) . . ?
C51 C44 C43 119.96(15) . . ?
C51 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C52 C45 C46 119.75(16) . . ?
C52 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C47 119.29(17) . . ?
C45 C46 C60 121.47(17) . . ?
C47 C46 C60 119.24(18) . . ?
C48 C47 C46 122.15(18) . . ?
C48 C47 H47 118.9 . . ?
C46 C47 H47 118.9 . . ?
C47 C48 C53 117.76(17) . . ?
C47 C48 H48 121.1 . . ?
C53 C48 H48 121.1 . . ?
C53 N49 C50 108.45(15) . . ?
C53 N49 H49 125.0(19) . . ?
C50 N49 H49 126.5(19) . . ?
N49 C50 C41 129.58(16) . . ?
N49 C50 C51 109.62(15) . . ?
C41 C50 C51 120.77(17) . . ?
C44 C51 C50 119.85(16) . . ?
C44 C51 C52 134.17(16) . . ?
C50 C51 C52 105.98(15) . . ?
C45 C52 C53 119.50(16) . . ?
C45 C52 C51 134.29(16) . . ?
C53 C52 C51 106.17(15) . . ?
N49 C53 C48 128.62(16) . . ?
N49 C53 C52 109.77(16) . . ?
C48 C53 C52 121.54(16) . . ?
C59 C54 C55 117.66(17) . . ?
C59 C54 C43 121.67(16) . . ?
C55 C54 C43 120.67(16) . . ?
C56 C55 C54 119.07(19) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
F41 C56 C57 118.2(2) . . ?
F41 C56 C55 117.4(2) . . ?
C57 C56 C55 124.4(2) . . ?
C56 C57 C58 115.22(19) . . ?
C56 C57 H57 122.4 . . ?
C58 C57 H57 122.4 . . ?
F42 C58 C59 118.4(2) . . ?
F42 C58 C57 117.61(19) . . ?
C59 C58 C57 124.0(2) . . ?
C58 C59 C54 119.60(19) . . ?
C58 C59 H59 120.2 . . ?
C54 C59 H59 120.2 . . ?
C61 C60 C65 118.7(2) . . ?
C61 C60 C46 120.6(2) . . ?
C65 C60 C46 120.7(2) . . ?
C62 C61 C60 119.3(3) . . ?
C62 C61 H61 120.3 . . ?
C60 C61 H61 120.3 . . ?
F43 C62 C63 118.7(2) . . ?
F43 C62 C61 117.7(3) . . ?
C63 C62 C61 123.6(3) . . ?
C62 C63 C64 115.9(2) . . ?
C62 C63 H63 122.1 . . ?
C64 C63 H63 122.1 . . ?
F44 C64 C63 118.3(2) . . ?
F44 C64 C65 117.8(3) . . ?
C63 C64 C65 123.9(3) . . ?
C64 C65 C60 118.6(3) . . ?
C64 C65 H65 120.7 . . ?
C60 C65 H65 120.7 . . ?
C72 C71 C80 118.14(17) . . ?
C72 C71 H71 120.9 . . ?
C80 C71 H71 120.9 . . ?
C71 C72 C73 122.35(18) . . ?
C71 C72 H72 118.8 . . ?
C73 C72 H72 118.8 . . ?
C74 C73 C72 118.52(17) . . ?
C74 C73 C84 121.72(16) . . ?
C72 C73 C84 119.76(17) . . ?
C73 C74 C81 120.33(16) . . ?
C73 C74 H74 119.8 . . ?
C81 C74 H74 119.8 . . ?
C82 C75 C76 119.67(16) . . ?
C82 C75 H75 120.2 . . ?
C76 C75 H75 120.2 . . ?
C75 C76 C77 119.14(17) . . ?
C75 C76 C90 121.65(16) . . ?
C77 C76 C90 119.20(17) . . ?
C78 C77 C76 122.53(18) . . ?
C78 C77 H77 118.7 . . ?
C76 C77 H77 118.7 . . ?
C77 C78 C83 117.61(17) . . ?
C77 C78 H78 121.2 . . ?
C83 C78 H78 121.2 . . ?
C83 N79 C80 108.53(15) . . ?
C83 N79 H79 127.1(18) . . ?
C80 N79 H79 124.3(18) . . ?
N79 C80 C71 129.24(17) . . ?
N79 C80 C81 109.64(16) . . ?
C71 C80 C81 121.12(18) . . ?
C74 C81 C80 119.54(17) . . ?
C74 C81 C82 134.30(16) . . ?
C80 C81 C82 106.16(15) . . ?
C75 C82 C83 119.59(16) . . ?
C75 C82 C81 134.43(16) . . ?
C83 C82 C81 105.97(15) . . ?
N79 C83 C78 128.87(17) . . ?
N79 C83 C82 109.70(16) . . ?
C78 C83 C82 121.42(16) . . ?
C85 C84 C89 117.33(19) . . ?
C85 C84 C73 121.26(18) . . ?
C89 C84 C73 121.40(17) . . ?
C86 C85 C84 119.4(2) . . ?
C86 C85 H85 120.3 . . ?
C84 C85 H85 120.3 . . ?
F71 C86 C87 117.9(2) . . ?
F71 C86 C85 117.9(3) . . ?
C87 C86 C85 124.3(2) . . ?
C86 C87 C88 115.7(2) . . ?
C86 C87 H87 122.2 . . ?
C88 C87 H87 122.2 . . ?
F72 C88 C87 118.2(2) . . ?
F72 C88 C89 118.7(2) . . ?
C87 C88 C89 123.1(2) . . ?
C88 C89 C84 120.2(2) . . ?
C88 C89 H89 119.9 . . ?
C84 C89 H89 119.9 . . ?
C91 C90 C95 118.75(18) . . ?
C91 C90 C76 120.24(18) . . ?
C95 C90 C76 121.00(18) . . ?
C92 C91 C90 119.1(2) . . ?
C92 C91 H91 120.5 . . ?
C90 C91 H91 120.5 . . ?
F73 C92 C93 118.5(2) . . ?
F73 C92 C91 117.6(2) . . ?
C93 C92 C91 123.9(2) . . ?
C92 C93 C94 115.5(2) . . ?
C92 C93 H93 122.3 . . ?
C94 C93 H93 122.3 . . ?
F74 C94 C93 118.3(2) . . ?
F74 C94 C95 117.3(2) . . ?
C93 C94 C95 124.4(2) . . ?
C94 C95 C90 118.4(2) . . ?
C94 C95 H95 120.8 . . ?
C90 C95 H95 120.8 . . ?
C105 N101 C103 109.85(18) . . ?
C105 N101 C101 108.12(19) . . ?
C103 N101 C101 108.32(19) . . ?
N101 C101 C102 109.89(16) . . ?
N101 C101 H101 109.7 . . ?
C102 C101 H101 109.7 . . ?
N101 C101 H102 109.7 . . ?
C102 C101 H102 109.7 . . ?
H101 C101 H102 108.2 . . ?
N102 C102 C101 110.11(16) . . ?
N102 C102 H103 109.6 . . ?
C101 C102 H103 109.6 . . ?
N102 C102 H104 109.6 . . ?
C101 C102 H104 109.6 . . ?
H103 C102 H104 108.2 . . ?
N101 C103 C104 110.10(19) . . ?
N101 C103 H105 109.6 . . ?
C104 C103 H105 109.6 . . ?
N101 C103 H106 109.6 . . ?
C104 C103 H106 109.6 . . ?
H105 C103 H106 108.2 . . ?
N102 C104 C103 110.35(18) . . ?
N102 C104 H107 109.6 . . ?
C103 C104 H107 109.6 . . ?
N102 C104 H108 109.6 . . ?
C103 C104 H108 109.6 . . ?
H107 C104 H108 108.1 . . ?
N101 C105 C106 110.92(18) . . ?
N101 C105 H109 109.5 . . ?
C106 C105 H109 109.5 . . ?
N101 C105 H110 109.5 . . ?
C106 C105 H110 109.5 . . ?
H109 C105 H110 108.0 . . ?
N102 C106 C105 109.99(18) . . ?
N102 C106 H111 109.7 . . ?
C105 C106 H111 109.7 . . ?
N102 C106 H112 109.7 . . ?
C105 C106 H112 109.7 . . ?
H111 C106 H112 108.2 . . ?
C106 N102 C104 108.77(18) . . ?
C106 N102 C102 108.65(18) . . ?
C104 N102 C102 108.48(18) . . ?
C112 C111 C120 118.19(17) . . ?
C112 C111 H113 120.9 . . ?
C120 C111 H113 120.9 . . ?
C111 C112 C113 122.18(17) . . ?
C111 C112 H114 118.9 . . ?
C113 C112 H114 118.9 . . ?
C114 C113 C112 118.79(17) . . ?
C114 C113 C124 121.06(16) . . ?
C112 C113 C124 120.14(16) . . ?
C121 C114 C113 119.84(16) . . ?
C121 C114 H115 120.1 . . ?
C113 C114 H115 120.1 . . ?
C122 C115 C116 119.26(16) . . ?
C122 C115 H116 120.4 . . ?
C116 C115 H116 120.4 . . ?
C115 C116 C117 119.27(16) . . ?
C115 C116 C130 121.27(16) . . ?
C117 C116 C130 119.41(16) . . ?
C118 C117 C116 122.39(18) . . ?
C118 C117 H117 118.8 . . ?
C116 C117 H117 118.8 . . ?
C117 C118 C123 117.64(17) . . ?
C117 C118 H118 121.2 . . ?
C123 C118 H118 121.2 . . ?
C120 N119 C123 108.72(15) . . ?
C120 N119 H119 123.5(19) . . ?
C123 N119 H119 126.9(19) . . ?
N119 C120 C111 129.73(17) . . ?
N119 C120 C121 109.52(16) . . ?
C111 C120 C121 120.73(17) . . ?
C114 C121 C120 120.14(16) . . ?
C114 C121 C122 133.66(16) . . ?
C120 C121 C122 106.18(15) . . ?
C115 C122 C123 119.89(16) . . ?
C115 C122 C121 133.68(16) . . ?
C123 C122 C121 106.36(15) . . ?
N119 C123 C118 129.17(17) . . ?
N119 C123 C122 109.21(16) . . ?
C118 C123 C122 121.55(16) . . ?
C125 C124 C129 118.43(17) . . ?
C125 C124 C113 121.09(16) . . ?
C129 C124 C113 120.48(17) . . ?
C126 C125 C124 119.02(18) . . ?
C126 C125 H125 120.5 . . ?
C124 C125 H125 120.5 . . ?
F111 C126 C125 118.3(2) . . ?
F111 C126 C127 117.42(19) . . ?
C125 C126 C127 124.3(2) . . ?
C128 C127 C126 115.26(19) . . ?
C128 C127 H127 122.4 . . ?
C126 C127 H127 122.4 . . ?
F112 C128 C127 117.91(19) . . ?
F112 C128 C129 118.14(19) . . ?
C127 C128 C129 123.9(2) . . ?
C128 C129 C124 119.05(18) . . ?
C128 C129 H129 120.5 . . ?
C124 C129 H129 120.5 . . ?
C131 C130 C135 118.72(18) . . ?
C131 C130 C116 120.62(18) . . ?
C135 C130 C116 120.65(18) . . ?
C132 C131 C130 118.9(2) . . ?
C132 C131 H131 120.5 . . ?
C130 C131 H131 120.5 . . ?
F113 C132 C133 118.0(2) . . ?
F113 C132 C131 117.9(3) . . ?
C133 C132 C131 124.1(2) . . ?
C132 C133 C134 115.4(2) . . ?
C132 C133 H133 122.3 . . ?
C134 C133 H133 122.3 . . ?
F114 C134 C133 118.3(2) . . ?
F114 C134 C135 117.7(2) . . ?
C133 C134 C135 124.0(2) . . ?
C134 C135 C130 118.8(2) . . ?
C134 C135 H135 120.6 . . ?
C130 C135 H135 120.6 . . ?

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
C10 C1 C2 C3 1.0(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C14 179.54(19) . . . . ?
C2 C3 C4 C11 -0.5(3) . . . . ?
C14 C3 C4 C11 178.91(17) . . . . ?
C12 C5 C6 C7 -0.8(3) . . . . ?
C12 C5 C6 C20 179.74(18) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C20 C6 C7 C8 -179.98(19) . . . . ?
C6 C7 C8 C13 -0.1(3) . . . . ?
C13 N9 C10 C1 -179.2(2) . . . . ?
C13 N9 C10 C11 -0.3(2) . . . . ?
C2 C1 C10 N9 179.3(2) . . . . ?
C2 C1 C10 C11 0.6(3) . . . . ?
C3 C4 C11 C10 2.0(3) . . . . ?
C3 C4 C11 C12 -179.4(2) . . . . ?
N9 C10 C11 C4 178.96(17) . . . . ?
C1 C10 C11 C4 -2.1(3) . . . . ?
N9 C10 C11 C12 0.0(2) . . . . ?
C1 C10 C11 C12 178.98(19) . . . . ?
C6 C5 C12 C13 0.6(3) . . . . ?
C6 C5 C12 C11 178.6(2) . . . . ?
C4 C11 C12 C5 3.3(4) . . . . ?
C10 C11 C12 C5 -177.9(2) . . . . ?
C4 C11 C12 C13 -178.5(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C10 N9 C13 C8 178.4(2) . . . . ?
C10 N9 C13 C12 0.5(2) . . . . ?
C7 C8 C13 N9 -177.9(2) . . . . ?
C7 C8 C13 C12 -0.1(3) . . . . ?
C5 C12 C13 N9 178.06(18) . . . . ?
C11 C12 C13 N9 -0.4(2) . . . . ?
C5 C12 C13 C8 -0.1(3) . . . . ?
C11 C12 C13 C8 -178.63(19) . . . . ?
C4 C3 C14 C15 160.73(19) . . . . ?
C2 C3 C14 C15 -19.8(3) . . . . ?
C4 C3 C14 C19 -19.5(3) . . . . ?
C2 C3 C14 C19 159.91(19) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C3 C14 C15 C16 179.6(2) . . . . ?
C14 C15 C16 F1 -179.7(2) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
F1 C16 C17 C18 -179.7(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 F2 -179.4(2) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
F2 C18 C19 C14 179.3(2) . . . . ?
C17 C18 C19 C14 1.0(4) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C3 C14 C19 C18 179.9(2) . . . . ?
C5 C6 C20 C21 -146.2(2) . . . . ?
C7 C6 C20 C21 34.4(3) . . . . ?
C5 C6 C20 C25 33.8(3) . . . . ?
C7 C6 C20 C25 -145.6(2) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C6 C20 C21 C22 179.9(2) . . . . ?
C20 C21 C22 F3 -179.1(2) . . . . ?
C20 C21 C22 C23 0.0(4) . . . . ?
F3 C22 C23 C24 179.0(2) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 F4 -178.4(2) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
F4 C24 C25 C20 178.3(2) . . . . ?
C23 C24 C25 C20 -0.4(4) . . . . ?
C21 C20 C25 C24 0.3(3) . . . . ?
C6 C20 C25 C24 -179.71(19) . . . . ?
C33 N31 C31 C32 -59.9(2) . . . . ?
C35 N31 C31 C32 58.2(2) . . . . ?
N31 C31 C32 N32 1.3(3) . . . . ?
C31 N31 C33 C34 58.8(2) . . . . ?
C35 N31 C33 C34 -59.6(2) . . . . ?
N31 C33 C34 N32 0.7(3) . . . . ?
C33 N31 C35 C36 58.1(2) . . . . ?
C31 N31 C35 C36 -60.2(2) . . . . ?
N31 C35 C36 N32 1.9(3) . . . . ?
C31 C32 N32 C36 -59.6(2) . . . . ?
C31 C32 N32 C34 57.8(2) . . . . ?
C35 C36 N32 C32 57.5(2) . . . . ?
C35 C36 N32 C34 -60.4(2) . . . . ?
C33 C34 N32 C32 -59.0(2) . . . . ?
C33 C34 N32 C36 59.1(2) . . . . ?
C50 C41 C42 C43 1.9(4) . . . . ?
C41 C42 C43 C44 -1.9(3) . . . . ?
C41 C42 C43 C54 177.8(2) . . . . ?
C42 C43 C44 C51 -0.3(3) . . . . ?
C54 C43 C44 C51 -179.98(17) . . . . ?
C52 C45 C46 C47 0.3(3) . . . . ?
C52 C45 C46 C60 -178.79(19) . . . . ?
C45 C46 C47 C48 0.7(3) . . . . ?
C60 C46 C47 C48 179.8(2) . . . . ?
C46 C47 C48 C53 -0.8(3) . . . . ?
C53 N49 C50 C41 -177.6(2) . . . . ?
C53 N49 C50 C51 0.5(2) . . . . ?
C42 C41 C50 N49 178.1(2) . . . . ?
C42 C41 C50 C51 0.2(3) . . . . ?
C43 C44 C51 C50 2.3(3) . . . . ?
C43 C44 C51 C52 -177.7(2) . . . . ?
N49 C50 C51 C44 179.38(18) . . . . ?
C41 C50 C51 C44 -2.3(3) . . . . ?
N49 C50 C51 C52 -0.6(2) . . . . ?
C41 C50 C51 C52 177.7(2) . . . . ?
C46 C45 C52 C53 -1.0(3) . . . . ?
C46 C45 C52 C51 176.7(2) . . . . ?
C44 C51 C52 C45 2.6(4) . . . . ?
C50 C51 C52 C45 -177.4(2) . . . . ?
C44 C51 C52 C53 -179.5(2) . . . . ?
C50 C51 C52 C53 0.5(2) . . . . ?
C50 N49 C53 C48 176.8(2) . . . . ?
C50 N49 C53 C52 -0.2(2) . . . . ?
C47 C48 C53 N49 -176.6(2) . . . . ?
C47 C48 C53 C52 0.0(3) . . . . ?
C45 C52 C53 N49 178.07(18) . . . . ?
C51 C52 C53 N49 -0.2(2) . . . . ?
C45 C52 C53 C48 0.9(3) . . . . ?
C51 C52 C53 C48 -177.41(19) . . . . ?
C44 C43 C54 C59 -12.2(3) . . . . ?
C42 C43 C54 C59 168.1(2) . . . . ?
C44 C43 C54 C55 167.09(19) . . . . ?
C42 C43 C54 C55 -12.6(3) . . . . ?
C59 C54 C55 C56 -0.1(3) . . . . ?
C43 C54 C55 C56 -179.4(2) . . . . ?
C54 C55 C56 F41 179.5(2) . . . . ?
C54 C55 C56 C57 0.7(4) . . . . ?
F41 C56 C57 C58 -178.7(2) . . . . ?
C55 C56 C57 C58 0.2(4) . . . . ?
C56 C57 C58 F42 179.7(2) . . . . ?
C56 C57 C58 C59 -1.7(4) . . . . ?
F42 C58 C59 C54 -179.1(2) . . . . ?
C57 C58 C59 C54 2.3(4) . . . . ?
C55 C54 C59 C58 -1.3(3) . . . . ?
C43 C54 C59 C58 178.0(2) . . . . ?
C45 C46 C60 C61 -154.4(2) . . . . ?
C47 C46 C60 C61 26.5(3) . . . . ?
C45 C46 C60 C65 25.9(3) . . . . ?
C47 C46 C60 C65 -153.2(2) . . . . ?
C65 C60 C61 C62 0.2(4) . . . . ?
C46 C60 C61 C62 -179.5(2) . . . . ?
C60 C61 C62 F43 -179.4(2) . . . . ?
C60 C61 C62 C63 -0.1(4) . . . . ?
F43 C62 C63 C64 178.7(3) . . . . ?
C61 C62 C63 C64 -0.6(5) . . . . ?
C62 C63 C64 F44 -179.4(3) . . . . ?
C62 C63 C64 C65 1.3(5) . . . . ?
F44 C64 C65 C60 179.5(3) . . . . ?
C63 C64 C65 C60 -1.2(4) . . . . ?
C61 C60 C65 C64 0.4(4) . . . . ?
C46 C60 C65 C64 -179.9(2) . . . . ?
C80 C71 C72 C73 -0.3(4) . . . . ?
C71 C72 C73 C74 -0.3(3) . . . . ?
C71 C72 C73 C84 179.0(2) . . . . ?
C72 C73 C74 C81 0.1(3) . . . . ?
C84 C73 C74 C81 -179.09(18) . . . . ?
C82 C75 C76 C77 0.9(3) . . . . ?
C82 C75 C76 C90 -179.79(18) . . . . ?
C75 C76 C77 C78 -1.4(3) . . . . ?
C90 C76 C77 C78 179.2(2) . . . . ?
C76 C77 C78 C83 0.6(3) . . . . ?
C83 N79 C80 C71 -179.4(2) . . . . ?
C83 N79 C80 C81 0.2(3) . . . . ?
C72 C71 C80 N79 -179.5(2) . . . . ?
C72 C71 C80 C81 0.9(4) . . . . ?
C73 C74 C81 C80 0.5(3) . . . . ?
C73 C74 C81 C82 179.8(2) . . . . ?
N79 C80 C81 C74 179.27(19) . . . . ?
C71 C80 C81 C74 -1.1(3) . . . . ?
N79 C80 C81 C82 -0.2(2) . . . . ?
C71 C80 C81 C82 179.5(2) . . . . ?
C76 C75 C82 C83 0.4(3) . . . . ?
C76 C75 C82 C81 -179.9(2) . . . . ?
C74 C81 C82 C75 1.1(4) . . . . ?
C80 C81 C82 C75 -179.6(2) . . . . ?
C74 C81 C82 C83 -179.2(2) . . . . ?
C80 C81 C82 C83 0.1(2) . . . . ?
C80 N79 C83 C78 -179.0(2) . . . . ?
C80 N79 C83 C82 -0.2(3) . . . . ?
C77 C78 C83 N79 179.5(2) . . . . ?
C77 C78 C83 C82 0.8(3) . . . . ?
C75 C82 C83 N79 179.80(18) . . . . ?
C81 C82 C83 N79 0.0(2) . . . . ?
C75 C82 C83 C78 -1.3(3) . . . . ?
C81 C82 C83 C78 178.98(19) . . . . ?
C74 C73 C84 C85 173.3(2) . . . . ?
C72 C73 C84 C85 -5.9(3) . . . . ?
C74 C73 C84 C89 -5.4(3) . . . . ?
C72 C73 C84 C89 175.3(2) . . . . ?
C89 C84 C85 C86 0.5(4) . . . . ?
C73 C84 C85 C86 -178.3(2) . . . . ?
C84 C85 C86 F71 179.8(3) . . . . ?
C84 C85 C86 C87 0.3(5) . . . . ?
F71 C86 C87 C88 179.8(3) . . . . ?
C85 C86 C87 C88 -0.7(5) . . . . ?
C86 C87 C88 F72 -179.3(2) . . . . ?
C86 C87 C88 C89 0.3(4) . . . . ?
F72 C88 C89 C84 -179.9(2) . . . . ?
C87 C88 C89 C84 0.5(4) . . . . ?
C85 C84 C89 C88 -0.9(3) . . . . ?
C73 C84 C89 C88 177.9(2) . . . . ?
C75 C76 C90 C91 151.8(2) . . . . ?
C77 C76 C90 C91 -28.8(3) . . . . ?
C75 C76 C90 C95 -29.1(3) . . . . ?
C77 C76 C90 C95 150.3(2) . . . . ?
C95 C90 C91 C92 -0.8(3) . . . . ?
C76 C90 C91 C92 178.34(19) . . . . ?
C90 C91 C92 F73 -179.2(2) . . . . ?
C90 C91 C92 C93 1.6(4) . . . . ?
F73 C92 C93 C94 179.8(2) . . . . ?
C91 C92 C93 C94 -1.0(4) . . . . ?
C92 C93 C94 F74 179.3(2) . . . . ?
C92 C93 C94 C95 -0.4(4) . . . . ?
F74 C94 C95 C90 -178.65(19) . . . . ?
C93 C94 C95 C90 1.1(3) . . . . ?
C91 C90 C95 C94 -0.5(3) . . . . ?
C76 C90 C95 C94 -179.57(19) . . . . ?
C105 N101 C101 C102 -59.0(3) . . . . ?
C103 N101 C101 C102 60.0(3) . . . . ?
N101 C101 C102 N102 -0.2(3) . . . . ?
C105 N101 C103 C104 57.4(3) . . . . ?
C101 N101 C103 C104 -60.5(3) . . . . ?
N101 C103 C104 N102 1.0(3) . . . . ?
C103 N101 C105 C106 -57.8(3) . . . . ?
C101 N101 C105 C106 60.3(3) . . . . ?
N101 C105 C106 N102 -1.1(3) . . . . ?
C105 C106 N102 C104 59.3(2) . . . . ?
C105 C106 N102 C102 -58.6(3) . . . . ?
C103 C104 N102 C106 -59.4(2) . . . . ?
C103 C104 N102 C102 58.6(2) . . . . ?
C101 C102 N102 C106 59.3(3) . . . . ?
C101 C102 N102 C104 -58.8(3) . . . . ?
C120 C111 C112 C113 -1.2(3) . . . . ?
C111 C112 C113 C114 2.8(3) . . . . ?
C111 C112 C113 C124 -177.0(2) . . . . ?
C112 C113 C114 C121 -1.1(3) . . . . ?
C124 C113 C114 C121 178.77(17) . . . . ?
C122 C115 C116 C117 -0.5(3) . . . . ?
C122 C115 C116 C130 176.82(17) . . . . ?
C115 C116 C117 C118 0.5(3) . . . . ?
C130 C116 C117 C118 -176.9(2) . . . . ?
C116 C117 C118 C123 0.3(3) . . . . ?
C123 N119 C120 C111 178.3(2) . . . . ?
C123 N119 C120 C121 -0.1(2) . . . . ?
C112 C111 C120 N119 179.7(2) . . . . ?
C112 C111 C120 C121 -2.0(3) . . . . ?
C113 C114 C121 C120 -2.1(3) . . . . ?
C113 C114 C121 C122 179.9(2) . . . . ?
N119 C120 C121 C114 -177.69(18) . . . . ?
C111 C120 C121 C114 3.7(3) . . . . ?
N119 C120 C121 C122 0.9(2) . . . . ?
C111 C120 C121 C122 -177.79(19) . . . . ?
C116 C115 C122 C123 -0.3(3) . . . . ?
C116 C115 C122 C121 -176.6(2) . . . . ?
C114 C121 C122 C115 -6.3(4) . . . . ?
C120 C121 C122 C115 175.5(2) . . . . ?
C114 C121 C122 C123 177.0(2) . . . . ?
C120 C121 C122 C123 -1.2(2) . . . . ?
C120 N119 C123 C118 -177.5(2) . . . . ?
C120 N119 C123 C122 -0.7(2) . . . . ?
C117 C118 C123 N119 175.4(2) . . . . ?
C117 C118 C123 C122 -1.1(3) . . . . ?
C115 C122 C123 N119 -176.06(18) . . . . ?
C121 C122 C123 N119 1.2(2) . . . . ?
C115 C122 C123 C118 1.1(3) . . . . ?
C121 C122 C123 C118 178.31(19) . . . . ?
C114 C113 C124 C125 -157.02(19) . . . . ?
C112 C113 C124 C125 22.8(3) . . . . ?
C114 C113 C124 C129 22.9(3) . . . . ?
C112 C113 C124 C129 -157.25(19) . . . . ?
C129 C124 C125 C126 1.2(3) . . . . ?
C113 C124 C125 C126 -178.85(19) . . . . ?
C124 C125 C126 F111 178.9(2) . . . . ?
C124 C125 C126 C127 -2.2(3) . . . . ?
F111 C126 C127 C128 -179.9(2) . . . . ?
C125 C126 C127 C128 1.2(4) . . . . ?
C126 C127 C128 F112 179.2(2) . . . . ?
C126 C127 C128 C129 0.7(4) . . . . ?
F112 C128 C129 C124 179.92(19) . . . . ?
C127 C128 C129 C124 -1.6(4) . . . . ?
C125 C124 C129 C128 0.6(3) . . . . ?
C113 C124 C129 C128 -179.35(19) . . . . ?
C115 C116 C130 C131 149.2(2) . . . . ?
C117 C116 C130 C131 -33.5(3) . . . . ?
C115 C116 C130 C135 -32.0(3) . . . . ?
C117 C116 C130 C135 145.3(2) . . . . ?
C135 C130 C131 C132 -1.4(3) . . . . ?
C116 C130 C131 C132 177.4(2) . . . . ?
C130 C131 C132 F113 -179.7(2) . . . . ?
C130 C131 C132 C133 1.2(4) . . . . ?
F113 C132 C133 C134 -179.1(2) . . . . ?
C131 C132 C133 C134 -0.1(4) . . . . ?
C132 C133 C134 F114 178.7(2) . . . . ?
C132 C133 C134 C135 -0.9(4) . . . . ?
F114 C134 C135 C130 -178.9(2) . . . . ?
C133 C134 C135 C130 0.8(4) . . . . ?
C131 C130 C135 C134 0.4(3) . . . . ?
C116 C130 C135 C134 -178.3(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
_geom_hbond_publ_flag
N9 H9 N31 0.90(3) 1.96(3) 2.849(2) 171(3) . yes
C34 H34A F41 0.99 2.66 3.566(3) 151.4 1_455 yes
C34 H34A F72 0.99 2.61 3.240(3) 121.4 . yes
C36 H36A F74 0.99 2.66 3.636(3) 170.0 2_656 yes
N49 H49 N32 0.84(3) 2.05(3) 2.885(2) 176(3) . yes
C55 H55 F114 0.95 2.52 3.308(3) 139.9 1_654 yes
N79 H79 N101 0.89(3) 1.96(3) 2.843(2) 172(3) . yes
C101 H101 F2 0.99 2.66 3.602(3) 158.5 2_546 yes
C104 H107 F43 0.99 2.69 3.539(4) 144.3 2_647 yes
N119 H119 N102 0.83(3) 2.03(3) 2.863(2) 176(3) . yes
C125 H125 F4 0.95 2.63 3.256(3) 124.1 2_546 yes

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.055


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3II-200K
_database_code_depnum_ccdc_archive 'CCDC 2022184'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   19.1580(7)
_cell_length_b                   6.7794(3)
_cell_length_c                   17.4666(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.3620(10)
_cell_angle_gamma                90
_cell_volume                     2140.25(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9996
_cell_measurement_theta_min      2.4121
_cell_measurement_theta_max      30.4377

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            65803
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.311
_diffrn_reflns_theta_max         30.468
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6030
_reflns_number_gt                5405
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0797P)²+0.7061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.050(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6030
_refine_ls_number_parameters     338
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1407
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.092
_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
F1 F 0.07617(4) 1.15667(13) 0.77557(5) 0.0424(2) Uani 1 1 d . . . . .
F2 F 0.09726(6) 1.44971(13) 0.88119(6) 0.0516(2) Uani 1 1 d . . . . .
F3 F 0.44254(5) 0.79879(13) 0.60454(7) 0.0568(3) Uani 1 1 d . . . . .
F4 F 0.57345(6) 0.83906(16) 0.58807(9) 0.0737(4) Uani 1 1 d . . . . .
N9 N 0.17172(6) 0.35839(15) 0.64284(7) 0.0335(2) Uani 1 1 d . . . . .
H9 H 0.1331(9) 0.285(3) 0.6132(10) 0.040 Uiso 1 1 d . U . . .
C1 C 0.10848(6) 0.58079(18) 0.71409(7) 0.0322(2) Uani 1 1 d . . . . .
H1 H 0.063255 0.509461 0.699023 0.039 Uiso 1 1 calc R U . . .
C2 C 0.11867(6) 0.74704(18) 0.76232(7) 0.0307(2) Uani 1 1 d . . . . .
H2 H 0.079624 0.789249 0.780638 0.037 Uiso 1 1 calc R U . . .
C3 C 0.18504(6) 0.85612(16) 0.78526(7) 0.0272(2) Uani 1 1 d . . . . .
C4 C 0.24233(6) 0.79636(17) 0.75798(7) 0.0286(2) Uani 1 1 d . . . . .
H4 H 0.287056 0.869770 0.772123 0.034 Uiso 1 1 calc R U . . .
C5 C 0.35239(6) 0.55788(18) 0.67247(7) 0.0312(2) Uani 1 1 d . . . . .
H5 H 0.379579 0.670017 0.698859 0.037 Uiso 1 1 calc R U . . .
C6 C 0.38341(6) 0.42602(18) 0.63194(7) 0.0320(2) Uani 1 1 d . . . . .
C7 C 0.34220(7) 0.25923(19) 0.59370(8) 0.0367(3) Uani 1 1 d . . . . .
H7 H 0.363867 0.168773 0.566612 0.044 Uiso 1 1 calc R U . . .
C8 C 0.27140(7) 0.22351(18) 0.59446(8) 0.0362(3) Uani 1 1 d . . . . .
H8 H 0.244501 0.110491 0.568580 0.043 Uiso 1 1 calc R U . . .
C10 C 0.16660(6) 0.52106(17) 0.68826(7) 0.0296(2) Uani 1 1 d . . . . .
C11 C 0.23356(6) 0.62813(17) 0.70979(7) 0.0281(2) Uani 1 1 d . . . . .
C12 C 0.28117(6) 0.52450(17) 0.67414(7) 0.0290(2) Uani 1 1 d . . . . .
C13 C 0.24079(7) 0.35822(17) 0.63430(7) 0.0308(2) Uani 1 1 d . . . . .
C14 C 0.19624(6) 1.02630(16) 0.84134(6) 0.0268(2) Uani 1 1 d . . . . .
C15 C 0.14208(6) 1.16689(18) 0.83543(7) 0.0297(2) Uani 1 1 d . . . . .
C16 C 0.15342(7) 1.32180(18) 0.88956(8) 0.0357(3) Uani 1 1 d . . . . .
C17 C 0.21927(9) 1.3446(2) 0.95139(9) 0.0427(3) Uani 1 1 d . . . . .
H17 H 0.226817 1.451847 0.988248 0.051 Uiso 1 1 calc R U . . .
C18 C 0.27431(8) 1.2075(2) 0.95863(8) 0.0425(3) Uani 1 1 d . . . . .
H18 H 0.320478 1.220447 1.000916 0.051 Uiso 1 1 calc R U . . .
C19 C 0.26291(7) 1.05133(19) 0.90491(7) 0.0341(2) Uani 1 1 d . . . . .
H19 H 0.301555 0.958352 0.911413 0.041 Uiso 1 1 calc R U . . .
C20 C 0.45879(7) 0.45388(19) 0.62763(8) 0.0342(3) Uani 1 1 d . . . . .
C21 C 0.48474(7) 0.6352(2) 0.61306(9) 0.0387(3) Uani 1 1 d . . . . .
C22 C 0.55328(8) 0.6570(2) 0.60408(10) 0.0457(3) Uani 1 1 d . . . . .
C23 C 0.59976(8) 0.5008(3) 0.61075(11) 0.0518(4) Uani 1 1 d . . . . .
H23 H 0.646896 0.517228 0.604686 0.062 Uiso 1 1 calc R U . . .
C24 C 0.57597(9) 0.3185(3) 0.62660(12) 0.0561(4) Uani 1 1 d . . . . .
H24 H 0.607404 0.207256 0.632058 0.067 Uiso 1 1 calc R U . . .
C25 C 0.50692(8) 0.2946(2) 0.63473(11) 0.0473(3) Uani 1 1 d . . . . .
H25 H 0.491922 0.166879 0.645389 0.057 Uiso 1 1 calc R U . . .
N31 N 0.0500(10) 0.115(3) 0.5393(10) 0.0430(15) Uani 0.5 1 d . U P . .
C31 C 0.0771(3) -0.0868(6) 0.5632(3) 0.0883(15) Uani 0.5 1 d . U P A -1
H31A H 0.091783 -0.102528 0.622842 0.106 Uiso 0.5 1 calc R U P A -1
H31B H 0.120528 -0.115457 0.546298 0.106 Uiso 0.5 1 calc R U P A -1
C32 C 0.0119(2) -0.2286(5) 0.5196(2) 0.0694(11) Uani 0.5 1 d . U P A -1
H32A H 0.029829 -0.331368 0.490412 0.083 Uiso 0.5 1 calc R U P A -1
H32B H -0.004923 -0.295150 0.560854 0.083 Uiso 0.5 1 calc R U P A -1
C33 C 0.0469(3) 0.1220(7) 0.4545(2) 0.0732(12) Uani 0.5 1 d . U P A -1
H33A H 0.095732 0.088194 0.450250 0.088 Uiso 0.5 1 calc R U P A -1
H33B H 0.033120 0.256046 0.432078 0.088 Uiso 0.5 1 calc R U P A -1
C34 C -0.0117(2) -0.0286(6) 0.40708(18) 0.0575(9) Uani 0.5 1 d . U P A -1
H34A H -0.047646 0.037869 0.359886 0.069 Uiso 0.5 1 calc R U P A -1
H34B H 0.012798 -0.134276 0.386215 0.069 Uiso 0.5 1 calc R U P A -1
C35 C -0.0101(2) 0.1615(10) 0.5527(4) 0.1020(18) Uani 0.5 1 d . U P A -1
H35A H -0.021691 0.302290 0.539502 0.122 Uiso 0.5 1 calc R U P A -1
H35B H -0.003566 0.141713 0.610871 0.122 Uiso 0.5 1 calc R U P A -1
C36 C -0.0752(2) 0.0301(10) 0.4995(4) 0.0999(18) Uani 0.5 1 d . U P A -1
H36A H -0.101257 -0.027201 0.534677 0.120 Uiso 0.5 1 calc R U P A -1
H36B H -0.110900 0.114803 0.458819 0.120 Uiso 0.5 1 calc R U P A -1
N32 N -0.0534(9) -0.121(2) 0.4596(9) 0.0377(12) Uani 0.5 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.3479(14) . ?
F2 C16 1.3515(15) . ?
F3 C21 1.3513(15) . ?
F4 C22 1.3498(18) . ?
N9 C13 1.3799(15) . ?
N9 C10 1.3808(15) . ?
N9 H9 0.899(18) . ?
C1 C2 1.3817(17) . ?
C1 C10 1.3932(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4093(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3939(15) . ?
C3 C14 1.4823(15) . ?
C4 C11 1.3941(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3902(16) . ?
C5 C12 1.3927(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4136(17) . ?
C6 C20 1.4830(16) . ?
C7 C8 1.3823(18) . ?
C7 H7 0.9500 . ?
C8 C13 1.3901(17) . ?
C8 H8 0.9500 . ?
C10 C11 1.4121(15) . ?
C11 C12 1.4457(15) . ?
C12 C13 1.4129(15) . ?
C14 C15 1.3872(16) . ?
C14 C19 1.3974(16) . ?
C15 C16 1.3813(17) . ?
C16 C17 1.371(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3830(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3808(19) . ?
C20 C25 1.3985(18) . ?
C21 C22 1.3812(18) . ?
C22 C23 1.363(2) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.386(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 N32 0.07(3) 3_556 ?
N31 C35 1.29(2) . ?
N31 C33 1.463(18) . ?
N31 C31 1.474(19) . ?
C31 C32 1.560(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.525(17) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.539(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.536(16) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.564(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.381(17) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N9 C10 108.42(10) . . ?
C13 N9 H9 125.0(11) . . ?
C10 N9 H9 124.7(11) . . ?
C2 C1 C10 117.90(10) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C1 C2 C3 122.22(10) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 119.26(10) . . ?
C4 C3 C14 119.62(10) . . ?
C2 C3 C14 121.03(10) . . ?
C3 C4 C11 119.55(10) . . ?
C3 C4 H4 120.2 . . ?
C11 C4 H4 120.2 . . ?
C6 C5 C12 119.56(11) . . ?
C6 C5 H5 120.2 . . ?
C12 C5 H5 120.2 . . ?
C5 C6 C7 119.27(11) . . ?
C5 C6 C20 122.14(11) . . ?
C7 C6 C20 118.59(11) . . ?
C8 C7 C6 122.12(11) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C13 117.89(11) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
N9 C10 C1 129.41(11) . . ?
N9 C10 C11 109.41(10) . . ?
C1 C10 C11 121.16(10) . . ?
C4 C11 C10 119.89(10) . . ?
C4 C11 C12 133.68(10) . . ?
C10 C11 C12 106.42(10) . . ?
C5 C12 C13 119.97(10) . . ?
C5 C12 C11 133.81(10) . . ?
C13 C12 C11 106.21(10) . . ?
N9 C13 C8 129.30(11) . . ?
N9 C13 C12 109.52(10) . . ?
C8 C13 C12 121.18(11) . . ?
C15 C14 C19 116.10(10) . . ?
C15 C14 C3 123.00(10) . . ?
C19 C14 C3 120.89(10) . . ?
F1 C15 C16 117.66(11) . . ?
F1 C15 C14 120.51(10) . . ?
C16 C15 C14 121.83(11) . . ?
F2 C16 C17 120.32(12) . . ?
F2 C16 C15 118.35(12) . . ?
C17 C16 C15 121.32(12) . . ?
C16 C17 C18 118.18(12) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.64(13) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.94(12) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C21 C20 C25 115.89(12) . . ?
C21 C20 C6 122.61(11) . . ?
C25 C20 C6 121.45(12) . . ?
F3 C21 C20 120.81(11) . . ?
F3 C21 C22 117.13(13) . . ?
C20 C21 C22 122.03(13) . . ?
F4 C22 C23 120.27(13) . . ?
F4 C22 C21 118.01(13) . . ?
C23 C22 C21 121.71(14) . . ?
C22 C23 C24 117.65(14) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C23 C24 C25 121.09(14) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 121.62(15) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
N32 N31 C35 125(10) 3_556 . ?
N32 N31 C33 90(10) 3_556 . ?
C35 N31 C33 116.0(13) . . ?
N32 N31 C31 105(10) 3_556 . ?
C35 N31 C31 115.3(13) . . ?
C33 N31 C31 102.1(12) . . ?
N31 C31 C32 106.5(7) . . ?
N31 C31 H31A 110.4 . . ?
C32 C31 H31A 110.4 . . ?
N31 C31 H31B 110.4 . . ?
C32 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
N32 C32 C31 112.5(7) . . ?
N32 C32 H32A 109.1 . . ?
C31 C32 H32A 109.1 . . ?
N32 C32 H32B 109.1 . . ?
C31 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
N31 C33 C34 107.5(7) . . ?
N31 C33 H33A 110.2 . . ?
C34 C33 H33A 110.2 . . ?
N31 C33 H33B 110.2 . . ?
C34 C33 H33B 110.2 . . ?
H33A C33 H33B 108.5 . . ?
N32 C34 C33 112.4(6) . . ?
N32 C34 H34A 109.1 . . ?
C33 C34 H34A 109.1 . . ?
N32 C34 H34B 109.1 . . ?
C33 C34 H34B 109.1 . . ?
H34A C34 H34B 107.9 . . ?
N31 C35 C36 109.7(8) . . ?
N31 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N31 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N32 C36 C35 114.1(7) . . ?
N32 C36 H36A 108.7 . . ?
C35 C36 H36A 108.7 . . ?
N32 C36 H36B 108.7 . . ?
C35 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
N31 N32 C36 80(10) 3_556 . ?
N31 N32 C32 69(10) 3_556 . ?
C36 N32 C32 108.9(10) . . ?
N31 N32 C34 49(10) 3_556 . ?
C36 N32 C34 107.6(11) . . ?
C32 N32 C34 97.8(10) . . ?

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
C10 C1 C2 C3 0.30(18) . . . . ?
C1 C2 C3 C4 0.64(18) . . . . ?
C1 C2 C3 C14 -176.03(11) . . . . ?
C2 C3 C4 C11 -1.15(17) . . . . ?
C14 C3 C4 C11 175.58(10) . . . . ?
C12 C5 C6 C7 -0.55(19) . . . . ?
C12 C5 C6 C20 179.68(11) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C20 C6 C7 C8 -179.52(12) . . . . ?
C6 C7 C8 C13 0.2(2) . . . . ?
C13 N9 C10 C1 -178.41(12) . . . . ?
C13 N9 C10 C11 -0.16(14) . . . . ?
C2 C1 C10 N9 177.32(12) . . . . ?
C2 C1 C10 C11 -0.75(18) . . . . ?
C3 C4 C11 C10 0.72(17) . . . . ?
C3 C4 C11 C12 -177.91(12) . . . . ?
N9 C10 C11 C4 -178.17(11) . . . . ?
C1 C10 C11 C4 0.25(18) . . . . ?
N9 C10 C11 C12 0.79(13) . . . . ?
C1 C10 C11 C12 179.21(11) . . . . ?
C6 C5 C12 C13 -0.45(18) . . . . ?
C6 C5 C12 C11 179.79(12) . . . . ?
C4 C11 C12 C5 -2.5(2) . . . . ?
C10 C11 C12 C5 178.69(13) . . . . ?
C4 C11 C12 C13 177.66(13) . . . . ?
C10 C11 C12 C13 -1.10(13) . . . . ?
C10 N9 C13 C8 179.28(13) . . . . ?
C10 N9 C13 C12 -0.56(14) . . . . ?
C7 C8 C13 N9 178.98(13) . . . . ?
C7 C8 C13 C12 -1.19(19) . . . . ?
C5 C12 C13 N9 -178.79(11) . . . . ?
C11 C12 C13 N9 1.04(13) . . . . ?
C5 C12 C13 C8 1.35(18) . . . . ?
C11 C12 C13 C8 -178.82(11) . . . . ?
C4 C3 C14 C15 140.09(11) . . . . ?
C2 C3 C14 C15 -43.24(16) . . . . ?
C4 C3 C14 C19 -41.01(16) . . . . ?
C2 C3 C14 C19 135.65(12) . . . . ?
C19 C14 C15 F1 179.26(10) . . . . ?
C3 C14 C15 F1 -1.80(17) . . . . ?
C19 C14 C15 C16 -0.35(17) . . . . ?
C3 C14 C15 C16 178.60(11) . . . . ?
F1 C15 C16 F2 2.22(16) . . . . ?
C14 C15 C16 F2 -178.17(10) . . . . ?
F1 C15 C16 C17 -178.99(11) . . . . ?
C14 C15 C16 C17 0.62(19) . . . . ?
F2 C16 C17 C18 178.42(12) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C15 C14 C19 C18 -0.18(18) . . . . ?
C3 C14 C19 C18 -179.15(12) . . . . ?
C5 C6 C20 C21 -42.67(19) . . . . ?
C7 C6 C20 C21 137.57(14) . . . . ?
C5 C6 C20 C25 140.13(14) . . . . ?
C7 C6 C20 C25 -39.64(19) . . . . ?
C25 C20 C21 F3 179.49(13) . . . . ?
C6 C20 C21 F3 2.1(2) . . . . ?
C25 C20 C21 C22 1.5(2) . . . . ?
C6 C20 C21 C22 -175.81(13) . . . . ?
F3 C21 C22 F4 0.4(2) . . . . ?
C20 C21 C22 F4 178.46(14) . . . . ?
F3 C21 C22 C23 -179.38(15) . . . . ?
C20 C21 C22 C23 -1.3(2) . . . . ?
F4 C22 C23 C24 -179.57(17) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C20 -0.3(3) . . . . ?
C21 C20 C25 C24 -0.7(2) . . . . ?
C6 C20 C25 C24 176.66(15) . . . . ?
N32 N31 C31 C32 -165(26) 3_556 . . . ?
C35 N31 C31 C32 54.7(14) . . . . ?
C33 N31 C31 C32 -71.9(10) . . . . ?
N31 C31 C32 N32 7.3(7) . . . . ?
N32 N31 C33 C34 169(29) 3_556 . . . ?
C35 N31 C33 C34 -61.6(14) . . . . ?
C31 N31 C33 C34 64.6(11) . . . . ?
N31 C33 C34 N32 5.8(6) . . . . ?
N32 N31 C35 C36 164(30) 3_556 . . . ?
C33 N31 C35 C36 54.8(15) . . . . ?
C31 N31 C35 C36 -64.5(14) . . . . ?
N31 C35 C36 N32 8.5(10) . . . . ?
C35 C36 N32 N31 -16(25) . . . 3_556 ?
C35 C36 N32 C32 47.8(13) . . . . ?
C35 C36 N32 C34 -57.2(12) . . . . ?
C31 C32 N32 N31 16(29) . . . 3_556 ?
C31 C32 N32 C36 -55.0(12) . . . . ?
C31 C32 N32 C34 56.7(10) . . . . ?
C33 C34 N32 N31 -11(38) . . . 3_556 ?
C33 C34 N32 C36 48.0(12) . . . . ?
C33 C34 N32 C32 -64.8(9) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.899(18) 2.04(2) 2.939(16) 175.2(16) . yes
C34 H34A F1 0.99 2.60 3.138(3) 113.9 3_566 yes
C34 H34B F1 0.99 2.61 3.381(4) 135.2 4_565 yes
C35 H35A F2 0.99 2.52 3.036(4) 112.3 2_546 yes

_refine_diff_density_max         0.666
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-2-200K
_database_code_depnum_ccdc_archive 'CCDC 2022176'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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                   6.6696(2)
_cell_length_b                   14.9431(5)
_cell_length_c                   21.3309(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.362(2)
_cell_angle_gamma                90
_cell_volume                     2116.63(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9763
_cell_measurement_theta_min      2.9636
_cell_measurement_theta_max      29.5342

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            58731
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.967
_diffrn_reflns_theta_max         29.545
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5448
_reflns_number_gt                4928
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0659P)²+0.4156P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.082(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5448
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1218
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
F1 F -0.02505(11) 0.23714(6) 0.15438(3) 0.0481(2) Uani 1 1 d . . . . .
F2 F 0.03766(13) 0.15513(6) 0.40247(4) 0.0559(2) Uani 1 1 d . . . . .
F3 F 1.39926(11) 0.53814(6) 0.42286(4) 0.0560(2) Uani 1 1 d . . . . .
F4 F 0.77765(13) 0.68761(7) 0.53093(4) 0.0650(3) Uani 1 1 d . . . . .
C1 C 0.54558(19) 0.33046(8) 0.14370(5) 0.0389(3) Uani 1 1 d . . . . .
H1 H 0.572349 0.324296 0.100947 0.047 Uiso 1 1 calc R U . . .
C2 C 0.38302(17) 0.28818(8) 0.16607(5) 0.0366(2) Uani 1 1 d . . . . .
H2 H 0.298923 0.251795 0.138157 0.044 Uiso 1 1 calc R U . . .
C3 C 0.33713(15) 0.29710(7) 0.22912(5) 0.0315(2) Uani 1 1 d . . . . .
C4 C 0.46027(15) 0.35124(7) 0.26971(5) 0.0301(2) Uani 1 1 d . . . . .
H4 H 0.429832 0.359556 0.311946 0.036 Uiso 1 1 calc R U . . .
C5 C 0.83346(15) 0.48060(7) 0.33886(5) 0.0299(2) Uani 1 1 d . . . . .
H5 H 0.743370 0.470721 0.370127 0.036 Uiso 1 1 calc R U . . .
C6 C 1.01026(15) 0.52936(7) 0.35331(5) 0.0313(2) Uani 1 1 d . . . . .
C7 C 1.14219(16) 0.54325(7) 0.30617(5) 0.0346(2) Uani 1 1 d . . . . .
H7 H 1.263818 0.575293 0.316515 0.042 Uiso 1 1 calc R U . . .
C8 C 1.10014(16) 0.51183(7) 0.24571(5) 0.0356(2) Uani 1 1 d . . . . .
H8 H 1.189395 0.522671 0.214345 0.043 Uiso 1 1 calc R U . . .
N9 N 0.84603(15) 0.42592(6) 0.17603(4) 0.0363(2) Uani 1 1 d . . . . .
H9 H 0.894(2) 0.4310(10) 0.1384(7) 0.044 Uiso 1 1 d . U . . .
C10 C 0.66935(17) 0.38233(7) 0.18523(5) 0.0336(2) Uani 1 1 d . . . . .
C11 C 0.62758(15) 0.39310(7) 0.24847(5) 0.0294(2) Uani 1 1 d . . . . .
C12 C 0.78998(15) 0.44662(7) 0.27855(5) 0.0290(2) Uani 1 1 d . . . . .
C13 C 0.92252(16) 0.46361(7) 0.23191(5) 0.0318(2) Uani 1 1 d . . . . .
C14 C 0.16853(15) 0.24771(7) 0.25373(5) 0.0323(2) Uani 1 1 d . . . . .
C15 C -0.00576(17) 0.22032(8) 0.21728(6) 0.0367(2) Uani 1 1 d . . . . .
C16 C -0.16319(18) 0.17601(8) 0.24101(7) 0.0451(3) Uani 1 1 d . . . . .
H16 H -0.279302 0.160370 0.214019 0.054 Uiso 1 1 calc R U . . .
C17 C -0.15171(19) 0.15450(9) 0.30393(7) 0.0465(3) Uani 1 1 d . . . . .
H17 H -0.258626 0.124171 0.321404 0.056 Uiso 1 1 calc R U . . .
C18 C 0.02006(18) 0.17851(8) 0.34052(6) 0.0409(3) Uani 1 1 d . . . . .
C19 C 0.17677(17) 0.22413(7) 0.31746(5) 0.0359(2) Uani 1 1 d . . . . .
H19 H 0.291563 0.239758 0.345030 0.043 Uiso 1 1 calc R U . . .
C20 C 1.05069(15) 0.57162(7) 0.41597(5) 0.0323(2) Uani 1 1 d . . . . .
C21 C 0.89471(16) 0.61010(8) 0.44595(5) 0.0373(2) Uani 1 1 d . . . . .
H21 H 0.760531 0.607545 0.426680 0.045 Uiso 1 1 calc R U . . .
C22 C 0.93438(18) 0.65176(9) 0.50334(6) 0.0425(3) Uani 1 1 d . . . . .
C23 C 1.1259(2) 0.65894(9) 0.53350(6) 0.0455(3) Uani 1 1 d . . . . .
H23 H 1.149356 0.689131 0.572695 0.055 Uiso 1 1 calc R U . . .
C24 C 1.28206(19) 0.62079(9) 0.50485(6) 0.0459(3) Uani 1 1 d . . . . .
H24 H 1.416110 0.624243 0.524134 0.055 Uiso 1 1 calc R U . . .
C25 C 1.24185(16) 0.57778(8) 0.44816(6) 0.0385(3) Uani 1 1 d . . . . .
N31 N 0.977(2) 0.4618(10) 0.0507(7) 0.0426(15) Uani 0.5 1 d . . P A -1
C31 C 0.8356(6) 0.4339(3) 0.00198(14) 0.0676(10) Uani 0.5 1 d . . P A -1
H31A H 0.699134 0.451620 0.011976 0.081 Uiso 0.5 1 calc R U P A -1
H31B H 0.838875 0.367833 -0.001043 0.081 Uiso 0.5 1 calc R U P A -1
C32 C 0.8767(6) 0.4747(3) -0.06238(13) 0.0623(9) Uani 0.5 1 d . . P A -1
H32A H 0.900282 0.426067 -0.092320 0.075 Uiso 0.5 1 calc R U P A -1
H32B H 0.757488 0.509187 -0.079779 0.075 Uiso 0.5 1 calc R U P A -1
C33 C 0.9358(5) 0.5710(2) 0.05277(14) 0.0602(8) Uani 0.5 1 d . . P A -1
H33A H 0.796469 0.582629 0.063067 0.072 Uiso 0.5 1 calc R U P A -1
H33B H 1.029777 0.598855 0.085794 0.072 Uiso 0.5 1 calc R U P A -1
C34 C 0.9677(6) 0.6122(2) -0.01226(14) 0.0612(8) Uani 0.5 1 d . . P A -1
H34A H 1.071574 0.659667 -0.007699 0.073 Uiso 0.5 1 calc R U P A -1
H34B H 0.840632 0.638554 -0.031743 0.073 Uiso 0.5 1 calc R U P A -1
C35 C 1.1765(5) 0.4585(3) 0.03880(15) 0.0609(8) Uani 0.5 1 d . . P A -1
H35A H 1.219634 0.395162 0.037890 0.073 Uiso 0.5 1 calc R U P A -1
H35B H 1.259080 0.488454 0.073676 0.073 Uiso 0.5 1 calc R U P A -1
C36 C 1.2169(5) 0.5034(3) -0.02379(15) 0.0641(9) Uani 0.5 1 d . . P A -1
H36A H 1.305573 0.555960 -0.015207 0.077 Uiso 0.5 1 calc R U P A -1
H36B H 1.286788 0.460691 -0.049803 0.077 Uiso 0.5 1 calc R U P A -1
N32 N 1.041(3) 0.5297(11) -0.0557(7) 0.054(3) Uani 0.5 1 d . . P A -1


_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
F1 C15 1.3592(14) . ?
F2 C18 1.3613(15) . ?
F3 C25 1.3602(14) . ?
F4 C22 1.3569(15) . ?
C1 C2 1.3781(16) . ?
C1 C10 1.3894(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.4130(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3949(14) . ?
C3 C14 1.4817(15) . ?
C4 C11 1.3915(14) . ?
C4 H4 0.9500 . ?
C5 C12 1.3882(14) . ?
C5 C6 1.3959(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4120(15) . ?
C6 C20 1.4801(15) . ?
C7 C8 1.3767(16) . ?
C7 H7 0.9500 . ?
C8 C13 1.3944(15) . ?
C8 H8 0.9500 . ?
N9 C13 1.3728(14) . ?
N9 C10 1.3764(14) . ?
N9 H9 0.895(16) . ?
C10 C11 1.4118(14) . ?
C11 C12 1.4473(14) . ?
C12 C13 1.4142(13) . ?
C14 C15 1.3981(15) . ?
C14 C19 1.4003(16) . ?
C15 C16 1.3771(17) . ?
C16 C17 1.375(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3723(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3767(16) . ?
C19 H19 0.9500 . ?
C20 C25 1.3935(15) . ?
C20 C21 1.3950(16) . ?
C21 C22 1.3768(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.3795(17) . ?
C23 C24 1.379(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3735(18) . ?
C24 H24 0.9500 . ?
N31 C35 1.382(18) . ?
N31 C31 1.398(15) . ?
N31 C33 1.656(15) . ?
C31 C32 1.550(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.367(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.550(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.64(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.540(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.358(16) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
C2 C1 C10 118.34(10) . . ?
C2 C1 H1 120.8 . . ?
C10 C1 H1 120.8 . . ?
C1 C2 C3 122.26(10) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.56(10) . . ?
C4 C3 C14 119.42(9) . . ?
C2 C3 C14 121.96(9) . . ?
C11 C4 C3 120.14(9) . . ?
C11 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C5 C6 119.64(9) . . ?
C12 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.29(10) . . ?
C5 C6 C20 120.07(9) . . ?
C7 C6 C20 120.48(9) . . ?
C8 C7 C6 122.08(10) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.95(9) . . ?
C7 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
C13 N9 C10 108.90(9) . . ?
C13 N9 H9 127.4(10) . . ?
C10 N9 H9 123.6(10) . . ?
N9 C10 C1 129.68(10) . . ?
N9 C10 C11 109.29(9) . . ?
C1 C10 C11 120.95(10) . . ?
C4 C11 C10 119.72(9) . . ?
C4 C11 C12 133.93(9) . . ?
C10 C11 C12 106.27(9) . . ?
C5 C12 C13 119.74(9) . . ?
C5 C12 C11 134.09(9) . . ?
C13 C12 C11 106.16(9) . . ?
N9 C13 C8 129.40(10) . . ?
N9 C13 C12 109.34(9) . . ?
C8 C13 C12 121.26(10) . . ?
C15 C14 C19 114.92(10) . . ?
C15 C14 C3 124.60(10) . . ?
C19 C14 C3 120.47(9) . . ?
F1 C15 C16 116.53(10) . . ?
F1 C15 C14 119.47(10) . . ?
C16 C15 C14 124.00(11) . . ?
C17 C16 C15 119.76(11) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 117.47(12) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
F2 C18 C17 118.47(11) . . ?
F2 C18 C19 118.33(11) . . ?
C17 C18 C19 123.20(12) . . ?
C18 C19 C14 120.62(10) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C25 C20 C21 115.73(10) . . ?
C25 C20 C6 123.66(10) . . ?
C21 C20 C6 120.60(9) . . ?
C22 C21 C20 120.29(10) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
F4 C22 C21 118.19(10) . . ?
F4 C22 C23 118.96(11) . . ?
C21 C22 C23 122.85(12) . . ?
C24 C23 C22 117.76(12) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C25 C24 C23 119.34(11) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
F3 C25 C24 117.30(10) . . ?
F3 C25 C20 118.70(11) . . ?
C24 C25 C20 123.99(11) . . ?
C35 N31 C31 116.5(13) . . ?
C35 N31 C33 101.7(8) . . ?
C31 N31 C33 102.3(8) . . ?
N31 C31 C32 112.3(5) . . ?
N31 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
N31 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
N32 C32 C31 110.6(6) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 N31 109.3(5) . . ?
C34 C33 H33A 109.8 . . ?
N31 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
N31 C33 H33B 109.8 . . ?
H33A C33 H33B 108.3 . . ?
C33 C34 N32 106.3(5) . . ?
C33 C34 H34A 110.5 . . ?
N32 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
N32 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 113.2(5) . . ?
N31 C35 H35A 108.9 . . ?
C36 C35 H35A 108.9 . . ?
N31 C35 H35B 108.9 . . ?
C36 C35 H35B 108.9 . . ?
H35A C35 H35B 107.8 . . ?
N32 C36 C35 110.4(7) . . ?
N32 C36 H36A 109.6 . . ?
C35 C36 H36A 109.6 . . ?
N32 C36 H36B 109.6 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.1 . . ?
C36 N32 C32 121.6(10) . . ?
C36 N32 C34 102.9(10) . . ?
C32 N32 C34 103.3(12) . . ?

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
C10 C1 C2 C3 1.03(17) . . . . ?
C1 C2 C3 C4 0.53(16) . . . . ?
C1 C2 C3 C14 -176.72(10) . . . . ?
C2 C3 C4 C11 -1.83(15) . . . . ?
C14 C3 C4 C11 175.49(9) . . . . ?
C12 C5 C6 C7 -0.03(15) . . . . ?
C12 C5 C6 C20 175.42(9) . . . . ?
C5 C6 C7 C8 1.44(16) . . . . ?
C20 C6 C7 C8 -173.99(10) . . . . ?
C6 C7 C8 C13 -1.13(16) . . . . ?
C13 N9 C10 C1 -175.80(11) . . . . ?
C13 N9 C10 C11 1.01(12) . . . . ?
C2 C1 C10 N9 175.18(11) . . . . ?
C2 C1 C10 C11 -1.31(17) . . . . ?
C3 C4 C11 C10 1.57(15) . . . . ?
C3 C4 C11 C12 -174.68(11) . . . . ?
N9 C10 C11 C4 -177.10(9) . . . . ?
C1 C10 C11 C4 0.03(16) . . . . ?
N9 C10 C11 C12 0.08(12) . . . . ?
C1 C10 C11 C12 177.22(10) . . . . ?
C6 C5 C12 C13 -1.59(15) . . . . ?
C6 C5 C12 C11 178.46(10) . . . . ?
C4 C11 C12 C5 -4.5(2) . . . . ?
C10 C11 C12 C5 178.86(11) . . . . ?
C4 C11 C12 C13 175.51(11) . . . . ?
C10 C11 C12 C13 -1.09(11) . . . . ?
C10 N9 C13 C8 178.11(11) . . . . ?
C10 N9 C13 C12 -1.73(12) . . . . ?
C7 C8 C13 N9 179.63(11) . . . . ?
C7 C8 C13 C12 -0.55(16) . . . . ?
C5 C12 C13 N9 -178.23(9) . . . . ?
C11 C12 C13 N9 1.73(11) . . . . ?
C5 C12 C13 C8 1.92(15) . . . . ?
C11 C12 C13 C8 -178.12(9) . . . . ?
C4 C3 C14 C15 154.44(10) . . . . ?
C2 C3 C14 C15 -28.33(16) . . . . ?
C4 C3 C14 C19 -26.28(14) . . . . ?
C2 C3 C14 C19 150.96(11) . . . . ?
C19 C14 C15 F1 -177.66(9) . . . . ?
C3 C14 C15 F1 1.66(16) . . . . ?
C19 C14 C15 C16 2.05(16) . . . . ?
C3 C14 C15 C16 -178.63(10) . . . . ?
F1 C15 C16 C17 178.19(11) . . . . ?
C14 C15 C16 C17 -1.52(18) . . . . ?
C15 C16 C17 C18 -0.25(19) . . . . ?
C16 C17 C18 F2 -177.74(11) . . . . ?
C16 C17 C18 C19 1.4(2) . . . . ?
F2 C18 C19 C14 178.33(10) . . . . ?
C17 C18 C19 C14 -0.80(18) . . . . ?
C15 C14 C19 C18 -0.88(16) . . . . ?
C3 C14 C19 C18 179.77(10) . . . . ?
C5 C6 C20 C25 143.72(11) . . . . ?
C7 C6 C20 C25 -40.89(15) . . . . ?
C5 C6 C20 C21 -37.69(15) . . . . ?
C7 C6 C20 C21 137.70(11) . . . . ?
C25 C20 C21 C22 0.73(16) . . . . ?
C6 C20 C21 C22 -177.96(11) . . . . ?
C20 C21 C22 F4 -179.50(11) . . . . ?
C20 C21 C22 C23 0.91(19) . . . . ?
F4 C22 C23 C24 179.09(12) . . . . ?
C21 C22 C23 C24 -1.3(2) . . . . ?
C22 C23 C24 C25 0.05(19) . . . . ?
C23 C24 C25 F3 -177.48(11) . . . . ?
C23 C24 C25 C20 1.68(19) . . . . ?
C21 C20 C25 F3 177.11(10) . . . . ?
C6 C20 C25 F3 -4.25(16) . . . . ?
C21 C20 C25 C24 -2.04(17) . . . . ?
C6 C20 C25 C24 176.61(11) . . . . ?
C35 N31 C31 C32 -46.3(11) . . . . ?
C33 N31 C31 C32 63.6(10) . . . . ?
N31 C31 C32 N32 -0.9(5) . . . . ?
C35 N31 C33 C34 62.0(8) . . . . ?
C31 N31 C33 C34 -58.8(10) . . . . ?
N31 C33 C34 N32 -2.9(4) . . . . ?
C31 N31 C35 C36 49.8(11) . . . . ?
C33 N31 C35 C36 -60.5(9) . . . . ?
N31 C35 C36 N32 -5.0(5) . . . . ?
C35 C36 N32 C32 -45.7(17) . . . . ?
C35 C36 N32 C34 69.1(8) . . . . ?
C31 C32 N32 C36 48.7(17) . . . . ?
C31 C32 N32 C34 -65.9(8) . . . . ?
C33 C34 N32 C36 -61.8(9) . . . . ?
C33 C34 N32 C32 65.6(8) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.895(16) 2.05(2) 2.937(14) 170.4(15) . yes
N9 H9 N32 0.895(16) 1.94(2) 2.820(15) 165.2(15) 3_765 yes
C21 H21 F3 0.95 2.62 3.4661(13) 148.9 1_455 yes
C24 H24 F4 0.95 2.58 3.4480(15) 151.7 1_655 yes

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.079


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3I-200K
_database_code_depnum_ccdc_archive 'CCDC 2022180'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

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'

_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                   6.7928(4)
_cell_length_b                   14.5649(8)
_cell_length_c                   21.3902(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.7754(16)
_cell_angle_gamma                90
_cell_volume                     2105.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    8413
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      29.94

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.386
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.208
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6963
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            29489
_diffrn_reflns_av_unetI/netI     0.0989
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.370
_diffrn_reflns_theta_max         30.095
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6161
_reflns_number_gt                2751
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0474P)²+0.2656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6161
_refine_ls_number_parameters     356
_refine_ls_number_restraints     342
_refine_ls_R_factor_all          0.1748
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.001
_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
F3 F 1.44316(18) 0.55398(12) 0.40704(7) 0.0762(6) Uani 0.914(2) 1 d D . P A 1
F4 F 1.5410(2) 0.63005(13) 0.51746(7) 0.0973(6) Uani 1 1 d D . . B 1
F3B F 0.7790(17) 0.6479(15) 0.4228(8) 0.098(7) Uani 0.086(2) 1 d D . P A 2
F2 F 0.0505(2) 0.15847(10) 0.40913(6) 0.0685(4) Uani 1 1 d D . . . .
F1 F 0.35009(18) 0.24359(9) 0.36748(6) 0.0537(4) Uani 0.914(2) 1 d D . P A 1
F1B F -0.007(2) 0.2568(10) 0.1628(4) 0.062(4) Uani 0.086(2) 1 d D . P A 2
C1 C 0.5246(3) 0.34695(14) 0.14986(10) 0.0427(5) Uani 1 1 d . . . . .
H1 H 0.539646 0.340344 0.106408 0.051 Uiso 1 1 calc R U . . .
C2 C 0.3714(3) 0.30448(14) 0.17631(10) 0.0411(5) Uani 1 1 d . . . . .
H2 H 0.281636 0.267333 0.150441 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3435(3) 0.31423(13) 0.23998(9) 0.0347(5) Uani 1 1 d . . . . .
C4 C 0.4741(3) 0.36869(13) 0.27786(9) 0.0339(5) Uani 1 1 d . . . . .
H4 H 0.455428 0.377222 0.320901 0.041 Uiso 1 1 calc R U . . .
C5 C 0.8625(3) 0.49574(13) 0.33920(9) 0.0344(5) Uani 1 1 d . . . . .
H5 H 0.784482 0.484367 0.372827 0.041 Uiso 1 1 calc R U . . .
C6 C 1.0389(3) 0.54400(13) 0.35015(10) 0.0365(5) Uani 1 1 d . . . . .
C7 C 1.1527(3) 0.55855(13) 0.29965(10) 0.0389(5) Uani 1 1 d . . . . .
H7 H 1.274450 0.590674 0.307191 0.047 Uiso 1 1 calc R U . . .
C8 C 1.0947(3) 0.52821(13) 0.23992(10) 0.0404(5) Uani 1 1 d . . . . .
H8 H 1.173800 0.539212 0.206499 0.048 Uiso 1 1 calc R U . . .
N9 N 0.8270(2) 0.44362(11) 0.17528(8) 0.0403(4) Uani 1 1 d . . . . .
H9 H 0.873(3) 0.4475(13) 0.1333(10) 0.048 Uiso 1 1 d . U . . .
C10 C 0.6557(3) 0.39943(13) 0.18857(9) 0.0365(5) Uani 1 1 d . . . . .
C11 C 0.6322(3) 0.41074(13) 0.25272(9) 0.0326(5) Uani 1 1 d . . . . .
C12 C 0.8000(3) 0.46412(12) 0.27937(9) 0.0321(4) Uani 1 1 d . . . . .
C13 C 0.9173(3) 0.48102(13) 0.22988(9) 0.0343(5) Uani 1 1 d . . . . .
C14 C 0.1759(3) 0.26564(13) 0.26540(10) 0.0354(5) Uani 1 1 d . . . . .
C15 C 0.1848(3) 0.23411(13) 0.32644(10) 0.0384(5) Uani 1 1 d D . . . .
H15 H 0.301293 0.244666 0.353945 0.046 Uiso 0.086(2) 1 calc R U P A 2
C16 C 0.0296(3) 0.18787(14) 0.34849(10) 0.0452(5) Uani 1 1 d D . . . .
C17 C -0.1405(3) 0.17021(15) 0.31153(12) 0.0497(6) Uani 1 1 d . . . . .
H17 H -0.246759 0.138547 0.327629 0.060 Uiso 1 1 calc R U . . .
C18 C -0.1545(3) 0.19933(14) 0.25042(12) 0.0491(6) Uani 1 1 d . . . . .
H18 H -0.271153 0.187063 0.223342 0.059 Uiso 1 1 calc R U . . .
C19 C 0.0004(3) 0.24655(14) 0.22789(11) 0.0427(5) Uani 1 1 d D . . . .
H19 H -0.012291 0.266251 0.186538 0.051 Uiso 0.914(2) 1 d R U P A 1
C20 C 1.0997(3) 0.58249(13) 0.41305(9) 0.0379(5) Uani 1 1 d . . . . .
C21 C 1.2942(3) 0.58822(16) 0.43866(11) 0.0498(6) Uani 1 1 d D . . . .
H21 H 1.395078 0.564537 0.415471 0.060 Uiso 0.086(2) 1 calc R U P A 2
C22 C 1.3469(3) 0.62687(18) 0.49634(12) 0.0562(6) Uani 1 1 d D . . . .
C23 C 1.2108(3) 0.66153(16) 0.53204(11) 0.0565(6) Uani 1 1 d . . . . .
H23 H 1.249022 0.688683 0.571796 0.068 Uiso 1 1 calc R U . . .
C24 C 1.0148(3) 0.65588(17) 0.50843(11) 0.0594(7) Uani 1 1 d . . . . .
H24 H 0.915145 0.678435 0.532549 0.071 Uiso 1 1 calc R U . . .
C25 C 0.9623(3) 0.61808(16) 0.45054(10) 0.0499(6) Uani 1 1 d D . . . .
H25 H 0.829721 0.615719 0.435866 0.060 Uiso 0.914(2) 1 d R U P A 1
N31 N 0.961(3) 0.4657(16) 0.0558(9) 0.055(3) Uani 0.5 1 d . . P C -1
C31 C 0.9195(8) 0.5766(4) 0.0455(2) 0.0629(14) Uani 0.5 1 d . . P C -1
H31A H 0.777525 0.589110 0.048452 0.076 Uiso 0.5 1 calc R U P C -1
H31B H 0.996469 0.610858 0.079692 0.076 Uiso 0.5 1 calc R U P C -1
C32 C 0.9759(8) 0.6119(3) -0.0181(2) 0.0596(13) Uani 0.5 1 d . . P C -1
H32A H 1.079607 0.655958 -0.011324 0.072 Uiso 0.5 1 d R U P C -1
H32B H 0.865480 0.639444 -0.042054 0.072 Uiso 0.5 1 d R U P C -1
C33 C 0.8259(8) 0.4330(4) 0.0001(2) 0.0656(14) Uani 0.5 1 d . . P C -1
H33A H 0.689554 0.447735 0.004921 0.079 Uiso 0.5 1 d R U P C -1
H33B H 0.839459 0.367247 0.001321 0.079 Uiso 0.5 1 d R U P C -1
C34 C 0.8833(8) 0.4677(4) -0.0643(2) 0.0572(13) Uani 0.5 1 d . . P C -1
H34A H 0.774948 0.500975 -0.085010 0.069 Uiso 0.5 1 d R U P C -1
H34B H 0.913972 0.417786 -0.090530 0.069 Uiso 0.5 1 d R U P C -1
C35 C 1.1549(8) 0.4559(5) 0.0442(3) 0.0725(16) Uani 0.5 1 d . . P C -1
H35A H 1.188653 0.389793 0.046882 0.087 Uiso 0.5 1 calc R U P C -1
H35B H 1.238681 0.487554 0.078097 0.087 Uiso 0.5 1 calc R U P C -1
C36 C 1.2109(8) 0.4923(5) -0.0192(3) 0.0689(15) Uani 0.5 1 d . . P C -1
H36A H 1.265818 0.443772 -0.041957 0.083 Uiso 0.5 1 d R U P C -1
H36B H 1.307988 0.539373 -0.012067 0.083 Uiso 0.5 1 d R U P C -1
N32 N 1.053(3) 0.5232(16) -0.0504(8) 0.048(3) Uani 0.5 1 d . . P C -1


_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
F3 C21 1.366(2) . ?
F4 C22 1.351(2) . ?
F3B C25 1.394(7) . ?
F2 C16 1.360(2) . ?
F1 C15 1.361(2) . ?
F1B C19 1.397(7) . ?
C1 C2 1.380(3) . ?
C1 C10 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C14 1.489(3) . ?
C4 C11 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.386(3) . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(3) . ?
C6 C20 1.477(3) . ?
C7 C8 1.371(3) . ?
C7 H7 0.9500 . ?
C8 C13 1.385(3) . ?
C8 H8 0.9500 . ?
N9 C13 1.376(2) . ?
N9 C10 1.384(2) . ?
N9 H9 0.98(2) . ?
C10 C11 1.407(3) . ?
C11 C12 1.448(3) . ?
C12 C13 1.409(2) . ?
C14 C15 1.379(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.374(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.357(3) . ?
C17 C18 1.368(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9257 . ?
C20 C21 1.381(3) . ?
C20 C25 1.390(3) . ?
C21 C22 1.371(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.354(3) . ?
C23 C24 1.378(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.369(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9238 . ?
N31 C35 1.37(2) . ?
N31 C33 1.50(2) . ?
N31 C31 1.65(2) . ?
C31 C32 1.539(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.58(2) . ?
C32 H32A 0.9537 . ?
C32 H32B 0.9527 . ?
C33 C34 1.553(6) . ?
C33 H33A 0.9661 . ?
C33 H33B 0.9624 . ?
C34 N32 1.42(2) . ?
C34 H34A 0.9527 . ?
C34 H34B 0.9548 . ?
C35 C36 1.538(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.28(2) . ?
C36 H36A 0.9553 . ?
C36 H36B 0.9532 . ?

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
C2 C1 C10 117.95(19) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C1 C2 C3 122.31(19) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.96(18) . . ?
C4 C3 C14 121.69(18) . . ?
C2 C3 C14 119.34(18) . . ?
C3 C4 C11 119.92(18) . . ?
C3 C4 H4 120.0 . . ?
C11 C4 H4 120.0 . . ?
C12 C5 C6 120.20(17) . . ?
C12 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 118.58(19) . . ?
C5 C6 C20 120.18(17) . . ?
C7 C6 C20 121.18(17) . . ?
C8 C7 C6 122.60(18) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C13 117.90(17) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.79(16) . . ?
C13 N9 H9 126.9(11) . . ?
C10 N9 H9 124.3(11) . . ?
C1 C10 N9 129.62(18) . . ?
C1 C10 C11 121.27(17) . . ?
N9 C10 C11 109.03(18) . . ?
C4 C11 C10 119.56(18) . . ?
C4 C11 C12 133.79(18) . . ?
C10 C11 C12 106.54(16) . . ?
C5 C12 C13 119.43(17) . . ?
C5 C12 C11 134.25(17) . . ?
C13 C12 C11 106.28(17) . . ?
N9 C13 C8 129.40(17) . . ?
N9 C13 C12 109.32(17) . . ?
C8 C13 C12 121.28(18) . . ?
C15 C14 C19 115.54(18) . . ?
C15 C14 C3 122.79(18) . . ?
C19 C14 C3 121.64(19) . . ?
F1 C15 C16 116.10(19) . . ?
F1 C15 C14 122.11(17) . . ?
C16 C15 C14 121.74(19) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 F2 119.80(19) . . ?
C17 C16 C15 122.0(2) . . ?
F2 C16 C15 118.2(2) . . ?
C16 C17 C18 118.1(2) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 122.3(2) . . ?
C18 C19 F1B 116.6(6) . . ?
C14 C19 F1B 119.7(6) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 118.6 . . ?
C21 C20 C25 114.82(19) . . ?
C21 C20 C6 123.53(18) . . ?
C25 C20 C6 121.63(18) . . ?
F3 C21 C22 117.15(19) . . ?
F3 C21 C20 120.5(2) . . ?
C22 C21 C20 122.31(19) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
F4 C22 C23 119.8(2) . . ?
F4 C22 C21 118.2(2) . . ?
C23 C22 C21 122.0(2) . . ?
C22 C23 C24 117.4(2) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C20 122.9(2) . . ?
C24 C25 F3B 113.6(8) . . ?
C20 C25 F3B 119.5(7) . . ?
C24 C25 H25 118.6 . . ?
C20 C25 H25 118.6 . . ?
C35 N31 C33 110.1(14) . . ?
C35 N31 C31 103.3(15) . . ?
C33 N31 C31 97.0(12) . . ?
C32 C31 N31 113.0(7) . . ?
C32 C31 H31A 109.0 . . ?
N31 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
N31 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 N32 103.7(7) . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32A 110.1 . . ?
C31 C32 H32B 111.3 . . ?
N32 C32 H32B 112.9 . . ?
H32A C32 H32B 109.1 . . ?
N31 C33 C34 114.3(9) . . ?
N31 C33 H33A 111.1 . . ?
C34 C33 H33A 110.6 . . ?
N31 C33 H33B 104.1 . . ?
C34 C33 H33B 108.4 . . ?
H33A C33 H33B 108.0 . . ?
N32 C34 C33 105.8(8) . . ?
N32 C34 H34A 112.6 . . ?
C33 C34 H34A 109.1 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 111.2 . . ?
H34A C34 H34B 108.5 . . ?
N31 C35 C36 116.8(9) . . ?
N31 C35 H35A 108.1 . . ?
C36 C35 H35A 108.1 . . ?
N31 C35 H35B 108.1 . . ?
C36 C35 H35B 108.1 . . ?
H35A C35 H35B 107.3 . . ?
N32 C36 C35 108.2(8) . . ?
N32 C36 H36A 110.0 . . ?
C35 C36 H36A 109.8 . . ?
N32 C36 H36B 110.9 . . ?
C35 C36 H36B 109.6 . . ?
H36A C36 H36B 108.3 . . ?
C36 N32 C34 121.9(17) . . ?
C36 N32 C32 110.9(14) . . ?
C34 N32 C32 104.9(12) . . ?

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
C10 C1 C2 C3 1.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C14 -179.43(18) . . . . ?
C2 C3 C4 C11 -1.5(3) . . . . ?
C14 C3 C4 C11 178.09(17) . . . . ?
C12 C5 C6 C7 -1.0(3) . . . . ?
C12 C5 C6 C20 176.34(18) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C20 C6 C7 C8 -176.23(19) . . . . ?
C6 C7 C8 C13 -0.4(3) . . . . ?
C2 C1 C10 N9 175.22(19) . . . . ?
C2 C1 C10 C11 -1.1(3) . . . . ?
C13 N9 C10 C1 -175.0(2) . . . . ?
C13 N9 C10 C11 1.6(2) . . . . ?
C3 C4 C11 C10 1.5(3) . . . . ?
C3 C4 C11 C12 -174.12(19) . . . . ?
C1 C10 C11 C4 -0.2(3) . . . . ?
N9 C10 C11 C4 -177.19(17) . . . . ?
C1 C10 C11 C12 176.53(18) . . . . ?
N9 C10 C11 C12 -0.5(2) . . . . ?
C6 C5 C12 C13 0.3(3) . . . . ?
C6 C5 C12 C11 177.75(19) . . . . ?
C4 C11 C12 C5 -2.5(4) . . . . ?
C10 C11 C12 C5 -178.5(2) . . . . ?
C4 C11 C12 C13 175.2(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C10 N9 C13 C8 177.35(19) . . . . ?
C10 N9 C13 C12 -2.2(2) . . . . ?
C7 C8 C13 N9 -179.81(19) . . . . ?
C7 C8 C13 C12 -0.3(3) . . . . ?
C5 C12 C13 N9 179.95(17) . . . . ?
C11 C12 C13 N9 1.8(2) . . . . ?
C5 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 C8 -177.73(17) . . . . ?
C4 C3 C14 C15 -31.3(3) . . . . ?
C2 C3 C14 C15 148.3(2) . . . . ?
C4 C3 C14 C19 150.72(19) . . . . ?
C2 C3 C14 C19 -29.7(3) . . . . ?
C19 C14 C15 F1 176.64(17) . . . . ?
C3 C14 C15 F1 -1.5(3) . . . . ?
C19 C14 C15 C16 -0.6(3) . . . . ?
C3 C14 C15 C16 -178.70(18) . . . . ?
F1 C15 C16 C17 -177.09(19) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
F1 C15 C16 F2 2.2(3) . . . . ?
C14 C15 C16 F2 179.56(18) . . . . ?
F2 C16 C17 C18 -178.76(19) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C17 C18 C19 F1B 166.9(7) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C3 C14 C19 C18 178.25(18) . . . . ?
C15 C14 C19 F1B -165.7(8) . . . . ?
C3 C14 C19 F1B 12.4(8) . . . . ?
C5 C6 C20 C21 145.6(2) . . . . ?
C7 C6 C20 C21 -37.2(3) . . . . ?
C5 C6 C20 C25 -36.0(3) . . . . ?
C7 C6 C20 C25 141.2(2) . . . . ?
C25 C20 C21 F3 178.7(2) . . . . ?
C6 C20 C21 F3 -2.8(3) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
C6 C20 C21 C22 177.9(2) . . . . ?
F3 C21 C22 F4 1.2(4) . . . . ?
C20 C21 C22 F4 -179.6(2) . . . . ?
F3 C21 C22 C23 -178.9(2) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
F4 C22 C23 C24 -179.5(2) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -1.2(4) . . . . ?
C23 C24 C25 C20 1.0(4) . . . . ?
C23 C24 C25 F3B -156.3(10) . . . . ?
C21 C20 C25 C24 -0.1(3) . . . . ?
C6 C20 C25 C24 -178.6(2) . . . . ?
C21 C20 C25 F3B 155.9(11) . . . . ?
C6 C20 C25 F3B -22.6(11) . . . . ?
C35 N31 C31 C32 52.6(14) . . . . ?
C33 N31 C31 C32 -60.0(12) . . . . ?
N31 C31 C32 N32 0.4(6) . . . . ?
C35 N31 C33 C34 -45.6(18) . . . . ?
C31 N31 C33 C34 61.4(12) . . . . ?
N31 C33 C34 N32 -0.5(7) . . . . ?
C33 N31 C35 C36 48.3(19) . . . . ?
C31 N31 C35 C36 -54.5(15) . . . . ?
N31 C35 C36 N32 -2.2(9) . . . . ?
C35 C36 N32 C34 -56.4(16) . . . . ?
C35 C36 N32 C32 67.6(14) . . . . ?
C33 C34 N32 C36 56.6(15) . . . . ?
C33 C34 N32 C32 -70.1(12) . . . . ?
C31 C32 N32 C36 -64.3(13) . . . . ?
C31 C32 N32 C34 69.0(11) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.98(2) 1.84(3) 2.817(19) 174.9(19) . yes
N9 H9 N32 0.98(2) 1.94(3) 2.909(16) 170.1(18) 3_765 yes
C24 H24 F4 0.95 2.63 3.265(3) 125.0 1_455 yes

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_ANH-BRM-2-300K
_database_code_depnum_ccdc_archive 'CCDC 2022178'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

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'

_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                   6.6763(5)
_cell_length_b                   15.0587(11)
_cell_length_c                   21.4299(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.940(2)
_cell_angle_gamma                90
_cell_volume                     2146.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    6890
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      28.74

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.413
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.298
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6622
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  'Bruker D8 Venture κ-geometry diffractometer'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            27821
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.339
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4923
_reflns_number_gt                2032
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0379P)²+0.3103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4923
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1814
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
F1 F -0.0199(2) 0.23893(10) 0.15508(7) 0.0777(5) Uani 1 1 d . . . . .
F2 F 0.0358(2) 0.15761(11) 0.40099(8) 0.0911(6) Uani 1 1 d . . . . .
F3 F 1.3919(2) 0.53673(12) 0.42066(7) 0.0921(6) Uani 1 1 d . . . . .
F4 F 0.7748(3) 0.68674(13) 0.52834(8) 0.1071(6) Uani 1 1 d . . . . .
C1 C 0.5466(4) 0.33198(17) 0.14440(11) 0.0594(7) Uani 1 1 d . . . . .
H1 H 0.572690 0.326110 0.102666 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3858(4) 0.28993(17) 0.16676(11) 0.0570(7) Uani 1 1 d . . . . .
H2 H 0.304542 0.254314 0.139651 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3386(3) 0.29854(15) 0.22917(11) 0.0464(6) Uani 1 1 d . . . . .
C4 C 0.4605(3) 0.35209(15) 0.26889(11) 0.0469(6) Uani 1 1 d . . . . .
H4 H 0.429804 0.360247 0.310020 0.056 Uiso 1 1 calc R U . . .
C5 C 0.8317(3) 0.48077(15) 0.33750(11) 0.0472(6) Uani 1 1 d . . . . .
H5 H 0.744196 0.470388 0.368196 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0056(3) 0.52963(15) 0.35168(11) 0.0473(6) Uani 1 1 d . . . . .
C7 C 1.1365(4) 0.54389(16) 0.30493(12) 0.0542(7) Uani 1 1 d . . . . .
H7 H 1.254576 0.575597 0.314729 0.065 Uiso 1 1 calc R U . . .
C8 C 1.0955(4) 0.51246(16) 0.24521(12) 0.0546(7) Uani 1 1 d . . . . .
H8 H 1.183449 0.522827 0.214633 0.066 Uiso 1 1 calc R U . . .
N9 N 0.8453(3) 0.42757(14) 0.17620(10) 0.0575(6) Uani 1 1 d . . . . .
H9 H 0.902(3) 0.4313(15) 0.1402(11) 0.069 Uiso 1 1 d . U . . .
C10 C 0.6699(4) 0.38356(16) 0.18530(11) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.6278(3) 0.39374(15) 0.24808(10) 0.0431(6) Uani 1 1 d . . . . .
C12 C 0.7882(3) 0.44736(14) 0.27758(10) 0.0429(6) Uani 1 1 d . . . . .
C13 C 0.9201(4) 0.46497(16) 0.23156(11) 0.0487(6) Uani 1 1 d . . . . .
C14 C 0.1697(3) 0.24940(15) 0.25332(12) 0.0479(6) Uani 1 1 d . . . . .
C15 C -0.0023(4) 0.22182(17) 0.21809(13) 0.0573(7) Uani 1 1 d . . . . .
C16 C -0.1587(4) 0.17757(18) 0.24088(16) 0.0695(8) Uani 1 1 d . . . . .
H16 H -0.270858 0.161980 0.214403 0.083 Uiso 1 1 calc R U . . .
C17 C -0.1485(4) 0.15641(18) 0.30310(16) 0.0727(9) Uani 1 1 d . . . . .
H17 H -0.252966 0.126533 0.320096 0.087 Uiso 1 1 calc R U . . .
C18 C 0.0201(4) 0.18074(17) 0.33921(14) 0.0631(8) Uani 1 1 d . . . . .
C19 C 0.1761(4) 0.22594(16) 0.31650(12) 0.0564(7) Uani 1 1 d . . . . .
H19 H 0.287542 0.241196 0.343411 0.068 Uiso 1 1 calc R U . . .
C20 C 1.0456(4) 0.57109(16) 0.41402(11) 0.0505(6) Uani 1 1 d . . . . .
C21 C 0.8926(4) 0.61007(18) 0.44408(12) 0.0589(7) Uani 1 1 d . . . . .
H21 H 0.761743 0.608767 0.425310 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9311(4) 0.65019(18) 0.50062(14) 0.0670(8) Uani 1 1 d . . . . .
C23 C 1.1197(5) 0.65638(19) 0.53056(13) 0.0734(8) Uani 1 1 d . . . . .
H23 H 1.142126 0.685576 0.568764 0.088 Uiso 1 1 calc R U . . .
C24 C 1.2742(5) 0.6181(2) 0.50235(14) 0.0745(8) Uani 1 1 d . . . . .
H24 H 1.404749 0.620408 0.521322 0.089 Uiso 1 1 calc R U . . .
C25 C 1.2348(4) 0.57666(18) 0.44612(13) 0.0613(7) Uani 1 1 d . . . . .
N31 N 0.948(3) 0.4549(10) 0.0508(10) 0.050(3) Uani 0.5 1 d . . P A -1
C31 C 0.8356(18) 0.4336(8) 0.0033(4) 0.109(3) Uani 0.5 1 d . . P A -1
H31A H 0.699631 0.451331 0.010285 0.131 Uiso 0.5 1 calc R U P A -1
H31B H 0.836224 0.369385 -0.000028 0.131 Uiso 0.5 1 calc R U P A -1
C32 C 0.885(2) 0.4726(8) -0.0613(3) 0.109(3) Uani 0.5 1 d . . P A -1
H32A H 0.918050 0.424448 -0.088740 0.130 Uiso 0.5 1 calc R U P A -1
H32B H 0.768095 0.503066 -0.080731 0.130 Uiso 0.5 1 calc R U P A -1
C33 C 0.9313(16) 0.5715(6) 0.0510(3) 0.094(2) Uani 0.5 1 d . . P A -1
H33A H 0.798934 0.588992 0.061953 0.113 Uiso 0.5 1 calc R U P A -1
H33B H 1.029898 0.595331 0.082469 0.113 Uiso 0.5 1 calc R U P A -1
C34 C 0.9680(17) 0.6105(5) -0.0136(3) 0.092(2) Uani 0.5 1 d . . P A -1
H34A H 1.082225 0.650538 -0.010533 0.111 Uiso 0.5 1 calc R U P A -1
H34B H 0.850372 0.642027 -0.031760 0.111 Uiso 0.5 1 calc R U P A -1
C35 C 1.1740(13) 0.4587(8) 0.0388(4) 0.102(3) Uani 0.5 1 d . . P A -1
H35A H 1.245439 0.492940 0.072008 0.123 Uiso 0.5 1 calc R U P A -1
H35B H 1.228184 0.398888 0.040819 0.123 Uiso 0.5 1 calc R U P A -1
C36 C 1.2136(15) 0.4995(8) -0.0240(4) 0.103(3) Uani 0.5 1 d . . P A -1
H36A H 1.293054 0.553226 -0.017852 0.123 Uiso 0.5 1 calc R U P A -1
H36B H 1.285214 0.458028 -0.048590 0.123 Uiso 0.5 1 calc R U P A -1
N32 N 1.014(3) 0.5198(11) -0.0557(10) 0.064(4) Uani 0.5 1 d . . P A -1


_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
F1 C15 1.370(3) . ?
F2 C18 1.364(3) . ?
F3 C25 1.363(3) . ?
F4 C22 1.361(3) . ?
C1 C2 1.368(3) . ?
C1 C10 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 C14 1.479(3) . ?
C4 C11 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(3) . ?
C5 C12 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.401(3) . ?
C6 C20 1.478(3) . ?
C7 C8 1.370(3) . ?
C7 H7 0.9300 . ?
C8 C13 1.382(3) . ?
C8 H8 0.9300 . ?
N9 C13 1.368(3) . ?
N9 C10 1.374(3) . ?
N9 H9 0.89(2) . ?
C10 C11 1.406(3) . ?
C11 C12 1.443(3) . ?
C12 C13 1.403(3) . ?
C14 C15 1.383(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.364(3) . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 C25 1.387(3) . ?
C21 C22 1.359(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.366(3) . ?
C23 C24 1.367(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(3) . ?
C24 H24 0.9300 . ?
N31 C31 1.254(19) . ?
N31 C35 1.55(2) . ?
N31 C33 1.760(16) . ?
C31 C32 1.565(10) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.114(16) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.542(8) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N32 1.68(2) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.523(10) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.47(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?

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
C2 C1 C10 118.6(2) . . ?
C2 C1 H1 120.7 . . ?
C10 C1 H1 120.7 . . ?
C1 C2 C3 122.5(2) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 C14 120.1(2) . . ?
C2 C3 C14 121.8(2) . . ?
C3 C4 C11 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C11 C4 H4 119.6 . . ?
C6 C5 C12 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C12 C5 H5 120.0 . . ?
C5 C6 C7 119.1(2) . . ?
C5 C6 C20 120.3(2) . . ?
C7 C6 C20 120.4(2) . . ?
C8 C7 C6 121.9(2) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C13 118.3(2) . . ?
C7 C8 H8 120.8 . . ?
C13 C8 H8 120.8 . . ?
C13 N9 C10 109.1(2) . . ?
C13 N9 H9 125.1(16) . . ?
C10 N9 H9 125.8(16) . . ?
N9 C10 C1 130.3(2) . . ?
N9 C10 C11 109.0(2) . . ?
C1 C10 C11 120.6(2) . . ?
C4 C11 C10 119.4(2) . . ?
C4 C11 C12 134.4(2) . . ?
C10 C11 C12 106.2(2) . . ?
C5 C12 C13 119.2(2) . . ?
C5 C12 C11 134.2(2) . . ?
C13 C12 C11 106.6(2) . . ?
N9 C13 C8 129.5(2) . . ?
N9 C13 C12 109.1(2) . . ?
C8 C13 C12 121.4(2) . . ?
C15 C14 C19 114.1(2) . . ?
C15 C14 C3 125.6(2) . . ?
C19 C14 C3 120.3(2) . . ?
C16 C15 F1 116.2(3) . . ?
C16 C15 C14 125.2(3) . . ?
F1 C15 C14 118.6(2) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 117.5(3) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
C17 C18 F2 118.3(3) . . ?
C17 C18 C19 123.3(3) . . ?
F2 C18 C19 118.4(3) . . ?
C18 C19 C14 120.7(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
C21 C20 C25 114.9(2) . . ?
C21 C20 C6 121.1(2) . . ?
C25 C20 C6 124.0(2) . . ?
C22 C21 C20 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 F4 118.4(3) . . ?
C21 C22 C23 123.0(3) . . ?
F4 C22 C23 118.5(3) . . ?
C22 C23 C24 117.6(3) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C24 C25 F3 117.4(3) . . ?
C24 C25 C20 124.4(3) . . ?
F3 C25 C20 118.3(3) . . ?
C31 N31 C35 113.5(16) . . ?
C31 N31 C33 102.9(13) . . ?
C35 N31 C33 91.5(10) . . ?
N31 C31 C32 117.6(10) . . ?
N31 C31 H31A 107.9 . . ?
C32 C31 H31A 107.9 . . ?
N31 C31 H31B 107.9 . . ?
C32 C31 H31B 107.9 . . ?
H31A C31 H31B 107.2 . . ?
N32 C32 C31 111.4(11) . . ?
N32 C32 H32A 109.4 . . ?
C31 C32 H32A 109.4 . . ?
N32 C32 H32B 109.4 . . ?
C31 C32 H32B 109.4 . . ?
H32A C32 H32B 108.0 . . ?
C34 C33 N31 111.3(9) . . ?
C34 C33 H33A 109.4 . . ?
N31 C33 H33A 109.4 . . ?
C34 C33 H33B 109.4 . . ?
N31 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C33 C34 N32 102.9(8) . . ?
C33 C34 H34A 111.2 . . ?
N32 C34 H34A 111.2 . . ?
C33 C34 H34B 111.2 . . ?
N32 C34 H34B 111.2 . . ?
H34A C34 H34B 109.1 . . ?
C36 C35 N31 113.9(10) . . ?
C36 C35 H35A 108.8 . . ?
N31 C35 H35A 108.8 . . ?
C36 C35 H35B 108.8 . . ?
N31 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
N32 C36 C35 105.8(10) . . ?
N32 C36 H36A 110.6 . . ?
C35 C36 H36A 110.6 . . ?
N32 C36 H36B 110.6 . . ?
C35 C36 H36B 110.6 . . ?
H36A C36 H36B 108.7 . . ?
C32 N32 C36 125.1(18) . . ?
C32 N32 C34 113.7(19) . . ?
C36 N32 C34 97.0(11) . . ?

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
C10 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C2 C3 C14 -177.2(2) . . . . ?
C2 C3 C4 C11 -2.0(3) . . . . ?
C14 C3 C4 C11 175.5(2) . . . . ?
C12 C5 C6 C7 -0.6(3) . . . . ?
C12 C5 C6 C20 175.4(2) . . . . ?
C5 C6 C7 C8 1.4(4) . . . . ?
C20 C6 C7 C8 -174.6(2) . . . . ?
C6 C7 C8 C13 -0.4(4) . . . . ?
C13 N9 C10 C1 -176.1(3) . . . . ?
C13 N9 C10 C11 0.9(3) . . . . ?
C2 C1 C10 N9 175.4(2) . . . . ?
C2 C1 C10 C11 -1.3(4) . . . . ?
C3 C4 C11 C10 2.1(3) . . . . ?
C3 C4 C11 C12 -175.2(2) . . . . ?
N9 C10 C11 C4 -177.7(2) . . . . ?
C1 C10 C11 C4 -0.4(4) . . . . ?
N9 C10 C11 C12 0.2(3) . . . . ?
C1 C10 C11 C12 177.6(2) . . . . ?
C6 C5 C12 C13 -1.1(3) . . . . ?
C6 C5 C12 C11 178.3(2) . . . . ?
C4 C11 C12 C5 -3.2(5) . . . . ?
C10 C11 C12 C5 179.3(2) . . . . ?
C4 C11 C12 C13 176.3(3) . . . . ?
C10 C11 C12 C13 -1.2(2) . . . . ?
C10 N9 C13 C8 177.5(2) . . . . ?
C10 N9 C13 C12 -1.7(3) . . . . ?
C7 C8 C13 N9 179.6(2) . . . . ?
C7 C8 C13 C12 -1.3(4) . . . . ?
C5 C12 C13 N9 -178.6(2) . . . . ?
C11 C12 C13 N9 1.8(3) . . . . ?
C5 C12 C13 C8 2.1(3) . . . . ?
C11 C12 C13 C8 -177.5(2) . . . . ?
C4 C3 C14 C15 154.5(2) . . . . ?
C2 C3 C14 C15 -28.1(4) . . . . ?
C4 C3 C14 C19 -26.3(3) . . . . ?
C2 C3 C14 C19 151.1(2) . . . . ?
C19 C14 C15 C16 1.7(4) . . . . ?
C3 C14 C15 C16 -179.1(2) . . . . ?
C19 C14 C15 F1 -177.8(2) . . . . ?
C3 C14 C15 F1 1.5(4) . . . . ?
F1 C15 C16 C17 178.4(2) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 F2 -177.9(2) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 C14 -0.4(4) . . . . ?
F2 C18 C19 C14 178.5(2) . . . . ?
C15 C14 C19 C18 -0.9(3) . . . . ?
C3 C14 C19 C18 179.8(2) . . . . ?
C5 C6 C20 C21 -39.3(3) . . . . ?
C7 C6 C20 C21 136.6(2) . . . . ?
C5 C6 C20 C25 142.5(3) . . . . ?
C7 C6 C20 C25 -41.5(4) . . . . ?
C25 C20 C21 C22 0.1(4) . . . . ?
C6 C20 C21 C22 -178.2(2) . . . . ?
C20 C21 C22 F4 -179.4(2) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C21 C22 C23 C24 -1.7(4) . . . . ?
F4 C22 C23 C24 179.1(2) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C24 C25 F3 -177.8(2) . . . . ?
C23 C24 C25 C20 0.9(4) . . . . ?
C21 C20 C25 C24 -1.2(4) . . . . ?
C6 C20 C25 C24 177.0(2) . . . . ?
C21 C20 C25 F3 177.4(2) . . . . ?
C6 C20 C25 F3 -4.3(4) . . . . ?
C35 N31 C31 C32 -39.4(18) . . . . ?
C33 N31 C31 C32 58.1(16) . . . . ?
N31 C31 C32 N32 -4.0(19) . . . . ?
C31 N31 C33 C34 -50.2(16) . . . . ?
C35 N31 C33 C34 64.3(12) . . . . ?
N31 C33 C34 N32 -1.3(11) . . . . ?
C31 N31 C35 C36 40.4(17) . . . . ?
C33 N31 C35 C36 -64.4(13) . . . . ?
N31 C35 C36 N32 -2.3(15) . . . . ?
C31 C32 N32 C36 54(3) . . . . ?
C31 C32 N32 C34 -64(2) . . . . ?
C35 C36 N32 C32 -50(3) . . . . ?
C35 C36 N32 C34 75.9(11) . . . . ?
C33 C34 N32 C32 62.2(19) . . . . ?
C33 C34 N32 C36 -71.1(11) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.89(2) 2.00(3) 2.86(2) 163(2) . yes
N9 H9 N32 0.89(2) 2.08(3) 2.93(2) 161(2) 3_765 yes
C24 H24 F4 0.93 2.66 3.496(3) 150.5 1_655 yes

_refine_diff_density_max         0.187
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-2-100K
_database_code_depnum_ccdc_archive 'CCDC 2022174'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H37 F8 N4'
_chemical_formula_weight         893.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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                   6.6570(3)
_cell_length_b                   14.8520(6)
_cell_length_c                   21.2537(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.7210(10)
_cell_angle_gamma                90
_cell_volume                     2090.88(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9418
_cell_measurement_theta_min      2.9812
_cell_measurement_theta_max      32.9545

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             922
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            73120
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0686
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.975
_diffrn_reflns_theta_max         32.966
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7264
_reflns_number_gt                6595
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0720P)²+0.4843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7264
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1231
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
F1 F -0.02982(8) 0.23566(4) 0.15420(3) 0.02471(13) Uani 1 1 d . . . . .
F2 F 0.04044(10) 0.15279(4) 0.40387(3) 0.02865(14) Uani 1 1 d . . . . .
F3 F 1.40512(8) 0.53934(4) 0.42479(3) 0.02702(13) Uani 1 1 d . . . . .
F4 F 0.77975(9) 0.68865(5) 0.53287(3) 0.03119(15) Uani 1 1 d . . . . .
C1 C 0.54392(14) 0.32946(6) 0.14329(4) 0.02025(16) Uani 1 1 d . . . . .
H1 H 0.570376 0.323120 0.100412 0.024 Uiso 1 1 calc R U . . .
C2 C 0.37970(13) 0.28705(6) 0.16578(4) 0.01928(15) Uani 1 1 d . . . . .
H2 H 0.294167 0.250809 0.137693 0.023 Uiso 1 1 calc R U . . .
C3 C 0.33558(12) 0.29611(5) 0.22931(4) 0.01643(14) Uani 1 1 d . . . . .
C4 C 0.45976(12) 0.35081(5) 0.27028(4) 0.01568(14) Uani 1 1 d . . . . .
H4 H 0.429735 0.359387 0.312636 0.019 Uiso 1 1 calc R U . . .
C5 C 0.83518(12) 0.48084(5) 0.33992(4) 0.01539(14) Uani 1 1 d . . . . .
H5 H 0.744838 0.471272 0.371166 0.018 Uiso 1 1 calc R U . . .
C6 C 1.01344(12) 0.52963(5) 0.35458(4) 0.01580(14) Uani 1 1 d . . . . .
C7 C 1.14624(12) 0.54318(5) 0.30750(4) 0.01760(15) Uani 1 1 d . . . . .
H7 H 1.268649 0.575060 0.318132 0.021 Uiso 1 1 calc R U . . .
C8 C 1.10335(12) 0.51139(6) 0.24635(4) 0.01828(15) Uani 1 1 d . . . . .
H8 H 1.192660 0.522067 0.214970 0.022 Uiso 1 1 calc R U . . .
N9 N 0.84691(11) 0.42514(5) 0.17605(3) 0.01886(14) Uani 1 1 d . . . . .
H9 H 0.899(2) 0.4312(9) 0.1382(6) 0.023 Uiso 1 1 d . U . . .
C10 C 0.66906(12) 0.38161(5) 0.18528(4) 0.01726(15) Uani 1 1 d . . . . .
C11 C 0.62770(12) 0.39273(5) 0.24886(4) 0.01537(14) Uani 1 1 d . . . . .
C12 C 0.79113(12) 0.44635(5) 0.27908(4) 0.01499(14) Uani 1 1 d . . . . .
C13 C 0.92433(12) 0.46312(5) 0.23239(4) 0.01639(14) Uani 1 1 d . . . . .
C14 C 0.16689(12) 0.24657(5) 0.25408(4) 0.01675(14) Uani 1 1 d . . . . .
C15 C -0.00911(13) 0.21911(6) 0.21737(4) 0.01930(15) Uani 1 1 d . . . . .
C16 C -0.16774(13) 0.17475(6) 0.24148(5) 0.02339(17) Uani 1 1 d . . . . .
H16 H -0.285355 0.159497 0.214553 0.028 Uiso 1 1 calc R U . . .
C17 C -0.15364(14) 0.15280(6) 0.30510(5) 0.02427(18) Uani 1 1 d . . . . .
H17 H -0.260152 0.122370 0.322843 0.029 Uiso 1 1 calc R U . . .
C18 C 0.02081(14) 0.17680(6) 0.34172(4) 0.02107(16) Uani 1 1 d . . . . .
C19 C 0.17794(12) 0.22267(6) 0.31836(4) 0.01862(15) Uani 1 1 d . . . . .
H19 H 0.294107 0.238151 0.345869 0.022 Uiso 1 1 calc R U . . .
C20 C 1.05447(12) 0.57229(5) 0.41753(4) 0.01602(14) Uani 1 1 d . . . . .
C21 C 0.89698(12) 0.61087(6) 0.44746(4) 0.01862(15) Uani 1 1 d . . . . .
H21 H 0.762357 0.608012 0.427966 0.022 Uiso 1 1 calc R U . . .
C22 C 0.93731(13) 0.65299(6) 0.50520(4) 0.02078(16) Uani 1 1 d . . . . .
C23 C 1.12985(14) 0.66126(6) 0.53582(4) 0.02209(16) Uani 1 1 d . . . . .
H23 H 1.153213 0.692090 0.575032 0.027 Uiso 1 1 calc R U . . .
C24 C 1.28782(13) 0.62282(6) 0.50710(4) 0.02229(17) Uani 1 1 d . . . . .
H24 H 1.422317 0.626630 0.526592 0.027 Uiso 1 1 calc R U . . .
C25 C 1.24711(12) 0.57901(6) 0.44993(4) 0.01880(15) Uani 1 1 d . . . . .
N31 N 0.9752(19) 0.4599(8) 0.0503(5) 0.0230(10) Uani 0.5 1 d . . P A -1
C31 C 0.8331(3) 0.43472(15) 0.00116(9) 0.0296(4) Uani 0.5 1 d . . P A -1
H31A H 0.697734 0.454434 0.011104 0.035 Uiso 0.5 1 calc R U P A -1
H31B H 0.831254 0.368240 -0.002242 0.035 Uiso 0.5 1 calc R U P A -1
C32 C 0.8763(3) 0.47549(14) -0.06345(8) 0.0266(4) Uani 0.5 1 d . . P A -1
H32A H 0.902523 0.426349 -0.093024 0.032 Uiso 0.5 1 calc R U P A -1
H32B H 0.756459 0.509358 -0.081829 0.032 Uiso 0.5 1 calc R U P A -1
C33 C 0.9365(3) 0.57199(14) 0.05361(9) 0.0272(4) Uani 0.5 1 d . . P A -1
H33A H 0.798007 0.584095 0.064603 0.033 Uiso 0.5 1 calc R U P A -1
H33B H 1.033149 0.598996 0.086743 0.033 Uiso 0.5 1 calc R U P A -1
C34 C 0.9657(3) 0.61464(13) -0.01148(9) 0.0275(4) Uani 0.5 1 d . . P A -1
H34A H 1.070305 0.662211 -0.006789 0.033 Uiso 0.5 1 calc R U P A -1
H34B H 0.837806 0.641559 -0.030547 0.033 Uiso 0.5 1 calc R U P A -1
C35 C 1.1801(3) 0.45773(15) 0.03862(9) 0.0281(4) Uani 0.5 1 d . . P A -1
H35A H 1.224552 0.394229 0.037086 0.034 Uiso 0.5 1 calc R U P A -1
H35B H 1.262100 0.487386 0.074153 0.034 Uiso 0.5 1 calc R U P A -1
C36 C 1.2202(3) 0.50492(16) -0.02400(9) 0.0286(4) Uani 0.5 1 d . . P A -1
H36 H 1.349483 0.514495 -0.038108 0.034 Uiso 0.5 1 calc R U P A -1
N32 N 1.037(2) 0.5311(9) -0.0563(5) 0.0303(19) Uani 0.5 1 d . . P A -1


_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
F1 C15 1.3583(10) . ?
F2 C18 1.3618(11) . ?
F3 C25 1.3606(10) . ?
F4 C22 1.3598(10) . ?
C1 C2 1.3872(12) . ?
C1 C10 1.3935(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.4167(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3993(11) . ?
C3 C14 1.4823(11) . ?
C4 C11 1.3951(11) . ?
C4 H4 0.9500 . ?
C5 C12 1.3946(11) . ?
C5 C6 1.3988(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.4141(11) . ?
C6 C20 1.4809(11) . ?
C7 C8 1.3855(12) . ?
C7 H7 0.9500 . ?
C8 C13 1.3971(11) . ?
C8 H8 0.9500 . ?
N9 C13 1.3764(10) . ?
N9 C10 1.3800(11) . ?
N9 H9 0.911(13) . ?
C10 C11 1.4154(11) . ?
C11 C12 1.4460(11) . ?
C12 C13 1.4172(11) . ?
C14 C15 1.4020(11) . ?
C14 C19 1.4064(12) . ?
C15 C16 1.3854(12) . ?
C16 C17 1.3851(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3789(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.3815(11) . ?
C19 H19 0.9500 . ?
C20 C25 1.3974(11) . ?
C20 C21 1.4018(11) . ?
C21 C22 1.3799(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.3839(12) . ?
C23 C24 1.3901(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.3811(12) . ?
C24 H24 0.9500 . ?
N31 C31 1.389(12) . ?
N31 C35 1.411(13) . ?
N31 C33 1.687(12) . ?
C31 C32 1.554(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.350(13) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.551(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.664(14) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.551(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.392(12) . ?
C36 H36 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
C2 C1 C10 118.24(7) . . ?
C2 C1 H1 120.9 . . ?
C10 C1 H1 120.9 . . ?
C1 C2 C3 122.05(7) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 118.85(7) . . ?
C4 C3 C14 119.25(7) . . ?
C2 C3 C14 121.86(7) . . ?
C11 C4 C3 119.93(7) . . ?
C11 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C12 C5 C6 119.48(7) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.50(7) . . ?
C5 C6 C20 119.93(7) . . ?
C7 C6 C20 120.42(7) . . ?
C8 C7 C6 122.03(7) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.76(7) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.69(7) . . ?
C13 N9 H9 125.9(9) . . ?
C10 N9 H9 125.2(9) . . ?
N9 C10 C1 129.49(7) . . ?
N9 C10 C11 109.41(7) . . ?
C1 C10 C11 121.03(8) . . ?
C4 C11 C10 119.86(7) . . ?
C4 C11 C12 133.84(7) . . ?
C10 C11 C12 106.20(7) . . ?
C5 C12 C13 119.75(7) . . ?
C5 C12 C11 133.91(7) . . ?
C13 C12 C11 106.34(7) . . ?
N9 C13 C8 129.24(7) . . ?
N9 C13 C12 109.33(7) . . ?
C8 C13 C12 121.43(7) . . ?
C15 C14 C19 115.28(8) . . ?
C15 C14 C3 124.57(8) . . ?
C19 C14 C3 120.14(7) . . ?
F1 C15 C16 116.46(7) . . ?
F1 C15 C14 119.62(8) . . ?
C16 C15 C14 123.92(8) . . ?
C17 C16 C15 119.54(8) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 117.49(8) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
F2 C18 C17 118.28(8) . . ?
F2 C18 C19 118.35(8) . . ?
C17 C18 C19 123.36(9) . . ?
C18 C19 C14 120.36(8) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C25 C20 C21 116.00(7) . . ?
C25 C20 C6 123.60(7) . . ?
C21 C20 C6 120.39(7) . . ?
C22 C21 C20 120.06(7) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
F4 C22 C21 118.10(7) . . ?
F4 C22 C23 118.70(8) . . ?
C21 C22 C23 123.19(8) . . ?
C22 C23 C24 117.57(8) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 119.28(8) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
F3 C25 C24 117.26(7) . . ?
F3 C25 C20 118.87(7) . . ?
C24 C25 C20 123.86(8) . . ?
C31 N31 C35 117.4(9) . . ?
C31 N31 C33 101.7(6) . . ?
C35 N31 C33 100.6(7) . . ?
N31 C31 C32 112.8(4) . . ?
N31 C31 H31A 109.0 . . ?
C32 C31 H31A 109.0 . . ?
N31 C31 H31B 109.0 . . ?
C32 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
N32 C32 C31 110.8(5) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 N31 109.4(4) . . ?
C34 C33 H33A 109.8 . . ?
N31 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
N31 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 N32 106.0(4) . . ?
C33 C34 H34A 110.5 . . ?
N32 C34 H34A 110.5 . . ?
C33 C34 H34B 110.5 . . ?
N32 C34 H34B 110.5 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 113.1(4) . . ?
N31 C35 H35A 109.0 . . ?
C36 C35 H35A 109.0 . . ?
N31 C35 H35B 109.0 . . ?
C36 C35 H35B 109.0 . . ?
H35A C35 H35B 107.8 . . ?
N32 C36 C35 109.5(5) . . ?
N32 C36 H36 125.3 . . ?
C35 C36 H36 125.3 . . ?
C32 N32 C36 122.0(9) . . ?
C32 N32 C34 104.5(8) . . ?
C36 N32 C34 102.2(8) . . ?

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
C10 C1 C2 C3 0.66(13) . . . . ?
C1 C2 C3 C4 1.12(12) . . . . ?
C1 C2 C3 C14 -176.46(8) . . . . ?
C2 C3 C4 C11 -2.23(11) . . . . ?
C14 C3 C4 C11 175.41(7) . . . . ?
C12 C5 C6 C7 -0.04(11) . . . . ?
C12 C5 C6 C20 175.47(7) . . . . ?
C5 C6 C7 C8 1.60(12) . . . . ?
C20 C6 C7 C8 -173.88(7) . . . . ?
C6 C7 C8 C13 -1.31(12) . . . . ?
C13 N9 C10 C1 -175.85(9) . . . . ?
C13 N9 C10 C11 1.00(9) . . . . ?
C2 C1 C10 N9 175.20(8) . . . . ?
C2 C1 C10 C11 -1.33(12) . . . . ?
C3 C4 C11 C10 1.59(11) . . . . ?
C3 C4 C11 C12 -174.49(8) . . . . ?
N9 C10 C11 C4 -176.93(7) . . . . ?
C1 C10 C11 C4 0.23(12) . . . . ?
N9 C10 C11 C12 0.12(9) . . . . ?
C1 C10 C11 C12 177.28(8) . . . . ?
C6 C5 C12 C13 -1.71(11) . . . . ?
C6 C5 C12 C11 178.41(8) . . . . ?
C4 C11 C12 C5 -4.80(16) . . . . ?
C10 C11 C12 C5 178.75(8) . . . . ?
C4 C11 C12 C13 175.31(8) . . . . ?
C10 C11 C12 C13 -1.15(8) . . . . ?
C10 N9 C13 C8 178.10(8) . . . . ?
C10 N9 C13 C12 -1.75(9) . . . . ?
C7 C8 C13 N9 179.67(8) . . . . ?
C7 C8 C13 C12 -0.49(12) . . . . ?
C5 C12 C13 N9 -178.12(7) . . . . ?
C11 C12 C13 N9 1.79(9) . . . . ?
C5 C12 C13 C8 2.01(12) . . . . ?
C11 C12 C13 C8 -178.08(7) . . . . ?
C4 C3 C14 C15 154.24(8) . . . . ?
C2 C3 C14 C15 -28.20(12) . . . . ?
C4 C3 C14 C19 -26.76(11) . . . . ?
C2 C3 C14 C19 150.81(8) . . . . ?
C19 C14 C15 F1 -177.17(7) . . . . ?
C3 C14 C15 F1 1.88(12) . . . . ?
C19 C14 C15 C16 2.58(12) . . . . ?
C3 C14 C15 C16 -178.37(8) . . . . ?
F1 C15 C16 C17 177.68(8) . . . . ?
C14 C15 C16 C17 -2.08(13) . . . . ?
C15 C16 C17 C18 0.04(13) . . . . ?
C16 C17 C18 F2 -177.59(8) . . . . ?
C16 C17 C18 C19 1.35(14) . . . . ?
F2 C18 C19 C14 178.17(8) . . . . ?
C17 C18 C19 C14 -0.77(13) . . . . ?
C15 C14 C19 C18 -1.15(12) . . . . ?
C3 C14 C19 C18 179.76(7) . . . . ?
C5 C6 C20 C25 144.43(8) . . . . ?
C7 C6 C20 C25 -40.11(11) . . . . ?
C5 C6 C20 C21 -37.16(11) . . . . ?
C7 C6 C20 C21 138.30(8) . . . . ?
C25 C20 C21 C22 0.56(12) . . . . ?
C6 C20 C21 C22 -177.97(8) . . . . ?
C20 C21 C22 F4 -179.31(8) . . . . ?
C20 C21 C22 C23 1.28(14) . . . . ?
F4 C22 C23 C24 178.86(8) . . . . ?
C21 C22 C23 C24 -1.73(14) . . . . ?
C22 C23 C24 C25 0.33(13) . . . . ?
C23 C24 C25 F3 -177.46(8) . . . . ?
C23 C24 C25 C20 1.56(13) . . . . ?
C21 C20 C25 F3 177.03(7) . . . . ?
C6 C20 C25 F3 -4.50(12) . . . . ?
C21 C20 C25 C24 -1.98(12) . . . . ?
C6 C20 C25 C24 176.49(8) . . . . ?
C35 N31 C31 C32 -43.7(9) . . . . ?
C33 N31 C31 C32 64.9(7) . . . . ?
N31 C31 C32 N32 -3.7(3) . . . . ?
C31 N31 C33 C34 -57.9(7) . . . . ?
C35 N31 C33 C34 63.2(6) . . . . ?
N31 C33 C34 N32 -3.4(2) . . . . ?
C31 N31 C35 C36 48.5(9) . . . . ?
C33 N31 C35 C36 -60.7(7) . . . . ?
N31 C35 C36 N32 -5.3(3) . . . . ?
C31 C32 N32 C36 50.6(12) . . . . ?
C31 C32 N32 C34 -64.2(6) . . . . ?
C35 C36 N32 C32 -45.6(12) . . . . ?
C35 C36 N32 C34 70.4(6) . . . . ?
C33 C34 N32 C32 65.4(6) . . . . ?
C33 C34 N32 C36 -62.7(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
_geom_hbond_publ_flag
N9 H9 N31 0.911(13) 2.029(17) 2.932(11) 170.2(13) . yes
N9 H9 N32 0.911(13) 1.915(17) 2.807(11) 165.7(13) 3_765 yes
C24 H24 F4 0.95 2.54 3.4092(10) 151.7 1_655 yes

_refine_diff_density_max         0.558
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.121


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3II-100K
_database_code_depnum_ccdc_archive 'CCDC 2022182'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

_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+1/2'

_cell_length_a                   19.0865(8)
_cell_length_b                   6.7670(3)
_cell_length_c                   17.3518(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.3540(10)
_cell_angle_gamma                90
_cell_volume                     2114.48(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9810
_cell_measurement_theta_min      2.5515
_cell_measurement_theta_max      31.3837

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            71153
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         31.393
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             12908
_reflns_number_gt                12540
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.995
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.993

_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0641P)²+0.3386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 6027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.50(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         12908
_refine_ls_number_parameters     601
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
F1 F 0.57420(6) -0.13629(17) 0.59368(7) 0.0214(2) Uani 1 1 d . . . . .
F2 F 0.59191(7) -0.43384(17) 0.69806(8) 0.0261(3) Uani 1 1 d . . . . .
F3 F 0.94322(6) 0.19635(17) 0.41875(9) 0.0279(3) Uani 1 1 d . . . . .
F4 F 1.07379(7) 0.1506(2) 0.39956(11) 0.0354(3) Uani 1 1 d . . . . .
C1 C 0.61184(9) 0.4371(2) 0.53563(10) 0.0160(3) Uani 1 1 d . . . . .
H1 H 0.567254 0.511907 0.521729 0.019 Uiso 1 1 calc R U . . .
C2 C 0.62107(9) 0.2686(2) 0.58330(10) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.581891 0.228025 0.602092 0.018 Uiso 1 1 calc R U . . .
C3 C 0.68701(9) 0.1550(2) 0.60489(10) 0.0138(3) Uani 1 1 d . . . . .
C4 C 0.74470(9) 0.2118(2) 0.57677(10) 0.0137(3) Uani 1 1 d . . . . .
H4 H 0.788953 0.135731 0.590068 0.016 Uiso 1 1 calc R U . . .
C5 C 0.85519(9) 0.4444(2) 0.48867(10) 0.0150(3) Uani 1 1 d . . . . .
H5 H 0.882082 0.331220 0.514963 0.018 Uiso 1 1 calc R U . . .
C6 C 0.88615(9) 0.5751(2) 0.44655(10) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.84560(10) 0.7432(3) 0.40861(11) 0.0177(3) Uani 1 1 d . . . . .
H7 H 0.867410 0.831872 0.380643 0.021 Uiso 1 1 calc R U . . .
C8 C 0.77513(10) 0.7837(3) 0.41069(11) 0.0179(3) Uani 1 1 d . . . . .
H8 H 0.748698 0.897880 0.384869 0.022 Uiso 1 1 calc R U . . .
N9 N 0.67588(8) 0.6558(2) 0.46275(9) 0.0161(3) Uani 1 1 d . . . . .
H9 H 0.6387(14) 0.738(4) 0.4377(16) 0.019 Uiso 1 1 d . U . . .
C10 C 0.67022(9) 0.4935(2) 0.50866(10) 0.0139(3) Uani 1 1 d . . . . .
C11 C 0.73653(9) 0.3817(2) 0.52893(10) 0.0140(3) Uani 1 1 d . . . . .
C12 C 0.78426(9) 0.4822(2) 0.49161(10) 0.0140(3) Uani 1 1 d . . . . .
C13 C 0.74430(9) 0.6511(2) 0.45200(10) 0.0154(3) Uani 1 1 d . . . . .
C14 C 0.69686(9) -0.0182(2) 0.65988(10) 0.0130(3) Uani 1 1 d . . . . .
C15 C 0.64054(9) -0.1540(2) 0.65350(10) 0.0148(3) Uani 1 1 d . . . . .
C16 C 0.64996(10) -0.3116(2) 0.70657(11) 0.0175(3) Uani 1 1 d . . . . .
C17 C 0.71649(11) -0.3444(3) 0.76782(12) 0.0214(3) Uani 1 1 d . . . . .
H17 H 0.722796 -0.453829 0.803776 0.026 Uiso 1 1 calc R U . . .
C18 C 0.77429(10) -0.2118(3) 0.77535(11) 0.0200(3) Uani 1 1 d . . . . .
H18 H 0.820883 -0.231252 0.816864 0.024 Uiso 1 1 calc R U . . .
C19 C 0.76447(9) -0.0517(2) 0.72282(11) 0.0161(3) Uani 1 1 d . . . . .
H19 H 0.804474 0.037634 0.729600 0.019 Uiso 1 1 calc R U . . .
C20 C 0.96117(9) 0.5433(2) 0.44073(11) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.98609(10) 0.3587(3) 0.42609(12) 0.0186(3) Uani 1 1 d . . . . .
C22 C 1.05457(10) 0.3340(3) 0.41581(13) 0.0219(4) Uani 1 1 d . . . . .
C23 C 1.10168(11) 0.4903(3) 0.42118(14) 0.0245(4) Uani 1 1 d . . . . .
H23 H 1.148530 0.471931 0.414128 0.029 Uiso 1 1 calc R U . . .
C24 C 1.07898(11) 0.6758(3) 0.43718(14) 0.0265(4) Uani 1 1 d . . . . .
H24 H 1.110822 0.786216 0.441644 0.032 Uiso 1 1 calc R U . . .
C25 C 1.01011(11) 0.7020(3) 0.44678(13) 0.0223(4) Uani 1 1 d . . . . .
H25 H 0.995782 0.830597 0.457718 0.027 Uiso 1 1 calc R U . . .
N31 N 0.55796(9) -0.0988(2) 0.36112(9) 0.0183(3) Uani 1 1 d . . . . .
C31 C 0.49243(13) -0.1266(5) 0.3844(2) 0.0589(10) Uani 1 1 d . . . . .
H31A H 0.503697 -0.089493 0.442407 0.071 Uiso 1 1 calc R U . . .
H31B H 0.477906 -0.267699 0.378378 0.071 Uiso 1 1 calc R U . . .
C32 C 0.42692(12) 0.0019(5) 0.33006(19) 0.0503(8) Uani 1 1 d . . . . .
H32A H 0.388300 -0.084516 0.293306 0.060 Uiso 1 1 calc R U . . .
H32B H 0.404354 0.076084 0.365058 0.060 Uiso 1 1 calc R U . . .
C33 C 0.53904(16) -0.1315(3) 0.27281(14) 0.0401(6) Uani 1 1 d . . . . .
H33A H 0.517162 -0.264709 0.258406 0.048 Uiso 1 1 calc R U . . .
H33B H 0.584548 -0.124124 0.257514 0.048 Uiso 1 1 calc R U . . .
C34 C 0.48275(14) 0.0275(3) 0.22534(12) 0.0324(5) Uani 1 1 d . . . . .
H34A H 0.507320 0.119075 0.197837 0.039 Uiso 1 1 calc R U . . .
H34B H 0.440960 -0.037025 0.182873 0.039 Uiso 1 1 calc R U . . .
C35 C 0.58333(11) 0.1076(3) 0.37622(14) 0.0305(4) Uani 1 1 d . . . . .
H35A H 0.622933 0.132229 0.352273 0.037 Uiso 1 1 calc R U . . .
H35B H 0.604142 0.131754 0.435767 0.037 Uiso 1 1 calc R U . . .
C36 C 0.51709(11) 0.2503(3) 0.33735(13) 0.0280(4) Uani 1 1 d . . . . .
H36A H 0.501947 0.313269 0.380879 0.034 Uiso 1 1 calc R U . . .
H36B H 0.532474 0.355778 0.306778 0.034 Uiso 1 1 calc R U . . .
N32 N 0.45403(8) 0.1399(2) 0.28166(10) 0.0184(3) Uani 1 1 d . . . . .
F41 F 0.42370(6) -0.17714(16) 0.54103(7) 0.0194(2) Uani 1 1 d . . . . .
F42 F 0.40090(7) -0.46930(16) 0.43294(8) 0.0227(2) Uani 1 1 d . . . . .
F43 F 0.05713(6) 0.20443(17) 0.70843(9) 0.0262(3) Uani 1 1 d . . . . .
F44 F -0.07335(7) 0.16558(19) 0.72790(10) 0.0333(3) Uani 1 1 d . . . . .
C41 C 0.39523(9) 0.4045(2) 0.60416(10) 0.0153(3) Uani 1 1 d . . . . .
H41 H 0.441405 0.472435 0.620952 0.018 Uiso 1 1 calc R U . . .
C42 C 0.38438(9) 0.2377(2) 0.55504(10) 0.0147(3) Uani 1 1 d . . . . .
H42 H 0.423851 0.192641 0.537641 0.018 Uiso 1 1 calc R U . . .
C43 C 0.31677(9) 0.1332(2) 0.53014(10) 0.0133(3) Uani 1 1 d . . . . .
C44 C 0.25845(9) 0.1970(2) 0.55585(10) 0.0146(3) Uani 1 1 d . . . . .
H44 H 0.212942 0.125999 0.540425 0.018 Uiso 1 1 calc R U . . .
C45 C 0.14730(9) 0.4432(2) 0.63925(10) 0.0155(3) Uani 1 1 d . . . . .
H45 H 0.119548 0.331781 0.612422 0.019 Uiso 1 1 calc R U . . .
C46 C 0.11646(9) 0.5778(2) 0.67960(10) 0.0158(3) Uani 1 1 d . . . . .
C47 C 0.15827(10) 0.7456(2) 0.71798(11) 0.0176(3) Uani 1 1 d . . . . .
H47 H 0.136432 0.837995 0.744435 0.021 Uiso 1 1 calc R U . . .
C48 C 0.23000(10) 0.7786(2) 0.71805(11) 0.0172(3) Uani 1 1 d . . . . .
H48 H 0.257292 0.891748 0.743764 0.021 Uiso 1 1 calc R U . . .
N49 N 0.33131(8) 0.6346(2) 0.67294(9) 0.0161(3) Uani 1 1 d . . . . .
H49 H 0.3717(14) 0.702(4) 0.7066(15) 0.019 Uiso 1 1 d . U . . .
C50 C 0.33611(9) 0.4693(2) 0.62811(10) 0.0142(3) Uani 1 1 d . . . . .
C51 C 0.26769(9) 0.3659(2) 0.60445(10) 0.0138(3) Uani 1 1 d . . . . .
C52 C 0.21959(9) 0.4739(2) 0.63866(10) 0.0142(3) Uani 1 1 d . . . . .
C53 C 0.26066(9) 0.6399(2) 0.67901(10) 0.0144(3) Uani 1 1 d . . . . .
C54 C 0.30476(9) -0.0367(2) 0.47288(10) 0.0131(3) Uani 1 1 d . . . . .
C55 C 0.35808(9) -0.1824(2) 0.47973(10) 0.0143(3) Uani 1 1 d . . . . .
C56 C 0.34584(10) -0.3368(2) 0.42404(11) 0.0166(3) Uani 1 1 d . . . . .
C57 C 0.28030(11) -0.3534(3) 0.36000(11) 0.0201(3) Uani 1 1 d . . . . .
H57 H 0.272288 -0.459752 0.322298 0.024 Uiso 1 1 calc R U . . .
C58 C 0.22619(10) -0.2106(3) 0.35198(11) 0.0211(3) Uani 1 1 d . . . . .
H58 H 0.180382 -0.219154 0.308339 0.025 Uiso 1 1 calc R U . . .
C59 C 0.23836(9) -0.0550(3) 0.40716(11) 0.0173(3) Uani 1 1 d . . . . .
H59 H 0.200638 0.041607 0.400143 0.021 Uiso 1 1 calc R U . . .
C60 C 0.04092(10) 0.5517(3) 0.68476(10) 0.0166(3) Uani 1 1 d . . . . .
C61 C 0.01510(10) 0.3692(3) 0.70030(11) 0.0177(3) Uani 1 1 d . . . . .
C62 C -0.05325(10) 0.3480(3) 0.71118(12) 0.0212(3) Uani 1 1 d . . . . .
C63 C -0.09997(11) 0.5065(3) 0.70505(13) 0.0244(4) Uani 1 1 d . . . . .
H63 H -0.146842 0.490891 0.712343 0.029 Uiso 1 1 calc R U . . .
C64 C -0.07620(11) 0.6900(3) 0.68784(15) 0.0264(4) Uani 1 1 d . . . . .
H64 H -0.107495 0.801894 0.682657 0.032 Uiso 1 1 calc R U . . .
C65 C -0.00707(11) 0.7123(3) 0.67805(13) 0.0225(3) Uani 1 1 d . . . . .
H65 H 0.007915 0.839649 0.666540 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.351(2) . ?
F2 C16 1.351(2) . ?
F3 C21 1.351(2) . ?
F4 C22 1.350(2) . ?
C1 C2 1.385(2) . ?
C1 C10 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 C14 1.483(2) . ?
C4 C11 1.396(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.395(2) . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.410(2) . ?
C6 C20 1.484(2) . ?
C7 C8 1.385(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.395(2) . ?
C8 H8 0.9500 . ?
N9 C13 1.379(2) . ?
N9 C10 1.382(2) . ?
N9 H9 0.89(3) . ?
C10 C11 1.415(2) . ?
C11 C12 1.450(2) . ?
C12 C13 1.419(2) . ?
C14 C15 1.391(2) . ?
C14 C19 1.405(2) . ?
C15 C16 1.381(2) . ?
C16 C17 1.377(3) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.390(2) . ?
C20 C25 1.404(2) . ?
C21 C22 1.387(2) . ?
C22 C23 1.371(3) . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C31 1.448(3) . ?
N31 C33 1.470(3) . ?
N31 C35 1.473(3) . ?
C31 C32 1.558(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.461(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.551(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.480(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.556(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.473(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
F41 C55 1.3485(19) . ?
F42 C56 1.351(2) . ?
F43 C61 1.353(2) . ?
F44 C62 1.352(2) . ?
C41 C42 1.388(2) . ?
C41 C50 1.396(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.408(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.398(2) . ?
C43 C54 1.487(2) . ?
C44 C51 1.397(2) . ?
C44 H44 0.9500 . ?
C45 C46 1.393(2) . ?
C45 C52 1.399(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.420(2) . ?
C46 C60 1.484(2) . ?
C47 C48 1.387(2) . ?
C47 H47 0.9500 . ?
C48 C53 1.395(2) . ?
C48 H48 0.9500 . ?
N49 C50 1.383(2) . ?
N49 C53 1.388(2) . ?
N49 H49 0.92(3) . ?
C50 C51 1.417(2) . ?
C51 C52 1.446(2) . ?
C52 C53 1.415(2) . ?
C54 C55 1.393(2) . ?
C54 C59 1.401(2) . ?
C55 C56 1.390(2) . ?
C56 C57 1.375(3) . ?
C57 C58 1.388(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.390(2) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 C61 1.389(2) . ?
C60 C65 1.401(2) . ?
C61 C62 1.386(2) . ?
C62 C63 1.376(3) . ?
C63 C64 1.388(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.393(3) . ?
C64 H64 0.9500 . ?
C65 H65 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
C2 C1 C10 117.86(15) . . ?
C2 C1 H1 121.1 . . ?
C10 C1 H1 121.1 . . ?
C1 C2 C3 122.09(15) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 119.49(15) . . ?
C4 C3 C14 119.69(14) . . ?
C2 C3 C14 120.77(15) . . ?
C11 C4 C3 119.23(15) . . ?
C11 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C12 C5 C6 119.12(15) . . ?
C12 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 119.55(15) . . ?
C5 C6 C20 121.92(15) . . ?
C7 C6 C20 118.53(15) . . ?
C8 C7 C6 122.33(15) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C13 117.72(15) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.53(13) . . ?
C13 N9 H9 125.7(16) . . ?
C10 N9 H9 125.1(17) . . ?
N9 C10 C1 129.32(15) . . ?
N9 C10 C11 109.51(14) . . ?
C1 C10 C11 121.16(15) . . ?
C4 C11 C10 120.17(15) . . ?
C4 C11 C12 133.52(15) . . ?
C10 C11 C12 106.31(14) . . ?
C5 C12 C13 120.16(15) . . ?
C5 C12 C11 133.73(15) . . ?
C13 C12 C11 106.11(14) . . ?
N9 C13 C8 129.36(15) . . ?
N9 C13 C12 109.53(14) . . ?
C8 C13 C12 121.11(15) . . ?
C15 C14 C19 116.22(15) . . ?
C15 C14 C3 122.76(14) . . ?
C19 C14 C3 121.01(15) . . ?
F1 C15 C16 117.57(15) . . ?
F1 C15 C14 120.37(14) . . ?
C16 C15 C14 122.06(16) . . ?
F2 C16 C17 119.91(15) . . ?
F2 C16 C15 118.62(16) . . ?
C17 C16 C15 121.47(16) . . ?
C16 C17 C18 117.86(16) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C19 C18 C17 120.69(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 121.70(16) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?
C21 C20 C25 116.20(16) . . ?
C21 C20 C6 122.62(15) . . ?
C25 C20 C6 121.14(15) . . ?
F3 C21 C22 117.21(16) . . ?
F3 C21 C20 121.00(15) . . ?
C22 C21 C20 121.76(16) . . ?
F4 C22 C23 120.38(17) . . ?
F4 C22 C21 118.08(17) . . ?
C23 C22 C21 121.54(18) . . ?
C22 C23 C24 118.08(17) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C23 C24 C25 120.69(18) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C20 121.71(18) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
C31 N31 C33 109.5(2) . . ?
C31 N31 C35 109.7(2) . . ?
C33 N31 C35 106.32(17) . . ?
N31 C31 C32 110.68(17) . . ?
N31 C31 H31A 109.5 . . ?
C32 C31 H31A 109.5 . . ?
N31 C31 H31B 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 108.1 . . ?
N32 C32 C31 109.79(16) . . ?
N32 C32 H32A 109.7 . . ?
C31 C32 H32A 109.7 . . ?
N32 C32 H32B 109.7 . . ?
C31 C32 H32B 109.7 . . ?
H32A C32 H32B 108.2 . . ?
N31 C33 C34 109.68(16) . . ?
N31 C33 H33A 109.7 . . ?
C34 C33 H33A 109.7 . . ?
N31 C33 H33B 109.7 . . ?
C34 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
N32 C34 C33 110.43(16) . . ?
N32 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 109.84(15) . . ?
N31 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N31 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N32 C36 C35 109.83(15) . . ?
N32 C36 H36A 109.7 . . ?
C35 C36 H36A 109.7 . . ?
N32 C36 H36B 109.7 . . ?
C35 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C32 N32 C36 108.38(19) . . ?
C32 N32 C34 109.3(2) . . ?
C36 N32 C34 107.04(16) . . ?
C42 C41 C50 117.86(15) . . ?
C42 C41 H41 121.1 . . ?
C50 C41 H41 121.1 . . ?
C41 C42 C43 122.14(15) . . ?
C41 C42 H42 118.9 . . ?
C43 C42 H42 118.9 . . ?
C44 C43 C42 119.53(15) . . ?
C44 C43 C54 119.30(14) . . ?
C42 C43 C54 121.07(14) . . ?
C51 C44 C43 119.39(15) . . ?
C51 C44 H44 120.3 . . ?
C43 C44 H44 120.3 . . ?
C46 C45 C52 119.27(15) . . ?
C46 C45 H45 120.4 . . ?
C52 C45 H45 120.4 . . ?
C45 C46 C47 119.54(15) . . ?
C45 C46 C60 122.23(15) . . ?
C47 C46 C60 118.23(15) . . ?
C48 C47 C46 122.04(15) . . ?
C48 C47 H47 119.0 . . ?
C46 C47 H47 119.0 . . ?
C47 C48 C53 117.64(15) . . ?
C47 C48 H48 121.2 . . ?
C53 C48 H48 121.2 . . ?
C50 N49 C53 108.10(14) . . ?
C50 N49 H49 124.2(16) . . ?
C53 N49 H49 124.7(16) . . ?
N49 C50 C41 129.21(15) . . ?
N49 C50 C51 109.63(14) . . ?
C41 C50 C51 121.14(15) . . ?
C44 C51 C50 119.92(15) . . ?
C44 C51 C52 133.74(15) . . ?
C50 C51 C52 106.33(14) . . ?
C45 C52 C53 120.02(15) . . ?
C45 C52 C51 133.63(15) . . ?
C53 C52 C51 106.34(14) . . ?
N49 C53 C48 128.97(15) . . ?
N49 C53 C52 109.57(14) . . ?
C48 C53 C52 121.46(15) . . ?
C55 C54 C59 116.43(15) . . ?
C55 C54 C43 122.93(15) . . ?
C59 C54 C43 120.62(15) . . ?
F41 C55 C56 117.80(15) . . ?
F41 C55 C54 120.66(14) . . ?
C56 C55 C54 121.53(15) . . ?
F42 C56 C57 120.21(16) . . ?
F42 C56 C55 118.32(16) . . ?
C57 C56 C55 121.45(16) . . ?
C56 C57 C58 118.13(16) . . ?
C56 C57 H57 120.9 . . ?
C58 C57 H57 120.9 . . ?
C57 C58 C59 120.65(17) . . ?
C57 C58 H58 119.7 . . ?
C59 C58 H58 119.7 . . ?
C58 C59 C54 121.80(16) . . ?
C58 C59 H59 119.1 . . ?
C54 C59 H59 119.1 . . ?
C61 C60 C65 116.20(16) . . ?
C61 C60 C46 122.13(15) . . ?
C65 C60 C46 121.60(16) . . ?
F43 C61 C62 116.91(16) . . ?
F43 C61 C60 121.11(15) . . ?
C62 C61 C60 121.94(16) . . ?
F44 C62 C63 120.36(17) . . ?
F44 C62 C61 118.06(17) . . ?
C63 C62 C61 121.58(17) . . ?
C62 C63 C64 117.66(17) . . ?
C62 C63 H63 121.2 . . ?
C64 C63 H63 121.2 . . ?
C63 C64 C65 120.88(18) . . ?
C63 C64 H64 119.6 . . ?
C65 C64 H64 119.6 . . ?
C64 C65 C60 121.70(18) . . ?
C64 C65 H65 119.1 . . ?
C60 C65 H65 119.1 . . ?

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
C10 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C14 176.50(16) . . . . ?
C2 C3 C4 C11 1.0(2) . . . . ?
C14 C3 C4 C11 -176.30(15) . . . . ?
C12 C5 C6 C7 0.6(3) . . . . ?
C12 C5 C6 C20 -179.75(16) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C20 C6 C7 C8 179.69(17) . . . . ?
C6 C7 C8 C13 -0.1(3) . . . . ?
C13 N9 C10 C1 179.27(17) . . . . ?
C13 N9 C10 C11 0.56(19) . . . . ?
C2 C1 C10 N9 -178.22(17) . . . . ?
C2 C1 C10 C11 0.3(2) . . . . ?
C3 C4 C11 C10 -0.6(2) . . . . ?
C3 C4 C11 C12 178.96(17) . . . . ?
N9 C10 C11 C4 178.73(15) . . . . ?
C1 C10 C11 C4 -0.1(2) . . . . ?
N9 C10 C11 C12 -0.94(19) . . . . ?
C1 C10 C11 C12 -179.76(15) . . . . ?
C6 C5 C12 C13 0.2(3) . . . . ?
C6 C5 C12 C11 -179.70(17) . . . . ?
C4 C11 C12 C5 1.2(3) . . . . ?
C10 C11 C12 C5 -179.16(19) . . . . ?
C4 C11 C12 C13 -178.66(18) . . . . ?
C10 C11 C12 C13 0.94(18) . . . . ?
C10 N9 C13 C8 -179.42(18) . . . . ?
C10 N9 C13 C12 0.05(19) . . . . ?
C7 C8 C13 N9 -179.61(18) . . . . ?
C7 C8 C13 C12 1.0(3) . . . . ?
C5 C12 C13 N9 179.45(16) . . . . ?
C11 C12 C13 N9 -0.62(19) . . . . ?
C5 C12 C13 C8 -1.0(3) . . . . ?
C11 C12 C13 C8 178.90(16) . . . . ?
C4 C3 C14 C15 -140.49(17) . . . . ?
C2 C3 C14 C15 42.2(2) . . . . ?
C4 C3 C14 C19 40.5(2) . . . . ?
C2 C3 C14 C19 -136.77(17) . . . . ?
C19 C14 C15 F1 -178.49(14) . . . . ?
C3 C14 C15 F1 2.5(2) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C3 C14 C15 C16 -178.23(15) . . . . ?
F1 C15 C16 F2 -2.7(2) . . . . ?
C14 C15 C16 F2 177.97(15) . . . . ?
F1 C15 C16 C17 178.04(15) . . . . ?
C14 C15 C16 C17 -1.3(3) . . . . ?
F2 C16 C17 C18 -178.59(16) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C14 -0.8(3) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
C3 C14 C19 C18 179.28(16) . . . . ?
C5 C6 C20 C21 42.3(3) . . . . ?
C7 C6 C20 C21 -138.06(18) . . . . ?
C5 C6 C20 C25 -140.16(19) . . . . ?
C7 C6 C20 C25 39.5(2) . . . . ?
C25 C20 C21 F3 -179.63(17) . . . . ?
C6 C20 C21 F3 -2.0(3) . . . . ?
C25 C20 C21 C22 -1.7(3) . . . . ?
C6 C20 C21 C22 175.92(18) . . . . ?
F3 C21 C22 F4 -0.2(3) . . . . ?
C20 C21 C22 F4 -178.20(18) . . . . ?
F3 C21 C22 C23 179.26(18) . . . . ?
C20 C21 C22 C23 1.3(3) . . . . ?
F4 C22 C23 C24 179.4(2) . . . . ?
C21 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C20 0.0(3) . . . . ?
C21 C20 C25 C24 1.1(3) . . . . ?
C6 C20 C25 C24 -176.58(19) . . . . ?
C33 N31 C31 C32 -52.6(4) . . . . ?
C35 N31 C31 C32 63.7(3) . . . . ?
N31 C31 C32 N32 -10.3(4) . . . . ?
C31 N31 C33 C34 64.3(3) . . . . ?
C35 N31 C33 C34 -54.2(3) . . . . ?
N31 C33 C34 N32 -10.8(3) . . . . ?
C31 N31 C35 C36 -50.3(2) . . . . ?
C33 N31 C35 C36 68.1(2) . . . . ?
N31 C35 C36 N32 -13.1(2) . . . . ?
C31 C32 N32 C36 -52.9(3) . . . . ?
C31 C32 N32 C34 63.4(3) . . . . ?
C35 C36 N32 C32 66.1(2) . . . . ?
C35 C36 N32 C34 -51.7(2) . . . . ?
C33 C34 N32 C32 -51.6(3) . . . . ?
C33 C34 N32 C36 65.6(2) . . . . ?
C50 C41 C42 C43 -0.8(2) . . . . ?
C41 C42 C43 C44 -0.5(2) . . . . ?
C41 C42 C43 C54 175.75(15) . . . . ?
C42 C43 C44 C51 1.4(2) . . . . ?
C54 C43 C44 C51 -175.00(15) . . . . ?
C52 C45 C46 C47 1.2(3) . . . . ?
C52 C45 C46 C60 -178.22(16) . . . . ?
C45 C46 C47 C48 -1.2(3) . . . . ?
C60 C46 C47 C48 178.24(16) . . . . ?
C46 C47 C48 C53 -0.3(3) . . . . ?
C53 N49 C50 C41 178.13(17) . . . . ?
C53 N49 C50 C51 0.19(19) . . . . ?
C42 C41 C50 N49 -176.48(17) . . . . ?
C42 C41 C50 C51 1.3(2) . . . . ?
C43 C44 C51 C50 -0.9(2) . . . . ?
C43 C44 C51 C52 177.66(17) . . . . ?
N49 C50 C51 C44 177.68(15) . . . . ?
C41 C50 C51 C44 -0.5(2) . . . . ?
N49 C50 C51 C52 -1.22(19) . . . . ?
C41 C50 C51 C52 -179.35(15) . . . . ?
C46 C45 C52 C53 0.2(3) . . . . ?
C46 C45 C52 C51 179.25(18) . . . . ?
C44 C51 C52 C45 3.9(3) . . . . ?
C50 C51 C52 C45 -177.38(19) . . . . ?
C44 C51 C52 C53 -176.93(18) . . . . ?
C50 C51 C52 C53 1.74(19) . . . . ?
C50 N49 C53 C48 -179.75(18) . . . . ?
C50 N49 C53 C52 0.96(19) . . . . ?
C47 C48 C53 N49 -177.46(17) . . . . ?
C47 C48 C53 C52 1.8(3) . . . . ?
C45 C52 C53 N49 177.58(16) . . . . ?
C51 C52 C53 N49 -1.68(19) . . . . ?
C45 C52 C53 C48 -1.8(3) . . . . ?
C51 C52 C53 C48 178.96(16) . . . . ?
C44 C43 C54 C55 -140.11(17) . . . . ?
C42 C43 C54 C55 43.6(2) . . . . ?
C44 C43 C54 C59 41.3(2) . . . . ?
C42 C43 C54 C59 -134.95(17) . . . . ?
C59 C54 C55 F41 -179.99(14) . . . . ?
C43 C54 C55 F41 1.4(2) . . . . ?
C59 C54 C55 C56 0.2(2) . . . . ?
C43 C54 C55 C56 -178.42(15) . . . . ?
F41 C55 C56 F42 -1.9(2) . . . . ?
C54 C55 C56 F42 177.93(14) . . . . ?
F41 C55 C56 C57 179.72(15) . . . . ?
C54 C55 C56 C57 -0.5(3) . . . . ?
F42 C56 C57 C58 -178.12(16) . . . . ?
C55 C56 C57 C58 0.2(3) . . . . ?
C56 C57 C58 C59 0.2(3) . . . . ?
C57 C58 C59 C54 -0.5(3) . . . . ?
C55 C54 C59 C58 0.3(3) . . . . ?
C43 C54 C59 C58 178.93(16) . . . . ?
C45 C46 C60 C61 42.1(3) . . . . ?
C47 C46 C60 C61 -137.33(18) . . . . ?
C45 C46 C60 C65 -140.98(19) . . . . ?
C47 C46 C60 C65 39.6(2) . . . . ?
C65 C60 C61 F43 -179.58(17) . . . . ?
C46 C60 C61 F43 -2.5(3) . . . . ?
C65 C60 C61 C62 -2.0(3) . . . . ?
C46 C60 C61 C62 175.04(17) . . . . ?
F43 C61 C62 F44 -0.9(3) . . . . ?
C60 C61 C62 F44 -178.53(17) . . . . ?
F43 C61 C62 C63 179.36(18) . . . . ?
C60 C61 C62 C63 1.7(3) . . . . ?
F44 C62 C63 C64 180.0(2) . . . . ?
C61 C62 C63 C64 -0.3(3) . . . . ?
C62 C63 C64 C65 -0.7(3) . . . . ?
C63 C64 C65 C60 0.3(3) . . . . ?
C61 C60 C65 C64 1.0(3) . . . . ?
C46 C60 C65 C64 -176.02(19) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.89(3) 2.00(3) 2.881(2) 169(2) 1_565 yes
C31 H31A F1 0.99 2.54 3.446(4) 151.8 . yes
C31 H31B F42 0.99 2.42 3.181(3) 133.5 . yes
C34 H34A F1 0.99 2.54 3.384(3) 143.4 2_554 yes
C36 H36B F2 0.99 2.56 3.422(3) 145.8 2_554 yes
N49 H49 N32 0.92(3) 1.99(3) 2.906(2) 176(2) 2_565 yes

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.077


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-2-250K
_database_code_depnum_ccdc_archive 'CCDC 2022177'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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                   6.6803(2)
_cell_length_b                   15.0128(5)
_cell_length_c                   21.3972(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.1430(10)
_cell_angle_gamma                90
_cell_volume                     2137.29(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9191
_cell_measurement_theta_min      2.9502
_cell_measurement_theta_max      29.9601

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            60892
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.960
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5759
_reflns_number_gt                4978
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0749P)²+0.3414P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5759
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1439
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
F1 F -0.02270(12) 0.23797(6) 0.15472(4) 0.0615(2) Uani 1 1 d . . . . .
F2 F 0.03655(15) 0.15642(7) 0.40183(4) 0.0718(3) Uani 1 1 d . . . . .
F3 F 1.39590(13) 0.53751(8) 0.42179(5) 0.0727(3) Uani 1 1 d . . . . .
F4 F 0.77607(15) 0.68712(9) 0.52976(5) 0.0845(3) Uani 1 1 d . . . . .
C1 C 0.5467(2) 0.33113(9) 0.14401(6) 0.0489(3) Uani 1 1 d . . . . .
H1 H 0.573682 0.325004 0.101860 0.059 Uiso 1 1 calc R U . . .
C2 C 0.38427(19) 0.28894(9) 0.16631(6) 0.0461(3) Uani 1 1 d . . . . .
H2 H 0.301562 0.253091 0.138775 0.055 Uiso 1 1 calc R U . . .
C3 C 0.33787(16) 0.29772(8) 0.22905(5) 0.0398(2) Uani 1 1 d . . . . .
C4 C 0.46057(16) 0.35168(7) 0.26954(5) 0.0377(2) Uani 1 1 d . . . . .
H4 H 0.430291 0.359724 0.311233 0.045 Uiso 1 1 calc R U . . .
C5 C 0.83227(16) 0.48068(7) 0.33829(5) 0.0376(2) Uani 1 1 d . . . . .
H5 H 0.743307 0.470734 0.369210 0.045 Uiso 1 1 calc R U . . .
C6 C 1.00811(17) 0.52935(7) 0.35258(5) 0.0392(2) Uani 1 1 d . . . . .
C7 C 1.13999(18) 0.54330(8) 0.30548(6) 0.0438(3) Uani 1 1 d . . . . .
H7 H 1.260117 0.574816 0.315613 0.053 Uiso 1 1 calc R U . . .
C8 C 1.09829(18) 0.51231(8) 0.24538(6) 0.0451(3) Uani 1 1 d . . . . .
H8 H 1.186424 0.523276 0.214385 0.054 Uiso 1 1 calc R U . . .
N9 N 0.84555(17) 0.42655(7) 0.17606(5) 0.0461(2) Uani 1 1 d . . . . .
H9 H 0.893(2) 0.4313(11) 0.1395(8) 0.055 Uiso 1 1 d . U . . .
C10 C 0.66956(18) 0.38286(8) 0.18526(5) 0.0420(3) Uani 1 1 d . . . . .
C11 C 0.62748(16) 0.39353(7) 0.24830(5) 0.0374(2) Uani 1 1 d . . . . .
C12 C 0.78915(16) 0.44698(7) 0.27818(5) 0.0365(2) Uani 1 1 d . . . . .
C13 C 0.92147(17) 0.46410(7) 0.23163(5) 0.0398(2) Uani 1 1 d . . . . .
C14 C 0.16937(17) 0.24844(7) 0.25369(6) 0.0408(2) Uani 1 1 d . . . . .
C15 C -0.00393(18) 0.22104(8) 0.21729(6) 0.0464(3) Uani 1 1 d . . . . .
C16 C -0.1609(2) 0.17661(10) 0.24111(8) 0.0576(4) Uani 1 1 d . . . . .
H16 H -0.275020 0.160920 0.214492 0.069 Uiso 1 1 calc R U . . .
C17 C -0.1505(2) 0.15532(10) 0.30357(8) 0.0590(4) Uani 1 1 d . . . . .
H17 H -0.256214 0.125324 0.320768 0.071 Uiso 1 1 calc R U . . .
C18 C 0.0201(2) 0.17947(9) 0.34002(7) 0.0520(3) Uani 1 1 d . . . . .
C19 C 0.17652(18) 0.22500(8) 0.31702(6) 0.0458(3) Uani 1 1 d . . . . .
H19 H 0.289452 0.240494 0.344228 0.055 Uiso 1 1 calc R U . . .
C20 C 1.04829(17) 0.57130(8) 0.41506(6) 0.0411(2) Uani 1 1 d . . . . .
C21 C 0.89305(18) 0.60995(9) 0.44498(6) 0.0475(3) Uani 1 1 d . . . . .
H21 H 0.760756 0.607888 0.425928 0.057 Uiso 1 1 calc R U . . .
C22 C 0.9321(2) 0.65115(10) 0.50225(7) 0.0549(3) Uani 1 1 d . . . . .
C23 C 1.1230(2) 0.65767(10) 0.53228(7) 0.0587(4) Uani 1 1 d . . . . .
H23 H 1.146160 0.687103 0.571023 0.070 Uiso 1 1 calc R U . . .
C24 C 1.2784(2) 0.61961(11) 0.50360(7) 0.0596(4) Uani 1 1 d . . . . .
H24 H 1.410724 0.622769 0.522572 0.072 Uiso 1 1 calc R U . . .
C25 C 1.23873(18) 0.57708(9) 0.44718(7) 0.0499(3) Uani 1 1 d . . . . .
N31 N 0.978(2) 0.4623(8) 0.0506(6) 0.0535(16) Uani 0.5 1 d . . P A -1
C31 C 0.8371(8) 0.4335(4) 0.00254(17) 0.0907(15) Uani 0.5 1 d . . P A -1
H31A H 0.702034 0.450282 0.012756 0.109 Uiso 0.5 1 calc R U P A -1
H31B H 0.842107 0.368423 -0.000429 0.109 Uiso 0.5 1 calc R U P A -1
C32 C 0.8771(7) 0.4747(3) -0.06176(15) 0.0828(12) Uani 0.5 1 d . . P A -1
H32A H 0.897672 0.426990 -0.091746 0.099 Uiso 0.5 1 calc R U P A -1
H32B H 0.759891 0.509557 -0.078141 0.099 Uiso 0.5 1 calc R U P A -1
C33 C 0.9351(7) 0.5705(3) 0.05210(16) 0.0786(10) Uani 0.5 1 d . . P A -1
H33A H 0.796823 0.581492 0.061967 0.094 Uiso 0.5 1 calc R U P A -1
H33B H 1.026529 0.598734 0.084632 0.094 Uiso 0.5 1 calc R U P A -1
C34 C 0.9679(7) 0.6106(3) -0.01272(17) 0.0795(10) Uani 0.5 1 d . . P A -1
H34A H 1.069519 0.657833 -0.008345 0.095 Uiso 0.5 1 calc R U P A -1
H34B H 0.842245 0.636033 -0.032194 0.095 Uiso 0.5 1 calc R U P A -1
C35 C 1.1751(6) 0.4591(3) 0.03883(18) 0.0790(11) Uani 0.5 1 d . . P A -1
H35A H 1.218067 0.396708 0.038355 0.095 Uiso 0.5 1 calc R U P A -1
H35B H 1.256248 0.489157 0.072977 0.095 Uiso 0.5 1 calc R U P A -1
C36 C 1.2153(6) 0.5026(4) -0.02345(19) 0.0840(12) Uani 0.5 1 d . . P A -1
H36A H 1.303367 0.554268 -0.015246 0.101 Uiso 0.5 1 calc R U P A -1
H36B H 1.284728 0.460038 -0.048723 0.101 Uiso 0.5 1 calc R U P A -1
N32 N 1.044(2) 0.5288(9) -0.0557(6) 0.066(3) Uani 0.5 1 d . . P A -1


_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
F1 C15 1.3575(16) . ?
F2 C18 1.3620(17) . ?
F3 C25 1.3612(16) . ?
F4 C22 1.3545(17) . ?
C1 C2 1.3781(18) . ?
C1 C10 1.3877(17) . ?
C1 H1 0.9400 . ?
C2 C3 1.4107(17) . ?
C2 H2 0.9400 . ?
C3 C4 1.3969(15) . ?
C3 C14 1.4828(16) . ?
C4 C11 1.3913(15) . ?
C4 H4 0.9400 . ?
C5 C12 1.3882(16) . ?
C5 C6 1.3938(15) . ?
C5 H5 0.9400 . ?
C6 C7 1.4126(16) . ?
C6 C20 1.4804(17) . ?
C7 C8 1.3723(18) . ?
C7 H7 0.9400 . ?
C8 C13 1.3941(17) . ?
C8 H8 0.9400 . ?
N9 C13 1.3713(16) . ?
N9 C10 1.3758(16) . ?
N9 H9 0.871(17) . ?
C10 C11 1.4114(15) . ?
C11 C12 1.4475(15) . ?
C12 C13 1.4133(15) . ?
C14 C19 1.3966(18) . ?
C14 C15 1.3980(16) . ?
C15 C16 1.3781(19) . ?
C16 C17 1.370(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.371(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.3760(18) . ?
C19 H19 0.9400 . ?
C20 C21 1.3932(17) . ?
C20 C25 1.3934(16) . ?
C21 C22 1.3767(19) . ?
C21 H21 0.9400 . ?
C22 C23 1.379(2) . ?
C23 C24 1.377(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.370(2) . ?
C24 H24 0.9400 . ?
N31 C35 1.360(16) . ?
N31 C31 1.401(14) . ?
N31 C33 1.651(13) . ?
C31 C32 1.553(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C32 N32 1.374(14) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C33 C34 1.546(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C34 N32 1.643(17) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C35 C36 1.529(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 N32 1.343(14) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C10 118.44(11) . . ?
C2 C1 H1 120.8 . . ?
C10 C1 H1 120.8 . . ?
C1 C2 C3 122.24(11) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.53(11) . . ?
C4 C3 C14 119.38(10) . . ?
C2 C3 C14 122.03(10) . . ?
C11 C4 C3 120.14(10) . . ?
C11 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C5 C6 119.68(10) . . ?
C12 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.24(11) . . ?
C5 C6 C20 120.15(10) . . ?
C7 C6 C20 120.47(10) . . ?
C8 C7 C6 122.08(11) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 118.09(10) . . ?
C7 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
C13 N9 C10 109.05(9) . . ?
C13 N9 H9 127.5(11) . . ?
C10 N9 H9 123.3(11) . . ?
N9 C10 C1 129.80(11) . . ?
N9 C10 C11 109.18(10) . . ?
C1 C10 C11 120.95(11) . . ?
C4 C11 C10 119.67(10) . . ?
C4 C11 C12 133.96(10) . . ?
C10 C11 C12 106.29(10) . . ?
C5 C12 C13 119.72(10) . . ?
C5 C12 C11 134.11(10) . . ?
C13 C12 C11 106.17(10) . . ?
N9 C13 C8 129.57(10) . . ?
N9 C13 C12 109.28(10) . . ?
C8 C13 C12 121.15(11) . . ?
C19 C14 C15 114.89(11) . . ?
C19 C14 C3 120.65(10) . . ?
C15 C14 C3 124.46(11) . . ?
F1 C15 C16 116.69(11) . . ?
F1 C15 C14 119.54(12) . . ?
C16 C15 C14 123.77(13) . . ?
C17 C16 C15 120.00(12) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 117.39(13) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 H17 121.3 . . ?
F2 C18 C17 118.41(12) . . ?
F2 C18 C19 118.42(12) . . ?
C17 C18 C19 123.17(14) . . ?
C18 C19 C14 120.75(12) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C21 C20 C25 115.58(12) . . ?
C21 C20 C6 120.66(10) . . ?
C25 C20 C6 123.75(11) . . ?
C22 C21 C20 120.44(11) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
F4 C22 C21 118.30(12) . . ?
F4 C22 C23 119.00(13) . . ?
C21 C22 C23 122.70(14) . . ?
C24 C23 C22 117.77(13) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
C25 C24 C23 119.45(12) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
F3 C25 C24 117.36(11) . . ?
F3 C25 C20 118.60(12) . . ?
C24 C25 C20 124.03(13) . . ?
C35 N31 C31 116.8(11) . . ?
C35 N31 C33 102.3(7) . . ?
C31 N31 C33 102.1(8) . . ?
N31 C31 C32 111.6(5) . . ?
N31 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
N31 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 108.0 . . ?
N32 C32 C31 110.8(6) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 N31 109.1(5) . . ?
C34 C33 H33A 109.9 . . ?
N31 C33 H33A 109.9 . . ?
C34 C33 H33B 109.9 . . ?
N31 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
C33 C34 N32 106.7(5) . . ?
C33 C34 H34A 110.4 . . ?
N32 C34 H34A 110.4 . . ?
C33 C34 H34B 110.4 . . ?
N32 C34 H34B 110.4 . . ?
H34A C34 H34B 108.6 . . ?
N31 C35 C36 113.2(5) . . ?
N31 C35 H35A 108.9 . . ?
C36 C35 H35A 108.9 . . ?
N31 C35 H35B 108.9 . . ?
C36 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
N32 C36 C35 111.4(6) . . ?
N32 C36 H36A 109.4 . . ?
C35 C36 H36A 109.4 . . ?
N32 C36 H36B 109.4 . . ?
C35 C36 H36B 109.4 . . ?
H36A C36 H36B 108.0 . . ?
C36 N32 C32 121.5(10) . . ?
C36 N32 C34 102.9(9) . . ?
C32 N32 C34 101.9(10) . . ?

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
C10 C1 C2 C3 0.92(19) . . . . ?
C1 C2 C3 C4 0.50(18) . . . . ?
C1 C2 C3 C14 -176.70(11) . . . . ?
C2 C3 C4 C11 -1.69(16) . . . . ?
C14 C3 C4 C11 175.59(10) . . . . ?
C12 C5 C6 C7 -0.18(16) . . . . ?
C12 C5 C6 C20 175.43(10) . . . . ?
C5 C6 C7 C8 1.66(18) . . . . ?
C20 C6 C7 C8 -173.94(11) . . . . ?
C6 C7 C8 C13 -1.34(18) . . . . ?
C13 N9 C10 C1 -175.77(13) . . . . ?
C13 N9 C10 C11 1.08(13) . . . . ?
C2 C1 C10 N9 175.37(12) . . . . ?
C2 C1 C10 C11 -1.17(19) . . . . ?
C3 C4 C11 C10 1.45(16) . . . . ?
C3 C4 C11 C12 -174.79(12) . . . . ?
N9 C10 C11 C4 -177.18(10) . . . . ?
C1 C10 C11 C4 0.00(17) . . . . ?
N9 C10 C11 C12 0.00(13) . . . . ?
C1 C10 C11 C12 177.19(11) . . . . ?
C6 C5 C12 C13 -1.50(16) . . . . ?
C6 C5 C12 C11 178.42(11) . . . . ?
C4 C11 C12 C5 -4.4(2) . . . . ?
C10 C11 C12 C5 179.04(12) . . . . ?
C4 C11 C12 C13 175.56(12) . . . . ?
C10 C11 C12 C13 -1.04(12) . . . . ?
C10 N9 C13 C8 178.05(12) . . . . ?
C10 N9 C13 C12 -1.77(13) . . . . ?
C7 C8 C13 N9 179.80(12) . . . . ?
C7 C8 C13 C12 -0.40(17) . . . . ?
C5 C12 C13 N9 -178.34(10) . . . . ?
C11 C12 C13 N9 1.73(13) . . . . ?
C5 C12 C13 C8 1.83(17) . . . . ?
C11 C12 C13 C8 -178.11(10) . . . . ?
C4 C3 C14 C19 -26.17(16) . . . . ?
C2 C3 C14 C19 151.01(12) . . . . ?
C4 C3 C14 C15 154.62(11) . . . . ?
C2 C3 C14 C15 -28.20(17) . . . . ?
C19 C14 C15 F1 -177.86(10) . . . . ?
C3 C14 C15 F1 1.39(17) . . . . ?
C19 C14 C15 C16 1.92(18) . . . . ?
C3 C14 C15 C16 -178.83(12) . . . . ?
F1 C15 C16 C17 178.44(13) . . . . ?
C14 C15 C16 C17 -1.3(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C17 C18 F2 -177.89(13) . . . . ?
C16 C17 C18 C19 1.4(2) . . . . ?
F2 C18 C19 C14 178.53(12) . . . . ?
C17 C18 C19 C14 -0.7(2) . . . . ?
C15 C14 C19 C18 -0.89(17) . . . . ?
C3 C14 C19 C18 179.83(11) . . . . ?
C5 C6 C20 C21 -38.23(16) . . . . ?
C7 C6 C20 C21 137.33(12) . . . . ?
C5 C6 C20 C25 143.24(12) . . . . ?
C7 C6 C20 C25 -41.21(17) . . . . ?
C25 C20 C21 C22 0.53(18) . . . . ?
C6 C20 C21 C22 -178.12(12) . . . . ?
C20 C21 C22 F4 -179.46(13) . . . . ?
C20 C21 C22 C23 1.0(2) . . . . ?
F4 C22 C23 C24 179.26(14) . . . . ?
C21 C22 C23 C24 -1.2(2) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 F3 -177.53(13) . . . . ?
C23 C24 C25 C20 1.7(2) . . . . ?
C21 C20 C25 F3 177.36(12) . . . . ?
C6 C20 C25 F3 -4.04(18) . . . . ?
C21 C20 C25 C24 -1.91(19) . . . . ?
C6 C20 C25 C24 176.69(13) . . . . ?
C35 N31 C31 C32 -47.3(11) . . . . ?
C33 N31 C31 C32 63.3(10) . . . . ?
N31 C31 C32 N32 0.7(7) . . . . ?
C35 N31 C33 C34 61.6(8) . . . . ?
C31 N31 C33 C34 -59.6(9) . . . . ?
N31 C33 C34 N32 -2.7(4) . . . . ?
C31 N31 C35 C36 50.0(10) . . . . ?
C33 N31 C35 C36 -60.5(9) . . . . ?
N31 C35 C36 N32 -4.8(7) . . . . ?
C35 C36 N32 C32 -44.7(15) . . . . ?
C35 C36 N32 C34 68.2(8) . . . . ?
C31 C32 N32 C36 46.3(16) . . . . ?
C31 C32 N32 C34 -67.0(8) . . . . ?
C33 C34 N32 C36 -60.7(8) . . . . ?
C33 C34 N32 C32 65.9(8) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.871(17) 2.09(2) 2.951(12) 170.5(16) . yes
N9 H9 N32 0.871(17) 1.97(2) 2.823(13) 164.7(16) 3_765 yes
C24 H24 F4 0.94 2.62 3.4725(17) 151.6 1_655 yes

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.120


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3I-100K
_database_code_depnum_ccdc_archive 'CCDC 2022179'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

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'

_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                   6.7657(3)
_cell_length_b                   14.4934(6)
_cell_length_c                   21.3307(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.1667(13)
_cell_angle_gamma                90
_cell_volume                     2079.54(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.40

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.393
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.198
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5421
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus X-ray source'
_diffrn_radiation_monochromator  'Helios multilayer mirror'
_diffrn_measurement_device_type  
'Bruker D8 Venture κ-geometry diffractometer 208039-01'
_diffrn_measurement_method       'φ and ω-scans'
_diffrn_detector_area_resol_mean 52.0833
_diffrn_reflns_number            49708
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_max         31.411
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6833
_reflns_number_gt                5614
_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       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_cell_refinement       'APEX3 v2018.1-0(Bruker, 2018)'
_computing_data_reduction        'SAINT V8.34A (Bruker, 2014)'
_computing_structure_solution    'SHELXS-2012 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLe (Hübschle et al, 2011)'
_computing_publication_material  'CIFTAB V 2013/2 (Sheldrick, 2013)'
_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)+(0.0483P)²+1.5037P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6833
_refine_ls_number_parameters     356
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.1503
_refine_ls_wR_factor_gt          0.1430
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_restrained_S_all      1.143
_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
F3 F 1.45140(16) 0.55279(11) 0.40839(6) 0.0426(4) Uani 0.909(3) 1 d D . P A 1
F4 F 1.55177(17) 0.62984(11) 0.51924(6) 0.0541(4) Uani 1 1 d D . . B 1
F3B F 0.7811(16) 0.6457(13) 0.4217(7) 0.065(5) Uani 0.091(3) 1 d D . P A 2
F2 F 0.05106(18) 0.15705(9) 0.41039(5) 0.0416(3) Uani 1 1 d D . . . .
F1 F 0.35129(16) 0.24278(8) 0.36825(5) 0.0296(3) Uani 0.909(3) 1 d D . P A 1
F1B F -0.0129(17) 0.2532(9) 0.1616(3) 0.037(3) Uani 0.091(3) 1 d D . P A 2
C1 C 0.5228(2) 0.34512(11) 0.14901(7) 0.0252(3) Uani 1 1 d . . . . .
H1 H 0.537223 0.338407 0.105430 0.030 Uiso 1 1 calc R U . . .
C2 C 0.3691(2) 0.30254(10) 0.17569(7) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.278700 0.265020 0.149777 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3414(2) 0.31276(10) 0.23995(7) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.4738(2) 0.36800(9) 0.27830(7) 0.0190(3) Uani 1 1 d . . . . .
H4 H 0.455571 0.377038 0.321416 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8647(2) 0.49486(10) 0.34009(7) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.785930 0.484163 0.373653 0.024 Uiso 1 1 calc R U . . .
C6 C 1.0438(2) 0.54297(10) 0.35098(7) 0.0205(3) Uani 1 1 d . . . . .
C7 C 1.1587(2) 0.55788(10) 0.30044(8) 0.0226(3) Uani 1 1 d . . . . .
H7 H 1.280964 0.590248 0.308138 0.027 Uiso 1 1 calc R U . . .
C8 C 1.0989(2) 0.52695(10) 0.24025(8) 0.0232(3) Uani 1 1 d . . . . .
H8 H 1.177848 0.537751 0.206757 0.028 Uiso 1 1 calc R U . . .
N9 N 0.8281(2) 0.44196(9) 0.17490(6) 0.0234(3) Uani 1 1 d . . . . .
H9 H 0.875(3) 0.4448(14) 0.1371(10) 0.028 Uiso 1 1 d . U . . .
C10 C 0.6560(2) 0.39824(10) 0.18833(7) 0.0215(3) Uani 1 1 d . . . . .
C11 C 0.6326(2) 0.40970(10) 0.25283(7) 0.0188(3) Uani 1 1 d . . . . .
C12 C 0.8022(2) 0.46264(9) 0.27969(7) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.9197(2) 0.47949(10) 0.22998(7) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.1746(2) 0.26417(10) 0.26539(7) 0.0203(3) Uani 1 1 d . . . . .
C15 C 0.1848(2) 0.23298(10) 0.32726(7) 0.0225(3) Uani 1 1 d D . . . .
H15 H 0.301980 0.244042 0.354929 0.027 Uiso 0.091(3) 1 calc R U P A 2
C16 C 0.0283(3) 0.18620(11) 0.34955(8) 0.0277(3) Uani 1 1 d D . . . .
C17 C -0.1449(2) 0.16805(12) 0.31227(9) 0.0290(3) Uani 1 1 d . . . . .
H17 H -0.251573 0.136526 0.328463 0.035 Uiso 1 1 calc R U . . .
C18 C -0.1591(2) 0.19713(11) 0.25031(9) 0.0289(3) Uani 1 1 d . . . . .
H18 H -0.276597 0.184784 0.223048 0.035 Uiso 1 1 calc R U . . .
C19 C -0.0031(2) 0.24428(10) 0.22757(8) 0.0243(3) Uani 1 1 d D . . . .
H19 H -0.015807 0.263986 0.186216 0.029 Uiso 0.909(3) 1 d R U P A 1
C20 C 1.1054(2) 0.58222(10) 0.41414(7) 0.0222(3) Uani 1 1 d . . . . .
C21 C 1.3026(2) 0.58710(12) 0.43986(8) 0.0290(3) Uani 1 1 d D . . . .
H21 H 1.403101 0.562323 0.416917 0.035 Uiso 0.091(3) 1 calc R U P A 2
C22 C 1.3561(2) 0.62713(14) 0.49800(9) 0.0332(4) Uani 1 1 d D . . . .
C23 C 1.2183(3) 0.66276(13) 0.53395(9) 0.0319(4) Uani 1 1 d . . . . .
H23 H 1.257226 0.690442 0.573731 0.038 Uiso 1 1 calc R U . . .
C24 C 1.0199(3) 0.65684(14) 0.51002(9) 0.0328(4) Uani 1 1 d . . . . .
H24 H 0.920195 0.679784 0.534053 0.039 Uiso 1 1 calc R U . . .
C25 C 0.9656(2) 0.61784(12) 0.45144(8) 0.0283(3) Uani 1 1 d D . . . .
H25 H 0.833026 0.615478 0.436770 0.034 Uiso 0.909(3) 1 d R U P A 1
N31 N 0.955(2) 0.4620(15) 0.0547(10) 0.0244(19) Uani 0.5 1 d . . P C -1
C31 C 0.9181(6) 0.5758(3) 0.04675(17) 0.0335(7) Uani 0.5 1 d . . P C -1
H31A H 0.776490 0.589494 0.050472 0.040 Uiso 0.5 1 calc R U P C -1
H31B H 0.998719 0.608059 0.081545 0.040 Uiso 0.5 1 calc R U P C -1
C32 C 0.9732(6) 0.6139(3) -0.01706(16) 0.0315(7) Uani 0.5 1 d . . P C -1
H32A H 1.076941 0.657965 -0.010239 0.038 Uiso 0.5 1 d R U P C -1
H32B H 0.862816 0.641451 -0.040969 0.038 Uiso 0.5 1 d R U P C -1
C33 C 0.8241(6) 0.4312(3) -0.00163(16) 0.0333(7) Uani 0.5 1 d . . P C -1
H33A H 0.687796 0.445895 0.003197 0.040 Uiso 0.5 1 d R U P C -1
H33B H 0.837701 0.365406 -0.000403 0.040 Uiso 0.5 1 d R U P C -1
C34 C 0.8789(5) 0.4697(3) -0.06541(15) 0.0302(7) Uani 0.5 1 d . . P C -1
H34A H 0.770543 0.502960 -0.086148 0.036 Uiso 0.5 1 d R U P C -1
H34B H 0.909567 0.419771 -0.091668 0.036 Uiso 0.5 1 d R U P C -1
C35 C 1.1581(6) 0.4552(3) 0.04327(18) 0.0367(8) Uani 0.5 1 d . . P C -1
H35A H 1.196546 0.389305 0.045737 0.044 Uiso 0.5 1 calc R U P C -1
H35B H 1.239566 0.487686 0.077781 0.044 Uiso 0.5 1 calc R U P C -1
C36 C 1.2136(5) 0.4941(3) -0.02036(17) 0.0352(8) Uani 0.5 1 d . . P C -1
H36A H 1.268551 0.445588 -0.043142 0.042 Uiso 0.5 1 d R U P C -1
H36B H 1.310722 0.541189 -0.013252 0.042 Uiso 0.5 1 d R U P C -1
N32 N 1.045(3) 0.5233(15) -0.0508(10) 0.033(3) Uani 0.5 1 d . . P C -1


_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
F3 C21 1.3626(19) . ?
F4 C22 1.3527(19) . ?
F3B C25 1.398(7) . ?
F2 C16 1.358(2) . ?
F1 C15 1.3574(17) . ?
F1B C19 1.408(7) . ?
C1 C2 1.384(2) . ?
C1 C10 1.395(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.411(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(2) . ?
C3 C14 1.482(2) . ?
C4 C11 1.3930(19) . ?
C4 H4 0.9500 . ?
C5 C12 1.393(2) . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(2) . ?
C6 C20 1.480(2) . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.390(2) . ?
C8 H8 0.9500 . ?
N9 C13 1.380(2) . ?
N9 C10 1.3823(19) . ?
N9 H9 0.90(2) . ?
C10 C11 1.411(2) . ?
C11 C12 1.446(2) . ?
C12 C13 1.4133(19) . ?
C14 C15 1.390(2) . ?
C14 C19 1.404(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.369(2) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9224 . ?
C20 C21 1.388(2) . ?
C20 C25 1.399(2) . ?
C21 C22 1.382(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.370(3) . ?
C23 C24 1.387(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9182 . ?
N31 C35 1.424(14) . ?
N31 C33 1.48(2) . ?
N31 C31 1.67(2) . ?
C31 C32 1.551(5) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.60(2) . ?
C32 H32A 0.9487 . ?
C32 H32B 0.9463 . ?
C33 C34 1.552(4) . ?
C33 H33A 0.9629 . ?
C33 H33B 0.9577 . ?
C34 N32 1.37(2) . ?
C34 H34A 0.9465 . ?
C34 H34B 0.9517 . ?
C35 C36 1.552(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.319(19) . ?
C36 H36A 0.9526 . ?
C36 H36B 0.9482 . ?

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
C2 C1 C10 117.67(14) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 122.47(14) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.01(14) . . ?
C4 C3 C14 121.53(13) . . ?
C2 C3 C14 119.45(13) . . ?
C11 C4 C3 119.52(14) . . ?
C11 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C12 C5 C6 119.56(13) . . ?
C12 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.26(14) . . ?
C5 C6 C20 119.87(13) . . ?
C7 C6 C20 120.78(13) . . ?
C8 C7 C6 122.06(14) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 118.11(13) . . ?
C7 C8 H8 120.9 . . ?
C13 C8 H8 120.9 . . ?
C13 N9 C10 108.41(12) . . ?
C13 N9 H9 125.1(13) . . ?
C10 N9 H9 126.5(13) . . ?
N9 C10 C1 129.22(14) . . ?
N9 C10 C11 109.45(13) . . ?
C1 C10 C11 121.23(14) . . ?
C4 C11 C10 120.07(13) . . ?
C4 C11 C12 133.47(13) . . ?
C10 C11 C12 106.34(12) . . ?
C5 C12 C13 119.78(13) . . ?
C5 C12 C11 133.89(13) . . ?
C13 C12 C11 106.31(12) . . ?
N9 C13 C8 129.32(14) . . ?
N9 C13 C12 109.44(13) . . ?
C8 C13 C12 121.24(14) . . ?
C15 C14 C19 115.50(14) . . ?
C15 C14 C3 122.74(13) . . ?
C19 C14 C3 121.74(14) . . ?
F1 C15 C16 116.28(14) . . ?
F1 C15 C14 122.03(13) . . ?
C16 C15 C14 121.62(14) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
F2 C16 C17 119.84(15) . . ?
F2 C16 C15 117.93(15) . . ?
C17 C16 C15 122.22(16) . . ?
C16 C17 C18 117.69(15) . . ?
C16 C17 H17 121.2 . . ?
C18 C17 H17 121.2 . . ?
C17 C18 C19 120.49(15) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 122.47(15) . . ?
C18 C19 F1B 116.0(5) . . ?
C14 C19 F1B 120.1(5) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 118.1 . . ?
C21 C20 C25 115.86(15) . . ?
C21 C20 C6 122.94(14) . . ?
C25 C20 C6 121.19(14) . . ?
F3 C21 C22 117.31(15) . . ?
F3 C21 C20 121.07(15) . . ?
C22 C21 C20 121.62(15) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
F4 C22 C23 120.11(16) . . ?
F4 C22 C21 117.76(16) . . ?
C23 C22 C21 122.13(16) . . ?
C22 C23 C24 117.44(16) . . ?
C22 C23 H23 121.3 . . ?
C24 C23 H23 121.3 . . ?
C25 C24 C23 120.66(16) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 F3B 115.4(7) . . ?
C24 C25 C20 122.27(15) . . ?
F3B C25 C20 118.3(7) . . ?
C24 C25 H25 118.5 . . ?
C20 C25 H25 119.2 . . ?
C35 N31 C33 110.1(12) . . ?
C35 N31 C31 100.8(12) . . ?
C33 N31 C31 98.3(11) . . ?
C32 C31 N31 113.1(7) . . ?
C32 C31 H31A 109.0 . . ?
N31 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
N31 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 N32 102.5(8) . . ?
C31 C32 H32A 110.4 . . ?
N32 C32 H32A 111.5 . . ?
C31 C32 H32B 111.9 . . ?
N32 C32 H32B 111.4 . . ?
H32A C32 H32B 109.1 . . ?
N31 C33 C34 115.1(8) . . ?
N31 C33 H33A 110.0 . . ?
C34 C33 H33A 109.6 . . ?
N31 C33 H33B 103.3 . . ?
C34 C33 H33B 110.5 . . ?
H33A C33 H33B 107.9 . . ?
N32 C34 C33 105.7(9) . . ?
N32 C34 H34A 113.1 . . ?
C33 C34 H34A 110.3 . . ?
N32 C34 H34B 109.8 . . ?
C33 C34 H34B 109.2 . . ?
H34A C34 H34B 108.6 . . ?
N31 C35 C36 117.0(9) . . ?
N31 C35 H35A 108.1 . . ?
C36 C35 H35A 108.1 . . ?
N31 C35 H35B 108.1 . . ?
C36 C35 H35B 108.1 . . ?
H35A C35 H35B 107.3 . . ?
N32 C36 C35 105.6(9) . . ?
N32 C36 H36A 110.5 . . ?
C35 C36 H36A 108.8 . . ?
N32 C36 H36B 113.3 . . ?
C35 C36 H36B 110.5 . . ?
H36A C36 H36B 108.1 . . ?
C36 N32 C34 124.9(17) . . ?
C36 N32 C32 109.3(14) . . ?
C34 N32 C32 106.6(11) . . ?

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
C10 C1 C2 C3 1.3(2) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C2 C3 C14 -179.30(14) . . . . ?
C2 C3 C4 C11 -1.7(2) . . . . ?
C14 C3 C4 C11 177.70(13) . . . . ?
C12 C5 C6 C7 -0.1(2) . . . . ?
C12 C5 C6 C20 176.38(13) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
C20 C6 C7 C8 -176.01(14) . . . . ?
C6 C7 C8 C13 -0.2(2) . . . . ?
C13 N9 C10 C1 -174.83(16) . . . . ?
C13 N9 C10 C11 1.62(17) . . . . ?
C2 C1 C10 N9 174.87(15) . . . . ?
C2 C1 C10 C11 -1.2(2) . . . . ?
C3 C4 C11 C10 1.8(2) . . . . ?
C3 C4 C11 C12 -173.55(15) . . . . ?
N9 C10 C11 C4 -177.12(13) . . . . ?
C1 C10 C11 C4 -0.3(2) . . . . ?
N9 C10 C11 C12 -0.64(16) . . . . ?
C1 C10 C11 C12 176.14(14) . . . . ?
C6 C5 C12 C13 -0.5(2) . . . . ?
C6 C5 C12 C11 178.02(15) . . . . ?
C4 C11 C12 C5 -3.4(3) . . . . ?
C10 C11 C12 C5 -179.18(16) . . . . ?
C4 C11 C12 C13 175.25(15) . . . . ?
C10 C11 C12 C13 -0.55(16) . . . . ?
C10 N9 C13 C8 177.64(15) . . . . ?
C10 N9 C13 C12 -1.98(17) . . . . ?
C7 C8 C13 N9 179.99(15) . . . . ?
C7 C8 C13 C12 -0.4(2) . . . . ?
C5 C12 C13 N9 -179.59(13) . . . . ?
C11 C12 C13 N9 1.56(16) . . . . ?
C5 C12 C13 C8 0.8(2) . . . . ?
C11 C12 C13 C8 -178.10(13) . . . . ?
C4 C3 C14 C15 -30.9(2) . . . . ?
C2 C3 C14 C15 148.47(15) . . . . ?
C4 C3 C14 C19 150.97(14) . . . . ?
C2 C3 C14 C19 -29.7(2) . . . . ?
C19 C14 C15 F1 176.37(14) . . . . ?
C3 C14 C15 F1 -1.9(2) . . . . ?
C19 C14 C15 C16 -0.5(2) . . . . ?
C3 C14 C15 C16 -178.74(14) . . . . ?
F1 C15 C16 F2 2.2(2) . . . . ?
C14 C15 C16 F2 179.20(14) . . . . ?
F1 C15 C16 C17 -177.12(15) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
F2 C16 C17 C18 -178.46(15) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -0.9(2) . . . . ?
C17 C18 C19 C14 0.4(2) . . . . ?
C17 C18 C19 F1B 166.6(6) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C3 C14 C19 C18 178.62(14) . . . . ?
C15 C14 C19 F1B -165.3(6) . . . . ?
C3 C14 C19 F1B 12.9(7) . . . . ?
C5 C6 C20 C21 145.59(16) . . . . ?
C7 C6 C20 C21 -37.9(2) . . . . ?
C5 C6 C20 C25 -35.1(2) . . . . ?
C7 C6 C20 C25 141.40(16) . . . . ?
C25 C20 C21 F3 178.59(16) . . . . ?
C6 C20 C21 F3 -2.0(3) . . . . ?
C25 C20 C21 C22 -1.7(3) . . . . ?
C6 C20 C21 C22 177.65(16) . . . . ?
F3 C21 C22 F4 0.4(3) . . . . ?
C20 C21 C22 F4 -179.32(17) . . . . ?
F3 C21 C22 C23 -179.19(18) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
F4 C22 C23 C24 -179.16(18) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C23 C24 C25 F3B -156.5(9) . . . . ?
C23 C24 C25 C20 0.5(3) . . . . ?
C21 C20 C25 C24 0.9(3) . . . . ?
C6 C20 C25 C24 -178.47(16) . . . . ?
C21 C20 C25 F3B 157.3(10) . . . . ?
C6 C20 C25 F3B -22.1(10) . . . . ?
C35 N31 C31 C32 54.4(12) . . . . ?
C33 N31 C31 C32 -58.1(8) . . . . ?
N31 C31 C32 N32 0.4(4) . . . . ?
C35 N31 C33 C34 -45.4(16) . . . . ?
C31 N31 C33 C34 59.3(8) . . . . ?
N31 C33 C34 N32 1.1(5) . . . . ?
C33 N31 C35 C36 46.6(17) . . . . ?
C31 N31 C35 C36 -56.5(12) . . . . ?
N31 C35 C36 N32 -1.9(5) . . . . ?
C35 C36 N32 C34 -57.0(18) . . . . ?
C35 C36 N32 C32 70.8(13) . . . . ?
C33 C34 N32 C36 57.2(17) . . . . ?
C33 C34 N32 C32 -71.7(12) . . . . ?
C31 C32 N32 C36 -68.3(13) . . . . ?
C31 C32 N32 C34 69.3(13) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.90(2) 1.91(3) 2.805(19) 174(2) . yes
N9 H9 N32 0.90(2) 2.03(3) 2.91(2) 168(2) 3_765 yes
C24 H24 F4 0.95 2.58 3.218(2) 124.6 1_455 yes
C31 H31A F2 0.99 2.64 3.595(4) 162.3 2 yes

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.061


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-7s-100K
_database_code_depnum_ccdc_archive 'CCDC 2022187'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 N, C6 H12 N2'
_chemical_formula_sum            'C30 H29 N3'
_chemical_formula_weight         431.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.1480(4)
_cell_length_b                   22.6374(10)
_cell_length_c                   11.7158(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.813(2)
_cell_angle_gamma                90
_cell_volume                     2334.37(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9674
_cell_measurement_theta_min      2.5459
_cell_measurement_theta_max      31.3987

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            66651
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.070
_diffrn_reflns_theta_max         31.434
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7141
_reflns_number_gt                6256
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0587P)²+0.6319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7141
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.56232(10) 0.85224(4) 0.42540(8) 0.02256(17) Uani 1 1 d . . . . .
H1 H 0.626908 0.863558 0.377962 0.027 Uiso 1 1 calc R U . . .
C2 C 0.48143(10) 0.89390(4) 0.46985(8) 0.02285(17) Uani 1 1 d . . . . .
H2 H 0.491709 0.934404 0.452280 0.027 Uiso 1 1 calc R U . . .
C3 C 0.38400(9) 0.87840(4) 0.54049(8) 0.01971(16) Uani 1 1 d . . . . .
C4 C 0.36616(9) 0.81898(4) 0.56533(7) 0.01879(15) Uani 1 1 d . . . . .
H4 H 0.300145 0.807738 0.611642 0.023 Uiso 1 1 calc R U . . .
C5 C 0.38043(9) 0.67076(4) 0.58177(7) 0.01903(15) Uani 1 1 d . . . . .
H5 H 0.306420 0.682740 0.620317 0.023 Uiso 1 1 calc R U . . .
C6 C 0.41576(9) 0.61109(4) 0.57580(8) 0.01964(16) Uani 1 1 d . . . . .
C7 C 0.52949(10) 0.59434(4) 0.52104(8) 0.02230(17) Uani 1 1 d . . . . .
H7 H 0.556659 0.553837 0.520966 0.027 Uiso 1 1 calc R U . . .
C8 C 0.60256(10) 0.63515(4) 0.46747(8) 0.02213(17) Uani 1 1 d . . . . .
H8 H 0.677328 0.623099 0.429729 0.027 Uiso 1 1 calc R U . . .
N9 N 0.61472(8) 0.74325(3) 0.42272(7) 0.02093(15) Uani 1 1 d . . . . .
H9 H 0.6934(15) 0.7432(5) 0.3887(12) 0.025 Uiso 1 1 d . U . . .
C10 C 0.54560(9) 0.79298(4) 0.45277(7) 0.01918(15) Uani 1 1 d . . . . .
C11 C 0.44656(9) 0.77623(4) 0.52127(7) 0.01792(15) Uani 1 1 d . . . . .
C12 C 0.45489(9) 0.71268(4) 0.53055(7) 0.01796(15) Uani 1 1 d . . . . .
C13 C 0.56270(9) 0.69444(4) 0.47080(7) 0.01944(16) Uani 1 1 d . . . . .
C14 C 0.30422(9) 0.92523(4) 0.58872(8) 0.02028(16) Uani 1 1 d . . . . .
C15 C 0.28400(9) 0.92052(4) 0.70276(8) 0.02154(16) Uani 1 1 d . . . . .
H15 H 0.319926 0.886436 0.749249 0.026 Uiso 1 1 calc R U . . .
C16 C 0.21207(10) 0.96507(4) 0.74873(9) 0.02483(18) Uani 1 1 d . . . . .
H16 H 0.198869 0.961156 0.826045 0.030 Uiso 1 1 calc R U . . .
C17 C 0.15944(11) 1.01529(4) 0.68203(10) 0.0285(2) Uani 1 1 d . . . . .
H17 H 0.110791 1.045815 0.713633 0.034 Uiso 1 1 calc R U . . .
C18 C 0.17840(11) 1.02057(4) 0.56889(10) 0.0291(2) Uani 1 1 d . . . . .
H18 H 0.142362 1.054789 0.522886 0.035 Uiso 1 1 calc R U . . .
C19 C 0.24987(10) 0.97602(4) 0.52258(9) 0.02553(18) Uani 1 1 d . . . . .
H19 H 0.262011 0.980106 0.444981 0.031 Uiso 1 1 calc R U . . .
C20 C 0.32980(9) 0.56552(4) 0.62142(8) 0.01950(16) Uani 1 1 d . . . . .
C21 C 0.17104(9) 0.56884(4) 0.59323(8) 0.02216(17) Uani 1 1 d . . . . .
H21 H 0.119782 0.600570 0.545800 0.027 Uiso 1 1 calc R U . . .
C22 C 0.08759(10) 0.52639(4) 0.63369(8) 0.02423(18) Uani 1 1 d . . . . .
H22 H -0.019996 0.529316 0.613927 0.029 Uiso 1 1 calc R U . . .
C23 C 0.16073(10) 0.47969(4) 0.70290(8) 0.02428(17) Uani 1 1 d . . . . .
H23 H 0.103665 0.450756 0.730909 0.029 Uiso 1 1 calc R U . . .
C24 C 0.31834(10) 0.47559(4) 0.73093(8) 0.02368(17) Uani 1 1 d . . . . .
H24 H 0.368966 0.443581 0.777796 0.028 Uiso 1 1 calc R U . . .
C25 C 0.40207(10) 0.51816(4) 0.69064(8) 0.02224(17) Uani 1 1 d . . . . .
H25 H 0.509610 0.514997 0.710418 0.027 Uiso 1 1 calc R U . . .
N31 N 0.12927(8) 0.24201(4) 0.18134(7) 0.02179(15) Uani 1 1 d . . . . .
C31 C 0.16990(12) 0.19396(5) 0.26920(9) 0.0300(2) Uani 1 1 d . . . . .
H31A H 0.275981 0.199242 0.317945 0.036 Uiso 1 1 calc R U . . .
H31B H 0.163019 0.155550 0.227659 0.036 Uiso 1 1 calc R U . . .
C32 C 0.06169(11) 0.19379(5) 0.35072(8) 0.02805(19) Uani 1 1 d . . . . .
H32A H 0.003647 0.156342 0.340057 0.034 Uiso 1 1 calc R U . . .
H32B H 0.122087 0.196362 0.434687 0.034 Uiso 1 1 calc R U . . .
C33 C 0.14498(12) 0.29846(5) 0.24575(9) 0.0286(2) Uani 1 1 d . . . . .
H33A H 0.114354 0.331320 0.188457 0.034 Uiso 1 1 calc R U . . .
H33B H 0.252566 0.304501 0.290341 0.034 Uiso 1 1 calc R U . . .
C34 C 0.04428(11) 0.29872(5) 0.33308(9) 0.0288(2) Uani 1 1 d . . . . .
H34A H 0.109447 0.302828 0.415362 0.035 Uiso 1 1 calc R U . . .
H34B H -0.025659 0.332948 0.315733 0.035 Uiso 1 1 calc R U . . .
C35 C -0.03139(11) 0.23431(6) 0.11414(9) 0.0342(2) Uani 1 1 d . . . . .
H35A H -0.044804 0.195410 0.073997 0.041 Uiso 1 1 calc R U . . .
H35B H -0.060386 0.265335 0.052546 0.041 Uiso 1 1 calc R U . . .
C36 C -0.13551(11) 0.23819(6) 0.19844(8) 0.0330(2) Uani 1 1 d . . . . .
H36A H -0.203733 0.272760 0.176665 0.040 Uiso 1 1 calc R U . . .
H36B H -0.199272 0.202255 0.189690 0.040 Uiso 1 1 calc R U . . .
N32 N -0.04413(9) 0.24386(4) 0.32235(7) 0.02666(17) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3850(12) . ?
C1 C10 1.3973(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.4158(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3952(12) . ?
C3 C14 1.4833(12) . ?
C4 C11 1.3968(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3952(12) . ?
C5 C12 1.3955(11) . ?
C5 H5 0.9500 . ?
C6 C7 1.4148(11) . ?
C6 C20 1.4822(12) . ?
C7 C8 1.3867(12) . ?
C7 H7 0.9500 . ?
C8 C13 1.3942(12) . ?
C8 H8 0.9500 . ?
N9 C13 1.3823(11) . ?
N9 C10 1.3829(11) . ?
N9 H9 0.913(14) . ?
C10 C11 1.4160(11) . ?
C11 C12 1.4430(12) . ?
C12 C13 1.4176(11) . ?
C14 C19 1.4000(13) . ?
C14 C15 1.4018(12) . ?
C15 C16 1.3905(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.3891(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3880(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3899(13) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.3971(12) . ?
C20 C21 1.4009(11) . ?
C21 C22 1.3887(12) . ?
C21 H21 0.9500 . ?
C22 C23 1.3882(13) . ?
C22 H22 0.9500 . ?
C23 C24 1.3918(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.3912(12) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C33 1.4709(12) . ?
N31 C31 1.4740(13) . ?
N31 C35 1.4763(12) . ?
C31 C32 1.5516(13) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.4686(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.5521(13) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.4686(14) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5502(13) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.4701(12) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

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
C2 C1 C10 117.66(8) . . ?
C2 C1 H1 121.2 . . ?
C10 C1 H1 121.2 . . ?
C1 C2 C3 122.49(8) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.27(8) . . ?
C4 C3 C14 120.79(7) . . ?
C2 C3 C14 119.94(8) . . ?
C3 C4 C11 119.19(7) . . ?
C3 C4 H4 120.4 . . ?
C11 C4 H4 120.4 . . ?
C6 C5 C12 119.34(7) . . ?
C6 C5 H5 120.3 . . ?
C12 C5 H5 120.3 . . ?
C5 C6 C7 119.42(8) . . ?
C5 C6 C20 120.19(7) . . ?
C7 C6 C20 120.33(8) . . ?
C8 C7 C6 122.11(8) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C13 117.82(8) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.36(7) . . ?
C13 N9 H9 125.2(8) . . ?
C10 N9 H9 125.6(8) . . ?
N9 C10 C1 129.55(8) . . ?
N9 C10 C11 109.50(7) . . ?
C1 C10 C11 120.95(8) . . ?
C4 C11 C10 120.43(8) . . ?
C4 C11 C12 133.26(7) . . ?
C10 C11 C12 106.31(7) . . ?
C5 C12 C13 120.07(8) . . ?
C5 C12 C11 133.49(7) . . ?
C13 C12 C11 106.43(7) . . ?
N9 C13 C8 129.53(8) . . ?
N9 C13 C12 109.35(8) . . ?
C8 C13 C12 121.11(8) . . ?
C19 C14 C15 118.08(8) . . ?
C19 C14 C3 120.90(8) . . ?
C15 C14 C3 121.01(8) . . ?
C16 C15 C14 120.89(8) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 120.24(9) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.56(9) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.32(9) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.91(9) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C25 C20 C21 118.31(8) . . ?
C25 C20 C6 121.98(7) . . ?
C21 C20 C6 119.70(8) . . ?
C22 C21 C20 120.89(8) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 120.28(8) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.47(8) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.30(8) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 120.75(8) . . ?
C24 C25 H25 119.6 . . ?
C20 C25 H25 119.6 . . ?
C33 N31 C31 108.18(8) . . ?
C33 N31 C35 108.67(8) . . ?
C31 N31 C35 108.07(8) . . ?
N31 C31 C32 110.48(8) . . ?
N31 C31 H31A 109.6 . . ?
C32 C31 H31A 109.6 . . ?
N31 C31 H31B 109.6 . . ?
C32 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
N32 C32 C31 110.52(8) . . ?
N32 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 . . ?
N32 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 110.43(8) . . ?
N31 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
N31 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N32 C34 C33 110.62(8) . . ?
N32 C34 H34A 109.5 . . ?
C33 C34 H34A 109.5 . . ?
N32 C34 H34B 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.41(8) . . ?
N31 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N31 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 110.57(7) . . ?
N32 C36 H36A 109.5 . . ?
C35 C36 H36A 109.5 . . ?
N32 C36 H36B 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C32 N32 C34 108.64(8) . . ?
C32 N32 C36 108.58(8) . . ?
C34 N32 C36 108.06(8) . . ?

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
C10 C1 C2 C3 -0.18(13) . . . . ?
C1 C2 C3 C4 -1.00(13) . . . . ?
C1 C2 C3 C14 178.03(8) . . . . ?
C2 C3 C4 C11 0.89(12) . . . . ?
C14 C3 C4 C11 -178.13(7) . . . . ?
C12 C5 C6 C7 1.84(12) . . . . ?
C12 C5 C6 C20 -175.31(7) . . . . ?
C5 C6 C7 C8 -3.25(13) . . . . ?
C20 C6 C7 C8 173.89(8) . . . . ?
C6 C7 C8 C13 1.22(13) . . . . ?
C13 N9 C10 C1 179.62(9) . . . . ?
C13 N9 C10 C11 -0.18(10) . . . . ?
C2 C1 C10 N9 -178.34(9) . . . . ?
C2 C1 C10 C11 1.44(13) . . . . ?
C3 C4 C11 C10 0.34(12) . . . . ?
C3 C4 C11 C12 179.62(8) . . . . ?
N9 C10 C11 C4 178.26(7) . . . . ?
C1 C10 C11 C4 -1.55(12) . . . . ?
N9 C10 C11 C12 -1.19(9) . . . . ?
C1 C10 C11 C12 178.99(8) . . . . ?
C6 C5 C12 C13 1.44(12) . . . . ?
C6 C5 C12 C11 -179.68(8) . . . . ?
C4 C11 C12 C5 3.71(16) . . . . ?
C10 C11 C12 C5 -176.94(9) . . . . ?
C4 C11 C12 C13 -177.30(9) . . . . ?
C10 C11 C12 C13 2.05(9) . . . . ?
C10 N9 C13 C8 -177.97(9) . . . . ?
C10 N9 C13 C12 1.53(9) . . . . ?
C7 C8 C13 N9 -178.40(8) . . . . ?
C7 C8 C13 C12 2.16(13) . . . . ?
C5 C12 C13 N9 176.93(7) . . . . ?
C11 C12 C13 N9 -2.23(9) . . . . ?
C5 C12 C13 C8 -3.53(12) . . . . ?
C11 C12 C13 C8 177.32(8) . . . . ?
C4 C3 C14 C19 -144.54(9) . . . . ?
C2 C3 C14 C19 36.44(12) . . . . ?
C4 C3 C14 C15 36.87(12) . . . . ?
C2 C3 C14 C15 -142.14(9) . . . . ?
C19 C14 C15 C16 -0.02(13) . . . . ?
C3 C14 C15 C16 178.60(8) . . . . ?
C14 C15 C16 C17 -0.25(13) . . . . ?
C15 C16 C17 C18 0.34(14) . . . . ?
C16 C17 C18 C19 -0.16(15) . . . . ?
C17 C18 C19 C14 -0.12(15) . . . . ?
C15 C14 C19 C18 0.21(13) . . . . ?
C3 C14 C19 C18 -178.41(8) . . . . ?
C5 C6 C20 C25 -135.96(9) . . . . ?
C7 C6 C20 C25 46.93(12) . . . . ?
C5 C6 C20 C21 45.24(12) . . . . ?
C7 C6 C20 C21 -131.88(9) . . . . ?
C25 C20 C21 C22 0.43(13) . . . . ?
C6 C20 C21 C22 179.28(8) . . . . ?
C20 C21 C22 C23 -0.12(14) . . . . ?
C21 C22 C23 C24 -0.32(14) . . . . ?
C22 C23 C24 C25 0.44(14) . . . . ?
C23 C24 C25 C20 -0.13(14) . . . . ?
C21 C20 C25 C24 -0.30(13) . . . . ?
C6 C20 C25 C24 -179.13(8) . . . . ?
C33 N31 C31 C32 60.86(10) . . . . ?
C35 N31 C31 C32 -56.63(10) . . . . ?
N31 C31 C32 N32 -3.68(12) . . . . ?
C31 N31 C33 C34 -57.05(10) . . . . ?
C35 N31 C33 C34 60.06(10) . . . . ?
N31 C33 C34 N32 -2.92(12) . . . . ?
C33 N31 C35 C36 -55.98(12) . . . . ?
C31 N31 C35 C36 61.19(12) . . . . ?
N31 C35 C36 N32 -4.35(14) . . . . ?
C31 C32 N32 C34 -56.47(10) . . . . ?
C31 C32 N32 C36 60.82(10) . . . . ?
C33 C34 N32 C32 60.31(10) . . . . ?
C33 C34 N32 C36 -57.31(10) . . . . ?
C35 C36 N32 C32 -56.25(12) . . . . ?
C35 C36 N32 C34 61.41(12) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.913(14) 2.008(14) 2.9203(10) 178.1(12) 2_655 yes

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3II-150K
_database_code_depnum_ccdc_archive 'CCDC 2022183'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0037 0.0018 '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 0.0071 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0190 0.0112 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   19.1368(8)
_cell_length_b                   6.7789(3)
_cell_length_c                   17.4066(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.3730(10)
_cell_angle_gamma                90
_cell_volume                     2130.24(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9624
_cell_measurement_theta_min      2.3136
_cell_measurement_theta_max      31.3857

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            73488
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.314
_diffrn_reflns_theta_max         31.414
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             6498
_reflns_number_gt                6097
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0852P)²+0.8046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.072(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6498
_refine_ls_number_parameters     338
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1484
_refine_ls_wR_factor_gt          0.1458
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.091
_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
F1 F 0.07590(4) 1.15793(11) 0.77569(5) 0.03225(18) Uani 1 1 d . . . . .
F2 F 0.09685(5) 1.45192(12) 0.88183(6) 0.0396(2) Uani 1 1 d . . . . .
F3 F 0.44291(4) 0.79891(11) 0.60508(6) 0.0415(2) Uani 1 1 d . . . . .
F4 F 0.57368(5) 0.83998(14) 0.58724(8) 0.0531(3) Uani 1 1 d . . . . .
N9 N 0.17193(5) 0.35713(14) 0.64372(6) 0.02483(19) Uani 1 1 d . . . . .
H9 H 0.1343(9) 0.284(3) 0.6139(10) 0.030 Uiso 1 1 d . U . . .
C1 C 0.10820(6) 0.58090(16) 0.71456(7) 0.0245(2) Uani 1 1 d . . . . .
H1 H 0.062864 0.509846 0.699267 0.029 Uiso 1 1 calc R U . . .
C2 C 0.11844(6) 0.74813(16) 0.76292(6) 0.0232(2) Uani 1 1 d . . . . .
H2 H 0.079292 0.790915 0.781092 0.028 Uiso 1 1 calc R U . . .
C3 C 0.18507(5) 0.85682(15) 0.78602(6) 0.02023(19) Uani 1 1 d . . . . .
C4 C 0.24279(5) 0.79659(15) 0.75911(6) 0.02111(19) Uani 1 1 d . . . . .
H4 H 0.287626 0.869771 0.773504 0.025 Uiso 1 1 calc R U . . .
C5 C 0.35321(6) 0.55711(15) 0.67358(6) 0.0228(2) Uani 1 1 d . . . . .
H5 H 0.380476 0.669221 0.700037 0.027 Uiso 1 1 calc R U . . .
C6 C 0.38418(6) 0.42455(15) 0.63271(6) 0.0232(2) Uani 1 1 d . . . . .
C7 C 0.34298(6) 0.25731(16) 0.59456(7) 0.0265(2) Uani 1 1 d . . . . .
H7 H 0.364728 0.166781 0.567463 0.032 Uiso 1 1 calc R U . . .
C8 C 0.27200(6) 0.22109(16) 0.59539(7) 0.0265(2) Uani 1 1 d . . . . .
H8 H 0.245161 0.107755 0.569611 0.032 Uiso 1 1 calc R U . . .
C10 C 0.16677(6) 0.52039(15) 0.68908(6) 0.02211(19) Uani 1 1 d . . . . .
C11 C 0.23398(5) 0.62769(15) 0.71083(6) 0.02073(19) Uani 1 1 d . . . . .
C12 C 0.28174(5) 0.52343(15) 0.67522(6) 0.02117(19) Uani 1 1 d . . . . .
C13 C 0.24124(6) 0.35671(15) 0.63538(6) 0.0226(2) Uani 1 1 d . . . . .
C14 C 0.19620(5) 1.02744(15) 0.84224(6) 0.01981(18) Uani 1 1 d . . . . .
C15 C 0.14183(6) 1.16838(16) 0.83594(6) 0.0223(2) Uani 1 1 d . . . . .
C16 C 0.15312(7) 1.32378(16) 0.89037(7) 0.0269(2) Uani 1 1 d . . . . .
C17 C 0.21898(8) 1.34706(18) 0.95278(7) 0.0320(3) Uani 1 1 d . . . . .
H17 H 0.226359 1.454398 0.989713 0.038 Uiso 1 1 calc R U . . .
C18 C 0.27440(7) 1.20931(19) 0.96029(7) 0.0313(2) Uani 1 1 d . . . . .
H18 H 0.320590 1.222485 1.002782 0.038 Uiso 1 1 calc R U . . .
C19 C 0.26306(6) 1.05240(17) 0.90635(6) 0.0246(2) Uani 1 1 d . . . . .
H19 H 0.301724 0.959227 0.913073 0.030 Uiso 1 1 calc R U . . .
C20 C 0.45944(6) 0.45277(16) 0.62791(7) 0.0246(2) Uani 1 1 d . . . . .
C21 C 0.48526(6) 0.63536(17) 0.61316(7) 0.0279(2) Uani 1 1 d . . . . .
C22 C 0.55370(7) 0.65754(19) 0.60339(9) 0.0331(3) Uani 1 1 d . . . . .
C23 C 0.60038(7) 0.5009(2) 0.60942(9) 0.0372(3) Uani 1 1 d . . . . .
H23 H 0.647325 0.517572 0.602752 0.045 Uiso 1 1 calc R U . . .
C24 C 0.57678(8) 0.3175(2) 0.62558(10) 0.0405(3) Uani 1 1 d . . . . .
H24 H 0.608207 0.206333 0.630626 0.049 Uiso 1 1 calc R U . . .
C25 C 0.50776(7) 0.29349(19) 0.63455(9) 0.0343(3) Uani 1 1 d . . . . .
H25 H 0.492954 0.165695 0.645459 0.041 Uiso 1 1 calc R U . . .
N31 N 0.0495(9) 0.116(2) 0.5396(9) 0.0341(14) Uani 0.5 1 d . U P . .
C31 C 0.0797(2) -0.0922(5) 0.5609(3) 0.0670(12) Uani 0.5 1 d . U P A -1
H31A H 0.098082 -0.111544 0.620635 0.080 Uiso 0.5 1 calc R U P A -1
H31B H 0.120835 -0.117278 0.539574 0.080 Uiso 0.5 1 calc R U P A -1
C32 C 0.0133(2) -0.2331(5) 0.5199(2) 0.0559(9) Uani 0.5 1 d . U P A -1
H32A H 0.029691 -0.338080 0.490129 0.067 Uiso 0.5 1 calc R U P A -1
H32B H -0.002469 -0.296850 0.562586 0.067 Uiso 0.5 1 calc R U P A -1
C33 C 0.0445(3) 0.1262(7) 0.4543(2) 0.0638(11) Uani 0.5 1 d . U P A -1
H33A H 0.093467 0.099053 0.448851 0.077 Uiso 0.5 1 calc R U P A -1
H33B H 0.028351 0.259470 0.432226 0.077 Uiso 0.5 1 calc R U P A -1
C34 C -0.0122(2) -0.0292(5) 0.40707(15) 0.0486(8) Uani 0.5 1 d . U P A -1
H34A H -0.048264 0.033499 0.358714 0.058 Uiso 0.5 1 calc R U P A -1
H34B H 0.013831 -0.134281 0.387720 0.058 Uiso 0.5 1 calc R U P A -1
C35 C -0.0096(2) 0.1535(9) 0.5562(4) 0.0903(17) Uani 0.5 1 d . U P A -1
H35A H -0.023232 0.294002 0.544739 0.108 Uiso 0.5 1 calc R U P A -1
H35B H -0.000657 0.129434 0.614839 0.108 Uiso 0.5 1 calc R U P A -1
C36 C -0.07451(19) 0.0198(9) 0.5041(4) 0.0881(17) Uani 0.5 1 d . U P A -1
H36A H -0.097137 -0.046073 0.540867 0.106 Uiso 0.5 1 calc R U P A -1
H36B H -0.112891 0.104587 0.466440 0.106 Uiso 0.5 1 calc R U P A -1
N32 N -0.0538(9) -0.122(2) 0.4595(8) 0.0302(12) Uani 0.5 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.3487(12) . ?
F2 C16 1.3528(13) . ?
F3 C21 1.3527(13) . ?
F4 C22 1.3514(15) . ?
N9 C13 1.3813(13) . ?
N9 C10 1.3820(13) . ?
N9 H9 0.885(17) . ?
C1 C2 1.3866(15) . ?
C1 C10 1.3968(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.4108(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3962(13) . ?
C3 C14 1.4841(13) . ?
C4 C11 1.3970(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3943(14) . ?
C5 C12 1.3963(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.4144(15) . ?
C6 C20 1.4826(14) . ?
C7 C8 1.3852(15) . ?
C7 H7 0.9500 . ?
C8 C13 1.3958(14) . ?
C8 H8 0.9500 . ?
C10 C11 1.4154(13) . ?
C11 C12 1.4474(13) . ?
C12 C13 1.4151(13) . ?
C14 C15 1.3899(14) . ?
C14 C19 1.4014(14) . ?
C15 C16 1.3851(15) . ?
C16 C17 1.3730(18) . ?
C17 C18 1.3863(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3874(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3878(16) . ?
C20 C25 1.4012(16) . ?
C21 C22 1.3839(16) . ?
C22 C23 1.3691(18) . ?
C23 C24 1.383(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.3901(18) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 N32 0.09(3) 3_556 ?
N31 C35 1.284(18) . ?
N31 C33 1.458(15) . ?
N31 C31 1.526(18) . ?
C31 C32 1.560(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.559(16) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.540(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.530(14) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.562(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.372(15) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N9 C10 108.34(8) . . ?
C13 N9 H9 124.2(11) . . ?
C10 N9 H9 125.6(11) . . ?
C2 C1 C10 117.79(9) . . ?
C2 C1 H1 121.1 . . ?
C10 C1 H1 121.1 . . ?
C1 C2 C3 122.16(9) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 119.51(9) . . ?
C4 C3 C14 119.51(9) . . ?
C2 C3 C14 120.89(9) . . ?
C3 C4 C11 119.37(9) . . ?
C3 C4 H4 120.3 . . ?
C11 C4 H4 120.3 . . ?
C6 C5 C12 119.34(9) . . ?
C6 C5 H5 120.3 . . ?
C12 C5 H5 120.3 . . ?
C5 C6 C7 119.42(10) . . ?
C5 C6 C20 122.06(9) . . ?
C7 C6 C20 118.52(9) . . ?
C8 C7 C6 122.21(10) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C13 117.76(10) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
N9 C10 C1 129.31(9) . . ?
N9 C10 C11 109.49(9) . . ?
C1 C10 C11 121.18(9) . . ?
C4 C11 C10 119.98(9) . . ?
C4 C11 C12 133.67(9) . . ?
C10 C11 C12 106.34(8) . . ?
C5 C12 C13 120.10(9) . . ?
C5 C12 C11 133.70(9) . . ?
C13 C12 C11 106.19(9) . . ?
N9 C13 C8 129.22(10) . . ?
N9 C13 C12 109.62(9) . . ?
C8 C13 C12 121.16(10) . . ?
C15 C14 C19 116.22(9) . . ?
C15 C14 C3 122.94(9) . . ?
C19 C14 C3 120.84(9) . . ?
F1 C15 C16 117.74(9) . . ?
F1 C15 C14 120.53(9) . . ?
C16 C15 C14 121.73(10) . . ?
F2 C16 C17 120.10(10) . . ?
F2 C16 C15 118.38(11) . . ?
C17 C16 C15 121.51(10) . . ?
C16 C17 C18 118.03(10) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C17 C18 C19 120.63(11) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 121.87(10) . . ?
C18 C19 H19 119.1 . . ?
C14 C19 H19 119.1 . . ?
C21 C20 C25 115.91(10) . . ?
C21 C20 C6 122.52(10) . . ?
C25 C20 C6 121.52(10) . . ?
F3 C21 C22 117.19(11) . . ?
F3 C21 C20 120.83(10) . . ?
C22 C21 C20 121.95(11) . . ?
F4 C22 C23 120.22(11) . . ?
F4 C22 C21 118.02(11) . . ?
C23 C22 C21 121.76(12) . . ?
C22 C23 C24 117.64(11) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C23 C24 C25 120.98(12) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 121.74(12) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
N32 N31 C35 137(10) 3_556 . ?
N32 N31 C33 84(10) 3_556 . ?
C35 N31 C33 117.1(12) . . ?
N32 N31 C31 95(10) 3_556 . ?
C35 N31 C31 114.7(11) . . ?
C33 N31 C31 100.5(10) . . ?
N31 C31 C32 105.8(6) . . ?
N31 C31 H31A 110.6 . . ?
C32 C31 H31A 110.6 . . ?
N31 C31 H31B 110.6 . . ?
C32 C31 H31B 110.6 . . ?
H31A C31 H31B 108.7 . . ?
N32 C32 C31 112.1(6) . . ?
N32 C32 H32A 109.2 . . ?
C31 C32 H32A 109.2 . . ?
N32 C32 H32B 109.2 . . ?
C31 C32 H32B 109.2 . . ?
H32A C32 H32B 107.9 . . ?
N31 C33 C34 108.0(6) . . ?
N31 C33 H33A 110.1 . . ?
C34 C33 H33A 110.1 . . ?
N31 C33 H33B 110.1 . . ?
C34 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?
N32 C34 C33 112.1(6) . . ?
N32 C34 H34A 109.2 . . ?
C33 C34 H34A 109.2 . . ?
N32 C34 H34B 109.2 . . ?
C33 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
N31 C35 C36 110.2(7) . . ?
N31 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N31 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 114.3(7) . . ?
N32 C36 H36A 108.7 . . ?
C35 C36 H36A 108.7 . . ?
N32 C36 H36B 108.7 . . ?
C35 C36 H36B 108.7 . . ?
H36A C36 H36B 107.6 . . ?
N31 N32 C36 92(10) 3_556 . ?
N31 N32 C34 44(10) 3_556 . ?
C36 N32 C34 110.9(10) . . ?
N31 N32 C32 64(10) 3_556 . ?
C36 N32 C32 106.6(9) . . ?
C34 N32 C32 97.1(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
C10 C1 C2 C3 0.40(16) . . . . ?
C1 C2 C3 C4 0.59(16) . . . . ?
C1 C2 C3 C14 -175.95(10) . . . . ?
C2 C3 C4 C11 -1.04(15) . . . . ?
C14 C3 C4 C11 175.54(9) . . . . ?
C12 C5 C6 C7 -0.76(16) . . . . ?
C12 C5 C6 C20 179.34(10) . . . . ?
C5 C6 C7 C8 0.82(17) . . . . ?
C20 C6 C7 C8 -179.28(11) . . . . ?
C6 C7 C8 C13 0.21(17) . . . . ?
C13 N9 C10 C1 -178.63(11) . . . . ?
C13 N9 C10 C11 -0.18(12) . . . . ?
C2 C1 C10 N9 177.37(11) . . . . ?
C2 C1 C10 C11 -0.92(16) . . . . ?
C3 C4 C11 C10 0.53(15) . . . . ?
C3 C4 C11 C12 -178.12(11) . . . . ?
N9 C10 C11 C4 -178.13(9) . . . . ?
C1 C10 C11 C4 0.47(16) . . . . ?
N9 C10 C11 C12 0.86(12) . . . . ?
C1 C10 C11 C12 179.46(10) . . . . ?
C6 C5 C12 C13 -0.30(16) . . . . ?
C6 C5 C12 C11 -179.95(11) . . . . ?
C4 C11 C12 C5 -2.7(2) . . . . ?
C10 C11 C12 C5 178.50(11) . . . . ?
C4 C11 C12 C13 177.60(11) . . . . ?
C10 C11 C12 C13 -1.19(11) . . . . ?
C10 N9 C13 C8 179.41(11) . . . . ?
C10 N9 C13 C12 -0.61(12) . . . . ?
C7 C8 C13 N9 178.68(11) . . . . ?
C7 C8 C13 C12 -1.30(17) . . . . ?
C5 C12 C13 N9 -178.62(9) . . . . ?
C11 C12 C13 N9 1.12(12) . . . . ?
C5 C12 C13 C8 1.37(16) . . . . ?
C11 C12 C13 C8 -178.89(10) . . . . ?
C4 C3 C14 C15 140.25(10) . . . . ?
C2 C3 C14 C15 -43.22(14) . . . . ?
C4 C3 C14 C19 -40.87(14) . . . . ?
C2 C3 C14 C19 135.67(11) . . . . ?
C19 C14 C15 F1 179.31(9) . . . . ?
C3 C14 C15 F1 -1.76(15) . . . . ?
C19 C14 C15 C16 -0.40(15) . . . . ?
C3 C14 C15 C16 178.53(10) . . . . ?
F1 C15 C16 F2 2.21(15) . . . . ?
C14 C15 C16 F2 -178.06(9) . . . . ?
F1 C15 C16 C17 -179.06(10) . . . . ?
C14 C15 C16 C17 0.67(17) . . . . ?
F2 C16 C17 C18 178.43(11) . . . . ?
C15 C16 C17 C18 -0.28(17) . . . . ?
C16 C17 C18 C19 -0.34(18) . . . . ?
C17 C18 C19 C14 0.59(18) . . . . ?
C15 C14 C19 C18 -0.21(16) . . . . ?
C3 C14 C19 C18 -179.17(10) . . . . ?
C5 C6 C20 C21 -42.34(16) . . . . ?
C7 C6 C20 C21 137.76(12) . . . . ?
C5 C6 C20 C25 140.51(12) . . . . ?
C7 C6 C20 C25 -39.39(16) . . . . ?
C25 C20 C21 F3 179.51(11) . . . . ?
C6 C20 C21 F3 2.21(17) . . . . ?
C25 C20 C21 C22 1.73(17) . . . . ?
C6 C20 C21 C22 -175.57(11) . . . . ?
F3 C21 C22 F4 0.55(18) . . . . ?
C20 C21 C22 F4 178.41(12) . . . . ?
F3 C21 C22 C23 -179.24(12) . . . . ?
C20 C21 C22 C23 -1.4(2) . . . . ?
F4 C22 C23 C24 -179.63(14) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 0.6(2) . . . . ?
C23 C24 C25 C20 -0.2(2) . . . . ?
C21 C20 C25 C24 -0.96(19) . . . . ?
C6 C20 C25 C24 176.37(12) . . . . ?
N32 N31 C31 C32 -159(18) 3_556 . . . ?
C35 N31 C31 C32 52.2(11) . . . . ?
C33 N31 C31 C32 -74.3(9) . . . . ?
N31 C31 C32 N32 11.0(5) . . . . ?
N32 N31 C33 C34 157(23) 3_556 . . . ?
C35 N31 C33 C34 -61.5(14) . . . . ?
C31 N31 C33 C34 63.4(9) . . . . ?
N31 C33 C34 N32 8.8(5) . . . . ?
N32 N31 C35 C36 167(31) 3_556 . . . ?
C33 N31 C35 C36 53.7(14) . . . . ?
C31 N31 C35 C36 -63.7(12) . . . . ?
N31 C35 C36 N32 7.0(9) . . . . ?
C35 C36 N32 N31 -12(21) . . . 3_556 ?
C35 C36 N32 C34 -53.3(12) . . . . ?
C35 C36 N32 C32 51.3(11) . . . . ?
C33 C34 N32 N31 -28(32) . . . 3_556 ?
C33 C34 N32 C36 43.3(12) . . . . ?
C33 C34 N32 C32 -67.5(8) . . . . ?
C31 C32 N32 N31 25(22) . . . 3_556 ?
C31 C32 N32 C36 -59.5(10) . . . . ?
C31 C32 N32 C34 54.8(8) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.885(17) 2.05(2) 2.936(14) 176.7(16) . yes
C34 H34A F1 0.99 2.57 3.130(3) 115.6 3_566 yes
C34 H34B F1 0.99 2.60 3.375(4) 134.9 4_565 yes
C35 H35A F2 0.99 2.44 3.039(4) 118.3 2_546 yes

_refine_diff_density_max         0.863
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.105


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-2-150K
_database_code_depnum_ccdc_archive 'CCDC 2022175'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H37 F8 N4'
_chemical_formula_weight         893.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 '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                   6.6613(3)
_cell_length_b                   14.8875(6)
_cell_length_c                   21.2797(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.554(2)
_cell_angle_gamma                90
_cell_volume                     2100.40(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9892
_cell_measurement_theta_min      2.9744
_cell_measurement_theta_max      31.3891

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             922
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            60836
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.420
_diffrn_reflns_theta_max         31.412
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6418
_reflns_number_gt                5748
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0778P)²+0.4199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.061(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6418
_refine_ls_number_parameters     338
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
F1 F -0.02751(10) 0.23637(5) 0.15421(3) 0.03550(17) Uani 1 1 d . . . . .
F2 F 0.03915(12) 0.15385(5) 0.40322(3) 0.04126(19) Uani 1 1 d . . . . .
F3 F 1.40242(10) 0.53879(5) 0.42388(4) 0.04063(18) Uani 1 1 d . . . . .
F4 F 0.77892(11) 0.68813(6) 0.53196(4) 0.0467(2) Uani 1 1 d . . . . .
C1 C 0.54467(17) 0.32993(7) 0.14345(5) 0.0289(2) Uani 1 1 d . . . . .
H1 H 0.571218 0.323706 0.100596 0.035 Uiso 1 1 calc R U . . .
C2 C 0.38123(16) 0.28752(7) 0.16589(5) 0.0274(2) Uani 1 1 d . . . . .
H2 H 0.296331 0.251196 0.137871 0.033 Uiso 1 1 calc R U . . .
C3 C 0.33635(14) 0.29650(6) 0.22928(4) 0.02344(18) Uani 1 1 d . . . . .
C4 C 0.46021(14) 0.35102(6) 0.27000(4) 0.02268(18) Uani 1 1 d . . . . .
H4 H 0.430092 0.359500 0.312332 0.027 Uiso 1 1 calc R U . . .
C5 C 0.83444(13) 0.48065(6) 0.33945(4) 0.02236(18) Uani 1 1 d . . . . .
H5 H 0.744288 0.470848 0.370740 0.027 Uiso 1 1 calc R U . . .
C6 C 1.01196(14) 0.52945(6) 0.35402(4) 0.02302(18) Uani 1 1 d . . . . .
C7 C 1.14444(14) 0.54321(6) 0.30690(5) 0.02569(19) Uani 1 1 d . . . . .
H7 H 1.266502 0.575188 0.317396 0.031 Uiso 1 1 calc R U . . .
C8 C 1.10186(15) 0.51157(7) 0.24604(5) 0.0266(2) Uani 1 1 d . . . . .
H8 H 1.191142 0.522296 0.214645 0.032 Uiso 1 1 calc R U . . .
N9 N 0.84652(14) 0.42546(6) 0.17598(4) 0.02721(18) Uani 1 1 d . . . . .
H9 H 0.898(2) 0.4326(10) 0.1385(7) 0.033 Uiso 1 1 d . U . . .
C10 C 0.66924(15) 0.38194(6) 0.18524(4) 0.02488(19) Uani 1 1 d . . . . .
C11 C 0.62746(14) 0.39289(6) 0.24869(4) 0.02210(18) Uani 1 1 d . . . . .
C12 C 0.79048(13) 0.44646(6) 0.27876(4) 0.02145(17) Uani 1 1 d . . . . .
C13 C 0.92350(14) 0.46335(6) 0.23218(4) 0.02365(18) Uani 1 1 d . . . . .
C14 C 0.16760(14) 0.24704(6) 0.25382(5) 0.02388(18) Uani 1 1 d . . . . .
C15 C -0.00749(15) 0.21959(7) 0.21727(5) 0.0276(2) Uani 1 1 d . . . . .
C16 C -0.16555(16) 0.17532(7) 0.24117(6) 0.0334(2) Uani 1 1 d . . . . .
H16 H -0.282462 0.159863 0.214195 0.040 Uiso 1 1 calc R U . . .
C17 C -0.15273(17) 0.15362(8) 0.30454(6) 0.0349(2) Uani 1 1 d . . . . .
H17 H -0.259510 0.123275 0.322174 0.042 Uiso 1 1 calc R U . . .
C18 C 0.02052(16) 0.17761(7) 0.34115(5) 0.0305(2) Uani 1 1 d . . . . .
C19 C 0.17753(15) 0.22335(7) 0.31796(5) 0.02670(19) Uani 1 1 d . . . . .
H19 H 0.293077 0.238942 0.345506 0.032 Uiso 1 1 calc R U . . .
C20 C 1.05293(14) 0.57194(6) 0.41678(4) 0.02370(18) Uani 1 1 d . . . . .
C21 C 0.89569(14) 0.61050(7) 0.44672(5) 0.0273(2) Uani 1 1 d . . . . .
H21 H 0.761269 0.607779 0.427302 0.033 Uiso 1 1 calc R U . . .
C22 C 0.93586(16) 0.65241(8) 0.50437(5) 0.0309(2) Uani 1 1 d . . . . .
C23 C 1.12798(17) 0.66017(8) 0.53482(5) 0.0329(2) Uani 1 1 d . . . . .
H23 H 1.151429 0.690649 0.574065 0.039 Uiso 1 1 calc R U . . .
C24 C 1.28509(16) 0.62190(8) 0.50606(5) 0.0331(2) Uani 1 1 d . . . . .
H24 H 1.419435 0.625632 0.525434 0.040 Uiso 1 1 calc R U . . .
C25 C 1.24474(15) 0.57837(7) 0.44911(5) 0.0281(2) Uani 1 1 d . . . . .
N31 N 0.978(2) 0.4613(8) 0.0511(5) 0.0313(11) Uani 0.5 1 d . . P A -1
C31 C 0.8334(5) 0.4342(2) 0.00143(12) 0.0460(6) Uani 0.5 1 d . . P A -1
H31A H 0.697560 0.453197 0.011398 0.055 Uiso 0.5 1 calc R U P A -1
H31B H 0.833680 0.367895 -0.001729 0.055 Uiso 0.5 1 calc R U P A -1
C32 C 0.8763(4) 0.4750(2) -0.06309(11) 0.0432(6) Uani 0.5 1 d . . P A -1
H32A H 0.901146 0.426139 -0.092909 0.052 Uiso 0.5 1 calc R U P A -1
H32B H 0.757338 0.509562 -0.081071 0.052 Uiso 0.5 1 calc R U P A -1
C33 C 0.9361(4) 0.57140(19) 0.05311(11) 0.0422(5) Uani 0.5 1 d . . P A -1
H33A H 0.796661 0.582763 0.063462 0.051 Uiso 0.5 1 calc R U P A -1
H33B H 1.030222 0.599389 0.086323 0.051 Uiso 0.5 1 calc R U P A -1
C34 C 0.9669(5) 0.61357(18) -0.01183(12) 0.0426(5) Uani 0.5 1 d . . P A -1
H34A H 1.070169 0.661535 -0.007067 0.051 Uiso 0.5 1 calc R U P A -1
H34B H 0.839076 0.639659 -0.031387 0.051 Uiso 0.5 1 calc R U P A -1
C35 C 1.1788(4) 0.4580(2) 0.03879(12) 0.0432(6) Uani 0.5 1 d . . P A -1
H35A H 1.221368 0.394420 0.037277 0.052 Uiso 0.5 1 calc R U P A -1
H35B H 1.262400 0.487373 0.073943 0.052 Uiso 0.5 1 calc R U P A -1
C36 C 1.2186(4) 0.5042(2) -0.02377(12) 0.0465(6) Uani 0.5 1 d . . P A -1
H36 H 1.348043 0.512840 -0.037995 0.056 Uiso 0.5 1 calc R U P A -1
N32 N 1.042(2) 0.5306(9) -0.0555(6) 0.042(3) Uani 0.5 1 d . . P A -1


_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
F1 C15 1.3590(12) . ?
F2 C18 1.3614(13) . ?
F3 C25 1.3594(12) . ?
F4 C22 1.3561(13) . ?
C1 C2 1.3830(14) . ?
C1 C10 1.3915(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.4159(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3972(13) . ?
C3 C14 1.4807(13) . ?
C4 C11 1.3904(12) . ?
C4 H4 0.9500 . ?
C5 C12 1.3927(13) . ?
C5 C6 1.3969(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.4134(13) . ?
C6 C20 1.4790(13) . ?
C7 C8 1.3815(14) . ?
C7 H7 0.9500 . ?
C8 C13 1.3950(13) . ?
C8 H8 0.9500 . ?
N9 C13 1.3756(13) . ?
N9 C10 1.3777(13) . ?
N9 H9 0.904(15) . ?
C10 C11 1.4141(13) . ?
C11 C12 1.4458(13) . ?
C12 C13 1.4146(12) . ?
C14 C15 1.3987(13) . ?
C14 C19 1.4051(14) . ?
C15 C16 1.3803(15) . ?
C16 C17 1.3812(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3756(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3788(14) . ?
C19 H19 0.9500 . ?
C20 C25 1.3946(13) . ?
C20 C21 1.4006(13) . ?
C21 C22 1.3794(14) . ?
C21 H21 0.9500 . ?
C22 C23 1.3822(15) . ?
C23 C24 1.3850(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.3776(15) . ?
C24 H24 0.9500 . ?
N31 C35 1.389(15) . ?
N31 C31 1.418(13) . ?
N31 C33 1.664(13) . ?
C31 C32 1.553(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.376(14) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.549(4) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.652(16) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.544(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.357(14) . ?
C36 H36 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
C2 C1 C10 118.30(9) . . ?
C2 C1 H1 120.9 . . ?
C10 C1 H1 120.9 . . ?
C1 C2 C3 122.12(9) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 118.64(9) . . ?
C4 C3 C14 119.54(8) . . ?
C2 C3 C14 121.77(8) . . ?
C11 C4 C3 120.12(8) . . ?
C11 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C12 C5 C6 119.56(8) . . ?
C12 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 119.42(9) . . ?
C5 C6 C20 120.07(8) . . ?
C7 C6 C20 120.35(8) . . ?
C8 C7 C6 122.01(9) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.85(9) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C13 N9 C10 108.73(8) . . ?
C13 N9 H9 125.3(10) . . ?
C10 N9 H9 125.8(10) . . ?
N9 C10 C1 129.54(9) . . ?
N9 C10 C11 109.45(8) . . ?
C1 C10 C11 120.93(9) . . ?
C4 C11 C10 119.85(8) . . ?
C4 C11 C12 133.96(8) . . ?
C10 C11 C12 106.10(8) . . ?
C5 C12 C13 119.68(8) . . ?
C5 C12 C11 133.91(8) . . ?
C13 C12 C11 106.40(8) . . ?
N9 C13 C8 129.27(9) . . ?
N9 C13 C12 109.28(8) . . ?
C8 C13 C12 121.44(9) . . ?
C15 C14 C19 115.16(9) . . ?
C15 C14 C3 124.74(9) . . ?
C19 C14 C3 120.09(8) . . ?
F1 C15 C16 116.50(9) . . ?
F1 C15 C14 119.48(9) . . ?
C16 C15 C14 124.01(10) . . ?
C15 C16 C17 119.61(10) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 117.48(10) . . ?
C18 C17 H17 121.3 . . ?
C16 C17 H17 121.3 . . ?
F2 C18 C17 118.34(10) . . ?
F2 C18 C19 118.33(9) . . ?
C17 C18 C19 123.33(10) . . ?
C18 C19 C14 120.37(9) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C25 C20 C21 115.93(9) . . ?
C25 C20 C6 123.71(9) . . ?
C21 C20 C6 120.35(8) . . ?
C22 C21 C20 120.05(9) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
F4 C22 C21 118.11(9) . . ?
F4 C22 C23 118.81(10) . . ?
C21 C22 C23 123.08(10) . . ?
C22 C23 C24 117.61(10) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C25 C24 C23 119.39(9) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
F3 C25 C24 117.32(9) . . ?
F3 C25 C20 118.78(9) . . ?
C24 C25 C20 123.90(10) . . ?
C35 N31 C31 116.5(10) . . ?
C35 N31 C33 101.9(7) . . ?
C31 N31 C33 101.3(7) . . ?
N31 C31 C32 112.2(5) . . ?
N31 C31 H31A 109.2 . . ?
C32 C31 H31A 109.2 . . ?
N31 C31 H31B 109.2 . . ?
C32 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
N32 C32 C31 110.2(5) . . ?
N32 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 N31 109.8(4) . . ?
C34 C33 H33A 109.7 . . ?
N31 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
N31 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 N32 105.8(4) . . ?
C33 C34 H34A 110.6 . . ?
N32 C34 H34A 110.6 . . ?
C33 C34 H34B 110.6 . . ?
N32 C34 H34B 110.6 . . ?
H34A C34 H34B 108.7 . . ?
N31 C35 C36 113.3(4) . . ?
N31 C35 H35A 108.9 . . ?
C36 C35 H35A 108.9 . . ?
N31 C35 H35B 108.9 . . ?
C36 C35 H35B 108.9 . . ?
H35A C35 H35B 107.7 . . ?
N32 C36 C35 110.2(6) . . ?
N32 C36 H36 124.9 . . ?
C35 C36 H36 124.9 . . ?
C36 N32 C32 122.0(9) . . ?
C36 N32 C34 103.4(8) . . ?
C32 N32 C34 103.4(10) . . ?

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
C10 C1 C2 C3 0.85(15) . . . . ?
C1 C2 C3 C4 0.87(15) . . . . ?
C1 C2 C3 C14 -176.67(9) . . . . ?
C2 C3 C4 C11 -2.06(14) . . . . ?
C14 C3 C4 C11 175.54(8) . . . . ?
C12 C5 C6 C7 -0.12(13) . . . . ?
C12 C5 C6 C20 175.36(8) . . . . ?
C5 C6 C7 C8 1.53(14) . . . . ?
C20 C6 C7 C8 -173.94(9) . . . . ?
C6 C7 C8 C13 -1.20(14) . . . . ?
C13 N9 C10 C1 -175.86(10) . . . . ?
C13 N9 C10 C11 1.00(11) . . . . ?
C2 C1 C10 N9 175.15(10) . . . . ?
C2 C1 C10 C11 -1.40(15) . . . . ?
C3 C4 C11 C10 1.54(14) . . . . ?
C3 C4 C11 C12 -174.54(10) . . . . ?
N9 C10 C11 C4 -176.95(8) . . . . ?
C1 C10 C11 C4 0.23(14) . . . . ?
N9 C10 C11 C12 0.11(11) . . . . ?
C1 C10 C11 C12 177.29(9) . . . . ?
C6 C5 C12 C13 -1.52(13) . . . . ?
C6 C5 C12 C11 178.41(9) . . . . ?
C4 C11 C12 C5 -4.61(18) . . . . ?
C10 C11 C12 C5 178.93(10) . . . . ?
C4 C11 C12 C13 175.32(10) . . . . ?
C10 C11 C12 C13 -1.14(10) . . . . ?
C10 N9 C13 C8 178.10(10) . . . . ?
C10 N9 C13 C12 -1.75(11) . . . . ?
C7 C8 C13 N9 179.67(9) . . . . ?
C7 C8 C13 C12 -0.50(14) . . . . ?
C5 C12 C13 N9 -178.27(8) . . . . ?
C11 C12 C13 N9 1.78(10) . . . . ?
C5 C12 C13 C8 1.87(14) . . . . ?
C11 C12 C13 C8 -178.08(9) . . . . ?
C4 C3 C14 C15 154.29(9) . . . . ?
C2 C3 C14 C15 -28.18(14) . . . . ?
C4 C3 C14 C19 -26.53(13) . . . . ?
C2 C3 C14 C19 150.99(9) . . . . ?
C19 C14 C15 F1 -177.50(8) . . . . ?
C3 C14 C15 F1 1.71(14) . . . . ?
C19 C14 C15 C16 2.34(15) . . . . ?
C3 C14 C15 C16 -178.44(9) . . . . ?
F1 C15 C16 C17 178.03(10) . . . . ?
C14 C15 C16 C17 -1.82(16) . . . . ?
C15 C16 C17 C18 -0.13(16) . . . . ?
C16 C17 C18 F2 -177.59(10) . . . . ?
C16 C17 C18 C19 1.42(17) . . . . ?
F2 C18 C19 C14 178.18(9) . . . . ?
C17 C18 C19 C14 -0.83(16) . . . . ?
C15 C14 C19 C18 -1.01(14) . . . . ?
C3 C14 C19 C18 179.74(9) . . . . ?
C5 C6 C20 C25 144.02(10) . . . . ?
C7 C6 C20 C25 -40.54(14) . . . . ?
C5 C6 C20 C21 -37.39(13) . . . . ?
C7 C6 C20 C21 138.05(10) . . . . ?
C25 C20 C21 C22 0.66(14) . . . . ?
C6 C20 C21 C22 -178.04(9) . . . . ?
C20 C21 C22 F4 -179.41(10) . . . . ?
C20 C21 C22 C23 1.10(17) . . . . ?
F4 C22 C23 C24 179.04(10) . . . . ?
C21 C22 C23 C24 -1.48(17) . . . . ?
C22 C23 C24 C25 0.08(16) . . . . ?
C23 C24 C25 F3 -177.46(10) . . . . ?
C23 C24 C25 C20 1.76(17) . . . . ?
C21 C20 C25 F3 177.11(9) . . . . ?
C6 C20 C25 F3 -4.24(14) . . . . ?
C21 C20 C25 C24 -2.10(15) . . . . ?
C6 C20 C25 C24 176.55(10) . . . . ?
C35 N31 C31 C32 -45.0(9) . . . . ?
C33 N31 C31 C32 64.5(8) . . . . ?
N31 C31 C32 N32 -2.2(4) . . . . ?
C35 N31 C33 C34 61.7(7) . . . . ?
C31 N31 C33 C34 -58.8(8) . . . . ?
N31 C33 C34 N32 -3.1(3) . . . . ?
C31 N31 C35 C36 49.6(9) . . . . ?
C33 N31 C35 C36 -59.6(7) . . . . ?
N31 C35 C36 N32 -5.6(4) . . . . ?
C35 C36 N32 C32 -46.0(14) . . . . ?
C35 C36 N32 C34 69.5(7) . . . . ?
C31 C32 N32 C36 49.9(14) . . . . ?
C31 C32 N32 C34 -65.6(7) . . . . ?
C33 C34 N32 C36 -61.8(8) . . . . ?
C33 C34 N32 C32 66.3(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
_geom_hbond_publ_flag
N9 H9 N31 0.904(15) 2.029(19) 2.926(11) 171.4(14) . yes
N9 H9 N32 0.904(15) 1.927(19) 2.814(13) 166.3(14) 3_765 yes
C24 H24 F4 0.95 2.56 3.4273(13) 151.8 1_655 yes

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.110


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3II-250K
_database_code_depnum_ccdc_archive 'CCDC 2022185'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   19.2225(9)
_cell_length_b                   6.7835(3)
_cell_length_c                   17.5663(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.337(2)
_cell_angle_gamma                90
_cell_volume                     2161.35(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9435
_cell_measurement_theta_min      3.3275
_cell_measurement_theta_max      29.9785

_exptl_crystal_description       plate
_exptl_crystal_colour            colourles
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            69239
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.303
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5831
_reflns_number_gt                5268
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0864P)²+0.5245P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.067(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5831
_refine_ls_number_parameters     338
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.114
_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
F1 F 0.07642(4) 1.15506(13) 0.77553(5) 0.0532(2) Uani 1 1 d . . . . .
F2 F 0.09749(6) 1.44765(14) 0.88063(7) 0.0645(3) Uani 1 1 d . . . . .
F3 F 0.44202(5) 0.79900(14) 0.60365(8) 0.0731(3) Uani 1 1 d . . . . .
F4 F 0.57324(6) 0.83849(18) 0.58888(11) 0.0963(5) Uani 1 1 d . . . . .
N9 N 0.17162(6) 0.35925(16) 0.64181(7) 0.0422(2) Uani 1 1 d . . . . .
H9 H 0.1334(9) 0.287(3) 0.6114(11) 0.051 Uiso 1 1 d . U . . .
C1 C 0.10876(7) 0.58024(19) 0.71351(8) 0.0402(3) Uani 1 1 d . . . . .
H1 H 0.064194 0.509589 0.698724 0.048 Uiso 1 1 calc R U . . .
C2 C 0.11900(6) 0.74591(18) 0.76171(7) 0.0380(2) Uani 1 1 d . . . . .
H2 H 0.080607 0.787086 0.780036 0.046 Uiso 1 1 calc R U . . .
C3 C 0.18502(6) 0.85530(17) 0.78434(7) 0.0341(2) Uani 1 1 d . . . . .
C4 C 0.24198(6) 0.79640(17) 0.75693(7) 0.0356(2) Uani 1 1 d . . . . .
H4 H 0.286007 0.869291 0.770788 0.043 Uiso 1 1 calc R U . . .
C5 C 0.35170(7) 0.55880(18) 0.67135(7) 0.0397(3) Uani 1 1 d . . . . .
H5 H 0.378540 0.669603 0.697351 0.048 Uiso 1 1 calc R U . . .
C6 C 0.38262(7) 0.42720(19) 0.63110(8) 0.0410(3) Uani 1 1 d . . . . .
C7 C 0.34155(8) 0.2611(2) 0.59290(8) 0.0466(3) Uani 1 1 d . . . . .
H7 H 0.363000 0.171801 0.566273 0.056 Uiso 1 1 calc R U . . .
C8 C 0.27098(8) 0.22526(19) 0.59328(8) 0.0461(3) Uani 1 1 d . . . . .
H8 H 0.244448 0.113898 0.567432 0.055 Uiso 1 1 calc R U . . .
C10 C 0.16659(6) 0.52126(17) 0.68753(7) 0.0369(2) Uani 1 1 d . . . . .
C11 C 0.23328(6) 0.62852(17) 0.70877(7) 0.0354(2) Uani 1 1 d . . . . .
C12 C 0.28063(6) 0.52563(17) 0.67297(7) 0.0363(2) Uani 1 1 d . . . . .
C13 C 0.24039(7) 0.35942(18) 0.63319(7) 0.0390(3) Uani 1 1 d . . . . .
C14 C 0.19622(6) 1.02525(17) 0.84037(6) 0.0338(2) Uani 1 1 d . . . . .
C15 C 0.14222(6) 1.16535(18) 0.83481(7) 0.0374(2) Uani 1 1 d . . . . .
C16 C 0.15360(8) 1.32001(19) 0.88876(8) 0.0447(3) Uani 1 1 d . . . . .
C17 C 0.21937(10) 1.3428(2) 0.95002(9) 0.0539(4) Uani 1 1 d . . . . .
H17 H 0.226883 1.448604 0.986435 0.065 Uiso 1 1 calc R U . . .
C18 C 0.27419(9) 1.2061(2) 0.95669(9) 0.0536(3) Uani 1 1 d . . . . .
H18 H 0.319855 1.219186 0.998041 0.064 Uiso 1 1 calc R U . . .
C19 C 0.26282(7) 1.0506(2) 0.90343(8) 0.0431(3) Uani 1 1 d . . . . .
H19 H 0.300957 0.958785 0.909692 0.052 Uiso 1 1 calc R U . . .
C20 C 0.45806(7) 0.4547(2) 0.62723(8) 0.0439(3) Uani 1 1 d . . . . .
C21 C 0.48414(7) 0.6354(2) 0.61292(10) 0.0498(3) Uani 1 1 d . . . . .
C22 C 0.55266(8) 0.6570(3) 0.60460(12) 0.0594(4) Uani 1 1 d . . . . .
C23 C 0.59909(9) 0.5011(3) 0.61205(13) 0.0671(5) Uani 1 1 d . . . . .
H23 H 0.645790 0.517123 0.606606 0.081 Uiso 1 1 calc R U . . .
C24 C 0.57527(10) 0.3200(3) 0.62776(14) 0.0731(5) Uani 1 1 d . . . . .
H24 H 0.606400 0.210069 0.633737 0.088 Uiso 1 1 calc R U . . .
C25 C 0.50622(9) 0.2960(3) 0.63500(12) 0.0616(4) Uani 1 1 d . . . . .
H25 H 0.491362 0.169658 0.645407 0.074 Uiso 1 1 calc R U . . .
N31 N 0.0497(10) 0.115(3) 0.5395(9) 0.0511(15) Uani 0.5 1 d . U P . .
C31 C 0.0751(3) -0.0842(6) 0.5639(4) 0.1029(17) Uani 0.5 1 d . U P A -1
H31A H 0.087788 -0.098795 0.622462 0.123 Uiso 0.5 1 calc R U P A -1
H31B H 0.118944 -0.113649 0.549267 0.123 Uiso 0.5 1 calc R U P A -1
C32 C 0.0111(3) -0.2260(6) 0.5193(3) 0.0823(13) Uani 0.5 1 d . U P A -1
H32A H 0.029596 -0.325367 0.490295 0.099 Uiso 0.5 1 calc R U P A -1
H32B H -0.005583 -0.294671 0.559205 0.099 Uiso 0.5 1 calc R U P A -1
C33 C 0.0479(3) 0.1199(8) 0.4549(2) 0.0802(12) Uani 0.5 1 d . U P A -1
H33A H 0.096036 0.082434 0.451520 0.096 Uiso 0.5 1 calc R U P A -1
H33B H 0.035856 0.252954 0.432667 0.096 Uiso 0.5 1 calc R U P A -1
C34 C -0.0117(2) -0.0275(6) 0.40752(18) 0.0663(9) Uani 0.5 1 d . U P A -1
H34A H 0.011533 -0.132597 0.386124 0.080 Uiso 0.5 1 calc R U P A -1
H34B H -0.047010 0.040474 0.361647 0.080 Uiso 0.5 1 calc R U P A -1
C35 C -0.0104(3) 0.1647(10) 0.5512(4) 0.1089(18) Uani 0.5 1 d . U P A -1
H35A H -0.021128 0.303682 0.536902 0.131 Uiso 0.5 1 calc R U P A -1
H35B H -0.004999 0.148370 0.608292 0.131 Uiso 0.5 1 calc R U P A -1
C36 C -0.0751(2) 0.0334(10) 0.4983(4) 0.1088(18) Uani 0.5 1 d . U P A -1
H36A H -0.101599 -0.020238 0.532710 0.131 Uiso 0.5 1 calc R U P A -1
H36B H -0.109614 0.116749 0.457427 0.131 Uiso 0.5 1 calc R U P A -1
N32 N -0.0537(10) -0.120(2) 0.4602(8) 0.0458(12) Uani 0.5 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.3479(14) . ?
F2 C16 1.3533(16) . ?
F3 C21 1.3514(17) . ?
F4 C22 1.349(2) . ?
N9 C13 1.3794(16) . ?
N9 C10 1.3834(15) . ?
N9 H9 0.898(18) . ?
C1 C2 1.3814(17) . ?
C1 C10 1.3929(17) . ?
C1 H1 0.9400 . ?
C2 C3 1.4090(15) . ?
C2 H2 0.9400 . ?
C3 C4 1.3925(15) . ?
C3 C14 1.4845(15) . ?
C4 C11 1.3954(15) . ?
C4 H4 0.9400 . ?
C5 C6 1.3886(17) . ?
C5 C12 1.3941(16) . ?
C5 H5 0.9400 . ?
C6 C7 1.4114(18) . ?
C6 C20 1.4859(17) . ?
C7 C8 1.3802(19) . ?
C7 H7 0.9400 . ?
C8 C13 1.3924(17) . ?
C8 H8 0.9400 . ?
C10 C11 1.4127(15) . ?
C11 C12 1.4457(16) . ?
C12 C13 1.4142(16) . ?
C14 C15 1.3868(16) . ?
C14 C19 1.3987(16) . ?
C15 C16 1.3818(18) . ?
C16 C17 1.371(2) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.3790(19) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C20 C21 1.379(2) . ?
C20 C25 1.397(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.362(2) . ?
C23 C24 1.371(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.384(2) . ?
C24 H24 0.9400 . ?
C25 H25 0.9400 . ?
N31 N32 0.08(3) 3_556 ?
N31 C35 1.28(2) . ?
N31 C31 1.450(19) . ?
N31 C33 1.476(16) . ?
C31 C32 1.553(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C32 N32 1.512(17) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C33 C34 1.541(5) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C34 N32 1.548(15) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C35 C36 1.561(5) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C36 N32 1.375(18) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N9 C10 108.48(10) . . ?
C13 N9 H9 124.1(11) . . ?
C10 N9 H9 125.4(11) . . ?
C2 C1 C10 117.86(11) . . ?
C2 C1 H1 121.1 . . ?
C10 C1 H1 121.1 . . ?
C1 C2 C3 122.25(11) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 119.29(10) . . ?
C4 C3 C14 119.60(10) . . ?
C2 C3 C14 121.02(10) . . ?
C3 C4 C11 119.59(10) . . ?
C3 C4 H4 120.2 . . ?
C11 C4 H4 120.2 . . ?
C6 C5 C12 119.61(11) . . ?
C6 C5 H5 120.2 . . ?
C12 C5 H5 120.2 . . ?
C5 C6 C7 119.27(12) . . ?
C5 C6 C20 122.09(11) . . ?
C7 C6 C20 118.64(11) . . ?
C8 C7 C6 122.29(12) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C13 117.83(11) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
N9 C10 C1 129.45(11) . . ?
N9 C10 C11 109.30(10) . . ?
C1 C10 C11 121.23(11) . . ?
C4 C11 C10 119.77(10) . . ?
C4 C11 C12 133.75(10) . . ?
C10 C11 C12 106.47(10) . . ?
C5 C12 C13 119.87(11) . . ?
C5 C12 C11 133.89(10) . . ?
C13 C12 C11 106.24(10) . . ?
N9 C13 C8 129.39(11) . . ?
N9 C13 C12 109.49(10) . . ?
C8 C13 C12 121.12(12) . . ?
C15 C14 C19 116.05(11) . . ?
C15 C14 C3 123.00(10) . . ?
C19 C14 C3 120.94(10) . . ?
F1 C15 C16 117.66(11) . . ?
F1 C15 C14 120.53(11) . . ?
C16 C15 C14 121.82(12) . . ?
F2 C16 C17 120.41(13) . . ?
F2 C16 C15 118.28(13) . . ?
C17 C16 C15 121.30(13) . . ?
C16 C17 C18 118.09(12) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 120.79(13) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 121.95(13) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C21 C20 C25 115.72(13) . . ?
C21 C20 C6 122.65(12) . . ?
C25 C20 C6 121.59(13) . . ?
F3 C21 C20 120.83(12) . . ?
F3 C21 C22 117.06(14) . . ?
C20 C21 C22 122.08(14) . . ?
F4 C22 C23 120.06(15) . . ?
F4 C22 C21 118.24(15) . . ?
C23 C22 C21 121.70(16) . . ?
C22 C23 C24 117.60(15) . . ?
C22 C23 H23 121.2 . . ?
C24 C23 H23 121.2 . . ?
C23 C24 C25 121.23(16) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C20 121.65(17) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
C35 N31 C31 115.6(12) . . ?
C35 N31 C33 115.6(13) . . ?
C31 N31 C33 102.3(12) . . ?
N31 C31 C32 107.1(7) . . ?
N31 C31 H31A 110.3 . . ?
C32 C31 H31A 110.3 . . ?
N31 C31 H31B 110.3 . . ?
C32 C31 H31B 110.3 . . ?
H31A C31 H31B 108.6 . . ?
N32 C32 C31 112.8(7) . . ?
N32 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
N32 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
N31 C33 C34 107.0(7) . . ?
N31 C33 H33A 110.3 . . ?
C34 C33 H33A 110.3 . . ?
N31 C33 H33B 110.3 . . ?
C34 C33 H33B 110.3 . . ?
H33A C33 H33B 108.6 . . ?
C33 C34 N32 112.5(6) . . ?
C33 C34 H34A 109.1 . . ?
N32 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
N32 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
N31 C35 C36 109.6(7) . . ?
N31 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N31 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N32 C36 C35 114.5(8) . . ?
N32 C36 H36A 108.6 . . ?
C35 C36 H36A 108.6 . . ?
N32 C36 H36B 108.6 . . ?
C35 C36 H36B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C36 N32 C32 109.6(10) . . ?
C36 N32 C34 106.4(10) . . ?
C32 N32 C34 97.5(11) . . ?

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
C10 C1 C2 C3 0.43(18) . . . . ?
C1 C2 C3 C4 0.53(18) . . . . ?
C1 C2 C3 C14 -176.11(11) . . . . ?
C2 C3 C4 C11 -1.10(17) . . . . ?
C14 C3 C4 C11 175.60(10) . . . . ?
C12 C5 C6 C7 -0.4(2) . . . . ?
C12 C5 C6 C20 179.96(12) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C20 C6 C7 C8 -179.64(13) . . . . ?
C6 C7 C8 C13 -0.1(2) . . . . ?
C13 N9 C10 C1 -178.39(12) . . . . ?
C13 N9 C10 C11 0.12(14) . . . . ?
C2 C1 C10 N9 177.52(12) . . . . ?
C2 C1 C10 C11 -0.83(18) . . . . ?
C3 C4 C11 C10 0.71(17) . . . . ?
C3 C4 C11 C12 -177.92(12) . . . . ?
N9 C10 C11 C4 -178.38(11) . . . . ?
C1 C10 C11 C4 0.27(18) . . . . ?
N9 C10 C11 C12 0.59(13) . . . . ?
C1 C10 C11 C12 179.24(11) . . . . ?
C6 C5 C12 C13 -0.48(19) . . . . ?
C6 C5 C12 C11 179.36(13) . . . . ?
C4 C11 C12 C5 -2.1(2) . . . . ?
C10 C11 C12 C5 179.10(13) . . . . ?
C4 C11 C12 C13 177.71(13) . . . . ?
C10 C11 C12 C13 -1.04(13) . . . . ?
C10 N9 C13 C8 179.09(13) . . . . ?
C10 N9 C13 C12 -0.80(14) . . . . ?
C7 C8 C13 N9 179.30(13) . . . . ?
C7 C8 C13 C12 -0.8(2) . . . . ?
C5 C12 C13 N9 -178.98(11) . . . . ?
C11 C12 C13 N9 1.14(14) . . . . ?
C5 C12 C13 C8 1.12(19) . . . . ?
C11 C12 C13 C8 -178.76(12) . . . . ?
C4 C3 C14 C15 140.06(12) . . . . ?
C2 C3 C14 C15 -43.30(16) . . . . ?
C4 C3 C14 C19 -40.96(16) . . . . ?
C2 C3 C14 C19 135.67(12) . . . . ?
C19 C14 C15 F1 179.25(11) . . . . ?
C3 C14 C15 F1 -1.73(17) . . . . ?
C19 C14 C15 C16 -0.33(17) . . . . ?
C3 C14 C15 C16 178.69(11) . . . . ?
F1 C15 C16 F2 2.17(17) . . . . ?
C14 C15 C16 F2 -178.24(11) . . . . ?
F1 C15 C16 C17 -178.98(12) . . . . ?
C14 C15 C16 C17 0.60(19) . . . . ?
F2 C16 C17 C18 178.58(13) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C15 C14 C19 C18 -0.28(19) . . . . ?
C3 C14 C19 C18 -179.33(12) . . . . ?
C5 C6 C20 C21 -42.9(2) . . . . ?
C7 C6 C20 C21 137.45(15) . . . . ?
C5 C6 C20 C25 139.53(15) . . . . ?
C7 C6 C20 C25 -40.1(2) . . . . ?
C25 C20 C21 F3 179.41(15) . . . . ?
C6 C20 C21 F3 1.7(2) . . . . ?
C25 C20 C21 C22 1.7(2) . . . . ?
C6 C20 C21 C22 -175.99(14) . . . . ?
F3 C21 C22 F4 0.8(2) . . . . ?
C20 C21 C22 F4 178.54(16) . . . . ?
F3 C21 C22 C23 -179.39(17) . . . . ?
C20 C21 C22 C23 -1.6(3) . . . . ?
F4 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C20 -0.5(3) . . . . ?
C21 C20 C25 C24 -0.7(2) . . . . ?
C6 C20 C25 C24 177.02(16) . . . . ?
N32 N31 C31 C32 -150(21) 3_556 . . . ?
C35 N31 C31 C32 55.7(13) . . . . ?
C33 N31 C31 C32 -70.9(11) . . . . ?
N31 C31 C32 N32 5.0(7) . . . . ?
N32 N31 C33 C34 165(26) 3_556 . . . ?
C35 N31 C33 C34 -61.1(14) . . . . ?
C31 N31 C33 C34 65.4(11) . . . . ?
N31 C33 C34 N32 4.1(6) . . . . ?
N32 N31 C35 C36 153(29) 3_556 . . . ?
C31 N31 C35 C36 -63.8(14) . . . . ?
C33 N31 C35 C36 55.7(14) . . . . ?
N31 C35 C36 N32 8.2(10) . . . . ?
C35 C36 N32 N31 -22(21) . . . 3_556 ?
C35 C36 N32 C32 46.5(13) . . . . ?
C35 C36 N32 C34 -57.9(12) . . . . ?
C31 C32 N32 N31 32(25) . . . 3_556 ?
C31 C32 N32 C36 -52.3(12) . . . . ?
C31 C32 N32 C34 58.1(10) . . . . ?
C33 C34 N32 N31 -21(42) . . . 3_556 ?
C33 C34 N32 C36 49.6(12) . . . . ?
C33 C34 N32 C32 -63.4(10) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.898(18) 2.05(2) 2.948(15) 177.1(17) . yes
C34 H34B F1 0.98 2.64 3.160(3) 113.2 3_566 yes
C34 H34A F1 0.98 2.64 3.405(4) 135.4 4_565 yes
C35 H35A F2 0.98 2.57 3.041(4) 109.4 2_546 yes

_refine_diff_density_max         0.462
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-3II-300K
_database_code_depnum_ccdc_archive 'CCDC 2022186'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N),C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

_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+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   19.2767(6)
_cell_length_b                   6.7799(2)
_cell_length_c                   17.6615(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.2900(10)
_cell_angle_gamma                90
_cell_volume                     2178.66(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.3866
_cell_measurement_theta_max      29.0781

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      301(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            67379
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.296
_diffrn_reflns_theta_max         29.118
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5405
_reflns_number_gt                4757
_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0949P)²+0.4430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.038(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5405
_refine_ls_number_parameters     338
_refine_ls_number_restraints     75
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.114
_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
F1 F 0.07664(5) 1.15364(15) 0.77552(6) 0.0656(3) Uani 1 1 d . . . . .
F2 F 0.09779(7) 1.44573(16) 0.88002(8) 0.0793(3) Uani 1 1 d . . . . .
F3 F 0.44135(6) 0.79901(17) 0.60242(10) 0.0937(4) Uani 1 1 d . . . . .
F4 F 0.57293(8) 0.8384(2) 0.58939(14) 0.1242(6) Uani 1 1 d . . . . .
N9 N 0.17156(7) 0.36018(18) 0.64083(8) 0.0529(3) Uani 1 1 d . . . . .
H9 H 0.1335(10) 0.288(3) 0.6115(11) 0.063 Uiso 1 1 d . U . . .
C1 C 0.10909(7) 0.5798(2) 0.71282(8) 0.0496(3) Uani 1 1 d . . . . .
H1 H 0.065118 0.509972 0.698261 0.059 Uiso 1 1 calc R U . . .
C2 C 0.11935(7) 0.7446(2) 0.76097(8) 0.0471(3) Uani 1 1 d . . . . .
H2 H 0.081553 0.784613 0.779287 0.057 Uiso 1 1 calc R U . . .
C3 C 0.18500(7) 0.85454(19) 0.78345(7) 0.0423(3) Uani 1 1 d . . . . .
C4 C 0.24157(7) 0.7963(2) 0.75580(8) 0.0443(3) Uani 1 1 d . . . . .
H4 H 0.284959 0.868641 0.769398 0.053 Uiso 1 1 calc R U . . .
C5 C 0.35084(7) 0.5600(2) 0.67013(8) 0.0499(3) Uani 1 1 d . . . . .
H5 H 0.377214 0.669733 0.695720 0.060 Uiso 1 1 calc R U . . .
C6 C 0.38193(8) 0.4286(2) 0.63023(9) 0.0520(3) Uani 1 1 d . . . . .
C7 C 0.34081(9) 0.2629(2) 0.59205(10) 0.0593(4) Uani 1 1 d . . . . .
H7 H 0.361959 0.174533 0.565796 0.071 Uiso 1 1 calc R U . . .
C8 C 0.27063(9) 0.2272(2) 0.59224(10) 0.0581(4) Uani 1 1 d . . . . .
H8 H 0.244462 0.117203 0.566594 0.070 Uiso 1 1 calc R U . . .
C10 C 0.16648(7) 0.52133(19) 0.68670(8) 0.0457(3) Uani 1 1 d . . . . .
C11 C 0.23295(7) 0.62908(19) 0.70760(8) 0.0437(3) Uani 1 1 d . . . . .
C12 C 0.28010(7) 0.52677(19) 0.67168(8) 0.0457(3) Uani 1 1 d . . . . .
C13 C 0.23996(8) 0.3610(2) 0.63201(8) 0.0491(3) Uani 1 1 d . . . . .
C14 C 0.19620(7) 1.02433(19) 0.83920(7) 0.0423(3) Uani 1 1 d . . . . .
C15 C 0.14241(7) 1.1638(2) 0.83420(8) 0.0464(3) Uani 1 1 d . . . . .
C16 C 0.15373(9) 1.3180(2) 0.88791(9) 0.0553(4) Uani 1 1 d . . . . .
C17 C 0.21941(11) 1.3408(3) 0.94844(10) 0.0670(4) Uani 1 1 d . . . . .
H17 H 0.226921 1.445447 0.984323 0.080 Uiso 1 1 calc R U . . .
C18 C 0.27382(10) 1.2052(3) 0.95470(10) 0.0671(4) Uani 1 1 d . . . . .
H18 H 0.318883 1.218150 0.995291 0.081 Uiso 1 1 calc R U . . .
C19 C 0.26260(8) 1.0499(2) 0.90167(9) 0.0539(3) Uani 1 1 d . . . . .
H19 H 0.300326 0.959541 0.907609 0.065 Uiso 1 1 calc R U . . .
C20 C 0.45732(8) 0.4558(2) 0.62692(10) 0.0568(4) Uani 1 1 d . . . . .
C21 C 0.48347(8) 0.6356(3) 0.61234(11) 0.0639(4) Uani 1 1 d . . . . .
C22 C 0.55223(10) 0.6569(3) 0.60517(14) 0.0764(5) Uani 1 1 d . . . . .
C23 C 0.59850(10) 0.5016(4) 0.61376(15) 0.0866(7) Uani 1 1 d . . . . .
H23 H 0.644851 0.517254 0.609110 0.104 Uiso 1 1 calc R U . . .
C24 C 0.57478(12) 0.3218(4) 0.62944(17) 0.0940(7) Uani 1 1 d . . . . .
H24 H 0.605700 0.213145 0.636160 0.113 Uiso 1 1 calc R U . . .
C25 C 0.50557(11) 0.2977(3) 0.63555(14) 0.0793(6) Uani 1 1 d . . . . .
H25 H 0.490828 0.172716 0.645691 0.095 Uiso 1 1 calc R U . . .
N31 N 0.0498(12) 0.115(3) 0.5391(10) 0.0604(16) Uani 0.5 1 d . U P . .
C31 C 0.0742(3) -0.0833(7) 0.5638(4) 0.1112(18) Uani 0.5 1 d . U P A -1
H31A H 0.085628 -0.097349 0.621268 0.133 Uiso 0.5 1 calc R U P A -1
H31B H 0.118096 -0.113241 0.550549 0.133 Uiso 0.5 1 calc R U P A -1
C32 C 0.0110(3) -0.2245(6) 0.5185(3) 0.0943(14) Uani 0.5 1 d . U P A -1
H32A H 0.029536 -0.321089 0.489496 0.113 Uiso 0.5 1 calc R U P A -1
H32B H -0.005476 -0.294859 0.557321 0.113 Uiso 0.5 1 calc R U P A -1
C33 C 0.0483(3) 0.1181(8) 0.4552(2) 0.0900(13) Uani 0.5 1 d . U P A -1
H33A H 0.095573 0.077521 0.452133 0.108 Uiso 0.5 1 calc R U P A -1
H33B H 0.037660 0.250065 0.433290 0.108 Uiso 0.5 1 calc R U P A -1
C34 C -0.0120(3) -0.0258(7) 0.4080(2) 0.0768(10) Uani 0.5 1 d . U P A -1
H34A H 0.009988 -0.129810 0.385852 0.092 Uiso 0.5 1 calc R U P A -1
H34B H -0.046839 0.043945 0.363655 0.092 Uiso 0.5 1 calc R U P A -1
C35 C -0.0105(3) 0.1663(10) 0.5502(5) 0.1176(18) Uani 0.5 1 d . U P A -1
H35A H -0.020772 0.303984 0.535962 0.141 Uiso 0.5 1 calc R U P A -1
H35B H -0.005647 0.150644 0.606301 0.141 Uiso 0.5 1 calc R U P A -1
C36 C -0.0747(3) 0.0364(10) 0.4977(5) 0.1170(19) Uani 0.5 1 d . U P A -1
H36A H -0.101467 -0.014961 0.531254 0.140 Uiso 0.5 1 calc R U P A -1
H36B H -0.108207 0.119134 0.457028 0.140 Uiso 0.5 1 calc R U P A -1
N32 N -0.0536(12) -0.119(3) 0.4604(10) 0.0558(14) Uani 0.5 1 d . U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C15 1.3484(16) . ?
F2 C16 1.3537(18) . ?
F3 C21 1.350(2) . ?
F4 C22 1.351(3) . ?
N9 C13 1.3779(19) . ?
N9 C10 1.3828(18) . ?
N9 H9 0.89(2) . ?
C1 C2 1.378(2) . ?
C1 C10 1.390(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.4081(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3912(17) . ?
C3 C14 1.4835(17) . ?
C4 C11 1.3944(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3885(19) . ?
C5 C12 1.3913(19) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(2) . ?
C6 C20 1.485(2) . ?
C7 C8 1.375(2) . ?
C7 H7 0.9300 . ?
C8 C13 1.393(2) . ?
C8 H8 0.9300 . ?
C10 C11 1.4139(17) . ?
C11 C12 1.4460(18) . ?
C12 C13 1.4125(18) . ?
C14 C15 1.3847(18) . ?
C14 C19 1.3974(18) . ?
C15 C16 1.380(2) . ?
C16 C17 1.370(3) . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.375(3) . ?
C20 C25 1.394(2) . ?
C21 C22 1.380(2) . ?
C22 C23 1.356(3) . ?
C23 C24 1.362(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.383(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N31 C35 1.29(2) . ?
N31 C31 1.44(2) . ?
N31 C33 1.472(19) . ?
C31 C32 1.549(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 N32 1.51(2) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.536(5) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 N32 1.545(18) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C36 1.551(6) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 N32 1.38(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N9 C10 108.59(11) . . ?
C13 N9 H9 124.7(12) . . ?
C10 N9 H9 124.9(12) . . ?
C2 C1 C10 117.93(12) . . ?
C2 C1 H1 121.0 . . ?
C10 C1 H1 121.0 . . ?
C1 C2 C3 122.38(12) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 119.11(12) . . ?
C4 C3 C14 119.61(11) . . ?
C2 C3 C14 121.20(11) . . ?
C3 C4 C11 119.72(11) . . ?
C3 C4 H4 120.1 . . ?
C11 C4 H4 120.1 . . ?
C6 C5 C12 119.76(12) . . ?
C6 C5 H5 120.1 . . ?
C12 C5 H5 120.1 . . ?
C5 C6 C7 118.99(13) . . ?
C5 C6 C20 122.15(13) . . ?
C7 C6 C20 118.86(13) . . ?
C8 C7 C6 122.44(14) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C13 117.93(13) . . ?
C7 C8 H8 121.0 . . ?
C13 C8 H8 121.0 . . ?
N9 C10 C1 129.66(12) . . ?
N9 C10 C11 109.14(12) . . ?
C1 C10 C11 121.20(12) . . ?
C4 C11 C10 119.64(12) . . ?
C4 C11 C12 133.83(12) . . ?
C10 C11 C12 106.52(11) . . ?
C5 C12 C13 119.92(12) . . ?
C5 C12 C11 133.90(12) . . ?
C13 C12 C11 106.18(11) . . ?
N9 C13 C8 129.49(13) . . ?
N9 C13 C12 109.57(12) . . ?
C8 C13 C12 120.94(13) . . ?
C15 C14 C19 115.91(12) . . ?
C15 C14 C3 123.10(11) . . ?
C19 C14 C3 120.98(12) . . ?
F1 C15 C16 117.54(13) . . ?
F1 C15 C14 120.54(12) . . ?
C16 C15 C14 121.92(13) . . ?
F2 C16 C17 120.51(14) . . ?
F2 C16 C15 118.30(15) . . ?
C17 C16 C15 121.18(14) . . ?
C16 C17 C18 118.18(14) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C17 C18 C19 120.89(15) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 121.92(15) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C21 C20 C25 115.42(16) . . ?
C21 C20 C6 122.79(14) . . ?
C25 C20 C6 121.75(16) . . ?
F3 C21 C20 120.63(14) . . ?
F3 C21 C22 117.17(17) . . ?
C20 C21 C22 122.17(16) . . ?
F4 C22 C23 120.16(18) . . ?
F4 C22 C21 118.20(18) . . ?
C23 C22 C21 121.6(2) . . ?
C22 C23 C24 117.73(18) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C23 C24 C25 121.2(2) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C24 C25 C20 121.8(2) . . ?
C24 C25 H25 119.1 . . ?
C20 C25 H25 119.1 . . ?
C35 N31 C31 115.3(14) . . ?
C35 N31 C33 115.5(14) . . ?
C31 N31 C33 102.3(13) . . ?
N31 C31 C32 107.2(8) . . ?
N31 C31 H31A 110.3 . . ?
C32 C31 H31A 110.3 . . ?
N31 C31 H31B 110.3 . . ?
C32 C31 H31B 110.3 . . ?
H31A C31 H31B 108.5 . . ?
N32 C32 C31 113.0(7) . . ?
N32 C32 H32A 109.0 . . ?
C31 C32 H32A 109.0 . . ?
N32 C32 H32B 109.0 . . ?
C31 C32 H32B 109.0 . . ?
H32A C32 H32B 107.8 . . ?
N31 C33 C34 107.2(7) . . ?
N31 C33 H33A 110.3 . . ?
C34 C33 H33A 110.3 . . ?
N31 C33 H33B 110.3 . . ?
C34 C33 H33B 110.3 . . ?
H33A C33 H33B 108.5 . . ?
C33 C34 N32 112.7(7) . . ?
C33 C34 H34A 109.1 . . ?
N32 C34 H34A 109.1 . . ?
C33 C34 H34B 109.1 . . ?
N32 C34 H34B 109.1 . . ?
H34A C34 H34B 107.8 . . ?
N31 C35 C36 109.7(8) . . ?
N31 C35 H35A 109.7 . . ?
C36 C35 H35A 109.7 . . ?
N31 C35 H35B 109.7 . . ?
C36 C35 H35B 109.7 . . ?
H35A C35 H35B 108.2 . . ?
N32 C36 C35 114.7(9) . . ?
N32 C36 H36A 108.6 . . ?
C35 C36 H36A 108.6 . . ?
N32 C36 H36B 108.6 . . ?
C35 C36 H36B 108.6 . . ?
H36A C36 H36B 107.6 . . ?
C36 N32 C32 110.2(12) . . ?
C36 N32 C34 105.5(11) . . ?
C32 N32 C34 97.3(13) . . ?

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
C10 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C3 C14 -176.37(12) . . . . ?
C2 C3 C4 C11 -1.05(19) . . . . ?
C14 C3 C4 C11 175.84(12) . . . . ?
C12 C5 C6 C7 -0.2(2) . . . . ?
C12 C5 C6 C20 -179.69(14) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C20 C6 C7 C8 -179.88(16) . . . . ?
C6 C7 C8 C13 -0.1(3) . . . . ?
C13 N9 C10 C1 -178.48(14) . . . . ?
C13 N9 C10 C11 0.31(16) . . . . ?
C2 C1 C10 N9 177.59(14) . . . . ?
C2 C1 C10 C11 -1.1(2) . . . . ?
C3 C4 C11 C10 0.6(2) . . . . ?
C3 C4 C11 C12 -177.79(14) . . . . ?
N9 C10 C11 C4 -178.41(12) . . . . ?
C1 C10 C11 C4 0.5(2) . . . . ?
N9 C10 C11 C12 0.36(15) . . . . ?
C1 C10 C11 C12 179.28(13) . . . . ?
C6 C5 C12 C13 -0.7(2) . . . . ?
C6 C5 C12 C11 178.92(15) . . . . ?
C4 C11 C12 C5 -2.0(3) . . . . ?
C10 C11 C12 C5 179.51(15) . . . . ?
C4 C11 C12 C13 177.65(15) . . . . ?
C10 C11 C12 C13 -0.87(15) . . . . ?
C10 N9 C13 C8 178.73(15) . . . . ?
C10 N9 C13 C12 -0.88(16) . . . . ?
C7 C8 C13 N9 179.72(16) . . . . ?
C7 C8 C13 C12 -0.7(2) . . . . ?
C5 C12 C13 N9 -179.23(13) . . . . ?
C11 C12 C13 N9 1.09(16) . . . . ?
C5 C12 C13 C8 1.1(2) . . . . ?
C11 C12 C13 C8 -178.56(14) . . . . ?
C4 C3 C14 C15 140.12(13) . . . . ?
C2 C3 C14 C15 -43.06(18) . . . . ?
C4 C3 C14 C19 -41.07(18) . . . . ?
C2 C3 C14 C19 135.74(14) . . . . ?
C19 C14 C15 F1 179.26(12) . . . . ?
C3 C14 C15 F1 -1.88(19) . . . . ?
C19 C14 C15 C16 -0.29(19) . . . . ?
C3 C14 C15 C16 178.58(12) . . . . ?
F1 C15 C16 F2 1.91(19) . . . . ?
C14 C15 C16 F2 -178.53(12) . . . . ?
F1 C15 C16 C17 -178.92(13) . . . . ?
C14 C15 C16 C17 0.6(2) . . . . ?
F2 C16 C17 C18 178.76(15) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C14 0.5(3) . . . . ?
C15 C14 C19 C18 -0.3(2) . . . . ?
C3 C14 C19 C18 -179.18(14) . . . . ?
C5 C6 C20 C21 -43.6(2) . . . . ?
C7 C6 C20 C21 136.86(17) . . . . ?
C5 C6 C20 C25 138.83(19) . . . . ?
C7 C6 C20 C25 -40.7(2) . . . . ?
C25 C20 C21 F3 179.56(18) . . . . ?
C6 C20 C21 F3 1.9(3) . . . . ?
C25 C20 C21 C22 1.3(3) . . . . ?
C6 C20 C21 C22 -176.45(17) . . . . ?
F3 C21 C22 F4 0.5(3) . . . . ?
C20 C21 C22 F4 178.82(19) . . . . ?
F3 C21 C22 C23 -179.7(2) . . . . ?
C20 C21 C22 C23 -1.4(3) . . . . ?
F4 C22 C23 C24 -179.8(2) . . . . ?
C21 C22 C23 C24 0.3(4) . . . . ?
C22 C23 C24 C25 0.7(4) . . . . ?
C23 C24 C25 C20 -0.7(4) . . . . ?
C21 C20 C25 C24 -0.2(3) . . . . ?
C6 C20 C25 C24 177.5(2) . . . . ?
N32 N31 C31 C32 -150(26) 3_556 . . . ?
C35 N31 C31 C32 56.5(15) . . . . ?
C33 N31 C31 C32 -69.7(13) . . . . ?
N31 C31 C32 N32 3.3(8) . . . . ?
N32 N31 C33 C34 161(31) 3_556 . . . ?
C35 N31 C33 C34 -59.9(15) . . . . ?
C31 N31 C33 C34 66.2(13) . . . . ?
N31 C33 C34 N32 2.5(6) . . . . ?
N32 N31 C35 C36 159(39) 3_556 . . . ?
C31 N31 C35 C36 -63.9(15) . . . . ?
C33 N31 C35 C36 55.3(15) . . . . ?
N31 C35 C36 N32 8.6(11) . . . . ?
C35 C36 N32 N31 -18(26) . . . 3_556 ?
C35 C36 N32 C32 45.4(14) . . . . ?
C35 C36 N32 C34 -58.7(14) . . . . ?
C31 C32 N32 N31 34(32) . . . 3_556 ?
C31 C32 N32 C36 -50.5(14) . . . . ?
C31 C32 N32 C34 59.0(11) . . . . ?
C33 C34 N32 N31 -27(46) . . . 3_556 ?
C33 C34 N32 C36 51.1(14) . . . . ?
C33 C34 N32 C32 -62.3(11) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.89(2) 2.06(3) 2.953(17) 176.2(18) . yes
C34 H34B F1 0.97 2.69 3.185(3) 112.2 3_566 yes
C34 H34A F1 0.97 2.67 3.434(5) 136.0 4_565 yes
C35 H35A F2 0.97 2.60 3.051(5) 108.2 2_546 yes

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.081


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
####################################################################### 
# 
# 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_ANH-BRM-1LT-150K
_database_code_depnum_ccdc_archive 'CCDC 2022171'
loop_
_audit_author_name
_audit_author_address
'Ruben A. Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-12-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-21
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H13 F4 N), C6 H12 N2'
_chemical_formula_sum            'C54 H38 F8 N4'
_chemical_formula_weight         894.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0065 0.0035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0185 0.0109 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   14.0331(4)
_cell_length_b                   13.6998(4)
_cell_length_c                   22.8049(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.5550(10)
_cell_angle_gamma                90
_cell_volume                     4180.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9562
_cell_measurement_theta_min      2.4525
_cell_measurement_theta_max      29.9751

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'SADABS 2016/2 Bruker AXS Madison WI USA'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7288
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source beamline 12.2.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTONII detector'
_diffrn_measurement_method       'ω/θ shutterless scans'
_diffrn_detector_area_resol_mean 7.39
_diffrn_reflns_number            145863
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.802
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_full        25.930
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             22549
_reflns_number_gt                21589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_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 APEX 3'
_computing_cell_refinement       'Bruker SAINT v8.38a'
_computing_data_reduction        'Bruker SAINT v8.38a'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL & local programs'
_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)+(0.0607P)²+0.4693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'Dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 9826 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         22549
_refine_ls_number_parameters     1201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
F1 F -0.04596(9) 0.58337(12) 0.36095(6) 0.0442(3) Uani 1 1 d . . . . .
F2 F -0.07447(9) 0.67260(12) 0.15828(6) 0.0460(3) Uani 1 1 d . . . . .
F3 F 0.67194(11) 0.50678(13) -0.01424(6) 0.0483(3) Uani 1 1 d . . . . .
F4 F 0.37700(10) 0.69026(12) -0.06231(6) 0.0444(3) Uani 1 1 d . . . . .
C1 C 0.42091(13) 0.63686(14) 0.37964(8) 0.0260(3) Uani 1 1 d . . . . .
H1 H 0.460575 0.641427 0.421444 0.031 Uiso 1 1 calc R U . . .
C2 C 0.31770(13) 0.63638(14) 0.36358(7) 0.0247(3) Uani 1 1 d . . . . .
H2 H 0.286655 0.642185 0.395124 0.030 Uiso 1 1 calc R U . . .
C3 C 0.25673(12) 0.62755(13) 0.30193(7) 0.0214(3) Uani 1 1 d . . . . .
C4 C 0.30239(12) 0.62096(12) 0.25548(7) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.262621 0.614490 0.213810 0.025 Uiso 1 1 calc R U . . .
C5 C 0.46417(12) 0.61620(13) 0.17163(7) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.399394 0.614097 0.142591 0.026 Uiso 1 1 calc R U . . .
C6 C 0.54919(12) 0.61532(13) 0.15177(7) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.64497(12) 0.61966(14) 0.19559(7) 0.0240(3) Uani 1 1 d . . . . .
H7 H 0.702327 0.619379 0.181689 0.029 Uiso 1 1 calc R U . . .
C8 C 0.65776(12) 0.62431(14) 0.25810(8) 0.0239(3) Uani 1 1 d . . . . .
H8 H 0.722614 0.627365 0.286997 0.029 Uiso 1 1 calc R U . . .
N9 N 0.56466(11) 0.63108(12) 0.33597(7) 0.0251(3) Uani 1 1 d . . . . .
H9 H 0.6099(19) 0.6286(19) 0.3708(11) 0.030 Uiso 1 1 d . U . . .
C10 C 0.46502(12) 0.63043(13) 0.33241(7) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.40579(12) 0.62385(12) 0.27012(7) 0.0204(3) Uani 1 1 d . . . . .
C12 C 0.47531(11) 0.62019(12) 0.23439(7) 0.0201(3) Uani 1 1 d . . . . .
C13 C 0.57251(12) 0.62436(13) 0.27730(7) 0.0216(3) Uani 1 1 d . . . . .
C14 C 0.14644(12) 0.62691(12) 0.28757(7) 0.0214(3) Uani 1 1 d . . . . .
C15 C 0.10026(13) 0.60387(14) 0.33218(8) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.139392 0.587511 0.372789 0.031 Uiso 1 1 calc R U . . .
C16 C -0.00276(14) 0.60508(15) 0.31674(9) 0.0288(4) Uani 1 1 d . . . . .
C17 C -0.06470(13) 0.62734(15) 0.25896(9) 0.0301(4) Uani 1 1 d . . . . .
H17 H -0.135427 0.627853 0.249472 0.036 Uiso 1 1 calc R U . . .
C18 C -0.01718(14) 0.64878(14) 0.21591(9) 0.0291(4) Uani 1 1 d . . . . .
C19 C 0.08528(13) 0.65016(14) 0.22841(8) 0.0260(3) Uani 1 1 d . . . . .
H19 H 0.114186 0.666789 0.197062 0.031 Uiso 1 1 calc R U . . .
C20 C 0.54034(12) 0.61044(13) 0.08539(7) 0.0228(3) Uani 1 1 d . . . . .
C21 C 0.61191(14) 0.56038(14) 0.06552(8) 0.0269(3) Uani 1 1 d . . . . .
H21 H 0.666693 0.529331 0.094516 0.032 Uiso 1 1 calc R U . . .
C22 C 0.60240(15) 0.55641(16) 0.00370(9) 0.0320(4) Uani 1 1 d . . . . .
C23 C 0.52482(16) 0.59973(17) -0.04082(8) 0.0336(4) Uani 1 1 d . . . . .
H23 H 0.519460 0.596236 -0.083304 0.040 Uiso 1 1 calc R U . . .
C24 C 0.45584(14) 0.64820(15) -0.01993(8) 0.0307(4) Uani 1 1 d . . . . .
C25 C 0.46065(13) 0.65553(14) 0.04129(8) 0.0265(3) Uani 1 1 d . . . . .
H25 H 0.411019 0.690383 0.053264 0.032 Uiso 1 1 calc R U . . .
N31 N 0.71296(10) 0.60901(12) 0.45204(6) 0.0247(3) Uani 1 1 d . . . . .
C31 C 0.81190(13) 0.60765(15) 0.44238(8) 0.0263(3) Uani 1 1 d . . . . .
H31A H 0.819398 0.665618 0.418224 0.032 Uiso 1 1 calc R U . . .
H31B H 0.818405 0.548569 0.418884 0.032 Uiso 1 1 calc R U . . .
C32 C 0.89449(12) 0.60793(15) 0.50509(8) 0.0267(3) Uani 1 1 d . . . . .
H32A H 0.937903 0.550045 0.507997 0.032 Uiso 1 1 calc R U . . .
H32B H 0.936379 0.667031 0.508380 0.032 Uiso 1 1 calc R U . . .
C33 C 0.70277(15) 0.52175(15) 0.48699(10) 0.0327(4) Uani 1 1 d . . . . .
H33A H 0.707292 0.462545 0.463083 0.039 Uiso 1 1 calc R U . . .
H33B H 0.636508 0.521988 0.494015 0.039 Uiso 1 1 calc R U . . .
C34 C 0.78565(16) 0.51953(15) 0.54928(9) 0.0309(4) Uani 1 1 d . . . . .
H34A H 0.755107 0.517809 0.583140 0.037 Uiso 1 1 calc R U . . .
H34B H 0.826519 0.459838 0.551968 0.037 Uiso 1 1 calc R U . . .
C35 C 0.70563(14) 0.69619(15) 0.48829(9) 0.0290(4) Uani 1 1 d . . . . .
H35A H 0.638617 0.698775 0.494202 0.035 Uiso 1 1 calc R U . . .
H35B H 0.714246 0.755648 0.465746 0.035 Uiso 1 1 calc R U . . .
C36 C 0.78667(14) 0.69331(14) 0.55160(8) 0.0268(3) Uani 1 1 d . . . . .
H36A H 0.828368 0.752884 0.557025 0.032 Uiso 1 1 calc R U . . .
H36B H 0.754488 0.691669 0.584701 0.032 Uiso 1 1 calc R U . . .
N32 N 0.84998(11) 0.60645(12) 0.55588(6) 0.0253(3) Uani 1 1 d . . . . .
F41 F 1.62450(10) 0.58120(13) 0.63607(6) 0.0487(4) Uani 1 1 d . . . . .
F42 F 1.66129(9) 0.64811(12) 0.84279(6) 0.0465(4) Uani 1 1 d . . . . .
F43 F 0.89541(12) 0.59714(15) 1.01899(7) 0.0596(5) Uani 1 1 d . . . . .
F44 F 1.21630(13) 0.73087(16) 1.05937(7) 0.0651(5) Uani 1 1 d . . . . .
C41 C 1.16138(13) 0.62462(15) 0.62157(7) 0.0263(3) Uani 1 1 d . . . . .
H41 H 1.121499 0.623931 0.579706 0.032 Uiso 1 1 calc R U . . .
C42 C 1.26451(13) 0.62646(14) 0.63728(7) 0.0252(3) Uani 1 1 d . . . . .
H42 H 1.295105 0.629170 0.605399 0.030 Uiso 1 1 calc R U . . .
C43 C 1.32607(12) 0.62446(13) 0.69904(7) 0.0212(3) Uani 1 1 d . . . . .
C44 C 1.28078(12) 0.62365(12) 0.74595(7) 0.0206(3) Uani 1 1 d . . . . .
H44 H 1.320800 0.622319 0.787778 0.025 Uiso 1 1 calc R U . . .
C45 C 1.11842(12) 0.63380(13) 0.82990(7) 0.0220(3) Uani 1 1 d . . . . .
H45 H 1.183086 0.633056 0.859099 0.026 Uiso 1 1 calc R U . . .
C46 C 1.03335(13) 0.64092(13) 0.84958(7) 0.0237(3) Uani 1 1 d . . . . .
C47 C 0.93773(13) 0.64153(14) 0.80543(8) 0.0268(3) Uani 1 1 d . . . . .
H47 H 0.880255 0.646992 0.818997 0.032 Uiso 1 1 calc R U . . .
C48 C 0.92538(13) 0.63441(14) 0.74311(8) 0.0261(3) Uani 1 1 d . . . . .
H48 H 0.860626 0.634164 0.714010 0.031 Uiso 1 1 calc R U . . .
N49 N 1.01784(11) 0.62475(12) 0.66538(6) 0.0245(3) Uani 1 1 d . . . . .
H49 H 0.9647(19) 0.6231(19) 0.6322(11) 0.029 Uiso 1 1 d . U . . .
C50 C 1.11762(12) 0.62379(13) 0.66881(7) 0.0220(3) Uani 1 1 d . . . . .
C51 C 1.17700(12) 0.62479(12) 0.73125(7) 0.0203(3) Uani 1 1 d . . . . .
C52 C 1.10776(12) 0.62779(12) 0.76720(7) 0.0205(3) Uani 1 1 d . . . . .
C53 C 1.01086(12) 0.62760(13) 0.72429(7) 0.0220(3) Uani 1 1 d . . . . .
C54 C 1.43665(12) 0.62293(12) 0.71332(7) 0.0209(3) Uani 1 1 d . . . . .
C55 C 1.48111(13) 0.60304(14) 0.66712(8) 0.0262(3) Uani 1 1 d . . . . .
H55 H 1.440841 0.591180 0.626084 0.031 Uiso 1 1 calc R U . . .
C56 C 1.58388(14) 0.60090(15) 0.68198(9) 0.0296(4) Uani 1 1 d . . . . .
C57 C 1.64742(13) 0.61565(15) 0.73999(9) 0.0299(4) Uani 1 1 d . . . . .
H57 H 1.718034 0.613516 0.748922 0.036 Uiso 1 1 calc R U . . .
C58 C 1.60174(13) 0.63374(15) 0.78436(8) 0.0286(4) Uani 1 1 d . . . . .
C59 C 1.50005(13) 0.63924(13) 0.77305(8) 0.0254(3) Uani 1 1 d . . . . .
H59 H 1.472868 0.653975 0.805454 0.030 Uiso 1 1 calc R U . . .
C60 C 1.04161(14) 0.64901(14) 0.91584(8) 0.0275(4) Uani 1 1 d . . . . .
C61 C 0.96326(15) 0.61859(17) 0.93760(9) 0.0344(4) Uani 1 1 d . . . . .
H61 H 0.904164 0.591625 0.910169 0.041 Uiso 1 1 calc R U . . .
C62 C 0.97278(18) 0.6282(2) 0.99940(10) 0.0428(5) Uani 1 1 d . . . . .
C63 C 1.0556(2) 0.6654(2) 1.04183(10) 0.0490(6) Uani 1 1 d . . . . .
H63 H 1.060223 0.671077 1.084115 0.059 Uiso 1 1 calc R U . . .
C64 C 1.13214(18) 0.6940(2) 1.01932(9) 0.0436(5) Uani 1 1 d . . . . .
C65 C 1.12790(16) 0.68782(16) 0.95800(9) 0.0341(4) Uani 1 1 d . . . . .
H65 H 1.182331 0.709418 0.944710 0.041 Uiso 1 1 calc R U . . .
F71 F 0.92934(10) 0.41572(17) 0.85509(8) 0.0642(5) Uani 1 1 d . . . . .
F72 F 0.76039(10) 0.35919(11) 0.64744(6) 0.0431(3) Uani 1 1 d . . . . .
F73 F -0.17227(9) 0.27517(12) 0.48284(6) 0.0472(3) Uani 1 1 d . . . . .
F74 F 0.08812(11) 0.42730(11) 0.42793(5) 0.0423(3) Uani 1 1 d . . . . .
C71 C 0.48128(14) 0.37922(16) 0.87075(8) 0.0292(4) Uani 1 1 d . . . . .
H71 H 0.482815 0.380767 0.912675 0.035 Uiso 1 1 calc R U . . .
C72 C 0.56854(13) 0.37874(15) 0.85468(8) 0.0278(3) Uani 1 1 d . . . . .
H72 H 0.630626 0.380034 0.886396 0.033 Uiso 1 1 calc R U . . .
C73 C 0.56900(12) 0.37641(13) 0.79275(7) 0.0212(3) Uani 1 1 d . . . . .
C74 C 0.47756(12) 0.37374(13) 0.74641(7) 0.0206(3) Uani 1 1 d . . . . .
H74 H 0.476186 0.372050 0.704516 0.025 Uiso 1 1 calc R U . . .
C75 C 0.23201(12) 0.36627(13) 0.66311(7) 0.0215(3) Uani 1 1 d . . . . .
H75 H 0.267599 0.363853 0.633701 0.026 Uiso 1 1 calc R U . . .
C76 C 0.12776(12) 0.36503(13) 0.64391(7) 0.0218(3) Uani 1 1 d . . . . .
C77 C 0.07627(12) 0.36985(14) 0.68851(8) 0.0248(3) Uani 1 1 d . . . . .
H77 H 0.005269 0.370086 0.675104 0.030 Uiso 1 1 calc R U . . .
C78 C 0.12540(13) 0.37422(14) 0.75058(8) 0.0255(3) Uani 1 1 d . . . . .
H78 H 0.089500 0.377369 0.779808 0.031 Uiso 1 1 calc R U . . .
N79 N 0.29498(11) 0.37762(13) 0.82757(7) 0.0267(3) Uani 1 1 d . . . . .
H79 H 0.2784(18) 0.3819(19) 0.8625(12) 0.032 Uiso 1 1 d . U . . .
C80 C 0.39086(13) 0.37736(14) 0.82368(7) 0.0232(3) Uani 1 1 d . . . . .
C81 C 0.38828(12) 0.37356(12) 0.76125(7) 0.0205(3) Uani 1 1 d . . . . .
C82 C 0.28374(12) 0.37107(12) 0.72577(7) 0.0201(3) Uani 1 1 d . . . . .
C83 C 0.22955(12) 0.37385(13) 0.76914(7) 0.0219(3) Uani 1 1 d . . . . .
C84 C 0.66524(12) 0.37863(12) 0.77838(8) 0.0220(3) Uani 1 1 d . . . . .
C85 C 0.75550(14) 0.39582(16) 0.82444(9) 0.0320(4) Uani 1 1 d . . . . .
H85 H 0.756283 0.404754 0.865892 0.038 Uiso 1 1 calc R U . . .
C86 C 0.84312(15) 0.39965(19) 0.80910(11) 0.0391(5) Uani 1 1 d . . . . .
C87 C 0.84865(15) 0.38896(16) 0.75060(11) 0.0364(4) Uani 1 1 d . . . . .
H87 H 0.910126 0.393211 0.741315 0.044 Uiso 1 1 calc R U . . .
C88 C 0.75918(14) 0.37161(14) 0.70604(9) 0.0291(4) Uani 1 1 d . . . . .
C89 C 0.66906(14) 0.36562(14) 0.71826(8) 0.0268(3) Uani 1 1 d . . . . .
H89 H 0.609508 0.352665 0.685895 0.032 Uiso 1 1 calc R U . . .
C90 C 0.06946(12) 0.35956(13) 0.57797(7) 0.0232(3) Uani 1 1 d . . . . .
C91 C -0.02574(13) 0.31691(15) 0.56007(8) 0.0278(3) Uani 1 1 d . . . . .
H91 H -0.052691 0.289541 0.589923 0.033 Uiso 1 1 calc R U . . .
C92 C -0.07996(14) 0.31517(16) 0.49840(9) 0.0329(4) Uani 1 1 d . . . . .
C93 C -0.04525(15) 0.35106(17) 0.45239(8) 0.0345(4) Uani 1 1 d . . . . .
H93 H -0.083591 0.348246 0.410251 0.041 Uiso 1 1 calc R U . . .
C94 C 0.04904(15) 0.39141(15) 0.47163(8) 0.0309(4) Uani 1 1 d . . . . .
C95 C 0.10722(14) 0.39766(14) 0.53229(8) 0.0265(3) Uani 1 1 d . . . . .
H95 H 0.171460 0.427124 0.542899 0.032 Uiso 1 1 calc R U . . .
N101 N 0.25386(11) 0.37393(13) 0.94184(6) 0.0254(3) Uani 1 1 d . . . . .
C101 C 0.14635(13) 0.38745(15) 0.93328(8) 0.0285(4) Uani 1 1 d . . . . .
H101 H 0.108378 0.331967 0.909587 0.034 Uiso 1 1 calc R U . . .
H102 H 0.122906 0.448083 0.909727 0.034 Uiso 1 1 calc R U . . .
C102 C 0.12746(13) 0.39378(16) 0.99654(9) 0.0296(4) Uani 1 1 d . . . . .
H103 H 0.096287 0.457345 1.000335 0.035 Uiso 1 1 calc R U . . .
H104 H 0.080848 0.341365 0.999932 0.035 Uiso 1 1 calc R U . . .
C103 C 0.28629(16) 0.28312(15) 0.97614(9) 0.0331(4) Uani 1 1 d . . . . .
H105 H 0.358144 0.272066 0.981529 0.040 Uiso 1 1 calc R U . . .
H106 H 0.248289 0.227400 0.952748 0.040 Uiso 1 1 calc R U . . .
C104 C 0.26878(16) 0.28941(15) 1.03973(9) 0.0326(4) Uani 1 1 d . . . . .
H107 H 0.224500 0.235426 1.044090 0.039 Uiso 1 1 calc R U . . .
H108 H 0.333331 0.282412 1.072509 0.039 Uiso 1 1 calc R U . . .
C105 C 0.30851(15) 0.45640(16) 0.97744(9) 0.0324(4) Uani 1 1 d . . . . .
H109 H 0.286093 0.517868 0.954624 0.039 Uiso 1 1 calc R U . . .
H110 H 0.380874 0.448650 0.983096 0.039 Uiso 1 1 calc R U . . .
C106 C 0.29054(15) 0.46198(15) 1.04082(8) 0.0309(4) Uani 1 1 d . . . . .
H111 H 0.354998 0.455667 1.073762 0.037 Uiso 1 1 calc R U . . .
H112 H 0.261062 0.526085 1.045489 0.037 Uiso 1 1 calc R U . . .
N102 N 0.22276(11) 0.38359(13) 1.04663(6) 0.0264(3) Uani 1 1 d . . . . .
F111 F -0.46265(9) 0.33079(11) 1.13605(6) 0.0402(3) Uani 1 1 d . . . . .
F112 F -0.29299(10) 0.40874(11) 1.34094(5) 0.0403(3) Uani 1 1 d . . . . .
F113 F 0.63089(10) 0.27999(15) 1.50661(7) 0.0585(4) Uani 1 1 d . . . . .
F114 F 0.37492(13) 0.45416(13) 1.55244(6) 0.0517(4) Uani 1 1 d . . . . .
C111 C -0.01860(13) 0.40964(14) 1.11600(8) 0.0258(3) Uani 1 1 d . . . . .
H113 H -0.020715 0.420328 1.074468 0.031 Uiso 1 1 calc R U . . .
C112 C -0.10545(13) 0.40677(14) 1.13277(8) 0.0249(3) Uani 1 1 d . . . . .
H114 H -0.167683 0.417015 1.102130 0.030 Uiso 1 1 calc R U . . .
C113 C -0.10462(12) 0.38907(12) 1.19408(7) 0.0208(3) Uani 1 1 d . . . . .
C114 C -0.01311(12) 0.37844(12) 1.23963(7) 0.0200(3) Uani 1 1 d . . . . .
H115 H -0.011092 0.367712 1.281145 0.024 Uiso 1 1 calc R U . . .
C115 C 0.23116(12) 0.36861(13) 1.32116(7) 0.0203(3) Uani 1 1 d . . . . .
H116 H 0.195370 0.364408 1.350412 0.024 Uiso 1 1 calc R U . . .
C116 C 0.33586(12) 0.36757(13) 1.34051(7) 0.0214(3) Uani 1 1 d . . . . .
C117 C 0.38722(12) 0.37242(14) 1.29606(8) 0.0250(3) Uani 1 1 d . . . . .
H117 H 0.458201 0.370665 1.309404 0.030 Uiso 1 1 calc R U . . .
C118 C 0.33790(13) 0.37965(14) 1.23371(8) 0.0251(3) Uani 1 1 d . . . . .
H118 H 0.373782 0.382840 1.204479 0.030 Uiso 1 1 calc R U . . .
N119 N 0.16810(11) 0.39500(12) 1.15724(7) 0.0252(3) Uani 1 1 d . . . . .
H119 H 0.1886(18) 0.3927(18) 1.1243(11) 0.030 Uiso 1 1 d . U . . .
C120 C 0.07205(13) 0.39640(13) 1.16183(7) 0.0225(3) Uani 1 1 d . . . . .
C121 C 0.07545(12) 0.38364(12) 1.22396(7) 0.0198(3) Uani 1 1 d . . . . .
C122 C 0.18008(11) 0.37584(12) 1.25874(7) 0.0194(3) Uani 1 1 d . . . . .
C123 C 0.23415(12) 0.38207(13) 1.21540(7) 0.0218(3) Uani 1 1 d . . . . .
C124 C -0.19993(12) 0.38190(12) 1.20957(7) 0.0216(3) Uani 1 1 d . . . . .
C125 C -0.28919(13) 0.35703(13) 1.16459(8) 0.0246(3) Uani 1 1 d . . . . .
H125 H -0.289642 0.343045 1.123708 0.030 Uiso 1 1 calc R U . . .
C126 C -0.37615(13) 0.35317(14) 1.18050(9) 0.0282(4) Uani 1 1 d . . . . .
C127 C -0.38123(13) 0.36884(15) 1.23913(9) 0.0295(4) Uani 1 1 d . . . . .
H127 H -0.442202 0.364426 1.248999 0.035 Uiso 1 1 calc R U . . .
C128 C -0.29198(14) 0.39132(14) 1.28245(8) 0.0278(4) Uani 1 1 d . . . . .
C129 C -0.20237(13) 0.39964(13) 1.26966(8) 0.0242(3) Uani 1 1 d . . . . .
H129 H -0.143149 0.417140 1.301096 0.029 Uiso 1 1 calc R U . . .
C130 C 0.39326(12) 0.36581(13) 1.40648(7) 0.0232(3) Uani 1 1 d . . . . .
C131 C 0.48702(14) 0.32061(16) 1.42655(8) 0.0298(4) Uani 1 1 d . . . . .
H131 H 0.513538 0.288144 1.398110 0.036 Uiso 1 1 calc R U . . .
C132 C 0.54035(14) 0.32388(18) 1.48820(9) 0.0371(5) Uani 1 1 d . . . . .
C133 C 0.50659(16) 0.36852(19) 1.53218(9) 0.0392(5) Uani 1 1 d . . . . .
H133 H 0.544886 0.370095 1.574352 0.047 Uiso 1 1 calc R U . . .
C134 C 0.41326(16) 0.41087(16) 1.51085(8) 0.0338(4) Uani 1 1 d . . . . .
C135 C 0.35613(14) 0.41147(14) 1.45005(8) 0.0273(3) Uani 1 1 d . . . . .
H135 H 0.292551 0.442341 1.437842 0.033 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
F1 C16 1.357(2) . ?
F2 C18 1.357(2) . ?
F3 C22 1.350(2) . ?
F4 C24 1.358(2) . ?
C1 C2 1.383(2) . ?
C1 C10 1.397(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.413(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.397(2) . ?
C3 C14 1.482(2) . ?
C4 C11 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C12 1.393(2) . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.414(2) . ?
C6 C20 1.483(2) . ?
C7 C8 1.383(2) . ?
C7 H7 0.9500 . ?
C8 C13 1.392(2) . ?
C8 H8 0.9500 . ?
N9 C10 1.376(2) . ?
N9 C13 1.378(2) . ?
N9 H9 0.86(2) . ?
C10 C11 1.416(2) . ?
C11 C12 1.448(2) . ?
C12 C13 1.420(2) . ?
C14 C15 1.397(2) . ?
C14 C19 1.400(2) . ?
C15 C16 1.381(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(3) . ?
C17 C18 1.375(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(3) . ?
C20 C25 1.402(2) . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(3) . ?
C23 C24 1.372(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9500 . ?
N31 C33 1.467(3) . ?
N31 C31 1.470(2) . ?
N31 C35 1.474(2) . ?
C31 C32 1.545(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 N32 1.473(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.541(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 N32 1.474(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.546(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 N32 1.471(2) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
F41 C56 1.362(2) . ?
F42 C58 1.357(2) . ?
F43 C62 1.361(3) . ?
F44 C64 1.354(3) . ?
C41 C42 1.382(2) . ?
C41 C50 1.392(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.413(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.399(2) . ?
C43 C54 1.487(2) . ?
C44 C51 1.393(2) . ?
C44 H44 0.9500 . ?
C45 C52 1.394(2) . ?
C45 C46 1.400(2) . ?
C45 H45 0.9500 . ?
C46 C47 1.414(2) . ?
C46 C60 1.484(2) . ?
C47 C48 1.382(2) . ?
C47 H47 0.9500 . ?
C48 C53 1.394(2) . ?
C48 H48 0.9500 . ?
N49 C53 1.377(2) . ?
N49 C50 1.379(2) . ?
N49 H49 0.89(2) . ?
C50 C51 1.417(2) . ?
C51 C52 1.449(2) . ?
C52 C53 1.416(2) . ?
C54 C59 1.402(2) . ?
C54 C55 1.403(2) . ?
C55 C56 1.379(2) . ?
C55 H55 0.9500 . ?
C56 C57 1.369(3) . ?
C57 C58 1.374(3) . ?
C57 H57 0.9500 . ?
C58 C59 1.374(2) . ?
C59 H59 0.9500 . ?
C60 C61 1.399(3) . ?
C60 C65 1.404(3) . ?
C61 C62 1.381(3) . ?
C61 H61 0.9500 . ?
C62 C63 1.367(4) . ?
C63 C64 1.379(4) . ?
C63 H63 0.9500 . ?
C64 C65 1.384(3) . ?
C65 H65 0.9500 . ?
F71 C86 1.359(2) . ?
F72 C88 1.352(2) . ?
F73 C92 1.352(2) . ?
F74 C94 1.366(2) . ?
C71 C72 1.380(3) . ?
C71 C80 1.393(2) . ?
C71 H71 0.9500 . ?
C72 C73 1.414(2) . ?
C72 H72 0.9500 . ?
C73 C74 1.395(2) . ?
C73 C84 1.483(2) . ?
C74 C81 1.393(2) . ?
C74 H74 0.9500 . ?
C75 C76 1.395(2) . ?
C75 C82 1.395(2) . ?
C75 H75 0.9500 . ?
C76 C77 1.416(2) . ?
C76 C90 1.481(2) . ?
C77 C78 1.376(2) . ?
C77 H77 0.9500 . ?
C78 C83 1.394(2) . ?
C78 H78 0.9500 . ?
N79 C83 1.372(2) . ?
N79 C80 1.375(2) . ?
N79 H79 0.90(3) . ?
C80 C81 1.414(2) . ?
C81 C82 1.446(2) . ?
C82 C83 1.418(2) . ?
C84 C89 1.400(2) . ?
C84 C85 1.400(2) . ?
C85 C86 1.377(3) . ?
C85 H85 0.9500 . ?
C86 C87 1.367(3) . ?
C87 C88 1.377(3) . ?
C87 H87 0.9500 . ?
C88 C89 1.377(2) . ?
C89 H89 0.9500 . ?
C90 C91 1.401(3) . ?
C90 C95 1.404(2) . ?
C91 C92 1.383(3) . ?
C91 H91 0.9500 . ?
C92 C93 1.374(3) . ?
C93 C94 1.378(3) . ?
C93 H93 0.9500 . ?
C94 C95 1.381(3) . ?
C95 H95 0.9500 . ?
N101 C105 1.466(3) . ?
N101 C103 1.467(3) . ?
N101 C101 1.473(2) . ?
C101 C102 1.546(3) . ?
C101 H101 0.9900 . ?
C101 H102 0.9900 . ?
C102 N102 1.480(2) . ?
C102 H103 0.9900 . ?
C102 H104 0.9900 . ?
C103 C104 1.545(3) . ?
C103 H105 0.9900 . ?
C103 H106 0.9900 . ?
C104 N102 1.472(3) . ?
C104 H107 0.9900 . ?
C104 H108 0.9900 . ?
C105 C106 1.542(3) . ?
C105 H109 0.9900 . ?
C105 H110 0.9900 . ?
C106 N102 1.467(3) . ?
C106 H111 0.9900 . ?
C106 H112 0.9900 . ?
F111 C126 1.361(2) . ?
F112 C128 1.359(2) . ?
F113 C132 1.353(3) . ?
F114 C134 1.360(2) . ?
C111 C112 1.383(2) . ?
C111 C120 1.393(2) . ?
C111 H113 0.9500 . ?
C112 C113 1.416(2) . ?
C112 H114 0.9500 . ?
C113 C114 1.395(2) . ?
C113 C124 1.486(2) . ?
C114 C121 1.395(2) . ?
C114 H115 0.9500 . ?
C115 C122 1.391(2) . ?
C115 C116 1.401(2) . ?
C115 H116 0.9500 . ?
C116 C117 1.412(2) . ?
C116 C130 1.477(2) . ?
C117 C118 1.384(2) . ?
C117 H117 0.9500 . ?
C118 C123 1.389(2) . ?
C118 H118 0.9500 . ?
N119 C123 1.381(2) . ?
N119 C120 1.383(2) . ?
N119 H119 0.88(3) . ?
C120 C121 1.414(2) . ?
C121 C122 1.447(2) . ?
C122 C123 1.418(2) . ?
C124 C125 1.401(2) . ?
C124 C129 1.402(2) . ?
C125 C126 1.375(3) . ?
C125 H125 0.9500 . ?
C126 C127 1.377(3) . ?
C127 C128 1.376(3) . ?
C127 H127 0.9500 . ?
C128 C129 1.379(2) . ?
C129 H129 0.9500 . ?
C130 C131 1.400(3) . ?
C130 C135 1.401(2) . ?
C131 C132 1.380(3) . ?
C131 H131 0.9500 . ?
C132 C133 1.375(3) . ?
C133 C134 1.380(3) . ?
C133 H133 0.9500 . ?
C134 C135 1.376(3) . ?
C135 H135 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
C2 C1 C10 117.89(15) . . ?
C2 C1 H1 121.1 . . ?
C10 C1 H1 121.1 . . ?
C1 C2 C3 122.36(16) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C4 C3 C2 118.78(15) . . ?
C4 C3 C14 121.30(14) . . ?
C2 C3 C14 119.92(15) . . ?
C11 C4 C3 120.09(14) . . ?
C11 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C12 C5 C6 119.39(14) . . ?
C12 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 119.53(15) . . ?
C5 C6 C20 120.95(14) . . ?
C7 C6 C20 119.52(15) . . ?
C8 C7 C6 122.04(15) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 117.86(15) . . ?
C7 C8 H8 121.1 . . ?
C13 C8 H8 121.1 . . ?
C10 N9 C13 108.65(13) . . ?
C10 N9 H9 120.7(17) . . ?
C13 N9 H9 130.2(17) . . ?
N9 C10 C1 129.25(15) . . ?
N9 C10 C11 109.76(14) . . ?
C1 C10 C11 120.99(15) . . ?
C4 C11 C10 119.85(15) . . ?
C4 C11 C12 134.15(14) . . ?
C10 C11 C12 105.99(13) . . ?
C5 C12 C13 119.76(15) . . ?
C5 C12 C11 133.89(14) . . ?
C13 C12 C11 106.33(13) . . ?
N9 C13 C8 129.28(14) . . ?
N9 C13 C12 109.28(14) . . ?
C8 C13 C12 121.41(15) . . ?
C15 C14 C19 117.97(15) . . ?
C15 C14 C3 121.54(15) . . ?
C19 C14 C3 120.49(15) . . ?
C16 C15 C14 119.43(16) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
F1 C16 C17 117.74(16) . . ?
F1 C16 C15 118.41(17) . . ?
C17 C16 C15 123.85(17) . . ?
C18 C17 C16 115.40(16) . . ?
C18 C17 H17 122.3 . . ?
C16 C17 H17 122.3 . . ?
F2 C18 C17 118.01(17) . . ?
F2 C18 C19 118.23(17) . . ?
C17 C18 C19 123.74(17) . . ?
C18 C19 C14 119.61(17) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?
C21 C20 C25 118.61(16) . . ?
C21 C20 C6 120.35(15) . . ?
C25 C20 C6 121.04(16) . . ?
C22 C21 C20 119.57(17) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
F3 C22 C21 118.34(18) . . ?
F3 C22 C23 118.41(17) . . ?
C21 C22 C23 123.25(19) . . ?
C24 C23 C22 115.81(17) . . ?
C24 C23 H23 122.1 . . ?
C22 C23 H23 122.1 . . ?
F4 C24 C23 117.82(17) . . ?
F4 C24 C25 118.00(19) . . ?
C23 C24 C25 124.18(18) . . ?
C24 C25 C20 118.58(18) . . ?
C24 C25 H25 120.7 . . ?
C20 C25 H25 120.7 . . ?
C33 N31 C31 108.80(15) . . ?
C33 N31 C35 108.71(14) . . ?
C31 N31 C35 108.86(15) . . ?
N31 C31 C32 109.87(13) . . ?
N31 C31 H31A 109.7 . . ?
C32 C31 H31A 109.7 . . ?
N31 C31 H31B 109.7 . . ?
C32 C31 H31B 109.7 . . ?
H31A C31 H31B 108.2 . . ?
N32 C32 C31 110.50(13) . . ?
N32 C32 H32A 109.6 . . ?
C31 C32 H32A 109.6 . . ?
N32 C32 H32B 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
N31 C33 C34 110.28(15) . . ?
N31 C33 H33A 109.6 . . ?
C34 C33 H33A 109.6 . . ?
N31 C33 H33B 109.6 . . ?
C34 C33 H33B 109.6 . . ?
H33A C33 H33B 108.1 . . ?
N32 C34 C33 110.28(15) . . ?
N32 C34 H34A 109.6 . . ?
C33 C34 H34A 109.6 . . ?
N32 C34 H34B 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
N31 C35 C36 110.31(14) . . ?
N31 C35 H35A 109.6 . . ?
C36 C35 H35A 109.6 . . ?
N31 C35 H35B 109.6 . . ?
C36 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
N32 C36 C35 110.01(14) . . ?
N32 C36 H36A 109.7 . . ?
C35 C36 H36A 109.7 . . ?
N32 C36 H36B 109.7 . . ?
C35 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C36 N32 C32 109.13(15) . . ?
C36 N32 C34 107.93(14) . . ?
C32 N32 C34 108.83(14) . . ?
C42 C41 C50 118.13(15) . . ?
C42 C41 H41 120.9 . . ?
C50 C41 H41 120.9 . . ?
C41 C42 C43 122.37(15) . . ?
C41 C42 H42 118.8 . . ?
C43 C42 H42 118.8 . . ?
C44 C43 C42 118.69(15) . . ?
C44 C43 C54 121.15(14) . . ?
C42 C43 C54 120.17(14) . . ?
C51 C44 C43 119.93(14) . . ?
C51 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C52 C45 C46 119.66(15) . . ?
C52 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C45 C46 C47 119.33(15) . . ?
C45 C46 C60 121.29(15) . . ?
C47 C46 C60 119.37(15) . . ?
C48 C47 C46 121.97(16) . . ?
C48 C47 H47 119.0 . . ?
C46 C47 H47 119.0 . . ?
C47 C48 C53 117.95(15) . . ?
C47 C48 H48 121.0 . . ?
C53 C48 H48 121.0 . . ?
C53 N49 C50 108.35(13) . . ?
C53 N49 H49 122.9(16) . . ?
C50 N49 H49 128.7(16) . . ?
N49 C50 C41 129.33(15) . . ?
N49 C50 C51 109.66(14) . . ?
C41 C50 C51 120.99(15) . . ?
C44 C51 C50 119.82(14) . . ?
C44 C51 C52 134.06(14) . . ?
C50 C51 C52 106.11(13) . . ?
C45 C52 C53 119.50(15) . . ?
C45 C52 C51 134.35(15) . . ?
C53 C52 C51 106.10(13) . . ?
N49 C53 C48 128.58(15) . . ?
N49 C53 C52 109.77(14) . . ?
C48 C53 C52 121.57(15) . . ?
C59 C54 C55 117.69(15) . . ?
C59 C54 C43 121.68(15) . . ?
C55 C54 C43 120.62(15) . . ?
C56 C55 C54 119.24(16) . . ?
C56 C55 H55 120.4 . . ?
C54 C55 H55 120.4 . . ?
F41 C56 C57 118.07(17) . . ?
F41 C56 C55 117.69(17) . . ?
C57 C56 C55 124.23(17) . . ?
C56 C57 C58 115.20(16) . . ?
C56 C57 H57 122.4 . . ?
C58 C57 H57 122.4 . . ?
F42 C58 C59 118.27(17) . . ?
F42 C58 C57 117.62(16) . . ?
C59 C58 C57 124.10(17) . . ?
C58 C59 C54 119.51(16) . . ?
C58 C59 H59 120.2 . . ?
C54 C59 H59 120.2 . . ?
C61 C60 C65 118.52(17) . . ?
C61 C60 C46 120.69(17) . . ?
C65 C60 C46 120.79(17) . . ?
C62 C61 C60 119.3(2) . . ?
C62 C61 H61 120.4 . . ?
C60 C61 H61 120.4 . . ?
F43 C62 C63 118.45(19) . . ?
F43 C62 C61 117.6(2) . . ?
C63 C62 C61 123.9(2) . . ?
C62 C63 C64 115.70(19) . . ?
C62 C63 H63 122.2 . . ?
C64 C63 H63 122.2 . . ?
F44 C64 C63 118.3(2) . . ?
F44 C64 C65 117.8(2) . . ?
C63 C64 C65 123.9(2) . . ?
C64 C65 C60 118.7(2) . . ?
C64 C65 H65 120.6 . . ?
C60 C65 H65 120.6 . . ?
C72 C71 C80 118.03(15) . . ?
C72 C71 H71 121.0 . . ?
C80 C71 H71 121.0 . . ?
C71 C72 C73 122.47(16) . . ?
C71 C72 H72 118.8 . . ?
C73 C72 H72 118.8 . . ?
C74 C73 C72 118.47(15) . . ?
C74 C73 C84 121.59(14) . . ?
C72 C73 C84 119.93(15) . . ?
C81 C74 C73 120.34(14) . . ?
C81 C74 H74 119.8 . . ?
C73 C74 H74 119.8 . . ?
C76 C75 C82 119.63(14) . . ?
C76 C75 H75 120.2 . . ?
C82 C75 H75 120.2 . . ?
C75 C76 C77 119.22(15) . . ?
C75 C76 C90 121.68(14) . . ?
C77 C76 C90 119.10(15) . . ?
C78 C77 C76 122.35(15) . . ?
C78 C77 H77 118.8 . . ?
C76 C77 H77 118.8 . . ?
C77 C78 C83 117.80(15) . . ?
C77 C78 H78 121.1 . . ?
C83 C78 H78 121.1 . . ?
C83 N79 C80 108.56(13) . . ?
C83 N79 H79 126.0(16) . . ?
C80 N79 H79 125.4(16) . . ?
N79 C80 C71 129.17(15) . . ?
N79 C80 C81 109.68(14) . . ?
C71 C80 C81 121.14(15) . . ?
C74 C81 C80 119.53(15) . . ?
C74 C81 C82 134.35(15) . . ?
C80 C81 C82 106.12(14) . . ?
C75 C82 C83 119.51(14) . . ?
C75 C82 C81 134.46(15) . . ?
C83 C82 C81 106.02(13) . . ?
N79 C83 C78 128.90(15) . . ?
N79 C83 C82 109.62(14) . . ?
C78 C83 C82 121.47(15) . . ?
C89 C84 C85 117.58(16) . . ?
C89 C84 C73 121.36(15) . . ?
C85 C84 C73 121.04(16) . . ?
C86 C85 C84 119.40(18) . . ?
C86 C85 H85 120.3 . . ?
C84 C85 H85 120.3 . . ?
F71 C86 C87 118.10(19) . . ?
F71 C86 C85 117.7(2) . . ?
C87 C86 C85 124.16(19) . . ?
C86 C87 C88 115.53(18) . . ?
C86 C87 H87 122.2 . . ?
C88 C87 H87 122.2 . . ?
F72 C88 C87 118.06(17) . . ?
F72 C88 C89 118.58(17) . . ?
C87 C88 C89 123.35(18) . . ?
C88 C89 C84 119.97(17) . . ?
C88 C89 H89 120.0 . . ?
C84 C89 H89 120.0 . . ?
C91 C90 C95 118.61(16) . . ?
C91 C90 C76 120.19(15) . . ?
C95 C90 C76 121.19(16) . . ?
C92 C91 C90 119.16(18) . . ?
C92 C91 H91 120.4 . . ?
C90 C91 H91 120.4 . . ?
F73 C92 C93 118.49(17) . . ?
F73 C92 C91 117.62(19) . . ?
C93 C92 C91 123.88(19) . . ?
C92 C93 C94 115.34(17) . . ?
C92 C93 H93 122.3 . . ?
C94 C93 H93 122.3 . . ?
F74 C94 C93 118.07(17) . . ?
F74 C94 C95 117.54(18) . . ?
C93 C94 C95 124.39(18) . . ?
C94 C95 C90 118.61(18) . . ?
C94 C95 H95 120.7 . . ?
C90 C95 H95 120.7 . . ?
C105 N101 C103 109.39(15) . . ?
C105 N101 C101 108.68(15) . . ?
C103 N101 C101 108.53(15) . . ?
N101 C101 C102 109.90(13) . . ?
N101 C101 H101 109.7 . . ?
C102 C101 H101 109.7 . . ?
N101 C101 H102 109.7 . . ?
C102 C101 H102 109.7 . . ?
H101 C101 H102 108.2 . . ?
N102 C102 C101 110.22(14) . . ?
N102 C102 H103 109.6 . . ?
C101 C102 H103 109.6 . . ?
N102 C102 H104 109.6 . . ?
C101 C102 H104 109.6 . . ?
H103 C102 H104 108.1 . . ?
N101 C103 C104 109.99(15) . . ?
N101 C103 H105 109.7 . . ?
C104 C103 H105 109.7 . . ?
N101 C103 H106 109.7 . . ?
C104 C103 H106 109.7 . . ?
H105 C103 H106 108.2 . . ?
N102 C104 C103 110.38(15) . . ?
N102 C104 H107 109.6 . . ?
C103 C104 H107 109.6 . . ?
N102 C104 H108 109.6 . . ?
C103 C104 H108 109.6 . . ?
H107 C104 H108 108.1 . . ?
N101 C105 C106 110.56(15) . . ?
N101 C105 H109 109.5 . . ?
C106 C105 H109 109.5 . . ?
N101 C105 H110 109.5 . . ?
C106 C105 H110 109.5 . . ?
H109 C105 H110 108.1 . . ?
N102 C106 C105 110.00(15) . . ?
N102 C106 H111 109.7 . . ?
C105 C106 H111 109.7 . . ?
N102 C106 H112 109.7 . . ?
C105 C106 H112 109.7 . . ?
H111 C106 H112 108.2 . . ?
C106 N102 C104 108.34(15) . . ?
C106 N102 C102 108.71(15) . . ?
C104 N102 C102 108.87(15) . . ?
C112 C111 C120 118.04(15) . . ?
C112 C111 H113 121.0 . . ?
C120 C111 H113 121.0 . . ?
C111 C112 C113 122.16(15) . . ?
C111 C112 H114 118.9 . . ?
C113 C112 H114 118.9 . . ?
C114 C113 C112 119.01(15) . . ?
C114 C113 C124 120.58(14) . . ?
C112 C113 C124 120.41(14) . . ?
C113 C114 C121 119.69(14) . . ?
C113 C114 H115 120.2 . . ?
C121 C114 H115 120.2 . . ?
C122 C115 C116 119.40(14) . . ?
C122 C115 H116 120.3 . . ?
C116 C115 H116 120.3 . . ?
C115 C116 C117 119.18(14) . . ?
C115 C116 C130 121.26(14) . . ?
C117 C116 C130 119.51(15) . . ?
C118 C117 C116 122.38(16) . . ?
C118 C117 H117 118.8 . . ?
C116 C117 H117 118.8 . . ?
C117 C118 C123 117.68(15) . . ?
C117 C118 H118 121.2 . . ?
C123 C118 H118 121.2 . . ?
C123 N119 C120 108.42(14) . . ?
C123 N119 H119 121.0(16) . . ?
C120 N119 H119 129.9(16) . . ?
N119 C120 C111 129.42(15) . . ?
N119 C120 C121 109.58(14) . . ?
C111 C120 C121 120.99(15) . . ?
C114 C121 C120 119.99(14) . . ?
C114 C121 C122 133.71(14) . . ?
C120 C121 C122 106.28(13) . . ?
C115 C122 C123 119.90(14) . . ?
C115 C122 C121 133.69(14) . . ?
C123 C122 C121 106.34(13) . . ?
N119 C123 C118 129.11(15) . . ?
N119 C123 C122 109.37(14) . . ?
C118 C123 C122 121.44(15) . . ?
C125 C124 C129 118.54(15) . . ?
C125 C124 C113 120.81(15) . . ?
C129 C124 C113 120.65(15) . . ?
C126 C125 C124 119.01(16) . . ?
C126 C125 H125 120.5 . . ?
C124 C125 H125 120.5 . . ?
F111 C126 C125 118.38(17) . . ?
F111 C126 C127 117.54(16) . . ?
C125 C126 C127 124.07(17) . . ?
C128 C127 C126 115.43(16) . . ?
C128 C127 H127 122.3 . . ?
C126 C127 H127 122.3 . . ?
F112 C128 C127 117.85(16) . . ?
F112 C128 C129 118.24(16) . . ?
C127 C128 C129 123.89(17) . . ?
C128 C129 C124 119.01(16) . . ?
C128 C129 H129 120.5 . . ?
C124 C129 H129 120.5 . . ?
C131 C130 C135 118.66(16) . . ?
C131 C130 C116 120.66(16) . . ?
C135 C130 C116 120.66(16) . . ?
C132 C131 C130 119.08(19) . . ?
C132 C131 H131 120.5 . . ?
C130 C131 H131 120.5 . . ?
F113 C132 C133 118.00(18) . . ?
F113 C132 C131 118.1(2) . . ?
C133 C132 C131 123.9(2) . . ?
C132 C133 C134 115.41(17) . . ?
C132 C133 H133 122.3 . . ?
C134 C133 H133 122.3 . . ?
F114 C134 C135 117.9(2) . . ?
F114 C134 C133 118.07(18) . . ?
C135 C134 C133 124.07(19) . . ?
C134 C135 C130 118.91(18) . . ?
C134 C135 H135 120.5 . . ?
C130 C135 H135 120.5 . . ?

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
C10 C1 C2 C3 1.4(3) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 C14 179.65(17) . . . . ?
C2 C3 C4 C11 -0.5(3) . . . . ?
C14 C3 C4 C11 178.61(15) . . . . ?
C12 C5 C6 C7 -0.7(3) . . . . ?
C12 C5 C6 C20 179.58(15) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C20 C6 C7 C8 -179.99(17) . . . . ?
C6 C7 C8 C13 0.2(3) . . . . ?
C13 N9 C10 C1 -179.19(18) . . . . ?
C13 N9 C10 C11 -0.4(2) . . . . ?
C2 C1 C10 N9 178.79(18) . . . . ?
C2 C1 C10 C11 0.1(3) . . . . ?
C3 C4 C11 C10 2.0(3) . . . . ?
C3 C4 C11 C12 -179.11(18) . . . . ?
N9 C10 C11 C4 179.29(16) . . . . ?
C1 C10 C11 C4 -1.8(3) . . . . ?
N9 C10 C11 C12 0.1(2) . . . . ?
C1 C10 C11 C12 178.99(16) . . . . ?
C6 C5 C12 C13 0.7(2) . . . . ?
C6 C5 C12 C11 178.71(18) . . . . ?
C4 C11 C12 C5 3.0(3) . . . . ?
C10 C11 C12 C5 -177.98(19) . . . . ?
C4 C11 C12 C13 -178.78(19) . . . . ?
C10 C11 C12 C13 0.25(19) . . . . ?
C10 N9 C13 C8 178.59(18) . . . . ?
C10 N9 C13 C12 0.6(2) . . . . ?
C7 C8 C13 N9 -178.04(18) . . . . ?
C7 C8 C13 C12 -0.2(3) . . . . ?
C5 C12 C13 N9 178.02(16) . . . . ?
C11 C12 C13 N9 -0.51(19) . . . . ?
C5 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 C8 -178.70(16) . . . . ?
C4 C3 C14 C15 160.30(17) . . . . ?
C2 C3 C14 C15 -20.6(3) . . . . ?
C4 C3 C14 C19 -20.1(3) . . . . ?
C2 C3 C14 C19 159.02(17) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C3 C14 C15 C16 179.43(17) . . . . ?
C14 C15 C16 F1 -179.38(18) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
F1 C16 C17 C18 179.99(18) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 F2 -179.12(18) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
F2 C18 C19 C14 179.36(17) . . . . ?
C17 C18 C19 C14 1.3(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C3 C14 C19 C18 179.75(17) . . . . ?
C5 C6 C20 C21 -146.20(18) . . . . ?
C7 C6 C20 C21 34.1(2) . . . . ?
C5 C6 C20 C25 33.8(3) . . . . ?
C7 C6 C20 C25 -145.87(18) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C6 C20 C21 C22 179.87(17) . . . . ?
C20 C21 C22 F3 -179.33(18) . . . . ?
C20 C21 C22 C23 0.0(3) . . . . ?
F3 C22 C23 C24 179.29(19) . . . . ?
C21 C22 C23 C24 0.0(3) . . . . ?
C22 C23 C24 F4 -178.66(18) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
F4 C24 C25 C20 178.48(17) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 0.3(3) . . . . ?
C6 C20 C25 C24 -179.66(16) . . . . ?
C33 N31 C31 C32 -60.29(19) . . . . ?
C35 N31 C31 C32 58.03(19) . . . . ?
N31 C31 C32 N32 1.7(2) . . . . ?
C31 N31 C33 C34 58.94(19) . . . . ?
C35 N31 C33 C34 -59.48(19) . . . . ?
N31 C33 C34 N32 0.8(2) . . . . ?
C33 N31 C35 C36 57.70(19) . . . . ?
C31 N31 C35 C36 -60.67(19) . . . . ?
N31 C35 C36 N32 2.5(2) . . . . ?
C35 C36 N32 C32 57.27(19) . . . . ?
C35 C36 N32 C34 -60.85(18) . . . . ?
C31 C32 N32 C36 -59.92(19) . . . . ?
C31 C32 N32 C34 57.63(19) . . . . ?
C33 C34 N32 C36 59.21(18) . . . . ?
C33 C34 N32 C32 -59.10(19) . . . . ?
C50 C41 C42 C43 2.0(3) . . . . ?
C41 C42 C43 C44 -2.0(3) . . . . ?
C41 C42 C43 C54 177.77(17) . . . . ?
C42 C43 C44 C51 0.0(3) . . . . ?
C54 C43 C44 C51 -179.79(15) . . . . ?
C52 C45 C46 C47 0.2(3) . . . . ?
C52 C45 C46 C60 -179.03(16) . . . . ?
C45 C46 C47 C48 0.6(3) . . . . ?
C60 C46 C47 C48 179.87(18) . . . . ?
C46 C47 C48 C53 -0.7(3) . . . . ?
C53 N49 C50 C41 -177.42(19) . . . . ?
C53 N49 C50 C51 0.8(2) . . . . ?
C42 C41 C50 N49 177.98(19) . . . . ?
C42 C41 C50 C51 0.0(3) . . . . ?
C43 C44 C51 C50 1.9(3) . . . . ?
C43 C44 C51 C52 -177.46(18) . . . . ?
N49 C50 C51 C44 179.71(16) . . . . ?
C41 C50 C51 C44 -1.9(3) . . . . ?
N49 C50 C51 C52 -0.8(2) . . . . ?
C41 C50 C51 C52 177.59(17) . . . . ?
C46 C45 C52 C53 -0.9(3) . . . . ?
C46 C45 C52 C51 176.29(18) . . . . ?
C44 C51 C52 C45 2.5(3) . . . . ?
C50 C51 C52 C45 -176.97(19) . . . . ?
C44 C51 C52 C53 179.90(19) . . . . ?
C50 C51 C52 C53 0.47(19) . . . . ?
C50 N49 C53 C48 176.42(19) . . . . ?
C50 N49 C53 C52 -0.4(2) . . . . ?
C47 C48 C53 N49 -176.48(18) . . . . ?
C47 C48 C53 C52 0.1(3) . . . . ?
C45 C52 C53 N49 177.87(16) . . . . ?
C51 C52 C53 N49 0.0(2) . . . . ?
C45 C52 C53 C48 0.7(3) . . . . ?
C51 C52 C53 C48 -177.16(17) . . . . ?
C44 C43 C54 C59 -12.3(3) . . . . ?
C42 C43 C54 C59 167.89(17) . . . . ?
C44 C43 C54 C55 166.43(17) . . . . ?
C42 C43 C54 C55 -13.4(3) . . . . ?
C59 C54 C55 C56 -0.4(3) . . . . ?
C43 C54 C55 C56 -179.17(17) . . . . ?
C54 C55 C56 F41 179.88(18) . . . . ?
C54 C55 C56 C57 1.0(3) . . . . ?
F41 C56 C57 C58 -179.06(19) . . . . ?
C55 C56 C57 C58 -0.2(3) . . . . ?
C56 C57 C58 F42 179.49(18) . . . . ?
C56 C57 C58 C59 -1.3(3) . . . . ?
F42 C58 C59 C54 -178.84(17) . . . . ?
C57 C58 C59 C54 1.9(3) . . . . ?
C55 C54 C59 C58 -1.0(3) . . . . ?
C43 C54 C59 C58 177.75(17) . . . . ?
C45 C46 C60 C61 -154.86(19) . . . . ?
C47 C46 C60 C61 25.9(3) . . . . ?
C45 C46 C60 C65 25.5(3) . . . . ?
C47 C46 C60 C65 -153.78(19) . . . . ?
C65 C60 C61 C62 0.4(3) . . . . ?
C46 C60 C61 C62 -179.21(19) . . . . ?
C60 C61 C62 F43 -179.5(2) . . . . ?
C60 C61 C62 C63 -0.7(4) . . . . ?
F43 C62 C63 C64 178.9(2) . . . . ?
C61 C62 C63 C64 0.1(4) . . . . ?
C62 C63 C64 F44 -179.7(2) . . . . ?
C62 C63 C64 C65 0.7(4) . . . . ?
F44 C64 C65 C60 179.5(2) . . . . ?
C63 C64 C65 C60 -0.9(4) . . . . ?
C61 C60 C65 C64 0.3(3) . . . . ?
C46 C60 C65 C64 179.95(19) . . . . ?
C80 C71 C72 C73 0.0(3) . . . . ?
C71 C72 C73 C74 -0.5(3) . . . . ?
C71 C72 C73 C84 178.40(19) . . . . ?
C72 C73 C74 C81 0.1(3) . . . . ?
C84 C73 C74 C81 -178.78(16) . . . . ?
C82 C75 C76 C77 0.7(3) . . . . ?
C82 C75 C76 C90 -179.73(16) . . . . ?
C75 C76 C77 C78 -1.0(3) . . . . ?
C90 C76 C77 C78 179.42(17) . . . . ?
C76 C77 C78 C83 0.0(3) . . . . ?
C83 N79 C80 C71 -179.1(2) . . . . ?
C83 N79 C80 C81 0.1(2) . . . . ?
C72 C71 C80 N79 -179.8(2) . . . . ?
C72 C71 C80 C81 1.0(3) . . . . ?
C73 C74 C81 C80 0.8(3) . . . . ?
C73 C74 C81 C82 -179.89(18) . . . . ?
N79 C80 C81 C74 179.28(16) . . . . ?
C71 C80 C81 C74 -1.4(3) . . . . ?
N79 C80 C81 C82 -0.2(2) . . . . ?
C71 C80 C81 C82 179.15(18) . . . . ?
C76 C75 C82 C83 0.5(3) . . . . ?
C76 C75 C82 C81 179.98(18) . . . . ?
C74 C81 C82 C75 1.3(4) . . . . ?
C80 C81 C82 C75 -179.35(19) . . . . ?
C74 C81 C82 C83 -179.18(19) . . . . ?
C80 C81 C82 C83 0.18(19) . . . . ?
C80 N79 C83 C78 -178.88(19) . . . . ?
C80 N79 C83 C82 0.0(2) . . . . ?
C77 C78 C83 N79 179.99(18) . . . . ?
C77 C78 C83 C82 1.2(3) . . . . ?
C75 C82 C83 N79 179.50(16) . . . . ?
C81 C82 C83 N79 -0.1(2) . . . . ?
C75 C82 C83 C78 -1.5(3) . . . . ?
C81 C82 C83 C78 178.86(17) . . . . ?
C74 C73 C84 C89 -8.3(3) . . . . ?
C72 C73 C84 C89 172.87(17) . . . . ?
C74 C73 C84 C85 170.44(18) . . . . ?
C72 C73 C84 C85 -8.4(3) . . . . ?
C89 C84 C85 C86 0.3(3) . . . . ?
C73 C84 C85 C86 -178.47(19) . . . . ?
C84 C85 C86 F71 -179.5(2) . . . . ?
C84 C85 C86 C87 0.9(4) . . . . ?
F71 C86 C87 C88 179.2(2) . . . . ?
C85 C86 C87 C88 -1.2(4) . . . . ?
C86 C87 C88 F72 -179.17(19) . . . . ?
C86 C87 C88 C89 0.3(3) . . . . ?
F72 C88 C89 C84 -179.67(17) . . . . ?
C87 C88 C89 C84 0.8(3) . . . . ?
C85 C84 C89 C88 -1.1(3) . . . . ?
C73 C84 C89 C88 177.64(17) . . . . ?
C75 C76 C90 C91 152.06(18) . . . . ?
C77 C76 C90 C91 -28.4(2) . . . . ?
C75 C76 C90 C95 -28.7(3) . . . . ?
C77 C76 C90 C95 150.79(18) . . . . ?
C95 C90 C91 C92 -1.1(3) . . . . ?
C76 C90 C91 C92 178.14(17) . . . . ?
C90 C91 C92 F73 -178.76(17) . . . . ?
C90 C91 C92 C93 1.6(3) . . . . ?
F73 C92 C93 C94 179.52(18) . . . . ?
C91 C92 C93 C94 -0.9(3) . . . . ?
C92 C93 C94 F74 179.24(17) . . . . ?
C92 C93 C94 C95 -0.4(3) . . . . ?
F74 C94 C95 C90 -178.78(16) . . . . ?
C93 C94 C95 C90 0.9(3) . . . . ?
C91 C90 C95 C94 -0.1(3) . . . . ?
C76 C90 C95 C94 -179.30(16) . . . . ?
C105 N101 C101 C102 -58.8(2) . . . . ?
C103 N101 C101 C102 60.0(2) . . . . ?
N101 C101 C102 N102 -0.4(2) . . . . ?
C105 N101 C103 C104 57.9(2) . . . . ?
C101 N101 C103 C104 -60.6(2) . . . . ?
N101 C103 C104 N102 1.2(2) . . . . ?
C103 N101 C105 C106 -58.4(2) . . . . ?
C101 N101 C105 C106 59.9(2) . . . . ?
N101 C105 C106 N102 -0.7(2) . . . . ?
C105 C106 N102 C104 59.53(19) . . . . ?
C105 C106 N102 C102 -58.6(2) . . . . ?
C103 C104 N102 C106 -60.0(2) . . . . ?
C103 C104 N102 C102 58.0(2) . . . . ?
C101 C102 N102 C106 59.4(2) . . . . ?
C101 C102 N102 C104 -58.4(2) . . . . ?
C120 C111 C112 C113 -1.3(3) . . . . ?
C111 C112 C113 C114 2.9(3) . . . . ?
C111 C112 C113 C124 -177.07(17) . . . . ?
C112 C113 C114 C121 -1.1(3) . . . . ?
C124 C113 C114 C121 178.82(15) . . . . ?
C122 C115 C116 C117 -0.9(3) . . . . ?
C122 C115 C116 C130 176.37(16) . . . . ?
C115 C116 C117 C118 1.0(3) . . . . ?
C130 C116 C117 C118 -176.40(17) . . . . ?
C116 C117 C118 C123 0.0(3) . . . . ?
C123 N119 C120 C111 178.46(19) . . . . ?
C123 N119 C120 C121 -0.3(2) . . . . ?
C112 C111 C120 N119 179.28(18) . . . . ?
C112 C111 C120 C121 -2.1(3) . . . . ?
C113 C114 C121 C120 -2.1(3) . . . . ?
C113 C114 C121 C122 -179.91(18) . . . . ?
N119 C120 C121 C114 -177.33(16) . . . . ?
C111 C120 C121 C114 3.8(3) . . . . ?
N119 C120 C121 C122 1.0(2) . . . . ?
C111 C120 C121 C122 -177.87(17) . . . . ?
C116 C115 C122 C123 0.0(3) . . . . ?
C116 C115 C122 C121 -176.41(18) . . . . ?
C114 C121 C122 C115 -6.5(3) . . . . ?
C120 C121 C122 C115 175.44(18) . . . . ?
C114 C121 C122 C123 176.71(19) . . . . ?
C120 C121 C122 C123 -1.32(19) . . . . ?
C120 N119 C123 C118 -177.38(18) . . . . ?
C120 N119 C123 C122 -0.5(2) . . . . ?
C117 C118 C123 N119 175.52(18) . . . . ?
C117 C118 C123 C122 -1.0(3) . . . . ?
C115 C122 C123 N119 -176.13(15) . . . . ?
C121 C122 C123 N119 1.2(2) . . . . ?
C115 C122 C123 C118 1.0(3) . . . . ?
C121 C122 C123 C118 178.29(17) . . . . ?
C114 C113 C124 C125 -156.61(17) . . . . ?
C112 C113 C124 C125 23.4(2) . . . . ?
C114 C113 C124 C129 23.2(3) . . . . ?
C112 C113 C124 C129 -156.83(17) . . . . ?
C129 C124 C125 C126 1.5(3) . . . . ?
C113 C124 C125 C126 -178.65(17) . . . . ?
C124 C125 C126 F111 178.73(17) . . . . ?
C124 C125 C126 C127 -2.5(3) . . . . ?
F111 C126 C127 C128 -179.94(17) . . . . ?
C125 C126 C127 C128 1.3(3) . . . . ?
C126 C127 C128 F112 179.17(17) . . . . ?
C126 C127 C128 C129 0.9(3) . . . . ?
F112 C128 C129 C124 179.98(16) . . . . ?
C127 C128 C129 C124 -1.8(3) . . . . ?
C125 C124 C129 C128 0.5(3) . . . . ?
C113 C124 C129 C128 -179.34(16) . . . . ?
C115 C116 C130 C131 149.81(18) . . . . ?
C117 C116 C130 C131 -32.9(3) . . . . ?
C115 C116 C130 C135 -31.8(3) . . . . ?
C117 C116 C130 C135 145.50(18) . . . . ?
C135 C130 C131 C132 -1.1(3) . . . . ?
C116 C130 C131 C132 177.34(18) . . . . ?
C130 C131 C132 F113 -179.83(19) . . . . ?
C130 C131 C132 C133 0.7(3) . . . . ?
F113 C132 C133 C134 -179.1(2) . . . . ?
C131 C132 C133 C134 0.3(3) . . . . ?
C132 C133 C134 F114 178.50(19) . . . . ?
C132 C133 C134 C135 -1.0(3) . . . . ?
F114 C134 C135 C130 -178.88(18) . . . . ?
C133 C134 C135 C130 0.7(3) . . . . ?
C131 C130 C135 C134 0.4(3) . . . . ?
C116 C130 C135 C134 -177.98(17) . . . . ?

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
_geom_hbond_publ_flag
N9 H9 N31 0.86(2) 1.99(2) 2.847(2) 174(2) . yes
C34 H34A F41 0.99 2.63 3.528(2) 151.2 1_455 yes
C34 H34A F72 0.99 2.61 3.231(2) 120.8 . yes
C36 H36A F74 0.99 2.64 3.617(2) 170.3 2_656 yes
N49 H49 N32 0.89(2) 2.00(2) 2.8808(19) 174(2) . yes
C55 H55 F114 0.95 2.50 3.297(2) 141.2 1_654 yes
N79 H79 N101 0.90(3) 1.94(3) 2.834(2) 172(2) . yes
C101 H101 F2 0.99 2.64 3.574(2) 158.3 2_546 yes
C104 H107 F43 0.99 2.65 3.490(3) 142.6 2_647 yes
N119 H119 N102 0.88(3) 1.97(3) 2.854(2) 175(2) . yes
C125 H125 F4 0.95 2.61 3.232(2) 123.5 2_546 yes

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes/ethyl acetate'
