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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_d69
_database_code_depnum_ccdc_archive 'CCDC 2189961'
loop_
_audit_author_name
_audit_author_address
'Natalie E Pridmore'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-01-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H48 F6 N6 O3'
_chemical_formula_sum            'C34 H48 F6 N6 O3'
_chemical_formula_weight         702.78
_chemical_melting_point          410
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.5304(3)
_cell_length_b                   14.4783(4)
_cell_length_c                   19.2467(5)
_cell_angle_alpha                86.9520(10)
_cell_angle_beta                 73.8210(10)
_cell_angle_gamma                84.3910(10)
_cell_volume                     3602.39(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9522
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.29
_cell_measurement_theta_min      3.41
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.641
_exptl_absorpt_coefficient_mu    0.891
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.3358
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1548 before and 0.0644 after correction.
The Ratio of minimum to maximum transmission is 0.4459.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            77150
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.498
_diffrn_reflns_theta_min         2.391
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON III C7'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'Bruker D8 Venture dual source kappa CPAD'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\uS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12122
_reflns_number_total             13215
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.39.0 (Bruker, 2018)'
_computing_data_collection       'Bruker SC-XRD Suite'
_computing_data_reduction        'SAINT v8.39.0 (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1207
_refine_ls_number_reflns         13215
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+1.4242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0887
_refine_special_details          
;
 One of the CF3 groups is disordered, due to spinning and has been modelled with
 the fluorine atoms in two positions, with a refined occupancy ratio of
 0.60:0.40(2). Atom distances have been restrained to be the same in the major
 and minor component (SADI). Due to proximity, equivalent atoms in the major
 and minor component have been restrained to have the same ADP (SIMU).

 Hydrogen atoms on nitrogens were found by difference map. All other 
 hydrogens were placed geometrically and refined using a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C41-F7 \\sim C41-F7A \\sim C41-F8 \\sim C41-F8A \\sim C41-F9 \\sim C41-F9A
 with sigma of 0.01
 F7-F8 \\sim F7A-F8A \\sim F8-F9 \\sim F8A-F9A \\sim F9-F7 \\sim F9A-F7A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F7 \\sim F7A \\sim F8 \\sim F8A \\sim F9 \\sim F9A: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(1)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.43748(9) -0.24431(8) 1.01905(6) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.46497(9) -0.32898(8) 1.05019(6) 0.0176(2) Uani 1 1 d . . . . .
H2 H 0.5370(12) -0.3516(10) 1.0385(8) 0.021 Uiso 1 1 d . U . . .
C3 C 0.38954(9) -0.37891(8) 1.09685(6) 0.0170(2) Uani 1 1 d . . . . .
C4 C 0.28575(9) -0.34629(8) 1.11419(6) 0.0180(2) Uani 1 1 d . . . . .
H4 H 0.2324(12) -0.3781(10) 1.1461(8) 0.022 Uiso 1 1 d . U . . .
C5 C 0.26003(9) -0.26104(8) 1.08344(6) 0.0175(2) Uani 1 1 d . . . . .
C6 C 0.33361(9) -0.20999(8) 1.03639(6) 0.0178(2) Uani 1 1 d . . . . .
H6 H 0.3122(11) -0.1522(11) 1.0172(8) 0.021 Uiso 1 1 d . U . . .
C7 C 0.42334(9) -0.47013(8) 1.12784(6) 0.0195(2) Uani 1 1 d . . . . .
C8 C 0.14928(9) -0.22253(9) 1.10340(7) 0.0201(2) Uani 1 1 d . . . . .
C9 C 0.51169(9) -0.10921(8) 0.94400(6) 0.0171(2) Uani 1 1 d . . . . .
C10 C 0.60953(9) 0.00677(8) 0.86667(6) 0.0182(2) Uani 1 1 d . . . . .
H10A H 0.6844(12) 0.0168(10) 0.8479(8) 0.022 Uiso 1 1 d . U . . .
H10B H 0.5754(11) 0.0519(11) 0.9034(8) 0.022 Uiso 1 1 d . U . . .
C11 C 0.55804(9) 0.01348(8) 0.80479(6) 0.0180(2) Uani 1 1 d . . . . .
H11A H 0.6039(12) -0.0180(10) 0.7620(8) 0.022 Uiso 1 1 d . U . . .
H11B H 0.4941(12) -0.0167(10) 0.8200(8) 0.022 Uiso 1 1 d . U . . .
C12 C 0.60715(9) 0.15318(8) 0.72293(6) 0.0171(2) Uani 1 1 d . . . . .
H12A H 0.5692(11) 0.1859(10) 0.6909(8) 0.021 Uiso 1 1 d . U . . .
H12B H 0.6556(11) 0.1055(10) 0.6950(8) 0.021 Uiso 1 1 d . U . . .
C13 C 0.66620(9) 0.22145(8) 0.75100(6) 0.0176(2) Uani 1 1 d . . . . .
H13A H 0.6189(12) 0.2534(10) 0.7914(8) 0.021 Uiso 1 1 d . U . . .
H13B H 0.7233(12) 0.1864(10) 0.7673(8) 0.021 Uiso 1 1 d . U . . .
C14 C 0.82463(9) 0.28802(9) 0.66692(6) 0.0191(2) Uani 1 1 d . . . . .
H14A H 0.8559(12) 0.2496(10) 0.7001(8) 0.023 Uiso 1 1 d . U . . .
H14B H 0.8450(12) 0.3507(11) 0.6669(8) 0.023 Uiso 1 1 d . U . . .
C15 C 0.86585(9) 0.25006(8) 0.59125(6) 0.0181(2) Uani 1 1 d . . . . .
C16 C 0.97209(10) 0.24263(9) 0.55936(7) 0.0248(3) Uani 1 1 d . . . . .
H16 H 1.0174(13) 0.2624(11) 0.5856(9) 0.030 Uiso 1 1 d . U . . .
C17 C 1.01314(11) 0.20689(11) 0.49069(8) 0.0328(3) Uani 1 1 d . . . . .
H17 H 1.0868(14) 0.2008(12) 0.4707(9) 0.039 Uiso 1 1 d . U . . .
C18 C 0.94854(11) 0.17788(10) 0.45287(8) 0.0308(3) Uani 1 1 d . . . . .
H18 H 0.9756(13) 0.1514(12) 0.4064(10) 0.037 Uiso 1 1 d . U . . .
C19 C 0.84297(11) 0.18554(10) 0.48429(7) 0.0285(3) Uani 1 1 d . . . . .
H19 H 0.7964(13) 0.1657(12) 0.4596(9) 0.034 Uiso 1 1 d . U . . .
C20 C 0.80176(10) 0.22178(9) 0.55269(7) 0.0226(3) Uani 1 1 d . . . . .
H20 H 0.7284(13) 0.2266(11) 0.5735(8) 0.027 Uiso 1 1 d . U . . .
C21 C 0.44877(9) 0.16259(8) 0.82024(6) 0.0180(2) Uani 1 1 d . . . . .
C22 C 0.29618(9) 0.17872(9) 0.92393(7) 0.0204(2) Uani 1 1 d . . . . .
H22A H 0.2724(12) 0.2245(11) 0.8930(8) 0.024 Uiso 1 1 d . U . . .
H22B H 0.3179(12) 0.2117(11) 0.9609(8) 0.024 Uiso 1 1 d . U . . .
C23 C 0.20944(9) 0.11904(9) 0.96084(7) 0.0215(3) Uani 1 1 d . . . . .
H23A H 0.2337(12) 0.0705(11) 0.9911(8) 0.026 Uiso 1 1 d . U . . .
H23B H 0.1890(12) 0.0864(11) 0.9234(8) 0.026 Uiso 1 1 d . U . . .
C24 C 0.11627(9) 0.17675(9) 1.00691(7) 0.0220(3) Uani 1 1 d . . . . .
H24A H 0.1363(12) 0.2073(11) 1.0441(9) 0.026 Uiso 1 1 d . U . . .
H24B H 0.0950(12) 0.2275(11) 0.9752(8) 0.026 Uiso 1 1 d . U . . .
C25 C 0.02521(10) 0.12051(10) 1.04261(7) 0.0241(3) Uani 1 1 d . . . . .
H25A H 0.0041(12) 0.0929(11) 1.0050(9) 0.029 Uiso 1 1 d . U . . .
H25B H 0.0484(12) 0.0665(11) 1.0716(9) 0.029 Uiso 1 1 d . U . . .
C26 C -0.06527(11) 0.17742(11) 1.09169(8) 0.0322(3) Uani 1 1 d . . . . .
H26A H -0.0850(14) 0.2312(13) 1.0650(10) 0.039 Uiso 1 1 d . U . . .
H26B H -0.0429(14) 0.2051(12) 1.1298(10) 0.039 Uiso 1 1 d . U . . .
C27 C -0.15927(13) 0.12248(16) 1.12279(11) 0.0495(5) Uani 1 1 d . . . . .
H27A H -0.1880(19) 0.0989(17) 1.0826(13) 0.074 Uiso 1 1 d . U . . .
H27B H -0.214(2) 0.1588(17) 1.1560(13) 0.074 Uiso 1 1 d . U . . .
H27C H -0.1416(19) 0.0681(18) 1.1509(13) 0.074 Uiso 1 1 d . U . . .
C28 C 0.65499(9) 0.36275(8) 0.67452(6) 0.0167(2) Uani 1 1 d . . . . .
C29 C 0.48297(9) 0.43373(8) 0.67373(7) 0.0207(2) Uani 1 1 d . . . . .
H29A H 0.5270(12) 0.4715(11) 0.6345(8) 0.025 Uiso 1 1 d . U . . .
H29B H 0.4442(12) 0.4755(11) 0.7126(8) 0.025 Uiso 1 1 d . U . . .
C30 C 0.40784(10) 0.38389(9) 0.64550(7) 0.0246(3) Uani 1 1 d . . . . .
H30A H 0.3624(12) 0.3473(11) 0.6871(9) 0.030 Uiso 1 1 d . U . . .
H30B H 0.3618(13) 0.4320(11) 0.6287(8) 0.030 Uiso 1 1 d . U . . .
C31 C 0.45948(10) 0.31662(9) 0.58486(7) 0.0244(3) Uani 1 1 d . . . . .
H31A H 0.5015(12) 0.2656(11) 0.6031(8) 0.029 Uiso 1 1 d . U . . .
H31B H 0.4052(13) 0.2842(11) 0.5722(8) 0.029 Uiso 1 1 d . U . . .
C32 C 0.52752(10) 0.36041(9) 0.51674(7) 0.0248(3) Uani 1 1 d . . . . .
H32A H 0.4844(13) 0.4085(11) 0.4955(9) 0.030 Uiso 1 1 d . U . . .
H32B H 0.5789(13) 0.3932(11) 0.5285(9) 0.030 Uiso 1 1 d . U . . .
C33 C 0.58204(10) 0.29020(9) 0.45948(7) 0.0240(3) Uani 1 1 d . . . . .
H33A H 0.5298(13) 0.2581(11) 0.4454(8) 0.029 Uiso 1 1 d . U . . .
H33B H 0.6219(12) 0.2418(11) 0.4812(8) 0.029 Uiso 1 1 d . U . . .
C34 C 0.65405(12) 0.33349(11) 0.39316(8) 0.0317(3) Uani 1 1 d . . . . .
H34A H 0.6902(15) 0.2869(14) 0.3562(11) 0.047 Uiso 1 1 d . U . . .
H34B H 0.7071(15) 0.3628(13) 0.4074(10) 0.047 Uiso 1 1 d . U . . .
H34C H 0.6149(15) 0.3833(14) 0.3693(10) 0.047 Uiso 1 1 d . U . . .
F1 F 0.51429(6) -0.46907(5) 1.14213(4) 0.03030(18) Uani 1 1 d . . . . .
F2 F 0.43421(7) -0.53980(5) 1.08283(5) 0.0370(2) Uani 1 1 d . . . . .
F3 F 0.35630(6) -0.49433(6) 1.18997(4) 0.0353(2) Uani 1 1 d . . . . .
F4 F 0.08808(6) -0.27602(6) 1.08221(4) 0.02933(17) Uani 1 1 d . . . . .
F5 F 0.13523(6) -0.13752(6) 1.07484(5) 0.0348(2) Uani 1 1 d . . . . .
F6 F 0.10979(6) -0.21510(6) 1.17539(4) 0.02902(17) Uani 1 1 d . . . . .
N1 N 0.51692(8) -0.19884(7) 0.97199(6) 0.0193(2) Uani 1 1 d . . . . .
H1 H 0.5766(13) -0.2304(11) 0.9568(8) 0.026(4) Uiso 1 1 d . . . . .
N2 N 0.60359(8) -0.08472(7) 0.90133(6) 0.0193(2) Uani 1 1 d . . . . .
H2A H 0.6557(12) -0.1257(11) 0.8929(8) 0.022(4) Uiso 1 1 d . . . . .
N3 N 0.53373(8) 0.10851(7) 0.78248(5) 0.0181(2) Uani 1 1 d . . . . .
N4 N 0.71286(7) 0.29088(7) 0.69709(5) 0.0173(2) Uani 1 1 d . . . . .
N5 N 0.38454(8) 0.12353(8) 0.87906(6) 0.0203(2) Uani 1 1 d . . . . .
H5 H 0.4026(12) 0.0720(12) 0.8968(9) 0.026(4) Uiso 1 1 d . . . . .
N6 N 0.55216(8) 0.36815(7) 0.70194(5) 0.0184(2) Uani 1 1 d . . . . .
H6A H 0.5235(13) 0.3263(12) 0.7327(9) 0.029(4) Uiso 1 1 d . . . . .
O1 O 0.43239(6) -0.05605(6) 0.95680(4) 0.01981(18) Uani 1 1 d . . . . .
O2 O 0.43115(6) 0.24380(6) 0.79983(5) 0.02121(18) Uani 1 1 d . . . . .
O3 O 0.69990(6) 0.42042(6) 0.62850(5) 0.02136(18) Uani 1 1 d . . . . .
C35 C 0.66343(9) 0.67612(8) 0.59452(6) 0.0164(2) Uani 1 1 d . . . . .
C36 C 0.59642(9) 0.67334(8) 0.66460(6) 0.0175(2) Uani 1 1 d . . . . .
H36 H 0.5879(11) 0.6146(11) 0.6913(8) 0.021 Uiso 1 1 d . U . . .
C37 C 0.54285(9) 0.75409(9) 0.69598(6) 0.0188(2) Uani 1 1 d . . . . .
C38 C 0.55440(9) 0.83921(9) 0.65913(7) 0.0197(2) Uani 1 1 d . . . . .
H38 H 0.5186(12) 0.8945(11) 0.6804(8) 0.024 Uiso 1 1 d . U . . .
C39 C 0.62221(9) 0.84139(8) 0.59026(7) 0.0190(2) Uani 1 1 d . . . . .
C40 C 0.67714(9) 0.76148(8) 0.55731(6) 0.0176(2) Uani 1 1 d . . . . .
H40 H 0.7213(12) 0.7655(10) 0.5093(8) 0.021 Uiso 1 1 d . U . . .
C41 C 0.47121(10) 0.74643(9) 0.77069(7) 0.0231(3) Uani 1 1 d D . . . .
C42 C 0.63518(10) 0.93094(9) 0.54685(7) 0.0243(3) Uani 1 1 d . . . . .
C43 C 0.77726(9) 0.57409(8) 0.49930(6) 0.0165(2) Uani 1 1 d . . . . .
C44 C 0.88508(9) 0.45467(8) 0.42172(6) 0.0186(2) Uani 1 1 d . . . . .
H44A H 0.8537(11) 0.4738(10) 0.3828(8) 0.022 Uiso 1 1 d . U . . .
H44B H 0.8932(11) 0.3865(11) 0.4232(8) 0.022 Uiso 1 1 d . U . . .
C45 C 0.99040(9) 0.49497(8) 0.40618(6) 0.0173(2) Uani 1 1 d . . . . .
H45A H 0.9813(11) 0.5585(11) 0.4235(8) 0.021 Uiso 1 1 d . U . . .
H45B H 1.0354(11) 0.4581(10) 0.4319(8) 0.021 Uiso 1 1 d . U . . .
C46 C 1.13016(9) 0.42428(8) 0.30211(6) 0.0179(2) Uani 1 1 d . . . . .
H46A H 1.1580(11) 0.4001(10) 0.3430(8) 0.022 Uiso 1 1 d . U . . .
H46B H 1.1848(12) 0.4505(10) 0.2659(8) 0.022 Uiso 1 1 d . U . . .
C47 C 1.09329(9) 0.34371(8) 0.26989(6) 0.0174(2) Uani 1 1 d . . . . .
H47A H 1.0571(11) 0.3014(10) 0.3090(8) 0.021 Uiso 1 1 d . U . . .
H47B H 1.0443(12) 0.3682(10) 0.2437(8) 0.021 Uiso 1 1 d . U . . .
C48 C 1.23048(9) 0.21266(8) 0.25235(6) 0.0171(2) Uani 1 1 d . . . . .
H48A H 1.2369(11) 0.2327(10) 0.2992(8) 0.021 Uiso 1 1 d . U . . .
H48B H 1.3003(12) 0.2017(10) 0.2191(8) 0.021 Uiso 1 1 d . U . . .
C49 C 1.17392(9) 0.12536(8) 0.26630(6) 0.0170(2) Uani 1 1 d . . . . .
C50 C 1.12332(10) 0.09750(9) 0.21796(7) 0.0232(3) Uani 1 1 d . . . . .
H50 H 1.1241(12) 0.1359(11) 0.1748(9) 0.028 Uiso 1 1 d . U . . .
C51 C 1.07408(11) 0.01617(10) 0.23110(8) 0.0286(3) Uani 1 1 d . . . . .
H51 H 1.0407(13) -0.0025(12) 0.1962(9) 0.034 Uiso 1 1 d . U . . .
C52 C 1.07396(10) -0.03817(9) 0.29268(8) 0.0287(3) Uani 1 1 d . . . . .
H52 H 1.0376(13) -0.0932(12) 0.3028(9) 0.034 Uiso 1 1 d . U . . .
C53 C 1.12409(10) -0.01140(9) 0.34107(8) 0.0266(3) Uani 1 1 d . . . . .
H53 H 1.1226(13) -0.0451(12) 0.3855(9) 0.032 Uiso 1 1 d . U . . .
C54 C 1.17385(9) 0.07000(9) 0.32756(7) 0.0211(2) Uani 1 1 d . . . . .
H54 H 1.2060(12) 0.0898(11) 0.3619(8) 0.025 Uiso 1 1 d . U . . .
C55 C 1.01880(9) 0.55623(8) 0.27970(6) 0.0162(2) Uani 1 1 d . . . . .
C56 C 0.89461(10) 0.68080(8) 0.25619(6) 0.0199(2) Uani 1 1 d . . . . .
H56A H 0.8440(12) 0.6460(10) 0.2411(8) 0.024 Uiso 1 1 d . U . . .
H56B H 0.9501(12) 0.6943(10) 0.2134(8) 0.024 Uiso 1 1 d . U . . .
C57 C 0.84049(10) 0.76897(9) 0.29317(7) 0.0217(3) Uani 1 1 d . . . . .
H57A H 0.8903(12) 0.8023(11) 0.3079(8) 0.026 Uiso 1 1 d . U . . .
H57B H 0.7864(12) 0.7522(11) 0.3384(9) 0.026 Uiso 1 1 d . U . . .
C58 C 0.78990(11) 0.83153(9) 0.24430(8) 0.0274(3) Uani 1 1 d . . . . .
H58A H 0.7453(13) 0.7935(12) 0.2264(9) 0.033 Uiso 1 1 d . U . . .
H58B H 0.8450(13) 0.8521(12) 0.2017(9) 0.033 Uiso 1 1 d . U . . .
C59 C 0.72276(11) 0.91580(10) 0.28186(8) 0.0318(3) Uani 1 1 d . . . . .
H59A H 0.6929(13) 0.9541(12) 0.2466(9) 0.038 Uiso 1 1 d . U . . .
H59B H 0.6605(14) 0.8972(12) 0.3240(10) 0.038 Uiso 1 1 d . U . . .
C60 C 0.78065(12) 0.98029(10) 0.31237(9) 0.0343(3) Uani 1 1 d . . . . .
H60A H 0.8477(14) 0.9926(12) 0.2718(10) 0.041 Uiso 1 1 d . U . . .
H60B H 0.8004(14) 0.9484(12) 0.3543(10) 0.041 Uiso 1 1 d . U . . .
C61 C 0.71673(17) 1.07043(12) 0.33864(11) 0.0470(4) Uani 1 1 d . . . . .
H61A H 0.6942(18) 1.1039(16) 0.2986(13) 0.071 Uiso 1 1 d . U . . .
H61B H 0.7602(19) 1.1128(17) 0.3534(13) 0.071 Uiso 1 1 d . U . . .
H61C H 0.6537(19) 1.0579(16) 0.3784(13) 0.071 Uiso 1 1 d . U . . .
C62 C 1.21430(9) 0.31293(8) 0.14905(6) 0.0163(2) Uani 1 1 d . . . . .
C63 C 1.20828(10) 0.42206(9) 0.04909(6) 0.0200(2) Uani 1 1 d . . . . .
H63A H 1.2201(12) 0.3680(11) 0.0202(8) 0.024 Uiso 1 1 d . U . . .
H63B H 1.2758(12) 0.4499(10) 0.0390(8) 0.024 Uiso 1 1 d . U . . .
C64 C 1.12841(11) 0.49129(9) 0.02940(7) 0.0241(3) Uani 1 1 d . . . . .
H64A H 1.1087(12) 0.5382(11) 0.0662(9) 0.029 Uiso 1 1 d . U . . .
H64B H 1.0670(13) 0.4585(11) 0.0316(8) 0.029 Uiso 1 1 d . U . . .
C65 C 1.16962(11) 0.53658(9) -0.04542(7) 0.0262(3) Uani 1 1 d . . . . .
H65A H 1.1165(13) 0.5863(12) -0.0541(9) 0.031 Uiso 1 1 d . U . . .
H65B H 1.2337(13) 0.5686(11) -0.0472(9) 0.031 Uiso 1 1 d . U . . .
C66 C 1.19851(11) 0.46852(9) -0.10696(7) 0.0243(3) Uani 1 1 d . . . . .
H66A H 1.1366(13) 0.4342(11) -0.1042(8) 0.029 Uiso 1 1 d . U . . .
H66B H 1.2542(13) 0.4198(11) -0.0995(8) 0.029 Uiso 1 1 d . U . . .
C67 C 1.23704(11) 0.51433(10) -0.18170(7) 0.0269(3) Uani 1 1 d . . . . .
H67A H 1.2960(13) 0.5479(12) -0.1824(9) 0.032 Uiso 1 1 d . U . . .
H67B H 1.2638(13) 0.4651(12) -0.2181(9) 0.032 Uiso 1 1 d . U . . .
C68 C 1.15452(13) 0.57686(12) -0.20477(8) 0.0363(3) Uani 1 1 d . . . . .
H68A H 1.1815(16) 0.6018(14) -0.2556(11) 0.054 Uiso 1 1 d . U . . .
H68B H 1.1328(16) 0.6310(15) -0.1734(11) 0.054 Uiso 1 1 d . U . . .
H68C H 1.0934(17) 0.5436(14) -0.2009(11) 0.054 Uiso 1 1 d . U . . .
F7 F 0.5225(4) 0.7112(6) 0.8169(3) 0.0514(12) Uani 0.60(2) 1 d D U P A 1
F7A F 0.5057(9) 0.6854(8) 0.8146(4) 0.057(2) Uani 0.40(2) 1 d D U P A 2
F8 F 0.3951(5) 0.6944(5) 0.7750(5) 0.0446(12) Uani 0.60(2) 1 d D U P A 1
F8A F 0.3827(7) 0.7155(10) 0.7680(8) 0.0457(19) Uani 0.40(2) 1 d D U P A 2
F9 F 0.4284(6) 0.8287(4) 0.7962(5) 0.0404(13) Uani 0.60(2) 1 d D U P A 1
F9A F 0.4449(11) 0.8259(5) 0.8046(7) 0.044(2) Uani 0.40(2) 1 d D U P A 2
F10 F 0.59276(9) 1.00492(6) 0.58612(5) 0.0482(3) Uani 1 1 d . . . . .
F11 F 0.59229(8) 0.93236(6) 0.49225(5) 0.0423(2) Uani 1 1 d . . . . .
F12 F 0.73456(7) 0.94479(6) 0.51675(5) 0.0387(2) Uani 1 1 d . . . . .
N7 N 0.71289(8) 0.59139(7) 0.56728(5) 0.0180(2) Uani 1 1 d . . . . .
H7 H 0.6986(12) 0.5413(12) 0.5959(9) 0.028(4) Uiso 1 1 d . . . . .
N8 N 0.81663(8) 0.48439(7) 0.49077(5) 0.0194(2) Uani 1 1 d . . . . .
H8 H 0.7962(12) 0.4448(11) 0.5256(9) 0.025(4) Uiso 1 1 d . . . . .
N9 N 1.04701(7) 0.49566(7) 0.32983(5) 0.0172(2) Uani 1 1 d . . . . .
N10 N 1.17831(8) 0.28976(7) 0.22098(5) 0.0174(2) Uani 1 1 d . . . . .
N11 N 0.93982(8) 0.62121(7) 0.30500(6) 0.0181(2) Uani 1 1 d . . . . .
H11 H 0.9028(12) 0.6194(10) 0.3485(9) 0.021(4) Uiso 1 1 d . . . . .
N12 N 1.17331(8) 0.39255(7) 0.12503(6) 0.0189(2) Uani 1 1 d . . . . .
H12 H 1.1413(12) 0.4312(11) 0.1545(8) 0.022(4) Uiso 1 1 d . . . . .
O4 O 0.79868(6) 0.63416(6) 0.45078(4) 0.02053(18) Uani 1 1 d . . . . .
O5 O 1.06633(6) 0.55118(6) 0.21455(4) 0.02039(18) Uani 1 1 d . . . . .
O6 O 1.28023(6) 0.26000(6) 0.10738(4) 0.01918(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 1.3991(17) . ?
C1 C6 1.3976(17) . ?
C1 N1 1.3933(15) . ?
C2 H2 0.965(15) . ?
C2 C3 1.3910(16) . ?
C3 C4 1.3901(17) . ?
C3 C7 1.5031(16) . ?
C4 H4 0.947(15) . ?
C4 C5 1.3957(17) . ?
C5 C6 1.3884(16) . ?
C5 C8 1.4975(17) . ?
C6 H6 0.949(15) . ?
C7 F1 1.3352(14) . ?
C7 F2 1.3351(15) . ?
C7 F3 1.3375(14) . ?
C8 F4 1.3412(14) . ?
C8 F5 1.3393(14) . ?
C8 F6 1.3450(14) . ?
C9 N1 1.3814(15) . ?
C9 N2 1.3536(15) . ?
C9 O1 1.2312(15) . ?
C10 H10A 0.999(15) . ?
C10 H10B 0.974(16) . ?
C10 C11 1.5330(17) . ?
C10 N2 1.4502(15) . ?
C11 H11A 0.985(15) . ?
C11 H11B 0.971(15) . ?
C11 N3 1.4537(15) . ?
C12 H12A 0.982(15) . ?
C12 H12B 0.975(15) . ?
C12 C13 1.5359(16) . ?
C12 N3 1.4598(14) . ?
C13 H13A 0.966(15) . ?
C13 H13B 0.998(15) . ?
C13 N4 1.4608(14) . ?
C14 H14A 0.982(16) . ?
C14 H14B 0.974(16) . ?
C14 C15 1.5189(17) . ?
C14 N4 1.4583(15) . ?
C15 C16 1.3927(17) . ?
C15 C20 1.3895(18) . ?
C16 H16 0.967(17) . ?
C16 C17 1.389(2) . ?
C17 H17 0.960(19) . ?
C17 C18 1.389(2) . ?
C18 H18 0.953(18) . ?
C18 C19 1.383(2) . ?
C19 H19 0.960(18) . ?
C19 C20 1.3880(19) . ?
C20 H20 0.958(16) . ?
C21 N3 1.3717(16) . ?
C21 N5 1.3551(15) . ?
C21 O2 1.2417(15) . ?
C22 H22A 0.959(16) . ?
C22 H22B 1.001(16) . ?
C22 C23 1.5155(16) . ?
C22 N5 1.4578(16) . ?
C23 H23A 0.979(16) . ?
C23 H23B 0.995(16) . ?
C23 C24 1.5243(17) . ?
C24 H24A 0.973(16) . ?
C24 H24B 1.002(16) . ?
C24 C25 1.5225(17) . ?
C25 H25A 0.966(17) . ?
C25 H25B 1.012(16) . ?
C25 C26 1.5202(19) . ?
C26 H26A 0.967(19) . ?
C26 H26B 0.984(19) . ?
C26 C27 1.527(2) . ?
C27 H27A 1.04(3) . ?
C27 H27B 0.97(3) . ?
C27 H27C 0.98(3) . ?
C28 N4 1.3663(15) . ?
C28 N6 1.3395(16) . ?
C28 O3 1.2536(14) . ?
C29 H29A 0.997(16) . ?
C29 H29B 0.984(16) . ?
C29 C30 1.5305(18) . ?
C29 N6 1.4586(16) . ?
C30 H30A 1.021(16) . ?
C30 H30B 0.991(17) . ?
C30 C31 1.5271(19) . ?
C31 H31A 0.997(17) . ?
C31 H31B 0.999(17) . ?
C31 C32 1.5236(18) . ?
C32 H32A 1.007(17) . ?
C32 H32B 0.961(17) . ?
C32 C33 1.5204(19) . ?
C33 H33A 0.986(17) . ?
C33 H33B 0.989(17) . ?
C33 C34 1.5208(19) . ?
C34 H34A 1.00(2) . ?
C34 H34B 0.98(2) . ?
C34 H34C 1.02(2) . ?
N1 H1 0.870(17) . ?
N2 H2A 0.860(16) . ?
N5 H5 0.847(17) . ?
N6 H6A 0.865(17) . ?
C35 C36 1.4009(17) . ?
C35 C40 1.3969(17) . ?
C35 N7 1.3929(15) . ?
C36 H36 0.970(15) . ?
C36 C37 1.3865(17) . ?
C37 C38 1.3890(18) . ?
C37 C41 1.4990(17) . ?
C38 H38 0.944(16) . ?
C38 C39 1.3868(18) . ?
C39 C40 1.3929(17) . ?
C39 C42 1.5025(17) . ?
C40 H40 0.952(15) . ?
C41 F7 1.326(4) . ?
C41 F7A 1.331(5) . ?
C41 F8 1.316(4) . ?
C41 F8A 1.334(6) . ?
C41 F9 1.328(4) . ?
C41 F9A 1.321(6) . ?
C42 F10 1.3311(16) . ?
C42 F11 1.3330(15) . ?
C42 F12 1.3379(16) . ?
C43 N7 1.3748(15) . ?
C43 N8 1.3551(16) . ?
C43 O4 1.2349(14) . ?
C44 H44A 0.975(15) . ?
C44 H44B 0.982(15) . ?
C44 C45 1.5385(16) . ?
C44 N8 1.4512(15) . ?
C45 H45A 0.979(15) . ?
C45 H45B 0.989(15) . ?
C45 N9 1.4556(15) . ?
C46 H46A 0.997(15) . ?
C46 H46B 0.957(15) . ?
C46 C47 1.5353(17) . ?
C46 N9 1.4545(15) . ?
C47 H47A 0.993(15) . ?
C47 H47B 0.969(15) . ?
C47 N10 1.4556(15) . ?
C48 H48A 0.990(15) . ?
C48 H48B 0.986(15) . ?
C48 C49 1.5144(16) . ?
C48 N10 1.4562(15) . ?
C49 C50 1.3950(17) . ?
C49 C54 1.3899(17) . ?
C50 H50 0.973(16) . ?
C50 C51 1.3864(19) . ?
C51 H51 0.969(18) . ?
C51 C52 1.387(2) . ?
C52 H52 0.960(18) . ?
C52 C53 1.386(2) . ?
C53 H53 0.958(17) . ?
C53 C54 1.3909(19) . ?
C54 H54 0.955(16) . ?
C55 N9 1.3768(15) . ?
C55 N11 1.3514(16) . ?
C55 O5 1.2419(14) . ?
C56 H56A 1.001(16) . ?
C56 H56B 0.973(16) . ?
C56 C57 1.5151(17) . ?
C56 N11 1.4602(15) . ?
C57 H57A 0.975(16) . ?
C57 H57B 1.005(16) . ?
C57 C58 1.5233(17) . ?
C58 H58A 0.993(17) . ?
C58 H58B 0.996(17) . ?
C58 C59 1.532(2) . ?
C59 H59A 1.000(18) . ?
C59 H59B 1.040(18) . ?
C59 C60 1.513(2) . ?
C60 H60A 1.042(19) . ?
C60 H60B 0.996(19) . ?
C60 C61 1.521(2) . ?
C61 H61A 0.99(2) . ?
C61 H61B 0.99(3) . ?
C61 H61C 1.00(2) . ?
C62 N10 1.3686(15) . ?
C62 N12 1.3459(16) . ?
C62 O6 1.2487(14) . ?
C63 H63A 0.959(16) . ?
C63 H63B 1.000(16) . ?
C63 C64 1.5140(17) . ?
C63 N12 1.4596(15) . ?
C64 H64A 0.971(17) . ?
C64 H64B 0.987(17) . ?
C64 C65 1.5292(17) . ?
C65 H65A 1.009(17) . ?
C65 H65B 1.013(17) . ?
C65 C66 1.5223(19) . ?
C66 H66A 1.002(17) . ?
C66 H66B 1.015(17) . ?
C66 C67 1.5262(17) . ?
C67 H67A 0.971(17) . ?
C67 H67B 0.995(17) . ?
C67 C68 1.516(2) . ?
C68 H68A 1.00(2) . ?
C68 H68B 0.99(2) . ?
C68 H68C 0.98(2) . ?
N7 H7 0.890(17) . ?
N8 H8 0.861(16) . ?
N11 H11 0.848(16) . ?
N12 H12 0.819(16) . ?

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
C6 C1 C2 119.12(11) . . ?
N1 C1 C2 117.14(11) . . ?
N1 C1 C6 123.74(11) . . ?
C1 C2 H2 118.5(9) . . ?
C3 C2 C1 120.30(11) . . ?
C3 C2 H2 121.2(9) . . ?
C2 C3 C7 118.00(11) . . ?
C4 C3 C2 121.39(11) . . ?
C4 C3 C7 120.60(10) . . ?
C3 C4 H4 123.8(9) . . ?
C3 C4 C5 117.46(11) . . ?
C5 C4 H4 118.8(9) . . ?
C4 C5 C8 118.59(10) . . ?
C6 C5 C4 122.38(11) . . ?
C6 C5 C8 119.02(11) . . ?
C1 C6 H6 121.6(9) . . ?
C5 C6 C1 119.34(11) . . ?
C5 C6 H6 119.1(9) . . ?
F1 C7 C3 112.53(10) . . ?
F1 C7 F3 106.26(10) . . ?
F2 C7 C3 112.30(10) . . ?
F2 C7 F1 106.12(10) . . ?
F2 C7 F3 106.65(10) . . ?
F3 C7 C3 112.50(10) . . ?
F4 C8 C5 112.68(10) . . ?
F4 C8 F6 105.85(9) . . ?
F5 C8 C5 113.12(10) . . ?
F5 C8 F4 106.58(10) . . ?
F5 C8 F6 106.04(10) . . ?
F6 C8 C5 112.03(10) . . ?
N2 C9 N1 113.07(10) . . ?
O1 C9 N1 124.03(11) . . ?
O1 C9 N2 122.90(11) . . ?
H10A C10 H10B 109.9(12) . . ?
C11 C10 H10A 110.6(8) . . ?
C11 C10 H10B 110.7(9) . . ?
N2 C10 H10A 106.9(8) . . ?
N2 C10 H10B 107.7(9) . . ?
N2 C10 C11 110.91(10) . . ?
C10 C11 H11A 110.1(9) . . ?
C10 C11 H11B 109.3(9) . . ?
H11A C11 H11B 108.6(12) . . ?
N3 C11 C10 113.28(10) . . ?
N3 C11 H11A 107.4(8) . . ?
N3 C11 H11B 108.0(9) . . ?
H12A C12 H12B 107.9(12) . . ?
C13 C12 H12A 110.2(8) . . ?
C13 C12 H12B 109.8(9) . . ?
N3 C12 H12A 108.7(8) . . ?
N3 C12 H12B 108.9(9) . . ?
N3 C12 C13 111.26(9) . . ?
C12 C13 H13A 108.6(9) . . ?
C12 C13 H13B 109.4(8) . . ?
H13A C13 H13B 109.4(12) . . ?
N4 C13 C12 114.08(9) . . ?
N4 C13 H13A 108.3(9) . . ?
N4 C13 H13B 107.1(8) . . ?
H14A C14 H14B 107.4(12) . . ?
C15 C14 H14A 109.2(9) . . ?
C15 C14 H14B 109.4(9) . . ?
N4 C14 H14A 107.3(9) . . ?
N4 C14 H14B 108.1(9) . . ?
N4 C14 C15 115.24(10) . . ?
C16 C15 C14 118.81(11) . . ?
C20 C15 C14 122.58(11) . . ?
C20 C15 C16 118.61(12) . . ?
C15 C16 H16 119.3(10) . . ?
C17 C16 C15 120.67(13) . . ?
C17 C16 H16 120.0(10) . . ?
C16 C17 H17 118.8(11) . . ?
C18 C17 C16 120.32(13) . . ?
C18 C17 H17 120.8(11) . . ?
C17 C18 H18 121.4(11) . . ?
C19 C18 C17 119.14(13) . . ?
C19 C18 H18 119.4(11) . . ?
C18 C19 H19 121.1(10) . . ?
C18 C19 C20 120.63(13) . . ?
C20 C19 H19 118.3(10) . . ?
C15 C20 H20 120.0(9) . . ?
C19 C20 C15 120.64(12) . . ?
C19 C20 H20 119.4(9) . . ?
N5 C21 N3 117.65(10) . . ?
O2 C21 N3 120.54(10) . . ?
O2 C21 N5 121.79(11) . . ?
H22A C22 H22B 108.2(12) . . ?
C23 C22 H22A 109.4(9) . . ?
C23 C22 H22B 110.1(9) . . ?
N5 C22 H22A 107.6(9) . . ?
N5 C22 H22B 110.0(9) . . ?
N5 C22 C23 111.42(10) . . ?
C22 C23 H23A 110.1(9) . . ?
C22 C23 H23B 109.1(9) . . ?
C22 C23 C24 111.57(11) . . ?
H23A C23 H23B 106.3(12) . . ?
C24 C23 H23A 109.6(9) . . ?
C24 C23 H23B 110.0(9) . . ?
C23 C24 H24A 109.7(9) . . ?
C23 C24 H24B 108.0(9) . . ?
H24A C24 H24B 106.2(13) . . ?
C25 C24 C23 113.57(11) . . ?
C25 C24 H24A 109.1(9) . . ?
C25 C24 H24B 110.0(9) . . ?
C24 C25 H25A 108.3(9) . . ?
C24 C25 H25B 109.7(9) . . ?
H25A C25 H25B 105.4(13) . . ?
C26 C25 C24 113.30(12) . . ?
C26 C25 H25A 110.7(10) . . ?
C26 C25 H25B 109.2(9) . . ?
C25 C26 H26A 109.5(11) . . ?
C25 C26 H26B 109.9(10) . . ?
C25 C26 C27 113.01(14) . . ?
H26A C26 H26B 102.8(14) . . ?
C27 C26 H26A 108.9(11) . . ?
C27 C26 H26B 112.1(10) . . ?
C26 C27 H27A 112.4(13) . . ?
C26 C27 H27B 111.6(14) . . ?
C26 C27 H27C 110.6(14) . . ?
H27A C27 H27B 108.6(19) . . ?
H27A C27 H27C 107.5(19) . . ?
H27B C27 H27C 106(2) . . ?
N6 C28 N4 118.55(10) . . ?
O3 C28 N4 118.88(10) . . ?
O3 C28 N6 122.57(11) . . ?
H29A C29 H29B 108.3(12) . . ?
C30 C29 H29A 111.1(9) . . ?
C30 C29 H29B 109.9(9) . . ?
N6 C29 H29A 107.2(9) . . ?
N6 C29 H29B 108.6(9) . . ?
N6 C29 C30 111.60(10) . . ?
C29 C30 H30A 109.4(9) . . ?
C29 C30 H30B 107.7(9) . . ?
H30A C30 H30B 107.2(13) . . ?
C31 C30 C29 114.58(10) . . ?
C31 C30 H30A 107.9(9) . . ?
C31 C30 H30B 109.9(9) . . ?
C30 C31 H31A 109.7(9) . . ?
C30 C31 H31B 109.1(9) . . ?
H31A C31 H31B 103.9(13) . . ?
C32 C31 C30 115.06(11) . . ?
C32 C31 H31A 108.9(9) . . ?
C32 C31 H31B 109.7(9) . . ?
C31 C32 H32A 109.5(9) . . ?
C31 C32 H32B 110.3(9) . . ?
H32A C32 H32B 105.9(13) . . ?
C33 C32 C31 113.28(11) . . ?
C33 C32 H32A 109.2(9) . . ?
C33 C32 H32B 108.4(10) . . ?
C32 C33 H33A 109.1(9) . . ?
C32 C33 H33B 108.8(9) . . ?
C32 C33 C34 113.12(11) . . ?
H33A C33 H33B 105.9(13) . . ?
C34 C33 H33A 110.4(9) . . ?
C34 C33 H33B 109.3(9) . . ?
C33 C34 H34A 112.6(11) . . ?
C33 C34 H34B 109.7(11) . . ?
C33 C34 H34C 111.1(11) . . ?
H34A C34 H34B 107.2(16) . . ?
H34A C34 H34C 108.3(15) . . ?
H34B C34 H34C 107.7(15) . . ?
C1 N1 H1 117.3(10) . . ?
C9 N1 C1 127.55(10) . . ?
C9 N1 H1 115.1(10) . . ?
C9 N2 C10 119.32(10) . . ?
C9 N2 H2A 118.6(10) . . ?
C10 N2 H2A 121.9(10) . . ?
C11 N3 C12 119.83(10) . . ?
C21 N3 C11 122.45(9) . . ?
C21 N3 C12 117.34(10) . . ?
C14 N4 C13 120.89(10) . . ?
C28 N4 C13 122.04(10) . . ?
C28 N4 C14 117.03(9) . . ?
C21 N5 C22 120.38(10) . . ?
C21 N5 H5 120.6(11) . . ?
C22 N5 H5 117.1(11) . . ?
C28 N6 C29 122.55(10) . . ?
C28 N6 H6A 120.2(11) . . ?
C29 N6 H6A 116.6(11) . . ?
C40 C35 C36 119.15(11) . . ?
N7 C35 C36 116.20(10) . . ?
N7 C35 C40 124.65(11) . . ?
C35 C36 H36 119.6(9) . . ?
C37 C36 C35 120.35(11) . . ?
C37 C36 H36 120.0(9) . . ?
C36 C37 C38 121.10(11) . . ?
C36 C37 C41 117.85(11) . . ?
C38 C37 C41 121.05(11) . . ?
C37 C38 H38 121.4(9) . . ?
C39 C38 C37 118.06(11) . . ?
C39 C38 H38 120.5(9) . . ?
C38 C39 C40 122.17(11) . . ?
C38 C39 C42 120.41(11) . . ?
C40 C39 C42 117.36(11) . . ?
C35 C40 H40 121.1(9) . . ?
C39 C40 C35 119.15(11) . . ?
C39 C40 H40 119.7(9) . . ?
F7 C41 C37 110.5(3) . . ?
F7 C41 F9 105.5(4) . . ?
F7A C41 C37 114.5(4) . . ?
F7A C41 F8A 104.1(5) . . ?
F8 C41 C37 113.6(4) . . ?
F8 C41 F7 107.8(4) . . ?
F8 C41 F9 106.8(4) . . ?
F8A C41 C37 110.2(6) . . ?
F9 C41 C37 112.2(4) . . ?
F9A C41 C37 114.3(6) . . ?
F9A C41 F7A 107.3(6) . . ?
F9A C41 F8A 105.6(6) . . ?
F10 C42 C39 112.87(11) . . ?
F10 C42 F11 106.84(11) . . ?
F10 C42 F12 106.80(11) . . ?
F11 C42 C39 111.67(11) . . ?
F11 C42 F12 105.88(11) . . ?
F12 C42 C39 112.33(10) . . ?
N8 C43 N7 113.37(10) . . ?
O4 C43 N7 123.75(11) . . ?
O4 C43 N8 122.87(11) . . ?
H44A C44 H44B 107.1(12) . . ?
C45 C44 H44A 109.3(9) . . ?
C45 C44 H44B 111.0(9) . . ?
N8 C44 H44A 110.2(9) . . ?
N8 C44 H44B 107.6(9) . . ?
N8 C44 C45 111.54(10) . . ?
C44 C45 H45A 110.2(9) . . ?
C44 C45 H45B 110.7(8) . . ?
H45A C45 H45B 107.2(12) . . ?
N9 C45 C44 113.38(10) . . ?
N9 C45 H45A 108.6(8) . . ?
N9 C45 H45B 106.5(8) . . ?
H46A C46 H46B 108.1(12) . . ?
C47 C46 H46A 109.3(8) . . ?
C47 C46 H46B 109.2(9) . . ?
N9 C46 H46A 107.9(8) . . ?
N9 C46 H46B 110.1(9) . . ?
N9 C46 C47 112.21(9) . . ?
C46 C47 H47A 110.4(8) . . ?
C46 C47 H47B 109.3(9) . . ?
H47A C47 H47B 107.5(12) . . ?
N10 C47 C46 112.19(9) . . ?
N10 C47 H47A 108.4(8) . . ?
N10 C47 H47B 109.0(9) . . ?
H48A C48 H48B 108.6(12) . . ?
C49 C48 H48A 108.1(8) . . ?
C49 C48 H48B 111.6(8) . . ?
N10 C48 H48A 107.7(8) . . ?
N10 C48 H48B 106.6(8) . . ?
N10 C48 C49 113.99(10) . . ?
C50 C49 C48 121.47(11) . . ?
C54 C49 C48 119.86(11) . . ?
C54 C49 C50 118.65(11) . . ?
C49 C50 H50 118.6(9) . . ?
C51 C50 C49 120.38(12) . . ?
C51 C50 H50 121.0(9) . . ?
C50 C51 H51 119.0(10) . . ?
C50 C51 C52 120.43(13) . . ?
C52 C51 H51 120.6(10) . . ?
C51 C52 H52 120.4(10) . . ?
C53 C52 C51 119.78(12) . . ?
C53 C52 H52 119.7(10) . . ?
C52 C53 H53 122.4(10) . . ?
C52 C53 C54 119.65(12) . . ?
C54 C53 H53 117.9(10) . . ?
C49 C54 C53 121.10(12) . . ?
C49 C54 H54 119.2(9) . . ?
C53 C54 H54 119.6(9) . . ?
N11 C55 N9 117.05(10) . . ?
O5 C55 N9 120.35(11) . . ?
O5 C55 N11 122.58(11) . . ?
H56A C56 H56B 108.4(12) . . ?
C57 C56 H56A 109.8(9) . . ?
C57 C56 H56B 111.4(9) . . ?
N11 C56 H56A 108.8(9) . . ?
N11 C56 H56B 107.7(9) . . ?
N11 C56 C57 110.70(10) . . ?
C56 C57 H57A 109.2(9) . . ?
C56 C57 H57B 109.1(9) . . ?
C56 C57 C58 112.00(11) . . ?
H57A C57 H57B 107.2(12) . . ?
C58 C57 H57A 109.8(9) . . ?
C58 C57 H57B 109.3(9) . . ?
C57 C58 H58A 107.5(10) . . ?
C57 C58 H58B 108.5(10) . . ?
C57 C58 C59 114.26(11) . . ?
H58A C58 H58B 107.9(13) . . ?
C59 C58 H58A 108.1(10) . . ?
C59 C58 H58B 110.3(10) . . ?
C58 C59 H59A 110.0(10) . . ?
C58 C59 H59B 112.7(10) . . ?
H59A C59 H59B 106.4(14) . . ?
C60 C59 C58 114.08(12) . . ?
C60 C59 H59A 106.2(10) . . ?
C60 C59 H59B 107.1(10) . . ?
C59 C60 H60A 106.9(10) . . ?
C59 C60 H60B 108.8(10) . . ?
C59 C60 C61 112.86(14) . . ?
H60A C60 H60B 108.8(14) . . ?
C61 C60 H60A 111.5(10) . . ?
C61 C60 H60B 107.9(10) . . ?
C60 C61 H61A 110.5(13) . . ?
C60 C61 H61B 109.7(14) . . ?
C60 C61 H61C 110.7(14) . . ?
H61A C61 H61B 105.3(19) . . ?
H61A C61 H61C 108.1(19) . . ?
H61B C61 H61C 112.3(19) . . ?
N12 C62 N10 117.54(10) . . ?
O6 C62 N10 120.58(10) . . ?
O6 C62 N12 121.84(11) . . ?
H63A C63 H63B 107.0(13) . . ?
C64 C63 H63A 110.6(9) . . ?
C64 C63 H63B 110.1(9) . . ?
N12 C63 H63A 108.1(9) . . ?
N12 C63 H63B 110.5(9) . . ?
N12 C63 C64 110.55(10) . . ?
C63 C64 H64A 107.5(9) . . ?
C63 C64 H64B 108.0(9) . . ?
C63 C64 C65 112.09(11) . . ?
H64A C64 H64B 108.0(13) . . ?
C65 C64 H64A 110.2(9) . . ?
C65 C64 H64B 110.9(9) . . ?
C64 C65 H65A 109.2(9) . . ?
C64 C65 H65B 109.9(9) . . ?
H65A C65 H65B 106.7(13) . . ?
C66 C65 C64 113.87(11) . . ?
C66 C65 H65A 109.5(9) . . ?
C66 C65 H65B 107.3(9) . . ?
C65 C66 H66A 108.0(9) . . ?
C65 C66 H66B 109.8(9) . . ?
C65 C66 C67 113.71(11) . . ?
H66A C66 H66B 106.0(13) . . ?
C67 C66 H66A 110.6(9) . . ?
C67 C66 H66B 108.4(9) . . ?
C66 C67 H67A 108.7(10) . . ?
C66 C67 H67B 109.0(9) . . ?
H67A C67 H67B 105.6(13) . . ?
C68 C67 C66 113.66(12) . . ?
C68 C67 H67A 111.3(10) . . ?
C68 C67 H67B 108.3(9) . . ?
C67 C68 H68A 111.1(12) . . ?
C67 C68 H68B 110.2(12) . . ?
C67 C68 H68C 110.8(12) . . ?
H68A C68 H68B 106.8(16) . . ?
H68A C68 H68C 109.9(16) . . ?
H68B C68 H68C 107.9(17) . . ?
C35 N7 H7 117.0(10) . . ?
C43 N7 C35 127.90(10) . . ?
C43 N7 H7 115.0(10) . . ?
C43 N8 C44 120.11(10) . . ?
C43 N8 H8 118.9(10) . . ?
C44 N8 H8 120.8(10) . . ?
C46 N9 C45 120.20(9) . . ?
C55 N9 C45 122.65(10) . . ?
C55 N9 C46 116.82(9) . . ?
C47 N10 C48 117.40(9) . . ?
C62 N10 C47 122.52(10) . . ?
C62 N10 C48 119.92(10) . . ?
C55 N11 C56 121.59(10) . . ?
C55 N11 H11 121.5(10) . . ?
C56 N11 H11 114.6(10) . . ?
C62 N12 C63 120.63(10) . . ?
C62 N12 H12 118.9(11) . . ?
C63 N12 H12 118.3(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
C6 H6 O1 0.949(15) 2.270(15) 2.8598(14) 119.6(11) . yes
N1 H1 O6 0.870(17) 2.006(17) 2.8255(13) 156.6(14) 2_756 yes
N2 H2A O6 0.860(16) 2.050(16) 2.8386(13) 152.0(14) 2_756 yes
N6 H6A O2 0.865(17) 1.971(18) 2.8229(13) 167.9(15) . yes
C40 H40 O4 0.952(15) 2.272(15) 2.8700(15) 120.1(11) . yes
N7 H7 O3 0.890(17) 1.828(17) 2.6844(13) 160.8(15) . yes
N8 H8 O3 0.861(16) 2.079(16) 2.8410(13) 147.1(14) . yes
N11 H11 O4 0.848(16) 2.085(16) 2.9247(13) 170.7(14) . yes
N12 H12 O5 0.819(16) 2.145(17) 2.9529(14) 168.9(14) . yes

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
C1 C2 C3 C4 -0.45(18) . . . . ?
C1 C2 C3 C7 179.09(10) . . . . ?
C2 C1 C6 C5 -0.66(17) . . . . ?
C2 C1 N1 C9 -168.97(11) . . . . ?
C2 C3 C4 C5 -0.50(17) . . . . ?
C2 C3 C7 F1 36.16(15) . . . . ?
C2 C3 C7 F2 -83.52(13) . . . . ?
C2 C3 C7 F3 156.15(11) . . . . ?
C3 C4 C5 C6 0.88(18) . . . . ?
C3 C4 C5 C8 -177.71(11) . . . . ?
C4 C3 C7 F1 -144.29(11) . . . . ?
C4 C3 C7 F2 96.03(13) . . . . ?
C4 C3 C7 F3 -24.30(16) . . . . ?
C4 C5 C6 C1 -0.30(18) . . . . ?
C4 C5 C8 F4 -63.71(14) . . . . ?
C4 C5 C8 F5 175.32(11) . . . . ?
C4 C5 C8 F6 55.52(15) . . . . ?
C6 C1 C2 C3 1.04(17) . . . . ?
C6 C1 N1 C9 10.95(19) . . . . ?
C6 C5 C8 F4 117.65(12) . . . . ?
C6 C5 C8 F5 -3.32(16) . . . . ?
C6 C5 C8 F6 -123.12(12) . . . . ?
C7 C3 C4 C5 179.97(11) . . . . ?
C8 C5 C6 C1 178.28(11) . . . . ?
C10 C11 N3 C12 93.45(12) . . . . ?
C10 C11 N3 C21 -79.25(14) . . . . ?
C11 C10 N2 C9 -72.48(14) . . . . ?
C12 C13 N4 C14 -109.79(12) . . . . ?
C12 C13 N4 C28 72.51(14) . . . . ?
C13 C12 N3 C11 -103.13(12) . . . . ?
C13 C12 N3 C21 69.94(13) . . . . ?
C14 C15 C16 C17 178.97(12) . . . . ?
C14 C15 C20 C19 -178.53(12) . . . . ?
C15 C14 N4 C13 102.79(12) . . . . ?
C15 C14 N4 C28 -79.40(13) . . . . ?
C15 C16 C17 C18 -0.1(2) . . . . ?
C16 C15 C20 C19 0.99(19) . . . . ?
C16 C17 C18 C19 0.4(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 -0.7(2) . . . . ?
C20 C15 C16 C17 -0.57(19) . . . . ?
C22 C23 C24 C25 177.54(11) . . . . ?
C23 C22 N5 C21 151.98(11) . . . . ?
C23 C24 C25 C26 176.89(11) . . . . ?
C24 C25 C26 C27 175.64(13) . . . . ?
C29 C30 C31 C32 -60.17(15) . . . . ?
C30 C29 N6 C28 119.62(12) . . . . ?
C30 C31 C32 C33 176.79(11) . . . . ?
C31 C32 C33 C34 -177.10(11) . . . . ?
N1 C1 C2 C3 -179.04(11) . . . . ?
N1 C1 C6 C5 179.42(11) . . . . ?
N1 C9 N2 C10 178.53(10) . . . . ?
N2 C9 N1 C1 178.13(11) . . . . ?
N2 C10 C11 N3 162.57(10) . . . . ?
N3 C12 C13 N4 -159.81(10) . . . . ?
N3 C21 N5 C22 176.47(11) . . . . ?
N4 C14 C15 C16 -178.24(11) . . . . ?
N4 C14 C15 C20 1.27(16) . . . . ?
N4 C28 N6 C29 -170.76(11) . . . . ?
N5 C21 N3 C11 -2.08(17) . . . . ?
N5 C21 N3 C12 -174.95(10) . . . . ?
N5 C22 C23 C24 -179.13(10) . . . . ?
N6 C28 N4 C13 -1.31(17) . . . . ?
N6 C28 N4 C14 -179.09(10) . . . . ?
N6 C29 C30 C31 -59.19(14) . . . . ?
O1 C9 N1 C1 -1.1(2) . . . . ?
O1 C9 N2 C10 -2.26(18) . . . . ?
O2 C21 N3 C11 179.31(11) . . . . ?
O2 C21 N3 C12 6.43(16) . . . . ?
O2 C21 N5 C22 -4.93(18) . . . . ?
O3 C28 N4 C13 179.43(10) . . . . ?
O3 C28 N4 C14 1.65(16) . . . . ?
O3 C28 N6 C29 8.47(18) . . . . ?
C35 C36 C37 C38 -0.21(17) . . . . ?
C35 C36 C37 C41 179.18(10) . . . . ?
C36 C35 C40 C39 -1.31(17) . . . . ?
C36 C35 N7 C43 176.01(11) . . . . ?
C36 C37 C38 C39 -0.83(17) . . . . ?
C36 C37 C41 F7 59.5(4) . . . . ?
C36 C37 C41 F7A 38.1(8) . . . . ?
C36 C37 C41 F8 -61.8(4) . . . . ?
C36 C37 C41 F8A -78.8(7) . . . . ?
C36 C37 C41 F9 176.9(5) . . . . ?
C36 C37 C41 F9A 162.5(7) . . . . ?
C37 C38 C39 C40 0.80(17) . . . . ?
C37 C38 C39 C42 177.95(11) . . . . ?
C38 C37 C41 F7 -121.1(4) . . . . ?
C38 C37 C41 F7A -142.5(8) . . . . ?
C38 C37 C41 F8 117.6(4) . . . . ?
C38 C37 C41 F8A 100.6(7) . . . . ?
C38 C37 C41 F9 -3.7(5) . . . . ?
C38 C37 C41 F9A -18.1(7) . . . . ?
C38 C39 C40 C35 0.27(17) . . . . ?
C38 C39 C42 F10 12.39(17) . . . . ?
C38 C39 C42 F11 -108.01(13) . . . . ?
C38 C39 C42 F12 133.21(12) . . . . ?
C40 C35 C36 C37 1.29(17) . . . . ?
C40 C35 N7 C43 -4.60(19) . . . . ?
C40 C39 C42 F10 -170.33(11) . . . . ?
C40 C39 C42 F11 69.27(15) . . . . ?
C40 C39 C42 F12 -49.51(15) . . . . ?
C41 C37 C38 C39 179.81(11) . . . . ?
C42 C39 C40 C35 -176.96(11) . . . . ?
C44 C45 N9 C46 -100.63(12) . . . . ?
C44 C45 N9 C55 72.52(14) . . . . ?
C45 C44 N8 C43 69.84(14) . . . . ?
C46 C47 N10 C48 88.58(12) . . . . ?
C46 C47 N10 C62 -86.82(13) . . . . ?
C47 C46 N9 C45 95.37(12) . . . . ?
C47 C46 N9 C55 -78.17(13) . . . . ?
C48 C49 C50 C51 178.52(12) . . . . ?
C48 C49 C54 C53 -178.86(11) . . . . ?
C49 C48 N10 C47 80.24(13) . . . . ?
C49 C48 N10 C62 -104.23(12) . . . . ?
C49 C50 C51 C52 0.4(2) . . . . ?
C50 C49 C54 C53 -0.35(18) . . . . ?
C50 C51 C52 C53 -0.5(2) . . . . ?
C51 C52 C53 C54 0.2(2) . . . . ?
C52 C53 C54 C49 0.23(19) . . . . ?
C54 C49 C50 C51 0.03(18) . . . . ?
C56 C57 C58 C59 172.77(11) . . . . ?
C57 C56 N11 C55 -157.51(11) . . . . ?
C57 C58 C59 C60 60.04(17) . . . . ?
C58 C59 C60 C61 170.97(14) . . . . ?
C63 C64 C65 C66 62.65(16) . . . . ?
C64 C63 N12 C62 159.65(11) . . . . ?
C64 C65 C66 C67 178.54(11) . . . . ?
C65 C66 C67 C68 -67.31(16) . . . . ?
N7 C35 C36 C37 -179.29(10) . . . . ?
N7 C35 C40 C39 179.33(11) . . . . ?
N7 C43 N8 C44 179.28(10) . . . . ?
N8 C43 N7 C35 177.29(11) . . . . ?
N8 C44 C45 N9 -159.46(10) . . . . ?
N9 C46 C47 N10 160.17(9) . . . . ?
N9 C55 N11 C56 -171.75(10) . . . . ?
N10 C48 C49 C50 38.74(15) . . . . ?
N10 C48 C49 C54 -142.79(11) . . . . ?
N10 C62 N12 C63 179.63(10) . . . . ?
N11 C55 N9 C45 4.99(16) . . . . ?
N11 C55 N9 C46 178.35(10) . . . . ?
N11 C56 C57 C58 -178.44(11) . . . . ?
N12 C62 N10 C47 4.89(16) . . . . ?
N12 C62 N10 C48 -170.40(10) . . . . ?
N12 C63 C64 C65 170.01(11) . . . . ?
O4 C43 N7 C35 -1.76(19) . . . . ?
O4 C43 N8 C44 -1.67(18) . . . . ?
O5 C55 N9 C45 -176.38(10) . . . . ?
O5 C55 N9 C46 -3.01(16) . . . . ?
O5 C55 N11 C56 9.65(17) . . . . ?
O6 C62 N10 C47 -172.78(10) . . . . ?
O6 C62 N10 C48 11.93(16) . . . . ?
O6 C62 N12 C63 -2.73(18) . . . . ?

_olex2_date_sample_data_collection 2022-01-17
_olex2_date_sample_submission    2022-01-11
_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_testt1
_database_code_depnum_ccdc_archive 'CCDC 2189974'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H42 F6 N6 O3'
_chemical_formula_sum            'C31 H42 F6 N6 O3'
_chemical_formula_weight         660.70
_chemical_melting_point          441
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.5044(5)
_cell_length_b                   14.9547(5)
_cell_length_c                   17.2099(6)
_cell_angle_alpha                101.789(2)
_cell_angle_beta                 111.249(2)
_cell_angle_gamma                97.465(2)
_cell_volume                     3319.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6188
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0648 before and 0.0506 after correction. The Ratio of minimum to maximum transmission is 0.8302. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.396
_exptl_crystal_size_min          0.178
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48350
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         1.427
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7559
_reflns_number_total             12166
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     949
_refine_ls_number_reflns         12166
_refine_ls_number_restraints     328
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+1.7692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1565
_refine_special_details          
;
Occupancies of the disordered atoms were refined with their sum set to
equal 1. Restraints and constraints were applied to maintain sensible
thermal and geometric parameters.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C4 \\sim N2A-C4 \\sim N2A-C5 \\sim N2-C5
 with sigma of 0.01
 N2A-C12A \\sim N2-C12 \\sim N3-C13 \\sim N3A-C13A \\sim N3-C21 \\sim N3A-C21A
\\sim N5-C22 \\sim N5-C22A
 with sigma of 0.01
 C13A-C12A \\sim C13-C12 \\sim C22-C21 \\sim C22A-C21A
 with sigma of 0.01
 N3-C14 \\sim N3A-C14
 with sigma of 0.01
 N8A-C36 \\sim N8-C36 \\sim N8A-C35 \\sim N8-C35 \\sim N9-C45 \\sim N9A-C45
\\sim N9-C52 \\sim N9A-C52
 with sigma of 0.01
 N8A-C43A \\sim N8-C43 \\sim N9-C44 \\sim N9A-C44A
 with sigma of 0.01
 C44-C43 \\sim C44A-C43A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim N2A \\sim C12 \\sim C12A \\sim C13 \\sim C13A \\sim N3 \\sim C21 \\sim
N3A \\sim C22 \\sim C21A \\sim C22A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
N8 \\sim N9 \\sim C43 \\sim C44 \\sim C43A \\sim C44A \\sim N8A \\sim N9A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N8A) = Uanis(N8)
4. Others
 Sof(H5B)=Sof(H5BC)=Sof(H5BD)=Sof(N2A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=
 Sof(H13C)=Sof(H13D)=Sof(N3A)=Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=1-FVAR(1)
 Sof(N2)=Sof(N3)=Sof(H5A)=Sof(H5AA)=Sof(H5AB)=Sof(C12)=Sof(H12A)=Sof(H12B)=
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=FVAR(1)
 Sof(H36C)=Sof(H36D)=Sof(H52C)=Sof(H52D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=
 Sof(C44A)=Sof(H44C)=Sof(H44D)=Sof(N8A)=Sof(N9A)=1-FVAR(2)
 Sof(N8)=Sof(N9)=Sof(H36A)=Sof(H36B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=
 Sof(H44A)=Sof(H44B)=Sof(H52A)=Sof(H52B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1A), C32(H32)
5.b Secondary CH2 refined with riding coordinates:
 C5(H5AA,H5AB), C5(H5BC,H5BD), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B),
  C22(H22A,H22B), C36(H36A,H36B), C36(H36C,H36D), C43(H43A,H43B), C44(H44A,
 H44B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B),
 C50(H50A,H50B), C52(H52A,H52B), C52(H52C,H52D), C53(H53A,H53B), C12A(H12C,
 H12D), C13A(H13C,H13D), C21A(H21C,H21D), C22A(H22C,H22D), C43A(H43C,H43D),
 C44A(H44C,H44D)
5.c Aromatic/amide H refined with riding coordinates:
 N5(H5A), N5(H5B), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C25(H25),
 C27(H27), C29(H29), C38(H38), C39(H39), C40(H40), C41(H41), C42(H42), C56(H56),
  C58(H58), C60(H60)
5.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C20(H20A,H20B,H20C), C33(H33A,H33B,H33C),
 C34(H34A,H34B,H34C), C51(H51A,H51B,H51C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.41109(16) 0.21104(14) 0.72540(13) 0.0734(6) Uani 1 1 d . . . . .
F2 F 0.39856(16) 0.12662(16) 0.60659(14) 0.0686(6) Uani 1 1 d . . . . .
F3 F 0.31533(15) 0.07440(15) 0.67301(16) 0.0756(7) Uani 1 1 d . . . . .
F4 F -0.08454(13) 0.20740(12) 0.51352(14) 0.0576(5) Uani 1 1 d . . . . .
F5 F -0.03720(14) 0.09843(13) 0.57241(13) 0.0577(5) Uani 1 1 d . . . . .
F6 F -0.06319(13) 0.08457(12) 0.43938(13) 0.0560(5) Uani 1 1 d . . . . .
O1 O -0.05418(13) 0.84904(12) 0.09049(12) 0.0332(4) Uani 1 1 d . . . . .
O2 O -0.10835(14) 0.60928(15) 0.24404(13) 0.0453(5) Uani 1 1 d . . . . .
O3 O 0.08581(14) 0.42918(13) 0.44870(12) 0.0374(5) Uani 1 1 d . . . . .
N1 N -0.11683(18) 0.73713(17) 0.14095(17) 0.0375(6) Uani 1 1 d . . . . .
N2 N 0.0547(3) 0.7704(3) 0.1652(3) 0.0284(13) Uani 0.680(5) 1 d D U P A 1
N3 N 0.0617(3) 0.6203(3) 0.3143(3) 0.0347(11) Uani 0.680(5) 1 d D U P A 1
N4 N -0.06014(17) 0.50233(16) 0.31791(15) 0.0313(5) Uani 1 1 d . . . . .
N5 N 0.23153(17) 0.53658(15) 0.48742(16) 0.0420(6) Uani 1 1 d D . . . .
H5A H 0.298272 0.549041 0.508569 0.050 Uiso 0.680(5) 1 calc R . P A 1
H5B H 0.295295 0.558941 0.523899 0.050 Uiso 0.320(5) 1 calc R . P A 2
N6 N 0.23908(19) 0.40160(15) 0.52936(15) 0.0299(5) Uani 1 1 d . . . . .
C1 C -0.22262(19) 0.73901(19) 0.09504(18) 0.0333(6) Uani 1 1 d . . . . .
H1A H -0.225379 0.802929 0.086507 0.040 Uiso 1 1 calc R . . . .
C2 C -0.2817(2) 0.7211(3) 0.1489(2) 0.0540(9) Uani 1 1 d . . . . .
H2A H -0.280716 0.658284 0.157204 0.081 Uiso 1 1 calc GR . . . .
H2B H -0.351981 0.725579 0.119030 0.081 Uiso 1 1 calc GR . . . .
H2C H -0.250630 0.767882 0.205405 0.081 Uiso 1 1 calc GR . . . .
C3 C -0.2671(2) 0.6683(2) 0.0065(2) 0.0451(8) Uani 1 1 d . . . . .
H3A H -0.229235 0.684371 -0.027620 0.068 Uiso 1 1 calc GR . . . .
H3B H -0.338478 0.669530 -0.023515 0.068 Uiso 1 1 calc GR . . . .
H3C H -0.262214 0.605460 0.013471 0.068 Uiso 1 1 calc GR . . . .
C4 C -0.04073(19) 0.78986(19) 0.13259(18) 0.0337(7) Uani 1 1 d D . . . .
C5 C 0.1412(2) 0.83787(19) 0.17163(19) 0.0361(7) Uani 1 1 d D . . . .
H5AA H 0.118401 0.861320 0.119526 0.043 Uiso 0.680(5) 1 calc R . P A 1
H5AB H 0.193366 0.802751 0.167657 0.043 Uiso 0.680(5) 1 calc R . P A 1
H5BC H 0.114191 0.856313 0.117014 0.043 Uiso 0.320(5) 1 calc R . P A 2
H5BD H 0.187341 0.795584 0.167459 0.043 Uiso 0.320(5) 1 calc R . P A 2
C6 C 0.1937(2) 0.9228(2) 0.24941(18) 0.0333(7) Uani 1 1 d . . . . .
C7 C 0.1439(2) 0.9617(2) 0.29776(19) 0.0420(8) Uani 1 1 d . . . . .
H7 H 0.074707 0.934670 0.282821 0.050 Uiso 1 1 calc R . . . .
C8 C 0.1940(3) 1.0402(3) 0.3682(2) 0.0512(9) Uani 1 1 d . . . . .
H8 H 0.158772 1.066598 0.400849 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2946(3) 1.0800(2) 0.3908(2) 0.0493(8) Uani 1 1 d . . . . .
H9 H 0.328792 1.133398 0.439171 0.059 Uiso 1 1 calc R . . . .
C10 C 0.3452(2) 1.0420(2) 0.3432(2) 0.0452(8) Uani 1 1 d . . . . .
H10 H 0.414500 1.069134 0.358524 0.054 Uiso 1 1 calc R . . . .
C11 C 0.2951(2) 0.9640(2) 0.27276(19) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.330497 0.938282 0.239936 0.046 Uiso 1 1 calc R . . . .
C12 C 0.0726(3) 0.6908(3) 0.2004(2) 0.0299(10) Uani 0.680(5) 1 d D U P A 1
H12A H 0.135340 0.674457 0.197120 0.036 Uiso 0.680(5) 1 calc R . P A 1
H12B H 0.015682 0.636354 0.164007 0.036 Uiso 0.680(5) 1 calc R . P A 1
C13 C 0.0832(3) 0.7081(3) 0.2937(3) 0.0339(11) Uani 0.680(5) 1 d D U P A 1
H13A H 0.153042 0.743191 0.333072 0.041 Uiso 0.680(5) 1 calc R . P A 1
H13B H 0.035634 0.746852 0.302699 0.041 Uiso 0.680(5) 1 calc R . P A 1
C14 C -0.0405(2) 0.5752(2) 0.28748(19) 0.0415(8) Uani 1 1 d D . . . .
C15 C -0.1634(2) 0.46556(19) 0.30706(19) 0.0350(7) Uani 1 1 d . . . . .
H15A H -0.211028 0.459595 0.247078 0.042 Uiso 1 1 calc R . . . .
H15B H -0.182133 0.509602 0.347143 0.042 Uiso 1 1 calc R . . . .
C16 C -0.1721(2) 0.37032(19) 0.32544(18) 0.0351(7) Uani 1 1 d . . . . .
H16A H -0.116709 0.374800 0.381569 0.042 Uiso 1 1 calc R . . . .
H16B H -0.237306 0.353384 0.330944 0.042 Uiso 1 1 calc R . . . .
C17 C -0.1668(2) 0.29335(19) 0.25611(19) 0.0385(7) Uani 1 1 d . . . . .
H17A H -0.104144 0.312782 0.247418 0.046 Uiso 1 1 calc R . . . .
H17B H -0.225255 0.285814 0.200992 0.046 Uiso 1 1 calc R . . . .
C18 C -0.1673(2) 0.1992(2) 0.2765(2) 0.0435(8) Uani 1 1 d . . . . .
H18A H -0.099257 0.201036 0.319652 0.052 Uiso 1 1 calc R . . . .
H18B H -0.216422 0.189207 0.303306 0.052 Uiso 1 1 calc R . . . .
C19 C -0.1945(3) 0.1170(2) 0.1988(2) 0.0549(9) Uani 1 1 d . . . . .
H19A H -0.149962 0.130068 0.168541 0.066 Uiso 1 1 calc R . . . .
H19B H -0.265245 0.111318 0.158386 0.066 Uiso 1 1 calc R . . . .
C20 C -0.1852(4) 0.0243(2) 0.2194(3) 0.0826(14) Uani 1 1 d . . . . .
H20A H -0.207632 -0.025562 0.165458 0.124 Uiso 1 1 calc GR . . . .
H20B H -0.227745 0.011158 0.250692 0.124 Uiso 1 1 calc GR . . . .
H20C H -0.114306 0.027253 0.255563 0.124 Uiso 1 1 calc GR . . . .
C21 C 0.1437(4) 0.5770(4) 0.3563(4) 0.0334(13) Uani 0.680(5) 1 d D U P A 1
H21A H 0.202377 0.596532 0.342335 0.040 Uiso 0.680(5) 1 calc R . P A 1
H21B H 0.120725 0.507941 0.333867 0.040 Uiso 0.680(5) 1 calc R . P A 1
C22 C 0.1761(6) 0.6048(4) 0.4534(4) 0.0331(15) Uani 0.680(5) 1 d D U P A 1
H22A H 0.220210 0.668667 0.479083 0.040 Uiso 0.680(5) 1 calc R . P A 1
H22B H 0.115872 0.604505 0.467826 0.040 Uiso 0.680(5) 1 calc R . P A 1
C23 C 0.1788(2) 0.45404(18) 0.48589(17) 0.0325(6) Uani 1 1 d . . . . .
C24 C 0.2074(2) 0.31705(17) 0.54469(16) 0.0274(6) Uani 1 1 d . . . . .
C25 C 0.2826(2) 0.27332(18) 0.58542(16) 0.0292(6) Uani 1 1 d . . . . .
H25 H 0.351570 0.300540 0.599628 0.035 Uiso 1 1 calc R . . . .
C26 C 0.2589(2) 0.19047(18) 0.60577(17) 0.0297(6) Uani 1 1 d . . . . .
C27 C 0.1590(2) 0.14948(18) 0.58538(17) 0.0307(6) Uani 1 1 d . . . . .
H27 H 0.142298 0.093288 0.599813 0.037 Uiso 1 1 calc R . . . .
C28 C 0.0839(2) 0.19214(17) 0.54350(16) 0.0284(6) Uani 1 1 d . . . . .
C29 C 0.1063(2) 0.27529(18) 0.52293(17) 0.0300(6) Uani 1 1 d . . . . .
H29 H 0.053344 0.303362 0.494369 0.036 Uiso 1 1 calc R . . . .
C30 C 0.3440(2) 0.14987(19) 0.65169(19) 0.0354(7) Uani 1 1 d . . . . .
C31 C -0.0239(2) 0.1471(2) 0.5181(2) 0.0407(7) Uani 1 1 d . . . . .
F7 F 1.45749(14) 1.28506(12) 1.18967(12) 0.0546(5) Uani 1 1 d . . . . .
F8 F 1.49537(15) 1.26114(13) 1.08049(13) 0.0599(5) Uani 1 1 d . . . . .
F9 F 1.58555(13) 1.22694(14) 1.19509(14) 0.0707(6) Uani 1 1 d . . . . .
F10 F 1.54262(16) 0.89244(15) 1.11773(17) 0.0841(7) Uani 1 1 d . . . . .
F11 F 1.40408(17) 0.80947(14) 1.01774(15) 0.0730(6) Uani 1 1 d . . . . .
F12 F 1.41876(18) 0.83728(15) 1.14765(14) 0.0734(6) Uani 1 1 d . . . . .
O4 O 0.43214(14) 0.51606(13) 0.57839(13) 0.0410(5) Uani 1 1 d . . . . .
O5 O 0.78956(15) 0.58110(14) 0.78670(15) 0.0508(6) Uani 1 1 d . . . . .
O6 O 1.08538(13) 0.86682(12) 0.96360(12) 0.0317(4) Uani 1 1 d . . . . .
N7 N 0.5777(2) 0.52681(18) 0.69298(17) 0.0419(7) Uani 1 1 d . . . . .
N8 N 0.5634(2) 0.64197(19) 0.61896(18) 0.0347(9) Uani 0.849(5) 1 d D U P B 1
N9 N 0.8431(2) 0.7115(2) 0.75193(19) 0.0325(9) Uani 0.849(5) 1 d D U P B 1
N10 N 0.93993(18) 0.67590(18) 0.87780(17) 0.0375(6) Uani 1 1 d . . . . .
N11 N 0.98907(16) 0.95471(16) 0.89076(15) 0.0309(5) Uani 1 1 d . . . . .
N12 N 1.15340(16) 1.02205(16) 0.98354(14) 0.0298(5) Uani 1 1 d . . . . .
C32 C 0.5348(2) 0.4466(2) 0.7158(2) 0.0392(7) Uani 1 1 d . . . . .
H32 H 0.491759 0.396938 0.660855 0.047 Uiso 1 1 calc R . . . .
C33 C 0.6205(2) 0.4078(2) 0.7683(2) 0.0540(9) Uani 1 1 d . . . . .
H33A H 0.659594 0.388528 0.734248 0.081 Uiso 1 1 calc GR . . . .
H33B H 0.592547 0.353485 0.782958 0.081 Uiso 1 1 calc GR . . . .
H33C H 0.665058 0.456130 0.821622 0.081 Uiso 1 1 calc GR . . . .
C34 C 0.4679(3) 0.4737(2) 0.7628(2) 0.0505(8) Uani 1 1 d . . . . .
H34A H 0.509365 0.519611 0.818590 0.076 Uiso 1 1 calc GR . . . .
H34B H 0.435501 0.417814 0.772575 0.076 Uiso 1 1 calc GR . . . .
H34C H 0.415589 0.501124 0.727574 0.076 Uiso 1 1 calc GR . . . .
C35 C 0.5210(2) 0.55722(19) 0.62783(19) 0.0379(7) Uani 1 1 d D . . . .
C36 C 0.5176(2) 0.6618(2) 0.53543(19) 0.0432(8) Uani 1 1 d D . . . .
H36A H 0.473233 0.603142 0.491864 0.052 Uiso 0.849(5) 1 calc R . P B 1
H36B H 0.572058 0.682784 0.517034 0.052 Uiso 0.849(5) 1 calc R . P B 1
H36C H 0.470416 0.608897 0.485981 0.052 Uiso 0.151(5) 1 calc R . P B 2
H36D H 0.568853 0.687693 0.515691 0.052 Uiso 0.151(5) 1 calc R . P B 2
C37 C 0.4559(2) 0.7355(2) 0.53674(19) 0.0368(7) Uani 1 1 d . . . . .
C38 C 0.4234(2) 0.7627(2) 0.6020(2) 0.0448(8) Uani 1 1 d . . . . .
H38 H 0.439789 0.734589 0.648565 0.054 Uiso 1 1 calc R . . . .
C39 C 0.3665(2) 0.8312(2) 0.6002(3) 0.0566(9) Uani 1 1 d . . . . .
H39 H 0.345327 0.850228 0.645951 0.068 Uiso 1 1 calc R . . . .
C40 C 0.3410(3) 0.8710(2) 0.5323(3) 0.0589(10) Uani 1 1 d . . . . .
H40 H 0.301975 0.917468 0.531117 0.071 Uiso 1 1 calc R . . . .
C41 C 0.3715(3) 0.8440(2) 0.4666(2) 0.0538(9) Uani 1 1 d . . . . .
H41 H 0.353143 0.871152 0.419419 0.065 Uiso 1 1 calc R . . . .
C42 C 0.4294(2) 0.7769(2) 0.4687(2) 0.0443(8) Uani 1 1 d . . . . .
H42 H 0.451131 0.758987 0.423106 0.053 Uiso 1 1 calc R . . . .
C43 C 0.6589(2) 0.7036(2) 0.6855(2) 0.0324(8) Uani 0.849(5) 1 d D U P B 1
H43A H 0.664839 0.696531 0.742940 0.039 Uiso 0.849(5) 1 calc R . P B 1
H43B H 0.656066 0.769499 0.685865 0.039 Uiso 0.849(5) 1 calc R . P B 1
C44 C 0.7535(2) 0.6837(2) 0.6719(2) 0.0346(9) Uani 0.849(5) 1 d D U P B 1
H44A H 0.741987 0.615813 0.645116 0.042 Uiso 0.849(5) 1 calc R . P B 1
H44B H 0.764747 0.717688 0.631300 0.042 Uiso 0.849(5) 1 calc R . P B 1
C45 C 0.8545(2) 0.65448(19) 0.80715(19) 0.0388(7) Uani 1 1 d D . . . .
C46 C 0.9583(2) 0.6132(2) 0.9342(2) 0.0431(8) Uani 1 1 d . . . . .
H46A H 0.928656 0.547566 0.898366 0.052 Uiso 1 1 calc R . . . .
H46B H 0.923892 0.626793 0.974113 0.052 Uiso 1 1 calc R . . . .
C47 C 1.0691(2) 0.6241(2) 0.9859(2) 0.0436(8) Uani 1 1 d . . . . .
H47A H 1.096482 0.689560 1.022728 0.052 Uiso 1 1 calc R . . . .
H47B H 1.076073 0.583098 1.025164 0.052 Uiso 1 1 calc R . . . .
C48 C 1.1343(2) 0.6033(2) 0.9383(2) 0.0422(7) Uani 1 1 d . . . . .
H48A H 1.135893 0.650192 0.905419 0.051 Uiso 1 1 calc R . . . .
H48B H 1.102530 0.541096 0.895655 0.051 Uiso 1 1 calc R . . . .
C49 C 1.2411(2) 0.6030(2) 0.9930(2) 0.0401(7) Uani 1 1 d . . . . .
H49A H 1.271099 0.664058 1.037597 0.048 Uiso 1 1 calc R . . . .
H49B H 1.238969 0.554070 1.023726 0.048 Uiso 1 1 calc R . . . .
C50 C 1.3110(2) 0.5869(2) 0.9489(2) 0.0455(8) Uani 1 1 d . . . . .
H50A H 1.315361 0.637082 0.919921 0.055 Uiso 1 1 calc R . . . .
H50B H 1.280320 0.526781 0.903099 0.055 Uiso 1 1 calc R . . . .
C51 C 1.4160(2) 0.5840(2) 1.0043(2) 0.0496(8) Uani 1 1 d . . . . .
H51A H 1.455120 0.573653 0.968618 0.074 Uiso 1 1 calc GR . . . .
H51B H 1.413595 0.532717 1.031602 0.074 Uiso 1 1 calc GR . . . .
H51C H 1.448480 0.643573 1.049314 0.074 Uiso 1 1 calc GR . . . .
C52 C 0.9119(2) 0.80255(18) 0.77856(18) 0.0365(7) Uani 1 1 d D . . . .
H52A H 0.901138 0.825919 0.726812 0.044 Uiso 0.849(5) 1 calc R . P B 1
H52B H 0.982521 0.794080 0.800914 0.044 Uiso 0.849(5) 1 calc R . P B 1
H52C H 0.898237 0.819542 0.723403 0.044 Uiso 0.151(5) 1 calc R . P B 2
H52D H 0.978349 0.784843 0.798910 0.044 Uiso 0.151(5) 1 calc R . P B 2
C53 C 0.90060(19) 0.87721(19) 0.84757(19) 0.0355(7) Uani 1 1 d . . . . .
H53A H 0.840044 0.901578 0.820146 0.043 Uiso 1 1 calc R . . . .
H53B H 0.889602 0.848189 0.891220 0.043 Uiso 1 1 calc R . . . .
C54 C 1.07602(19) 0.94235(18) 0.94685(17) 0.0273(6) Uani 1 1 d . . . . .
C55 C 1.25586(19) 1.02793(18) 1.03075(16) 0.0279(6) Uani 1 1 d . . . . .
C56 C 1.32066(19) 1.11726(19) 1.06664(17) 0.0302(6) Uani 1 1 d . . . . .
H56 H 1.293154 1.171053 1.061111 0.036 Uiso 1 1 calc R . . . .
C57 C 1.4242(2) 1.12801(19) 1.11003(17) 0.0319(6) Uani 1 1 d . . . . .
C58 C 1.4666(2) 1.0512(2) 1.12001(18) 0.0367(7) Uani 1 1 d . . . . .
H58 H 1.537725 1.058586 1.149606 0.044 Uiso 1 1 calc R . . . .
C59 C 1.4018(2) 0.9627(2) 1.08537(19) 0.0372(7) Uani 1 1 d . . . . .
C60 C 1.2981(2) 0.95080(19) 1.04171(18) 0.0344(7) Uani 1 1 d . . . . .
H60 H 1.255582 0.889630 1.019137 0.041 Uiso 1 1 calc R . . . .
C61 C 1.4903(2) 1.2245(2) 1.1434(2) 0.0409(7) Uani 1 1 d . . . . .
C62 C 1.4447(2) 0.8774(2) 1.0936(2) 0.0527(9) Uani 1 1 d . . . . .
N2A N 0.0593(4) 0.7945(8) 0.1919(6) 0.031(3) Uani 0.320(5) 1 d D U P A 2
C12A C 0.0756(6) 0.7421(5) 0.2574(5) 0.0286(18) Uani 0.320(5) 1 d D U P A 2
H12C H 0.024093 0.748402 0.282081 0.034 Uiso 0.320(5) 1 calc R . P A 2
H12D H 0.143138 0.770950 0.304936 0.034 Uiso 0.320(5) 1 calc R . P A 2
C13A C 0.0701(6) 0.6390(5) 0.2239(5) 0.0302(18) Uani 0.320(5) 1 d D U P A 2
H13C H 0.013959 0.614328 0.165778 0.036 Uiso 0.320(5) 1 calc R . P A 2
H13D H 0.134036 0.631652 0.217497 0.036 Uiso 0.320(5) 1 calc R . P A 2
N3A N 0.0540(5) 0.5835(7) 0.2803(6) 0.0298(19) Uani 0.320(5) 1 d D U P A 2
C21A C 0.1344(9) 0.5428(8) 0.3299(7) 0.033(2) Uani 0.320(5) 1 d D U P A 2
H21C H 0.189291 0.548456 0.308725 0.040 Uiso 0.320(5) 1 calc R . P A 2
H21D H 0.106741 0.475225 0.318897 0.040 Uiso 0.320(5) 1 calc R . P A 2
C22A C 0.1794(13) 0.5877(9) 0.4266(7) 0.036(3) Uani 0.320(5) 1 d D U P A 2
H22C H 0.228249 0.646450 0.437865 0.043 Uiso 0.320(5) 1 calc R . P A 2
H22D H 0.123799 0.605901 0.442087 0.043 Uiso 0.320(5) 1 calc R . P A 2
H4 H -0.011(2) 0.484(2) 0.3564(19) 0.038(8) Uiso 1 1 d . . . . .
H7A H 0.637(2) 0.548(2) 0.7192(19) 0.037(9) Uiso 1 1 d . . . . .
H1 H -0.103(2) 0.707(2) 0.1743(19) 0.040(9) Uiso 1 1 d . . . . .
H10A H 0.976(2) 0.728(2) 0.9001(19) 0.036(9) Uiso 1 1 d . . . . .
H12 H 1.136(2) 1.072(2) 0.9694(18) 0.039(8) Uiso 1 1 d . . . . .
H6 H 0.299(2) 0.422(2) 0.5503(18) 0.032(8) Uiso 1 1 d . . . . .
H11A H 0.987(2) 1.008(2) 0.8843(19) 0.047(9) Uiso 1 1 d . . . . .
C43A C 0.6801(9) 0.6525(12) 0.6345(9) 0.033(3) Uani 0.151(5) 1 d D U P B 2
H43C H 0.699199 0.686367 0.596901 0.039 Uiso 0.151(5) 1 calc R . P B 2
H43D H 0.713487 0.598858 0.636617 0.039 Uiso 0.151(5) 1 calc R . P B 2
C44A C 0.7197(9) 0.7181(12) 0.7255(9) 0.032(3) Uani 0.151(5) 1 d D U P B 2
H44C H 0.703001 0.779477 0.721327 0.039 Uiso 0.151(5) 1 calc R . P B 2
H44D H 0.683998 0.692100 0.758074 0.039 Uiso 0.151(5) 1 calc R . P B 2
N8A N 0.5715(8) 0.6172(13) 0.5964(11) 0.0347(9) Uani 0.151(5) 1 d D U P B 2
N9A N 0.8295(7) 0.7328(9) 0.7745(13) 0.035(4) Uani 0.151(5) 1 d D U P B 2


_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 C30 1.339(3) . ?
F2 C30 1.325(3) . ?
F3 C30 1.319(3) . ?
F4 C31 1.333(3) . ?
F5 C31 1.346(3) . ?
F6 C31 1.349(4) . ?
O1 C4 1.245(3) . ?
O2 C14 1.241(3) . ?
O3 C23 1.230(3) . ?
N1 C1 1.456(3) . ?
N1 C4 1.340(3) . ?
N1 H1 0.78(3) . ?
N2 C4 1.388(4) . ?
N2 C5 1.458(4) . ?
N2 C12 1.453(5) . ?
N3 C13 1.453(5) . ?
N3 C14 1.408(4) . ?
N3 C21 1.458(5) . ?
N4 C14 1.344(3) . ?
N4 C15 1.457(3) . ?
N4 H4 0.89(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C22 1.466(5) . ?
N5 C23 1.355(3) . ?
N5 C22A 1.468(7) . ?
N6 C23 1.372(3) . ?
N6 C24 1.397(3) . ?
N6 H6 0.80(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.510(4) . ?
C1 C3 1.519(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 N2A 1.422(6) . ?
C5 H5AA 0.9900 . ?
C5 H5AB 0.9900 . ?
C5 H5BC 0.9900 . ?
C5 H5BD 0.9900 . ?
C5 C6 1.517(4) . ?
C5 N2A 1.465(6) . ?
C6 C7 1.378(4) . ?
C6 C11 1.393(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.518(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N3A 1.412(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.511(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.519(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.508(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.509(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.511(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 C25 1.388(4) . ?
C24 C29 1.396(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.389(3) . ?
C26 C27 1.382(4) . ?
C26 C30 1.484(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.382(4) . ?
C28 C29 1.391(3) . ?
C28 C31 1.485(4) . ?
C29 H29 0.9500 . ?
F7 C61 1.331(3) . ?
F8 C61 1.329(3) . ?
F9 C61 1.336(3) . ?
F10 C62 1.301(4) . ?
F11 C62 1.353(4) . ?
F12 C62 1.337(4) . ?
O4 C35 1.245(3) . ?
O5 C45 1.245(3) . ?
O6 C54 1.234(3) . ?
N7 C32 1.468(3) . ?
N7 C35 1.333(4) . ?
N7 H7A 0.79(3) . ?
N8 C35 1.397(3) . ?
N8 C36 1.459(4) . ?
N8 C43 1.472(4) . ?
N9 C44 1.445(4) . ?
N9 C45 1.383(4) . ?
N9 C52 1.456(3) . ?
N10 C45 1.327(4) . ?
N10 C46 1.463(3) . ?
N10 H10A 0.80(3) . ?
N11 C53 1.453(3) . ?
N11 C54 1.344(3) . ?
N11 H11A 0.83(3) . ?
N12 C54 1.382(3) . ?
N12 C55 1.392(3) . ?
N12 H12 0.87(3) . ?
C32 H32 1.0000 . ?
C32 C33 1.514(4) . ?
C32 C34 1.515(4) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 N8A 1.396(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 H36C 0.9900 . ?
C36 H36D 0.9900 . ?
C36 C37 1.509(4) . ?
C36 N8A 1.408(7) . ?
C37 C38 1.377(4) . ?
C37 C42 1.390(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.394(5) . ?
C39 H39 0.9500 . ?
C39 C40 1.372(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.364(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.387(5) . ?
C42 H42 0.9500 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.528(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 N9A 1.432(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 C47 1.496(4) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C47 C48 1.482(4) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.495(4) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.485(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.487(4) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C52 H52C 0.9900 . ?
C52 H52D 0.9900 . ?
C52 C53 1.527(4) . ?
C52 N9A 1.452(7) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C55 C56 1.402(4) . ?
C55 C60 1.389(4) . ?
C56 H56 0.9500 . ?
C56 C57 1.384(4) . ?
C57 C58 1.384(4) . ?
C57 C61 1.495(4) . ?
C58 H58 0.9500 . ?
C58 C59 1.392(4) . ?
C59 C60 1.385(4) . ?
C59 C62 1.499(4) . ?
C60 H60 0.9500 . ?
N2A C12A 1.469(7) . ?
C12A H12C 0.9900 . ?
C12A H12D 0.9900 . ?
C12A C13A 1.513(7) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C13A N3A 1.459(7) . ?
N3A C21A 1.461(7) . ?
C21A H21C 0.9900 . ?
C21A H21D 0.9900 . ?
C21A C22A 1.512(8) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C43A H43C 0.9900 . ?
C43A H43D 0.9900 . ?
C43A C44A 1.522(10) . ?
C43A N8A 1.444(8) . ?
C44A H44C 0.9900 . ?
C44A H44D 0.9900 . ?
C44A N9A 1.468(8) . ?

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
C1 N1 H1 120(2) . . ?
C4 N1 C1 122.2(2) . . ?
C4 N1 H1 118(2) . . ?
C4 N2 C5 118.0(3) . . ?
C4 N2 C12 122.6(3) . . ?
C12 N2 C5 119.2(3) . . ?
C13 N3 C21 120.8(4) . . ?
C14 N3 C13 118.2(3) . . ?
C14 N3 C21 120.9(3) . . ?
C14 N4 C15 120.0(2) . . ?
C14 N4 H4 122.3(18) . . ?
C15 N4 H4 115.8(18) . . ?
C22 N5 H5A 120.4 . . ?
C23 N5 H5A 120.4 . . ?
C23 N5 H5B 120.9 . . ?
C23 N5 C22 119.2(4) . . ?
C23 N5 C22A 118.2(7) . . ?
C22A N5 H5B 120.9 . . ?
C23 N6 C24 127.2(2) . . ?
C23 N6 H6 118(2) . . ?
C24 N6 H6 115(2) . . ?
N1 C1 H1A 108.3 . . ?
N1 C1 C2 109.8(2) . . ?
N1 C1 C3 110.1(2) . . ?
C2 C1 H1A 108.3 . . ?
C2 C1 C3 111.9(2) . . ?
C3 C1 H1A 108.3 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 122.7(2) . . ?
O1 C4 N2 119.2(3) . . ?
O1 C4 N2A 118.6(4) . . ?
N1 C4 N2 117.8(3) . . ?
N1 C4 N2A 116.7(4) . . ?
N2 C5 H5AA 107.1 . . ?
N2 C5 H5AB 107.1 . . ?
N2 C5 C6 120.9(3) . . ?
H5AA C5 H5AB 106.8 . . ?
H5BC C5 H5BD 109.3 . . ?
C6 C5 H5AA 107.1 . . ?
C6 C5 H5AB 107.1 . . ?
C6 C5 H5BC 111.5 . . ?
C6 C5 H5BD 111.5 . . ?
N2A C5 H5BC 111.5 . . ?
N2A C5 H5BD 111.5 . . ?
N2A C5 C6 101.3(5) . . ?
C7 C6 C5 122.1(2) . . ?
C7 C6 C11 118.4(3) . . ?
C11 C6 C5 119.5(3) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.6(3) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.7(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C6 C11 H11 119.5 . . ?
C10 C11 C6 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
N2 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
N2 C12 C13 113.9(4) . . ?
H12A C12 H12B 107.7 . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
N3 C13 C12 111.0(4) . . ?
N3 C13 H13A 109.4 . . ?
N3 C13 H13B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O2 C14 N3 119.2(3) . . ?
O2 C14 N4 122.6(3) . . ?
O2 C14 N3A 121.3(4) . . ?
N4 C14 N3 117.9(3) . . ?
N4 C14 N3A 111.8(4) . . ?
N4 C15 H15A 109.6 . . ?
N4 C15 H15B 109.6 . . ?
N4 C15 C16 110.4(2) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.4(2) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.2(2) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 C17 114.3(3) . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.6 . . ?
C18 C19 H19B 108.6 . . ?
C18 C19 C20 114.7(3) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 C22 110.9(4) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
N5 C22 C21 107.4(4) . . ?
N5 C22 H22A 110.2 . . ?
N5 C22 H22B 110.2 . . ?
C21 C22 H22A 110.2 . . ?
C21 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
O3 C23 N5 122.7(2) . . ?
O3 C23 N6 123.8(2) . . ?
N5 C23 N6 113.5(2) . . ?
C25 C24 N6 117.0(2) . . ?
C25 C24 C29 118.7(2) . . ?
C29 C24 N6 124.4(2) . . ?
C24 C25 H25 119.4 . . ?
C24 C25 C26 121.2(2) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 C30 117.8(2) . . ?
C27 C26 C25 120.3(3) . . ?
C27 C26 C30 121.9(2) . . ?
C26 C27 H27 120.8 . . ?
C26 C27 C28 118.5(2) . . ?
C28 C27 H27 120.8 . . ?
C27 C28 C29 122.0(2) . . ?
C27 C28 C31 119.1(2) . . ?
C29 C28 C31 118.9(2) . . ?
C24 C29 H29 120.3 . . ?
C28 C29 C24 119.3(3) . . ?
C28 C29 H29 120.3 . . ?
F1 C30 C26 111.9(2) . . ?
F2 C30 F1 104.3(3) . . ?
F2 C30 C26 113.2(2) . . ?
F3 C30 F1 106.2(2) . . ?
F3 C30 F2 106.6(2) . . ?
F3 C30 C26 113.9(2) . . ?
F4 C31 F5 106.7(2) . . ?
F4 C31 F6 105.8(2) . . ?
F4 C31 C28 113.7(2) . . ?
F5 C31 F6 105.3(2) . . ?
F5 C31 C28 113.0(2) . . ?
F6 C31 C28 111.8(2) . . ?
C32 N7 H7A 117(2) . . ?
C35 N7 C32 121.1(2) . . ?
C35 N7 H7A 122(2) . . ?
C35 N8 C36 117.4(2) . . ?
C35 N8 C43 122.3(2) . . ?
C36 N8 C43 119.8(2) . . ?
C44 N9 C52 120.8(3) . . ?
C45 N9 C44 117.8(2) . . ?
C45 N9 C52 120.9(3) . . ?
C45 N10 C46 119.8(2) . . ?
C45 N10 H10A 124(2) . . ?
C46 N10 H10A 114(2) . . ?
C53 N11 H11A 122(2) . . ?
C54 N11 C53 119.9(2) . . ?
C54 N11 H11A 118(2) . . ?
C54 N12 C55 127.2(2) . . ?
C54 N12 H12 114.9(19) . . ?
C55 N12 H12 117(2) . . ?
N7 C32 H32 108.1 . . ?
N7 C32 C33 108.9(2) . . ?
N7 C32 C34 111.2(3) . . ?
C33 C32 H32 108.1 . . ?
C33 C32 C34 112.4(3) . . ?
C34 C32 H32 108.1 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O4 C35 N7 123.0(2) . . ?
O4 C35 N8 119.7(2) . . ?
O4 C35 N8A 116.1(6) . . ?
N7 C35 N8 117.1(2) . . ?
N7 C35 N8A 117.4(5) . . ?
N8 C36 H36A 108.9 . . ?
N8 C36 H36B 108.9 . . ?
N8 C36 C37 113.6(3) . . ?
H36A C36 H36B 107.7 . . ?
H36C C36 H36D 105.3 . . ?
C37 C36 H36A 108.9 . . ?
C37 C36 H36B 108.9 . . ?
C37 C36 H36C 103.5 . . ?
C37 C36 H36D 103.5 . . ?
N8A C36 H36C 103.5 . . ?
N8A C36 H36D 103.5 . . ?
N8A C36 C37 134.9(9) . . ?
C38 C37 C36 122.8(3) . . ?
C38 C37 C42 118.4(3) . . ?
C42 C37 C36 118.8(3) . . ?
C37 C38 H38 119.7 . . ?
C37 C38 C39 120.6(3) . . ?
C39 C38 H38 119.7 . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.1(3) . . ?
C40 C39 H39 120.0 . . ?
C39 C40 H40 120.0 . . ?
C41 C40 C39 120.1(3) . . ?
C41 C40 H40 120.0 . . ?
C40 C41 H41 120.0 . . ?
C40 C41 C42 120.1(3) . . ?
C42 C41 H41 120.0 . . ?
C37 C42 H42 119.6 . . ?
C41 C42 C37 120.8(3) . . ?
C41 C42 H42 119.6 . . ?
N8 C43 H43A 108.8 . . ?
N8 C43 H43B 108.8 . . ?
N8 C43 C44 113.8(3) . . ?
H43A C43 H43B 107.7 . . ?
C44 C43 H43A 108.8 . . ?
C44 C43 H43B 108.8 . . ?
N9 C44 C43 112.5(3) . . ?
N9 C44 H44A 109.1 . . ?
N9 C44 H44B 109.1 . . ?
C43 C44 H44A 109.1 . . ?
C43 C44 H44B 109.1 . . ?
H44A C44 H44B 107.8 . . ?
O5 C45 N9 120.1(3) . . ?
O5 C45 N10 121.5(3) . . ?
O5 C45 N9A 121.6(5) . . ?
N10 C45 N9 118.2(2) . . ?
N10 C45 N9A 114.0(7) . . ?
N10 C46 H46A 109.2 . . ?
N10 C46 H46B 109.2 . . ?
N10 C46 C47 111.9(2) . . ?
H46A C46 H46B 107.9 . . ?
C47 C46 H46A 109.2 . . ?
C47 C46 H46B 109.2 . . ?
C46 C47 H47A 107.8 . . ?
C46 C47 H47B 107.8 . . ?
H47A C47 H47B 107.1 . . ?
C48 C47 C46 118.0(3) . . ?
C48 C47 H47A 107.8 . . ?
C48 C47 H47B 107.8 . . ?
C47 C48 H48A 108.4 . . ?
C47 C48 H48B 108.4 . . ?
C47 C48 C49 115.5(3) . . ?
H48A C48 H48B 107.5 . . ?
C49 C48 H48A 108.4 . . ?
C49 C48 H48B 108.4 . . ?
C48 C49 H49A 107.9 . . ?
C48 C49 H49B 107.9 . . ?
H49A C49 H49B 107.2 . . ?
C50 C49 C48 117.7(3) . . ?
C50 C49 H49A 107.9 . . ?
C50 C49 H49B 107.9 . . ?
C49 C50 H50A 108.1 . . ?
C49 C50 H50B 108.1 . . ?
C49 C50 C51 116.7(3) . . ?
H50A C50 H50B 107.3 . . ?
C51 C50 H50A 108.1 . . ?
C51 C50 H50B 108.1 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51B 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
N9 C52 H52A 108.5 . . ?
N9 C52 H52B 108.5 . . ?
N9 C52 C53 115.2(3) . . ?
H52A C52 H52B 107.5 . . ?
H52C C52 H52D 110.5 . . ?
C53 C52 H52A 108.5 . . ?
C53 C52 H52B 108.5 . . ?
C53 C52 H52C 113.1 . . ?
C53 C52 H52D 113.1 . . ?
N9A C52 H52C 113.1 . . ?
N9A C52 H52D 113.1 . . ?
N9A C52 C53 93.1(9) . . ?
N11 C53 C52 112.4(2) . . ?
N11 C53 H53A 109.1 . . ?
N11 C53 H53B 109.1 . . ?
C52 C53 H53A 109.1 . . ?
C52 C53 H53B 109.1 . . ?
H53A C53 H53B 107.9 . . ?
O6 C54 N11 122.9(2) . . ?
O6 C54 N12 123.5(2) . . ?
N11 C54 N12 113.6(2) . . ?
N12 C55 C56 117.6(2) . . ?
C60 C55 N12 124.1(2) . . ?
C60 C55 C56 118.2(2) . . ?
C55 C56 H56 119.6 . . ?
C57 C56 C55 120.8(3) . . ?
C57 C56 H56 119.6 . . ?
C56 C57 C58 121.1(3) . . ?
C56 C57 C61 118.5(3) . . ?
C58 C57 C61 120.4(3) . . ?
C57 C58 H58 121.0 . . ?
C57 C58 C59 118.0(3) . . ?
C59 C58 H58 121.0 . . ?
C58 C59 C62 119.7(3) . . ?
C60 C59 C58 121.6(3) . . ?
C60 C59 C62 118.6(3) . . ?
C55 C60 H60 119.8 . . ?
C59 C60 C55 120.3(3) . . ?
C59 C60 H60 119.8 . . ?
F7 C61 F9 106.1(2) . . ?
F7 C61 C57 112.6(2) . . ?
F8 C61 F7 105.5(3) . . ?
F8 C61 F9 106.8(2) . . ?
F8 C61 C57 112.9(2) . . ?
F9 C61 C57 112.4(3) . . ?
F10 C62 F11 106.3(3) . . ?
F10 C62 F12 109.3(3) . . ?
F10 C62 C59 114.5(3) . . ?
F11 C62 C59 111.4(3) . . ?
F12 C62 F11 103.6(3) . . ?
F12 C62 C59 111.0(3) . . ?
C4 N2A C5 115.4(5) . . ?
C4 N2A C12A 120.3(5) . . ?
C5 N2A C12A 123.2(6) . . ?
N2A C12A H12C 108.6 . . ?
N2A C12A H12D 108.6 . . ?
N2A C12A C13A 114.6(8) . . ?
H12C C12A H12D 107.6 . . ?
C13A C12A H12C 108.6 . . ?
C13A C12A H12D 108.6 . . ?
C12A C13A H13C 108.9 . . ?
C12A C13A H13D 108.9 . . ?
H13C C13A H13D 107.7 . . ?
N3A C13A C12A 113.3(7) . . ?
N3A C13A H13C 108.9 . . ?
N3A C13A H13D 108.9 . . ?
C14 N3A C13A 116.8(6) . . ?
C14 N3A C21A 122.2(7) . . ?
C13A N3A C21A 121.0(8) . . ?
N3A C21A H21C 108.7 . . ?
N3A C21A H21D 108.7 . . ?
N3A C21A C22A 114.3(9) . . ?
H21C C21A H21D 107.6 . . ?
C22A C21A H21C 108.7 . . ?
C22A C21A H21D 108.7 . . ?
N5 C22A C21A 120.7(9) . . ?
N5 C22A H22C 107.1 . . ?
N5 C22A H22D 107.1 . . ?
C21A C22A H22C 107.1 . . ?
C21A C22A H22D 107.1 . . ?
H22C C22A H22D 106.8 . . ?
H43C C43A H43D 107.7 . . ?
C44A C43A H43C 108.8 . . ?
C44A C43A H43D 108.8 . . ?
N8A C43A H43C 108.8 . . ?
N8A C43A H43D 108.8 . . ?
N8A C43A C44A 113.6(15) . . ?
C43A C44A H44C 108.7 . . ?
C43A C44A H44D 108.7 . . ?
H44C C44A H44D 107.6 . . ?
N9A C44A C43A 114.2(15) . . ?
N9A C44A H44C 108.7 . . ?
N9A C44A H44D 108.7 . . ?
C35 N8A C36 121.0(7) . . ?
C35 N8A C43A 123.4(9) . . ?
C36 N8A C43A 114.5(9) . . ?
C45 N9A C52 117.8(7) . . ?
C45 N9A C44A 111.4(9) . . ?
C52 N9A C44A 129.5(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_testr1
_database_code_depnum_ccdc_archive 'CCDC 2189987'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2019-07-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 F6 N4 O2'
_chemical_formula_sum            'C22 H24 F6 N4 O2'
_chemical_formula_weight         490.45
_chemical_melting_point          436
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.7595(6)
_cell_length_b                   31.7595(6)
_cell_length_c                   24.6991(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     21575.4(10)
_cell_formula_units_Z            36
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.44
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0682 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.8699. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             9144
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.455
_exptl_crystal_size_min          0.241
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58951
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.108
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7995
_reflns_number_total             9812
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     852
_refine_ls_number_reflns         9812
_refine_ls_number_restraints     598
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0626P)²+38.8182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1346
_refine_special_detail           
;
One of the molecules and some of the CF3 groups were disordered, 
the occupancies were refined with their sum set to equal 1.  
Restraints were applied to the part with smaller occupancy ~0.2 
and the CF3 groups to maintain sensible geometric parameters. 
Restraints or constraints were applied to thermal parameters to
maintain sensible values.  Refined as a twin 0 1 0 1 0 0 0 0 -1,
BASF 0.3245(10).
;
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6754(10)
 0.3246(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C32A-C26A = C23A-C22A = C22A-C21A = C33A-C25A
 1.54 with sigma of 0.01
 N7A-C33A = N6A-C25A = N6A-C32A
 1.47 with sigma of 0.01
 F1-F2 = F2-F3 = F3-F1 = F1A-F2A = F1A-F3A = F2A-F3A
 2.14 with sigma of 0.01
 F2A-C19 \\sim F2-C19 \\sim F3-C19 \\sim F3A-C19 \\sim F1-C19 \\sim F1A-C19
\\sim F4A-C20 \\sim F5-C20 ~
 F5A-C20 \\sim F6-C20 \\sim F6A-C20 \\sim F4-C20 \\sim F9-C41 \\sim F7A-C41
\\sim F7-C41 \\sim F8A-C41 \\sim F8-
 C41 \\sim F9A-C41
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
F4A \\sim F5 \\sim F5A \\sim F6 \\sim F6A \\sim F4: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F8 \\sim F9A \\sim F9 \\sim F7A \\sim F7 \\sim F8A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
F1A \\sim F1 \\sim F3A \\sim F3 \\sim F2A \\sim F2: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
N5A \\sim C22A \\sim C21A \\sim C23A \\sim O4A \\sim N7A \\sim C24A \\sim O3A
\\sim N6A \\sim C25A \\sim C32A \\sim C33A \\sim C26A \\sim C29A \\sim C28A
\\sim C27A \\sim C31A \\sim C30A \\sim O3 \\sim O4 \\sim N5 \\sim N6 \\sim N7
\\sim C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28
\\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C34A \\sim
N8: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
Uanis(C26A) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C30A) \\sim Ueq,
Uanis(C29A) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C27A) \\sim Ueq,
Uanis(C32A) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2A) = Uanis(F2)
5. Others
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(1)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
 Sof(H8B)=Sof(N5A)=Sof(H5A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C34A)=Sof(O4A)=Sof(N7A)=
 Sof(H7A)=Sof(C24A)=Sof(O3A)=Sof(N6A)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C32A)=
 Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=Sof(H33D)=Sof(C26A)=Sof(C31A)=
 Sof(H31A)=Sof(C30A)=Sof(H30A)=Sof(C29A)=Sof(H29A)=Sof(C28A)=Sof(H28A)=
 Sof(C27A)=Sof(H27A)=1-FVAR(2)
 Sof(O3)=Sof(O4)=Sof(N5)=Sof(H5)=Sof(N6)=Sof(N7)=Sof(H7)=Sof(H8A)=Sof(C21)=
 Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(H23C)=Sof(C24)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(C27)=Sof(H27)=
 Sof(C28)=Sof(H28)=Sof(C29)=Sof(H29)=Sof(C30)=Sof(H30)=Sof(C31)=Sof(H31)=
 Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=FVAR(2)
 Sof(F7A)=Sof(F9A)=Sof(F8A)=1-FVAR(3)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=1-FVAR(4)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C2(H2), C22(H22), C22A(H22A)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5B,H5C), C11(H11A,H11B), C12(H12A,H12B), C25(H25A,H25B), C32(H32A,H32B),
 C33(H33A,H33B), C25A(H25C,H25D), C32A(H32C,H32D), C33A(H33C,H33D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N4(H4), C0AA(H0AA), C1AA(H1AA), C7(H7B), C8(H8), C9(H9),
 C10(H10), C15(H15), C17(H17), N5(H5), N7(H7), N8(H8A), N8(H8B), C27(H27),
 C28(H28), C29(H29), C30(H30), C31(H31), C36(H36), C38(H38), C40(H40), N5A(H5A),
  N7A(H7A), C31A(H31A), C30A(H30A), C29A(H29A), C28A(H28A), C27A(H27A)
6.d Fitted hexagon refined as free rotating group:
 C26A(C31A,C30A,C29A,C28A,C27A)
6.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C),
 C21A(H21D,H21E,H21F), C23A(H23D,H23E,H23F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6404(4) 0.7816(4) 0.3064(3) 0.0421(14) Uani 0.555(13) 1 d D U P A 1
F2 F 0.6511(3) 0.7632(3) 0.3859(3) 0.0499(14) Uani 0.555(13) 1 d D U P A 1
F3 F 0.5991(2) 0.78413(19) 0.3760(4) 0.0659(19) Uani 0.555(13) 1 d D U P A 1
F4 F 0.43257(9) 0.65247(12) 0.36942(16) 0.0603(11) Uani 0.802(6) 1 d D U P B 1
F5 F 0.41770(10) 0.58022(11) 0.3582(2) 0.0661(13) Uani 0.802(6) 1 d D U P B 1
F6 F 0.42638(10) 0.62455(16) 0.29100(10) 0.0660(11) Uani 0.802(6) 1 d D U P B 1
O1 O 0.81710(6) 0.62967(7) 0.35470(8) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.65850(7) 0.63383(7) 0.31813(8) 0.0324(4) Uani 1 1 d . . . . .
N1 N 0.75963(8) 0.65176(8) 0.34306(9) 0.0265(5) Uani 1 1 d . . . . .
H1 H 0.728723 0.643329 0.344966 0.032 Uiso 1 1 calc R . . . .
N2 N 0.73737(8) 0.57241(8) 0.36613(9) 0.0253(5) Uani 1 1 d . . . . .
N3 N 0.61935(8) 0.55166(8) 0.30926(9) 0.0278(5) Uani 1 1 d . . . . .
H3 H 0.591398 0.524556 0.305325 0.033 Uiso 1 1 calc R . . . .
N4 N 0.57461(7) 0.58873(8) 0.31943(9) 0.0250(5) Uani 1 1 d . . . . .
H4 H 0.550179 0.558815 0.316089 0.030 Uiso 1 1 calc R . . . .
C0AA C 0.51260(9) 0.60933(9) 0.33004(10) 0.0229(5) Uani 1 1 d . . . . .
H0AA H 0.489287 0.575856 0.325754 0.028 Uiso 1 1 calc R . . . .
C1 C 0.77299(11) 0.73330(11) 0.33594(15) 0.0418(8) Uani 1 1 d . . . . .
H1A H 0.744809 0.722326 0.311993 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.797062 0.767095 0.327407 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.762585 0.731092 0.373688 0.063 Uiso 1 1 calc GR . . . .
C1AA C 0.76976(10) 0.52177(11) 0.27663(12) 0.0332(6) Uani 1 1 d . . . . .
H1AA H 0.796445 0.554091 0.277612 0.040 Uiso 1 1 calc R . . . .
C2 C 0.79557(10) 0.70123(10) 0.32773(13) 0.0321(6) Uani 1 1 d . . . . .
H2 H 0.824357 0.712894 0.352201 0.039 Uiso 1 1 calc R . . . .
C3 C 0.81220(12) 0.70362(12) 0.26991(14) 0.0446(8) Uani 1 1 d . . . . .
H3A H 0.824355 0.680937 0.265119 0.067 Uiso 1 1 calc GR . . . .
H3B H 0.838228 0.736740 0.261788 0.067 Uiso 1 1 calc GR . . . .
H3C H 0.784792 0.694741 0.245318 0.067 Uiso 1 1 calc GR . . . .
C4 C 0.77337(9) 0.61849(10) 0.35443(10) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.74867(10) 0.53327(10) 0.37200(11) 0.0285(6) Uani 1 1 d . . . . .
H5B H 0.729023 0.511766 0.402037 0.034 Uiso 1 1 calc R . . . .
H5C H 0.783362 0.547629 0.381970 0.034 Uiso 1 1 calc R . . . .
C6 C 0.73907(10) 0.50294(10) 0.32147(12) 0.0295(6) Uani 1 1 d . . . . .
C7 C 0.69959(10) 0.45595(11) 0.31861(14) 0.0383(7) Uani 1 1 d . . . . .
H7B H 0.678158 0.442791 0.348607 0.046 Uiso 1 1 calc R . . . .
C8 C 0.69125(12) 0.42817(13) 0.27237(16) 0.0507(9) Uani 1 1 d . . . . .
H8 H 0.663818 0.396326 0.270635 0.061 Uiso 1 1 calc R . . . .
C9 C 0.72228(13) 0.44631(13) 0.22913(15) 0.0495(9) Uani 1 1 d . . . . .
H9 H 0.717039 0.426651 0.198060 0.059 Uiso 1 1 calc R . . . .
C10 C 0.76154(13) 0.49363(13) 0.23075(13) 0.0440(8) Uani 1 1 d . . . . .
H10 H 0.782634 0.506563 0.200447 0.053 Uiso 1 1 calc R . . . .
C11 C 0.68630(9) 0.55876(10) 0.36568(11) 0.0260(6) Uani 1 1 d . . . . .
H11A H 0.682702 0.584622 0.383723 0.031 Uiso 1 1 calc R . . . .
H11B H 0.667612 0.528520 0.386927 0.031 Uiso 1 1 calc R . . . .
C12 C 0.66459(9) 0.55069(10) 0.30862(11) 0.0254(5) Uani 1 1 d . . . . .
H12A H 0.688054 0.576399 0.284116 0.031 Uiso 1 1 calc R . . . .
H12B H 0.658484 0.518910 0.294627 0.031 Uiso 1 1 calc R . . . .
C13 C 0.62045(9) 0.59430(9) 0.31592(11) 0.0243(5) Uani 1 1 d . . . . .
C14 C 0.56211(9) 0.62441(9) 0.32758(10) 0.0232(5) Uani 1 1 d . . . . .
C15 C 0.59585(10) 0.67360(9) 0.33449(11) 0.0285(6) Uani 1 1 d . . . . .
H15 H 0.629725 0.684822 0.333062 0.034 Uiso 1 1 calc R . . . .
C16 C 0.57913(10) 0.70611(9) 0.34352(12) 0.0299(6) Uani 1 1 d . . . . .
C17 C 0.53036(10) 0.69150(10) 0.34532(11) 0.0286(6) Uani 1 1 d . . . . .
H17 H 0.519800 0.714356 0.350987 0.034 Uiso 1 1 calc R . . . .
C18 C 0.49705(9) 0.64237(9) 0.33861(10) 0.0238(5) Uani 1 1 d . . . . .
C19 C 0.61649(10) 0.75896(10) 0.35012(12) 0.0400(7) Uani 1 1 d D . . . .
C20 C 0.44373(10) 0.62480(9) 0.33931(10) 0.0292(6) Uani 1 1 d D . . . .
F7 F 0.54478(16) 0.37612(18) 0.1651(2) 0.0680(17) Uani 0.813(11) 1 d D U P C 1
F8 F 0.57605(19) 0.39654(10) 0.08734(10) 0.0595(13) Uani 0.813(11) 1 d D U P C
1
F9 F 0.61599(19) 0.38966(17) 0.1521(3) 0.092(2) Uani 0.813(11) 1 d D U P C 1
F10 F 0.75050(7) 0.55685(7) 0.13306(8) 0.0510(5) Uani 1 1 d . . . . .
F11 F 0.73376(7) 0.61396(7) 0.12338(8) 0.0501(5) Uani 1 1 d . . . . .
F12 F 0.74476(7) 0.59371(8) 0.20277(8) 0.0539(5) Uani 1 1 d . . . . .
O3 O 0.30434(8) 0.39921(9) 0.13661(10) 0.0309(6) Uani 0.788(2) 1 d . U P D 1
O4 O 0.48345(9) 0.47129(9) 0.18539(10) 0.0328(6) Uani 0.788(2) 1 d . U P D 1
N5 N 0.38136(13) 0.41329(12) 0.14861(14) 0.0297(7) Uani 0.788(2) 1 d . U P D 1
H5 H 0.412623 0.434768 0.149675 0.036 Uiso 0.788(2) 1 calc R . P D 1
N6 N 0.36678(11) 0.47744(10) 0.13890(11) 0.0279(6) Uani 0.788(2) 1 d . U P D 1
N7 N 0.48952(10) 0.54372(10) 0.20449(12) 0.0287(6) Uani 0.788(2) 1 d . U P D 1
H7 H 0.508359 0.574309 0.213885 0.034 Uiso 0.788(2) 1 calc R . P D 1
N8 N 0.55959(8) 0.54103(8) 0.18865(9) 0.0274(5) Uani 1 1 d . U . . .
H8A H 0.573882 0.572400 0.195447 0.033 Uiso 0.788(2) 1 calc R . P D 1
H8B H 0.529050 0.519683 0.195844 0.033 Uiso 0.212(2) 1 calc R . P D 2
C21 C 0.40931(18) 0.35550(18) 0.1454(2) 0.0526(12) Uani 0.788(2) 1 d . U P D 1
H21A H 0.434288 0.374253 0.172501 0.079 Uiso 0.788(2) 1 calc GR . P D 1
H21B H 0.422405 0.367247 0.109088 0.079 Uiso 0.788(2) 1 calc GR . P D 1
H21C H 0.399549 0.321042 0.148467 0.079 Uiso 0.788(2) 1 calc GR . P D 1
C22 C 0.36510(13) 0.36168(13) 0.15486(15) 0.0325(8) Uani 0.788(2) 1 d . U P D 1
H22 H 0.339819 0.342737 0.126923 0.039 Uiso 0.788(2) 1 calc R . P D 1
C23 C 0.34370(16) 0.34371(15) 0.21109(17) 0.0424(10) Uani 0.788(2) 1 d . U P D
1
H23A H 0.314641 0.346671 0.215647 0.064 Uiso 0.788(2) 1 calc GR . P D 1
H23B H 0.367821 0.363330 0.238625 0.064 Uiso 0.788(2) 1 calc GR . P D 1
H23C H 0.334900 0.309567 0.215100 0.064 Uiso 0.788(2) 1 calc GR . P D 1
C24 C 0.34893(12) 0.42832(13) 0.14122(13) 0.0273(7) Uani 0.788(2) 1 d . U P D 1
C25 C 0.33354(13) 0.49627(13) 0.13524(14) 0.0303(8) Uani 0.788(2) 1 d . U P D 1
H25A H 0.303409 0.471736 0.117009 0.036 Uiso 0.788(2) 1 calc R . P D 1
H25B H 0.348549 0.525749 0.112251 0.036 Uiso 0.788(2) 1 calc R . P D 1
C26 C 0.32001(13) 0.50904(14) 0.18952(15) 0.0330(8) Uani 0.788(2) 1 d . U P D 1
C27 C 0.31866(15) 0.55184(16) 0.19481(18) 0.0448(10) Uani 0.788(2) 1 d . U P D
1
H27 H 0.326363 0.572897 0.164538 0.054 Uiso 0.788(2) 1 calc R . P D 1
C28 C 0.30629(19) 0.5643(2) 0.2434(2) 0.0564(12) Uani 0.788(2) 1 d . U P D 1
H28 H 0.305069 0.593500 0.246536 0.068 Uiso 0.788(2) 1 calc R . P D 1
C29 C 0.29601(17) 0.5346(2) 0.2862(2) 0.0495(12) Uani 0.788(2) 1 d . U P D 1
H29 H 0.288490 0.543908 0.319806 0.059 Uiso 0.788(2) 1 calc R . P D 1
C30 C 0.29594(15) 0.4913(2) 0.28326(18) 0.0525(12) Uani 0.788(2) 1 d . U P D 1
H30 H 0.287859 0.470600 0.313915 0.063 Uiso 0.788(2) 1 calc R . P D 1
C31 C 0.30818(14) 0.47853(17) 0.23357(16) 0.0415(9) Uani 0.788(2) 1 d . U P D 1
H31 H 0.308281 0.448770 0.230367 0.050 Uiso 0.788(2) 1 calc R . P D 1
C32 C 0.41843(12) 0.51246(13) 0.14352(14) 0.0283(7) Uani 0.788(2) 1 d . U P D 1
H32A H 0.424986 0.543449 0.126681 0.034 Uiso 0.788(2) 1 calc R . P D 1
H32B H 0.436927 0.500228 0.123049 0.034 Uiso 0.788(2) 1 calc R . P D 1
C33 C 0.43674(12) 0.52233(13) 0.20203(14) 0.0291(7) Uani 0.788(2) 1 d . U P D 1
H33A H 0.427501 0.544752 0.219129 0.035 Uiso 0.788(2) 1 calc R . P D 1
H33B H 0.421041 0.491475 0.222657 0.035 Uiso 0.788(2) 1 calc R . P D 1
C34 C 0.50854(12) 0.51548(12) 0.19203(13) 0.0267(7) Uani 0.788(2) 1 d . U P D 1
C35 C 0.59037(11) 0.52318(10) 0.17597(11) 0.0291(6) Uani 1 1 d . . . . .
C36 C 0.57321(12) 0.47402(11) 0.16630(11) 0.0339(7) Uani 1 1 d . . . . .
H36 H 0.539406 0.451294 0.168768 0.041 Uiso 1 1 calc R . . . .
C37 C 0.60550(12) 0.45831(11) 0.15307(12) 0.0344(6) Uani 1 1 d . . . . .
C38 C 0.65503(12) 0.49035(11) 0.14926(11) 0.0348(7) Uani 1 1 d . . . . .
H38 H 0.676860 0.479090 0.140567 0.042 Uiso 1 1 calc R . . . .
C39 C 0.67189(11) 0.53923(11) 0.15844(11) 0.0335(6) Uani 1 1 d . . . . .
C40 C 0.64016(11) 0.55588(11) 0.17202(11) 0.0302(6) Uani 1 1 d . . . . .
H40 H 0.652432 0.589500 0.178599 0.036 Uiso 1 1 calc R . . . .
C41 C 0.58590(11) 0.40570(11) 0.13968(12) 0.0376(7) Uani 1 1 d D . . . .
C42 C 0.72478(11) 0.57593(12) 0.15463(12) 0.0367(7) Uani 1 1 d . . . . .
F4A F 0.4242(3) 0.6059(6) 0.3864(3) 0.060(4) Uani 0.198(6) 1 d D U P B 2
F5A F 0.4194(3) 0.5877(5) 0.3056(6) 0.061(4) Uani 0.198(6) 1 d D U P B 2
F6A F 0.4317(4) 0.6578(4) 0.3272(8) 0.065(4) Uani 0.198(6) 1 d D U P B 2
N5A N 0.6473(5) 0.7302(5) 0.1628(6) 0.031(3) Uani 0.212(2) 1 d . U P D 2
H5A H 0.632797 0.698522 0.167619 0.037 Uiso 0.212(2) 1 calc R . P D 2
C22A C 0.7003(5) 0.7574(4) 0.1652(4) 0.027(3) Uani 0.212(2) 1 d D U P D 2
H22A H 0.713018 0.782616 0.135960 0.033 Uiso 0.212(2) 1 calc R . P D 2
C21A C 0.7157(6) 0.7825(6) 0.2204(5) 0.045(4) Uani 0.212(2) 1 d D U P D 2
H21D H 0.707280 0.757912 0.248749 0.067 Uiso 0.212(2) 1 calc GR . P D 2
H21E H 0.698805 0.800654 0.227306 0.067 Uiso 0.212(2) 1 calc GR . P D 2
H21F H 0.750906 0.804884 0.220616 0.067 Uiso 0.212(2) 1 calc GR . P D 2
C23A C 0.7195(6) 0.7218(5) 0.1560(7) 0.037(3) Uani 0.212(2) 1 d D U P D 2
H23D H 0.705306 0.703228 0.122685 0.055 Uiso 0.212(2) 1 calc GR . P D 2
H23E H 0.710231 0.699394 0.186736 0.055 Uiso 0.212(2) 1 calc GR . P D 2
H23F H 0.754951 0.740139 0.152688 0.055 Uiso 0.212(2) 1 calc GR . P D 2
C34A C 0.5733(4) 0.5904(5) 0.1909(6) 0.031(2) Uani 0.212(2) 1 d . U P D 2
O4A O 0.6140(3) 0.6258(3) 0.1910(4) 0.037(2) Uani 0.212(2) 1 d . U P D 2
N7A N 0.5322(4) 0.5935(4) 0.1960(6) 0.039(2) Uani 0.212(2) 1 d D U P D 2
H7A H 0.503241 0.567295 0.195460 0.047 Uiso 0.212(2) 1 calc R . P D 2
C24A C 0.6198(5) 0.7490(5) 0.1543(7) 0.038(3) Uani 0.212(2) 1 d . U P D 2
O3A O 0.6358(3) 0.7926(3) 0.1457(4) 0.030(2) Uani 0.212(2) 1 d . U P D 2
N6A N 0.5693(4) 0.7162(4) 0.1471(7) 0.050(3) Uani 0.212(2) 1 d D U P D 2
C25A C 0.5475(6) 0.6626(4) 0.1446(6) 0.048(3) Uani 0.212(2) 1 d D U P D 2
H25C H 0.570068 0.654259 0.126037 0.058 Uiso 0.212(2) 1 calc R . P D 2
H25D H 0.516739 0.648042 0.123887 0.058 Uiso 0.212(2) 1 calc R . P D 2
C32A C 0.5383(6) 0.7377(6) 0.1392(5) 0.052(3) Uani 0.212(2) 1 d D U P D 2
H32C H 0.510309 0.715455 0.116309 0.062 Uiso 0.212(2) 1 calc R . P D 2
H32D H 0.557030 0.768551 0.118948 0.062 Uiso 0.212(2) 1 calc R . P D 2
C33A C 0.5378(6) 0.6422(4) 0.2024(6) 0.047(3) Uani 0.212(2) 1 d D U P D 2
H33C H 0.565356 0.662803 0.226619 0.056 Uiso 0.212(2) 1 calc R . P D 2
H33D H 0.507770 0.640037 0.217211 0.056 Uiso 0.212(2) 1 calc R . P D 2
C26A C 0.5185(5) 0.7484(5) 0.1913(4) 0.062(3) Uani 0.212(2) 1 d D U P D 2
C31A C 0.4708(4) 0.7388(5) 0.1950(6) 0.070(4) Uani 0.212(2) 1 d G U P D 2
H31A H 0.448851 0.723268 0.165853 0.084 Uiso 0.212(2) 1 calc R . P D 2
C30A C 0.4552(4) 0.7518(7) 0.2413(7) 0.087(6) Uani 0.212(2) 1 d G U P D 2
H30A H 0.422612 0.745257 0.243852 0.105 Uiso 0.212(2) 1 calc R . P D 2
C29A C 0.4873(6) 0.7745(7) 0.2840(6) 0.082(6) Uani 0.212(2) 1 d G U P D 2
H29A H 0.476633 0.783421 0.315623 0.098 Uiso 0.212(2) 1 calc R . P D 2
C28A C 0.5350(5) 0.7841(6) 0.2803(5) 0.077(4) Uani 0.212(2) 1 d G U P D 2
H28A H 0.556893 0.799596 0.309396 0.093 Uiso 0.212(2) 1 calc R . P D 2
C27A C 0.5505(4) 0.7710(5) 0.2339(5) 0.065(4) Uani 0.212(2) 1 d G U P D 2
H27A H 0.583132 0.777606 0.231397 0.078 Uiso 0.212(2) 1 calc R . P D 2
F7A F 0.6033(8) 0.3904(7) 0.1791(7) 0.079(5) Uani 0.187(11) 1 d D U P C 2
F9A F 0.6068(10) 0.3997(6) 0.0967(8) 0.086(5) Uani 0.187(11) 1 d D U P C 2
F8A F 0.5390(3) 0.3772(7) 0.1494(11) 0.058(5) Uani 0.187(11) 1 d D U P C 2
F3A F 0.5965(2) 0.7876(2) 0.3480(5) 0.0526(19) Uani 0.445(13) 1 d D U P A 2
F1A F 0.6465(5) 0.7731(5) 0.3075(4) 0.0421(14) Uani 0.445(13) 1 d D U P A 2
F2A F 0.6435(4) 0.7697(4) 0.3936(3) 0.0499(14) Uani 0.445(13) 1 d D U P A 2


_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 C19 1.308(5) . ?
F2 C19 1.364(5) . ?
F3 C19 1.340(5) . ?
F4 C20 1.327(3) . ?
F5 C20 1.318(3) . ?
F6 C20 1.313(3) . ?
O1 C4 1.250(3) . ?
O2 C13 1.234(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.457(3) . ?
N1 C4 1.359(3) . ?
N2 C4 1.364(3) . ?
N2 C5 1.463(3) . ?
N2 C11 1.454(3) . ?
N3 H3 0.8800 . ?
N3 C12 1.452(3) . ?
N3 C13 1.347(3) . ?
N4 H4 0.8800 . ?
N4 C13 1.379(3) . ?
N4 C14 1.390(3) . ?
C0AA H0AA 0.9500 . ?
C0AA C14 1.397(4) . ?
C0AA C18 1.381(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.524(4) . ?
C1AA H1AA 0.9500 . ?
C1AA C6 1.397(4) . ?
C1AA C10 1.385(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.511(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 H5B 0.9900 . ?
C5 H5C 0.9900 . ?
C5 C6 1.511(4) . ?
C6 C7 1.390(4) . ?
C7 H7B 0.9500 . ?
C7 C8 1.385(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(5) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.533(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(4) . ?
C16 C17 1.378(4) . ?
C16 C19 1.504(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(4) . ?
C18 C20 1.495(4) . ?
C19 F3A 1.347(5) . ?
C19 F1A 1.339(6) . ?
C19 F2A 1.309(6) . ?
C20 F4A 1.313(6) . ?
C20 F5A 1.330(6) . ?
C20 F6A 1.317(6) . ?
F7 C41 1.325(4) . ?
F8 C41 1.328(4) . ?
F9 C41 1.325(4) . ?
F10 C42 1.347(4) . ?
F11 C42 1.338(3) . ?
F12 C42 1.333(4) . ?
O3 C24 1.250(4) . ?
O4 C34 1.230(4) . ?
N5 H5 0.8800 . ?
N5 C22 1.460(5) . ?
N5 C24 1.347(5) . ?
N6 C24 1.369(4) . ?
N6 C25 1.453(5) . ?
N6 C32 1.455(4) . ?
N7 H7 0.8800 . ?
N7 C33 1.462(4) . ?
N7 C34 1.344(4) . ?
N8 H8A 0.8800 . ?
N8 H8B 0.8800 . ?
N8 C34 1.407(4) . ?
N8 C35 1.389(4) . ?
N8 C34A 1.403(13) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C22 1.530(6) . ?
C22 H22 1.0000 . ?
C22 C23 1.526(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.523(5) . ?
C26 C27 1.388(6) . ?
C26 C31 1.378(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.343(7) . ?
C29 H29 0.9500 . ?
C29 C30 1.378(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.407(6) . ?
C31 H31 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.530(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 C36 1.393(4) . ?
C35 C40 1.395(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.385(4) . ?
C37 C38 1.385(5) . ?
C37 C41 1.499(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.384(4) . ?
C39 C40 1.393(4) . ?
C39 C42 1.494(4) . ?
C40 H40 0.9500 . ?
C41 F7A 1.325(7) . ?
C41 F9A 1.316(7) . ?
C41 F8A 1.321(7) . ?
N5A H5A 0.8800 . ?
N5A C22A 1.460(18) . ?
N5A C24A 1.299(19) . ?
C22A H22A 1.0000 . ?
C22A C21A 1.532(9) . ?
C22A C23A 1.546(9) . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C34A O4A 1.217(15) . ?
C34A N7A 1.364(17) . ?
N7A H7A 0.8800 . ?
N7A C33A 1.475(9) . ?
C24A O3A 1.231(16) . ?
C24A N6A 1.419(18) . ?
N6A C25A 1.486(9) . ?
N6A C32A 1.467(9) . ?
C25A H25C 0.9900 . ?
C25A H25D 0.9900 . ?
C25A C33A 1.533(10) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C32A C26A 1.542(9) . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C26A C31A 1.3900 . ?
C26A C27A 1.3900 . ?
C31A H31A 0.9500 . ?
C31A C30A 1.3900 . ?
C30A H30A 0.9500 . ?
C30A C29A 1.3900 . ?
C29A H29A 0.9500 . ?
C29A C28A 1.3900 . ?
C28A H28A 0.9500 . ?
C28A C27A 1.3900 . ?
C27A H27A 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 N1 H1 119.7 . . ?
C4 N1 H1 119.7 . . ?
C4 N1 C2 120.6(2) . . ?
C4 N2 C5 120.2(2) . . ?
C4 N2 C11 122.0(2) . . ?
C11 N2 C5 117.3(2) . . ?
C12 N3 H3 120.2 . . ?
C13 N3 H3 120.2 . . ?
C13 N3 C12 119.6(2) . . ?
C13 N4 H4 115.9 . . ?
C13 N4 C14 128.2(2) . . ?
C14 N4 H4 115.9 . . ?
C14 C0AA H0AA 119.5 . . ?
C18 C0AA H0AA 119.5 . . ?
C18 C0AA C14 121.0(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C6 C1AA H1AA 119.8 . . ?
C10 C1AA H1AA 119.8 . . ?
C10 C1AA C6 120.4(3) . . ?
N1 C2 C1 108.0(2) . . ?
N1 C2 H2 108.7 . . ?
N1 C2 C3 111.4(2) . . ?
C1 C2 H2 108.7 . . ?
C3 C2 C1 111.2(3) . . ?
C3 C2 H2 108.7 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O1 C4 N1 121.6(2) . . ?
O1 C4 N2 121.3(2) . . ?
N1 C4 N2 117.1(2) . . ?
N2 C5 H5B 108.8 . . ?
N2 C5 H5C 108.8 . . ?
N2 C5 C6 113.7(2) . . ?
H5B C5 H5C 107.7 . . ?
C6 C5 H5B 108.8 . . ?
C6 C5 H5C 108.8 . . ?
C1AA C6 C5 120.4(2) . . ?
C7 C6 C1AA 118.7(3) . . ?
C7 C6 C5 120.8(3) . . ?
C6 C7 H7B 119.7 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7B 119.7 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 H9 120.0 . . ?
C1AA C10 C9 119.9(3) . . ?
C1AA C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
N2 C11 H11A 108.9 . . ?
N2 C11 H11B 108.9 . . ?
N2 C11 C12 113.5(2) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
N3 C12 C11 110.7(2) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
O2 C13 N3 123.2(2) . . ?
O2 C13 N4 124.2(2) . . ?
N3 C13 N4 112.6(2) . . ?
N4 C14 C0AA 117.3(2) . . ?
N4 C14 C15 124.0(2) . . ?
C15 C14 C0AA 118.8(2) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(2) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C19 117.6(2) . . ?
C17 C16 C15 122.4(2) . . ?
C17 C16 C19 120.0(2) . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.1(2) . . ?
C18 C17 H17 121.0 . . ?
C0AA C18 C17 120.7(2) . . ?
C0AA C18 C20 119.1(2) . . ?
C17 C18 C20 120.1(2) . . ?
F1 C19 F2 105.2(5) . . ?
F1 C19 F3 111.4(4) . . ?
F1 C19 C16 116.1(5) . . ?
F2 C19 C16 109.1(4) . . ?
F3 C19 F2 100.6(4) . . ?
F3 C19 C16 112.8(3) . . ?
F3A C19 C16 112.0(3) . . ?
F1A C19 C16 108.8(6) . . ?
F1A C19 F3A 103.9(5) . . ?
F2A C19 C16 115.4(6) . . ?
F2A C19 F3A 109.0(5) . . ?
F2A C19 F1A 107.0(6) . . ?
F4 C20 C18 112.8(2) . . ?
F5 C20 F4 106.3(3) . . ?
F5 C20 C18 113.0(2) . . ?
F6 C20 F4 105.3(3) . . ?
F6 C20 F5 106.3(3) . . ?
F6 C20 C18 112.7(2) . . ?
F4A C20 C18 111.6(5) . . ?
F4A C20 F5A 102.5(9) . . ?
F4A C20 F6A 107.8(10) . . ?
F5A C20 C18 111.9(4) . . ?
F6A C20 C18 115.2(6) . . ?
F6A C20 F5A 106.9(10) . . ?
C22 N5 H5 119.7 . . ?
C24 N5 H5 119.7 . . ?
C24 N5 C22 120.6(3) . . ?
C24 N6 C25 120.0(3) . . ?
C24 N6 C32 122.3(3) . . ?
C25 N6 C32 117.6(3) . . ?
C33 N7 H7 120.8 . . ?
C34 N7 H7 120.8 . . ?
C34 N7 C33 118.3(3) . . ?
C34 N8 H8A 115.8 . . ?
C35 N8 H8A 115.8 . . ?
C35 N8 H8B 117.4 . . ?
C35 N8 C34 128.4(2) . . ?
C35 N8 C34A 125.2(6) . . ?
C34A N8 H8B 117.4 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
N5 C22 C21 107.2(3) . . ?
N5 C22 H22 109.2 . . ?
N5 C22 C23 111.0(3) . . ?
C21 C22 H22 109.2 . . ?
C23 C22 C21 110.9(4) . . ?
C23 C22 H22 109.2 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 N5 122.3(3) . . ?
O3 C24 N6 120.6(3) . . ?
N5 C24 N6 117.1(3) . . ?
N6 C25 H25A 108.6 . . ?
N6 C25 H25B 108.6 . . ?
N6 C25 C26 114.5(3) . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C27 C26 C25 119.6(4) . . ?
C31 C26 C25 121.4(4) . . ?
C31 C26 C27 118.9(4) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 121.0(5) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 120.4 . . ?
C29 C28 C27 119.1(5) . . ?
C29 C28 H28 120.4 . . ?
C28 C29 H29 118.7 . . ?
C28 C29 C30 122.5(5) . . ?
C30 C29 H29 118.7 . . ?
C29 C30 H30 120.9 . . ?
C29 C30 C31 118.1(4) . . ?
C31 C30 H30 120.9 . . ?
C26 C31 C30 120.2(4) . . ?
C26 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
N6 C32 H32A 108.9 . . ?
N6 C32 H32B 108.9 . . ?
N6 C32 C33 113.5(3) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
N7 C33 C32 111.4(3) . . ?
N7 C33 H33A 109.4 . . ?
N7 C33 H33B 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
O4 C34 N7 122.7(3) . . ?
O4 C34 N8 123.5(3) . . ?
N7 C34 N8 113.7(3) . . ?
N8 C35 C36 122.4(3) . . ?
N8 C35 C40 118.6(2) . . ?
C36 C35 C40 119.0(3) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C41 118.9(3) . . ?
C38 C37 C36 121.6(3) . . ?
C38 C37 C41 119.3(3) . . ?
C37 C38 H38 120.9 . . ?
C39 C38 C37 118.2(3) . . ?
C39 C38 H38 120.9 . . ?
C38 C39 C40 121.2(3) . . ?
C38 C39 C42 121.2(3) . . ?
C40 C39 C42 117.6(3) . . ?
C35 C40 H40 120.0 . . ?
C39 C40 C35 120.0(3) . . ?
C39 C40 H40 120.0 . . ?
F7 C41 F8 105.4(3) . . ?
F7 C41 C37 113.5(3) . . ?
F8 C41 C37 112.3(3) . . ?
F9 C41 F7 105.2(4) . . ?
F9 C41 F8 106.1(3) . . ?
F9 C41 C37 113.6(3) . . ?
F7A C41 C37 103.3(9) . . ?
F9A C41 C37 112.4(8) . . ?
F9A C41 F7A 102.0(12) . . ?
F9A C41 F8A 121.5(14) . . ?
F8A C41 C37 115.0(10) . . ?
F8A C41 F7A 98.5(13) . . ?
F10 C42 C39 111.9(3) . . ?
F11 C42 F10 105.9(2) . . ?
F11 C42 C39 112.9(3) . . ?
F12 C42 F10 106.0(3) . . ?
F12 C42 F11 106.9(3) . . ?
F12 C42 C39 112.7(2) . . ?
C22A N5A H5A 117.4 . . ?
C24A N5A H5A 117.4 . . ?
C24A N5A C22A 125.1(12) . . ?
N5A C22A H22A 109.3 . . ?
N5A C22A C21A 108.5(11) . . ?
N5A C22A C23A 108.7(11) . . ?
C21A C22A H22A 109.3 . . ?
C21A C22A C23A 111.7(12) . . ?
C23A C22A H22A 109.3 . . ?
C22A C21A H21D 109.5 . . ?
C22A C21A H21E 109.5 . . ?
C22A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O4A C34A N8 128.7(11) . . ?
O4A C34A N7A 123.1(12) . . ?
N7A C34A N8 108.1(10) . . ?
C34A N7A H7A 121.0 . . ?
C34A N7A C33A 118.0(12) . . ?
C33A N7A H7A 121.0 . . ?
N5A C24A N6A 117.1(12) . . ?
O3A C24A N5A 123.3(13) . . ?
O3A C24A N6A 119.0(12) . . ?
C24A N6A C25A 123.6(11) . . ?
C24A N6A C32A 116.8(12) . . ?
C32A N6A C25A 119.5(12) . . ?
N6A C25A H25C 109.9 . . ?
N6A C25A H25D 109.9 . . ?
N6A C25A C33A 108.9(11) . . ?
H25C C25A H25D 108.3 . . ?
C33A C25A H25C 109.9 . . ?
C33A C25A H25D 109.9 . . ?
N6A C32A H32C 108.4 . . ?
N6A C32A H32D 108.4 . . ?
N6A C32A C26A 115.7(12) . . ?
H32C C32A H32D 107.4 . . ?
C26A C32A H32C 108.4 . . ?
C26A C32A H32D 108.4 . . ?
N7A C33A C25A 103.6(10) . . ?
N7A C33A H33C 111.0 . . ?
N7A C33A H33D 111.0 . . ?
C25A C33A H33C 111.0 . . ?
C25A C33A H33D 111.0 . . ?
H33C C33A H33D 109.0 . . ?
C31A C26A C32A 121.7(11) . . ?
C31A C26A C27A 120.0 . . ?
C27A C26A C32A 118.2(11) . . ?
C26A C31A H31A 120.0 . . ?
C26A C31A C30A 120.0 . . ?
C30A C31A H31A 120.0 . . ?
C31A C30A H30A 120.0 . . ?
C29A C30A C31A 120.0 . . ?
C29A C30A H30A 120.0 . . ?
C30A C29A H29A 120.0 . . ?
C28A C29A C30A 120.0 . . ?
C28A C29A H29A 120.0 . . ?
C29A C28A H28A 120.0 . . ?
C29A C28A C27A 120.0 . . ?
C27A C28A H28A 120.0 . . ?
C26A C27A H27A 120.0 . . ?
C28A C27A C26A 120.0 . . ?
C28A C27A H27A 120.0 . . ?

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
N2 C5 C6 C1AA 73.0(3) . . . . ?
N2 C5 C6 C7 -106.9(3) . . . . ?
N2 C11 C12 N3 -162.9(2) . . . . ?
N4 C14 C15 C16 -178.7(3) . . . . ?
C0AA C14 C15 C16 -0.1(4) . . . . ?
C0AA C18 C20 F4 152.7(3) . . . . ?
C0AA C18 C20 F5 32.1(4) . . . . ?
C0AA C18 C20 F6 -88.3(4) . . . . ?
C0AA C18 C20 F4A 81.2(10) . . . . ?
C0AA C18 C20 F5A -33.0(9) . . . . ?
C0AA C18 C20 F6A -155.4(9) . . . . ?
C1AA C6 C7 C8 0.8(4) . . . . ?
C2 N1 C4 O1 3.5(4) . . . . ?
C2 N1 C4 N2 -177.2(2) . . . . ?
C4 N1 C2 C1 -161.4(3) . . . . ?
C4 N1 C2 C3 76.2(3) . . . . ?
C4 N2 C5 C6 -97.3(3) . . . . ?
C4 N2 C11 C12 78.1(3) . . . . ?
C5 N2 C4 O1 -8.5(4) . . . . ?
C5 N2 C4 N1 172.2(2) . . . . ?
C5 N2 C11 C12 -93.3(3) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
C6 C1AA C10 C9 0.3(4) . . . . ?
C6 C7 C8 C9 1.1(5) . . . . ?
C7 C8 C9 C10 -2.3(5) . . . . ?
C8 C9 C10 C1AA 1.6(5) . . . . ?
C10 C1AA C6 C5 178.7(3) . . . . ?
C10 C1AA C6 C7 -1.5(4) . . . . ?
C11 N2 C4 O1 -179.6(2) . . . . ?
C11 N2 C4 N1 1.0(4) . . . . ?
C11 N2 C5 C6 74.3(3) . . . . ?
C12 N3 C13 O2 4.8(4) . . . . ?
C12 N3 C13 N4 -175.7(2) . . . . ?
C13 N3 C12 C11 73.0(3) . . . . ?
C13 N4 C14 C0AA -179.5(3) . . . . ?
C13 N4 C14 C15 -0.9(4) . . . . ?
C14 N4 C13 O2 -2.2(4) . . . . ?
C14 N4 C13 N3 178.3(2) . . . . ?
C14 C0AA C18 C17 -0.4(4) . . . . ?
C14 C0AA C18 C20 178.2(2) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C14 C15 C16 C19 -179.3(3) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C15 C16 C19 F1 70.9(6) . . . . ?
C15 C16 C19 F2 -47.8(5) . . . . ?
C15 C16 C19 F3 -158.8(5) . . . . ?
C15 C16 C19 F3A 167.9(6) . . . . ?
C15 C16 C19 F1A 53.6(7) . . . . ?
C15 C16 C19 F2A -66.6(6) . . . . ?
C16 C17 C18 C0AA -0.4(4) . . . . ?
C16 C17 C18 C20 -179.0(2) . . . . ?
C17 C16 C19 F1 -107.7(6) . . . . ?
C17 C16 C19 F2 133.6(5) . . . . ?
C17 C16 C19 F3 22.6(6) . . . . ?
C17 C16 C19 F3A -10.7(6) . . . . ?
C17 C16 C19 F1A -125.0(6) . . . . ?
C17 C16 C19 F2A 114.8(6) . . . . ?
C17 C18 C20 F4 -28.8(4) . . . . ?
C17 C18 C20 F5 -149.3(3) . . . . ?
C17 C18 C20 F6 90.2(4) . . . . ?
C17 C18 C20 F4A -100.2(10) . . . . ?
C17 C18 C20 F5A 145.6(9) . . . . ?
C17 C18 C20 F6A 23.2(10) . . . . ?
C18 C0AA C14 N4 179.3(2) . . . . ?
C18 C0AA C14 C15 0.6(4) . . . . ?
C19 C16 C17 C18 179.5(3) . . . . ?
N6 C25 C26 C27 136.9(4) . . . . ?
N6 C25 C26 C31 -44.3(5) . . . . ?
N6 C32 C33 N7 160.7(3) . . . . ?
N8 C35 C36 C37 179.1(3) . . . . ?
N8 C35 C40 C39 -178.9(2) . . . . ?
N8 C34A N7A C33A 176.5(10) . . . . ?
C22 N5 C24 O3 -3.7(5) . . . . ?
C22 N5 C24 N6 176.2(3) . . . . ?
C24 N5 C22 C21 163.3(4) . . . . ?
C24 N5 C22 C23 -75.4(4) . . . . ?
C24 N6 C25 C26 93.5(4) . . . . ?
C24 N6 C32 C33 -81.1(4) . . . . ?
C25 N6 C24 O3 4.8(5) . . . . ?
C25 N6 C24 N5 -175.2(3) . . . . ?
C25 N6 C32 C33 94.9(4) . . . . ?
C25 C26 C27 C28 179.7(4) . . . . ?
C25 C26 C31 C30 179.8(3) . . . . ?
C26 C27 C28 C29 0.8(7) . . . . ?
C27 C26 C31 C30 -1.3(6) . . . . ?
C27 C28 C29 C30 -1.9(7) . . . . ?
C28 C29 C30 C31 1.4(7) . . . . ?
C29 C30 C31 C26 0.3(6) . . . . ?
C31 C26 C27 C28 0.8(6) . . . . ?
C32 N6 C24 O3 -179.4(3) . . . . ?
C32 N6 C24 N5 0.7(5) . . . . ?
C32 N6 C25 C26 -82.5(4) . . . . ?
C33 N7 C34 O4 -9.4(5) . . . . ?
C33 N7 C34 N8 172.0(3) . . . . ?
C34 N7 C33 C32 -70.5(4) . . . . ?
C34 N8 C35 C36 -2.5(4) . . . . ?
C34 N8 C35 C40 176.5(3) . . . . ?
C35 N8 C34 O4 2.4(5) . . . . ?
C35 N8 C34 N7 -179.0(3) . . . . ?
C35 N8 C34A O4A -12.8(19) . . . . ?
C35 N8 C34A N7A 170.5(8) . . . . ?
C35 C36 C37 C38 0.2(4) . . . . ?
C35 C36 C37 C41 -176.5(3) . . . . ?
C36 C35 C40 C39 0.2(4) . . . . ?
C36 C37 C38 C39 -0.7(4) . . . . ?
C36 C37 C41 F7 -30.2(5) . . . . ?
C36 C37 C41 F8 89.2(4) . . . . ?
C36 C37 C41 F9 -150.3(5) . . . . ?
C36 C37 C41 F7A -115.5(11) . . . . ?
C36 C37 C41 F9A 135.3(15) . . . . ?
C36 C37 C41 F8A -9.3(14) . . . . ?
C37 C38 C39 C40 1.0(4) . . . . ?
C37 C38 C39 C42 -179.6(3) . . . . ?
C38 C37 C41 F7 153.1(4) . . . . ?
C38 C37 C41 F8 -87.5(4) . . . . ?
C38 C37 C41 F9 32.9(6) . . . . ?
C38 C37 C41 F7A 67.7(11) . . . . ?
C38 C37 C41 F9A -41.4(16) . . . . ?
C38 C37 C41 F8A 173.9(13) . . . . ?
C38 C39 C40 C35 -0.8(4) . . . . ?
C38 C39 C42 F10 10.4(4) . . . . ?
C38 C39 C42 F11 129.8(3) . . . . ?
C38 C39 C42 F12 -109.0(3) . . . . ?
C40 C35 C36 C37 0.1(4) . . . . ?
C40 C39 C42 F10 -170.2(2) . . . . ?
C40 C39 C42 F11 -50.8(4) . . . . ?
C40 C39 C42 F12 70.5(3) . . . . ?
C41 C37 C38 C39 175.9(3) . . . . ?
C42 C39 C40 C35 179.8(3) . . . . ?
N5A C24A N6A C25A -5(2) . . . . ?
N5A C24A N6A C32A 178.1(14) . . . . ?
C22A N5A C24A O3A 2(3) . . . . ?
C22A N5A C24A N6A 172.8(13) . . . . ?
C34A N8 C35 C36 -169.9(7) . . . . ?
C34A N8 C35 C40 9.1(8) . . . . ?
C34A N7A C33A C25A 78.9(16) . . . . ?
O4A C34A N7A C33A -1(2) . . . . ?
C24A N5A C22A C21A 77.9(18) . . . . ?
C24A N5A C22A C23A -160.4(15) . . . . ?
C24A N6A C25A C33A 84.9(19) . . . . ?
C24A N6A C32A C26A -88.2(18) . . . . ?
O3A C24A N6A C25A 166.4(14) . . . . ?
O3A C24A N6A C32A -11(2) . . . . ?
N6A C25A C33A N7A -161.9(11) . . . . ?
N6A C32A C26A C31A -138.4(12) . . . . ?
N6A C32A C26A C27A 45.8(17) . . . . ?
C25A N6A C32A C26A 94.8(18) . . . . ?
C32A N6A C25A C33A -98.3(16) . . . . ?
C32A C26A C31A C30A -175.7(14) . . . . ?
C32A C26A C27A C28A 175.9(13) . . . . ?
C26A C31A C30A C29A 0.0 . . . . ?
C31A C26A C27A C28A 0.0 . . . . ?
C31A C30A C29A C28A 0.0 . . . . ?
C30A C29A C28A C27A 0.0 . . . . ?
C29A C28A C27A C26A 0.0 . . . . ?
C27A C26A C31A C30A 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6754(10)
2 0.3246(10)

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_g49
_database_code_depnum_ccdc_archive 'CCDC 2189976'
loop_
_audit_author_name
_audit_author_address
'Natalie E Pridmore'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2022-01-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
''
''
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1(C32 H36 F6 N6 O3)'
_chemical_formula_sum            'C32 H36 F6 N6 O3'
_chemical_formula_weight         666.67
_chemical_melting_point          448
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.5061(3)
_cell_length_b                   15.7206(4)
_cell_length_c                   17.2781(4)
_cell_angle_alpha                92.4420(10)
_cell_angle_beta                 113.7000(10)
_cell_angle_gamma                112.8530(10)
_cell_volume                     3231.16(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9979
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.64
_cell_measurement_theta_min      3.65
_shelx_estimated_absorpt_T_max   0.876
_shelx_estimated_absorpt_T_min   0.720
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.3825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.5074.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.363
_exptl_crystal_size_mid          0.317
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            67927
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.684
_diffrn_reflns_theta_min         2.874
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker PHOTON III C7'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CPAD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker D8 Venture dual source kappa CPAD'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω-scan'
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\uS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                12198
_reflns_number_total             13186
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.39.0 (Bruker, 2018)'
_computing_data_collection       'Bruker SC-XRD Suite'
_computing_data_reduction        'SAINT v8.39.0 (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1053
_refine_ls_number_reflns         13186
_refine_ls_number_restraints     750
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+1.2939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0991
_refine_special_details          
;
 One of the two molecules in the asymmetric unit was disordered. Part was
 modelled in two positions with a refined occupancy ratio of 0.529:0.471(3)
 and part was modelled in three positions with a refined occupancy ratio
 of 0.3591(19):0.321(2):0.3198(18). Restraints and constraints were applied to
 maintain sensible thermal and geometric parameters in the disordered atoms. 

 Hydrogen atoms on none disordered heteroatoms were found in the difference map
 after all other atoms had been refined. All other hydrogens were placed
 geometrically and refined using a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{N10, N10A}
3. Restrained distances
 N8-C41 = N8B-C41 = N8A-C41 = N11-C53A = N11-C53B = N11-C53 = N9A-C53A = N9B-
 C53B = N9-C53
 1.36 with sigma of 0.01
 N11-C54 = N11-C54A
 1.45 with sigma of 0.01
 N8-C42 = N8B-C42B = N8A-C42A = N9A-C43A = N9B-C43B = N9-C43 = N9A-C44A = N9B-
 C44B = N9-C44 = N10A-C45A = N10-C45 = N10B-C45B = N9A-C53A = N9B-C53B = N9-C53
 1.45 with sigma of 0.005
 C55-C54 = C55A-C54A = C56A-C55A = C56-C55 = C57A-C56A = C57-C56
 1.52 with sigma of 0.01
 C43A-C42A = C43B-C42B = C43-C42 = C45A-C44A = C45B-C44B = C45-C44
 1.53 with sigma of 0.01
 O5A-C53A = O5B-C53B = O5-C53
 1.2 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
C42 \\sim C42A \\sim C42B \\sim C43 \\sim C43A \\sim C43B \\sim C44 \\sim C44A
\\sim C44B \\sim C45 \\sim C45A \\sim C45B \\sim C53 \\sim C53A \\sim C53B
\\sim C54 \\sim C54A \\sim C55 \\sim C55A \\sim C56 \\sim C56A \\sim C57 \\sim
C57A \\sim N8 \\sim N8A \\sim N8B \\sim N9 \\sim N9A \\sim N9B \\sim N10 \\sim
N10A \\sim N10B \\sim N11 \\sim O5 \\sim O5A \\sim O5B: within 2A with sigma of
0.003 and sigma for terminal atoms of 0.006 within 2A
Uanis(C53B) = Uanis(C53) = Uanis(C53A)
Uanis(N10B) = Uanis(N10) = Uanis(N10A)
5. Others
 1*[Sof(C42)+Sof(H42A)+Sof(H42B)+Sof(C43)+Sof(H43A)+Sof(H43B)+Sof(C44)+
 Sof(H44A)+Sof(H44B)+Sof(C45)+Sof(H45A)+Sof(H45B)+Sof(H46A)+Sof(H46B)+Sof(C53)+
 Sof(N8)+Sof(H8)+Sof(N9)+Sof(N10)+Sof(O5)]+1*[Sof(C42B)+Sof(H42E)+Sof(H42F)+
 Sof(C43B)+Sof(H43E)+Sof(H43F)+Sof(C44B)+Sof(H44E)+Sof(H44F)+Sof(C45B)+
 Sof(H45E)+Sof(H45F)+Sof(H46E)+Sof(H46F)+Sof(C53B)+Sof(N8B)+Sof(H8B)+Sof(N9B)+
 Sof(N10B)+Sof(O5B)]+1*[Sof(C42A)+Sof(H42C)+Sof(H42D)+Sof(C43A)+Sof(H43C)+
 Sof(H43D)+Sof(C44A)+Sof(H44C)+Sof(H44D)+Sof(C45A)+Sof(H45C)+Sof(H45D)+
 Sof(H46C)+Sof(H46D)+Sof(C53A)+Sof(N8A)+Sof(H8A)+Sof(N9A)+Sof(N10A)+Sof(O5A)]=1
 with esd of 0
 Sof(C42)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=
 Sof(H44B)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H46A)=Sof(H46B)=Sof(C53)=Sof(N8)=
 Sof(H8)=Sof(N9)=Sof(N10)=Sof(O5)=FVAR(1)
 Sof(C42B)=Sof(H42E)=Sof(H42F)=Sof(C43B)=Sof(H43E)=Sof(H43F)=Sof(C44B)=
 Sof(H44E)=Sof(H44F)=Sof(C45B)=Sof(H45E)=Sof(H45F)=Sof(H46E)=Sof(H46F)=
 Sof(C53B)=Sof(N8B)=Sof(H8B)=Sof(N9B)=Sof(N10B)=Sof(O5B)=FVAR(2)
 Sof(C42A)=Sof(H42C)=Sof(H42D)=Sof(C43A)=Sof(H43C)=Sof(H43D)=Sof(C44A)=
 Sof(H44C)=Sof(H44D)=Sof(C45A)=Sof(H45C)=Sof(H45D)=Sof(H46C)=Sof(H46D)=
 Sof(C53A)=Sof(N8A)=Sof(H8A)=Sof(N9A)=Sof(N10A)=Sof(O5A)=FVAR(3)
 Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C56A)=
 Sof(H56C)=Sof(H56D)=Sof(C57A)=Sof(H57D)=Sof(H57E)=Sof(H57F)=1-FVAR(4)
 Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=Sof(C56)=Sof(H56A)=
 Sof(H56B)=Sof(C57)=Sof(H57A)=Sof(H57B)=Sof(H57C)=FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,
 H14B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C42(H42A,H42B),
 C42A(H42C,H42D), C42B(H42E,H42F), C43(H43A,H43B), C43A(H43C,H43D), C43B(H43E,
 H43F), C44(H44A,H44B), C44A(H44C,H44D), C44B(H44E,H44F), C45(H45A,H45B),
 C45A(H45C,H45D), C45B(H45E,H45F), C46(H46A,H46B), C46(H46C,H46D), C46(H46E,
 H46F), C54(H54A,H54B), C54A(H54C,H54D), C55(H55A,H55B), C55A(H55C,H55D),
 C56(H56A,H56B), C56A(H56C,H56D)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C34(H34), C36(H36), C38(H38),
  C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C60(H60), C61(H61),
 C62(H62), C63(H63), C64(H64), N8(H8), N8A(H8A), N8B(H8B)
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C57(H57A,H57B,H57C), C57A(H57D,H57E,H57F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.23531(10) -0.15100(9) 0.33677(8) 0.0249(2) Uani 1 1 d . . . . .
C2 C 0.19832(10) -0.22823(9) 0.27063(8) 0.0261(2) Uani 1 1 d . . . . .
H2 H 0.242714 -0.227124 0.242210 0.031 Uiso 1 1 calc R U . . .
C3 C 0.09632(11) -0.30662(9) 0.24665(8) 0.0265(2) Uani 1 1 d . . . . .
C4 C 0.02935(10) -0.31115(9) 0.28681(8) 0.0275(3) Uani 1 1 d . . . . .
H4 H -0.039465 -0.365861 0.270615 0.033 Uiso 1 1 calc R U . . .
C5 C 0.06594(10) -0.23318(9) 0.35152(8) 0.0261(2) Uani 1 1 d . . . . .
C6 C 0.16691(10) -0.15357(9) 0.37626(8) 0.0249(2) Uani 1 1 d . . . . .
H6 H 0.189798 -0.100706 0.420000 0.030 Uiso 1 1 calc R U . . .
C7 C 0.06142(11) -0.38897(9) 0.17675(9) 0.0305(3) Uani 1 1 d . . . . .
C8 C -0.00580(11) -0.23689(10) 0.39562(9) 0.0305(3) Uani 1 1 d . . . . .
C9 C 0.43233(10) -0.07118(9) 0.36200(8) 0.0237(2) Uani 1 1 d . . . . .
C10 C 0.62395(10) 0.02567(9) 0.39083(8) 0.0246(2) Uani 1 1 d . . . . .
H10A H 0.641169 -0.026959 0.410643 0.030 Uiso 1 1 calc R U . . .
H10B H 0.686989 0.086089 0.431111 0.030 Uiso 1 1 calc R U . . .
C11 C 0.61316(10) 0.02529(8) 0.29868(8) 0.0233(2) Uani 1 1 d . . . . .
H11A H 0.536718 -0.021782 0.255966 0.028 Uiso 1 1 calc R U . . .
H11B H 0.623214 0.088612 0.287092 0.028 Uiso 1 1 calc R U . . .
C12 C 0.79445(10) 0.07720(8) 0.28750(8) 0.0231(2) Uani 1 1 d . . . . .
H12A H 0.858739 0.061713 0.313631 0.028 Uiso 1 1 calc R U . . .
H12B H 0.813904 0.137885 0.323767 0.028 Uiso 1 1 calc R U . . .
C13 C 0.77380(9) 0.08881(8) 0.19467(8) 0.0225(2) Uani 1 1 d . . . . .
H13A H 0.722759 0.025798 0.153673 0.027 Uiso 1 1 calc R U . . .
H13B H 0.735341 0.130070 0.178970 0.027 Uiso 1 1 calc R U . . .
C14 C 0.92365(10) 0.23037(8) 0.18526(8) 0.0243(2) Uani 1 1 d . . . . .
H14A H 0.861278 0.246631 0.153135 0.029 Uiso 1 1 calc R U . . .
H14B H 0.969353 0.241791 0.153541 0.029 Uiso 1 1 calc R U . . .
C15 C 0.99622(10) 0.29718(8) 0.27477(8) 0.0226(2) Uani 1 1 d . . . . .
C16 C 1.05685(10) 0.27194(9) 0.34723(8) 0.0257(2) Uani 1 1 d . . . . .
H16 H 1.051475 0.209582 0.342200 0.031 Uiso 1 1 calc R U . . .
C17 C 1.12566(10) 0.33761(10) 0.42743(9) 0.0292(3) Uani 1 1 d . . . . .
H17 H 1.166494 0.319744 0.476882 0.035 Uiso 1 1 calc R U . . .
C18 C 1.13444(11) 0.42900(9) 0.43495(9) 0.0305(3) Uani 1 1 d . . . . .
H18 H 1.181205 0.473761 0.489502 0.037 Uiso 1 1 calc R U . . .
C19 C 1.07489(12) 0.45475(9) 0.36276(9) 0.0329(3) Uani 1 1 d . . . . .
H19 H 1.081188 0.517403 0.367655 0.040 Uiso 1 1 calc R U . . .
C20 C 1.00589(11) 0.38909(9) 0.28311(9) 0.0284(3) Uani 1 1 d . . . . .
H20 H 0.964916 0.407118 0.233858 0.034 Uiso 1 1 calc R U . . .
C21 C 0.67620(10) -0.08947(9) 0.26284(8) 0.0232(2) Uani 1 1 d . . . . .
C22 C 0.55122(11) -0.25903(9) 0.22897(9) 0.0279(3) Uani 1 1 d . . . . .
H22A H 0.570512 -0.289312 0.278388 0.033 Uiso 1 1 calc R U . . .
H22B H 0.592964 -0.263656 0.196875 0.033 Uiso 1 1 calc R U . . .
C23 C 0.42569(11) -0.31128(9) 0.16890(9) 0.0308(3) Uani 1 1 d . . . . .
H23A H 0.406505 -0.280015 0.120213 0.037 Uiso 1 1 calc R U . . .
H23B H 0.384248 -0.307141 0.201415 0.037 Uiso 1 1 calc R U . . .
C24 C 0.38866(13) -0.41523(10) 0.13244(10) 0.0394(3) Uani 1 1 d . . . . .
H24A H 0.410124 -0.445863 0.181255 0.047 Uiso 1 1 calc R U . . .
H24B H 0.428631 -0.419204 0.098577 0.047 Uiso 1 1 calc R U . . .
C25 C 0.26261(15) -0.46914(13) 0.07429(13) 0.0576(5) Uani 1 1 d . . . . .
H25A H 0.240356 -0.437664 0.027112 0.086 Uiso 1 1 calc R U . . .
H25B H 0.222661 -0.469998 0.108681 0.086 Uiso 1 1 calc R U . . .
H25C H 0.243671 -0.534444 0.049656 0.086 Uiso 1 1 calc R U . . .
C26 C 0.92055(9) 0.07531(8) 0.16208(7) 0.0211(2) Uani 1 1 d . . . . .
C27 C 0.88752(9) -0.09056(8) 0.12169(7) 0.0203(2) Uani 1 1 d . . . . .
C28 C 0.93879(9) -0.07777(9) 0.06702(8) 0.0227(2) Uani 1 1 d . . . . .
H28 H 0.966769 -0.017736 0.053828 0.027 Uiso 1 1 calc R U . . .
C29 C 0.94880(10) -0.15308(9) 0.03196(8) 0.0257(2) Uani 1 1 d . . . . .
H29 H 0.984020 -0.143925 -0.004996 0.031 Uiso 1 1 calc R U . . .
C30 C 0.90829(11) -0.24103(9) 0.05006(9) 0.0302(3) Uani 1 1 d . . . . .
H30 H 0.915359 -0.292183 0.025817 0.036 Uiso 1 1 calc R U . . .
C31 C 0.85714(12) -0.25349(9) 0.10416(9) 0.0322(3) Uani 1 1 d . . . . .
H31 H 0.828682 -0.313838 0.116693 0.039 Uiso 1 1 calc R U . . .
C32 C 0.84692(10) -0.17913(9) 0.14024(8) 0.0265(2) Uani 1 1 d . . . . .
H32 H 0.812252 -0.188584 0.177585 0.032 Uiso 1 1 calc R U . . .
F1 F 0.07491(9) -0.36198(6) 0.10851(5) 0.0443(2) Uani 1 1 d . . . . .
F2 F -0.04585(7) -0.45200(6) 0.14725(6) 0.0475(2) Uani 1 1 d . . . . .
F3 F 0.12191(8) -0.43742(6) 0.20585(6) 0.03973(19) Uani 1 1 d . . . . .
F4 F -0.05208(7) -0.32346(6) 0.40926(6) 0.03845(19) Uani 1 1 d . . . . .
F5 F -0.09119(7) -0.21749(7) 0.34838(6) 0.0406(2) Uani 1 1 d . . . . .
F6 F 0.05241(7) -0.17522(6) 0.47314(5) 0.0394(2) Uani 1 1 d . . . . .
N1 N 0.33822(9) -0.07096(8) 0.36538(7) 0.0274(2) Uani 1 1 d . . . . .
H1 H 0.3480(14) -0.0196(13) 0.3932(11) 0.033(4) Uiso 1 1 d . . . . .
N2 N 0.52162(9) 0.01512(8) 0.39355(7) 0.0271(2) Uani 1 1 d . . . . .
H2A H 0.5140(14) 0.0619(13) 0.4109(11) 0.035(4) Uiso 1 1 d . . . . .
N3 N 0.69545(9) 0.00227(7) 0.28697(7) 0.0249(2) Uani 1 1 d . . . . .
N4 N 0.87590(8) 0.12938(7) 0.18372(7) 0.0223(2) Uani 1 1 d . . . . .
N5 N 0.58475(9) -0.15942(7) 0.26188(7) 0.0257(2) Uani 1 1 d . . . . .
H5 H 0.5446(14) -0.1480(12) 0.2827(11) 0.033(4) Uiso 1 1 d . . . . .
N6 N 0.86773(8) -0.01982(7) 0.15598(6) 0.02066(19) Uani 1 1 d . . . . .
H6A H 0.8257(13) -0.0401(11) 0.1805(10) 0.023(4) Uiso 1 1 d . . . . .
O1 O 0.43373(7) -0.14313(6) 0.33305(6) 0.02500(18) Uani 1 1 d . . . . .
O2 O 0.74162(7) -0.10623(6) 0.24232(6) 0.02701(18) Uani 1 1 d . . . . .
O3 O 1.00353(7) 0.11172(6) 0.14831(6) 0.02611(18) Uani 1 1 d . . . . .
C33 C 0.72355(9) 0.89770(9) 0.88173(8) 0.0235(2) Uani 1 1 d . . . . .
C34 C 0.65363(10) 0.84477(9) 0.91654(8) 0.0253(2) Uani 1 1 d . . . . .
H34 H 0.636077 0.779560 0.914078 0.030 Uiso 1 1 calc R U . . .
C35 C 0.61020(10) 0.88797(9) 0.95455(8) 0.0260(2) Uani 1 1 d . . . . .
C36 C 0.63636(10) 0.98363(9) 0.96116(8) 0.0255(2) Uani 1 1 d . . . . .
H36 H 0.605274 1.012310 0.986702 0.031 Uiso 1 1 calc R U . . .
C37 C 0.70915(10) 1.03621(9) 0.92944(8) 0.0240(2) Uani 1 1 d . . . . .
C38 C 0.75190(10) 0.99397(9) 0.88902(8) 0.0241(2) Uani 1 1 d . . . . .
H38 H 0.800271 1.030839 0.866503 0.029 Uiso 1 1 calc R U . . .
C39 C 0.53017(11) 0.82909(10) 0.98712(9) 0.0313(3) Uani 1 1 d . . . . .
C40 C 0.73838(11) 1.13947(9) 0.93479(8) 0.0274(3) Uani 1 1 d . . . . .
C41 C 0.71687(11) 0.76239(10) 0.80041(10) 0.0345(3) Uani 1 1 d D . . . .
C42 C 0.7061(3) 0.6493(2) 0.6901(2) 0.0269(6) Uani 0.3591(19) 1 d D U P A 1
H42A H 0.749158 0.647701 0.658241 0.032 Uiso 0.3591(19) 1 calc R U P A 1
H42B H 0.633057 0.644874 0.647607 0.032 Uiso 0.3591(19) 1 calc R U P A 1
C42A C 0.7319(4) 0.6268(4) 0.7373(3) 0.0235(7) Uani 0.321(2) 1 d D U P A 2
H42C H 0.698063 0.586079 0.770041 0.028 Uiso 0.321(2) 1 calc R U P A 2
H42D H 0.792461 0.612243 0.737495 0.028 Uiso 0.321(2) 1 calc R U P A 2
C42B C 0.7480(4) 0.6323(4) 0.7633(3) 0.0251(7) Uani 0.3198(18) 1 d D U P A 3
H42E H 0.712255 0.597702 0.797869 0.030 Uiso 0.3198(18) 1 calc R U P A 3
H42F H 0.812139 0.618534 0.772266 0.030 Uiso 0.3198(18) 1 calc R U P A 3
C43 C 0.6858(3) 0.5643(2) 0.7315(2) 0.0256(6) Uani 0.3591(19) 1 d D U P A 1
H43A H 0.754824 0.555135 0.756525 0.031 Uiso 0.3591(19) 1 calc R U P A 1
H43B H 0.668641 0.577207 0.779505 0.031 Uiso 0.3591(19) 1 calc R U P A 1
C43A C 0.6423(4) 0.6036(3) 0.6436(3) 0.0248(7) Uani 0.321(2) 1 d D U P A 2
H43C H 0.593524 0.635529 0.636623 0.030 Uiso 0.321(2) 1 calc R U P A 2
H43D H 0.673686 0.615673 0.601628 0.030 Uiso 0.321(2) 1 calc R U P A 2
C43B C 0.6627(4) 0.5964(3) 0.6667(3) 0.0266(7) Uani 0.3198(18) 1 d D U P A 3
H43E H 0.633237 0.644208 0.656959 0.032 Uiso 0.3198(18) 1 calc R U P A 3
H43F H 0.711447 0.609629 0.637483 0.032 Uiso 0.3198(18) 1 calc R U P A 3
C44 C 0.6142(4) 0.4013(3) 0.6397(3) 0.0231(7) Uani 0.3591(19) 1 d D U P A 1
H44A H 0.570232 0.341803 0.651554 0.028 Uiso 0.3591(19) 1 calc R U P A 1
H44B H 0.694779 0.417476 0.673492 0.028 Uiso 0.3591(19) 1 calc R U P A 1
C44A C 0.6211(4) 0.4271(3) 0.6248(3) 0.0254(7) Uani 0.321(2) 1 d D U P A 2
H44C H 0.595916 0.374861 0.652635 0.031 Uiso 0.321(2) 1 calc R U P A 2
H44D H 0.704145 0.456487 0.652110 0.031 Uiso 0.321(2) 1 calc R U P A 2
C44B C 0.5730(3) 0.4442(2) 0.5500(2) 0.0239(6) Uani 0.3198(18) 1 d D U P A 3
H44E H 0.631848 0.482683 0.533802 0.029 Uiso 0.3198(18) 1 calc R U P A 3
H44F H 0.501169 0.411839 0.496089 0.029 Uiso 0.3198(18) 1 calc R U P A 3
C45 C 0.5823(7) 0.3852(3) 0.5422(4) 0.0244(8) Uani 0.3591(19) 1 d D U P A 1
H45A H 0.513658 0.393667 0.510360 0.029 Uiso 0.3591(19) 1 calc R U P A 1
H45B H 0.643623 0.432978 0.533273 0.029 Uiso 0.3591(19) 1 calc R U P A 1
C45A C 0.5744(8) 0.3857(4) 0.5277(4) 0.0238(8) Uani 0.321(2) 1 d D U P A 2
H45C H 0.500006 0.385110 0.496023 0.029 Uiso 0.321(2) 1 calc R U P A 2
H45D H 0.624871 0.428052 0.506087 0.029 Uiso 0.321(2) 1 calc R U P A 2
C45B C 0.6033(3) 0.3696(3) 0.5935(3) 0.0232(6) Uani 0.3198(18) 1 d D U P A 3
H45E H 0.684821 0.399449 0.633364 0.028 Uiso 0.3198(18) 1 calc R U P A 3
H45F H 0.563037 0.348740 0.628943 0.028 Uiso 0.3198(18) 1 calc R U P A 3
C46 C 0.66226(10) 0.27457(9) 0.52080(9) 0.0288(3) Uani 1 1 d . . . . .
H46A H 0.649120 0.210055 0.530187 0.035 Uiso 0.3591(19) 1 calc R U P A 1
H46B H 0.728728 0.321140 0.573279 0.035 Uiso 0.3591(19) 1 calc R U P A 1
H46C H 0.649120 0.210055 0.530187 0.035 Uiso 0.321(2) 1 calc R U P A 2
H46D H 0.728728 0.321140 0.573279 0.035 Uiso 0.321(2) 1 calc R U P A 2
H46E H 0.651696 0.209716 0.527585 0.035 Uiso 0.3198(18) 1 calc R U P A 3
H46F H 0.733474 0.318692 0.571521 0.035 Uiso 0.3198(18) 1 calc R U P A 3
C47 C 0.68463(10) 0.28564(8) 0.44273(8) 0.0241(2) Uani 1 1 d . . . . .
C48 C 0.79448(10) 0.31613(9) 0.45458(9) 0.0275(3) Uani 1 1 d . . . . .
H48 H 0.853978 0.333383 0.511672 0.033 Uiso 1 1 calc R U . . .
C49 C 0.81802(11) 0.32161(10) 0.38410(9) 0.0306(3) Uani 1 1 d . . . . .
H49 H 0.893088 0.341738 0.393069 0.037 Uiso 1 1 calc R U . . .
C50 C 0.73188(12) 0.29769(9) 0.30056(9) 0.0305(3) Uani 1 1 d . . . . .
H50 H 0.747685 0.301628 0.252184 0.037 Uiso 1 1 calc R U . . .
C51 C 0.62241(11) 0.26796(9) 0.28819(9) 0.0314(3) Uani 1 1 d . . . . .
H51 H 0.563158 0.251643 0.231135 0.038 Uiso 1 1 calc R U . . .
C52 C 0.59912(10) 0.26194(9) 0.35883(9) 0.0285(3) Uani 1 1 d . . . . .
H52 H 0.523912 0.241409 0.349650 0.034 Uiso 1 1 calc R U . . .
C53 C 0.4777(4) 0.4535(4) 0.6460(5) 0.0253(4) Uani 0.3591(19) 1 d D U P A 1
C53A C 0.4675(3) 0.4683(4) 0.6177(3) 0.0253(4) Uani 0.321(2) 1 d D U P A 2
C53B C 0.4849(5) 0.4626(5) 0.6420(5) 0.0253(4) Uani 0.3198(18) 1 d D U P A 3
C54 C 0.3481(5) 0.4943(8) 0.6717(4) 0.0295(8) Uani 0.529(3) 1 d D U P A 1
H54A H 0.292263 0.441609 0.619755 0.035 Uiso 0.529(3) 1 calc R U P A 1
H54B H 0.328938 0.548285 0.663266 0.035 Uiso 0.529(3) 1 calc R U P A 1
C54A C 0.3522(6) 0.4921(9) 0.6819(4) 0.0311(9) Uani 0.471(3) 1 d D U P A 2
H54C H 0.304404 0.423179 0.656133 0.037 Uiso 0.471(3) 1 calc R U P A 2
H54D H 0.309614 0.526845 0.651563 0.037 Uiso 0.471(3) 1 calc R U P A 2
C55 C 0.3338(2) 0.4626(2) 0.74980(18) 0.0337(5) Uani 0.529(3) 1 d D U P A 1
H55A H 0.348405 0.406241 0.757109 0.040 Uiso 0.529(3) 1 calc R U P A 1
H55B H 0.255003 0.443349 0.738134 0.040 Uiso 0.529(3) 1 calc R U P A 1
C55A C 0.3869(3) 0.5146(2) 0.7795(2) 0.0328(6) Uani 0.471(3) 1 d D U P A 2
H55C H 0.432048 0.481445 0.809147 0.039 Uiso 0.471(3) 1 calc R U P A 2
H55D H 0.434362 0.583710 0.804137 0.039 Uiso 0.471(3) 1 calc R U P A 2
C56 C 0.4114(2) 0.53915(19) 0.8343(2) 0.0358(6) Uani 0.529(3) 1 d D U P A 1
H56A H 0.399053 0.596537 0.826630 0.043 Uiso 0.529(3) 1 calc R U P A 1
H56B H 0.490435 0.556589 0.847636 0.043 Uiso 0.529(3) 1 calc R U P A 1
C56A C 0.2854(3) 0.4840(2) 0.7965(2) 0.0370(6) Uani 0.471(3) 1 d D U P A 2
H56C H 0.241699 0.414009 0.776622 0.044 Uiso 0.471(3) 1 calc R U P A 2
H56D H 0.236630 0.512350 0.762305 0.044 Uiso 0.471(3) 1 calc R U P A 2
C57 C 0.3915(4) 0.5062(3) 0.9107(2) 0.0565(9) Uani 0.529(3) 1 d D U P A 1
H57A H 0.316361 0.496421 0.900992 0.085 Uiso 0.529(3) 1 calc R U P A 1
H57B H 0.447979 0.554613 0.964621 0.085 Uiso 0.529(3) 1 calc R U P A 1
H57C H 0.397381 0.446397 0.915405 0.085 Uiso 0.529(3) 1 calc R U P A 1
C57A C 0.3183(4) 0.5137(3) 0.8919(3) 0.0542(10) Uani 0.471(3) 1 d D U P A 2
H57D H 0.250674 0.499397 0.899275 0.081 Uiso 0.471(3) 1 calc R U P A 2
H57E H 0.367735 0.582113 0.913260 0.081 Uiso 0.471(3) 1 calc R U P A 2
H57F H 0.357831 0.478981 0.925009 0.081 Uiso 0.471(3) 1 calc R U P A 2
C58 C 0.46551(10) 0.21110(9) 0.48550(8) 0.0254(2) Uani 1 1 d . . . . .
C59 C 0.27007(10) 0.15485(8) 0.45597(8) 0.0229(2) Uani 1 1 d . . . . .
C60 C 0.21759(11) 0.09649(9) 0.37303(8) 0.0284(3) Uani 1 1 d . . . . .
H60 H 0.257822 0.102501 0.340080 0.034 Uiso 1 1 calc R U . . .
C61 C 0.10633(11) 0.02963(10) 0.33894(9) 0.0340(3) Uani 1 1 d . . . . .
H61 H 0.070999 -0.011066 0.282921 0.041 Uiso 1 1 calc R U . . .
C62 C 0.04610(11) 0.02147(9) 0.38557(10) 0.0352(3) Uani 1 1 d . . . . .
H62 H -0.029992 -0.024742 0.361938 0.042 Uiso 1 1 calc R U . . .
C63 C 0.09791(11) 0.08141(9) 0.46711(10) 0.0327(3) Uani 1 1 d . . . . .
H63 H 0.056334 0.077141 0.498700 0.039 Uiso 1 1 calc R U . . .
C64 C 0.20982(10) 0.14755(9) 0.50306(8) 0.0258(2) Uani 1 1 d . . . . .
H64 H 0.245099 0.187574 0.559392 0.031 Uiso 1 1 calc R U . . .
F7 F 0.55108(9) 0.75848(7) 1.01641(8) 0.0543(3) Uani 1 1 d . . . . .
F8 F 0.42380(7) 0.78904(8) 0.92436(6) 0.0514(3) Uani 1 1 d . . . . .
F9 F 0.53117(7) 0.88032(6) 1.05160(6) 0.0416(2) Uani 1 1 d . . . . .
F10 F 0.71202(7) 1.17558(6) 0.98996(5) 0.03689(18) Uani 1 1 d . . . . .
F11 F 0.68323(8) 1.15448(6) 0.85757(5) 0.0415(2) Uani 1 1 d . . . . .
F12 F 0.84752(7) 1.19275(6) 0.96111(7) 0.0444(2) Uani 1 1 d . . . . .
N7 N 0.76866(9) 0.85669(7) 0.84180(7) 0.0253(2) Uani 1 1 d . . . . .
H7 H 0.8328(15) 0.8909(12) 0.8457(11) 0.034(4) Uiso 1 1 d . . . . .
N8 N 0.7679(4) 0.7390(3) 0.7552(3) 0.0243(7) Uani 0.3591(19) 1 d D U P A 1
H8 H 0.836758 0.777947 0.765842 0.029 Uiso 0.3591(19) 1 calc R U P A 1
N8A N 0.7800(6) 0.7263(5) 0.7810(5) 0.0238(9) Uani 0.321(2) 1 d D U P A 2
H8A H 0.850615 0.763995 0.795148 0.029 Uiso 0.321(2) 1 calc R U P A 2
N8B N 0.7893(6) 0.7333(5) 0.7942(5) 0.0250(9) Uani 0.3198(18) 1 d D U P A 3
H8B H 0.859027 0.773644 0.808367 0.030 Uiso 0.3198(18) 1 calc R U P A 3
N9 N 0.5927(3) 0.4775(2) 0.6680(2) 0.0234(5) Uani 0.3591(19) 1 d D U P A 1
N9A N 0.5852(3) 0.4984(2) 0.6412(3) 0.0253(7) Uani 0.321(2) 1 d D U P A 2
N9B N 0.5622(3) 0.5067(2) 0.6072(3) 0.0258(6) Uani 0.3198(18) 1 d D U P A 3
N10 N 0.5624(2) 0.28988(15) 0.50740(11) 0.0227(4) Uani 0.3591(19) 1 d D U P A 1
N10A N 0.5624(2) 0.28988(15) 0.50740(11) 0.0227(4) Uani 0.321(2) 1 d D U P A 2
N10B N 0.5761(5) 0.2865(4) 0.5324(3) 0.0227(4) Uani 0.3198(18) 1 d D U P A 3
N11 N 0.45635(9) 0.52268(8) 0.67427(8) 0.0290(2) Uani 1 1 d D U . . .
H11 H 0.5115(15) 0.5782(13) 0.7062(11) 0.035(4) Uiso 1 1 d . . . . .
N12 N 0.38223(9) 0.22559(7) 0.49259(7) 0.0262(2) Uani 1 1 d . . . . .
H12 H 0.3978(13) 0.2770(12) 0.5274(11) 0.030(4) Uiso 1 1 d . . . . .
O4 O 0.61947(8) 0.70976(7) 0.78479(8) 0.0440(3) Uani 1 1 d . . . . .
O5 O 0.4041(12) 0.3726(8) 0.6045(13) 0.0231(14) Uani 0.3591(19) 1 d D U P A 1
O5A O 0.3943(5) 0.3858(4) 0.5782(3) 0.0237(10) Uani 0.321(2) 1 d D U P A 2
O5B O 0.4162(13) 0.3793(9) 0.6050(15) 0.0235(16) Uani 0.3198(18) 1 d D U P A 3
O6 O 0.45072(7) 0.13259(6) 0.45261(6) 0.02714(19) 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 1.3967(17) . ?
C1 C6 1.4026(17) . ?
C1 N1 1.3967(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3881(17) . ?
C3 C4 1.3866(18) . ?
C3 C7 1.5023(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3910(18) . ?
C5 C6 1.3862(17) . ?
C5 C8 1.5038(17) . ?
C6 H6 0.9500 . ?
C7 F1 1.3312(16) . ?
C7 F2 1.3359(16) . ?
C7 F3 1.3416(17) . ?
C8 F4 1.3429(16) . ?
C8 F5 1.3399(16) . ?
C8 F6 1.3383(16) . ?
C9 N1 1.3910(16) . ?
C9 N2 1.3491(16) . ?
C9 O1 1.2279(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5355(17) . ?
C10 N2 1.4486(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N3 1.4561(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5417(17) . ?
C12 N3 1.4576(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 N4 1.4622(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5156(16) . ?
C14 N4 1.4590(15) . ?
C15 C16 1.3880(18) . ?
C15 C20 1.3917(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3958(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.3879(19) . ?
C18 H18 0.9500 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3893(19) . ?
C20 H20 0.9500 . ?
C21 N3 1.3690(16) . ?
C21 N5 1.3479(16) . ?
C21 O2 1.2459(15) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5211(18) . ?
C22 N5 1.4568(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5212(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N4 1.3701(15) . ?
C26 N6 1.3660(15) . ?
C26 O3 1.2408(14) . ?
C27 C28 1.3965(16) . ?
C27 C32 1.3932(17) . ?
C27 N6 1.4138(15) . ?
C28 H28 0.9500 . ?
C28 C29 1.3904(17) . ?
C29 H29 0.9500 . ?
C29 C30 1.3813(19) . ?
C30 H30 0.9500 . ?
C30 C31 1.3867(19) . ?
C31 H31 0.9500 . ?
C31 C32 1.3871(18) . ?
C32 H32 0.9500 . ?
N1 H1 0.852(18) . ?
N2 H2A 0.845(19) . ?
N5 H5 0.864(18) . ?
N6 H6A 0.850(16) . ?
C33 C34 1.4001(18) . ?
C33 C38 1.3908(18) . ?
C33 N7 1.4044(16) . ?
C34 H34 0.9500 . ?
C34 C35 1.3842(18) . ?
C35 C36 1.3877(19) . ?
C35 C39 1.5022(18) . ?
C36 H36 0.9500 . ?
C36 C37 1.3871(18) . ?
C37 C38 1.3935(17) . ?
C37 C40 1.4982(18) . ?
C38 H38 0.9500 . ?
C39 F7 1.3290(18) . ?
C39 F8 1.3399(16) . ?
C39 F9 1.3383(16) . ?
C40 F10 1.3388(15) . ?
C40 F11 1.3383(15) . ?
C40 F12 1.3317(15) . ?
C41 N7 1.3735(17) . ?
C41 N8 1.395(4) . ?
C41 N8A 1.382(7) . ?
C41 N8B 1.336(7) . ?
C41 O4 1.2329(16) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C42 C43 1.527(5) . ?
C42 N8 1.459(4) . ?
C42A H42C 0.9900 . ?
C42A H42D 0.9900 . ?
C42A C43A 1.527(6) . ?
C42A N8A 1.459(4) . ?
C42B H42E 0.9900 . ?
C42B H42F 0.9900 . ?
C42B C43B 1.533(5) . ?
C42B N8B 1.447(4) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 N9 1.463(3) . ?
C43A H43C 0.9900 . ?
C43A H43D 0.9900 . ?
C43A N9A 1.524(4) . ?
C43B H43E 0.9900 . ?
C43B H43F 0.9900 . ?
C43B N9B 1.499(4) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C44 C45 1.538(6) . ?
C44 N9 1.460(4) . ?
C44A H44C 0.9900 . ?
C44A H44D 0.9900 . ?
C44A C45A 1.533(6) . ?
C44A N9A 1.467(4) . ?
C44B H44E 0.9900 . ?
C44B H44F 0.9900 . ?
C44B C45B 1.530(5) . ?
C44B N9B 1.457(4) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 N10 1.462(4) . ?
C45A H45C 0.9900 . ?
C45A H45D 0.9900 . ?
C45A N10A 1.458(4) . ?
C45B H45E 0.9900 . ?
C45B H45F 0.9900 . ?
C45B N10B 1.458(4) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C46 H46C 0.9900 . ?
C46 H46D 0.9900 . ?
C46 H46E 0.9900 . ?
C46 H46F 0.9900 . ?
C46 C47 1.5110(18) . ?
C46 N10 1.489(3) . ?
C46 N10A 1.489(3) . ?
C46 N10B 1.421(6) . ?
C47 C48 1.3953(17) . ?
C47 C52 1.3886(18) . ?
C48 H48 0.9500 . ?
C48 C49 1.3884(19) . ?
C49 H49 0.9500 . ?
C49 C50 1.387(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.3885(19) . ?
C51 H51 0.9500 . ?
C51 C52 1.389(2) . ?
C52 H52 0.9500 . ?
C53 N9 1.436(4) . ?
C53 N11 1.361(6) . ?
C53 O5 1.235(7) . ?
C53A N9A 1.451(4) . ?
C53A N11 1.369(5) . ?
C53A O5A 1.244(6) . ?
C53B N9B 1.440(4) . ?
C53B N11 1.348(6) . ?
C53B O5B 1.233(8) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.521(6) . ?
C54 N11 1.437(6) . ?
C54A H54C 0.9900 . ?
C54A H54D 0.9900 . ?
C54A C55A 1.534(7) . ?
C54A N11 1.461(7) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C55 C56 1.524(4) . ?
C55A H55C 0.9900 . ?
C55A H55D 0.9900 . ?
C55A C56A 1.514(4) . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C56 C57 1.532(4) . ?
C56A H56C 0.9900 . ?
C56A H56D 0.9900 . ?
C56A C57A 1.515(4) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C57A H57D 0.9800 . ?
C57A H57E 0.9800 . ?
C57A H57F 0.9800 . ?
C58 N10 1.354(3) . ?
C58 N10A 1.354(3) . ?
C58 N10B 1.425(6) . ?
C58 N12 1.3625(15) . ?
C58 O6 1.2365(15) . ?
C59 C60 1.3940(17) . ?
C59 C64 1.3932(17) . ?
C59 N12 1.4111(15) . ?
C60 H60 0.9500 . ?
C60 C61 1.3864(19) . ?
C61 H61 0.9500 . ?
C61 C62 1.384(2) . ?
C62 H62 0.9500 . ?
C62 C63 1.387(2) . ?
C63 H63 0.9500 . ?
C63 C64 1.3876(18) . ?
C64 H64 0.9500 . ?
N7 H7 0.847(18) . ?
N8 H8 0.8800 . ?
N8A H8A 0.8800 . ?
N8B H8B 0.8800 . ?
N11 H11 0.877(19) . ?
N12 H12 0.880(18) . ?

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 C6 119.00(11) . . ?
C2 C1 N1 122.51(11) . . ?
N1 C1 C6 118.49(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.64(11) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C7 117.71(11) . . ?
C4 C3 C2 121.92(12) . . ?
C4 C3 C7 120.34(11) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.00(11) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 C8 118.67(11) . . ?
C6 C5 C4 121.34(11) . . ?
C6 C5 C8 119.99(12) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.06(11) . . ?
C5 C6 H6 120.0 . . ?
F1 C7 C3 112.63(11) . . ?
F1 C7 F2 107.35(11) . . ?
F1 C7 F3 106.33(11) . . ?
F2 C7 C3 112.59(11) . . ?
F2 C7 F3 105.88(11) . . ?
F3 C7 C3 111.62(11) . . ?
F4 C8 C5 111.54(11) . . ?
F5 C8 C5 112.49(11) . . ?
F5 C8 F4 106.28(10) . . ?
F6 C8 C5 112.48(10) . . ?
F6 C8 F4 106.89(11) . . ?
F6 C8 F5 106.75(11) . . ?
N2 C9 N1 113.52(11) . . ?
O1 C9 N1 123.10(11) . . ?
O1 C9 N2 123.38(11) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C11 111.44(10) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N3 C11 C10 112.20(10) . . ?
N3 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
N3 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
N3 C12 C13 111.20(10) . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N4 C13 C12 114.16(9) . . ?
N4 C13 H13A 108.7 . . ?
N4 C13 H13B 108.7 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 H14A 108.4 . . ?
C15 C14 H14B 108.4 . . ?
N4 C14 H14A 108.4 . . ?
N4 C14 H14B 108.4 . . ?
N4 C14 C15 115.69(10) . . ?
C16 C15 C14 122.89(11) . . ?
C16 C15 C20 119.04(11) . . ?
C20 C15 C14 118.00(11) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.40(12) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.00(12) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.81(12) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 120.09(12) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.64(12) . . ?
C19 C20 H20 119.7 . . ?
N5 C21 N3 117.65(10) . . ?
O2 C21 N3 120.22(11) . . ?
O2 C21 N5 122.13(11) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
N5 C22 H22A 109.5 . . ?
N5 C22 H22B 109.5 . . ?
N5 C22 C23 110.92(10) . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C22 C23 C24 112.03(11) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C23 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C23 C24 C25 112.60(13) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N6 C26 N4 116.06(10) . . ?
O3 C26 N4 121.12(11) . . ?
O3 C26 N6 122.82(11) . . ?
C28 C27 N6 123.67(11) . . ?
C32 C27 C28 119.25(11) . . ?
C32 C27 N6 116.97(10) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.85(11) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 120.99(11) . . ?
C30 C29 H29 119.5 . . ?
C29 C30 H30 120.5 . . ?
C29 C30 C31 118.97(12) . . ?
C31 C30 H30 120.5 . . ?
C30 C31 H31 119.5 . . ?
C30 C31 C32 120.96(12) . . ?
C32 C31 H31 119.5 . . ?
C27 C32 H32 120.0 . . ?
C31 C32 C27 119.98(12) . . ?
C31 C32 H32 120.0 . . ?
C1 N1 H1 118.5(11) . . ?
C9 N1 C1 124.72(11) . . ?
C9 N1 H1 116.2(11) . . ?
C9 N2 C10 119.24(10) . . ?
C9 N2 H2A 118.3(12) . . ?
C10 N2 H2A 122.3(12) . . ?
C11 N3 C12 120.10(10) . . ?
C21 N3 C11 122.15(10) . . ?
C21 N3 C12 117.08(10) . . ?
C14 N4 C13 117.88(10) . . ?
C26 N4 C13 123.02(10) . . ?
C26 N4 C14 118.64(10) . . ?
C21 N5 C22 121.57(10) . . ?
C21 N5 H5 122.1(11) . . ?
C22 N5 H5 116.3(11) . . ?
C26 N6 C27 125.75(10) . . ?
C26 N6 H6A 120.0(10) . . ?
C27 N6 H6A 113.7(10) . . ?
C34 C33 N7 121.66(11) . . ?
C38 C33 C34 119.33(11) . . ?
C38 C33 N7 118.98(11) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 C33 119.65(12) . . ?
C35 C34 H34 120.2 . . ?
C34 C35 C36 121.66(12) . . ?
C34 C35 C39 119.09(12) . . ?
C36 C35 C39 119.23(12) . . ?
C35 C36 H36 120.9 . . ?
C37 C36 C35 118.18(11) . . ?
C37 C36 H36 120.9 . . ?
C36 C37 C38 121.29(12) . . ?
C36 C37 C40 119.59(11) . . ?
C38 C37 C40 119.06(11) . . ?
C33 C38 C37 119.82(11) . . ?
C33 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
F7 C39 C35 113.08(12) . . ?
F7 C39 F8 106.33(12) . . ?
F7 C39 F9 106.94(11) . . ?
F8 C39 C35 111.59(11) . . ?
F9 C39 C35 112.65(11) . . ?
F9 C39 F8 105.76(11) . . ?
F10 C40 C37 112.84(11) . . ?
F11 C40 C37 111.49(10) . . ?
F11 C40 F10 106.08(10) . . ?
F12 C40 C37 112.57(10) . . ?
F12 C40 F10 106.38(11) . . ?
F12 C40 F11 107.04(11) . . ?
N7 C41 N8 114.14(19) . . ?
N7 C41 N8A 117.6(3) . . ?
N8B C41 N7 111.9(3) . . ?
O4 C41 N7 121.96(12) . . ?
O4 C41 N8 121.15(19) . . ?
O4 C41 N8A 120.4(3) . . ?
O4 C41 N8B 125.1(3) . . ?
H42A C42 H42B 108.0 . . ?
C43 C42 H42A 109.3 . . ?
C43 C42 H42B 109.3 . . ?
N8 C42 H42A 109.3 . . ?
N8 C42 H42B 109.3 . . ?
N8 C42 C43 111.6(3) . . ?
H42C C42A H42D 107.9 . . ?
C43A C42A H42C 109.2 . . ?
C43A C42A H42D 109.2 . . ?
N8A C42A H42C 109.2 . . ?
N8A C42A H42D 109.2 . . ?
N8A C42A C43A 112.3(5) . . ?
H42E C42B H42F 107.9 . . ?
C43B C42B H42E 109.1 . . ?
C43B C42B H42F 109.1 . . ?
N8B C42B H42E 109.1 . . ?
N8B C42B H42F 109.1 . . ?
N8B C42B C43B 112.4(5) . . ?
C42 C43 H43A 109.3 . . ?
C42 C43 H43B 109.3 . . ?
H43A C43 H43B 108.0 . . ?
N9 C43 C42 111.4(3) . . ?
N9 C43 H43A 109.3 . . ?
N9 C43 H43B 109.3 . . ?
C42A C43A H43C 113.1 . . ?
C42A C43A H43D 113.1 . . ?
H43C C43A H43D 110.5 . . ?
N9A C43A C42A 93.0(4) . . ?
N9A C43A H43C 113.1 . . ?
N9A C43A H43D 113.1 . . ?
C42B C43B H43E 102.6 . . ?
C42B C43B H43F 102.6 . . ?
H43E C43B H43F 105.0 . . ?
N9B C43B C42B 138.0(5) . . ?
N9B C43B H43E 102.6 . . ?
N9B C43B H43F 102.6 . . ?
H44A C44 H44B 108.0 . . ?
C45 C44 H44A 109.3 . . ?
C45 C44 H44B 109.3 . . ?
N9 C44 H44A 109.3 . . ?
N9 C44 H44B 109.3 . . ?
N9 C44 C45 111.6(3) . . ?
H44C C44A H44D 107.8 . . ?
C45A C44A H44C 109.0 . . ?
C45A C44A H44D 109.0 . . ?
N9A C44A H44C 109.0 . . ?
N9A C44A H44D 109.0 . . ?
N9A C44A C45A 112.9(4) . . ?
H44E C44B H44F 107.9 . . ?
C45B C44B H44E 109.3 . . ?
C45B C44B H44F 109.3 . . ?
N9B C44B H44E 109.3 . . ?
N9B C44B H44F 109.3 . . ?
N9B C44B C45B 111.8(3) . . ?
C44 C45 H45A 109.4 . . ?
C44 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
N10 C45 C44 111.0(4) . . ?
N10 C45 H45A 109.4 . . ?
N10 C45 H45B 109.4 . . ?
C44A C45A H45C 108.7 . . ?
C44A C45A H45D 108.7 . . ?
H45C C45A H45D 107.6 . . ?
N10A C45A C44A 114.2(4) . . ?
N10A C45A H45C 108.7 . . ?
N10A C45A H45D 108.7 . . ?
C44B C45B H45E 108.8 . . ?
C44B C45B H45F 108.8 . . ?
H45E C45B H45F 107.7 . . ?
N10B C45B C44B 114.0(4) . . ?
N10B C45B H45E 108.8 . . ?
N10B C45B H45F 108.8 . . ?
H46A C46 H46B 108.1 . . ?
H46C C46 H46D 108.1 . . ?
H46E C46 H46F 106.1 . . ?
C47 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
C47 C46 H46C 109.5 . . ?
C47 C46 H46D 109.5 . . ?
C47 C46 H46E 105.7 . . ?
C47 C46 H46F 105.7 . . ?
N10 C46 H46A 109.5 . . ?
N10 C46 H46B 109.5 . . ?
N10 C46 C47 110.51(13) . . ?
N10A C46 H46C 109.5 . . ?
N10A C46 H46D 109.5 . . ?
N10A C46 C47 110.51(13) . . ?
N10B C46 H46E 105.7 . . ?
N10B C46 H46F 105.7 . . ?
N10B C46 C47 126.5(2) . . ?
C48 C47 C46 118.91(11) . . ?
C52 C47 C46 122.42(11) . . ?
C52 C47 C48 118.59(12) . . ?
C47 C48 H48 119.5 . . ?
C49 C48 C47 120.91(12) . . ?
C49 C48 H48 119.5 . . ?
C48 C49 H49 120.0 . . ?
C50 C49 C48 119.98(12) . . ?
C50 C49 H49 120.0 . . ?
C49 C50 H50 120.2 . . ?
C49 C50 C51 119.51(13) . . ?
C51 C50 H50 120.2 . . ?
C50 C51 H51 119.8 . . ?
C50 C51 C52 120.32(13) . . ?
C52 C51 H51 119.8 . . ?
C47 C52 C51 120.68(12) . . ?
C47 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
N11 C53 N9 117.0(4) . . ?
O5 C53 N9 119.6(10) . . ?
O5 C53 N11 123.4(10) . . ?
N11 C53A N9A 110.4(3) . . ?
O5A C53A N9A 122.5(5) . . ?
O5A C53A N11 121.2(5) . . ?
N11 C53B N9B 114.0(5) . . ?
O5B C53B N9B 115.7(13) . . ?
O5B C53B N11 120.8(12) . . ?
H54A C54 H54B 107.2 . . ?
C55 C54 H54A 107.8 . . ?
C55 C54 H54B 107.8 . . ?
N11 C54 H54A 107.8 . . ?
N11 C54 H54B 107.8 . . ?
N11 C54 C55 117.9(5) . . ?
H54C C54A H54D 108.7 . . ?
C55A C54A H54C 110.5 . . ?
C55A C54A H54D 110.5 . . ?
N11 C54A H54C 110.5 . . ?
N11 C54A H54D 110.5 . . ?
N11 C54A C55A 106.2(5) . . ?
C54 C55 H55A 108.9 . . ?
C54 C55 H55B 108.9 . . ?
C54 C55 C56 113.5(4) . . ?
H55A C55 H55B 107.7 . . ?
C56 C55 H55A 108.9 . . ?
C56 C55 H55B 108.9 . . ?
C54A C55A H55C 109.4 . . ?
C54A C55A H55D 109.4 . . ?
H55C C55A H55D 108.0 . . ?
C56A C55A C54A 111.4(4) . . ?
C56A C55A H55C 109.4 . . ?
C56A C55A H55D 109.4 . . ?
C55 C56 H56A 109.2 . . ?
C55 C56 H56B 109.2 . . ?
C55 C56 C57 112.1(2) . . ?
H56A C56 H56B 107.9 . . ?
C57 C56 H56A 109.2 . . ?
C57 C56 H56B 109.2 . . ?
C55A C56A H56C 109.2 . . ?
C55A C56A H56D 109.2 . . ?
C55A C56A C57A 112.0(3) . . ?
H56C C56A H56D 107.9 . . ?
C57A C56A H56C 109.2 . . ?
C57A C56A H56D 109.2 . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56A C57A H57D 109.5 . . ?
C56A C57A H57E 109.5 . . ?
C56A C57A H57F 109.5 . . ?
H57D C57A H57E 109.5 . . ?
H57D C57A H57F 109.5 . . ?
H57E C57A H57F 109.5 . . ?
N10 C58 N12 115.97(14) . . ?
N10A C58 N12 115.97(14) . . ?
N12 C58 N10B 116.1(2) . . ?
O6 C58 N10 121.12(14) . . ?
O6 C58 N10A 121.12(14) . . ?
O6 C58 N10B 120.4(2) . . ?
O6 C58 N12 122.50(11) . . ?
C60 C59 N12 121.70(11) . . ?
C64 C59 C60 119.97(11) . . ?
C64 C59 N12 118.24(11) . . ?
C59 C60 H60 120.2 . . ?
C61 C60 C59 119.59(12) . . ?
C61 C60 H60 120.2 . . ?
C60 C61 H61 119.6 . . ?
C62 C61 C60 120.77(13) . . ?
C62 C61 H61 119.6 . . ?
C61 C62 H62 120.3 . . ?
C61 C62 C63 119.37(12) . . ?
C63 C62 H62 120.3 . . ?
C62 C63 H63 119.6 . . ?
C62 C63 C64 120.72(13) . . ?
C64 C63 H63 119.6 . . ?
C59 C64 H64 120.2 . . ?
C63 C64 C59 119.55(12) . . ?
C63 C64 H64 120.2 . . ?
C33 N7 H7 118.7(12) . . ?
C41 N7 C33 123.43(11) . . ?
C41 N7 H7 117.8(12) . . ?
C41 N8 C42 119.4(3) . . ?
C41 N8 H8 120.3 . . ?
C42 N8 H8 120.3 . . ?
C41 N8A C42A 121.2(6) . . ?
C41 N8A H8A 119.4 . . ?
C42A N8A H8A 119.4 . . ?
C41 N8B C42B 117.0(6) . . ?
C41 N8B H8B 121.5 . . ?
C42B N8B H8B 121.5 . . ?
C44 N9 C43 120.3(3) . . ?
C53 N9 C43 122.2(4) . . ?
C53 N9 C44 116.1(3) . . ?
C44A N9A C43A 125.6(4) . . ?
C53A N9A C43A 110.4(4) . . ?
C53A N9A C44A 118.8(4) . . ?
C44B N9B C43B 119.8(4) . . ?
C53B N9B C43B 114.1(5) . . ?
C53B N9B C44B 117.3(4) . . ?
C45 N10 C46 117.5(4) . . ?
C58 N10 C45 123.5(4) . . ?
C58 N10 C46 116.53(16) . . ?
C45A N10A C46 120.2(4) . . ?
C58 N10A C45A 122.9(4) . . ?
C58 N10A C46 116.53(16) . . ?
C46 N10B C45B 120.4(4) . . ?
C46 N10B C58 116.4(3) . . ?
C58 N10B C45B 123.1(5) . . ?
C53 N11 C54 117.5(5) . . ?
C53 N11 H11 120.5(12) . . ?
C53A N11 C54A 121.7(5) . . ?
C53A N11 H11 120.6(12) . . ?
C53B N11 H11 116.0(12) . . ?
C54 N11 H11 119.7(12) . . ?
C54A N11 H11 117.7(12) . . ?
C58 N12 C59 122.80(10) . . ?
C58 N12 H12 120.9(11) . . ?
C59 N12 H12 115.7(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
N1 H1 O6 0.852(18) 2.188(18) 2.9546(14) 149.5(15) . yes
N2 H2A O6 0.845(19) 1.962(19) 2.7691(14) 159.2(16) . yes
N5 H5 O1 0.864(18) 2.136(18) 2.9920(13) 171.0(16) . yes
N6 H6A O2 0.850(16) 1.966(17) 2.8026(13) 167.9(14) . yes
N7 H7 O3 0.847(18) 2.351(18) 3.0759(13) 143.9(15) 2_766 yes
N8 H8 O3 0.88 2.11 2.909(4) 149.7 2_766 yes
N8A H8A O3 0.88 2.05 2.877(7) 155.6 2_766 yes
N8B H8B O3 0.88 1.92 2.768(7) 161.9 2_766 yes
N11 H11 O4 0.877(19) 2.027(18) 2.8946(14) 170.2(16) . yes
N12 H12 O5 0.880(18) 1.91(3) 2.782(18) 168.2(16) . yes
N12 H12 O5A 0.880(18) 1.916(19) 2.773(6) 164.4(15) . yes
N12 H12 O5B 0.880(18) 1.91(3) 2.786(19) 173.0(17) . yes

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
C1 C2 C3 C4 -0.3(2) . . . . ?
C1 C2 C3 C7 -178.50(12) . . . . ?
C2 C1 C6 C5 2.07(19) . . . . ?
C2 C1 N1 C9 -28.2(2) . . . . ?
C2 C3 C4 C5 1.44(19) . . . . ?
C2 C3 C7 F1 -46.47(17) . . . . ?
C2 C3 C7 F2 -168.02(12) . . . . ?
C2 C3 C7 F3 73.06(15) . . . . ?
C3 C4 C5 C6 -0.81(19) . . . . ?
C3 C4 C5 C8 179.90(12) . . . . ?
C4 C3 C7 F1 135.31(13) . . . . ?
C4 C3 C7 F2 13.76(18) . . . . ?
C4 C3 C7 F3 -105.17(14) . . . . ?
C4 C5 C6 C1 -0.94(19) . . . . ?
C4 C5 C8 F4 38.94(16) . . . . ?
C4 C5 C8 F5 -80.37(15) . . . . ?
C4 C5 C8 F6 159.03(12) . . . . ?
C6 C1 C2 C3 -1.46(19) . . . . ?
C6 C1 N1 C9 151.77(12) . . . . ?
C6 C5 C8 F4 -140.36(12) . . . . ?
C6 C5 C8 F5 100.33(14) . . . . ?
C6 C5 C8 F6 -20.27(17) . . . . ?
C7 C3 C4 C5 179.59(12) . . . . ?
C8 C5 C6 C1 178.34(12) . . . . ?
C10 C11 N3 C12 -103.02(12) . . . . ?
C10 C11 N3 C21 86.61(14) . . . . ?
C11 C10 N2 C9 75.98(15) . . . . ?
C12 C13 N4 C14 -99.60(12) . . . . ?
C12 C13 N4 C26 88.30(13) . . . . ?
C13 C12 N3 C11 -92.82(13) . . . . ?
C13 C12 N3 C21 78.03(13) . . . . ?
C14 C15 C16 C17 177.57(11) . . . . ?
C14 C15 C20 C19 -177.31(12) . . . . ?
C15 C14 N4 C13 81.79(13) . . . . ?
C15 C14 N4 C26 -105.76(12) . . . . ?
C15 C16 C17 C18 -0.49(19) . . . . ?
C16 C15 C20 C19 -0.19(19) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C19 C20 C15 -0.3(2) . . . . ?
C20 C15 C16 C17 0.60(18) . . . . ?
C22 C23 C24 C25 178.31(14) . . . . ?
C23 C22 N5 C21 -134.18(12) . . . . ?
C27 C28 C29 C30 0.26(18) . . . . ?
C28 C27 C32 C31 -0.34(18) . . . . ?
C28 C27 N6 C26 -19.35(18) . . . . ?
C28 C29 C30 C31 -0.1(2) . . . . ?
C29 C30 C31 C32 -0.3(2) . . . . ?
C30 C31 C32 C27 0.5(2) . . . . ?
C32 C27 C28 C29 -0.05(17) . . . . ?
C32 C27 N6 C26 164.55(11) . . . . ?
N1 C1 C2 C3 178.47(12) . . . . ?
N1 C1 C6 C5 -177.86(12) . . . . ?
N1 C9 N2 C10 -177.66(11) . . . . ?
N2 C9 N1 C1 179.96(12) . . . . ?
N2 C10 C11 N3 -159.77(10) . . . . ?
N3 C12 C13 N4 -154.82(10) . . . . ?
N3 C21 N5 C22 173.84(11) . . . . ?
N4 C14 C15 C16 28.87(16) . . . . ?
N4 C14 C15 C20 -154.13(11) . . . . ?
N4 C26 N6 C27 169.46(10) . . . . ?
N5 C21 N3 C11 -9.19(18) . . . . ?
N5 C21 N3 C12 -179.84(11) . . . . ?
N5 C22 C23 C24 179.11(12) . . . . ?
N6 C26 N4 C13 -3.70(16) . . . . ?
N6 C26 N4 C14 -175.74(10) . . . . ?
N6 C27 C28 C29 -176.07(10) . . . . ?
N6 C27 C32 C31 175.94(11) . . . . ?
O1 C9 N1 C1 0.0(2) . . . . ?
O1 C9 N2 C10 2.33(19) . . . . ?
O2 C21 N3 C11 170.48(11) . . . . ?
O2 C21 N3 C12 -0.17(17) . . . . ?
O2 C21 N5 C22 -5.82(19) . . . . ?
O3 C26 N4 C13 175.68(11) . . . . ?
O3 C26 N4 C14 3.64(17) . . . . ?
O3 C26 N6 C27 -9.92(18) . . . . ?
C33 C34 C35 C36 -1.62(18) . . . . ?
C33 C34 C35 C39 176.60(11) . . . . ?
C34 C33 C38 C37 -1.04(17) . . . . ?
C34 C33 N7 C41 28.76(19) . . . . ?
C34 C35 C36 C37 -0.83(18) . . . . ?
C34 C35 C39 F7 32.29(17) . . . . ?
C34 C35 C39 F8 -87.53(15) . . . . ?
C34 C35 C39 F9 153.68(12) . . . . ?
C35 C36 C37 C38 2.38(17) . . . . ?
C35 C36 C37 C40 179.45(11) . . . . ?
C36 C35 C39 F7 -149.45(12) . . . . ?
C36 C35 C39 F8 90.74(15) . . . . ?
C36 C35 C39 F9 -28.06(17) . . . . ?
C36 C37 C38 C33 -1.46(18) . . . . ?
C36 C37 C40 F10 15.86(16) . . . . ?
C36 C37 C40 F11 -103.41(13) . . . . ?
C36 C37 C40 F12 136.28(12) . . . . ?
C38 C33 C34 C35 2.54(17) . . . . ?
C38 C33 N7 C41 -153.15(13) . . . . ?
C38 C37 C40 F10 -167.01(11) . . . . ?
C38 C37 C40 F11 73.73(14) . . . . ?
C38 C37 C40 F12 -46.58(15) . . . . ?
C39 C35 C36 C37 -179.05(11) . . . . ?
C40 C37 C38 C33 -178.54(11) . . . . ?
C42 C43 N9 C44 110.7(4) . . . . ?
C42 C43 N9 C53 -83.8(5) . . . . ?
C42A C43A N9A C44A -81.9(6) . . . . ?
C42A C43A N9A C53A 124.2(5) . . . . ?
C42B C43B N9B C44B -101.9(7) . . . . ?
C42B C43B N9B C53B 44.7(9) . . . . ?
C43 C42 N8 C41 -67.2(5) . . . . ?
C43A C42A N8A C41 67.7(8) . . . . ?
C43B C42B N8B C41 69.6(8) . . . . ?
C44 C45 N10 C46 -81.8(6) . . . . ?
C44 C45 N10 C58 79.8(6) . . . . ?
C44A C45A N10A C46 -78.8(7) . . . . ?
C44A C45A N10A C58 93.6(6) . . . . ?
C44B C45B N10B C46 104.5(4) . . . . ?
C44B C45B N10B C58 -79.2(5) . . . . ?
C45 C44 N9 C43 -116.2(5) . . . . ?
C45 C44 N9 C53 77.5(6) . . . . ?
C45A C44A N9A C43A -84.9(7) . . . . ?
C45A C44A N9A C53A 67.1(7) . . . . ?
C45B C44B N9B C43B 90.3(5) . . . . ?
C45B C44B N9B C53B -55.3(6) . . . . ?
C46 C47 C48 C49 175.93(12) . . . . ?
C46 C47 C52 C51 -176.26(12) . . . . ?
C47 C46 N10 C45 -94.6(4) . . . . ?
C47 C46 N10 C58 102.49(16) . . . . ?
C47 C46 N10A C45A -84.7(3) . . . . ?
C47 C46 N10A C58 102.49(16) . . . . ?
C47 C46 N10B C45B -107.2(4) . . . . ?
C47 C46 N10B C58 76.2(5) . . . . ?
C47 C48 C49 C50 0.8(2) . . . . ?
C48 C47 C52 C51 0.37(19) . . . . ?
C48 C49 C50 C51 -0.3(2) . . . . ?
C49 C50 C51 C52 -0.2(2) . . . . ?
C50 C51 C52 C47 0.1(2) . . . . ?
C52 C47 C48 C49 -0.82(19) . . . . ?
C54 C55 C56 C57 177.7(5) . . . . ?
C54A C55A C56A C57A -174.8(6) . . . . ?
C55 C54 N11 C53 87.1(8) . . . . ?
C55A C54A N11 C53A 136.8(6) . . . . ?
C59 C60 C61 C62 1.3(2) . . . . ?
C60 C59 C64 C63 0.56(19) . . . . ?
C60 C59 N12 C58 -42.09(18) . . . . ?
C60 C61 C62 C63 0.3(2) . . . . ?
C61 C62 C63 C64 -1.6(2) . . . . ?
C62 C63 C64 C59 1.1(2) . . . . ?
C64 C59 C60 C61 -1.78(19) . . . . ?
C64 C59 N12 C58 141.30(13) . . . . ?
N7 C33 C34 C35 -179.38(11) . . . . ?
N7 C33 C38 C37 -179.17(10) . . . . ?
N7 C41 N8 C42 -163.4(3) . . . . ?
N7 C41 N8A C42A 179.8(5) . . . . ?
N7 C41 N8B C42B 171.3(4) . . . . ?
N8 C41 N7 C33 171.8(2) . . . . ?
N8 C42 C43 N9 159.5(3) . . . . ?
N8A C41 N7 C33 -165.9(4) . . . . ?
N8A C42A C43A N9A -156.2(5) . . . . ?
N8B C41 N7 C33 -158.6(4) . . . . ?
N8B C42B C43B N9B -149.6(7) . . . . ?
N9 C44 C45 N10 -158.2(5) . . . . ?
N9 C53 N11 C54 -165.2(5) . . . . ?
N9A C44A C45A N10A -153.2(5) . . . . ?
N9A C53A N11 C54A -162.2(6) . . . . ?
N9B C44B C45B N10B 159.0(4) . . . . ?
N10 C46 C47 C48 151.58(13) . . . . ?
N10 C46 C47 C52 -31.80(18) . . . . ?
N10 C58 N12 C59 166.60(13) . . . . ?
N10A C46 C47 C48 151.58(13) . . . . ?
N10A C46 C47 C52 -31.80(18) . . . . ?
N10A C58 N12 C59 166.60(13) . . . . ?
N10B C46 C47 C48 149.8(3) . . . . ?
N10B C46 C47 C52 -33.6(3) . . . . ?
N10B C58 N12 C59 -174.6(3) . . . . ?
N11 C53 N9 C43 11.8(8) . . . . ?
N11 C53 N9 C44 177.9(4) . . . . ?
N11 C53A N9A C43A -56.6(6) . . . . ?
N11 C53A N9A C44A 147.5(4) . . . . ?
N11 C53B N9B C43B 49.3(8) . . . . ?
N11 C53B N9B C44B -163.2(5) . . . . ?
N11 C54 C55 C56 60.4(9) . . . . ?
N11 C54A C55A C56A -178.7(6) . . . . ?
N12 C58 N10 C45 3.9(4) . . . . ?
N12 C58 N10 C46 165.67(13) . . . . ?
N12 C58 N10A C45A -7.0(4) . . . . ?
N12 C58 N10A C46 165.67(13) . . . . ?
N12 C58 N10B C45B 7.6(6) . . . . ?
N12 C58 N10B C46 -176.0(3) . . . . ?
N12 C59 C60 C61 -178.33(12) . . . . ?
N12 C59 C64 C63 177.23(12) . . . . ?
O4 C41 N7 C33 10.4(2) . . . . ?
O4 C41 N8 C42 -1.8(5) . . . . ?
O4 C41 N8A C42A 3.4(9) . . . . ?
O4 C41 N8B C42B 2.7(8) . . . . ?
O5 C53 N9 C43 -167.0(13) . . . . ?
O5 C53 N9 C44 -1.0(15) . . . . ?
O5 C53 N11 C54 13.6(15) . . . . ?
O5A C53A N9A C43A 150.3(5) . . . . ?
O5A C53A N9A C44A -5.6(8) . . . . ?
O5A C53A N11 C54A -8.7(8) . . . . ?
O5B C53B N9B C43B -163.9(12) . . . . ?
O5B C53B N9B C44B -16.4(14) . . . . ?
O6 C58 N10 C45 176.6(3) . . . . ?
O6 C58 N10 C46 -21.6(2) . . . . ?
O6 C58 N10A C45A 165.8(3) . . . . ?
O6 C58 N10A C46 -21.6(2) . . . . ?
O6 C58 N10B C45B -161.3(4) . . . . ?
O6 C58 N10B C46 15.2(5) . . . . ?
O6 C58 N12 C59 -6.0(2) . . . . ?

_olex2_date_sample_data_collection 2022-01-12
_olex2_date_sample_submission    2022-01-11
_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_hklf5
_database_code_depnum_ccdc_archive 'CCDC 2195689'
loop_
_audit_author_name
_audit_author_address
'Dr Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C30 H26 F12 N6 O4'
_chemical_formula_sum            'C31 H27 Cl3 F12 N6 O4'
_chemical_formula_weight         881.93
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9480(4)
_cell_length_b                   12.5972(5)
_cell_length_c                   12.9273(4)
_cell_angle_alpha                80.719(2)
_cell_angle_beta                 76.811(2)
_cell_angle_gamma                73.555(2)
_cell_volume                     1807.12(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3077
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.846
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 43556 reflections, Rint = 0.0537
 (15599 with I > 3sig(I), Rint = 0.0322)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.476
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.868
_diffrn_reflns_theta_min         1.627
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5636
_reflns_number_total             7730
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.532
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         7730
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+1.6732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          
;
The structure was refined as a two component twin against an hklf 5 file,
the twin scale fraction refined to 0.4810(11).
Occupancies of the disordered chlorine atoms were refined with their sum
set to equal 1.  Restraints were used to maintain similar C-Cl distances
and thermal parameters for the Cl.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51902
 0.48098
2. Restrained distances
 Cl1A-C31 \\sim Cl1-C31 \\sim Cl3A-C31 \\sim Cl3-C31 \\sim Cl2A-C31 \\sim
Cl2-C31
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Cl1A \\sim Cl1 \\sim Cl3A \\sim Cl3 \\sim Cl2A \\sim Cl2: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(H31A)=Sof(Cl2A)=Sof(Cl1A)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl3)=Sof(Cl2)=Sof(Cl1)=Sof(H31)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C31(H31A)
5.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C10(H10A,H10B), C21(H21A,H21B), C11(H11A,H11B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C17(H17), C5(H5A), C18(H18), C3(H3), C15(H15), C14(H14), C28(H28),
 C24(H24), C26(H26)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl3 Cl 0.71777(10) 0.32097(9) 0.71713(9) 0.0410(3) Uani 0.845(2) 1 d D U P A 1
Cl2 Cl 0.61921(13) 0.19970(13) 0.90618(16) 0.0599(4) Uani 0.845(2) 1 d D U P A
1
Cl1 Cl 0.58148(16) 0.43764(13) 0.89684(12) 0.0716(5) Uani 0.845(2) 1 d D U P A
1
F1 F -0.07478(19) 1.04701(17) 0.19071(19) 0.0433(6) Uani 1 1 d . . . . .
O1 O 0.33973(19) 1.10596(18) 0.20968(16) 0.0227(5) Uani 1 1 d . . . . .
O2 O 0.6244(2) 0.95471(19) 0.43450(16) 0.0255(5) Uani 1 1 d . . . . .
F4 F -0.0535(2) 0.7676(2) 0.5738(2) 0.0540(7) Uani 1 1 d . . . . .
F5 F 0.0783(2) 0.7954(2) 0.64767(19) 0.0561(7) Uani 1 1 d . . . . .
O3 O 0.4795(2) 0.5353(2) 0.66203(18) 0.0331(6) Uani 1 1 d . . . . .
F6 F 0.1274(2) 0.67225(18) 0.5372(2) 0.0543(7) Uani 1 1 d . . . . .
O4 O 0.6935(2) 0.7170(2) 0.12505(17) 0.0368(6) Uani 1 1 d . . . . .
F3 F 0.0951(2) 0.9762(2) 0.09986(18) 0.0587(7) Uani 1 1 d . . . . .
F2 F -0.0203(2) 0.87213(19) 0.1803(2) 0.0618(8) Uani 1 1 d . . . . .
F10 F 0.9257(3) 0.5282(2) -0.38517(19) 0.0635(8) Uani 1 1 d . . . . .
N2 N 0.4359(2) 1.1310(2) 0.3322(2) 0.0232(6) Uani 1 1 d . . . . .
F12 F 1.0912(2) 0.4783(2) -0.3320(2) 0.0613(7) Uani 1 1 d . . . . .
F8 F 1.0111(2) 0.2504(2) 0.0536(2) 0.0695(8) Uani 1 1 d . . . . .
F7 F 0.9070(3) 0.3645(2) 0.1667(2) 0.0729(9) Uani 1 1 d . . . . .
N5 N 0.6487(2) 0.8767(2) 0.0168(2) 0.0216(6) Uani 1 1 d . . . . .
N3 N 0.6756(2) 0.9951(2) 0.25478(19) 0.0220(6) Uani 1 1 d . . . . .
N4 N 0.6683(3) 0.8151(2) 0.3293(2) 0.0259(6) Uani 1 1 d . . . . .
N1 N 0.2931(2) 1.0359(2) 0.3845(2) 0.0240(6) Uani 1 1 d . . . . .
F11 F 0.9986(3) 0.3572(2) -0.3329(2) 0.0813(11) Uani 1 1 d . . . . .
N6 N 0.7234(3) 0.7131(2) -0.0572(2) 0.0339(8) Uani 1 1 d . . . . .
F9 F 0.8231(3) 0.2751(2) 0.0968(3) 0.0909(11) Uani 1 1 d . . . . .
C9 C 0.3559(3) 1.0923(2) 0.3032(2) 0.0195(6) Uani 1 1 d . . . . .
C20 C 0.7100(3) 0.9595(3) 0.1478(2) 0.0237(7) Uani 1 1 d . . . . .
H20A H 0.771507 0.887756 0.148605 0.028 Uiso 1 1 calc R . . . .
H20B H 0.746064 1.014910 0.098617 0.028 Uiso 1 1 calc R . . . .
C13 C 0.6186(3) 0.7439(3) 0.4152(2) 0.0252(7) Uani 1 1 d . . . . .
C6 C 0.2066(3) 0.9834(3) 0.3771(2) 0.0216(7) Uani 1 1 d . . . . .
C22 C 0.6895(3) 0.7656(3) 0.0347(2) 0.0278(8) Uani 1 1 d . . . . .
C10 C 0.5241(3) 1.1774(3) 0.2562(2) 0.0249(7) Uani 1 1 d . . . . .
H10A H 0.511840 1.255968 0.267819 0.030 Uiso 1 1 calc R . . . .
H10B H 0.513264 1.175943 0.182797 0.030 Uiso 1 1 calc R . . . .
C1 C 0.1551(3) 0.9985(3) 0.2875(3) 0.0239(7) Uani 1 1 d . . . . .
H1A H 0.177547 1.046909 0.226723 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0709(3) 0.9420(3) 0.2882(3) 0.0274(7) Uani 1 1 d . . . . .
C21 C 0.6059(3) 0.9452(3) 0.1045(2) 0.0212(7) Uani 1 1 d . . . . .
H21A H 0.553615 0.910319 0.162517 0.025 Uiso 1 1 calc R . . . .
H21B H 0.558239 1.019174 0.079923 0.025 Uiso 1 1 calc R . . . .
C17 C 0.6372(3) 0.6094(3) 0.5690(2) 0.0297(8) Uani 1 1 d . . . . .
H17 H 0.683720 0.565181 0.618570 0.036 Uiso 1 1 calc R . . . .
C12 C 0.6543(3) 0.9235(3) 0.3437(2) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.1717(3) 0.9123(3) 0.4652(3) 0.0256(7) Uani 1 1 d . . . . .
H5A H 0.207014 0.901047 0.526180 0.031 Uiso 1 1 calc R . . . .
C16 C 0.5204(3) 0.6048(3) 0.5790(2) 0.0265(7) Uani 1 1 d . . . . .
C18 C 0.6863(3) 0.6779(3) 0.4872(2) 0.0264(7) Uani 1 1 d . . . . .
H18 H 0.766651 0.679770 0.480369 0.032 Uiso 1 1 calc R . . . .
C11 C 0.6499(3) 1.1131(3) 0.2670(3) 0.0255(7) Uani 1 1 d . . . . .
H11A H 0.706697 1.146270 0.212413 0.031 Uiso 1 1 calc R . . . .
H11B H 0.662657 1.120999 0.338113 0.031 Uiso 1 1 calc R . . . .
C3 C 0.0343(3) 0.8723(3) 0.3760(3) 0.0324(8) Uani 1 1 d . . . . .
H3 H -0.024741 0.835399 0.375611 0.039 Uiso 1 1 calc R . . . .
C15 C 0.4515(3) 0.6706(3) 0.5063(3) 0.0303(8) Uani 1 1 d . . . . .
H15 H 0.371455 0.668265 0.512172 0.036 Uiso 1 1 calc R . . . .
C14 C 0.5023(3) 0.7392(3) 0.4257(3) 0.0286(8) Uani 1 1 d . . . . .
H14 H 0.456009 0.784129 0.376263 0.034 Uiso 1 1 calc R . . . .
C7 C 0.0193(3) 0.9583(3) 0.1896(3) 0.0352(9) Uani 1 1 d . . . . .
C4 C 0.0866(3) 0.8580(3) 0.4649(3) 0.0293(8) Uani 1 1 d . . . . .
C23 C 0.7949(3) 0.6056(3) -0.0726(3) 0.0323(8) Uani 1 1 d . . . . .
C19 C 0.3582(3) 0.5323(3) 0.6765(3) 0.0369(9) Uani 1 1 d . . . . .
H19A H 0.345726 0.506979 0.613268 0.055 Uiso 1 1 calc GR . . . .
H19B H 0.306309 0.607041 0.686827 0.055 Uiso 1 1 calc GR . . . .
H19C H 0.339441 0.480958 0.739489 0.055 Uiso 1 1 calc GR . . . .
C27 C 0.9202(4) 0.4802(3) -0.1998(3) 0.0423(10) Uani 1 1 d . . . . .
C28 C 0.8468(3) 0.5843(3) -0.1785(3) 0.0360(9) Uani 1 1 d . . . . .
H28 H 0.831716 0.641066 -0.235403 0.043 Uiso 1 1 calc R . . . .
C24 C 0.8159(4) 0.5218(3) 0.0099(3) 0.0380(9) Uani 1 1 d . . . . .
H24 H 0.780406 0.535028 0.081873 0.046 Uiso 1 1 calc R . . . .
C8 C 0.0593(3) 0.7742(3) 0.5562(3) 0.0407(10) Uani 1 1 d . . . . .
C25 C 0.8897(4) 0.4181(3) -0.0144(3) 0.0437(10) Uani 1 1 d . . . . .
C30 C 0.9812(4) 0.4622(3) -0.3137(3) 0.0490(12) Uani 1 1 d . . . . .
C26 C 0.9430(4) 0.3965(3) -0.1188(3) 0.0439(10) Uani 1 1 d . . . . .
H26 H 0.994083 0.325593 -0.133895 0.053 Uiso 1 1 calc R . . . .
C31 C 0.5967(3) 0.3293(3) 0.8271(3) 0.0436(10) Uani 1 1 d D . . . .
H31 H 0.522232 0.341684 0.798789 0.052 Uiso 0.845(2) 1 calc R . P A 1
H31A H 0.560891 0.366484 0.763491 0.052 Uiso 0.155(2) 1 calc R . P A 2
C29 C 0.9080(4) 0.3271(4) 0.0748(4) 0.0559(13) Uani 1 1 d . . . . .
Cl2A Cl 0.6258(9) 0.1884(6) 0.8356(10) 0.078(3) Uani 0.155(2) 1 d D U P A 2
Cl1A Cl 0.4986(10) 0.3701(11) 0.9522(8) 0.111(4) Uani 0.155(2) 1 d D U P A 2
Cl3A Cl 0.7164(8) 0.3813(10) 0.8383(10) 0.097(3) Uani 0.155(2) 1 d D U P A 2
H2 H 0.445(3) 1.116(3) 0.390(3) 0.015(9) Uiso 1 1 d . . . . .
H5 H 0.648(3) 0.908(3) -0.043(3) 0.025(10) Uiso 1 1 d . . . . .
H1 H 0.318(3) 1.027(3) 0.444(3) 0.042(12) Uiso 1 1 d . . . . .
H6 H 0.716(3) 0.755(3) -0.108(3) 0.027(10) Uiso 1 1 d . . . . .
H4 H 0.680(3) 0.794(3) 0.272(3) 0.036(11) Uiso 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
Cl3 C31 1.774(3) . ?
Cl2 C31 1.767(4) . ?
Cl1 C31 1.701(4) . ?
F1 C7 1.342(4) . ?
O1 C9 1.245(3) . ?
O2 C12 1.241(3) . ?
F4 C8 1.339(4) . ?
F5 C8 1.334(5) . ?
O3 C16 1.363(4) . ?
O3 C19 1.428(4) . ?
F6 C8 1.339(4) . ?
O4 C22 1.233(4) . ?
F3 C7 1.330(4) . ?
F2 C7 1.332(4) . ?
F10 C30 1.305(5) . ?
N2 C9 1.333(4) . ?
N2 C10 1.452(4) . ?
N2 H2 0.76(3) . ?
F12 C30 1.348(5) . ?
F8 C29 1.335(5) . ?
F7 C29 1.344(6) . ?
N5 C22 1.346(4) . ?
N5 C21 1.446(4) . ?
N5 H5 0.81(3) . ?
N3 C20 1.455(4) . ?
N3 C12 1.363(4) . ?
N3 C11 1.458(4) . ?
N4 C13 1.439(4) . ?
N4 C12 1.366(4) . ?
N4 H4 0.80(4) . ?
N1 C9 1.369(4) . ?
N1 C6 1.403(4) . ?
N1 H1 0.86(4) . ?
F11 C30 1.334(4) . ?
N6 C22 1.376(4) . ?
N6 C23 1.400(4) . ?
N6 H6 0.78(4) . ?
F9 C29 1.313(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.540(4) . ?
C13 C18 1.387(4) . ?
C13 C14 1.383(5) . ?
C6 C1 1.395(4) . ?
C6 C5 1.392(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(5) . ?
C1 H1A 0.9500 . ?
C1 C2 1.386(5) . ?
C2 C3 1.385(5) . ?
C2 C7 1.500(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C17 H17 0.9500 . ?
C17 C16 1.388(5) . ?
C17 C18 1.385(5) . ?
C5 H5A 0.9500 . ?
C5 C4 1.377(5) . ?
C16 C15 1.402(5) . ?
C18 H18 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.393(5) . ?
C15 H15 0.9500 . ?
C15 C14 1.385(5) . ?
C14 H14 0.9500 . ?
C4 C8 1.493(5) . ?
C23 C28 1.403(5) . ?
C23 C24 1.387(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C27 C28 1.386(5) . ?
C27 C30 1.508(5) . ?
C27 C26 1.376(5) . ?
C28 H28 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.392(5) . ?
C25 C26 1.389(5) . ?
C25 C29 1.496(5) . ?
C26 H26 0.9500 . ?
C31 H31 1.0000 . ?
C31 H31A 1.0000 . ?
C31 Cl2A 1.699(7) . ?
C31 Cl1A 1.821(7) . ?
C31 Cl3A 1.776(7) . ?

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
C16 O3 C19 117.5(3) . . ?
C9 N2 C10 123.2(3) . . ?
C9 N2 H2 118(3) . . ?
C10 N2 H2 118(3) . . ?
C22 N5 C21 120.9(3) . . ?
C22 N5 H5 122(2) . . ?
C21 N5 H5 117(2) . . ?
C20 N3 C11 119.1(3) . . ?
C12 N3 C20 122.1(3) . . ?
C12 N3 C11 118.4(2) . . ?
C13 N4 H4 114(3) . . ?
C12 N4 C13 119.2(3) . . ?
C12 N4 H4 123(3) . . ?
C9 N1 C6 127.2(3) . . ?
C9 N1 H1 113(3) . . ?
C6 N1 H1 119(3) . . ?
C22 N6 C23 128.2(3) . . ?
C22 N6 H6 112(3) . . ?
C23 N6 H6 117(3) . . ?
O1 C9 N2 122.8(3) . . ?
O1 C9 N1 122.6(3) . . ?
N2 C9 N1 114.6(3) . . ?
N3 C20 H20A 108.8 . . ?
N3 C20 H20B 108.8 . . ?
N3 C20 C21 113.7(2) . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C18 C13 N4 121.0(3) . . ?
C14 C13 N4 119.9(3) . . ?
C14 C13 C18 119.1(3) . . ?
C1 C6 N1 123.8(3) . . ?
C5 C6 N1 117.1(3) . . ?
C5 C6 C1 119.2(3) . . ?
O4 C22 N5 122.5(3) . . ?
O4 C22 N6 124.3(3) . . ?
N5 C22 N6 113.2(3) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C11 111.8(3) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C6 C1 H1A 120.4 . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 H1A 120.4 . . ?
C1 C2 C7 117.7(3) . . ?
C3 C2 C1 122.1(3) . . ?
C3 C2 C7 120.2(3) . . ?
N5 C21 C20 111.0(3) . . ?
N5 C21 H21A 109.4 . . ?
N5 C21 H21B 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C18 C17 C16 120.5(3) . . ?
O2 C12 N3 121.7(3) . . ?
O2 C12 N4 120.8(3) . . ?
N3 C12 N4 117.5(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
O3 C16 C17 116.4(3) . . ?
O3 C16 C15 123.8(3) . . ?
C17 C16 C15 119.8(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
N3 C11 C10 113.5(3) . . ?
N3 C11 H11A 108.9 . . ?
N3 C11 H11B 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.1(3) . . ?
C4 C3 H3 120.9 . . ?
C16 C15 H15 120.7 . . ?
C14 C15 C16 118.7(3) . . ?
C14 C15 H15 120.7 . . ?
C13 C14 C15 121.8(3) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
F1 C7 C2 111.5(3) . . ?
F3 C7 F1 105.5(3) . . ?
F3 C7 F2 107.9(3) . . ?
F3 C7 C2 113.5(3) . . ?
F2 C7 F1 105.6(3) . . ?
F2 C7 C2 112.3(3) . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 C8 119.5(3) . . ?
C3 C4 C8 119.5(3) . . ?
N6 C23 C28 116.5(3) . . ?
C24 C23 N6 123.7(3) . . ?
C24 C23 C28 119.8(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C28 C27 C30 118.4(3) . . ?
C26 C27 C28 121.2(3) . . ?
C26 C27 C30 120.3(3) . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.7(3) . . ?
C27 C28 H28 120.1 . . ?
C23 C24 H24 120.5 . . ?
C23 C24 C25 118.9(3) . . ?
C25 C24 H24 120.5 . . ?
F4 C8 C4 112.7(3) . . ?
F5 C8 F4 107.1(3) . . ?
F5 C8 F6 106.9(3) . . ?
F5 C8 C4 112.8(3) . . ?
F6 C8 F4 106.2(3) . . ?
F6 C8 C4 110.8(3) . . ?
C24 C25 C29 118.5(3) . . ?
C26 C25 C24 121.8(3) . . ?
C26 C25 C29 119.7(3) . . ?
F10 C30 F12 107.1(3) . . ?
F10 C30 F11 108.6(4) . . ?
F10 C30 C27 114.2(3) . . ?
F12 C30 C27 110.1(4) . . ?
F11 C30 F12 104.8(3) . . ?
F11 C30 C27 111.6(3) . . ?
C27 C26 C25 118.6(3) . . ?
C27 C26 H26 120.7 . . ?
C25 C26 H26 120.7 . . ?
Cl3 C31 H31 108.2 . . ?
Cl2 C31 Cl3 107.87(19) . . ?
Cl2 C31 H31 108.2 . . ?
Cl1 C31 Cl3 111.3(2) . . ?
Cl1 C31 Cl2 112.8(2) . . ?
Cl1 C31 H31 108.2 . . ?
Cl2A C31 H31A 112.2 . . ?
Cl2A C31 Cl1A 106.1(6) . . ?
Cl2A C31 Cl3A 115.2(6) . . ?
Cl1A C31 H31A 112.2 . . ?
Cl3A C31 H31A 112.2 . . ?
Cl3A C31 Cl1A 97.8(6) . . ?
F8 C29 F7 106.2(4) . . ?
F8 C29 C25 113.1(3) . . ?
F7 C29 C25 112.9(4) . . ?
F9 C29 F8 107.2(4) . . ?
F9 C29 F7 105.4(4) . . ?
F9 C29 C25 111.5(4) . . ?

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
C1 H1A O1 0.95 2.22 2.819(4) 120.2 . yes
N5 H5 O1 0.81(3) 2.16(4) 2.875(3) 148(3) 2_675 yes
N1 H1 O2 0.86(4) 1.93(4) 2.769(3) 165(4) 2_676 yes
N6 H6 O1 0.78(4) 2.06(4) 2.811(4) 163(4) 2_675 yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51902
2 0.48098

####################################################################### 
# 
# 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_s5847a
_database_code_depnum_ccdc_archive 'CCDC 2189991'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica-Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H32 F6 N6 O3'
_chemical_formula_sum            'C34 H32 F6 N6 O3'
_chemical_formula_weight         686.65
_chemical_melting_point          490
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   18.9800(6)
_cell_length_b                   20.3627(6)
_cell_length_c                   16.4981(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.891(3)
_cell_angle_gamma                90
_cell_volume                     6368.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7879
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4900
_cell_measurement_theta_min      3.6570
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2848
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25400
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.284
_diffrn_reflns_theta_min         3.357
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -42.00   1.00   12.50    --  -19.09 -37.00 -90.00   46
  2  ω    -94.00 -40.00   1.00   12.50    --  -19.09 178.00-180.00   54
  3  ω    -42.00  13.00   1.00   12.50    --  -19.09 -77.00 -60.00   55
  4  ω    -78.00  51.00   1.00   12.50    --  -19.09   0.00  90.00  129
  5  ω    -67.00 -26.00   1.00   12.50    --  -19.09 -37.00-150.00   41
  6  ω     37.00  80.00   1.00   12.50    --   20.18-178.00-150.00   43
  7  ω     -3.00  39.00   1.00   12.50    --   20.18  77.00  60.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0216554000
_diffrn_orient_matrix_UB_12      -0.0231281000
_diffrn_orient_matrix_UB_13      -0.0191481000
_diffrn_orient_matrix_UB_21      0.0100423000
_diffrn_orient_matrix_UB_22      0.0245787000
_diffrn_orient_matrix_UB_23      -0.0276010000
_diffrn_orient_matrix_UB_31      0.0288174000
_diffrn_orient_matrix_UB_32      0.0087530000
_diffrn_orient_matrix_UB_33      0.0268539000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5595
_reflns_number_total             7599
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00024(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7599
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0335P)²+8.9127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 C13-N12 \\sim C13-N12A
 with sigma of 0.02
 N12-C20 \\sim N12A-C20
 with sigma of 0.02
 N12-C11 \\sim N12A-C11A
 with sigma of 0.02
 N9-C11 \\sim N9A-C11A
 with sigma of 0.04
 N9-C8 \\sim N9A-C8
 with sigma of 0.02
 N9-C10 \\sim N9A-C10A
 with sigma of 0.02
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C11-C10 \\sim C11A-C10A
 with sigma of 0.02
 C20-C11 \\sim C20-C11A
 with sigma of 0.04
 C13-C11 \\sim C13-C11A
 with sigma of 0.04
 N12-C10 \\sim N12A-C10A
 with sigma of 0.04
 F31-C28 \\sim F31A-C28
 with sigma of 0.02
 F30-C28 \\sim F30A-C28
 with sigma of 0.02
 F29-C28 \\sim F29A-C28
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N12 \\sim N9 \\sim C11 \\sim C10 \\sim N12A \\sim C11A \\sim C10A \\sim N9A:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
N12 \\sim N12A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
F29A \\sim F29 \\sim F30A \\sim F30 \\sim F31A \\sim F31: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 N15, C19, C32, C33, C34, C35, C36, C37
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H13C)=Sof(H13D)=Sof(N12A)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C10A)=
 Sof(H10C)=Sof(H10D)=Sof(N9A)=Sof(H9A)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(N12)=Sof(N9)=Sof(H9)=Sof(C11)=Sof(H11A)=Sof(H11B)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
 Sof(F31A)=Sof(F29A)=Sof(F30A)=1-FVAR(2)
 Sof(F29)=Sof(F30)=Sof(F31)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C13(H13C,H13D), C19(H19A,H19B), C11(H11A,
 H11B), C10(H10A,H10B), C11A(H11C,H11D), C10A(H10C,H10D)
6.b Aromatic/amide H refined with riding coordinates:
 N18(H18), N22(H22), C2(H2), C43(H43), N7(H7), C4(H4), C6(H6), C39(H39),
 C48(H48), C41(H41), C37(H37), C42(H42), C40(H40), C45(H45), C35(H35), N9(H9),
 C46(H46), C49(H49), C36(H36), C47(H47), C33(H33), C34(H34), N9A(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F25 F 0.09489(8) 0.16977(6) 0.06708(7) 0.0419(3) Uani 1 1 d . . . . .
F26 F 0.09593(7) 0.13580(6) -0.05450(7) 0.0392(3) Uani 1 1 d . . . . .
O17 O -0.31070(7) 0.82986(6) -0.31364(8) 0.0253(3) Uani 1 1 d . . . . .
N18 N -0.19717(8) 0.81518(7) -0.26415(9) 0.0220(3) Uani 1 1 d . . . . .
H18 H -0.169845 0.791091 -0.231330 0.026 Uiso 1 1 calc R U . . .
O21 O -0.07467(7) 0.72042(6) -0.18668(8) 0.0251(3) Uani 1 1 d . . . . .
O23 O -0.00940(7) 0.47728(6) -0.14886(9) 0.0295(3) Uani 1 1 d . . . . .
N22 N -0.02094(8) 0.62405(8) -0.14354(9) 0.0230(3) Uani 1 1 d . . . . .
H22 H -0.025481 0.581138 -0.147336 0.028 Uiso 1 1 calc R U . . .
C14 C -0.23622(10) 0.70234(10) -0.18414(11) 0.0271(4) Uani 1 1 d . . . . .
H14A H -0.261892 0.673735 -0.147097 0.032 Uiso 1 1 calc R U . . .
H14B H -0.203330 0.730015 -0.150530 0.032 Uiso 1 1 calc R U . . .
F27 F -0.00224(7) 0.15747(7) -0.00175(10) 0.0560(4) Uani 1 1 d . . . . .
F29 F 0.2291(5) 0.3953(4) -0.1256(3) 0.051(2) Uani 0.60(2) 1 d D U P A 1
C13 C -0.19382(10) 0.65949(10) -0.23956(12) 0.0281(4) Uani 1 1 d D . . . .
H13A H -0.225193 0.626869 -0.267470 0.034 Uiso 0.888(3) 1 calc R U P B 1
H13B H -0.172498 0.687021 -0.281285 0.034 Uiso 0.888(3) 1 calc R U P B 1
H13C H -0.189566 0.686374 -0.289070 0.034 Uiso 0.112(3) 1 calc R U P B 2
H13D H -0.226361 0.623222 -0.255571 0.034 Uiso 0.112(3) 1 calc R U P B 2
C2 C 0.08032(9) 0.37367(9) -0.09767(11) 0.0211(4) Uani 1 1 d . . . . .
H2 H 0.084845 0.416872 -0.118508 0.025 Uiso 1 1 calc R U . . .
C43 C -0.09041(10) 0.86683(9) -0.30027(11) 0.0248(4) Uani 1 1 d . . . . .
H43 H -0.065689 0.832954 -0.271247 0.030 Uiso 1 1 calc R U . . .
N15 N -0.28662(8) 0.74449(8) -0.22831(9) 0.0229(3) Uani 1 1 d . . . . .
C3 C 0.13794(9) 0.34250(9) -0.05977(11) 0.0218(4) Uani 1 1 d . . . . .
C1 C 0.01569(9) 0.34116(9) -0.10500(11) 0.0201(4) Uani 1 1 d . . . . .
C16 C -0.26694(9) 0.79785(9) -0.27087(11) 0.0204(4) Uani 1 1 d . . . . .
N7 N -0.04428(8) 0.36895(8) -0.14365(10) 0.0234(3) Uani 1 1 d . . . . .
H7 H -0.080137 0.342481 -0.154696 0.028 Uiso 1 1 calc R U . . .
C4 C 0.13338(10) 0.27968(9) -0.02860(11) 0.0229(4) Uani 1 1 d . . . . .
H4 H 0.173308 0.259141 -0.002456 0.028 Uiso 1 1 calc R U . . .
N12 N -0.13845(10) 0.62583(9) -0.19087(13) 0.0219(4) Uani 0.888(3) 1 d D U P B
1
C5 C 0.06883(10) 0.24733(9) -0.03651(11) 0.0221(4) Uani 1 1 d . . . . .
C19 C -0.35936(10) 0.72012(10) -0.23840(12) 0.0261(4) Uani 1 1 d . . . . .
H19A H -0.390011 0.755657 -0.261068 0.031 Uiso 1 1 calc R U . . .
H19B H -0.376310 0.708244 -0.184546 0.031 Uiso 1 1 calc R U . . .
C38 C -0.16414(10) 0.86730(9) -0.30389(10) 0.0210(4) Uani 1 1 d . . . . .
C6 C 0.01056(9) 0.27731(9) -0.07447(10) 0.0211(4) Uani 1 1 d . . . . .
H6 H -0.033062 0.254450 -0.079809 0.025 Uiso 1 1 calc R U . . .
C44 C 0.04285(9) 0.64703(9) -0.10578(10) 0.0210(4) Uani 1 1 d . . . . .
F30 F 0.2554(3) 0.3510(5) -0.0061(7) 0.053(2) Uani 0.60(2) 1 d D U P A 1
C20 C -0.07681(10) 0.66058(9) -0.17509(11) 0.0236(4) Uani 1 1 d D . . . .
C39 C -0.19929(10) 0.91834(10) -0.34525(11) 0.0268(4) Uani 1 1 d . . . . .
H39 H -0.249384 0.919738 -0.348114 0.032 Uiso 1 1 calc R U . . .
C32 C -0.36573(10) 0.66096(10) -0.29367(11) 0.0259(4) Uani 1 1 d . . . . .
C48 C 0.12729(10) 0.72969(10) -0.06376(11) 0.0270(4) Uani 1 1 d . . . . .
H48 H 0.141467 0.774433 -0.062478 0.032 Uiso 1 1 calc R U . . .
C41 C -0.08794(11) 0.96569(10) -0.37977(11) 0.0271(4) Uani 1 1 d . . . . .
H41 H -0.062154 0.998836 -0.405925 0.033 Uiso 1 1 calc R U . . .
C37 C -0.34526(10) 0.66437(10) -0.37327(11) 0.0277(4) Uani 1 1 d . . . . .
H37 H -0.329217 0.704949 -0.393953 0.033 Uiso 1 1 calc R U . . .
C42 C -0.05314(10) 0.91500(10) -0.33840(12) 0.0265(4) Uani 1 1 d . . . . .
H42 H -0.003057 0.913421 -0.336283 0.032 Uiso 1 1 calc R U . . .
C40 C -0.16111(11) 0.96715(10) -0.38229(12) 0.0293(4) Uani 1 1 d . . . . .
H40 H -0.185470 1.002044 -0.409748 0.035 Uiso 1 1 calc R U . . .
C45 C 0.08573(10) 0.59988(10) -0.06650(11) 0.0265(4) Uani 1 1 d . . . . .
H45 H 0.071581 0.555120 -0.067136 0.032 Uiso 1 1 calc R U . . .
F31 F 0.1975(4) 0.4388(3) -0.0186(5) 0.0444(14) Uani 0.60(2) 1 d D U P A 1
C35 C -0.37064(15) 0.55033(12) -0.39385(14) 0.0484(7) Uani 1 1 d . . . . .
H35 H -0.372590 0.512796 -0.428088 0.058 Uiso 1 1 calc R U . . .
N9 N -0.11327(9) 0.44567(9) -0.21200(13) 0.0212(4) Uani 0.888(3) 1 d D U P B 1
H9 H -0.143215 0.413678 -0.223866 0.025 Uiso 0.888(3) 1 calc R U P B 1
C24 C 0.06376(10) 0.17808(10) -0.00620(12) 0.0261(4) Uani 1 1 d . . . . .
C46 C 0.14873(11) 0.61791(11) -0.02664(12) 0.0321(5) Uani 1 1 d . . . . .
H46 H 0.177743 0.585399 -0.000574 0.039 Uiso 1 1 calc R U . . .
C49 C 0.06441(10) 0.71232(10) -0.10497(11) 0.0247(4) Uani 1 1 d . . . . .
H49 H 0.036322 0.744813 -0.132404 0.030 Uiso 1 1 calc R U . . .
C36 C -0.34790(12) 0.60960(11) -0.42275(12) 0.0340(5) Uani 1 1 d . . . . .
H36 H -0.333907 0.612908 -0.477078 0.041 Uiso 1 1 calc R U . . .
C11 C -0.14864(11) 0.55687(11) -0.17219(13) 0.0212(5) Uani 0.888(3) 1 d D U P B
1
H11A H -0.198909 0.549274 -0.161820 0.025 Uiso 0.888(3) 1 calc R U P B 1
H11B H -0.120342 0.545677 -0.122044 0.025 Uiso 0.888(3) 1 calc R U P B 1
C28 C 0.20613(10) 0.37950(10) -0.05458(12) 0.0277(4) Uani 1 1 d D . . . .
C8 C -0.05291(10) 0.43388(9) -0.16627(12) 0.0250(4) Uani 1 1 d D . . . .
C47 C 0.16968(11) 0.68305(11) -0.02454(12) 0.0302(5) Uani 1 1 d . . . . .
H47 H 0.212571 0.695558 0.003428 0.036 Uiso 1 1 calc R U . . .
C10 C -0.12732(11) 0.51172(11) -0.24075(13) 0.0217(5) Uani 0.888(3) 1 d D U P B
1
H10A H -0.165677 0.510636 -0.283687 0.026 Uiso 0.888(3) 1 calc R U P B 1
H10B H -0.084585 0.529501 -0.264881 0.026 Uiso 0.888(3) 1 calc R U P B 1
C33 C -0.38856(14) 0.60095(12) -0.26554(13) 0.0472(6) Uani 1 1 d . . . . .
H33 H -0.403104 0.597496 -0.211442 0.057 Uiso 1 1 calc R U . . .
C34 C -0.39058(18) 0.54577(13) -0.31493(15) 0.0623(9) Uani 1 1 d . . . . .
H34 H -0.405708 0.504848 -0.294314 0.075 Uiso 1 1 calc R U . . .
N12A N -0.1220(7) 0.6263(6) -0.2271(10) 0.0212(12) Uani 0.112(3) 1 d D U P B 2
C11A C -0.1172(8) 0.5557(6) -0.2375(9) 0.024(3) Uani 0.112(3) 1 d D U P B 2
H11C H -0.067091 0.543390 -0.241757 0.029 Uiso 0.112(3) 1 calc R U P B 2
H11D H -0.142756 0.543218 -0.289003 0.029 Uiso 0.112(3) 1 calc R U P B 2
C10A C -0.1472(9) 0.5174(7) -0.1691(11) 0.028(3) Uani 0.112(3) 1 d D U P B 2
H10C H -0.133364 0.539108 -0.117003 0.033 Uiso 0.112(3) 1 calc R U P B 2
H10D H -0.199362 0.518207 -0.175461 0.033 Uiso 0.112(3) 1 calc R U P B 2
N9A N -0.1239(7) 0.4504(7) -0.1659(12) 0.029(3) Uani 0.112(3) 1 d D U P B 2
H9A H -0.155416 0.418873 -0.163736 0.035 Uiso 0.112(3) 1 calc R U P B 2
F31A F 0.2139(9) 0.4228(10) 0.0002(9) 0.074(4) Uani 0.40(2) 1 d D U P A 2
F29A F 0.2224(7) 0.4041(7) -0.1239(6) 0.056(3) Uani 0.40(2) 1 d D U P A 2
F30A F 0.2631(3) 0.3367(3) -0.0489(14) 0.055(3) Uani 0.40(2) 1 d D U P A 2


_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
F25 C24 1.329(2) . ?
F26 C24 1.341(2) . ?
O17 C16 1.246(2) . ?
N18 H18 0.8800 . ?
N18 C16 1.370(2) . ?
N18 C38 1.411(2) . ?
O21 C20 1.234(2) . ?
O23 C8 1.234(2) . ?
N22 H22 0.8800 . ?
N22 C44 1.413(2) . ?
N22 C20 1.376(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.523(3) . ?
C14 N15 1.453(2) . ?
F27 C24 1.327(2) . ?
F29 C28 1.312(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 H13C 0.9900 . ?
C13 H13D 0.9900 . ?
C13 N12 1.461(2) . ?
C13 N12A 1.527(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C2 C1 1.394(2) . ?
C43 H43 0.9500 . ?
C43 C38 1.398(3) . ?
C43 C42 1.380(3) . ?
N15 C16 1.356(2) . ?
N15 C19 1.469(2) . ?
C3 C4 1.383(3) . ?
C3 C28 1.496(3) . ?
C1 N7 1.396(2) . ?
C1 C6 1.399(2) . ?
N7 H7 0.8800 . ?
N7 C8 1.381(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(3) . ?
N12 C20 1.381(3) . ?
N12 C11 1.453(3) . ?
C5 C6 1.385(3) . ?
C5 C24 1.501(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C32 1.512(3) . ?
C38 C39 1.395(3) . ?
C6 H6 0.9500 . ?
C44 C45 1.397(3) . ?
C44 C49 1.391(3) . ?
F30 C28 1.333(4) . ?
C20 N12A 1.373(12) . ?
C39 H39 0.9500 . ?
C39 C40 1.390(3) . ?
C32 C37 1.390(3) . ?
C32 C33 1.384(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.389(3) . ?
C48 C47 1.384(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.386(3) . ?
C41 C40 1.388(3) . ?
C37 H37 0.9500 . ?
C37 C36 1.381(3) . ?
C42 H42 0.9500 . ?
C40 H40 0.9500 . ?
C45 H45 0.9500 . ?
C45 C46 1.385(3) . ?
F31 C28 1.359(6) . ?
C35 H35 0.9500 . ?
C35 C36 1.375(3) . ?
C35 C34 1.377(3) . ?
N9 H9 0.8800 . ?
N9 C8 1.361(3) . ?
N9 C10 1.447(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.385(3) . ?
C49 H49 0.9500 . ?
C36 H36 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.528(3) . ?
C28 F31A 1.265(10) . ?
C28 F29A 1.300(9) . ?
C28 F30A 1.388(6) . ?
C8 N9A 1.388(13) . ?
C47 H47 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C33 H33 0.9500 . ?
C33 C34 1.387(3) . ?
C34 H34 0.9500 . ?
N12A C11A 1.451(14) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A C10A 1.506(16) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A N9A 1.435(15) . ?
N9A H9A 0.8800 . ?

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
C16 N18 H18 116.3 . . ?
C16 N18 C38 127.35(15) . . ?
C38 N18 H18 116.3 . . ?
C44 N22 H22 116.0 . . ?
C20 N22 H22 116.0 . . ?
C20 N22 C44 127.92(16) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
N15 C14 H14A 109.0 . . ?
N15 C14 H14B 109.0 . . ?
N15 C14 C13 113.06(15) . . ?
C14 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C14 C13 H13C 104.3 . . ?
C14 C13 H13D 104.3 . . ?
C14 C13 N12A 132.0(6) . . ?
H13A C13 H13B 108.3 . . ?
H13C C13 H13D 105.6 . . ?
N12 C13 C14 109.02(17) . . ?
N12 C13 H13A 109.9 . . ?
N12 C13 H13B 109.9 . . ?
N12A C13 H13C 104.3 . . ?
N12A C13 H13D 104.3 . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.51(17) . . ?
C1 C2 H2 120.2 . . ?
C38 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C42 C43 C38 120.72(18) . . ?
C14 N15 C19 116.64(16) . . ?
C16 N15 C14 122.77(16) . . ?
C16 N15 C19 119.59(15) . . ?
C2 C3 C28 117.11(17) . . ?
C4 C3 C2 121.91(17) . . ?
C4 C3 C28 120.98(17) . . ?
C2 C1 N7 122.73(16) . . ?
C2 C1 C6 119.15(16) . . ?
N7 C1 C6 118.10(16) . . ?
O17 C16 N18 121.68(17) . . ?
O17 C16 N15 121.26(16) . . ?
N15 C16 N18 117.06(16) . . ?
C1 N7 H7 116.8 . . ?
C8 N7 C1 126.46(16) . . ?
C8 N7 H7 116.8 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.32(17) . . ?
C5 C4 H4 120.8 . . ?
C20 N12 C13 116.25(17) . . ?
C20 N12 C11 125.17(17) . . ?
C11 N12 C13 118.06(17) . . ?
C4 C5 C24 118.98(16) . . ?
C6 C5 C4 120.86(17) . . ?
C6 C5 C24 120.11(17) . . ?
N15 C19 H19A 109.1 . . ?
N15 C19 H19B 109.1 . . ?
N15 C19 C32 112.56(15) . . ?
H19A C19 H19B 107.8 . . ?
C32 C19 H19A 109.1 . . ?
C32 C19 H19B 109.1 . . ?
C43 C38 N18 116.25(17) . . ?
C39 C38 N18 125.11(17) . . ?
C39 C38 C43 118.64(17) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.24(17) . . ?
C5 C6 H6 119.9 . . ?
C45 C44 N22 116.30(17) . . ?
C49 C44 N22 124.47(17) . . ?
C49 C44 C45 119.23(17) . . ?
O21 C20 N22 124.16(17) . . ?
O21 C20 N12 120.73(17) . . ?
O21 C20 N12A 115.5(6) . . ?
N22 C20 N12 115.07(17) . . ?
N12A C20 N22 114.0(5) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 C38 120.07(18) . . ?
C40 C39 H39 120.0 . . ?
C37 C32 C19 120.83(17) . . ?
C33 C32 C19 121.19(18) . . ?
C33 C32 C37 117.90(19) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C47 C48 C49 121.27(19) . . ?
C42 C41 H41 120.6 . . ?
C42 C41 C40 118.81(18) . . ?
C40 C41 H41 120.6 . . ?
C32 C37 H37 119.5 . . ?
C36 C37 C32 120.96(19) . . ?
C36 C37 H37 119.5 . . ?
C43 C42 C41 120.76(18) . . ?
C43 C42 H42 119.6 . . ?
C41 C42 H42 119.6 . . ?
C39 C40 H40 119.5 . . ?
C41 C40 C39 120.98(19) . . ?
C41 C40 H40 119.5 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.46(19) . . ?
C46 C45 H45 119.8 . . ?
C36 C35 H35 120.2 . . ?
C36 C35 C34 119.5(2) . . ?
C34 C35 H35 120.2 . . ?
C8 N9 H9 120.6 . . ?
C8 N9 C10 118.81(17) . . ?
C10 N9 H9 120.6 . . ?
F25 C24 F26 105.31(15) . . ?
F25 C24 C5 112.92(16) . . ?
F26 C24 C5 111.49(15) . . ?
F27 C24 F25 106.68(16) . . ?
F27 C24 F26 106.82(17) . . ?
F27 C24 C5 113.09(16) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 C45 120.39(19) . . ?
C47 C46 H46 119.8 . . ?
C44 C49 H49 120.2 . . ?
C48 C49 C44 119.55(18) . . ?
C48 C49 H49 120.2 . . ?
C37 C36 H36 119.8 . . ?
C35 C36 C37 120.4(2) . . ?
C35 C36 H36 119.8 . . ?
N12 C11 H11A 109.1 . . ?
N12 C11 H11B 109.1 . . ?
N12 C11 C10 112.43(18) . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
F29 C28 C3 113.5(4) . . ?
F29 C28 F30 112.9(6) . . ?
F29 C28 F31 103.0(5) . . ?
F30 C28 C3 113.2(2) . . ?
F30 C28 F31 102.8(5) . . ?
F31 C28 C3 110.5(4) . . ?
F31A C28 C3 117.4(7) . . ?
F31A C28 F29A 109.6(9) . . ?
F31A C28 F30A 109.1(5) . . ?
F29A C28 C3 112.8(6) . . ?
F29A C28 F30A 94.7(8) . . ?
F30A C28 C3 110.9(3) . . ?
O23 C8 N7 123.64(17) . . ?
O23 C8 N9 122.53(18) . . ?
O23 C8 N9A 117.6(6) . . ?
N7 C8 N9A 109.4(6) . . ?
N9 C8 N7 113.80(17) . . ?
C48 C47 C46 119.09(18) . . ?
C48 C47 H47 120.5 . . ?
C46 C47 H47 120.5 . . ?
N9 C10 C11 111.59(18) . . ?
N9 C10 H10A 109.3 . . ?
N9 C10 H10B 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C32 C33 H33 119.4 . . ?
C32 C33 C34 121.2(2) . . ?
C34 C33 H33 119.4 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C20 N12A C13 112.5(8) . . ?
C20 N12A C11A 122.5(10) . . ?
C11A N12A C13 118.9(10) . . ?
N12A C11A H11C 108.9 . . ?
N12A C11A H11D 108.9 . . ?
N12A C11A C10A 113.4(13) . . ?
H11C C11A H11D 107.7 . . ?
C10A C11A H11C 108.9 . . ?
C10A C11A H11D 108.9 . . ?
C11A C10A H10C 109.0 . . ?
C11A C10A H10D 109.0 . . ?
H10C C10A H10D 107.8 . . ?
N9A C10A C11A 113.0(14) . . ?
N9A C10A H10C 109.0 . . ?
N9A C10A H10D 109.0 . . ?
C8 N9A C10A 121.9(12) . . ?
C8 N9A H9A 119.1 . . ?
C10A N9A H9A 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
N18 C38 C39 C40 -179.95(17) . . . . ?
O21 C20 N12A C13 -45.3(13) . . . . ?
O21 C20 N12A C11A 162.5(12) . . . . ?
O23 C8 N9A C10A 18(2) . . . . ?
N22 C44 C45 C46 -178.94(17) . . . . ?
N22 C44 C49 C48 178.03(16) . . . . ?
N22 C20 N12A C13 161.6(7) . . . . ?
N22 C20 N12A C11A 9.3(17) . . . . ?
C14 C13 N12 C20 -84.4(2) . . . . ?
C14 C13 N12 C11 103.4(2) . . . . ?
C14 C13 N12A C20 -30.5(15) . . . . ?
C14 C13 N12A C11A 122.8(11) . . . . ?
C14 N15 C16 O17 173.91(16) . . . . ?
C14 N15 C16 N18 -6.6(2) . . . . ?
C14 N15 C19 C32 -68.0(2) . . . . ?
C13 C14 N15 C16 -72.6(2) . . . . ?
C13 C14 N15 C19 95.93(19) . . . . ?
C13 N12 C20 O21 14.6(3) . . . . ?
C13 N12 C20 N22 -167.64(17) . . . . ?
C13 N12 C11 C10 83.4(2) . . . . ?
C13 N12A C11A C10A -73.3(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C28 F29 -60.1(5) . . . . ?
C2 C3 C28 F30 169.6(7) . . . . ?
C2 C3 C28 F31 54.9(5) . . . . ?
C2 C3 C28 F31A 79.4(13) . . . . ?
C2 C3 C28 F29A -49.6(8) . . . . ?
C2 C3 C28 F30A -154.4(11) . . . . ?
C2 C1 N7 C8 -12.4(3) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C43 C38 C39 C40 0.4(3) . . . . ?
N15 C14 C13 N12 172.32(16) . . . . ?
N15 C14 C13 N12A 156.6(7) . . . . ?
N15 C19 C32 C37 -58.7(2) . . . . ?
N15 C19 C32 C33 117.9(2) . . . . ?
C3 C2 C1 N7 -178.84(16) . . . . ?
C3 C2 C1 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 C24 177.42(16) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C2 C3 C28 179.28(17) . . . . ?
C1 N7 C8 O23 -6.0(3) . . . . ?
C1 N7 C8 N9 172.13(18) . . . . ?
C1 N7 C8 N9A -151.6(9) . . . . ?
C16 N18 C38 C43 -167.20(17) . . . . ?
C16 N18 C38 C39 13.2(3) . . . . ?
C16 N15 C19 C32 100.9(2) . . . . ?
N7 C1 C6 C5 179.22(16) . . . . ?
N7 C8 N9A C10A 165.9(14) . . . . ?
C4 C3 C28 F29 119.3(5) . . . . ?
C4 C3 C28 F30 -11.1(8) . . . . ?
C4 C3 C28 F31 -125.7(4) . . . . ?
C4 C3 C28 F31A -101.3(13) . . . . ?
C4 C3 C28 F29A 129.8(8) . . . . ?
C4 C3 C28 F30A 25.0(11) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C24 F25 45.7(2) . . . . ?
C4 C5 C24 F26 -72.6(2) . . . . ?
C4 C5 C24 F27 166.98(17) . . . . ?
N12 C11 C10 N9 159.24(17) . . . . ?
C19 N15 C16 O17 5.7(3) . . . . ?
C19 N15 C16 N18 -174.82(15) . . . . ?
C19 C32 C37 C36 176.94(19) . . . . ?
C19 C32 C33 C34 -176.3(2) . . . . ?
C38 N18 C16 O17 -2.3(3) . . . . ?
C38 N18 C16 N15 178.24(16) . . . . ?
C38 C43 C42 C41 1.3(3) . . . . ?
C38 C39 C40 C41 0.8(3) . . . . ?
C6 C1 N7 C8 169.29(17) . . . . ?
C6 C5 C24 F25 -136.72(18) . . . . ?
C6 C5 C24 F26 104.94(19) . . . . ?
C6 C5 C24 F27 -15.4(3) . . . . ?
C44 N22 C20 O21 12.3(3) . . . . ?
C44 N22 C20 N12 -165.37(18) . . . . ?
C44 N22 C20 N12A 162.7(8) . . . . ?
C44 C45 C46 C47 0.6(3) . . . . ?
C20 N22 C44 C45 169.24(17) . . . . ?
C20 N22 C44 C49 -10.2(3) . . . . ?
C20 N12 C11 C10 -88.1(3) . . . . ?
C20 N12A C11A C10A 77.3(18) . . . . ?
C32 C37 C36 C35 -0.3(3) . . . . ?
C32 C33 C34 C35 -1.0(5) . . . . ?
C37 C32 C33 C34 0.4(4) . . . . ?
C42 C43 C38 N18 178.87(16) . . . . ?
C42 C43 C38 C39 -1.5(3) . . . . ?
C42 C41 C40 C39 -1.0(3) . . . . ?
C40 C41 C42 C43 -0.1(3) . . . . ?
C45 C44 C49 C48 -1.4(3) . . . . ?
C45 C46 C47 C48 -0.9(3) . . . . ?
C24 C5 C6 C1 -178.05(16) . . . . ?
C49 C44 C45 C46 0.5(3) . . . . ?
C49 C48 C47 C46 0.0(3) . . . . ?
C36 C35 C34 C33 0.9(5) . . . . ?
C11 N12 C20 O21 -173.78(19) . . . . ?
C11 N12 C20 N22 3.9(3) . . . . ?
C28 C3 C4 C5 -178.89(17) . . . . ?
C8 N9 C10 C11 -73.3(2) . . . . ?
C47 C48 C49 C44 1.1(3) . . . . ?
C10 N9 C8 O23 -0.6(3) . . . . ?
C10 N9 C8 N7 -178.72(18) . . . . ?
C33 C32 C37 C36 0.2(3) . . . . ?
C34 C35 C36 C37 -0.3(4) . . . . ?
N12A C11A C10A N9A -162.0(13) . . . . ?
C11A C10A N9A C8 51(2) . . . . ?

_olex2_date_sample_data_collection 2021-06-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.284
_oxdiff_exptl_absorpt_empirical_full_min 0.503
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_testt1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2195688'
loop_
_audit_author_name
_audit_author_address
'Dr Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
1,1-bis(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-hexylurea
_chemical_formula_moiety         'C29 H32 F12 N6 O3'
_chemical_formula_sum            'C29 H32 F12 N6 O3'
_chemical_formula_weight         740.60
_chemical_melting_point          506-508
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.9530(3)
_cell_length_b                   12.2425(3)
_cell_length_c                   12.9211(3)
_cell_angle_alpha                69.3810(10)
_cell_angle_beta                 84.162(2)
_cell_angle_gamma                85.716(2)
_cell_volume                     1611.81(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6757
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0707 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.8885. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.424
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29504
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.018
_diffrn_reflns_theta_min         1.689
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5756
_reflns_number_total             7764
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         7764
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0354P)²+0.5441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B)
1.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C7(H7), C9(H9), C23(H23), C25(H25), C27(H27)
1.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.45241(9) 0.38260(9) 0.94844(8) 0.0299(2) Uani 1 1 d . . . . .
F2 F 0.39776(10) 0.20611(9) 0.99171(8) 0.0368(3) Uani 1 1 d . . . . .
F3 F 0.26525(8) 0.34776(9) 0.93632(8) 0.0293(2) Uani 1 1 d . . . . .
F4 F 0.15169(8) 0.33459(9) 0.58997(8) 0.0335(2) Uani 1 1 d . . . . .
F5 F 0.25741(10) 0.18930(10) 0.56843(9) 0.0408(3) Uani 1 1 d . . . . .
F6 F 0.28848(10) 0.36140(12) 0.45306(8) 0.0476(3) Uani 1 1 d . . . . .
F7 F 1.06461(10) 1.07612(9) 0.25771(8) 0.0345(2) Uani 1 1 d . . . . .
F8 F 1.01717(10) 0.91364(8) 0.38443(8) 0.0318(2) Uani 1 1 d . . . . .
F9 F 0.88190(10) 1.05500(9) 0.33749(9) 0.0384(3) Uani 1 1 d . . . . .
F10 F 0.73355(9) 1.16655(8) -0.04795(9) 0.0372(3) Uani 1 1 d . . . . .
F11 F 0.61341(8) 1.02573(9) 0.03282(9) 0.0349(2) Uani 1 1 d . . . . .
F12 F 0.72878(10) 1.02677(9) -0.11206(8) 0.0366(3) Uani 1 1 d . . . . .
O1 O 0.69890(10) 0.36287(10) 0.43390(8) 0.0232(2) Uani 1 1 d . . . . .
O2 O 0.95746(10) 0.35914(9) 0.07936(8) 0.0208(2) Uani 1 1 d . . . . .
O3 O 1.11320(9) 0.63340(9) 0.26241(8) 0.0169(2) Uani 1 1 d . . . . .
N1 N 0.87383(12) 0.37900(12) 0.50648(10) 0.0200(3) Uani 1 1 d . . . . .
N2 N 0.69521(12) 0.34678(13) 0.61725(11) 0.0238(3) Uani 1 1 d . . . . .
N3 N 1.01401(11) 0.32469(11) 0.25248(9) 0.0162(3) Uani 1 1 d . . . . .
N4 N 0.80784(12) 0.33544(11) 0.21861(11) 0.0190(3) Uani 1 1 d . . . . .
N5 N 1.13184(12) 0.54579(11) 0.13298(10) 0.0168(3) Uani 1 1 d . . . . .
N6 N 1.01769(11) 0.71697(11) 0.10091(10) 0.0169(3) Uani 1 1 d . . . . .
C1 C 0.98168(14) 0.29644(13) 0.37103(11) 0.0170(3) Uani 1 1 d . . . . .
H1A H 1.052609 0.255103 0.412358 0.020 Uiso 1 1 calc R . . . .
H1B H 0.912433 0.243183 0.394346 0.020 Uiso 1 1 calc R . . . .
C2 C 0.94521(14) 0.40591(13) 0.40057(12) 0.0179(3) Uani 1 1 d . . . . .
H2A H 1.020410 0.444852 0.402839 0.022 Uiso 1 1 calc R . . . .
H2B H 0.896680 0.461050 0.341947 0.022 Uiso 1 1 calc R . . . .
C3 C 0.75190(14) 0.36275(14) 0.51332(12) 0.0196(3) Uani 1 1 d . . . . .
C4 C 0.57104(13) 0.33487(14) 0.65181(12) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.53653(14) 0.33190(14) 0.75985(12) 0.0194(3) Uani 1 1 d . . . . .
H5A H 0.597153 0.337629 0.805096 0.023 Uiso 1 1 calc R . . . .
C6 C 0.41496(14) 0.32071(13) 0.80150(12) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.32441(14) 0.31189(14) 0.73733(12) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.240861 0.304126 0.765942 0.024 Uiso 1 1 calc R . . . .
C8 C 0.35955(14) 0.31477(13) 0.63036(12) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.48112(14) 0.32603(14) 0.58649(12) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.502676 0.327672 0.512869 0.024 Uiso 1 1 calc R . . . .
C10 C 0.38271(14) 0.31401(14) 0.91870(13) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.26536(14) 0.30024(15) 0.56104(13) 0.0252(4) Uani 1 1 d . . . . .
C12 C 0.92705(14) 0.34121(12) 0.17961(12) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.71113(14) 0.35514(14) 0.14306(12) 0.0215(3) Uani 1 1 d . . . . .
H13A H 0.734097 0.312696 0.090909 0.026 Uiso 1 1 calc R . . . .
H13B H 0.703038 0.439487 0.099116 0.026 Uiso 1 1 calc R . . . .
C14 C 0.58884(14) 0.31386(14) 0.20625(13) 0.0236(3) Uani 1 1 d . . . . .
H14A H 0.522611 0.345024 0.155557 0.028 Uiso 1 1 calc R . . . .
H14B H 0.573359 0.346006 0.266993 0.028 Uiso 1 1 calc R . . . .
C15 C 0.58372(15) 0.18108(15) 0.25528(15) 0.0287(4) Uani 1 1 d . . . . .
H15A H 0.604816 0.148913 0.195036 0.034 Uiso 1 1 calc R . . . .
H15B H 0.646810 0.150641 0.309310 0.034 Uiso 1 1 calc R . . . .
C16 C 0.45979(15) 0.13731(16) 0.31285(15) 0.0316(4) Uani 1 1 d . . . . .
H16A H 0.440238 0.166306 0.375382 0.038 Uiso 1 1 calc R . . . .
H16B H 0.395991 0.170246 0.259888 0.038 Uiso 1 1 calc R . . . .
C17 C 0.45494(17) 0.00511(17) 0.35675(18) 0.0389(5) Uani 1 1 d . . . . .
H17A H 0.518797 -0.027971 0.409630 0.047 Uiso 1 1 calc R . . . .
H17B H 0.474075 -0.023998 0.294248 0.047 Uiso 1 1 calc R . . . .
C18 C 0.33035(19) -0.0379(2) 0.4147(2) 0.0503(6) Uani 1 1 d . . . . .
H18A H 0.267794 -0.011509 0.361012 0.075 Uiso 1 1 calc GR . . . .
H18B H 0.308997 -0.006367 0.474481 0.075 Uiso 1 1 calc GR . . . .
H18C H 0.334113 -0.123423 0.445799 0.075 Uiso 1 1 calc GR . . . .
C19 C 1.14294(13) 0.32999(13) 0.21140(12) 0.0176(3) Uani 1 1 d . . . . .
H19A H 1.150808 0.319710 0.138337 0.021 Uiso 1 1 calc R . . . .
H19B H 1.189324 0.264171 0.262887 0.021 Uiso 1 1 calc R . . . .
C20 C 1.20096(13) 0.44403(13) 0.19903(12) 0.0177(3) Uani 1 1 d . . . . .
H20A H 1.206128 0.448307 0.273551 0.021 Uiso 1 1 calc R . . . .
H20B H 1.285611 0.444310 0.163841 0.021 Uiso 1 1 calc R . . . .
C21 C 1.08979(13) 0.63188(12) 0.17108(11) 0.0146(3) Uani 1 1 d . . . . .
C22 C 0.96625(13) 0.81852(12) 0.11631(12) 0.0158(3) Uani 1 1 d . . . . .
C23 C 0.99543(14) 0.85741(13) 0.19974(12) 0.0178(3) Uani 1 1 d . . . . .
H23 H 1.054813 0.815065 0.249306 0.021 Uiso 1 1 calc R . . . .
C24 C 0.93764(14) 0.95775(13) 0.21002(12) 0.0190(3) Uani 1 1 d . . . . .
C25 C 0.85156(14) 1.02264(13) 0.13894(13) 0.0206(3) Uani 1 1 d . . . . .
H25 H 0.812498 1.091367 0.147200 0.025 Uiso 1 1 calc R . . . .
C26 C 0.82395(13) 0.98435(13) 0.05518(12) 0.0196(3) Uani 1 1 d . . . . .
C27 C 0.88053(13) 0.88424(13) 0.04280(12) 0.0175(3) Uani 1 1 d . . . . .
H27 H 0.861186 0.860082 -0.015668 0.021 Uiso 1 1 calc R . . . .
C28 C 0.97452(15) 0.99968(14) 0.29783(13) 0.0237(3) Uani 1 1 d . . . . .
C29 C 0.72579(15) 1.04978(14) -0.01814(14) 0.0252(3) Uani 1 1 d . . . . .
H2 H 0.7431(16) 0.3543(14) 0.6653(14) 0.023(4) Uiso 1 1 d . . . . .
H6 H 1.0077(16) 0.7090(15) 0.0388(15) 0.024(5) Uiso 1 1 d . . . . .
H4 H 0.7856(16) 0.3388(16) 0.2804(15) 0.027(5) Uiso 1 1 d . . . . .
H5 H 1.1121(16) 0.5500(15) 0.0721(15) 0.025(5) Uiso 1 1 d . . . . .
H1 H 0.9077(17) 0.3763(16) 0.5638(15) 0.029(5) Uiso 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
F1 C10 1.3484(18) . ?
F2 C10 1.3354(19) . ?
F3 C10 1.3436(18) . ?
F4 C11 1.3433(18) . ?
F5 C11 1.336(2) . ?
F6 C11 1.3387(18) . ?
F7 C28 1.3455(19) . ?
F8 C28 1.3352(19) . ?
F9 C28 1.3366(18) . ?
F10 C29 1.3502(19) . ?
F11 C29 1.3371(19) . ?
F12 C29 1.3358(18) . ?
O1 C3 1.2288(17) . ?
O2 C12 1.2490(16) . ?
O3 C21 1.2396(16) . ?
N1 C2 1.4477(18) . ?
N1 C3 1.3543(19) . ?
N1 H1 0.851(18) . ?
N2 C3 1.3749(18) . ?
N2 C4 1.3894(19) . ?
N2 H2 0.884(17) . ?
N3 C1 1.4582(17) . ?
N3 C12 1.3617(18) . ?
N3 C19 1.4550(18) . ?
N4 C12 1.3485(19) . ?
N4 C13 1.4627(19) . ?
N4 H4 0.825(18) . ?
N5 C20 1.4475(19) . ?
N5 C21 1.3461(18) . ?
N5 H5 0.820(18) . ?
N6 C21 1.3742(19) . ?
N6 C22 1.3962(18) . ?
N6 H6 0.860(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.533(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.397(2) . ?
C4 C9 1.394(2) . ?
C5 H5A 0.9500 . ?
C5 C6 1.382(2) . ?
C6 C7 1.389(2) . ?
C6 C10 1.494(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.385(2) . ?
C8 C9 1.390(2) . ?
C8 C11 1.492(2) . ?
C9 H9 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.518(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.526(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.518(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.524(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.527(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 C23 1.3947(19) . ?
C22 C27 1.400(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(2) . ?
C24 C25 1.383(2) . ?
C24 C28 1.500(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.388(2) . ?
C26 C27 1.384(2) . ?
C26 C29 1.496(2) . ?
C27 H27 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 N1 H1 120.1(12) . . ?
C3 N1 C2 119.86(12) . . ?
C3 N1 H1 119.9(12) . . ?
C3 N2 C4 128.36(13) . . ?
C3 N2 H2 114.9(11) . . ?
C4 N2 H2 116.3(11) . . ?
C12 N3 C1 121.80(12) . . ?
C12 N3 C19 118.94(11) . . ?
C19 N3 C1 119.20(12) . . ?
C12 N4 C13 120.42(12) . . ?
C12 N4 H4 121.6(13) . . ?
C13 N4 H4 115.9(13) . . ?
C20 N5 H5 120.1(12) . . ?
C21 N5 C20 122.27(12) . . ?
C21 N5 H5 117.4(12) . . ?
C21 N6 C22 127.00(12) . . ?
C21 N6 H6 116.2(12) . . ?
C22 N6 H6 116.7(12) . . ?
N3 C1 H1A 109.2 . . ?
N3 C1 H1B 109.2 . . ?
N3 C1 C2 112.01(12) . . ?
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
N1 C2 C1 112.24(12) . . ?
N1 C2 H2A 109.2 . . ?
N1 C2 H2B 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 N1 122.68(13) . . ?
O1 C3 N2 124.32(14) . . ?
N1 C3 N2 113.00(12) . . ?
N2 C4 C5 116.39(13) . . ?
N2 C4 C9 124.55(13) . . ?
C9 C4 C5 119.06(14) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 C4 120.60(13) . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C7 120.96(13) . . ?
C5 C6 C10 118.81(13) . . ?
C7 C6 C10 120.20(13) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.02(14) . . ?
C8 C7 H7 121.0 . . ?
C7 C8 C9 122.15(14) . . ?
C7 C8 C11 119.32(14) . . ?
C9 C8 C11 118.47(13) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 C4 119.21(13) . . ?
C8 C9 H9 120.4 . . ?
F1 C10 C6 112.07(13) . . ?
F2 C10 F1 106.32(13) . . ?
F2 C10 F3 106.16(13) . . ?
F2 C10 C6 112.77(13) . . ?
F3 C10 F1 106.49(12) . . ?
F3 C10 C6 112.55(13) . . ?
F4 C11 C8 112.82(13) . . ?
F5 C11 F4 105.62(13) . . ?
F5 C11 F6 106.08(13) . . ?
F5 C11 C8 112.78(14) . . ?
F6 C11 F4 106.32(13) . . ?
F6 C11 C8 112.64(13) . . ?
O2 C12 N3 120.56(13) . . ?
O2 C12 N4 120.94(13) . . ?
N4 C12 N3 118.49(12) . . ?
N4 C13 H13A 109.4 . . ?
N4 C13 H13B 109.4 . . ?
N4 C13 C14 111.23(12) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 113.07(13) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C14 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.16(14) . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.37(15) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
C16 C17 C18 112.94(16) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
N3 C19 C20 113.93(12) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
N5 C20 C19 112.39(12) . . ?
N5 C20 H20A 109.1 . . ?
N5 C20 H20B 109.1 . . ?
C19 C20 H20A 109.1 . . ?
C19 C20 H20B 109.1 . . ?
H20A C20 H20B 107.9 . . ?
O3 C21 N5 122.68(14) . . ?
O3 C21 N6 122.91(13) . . ?
N5 C21 N6 114.41(12) . . ?
N6 C22 C27 117.25(12) . . ?
C23 C22 N6 123.89(13) . . ?
C23 C22 C27 118.86(13) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.74(14) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 122.00(13) . . ?
C23 C24 C28 118.41(14) . . ?
C25 C24 C28 119.53(13) . . ?
C24 C25 H25 121.0 . . ?
C24 C25 C26 118.03(14) . . ?
C26 C25 H25 121.0 . . ?
C25 C26 C29 118.55(14) . . ?
C27 C26 C25 121.23(14) . . ?
C27 C26 C29 120.12(13) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.12(13) . . ?
C26 C27 H27 119.9 . . ?
F7 C28 C24 111.20(13) . . ?
F8 C28 F7 106.20(13) . . ?
F8 C28 F9 107.10(13) . . ?
F8 C28 C24 113.08(12) . . ?
F9 C28 F7 106.27(12) . . ?
F9 C28 C24 112.53(13) . . ?
F10 C29 C26 112.01(13) . . ?
F11 C29 F10 105.65(13) . . ?
F11 C29 C26 111.84(14) . . ?
F12 C29 F10 106.60(13) . . ?
F12 C29 F11 106.81(13) . . ?
F12 C29 C26 113.42(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
C9 H9 O1 0.95 2.29 2.8910(18) 120.8 . yes
C23 H23 O3 0.95 2.22 2.8214(18) 120.3 . yes
N2 H2 O3 0.884(17) 1.951(18) 2.8083(16) 162.8(15) 2_766 yes
N6 H6 O2 0.860(17) 1.976(17) 2.7803(15) 155.2(16) 2_765 yes
N5 H5 O2 0.820(18) 2.072(18) 2.8224(16) 152.1(17) 2_765 yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_testm1
_database_code_depnum_ccdc_archive 'CCDC 2190005'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C28 H31 F3 N6 O3'
_chemical_formula_sum            'C29 H32 Cl3 F3 N6 O3'
_chemical_formula_weight         675.95
_chemical_melting_point          457
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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9677(5)
_cell_length_b                   20.0581(8)
_cell_length_c                   14.2211(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.923(2)
_cell_angle_gamma                90
_cell_volume                     3166.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.28
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0753 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.7994. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.435
_exptl_crystal_size_mid          0.392
_exptl_crystal_size_min          0.256
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29238
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.164
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5128
_reflns_number_total             7652
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.630
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         7652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.8567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1392
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C10(H10A,H10B), C11(H11A,H11B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6A), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10650(8) 0.47342(4) 0.67869(7) 0.0569(2) Uani 1 1 d . . . . .
Cl2 Cl 0.28959(8) 0.43893(4) 0.87336(5) 0.0493(2) Uani 1 1 d . . . . .
Cl3 Cl 0.10906(7) 0.34241(3) 0.76630(6) 0.0467(2) Uani 1 1 d . . . . .
C29 C 0.1964(2) 0.40915(11) 0.75284(19) 0.0289(5) Uani 1 1 d . . . . .
H29 H 0.249374 0.392243 0.717843 0.035 Uiso 1 1 calc R . . . .
F1 F 0.38088(19) 0.19896(8) 1.02501(13) 0.0581(5) Uani 1 1 d . . . . .
F2 F 0.54077(17) 0.16510(11) 1.00856(15) 0.0722(6) Uani 1 1 d . . . . .
F3 F 0.37972(17) 0.10646(7) 0.95239(12) 0.0511(5) Uani 1 1 d . . . . .
O1 O 0.27722(15) 0.74473(7) 0.12830(12) 0.0247(4) Uani 1 1 d . . . . .
O2 O 0.36752(16) 0.64837(7) 0.47815(12) 0.0292(4) Uani 1 1 d . . . . .
O3 O 0.36696(14) 0.40534(7) 0.62043(12) 0.0242(4) Uani 1 1 d . . . . .
N1 N 0.28314(18) 0.63861(9) 0.18538(14) 0.0243(4) Uani 1 1 d . . . . .
N2 N 0.34614(18) 0.72644(9) 0.29933(15) 0.0221(4) Uani 1 1 d . . . . .
N3 N 0.26270(18) 0.55401(9) 0.41319(14) 0.0252(4) Uani 1 1 d . . . . .
N4 N 0.38628(18) 0.55958(9) 0.58442(14) 0.0245(4) Uani 1 1 d . . . . .
N5 N 0.30487(19) 0.37049(9) 0.45693(15) 0.0261(4) Uani 1 1 d . . . . .
N6 N 0.31250(18) 0.29567(9) 0.58000(15) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.3091(3) 0.58496(14) 0.0385(2) 0.0513(8) Uani 1 1 d . . . . .
H1A H 0.264190 0.568024 -0.029910 0.077 Uiso 1 1 calc GR . . . .
H1B H 0.354496 0.548428 0.081707 0.077 Uiso 1 1 calc GR . . . .
H1C H 0.364951 0.619833 0.035454 0.077 Uiso 1 1 calc GR . . . .
C2 C 0.2224(2) 0.61349(11) 0.08196(18) 0.0323(6) Uani 1 1 d . . . . .
H2A H 0.176751 0.650335 0.038006 0.039 Uiso 1 1 calc R . . . .
H2B H 0.164003 0.578565 0.082118 0.039 Uiso 1 1 calc R . . . .
C3 C 0.3003(2) 0.70577(10) 0.20083(17) 0.0215(5) Uani 1 1 d . . . . .
C4 C 0.37432(19) 0.79337(10) 0.33118(17) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.4227(2) 0.83781(10) 0.28133(17) 0.0232(5) Uani 1 1 d . . . . .
H5A H 0.436373 0.823963 0.222660 0.028 Uiso 1 1 calc R . . . .
C6 C 0.4509(2) 0.90256(11) 0.31760(18) 0.0291(5) Uani 1 1 d . . . . .
H6A H 0.485034 0.932628 0.284139 0.035 Uiso 1 1 calc R . . . .
C7 C 0.4295(2) 0.92336(12) 0.4020(2) 0.0356(6) Uani 1 1 d . . . . .
H7 H 0.446251 0.968067 0.425042 0.043 Uiso 1 1 calc R . . . .
C8 C 0.3839(3) 0.87908(13) 0.4527(2) 0.0392(7) Uani 1 1 d . . . . .
H8 H 0.370661 0.893114 0.511506 0.047 Uiso 1 1 calc R . . . .
C9 C 0.3573(2) 0.81401(12) 0.4181(2) 0.0319(6) Uani 1 1 d . . . . .
H9 H 0.327287 0.783490 0.454089 0.038 Uiso 1 1 calc R . . . .
C10 C 0.3148(2) 0.59022(10) 0.26851(18) 0.0251(5) Uani 1 1 d . . . . .
H10A H 0.392288 0.603249 0.321995 0.030 Uiso 1 1 calc R . . . .
H10B H 0.325426 0.545709 0.242929 0.030 Uiso 1 1 calc R . . . .
C11 C 0.2183(2) 0.58627(11) 0.31372(17) 0.0251(5) Uani 1 1 d . . . . .
H11A H 0.190361 0.631855 0.320401 0.030 Uiso 1 1 calc R . . . .
H11B H 0.148495 0.560926 0.267267 0.030 Uiso 1 1 calc R . . . .
C12 C 0.3405(2) 0.59052(10) 0.49185(17) 0.0243(5) Uani 1 1 d . . . . .
C13 C 0.4439(2) 0.59028(10) 0.67945(17) 0.0207(5) Uani 1 1 d . . . . .
C14 C 0.4910(2) 0.65505(11) 0.69279(19) 0.0270(5) Uani 1 1 d . . . . .
H14 H 0.487489 0.681136 0.635999 0.032 Uiso 1 1 calc R . . . .
C15 C 0.5429(2) 0.68058(11) 0.79039(19) 0.0299(6) Uani 1 1 d . . . . .
H15 H 0.574626 0.724554 0.799579 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5496(2) 0.64376(12) 0.87446(19) 0.0307(6) Uani 1 1 d . . . . .
H16 H 0.584731 0.662194 0.940587 0.037 Uiso 1 1 calc R . . . .
C17 C 0.5040(2) 0.57956(12) 0.86050(19) 0.0301(5) Uani 1 1 d . . . . .
H17 H 0.508468 0.553616 0.917678 0.036 Uiso 1 1 calc R . . . .
C18 C 0.4521(2) 0.55266(11) 0.76428(18) 0.0251(5) Uani 1 1 d . . . . .
H18 H 0.421928 0.508355 0.755948 0.030 Uiso 1 1 calc R . . . .
C19 C 0.2280(2) 0.48545(10) 0.42375(18) 0.0243(5) Uani 1 1 d . . . . .
H19A H 0.150467 0.475265 0.368141 0.029 Uiso 1 1 calc R . . . .
H19B H 0.216124 0.480816 0.488711 0.029 Uiso 1 1 calc R . . . .
C20 C 0.3231(2) 0.43559(10) 0.42107(18) 0.0267(5) Uani 1 1 d . . . . .
H20A H 0.319898 0.431647 0.350722 0.032 Uiso 1 1 calc R . . . .
H20B H 0.403971 0.452292 0.463865 0.032 Uiso 1 1 calc R . . . .
C21 C 0.3310(2) 0.36033(10) 0.55624(17) 0.0217(5) Uani 1 1 d . . . . .
C22 C 0.3363(2) 0.26841(10) 0.67637(17) 0.0210(5) Uani 1 1 d . . . . .
C23 C 0.4144(2) 0.29749(10) 0.76600(17) 0.0219(5) Uani 1 1 d . . . . .
H23 H 0.450586 0.339387 0.764333 0.026 Uiso 1 1 calc R . . . .
C24 C 0.4386(2) 0.26497(10) 0.85714(18) 0.0237(5) Uani 1 1 d . . . . .
H24 H 0.491691 0.284856 0.918082 0.028 Uiso 1 1 calc R . . . .
C25 C 0.3864(2) 0.20334(11) 0.86101(18) 0.0263(5) Uani 1 1 d . . . . .
C26 C 0.3056(2) 0.17540(11) 0.77194(18) 0.0269(5) Uani 1 1 d . . . . .
H26 H 0.267685 0.134088 0.773898 0.032 Uiso 1 1 calc R . . . .
C27 C 0.2808(2) 0.20779(10) 0.68114(18) 0.0257(5) Uani 1 1 d . . . . .
H27 H 0.225114 0.188694 0.620669 0.031 Uiso 1 1 calc R . . . .
C28 C 0.4213(2) 0.16852(12) 0.9601(2) 0.0336(6) Uani 1 1 d . . . . .
H2 H 0.346(2) 0.6999(11) 0.3478(19) 0.022(6) Uiso 1 1 d . . . . .
H4 H 0.372(2) 0.5205(12) 0.5877(19) 0.023(7) Uiso 1 1 d . . . . .
H5 H 0.282(2) 0.3378(13) 0.415(2) 0.035(7) Uiso 1 1 d . . . . .
H6 H 0.281(2) 0.2694(11) 0.5297(19) 0.023(6) Uiso 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
Cl1 C29 1.756(2) . ?
Cl2 C29 1.764(3) . ?
Cl3 C29 1.752(2) . ?
C29 H29 1.0000 . ?
F1 C28 1.339(3) . ?
F2 C28 1.337(3) . ?
F3 C28 1.330(3) . ?
O1 C3 1.240(3) . ?
O2 C12 1.239(3) . ?
O3 C21 1.241(3) . ?
N1 C2 1.465(3) . ?
N1 C3 1.368(3) . ?
N1 C10 1.466(3) . ?
N2 C3 1.364(3) . ?
N2 C4 1.417(3) . ?
N2 H2 0.87(2) . ?
N3 C11 1.463(3) . ?
N3 C12 1.370(3) . ?
N3 C19 1.460(3) . ?
N4 C12 1.371(3) . ?
N4 C13 1.409(3) . ?
N4 H4 0.81(2) . ?
N5 C20 1.447(3) . ?
N5 C21 1.343(3) . ?
N5 H5 0.86(3) . ?
N6 C21 1.379(3) . ?
N6 C22 1.402(3) . ?
N6 H6 0.85(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.505(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C4 C5 1.392(3) . ?
C4 C9 1.389(3) . ?
C5 H5A 0.9500 . ?
C5 C6 1.392(3) . ?
C6 H6A 0.9500 . ?
C6 C7 1.382(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.520(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C14 1.400(3) . ?
C13 C18 1.395(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.526(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 C23 1.396(3) . ?
C22 C27 1.399(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.381(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.395(3) . ?
C25 C26 1.393(3) . ?
C25 C28 1.486(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.375(3) . ?
C27 H27 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
Cl1 C29 Cl2 110.99(12) . . ?
Cl1 C29 H29 108.1 . . ?
Cl2 C29 H29 108.1 . . ?
Cl3 C29 Cl1 111.69(14) . . ?
Cl3 C29 Cl2 109.82(14) . . ?
Cl3 C29 H29 108.1 . . ?
C2 N1 C10 117.64(17) . . ?
C3 N1 C2 119.22(18) . . ?
C3 N1 C10 122.98(18) . . ?
C3 N2 C4 124.95(18) . . ?
C3 N2 H2 120.6(16) . . ?
C4 N2 H2 113.4(15) . . ?
C12 N3 C11 116.35(18) . . ?
C12 N3 C19 123.51(18) . . ?
C19 N3 C11 120.08(18) . . ?
C12 N4 C13 126.87(18) . . ?
C12 N4 H4 118.5(18) . . ?
C13 N4 H4 114.1(18) . . ?
C20 N5 H5 119.9(18) . . ?
C21 N5 C20 120.06(19) . . ?
C21 N5 H5 119.9(18) . . ?
C21 N6 C22 127.85(19) . . ?
C21 N6 H6 115.8(16) . . ?
C22 N6 H6 116.3(16) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C2 C1 112.5(2) . . ?
N1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 N1 120.89(19) . . ?
O1 C3 N2 122.80(19) . . ?
N2 C3 N1 116.29(18) . . ?
C5 C4 N2 122.6(2) . . ?
C9 C4 N2 118.1(2) . . ?
C9 C4 C5 119.3(2) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5A 120.1 . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6A 119.8 . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.3(2) . . ?
C4 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
N1 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
N1 C10 C11 111.54(19) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
N3 C11 C10 111.88(19) . . ?
N3 C11 H11A 109.2 . . ?
N3 C11 H11B 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
O2 C12 N3 120.7(2) . . ?
O2 C12 N4 122.7(2) . . ?
N3 C12 N4 116.62(19) . . ?
C14 C13 N4 124.3(2) . . ?
C18 C13 N4 116.37(19) . . ?
C18 C13 C14 119.3(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 119.0(2) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.8(2) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.6 . . ?
C15 C16 C17 118.7(2) . . ?
C17 C16 H16 120.6 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.8(2) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
N3 C19 H19A 109.3 . . ?
N3 C19 H19B 109.3 . . ?
N3 C19 C20 111.79(19) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
N5 C20 C19 111.75(19) . . ?
N5 C20 H20A 109.3 . . ?
N5 C20 H20B 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
O3 C21 N5 122.9(2) . . ?
O3 C21 N6 123.2(2) . . ?
N5 C21 N6 113.89(19) . . ?
C23 C22 N6 123.49(19) . . ?
C23 C22 C27 119.1(2) . . ?
C27 C22 N6 117.3(2) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.6(2) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.5 . . ?
C23 C24 C25 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C28 118.8(2) . . ?
C26 C25 C24 119.3(2) . . ?
C26 C25 C28 121.8(2) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 C25 119.8(2) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 H27 119.5 . . ?
C26 C27 C22 121.1(2) . . ?
C26 C27 H27 119.5 . . ?
F1 C28 C25 113.2(2) . . ?
F2 C28 F1 105.1(2) . . ?
F2 C28 C25 112.4(2) . . ?
F3 C28 F1 105.3(2) . . ?
F3 C28 F2 106.8(2) . . ?
F3 C28 C25 113.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C29 H29 O3 1.00 2.33 3.254(3) 153.4 . yes
C9 H9 O2 0.95 2.75 3.421(3) 128.2 . yes
C15 H15 F1 0.95 2.81 3.431(3) 124.3 3_667 yes
C16 H16 F1 0.95 2.83 3.435(3) 122.4 3_667 yes
N2 H2 O2 0.87(2) 2.05(3) 2.915(2) 170(2) . yes
N4 H4 O3 0.81(2) 2.36(2) 3.158(2) 169(2) . yes
N5 H5 O1 0.86(3) 2.01(3) 2.812(2) 155(3) 2_545 yes
N6 H6 O1 0.85(2) 2.15(3) 2.932(2) 153(2) 2_545 yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile chloroform'
####################################################################### 
# 
# 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_testm1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2189988'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2019-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 F6 N4 O2'
_chemical_formula_sum            'C23 H26 F6 N4 O2'
_chemical_formula_weight         504.48
_chemical_melting_point          422
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.0463(4)
_cell_length_b                   21.9267(6)
_cell_length_c                   18.6546(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.3610(10)
_cell_angle_gamma                90
_cell_volume                     7117.8(3)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    8952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0851 before and 0.0588 after correction. The Ratio of minimum to maximum transmission is 0.7409. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3144
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.426
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            64703
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.937
_diffrn_reflns_theta_min         1.464
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                10765
_reflns_number_total             17042
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1015
_refine_ls_number_reflns         17042
_refine_ls_number_restraints     70
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+4.5874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1395
_refine_special_details          
;
Occupancies of disordered atoms were refined with their sum set to equal 1.
Restraints were applied to maintain sensible thermal and geometric
parameters.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N10-C53 \\sim N10A-C53
 with sigma of 0.01
 N10A-C54A \\sim N10-C54
 with sigma of 0.01
 C55A-C54A \\sim C55-C54
 with sigma of 0.01
 N11-C55A \\sim N11-C55
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N10 \\sim C54 \\sim C55 \\sim C55A \\sim C54A \\sim N10A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C55A)=Sof(H55C)=Sof(H55D)=Sof(C54A)=Sof(H54C)=Sof(H54D)=Sof(N10A)=
 Sof(H10A)=1-FVAR(1)
 Sof(N10)=Sof(H10)=Sof(C54)=Sof(H54A)=Sof(H54B)=Sof(C55)=Sof(H55A)=Sof(H55B)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10B,H10C), C11(H11A,H11B), C17(H17A,H17B), C32(H32A,H32B), C33(H33A,
 H33B), C39(H39A,H39B), C54(H54A,H54B), C55(H55A,H55B), C61(H61A,H61B),
 C55A(H55C,H55D), C54A(H54C,H54D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C5(H5), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24), C26(H26), C28(H28), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45),
  N10(H10), C46(H46), C48(H48), C50(H50), C63(H63), C64(H64), C65(H65),
 C66(H66), C67(H67), N10A(H10A)
5.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C58(H58A,H58B,H58C), C59(H59A,
 H59B,H59C), C60(H60A,H60B,H60C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.17711(10) 0.39608(7) -0.35486(8) 0.0484(4) Uani 1 1 d . . . . .
F2 F 0.25832(11) 0.34559(7) -0.27143(8) 0.0553(5) Uani 1 1 d . . . . .
F3 F 0.29541(11) 0.39417(8) -0.35467(10) 0.0596(5) Uani 1 1 d . . . . .
F4 F 0.17915(9) 0.62289(7) -0.34476(8) 0.0407(4) Uani 1 1 d . . . . .
F5 F 0.29943(9) 0.64269(8) -0.30807(11) 0.0609(5) Uani 1 1 d . . . . .
F6 F 0.22603(12) 0.66433(7) -0.23952(9) 0.0577(5) Uani 1 1 d . . . . .
O1 O 0.39420(9) 0.59183(7) -0.04116(8) 0.0235(3) Uani 1 1 d . . . . .
O2 O 0.49722(9) 0.76526(6) 0.15016(8) 0.0233(3) Uani 1 1 d . . . . .
N1 N 0.35130(11) 0.49332(8) -0.06692(9) 0.0200(4) Uani 1 1 d . . . . .
N2 N 0.43051(11) 0.51918(8) 0.04721(10) 0.0227(4) Uani 1 1 d . . . . .
N3 N 0.47944(11) 0.66300(8) 0.15643(9) 0.0233(4) Uani 1 1 d . . . . .
N4 N 0.44247(11) 0.71292(8) 0.04339(10) 0.0208(4) Uani 1 1 d . . . . .
C1 C 0.29934(13) 0.44830(10) -0.18681(11) 0.0230(5) Uani 1 1 d . . . . .
H1A H 0.314325 0.409399 -0.165459 0.028 Uiso 1 1 calc R . . . .
C2 C 0.26282(13) 0.45318(10) -0.26192(12) 0.0249(5) Uani 1 1 d . . . . .
C3 C 0.24101(13) 0.50932(11) -0.29506(12) 0.0255(5) Uani 1 1 d . . . . .
H3 H 0.216669 0.512372 -0.346742 0.031 Uiso 1 1 calc R . . . .
C4 C 0.25576(13) 0.56076(10) -0.25057(12) 0.0223(5) Uani 1 1 d . . . . .
C5 C 0.29102(12) 0.55732(10) -0.17495(11) 0.0203(4) Uani 1 1 d . . . . .
H5 H 0.299437 0.593221 -0.145392 0.024 Uiso 1 1 calc R . . . .
C6 C 0.31410(12) 0.50040(10) -0.14260(11) 0.0198(4) Uani 1 1 d . . . . .
C7 C 0.24860(16) 0.39708(11) -0.31006(13) 0.0343(6) Uani 1 1 d . . . . .
C8 C 0.23909(14) 0.62227(11) -0.28530(13) 0.0297(5) Uani 1 1 d . . . . .
C9 C 0.39226(13) 0.53850(10) -0.02134(11) 0.0194(4) Uani 1 1 d . . . . .
C10 C 0.48029(13) 0.56271(10) 0.09628(12) 0.0244(5) Uani 1 1 d . . . . .
H10B H 0.511515 0.584752 0.068266 0.029 Uiso 1 1 calc R . . . .
H10C H 0.515846 0.540479 0.137536 0.029 Uiso 1 1 calc R . . . .
C11 C 0.43409(14) 0.60854(10) 0.12812(12) 0.0239(5) Uani 1 1 d . . . . .
H11A H 0.387738 0.620592 0.088923 0.029 Uiso 1 1 calc R . . . .
H11B H 0.417010 0.589150 0.168942 0.029 Uiso 1 1 calc R . . . .
C12 C 0.47368(13) 0.71662(10) 0.11737(11) 0.0206(5) Uani 1 1 d . . . . .
C13 C 0.41454(13) 0.76588(9) -0.00598(11) 0.0210(5) Uani 1 1 d . . . . .
C14 C 0.37944(15) 0.73927(10) -0.08323(12) 0.0285(5) Uani 1 1 d . . . . .
H14A H 0.418712 0.716261 -0.099361 0.043 Uiso 1 1 calc GR . . . .
H14B H 0.360173 0.772444 -0.118432 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.336916 0.712026 -0.081430 0.043 Uiso 1 1 calc GR . . . .
C15 C 0.48037(14) 0.80861(10) -0.00912(12) 0.0272(5) Uani 1 1 d . . . . .
H15A H 0.504715 0.824077 0.040859 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.460273 0.842872 -0.042313 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.518386 0.786307 -0.027928 0.041 Uiso 1 1 calc GR . . . .
C16 C 0.35249(14) 0.79946(11) 0.02072(13) 0.0287(5) Uani 1 1 d . . . . .
H16A H 0.310102 0.771427 0.020356 0.043 Uiso 1 1 calc GR . . . .
H16B H 0.333227 0.833912 -0.012447 0.043 Uiso 1 1 calc GR . . . .
H16C H 0.374400 0.814555 0.071362 0.043 Uiso 1 1 calc GR . . . .
C17 C 0.51829(14) 0.66339(10) 0.23559(11) 0.0234(5) Uani 1 1 d . . . . .
H17A H 0.560997 0.693188 0.244729 0.028 Uiso 1 1 calc R . . . .
H17B H 0.540889 0.622606 0.249960 0.028 Uiso 1 1 calc R . . . .
C18 C 0.46632(14) 0.67935(10) 0.28455(12) 0.0253(5) Uani 1 1 d . . . . .
C19 C 0.39874(15) 0.71189(12) 0.25846(14) 0.0345(6) Uani 1 1 d . . . . .
H19 H 0.383516 0.724010 0.207772 0.041 Uiso 1 1 calc R . . . .
C20 C 0.35266(18) 0.72720(14) 0.30493(17) 0.0474(7) Uani 1 1 d . . . . .
H20 H 0.307052 0.750243 0.286153 0.057 Uiso 1 1 calc R . . . .
C21 C 0.37314(19) 0.70902(14) 0.37769(17) 0.0491(8) Uani 1 1 d . . . . .
H21 H 0.341740 0.719472 0.409452 0.059 Uiso 1 1 calc R . . . .
C22 C 0.43900(18) 0.67569(12) 0.40486(14) 0.0411(7) Uani 1 1 d . . . . .
H22 H 0.452366 0.662316 0.455089 0.049 Uiso 1 1 calc R . . . .
C23 C 0.48657(16) 0.66129(11) 0.35893(12) 0.0318(6) Uani 1 1 d . . . . .
H23 H 0.532772 0.639152 0.378468 0.038 Uiso 1 1 calc R . . . .
F7 F 0.27063(9) -0.12104(7) 0.26683(10) 0.0471(4) Uani 1 1 d . . . . .
F8 F 0.38740(9) -0.09211(6) 0.28992(8) 0.0392(4) Uani 1 1 d . . . . .
F9 F 0.33757(10) -0.14181(6) 0.19051(8) 0.0452(4) Uani 1 1 d . . . . .
F10 F 0.08883(9) 0.01679(10) 0.01945(9) 0.0576(5) Uani 1 1 d . . . . .
F11 F 0.16104(11) -0.04297(8) -0.02074(8) 0.0550(5) Uani 1 1 d . . . . .
F12 F 0.17146(10) 0.05312(8) -0.03090(8) 0.0512(5) Uani 1 1 d . . . . .
O3 O 0.31731(9) 0.18310(7) 0.13003(8) 0.0232(3) Uani 1 1 d . . . . .
O4 O 0.40101(9) 0.38653(6) 0.03029(8) 0.0209(3) Uani 1 1 d . . . . .
N5 N 0.31387(12) 0.12463(8) 0.23098(10) 0.0235(4) Uani 1 1 d . . . . .
N6 N 0.35498(11) 0.22398(8) 0.24551(10) 0.0223(4) Uani 1 1 d . . . . .
N7 N 0.44517(10) 0.33344(7) 0.13801(9) 0.0175(4) Uani 1 1 d . . . . .
N8 N 0.35053(10) 0.29227(8) 0.04081(9) 0.0179(4) Uani 1 1 d . . . . .
C01A C 0.29071(13) 0.06962(10) 0.19340(11) 0.0208(5) Uani 1 1 d . . . . .
C24 C 0.31896(13) 0.01514(10) 0.22879(11) 0.0202(4) Uani 1 1 d . . . . .
H24 H 0.354057 0.016115 0.276773 0.024 Uiso 1 1 calc R . . . .
C25 C 0.29629(13) -0.04035(10) 0.19459(12) 0.0210(5) Uani 1 1 d . . . . .
C26 C 0.24607(13) -0.04257(10) 0.12414(12) 0.0231(5) Uani 1 1 d . . . . .
H26 H 0.231273 -0.080633 0.100306 0.028 Uiso 1 1 calc R . . . .
C27 C 0.21784(13) 0.01128(10) 0.08908(12) 0.0227(5) Uani 1 1 d . . . . .
C28 C 0.23918(13) 0.06761(10) 0.12281(12) 0.0215(5) Uani 1 1 d . . . . .
H28 H 0.218914 0.104245 0.098077 0.026 Uiso 1 1 calc R . . . .
C29 C 0.32311(14) -0.09867(10) 0.23483(13) 0.0255(5) Uani 1 1 d . . . . .
C30 C 0.16047(14) 0.01002(11) 0.01426(13) 0.0287(5) Uani 1 1 d . . . . .
C31 C 0.32784(13) 0.17766(9) 0.19782(11) 0.0202(5) Uani 1 1 d . . . . .
C32 C 0.37056(13) 0.28314(9) 0.21719(11) 0.0206(5) Uani 1 1 d . . . . .
H32A H 0.379716 0.313480 0.257905 0.025 Uiso 1 1 calc R . . . .
H32B H 0.324992 0.296456 0.177858 0.025 Uiso 1 1 calc R . . . .
C33 C 0.44068(12) 0.28115(9) 0.18530(11) 0.0190(4) Uani 1 1 d . . . . .
H33A H 0.487934 0.279695 0.226908 0.023 Uiso 1 1 calc R . . . .
H33B H 0.438630 0.243266 0.155957 0.023 Uiso 1 1 calc R . . . .
C34 C 0.39846(12) 0.33969(9) 0.06712(11) 0.0174(4) Uani 1 1 d . . . . .
C35 C 0.29702(12) 0.28974(9) -0.03448(11) 0.0193(4) Uani 1 1 d . . . . .
C36 C 0.23770(13) 0.34074(10) -0.04418(13) 0.0271(5) Uani 1 1 d . . . . .
H36A H 0.208656 0.336293 -0.006918 0.041 Uiso 1 1 calc GR . . . .
H36B H 0.202411 0.338399 -0.094072 0.041 Uiso 1 1 calc GR . . . .
H36C H 0.263921 0.380292 -0.037780 0.041 Uiso 1 1 calc GR . . . .
C37 C 0.25612(13) 0.22803(10) -0.03909(12) 0.0240(5) Uani 1 1 d . . . . .
H37A H 0.294286 0.195177 -0.029924 0.036 Uiso 1 1 calc GR . . . .
H37B H 0.220881 0.223072 -0.088681 0.036 Uiso 1 1 calc GR . . . .
H37C H 0.227025 0.226401 -0.001601 0.036 Uiso 1 1 calc GR . . . .
C38 C 0.34147(14) 0.29151(10) -0.09336(11) 0.0254(5) Uani 1 1 d . . . . .
H38A H 0.372196 0.328923 -0.087606 0.038 Uiso 1 1 calc GR . . . .
H38B H 0.305322 0.290755 -0.142891 0.038 Uiso 1 1 calc GR . . . .
H38C H 0.375521 0.255988 -0.087465 0.038 Uiso 1 1 calc GR . . . .
C39 C 0.50362(12) 0.37988(9) 0.16636(11) 0.0194(4) Uani 1 1 d . . . . .
H39A H 0.516069 0.400248 0.123636 0.023 Uiso 1 1 calc R . . . .
H39B H 0.550914 0.359471 0.195647 0.023 Uiso 1 1 calc R . . . .
C40 C 0.48070(12) 0.42807(9) 0.21455(11) 0.0167(4) Uani 1 1 d . . . . .
C41 C 0.53812(13) 0.46133(9) 0.26400(11) 0.0197(4) Uani 1 1 d . . . . .
H41 H 0.590558 0.453591 0.266576 0.024 Uiso 1 1 calc R . . . .
C42 C 0.51941(13) 0.50546(9) 0.30931(11) 0.0221(5) Uani 1 1 d . . . . .
H42 H 0.558949 0.527823 0.342723 0.027 Uiso 1 1 calc R . . . .
C43 C 0.44299(14) 0.51710(10) 0.30602(12) 0.0236(5) Uani 1 1 d . . . . .
H43 H 0.430101 0.546890 0.337682 0.028 Uiso 1 1 calc R . . . .
C44 C 0.38563(14) 0.48501(9) 0.25628(12) 0.0222(5) Uani 1 1 d . . . . .
H44 H 0.333243 0.493289 0.253366 0.027 Uiso 1 1 calc R . . . .
C45 C 0.40429(12) 0.44077(9) 0.21062(11) 0.0187(4) Uani 1 1 d . . . . .
H45 H 0.364582 0.419089 0.176532 0.022 Uiso 1 1 calc R . . . .
F13 F 0.57533(9) -0.02365(10) 1.03469(8) 0.0626(6) Uani 1 1 d . . . . .
F14 F 0.66425(9) 0.02663(7) 1.00459(8) 0.0438(4) Uani 1 1 d . . . . .
F15 F 0.65853(8) -0.07014(7) 0.99295(8) 0.0390(4) Uani 1 1 d . . . . .
F16 F 0.45752(11) -0.16255(6) 0.78761(10) 0.0607(5) Uani 1 1 d . . . . .
F17 F 0.49859(11) -0.12356(8) 0.70018(11) 0.0640(5) Uani 1 1 d . . . . .
F18 F 0.38471(9) -0.10451(6) 0.70794(9) 0.0443(4) Uani 1 1 d . . . . .
O5 O 0.40095(11) 0.08987(7) 0.66385(8) 0.0369(5) Uani 1 1 d . . . . .
O6 O 0.32303(10) 0.15004(8) 0.38565(8) 0.0309(4) Uani 1 1 d . . . . .
N9 N 0.47110(11) 0.11075(8) 0.78280(10) 0.0207(4) Uani 1 1 d . . . . .
N10 N 0.42192(17) 0.18868(11) 0.70261(14) 0.0232(6) Uani 0.786(4) 1 d D U P A 1
H10 H 0.444127 0.214311 0.738101 0.028 Uiso 0.786(4) 1 calc R . P A 1
N11 N 0.35941(14) 0.20200(9) 0.49487(10) 0.0337(5) Uani 1 1 d D . . . .
N12 N 0.34493(13) 0.09718(9) 0.49515(11) 0.0295(5) Uani 1 1 d . . . . .
C019 C 0.49130(12) 0.05166(9) 0.80868(11) 0.0186(4) Uani 1 1 d . . . . .
C46 C 0.54206(13) 0.04443(10) 0.87912(11) 0.0205(5) Uani 1 1 d . . . . .
H46 H 0.561456 0.079353 0.908192 0.025 Uiso 1 1 calc R . . . .
C47 C 0.56432(13) -0.01326(10) 0.90690(11) 0.0215(5) Uani 1 1 d . . . . .
C48 C 0.53797(13) -0.06530(10) 0.86538(12) 0.0235(5) Uani 1 1 d . . . . .
H48 H 0.554310 -0.104786 0.883959 0.028 Uiso 1 1 calc R . . . .
C49 C 0.48707(13) -0.05755(10) 0.79599(12) 0.0238(5) Uani 1 1 d . . . . .
C50 C 0.46297(13) -0.00015(10) 0.76725(12) 0.0230(5) Uani 1 1 d . . . . .
H50 H 0.427463 0.003661 0.719731 0.028 Uiso 1 1 calc R . . . .
C51 C 0.61506(14) -0.02022(11) 0.98426(12) 0.0280(5) Uani 1 1 d . . . . .
C52 C 0.45724(15) -0.11173(11) 0.74837(15) 0.0341(6) Uani 1 1 d . . . . .
C53 C 0.43122(15) 0.12692(11) 0.71236(12) 0.0310(6) Uani 1 1 d D . . . .
C54 C 0.37428(17) 0.21045(13) 0.63189(14) 0.0232(7) Uani 0.786(4) 1 d D U P A 1
H54A H 0.362422 0.254175 0.636159 0.028 Uiso 0.786(4) 1 calc R . P A 1
H54B H 0.325174 0.187658 0.618797 0.028 Uiso 0.786(4) 1 calc R . P A 1
C55 C 0.41521(18) 0.20211(13) 0.57076(15) 0.0224(7) Uani 0.786(4) 1 d D U P A 1
H55A H 0.452773 0.235532 0.573663 0.027 Uiso 0.786(4) 1 calc R . P A 1
H55B H 0.443843 0.163100 0.578593 0.027 Uiso 0.786(4) 1 calc R . P A 1
C56 C 0.34136(14) 0.14901(11) 0.45481(12) 0.0277(5) Uani 1 1 d . . . . .
C57 C 0.34726(14) 0.03522(10) 0.46501(12) 0.0268(5) Uani 1 1 d . . . . .
C58 C 0.36056(17) -0.00835(11) 0.53074(14) 0.0354(6) Uani 1 1 d . . . . .
H58A H 0.409340 0.001614 0.566740 0.053 Uiso 1 1 calc GR . . . .
H58B H 0.362447 -0.050324 0.513260 0.053 Uiso 1 1 calc GR . . . .
H58C H 0.318459 -0.004388 0.554527 0.053 Uiso 1 1 calc GR . . . .
C59 C 0.41492(14) 0.03118(12) 0.43003(13) 0.0317(6) Uani 1 1 d . . . . .
H59A H 0.407989 0.061110 0.389778 0.048 Uiso 1 1 calc GR . . . .
H59B H 0.417161 -0.009898 0.410024 0.048 Uiso 1 1 calc GR . . . .
H59C H 0.462901 0.039756 0.467926 0.048 Uiso 1 1 calc GR . . . .
C60 C 0.27097(15) 0.01988(12) 0.40883(14) 0.0353(6) Uani 1 1 d . . . . .
H60A H 0.229264 0.021874 0.433366 0.053 Uiso 1 1 calc GR . . . .
H60B H 0.273619 -0.021336 0.389343 0.053 Uiso 1 1 calc GR . . . .
H60C H 0.261187 0.049277 0.367823 0.053 Uiso 1 1 calc GR . . . .
C61 C 0.34896(15) 0.25942(11) 0.45401(13) 0.0286(5) Uani 1 1 d . . . . .
H61A H 0.335020 0.291461 0.485489 0.034 Uiso 1 1 calc R . . . .
H61B H 0.305414 0.254949 0.409105 0.034 Uiso 1 1 calc R . . . .
C62 C 0.41874(13) 0.28023(10) 0.43050(11) 0.0231(5) Uani 1 1 d . . . . .
C63 C 0.47566(13) 0.24126(10) 0.42126(12) 0.0256(5) Uani 1 1 d . . . . .
H63 H 0.471728 0.198896 0.430281 0.031 Uiso 1 1 calc R . . . .
C64 C 0.53830(14) 0.26269(12) 0.39913(13) 0.0328(6) Uani 1 1 d . . . . .
H64 H 0.576773 0.235076 0.393094 0.039 Uiso 1 1 calc R . . . .
C65 C 0.54496(15) 0.32404(12) 0.38582(13) 0.0327(6) Uani 1 1 d . . . . .
H65 H 0.588074 0.338915 0.370967 0.039 Uiso 1 1 calc R . . . .
C66 C 0.48874(15) 0.36343(12) 0.39422(13) 0.0321(6) Uani 1 1 d . . . . .
H66 H 0.492861 0.405662 0.384571 0.039 Uiso 1 1 calc R . . . .
C67 C 0.42641(15) 0.34241(11) 0.41649(13) 0.0308(6) Uani 1 1 d . . . . .
H67 H 0.388219 0.370339 0.422413 0.037 Uiso 1 1 calc R . . . .
C55A C 0.3587(6) 0.2065(5) 0.5737(4) 0.028(2) Uani 0.214(4) 1 d D U P A 2
H55C H 0.326307 0.174550 0.587637 0.033 Uiso 0.214(4) 1 calc R . P A 2
H55D H 0.341996 0.247193 0.586118 0.033 Uiso 0.214(4) 1 calc R . P A 2
C54A C 0.4442(6) 0.1956(5) 0.6090(5) 0.023(2) Uani 0.214(4) 1 d D U P A 2
H54C H 0.462418 0.161897 0.582645 0.028 Uiso 0.214(4) 1 calc R . P A 2
H54D H 0.473451 0.232754 0.603805 0.028 Uiso 0.214(4) 1 calc R . P A 2
N10A N 0.4582(6) 0.1802(4) 0.6873(4) 0.0195(19) Uani 0.214(4) 1 d D U P A 2
H10A H 0.485015 0.205827 0.720449 0.023 Uiso 0.214(4) 1 calc R . P A 2
H2 H 0.4285(14) 0.4814(12) 0.0586(14) 0.030(7) Uiso 1 1 d . . . . .
H1 H 0.3589(15) 0.4558(12) -0.0486(14) 0.034(7) Uiso 1 1 d . . . . .
H9 H 0.4880(13) 0.1393(11) 0.8114(13) 0.020(6) Uiso 1 1 d . . . . .
H12 H 0.3606(17) 0.0989(13) 0.5454(17) 0.048(8) Uiso 1 1 d . . . . .
H4 H 0.4328(15) 0.6807(12) 0.0236(14) 0.027(7) Uiso 1 1 d . . . . .
H6 H 0.3646(16) 0.2187(12) 0.2900(16) 0.038(8) Uiso 1 1 d . . . . .
H5A H 0.3217(16) 0.1264(13) 0.2773(16) 0.042(8) Uiso 1 1 d . . . . .
H8 H 0.3490(15) 0.2617(12) 0.0704(14) 0.033(7) Uiso 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
F1 C7 1.339(3) . ?
F2 C7 1.326(3) . ?
F3 C7 1.335(3) . ?
F4 C8 1.329(3) . ?
F5 C8 1.346(3) . ?
F6 C8 1.320(3) . ?
O1 C9 1.230(2) . ?
O2 C12 1.247(2) . ?
N1 C6 1.402(3) . ?
N1 C9 1.385(3) . ?
N1 H1 0.89(3) . ?
N2 C9 1.350(3) . ?
N2 C10 1.456(3) . ?
N2 H2 0.86(3) . ?
N3 C11 1.465(3) . ?
N3 C12 1.373(3) . ?
N3 C17 1.457(3) . ?
N4 C12 1.348(3) . ?
N4 C13 1.485(3) . ?
N4 H4 0.79(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.385(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.387(3) . ?
C2 C7 1.504(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C4 C5 1.387(3) . ?
C4 C8 1.492(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 C11 1.523(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 C14 1.528(3) . ?
C13 C15 1.526(3) . ?
C13 C16 1.530(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.513(3) . ?
C18 C19 1.385(4) . ?
C18 C23 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.392(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.368(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.373(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.400(4) . ?
C23 H23 0.9500 . ?
F7 C29 1.339(3) . ?
F8 C29 1.338(3) . ?
F9 C29 1.327(3) . ?
F10 C30 1.330(3) . ?
F11 C30 1.334(3) . ?
F12 C30 1.316(3) . ?
O3 C31 1.234(2) . ?
O4 C34 1.243(2) . ?
N5 C01A 1.402(3) . ?
N5 C31 1.371(3) . ?
N5 H5A 0.84(3) . ?
N6 C31 1.354(3) . ?
N6 C32 1.456(3) . ?
N6 H6 0.81(3) . ?
N7 C33 1.462(3) . ?
N7 C34 1.374(3) . ?
N7 C39 1.461(3) . ?
N8 C34 1.358(3) . ?
N8 C35 1.480(2) . ?
N8 H8 0.87(3) . ?
C01A C24 1.394(3) . ?
C01A C28 1.397(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(3) . ?
C25 C26 1.386(3) . ?
C25 C29 1.497(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(3) . ?
C27 C28 1.393(3) . ?
C27 C30 1.502(3) . ?
C28 H28 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.535(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C35 C36 1.525(3) . ?
C35 C37 1.533(3) . ?
C35 C38 1.523(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.514(3) . ?
C40 C41 1.397(3) . ?
C40 C45 1.389(3) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(3) . ?
C42 H42 0.9500 . ?
C42 C43 1.388(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.385(3) . ?
C44 H44 0.9500 . ?
C44 C45 1.390(3) . ?
C45 H45 0.9500 . ?
F13 C51 1.327(3) . ?
F14 C51 1.345(3) . ?
F15 C51 1.331(3) . ?
F16 C52 1.333(3) . ?
F17 C52 1.337(3) . ?
F18 C52 1.336(3) . ?
O5 C53 1.231(3) . ?
O6 C56 1.244(3) . ?
N9 C019 1.397(3) . ?
N9 C53 1.367(3) . ?
N9 H9 0.83(2) . ?
N10 H10 0.8800 . ?
N10 C53 1.371(3) . ?
N10 C54 1.451(3) . ?
N11 C55 1.504(3) . ?
N11 C56 1.373(3) . ?
N11 C61 1.458(3) . ?
N11 C55A 1.477(8) . ?
N12 C56 1.355(3) . ?
N12 C57 1.475(3) . ?
N12 H12 0.90(3) . ?
C019 C46 1.398(3) . ?
C019 C50 1.393(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.385(3) . ?
C47 C48 1.390(3) . ?
C47 C51 1.498(3) . ?
C48 H48 0.9500 . ?
C48 C49 1.385(3) . ?
C49 C50 1.392(3) . ?
C49 C52 1.496(3) . ?
C50 H50 0.9500 . ?
C53 N10A 1.393(7) . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?
C54 C55 1.525(4) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C57 C58 1.522(3) . ?
C57 C59 1.532(3) . ?
C57 C60 1.531(3) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C62 1.510(3) . ?
C62 C63 1.382(3) . ?
C62 C67 1.402(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.384(3) . ?
C64 H64 0.9500 . ?
C64 C65 1.379(4) . ?
C65 H65 0.9500 . ?
C65 C66 1.373(4) . ?
C66 H66 0.9500 . ?
C66 C67 1.378(3) . ?
C67 H67 0.9500 . ?
C55A H55C 0.9900 . ?
C55A H55D 0.9900 . ?
C55A C54A 1.527(9) . ?
C54A H54C 0.9900 . ?
C54A H54D 0.9900 . ?
C54A N10A 1.454(8) . ?
N10A H10A 0.8800 . ?

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
C6 N1 H1 118.3(17) . . ?
C9 N1 C6 125.06(18) . . ?
C9 N1 H1 115.1(17) . . ?
C9 N2 C10 117.72(18) . . ?
C9 N2 H2 119.5(17) . . ?
C10 N2 H2 122.4(17) . . ?
C12 N3 C11 123.39(17) . . ?
C12 N3 C17 118.76(17) . . ?
C17 N3 C11 116.30(17) . . ?
C12 N4 C13 124.68(18) . . ?
C12 N4 H4 120.7(18) . . ?
C13 N4 H4 114.2(18) . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 C6 120.1(2) . . ?
C6 C1 H1A 120.0 . . ?
C1 C2 C3 121.5(2) . . ?
C1 C2 C7 120.1(2) . . ?
C3 C2 C7 118.44(19) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.0(2) . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 C8 119.46(19) . . ?
C5 C4 C8 118.4(2) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 N1 118.10(19) . . ?
C1 C6 C5 119.16(19) . . ?
C5 C6 N1 122.74(19) . . ?
F1 C7 C2 111.7(2) . . ?
F2 C7 F1 107.0(2) . . ?
F2 C7 F3 106.5(2) . . ?
F2 C7 C2 113.25(19) . . ?
F3 C7 F1 105.93(19) . . ?
F3 C7 C2 112.0(2) . . ?
F4 C8 F5 106.32(19) . . ?
F4 C8 C4 113.4(2) . . ?
F5 C8 C4 110.5(2) . . ?
F6 C8 F4 106.7(2) . . ?
F6 C8 F5 105.7(2) . . ?
F6 C8 C4 113.63(19) . . ?
O1 C9 N1 123.28(19) . . ?
O1 C9 N2 122.33(19) . . ?
N2 C9 N1 114.39(18) . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 H10C 109.3 . . ?
N2 C10 C11 111.55(19) . . ?
H10B C10 H10C 108.0 . . ?
C11 C10 H10B 109.3 . . ?
C11 C10 H10C 109.3 . . ?
N3 C11 C10 111.54(19) . . ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O2 C12 N3 120.29(18) . . ?
O2 C12 N4 123.33(19) . . ?
N4 C12 N3 116.38(18) . . ?
N4 C13 C14 105.90(17) . . ?
N4 C13 C15 111.36(18) . . ?
N4 C13 C16 109.38(17) . . ?
C14 C13 C16 109.55(19) . . ?
C15 C13 C14 109.31(18) . . ?
C15 C13 C16 111.19(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N3 C17 H17A 108.8 . . ?
N3 C17 H17B 108.8 . . ?
N3 C17 C18 113.84(19) . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 C23 118.0(2) . . ?
C23 C18 C17 119.6(2) . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.2(3) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C01A N5 H5A 120(2) . . ?
C31 N5 C01A 124.75(18) . . ?
C31 N5 H5A 115(2) . . ?
C31 N6 C32 120.07(18) . . ?
C31 N6 H6 121(2) . . ?
C32 N6 H6 119(2) . . ?
C34 N7 C33 122.75(17) . . ?
C34 N7 C39 118.63(17) . . ?
C39 N7 C33 118.58(16) . . ?
C34 N8 C35 124.38(17) . . ?
C34 N8 H8 118.8(17) . . ?
C35 N8 H8 116.7(17) . . ?
C24 C01A N5 118.50(19) . . ?
C24 C01A C28 119.2(2) . . ?
C28 C01A N5 122.3(2) . . ?
C01A C24 H24 119.7 . . ?
C25 C24 C01A 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C24 C25 C26 120.5(2) . . ?
C24 C25 C29 120.20(19) . . ?
C26 C25 C29 119.3(2) . . ?
C25 C26 H26 120.5 . . ?
C27 C26 C25 119.1(2) . . ?
C27 C26 H26 120.5 . . ?
C26 C27 C28 121.4(2) . . ?
C26 C27 C30 120.1(2) . . ?
C28 C27 C30 118.4(2) . . ?
C01A C28 H28 120.4 . . ?
C27 C28 C01A 119.3(2) . . ?
C27 C28 H28 120.4 . . ?
F7 C29 C25 111.32(19) . . ?
F8 C29 F7 105.58(18) . . ?
F8 C29 C25 113.12(18) . . ?
F9 C29 F7 107.19(19) . . ?
F9 C29 F8 106.35(19) . . ?
F9 C29 C25 112.79(19) . . ?
F10 C30 F11 105.5(2) . . ?
F10 C30 C27 112.0(2) . . ?
F11 C30 C27 112.2(2) . . ?
F12 C30 F10 106.3(2) . . ?
F12 C30 F11 106.9(2) . . ?
F12 C30 C27 113.46(19) . . ?
O3 C31 N5 123.20(19) . . ?
O3 C31 N6 122.13(19) . . ?
N6 C31 N5 114.67(18) . . ?
N6 C32 H32A 109.2 . . ?
N6 C32 H32B 109.2 . . ?
N6 C32 C33 111.93(18) . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 H32A 109.2 . . ?
C33 C32 H32B 109.2 . . ?
N7 C33 C32 113.24(17) . . ?
N7 C33 H33A 108.9 . . ?
N7 C33 H33B 108.9 . . ?
C32 C33 H33A 108.9 . . ?
C32 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
O4 C34 N7 120.74(18) . . ?
O4 C34 N8 123.08(18) . . ?
N8 C34 N7 116.18(18) . . ?
N8 C35 C36 110.25(17) . . ?
N8 C35 C37 105.66(16) . . ?
N8 C35 C38 110.34(18) . . ?
C36 C35 C37 109.15(19) . . ?
C38 C35 C36 112.52(18) . . ?
C38 C35 C37 108.67(18) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N7 C39 H39A 108.6 . . ?
N7 C39 H39B 108.6 . . ?
N7 C39 C40 114.63(18) . . ?
H39A C39 H39B 107.6 . . ?
C40 C39 H39A 108.6 . . ?
C40 C39 H39B 108.6 . . ?
C41 C40 C39 119.02(19) . . ?
C45 C40 C39 122.13(18) . . ?
C45 C40 C41 118.85(19) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 C40 120.7(2) . . ?
C42 C41 H41 119.7 . . ?
C41 C42 H42 119.9 . . ?
C41 C42 C43 120.1(2) . . ?
C43 C42 H42 119.9 . . ?
C42 C43 H43 120.2 . . ?
C44 C43 C42 119.6(2) . . ?
C44 C43 H43 120.2 . . ?
C43 C44 H44 119.8 . . ?
C43 C44 C45 120.4(2) . . ?
C45 C44 H44 119.8 . . ?
C40 C45 C44 120.4(2) . . ?
C40 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C019 N9 H9 117.5(16) . . ?
C53 N9 C019 126.54(19) . . ?
C53 N9 H9 115.7(16) . . ?
C53 N10 H10 121.0 . . ?
C53 N10 C54 117.9(2) . . ?
C54 N10 H10 121.0 . . ?
C56 N11 C55 121.1(2) . . ?
C56 N11 C61 117.84(19) . . ?
C56 N11 C55A 122.3(5) . . ?
C61 N11 C55 116.9(2) . . ?
C61 N11 C55A 115.4(5) . . ?
C56 N12 C57 124.24(19) . . ?
C56 N12 H12 119.7(19) . . ?
C57 N12 H12 113.6(19) . . ?
N9 C019 C46 118.44(19) . . ?
C50 C019 N9 122.75(19) . . ?
C50 C019 C46 118.81(19) . . ?
C019 C46 H46 119.7 . . ?
C47 C46 C019 120.5(2) . . ?
C47 C46 H46 119.7 . . ?
C46 C47 C48 121.23(19) . . ?
C46 C47 C51 119.7(2) . . ?
C48 C47 C51 119.0(2) . . ?
C47 C48 H48 121.2 . . ?
C49 C48 C47 117.7(2) . . ?
C49 C48 H48 121.2 . . ?
C48 C49 C50 122.2(2) . . ?
C48 C49 C52 120.2(2) . . ?
C50 C49 C52 117.6(2) . . ?
C019 C50 H50 120.2 . . ?
C49 C50 C019 119.5(2) . . ?
C49 C50 H50 120.2 . . ?
F13 C51 F14 106.5(2) . . ?
F13 C51 F15 106.18(19) . . ?
F13 C51 C47 112.4(2) . . ?
F14 C51 C47 112.53(19) . . ?
F15 C51 F14 105.66(19) . . ?
F15 C51 C47 113.03(19) . . ?
F16 C52 F17 106.6(2) . . ?
F16 C52 F18 105.6(2) . . ?
F16 C52 C49 112.9(2) . . ?
F17 C52 C49 112.1(2) . . ?
F18 C52 F17 106.3(2) . . ?
F18 C52 C49 112.71(19) . . ?
O5 C53 N9 123.6(2) . . ?
O5 C53 N10 122.6(2) . . ?
O5 C53 N10A 115.6(4) . . ?
N9 C53 N10 113.5(2) . . ?
N9 C53 N10A 113.5(4) . . ?
N10 C54 H54A 109.5 . . ?
N10 C54 H54B 109.5 . . ?
N10 C54 C55 110.6(3) . . ?
H54A C54 H54B 108.1 . . ?
C55 C54 H54A 109.5 . . ?
C55 C54 H54B 109.5 . . ?
N11 C55 C54 111.6(2) . . ?
N11 C55 H55A 109.3 . . ?
N11 C55 H55B 109.3 . . ?
C54 C55 H55A 109.3 . . ?
C54 C55 H55B 109.3 . . ?
H55A C55 H55B 108.0 . . ?
O6 C56 N11 120.6(2) . . ?
O6 C56 N12 123.5(2) . . ?
N12 C56 N11 115.97(19) . . ?
N12 C57 C58 106.57(18) . . ?
N12 C57 C59 108.79(19) . . ?
N12 C57 C60 110.6(2) . . ?
C58 C57 C59 109.5(2) . . ?
C58 C57 C60 109.6(2) . . ?
C60 C57 C59 111.69(19) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
N11 C61 H61A 108.7 . . ?
N11 C61 H61B 108.7 . . ?
N11 C61 C62 114.2(2) . . ?
H61A C61 H61B 107.6 . . ?
C62 C61 H61A 108.7 . . ?
C62 C61 H61B 108.7 . . ?
C63 C62 C61 123.7(2) . . ?
C63 C62 C67 117.7(2) . . ?
C67 C62 C61 118.6(2) . . ?
C62 C63 H63 119.3 . . ?
C62 C63 C64 121.3(2) . . ?
C64 C63 H63 119.3 . . ?
C63 C64 H64 119.9 . . ?
C65 C64 C63 120.1(2) . . ?
C65 C64 H64 119.9 . . ?
C64 C65 H65 120.3 . . ?
C66 C65 C64 119.4(2) . . ?
C66 C65 H65 120.3 . . ?
C65 C66 H66 119.6 . . ?
C65 C66 C67 120.7(2) . . ?
C67 C66 H66 119.6 . . ?
C62 C67 H67 119.7 . . ?
C66 C67 C62 120.7(2) . . ?
C66 C67 H67 119.7 . . ?
N11 C55A H55C 112.1 . . ?
N11 C55A H55D 112.1 . . ?
N11 C55A C54A 98.3(6) . . ?
H55C C55A H55D 109.7 . . ?
C54A C55A H55C 112.1 . . ?
C54A C55A H55D 112.1 . . ?
C55A C54A H54C 109.5 . . ?
C55A C54A H54D 109.5 . . ?
H54C C54A H54D 108.1 . . ?
N10A C54A C55A 110.9(8) . . ?
N10A C54A H54C 109.5 . . ?
N10A C54A H54D 109.5 . . ?
C53 N10A C54A 123.3(7) . . ?
C53 N10A H10A 118.4 . . ?
C54A N10A H10A 118.4 . . ?

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
C15 H15A O2 0.98 2.45 3.057(3) 120.0 . yes
C38 H38A O4 0.98 2.47 3.083(3) 120.4 . yes
N10 H10 O2 0.88 2.12 2.927(3) 152.1 3_666 yes
C50 H50 O5 0.95 2.15 2.780(3) 122.6 . yes
C59 H59A O6 0.98 2.47 3.082(3) 120.3 . yes
C60 H60C O6 0.98 2.46 3.071(3) 120.3 . yes
N10A H10A O2 0.88 2.43 3.159(8) 140.1 3_666 yes
N2 H2 O4 0.86(3) 2.17(3) 2.959(2) 152(2) . yes
N1 H1 O4 0.89(3) 2.11(3) 2.952(2) 158(2) . yes
N9 H9 O2 0.83(2) 2.20(2) 2.984(2) 157(2) 3_666 yes
N12 H12 O5 0.90(3) 2.15(3) 3.044(2) 172(3) . yes
N4 H4 O1 0.79(3) 2.30(3) 3.093(2) 174(3) . yes
N5 H5A O6 0.84(3) 2.08(3) 2.900(2) 165(3) . yes
N8 H8 O3 0.87(3) 2.21(3) 3.064(2) 167(2) . yes

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
N2 C10 C11 N3 -161.18(17) . . . . ?
N3 C17 C18 C19 -22.8(3) . . . . ?
N3 C17 C18 C23 157.58(19) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C1 C2 C7 F1 134.8(2) . . . . ?
C1 C2 C7 F2 13.9(4) . . . . ?
C1 C2 C7 F3 -106.6(3) . . . . ?
C2 C1 C6 N1 -179.9(2) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C3 C4 C8 174.9(2) . . . . ?
C3 C2 C7 F1 -47.4(3) . . . . ?
C3 C2 C7 F2 -168.3(2) . . . . ?
C3 C2 C7 F3 71.2(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C8 F4 32.6(3) . . . . ?
C3 C4 C8 F5 -86.7(3) . . . . ?
C3 C4 C8 F6 154.8(2) . . . . ?
C4 C5 C6 N1 178.8(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C5 C4 C8 F4 -152.1(2) . . . . ?
C5 C4 C8 F5 88.6(3) . . . . ?
C5 C4 C8 F6 -29.9(3) . . . . ?
C6 N1 C9 O1 7.1(4) . . . . ?
C6 N1 C9 N2 -172.6(2) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
C6 C1 C2 C7 178.5(2) . . . . ?
C7 C2 C3 C4 -178.7(2) . . . . ?
C8 C4 C5 C6 -173.7(2) . . . . ?
C9 N1 C6 C1 157.5(2) . . . . ?
C9 N1 C6 C5 -22.9(3) . . . . ?
C9 N2 C10 C11 75.7(2) . . . . ?
C10 N2 C9 O1 -5.0(3) . . . . ?
C10 N2 C9 N1 174.78(19) . . . . ?
C11 N3 C12 O2 161.0(2) . . . . ?
C11 N3 C12 N4 -19.6(3) . . . . ?
C11 N3 C17 C18 -79.5(2) . . . . ?
C12 N3 C11 C10 99.5(2) . . . . ?
C12 N3 C17 C18 86.8(2) . . . . ?
C12 N4 C13 C14 -176.2(2) . . . . ?
C12 N4 C13 C15 65.0(3) . . . . ?
C12 N4 C13 C16 -58.3(3) . . . . ?
C13 N4 C12 O2 -15.5(4) . . . . ?
C13 N4 C12 N3 165.1(2) . . . . ?
C17 N3 C11 C10 -94.8(2) . . . . ?
C17 N3 C12 O2 -4.3(3) . . . . ?
C17 N3 C12 N4 175.1(2) . . . . ?
C17 C18 C19 C20 -178.6(2) . . . . ?
C17 C18 C23 C22 -179.9(2) . . . . ?
C18 C19 C20 C21 -1.3(4) . . . . ?
C19 C18 C23 C22 0.4(3) . . . . ?
C19 C20 C21 C22 0.0(4) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C21 C22 C23 C18 -1.7(4) . . . . ?
C23 C18 C19 C20 1.0(4) . . . . ?
N5 C01A C24 C25 178.5(2) . . . . ?
N5 C01A C28 C27 -179.2(2) . . . . ?
N6 C32 C33 N7 163.51(17) . . . . ?
N7 C39 C40 C41 158.45(18) . . . . ?
N7 C39 C40 C45 -22.2(3) . . . . ?
C01A N5 C31 O3 4.0(4) . . . . ?
C01A N5 C31 N6 -175.4(2) . . . . ?
C01A C24 C25 C26 1.0(3) . . . . ?
C01A C24 C25 C29 -176.3(2) . . . . ?
C24 C01A C28 C27 -0.7(3) . . . . ?
C24 C25 C26 C27 -1.2(3) . . . . ?
C24 C25 C29 F7 96.5(3) . . . . ?
C24 C25 C29 F8 -22.2(3) . . . . ?
C24 C25 C29 F9 -143.0(2) . . . . ?
C25 C26 C27 C28 0.4(3) . . . . ?
C25 C26 C27 C30 -177.1(2) . . . . ?
C26 C25 C29 F7 -80.8(3) . . . . ?
C26 C25 C29 F8 160.5(2) . . . . ?
C26 C25 C29 F9 39.7(3) . . . . ?
C26 C27 C28 C01A 0.5(3) . . . . ?
C26 C27 C30 F10 98.4(3) . . . . ?
C26 C27 C30 F11 -20.0(3) . . . . ?
C26 C27 C30 F12 -141.3(2) . . . . ?
C28 C01A C24 C25 -0.1(3) . . . . ?
C28 C27 C30 F10 -79.2(3) . . . . ?
C28 C27 C30 F11 162.4(2) . . . . ?
C28 C27 C30 F12 41.1(3) . . . . ?
C29 C25 C26 C27 176.1(2) . . . . ?
C30 C27 C28 C01A 178.1(2) . . . . ?
C31 N5 C01A C24 143.4(2) . . . . ?
C31 N5 C01A C28 -38.1(3) . . . . ?
C31 N6 C32 C33 -70.2(3) . . . . ?
C32 N6 C31 O3 1.9(3) . . . . ?
C32 N6 C31 N5 -178.7(2) . . . . ?
C33 N7 C34 O4 175.77(19) . . . . ?
C33 N7 C34 N8 -4.2(3) . . . . ?
C33 N7 C39 C40 -84.4(2) . . . . ?
C34 N7 C33 C32 -74.9(2) . . . . ?
C34 N7 C39 C40 97.8(2) . . . . ?
C34 N8 C35 C36 -62.8(3) . . . . ?
C34 N8 C35 C37 179.40(19) . . . . ?
C34 N8 C35 C38 62.1(3) . . . . ?
C35 N8 C34 O4 1.2(3) . . . . ?
C35 N8 C34 N7 -178.79(19) . . . . ?
C39 N7 C33 C32 107.4(2) . . . . ?
C39 N7 C34 O4 -6.5(3) . . . . ?
C39 N7 C34 N8 173.51(18) . . . . ?
C39 C40 C41 C42 -179.55(18) . . . . ?
C39 C40 C45 C44 179.44(19) . . . . ?
C40 C41 C42 C43 0.0(3) . . . . ?
C41 C40 C45 C44 -1.3(3) . . . . ?
C41 C42 C43 C44 -1.1(3) . . . . ?
C42 C43 C44 C45 0.9(3) . . . . ?
C43 C44 C45 C40 0.2(3) . . . . ?
C45 C40 C41 C42 1.1(3) . . . . ?
O5 C53 N10A C54A 7.2(12) . . . . ?
N9 C019 C46 C47 -179.4(2) . . . . ?
N9 C019 C50 C49 178.5(2) . . . . ?
N9 C53 N10A C54A 158.6(8) . . . . ?
N10 C54 C55 N11 159.1(2) . . . . ?
N11 C61 C62 C63 23.9(3) . . . . ?
N11 C61 C62 C67 -156.7(2) . . . . ?
N11 C55A C54A N10A -163.8(7) . . . . ?
C019 N9 C53 O5 7.6(4) . . . . ?
C019 N9 C53 N10 -178.1(2) . . . . ?
C019 N9 C53 N10A -141.2(5) . . . . ?
C019 C46 C47 C48 1.0(3) . . . . ?
C019 C46 C47 C51 -176.4(2) . . . . ?
C46 C019 C50 C49 -1.5(3) . . . . ?
C46 C47 C48 C49 -1.6(3) . . . . ?
C46 C47 C51 F13 87.9(3) . . . . ?
C46 C47 C51 F14 -32.4(3) . . . . ?
C46 C47 C51 F15 -151.9(2) . . . . ?
C47 C48 C49 C50 0.7(3) . . . . ?
C47 C48 C49 C52 179.4(2) . . . . ?
C48 C47 C51 F13 -89.6(3) . . . . ?
C48 C47 C51 F14 150.2(2) . . . . ?
C48 C47 C51 F15 30.6(3) . . . . ?
C48 C49 C50 C019 0.8(4) . . . . ?
C48 C49 C52 F16 25.8(3) . . . . ?
C48 C49 C52 F17 -94.7(3) . . . . ?
C48 C49 C52 F18 145.4(2) . . . . ?
C50 C019 C46 C47 0.6(3) . . . . ?
C50 C49 C52 F16 -155.5(2) . . . . ?
C50 C49 C52 F17 84.1(3) . . . . ?
C50 C49 C52 F18 -35.9(3) . . . . ?
C51 C47 C48 C49 175.8(2) . . . . ?
C52 C49 C50 C019 -177.9(2) . . . . ?
C53 N9 C019 C46 170.4(2) . . . . ?
C53 N9 C019 C50 -9.6(4) . . . . ?
C53 N10 C54 C55 -72.3(4) . . . . ?
C54 N10 C53 O5 0.0(5) . . . . ?
C54 N10 C53 N9 -174.4(3) . . . . ?
C55 N11 C56 O6 -150.4(2) . . . . ?
C55 N11 C56 N12 29.6(3) . . . . ?
C55 N11 C61 C62 67.2(3) . . . . ?
C56 N11 C55 C54 -106.5(3) . . . . ?
C56 N11 C61 C62 -90.1(3) . . . . ?
C56 N11 C55A C54A 96.3(7) . . . . ?
C56 N12 C57 C58 173.4(2) . . . . ?
C56 N12 C57 C59 55.5(3) . . . . ?
C56 N12 C57 C60 -67.5(3) . . . . ?
C57 N12 C56 O6 16.2(4) . . . . ?
C57 N12 C56 N11 -163.8(2) . . . . ?
C61 N11 C55 C54 96.9(3) . . . . ?
C61 N11 C56 O6 6.0(4) . . . . ?
C61 N11 C56 N12 -174.0(2) . . . . ?
C61 N11 C55A C54A -107.9(6) . . . . ?
C61 C62 C63 C64 179.6(2) . . . . ?
C61 C62 C67 C66 -179.4(2) . . . . ?
C62 C63 C64 C65 0.0(3) . . . . ?
C63 C62 C67 C66 0.1(3) . . . . ?
C63 C64 C65 C66 -0.5(4) . . . . ?
C64 C65 C66 C67 0.7(4) . . . . ?
C65 C66 C67 C62 -0.5(4) . . . . ?
C67 C62 C63 C64 0.2(3) . . . . ?
C55A N11 C56 O6 161.3(5) . . . . ?
C55A N11 C56 N12 -18.7(6) . . . . ?
C55A N11 C61 C62 112.9(5) . . . . ?
C55A C54A N10A C53 65.7(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_s5693l
_database_code_depnum_ccdc_archive 'CCDC 2195711'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica-Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
3-phenyl-1,1-bis(2-(3-phenyl-1-(2-(3-phenylureido)ethyl)ureido)ethyl)urea
_chemical_formula_moiety         'C43 H48 N10 O5'
_chemical_formula_sum            'C43 H48 N10 O5'
_chemical_formula_weight         784.91
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNHO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.8818(2)
_cell_length_b                   7.74130(10)
_cell_length_c                   40.5948(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.052(2)
_cell_angle_gamma                90
_cell_volume                     4008.28(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15293
_cell_measurement_temperature    174.9(3)
_cell_measurement_theta_max      76.1710
_cell_measurement_theta_min      2.1430
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89155
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            32727
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.364
_diffrn_reflns_theta_min         2.198
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      174.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00   0.00   1.00    1.00    --   44.70   3.00  68.00   34
  2  ω     20.00 198.00   1.00    1.00    --  108.20   3.00  68.00  178
  3  ω     61.00 133.00   1.00    1.00    --   44.70  30.00 -90.00   72
  4  ω     72.00 133.00   1.00    1.00    --   44.70  60.00 -90.00   61
  5  ω    -44.00   0.00   1.00    1.00    --   44.70  30.00 -90.00   44
  6  ω    -45.00  52.00   1.00    1.00    --   44.70  60.00 -90.00   97
  7  ω      8.00  46.00   1.00    1.00    --   44.70   3.00  68.00   38
  8  ω    111.00 142.00   1.00    1.00    --  108.20  50.00-180.00   31
  9  ω    100.00 198.00   1.00    1.00    --  108.20  50.00-120.00   98
 10  ω     19.00  45.00   1.00    1.00    --  108.20  50.00-180.00   26
 11  ω     80.00 194.00   1.00    1.00    --  108.20  50.00 -60.00  114
 12  ω     77.00 102.00   1.00    1.00    --  108.20  50.00-180.00   25
 13  ω     55.00 197.00   1.00    1.00    --  108.20  50.00-150.00  142
 14  ω    158.00 185.00   1.00    1.00    --  108.20  50.00-180.00   27
 15  ω     89.00 114.00   1.00    1.00    --  108.20  50.00 -90.00   25
 16  ω     24.00  49.00   1.00    1.00    --  108.20  50.00-150.00   25
 17  ω     27.00  52.00   1.00    1.00    --  108.20  50.00 -60.00   25
 18  ω    140.00 165.00   1.00    1.00    --  108.20  50.00 -90.00   25
 19  ω    138.00 163.00   1.00    1.00    --  108.20  50.00 -30.00   25
 20  ω     28.00  55.00   1.00    1.00    --  108.20  50.00-120.00   27
 21  ω     42.00  71.00   1.00    1.00    --   44.70   3.00  70.00   29
 22  ω    -45.00   1.00   1.00    1.00    --   44.70  50.00-120.00   46
 23  ω     67.00 108.00   1.00    1.00    --   44.70  60.00-180.00   41
 24  ω    -41.00 -11.00   1.00    1.00    --   44.70  10.00-120.00   30
 25  ω    -44.00 -18.00   1.00    1.00    --   44.70  40.00-180.00   26
 26  ω     72.00  98.00   1.00    1.00    --   44.70  60.00-120.00   26
 27  ω    -44.00 -18.00   1.00    1.00    --   44.70  60.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0721355000
_diffrn_orient_matrix_UB_12      -0.0109139000
_diffrn_orient_matrix_UB_13      -0.0271571000
_diffrn_orient_matrix_UB_21      -0.0967315000
_diffrn_orient_matrix_UB_22      0.0038601000
_diffrn_orient_matrix_UB_23      -0.0270144000
_diffrn_orient_matrix_UB_31      0.0058361000
_diffrn_orient_matrix_UB_32      0.1986822000
_diffrn_orient_matrix_UB_33      -0.0009577000
_diffrn_oxdiff_digest_frames     
;
01548706d9665846636e651417ee1f7382011399726
;
_diffrn_oxdiff_digest_hkl        
;
01c5229712f087e5b3bc9344380eae1f46a294
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7176
_reflns_number_total             7973
_reflns_odcompleteness_completeness 97.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         7973
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0705P)²+1.6066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          ?
_olex2_refinement_description    
;
1. Rigid body (RIGU) restrains
 C51A, C7A, C56, C12, C49, C51, C7, C55A, C12A, C56A, N48A, N48
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C47A, C47, N46, N46A, O52A, O52, N48A, N48
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
2. Others
 Sof(H45C)=Sof(H45D)=Sof(N46A)=Sof(N9A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=
 Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C49A)=Sof(C51A)=Sof(H51A)=Sof(C7A)=Sof(H7AA)=
 Sof(C55A)=Sof(H55A)=Sof(C56A)=Sof(H56A)=Sof(C12A)=Sof(H12A)=Sof(N48A)=
 Sof(H48A)=Sof(C47A)=Sof(O52A)=1-FVAR(1)
 Sof(O52)=Sof(N46)=Sof(N48)=Sof(H48)=Sof(C7)=Sof(H7A)=Sof(N9)=Sof(C12)=
 Sof(H12)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H45A)=
 Sof(H45B)=Sof(C47)=Sof(C49)=Sof(C51)=Sof(H51)=Sof(C55)=Sof(H55)=Sof(C56)=
 Sof(H56)=FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(N12B)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C10A)=
 Sof(H10C)=Sof(H10D)=1-FVAR(2)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H13C)=Sof(H13D)=
 Sof(N12A)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C13(H13C,H13D), C13(H13A,H13B), C14(H14A,
 H14B), C15(H15A,H15B), C17(H17A,H17B), C44(H44A,H44B), C45(H45A,H45B),
 C45(H45C,H45D), C15A(H15C,H15D), C17A(H17C,H17D), C11A(H11C,H11D), C10A(H10C,
 H10D)
3.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N15(H15), N18(H18), N21(H21), N41(H41), N43(H43), N48(H48), C2(H2),
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7A), C12(H12), C24(H24), C25(H25),
 C26(H26), C27(H27), C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
  C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C51(H51), C55(H55),
 C56(H56), C51A(H51A), C7A(H7AA), C55A(H55A), C56A(H56A), C12A(H12A), N48A(H48A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O17 O 0.90887(9) 0.86045(16) 0.76146(3) 0.0488(3) Uani 1 1 d . . . . .
O20 O 0.56728(10) 0.99198(19) 0.69050(3) 0.0629(4) Uani 1 1 d . . . . .
O22 O 0.35674(13) 0.7928(2) 0.58298(4) 0.0823(5) Uani 1 1 d . . . . .
O52 O 0.3549(15) 0.336(2) 0.4936(3) 0.0472(19) Uani 0.530(3) 1 d . U P A 1
O54 O 0.68012(13) 0.0569(2) 0.59341(4) 0.0768(5) Uani 1 1 d . . . . .
N7 N 0.42808(13) 0.9457(2) 0.62857(4) 0.0539(4) Uani 1 1 d . . . . .
H7 H 0.477494 0.944820 0.645176 0.065 Uiso 1 1 calc R . . . .
N15 N 0.94168(12) 0.6488(2) 0.72610(4) 0.0544(4) Uani 1 1 d . . . . .
H15 H 0.982223 0.566468 0.721593 0.065 Uiso 1 1 calc R . . . .
N18 N 1.03975(12) 0.6668(2) 0.77764(4) 0.0496(4) Uani 1 1 d . . . . .
H18 H 1.068897 0.573109 0.772179 0.060 Uiso 1 1 calc R . . . .
N21 N 0.69298(11) 0.9643(2) 0.73571(4) 0.0509(4) Uani 1 1 d . . . . .
H21 H 0.740621 0.896336 0.745352 0.061 Uiso 1 1 calc R . . . .
N41 N 0.75167(13) -0.1600(2) 0.56528(4) 0.0566(4) Uani 1 1 d . . . . .
H41 H 0.734725 -0.238420 0.550508 0.068 Uiso 1 1 calc R . . . .
N43 N 0.59379(12) -0.0382(2) 0.54455(4) 0.0531(4) Uani 1 1 d . . . . .
H43 H 0.592355 -0.108587 0.528103 0.064 Uiso 1 1 calc R . . . .
N46 N 0.4514(4) 0.3704(6) 0.54610(10) 0.0467(9) Uani 0.530(3) 1 d . U P A 1
N48 N 0.3191(12) 0.5702(19) 0.5244(2) 0.0459(19) Uani 0.530(3) 1 d . U P A 1
H48 H 0.345291 0.631487 0.541228 0.055 Uiso 0.530(3) 1 calc R . P A 1
C1 C 0.35956(14) 1.0887(2) 0.62639(4) 0.0478(4) Uani 1 1 d . . . . .
C2 C 0.27189(17) 1.1097(3) 0.60293(6) 0.0695(6) Uani 1 1 d . . . . .
H2 H 0.254484 1.026327 0.586593 0.083 Uiso 1 1 calc R . . . .
C3 C 0.20998(18) 1.2556(3) 0.60383(8) 0.0837(8) Uani 1 1 d . . . . .
H3 H 0.151331 1.269282 0.587867 0.100 Uiso 1 1 calc R . . . .
C4 C 0.23326(18) 1.3799(3) 0.62771(7) 0.0724(6) Uani 1 1 d . . . . .
H4 H 0.190109 1.475886 0.628274 0.087 Uiso 1 1 calc R . . . .
C5 C 0.32091(17) 1.3611(3) 0.65073(5) 0.0615(5) Uani 1 1 d . . . . .
H5 H 0.338109 1.445759 0.666829 0.074 Uiso 1 1 calc R . . . .
C6 C 0.38383(15) 1.2173(2) 0.65018(5) 0.0513(4) Uani 1 1 d . . . . .
H6 H 0.443283 1.206148 0.665913 0.062 Uiso 1 1 calc R . . . .
C7 C 0.1253(5) 0.9011(8) 0.49658(19) 0.097(2) Uani 0.530(3) 1 d . U P A 1
H7A H 0.104305 1.006851 0.504286 0.116 Uiso 0.530(3) 1 calc R . P A 1
C8 C 0.4248(2) 0.8087(3) 0.60728(5) 0.0712(6) Uani 1 1 d . . . . .
N9 N 0.4871(5) 0.6697(8) 0.61706(14) 0.0617(14) Uani 0.530(3) 1 d . . P A 1
C10 C 0.6039(3) 0.7262(5) 0.63805(9) 0.0634(10) Uani 0.740(6) 1 d . . P A 2
H10A H 0.624693 0.846472 0.640451 0.076 Uiso 0.740(6) 1 calc R . P A 2
H10B H 0.663969 0.662856 0.632428 0.076 Uiso 0.740(6) 1 calc R . P A 2
C11 C 0.5832(2) 0.6630(4) 0.67214(7) 0.0572(9) Uani 0.740(6) 1 d . . P A 2
H11A H 0.511811 0.692136 0.675036 0.069 Uiso 0.740(6) 1 calc R . P A 2
H11B H 0.589531 0.538132 0.672910 0.069 Uiso 0.740(6) 1 calc R . P A 2
C12 C 0.2022(3) 0.6138(6) 0.47287(10) 0.0713(13) Uani 0.530(3) 1 d . U P A 1
H12 H 0.232144 0.520747 0.463153 0.086 Uiso 0.530(3) 1 calc R . P A 1
C13 C 0.74849(16) 0.6434(3) 0.71319(6) 0.0652(6) Uani 1 1 d . . . . .
H13C H 0.737617 0.522288 0.707649 0.078 Uiso 0.740(6) 1 calc R . P A 2
H13D H 0.756049 0.652736 0.737234 0.078 Uiso 0.740(6) 1 calc R . P A 2
H13A H 0.744005 0.671056 0.736253 0.078 Uiso 0.260(6) 1 calc R . P A 1
H13B H 0.731793 0.522791 0.708687 0.078 Uiso 0.260(6) 1 calc R . P A 1
C14 C 0.85244(16) 0.6994(3) 0.70200(5) 0.0594(5) Uani 1 1 d . . . . .
H14A H 0.858708 0.647054 0.680661 0.071 Uiso 1 1 calc R . . . .
H14B H 0.852619 0.823857 0.699207 0.071 Uiso 1 1 calc R . . . .
C15 C 0.4787(3) 0.5160(5) 0.59692(9) 0.0541(10) Uani 0.530(3) 1 d . . P A 1
H15A H 0.406172 0.478222 0.593605 0.065 Uiso 0.530(3) 1 calc R . P A 1
H15B H 0.520174 0.425278 0.608861 0.065 Uiso 0.530(3) 1 calc R . P A 1
C16 C 0.96042(13) 0.7314(2) 0.75543(4) 0.0444(4) Uani 1 1 d . . . . .
C17 C 0.5150(2) 0.5402(4) 0.56299(9) 0.0419(8) Uani 0.530(3) 1 d . . P A 1
H17A H 0.590400 0.529978 0.563894 0.050 Uiso 0.530(3) 1 calc R . P A 1
H17B H 0.490647 0.647693 0.552314 0.050 Uiso 0.530(3) 1 calc R . P A 1
C19 C 0.63635(14) 0.9057(3) 0.70697(5) 0.0558(5) Uani 1 1 d . . . . .
C23 C 0.68161(14) 1.1246(3) 0.75126(4) 0.0495(4) Uani 1 1 d . . . . .
C24 C 0.75438(17) 1.1624(3) 0.77886(5) 0.0644(5) Uani 1 1 d . . . . .
H24 H 0.806824 1.083269 0.786231 0.077 Uiso 1 1 calc R . . . .
C25 C 0.7491(2) 1.3184(4) 0.79552(6) 0.0813(7) Uani 1 1 d . . . . .
H25 H 0.798607 1.343869 0.813813 0.098 Uiso 1 1 calc R . . . .
C26 C 0.6718(2) 1.4339(4) 0.78521(6) 0.0848(8) Uani 1 1 d . . . . .
H26 H 0.668095 1.537741 0.796487 0.102 Uiso 1 1 calc R . . . .
C27 C 0.5995(2) 1.3963(3) 0.75810(6) 0.0759(7) Uani 1 1 d . . . . .
H27 H 0.546597 1.475452 0.751204 0.091 Uiso 1 1 calc R . . . .
C28 C 0.60348(16) 1.2433(3) 0.74076(5) 0.0599(5) Uani 1 1 d . . . . .
H28 H 0.554242 1.220334 0.722256 0.072 Uiso 1 1 calc R . . . .
C29 C 1.07882(13) 0.7397(2) 0.80896(4) 0.0443(4) Uani 1 1 d . . . . .
C30 C 1.01452(15) 0.8181(3) 0.82922(4) 0.0558(5) Uani 1 1 d . . . . .
H30 H 0.942568 0.824891 0.822546 0.067 Uiso 1 1 calc R . . . .
C31 C 1.05885(18) 0.8865(3) 0.85965(5) 0.0676(6) Uani 1 1 d . . . . .
H31 H 1.016191 0.941970 0.873031 0.081 Uiso 1 1 calc R . . . .
C32 C 1.16491(18) 0.8735(3) 0.87030(5) 0.0665(6) Uani 1 1 d . . . . .
H32 H 1.193584 0.919851 0.890692 0.080 Uiso 1 1 calc R . . . .
C33 C 1.22825(16) 0.7912(3) 0.85049(5) 0.0559(5) Uani 1 1 d . . . . .
H33 H 1.299652 0.779420 0.857737 0.067 Uiso 1 1 calc R . . . .
C34 C 1.18558(14) 0.7262(2) 0.81990(4) 0.0474(4) Uani 1 1 d . . . . .
H34 H 1.228858 0.672766 0.806454 0.057 Uiso 1 1 calc R . . . .
C35 C 0.85399(15) -0.1685(2) 0.58276(4) 0.0523(4) Uani 1 1 d . . . . .
C36 C 0.9296(2) -0.2548(4) 0.56816(6) 0.0931(10) Uani 1 1 d . . . . .
H36 H 0.910864 -0.306410 0.547493 0.112 Uiso 1 1 calc R . . . .
C37 C 1.0315(2) -0.2665(4) 0.58329(6) 0.0922(9) Uani 1 1 d . . . . .
H37 H 1.080489 -0.326745 0.572957 0.111 Uiso 1 1 calc R . . . .
C38 C 1.06128(18) -0.1903(3) 0.61339(6) 0.0672(6) Uani 1 1 d . . . . .
H38 H 1.130716 -0.194251 0.623423 0.081 Uiso 1 1 calc R . . . .
C39 C 0.98683(18) -0.1081(3) 0.62849(6) 0.0724(6) Uani 1 1 d . . . . .
H39 H 1.006124 -0.058538 0.649313 0.087 Uiso 1 1 calc R . . . .
C40 C 0.88355(17) -0.0963(3) 0.61370(5) 0.0611(5) Uani 1 1 d . . . . .
H40 H 0.834346 -0.040013 0.624576 0.073 Uiso 1 1 calc R . . . .
C42 C 0.67595(15) -0.0396(3) 0.56930(4) 0.0541(5) Uani 1 1 d . . . . .
C44 C 0.50789(15) 0.0825(3) 0.54581(5) 0.0573(5) Uani 1 1 d . . . . .
H44A H 0.492519 0.090826 0.568478 0.069 Uiso 1 1 calc R . . . .
H44B H 0.445621 0.040072 0.531971 0.069 Uiso 1 1 calc R . . . .
C45 C 0.53521(15) 0.2580(3) 0.53394(5) 0.0600(5) Uani 1 1 d . . . . .
H45A H 0.530700 0.261526 0.509899 0.072 Uiso 0.530(3) 1 calc R . P A 1
H45B H 0.604988 0.292919 0.543829 0.072 Uiso 0.530(3) 1 calc R . P A 1
H45C H 0.605941 0.281741 0.544612 0.072 Uiso 0.470(3) 1 calc R . P A 2
H45D H 0.539374 0.245767 0.510384 0.072 Uiso 0.470(3) 1 calc R . P A 2
C47 C 0.3701(9) 0.4147(14) 0.52453(18) 0.0440(18) Uani 0.530(3) 1 d . U P A 1
C49 C 0.2380(4) 0.6591(7) 0.50546(11) 0.0432(9) Uani 0.530(3) 1 d . U P A 1
C51 C 0.2006(6) 0.8083(9) 0.51591(16) 0.083(2) Uani 0.530(3) 1 d . U P A 1
H51 H 0.226944 0.849630 0.536938 0.100 Uiso 0.530(3) 1 calc R . P A 1
C55 C 0.0802(4) 0.8431(7) 0.46641(13) 0.0790(16) Uani 0.530(3) 1 d . . P A 1
H55 H 0.022207 0.897925 0.454669 0.095 Uiso 0.530(3) 1 calc R . P A 1
C56 C 0.1218(4) 0.7071(7) 0.45465(11) 0.0821(15) Uani 0.530(3) 1 d . U P A 1
H56 H 0.096544 0.670910 0.433169 0.099 Uiso 0.530(3) 1 calc R . P A 1
N46A N 0.4747(3) 0.4171(6) 0.53731(10) 0.0353(9) Uani 0.470(3) 1 d . U P A 2
N9A N 0.5225(5) 0.7150(8) 0.60982(16) 0.0551(14) Uani 0.470(3) 1 d . . P A 2
C15A C 0.5372(4) 0.5984(6) 0.58169(12) 0.0574(11) Uani 0.470(3) 1 d . . P A 2
H15C H 0.609761 0.561031 0.584087 0.069 Uiso 0.470(3) 1 calc R . P A 2
H15D H 0.522459 0.661853 0.560958 0.069 Uiso 0.470(3) 1 calc R . P A 2
C17A C 0.4676(4) 0.4435(6) 0.58024(11) 0.0560(11) Uani 0.470(3) 1 d . . P A 2
H17C H 0.397564 0.469077 0.585010 0.067 Uiso 0.470(3) 1 calc R . P A 2
H17D H 0.497943 0.347979 0.593781 0.067 Uiso 0.470(3) 1 calc R . P A 2
C49A C 0.2139(4) 0.5941(8) 0.51214(13) 0.0482(12) Uani 0.470(3) 1 d . . P A -2
C51A C 0.2001(6) 0.7627(13) 0.5015(3) 0.103(3) Uani 0.470(3) 1 d . U P A -2
H51A H 0.255175 0.841123 0.504957 0.124 Uiso 0.470(3) 1 calc R . P A -2
C7A C 0.1006(7) 0.8145(16) 0.4851(3) 0.123(3) Uani 0.470(3) 1 d . U P A -2
H7AA H 0.089749 0.927257 0.477536 0.147 Uiso 0.470(3) 1 calc R . P A -2
C55A C 0.0211(5) 0.6977(13) 0.48064(14) 0.108(2) Uani 0.470(3) 1 d . U P A -2
H55A H -0.043480 0.729777 0.469061 0.129 Uiso 0.470(3) 1 calc R . P A -2
C56A C 0.0344(4) 0.5380(10) 0.49258(13) 0.0881(17) Uani 0.470(3) 1 d . U P A -2
H56A H -0.021982 0.461970 0.490554 0.106 Uiso 0.470(3) 1 calc R . P A -2
C12A C 0.1310(3) 0.4847(7) 0.50791(11) 0.0656(13) Uani 0.470(3) 1 d . U P A -2
H12A H 0.139669 0.371527 0.515507 0.079 Uiso 0.470(3) 1 calc R . P A -2
N48A N 0.3140(13) 0.556(2) 0.5320(3) 0.047(2) Uani 0.470(3) 1 d . U P A -2
H48A H 0.333685 0.601608 0.551216 0.057 Uiso 0.470(3) 1 calc R . P A -2
C47A C 0.3783(9) 0.4329(15) 0.51657(18) 0.0364(15) Uani 0.470(3) 1 d . U P A -2
O52A O 0.3414(18) 0.326(3) 0.4991(4) 0.053(3) Uani 0.470(3) 1 d . U P A -2
N12A N 0.6547(2) 0.7368(4) 0.69956(9) 0.0473(7) Uani 0.740(6) 1 d . . P A 2
N12B N 0.6836(8) 0.7711(12) 0.6877(2) 0.050(2) Uani 0.260(6) 1 d . . P A 1
C11A C 0.6386(8) 0.7334(11) 0.6530(2) 0.057(3) Uani 0.260(6) 1 d . . P A 1
H11C H 0.685551 0.657079 0.643188 0.069 Uiso 0.260(6) 1 calc R . P A 1
H11D H 0.632711 0.840003 0.640332 0.069 Uiso 0.260(6) 1 calc R . P A 1
C10A C 0.5312(7) 0.6493(10) 0.65068(19) 0.057(3) Uani 0.260(6) 1 d . . P A 1
H10C H 0.537410 0.527965 0.656594 0.068 Uiso 0.260(6) 1 calc R . P A 1
H10D H 0.488523 0.706334 0.665318 0.068 Uiso 0.260(6) 1 calc R . 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
O17 C16 1.243(2) . ?
O20 C19 1.232(2) . ?
O22 C8 1.231(2) . ?
O52 C47 1.387(18) . ?
O54 C42 1.227(2) . ?
N7 H7 0.8600 . ?
N7 C1 1.410(2) . ?
N7 C8 1.365(2) . ?
N15 H15 0.8600 . ?
N15 C14 1.455(2) . ?
N15 C16 1.343(2) . ?
N18 H18 0.8600 . ?
N18 C16 1.360(2) . ?
N18 C29 1.417(2) . ?
N21 H21 0.8600 . ?
N21 C19 1.364(2) . ?
N21 C23 1.409(2) . ?
N41 H41 0.8600 . ?
N41 C35 1.408(2) . ?
N41 C42 1.375(2) . ?
N43 H43 0.8600 . ?
N43 C42 1.353(2) . ?
N43 C44 1.455(2) . ?
N46 C17 1.647(5) . ?
N46 C45 1.521(5) . ?
N46 C47 1.314(11) . ?
N48 H48 0.8600 . ?
N48 C47 1.37(2) . ?
N48 C49 1.390(13) . ?
C1 C2 1.381(3) . ?
C1 C6 1.392(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9300 . ?
C7 C51 1.364(9) . ?
C7 C55 1.357(8) . ?
C8 N9 1.367(7) . ?
C8 N9A 1.444(7) . ?
N9 C15 1.439(7) . ?
N9 C10A 1.412(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(5) . ?
C10 N9A 1.443(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N12A 1.458(4) . ?
C12 H12 0.9300 . ?
C12 C49 1.384(6) . ?
C12 C56 1.389(6) . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.535(3) . ?
C13 N12A 1.449(3) . ?
C13 N12B 1.582(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C17 1.527(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C19 N12A 1.370(4) . ?
C19 N12B 1.483(9) . ?
C23 C24 1.388(3) . ?
C23 C28 1.385(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.390(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.359(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.370(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.382(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.387(3) . ?
C29 C34 1.389(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.391(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.378(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.379(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.381(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(3) . ?
C35 C40 1.379(3) . ?
C36 H36 0.9300 . ?
C36 C37 1.373(4) . ?
C37 H37 0.9300 . ?
C37 C38 1.362(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.366(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.384(3) . ?
C40 H40 0.9300 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 C45 1.500(3) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C45 H45C 0.9700 . ?
C45 H45D 0.9700 . ?
C45 N46A 1.474(5) . ?
C49 C51 1.342(8) . ?
C51 H51 0.9300 . ?
C55 H55 0.9300 . ?
C55 C56 1.302(7) . ?
C56 H56 0.9300 . ?
N46A C17A 1.769(6) . ?
N46A C47A 1.405(11) . ?
N9A C15A 1.488(8) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C15A C17A 1.494(7) . ?
C17A H17C 0.9700 . ?
C17A H17D 0.9700 . ?
C49A C51A 1.378(9) . ?
C49A C12A 1.355(7) . ?
C49A N48A 1.453(14) . ?
C51A H51A 0.9300 . ?
C51A C7A 1.416(12) . ?
C7A H7AA 0.9300 . ?
C7A C55A 1.359(14) . ?
C55A H55A 0.9300 . ?
C55A C56A 1.330(11) . ?
C56A H56A 0.9300 . ?
C56A C12A 1.375(7) . ?
C12A H12A 0.9300 . ?
N48A H48A 0.8600 . ?
N48A C47A 1.46(2) . ?
C47A O52A 1.15(3) . ?
N12B C11A 1.476(13) . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C10A 1.520(15) . ?
C10A H10C 0.9700 . ?
C10A H10D 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
C1 N7 H7 116.3 . . ?
C8 N7 H7 116.3 . . ?
C8 N7 C1 127.33(16) . . ?
C14 N15 H15 120.2 . . ?
C16 N15 H15 120.2 . . ?
C16 N15 C14 119.67(16) . . ?
C16 N18 H18 117.0 . . ?
C16 N18 C29 126.01(15) . . ?
C29 N18 H18 117.0 . . ?
C19 N21 H21 116.6 . . ?
C19 N21 C23 126.83(16) . . ?
C23 N21 H21 116.6 . . ?
C35 N41 H41 116.5 . . ?
C42 N41 H41 116.5 . . ?
C42 N41 C35 126.99(15) . . ?
C42 N43 H43 120.0 . . ?
C42 N43 C44 119.91(15) . . ?
C44 N43 H43 120.0 . . ?
C45 N46 C17 104.9(3) . . ?
C47 N46 C17 111.9(6) . . ?
C47 N46 C45 118.0(5) . . ?
C47 N48 H48 110.3 . . ?
C47 N48 C49 139.4(11) . . ?
C49 N48 H48 110.3 . . ?
C2 C1 N7 125.44(17) . . ?
C2 C1 C6 118.46(17) . . ?
C6 C1 N7 116.10(16) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(2) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.89(19) . . ?
C5 C6 H6 119.6 . . ?
C51 C7 H7A 119.1 . . ?
C55 C7 H7A 119.1 . . ?
C55 C7 C51 121.7(5) . . ?
O22 C8 N7 122.71(18) . . ?
O22 C8 N9 118.5(3) . . ?
O22 C8 N9A 121.5(3) . . ?
N7 C8 N9 117.6(3) . . ?
N7 C8 N9A 113.3(3) . . ?
C8 N9 C15 119.4(5) . . ?
C8 N9 C10A 120.6(5) . . ?
C10A N9 C15 116.4(5) . . ?
H10A C10 H10B 106.9 . . ?
C11 C10 H10A 107.3 . . ?
C11 C10 H10B 107.3 . . ?
N9A C10 H10A 107.3 . . ?
N9A C10 H10B 107.3 . . ?
N9A C10 C11 120.1(4) . . ?
C10 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
N12A C11 C10 113.2(3) . . ?
N12A C11 H11A 108.9 . . ?
N12A C11 H11B 108.9 . . ?
C49 C12 H12 120.0 . . ?
C49 C12 C56 120.0(4) . . ?
C56 C12 H12 120.0 . . ?
H13C C13 H13D 107.2 . . ?
H13A C13 H13B 110.6 . . ?
C14 C13 H13C 107.9 . . ?
C14 C13 H13D 107.9 . . ?
C14 C13 H13A 113.3 . . ?
C14 C13 H13B 113.3 . . ?
C14 C13 N12B 91.9(5) . . ?
N12A C13 H13C 107.9 . . ?
N12A C13 H13D 107.9 . . ?
N12A C13 C14 117.5(2) . . ?
N12B C13 H13A 113.3 . . ?
N12B C13 H13B 113.3 . . ?
N15 C14 C13 111.39(17) . . ?
N15 C14 H14A 109.3 . . ?
N15 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
N9 C15 H15A 108.8 . . ?
N9 C15 H15B 108.8 . . ?
N9 C15 C17 113.7(4) . . ?
H15A C15 H15B 107.7 . . ?
C17 C15 H15A 108.8 . . ?
C17 C15 H15B 108.8 . . ?
O17 C16 N15 121.49(15) . . ?
O17 C16 N18 122.53(15) . . ?
N15 C16 N18 115.97(16) . . ?
N46 C17 H17A 112.8 . . ?
N46 C17 H17B 112.8 . . ?
C15 C17 N46 94.6(3) . . ?
C15 C17 H17A 112.8 . . ?
C15 C17 H17B 112.8 . . ?
H17A C17 H17B 110.3 . . ?
O20 C19 N21 122.87(18) . . ?
O20 C19 N12A 122.15(19) . . ?
O20 C19 N12B 114.4(3) . . ?
N21 C19 N12A 114.7(2) . . ?
N21 C19 N12B 118.3(3) . . ?
C24 C23 N21 116.52(18) . . ?
C28 C23 N21 124.27(17) . . ?
C28 C23 C24 119.21(19) . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.3(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.6(2) . . ?
C27 C26 H26 120.2 . . ?
C26 C27 H27 119.3 . . ?
C26 C27 C28 121.4(2) . . ?
C28 C27 H27 119.3 . . ?
C23 C28 H28 120.4 . . ?
C27 C28 C23 119.3(2) . . ?
C27 C28 H28 120.4 . . ?
C30 C29 N18 122.68(16) . . ?
C30 C29 C34 119.37(16) . . ?
C34 C29 N18 117.93(16) . . ?
C29 C30 H30 120.4 . . ?
C29 C30 C31 119.24(18) . . ?
C31 C30 H30 120.4 . . ?
C30 C31 H31 119.5 . . ?
C32 C31 C30 121.1(2) . . ?
C32 C31 H31 119.5 . . ?
C31 C32 H32 120.2 . . ?
C31 C32 C33 119.51(18) . . ?
C33 C32 H32 120.2 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 119.95(18) . . ?
C34 C33 H33 120.0 . . ?
C29 C34 H34 119.6 . . ?
C33 C34 C29 120.80(18) . . ?
C33 C34 H34 119.6 . . ?
C36 C35 N41 118.23(17) . . ?
C40 C35 N41 124.01(17) . . ?
C40 C35 C36 117.76(19) . . ?
C35 C36 H36 119.1 . . ?
C37 C36 C35 121.9(2) . . ?
C37 C36 H36 119.1 . . ?
C36 C37 H37 119.9 . . ?
C38 C37 C36 120.2(2) . . ?
C38 C37 H37 119.9 . . ?
C37 C38 H38 120.7 . . ?
C37 C38 C39 118.5(2) . . ?
C39 C38 H38 120.7 . . ?
C38 C39 H39 119.0 . . ?
C38 C39 C40 121.9(2) . . ?
C40 C39 H39 119.0 . . ?
C35 C40 C39 119.62(19) . . ?
C35 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
O54 C42 N41 123.70(17) . . ?
O54 C42 N43 121.99(17) . . ?
N43 C42 N41 114.29(15) . . ?
N43 C44 H44A 109.5 . . ?
N43 C44 H44B 109.5 . . ?
N43 C44 C45 110.90(16) . . ?
H44A C44 H44B 108.0 . . ?
C45 C44 H44A 109.5 . . ?
C45 C44 H44B 109.5 . . ?
N46 C45 H45A 111.4 . . ?
N46 C45 H45B 111.4 . . ?
C44 C45 N46 101.8(2) . . ?
C44 C45 H45A 111.4 . . ?
C44 C45 H45B 111.4 . . ?
C44 C45 H45C 106.0 . . ?
C44 C45 H45D 106.0 . . ?
H45A C45 H45B 109.3 . . ?
H45C C45 H45D 106.3 . . ?
N46A C45 C44 125.2(2) . . ?
N46A C45 H45C 106.0 . . ?
N46A C45 H45D 106.0 . . ?
N46 C47 O52 119.1(12) . . ?
N46 C47 N48 124.6(10) . . ?
N48 C47 O52 112.2(11) . . ?
C12 C49 N48 121.8(6) . . ?
C51 C49 N48 121.7(6) . . ?
C51 C49 C12 115.7(5) . . ?
C7 C51 H51 119.0 . . ?
C49 C51 C7 121.9(5) . . ?
C49 C51 H51 119.0 . . ?
C7 C55 H55 121.6 . . ?
C56 C55 C7 116.9(5) . . ?
C56 C55 H55 121.6 . . ?
C12 C56 H56 118.6 . . ?
C55 C56 C12 122.7(4) . . ?
C55 C56 H56 118.6 . . ?
C45 N46A C17A 106.8(3) . . ?
C47A N46A C45 116.9(6) . . ?
C47A N46A C17A 114.6(5) . . ?
C8 N9A C15A 116.9(5) . . ?
C10 N9A C8 123.7(5) . . ?
C10 N9A C15A 119.3(5) . . ?
N9A C15A H15C 109.2 . . ?
N9A C15A H15D 109.2 . . ?
N9A C15A C17A 112.2(5) . . ?
H15C C15A H15D 107.9 . . ?
C17A C15A H15C 109.2 . . ?
C17A C15A H15D 109.2 . . ?
N46A C17A H17C 113.5 . . ?
N46A C17A H17D 113.5 . . ?
C15A C17A N46A 91.1(3) . . ?
C15A C17A H17C 113.5 . . ?
C15A C17A H17D 113.5 . . ?
H17C C17A H17D 110.8 . . ?
C51A C49A N48A 115.7(9) . . ?
C12A C49A C51A 119.1(6) . . ?
C12A C49A N48A 124.4(8) . . ?
C49A C51A H51A 120.5 . . ?
C49A C51A C7A 119.0(9) . . ?
C7A C51A H51A 120.5 . . ?
C51A C7A H7AA 120.3 . . ?
C55A C7A C51A 119.3(9) . . ?
C55A C7A H7AA 120.3 . . ?
C7A C55A H55A 119.6 . . ?
C56A C55A C7A 120.8(6) . . ?
C56A C55A H55A 119.6 . . ?
C55A C56A H56A 119.8 . . ?
C55A C56A C12A 120.5(6) . . ?
C12A C56A H56A 119.8 . . ?
C49A C12A C56A 121.1(6) . . ?
C49A C12A H12A 119.4 . . ?
C56A C12A H12A 119.4 . . ?
C49A N48A H48A 123.0 . . ?
C49A N48A C47A 113.9(10) . . ?
C47A N48A H48A 123.0 . . ?
N46A C47A N48A 107.8(9) . . ?
O52A C47A N46A 124.1(16) . . ?
O52A C47A N48A 121.7(16) . . ?
C13 N12A C11 120.0(2) . . ?
C19 N12A C11 115.6(2) . . ?
C19 N12A C13 123.5(2) . . ?
C19 N12B C13 108.2(6) . . ?
C11A N12B C13 126.9(6) . . ?
C11A N12B C19 120.5(6) . . ?
N12B C11A H11C 109.2 . . ?
N12B C11A H11D 109.2 . . ?
N12B C11A C10A 112.1(8) . . ?
H11C C11A H11D 107.9 . . ?
C10A C11A H11C 109.2 . . ?
C10A C11A H11D 109.2 . . ?
N9 C10A C11A 104.5(7) . . ?
N9 C10A H10C 110.8 . . ?
N9 C10A H10D 110.8 . . ?
C11A C10A H10C 110.8 . . ?
C11A C10A H10D 110.8 . . ?
H10C C10A H10D 108.9 . . ?

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
O20 C19 N12A C11 -3.4(4) . . . . ?
O20 C19 N12A C13 165.6(3) . . . . ?
O20 C19 N12B C13 -166.0(4) . . . . ?
O20 C19 N12B C11A -8.0(11) . . . . ?
O22 C8 N9 C15 6.2(7) . . . . ?
O22 C8 N9 C10A -151.6(6) . . . . ?
O22 C8 N9A C10 -178.7(4) . . . . ?
O22 C8 N9A C15A 0.0(7) . . . . ?
N7 C1 C2 C3 179.0(2) . . . . ?
N7 C1 C6 C5 -178.72(18) . . . . ?
N7 C8 N9 C15 174.0(4) . . . . ?
N7 C8 N9 C10A 16.1(8) . . . . ?
N7 C8 N9A C10 18.6(7) . . . . ?
N7 C8 N9A C15A -162.7(4) . . . . ?
N18 C29 C30 C31 179.95(19) . . . . ?
N18 C29 C34 C33 -178.59(16) . . . . ?
N21 C19 N12A C11 170.3(2) . . . . ?
N21 C19 N12A C13 -20.7(4) . . . . ?
N21 C19 N12B C13 36.8(8) . . . . ?
N21 C19 N12B C11A -165.1(7) . . . . ?
N21 C23 C24 C25 179.6(2) . . . . ?
N21 C23 C28 C27 179.6(2) . . . . ?
N41 C35 C36 C37 178.9(3) . . . . ?
N41 C35 C40 C39 -178.4(2) . . . . ?
N43 C44 C45 N46 -165.1(2) . . . . ?
N43 C44 C45 N46A -168.8(2) . . . . ?
N48 C49 C51 C7 176.1(10) . . . . ?
C1 N7 C8 O22 -1.6(4) . . . . ?
C1 N7 C8 N9 -168.8(3) . . . . ?
C1 N7 C8 N9A 160.9(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C55 C56 C12 5.9(10) . . . . ?
C8 N7 C1 C2 4.1(3) . . . . ?
C8 N7 C1 C6 -176.0(2) . . . . ?
C8 N9 C15 C17 66.8(6) . . . . ?
C8 N9 C10A C11A -93.1(7) . . . . ?
C8 N9A C15A C17A -70.0(6) . . . . ?
N9 C15 C17 N46 -160.1(4) . . . . ?
C10 C11 N12A C13 -94.8(3) . . . . ?
C10 C11 N12A C19 74.6(4) . . . . ?
C10 N9A C15A C17A 108.8(5) . . . . ?
C11 C10 N9A C8 64.2(6) . . . . ?
C11 C10 N9A C15A -114.5(5) . . . . ?
C12 C49 C51 C7 5.7(12) . . . . ?
C13 N12B C11A C10A 85.3(10) . . . . ?
C14 N15 C16 O17 -6.4(3) . . . . ?
C14 N15 C16 N18 174.57(17) . . . . ?
C14 C13 N12A C11 100.4(3) . . . . ?
C14 C13 N12A C19 -68.2(4) . . . . ?
C14 C13 N12B C19 -114.0(6) . . . . ?
C14 C13 N12B C11A 89.7(10) . . . . ?
C15 N9 C10A C11A 108.3(6) . . . . ?
C16 N15 C14 C13 -71.8(2) . . . . ?
C16 N18 C29 C30 37.4(3) . . . . ?
C16 N18 C29 C34 -144.65(18) . . . . ?
C17 N46 C45 C44 134.4(2) . . . . ?
C17 N46 C47 O52 132.4(12) . . . . ?
C17 N46 C47 N48 -23.2(12) . . . . ?
C19 N21 C23 C24 -174.5(2) . . . . ?
C19 N21 C23 C28 5.6(3) . . . . ?
C19 N12B C11A C10A -68.3(11) . . . . ?
C23 N21 C19 O20 1.4(3) . . . . ?
C23 N21 C19 N12A -172.3(2) . . . . ?
C23 N21 C19 N12B 156.5(5) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C24 C23 C28 C27 -0.3(3) . . . . ?
C24 C25 C26 C27 -0.5(4) . . . . ?
C25 C26 C27 C28 -0.3(4) . . . . ?
C26 C27 C28 C23 0.7(4) . . . . ?
C28 C23 C24 C25 -0.5(3) . . . . ?
C29 N18 C16 O17 -4.1(3) . . . . ?
C29 N18 C16 N15 174.89(17) . . . . ?
C29 C30 C31 C32 -1.7(3) . . . . ?
C30 C29 C34 C33 -0.6(3) . . . . ?
C30 C31 C32 C33 0.0(4) . . . . ?
C31 C32 C33 C34 1.5(3) . . . . ?
C32 C33 C34 C29 -1.2(3) . . . . ?
C34 C29 C30 C31 2.0(3) . . . . ?
C35 N41 C42 O54 -15.4(4) . . . . ?
C35 N41 C42 N43 165.96(19) . . . . ?
C35 C36 C37 C38 -0.8(5) . . . . ?
C36 C35 C40 C39 1.8(4) . . . . ?
C36 C37 C38 C39 2.3(5) . . . . ?
C37 C38 C39 C40 -1.8(4) . . . . ?
C38 C39 C40 C35 -0.3(4) . . . . ?
C40 C35 C36 C37 -1.3(4) . . . . ?
C42 N41 C35 C36 -157.2(2) . . . . ?
C42 N41 C35 C40 23.0(3) . . . . ?
C42 N43 C44 C45 81.0(2) . . . . ?
C44 N43 C42 O54 1.1(3) . . . . ?
C44 N43 C42 N41 179.73(18) . . . . ?
C44 C45 N46A C17A 57.1(4) . . . . ?
C44 C45 N46A C47A -72.7(6) . . . . ?
C45 N46 C17 C15 -122.9(3) . . . . ?
C45 N46 C47 O52 10.5(15) . . . . ?
C45 N46 C47 N48 -145.1(10) . . . . ?
C45 N46A C17A C15A 111.3(3) . . . . ?
C45 N46A C47A N48A 157.6(9) . . . . ?
C45 N46A C47A O52A 5.5(16) . . . . ?
C47 N46 C17 C15 108.1(5) . . . . ?
C47 N46 C45 C44 -100.2(6) . . . . ?
C47 N48 C49 C12 -18(2) . . . . ?
C47 N48 C49 C51 171.7(15) . . . . ?
C49 N48 C47 O52 19(3) . . . . ?
C49 N48 C47 N46 176.2(13) . . . . ?
C49 C12 C56 C55 3.2(9) . . . . ?
C51 C7 C55 C56 -9.2(12) . . . . ?
C55 C7 C51 C49 3.4(14) . . . . ?
C56 C12 C49 N48 -179.3(9) . . . . ?
C56 C12 C49 C51 -8.8(9) . . . . ?
N9A C10 C11 N12A -159.1(4) . . . . ?
N9A C15A C17A N46A 156.4(4) . . . . ?
C17A N46A C47A N48A 31.6(12) . . . . ?
C17A N46A C47A O52A -120.5(14) . . . . ?
C49A C51A C7A C55A 0.6(15) . . . . ?
C49A N48A C47A N46A 176.1(9) . . . . ?
C49A N48A C47A O52A -31(2) . . . . ?
C51A C49A C12A C56A 1.4(9) . . . . ?
C51A C49A N48A C47A -116.1(13) . . . . ?
C51A C7A C55A C56A 2.8(14) . . . . ?
C7A C55A C56A C12A -4.1(10) . . . . ?
C55A C56A C12A C49A 2.0(8) . . . . ?
C12A C49A C51A C7A -2.7(12) . . . . ?
C12A C49A N48A C47A 74.0(13) . . . . ?
N48A C49A C51A C7A -173.1(9) . . . . ?
N48A C49A C12A C56A 170.9(7) . . . . ?
C47A N46A C17A C15A -117.6(6) . . . . ?
N12A C13 C14 N15 157.0(2) . . . . ?
N12B C13 C14 N15 163.2(3) . . . . ?
N12B C11A C10A N9 162.9(7) . . . . ?
C10A N9 C15 C17 -134.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.149
_oxdiff_exptl_absorpt_empirical_full_min 0.757
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_s5690a
_database_code_depnum_ccdc_archive 'CCDC 2195693'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica-Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-1-(2-(1-(2-(1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-(4-methoxyphenyl)ureido)ethyl)-3-(4-methoxyphenyl)ureido)ethyl)-3-(4-methoxyphenyl)urea
_chemical_formula_moiety         'C50 H50 F12 N10 O8, 2(C2 H3 N)'
_chemical_formula_sum            'C54 H56 F12 N12 O8'
_chemical_formula_weight         1229.10
_chemical_melting_point          408-410
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.6563(7)
_cell_length_b                   15.0421(8)
_cell_length_c                   17.5808(9)
_cell_angle_alpha                71.522(5)
_cell_angle_beta                 75.149(5)
_cell_angle_gamma                81.278(5)
_cell_volume                     2817.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4070
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      25.1910
_cell_measurement_theta_min      3.5070
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.959
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21032
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.404
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  73.00   1.00    5.00    --   19.45  57.00  30.00   50
  2  ω    -49.00  41.00   1.00    5.00    --   19.45 -57.00  90.00   90
  3  ω    -11.00  15.00   1.00    5.00    --   19.45  77.00 120.00   26
  4  ω     -1.00  92.00   1.00    5.00    --   19.45  37.00-120.00   93
  5  ω     -6.00  90.00   1.00    5.00    --   19.45  37.00 -30.00   96
  6  ω     -6.00  32.00   1.00    5.00    --   19.45  77.00   0.00   38
  7  ω     32.00  61.00   1.00    5.00    --   19.45 -99.00-120.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0628435000
_diffrn_orient_matrix_UB_12      0.0038528000
_diffrn_orient_matrix_UB_13      0.0056892000
_diffrn_orient_matrix_UB_21      0.0056493000
_diffrn_orient_matrix_UB_22      0.0198801000
_diffrn_orient_matrix_UB_23      -0.0430230000
_diffrn_orient_matrix_UB_31      0.0024803000
_diffrn_orient_matrix_UB_32      -0.0455618000
_diffrn_orient_matrix_UB_33      -0.0044026000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6532
_reflns_number_total             10289
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     853
_refine_ls_number_reflns         10289
_refine_ls_number_restraints     406
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+1.0627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O14-C1Q \\sim O14A-C1
 with sigma of 0.02
 N9-C26 \\sim N9A-C26A
 with sigma of 0.04
 O16-C27 \\sim O16A-C27A
 with sigma of 0.02
 N1-C1Q \\sim N1-C1
 with sigma of 0.02
 N9-C1Q \\sim N9A-C1
 with sigma of 0.02
 N5-C25 \\sim N5A-C25A
 with sigma of 0.04
 N9-C1T \\sim N9A-C1T
 with sigma of 0.02
 C26-C27 \\sim C26A-C27A
 with sigma of 0.04
 N9-C25 \\sim N9A-C25A
 with sigma of 0.02
 C1Q-C25 \\sim C1-C25A
 with sigma of 0.04
 C1T-C25 \\sim C1T-C25A
 with sigma of 0.04
 N4-C27 \\sim N4-C27A
 with sigma of 0.02
 N5-C26 \\sim N5A-C26A
 with sigma of 0.02
 N5-C27 \\sim N5A-C27A
 with sigma of 0.02
 N1-N9 \\sim N1-N9A
 with sigma of 0.04
 C25-C26 \\sim C25A-C26A
 with sigma of 0.02
 C1Q-C1T \\sim C1-C1T
 with sigma of 0.04
 N4-N5 \\sim N4-N5A
 with sigma of 0.04
 O14-N1 \\sim O14A-N1
 with sigma of 0.04
 O14-N9 \\sim O14A-N9A
 with sigma of 0.04
 O16-N4 \\sim O16A-N4
 with sigma of 0.04
 O16-N5 \\sim O16A-N5A
 with sigma of 0.04
2. Uiso/Uaniso restraints and constraints
O14 \\sim O16 \\sim N1 \\sim N9 \\sim C1Q \\sim C1T \\sim N4 \\sim N5 \\sim C25
\\sim C26 \\sim C27 \\sim C27A \\sim O16A \\sim N5A \\sim C26A \\sim C25A \\sim
N9A \\sim C1 \\sim O14A: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2A
O16A \\sim O16: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C27A \\sim C27: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C25 \\sim C25A: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C1 \\sim C1Q: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
3. Rigid body (RIGU) restrains
 O14, O16, N1, N9, C1Q, C1T, N4, N5, C25, C26, C27, C27A, O16A, N5A, C26A,
 C25A, N9A, C1, O14A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H1B)=Sof(H1TC)=Sof(H1TD)=Sof(H4B)=Sof(C27A)=Sof(O16A)=Sof(N5A)=Sof(H5A)=
 Sof(C26A)=Sof(H26C)=Sof(H26D)=Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(N9A)=Sof(C1)=
 Sof(O14A)=1-FVAR(1)
 Sof(O14)=Sof(O16)=Sof(H1A)=Sof(N9)=Sof(C1Q)=Sof(H1TA)=Sof(H1TB)=Sof(H4A)=
 Sof(N5)=Sof(H5)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=
 Sof(C27)=FVAR(1)
5.a Riding coordinates:
 N4(H4B)
5.b Secondary CH2 refined with riding coordinates:
 C1H(H1HA,H1HB), C1L(H1LA,H1LB), C1T(H1TA,H1TB), C1T(H1TC,H1TD), C1Z(H1ZA,
 H1ZB), C21(H21A,H21B), C22(H22A,H22B), C25(H25A,H25B), C26(H26A,H26B),
 C26A(H26C,H26D), C25A(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N3(H3), N12(H12), N1(H1A), N1(H1B), N6(H6), C1D(H1D), C1E(H1E),
 C1F(H1F), C1I(H1I), C1J(H1J), C1K(H1K), C1M(H1M), C1N(H1N), C1O(H1O), C1P(H1P),
  C1R(H1R), C1W(H1W), C1X(H1X), N4(H4A), N5(H5), C8(H8), C9(H9), C11(H11),
 C15(H15), C17(H17), N5A(H5A)
5.d Idealised Me refined as rotating group:
 C2B(H2BA,H2BB,H2BC), C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C2C(H2CA,H2CB,
 H2CC), C2D(H2DA,H2DB,H2DC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4 F 0.31418(18) -0.16939(13) 1.10122(13) 0.0412(6) Uani 1 1 d . . . . .
F7 F -0.28464(17) 0.62631(14) 0.28078(13) 0.0384(5) Uani 1 1 d . . . . .
F5 F 0.44915(19) -0.23292(13) 1.16893(13) 0.0397(6) Uani 1 1 d . . . . .
F9 F -0.23027(18) 0.76613(14) 0.21905(12) 0.0391(5) Uani 1 1 d . . . . .
F6 F 0.69648(18) 0.11159(14) 1.15875(13) 0.0439(6) Uani 1 1 d . . . . .
F8 F -0.14225(18) 0.65075(15) 0.17413(13) 0.0451(6) Uani 1 1 d . . . . .
O7 O 0.51350(19) 0.92532(14) 0.66833(13) 0.0246(5) Uani 1 1 d . . . . .
O8 O 0.47363(19) 0.29171(14) 0.99265(13) 0.0251(6) Uani 1 1 d . . . . .
O9 O 1.03337(19) 0.36473(16) 1.01175(13) 0.0273(6) Uani 1 1 d . . . . .
F10 F 0.2881(2) -0.16935(14) 1.22639(13) 0.0527(7) Uani 1 1 d . . . . .
O11 O 0.6289(2) 0.60497(15) 0.83532(14) 0.0279(6) Uani 1 1 d . . . . .
O12 O 1.0374(2) 0.92274(16) 0.73237(14) 0.0310(6) Uani 1 1 d . . . . .
F13 F 0.7233(2) -0.03734(15) 1.20002(16) 0.0686(8) Uani 1 1 d . . . . .
O14 O 0.2131(3) 1.1026(2) 0.5061(2) 0.0239(8) Uani 0.876(4) 1 d D U P A 1
F15 F 0.78093(19) 0.03643(19) 1.07366(15) 0.0629(8) Uani 1 1 d . . . . .
O16 O 0.1564(3) 0.7408(3) 0.4622(2) 0.0333(10) Uani 0.876(4) 1 d D U P A 1
O1 O 0.4968(2) 1.39807(15) 0.56910(15) 0.0344(6) Uani 1 1 d . . . . .
N2 N 0.6148(2) 0.44736(18) 0.89651(16) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.570706 0.400284 0.907796 0.029 Uiso 1 1 calc R U . . .
N3 N 0.6142(2) 0.79255(17) 0.73378(16) 0.0237(7) Uani 1 1 d . . . . .
H3 H 0.607503 0.732807 0.761321 0.028 Uiso 1 1 calc R U . . .
N12 N 0.2929(2) 0.33453(17) 0.96153(16) 0.0245(7) Uani 1 1 d . . . . .
H12 H 0.226489 0.317127 0.957536 0.029 Uiso 1 1 calc R U . . .
N1 N 0.3648(2) 1.05517(17) 0.57448(16) 0.0244(7) Uani 1 1 d D U . . .
H1A H 0.403426 1.005687 0.602154 0.029 Uiso 0.876(4) 1 calc R U P A 1
H1B H 0.423700 1.011209 0.580329 0.029 Uiso 0.124(4) 1 calc R U P A 2
N6 N 0.3417(2) 0.17901(18) 1.02650(16) 0.0243(7) Uani 1 1 d . . . . .
H6 H 0.271199 0.169382 1.022452 0.029 Uiso 1 1 calc R U . . .
N7 N 0.4429(2) 0.78434(18) 0.69261(17) 0.0263(7) Uani 1 1 d . . . . .
N8 N 0.4670(2) 0.54031(18) 0.83302(17) 0.0280(7) Uani 1 1 d . . . . .
N9 N 0.2893(3) 0.9498(2) 0.5314(2) 0.0191(9) Uani 0.876(4) 1 d D U P A 1
F1 F 0.1737(2) 0.45031(14) 0.43418(14) 0.0483(6) Uani 1 1 d . . . . .
C1A C 0.5752(3) 0.0247(2) 1.12385(19) 0.0225(8) Uani 1 1 d . . . . .
C1B C -0.1021(3) 0.6594(2) 0.2959(2) 0.0224(8) Uani 1 1 d . . . . .
C1C C 0.3752(3) 0.2707(2) 0.99358(19) 0.0224(8) Uani 1 1 d . . . . .
C1D C 0.8223(3) 0.7746(2) 0.7305(2) 0.0248(8) Uani 1 1 d . . . . .
H1D H 0.821577 0.711928 0.729455 0.030 Uiso 1 1 calc R U . . .
C1E C 0.4963(3) 1.2275(2) 0.6283(2) 0.0246(8) Uani 1 1 d . . . . .
H1E H 0.543217 1.226629 0.665527 0.029 Uiso 1 1 calc R U . . .
C1F C 0.9244(3) 0.4548(2) 0.9150(2) 0.0222(8) Uani 1 1 d . . . . .
H1F H 0.992112 0.489806 0.887795 0.027 Uiso 1 1 calc R U . . .
C1G C 0.4657(3) 1.3115(2) 0.5740(2) 0.0245(8) Uani 1 1 d . . . . .
C1H C 0.3174(3) 0.4334(2) 0.9336(2) 0.0255(8) Uani 1 1 d . . . . .
H1HA H 0.354204 0.446708 0.973335 0.031 Uiso 1 1 calc R U . . .
H1HB H 0.241566 0.473028 0.931767 0.031 Uiso 1 1 calc R U . . .
C1I C 0.8260(3) 0.9564(2) 0.73165(19) 0.0224(8) Uani 1 1 d . . . . .
H1I H 0.826958 1.019420 0.731808 0.027 Uiso 1 1 calc R U . . .
C1J C 0.9273(3) 0.8063(2) 0.73071(19) 0.0258(8) Uani 1 1 d . . . . .
H1J H 0.998271 0.765739 0.730026 0.031 Uiso 1 1 calc R U . . .
C1K C 0.5157(3) 0.1053(2) 1.08506(19) 0.0211(8) Uani 1 1 d . . . . .
H1K H 0.547577 0.164245 1.071661 0.025 Uiso 1 1 calc R U . . .
C1L C 0.3391(3) 0.8331(2) 0.6613(2) 0.0274(9) Uani 1 1 d . . . . .
H1LA H 0.306962 0.884829 0.686187 0.033 Uiso 1 1 calc R U . . .
H1LB H 0.276458 0.788887 0.676993 0.033 Uiso 1 1 calc R U . . .
C1M C -0.1043(3) 0.7207(2) 0.3405(2) 0.0240(8) Uani 1 1 d . . . . .
H1M H -0.160310 0.773951 0.336599 0.029 Uiso 1 1 calc R U . . .
C1N C 0.3970(3) 1.3121(2) 0.5201(2) 0.0286(9) Uani 1 1 d . . . . .
H1N H 0.374917 1.370106 0.483545 0.034 Uiso 1 1 calc R U . . .
C1O C 0.8231(3) 0.4781(2) 0.8837(2) 0.0247(8) Uani 1 1 d . . . . .
H1O H 0.821645 0.528704 0.835066 0.030 Uiso 1 1 calc R U . . .
C1P C 0.5317(3) -0.0627(2) 1.14599(19) 0.0237(8) Uani 1 1 d . . . . .
H1P H 0.573700 -0.117853 1.173257 0.028 Uiso 1 1 calc R U . . .
C1Q C 0.2857(3) 1.0393(3) 0.5349(2) 0.0192(10) Uani 0.876(4) 1 d D U P A 1
C1R C 0.0556(3) 0.6260(2) 0.3980(2) 0.0282(8) Uani 1 1 d . . . . .
H1R H 0.109459 0.613998 0.433112 0.034 Uiso 1 1 calc R U . . .
C1S C -0.0245(3) 0.7047(2) 0.3913(2) 0.0242(8) Uani 1 1 d . . . . .
C1T C 0.3719(3) 0.8734(2) 0.5673(2) 0.0261(8) Uani 1 1 d D U . . .
H1TA H 0.452075 0.896949 0.551360 0.031 Uiso 0.876(4) 1 calc R U P A 1
H1TB H 0.376947 0.821622 0.542869 0.031 Uiso 0.876(4) 1 calc R U P A 1
H1TC H 0.444134 0.908746 0.547071 0.031 Uiso 0.124(4) 1 calc R U P A 2
H1TD H 0.378132 0.825761 0.538134 0.031 Uiso 0.124(4) 1 calc R U P A 2
C1U C 0.3700(3) -0.1592(2) 1.1558(2) 0.0299(9) Uani 1 1 d . . . . .
C1V C 0.0564(3) 0.5653(2) 0.3532(2) 0.0261(8) Uani 1 1 d . . . . .
C1W C 0.3599(3) 1.2293(2) 0.5188(2) 0.0276(8) Uani 1 1 d . . . . .
H1W H 0.315044 1.230325 0.480343 0.033 Uiso 1 1 calc R U . . .
C1X C -0.0211(3) 0.5811(2) 0.3018(2) 0.0281(9) Uani 1 1 d . . . . .
H1X H -0.018995 0.538960 0.270917 0.034 Uiso 1 1 calc R U . . .
C1Y C 0.6927(3) 0.0330(3) 1.1397(2) 0.0326(9) Uani 1 1 d . . . . .
C1Z C 0.4007(3) 0.4586(2) 0.8483(2) 0.0269(8) Uani 1 1 d . . . . .
H1ZA H 0.457921 0.403922 0.842936 0.032 Uiso 1 1 calc R U . . .
H1ZB H 0.353355 0.471960 0.806033 0.032 Uiso 1 1 calc R U . . .
F2 F 0.2476(2) 0.49965(19) 0.30560(16) 0.0692(8) Uani 1 1 d . . . . .
C2A C 0.1437(4) 0.4814(3) 0.3608(3) 0.0430(11) Uani 1 1 d . . . . .
C2B C 1.0421(3) 1.0165(3) 0.7316(3) 0.0570(13) Uani 1 1 d . . . . .
H2BA H 1.012727 1.059846 0.684688 0.086 Uiso 1 1 calc R U . . .
H2BB H 1.124555 1.027938 0.726915 0.086 Uiso 1 1 calc R U . . .
H2BC H 0.992350 1.026478 0.782803 0.086 Uiso 1 1 calc R U . . .
F3 F 0.1054(2) 0.40937(16) 0.34905(19) 0.0842(10) Uani 1 1 d . . . . .
N4 N -0.0314(3) 0.76868(19) 0.43588(18) 0.0318(7) Uani 1 1 d D U . . .
H4A H -0.099439 0.802533 0.444080 0.038 Uiso 0.876(4) 1 calc R U P A 1
H4B H -0.085694 0.815593 0.425343 0.038 Uiso 0.124(4) 1 d R U P A 2
N5 N 0.0285(3) 0.8552(2) 0.5034(2) 0.0237(9) Uani 0.876(4) 1 d D U P A 1
H5 H -0.039917 0.888643 0.500597 0.028 Uiso 0.876(4) 1 calc R U P A 1
C6 C 0.7187(3) 0.8323(2) 0.73168(19) 0.0201(8) Uani 1 1 d . . . . .
C7 C 0.9282(3) 0.8984(2) 0.73196(19) 0.0212(8) Uani 1 1 d . . . . .
C8 C 0.4583(3) 1.1446(2) 0.62823(19) 0.0229(8) Uani 1 1 d . . . . .
H8 H 0.479647 1.086954 0.665523 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7202(3) 0.9240(2) 0.73112(19) 0.0219(8) Uani 1 1 d . . . . .
H9 H 0.649618 0.964914 0.730366 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9284(3) 0.3815(2) 0.9852(2) 0.0221(8) Uani 1 1 d . . . . .
C11 C 0.3633(3) 0.0129(2) 1.08690(19) 0.0212(8) Uani 1 1 d . . . . .
H11 H 0.290593 0.008008 1.074096 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4083(3) 0.1011(2) 1.06514(19) 0.0210(8) Uani 1 1 d . . . . .
C13 C 0.5243(3) 0.8384(2) 0.6972(2) 0.0236(8) Uani 1 1 d . . . . .
C14 C 0.7227(3) 0.4275(2) 0.9234(2) 0.0207(8) Uani 1 1 d . . . . .
C15 C 0.8303(3) 0.3293(2) 1.0248(2) 0.0253(8) Uani 1 1 d . . . . .
H15 H 0.832827 0.278116 1.072853 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5738(3) 0.5346(2) 0.8542(2) 0.0236(8) Uani 1 1 d . . . . .
C17 C 0.7284(3) 0.3527(2) 0.9933(2) 0.0227(8) Uani 1 1 d . . . . .
H17 H 0.661326 0.316877 1.020202 0.027 Uiso 1 1 calc R U . . .
C18 C 0.4250(3) -0.0671(2) 1.12712(19) 0.0209(8) Uani 1 1 d . . . . .
C19 C 0.3892(3) 1.1447(2) 0.5742(2) 0.0211(8) Uani 1 1 d . . . . .
C20 C 1.0279(3) 0.3120(2) 1.0963(2) 0.0323(9) Uani 1 1 d . . . . .
H20A H 1.014475 0.246564 1.104328 0.048 Uiso 1 1 calc R U . . .
H20B H 0.962288 0.339303 1.131527 0.048 Uiso 1 1 calc R U . . .
H20C H 1.103055 0.314174 1.110626 0.048 Uiso 1 1 calc R U . . .
C21 C 0.4620(3) 0.6810(2) 0.7129(2) 0.0274(8) Uani 1 1 d . . . . .
H21A H 0.548301 0.662576 0.699221 0.033 Uiso 1 1 calc R U . . .
H21B H 0.422594 0.658429 0.679662 0.033 Uiso 1 1 calc R U . . .
C22 C 0.4120(3) 0.6357(2) 0.8038(2) 0.0294(9) Uani 1 1 d . . . . .
H22A H 0.425666 0.674985 0.835889 0.035 Uiso 1 1 calc R U . . .
H22B H 0.324942 0.633014 0.813124 0.035 Uiso 1 1 calc R U . . .
C23 C -0.1887(3) 0.6761(2) 0.2427(2) 0.0295(9) Uani 1 1 d . . . . .
C25 C 0.2121(3) 0.9292(3) 0.4864(2) 0.0209(9) Uani 0.876(4) 1 d D U P A 1
H25A H 0.258515 0.891048 0.450551 0.025 Uiso 0.876(4) 1 calc R U P A 1
H25B H 0.181611 0.988782 0.450926 0.025 Uiso 0.876(4) 1 calc R U P A 1
C26 C 0.1085(3) 0.8764(3) 0.5453(2) 0.0234(10) Uani 0.876(4) 1 d D U P A 1
H26A H 0.139691 0.816905 0.580408 0.028 Uiso 0.876(4) 1 calc R U P A 1
H26B H 0.063409 0.914499 0.581544 0.028 Uiso 0.876(4) 1 calc R U P A 1
C27 C 0.0586(4) 0.7843(3) 0.4687(3) 0.0243(10) Uani 0.876(4) 1 d D U P A 1
C28 C 0.5692(3) 1.3994(2) 0.6234(2) 0.0398(10) Uani 1 1 d . . . . .
H28A H 0.589305 1.463882 0.612515 0.060 Uiso 1 1 calc R U . . .
H28B H 0.642439 1.358898 0.614231 0.060 Uiso 1 1 calc R U . . .
H28C H 0.525323 1.376387 0.680526 0.060 Uiso 1 1 calc R U . . .
N10 N -0.1687(3) 0.3931(2) 0.2756(2) 0.0435(9) Uani 1 1 d . . . . .
C2C C -0.2694(4) 0.4260(3) 0.4150(2) 0.0503(11) Uani 1 1 d . . . . .
H2CA H -0.352121 0.450606 0.414651 0.075 Uiso 1 1 calc R U . . .
H2CB H -0.226400 0.472402 0.422910 0.075 Uiso 1 1 calc R U . . .
H2CC H -0.267665 0.367558 0.459900 0.075 Uiso 1 1 calc R U . . .
C24 C -0.2126(3) 0.4075(2) 0.3367(3) 0.0344(10) Uani 1 1 d . . . . .
N11 N 0.1094(3) 0.1392(2) 1.0001(2) 0.0514(10) Uani 1 1 d . . . . .
C2D C -0.0417(4) 0.1621(3) 0.9087(3) 0.0598(14) Uani 1 1 d . . . . .
H2DA H 0.001072 0.163412 0.852614 0.090 Uiso 1 1 calc R U . . .
H2DB H -0.089633 0.221789 0.907747 0.090 Uiso 1 1 calc R U . . .
H2DC H -0.094026 0.110314 0.931253 0.090 Uiso 1 1 calc R U . . .
C29 C 0.0436(4) 0.1486(3) 0.9600(3) 0.0429(11) Uani 1 1 d . . . . .
C27A C 0.0817(16) 0.7989(15) 0.429(2) 0.0244(16) Uani 0.124(4) 1 d D U P A 2
O16A O 0.174(2) 0.748(2) 0.4277(18) 0.033(3) Uani 0.124(4) 1 d D U P A 2
N5A N 0.0701(18) 0.8846(13) 0.4428(15) 0.025(4) Uani 0.124(4) 1 d D U P A 2
H5A H 0.000984 0.917528 0.442387 0.031 Uiso 0.124(4) 1 calc R U P A 2
C26A C 0.165(2) 0.925(2) 0.4578(13) 0.031(5) Uani 0.124(4) 1 d D U P A 2
H26C H 0.159215 0.993879 0.432395 0.037 Uiso 0.124(4) 1 calc R U P A 2
H26D H 0.242876 0.899294 0.431358 0.037 Uiso 0.124(4) 1 calc R U P A 2
C25A C 0.1594(19) 0.9043(18) 0.5482(14) 0.0210(16) Uani 0.124(4) 1 d D U P A 2
H25C H 0.084860 0.935619 0.573043 0.025 Uiso 0.124(4) 1 calc R U P A 2
H25D H 0.155666 0.835733 0.574274 0.025 Uiso 0.124(4) 1 calc R U P A 2
N9A N 0.2600(15) 0.9347(12) 0.5672(14) 0.018(4) Uani 0.124(4) 1 d D U P A 2
C1 C 0.2599(17) 1.0262(13) 0.5667(19) 0.0192(16) Uani 0.124(4) 1 d D U P A 2
O14A O 0.1736(17) 1.0817(15) 0.5511(14) 0.027(5) Uani 0.124(4) 1 d D U P A 2


_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
F4 C1U 1.345(4) . ?
F7 C23 1.346(4) . ?
F5 C1U 1.331(4) . ?
F9 C23 1.337(4) . ?
F6 C1Y 1.336(4) . ?
F8 C23 1.336(4) . ?
O7 C13 1.243(4) . ?
O8 C1C 1.230(4) . ?
O9 C10 1.379(4) . ?
O9 C20 1.435(4) . ?
F10 C1U 1.339(4) . ?
O11 C16 1.232(3) . ?
O12 C2B 1.415(4) . ?
O12 C7 1.379(3) . ?
F13 C1Y 1.319(4) . ?
O14 C1Q 1.244(4) . ?
F15 C1Y 1.332(4) . ?
O16 C27 1.223(4) . ?
O1 C1G 1.375(3) . ?
O1 C28 1.433(4) . ?
N2 C14 1.412(4) . ?
N2 C16 1.370(4) . ?
N3 C6 1.422(4) . ?
N3 C13 1.354(4) . ?
N12 C1C 1.347(4) . ?
N12 C1H 1.458(4) . ?
N1 C1Q 1.375(4) . ?
N1 C19 1.417(4) . ?
N1 C1 1.410(16) . ?
N6 C1C 1.389(4) . ?
N6 C12 1.388(4) . ?
N7 C1L 1.457(4) . ?
N7 C13 1.372(4) . ?
N7 C21 1.475(4) . ?
N8 C1Z 1.467(4) . ?
N8 C16 1.372(4) . ?
N8 C22 1.469(4) . ?
N9 C1Q 1.362(4) . ?
N9 C1T 1.471(4) . ?
N9 C25 1.461(4) . ?
F1 C2A 1.343(4) . ?
C1A C1K 1.371(4) . ?
C1A C1P 1.383(4) . ?
C1A C1Y 1.497(5) . ?
C1B C1M 1.381(4) . ?
C1B C1X 1.388(5) . ?
C1B C23 1.489(5) . ?
C1D C1J 1.381(4) . ?
C1D C6 1.376(4) . ?
C1E C1G 1.381(4) . ?
C1E C8 1.386(4) . ?
C1F C1O 1.380(4) . ?
C1F C10 1.376(4) . ?
C1G C1N 1.385(5) . ?
C1H C1Z 1.530(4) . ?
C1I C7 1.365(4) . ?
C1I C9 1.397(4) . ?
C1J C7 1.395(4) . ?
C1K C12 1.399(4) . ?
C1L C1T 1.534(4) . ?
C1M C1S 1.393(4) . ?
C1N C1W 1.388(4) . ?
C1O C14 1.396(4) . ?
C1P C18 1.383(4) . ?
C1R C1S 1.385(4) . ?
C1R C1V 1.380(4) . ?
C1S N4 1.403(4) . ?
C1T N9A 1.479(15) . ?
C1U C18 1.498(4) . ?
C1V C1X 1.381(5) . ?
C1V C2A 1.489(5) . ?
C1W C19 1.393(4) . ?
F2 C2A 1.347(5) . ?
C2A F3 1.322(4) . ?
N4 C27 1.399(4) . ?
N4 C27A 1.424(16) . ?
N5 C26 1.452(4) . ?
N5 C27 1.350(4) . ?
C6 C9 1.380(4) . ?
C8 C19 1.393(4) . ?
C10 C15 1.388(4) . ?
C11 C12 1.402(4) . ?
C11 C18 1.387(4) . ?
C14 C17 1.387(4) . ?
C15 C17 1.388(4) . ?
C21 C22 1.519(4) . ?
C25 C26 1.513(5) . ?
N10 C24 1.136(4) . ?
C2C C24 1.460(5) . ?
N11 C29 1.135(5) . ?
C2D C29 1.458(5) . ?
C27A O16A 1.218(17) . ?
C27A N5A 1.364(17) . ?
N5A C26A 1.455(17) . ?
C26A C25A 1.504(18) . ?
C25A N9A 1.469(16) . ?
N9A C1 1.374(16) . ?
C1 O14A 1.235(16) . ?

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
C10 O9 C20 116.8(2) . . ?
C7 O12 C2B 116.1(3) . . ?
C1G O1 C28 116.5(3) . . ?
C16 N2 C14 124.8(3) . . ?
C13 N3 C6 125.9(3) . . ?
C1C N12 C1H 118.0(3) . . ?
C1Q N1 C19 125.3(3) . . ?
C1 N1 C19 129.4(8) . . ?
C12 N6 C1C 126.6(3) . . ?
C1L N7 C21 120.3(2) . . ?
C13 N7 C1L 117.4(3) . . ?
C13 N7 C21 122.1(3) . . ?
C1Z N8 C22 120.0(3) . . ?
C16 N8 C1Z 123.8(3) . . ?
C16 N8 C22 115.8(3) . . ?
C1Q N9 C1T 122.9(3) . . ?
C1Q N9 C25 118.8(3) . . ?
C25 N9 C1T 118.2(3) . . ?
C1K C1A C1P 122.2(3) . . ?
C1K C1A C1Y 117.8(3) . . ?
C1P C1A C1Y 120.0(3) . . ?
C1M C1B C1X 120.3(3) . . ?
C1M C1B C23 120.0(3) . . ?
C1X C1B C23 119.7(3) . . ?
O8 C1C N12 122.4(3) . . ?
O8 C1C N6 122.4(3) . . ?
N12 C1C N6 115.2(3) . . ?
C6 C1D C1J 121.1(3) . . ?
C1G C1E C8 119.6(3) . . ?
C10 C1F C1O 120.8(3) . . ?
O1 C1G C1E 124.9(3) . . ?
O1 C1G C1N 115.3(3) . . ?
C1E C1G C1N 119.7(3) . . ?
N12 C1H C1Z 111.4(2) . . ?
C7 C1I C9 120.6(3) . . ?
C1D C1J C7 119.3(3) . . ?
C1A C1K C12 120.3(3) . . ?
N7 C1L C1T 110.7(3) . . ?
C1B C1M C1S 120.2(3) . . ?
C1G C1N C1W 121.0(3) . . ?
C1F C1O C14 120.2(3) . . ?
C18 C1P C1A 117.8(3) . . ?
O14 C1Q N1 121.9(3) . . ?
O14 C1Q N9 122.1(3) . . ?
N9 C1Q N1 116.0(3) . . ?
C1V C1R C1S 119.5(3) . . ?
C1M C1S N4 117.8(3) . . ?
C1R C1S C1M 119.6(3) . . ?
C1R C1S N4 122.5(3) . . ?
N9 C1T C1L 115.5(3) . . ?
N9A C1T C1L 91.6(9) . . ?
F4 C1U C18 112.4(3) . . ?
F5 C1U F4 106.3(3) . . ?
F5 C1U F10 106.1(3) . . ?
F5 C1U C18 113.0(3) . . ?
F10 C1U F4 106.0(3) . . ?
F10 C1U C18 112.5(3) . . ?
C1R C1V C1X 121.4(3) . . ?
C1R C1V C2A 118.7(3) . . ?
C1X C1V C2A 119.9(3) . . ?
C1N C1W C19 119.4(3) . . ?
C1V C1X C1B 119.0(3) . . ?
F6 C1Y C1A 113.1(3) . . ?
F13 C1Y F6 106.3(3) . . ?
F13 C1Y F15 106.6(3) . . ?
F13 C1Y C1A 113.4(3) . . ?
F15 C1Y F6 104.7(3) . . ?
F15 C1Y C1A 112.0(3) . . ?
N8 C1Z C1H 112.7(2) . . ?
F1 C2A C1V 113.3(3) . . ?
F1 C2A F2 104.7(3) . . ?
F2 C2A C1V 112.1(4) . . ?
F3 C2A F1 107.0(3) . . ?
F3 C2A C1V 113.1(3) . . ?
F3 C2A F2 106.1(3) . . ?
C1S N4 C27A 112.7(10) . . ?
C27 N4 C1S 126.8(3) . . ?
C27 N5 C26 120.2(3) . . ?
C1D C6 N3 117.1(3) . . ?
C1D C6 C9 119.5(3) . . ?
C9 C6 N3 123.4(3) . . ?
O12 C7 C1J 114.6(3) . . ?
C1I C7 O12 125.6(3) . . ?
C1I C7 C1J 119.8(3) . . ?
C1E C8 C19 121.0(3) . . ?
C6 C9 C1I 119.7(3) . . ?
O9 C10 C15 124.0(3) . . ?
C1F C10 O9 116.1(3) . . ?
C1F C10 C15 119.9(3) . . ?
C18 C11 C12 120.1(3) . . ?
N6 C12 C1K 124.2(3) . . ?
N6 C12 C11 117.6(3) . . ?
C1K C12 C11 118.2(3) . . ?
O7 C13 N3 123.1(3) . . ?
O7 C13 N7 120.0(3) . . ?
N3 C13 N7 117.0(3) . . ?
C1O C14 N2 124.0(3) . . ?
C17 C14 N2 117.4(3) . . ?
C17 C14 C1O 118.5(3) . . ?
C10 C15 C17 119.3(3) . . ?
O11 C16 N2 122.6(3) . . ?
O11 C16 N8 120.9(3) . . ?
N2 C16 N8 116.5(3) . . ?
C14 C17 C15 121.2(3) . . ?
C1P C18 C1U 119.5(3) . . ?
C1P C18 C11 121.5(3) . . ?
C11 C18 C1U 118.9(3) . . ?
C1W C19 N1 124.5(3) . . ?
C1W C19 C8 119.2(3) . . ?
C8 C19 N1 115.9(3) . . ?
N7 C21 C22 110.6(3) . . ?
N8 C22 C21 112.0(3) . . ?
F7 C23 C1B 112.2(3) . . ?
F9 C23 F7 106.3(3) . . ?
F9 C23 C1B 113.1(3) . . ?
F8 C23 F7 105.5(2) . . ?
F8 C23 F9 106.7(3) . . ?
F8 C23 C1B 112.6(3) . . ?
N9 C25 C26 110.7(3) . . ?
N5 C26 C25 112.7(3) . . ?
O16 C27 N4 122.7(3) . . ?
O16 C27 N5 124.0(4) . . ?
N5 C27 N4 113.2(3) . . ?
N10 C24 C2C 179.8(6) . . ?
N11 C29 C2D 179.0(5) . . ?
O16A C27A N4 124(2) . . ?
O16A C27A N5A 123(2) . . ?
N5A C27A N4 111.1(15) . . ?
C27A N5A C26A 124.0(19) . . ?
N5A C26A C25A 112.2(18) . . ?
N9A C25A C26A 114.7(18) . . ?
C25A N9A C1T 118.9(14) . . ?
C1 N9A C1T 119.4(14) . . ?
C1 N9A C25A 120.1(16) . . ?
N9A C1 N1 117.9(14) . . ?
O14A C1 N1 122.6(16) . . ?
O14A C1 N9A 119.0(16) . . ?

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
F4 C1U C18 C1P -144.7(3) . . . . ?
F4 C1U C18 C11 39.6(4) . . . . ?
F5 C1U C18 C1P -24.4(4) . . . . ?
F5 C1U C18 C11 159.9(3) . . . . ?
O9 C10 C15 C17 179.4(3) . . . . ?
F10 C1U C18 C1P 95.8(4) . . . . ?
F10 C1U C18 C11 -79.9(4) . . . . ?
O1 C1G C1N C1W 179.9(3) . . . . ?
N2 C14 C17 C15 -178.9(3) . . . . ?
N3 C6 C9 C1I 178.0(3) . . . . ?
N12 C1H C1Z N8 -155.4(3) . . . . ?
N7 C1L C1T N9 -159.7(3) . . . . ?
N7 C1L C1T N9A -164.8(7) . . . . ?
N7 C21 C22 N8 -158.0(3) . . . . ?
N9 C25 C26 N5 179.4(3) . . . . ?
C1A C1K C12 N6 179.5(3) . . . . ?
C1A C1K C12 C11 0.8(5) . . . . ?
C1A C1P C18 C1U -175.3(3) . . . . ?
C1A C1P C18 C11 0.4(5) . . . . ?
C1B C1M C1S C1R -1.2(5) . . . . ?
C1B C1M C1S N4 -179.4(3) . . . . ?
C1C N12 C1H C1Z 80.3(4) . . . . ?
C1C N6 C12 C1K 7.5(5) . . . . ?
C1C N6 C12 C11 -173.8(3) . . . . ?
C1D C1J C7 O12 179.8(3) . . . . ?
C1D C1J C7 C1I -1.0(5) . . . . ?
C1D C6 C9 C1I -1.8(5) . . . . ?
C1E C1G C1N C1W -1.1(5) . . . . ?
C1E C8 C19 N1 174.4(3) . . . . ?
C1E C8 C19 C1W 1.1(5) . . . . ?
C1F C1O C14 N2 178.9(3) . . . . ?
C1F C1O C14 C17 -1.3(4) . . . . ?
C1F C10 C15 C17 -0.8(5) . . . . ?
C1G C1E C8 C19 -0.2(5) . . . . ?
C1G C1N C1W C19 2.0(5) . . . . ?
C1H N12 C1C O8 -7.3(5) . . . . ?
C1H N12 C1C N6 173.8(3) . . . . ?
C1J C1D C6 N3 -178.2(3) . . . . ?
C1J C1D C6 C9 1.6(5) . . . . ?
C1K C1A C1P C18 0.5(5) . . . . ?
C1K C1A C1Y F6 36.3(4) . . . . ?
C1K C1A C1Y F13 157.5(3) . . . . ?
C1K C1A C1Y F15 -81.8(4) . . . . ?
C1L N7 C13 O7 -6.5(5) . . . . ?
C1L N7 C13 N3 173.8(3) . . . . ?
C1L N7 C21 C22 -94.6(4) . . . . ?
C1L C1T N9A C25A -98.8(18) . . . . ?
C1L C1T N9A C1 96(2) . . . . ?
C1M C1B C1X C1V 0.4(5) . . . . ?
C1M C1B C23 F7 -96.1(4) . . . . ?
C1M C1B C23 F9 24.0(4) . . . . ?
C1M C1B C23 F8 145.1(3) . . . . ?
C1M C1S N4 C27 -158.3(4) . . . . ?
C1M C1S N4 C27A -132.0(13) . . . . ?
C1N C1W C19 N1 -174.7(3) . . . . ?
C1N C1W C19 C8 -2.0(5) . . . . ?
C1O C1F C10 O9 -179.4(3) . . . . ?
C1O C1F C10 C15 0.8(5) . . . . ?
C1O C14 C17 C15 1.3(5) . . . . ?
C1P C1A C1K C12 -1.1(5) . . . . ?
C1P C1A C1Y F6 -145.6(3) . . . . ?
C1P C1A C1Y F13 -24.4(5) . . . . ?
C1P C1A C1Y F15 96.3(4) . . . . ?
C1Q N1 C19 C1W -16.6(5) . . . . ?
C1Q N1 C19 C8 170.5(3) . . . . ?
C1Q N9 C1T C1L 75.8(4) . . . . ?
C1Q N9 C25 C26 -105.4(4) . . . . ?
C1R C1S N4 C27 23.5(5) . . . . ?
C1R C1S N4 C27A 49.9(14) . . . . ?
C1R C1V C1X C1B -0.6(5) . . . . ?
C1R C1V C2A F1 28.6(5) . . . . ?
C1R C1V C2A F2 -89.5(4) . . . . ?
C1R C1V C2A F3 150.6(3) . . . . ?
C1S C1R C1V C1X -0.1(5) . . . . ?
C1S C1R C1V C2A 179.6(3) . . . . ?
C1S N4 C27 O16 -0.9(6) . . . . ?
C1S N4 C27 N5 175.5(3) . . . . ?
C1S N4 C27A O16A -38(4) . . . . ?
C1S N4 C27A N5A 155.3(17) . . . . ?
C1T N9 C1Q O14 -178.1(3) . . . . ?
C1T N9 C1Q N1 0.1(5) . . . . ?
C1T N9 C25 C26 77.6(4) . . . . ?
C1T N9A C1 N1 -6(3) . . . . ?
C1T N9A C1 O14A 166(2) . . . . ?
C1V C1R C1S C1M 1.0(5) . . . . ?
C1V C1R C1S N4 179.1(3) . . . . ?
C1X C1B C1M C1S 0.5(5) . . . . ?
C1X C1B C23 F7 82.5(4) . . . . ?
C1X C1B C23 F9 -157.3(3) . . . . ?
C1X C1B C23 F8 -36.3(4) . . . . ?
C1X C1V C2A F1 -151.6(3) . . . . ?
C1X C1V C2A F2 90.2(4) . . . . ?
C1X C1V C2A F3 -29.6(5) . . . . ?
C1Y C1A C1K C12 176.9(3) . . . . ?
C1Y C1A C1P C18 -177.5(3) . . . . ?
C1Z N8 C16 O11 175.5(3) . . . . ?
C1Z N8 C16 N2 -4.2(5) . . . . ?
C1Z N8 C22 C21 -104.7(3) . . . . ?
C2A C1V C1X C1B 179.7(3) . . . . ?
C2B O12 C7 C1I -0.6(5) . . . . ?
C2B O12 C7 C1J 178.5(3) . . . . ?
N4 C27A N5A C26A 166(2) . . . . ?
C6 N3 C13 O7 -12.1(5) . . . . ?
C6 N3 C13 N7 167.6(3) . . . . ?
C6 C1D C1J C7 -0.2(5) . . . . ?
C7 C1I C9 C6 0.6(5) . . . . ?
C8 C1E C1G O1 179.1(3) . . . . ?
C8 C1E C1G C1N 0.2(5) . . . . ?
C9 C1I C7 O12 179.9(3) . . . . ?
C9 C1I C7 C1J 0.8(5) . . . . ?
C10 C1F C1O C14 0.3(5) . . . . ?
C10 C15 C17 C14 -0.3(5) . . . . ?
C12 N6 C1C O8 3.1(5) . . . . ?
C12 N6 C1C N12 -178.0(3) . . . . ?
C12 C11 C18 C1P -0.7(5) . . . . ?
C12 C11 C18 C1U 175.0(3) . . . . ?
C13 N3 C6 C1D -145.8(3) . . . . ?
C13 N3 C6 C9 34.5(5) . . . . ?
C13 N7 C1L C1T 76.9(3) . . . . ?
C13 N7 C21 C22 89.6(4) . . . . ?
C14 N2 C16 O11 0.1(5) . . . . ?
C14 N2 C16 N8 179.9(3) . . . . ?
C16 N2 C14 C1O -28.9(5) . . . . ?
C16 N2 C14 C17 151.3(3) . . . . ?
C16 N8 C1Z C1H 87.5(4) . . . . ?
C16 N8 C22 C21 83.3(4) . . . . ?
C18 C11 C12 N6 -178.7(3) . . . . ?
C18 C11 C12 C1K 0.0(5) . . . . ?
C19 N1 C1Q O14 -12.2(5) . . . . ?
C19 N1 C1Q N9 169.6(3) . . . . ?
C19 N1 C1 N9A 178.7(15) . . . . ?
C19 N1 C1 O14A 6(4) . . . . ?
C20 O9 C10 C1F 159.9(3) . . . . ?
C20 O9 C10 C15 -20.3(4) . . . . ?
C21 N7 C1L C1T -99.1(3) . . . . ?
C21 N7 C13 O7 169.5(3) . . . . ?
C21 N7 C13 N3 -10.3(4) . . . . ?
C22 N8 C1Z C1H -83.9(4) . . . . ?
C22 N8 C16 O11 -12.7(5) . . . . ?
C22 N8 C16 N2 167.5(3) . . . . ?
C23 C1B C1M C1S 179.1(3) . . . . ?
C23 C1B C1X C1V -178.2(3) . . . . ?
C25 N9 C1Q O14 5.0(5) . . . . ?
C25 N9 C1Q N1 -176.7(3) . . . . ?
C25 N9 C1T C1L -107.3(3) . . . . ?
C26 N5 C27 O16 -7.9(6) . . . . ?
C26 N5 C27 N4 175.8(3) . . . . ?
C27 N5 C26 C25 77.0(4) . . . . ?
C28 O1 C1G C1E 1.8(5) . . . . ?
C28 O1 C1G C1N -179.2(3) . . . . ?
C27A N5A C26A C25A -94(3) . . . . ?
O16A C27A N5A C26A -1(5) . . . . ?
N5A C26A C25A N9A 173.9(19) . . . . ?
C26A C25A N9A C1T -82(3) . . . . ?
C26A C25A N9A C1 83(3) . . . . ?
C25A N9A C1 N1 -172(2) . . . . ?
C25A N9A C1 O14A 1(4) . . . . ?
C1 N1 C19 C1W -44.9(17) . . . . ?
C1 N1 C19 C8 142.2(16) . . . . ?

_olex2_date_sample_data_collection 2020-11-05
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.765
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_dte126
_database_code_depnum_ccdc_archive 'CCDC 2189998'
loop_
_audit_author_name
_audit_author_address
'Natalie E Pridmore'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2022-07-13 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2019-05-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C29 H30 F6 N6 O3'
_chemical_formula_sum            'C29 H30 F6 N6 O3'
_chemical_formula_weight         624.59
_chemical_melting_point          458
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2730(3)
_cell_length_b                   19.1589(4)
_cell_length_c                   15.2648(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.0383(13)
_cell_angle_gamma                90
_cell_volume                     2948.82(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8842
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0716 before and 0.0475 after correction. The Ratio of minimum to maximum transmission is 0.8428. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.382
_exptl_crystal_size_min          0.207
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            39105
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.725
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5101
_reflns_number_total             6760
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     356
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+1.6032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          
;
  The molecule shows disorder due to different optical orientations of the
 -N-CH2-N-CH2-N- chain. Consequently, some atoms have been modelled in two
 positions, with a refined occupancy ratio of 0.8898:0.1102(18). Equivalent atom 
 distances in the major and minor component have been restrained to be the same
 (e.g. N5-C20 and N5A-C20A) and due to close proximity, equivalent atoms in the
 major and minor component have been restrained to have the same ADP.

 One of the CF3 groups also shows disorder, due to spinning, and has been
 modelled with the fluorine atoms in two positions with a refined occupancy ratio
 of 0.893:0.107(3). Equivalent atom distances in the major and minor component 
 have been restrained to be the same (e.g. F1-F2 and F1A-F2A). Due to close
 proximity, equivalent atoms in the major and minor component have been 
 constrained to have the same ADP. 

 Hydrogen atoms on nitrogen atoms (except N2A and N4A, due to the low occupancy
 of the minor component) were found by difference map and their positions freely 
 refined. All other hydrogens (including N2A and N4A) were geometrically placed
 and refined using a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C19 \\sim C20A-C19A
 with sigma of 0.01
 C11-C10 \\sim C11A-C10A
 with sigma of 0.01
 C19-C11 \\sim C19A-C11A
 with sigma of 0.01
 C7-F1 \\sim C7-F1A \\sim C7-F2 \\sim C7-F2A \\sim C7-F3 \\sim C7-F3A
 with sigma of 0.01
 F1-F2 \\sim F1A-F2A \\sim F2-F3 \\sim F2A-F3A \\sim F3-F1 \\sim F3A-F1A
 with sigma of 0.01
 N3-C11 \\sim N3A-C11A
 with sigma of 0.01
 C20-N3 \\sim C20A-N3A
 with sigma of 0.01
 N3-C10 \\sim N3A-C10A
 with sigma of 0.01
 C27-N5 \\sim C27-N5A
 with sigma of 0.01
 C28-N5 \\sim C28A-N5A
 with sigma of 0.01
 C28-C29 \\sim C28A-C29A
 with sigma of 0.01
 N5-C29 \\sim N5A-C29A
 with sigma of 0.01
 N5-C20 \\sim N5A-C20A
 with sigma of 0.01
 N5-C19 \\sim N5A-C19A
 with sigma of 0.01
 C10-N2 \\sim C10A-N2A
 with sigma of 0.01
 C9-N2 \\sim C9-N2A
 with sigma of 0.01
 C11-N2 \\sim C11A-N2A
 with sigma of 0.01
 C12-N3 \\sim C12A-N3A
 with sigma of 0.01
 C12-O2 \\sim C12A-O2A
 with sigma of 0.01
 C12-N4 \\sim C12A-N4A
 with sigma of 0.01
 N4-O2 \\sim N4A-O2A
 with sigma of 0.01
 N4-C13 \\sim N4A-C13
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C10 \\sim C10A \\sim C11 \\sim C11A \\sim C12 \\sim C12A \\sim C19 \\sim C19A
\\sim C20 \\sim C20A \\sim C28 \\sim C28A \\sim C29 \\sim C29A \\sim N2 \\sim
N2A \\sim N3 \\sim N3A \\sim N4 \\sim N4A \\sim N5 \\sim N5A \\sim O2 \\sim
O2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(C10A)=Sof(H10C)=Sof(H10D)=Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C28A)=
 Sof(H28C)=Sof(H28D)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(N2A)=Sof(H2AA)=
 Sof(N3A)=Sof(N4A)=Sof(H4AA)=Sof(N5A)=Sof(O2A)=1-FVAR(1)
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(N2)=Sof(H2A)=Sof(N3)=Sof(N4)=
 Sof(H4A)=Sof(N5)=Sof(O2)=FVAR(1)
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(2)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D), C11(H11A,H11B), C11A(H11C,H11D), C19(H19A,
 H19B), C19A(H19C,H19D), C20(H20A,H20B), C20A(H20C,H20D), C28(H28A,H28B),
 C28A(H28C,H28D)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), N2A(H2AA), N4A(H4AA)
5.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.08598(15) 0.27232(8) 0.97069(10) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.02670(16) 0.20756(8) 0.94711(10) 0.0245(3) Uani 1 1 d . . . . .
H2 H 0.0510 0.1815 0.8997 0.029 Uiso 1 1 calc R . . . .
C3 C -0.06682(16) 0.18118(9) 0.99222(11) 0.0274(3) Uani 1 1 d . . . . .
C4 C -0.10315(16) 0.21758(9) 1.06254(11) 0.0286(4) Uani 1 1 d . . . . .
H4 H -0.1680 0.1995 1.0932 0.034 Uiso 1 1 calc R . . . .
C5 C -0.04195(16) 0.28083(8) 1.08640(10) 0.0251(3) Uani 1 1 d . . . . .
C6 C 0.05179(15) 0.30900(8) 1.04182(10) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.0920 0.3527 1.0596 0.027 Uiso 1 1 calc R . . . .
C7 C -0.1323(2) 0.11275(10) 0.96472(13) 0.0420(5) Uani 1 1 d D . . . .
C8 C -0.07079(19) 0.31900(10) 1.16569(12) 0.0346(4) Uani 1 1 d . . . . .
C9 C 0.23469(17) 0.36098(8) 0.92264(11) 0.0278(4) Uani 1 1 d D . . . .
C10 C 0.3839(2) 0.43261(9) 0.85551(14) 0.0279(4) Uani 0.8898(18) 1 d D U P A 1
H10A H 0.4490 0.4255 0.8162 0.034 Uiso 0.8898(18) 1 calc R . P A 1
H10B H 0.4336 0.4431 0.9162 0.034 Uiso 0.8898(18) 1 calc R . P A 1
C10A C 0.3052(12) 0.4503(6) 0.8285(8) 0.025(2) Uani 0.1102(18) 1 d D U P A 2
H10C H 0.2431 0.4873 0.8399 0.030 Uiso 0.1102(18) 1 calc R . P A 2
H10D H 0.3180 0.4554 0.7662 0.030 Uiso 0.1102(18) 1 calc R . P A 2
C11 C 0.29473(18) 0.49425(9) 0.82141(12) 0.0258(4) Uani 0.8898(18) 1 d D U P A
1
H11A H 0.2671 0.4908 0.7558 0.031 Uiso 0.8898(18) 1 calc R . P A 1
H11B H 0.2139 0.4925 0.8478 0.031 Uiso 0.8898(18) 1 calc R . P A 1
C11A C 0.4374(11) 0.4604(5) 0.8913(9) 0.026(2) Uani 0.1102(18) 1 d D U P A 2
H11C H 0.4319 0.4408 0.9505 0.031 Uiso 0.1102(18) 1 calc R . P A 2
H11D H 0.5067 0.4343 0.8681 0.031 Uiso 0.1102(18) 1 calc R . P A 2
C12 C 0.3689(2) 0.59329(10) 0.92444(13) 0.0250(4) Uani 0.8898(18) 1 d D U P A 1
C12A C 0.4233(18) 0.5805(8) 0.9533(12) 0.030(2) Uani 0.1102(18) 1 d D U P A 2
C13 C 0.26151(17) 0.59051(8) 1.05736(10) 0.0256(3) Uani 1 1 d D . . . .
C14 C 0.16245(17) 0.55388(9) 1.08940(11) 0.0279(4) Uani 1 1 d . . . . .
H14 H 0.1330 0.5100 1.0642 0.033 Uiso 1 1 calc R . . . .
C15 C 0.10733(18) 0.58133(10) 1.15754(12) 0.0343(4) Uani 1 1 d . . . . .
H15 H 0.0403 0.5561 1.1791 0.041 Uiso 1 1 calc R . . . .
C16 C 0.1490(2) 0.64519(10) 1.19466(12) 0.0383(4) Uani 1 1 d . . . . .
H16 H 0.1105 0.6642 1.2413 0.046 Uiso 1 1 calc R . . . .
C17 C 0.2472(2) 0.68118(9) 1.16325(12) 0.0356(4) Uani 1 1 d . . . . .
H17 H 0.2760 0.7250 1.1889 0.043 Uiso 1 1 calc R . . . .
C18 C 0.30465(18) 0.65465(9) 1.09511(11) 0.0311(4) Uani 1 1 d . . . . .
H18 H 0.3725 0.6799 1.0745 0.037 Uiso 1 1 calc R . . . .
C19 C 0.43237(19) 0.59289(9) 0.78047(12) 0.0243(4) Uani 0.8898(18) 1 d D U P A
1
H19A H 0.4106 0.6433 0.7762 0.029 Uiso 0.8898(18) 1 calc R . P A 1
H19B H 0.4013 0.5719 0.7209 0.029 Uiso 0.8898(18) 1 calc R . P A 1
C19A C 0.5701(13) 0.5620(6) 0.8505(8) 0.028(2) Uani 0.1102(18) 1 d D U P A 2
H19C H 0.6259 0.5238 0.8343 0.034 Uiso 0.1102(18) 1 calc R . P A 2
H19D H 0.6289 0.5958 0.8881 0.034 Uiso 0.1102(18) 1 calc R . P A 2
C20 C 0.58259(18) 0.58426(9) 0.80647(13) 0.0243(4) Uani 0.8898(18) 1 d D U P A
1
H20A H 0.6115 0.5947 0.8708 0.029 Uiso 0.8898(18) 1 calc R . P A 1
H20B H 0.6067 0.5353 0.7964 0.029 Uiso 0.8898(18) 1 calc R . P A 1
C20A C 0.4988(13) 0.5982(7) 0.7662(8) 0.029(2) Uani 0.1102(18) 1 d D U P A 2
H20C H 0.4612 0.5625 0.7215 0.034 Uiso 0.1102(18) 1 calc R . P A 2
H20D H 0.4244 0.6262 0.7803 0.034 Uiso 0.1102(18) 1 calc R . P A 2
C21 C 0.61580(16) 0.79542(8) 0.86988(10) 0.0249(3) Uani 1 1 d . . . . .
C22 C 0.50226(18) 0.82261(9) 0.89322(13) 0.0360(4) Uani 1 1 d . . . . .
H22 H 0.4271 0.7936 0.8924 0.043 Uiso 1 1 calc R . . . .
C23 C 0.4982(2) 0.89214(10) 0.91772(15) 0.0437(5) Uani 1 1 d . . . . .
H23 H 0.4197 0.9108 0.9330 0.052 Uiso 1 1 calc R . . . .
C24 C 0.6077(2) 0.93450(9) 0.92002(13) 0.0376(4) Uani 1 1 d . . . . .
H24 H 0.6047 0.9822 0.9365 0.045 Uiso 1 1 calc R . . . .
C25 C 0.72126(18) 0.90704(9) 0.89824(11) 0.0315(4) Uani 1 1 d . . . . .
H25 H 0.7969 0.9360 0.9005 0.038 Uiso 1 1 calc R . . . .
C26 C 0.72652(17) 0.83770(8) 0.87302(11) 0.0267(3) Uani 1 1 d . . . . .
H26 H 0.8052 0.8192 0.8580 0.032 Uiso 1 1 calc R . . . .
C27 C 0.66031(17) 0.70082(8) 0.77175(11) 0.0288(4) Uani 1 1 d D . . . .
C28 C 0.6676(2) 0.60561(12) 0.66549(14) 0.0288(5) Uani 0.8898(18) 1 d D U P A 1
H28A H 0.6856 0.6459 0.6290 0.035 Uiso 0.8898(18) 1 calc R . P A 1
H28B H 0.5838 0.5837 0.6350 0.035 Uiso 0.8898(18) 1 calc R . P A 1
C28A C 0.619(2) 0.6165(11) 0.6428(9) 0.033(3) Uani 0.1102(18) 1 d D U P A 2
H28C H 0.6533 0.6548 0.6101 0.040 Uiso 0.1102(18) 1 calc R . P A 2
H28D H 0.5367 0.5985 0.6048 0.040 Uiso 0.1102(18) 1 calc R . P A 2
C29 C 0.7785(3) 0.55368(15) 0.67113(19) 0.0398(6) Uani 0.8898(18) 1 d D U P A 1
H29A H 0.7872 0.5395 0.6108 0.060 Uiso 0.8898(18) 1 calc GR . P A 1
H29B H 0.7591 0.5126 0.7047 0.060 Uiso 0.8898(18) 1 calc GR . P A 1
H29C H 0.8617 0.5750 0.7016 0.060 Uiso 0.8898(18) 1 calc GR . P A 1
C29A C 0.720(2) 0.5591(11) 0.6602(15) 0.040(5) Uani 0.1102(18) 1 d D U P A 2
H29D H 0.7564 0.5507 0.6063 0.061 Uiso 0.1102(18) 1 calc GR . P A 2
H29E H 0.6777 0.5164 0.6764 0.061 Uiso 0.1102(18) 1 calc GR . P A 2
H29F H 0.7915 0.5727 0.7093 0.061 Uiso 0.1102(18) 1 calc GR . P A 2
F1 F -0.0974(2) 0.08430(9) 0.89431(15) 0.0764(7) Uani 0.893(3) 1 d D . P B 1
F1A F -0.1860(17) 0.0850(8) 1.0256(8) 0.0764(7) Uani 0.107(3) 1 d D . P B 2
F2 F -0.26321(16) 0.11837(11) 0.94352(17) 0.0842(7) Uani 0.893(3) 1 d D . P B 1
F2A F -0.0408(10) 0.0685(7) 0.9506(13) 0.0842(7) Uani 0.107(3) 1 d D . P B 2
F3 F -0.1111(3) 0.06621(11) 1.02889(13) 0.1060(10) Uani 0.893(3) 1 d D . P B 1
F3A F -0.2197(16) 0.1165(8) 0.8922(9) 0.1060(10) Uani 0.107(3) 1 d D . P B 2
F4 F 0.02031(13) 0.30437(7) 1.23937(7) 0.0548(3) Uani 1 1 d . . . . .
F5 F -0.18769(12) 0.30198(6) 1.18590(8) 0.0498(3) Uani 1 1 d . . . . .
F6 F -0.06881(12) 0.38851(6) 1.15643(8) 0.0444(3) Uani 1 1 d . . . . .
N1 N 0.17754(14) 0.29587(7) 0.92107(9) 0.0255(3) Uani 1 1 d . . . . .
H1 H 0.1935(18) 0.2692(10) 0.8812(13) 0.028(5) Uiso 1 1 d . . . . .
N2 N 0.3080(2) 0.36931(9) 0.85797(13) 0.0286(4) Uani 0.8898(18) 1 d D U P A 1
H2A H 0.316(2) 0.3352(11) 0.8231(14) 0.026(5) Uiso 0.8898(18) 1 d . . P A 1
N2A N 0.2468(13) 0.3828(6) 0.8388(6) 0.025(2) Uani 0.1102(18) 1 d D U P A 2
H2AA H 0.2194 0.3561 0.7920 0.030 Uiso 0.1102(18) 1 calc R . P A 2
N3 N 0.36241(15) 0.56040(7) 0.84420(10) 0.0247(3) Uani 0.8898(18) 1 d D U P A 1
N3A N 0.4750(11) 0.5333(5) 0.9014(7) 0.028(2) Uani 0.1102(18) 1 d D U P A 2
N4 N 0.3092(7) 0.5594(2) 0.9856(4) 0.0310(14) Uani 0.8898(18) 1 d D U P A 1
H4A H 0.283(2) 0.5187(11) 0.9741(14) 0.026(5) Uiso 0.8898(18) 1 d . . P A 1
N4A N 0.324(6) 0.5561(16) 0.995(4) 0.026(3) Uani 0.1102(18) 1 d D U P A 2
H4AA H 0.2964 0.5135 0.9803 0.031 Uiso 0.1102(18) 1 calc R . P A 2
N5 N 0.65094(17) 0.63081(8) 0.75425(11) 0.0251(4) Uani 0.8898(18) 1 d D U P A 1
N5A N 0.5880(12) 0.6440(5) 0.7280(7) 0.029(2) Uani 0.1102(18) 1 d D U P A 2
N6 N 0.61733(15) 0.72364(7) 0.84649(10) 0.0282(3) Uani 1 1 d . . . . .
H6A H 0.5661(19) 0.6960(10) 0.8709(13) 0.035(5) Uiso 1 1 d . . . . .
O1 O 0.22348(12) 0.40670(6) 0.97755(8) 0.0311(3) Uani 1 1 d . . . . .
O2 O 0.4259(3) 0.64997(12) 0.9395(2) 0.0292(7) Uani 0.8898(18) 1 d D U P A 1
O2A O 0.456(3) 0.6429(10) 0.956(2) 0.031(5) Uani 0.1102(18) 1 d D U P A 2
O3 O 0.70975(13) 0.74122(6) 0.72380(8) 0.0333(3) 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 1.399(2) . ?
C1 C6 1.393(2) . ?
C1 N1 1.3909(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 C4 1.390(2) . ?
C3 C7 1.496(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(2) . ?
C5 C6 1.390(2) . ?
C5 C8 1.492(2) . ?
C6 H6 0.9500 . ?
C7 F1 1.315(2) . ?
C7 F1A 1.284(6) . ?
C7 F2 1.326(3) . ?
C7 F2A 1.314(7) . ?
C7 F3 1.312(2) . ?
C7 F3A 1.287(7) . ?
C8 F4 1.348(2) . ?
C8 F5 1.336(2) . ?
C8 F6 1.340(2) . ?
C9 N1 1.377(2) . ?
C9 N2 1.361(2) . ?
C9 N2A 1.375(8) . ?
C9 O1 1.2330(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(3) . ?
C10 N2 1.446(2) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.517(9) . ?
C10A N2A 1.446(9) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N3 1.455(2) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C11A N3A 1.451(8) . ?
C12 N3 1.368(2) . ?
C12 N4 1.374(4) . ?
C12 O2 1.234(3) . ?
C12A N3A 1.374(9) . ?
C12A N4A 1.378(10) . ?
C12A O2A 1.240(9) . ?
C13 C14 1.399(2) . ?
C13 C18 1.393(2) . ?
C13 N4 1.415(2) . ?
C13 N4A 1.414(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.381(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.527(3) . ?
C19 N3 1.455(2) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C19A C20A 1.521(9) . ?
C19A N3A 1.466(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 N5 1.462(2) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C20A N5A 1.468(9) . ?
C21 C22 1.385(2) . ?
C21 C26 1.390(2) . ?
C21 N6 1.422(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(2) . ?
C26 H26 0.9500 . ?
C27 N5 1.367(2) . ?
C27 N5A 1.412(8) . ?
C27 N6 1.371(2) . ?
C27 O3 1.2389(19) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.503(3) . ?
C28 N5 1.479(2) . ?
C28A H28C 0.9900 . ?
C28A H28D 0.9900 . ?
C28A C29A 1.499(10) . ?
C28A N5A 1.493(9) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
N1 H1 0.834(19) . ?
N2 H2A 0.86(2) . ?
N2A H2AA 0.8800 . ?
N4 H4A 0.83(2) . ?
N4A H4AA 0.8800 . ?
N6 H6A 0.88(2) . ?

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
C6 C1 C2 119.05(14) . . ?
N1 C1 C2 117.01(13) . . ?
N1 C1 C6 123.94(14) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.44(15) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 121.13(15) . . ?
C2 C3 C7 119.94(15) . . ?
C4 C3 C7 118.92(15) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.89(14) . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 122.30(14) . . ?
C4 C5 C8 119.53(14) . . ?
C6 C5 C8 118.09(15) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 C1 119.16(14) . . ?
C5 C6 H6 120.4 . . ?
F1 C7 C3 114.48(15) . . ?
F1 C7 F2 104.89(18) . . ?
F1A C7 C3 113.0(7) . . ?
F1A C7 F2A 105.8(6) . . ?
F1A C7 F3A 108.7(6) . . ?
F2 C7 C3 112.18(18) . . ?
F2A C7 C3 108.3(6) . . ?
F3 C7 C3 112.62(17) . . ?
F3 C7 F1 107.2(2) . . ?
F3 C7 F2 104.66(19) . . ?
F3A C7 C3 113.3(6) . . ?
F3A C7 F2A 107.3(6) . . ?
F4 C8 C5 111.17(14) . . ?
F5 C8 C5 113.24(16) . . ?
F5 C8 F4 105.53(14) . . ?
F5 C8 F6 107.43(14) . . ?
F6 C8 C5 113.09(14) . . ?
F6 C8 F4 105.83(16) . . ?
N2 C9 N1 112.77(14) . . ?
N2A C9 N1 112.0(4) . . ?
O1 C9 N1 124.08(14) . . ?
O1 C9 N2 123.13(15) . . ?
O1 C9 N2A 117.0(5) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C11 111.55(17) . . ?
H10C C10A H10D 107.8 . . ?
C11A C10A H10C 109.1 . . ?
C11A C10A H10D 109.1 . . ?
N2A C10A H10C 109.1 . . ?
N2A C10A H10D 109.1 . . ?
N2A C10A C11A 112.6(8) . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N3 C11 C10 111.41(16) . . ?
N3 C11 H11A 109.3 . . ?
N3 C11 H11B 109.3 . . ?
C10A C11A H11C 109.2 . . ?
C10A C11A H11D 109.2 . . ?
H11C C11A H11D 107.9 . . ?
N3A C11A C10A 112.2(8) . . ?
N3A C11A H11C 109.2 . . ?
N3A C11A H11D 109.2 . . ?
N3 C12 N4 116.1(2) . . ?
O2 C12 N3 120.8(2) . . ?
O2 C12 N4 123.2(2) . . ?
N3A C12A N4A 116.3(11) . . ?
O2A C12A N3A 121.3(16) . . ?
O2A C12A N4A 122.1(12) . . ?
C14 C13 N4 116.26(18) . . ?
C14 C13 N4A 117.3(9) . . ?
C18 C13 C14 119.53(15) . . ?
C18 C13 N4 124.20(18) . . ?
C18 C13 N4A 122.7(11) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.21(16) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.48(17) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.27(16) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.42(17) . . ?
C18 C17 H17 119.3 . . ?
C13 C18 H18 120.5 . . ?
C17 C18 C13 119.09(16) . . ?
C17 C18 H18 120.5 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
N3 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
N3 C19 C20 112.56(15) . . ?
H19C C19A H19D 108.0 . . ?
C20A C19A H19C 109.5 . . ?
C20A C19A H19D 109.5 . . ?
N3A C19A H19C 109.5 . . ?
N3A C19A H19D 109.5 . . ?
N3A C19A C20A 110.9(9) . . ?
C19 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N5 C20 C19 111.04(15) . . ?
N5 C20 H20A 109.4 . . ?
N5 C20 H20B 109.4 . . ?
C19A C20A H20C 109.2 . . ?
C19A C20A H20D 109.2 . . ?
H20C C20A H20D 107.9 . . ?
N5A C20A C19A 111.9(9) . . ?
N5A C20A H20C 109.2 . . ?
N5A C20A H20D 109.2 . . ?
C22 C21 C26 119.73(15) . . ?
C22 C21 N6 118.61(15) . . ?
C26 C21 N6 121.61(15) . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.09(17) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.9 . . ?
C24 C23 C22 120.29(17) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.51(16) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.84(16) . . ?
C26 C25 H25 119.6 . . ?
C21 C26 H26 120.2 . . ?
C25 C26 C21 119.52(16) . . ?
C25 C26 H26 120.2 . . ?
N5 C27 N6 116.96(14) . . ?
N6 C27 N5A 114.6(4) . . ?
O3 C27 N5 121.25(15) . . ?
O3 C27 N5A 116.1(4) . . ?
O3 C27 N6 121.75(15) . . ?
H28A C28 H28B 107.8 . . ?
C29 C28 H28A 109.1 . . ?
C29 C28 H28B 109.1 . . ?
N5 C28 H28A 109.1 . . ?
N5 C28 H28B 109.1 . . ?
N5 C28 C29 112.5(2) . . ?
H28C C28A H28D 108.0 . . ?
C29A C28A H28C 109.4 . . ?
C29A C28A H28D 109.4 . . ?
N5A C28A H28C 109.4 . . ?
N5A C28A H28D 109.4 . . ?
N5A C28A C29A 111.1(9) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28A C29A H29D 109.5 . . ?
C28A C29A H29E 109.5 . . ?
C28A C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
C1 N1 H1 116.5(13) . . ?
C9 N1 C1 127.95(13) . . ?
C9 N1 H1 115.1(13) . . ?
C9 N2 C10 119.55(16) . . ?
C9 N2 H2A 119.7(14) . . ?
C10 N2 H2A 120.4(14) . . ?
C9 N2A C10A 119.1(9) . . ?
C9 N2A H2AA 120.4 . . ?
C10A N2A H2AA 120.4 . . ?
C11 N3 C19 119.15(14) . . ?
C12 N3 C11 123.67(15) . . ?
C12 N3 C19 117.13(14) . . ?
C11A N3A C19A 119.7(9) . . ?
C12A N3A C11A 124.8(11) . . ?
C12A N3A C19A 115.5(10) . . ?
C12 N4 C13 126.3(3) . . ?
C12 N4 H4A 117.8(14) . . ?
C13 N4 H4A 114.4(14) . . ?
C12A N4A C13 128.6(14) . . ?
C12A N4A H4AA 115.7 . . ?
C13 N4A H4AA 115.7 . . ?
C20 N5 C28 116.87(15) . . ?
C27 N5 C20 121.00(14) . . ?
C27 N5 C28 118.89(15) . . ?
C20A N5A C28A 112.9(12) . . ?
C27 N5A C20A 125.8(9) . . ?
C27 N5A C28A 120.3(11) . . ?
C21 N6 H6A 116.1(13) . . ?
C27 N6 C21 122.55(13) . . ?
C27 N6 H6A 118.4(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
C6 H6 O1 0.95 2.26 2.8704(19) 121.2 .
C11A H11C O2A 0.99 2.31 3.10(3) 136.1 3_667
C18 H18 O2A 0.95 2.26 2.87(3) 121.4 .
N1 H1 O3 0.834(19) 2.111(19) 2.8824(17) 153.7(17) 2_646
N2 H2A O3 0.86(2) 1.94(2) 2.743(2) 156.2(19) 2_646
N4 H4A O1 0.83(2) 2.23(2) 3.051(3) 166.7(19) .
N4A H4AA O1 0.88 2.18 3.04(2) 166.5 .
N6 H6A O2 0.88(2) 2.13(2) 2.991(3) 167.4(18) .
N6 H6A O2A 0.88(2) 2.13(3) 3.00(3) 167.3(19) .

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
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C7 178.30(16) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
C2 C1 N1 C9 170.12(16) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C3 C7 F1 -3.1(3) . . . . ?
C2 C3 C7 F1A 161.0(9) . . . . ?
C2 C3 C7 F2 -122.4(2) . . . . ?
C2 C3 C7 F2A 44.1(10) . . . . ?
C2 C3 C7 F3 119.8(2) . . . . ?
C2 C3 C7 F3A -74.8(11) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C5 C8 -175.52(15) . . . . ?
C4 C3 C7 F1 176.1(2) . . . . ?
C4 C3 C7 F1A -19.8(9) . . . . ?
C4 C3 C7 F2 56.7(2) . . . . ?
C4 C3 C7 F2A -136.7(10) . . . . ?
C4 C3 C7 F3 -61.1(3) . . . . ?
C4 C3 C7 F3A 104.4(11) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C4 C5 C8 F4 94.79(19) . . . . ?
C4 C5 C8 F5 -23.8(2) . . . . ?
C4 C5 C8 F6 -146.33(16) . . . . ?
C6 C1 C2 C3 1.6(2) . . . . ?
C6 C1 N1 C9 -10.4(3) . . . . ?
C6 C5 C8 F4 -81.88(19) . . . . ?
C6 C5 C8 F5 159.52(15) . . . . ?
C6 C5 C8 F6 37.0(2) . . . . ?
C7 C3 C4 C5 -179.62(16) . . . . ?
C8 C5 C6 C1 176.38(15) . . . . ?
C10 C11 N3 C12 -84.5(2) . . . . ?
C10 C11 N3 C19 92.87(19) . . . . ?
C10A C11A N3A C12A 77.4(18) . . . . ?
C10A C11A N3A C19A -99.5(13) . . . . ?
C11 C10 N2 C9 -74.1(2) . . . . ?
C11A C10A N2A C9 51.1(16) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C13 C18 C17 -0.7(3) . . . . ?
C14 C13 N4 C12 156.2(5) . . . . ?
C14 C13 N4A C12A 180(5) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C18 C13 C14 C15 0.4(3) . . . . ?
C18 C13 N4 C12 -22.2(10) . . . . ?
C18 C13 N4A C12A -8(9) . . . . ?
C19 C20 N5 C27 74.7(2) . . . . ?
C19 C20 N5 C28 -84.7(2) . . . . ?
C19A C20A N5A C27 -58.7(17) . . . . ?
C19A C20A N5A C28A 109.3(14) . . . . ?
C20 C19 N3 C11 -103.89(19) . . . . ?
C20 C19 N3 C12 73.7(2) . . . . ?
C20A C19A N3A C11A 96.9(13) . . . . ?
C20A C19A N3A C12A -80.3(16) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C21 C26 C25 -1.0(2) . . . . ?
C22 C21 N6 C27 132.24(18) . . . . ?
C22 C23 C24 C25 -0.3(3) . . . . ?
C23 C24 C25 C26 0.8(3) . . . . ?
C24 C25 C26 C21 -0.1(3) . . . . ?
C26 C21 C22 C23 1.4(3) . . . . ?
C26 C21 N6 C27 -50.2(2) . . . . ?
C29 C28 N5 C20 -78.1(2) . . . . ?
C29 C28 N5 C27 122.0(2) . . . . ?
C29A C28A N5A C20A -78(2) . . . . ?
C29A C28A N5A C27 91(2) . . . . ?
N1 C1 C2 C3 -178.91(15) . . . . ?
N1 C1 C6 C5 179.45(15) . . . . ?
N1 C9 N2 C10 -174.66(18) . . . . ?
N1 C9 N2A C10A -180.0(9) . . . . ?
N2 C9 N1 C1 -172.51(17) . . . . ?
N2 C9 N2A C10A -82.3(11) . . . . ?
N2 C10 C11 N3 162.38(15) . . . . ?
N2A C9 N1 C1 -140.8(7) . . . . ?
N2A C9 N2 C10 90.7(9) . . . . ?
N2A C10A C11A N3A -161.9(10) . . . . ?
N3 C12 N4 C13 -156.3(5) . . . . ?
N3 C19 C20 N5 -166.37(14) . . . . ?
N3A C12A N4A C13 174(5) . . . . ?
N3A C19A C20A N5A 163.6(10) . . . . ?
N4 C12 N3 C11 1.4(5) . . . . ?
N4 C12 N3 C19 -176.0(4) . . . . ?
N4 C13 C14 C15 -178.1(4) . . . . ?
N4 C13 C18 C17 177.7(5) . . . . ?
N4 C13 N4A C12A 95(10) . . . . ?
N4A C12A N3A C11A -3(4) . . . . ?
N4A C12A N3A C19A 174(4) . . . . ?
N4A C13 C14 C15 173(4) . . . . ?
N4A C13 C18 C17 -173(4) . . . . ?
N4A C13 N4 C12 -104(7) . . . . ?
N5 C27 N5A C20A 85.6(12) . . . . ?
N5 C27 N5A C28A -81.6(12) . . . . ?
N5 C27 N6 C21 -176.94(16) . . . . ?
N5A C27 N5 C20 -85.6(7) . . . . ?
N5A C27 N5 C28 73.4(8) . . . . ?
N5A C27 N6 C21 -142.8(6) . . . . ?
N6 C21 C22 C23 179.01(18) . . . . ?
N6 C21 C26 C25 -178.49(15) . . . . ?
N6 C27 N5 C20 7.6(3) . . . . ?
N6 C27 N5 C28 166.67(17) . . . . ?
N6 C27 N5A C20A -16.4(14) . . . . ?
N6 C27 N5A C28A 176.5(9) . . . . ?
O1 C9 N1 C1 8.9(3) . . . . ?
O1 C9 N2 C10 4.0(3) . . . . ?
O1 C9 N2A C10A 28.0(13) . . . . ?
O2 C12 N3 C11 -178.8(2) . . . . ?
O2 C12 N3 C19 3.8(3) . . . . ?
O2 C12 N4 C13 23.9(10) . . . . ?
O2A C12A N3A C11A -177(2) . . . . ?
O2A C12A N3A C19A 0(3) . . . . ?
O2A C12A N4A C13 -12(9) . . . . ?
O3 C27 N5 C20 -174.82(17) . . . . ?
O3 C27 N5 C28 -15.8(3) . . . . ?
O3 C27 N5A C20A -166.6(9) . . . . ?
O3 C27 N5A C28A 26.2(13) . . . . ?
O3 C27 N6 C21 5.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_s5691a_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2195712'
loop_
_audit_author_name
_audit_author_address
'Inigo Vitorica-Yrezabal'
;University of Manchester
United Kingdom
;
_audit_update_record             
;
2022-08-08 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        
1-(2-(3-(3,5-bis(trifluoromethyl)phenyl)ureido)ethyl)-3-hexyl-1-(2-(3-hexylureido)ethyl)urea
_chemical_formula_moiety         'C27 H42 F6 N6 O3'
_chemical_formula_sum            'C27 H42 F6 N6 O3'
_chemical_formula_weight         612.66
_chemical_melting_point          421-423
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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2341(13)
_cell_length_b                   13.1050(13)
_cell_length_c                   24.026(3)
_cell_angle_alpha                104.669(9)
_cell_angle_beta                 93.989(10)
_cell_angle_gamma                99.942(10)
_cell_volume                     3048.6(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2366
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      24.8220
_cell_measurement_theta_min      3.6210
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1873
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16786
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  12.00   1.00    5.00    --  -18.04 -77.00-150.00   44
  2  ω    -42.00  12.00   1.00    5.00    --  -18.04 -77.00  90.00   54
  3  ω     39.00  92.00   1.00    5.00    --   19.45 178.00 -60.00   53
  4  ω    -48.00  45.00   1.00    5.00    --   19.45 -37.00 -90.00   93
  5  ω     -6.00  90.00   1.00    5.00    --   19.45  37.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0177469000
_diffrn_orient_matrix_UB_12      -0.0389490000
_diffrn_orient_matrix_UB_13      -0.0271996000
_diffrn_orient_matrix_UB_21      -0.0028023000
_diffrn_orient_matrix_UB_22      -0.0417100000
_diffrn_orient_matrix_UB_23      0.0140574000
_diffrn_orient_matrix_UB_31      -0.0685517000
_diffrn_orient_matrix_UB_32      0.0001567000
_diffrn_orient_matrix_UB_33      0.0026893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6800
_reflns_number_total             16786
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     781
_refine_ls_number_reflns         16786
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      0.816
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1413
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.57899
 0.42101
2. Uiso/Uaniso restraints and constraints
C35 \\sim C32 \\sim C31 \\sim C33 \\sim C34: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
N7 \\sim C5 \\sim C3 \\sim N4: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004 within 2A
C8 \\sim N7 \\sim C5 \\sim N4 \\sim C3 \\sim C2: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004 within 2A
N1 \\sim C36 \\sim N38 \\sim C39 \\sim C40 \\sim C41: within 2A with sigma of
0.002 and sigma for terminal atoms of 0.004 within 2A
O126 \\sim C125 \\sim N127 \\sim C128 \\sim N124: within 2A with sigma of 0.002
and sigma for terminal atoms of 0.004 within 2A
C35 \\sim C32 \\sim C33 \\sim C31: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
Uanis(N4) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(N38) \\sim Ueq, Uanis(N1) \\sim
Ueq, Uanis(N24) \\sim Ueq, Uanis(N104) \\sim Ueq: with sigma of 0.002 and sigma
for terminal atoms of 0.004
Uanis(C113) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3. Others
 Sof(H30C)=Sof(H30D)=Sof(H35D)=Sof(H35E)=Sof(H35F)=Sof(C33)=Sof(H33A)=
 Sof(H33B)=Sof(C34)=Sof(H34A)=Sof(H34B)=1-FVAR(1)
 Sof(H30A)=Sof(H30B)=Sof(H35A)=Sof(H35B)=Sof(H35C)=Sof(C32)=Sof(H32A)=
 Sof(H32B)=Sof(C31)=Sof(H31A)=Sof(H31B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C103(H10A,H10B), C2(H2A,H2B), C129(H12A,H12B), C102(H10C,H10D),
 C23(H23A,H23B), C123(H12C,H12D), C22(H22A,H22B), C39(H39A,H39B), C28(H28A,
 H28B), C128(H12E,H12F), C137(H13A,H13B), C138(H13C,H13D), C40(H40A,H40B),
 C41(H41A,H41B), C139(H13E,H13F), C131(H13G,H13H), C43(H43A,H43B), C140(H14A,
 H14B), C130(H13I,H13J), C132(H13N,H13O), C122(H12G,H12H), C42(H42A,H42B),
 C29(H29A,H29B), C30(H30A,H30B), C30(H30C,H30D), C141(H14F,H14G), C32(H32A,
 H32B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B)
4.b Aromatic/amide H refined with riding coordinates:
 N7(H7), N24(H24), N107(H107), N124(H124), N38(H38), N104(H104), N4(H4),
 N127(H127), N136(H136), N27(H27), C9(H9), C113(H113), C13(H13), C11(H11),
 C111(H111), C109(H109)
4.c Idealised Me refined as rotating group:
 C133(H13K,H13L,H13M), C142(H14C,H14D,H14E), C44(H44A,H44B,H44C), C35(H35A,
 H35B,H35C), C35(H35D,H35E,H35F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F19 F -0.3450(3) -0.1695(2) 0.68731(11) 0.0229(8) Uani 1 1 d . . . . .
F120 F 1.3770(3) 0.6749(2) 0.80687(11) 0.0250(8) Uani 1 1 d . . . . .
F20 F -0.3477(3) -0.2113(2) 0.59462(11) 0.0285(8) Uani 1 1 d . . . . .
F121 F 1.2113(3) 0.7306(3) 0.84704(13) 0.0312(8) Uani 1 1 d . . . . .
F21 F -0.1741(3) -0.2178(3) 0.64922(12) 0.0320(8) Uani 1 1 d . . . . .
F119 F 1.3886(3) 0.7271(2) 0.89950(11) 0.0280(8) Uani 1 1 d . . . . .
O106 O 0.9104(3) 0.1926(3) 0.80784(13) 0.0181(9) Uani 1 1 d . . . . .
O37 O 0.3764(3) 0.6759(3) 0.67933(13) 0.0158(9) Uani 1 1 d . . . . .
F17 F -0.4436(3) 0.1928(3) 0.65388(12) 0.0359(9) Uani 1 1 d . . . . .
O135 O 0.6453(3) -0.1661(3) 0.81553(13) 0.0173(9) Uani 1 1 d . . . . .
F116 F 1.4854(3) 0.3326(3) 0.85595(13) 0.0411(10) Uani 1 1 d . . . . .
O6 O 0.1234(3) 0.3266(3) 0.70271(12) 0.0162(9) Uani 1 1 d . . . . .
F16 F -0.3931(3) 0.1551(3) 0.56763(12) 0.0416(10) Uani 1 1 d . . . . .
O26 O 0.7184(3) 0.4888(3) 0.80650(13) 0.0201(9) Uani 1 1 d . . . . .
O126 O 0.3162(3) 0.0248(3) 0.68900(13) 0.0188(8) Uani 1 1 d . U . . .
F15 F -0.2815(3) 0.2946(3) 0.63015(15) 0.0465(10) Uani 1 1 d . . . . .
F115 F 1.4192(3) 0.3586(3) 0.93957(13) 0.0533(11) Uani 1 1 d . . . . .
F117 F 1.3215(3) 0.2229(3) 0.87222(15) 0.0503(10) Uani 1 1 d . . . . .
N7 N 0.1092(4) 0.1452(3) 0.69196(14) 0.0135(8) Uani 1 1 d . U . . .
H7 H 0.155181 0.098844 0.697572 0.016 Uiso 1 1 calc R U . . .
N24 N 0.6661(4) 0.6122(3) 0.76098(15) 0.0179(11) Uani 1 1 d . U . . .
H24 H 0.641468 0.672970 0.765130 0.022 Uiso 1 1 calc R U . . .
N107 N 0.9244(4) 0.3735(3) 0.81894(15) 0.0149(10) Uani 1 1 d . . . . .
H107 H 0.877612 0.420786 0.815914 0.018 Uiso 1 1 calc R U . . .
N1 N 0.4379(4) 0.5128(3) 0.66857(15) 0.0141(9) Uani 1 1 d . U . . .
N101 N 0.5883(4) -0.0008(3) 0.83047(16) 0.0141(10) Uani 1 1 d . . . . .
N124 N 0.3659(3) -0.0989(3) 0.73455(15) 0.0145(9) Uani 1 1 d . U . . .
H124 H 0.391013 -0.159362 0.730914 0.017 Uiso 1 1 calc R U . . .
N38 N 0.2209(4) 0.5333(4) 0.68470(14) 0.0167(8) Uani 1 1 d . U . . .
H38 H 0.202022 0.465559 0.681972 0.020 Uiso 1 1 calc R U . . .
N104 N 0.7215(4) 0.2568(3) 0.79524(14) 0.0147(10) Uani 1 1 d . U . . .
H104 H 0.686147 0.311145 0.793628 0.018 Uiso 1 1 calc R U . . .
N4 N 0.3127(4) 0.2615(3) 0.71171(14) 0.0153(8) Uani 1 1 d . U . . .
H4 H 0.348772 0.207777 0.713785 0.018 Uiso 1 1 calc R U . . .
N127 N 0.3599(4) -0.1352(3) 0.63595(15) 0.0156(8) Uani 1 1 d . U . . .
H127 H 0.400457 -0.187210 0.636721 0.019 Uiso 1 1 calc R U . . .
N136 N 0.8049(4) -0.0229(3) 0.81420(15) 0.0151(10) Uani 1 1 d . . . . .
H136 H 0.825287 0.045184 0.818050 0.018 Uiso 1 1 calc R U . . .
N27 N 0.6770(4) 0.6477(3) 0.85905(15) 0.0167(10) Uani 1 1 d . . . . .
H27 H 0.647275 0.704795 0.857989 0.020 Uiso 1 1 calc R U . . .
C8 C -0.0285(5) 0.1061(4) 0.67345(19) 0.0112(10) Uani 1 1 d . U . . .
C9 C -0.1130(4) 0.1713(4) 0.65908(18) 0.0139(13) Uani 1 1 d . . . . .
H9 H -0.080779 0.243834 0.662909 0.017 Uiso 1 1 calc R U . . .
C108 C 1.0621(5) 0.4118(4) 0.83497(19) 0.0139(12) Uani 1 1 d . . . . .
C110 C 1.2822(5) 0.3934(4) 0.8662(2) 0.0130(12) Uani 1 1 d . . . . .
C10 C -0.2471(5) 0.1247(4) 0.63881(19) 0.0136(13) Uani 1 1 d . . . . .
C25 C 0.6893(5) 0.5794(5) 0.8084(2) 0.0151(12) Uani 1 1 d . . . . .
C105 C 0.8558(5) 0.2699(5) 0.80758(19) 0.0153(12) Uani 1 1 d . . . . .
C113 C 1.1140(5) 0.5172(4) 0.83655(18) 0.0150(13) Uani 1 1 d . U . . .
H113 H 1.057562 0.559971 0.826649 0.018 Uiso 1 1 calc R U . . .
C3 C 0.3952(5) 0.3659(4) 0.71861(18) 0.0147(9) Uani 1 1 d . U . . .
H3A H 0.485065 0.365692 0.734299 0.018 Uiso 1 1 calc R U . . .
H3B H 0.360596 0.419311 0.746303 0.018 Uiso 1 1 calc R U . . .
C14 C -0.3412(5) 0.1926(5) 0.6226(2) 0.0170(13) Uani 1 1 d . . . . .
C112 C 1.2488(5) 0.5602(4) 0.85265(19) 0.0151(13) Uani 1 1 d . . . . .
C18 C -0.2716(5) -0.1607(5) 0.6446(2) 0.0224(14) Uani 1 1 d . . . . .
C118 C 1.3050(5) 0.6711(5) 0.8514(2) 0.0176(13) Uani 1 1 d . . . . .
C13 C -0.0799(5) -0.0014(4) 0.66849(18) 0.0137(12) Uani 1 1 d . . . . .
H13 H -0.023965 -0.044403 0.678519 0.016 Uiso 1 1 calc R U . . .
C11 C -0.2986(5) 0.0179(4) 0.63382(18) 0.0150(13) Uani 1 1 d . . . . .
H11 H -0.388240 -0.011168 0.620716 0.018 Uiso 1 1 calc R U . . .
C134 C 0.6788(5) -0.0685(4) 0.81943(19) 0.0128(12) Uani 1 1 d . . . . .
C103 C 0.6374(4) 0.1505(4) 0.78473(19) 0.0163(12) Uani 1 1 d . . . . .
H10A H 0.673834 0.098995 0.756647 0.020 Uiso 1 1 calc R U . . .
H10B H 0.548547 0.151791 0.768401 0.020 Uiso 1 1 calc R U . . .
C2 C 0.4009(5) 0.3978(4) 0.66160(19) 0.0166(11) Uani 1 1 d . U . . .
H2A H 0.464749 0.362561 0.639926 0.020 Uiso 1 1 calc R U . . .
H2B H 0.313982 0.371222 0.638803 0.020 Uiso 1 1 calc R U . . .
C12 C -0.2128(5) -0.0456(4) 0.64892(19) 0.0105(12) Uani 1 1 d . . . . .
C111 C 1.3347(5) 0.4970(4) 0.86733(19) 0.0156(13) Uani 1 1 d . . . . .
H111 H 1.425666 0.524757 0.877635 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1773(5) 0.2483(4) 0.7019(2) 0.0143(9) Uani 1 1 d . U . . .
C129 C 0.1568(4) -0.1427(4) 0.57119(18) 0.0186(13) Uani 1 1 d . . . . .
H12A H 0.121901 -0.210049 0.579680 0.022 Uiso 1 1 calc R U . . .
H12B H 0.127857 -0.085929 0.599034 0.022 Uiso 1 1 calc R U . . .
C102 C 0.6279(5) 0.1141(4) 0.84027(18) 0.0144(12) Uani 1 1 d . . . . .
H10C H 0.714105 0.138201 0.863736 0.017 Uiso 1 1 calc R U . . .
H10D H 0.563901 0.148806 0.862143 0.017 Uiso 1 1 calc R U . . .
C125 C 0.3449(5) -0.0657(4) 0.6868(2) 0.0143(9) Uani 1 1 d . U . . .
C23 C 0.6800(4) 0.5517(4) 0.70313(18) 0.0169(13) Uani 1 1 d . . . . .
H23A H 0.678298 0.477333 0.702837 0.020 Uiso 1 1 calc R U . . .
H23B H 0.766155 0.580072 0.692796 0.020 Uiso 1 1 calc R U . . .
C123 C 0.3481(4) -0.0378(4) 0.79189(18) 0.0155(13) Uani 1 1 d . . . . .
H12C H 0.260119 -0.064832 0.800990 0.019 Uiso 1 1 calc R U . . .
H12D H 0.353146 0.036954 0.792258 0.019 Uiso 1 1 calc R U . . .
C22 C 0.5715(5) 0.5555(4) 0.65813(19) 0.0175(13) Uani 1 1 d . . . . .
H22A H 0.576434 0.629556 0.657107 0.021 Uiso 1 1 calc R U . . .
H22B H 0.587943 0.514926 0.620390 0.021 Uiso 1 1 calc R U . . .
C39 C 0.1189(5) 0.5980(4) 0.69646(19) 0.0173(9) Uani 1 1 d . U . . .
H39A H 0.160170 0.668266 0.721646 0.021 Uiso 1 1 calc R U . . .
H39B H 0.053629 0.564222 0.717026 0.021 Uiso 1 1 calc R U . . .
C36 C 0.3468(5) 0.5800(4) 0.6780(2) 0.0156(9) Uani 1 1 d . U . . .
C109 C 1.1484(5) 0.3471(4) 0.85020(18) 0.0145(13) Uani 1 1 d . . . . .
H109 H 1.116241 0.275815 0.849454 0.017 Uiso 1 1 calc R U . . .
C114 C 1.3753(6) 0.3265(5) 0.8833(2) 0.0264(15) Uani 1 1 d . . . . .
C28 C 0.7109(5) 0.6313(5) 0.91559(19) 0.0225(14) Uani 1 1 d . . . . .
H28A H 0.676978 0.556695 0.914066 0.027 Uiso 1 1 calc R U . . .
H28B H 0.666274 0.675441 0.943894 0.027 Uiso 1 1 calc R U . . .
C128 C 0.3088(4) -0.1233(4) 0.58038(18) 0.0167(10) Uani 1 1 d . U . . .
H12E H 0.339631 -0.173703 0.549556 0.020 Uiso 1 1 calc R U . . .
H12F H 0.344805 -0.051196 0.578006 0.020 Uiso 1 1 calc R U . . .
C137 C 0.9063(5) -0.0884(4) 0.80212(19) 0.0188(13) Uani 1 1 d . . . . .
H13A H 0.972866 -0.053864 0.782367 0.023 Uiso 1 1 calc R U . . .
H13B H 0.864787 -0.157782 0.776080 0.023 Uiso 1 1 calc R U . . .
C138 C 0.9752(5) -0.1058(5) 0.85549(19) 0.0217(14) Uani 1 1 d . . . . .
H13C H 0.907510 -0.135881 0.876385 0.026 Uiso 1 1 calc R U . . .
H13D H 1.030140 -0.158903 0.843310 0.026 Uiso 1 1 calc R U . . .
C40 C 0.0469(5) 0.6126(4) 0.64216(19) 0.0174(9) Uani 1 1 d . U . . .
H40A H 0.112989 0.641873 0.620338 0.021 Uiso 1 1 calc R U . . .
H40B H -0.009362 0.664836 0.653757 0.021 Uiso 1 1 calc R U . . .
C41 C -0.0396(5) 0.5090(4) 0.60236(19) 0.0170(10) Uani 1 1 d . U . . .
H41A H -0.095267 0.472099 0.625167 0.020 Uiso 1 1 calc R U . . .
H41B H 0.017528 0.461602 0.584185 0.020 Uiso 1 1 calc R U . . .
C139 C 1.0615(5) -0.0075(4) 0.89655(19) 0.0223(14) Uani 1 1 d . . . . .
H13E H 1.005076 0.042010 0.913003 0.027 Uiso 1 1 calc R U . . .
H13F H 1.122268 0.028028 0.874912 0.027 Uiso 1 1 calc R U . . .
C131 C -0.0568(5) -0.1562(5) 0.50952(19) 0.0250(14) Uani 1 1 d . . . . .
H13G H -0.094296 -0.221247 0.519747 0.030 Uiso 1 1 calc R U . . .
H13H H -0.074532 -0.095735 0.538813 0.030 Uiso 1 1 calc R U . . .
C43 C -0.2232(5) 0.4355(5) 0.5159(2) 0.0254(15) Uani 1 1 d . . . . .
H43A H -0.276483 0.398583 0.539371 0.031 Uiso 1 1 calc R U . . .
H43B H -0.171142 0.386397 0.494975 0.031 Uiso 1 1 calc R U . . .
C140 C 1.1426(5) -0.0312(5) 0.9457(2) 0.0256(15) Uani 1 1 d . . . . .
H14A H 1.081159 -0.063419 0.968284 0.031 Uiso 1 1 calc R U . . .
H14B H 1.194723 -0.083964 0.928981 0.031 Uiso 1 1 calc R U . . .
C130 C 0.0954(4) -0.1472(4) 0.51148(19) 0.0203(13) Uani 1 1 d . . . . .
H13I H 0.114765 -0.208782 0.483524 0.024 Uiso 1 1 calc R U . . .
H13J H 0.134369 -0.082801 0.500988 0.024 Uiso 1 1 calc R U . . .
C133 C -0.2770(5) -0.1601(5) 0.4551(2) 0.0307(15) Uani 1 1 d . . . . .
H13K H -0.317366 -0.155403 0.418745 0.046 Uiso 1 1 calc R U . . .
H13L H -0.288645 -0.100023 0.485515 0.046 Uiso 1 1 calc R U . . .
H13M H -0.318701 -0.225843 0.462678 0.046 Uiso 1 1 calc R U . . .
C132 C -0.1281(5) -0.1585(4) 0.45232(19) 0.0261(13) Uani 1 1 d . . . . .
H13N H -0.116867 -0.221825 0.423233 0.031 Uiso 1 1 calc R U . . .
H13O H -0.088235 -0.095660 0.440613 0.031 Uiso 1 1 calc R U . . .
C122 C 0.4534(4) -0.0449(4) 0.83801(19) 0.0171(13) Uani 1 1 d . . . . .
H12G H 0.433855 -0.006914 0.875748 0.021 Uiso 1 1 calc R U . . .
H12H H 0.447596 -0.119786 0.837521 0.021 Uiso 1 1 calc R U . . .
C42 C -0.1284(5) 0.5341(4) 0.55542(19) 0.0209(14) Uani 1 1 d . . . . .
H42A H -0.180719 0.585202 0.574042 0.025 Uiso 1 1 calc R U . . .
H42B H -0.071599 0.568176 0.531875 0.025 Uiso 1 1 calc R U . . .
C29 C 0.8598(5) 0.6582(5) 0.93591(19) 0.0268(15) Uani 1 1 d . . . . .
H29A H 0.903930 0.609252 0.909945 0.032 Uiso 1 1 calc R U . . .
H29B H 0.895985 0.730669 0.934210 0.032 Uiso 1 1 calc R U . . .
C30 C 0.8894(5) 0.6502(5) 0.99711(19) 0.0306(16) Uani 1 1 d . . . . .
H30A H 0.869650 0.575011 0.996937 0.037 Uiso 0.453(15) 1 calc R U P A 1
H30B H 0.830351 0.686787 1.021293 0.037 Uiso 0.453(15) 1 calc R U P A 1
H30C H 0.822146 0.594239 1.003924 0.037 Uiso 0.547(15) 1 calc R U P A 2
H30D H 0.883711 0.717687 1.024199 0.037 Uiso 0.547(15) 1 calc R U P A 2
C142 C 1.3179(5) 0.0361(5) 1.0324(2) 0.0383(18) Uani 1 1 d . . . . .
H14C H 1.371284 -0.013661 1.014492 0.057 Uiso 1 1 calc R U . . .
H14D H 1.259367 0.003573 1.055301 0.057 Uiso 1 1 calc R U . . .
H14E H 1.375235 0.099961 1.056756 0.057 Uiso 1 1 calc R U . . .
C44 C -0.3166(5) 0.4648(5) 0.4721(2) 0.0376(18) Uani 1 1 d . . . . .
H44A H -0.264497 0.498326 0.447481 0.056 Uiso 1 1 calc R U . . .
H44B H -0.368012 0.513768 0.492535 0.056 Uiso 1 1 calc R U . . .
H44C H -0.375762 0.400789 0.448951 0.056 Uiso 1 1 calc R U . . .
C35 C 1.2798(5) 0.6838(5) 1.0205(2) 0.0422(18) Uani 1 1 d . U . . .
H35A H 1.334394 0.637162 1.000515 0.063 Uiso 0.453(15) 1 calc R U P A 1
H35B H 1.276832 0.676863 1.059232 0.063 Uiso 0.453(15) 1 calc R U P A 1
H35C H 1.317104 0.756907 1.021826 0.063 Uiso 0.453(15) 1 calc R U P A 1
H35D H 1.289584 0.624834 0.988934 0.063 Uiso 0.547(15) 1 calc R U P A 2
H35E H 1.281714 0.662071 1.055767 0.063 Uiso 0.547(15) 1 calc R U P A 2
H35F H 1.351798 0.743574 1.024090 0.063 Uiso 0.547(15) 1 calc R U P A 2
C141 C 1.2363(5) 0.0651(5) 0.9861(2) 0.0345(17) Uani 1 1 d . . . . .
H14F H 1.296129 0.099320 0.963691 0.041 Uiso 1 1 calc R U . . .
H14G H 1.184379 0.116791 1.004540 0.041 Uiso 1 1 calc R U . . .
C32 C 1.1358(15) 0.6519(15) 0.9878(6) 0.026(4) Uani 0.453(15) 1 d . U P A 1
H32A H 1.135672 0.676689 0.953054 0.031 Uiso 0.453(15) 1 calc R U P A 1
H32B H 1.109029 0.574148 0.976111 0.031 Uiso 0.453(15) 1 calc R U P A 1
C31 C 1.0358(13) 0.6988(15) 1.0244(6) 0.023(4) Uani 0.453(15) 1 d . U P A 1
H31A H 1.052232 0.776033 1.029714 0.028 Uiso 0.453(15) 1 calc R U P A 1
H31B H 1.048239 0.686129 1.062297 0.028 Uiso 0.453(15) 1 calc R U P A 1
C33 C 1.0321(11) 0.6242(12) 1.0090(5) 0.028(3) Uani 0.547(15) 1 d . U P A 2
H33A H 1.040311 0.608706 1.046318 0.034 Uiso 0.547(15) 1 calc R U P A 2
H33B H 1.041160 0.560539 0.979586 0.034 Uiso 0.547(15) 1 calc R U P A 2
C34 C 1.1442(14) 0.7175(14) 1.0086(6) 0.035(4) Uani 0.547(15) 1 d . U P A 2
H34A H 1.137321 0.781513 1.038245 0.042 Uiso 0.547(15) 1 calc R U P A 2
H34B H 1.137942 0.733327 0.971256 0.042 Uiso 0.547(15) 1 calc R U P A 2


_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
F19 C18 1.328(5) . ?
F120 C118 1.348(5) . ?
F20 C18 1.333(6) . ?
F121 C118 1.351(6) . ?
F21 C18 1.361(6) . ?
F119 C118 1.349(6) . ?
O106 C105 1.240(6) . ?
O37 C36 1.232(6) . ?
F17 C14 1.332(5) . ?
O135 C134 1.244(6) . ?
F116 C114 1.343(5) . ?
O6 C5 1.242(6) . ?
F16 C14 1.323(5) . ?
O26 C25 1.263(6) . ?
O126 C125 1.259(6) . ?
F15 C14 1.332(6) . ?
F115 C114 1.331(6) . ?
F117 C114 1.324(6) . ?
N7 H7 0.8600 . ?
N7 C8 1.413(6) . ?
N7 C5 1.363(6) . ?
N24 H24 0.8600 . ?
N24 C25 1.336(5) . ?
N24 C23 1.446(5) . ?
N107 H107 0.8600 . ?
N107 C108 1.403(6) . ?
N107 C105 1.366(6) . ?
N1 C2 1.452(6) . ?
N1 C22 1.449(5) . ?
N1 C36 1.382(6) . ?
N101 C134 1.384(6) . ?
N101 C102 1.443(6) . ?
N101 C122 1.444(5) . ?
N124 H124 0.8600 . ?
N124 C125 1.343(5) . ?
N124 C123 1.449(5) . ?
N38 H38 0.8600 . ?
N38 C39 1.454(5) . ?
N38 C36 1.367(6) . ?
N104 H104 0.8600 . ?
N104 C105 1.357(6) . ?
N104 C103 1.457(6) . ?
N4 H4 0.8600 . ?
N4 C3 1.442(6) . ?
N4 C5 1.363(6) . ?
N127 H127 0.8600 . ?
N127 C125 1.363(6) . ?
N127 C128 1.455(5) . ?
N136 H136 0.8600 . ?
N136 C134 1.354(6) . ?
N136 C137 1.456(5) . ?
N27 H27 0.8600 . ?
N27 C25 1.345(6) . ?
N27 C28 1.456(5) . ?
C8 C9 1.399(6) . ?
C8 C13 1.388(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.401(6) . ?
C108 C113 1.382(7) . ?
C108 C109 1.416(6) . ?
C110 C111 1.364(7) . ?
C110 C109 1.383(6) . ?
C110 C114 1.504(7) . ?
C10 C14 1.513(7) . ?
C10 C11 1.379(7) . ?
C113 H113 0.9300 . ?
C113 C112 1.384(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.532(5) . ?
C112 C118 1.477(7) . ?
C112 C111 1.393(7) . ?
C18 C12 1.499(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.399(7) . ?
C103 H10A 0.9700 . ?
C103 H10B 0.9700 . ?
C103 C102 1.530(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C111 H111 0.9300 . ?
C129 H12A 0.9700 . ?
C129 H12B 0.9700 . ?
C129 C128 1.523(6) . ?
C129 C130 1.509(6) . ?
C102 H10C 0.9700 . ?
C102 H10D 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.511(6) . ?
C123 H12C 0.9700 . ?
C123 H12D 0.9700 . ?
C123 C122 1.523(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.524(6) . ?
C109 H109 0.9300 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C29 1.520(6) . ?
C128 H12E 0.9700 . ?
C128 H12F 0.9700 . ?
C137 H13A 0.9700 . ?
C137 H13B 0.9700 . ?
C137 C138 1.508(6) . ?
C138 H13C 0.9700 . ?
C138 H13D 0.9700 . ?
C138 C139 1.502(7) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.534(6) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.535(6) . ?
C139 H13E 0.9700 . ?
C139 H13F 0.9700 . ?
C139 C140 1.522(6) . ?
C131 H13G 0.9700 . ?
C131 H13H 0.9700 . ?
C131 C130 1.538(6) . ?
C131 C132 1.501(6) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C42 1.527(7) . ?
C43 C44 1.536(6) . ?
C140 H14A 0.9700 . ?
C140 H14B 0.9700 . ?
C140 C141 1.513(7) . ?
C130 H13I 0.9700 . ?
C130 H13J 0.9700 . ?
C133 H13K 0.9600 . ?
C133 H13L 0.9600 . ?
C133 H13M 0.9600 . ?
C133 C132 1.527(6) . ?
C132 H13N 0.9700 . ?
C132 H13O 0.9700 . ?
C122 H12G 0.9700 . ?
C122 H12H 0.9700 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C29 C30 1.514(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
C30 H30D 0.9700 . ?
C30 C31 1.550(15) . ?
C30 C33 1.578(12) . ?
C142 H14C 0.9600 . ?
C142 H14D 0.9600 . ?
C142 H14E 0.9600 . ?
C142 C141 1.507(6) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C35 H35D 0.9600 . ?
C35 H35E 0.9600 . ?
C35 H35F 0.9600 . ?
C35 C32 1.557(15) . ?
C35 C34 1.557(13) . ?
C141 H14F 0.9700 . ?
C141 H14G 0.9700 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C31 1.50(2) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.53(2) . ?
C34 H34A 0.9700 . ?
C34 H34B 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
C8 N7 H7 116.4 . . ?
C5 N7 H7 116.4 . . ?
C5 N7 C8 127.1(4) . . ?
C25 N24 H24 118.1 . . ?
C25 N24 C23 123.8(5) . . ?
C23 N24 H24 118.1 . . ?
C108 N107 H107 116.1 . . ?
C105 N107 H107 116.1 . . ?
C105 N107 C108 127.7(5) . . ?
C22 N1 C2 118.1(4) . . ?
C36 N1 C2 122.5(4) . . ?
C36 N1 C22 118.9(4) . . ?
C134 N101 C102 121.9(4) . . ?
C134 N101 C122 119.0(4) . . ?
C102 N101 C122 118.8(4) . . ?
C125 N124 H124 118.4 . . ?
C125 N124 C123 123.1(4) . . ?
C123 N124 H124 118.4 . . ?
C39 N38 H38 120.0 . . ?
C36 N38 H38 120.0 . . ?
C36 N38 C39 120.1(4) . . ?
C105 N104 H104 120.1 . . ?
C105 N104 C103 119.8(4) . . ?
C103 N104 H104 120.1 . . ?
C3 N4 H4 120.1 . . ?
C5 N4 H4 120.1 . . ?
C5 N4 C3 119.7(4) . . ?
C125 N127 H127 119.3 . . ?
C125 N127 C128 121.3(4) . . ?
C128 N127 H127 119.3 . . ?
C134 N136 H136 119.8 . . ?
C134 N136 C137 120.5(4) . . ?
C137 N136 H136 119.8 . . ?
C25 N27 H27 117.9 . . ?
C25 N27 C28 124.2(5) . . ?
C28 N27 H27 117.9 . . ?
C9 C8 N7 122.3(5) . . ?
C13 C8 N7 118.2(5) . . ?
C13 C8 C9 119.5(5) . . ?
C8 C9 H9 120.8 . . ?
C8 C9 C10 118.5(5) . . ?
C10 C9 H9 120.8 . . ?
N107 C108 C109 122.5(5) . . ?
C113 C108 N107 118.3(5) . . ?
C113 C108 C109 119.3(5) . . ?
C111 C110 C109 123.4(5) . . ?
C111 C110 C114 118.0(5) . . ?
C109 C110 C114 118.6(5) . . ?
C9 C10 C14 119.9(5) . . ?
C11 C10 C9 122.2(5) . . ?
C11 C10 C14 117.9(5) . . ?
O26 C25 N24 122.9(5) . . ?
O26 C25 N27 121.1(4) . . ?
N24 C25 N27 116.0(5) . . ?
O106 C105 N107 123.4(5) . . ?
O106 C105 N104 121.7(5) . . ?
N104 C105 N107 114.9(5) . . ?
C108 C113 H113 119.5 . . ?
C108 C113 C112 121.0(5) . . ?
C112 C113 H113 119.5 . . ?
N4 C3 H3A 109.0 . . ?
N4 C3 H3B 109.0 . . ?
N4 C3 C2 112.8(4) . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
F17 C14 F15 107.4(5) . . ?
F17 C14 C10 111.3(4) . . ?
F16 C14 F17 106.5(4) . . ?
F16 C14 F15 107.0(4) . . ?
F16 C14 C10 111.6(4) . . ?
F15 C14 C10 112.8(4) . . ?
C113 C112 C118 120.8(5) . . ?
C113 C112 C111 120.2(5) . . ?
C111 C112 C118 118.9(5) . . ?
F19 C18 F20 107.9(4) . . ?
F19 C18 F21 105.9(4) . . ?
F19 C18 C12 111.8(4) . . ?
F20 C18 F21 106.6(4) . . ?
F20 C18 C12 113.2(4) . . ?
F21 C18 C12 111.0(4) . . ?
F120 C118 F121 105.9(4) . . ?
F120 C118 F119 105.3(4) . . ?
F120 C118 C112 112.9(4) . . ?
F121 C118 C112 113.5(4) . . ?
F119 C118 F121 105.6(4) . . ?
F119 C118 C112 112.8(4) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.1(5) . . ?
C12 C13 H13 119.4 . . ?
C10 C11 H11 120.8 . . ?
C10 C11 C12 118.5(5) . . ?
C12 C11 H11 120.8 . . ?
O135 C134 N101 121.0(5) . . ?
O135 C134 N136 122.1(5) . . ?
N136 C134 N101 116.8(5) . . ?
N104 C103 H10A 109.2 . . ?
N104 C103 H10B 109.2 . . ?
N104 C103 C102 112.0(4) . . ?
H10A C103 H10B 107.9 . . ?
C102 C103 H10A 109.2 . . ?
C102 C103 H10B 109.2 . . ?
N1 C2 C3 114.4(4) . . ?
N1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C13 C12 C18 122.2(5) . . ?
C13 C12 C11 120.2(5) . . ?
C11 C12 C18 117.6(5) . . ?
C110 C111 C112 118.3(5) . . ?
C110 C111 H111 120.8 . . ?
C112 C111 H111 120.8 . . ?
O6 C5 N7 124.2(5) . . ?
O6 C5 N4 120.8(5) . . ?
N7 C5 N4 115.0(5) . . ?
H12A C129 H12B 107.4 . . ?
C128 C129 H12A 108.3 . . ?
C128 C129 H12B 108.3 . . ?
C130 C129 H12A 108.3 . . ?
C130 C129 H12B 108.3 . . ?
C130 C129 C128 116.0(3) . . ?
N101 C102 C103 114.1(4) . . ?
N101 C102 H10C 108.7 . . ?
N101 C102 H10D 108.7 . . ?
C103 C102 H10C 108.7 . . ?
C103 C102 H10D 108.7 . . ?
H10C C102 H10D 107.6 . . ?
O126 C125 N124 122.2(5) . . ?
O126 C125 N127 122.2(4) . . ?
N124 C125 N127 115.6(5) . . ?
N24 C23 H23A 109.0 . . ?
N24 C23 H23B 109.0 . . ?
N24 C23 C22 113.1(4) . . ?
H23A C23 H23B 107.8 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
N124 C123 H12C 109.2 . . ?
N124 C123 H12D 109.2 . . ?
N124 C123 C122 111.9(4) . . ?
H12C C123 H12D 107.9 . . ?
C122 C123 H12C 109.2 . . ?
C122 C123 H12D 109.2 . . ?
N1 C22 C23 113.8(4) . . ?
N1 C22 H22A 108.8 . . ?
N1 C22 H22B 108.8 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
N38 C39 H39A 108.8 . . ?
N38 C39 H39B 108.8 . . ?
N38 C39 C40 113.7(4) . . ?
H39A C39 H39B 107.7 . . ?
C40 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
O37 C36 N1 122.2(5) . . ?
O37 C36 N38 121.9(5) . . ?
N38 C36 N1 115.9(5) . . ?
C108 C109 H109 121.1 . . ?
C110 C109 C108 117.8(5) . . ?
C110 C109 H109 121.1 . . ?
F116 C114 C110 111.8(4) . . ?
F115 C114 F116 105.5(5) . . ?
F115 C114 C110 112.5(5) . . ?
F117 C114 F116 106.6(5) . . ?
F117 C114 F115 105.8(5) . . ?
F117 C114 C110 114.0(5) . . ?
N27 C28 H28A 108.7 . . ?
N27 C28 H28B 108.7 . . ?
N27 C28 C29 114.0(4) . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
N127 C128 C129 112.8(3) . . ?
N127 C128 H12E 109.0 . . ?
N127 C128 H12F 109.0 . . ?
C129 C128 H12E 109.0 . . ?
C129 C128 H12F 109.0 . . ?
H12E C128 H12F 107.8 . . ?
N136 C137 H13A 108.8 . . ?
N136 C137 H13B 108.8 . . ?
N136 C137 C138 113.8(4) . . ?
H13A C137 H13B 107.7 . . ?
C138 C137 H13A 108.8 . . ?
C138 C137 H13B 108.8 . . ?
C137 C138 H13C 108.4 . . ?
C137 C138 H13D 108.4 . . ?
H13C C138 H13D 107.4 . . ?
C139 C138 C137 115.7(5) . . ?
C139 C138 H13C 108.4 . . ?
C139 C138 H13D 108.4 . . ?
C39 C40 H40A 108.7 . . ?
C39 C40 H40B 108.7 . . ?
C39 C40 C41 114.4(4) . . ?
H40A C40 H40B 107.6 . . ?
C41 C40 H40A 108.7 . . ?
C41 C40 H40B 108.7 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 C42 110.8(4) . . ?
H41A C41 H41B 108.1 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C138 C139 H13E 108.8 . . ?
C138 C139 H13F 108.8 . . ?
C138 C139 C140 113.8(5) . . ?
H13E C139 H13F 107.7 . . ?
C140 C139 H13E 108.8 . . ?
C140 C139 H13F 108.8 . . ?
H13G C131 H13H 107.5 . . ?
C130 C131 H13G 108.4 . . ?
C130 C131 H13H 108.4 . . ?
C132 C131 H13G 108.4 . . ?
C132 C131 H13H 108.4 . . ?
C132 C131 C130 115.4(4) . . ?
H43A C43 H43B 107.9 . . ?
C42 C43 H43A 109.1 . . ?
C42 C43 H43B 109.1 . . ?
C42 C43 C44 112.4(5) . . ?
C44 C43 H43A 109.1 . . ?
C44 C43 H43B 109.1 . . ?
C139 C140 H14A 108.4 . . ?
C139 C140 H14B 108.4 . . ?
H14A C140 H14B 107.5 . . ?
C141 C140 C139 115.4(5) . . ?
C141 C140 H14A 108.4 . . ?
C141 C140 H14B 108.4 . . ?
C129 C130 C131 110.8(3) . . ?
C129 C130 H13I 109.5 . . ?
C129 C130 H13J 109.5 . . ?
C131 C130 H13I 109.5 . . ?
C131 C130 H13J 109.5 . . ?
H13I C130 H13J 108.1 . . ?
H13K C133 H13L 109.5 . . ?
H13K C133 H13M 109.5 . . ?
H13L C133 H13M 109.5 . . ?
C132 C133 H13K 109.5 . . ?
C132 C133 H13L 109.5 . . ?
C132 C133 H13M 109.5 . . ?
C131 C132 C133 112.1(4) . . ?
C131 C132 H13N 109.2 . . ?
C131 C132 H13O 109.2 . . ?
C133 C132 H13N 109.2 . . ?
C133 C132 H13O 109.2 . . ?
H13N C132 H13O 107.9 . . ?
N101 C122 C123 113.8(4) . . ?
N101 C122 H12G 108.8 . . ?
N101 C122 H12H 108.8 . . ?
C123 C122 H12G 108.8 . . ?
C123 C122 H12H 108.8 . . ?
H12G C122 H12H 107.7 . . ?
C41 C42 H42A 108.7 . . ?
C41 C42 H42B 108.7 . . ?
C43 C42 C41 114.0(4) . . ?
C43 C42 H42A 108.7 . . ?
C43 C42 H42B 108.7 . . ?
H42A C42 H42B 107.6 . . ?
C28 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 C28 112.1(4) . . ?
C30 C29 H29A 109.2 . . ?
C30 C29 H29B 109.2 . . ?
C29 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C29 C30 H30C 109.1 . . ?
C29 C30 H30D 109.1 . . ?
C29 C30 C31 114.1(6) . . ?
C29 C30 C33 112.7(5) . . ?
H30A C30 H30B 107.6 . . ?
H30C C30 H30D 107.8 . . ?
C31 C30 H30A 108.7 . . ?
C31 C30 H30B 108.7 . . ?
C33 C30 H30C 109.1 . . ?
C33 C30 H30D 109.1 . . ?
H14C C142 H14D 109.5 . . ?
H14C C142 H14E 109.5 . . ?
H14D C142 H14E 109.5 . . ?
C141 C142 H14C 109.5 . . ?
C141 C142 H14D 109.5 . . ?
C141 C142 H14E 109.5 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
H35D C35 H35E 109.5 . . ?
H35D C35 H35F 109.5 . . ?
H35E C35 H35F 109.5 . . ?
C32 C35 H35A 109.5 . . ?
C32 C35 H35B 109.5 . . ?
C32 C35 H35C 109.5 . . ?
C34 C35 H35D 109.5 . . ?
C34 C35 H35E 109.5 . . ?
C34 C35 H35F 109.5 . . ?
C140 C141 H14F 109.0 . . ?
C140 C141 H14G 109.0 . . ?
C142 C141 C140 113.0(5) . . ?
C142 C141 H14F 109.0 . . ?
C142 C141 H14G 109.0 . . ?
H14F C141 H14G 107.8 . . ?
C35 C32 H32A 109.1 . . ?
C35 C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C31 C32 C35 112.5(14) . . ?
C31 C32 H32A 109.1 . . ?
C31 C32 H32B 109.1 . . ?
C30 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C32 C31 C30 112.7(14) . . ?
C32 C31 H31A 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C30 C33 H33A 109.2 . . ?
C30 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C34 C33 C30 112.0(11) . . ?
C34 C33 H33A 109.2 . . ?
C34 C33 H33B 109.2 . . ?
C35 C34 H34A 110.1 . . ?
C35 C34 H34B 110.1 . . ?
C33 C34 C35 107.9(12) . . ?
C33 C34 H34A 110.1 . . ?
C33 C34 H34B 110.1 . . ?
H34A C34 H34B 108.4 . . ?

